WO2007066309A2 - Cosmetic composition comprising an ester of dimerdilinoleic acid and of polyol(s) and a semi-crystalline polymer - Google Patents

Cosmetic composition comprising an ester of dimerdilinoleic acid and of polyol(s) and a semi-crystalline polymer Download PDF

Info

Publication number
WO2007066309A2
WO2007066309A2 PCT/IB2006/054663 IB2006054663W WO2007066309A2 WO 2007066309 A2 WO2007066309 A2 WO 2007066309A2 IB 2006054663 W IB2006054663 W IB 2006054663W WO 2007066309 A2 WO2007066309 A2 WO 2007066309A2
Authority
WO
WIPO (PCT)
Prior art keywords
composition according
ester
acid
residue
semi
Prior art date
Application number
PCT/IB2006/054663
Other languages
French (fr)
Other versions
WO2007066309A3 (en
Inventor
Momoko Shimizu
Emiko Tokunaga
Original Assignee
L'oreal
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from FR0553799A external-priority patent/FR2894472B1/en
Application filed by L'oreal filed Critical L'oreal
Priority to CN200680045929.XA priority Critical patent/CN101355985B/en
Priority to JP2008543985A priority patent/JP5840339B2/en
Publication of WO2007066309A2 publication Critical patent/WO2007066309A2/en
Publication of WO2007066309A3 publication Critical patent/WO2007066309A3/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • A61K8/375Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39Derivatives containing from 2 to 10 oxyalkylene groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8105Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • A61K8/8111Homopolymers or copolymers of aliphatic olefines, e.g. polyethylene, polyisobutene; Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/85Polyesters
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/891Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/893Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • A61Q1/04Preparations containing skin colorants, e.g. pigments for lips
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • A61Q1/04Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06Lipsticks
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • A61Q1/08Preparations containing skin colorants, e.g. pigments for cheeks, e.g. rouge
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30Characterized by the absence of a particular group of ingredients
    • A61K2800/31Anhydrous
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54Polymers characterized by specific structures/properties

Definitions

  • Cosmetic composition comprising an ester of dimerdilinoleic acid and of polyol(s) and a semi-crystalline polymer
  • the present invention relates to cosmetic make-up and/or care compositions, intended to be applied to the skin and/or the lips, comprising an ester of dimerdilinoleic acid and of polyol(s), or an ester thereof, and having improved gloss staying power.
  • a composition according to the invention may in particular be a makeup and/or care product intended to be applied to the body, especially the face, and/or the lips, and may especially be a lipstick, a lip balm, a lip pencil, a liquid or solid foundation, especially cast as a stick or a dish, a concealer product, a skin colouring product, an eye makeup product, for instance eyeliners, in particular in pencil form, a mascara especially in cake form, an eyeshadow or a lip gloss.
  • compositions for which the properties of gloss and/or colour effect of the deposited film, after application on the skin and/or the lips, are desired. These properties generally contribute towards the desired aesthetic effect.
  • gloss oils such as oily polymers, for instance high- viscosity polybutenes, esters of fatty acids or of fatty alcohols of high carbon number (typically greater than 16) or certain plant oils.
  • the inventors have observed, surprisingly, that the use of certain esters of dimerdilinoleic acids and of polyol(s) or an ester thereof, for preparing cosmetic compositions, makes it possible to give these compositions improved mean gloss staying power, without affecting their combination of aesthetic properties, while at the same time affording a comfortable sensation on application.
  • the cosmetic compositions according to the invention do not cause any tacky sensation after they have been applied.
  • one subject of the present invention is a cosmetic composition for caring for and/or making up the skin and/or the lips, comprising at least one ester of dimerdilinoleic acid and of polyol(s), or an ester thereof, the viscosity of which, measured at about 25°C, is greater than or equal to about 20 000 mPa.s, and having a mean gloss staying power of greater than or equal to about 7.
  • a subject of the present invention is an anhydrous cosmetic composition for caring for and/or making up the skin and/or the lips, comprising at least one ester of dimerdilinoleic acid and of polyol(s), or an ester thereof, the viscosity of which, measured at about 25°C, is greater than or equal to about
  • an anhydrous cosmetic composition according to the invention comprises less than 5% by weight of water, or even less than 3% by weight of water and more particularly less than 1% by weight of water, relative to its total weight.
  • a subject of the present invention is a cosmetic composition for caring for and/or making up the skin and/or the lips comprising at least one ester of general formula (I) below:
  • OR 2 O represents a fatty alcohol dimer residue
  • OR 3 represents a hydrocarbon-based monoalcohol residue
  • - n is an integer ranging from 1 to 15,
  • a subject of the present invention is a cosmetic composition for caring for and/or making up the skin and/or the lips comprising at least one ester of general formula (II) below:
  • - n is an integer ranging from 1 to 15,
  • R'3 represents H or OR'3 represents a fatty acid residue
  • a subject of the present invention is the use of at least one ester of dimerdilinoleic acid and of polyol(s) or an ester thereof, in accordance with the invention, in combination with at least one semi-crystalline polymer, for the preparation of a cosmetic composition for caring for and/or making up the skin and/or the lips having improved gloss staying power.
  • the present invention makes it possible to provide cosmetic compositions whose gloss is also improved, while at the same time not causing any sensation of tack or of discomfort on application.
  • the present invention makes it possible to provide cosmetic compositions whose gloss staying power is also improved over time, and especially with regard to various external attacking factors, such as mealtimes or contact with a fabric.
  • the staying power colour of the composition according to the invention is advantageously not affected, or is even improved.
  • gloss is intended to denote the gloss of a composition as may be conventionally measured using a glossmeter, via the following method.
  • the gloss may be measured by means of a test performed in vitro using a Multi-Gloss 268 glossmeter (Minolta, Tokyo, Japan).
  • a first coat of cosmetic composition for example in the form of a lipstick, is applied to a sample of Bio-Skin synthetic skin (of the type Fat-Skin Beaulax, Tokyo, Japan) 3 cm x 4.5 cm in size, by application in the direction of the length of the support of contiguous strips of the said composition, so as to cover an area of 2.5 cm x 4 cm.
  • a second coat of composition is applied over the first coat in a similar manner to the first, offset widthwise by about half the width of a strip in order to obtain a surface uniformly covered with the said composition.
  • the gloss is measured using a Multi-Gloss glossmeter (Minolta, Tokyo, Japan) by measuring the reflectance at an angle of about 60° taken relative to the perpendicular to the surface.
  • the gloss is preferably measured about 10 minutes after applying the cosmetic composition.
  • the measurement is repeated at least five times.
  • the gloss of a cosmetic composition according to the present invention may be greater than or equal to about 20 and more particularly greater than or equal to about 22.
  • gloss staying power is intended to denote the staying power of the gloss of a composition as may conventionally be measured using a glossmeter via the following method.
  • a tissue is applied onto the sample of synthetic skin comprising the two coats of cosmetic compositions applied as defined above.
  • a tissue may be, for example, a Kleenex tissue.
  • the pressure of the tissue on the sample is applied by means of a press of mass
  • the measurement is repeated at least 5 times.
  • the lowest gloss value and the highest gloss value are removed, and a mean is determined on the remaining three values.
  • the gloss staying power of a cosmetic composition according to the present invention may be greater than or equal to about 7 and more particularly greater than or equal to about 8.
  • esters of dimerdilinoleic acid and of polyol(s) or an ester thereof the term "or an ester thereof is intended to denote one of the derivatives of these dimerdilinoleic acid esters of polyol(s) obtained either by reaction of alcohol function(s) of the polyol, which are not employed in bonds of ester type with acid functions of the dilinoleic acid, with one or more carboxylic functions of acid molecules other than dilinoleic acid or alternatively by reaction of acid functions of the dilinoleic dimer, which are not employed in bonds of ester type with alcohol functions of the polyol, with alcohol functions of alcohol molecules other than the polyol.
  • the dimerdilinoleic acid that is suitable for use in the present invention may be obtained by polymerization reaction, especially by intermolecular dimerization of at least one linoleic acid.
  • the oxidation stability of the compound may be improved by hydrogenating the double bonds remaining after the dimerization reaction.
  • the linoleic acid dimer may also be obtained by dimerization of the hydrogenated form of linoleic acid.
  • the hydrogenated form of the acid or of the diacid may be partial or total, and may correspond, for example, to the saturated form, which is more oxidation-stable.
  • the carboxylic functions of the dimerdilinoleic acid residue not engaged in the ester bond with the polyol residue (s) may be engaged in other ester bonds with other alcohol functions of alcohol molecules other than the polyol(s).
  • These alcohol molecules or residues may be monoalcohols or polyols.
  • hydrocarbon-based compounds comprising a hydroxyl function and containing from 4 to 40 carbon atoms, in particular from 6 to 36 carbon atoms, in particular from 8 to 32 carbon atoms, in particular from 16 to 28 carbon atoms and more particularly from 18 to 24 carbon atoms.
  • monoalcohols that are suitable for the invention, mention may be made, in a non-limiting manner, of butanol, pentanol, propanol, hexanol, heptanol, octanol, decanol, dodecanol, hexadecanol, octadecanol, eicosadecanol, phytosterol, isostearol, stearol, cetol, behenol, etc.
  • Polyo Is polyo Is
  • polyol is intended to denote any hydrocarbon-based compound comprising at least two hydroxyl functions and containing from 4 to 40 carbon atoms, in particular from 6 to 36 carbon atoms, in particular from 8 to 32 carbon atoms, in particular from 16 to 28 carbon atoms and more particularly from 18 to 24 carbon atoms.
  • the hydrocarbon-based chains may be interrupted, where appropriate, by the presence of at least one hetero atom, and especially an oxygen atom.
  • a polyol or a polyol ester that is suitable for use in the present invention may comprise, for example, from 2 to 12 hydroxyl functions, in particular from 2 to 8 hydroxyl functions, and more particularly from 4 to 6 hydroxyl functions.
  • the hydroxyl functions other than those already employed in an ester bond with the dimerdilinoleic acid, may also be employed, wholly or partly with other ester bonds via reactivity with acid molecules other than the dimerdilinoleic acid.
  • the polyol or an ester thereof that is suitable for use in the present invention may be chosen especially from linear, branched, cyclic or polycyclic, saturated or unsaturated alcohols.
  • the polyol may be chosen, for example, from a diol, a triol, a tetraol, or a pentaol, or an ester thereof.
  • the polyol may be a diol, or an ester thereof, chosen especially from a fatty alcohol dimer, a monoglycerol or polyglycerol, a C2-4 monoalkylene or polyalkylene glycol, 1,4-butanediol and pentaerythritol.
  • diols that are also suitable for use in the invention, mention may be made, in a non-exhaustive manner, of butanediol, pentanediol, propanediol, hexanediol, hexylene glycol, heptanediol, octanediol, nonanediol, decanediol, 1-decanediol, dodecanediol, tridecanediol, tetradecanediol, pentadecanediol, hexadecanediol, nonadecanediol, octadecanediol, cyclohexanediol, diglycerol, erythritol, pentaerythritol, xylitol, sorbitol, ethylene glycol and xylene glycol,
  • a fatty alcohol dimer may also be the product of hydrogenation, for example catalytic hydrogenation, of a fatty acid dimer, which is itself obtained by dimerization of at least one unsaturated fatty acid, especially of Cs to C34, especially of C 12 to C22, in particular of C 16 to C20 and more particularly of C 18 .
  • a fatty alcohol dimer may range from C 16 to C ⁇ s, especially from C24 to C44, in particular from C32 to C40 and more particularly may be of C36.
  • a fatty alcohol dimer may be a diol dimer that can be the product of hydrogenation of dilinoleic diacid. It may be in a saturated form.
  • a fatty alcohol dimer may be, for example, a dilinoleol dimer.
  • This compound is a glycerol dimer resulting from the condensation of two molecules of glycerol, with the loss of a water molecule.
  • diglycerol denotes any isomer combination that can result from such a condensation, for instance linear isomers, branched isomers and, where appropriate, cyclic isomers resulting from an intramolecular dehydration of a diglycerol molecule.
  • the diglycerol may be obtained via any process known to those skilled in the art and especially those described in patent EP 0 750 848.
  • An ester that is suitable for use in the present invention may be obtained by reacting a polyol or an ester thereof with a dimerdilinoleic acid, in a molar ratio of about 1.0:0.2-1.0.
  • An ester that may be suitable for use in the present invention may especially be obtained by reacting a dimerdilinoleic acid with a dilinoleol and, where appropriate, at least one additional monoalcohol chosen especially from behenol, isostearol, phytosterol, stearol and cetol, and mixtures thereof.
  • an ester used in the context of the present invention may be used in the form of a mixture of various esters, for example.
  • An ester that is suitable for the invention may be obtained, for example, by reacting a glycerol, an isostearic acid and a dimerdilinoleic acid, especially, in a molar ratio of 1.0:0.2-1.0:0.5-0.9.
  • esters of dimerdilinoleic acid and of polyol(s) or an ester thereof suitable for the invention mention may be made of the esters described in patent applications JP 2004-256515 and JP 2005-179377.
  • An ester of dilinoleic acid and of polyol(s) or an ester thereof suitable for use in the present invention may have a molecular weight ranging from about 2000 to about 25 000 g/mol, in particular from about 4000 to about 20 000 g/mol, in particular from about 7000 to about 15 000 g/mol and more particularly from about 8000 to about
  • an ester in accordance with the invention may comprise an alternating sequence of dimerdilinoleate residue(s) and of residue (s) related to the said polyol(s), and especially to the said diol(s), the said polyols or diols being, for example, as defined above.
  • each of the two ends of the said sequence may bear, respectively, a unit OR' and OR" with R' and R" representing, independently of each other, a hydrogen atom or OR' and OR" representing, independently of each other, a C 2 to C36, especially Cs to C24, in particular C 12 to C20 and more particularly C 16 to C 18 hydrocarbon-based monoalcohol residue.
  • R' and R" may both represent a hydrogen atom.
  • OR' and OR" may both represent an identical or different hydrocarbon-based monoalcohol residue.
  • hydrocarbon-based monoalcohol residues OR' and OR that may be suitable for the invention, mention may be made of fatty alcohol residues.
  • an ester of dimer dilinoleic acid and of polyol(s) or an ester thereof that may be suitable for use in the present invention may have the general formula (I) below:
  • - OR 2 O represents a fatty alcohol dimer residue, may range from C 16 to C 6 8, especially from C 24 to C44, in particular from C 32 to C40 and more particularly may be of C 36 .
  • - OR-3 represents a monoalcohol residue may range from 4 to 40 carbon atoms, in particular from 6 to 36 carbon atoms, in particular from 8 to 32, in particular from 16 to 28, and more particularly from 18 to 24 carbon atoms, and
  • - n is an integer ranging from 1 to 15, in particular from 2 to 10 and more particularly from 5 to 7.
  • OR 2 O may represent a dimerdilinoleyl residue.
  • OR3 may represent a hydrocarbon-based monoalcohol residue chosen, for example, from behenyl, isostearyl and phytosteryl residues, and mixtures thereof.
  • ester of dimerdilinoleic acid and of polyol(s) or an ester thereof that may be suitable for use in the invention may, especially, have the general formula (II) below:
  • - n is an integer ranging from 1 to 15, especially from 2 to 10 and in particular from
  • R'3 represents H or OR'3 represents a fatty acid residue that may range from Cs to C34, especially from C12 to C 22 , in particular of C 16 to C 2 o and more particularly may be C 18 ..
  • the fatty acid residue represented by OR3 may be an isostearyl residue.
  • the viscosity of an ester of dimerdilinoleic acid and of polyol(s) or an ester thereof, according to the invention may be measured according to any process known to those skilled in the art, and especially according to the conventional process described hereinbelow.
  • the viscosity may be measured using a cone/plate or parallel plate viscometer of Ares type (TA-Instrument) operating in kinetic sweep mode over a shear range of about 1-1000 s "1 to induce a flow tension at about 1000 Pa.
  • Ares type TA-Instrument
  • the cone/plate or parallel plates may consist of a material selected from the group constituted of stainless steel, acrylic resins or polyphenylene sulfide (PPS resin).
  • the cone/plate diameter may be 25 mm (cone angle 0.10 radiants).
  • the measurement is performed at about 25°C.
  • the stability of the sample is checked by means of the dynamic sweep period test, which makes it possible to determine if the sample is stable per se.
  • the shear viscosity is determined using the ETA value in the plateau region according to the flow.
  • the dynamic sweep period is determined at a frequency of 1.0 Hz over a period of 600 seconds.
  • the measurements at constant sweep rate are performed with a rate ranging from 1.0 to 1000 s "1 and in particular from 1.0 to 100 s "1 .
  • the viscosity of an ester of dimerdilinoleic acid and of polyol or an ester thereof suitable for use in the invention may range from about 20 000 mPa.s to about 150 000 mPa.s, especially from about 40 000 mPa.s to about lOO OOO mPa.s and in particular from about 60 000 mPa.s to about 80 000 mPa.s.
  • esters having the following INCI nomenclature: polyglyceryl-2 isostearate dimerdilinoleate copolymer, bis-behenyl/isostearyl/phytosteryl dimerdilinoleyl dimerdilinoleate, and mixtures thereof.
  • Such compounds may be obtained, for example, under the reference Hailucent ISDA (Kokyu Alcohol) and Plandool-G (Nippon Fine Chemical Company Ltd).
  • an ester of dimerdilinoleic acid and of polyol(s) or an ester thereof suitable for use in the invention may be advantageously present in the cosmetic compositions according to the invention in an amount sufficient to give these compositions improved cosmetic properties, especially in terms of mean gloss staying power.
  • the ester may be present in a content ranging from about 5% to about 90% by weight, in particular from about 15% to about 80% by weight and more particularly from about 20% to about 50% by weight relative to the total weight of the composition.
  • compositions according to the invention may also advantageously comprise at least one semi-crystalline polymer.
  • polymer means a compound comprising at least 2 repeating units, especially at least 3 repeating units, and in particular at least 10 repeating units.
  • the term "semi-crystalline polymer” means a polymer comprising a crystallizable portion and an amorphous portion in the backbone and having a first-order reversible temperature of phase change, in particular of melting
  • the crystallizable portion may be either a side chain (or pendent chain) or a block in the backbone.
  • this crystallizable block is of different chemical nature from that of the amorphous blocks.
  • the semi-crystalline polymer may be a block copolymer, for example of the diblock, triblock or multiblock type.
  • the semi- crystalline polymer may be a homopolymer or a copolymer.
  • the crystallizable blocks or chains of the semi-crystalline polymers may represent at least 30% and better still at least 40% of the total weight of each polymer.
  • organic compound and “of organic structure” mean a compound comprising carbon atoms and hydrogen atoms and possibly hetero atoms, for instance S, O, N or P, alone or in combination.
  • the semi-crystalline polymer(s) according to the invention preferably has (have) a melting point higher than the temperature of the keratin support intended to receive the said composition, in particular the skin or the lips.
  • the melting point of a semi-crystalline polymer that is suitable for the invention may be, for example, less than about 50 0 C.
  • the melting point of a semi-crystalline polymer that is suitable for the invention may especially be greater than or equal to about 25°C and less than about 45°C.
  • the melting point of the semi-crystalline polymer may be greater than or equal to about 35°C and less than about 40 0 C.
  • the melting point values correspond to the melting point measured using a differential scanning calorimeter (D. S. C.) such as the calorimeter sold under the name DSC 30 by the company Mettler, with a temperature rise of 5 or 10 0 C per minute.
  • the melting point under consideration is the point corresponding to the temperature of the most endothermic peak in the thermogram.
  • the semi-crystalline polymers may be soluble in a fatty phase, especially to at least 1% by weight, at a temperature above their melting point.
  • the semi- crystalline polymers of the invention containing crystallizable blocks may be block or multiblock copolymers. They may be obtained via polymerization of a monomer containing reactive double bonds (or ethylenic bonds) or via poly condensation.
  • polymers of the invention are polymers containing crystallizable side chains, these polymers may advantageously be in random form.
  • a semi-crystalline polymer that may be suitable for use in the present invention may be selected from the group constituted of a polymer comprising a) a hydrocarbon-based or silicone polymer backbone and b) at least one crystallizable organic side chain and/or a crystallizable organic block forming part of the polymer backbone of the said polymer, the said polymer having a number-average molecular mass of greater than 2000.
  • the semi-crystalline polymers of the invention may be of synthetic origin.
  • the semi-crystalline polymers that may be used in the invention may in particular be selected from the group constituted of:
  • They are homopolymers or copolymers comprising from 50% to 100% by weight of units resulting from the polymerization of one or more monomers bearing a crystallizable hydrophobic side chain.
  • homopolymers or copolymers may be of any nature, provided that they meet the conditions mentioned hereinbelow with, in particular, the characteristic of being soluble or dispersible in the fatty phase, by heating above their melting point mp. They can result:
  • the crystallizable units (chains or blocks) of semi-crystalline polymers according to the invention are derived from monomer(s) containing crystallizable block(s) or chain(s), used for manufacturing semi- crystalline polymers. These polymers are chosen especially from homopolymers and copolymers resulting from the polymerization of at least one monomer containing crystallizable chain(s) that may be represented by the formula: — M—
  • crystallizable chains "-S-C” may be aliphatic or aromatic, and optionally fluorinated or perfluorinated.
  • S especially represents a group (CH 2 ) n or (CH 2 CH 2 O) n or (CH 2 O), which may be linear or branched or cyclic, with n being an integer ranging from 0 to 22.
  • S is a linear group.
  • the crystallizable chains are hydrocarbon-based aliphatic chains, they may comprise hydrocarbon-based alkyl chains containing at least 11 carbon atoms and not more than 40 carbon atoms and better still not more than 24 carbon atoms. They may especially be aliphatic chains or alkyl chains containing at least 12 carbon atoms, and they may be, in particular Cw-C 24 , in particular Ci 6 -C 22 , alkyl chains. When they are fluoroalkyl or perfluoroalkyl chains, they may contain at least 11 carbon atoms, at least 6 of which carbon atoms are fluorinated.
  • the hydrocarbon-based and/or fluorinated crystallizable chains as defined above may be borne by a monomer that may be a diacid, a diol, a diamine or a diisocyanate.
  • the polymers that are the subject of the invention are copolymers, they additionally contain from 0 to 50% of groups Y or Z resulting from the copolymerization: ⁇ ) of Y which is a polar or non-polar monomer or a mixture of the two:
  • Y is a polar monomer, it is either a monomer bearing polyoxyalkylenated groups (especially oxyethylenated and/or oxypropylenated groups), a hydroxyalkyl (meth)acrylate, for instance hydroxyethyl acrylate, (meth)acrylamide, an N-alkyl(meth)acrylamide, an N,N-dialkyl(meth)acrylamide such as, for example, N,N-diisopropylacrylamide or N-vinylpyrrolidone (NVP), N- vinylcapro lactam, a monomer bearing at least one carboxylic acid group, for instance (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid or fumaric acid, or bearing a carboxylic acid anhydride group, for instance maleic anhydride, and mixtures thereof.
  • a monomer bearing polyoxyalkylenated groups especially oxyethylenated and/or oxypropyl
  • Y When Y is a non-polar monomer, it may be an ester of the linear, branched or cyclic alkyl (meth)acrylate type, a vinyl ester, an alkyl vinyl ether, an ⁇ -olefm, styrene or styrene substituted with a Ci to C 10 alkyl group, for instance ⁇ -methylstyrene, or a macromonomer of the polyorganosiloxane type containing vinyl unsaturation.
  • a non-polar monomer it may be an ester of the linear, branched or cyclic alkyl (meth)acrylate type, a vinyl ester, an alkyl vinyl ether, an ⁇ -olefm, styrene or styrene substituted with a Ci to C 10 alkyl group, for instance ⁇ -methylstyrene, or a macromonomer of the polyorganosiloxane type containing vinyl unsaturation.
  • alkyl means a saturated group especially of Cs to C 24 , except where otherwise mentioned.
  • ⁇ ) of Z which is a polar monomer or a mixture of polar monomers.
  • Z has the same definition as the "polar Y" defined above.
  • the semi-crystalline polymers containing a crystallizable side chain are alkyl (meth)acrylate or alkyl(meth)acrylamide homopolymers with an alkyl group as defined above, and especially of Ci 4 -C 24 , especially of Ci 6 -C 2 O, copolymers of these monomers with a hydrophilic monomer preferably of different nature from (meth)acrylic acid, for instance N-vinylpyrrolidone or hydroxyethyl (meth)acrylate, and mixtures thereof.
  • the semi-crystalline polymer(s) containing a crystallizable side chain has (have) a weight-average molecular mass Mp ranging from 5000 to 1 000 000 g/mol, preferably from 10 000 to 800 000 g/mol, preferentially from 15 000 to 500 000 g/mol and more preferably from 100 000 to 200 000 g/mol.
  • the Intelimer product IPA 13-1 from the company Landec is chosen, which is a polystearyl acrylate with a molecular weight of about 145 000 and a melting point of 49°C.
  • the semi-crystalline polymers may especially be those described in Examples 3, 4, 5, 7 and 9 of patent US-A-5 156 911, containing a -COOH group, resulting from the copolymerization of acrylic acid and of a Cs to Ci 6 alkyl (meth)acrylate with a melting point ranging from 20 0 C to 35°C, and more particularly from the copolymerization:
  • the semi-crystalline polymers may especially be semi- crystalline polymers with crystallizable pendent chains comprising fluoro groups, as described in Examples 1, 4, 6, 7 and 8 of document WO-A-01/19333.
  • polymers that are soluble or dispersible in the fatty phase by heating above their melting point mp.
  • These polymers are especially block copolymers consisting of at least two blocks of different chemical nature, one of which is crystallizable.
  • the polymer bearing at least one crystallizable block in the backbone may be selected from the group constituted of block copolymers of olefin or of cycloolef ⁇ n containing a crystallizable chain, for instance those derived from the block polymerization of:
  • the polymer bearing at least one crystallizable block in the backbone may be selected from the group constituted of copolymers containing at least one crystallizable block, the rest of the copolymer being amorphous at room temperature. These copolymers may also contain two crystallizable blocks of different chemical nature.
  • the preferred copolymers are those that simultaneously contain, at room temperature, a crystallizable block and an amorphous block that are both hydrophobic and lipophilic, sequentially distributed. Mention may be made, for example, of polymers containing one of the crystallizable blocks and one of the amorphous blocks below:
  • polyester type for instance poly(alkylene terephthalate), or of polyolef ⁇ n type, for instance polyethylenes or polypropylenes,
  • amorphous and lipophilic block for instance amorphous polyolefms or copoly(olef ⁇ n)s such as poly(isobutylene), hydrogenated polybutadiene or hydrogenated poly(isoprene).
  • poly( ⁇ -caprolactone)-b-poly(butadiene) block copolymers preferably used hydrogenated, such as those described in the article "Melting behaviour of poly(-caprolactone)-block-polybutadiene copolymers" from S. Nojima, Macromolecules, 32, 3727-3734 (1999),
  • the polyester poly condensates may be selected from the group constituted of aliphatic polyesters.
  • Their molecular mass is, for example, greater than or equal to about 200 g/mol and less than or equal to about 15 000 g/mol, and more particularly greater than or equal to about 1000 g/mol and less than or equal to 10 000 g/mol, in particular greater than or equal to about 2000 g/mol and less than or equal to about 5000 g/mol.
  • the polyester polycondensates are in particular selected from the group constituted of polycapro lactones.
  • the polycapro lactones may be selected from the group constituted of ⁇ -capro lactone homopolymers.
  • the homopolymerization may be initiated with a diol, especially a diol containing from 2 to 10 atoms, such as diethylene glycol, 1,4-butanediol or neopentyl glycol.
  • Polycapro lactones may be used for example, especially those sold under the name CAP A ® 240 (melting point of 68°C and molecular weight of 4000 g/mol), 223 (melting point of 48°C and molecular weight of 2000 g/mol), 222 (melting point of 48°C and molecular weight of 2000 g/mol), 217 (melting point of 44°C and molecular weight of 1250 g/mol), 2125 (melting point of 45°C and molecular weight of 1250) g/mol, 212 (melting point of 45°C and molecular weight of 1000 g/mol), 210 (melting point of 38°C and molecular weight of 1000 g/mol), 205 (melting point of 39°C and molecular weight of 830 g/mol) by the company Solvay, or PCL-300 and PCL-700 by the company Union Carbide.
  • CAP A ® 240 melting point of 68°C and molecular weight of 4000
  • the CAPA 2125 whose melting point is between 35 and 45°C and whose weight-average molecular mass is equal to 1250 g/mol may be used in particular.
  • copolymer comprising carboxylate groups and poly dimethylsiloxane groups means a copolymer obtained from the polymerization of (a) one or more carboxylic (acid or ester) monomers, with (b) one or more poly dimethylsiloxane (PDMS) chains comprising at least one polymerizable radical.
  • carboxylic monomers that are suitable for use in the invention, mention may be made of carboxylic acid monomers and carboxylic acid ester monomers.
  • the monomer (a) may be chosen, for example, from acrylic acid, methacrylic acid, maleic acid, fumaric acid, itaconic acid, crotonic acid, esters thereof and mixtures of these monomers.
  • Esters that may be mentioned include the following monomers methyl, ethyl, stearyl, butyl or 2-ethylhexyl acrylate, methacrylate, maleate, fumarate, itaconate and/or crotonate, and mixtures thereof.
  • the monomers in ester form may be selected from the group constituted of linear or branched, preferably C1-C24 and better still C1-C22 alkyl acrylates and methacrylates, the alkyl radical being selected from the group constituted of methyl, ethyl, stearyl, butyl and 2-ethylhexyl radicals, and mixtures thereof.
  • the copolymer may comprise as carboxylate groups at least one group selected from the group constituted of acrylic acid and methacrylic acid, and methyl, ethyl, stearyl, butyl or 2-ethylhexyl acrylate or methacrylate, and mixtures thereof.
  • polydimethylsiloxanes also known as organopolysiloxanes and abbreviated as PDMS
  • PDMS polydimethylsiloxanes
  • the PDMS chains that may be used to obtain the copolymer used according to the invention comprise at least one polymerizable radical group, preferably located on at least one of the ends of the chain, i.e. the PDMS may contain, for example, a polymerizable radical group on the two ends of the chain or one polymerizable radical group on one end of the chain and one trimethylsilyl end group on the other end of the chain.
  • copolymers that may be used in the composition of the invention may be obtained according to the usual methods of polymerization and grafting, for example by free-radical polymerization (a) of a PDMS comprising at least one polymerizable radical group (for example on one of the ends of the chain or on both ends) and (b) of at least one carboxylic monomer, as described, for example, in documents US-A-5 061 481 and US- A-5 219 560.
  • the copolymers obtained may have a molecular weight ranging from about 3000 g/mol to about 200 000 g/mol and especially from about 5000 g/mol to about 100 000 g/mol.
  • a copolymer that may be used in a composition of the invention may be in its native form or in dispersed form in a solvent such as lower alcohols containing from 2 to 8 carbon atoms, for instance isopropyl alcohol, or oils, for instance volatile silicone oils (for example cyclopentasiloxane).
  • a solvent such as lower alcohols containing from 2 to 8 carbon atoms, for instance isopropyl alcohol, or oils, for instance volatile silicone oils (for example cyclopentasiloxane).
  • copolymers that may be used in a composition of the invention mention may be made, for example, of copolymers of acrylic acid and of stearyl acrylate containing polydimethylsiloxane grafts, copolymers of stearyl methacrylate containing polydimethylsiloxane grafts, copolymers of acrylic acid and of stearyl methacrylate containing polydimethylsiloxane grafts, copolymers of methyl methacrylate, butyl methacrylate, 2-ethylhexyl acrylate and stearyl methacrylate containing polydimethylsiloxane grafts.
  • copolymer that may be used in the composition of the invention
  • a copolymer of acrylate and of dimethicone, such as KP-561 may be used; this copolymer is not dispersed in a solvent, but is in waxy form, its melting point being about 30 0 C.
  • the crystallizable side chain(s) or block(s) are hydrophobic.
  • the semi-crystalline polymers of the composition of the invention may or may not be partially crosslinked provided that the degree of crosslinking does not interfere with their dissolution or dispersion in the fatty phase by heating above their melting point. This may then be a case of chemical crosslinking, by reaction with a multifunctional monomer during polymerization. It may also be a case of physical crosslinking, which may then be due either to the establishment of bonds of hydrogen or dipolar type between groups borne by the polymer, for instance dipolar interactions between carboxylate ionomers, these interactions being in small amount and borne by the polymer backbone; or to a phase separation between the crystallizable blocks and the amorphous blocks, borne by the polymer.
  • the semi-crystalline polymers of the composition according to the invention are not crosslinked.
  • the total amount of semi-crystalline polymer(s) may represent from about 1% to about 8%, in particular from about 2% to about 6% and more particularly from about 3% to about 6% by weight relative to the total weight of the composition. In particular, it may represent from about 4% to about 5% by weight relative to the total weight of the composition.
  • the semi- crystalline polymer When introduced in sufficient amount, and in combination with an ester of dimerdilinoleic acid and of polyol(s), or an ester thereof as defined above, the semi- crystalline polymer especially has the advantage of being able to afford an improvement in the gloss staying power, or even also in the colour staying power, to the cosmetic compositions according to the invention.
  • the ester of dimerdilinoleic acid and of polyol(s), or an ester thereof, and the semi-crystalline polymer are present, in the compositions according to the invention, in a weight ratio that may range from about 15:1 to about 2:1, in particular from about 10:1 to about 4:1 and more particularly from about 8:1 to about 6:1.
  • physiologically acceptable medium is intended to denote a medium that is particularly suitable for the application of a composition according to the invention to the skin and/or the lips.
  • the physiologically acceptable medium is generally suited to the nature of the support onto which the composition is to be applied, and to the aspect in which the composition is intended to be conditioned.
  • the physiologically acceptable medium may comprise an aqueous and/or water-soluble phase and/or a fatty phase.
  • the aqueous phase or the fatty phase may form the continuous phase of the composition.
  • This aqueous phase may, where appropriate, be thickened, gelled or structured by also incorporating therein a conventional aqueous gelling agent especially of mineral origin, for instance clay, and/or of organic origin, for instance an aqueous gelling polymer.
  • a composition in accordance with the invention may be in the form of a suspension, a dispersion, a solution, a gel or an emulsion, especially an oil-in-water (O/W) or water-in-oil (W/O) emulsion, or a multiple emulsion (W/O/W, polyol/O/W or 0/W/O), or in the form of a cream, a stick, a paste, a mousse, a dispersion of vesicles, especially of ionic or nonionic lipids, a two-phase or multi-phase lotion or a powder.
  • O/W oil-in-water
  • W/O water-in-oil
  • W/O multiple emulsion
  • a cream, a stick, a paste, a mousse a dispersion of vesicles, especially of ionic or nonionic lipids, a two-phase or multi-phase lotion or a powder.
  • the emulsions contain a lipophilic phase and a hydrophilic phase, the latter phase not systematically being water.
  • the cosmetic compositions in accordance with the invention may be in the form of an anhydrous emulsion.
  • the composition may have, for example, a continuous fatty phase, which may contain less than 10% by weight of water, especially less than 5% by weight of water or even less than 1% by weight of water relative to the total weight of the composition.
  • a cosmetic composition according to the invention may be anhydrous, i.e. may contain less than 5%, in particular less than 3%, in particular less than 2% and more particularly less than 1% by weight of water relative to the total weight of the composition.
  • This composition may then especially be in the form of oily gels, oily liquids, pastes or sticks or alternatively in the form of a vesicular dispersion containing ionic and/or nonionic liquids.
  • a cosmetic composition in accordance with the present invention may comprise at least one fatty phase, for example a liquid fatty phase, selected from the group constituted of volatile and non-volatile oils, and a fatty substance that is solid at room temperature (20-25 0 C) and atmospheric pressure, and mixtures thereof.
  • a liquid fatty phase selected from the group constituted of volatile and non-volatile oils, and a fatty substance that is solid at room temperature (20-25 0 C) and atmospheric pressure, and mixtures thereof.
  • a composition according to the invention may comprise at least one liquid fatty phase selected from the group constituted of volatile oils and non- volatile oils, and mixtures thereof.
  • the term "oil” means any fatty substance that is in liquid form at room temperature (20-25 0 C) and at atmospheric pressure.
  • the liquid fatty phase may also contain, in addition to oils, other compounds dissolved in the oils, such as gelling agents and/or structuring agents.
  • the oil(s) may be present in a proportion of from 0.1% to 99% by weight, in particular from at least 1% to 90% by weight, more particularly from 5% to 70% by weight, especially from 10% to 60% by weight or even from 20% to 50% by weight relative to the total weight of the cosmetic composition according to the invention.
  • the liquid fatty phase that may be suitable for preparing a cosmetic composition according to the invention may be selected from the group constituted of volatile or non-volatile, silicone or non-silicone oils, and mixtures thereof.
  • the volatile or non-volatile oils may be hydrocarbon-based oils especially of animal or plant origin, synthetic oils, silicone oils or fluoro oils, or mixtures thereof.
  • silicon oil means an oil comprising at least one silicon atom, and especially at least one Si-O group.
  • hydrocarbon-based oil means an oil mainly containing hydrogen and carbon atoms, and possibly oxygen, nitrogen, sulfur and/or phosphorus atoms.
  • volatile oil means an oil
  • the volatile oil is a volatile cosmetic oil, which is liquid at room temperature, especially having a non-zero vapour pressure, at room temperature and atmospheric pressure, in particular having a vapour pressure ranging from 0.13 Pa to 40 000 Pa (10 ⁇ 3 to 300 mmHg), preferably ranging from 1.3 Pa to 13 000 Pa (0.01 to 100 mmHg) and preferably ranging from 1.3 Pa to 1300 Pa (0.01 to 10 mmHg).
  • the volatile hydrocarbon-based oils may be selected from the group constituted of hydrocarbon-based oils containing from 8 to 16 carbon atoms, and especially branched Cs-Ci 6 alkanes (also known as isoparaffins), for instance isododecane (also known as 2,2,4,4, 6-pentamethylheptane), isodecane, isohexadecane and, for example, the oils sold under the trade names Isopar ® or Permethyl ® .
  • Volatile oils that may also be used include volatile silicones, for instance volatile linear or cyclic silicone oils, especially those with a viscosity ⁇ 8 centistokes
  • silicones optionally comprising alkyl or alkoxy groups containing from 1 to 10 carbon atoms.
  • a volatile silicone oil that may be used in the invention, mention may be made especially of dimethicones with a viscosity of 5 and
  • Volatile fluoro oils such as nonafluoromethoxybutane or perfluoromethyl- cyclopentane, and mixtures thereof, may also be used.
  • Non-volatile oils are also possible to use a mixture of the oils mentioned above.
  • the fatty phase of the cosmetic compositions according to the present invention may also comprise at least one non-volatile oil, especially an oil of high molar mass.
  • non-volatile oil means an oil with a vapour pressure of less than 0.13 Pa and especially oils of high molar mass.
  • the non- volatile oils may be chosen especially from non- volatile hydrocarbon-based oils, which may be fluorinated, and/or non-volatile silicone oils.
  • oil of high molar mass means oils with a molar mass ranging from about 650 to about 10 000 g/mol, in particular from about 750 to about 7500 g/mol, and more particularly ranging from about 1000 to about 5000 g/mol.
  • oils of high molar mass that may be used in the present invention, mention may especially be made of oils selected from the group constituted of:
  • an oil of high molar mass may be selected from the group constituted of:
  • a) lipophilic polymers such as:
  • polyisobutylenes for example hydrogenated polyisobutylenes, such as
  • PVP polyvinylpyrrolidone
  • PVP copolymers that may be used in the invention, mention may be made of PVP/vinyl laurate, PVP/vinyl stearate, butylated polyvinylpyrrolidone, PVP/hexadecene, PVP/triacontene or PVP/acrylic acid/lauryl methacrylate copolymer,
  • esters such as:
  • esters of diol dimer and of fatty acid such as esters of diol dimer and of diacid, sold by the company Nippon Fine Chemical and described in the patent application FR 03 02809 filed on 6 March 2003, the content of which is incorporated into the present patent application by reference,
  • oils of plant origin such as sesame oil (MM820 g/mol)
  • esters of diol dimer and of monocarboxylic acid may be obtained from a monocarboxylic acid containing from 4 to 34 carbon atoms and especially from 10 to 32 carbon atoms, these acids being linear or branched, and saturated or unsaturated.
  • esters of diol dimer and of dicarboxylic acid may be obtained from a diacid dimer derived in particular from the dimerization of an unsaturated fatty acid especially of Cs to C34, especially of C 12 to C22, in particular of C 16 to C20 and more particularly of Ci 8.
  • it may more particularly be the diacid dimer from which the diol dimer to be esterified is also derived.
  • the diol dimer esters may be obtained from a diol dimer produced by catalytic hydrogenation of a diacid dimer as described above, for example hydrogenated dilinoleic diacid.
  • esters of a diol dimer that may especially be mentioned include the esters of dilinoleic diacids and of dilinoleyl diol dimers sold by the company Nippon Fine Chemical under the trade names Lusplan DD-DA5 ® and DD-D A7 ® .
  • An oil of high molar mass may be chosen especially from polybutylenes, polyisobutylenes, hydrogenated polyisobutylenes, polydecenes, hydrogenated polydecenes, vinylpyrrolidone copolymers such as PVP/hexadecene copolymer, pentaerythrityl tetrapelargonate, polyglyceryl-2 triisostearate, tridecyl trimellitate, triisoarachidyl citrate, pentaerythrityl tetraisononanoate, glyceryl triisostearate, glyceryl tris(2-decyl)tetradecanoate, pentaerythrityl tetraisostearate, polyglyceryl-2 tetraisostearate, pentaerythrityl tetrakis(2-decyl)tetradecanoate, phenyl silicones, sesame oil and oils of ester of acid dim
  • non-volatile hydrocarbon-based oils that are also suitable for use in the invention, mention may be made especially of:
  • oils of plant origin such as phytostearyl esters, such as phytostearyl oleate, phytostearyl isostearate and lauroyl/octyldodecyl/phytostearyl glutamate, for example sold under the name Eldew PS203 by Ajinomoto, triglycerides consisting of fatty acid esters of glycerol, the fatty acids of which may have chain lengths ranging from C 4 to C 24 , these chains possibly being linear or branched, and saturated or unsaturated; these oils are especially heptanoic or octanoic triglycerides, wheatgerm oil, sunflower oil, grapeseed oil, corn oil, apricot oil, castor oil, shea oil, avocado oil, olive oil, soybean oil, sweet almond oil, palm oil, rapeseed oil, cotton seed oil, hazelnut oil, macadamia oil, jojoba oil, alfalfa oil, poppy oil, pumpkin oil
  • linear or branched hydrocarbons of mineral or synthetic origin such as petroleum jelly, polydecenes, hydrogenated polyisobutene such as
  • esters for instance oils of formula RiCOOR 2 in which Ri represents a linear or branched fatty acid residue containing from 1 to 40 carbon atoms and R 2 represents a hydrocarbon-based chain that is especially branched, containing from 1 to 40 carbon atoms provided that Ri + R 2 > 10.
  • the esters may be chosen especially from fatty acid esters, for example:
  • cetostearyl octanoate isopropyl alcohol esters, such as isopropyl myristate or isopropyl palmitate, ethyl palmitate, 2-ethylhexyl palmitate, isopropyl stearate or isostearate, isostearyl isostearate, octyl stearate, hydroxylated esters, for instance isostearyl lactate, octyl hydroxystearate, diisopropyl adipate, heptanoates, and especially isostearyl heptanoate, alcohol or polyalcohol octanoates, decanoates or ricinoleates, for instance propylene glycol dioctanoate, cetyl octanoate, tridecyl octanoate, 2-ethylhexyl A- diheptanoate and palmitate, alkyl benzoate, polyethylene
  • C 12 to C 15 alcohol benzoates hexyl laurate, neopentanoic acid esters, for instance isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate and octyldodecyl neopentanoate, isononanoic acid esters, for instance isononyl isononanoate, isotridecyl isononanoate and octyl isononanoate, and hydroxylated esters, for instance isostearyl lactate and diisostearyl malate;
  • neopentanoic acid esters for instance isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate and octyldodecyl neopentan
  • polyol esters and pentaerythritol esters for instance dipentaerythrityl tetrahydroxystearate/tetraisostearate
  • esters of diol dimers and of diacid dimers such as Lusplan DD-D A5 ® and Lusplan DD-DA7 ® , sold by the company Nippon Fine Chemical and described in patent application FR 03/02809 filed on March 2003, the content of which is incorporated in the present application by reference;
  • fatty alcohols that are liquid at room temperature, with a branched and/or unsaturated carbon-based chain containing from 12 to 26 carbon atoms, for instance 2-octyldodecanol, isostearyl alcohol, oleyl alcohol, 2-hexyl- decanol, 2-butyloctanol and 2-undecylpentadecanol;
  • dialkyl carbonates the two alkyl chains possibly being identical or different, such as dicaprylyl carbonate sold under the name Cetiol CC ® by
  • non-volatile silicone oils for instance non-volatile polydimethylsiloxanes (PDMS), polydimethylsiloxanes comprising alkyl or alkoxy groups that are pendent and/or at the end of a silicone chain, these groups each containing from 2 to 24 carbon atoms, phenyl silicones, for instance phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyl- trisiloxanes and 2-phenylethyl trimethylsiloxysilicates, and dimethicones or phenyltrimethicones with a viscosity of less than or equal to 100 cSt, and mixtures thereof;
  • PDMS non-volatile polydimethylsiloxanes
  • phenyl silicones for instance phenyl trimethicones, phenyl dime
  • the non- volatile oils may be present in a composition according to the invention in a content ranging from 5% to 90% by weight, especially from 25% to 80% by weight and in particular from 40% to 70% by weight relative to the total weight of the composition.
  • An oil of high molar mass that may be used in a composition according to the invention may be present in a proportion of from 5% to 40%, preferably from 10% to 30% and better still from 15% to 20% of the total weight of the composition.
  • compositions according to the invention may also comprise at least one solid fatty phase selected from the group constituted of waxes and pasty fatty substances, and mixtures thereof.
  • the wax is solid at room temperature (25°C), with a reversible solid/liquid change of state, having a melting point of greater than 30 0 C, which may be up to 200 0 C, a hardness of greater than 0.5 MPa and having in the solid state an anisotropic crystal organization.
  • It may be a hydrocarbon-based wax, a fluoro wax and/or a silicone wax and may be of animal, plant, mineral or synthetic origin.
  • the wax(es) used in the cosmetic compositions in accordance with the present invention may be present in a content ranging from about 5% to about 30%, in particular from about 5% to about 25%, in particular from about 10% to about 20% and more particularly from about 10% to about 15% by weight relative to the total weight of the composition.
  • the cosmetic compositions in accordance with the present invention may also comprise at least one pasty compound.
  • pasty compound means a fatty compound with a reversible solid/liquid change of state, and comprising at a temperature of 23°C a liquid fraction and a solid fraction.
  • pasty substance also means polyvinyl laurate.
  • the pasty compound advantageously has a hardness at 20 0 C ranging from 0.001 to 0.5 MPa and preferably from 0.002 to 0.4 MPa.
  • lanolins and lanolin derivatives for instance acetylated lanolins, oxypropylenated lanolins or isopropyl lanolate, and mixtures thereof.
  • Esters of fatty acids or of fatty alcohols may also be used, especially those containing from
  • Triglycerides of plant origin such as hydrogenated plant oils, viscous polyesters and mixtures thereof.
  • Triglycerides of plant origin include hydrogenated castor oil derivatives, such as Thixinr ® from
  • polyesters resulting from the esterification of a carboxylic acid and of an aliphatic hydroxycarboxylic acid ester For example, Risocast ® DA-L (ester derived from the esterification reaction of hydrogenated castor oil with dilinoleic acid in proportions of 2 to 1) and Risocast ® DA-H (ester resulting from the esterification of hydrogenated castor oil with isostearic acid in proportions of 4 to 3) sold by the Japanese company Kokyu Alcohol Kogyo.
  • silicone compounds such as high molecular weight polydimethylsiloxanes (PDMS) and in particular those containing pendent chains of the alkyl or alkoxy type containing from 8 to 24 carbon atoms, and having a melting point of 20-55 0 C, for instance stearyl dimethicones, especially those sold by the company Dow Corning under the trade names DC2503 ® and DC25514 ® , and mixtures thereof.
  • PDMS high molecular weight polydimethylsiloxanes
  • stearyl dimethicones especially those sold by the company Dow Corning under the trade names DC2503 ® and DC25514 ® , and mixtures thereof.
  • a composition according to the invention may also contain at least one gelling agent.
  • Such a gelling agent may be used to gel the liquid fatty phase and/or the aqueous phase of the composition.
  • the fatty-phase gelling agent may increase the viscosity of the liquid fatty phase and may lead to a solid or flowable composition, during its introduction into the said liquid fatty phase.
  • the fatty-phase gelling agent may be selected from the group constituted of gelling agents in polymer form and gelling agents in mineral form.
  • the fatty-phase gelling agent is insoluble in an aqueous phase or in water.
  • the fatty-phase gelling agent may be selected from the group constituted of crosslinked elastomeric polyorganosiloxanes of three- dimensional structure, silicone gums, amino silicone polymers, silicone polyamides, non- silicone polyamides, polyurethanes, (meth)acrylic and/or vinyl polymers, copolymers such as polystyrene-silicone or poly ethylene-silicone, copolymers comprising a silicone block and another block or graft that is polyvinyl or poly(meth)acrylic, polymers or copolymers resulting from the polymerization or copolymerization of an ethylenic monomer, a modified clay and a fumed silica, and a mixture thereof.
  • the fatty-phase gelling agent may be selected from the group constituted of the group consisting of:
  • crosslinked elastomeric polyorganosiloxanes of three-dimensional structure such as the MQ silicone resins, and polyalkylsesquioxanes, in particular polymethylsesquioxanes and resins crosslinked via hydrosilylation.
  • silicone resins may bear hydrophilic groups, such as polyoxyethylene or copoly(oxyethylene/ oxypropylene).
  • polyorganosiloxanes that may be used according to the invention, mention may be made of those sold or manufactured under the names KSG6 from Shin-Etsu, Trefil E-505C or Trefil E-506C from Dow Corning, Gransil from Grant
  • silicone gums such as the product sold or manufactured under the name SE30 by the company General Electric, the product sold or manufactured under the name AK 500 000 by the company Wacker, the product sold or manufactured under the name Q2-1401 by the company Dow Corning, the product sold or manufactured under the name Q2-1403 by the company Dow Corning, and the product sold or manufactured under the name 761 by the company Rh ⁇ ne-Poulenc (Rhodia Chimie),
  • copolymers comprising a silicone block and another block or graft that is polyvinylic or poly(meth)acrylic, such as those described in patents US 5 468 477 and
  • k) polymers or copolymers resulting from the polymerization or copolymerization of an ethylenic monomer such as those sold or manufactured under the name "Luvitol HSB” by BASF or those sold or manufactured under the brand name “Kraton” by Shell Chemical Co. or Gelled Permethyl 99A by Penreco, or those sold by the company Penreco under the name Versagel ® .
  • liquid fatty-phase gelling agent may be in mineral form.
  • a mineral gelling agent that is suitable for the invention may or may not be used in combination with a gelling agent as defined above, and may be selected from the group constituted of:
  • a modified clay for instance hectorites modified with an ammonium chloride of a C 10 to C22 fatty acid, for instance the products sold or manufactured under the names Bentone 34 by the company Rheox, Claytone XL, Claytone 34 and Claytone 40 sold or manufactured by the company Southern Clay, benzalkonium quaternium-18 bentonites, sold or manufactured under the names Claytone HT, Claytone GR and Claytone PS by the company Southern Clay, clays modified with stearyldimethylbenzoylammonium chloride, for instance the products sold or manufactured under the names Claytone APA and Claytone AF by the company Southern Clay, and Baragel 24 sold or manufactured by the company Rheox.
  • a modified clay for instance hectorites modified with an ammonium chloride of a C 10 to C22 fatty acid, for instance the products sold or manufactured under the names Bentone 34 by the company Rheox, Claytone XL, Claytone 34 and Claytone 40 sold or manufactured by the company Southern Clay, benzalkonium
  • the fumed silica may have a particle size that may be nanometric or micrometric, for example ranging from about 5 nm to 200 nm.
  • Fumed silicas may be obtained by high-temperature hydrolysis of a volatile silicon compound in an oxyhydric flame, producing a finely divided silica. This process allows the production of hydrophilic silicas having a large number of silanol groups at their surface.
  • the silanol groups may be replaced, for example, with hydrophobic groups: this then gives a hydrophobic silica.
  • the hydrophobic groups may be:
  • silica thus treated are known as "silica silylate” according to the CTFA (6th edition, 1995). They are sold or manufactured, for example, under the references “Aerosil R812 ® “ by the company Degussa, and "Cab-O-Sil TS-530 ® " by the company Cabot;
  • a liquid fatty-phase gelling agent may be used, for example, in concentrations ranging from 1% to 30%, preferably from 5% to 20% and better still from 10% to 15% by weight relative to the total weight of the composition.
  • the composition according to the invention may also comprise, where appropriate, a hydrophilic or water-soluble gelling agent.
  • Hydrophilic or water-soluble gelling agents that may be mentioned include:
  • water-soluble gelling polymers As other examples of water-soluble gelling polymers, mention may be made of:
  • proteins for instance proteins of plant origin, such as wheat or soybean proteins; proteins of animal origin such as keratins, for example keratin hydro lysates and sulfonic keratins; - anionic, cationic, amphoteric or nonionic chitin or chitosan polymers;
  • cellulose polymers such as hydroxyethylcellulose, hydroxypropylcellulose, methylcellulose, ethylhydroxyethylcellulose and carboxymethylcellulose, and also quaternized cellulose derivatives;
  • vinyl polymers for instance polyvinylpyrrolidones, copolymers of methyl vinyl ether and of malic anhydride, the copolymer of vinyl acetate and of crotonic acid, copolymers of vinylpyrrolidone and of vinyl acetate; copolymers of vinylpyrrolidone and of capro lactam; polyvinyl alcohol;
  • - associative polyurethanes such as the C16-OE120-C16 polymer from the company Servo Delden (sold under the name Ser Ad FXI lOO, which is a molecule containing urethane functions and having a weight-average molecular weight of 1300 g/mol), OE being an oxyethylene unit, Rheolate 205 containing urea functions, sold by the company Rheox, or Rheolate 208 or 204 (these polymers being sold in pure form) or DW 1206B from Rohm & Haas, containing a C20 alkyl chain and a urethane bond, sold at a solids content of 20% in water.
  • Ser Ad FXI lOO which is a molecule containing urethane functions and having a weight-average molecular weight of 1300 g/mol
  • OE being an oxyethylene unit
  • Rheolate 205 containing urea functions sold by the company Rheox
  • solutions or dispersions of these associative polyurethanes especially in water or in aqueous-alcoholic medium.
  • examples of such polymers include Ser Ad FXlOlO, Ser Ad FXl 035 and Ser Ad 1070 from the company Servo Delden, and Rheolate 255, Rheolate 278 and Rheolate 244 sold by the company Rheox.
  • Rheolate 255, Rheolate 278 and Rheolate 244 sold by the company Rheox.
  • a cosmetic composition according to the invention may also comprise at least one dyestuff.
  • Such a dyestuff may be chosen, for example, from a water-soluble or water- insoluble, liposoluble or non-liposoluble, organic or mineral dyestuff, for example of the type such as pigments or nacres, conventionally used in cosmetic compositions.
  • pigments should be understood as meaning white or coloured, mineral or organic particles that are insoluble in an aqueous solution, which are intended to colour and/or opacify the resulting film.
  • the pigments may be present in a proportion of from 0.5% to 30% by weight, especially from 5% to 25% by weight and in particular from 10% to 20% by weight relative to the total weight of the cosmetic composition.
  • mineral pigments that may be used in the invention, mention may be made of titanium oxide, zirconium oxide or cerium oxide, and also zinc oxide, iron oxide or chromium oxide, ferric blue, manganese violet, ultramarine blue and chromium hydrate.
  • a pigment is sold, for example, under the reference Coverleaf ® NS or JS by the company Chemicals and Catalysts, and has a contrast ratio in the region of 30.
  • the dyestuff may also comprise a pigment having a structure that may be, for example, of silica microsphere type containing iron oxide.
  • a pigment having this structure is the product sold by the company Miyoshi under the reference
  • PC BALL ® PC-LL-100 P this pigment consisting of silica microspheres containing yellow iron oxide.
  • DPP diketopyrrolopyrroles
  • nacres should be understood as meaning coloured particles of any form, which may or may not be iridescent, especially produced by certain molluscs in their shell, or alternatively synthesized, and which have a colour effect via optical interference.
  • the nacres may be selected from the group constituted of nacreous pigments such as titanium mica coated with an iron oxide, mica coated with bismuth oxychloride, titanium mica coated with chromium oxide, titanium mica coated with an organic dye and also nacreous pigments based on bismuth oxychloride. They may also be mica particles at the surface of which are superposed at least two successive layers of metal oxides and/or of organic dyestuffs.
  • nacres examples include natural mica coated with titanium oxide, with iron oxide, with natural pigment or with bismuth oxychloride.
  • nacres Timica ® , Flamenco ® and Duochrome ® on mica base
  • Engelhard the Timiron ® nacres sold by the company Merck
  • Prestige ® nacres on mica base sold by the company Eckart the Prestige ® nacres on synthetic mica base sold by the company Sun Chemical.
  • the nacres may more particularly have a yellow, pink, red, bronze, orange, brown and/or coppery colour or glint.
  • nacres that may be used in the context of the present invention, mention may be made in particular of gold-coloured nacres sold especially by the company Engelhard under the name Brilliant gold 212G (Timica), Gold 222C (Cloisonne), Sparkle gold (Timica), Gold 4504 (Chromalite) and Monarch gold 233X (Cloisonne); the bronze nacres sold especially by the company Merck under the names Bronze fine (17384) (Colorona) and Bronze (17353) (Colorona) and by the company Engelhard under the name Super bronze (Cloisonne); the orange nacres sold especially by the company Engelhard under the names Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by the company Merck under the names Passion orange (Colorona) and Matte orange (17449) (Microna); the brown-tinted nacres sold especially by the company Engelhard under the names Nu-antique copper 340XB (Cloisonne) and Brown CL4509 (Chromalite
  • the cosmetic composition according to the invention may also comprise at least one water-soluble or liposoluble dye in a content ranging from 0.5% to 30% by weight and especially ranging from 5% to 25% by weight relative to the total weight of the cosmetic composition.
  • the liposoluble dyes are, for example, Sudan Red, DC Red 17, DC Green 6, ⁇ -carotene, soybean oil, Sudan Brown, DC Yellow 11, DC Violet 2, DC Orange 5 and quinoline yellow.
  • the water-soluble dyes are, for example, beetroot juice or methylene blue.
  • the cosmetic composition according to the invention may also contain at least one material with a specific optical effect.
  • This effect is different from a simple conventional hue effect, i.e. a unified and stabilized effect as produced by standard dyestuffs, for instance monochromatic pigments.
  • stabilized means lacking the effect of variability of the colour with the angle of observation or in response to a temperature change.
  • this material may be selected from the group constituted of particles with a metallic glint, gonio chromatic colouring agents, diffracting pigments, thermochromic agents, optical brighteners, and also fibres, especially interference fibres.
  • the particles with a metallic glint that may be used in the invention are in particular selected from the group constituted of:
  • particles of at least one metal and/or of at least one metal derivative particles comprising a monomaterial or multimaterial organic or mineral substrate, at least partially coated with at least one layer with a metallic glint comprising at least one metal and/or at least one metal derivative, and
  • metals that may be present in the said particles, mention may be made, for example, of Ag, Au, Cu, Al, Ni, Sn, Mg, Cr, Mo, Ti, Zr, Pt, Va, Rb, W, Zn, Ge, Te and Se and mixtures or alloys thereof.
  • Ag, Au, Cu, Al, Zn, Ni, Mo and Cr, and mixtures or alloys thereof (for example bronzes and brasses) are preferred metals.
  • metal derivatives is intended to denote compounds derived from metals, especially oxides, fluorides, chlorides and sulfides.
  • metal powders of copper or of alloy mixtures such as the references 2844 sold by the company Radium Bronze, metallic pigments, for instance aluminium or bronze, such as those sold under the names Rotosafe ® 700 from the company Eckart, silica-coated aluminium particles sold under the name Visionaire Bright
  • Silver ® from the company Eckart and metal alloy particles, for instance the silica-coated bronze (alloy of copper and zinc) powders sold under the name Visionaire Bright Natural Gold ® from the company Eckart.
  • silica-coated bronze alloy of copper and zinc
  • They may also be particles comprising a glass substrate, for instance those sold by the company Nippon Sheet Glass under the name Microglass Metashine ® .
  • the goniochromatic colouring agent may be chosen, for example, from interference multilayer structures and liquid-crystal colouring agents.
  • Examples of symmetrical interference multilayer structures that may be used in compositions produced in accordance with the invention are, for example, the following structures: AlZSiO 2 ZAlZSiO 2 ZAl, pigments having this structure being sold by the company Dupont de Nemours; CrZMgF 2 / Al/MgF 2 /Cr, pigments having this structure being sold under the name Chromaflair ® by the company Flex; MoS 2 ZSiO 2 ZAlZSiO 2 ZMoS 2 ; Fe 2 O 3 ZSiO 2 ZAlZSiO 2 ZFe 2 O 3 and Fe 2 O 3 ZSiO 2 ZFe 2 O 3 ZSiO 2 ZFe 2 O 3 , pigments having these structures being sold under the name Sicopearl ® by the company BASF; MoS 2 ZSiO 2 Zmica oxideZSiO 2 ZMoS 2 ; Fe 2 O 3 ZSiO 2 Zmica oxideZSiO 2 ZFe 2
  • these pigments may be the pigments of silicaZtitanium oxideZtin oxide structure sold under the name Xirona Magic ® by the company Merck, the pigments of silicaZbrown iron oxide structure sold under the name Xirona Indian Summer ® by the company Merck and the pigments of silicaZtitanium oxideZmicaZtin oxide structure sold under the name Xirona Caribbean Blue ® by the company Merck.
  • Infinite Colors ® pigments from the company Shiseido. Depending on the thickness and the nature of the various coats, different effects are obtained.
  • the colour changes from green-golden to red-grey for SiO 2 layers of from 320 to 350 nm; from red to golden for SiO 2 layers of from 380 to 400 nm; from violet to green for SiO 2 layers of from 410 to 420 nm; from copper to red for SiO 2 layers of from 430 to 440 nm.
  • pigments with a polymeric multilayer structure examples include those sold by the company 3M under the name Color Glitter ® .
  • liquid-crystal goniochromatic particles examples include those sold by the company Chenix and also the product sold under the name Helicone ® HC by the company Wacker.
  • a composition according to the invention may comprise not more than 30% by weight of dyestuff relative to the total weight of the composition.
  • the cosmetic compositions in accordance with the invention may also comprise at least one filler, of organic or mineral nature, which especially makes it possible to give them improved stability with regard to exudation.
  • filler should be understood as meaning colourless or white solid particles of any form, which are in an insoluble form and dispersed in the medium of the composition. Being of mineral or organic nature they make it possible to impart body or rigidity to the composition, andZor softness, a matt effect and uniformity to the makeup.
  • the fillers used in the compositions according to the present invention may be of lamellar, globular or spherical form, fibres or in any other form intermediate between these defined forms.
  • the fillers according to the invention may or may not be surface-coated, and in particular they may be surface-treated with silicones, amino acids, fluoro derivatives or any other substance that promotes the dispersion and compatibility of the filler in the composition.
  • mineral fillers and “inorganic fillers” are used interchangeably.
  • mineral fillers that may be used in the compositions according to the invention, mention may be made of talc, mica, silica, trimethyl siloxysilicate, kaolin, bentone, precipitated calcium carbonate, magnesium carbonate, magnesium hydrogen carbonate, hydroxyapatite, boron nitride, hollow silica microspheres (Silica Beads from Maprecos), glass or ceramic microcapsules, silica-based fillers, for instance Aerosil 200 or Aerosil 300; Sunsphere L-31 and Sunsphere H-31 sold by Asahi Glass; Chemicelen sold by Asahi Chemical; composites of silica and of titanium dioxide, for instance the TSG series sold by Nippon Sheet Glass, and mixtures thereof.
  • organic fillers that may be used in the compositions according to the invention, mention may be made of polyamide powders (Nylon ® Orgasol from Atochem), poly- ⁇ -alanine powder and polyethylene powder, polytetrafluoroethylene powders (Teflon ® ), lauroyllysine, starch, tetrafluoroethylene polymer powders, hollow polymer microspheres such as Expancel ® (Nobel Industrie), precipitated calcium carbonate, magnesium carbonate, magnesium hydrogen carbonate, metal soaps derived from organic carboxylic acids containing from 8 to 22 carbon atoms and preferably from 12 to 18 carbon atoms, for example zinc stearate, magnesium stearate or lithium stearate, zinc laurate or magnesium myristate, Polypore ® L 200 (Chemdal Corporation), silicone resin microbeads (for example Tospearl ® from Toshiba), polyurethane powders, in particular powders of crosslinked polyurethane comprising a copoly
  • it may be a polymer of hexamethylene diisocyanate/trimethylol hexyllactone.
  • Such particles are especially commercially available, for example, under the name Plastic Powder D-400 ® or Plastic Powder D-800 ® from the company Toshiki, and mixtures thereof.
  • a filler may be present in a cosmetic composition in accordance with the invention in a proportion of from 0.5% to 40% by weight and preferably from 5% to 30% by weight of filler relative to the total weight of the composition.
  • a filler that is suitable for the invention may be, for example, a filler whose mean particle size is less than 100 ⁇ m and especially between 1 and 50 ⁇ m, for example between 4 and 20 ⁇ m.
  • the cosmetic compositions according to the invention may, furthermore, also comprise any additive usually used in the field under consideration, selected from the group constituted of film- forming agents and, where appropriate, auxiliary film- forming agents, gums, antioxidants, surfactants, essential oils, preserving agents, fragrances, neutralizers, moisturizers, antiseptics, vitamins such as vitamin B3 or E and derivatives thereof, and anti-UV agents, and mixtures thereof.
  • any additive usually used in the field under consideration selected from the group constituted of film- forming agents and, where appropriate, auxiliary film- forming agents, gums, antioxidants, surfactants, essential oils, preserving agents, fragrances, neutralizers, moisturizers, antiseptics, vitamins such as vitamin B3 or E and derivatives thereof, and anti-UV agents, and mixtures thereof.
  • One subject of the present invention is the use of at least one ester of dimerdilinoleic acid and of polyol(s), or an ester thereof, in accordance with the invention, in combination with at least one semi-crystalline polymer, for the preparation of a cosmetic composition for caring for and/or making up the skin and/or the lips, which shows improved gloss staying power, or even also improved colourfastness.
  • the semi-crystalline polymer used in the use in accordance with the invention may be as defined above.
  • a subject of the present invention is a synthetic support comprising at least one coat of a composition in accordance with the invention.
  • a composition in accordance with the invention may be prepared in the usual manner for those skilled in the art. It may thus be in cast form, for example in the form of a stick or wand, in the form of a soft paste in a heating bag or in the form of dishes that may be used by direct contact or with a sponge.
  • it may constitute a cast foundation, a cast makeup rouge or eyeshadow, which is especially coloured, a lipstick, a lip gloss or a concealer product.
  • a composition in accordance with the invention may be obtained by heating the various constituents to the melting point of the highest-melting waxes, followed by pouring the molten mixture into a mould (dish or finger stall). It may also be obtained by extrusion, as described in patent application EP-A-O 667 146.
  • the present invention also relates to a process for making up and/or caring for the skin and/or the lips, comprising at least one step that consists in applying a composition in accordance with the invention to at least part of a support.
  • the cosmetic composition according to the invention may especially be in the form of a lip makeup and/or care composition, in particular a lipstick, a lip balm or a gloss.
  • composition example below is given as a non-limiting illustration of the invention.
  • An oily phase is prepared by mixing together the oils and the polyglyceryl-2 isostearate/dimerdilinoleate copolymer (Hailucent ISDA) for the composition according to the invention, with heating (about 95°C).
  • Hailucent ISDA polyglyceryl-2 isostearate/dimerdilinoleate copolymer
  • the oily phase thus prepared is stirred at about 95°C and the fillers are added to the mixture.
  • the waxes, the pigments in the form of a pigmentary paste prepared by mixing the dyestuffs with the polyglyceryl triisostearate and the isononyl isononanoate, the simethicone and the bis-behenyl/isostearyl/phytosteryl dimerdilinoleyl dimerdilinoleate are then added to the mixture.
  • the mixture thus obtained is then poured into a lipstick mould and is left to cool until a solid composition is obtained.
  • the mean gloss and the mean gloss staying power of composition 1 are measured according to the protocol described previously.

Abstract

The present invention relates to a cosmetic composition for caring for and/or making up the skin and/or the lips, comprising at least one ester of dimerdilinoleic acid and of polyol(s) or an ester thereof, whose viscosity, measured at about 25°C, is greater than or equal to about 20 000 mPa.s, and having a gloss staying power of greater than or equal to 7.

Description

Cosmetic composition comprising an ester of dimerdilinoleic acid and of polyol(s) and a semi-crystalline polymer
The present invention relates to cosmetic make-up and/or care compositions, intended to be applied to the skin and/or the lips, comprising an ester of dimerdilinoleic acid and of polyol(s), or an ester thereof, and having improved gloss staying power.
A composition according to the invention may in particular be a makeup and/or care product intended to be applied to the body, especially the face, and/or the lips, and may especially be a lipstick, a lip balm, a lip pencil, a liquid or solid foundation, especially cast as a stick or a dish, a concealer product, a skin colouring product, an eye makeup product, for instance eyeliners, in particular in pencil form, a mascara especially in cake form, an eyeshadow or a lip gloss.
There are many cosmetic compositions for which the properties of gloss and/or colour effect of the deposited film, after application on the skin and/or the lips, are desired. These properties generally contribute towards the desired aesthetic effect.
Moreover, it is also required for this aesthetic effect to be maintained over time, especially with regard to the various external factors liable to affect its gloss and/or colour characteristics.
In order to give cosmetic compositions good gloss properties and especially good mean gloss staying power, it has been proposed to use "glossy" oils such as oily polymers, for instance high- viscosity polybutenes, esters of fatty acids or of fatty alcohols of high carbon number (typically greater than 16) or certain plant oils.
However, these compounds may, under certain circumstances, be tacky on application and over time, which may cause considerable discomfort to the user.
The inventors have observed, surprisingly, that the use of certain esters of dimerdilinoleic acids and of polyol(s) or an ester thereof, for preparing cosmetic compositions, makes it possible to give these compositions improved mean gloss staying power, without affecting their combination of aesthetic properties, while at the same time affording a comfortable sensation on application.
Moreover, the cosmetic compositions according to the invention do not cause any tacky sensation after they have been applied.
Thus, according to one of its aspects, one subject of the present invention is a cosmetic composition for caring for and/or making up the skin and/or the lips, comprising at least one ester of dimerdilinoleic acid and of polyol(s), or an ester thereof, the viscosity of which, measured at about 25°C, is greater than or equal to about 20 000 mPa.s, and having a mean gloss staying power of greater than or equal to about 7.
According to yet another of its aspects, a subject of the present invention is an anhydrous cosmetic composition for caring for and/or making up the skin and/or the lips, comprising at least one ester of dimerdilinoleic acid and of polyol(s), or an ester thereof, the viscosity of which, measured at about 25°C, is greater than or equal to about
20 000 mPa.s, and at least one semi-crystalline polymer.
According to one particular embodiment, an anhydrous cosmetic composition according to the invention comprises less than 5% by weight of water, or even less than 3% by weight of water and more particularly less than 1% by weight of water, relative to its total weight.
According to yet another of its aspects, a subject of the present invention is a cosmetic composition for caring for and/or making up the skin and/or the lips comprising at least one ester of general formula (I) below:
R3-OCO-Ri(-COO-R2-OCO-Ri)n-COO-R3 (I) in which:
- CORiCO represents a dimerdilinoleate residue,
- OR2O represents a fatty alcohol dimer residue,
- OR3 represents a hydrocarbon-based monoalcohol residue, and
- n is an integer ranging from 1 to 15,
and having a gloss staying power of greater than or equal to 7.
According to yet another of its aspects, a subject of the present invention is a cosmetic composition for caring for and/or making up the skin and/or the lips comprising at least one ester of general formula (II) below:
HO-R', 2 -TV O— C R\ C— O R2 ) n OH
(H)
O O
in which:
- n is an integer ranging from 1 to 15,
- OCR' i CO represents a dimerdilinoleate residue,
- OR'2O represents a diglyceryl residue of general formula (III) below:
Figure imgf000004_0001
in which:
R'3 represents H or OR'3 represents a fatty acid residue,
and having a gloss staying power of greater than or equal to 7.
According to yet another of its aspects, a subject of the present invention is the use of at least one ester of dimerdilinoleic acid and of polyol(s) or an ester thereof, in accordance with the invention, in combination with at least one semi-crystalline polymer, for the preparation of a cosmetic composition for caring for and/or making up the skin and/or the lips having improved gloss staying power.
According to one of its advantages, the present invention makes it possible to provide cosmetic compositions whose gloss is also improved, while at the same time not causing any sensation of tack or of discomfort on application.
According to yet another advantage, the present invention makes it possible to provide cosmetic compositions whose gloss staying power is also improved over time, and especially with regard to various external attacking factors, such as mealtimes or contact with a fabric.
Moreover, the staying power colour of the composition according to the invention is advantageously not affected, or is even improved. GLOSS AND GLOSS STAYING POWER
The term "gloss" is intended to denote the gloss of a composition as may be conventionally measured using a glossmeter, via the following method.
The gloss may be measured by means of a test performed in vitro using a Multi-Gloss 268 glossmeter (Minolta, Tokyo, Japan).
A first coat of cosmetic composition, for example in the form of a lipstick, is applied to a sample of Bio-Skin synthetic skin (of the type Fat-Skin Beaulax, Tokyo, Japan) 3 cm x 4.5 cm in size, by application in the direction of the length of the support of contiguous strips of the said composition, so as to cover an area of 2.5 cm x 4 cm. A second coat of composition is applied over the first coat in a similar manner to the first, offset widthwise by about half the width of a strip in order to obtain a surface uniformly covered with the said composition.
After applying the two coats of composition, the gloss is measured using a Multi-Gloss glossmeter (Minolta, Tokyo, Japan) by measuring the reflectance at an angle of about 60° taken relative to the perpendicular to the surface. The gloss is preferably measured about 10 minutes after applying the cosmetic composition.
The measurement is repeated at least five times.
The lowest and the highest gloss values are removed and a mean is determined on the remaining three values.
The gloss of a cosmetic composition according to the present invention may be greater than or equal to about 20 and more particularly greater than or equal to about 22.
The term "gloss staying power" is intended to denote the staying power of the gloss of a composition as may conventionally be measured using a glossmeter via the following method.
After measuring the gloss of a cosmetic composition by means of a protocol as defined above, a tissue is applied onto the sample of synthetic skin comprising the two coats of cosmetic compositions applied as defined above. Such a tissue may be, for example, a Kleenex tissue.
The pressure of the tissue on the sample is applied by means of a press of mass
1.5 kg, for 2 seconds. The application of the pressure is controlled by means of a rheometer (Exponet 32 texture).
Next, the gloss of the sample is measured as defined above.
The measurement is repeated at least 5 times.
The lowest gloss value and the highest gloss value are removed, and a mean is determined on the remaining three values.
The gloss staying power of a cosmetic composition according to the present invention may be greater than or equal to about 7 and more particularly greater than or equal to about 8.
ESTER OF DIMERDILINOLEIC ACID AND OF POLYOL(S)
In the expression "ester of dimerdilinoleic acid and of polyol(s) or an ester thereof, the term "or an ester thereof is intended to denote one of the derivatives of these dimerdilinoleic acid esters of polyol(s) obtained either by reaction of alcohol function(s) of the polyol, which are not employed in bonds of ester type with acid functions of the dilinoleic acid, with one or more carboxylic functions of acid molecules other than dilinoleic acid or alternatively by reaction of acid functions of the dilinoleic dimer, which are not employed in bonds of ester type with alcohol functions of the polyol, with alcohol functions of alcohol molecules other than the polyol.
Dimerdilinoleic acid
The dimerdilinoleic acid that is suitable for use in the present invention may be obtained by polymerization reaction, especially by intermolecular dimerization of at least one linoleic acid.
The oxidation stability of the compound may be improved by hydrogenating the double bonds remaining after the dimerization reaction.
The linoleic acid dimer may also be obtained by dimerization of the hydrogenated form of linoleic acid.
The hydrogenated form of the acid or of the diacid may be partial or total, and may correspond, for example, to the saturated form, which is more oxidation-stable.
As indicated previously, the carboxylic functions of the dimerdilinoleic acid residue not engaged in the ester bond with the polyol residue (s) may be engaged in other ester bonds with other alcohol functions of alcohol molecules other than the polyol(s).
These alcohol molecules or residues may be monoalcohols or polyols.
As examples of alcohol residues that are suitable for use in the invention, mention may be made of hydrocarbon-based compounds comprising a hydroxyl function and containing from 4 to 40 carbon atoms, in particular from 6 to 36 carbon atoms, in particular from 8 to 32 carbon atoms, in particular from 16 to 28 carbon atoms and more particularly from 18 to 24 carbon atoms.
As examples of monoalcohols that are suitable for the invention, mention may be made, in a non-limiting manner, of butanol, pentanol, propanol, hexanol, heptanol, octanol, decanol, dodecanol, hexadecanol, octadecanol, eicosadecanol, phytosterol, isostearol, stearol, cetol, behenol, etc. Polyo Is
The term "polyol" is intended to denote any hydrocarbon-based compound comprising at least two hydroxyl functions and containing from 4 to 40 carbon atoms, in particular from 6 to 36 carbon atoms, in particular from 8 to 32 carbon atoms, in particular from 16 to 28 carbon atoms and more particularly from 18 to 24 carbon atoms.
The hydrocarbon-based chains may be interrupted, where appropriate, by the presence of at least one hetero atom, and especially an oxygen atom.
A polyol or a polyol ester that is suitable for use in the present invention may comprise, for example, from 2 to 12 hydroxyl functions, in particular from 2 to 8 hydroxyl functions, and more particularly from 4 to 6 hydroxyl functions.
Where appropriate, the hydroxyl functions, other than those already employed in an ester bond with the dimerdilinoleic acid, may also be employed, wholly or partly with other ester bonds via reactivity with acid molecules other than the dimerdilinoleic acid.
The polyol or an ester thereof that is suitable for use in the present invention may be chosen especially from linear, branched, cyclic or polycyclic, saturated or unsaturated alcohols.
Thus, the polyol may be chosen, for example, from a diol, a triol, a tetraol, or a pentaol, or an ester thereof.
The polyol may be a diol, or an ester thereof, chosen especially from a fatty alcohol dimer, a monoglycerol or polyglycerol, a C2-4 monoalkylene or polyalkylene glycol, 1,4-butanediol and pentaerythritol.
As examples of diols that are also suitable for use in the invention, mention may be made, in a non-exhaustive manner, of butanediol, pentanediol, propanediol, hexanediol, hexylene glycol, heptanediol, octanediol, nonanediol, decanediol, 1-decanediol, dodecanediol, tridecanediol, tetradecanediol, pentadecanediol, hexadecanediol, nonadecanediol, octadecanediol, cyclohexanediol, diglycerol, erythritol, pentaerythritol, xylitol, sorbitol, ethylene glycol and xylene glycol, and isomers thereof.
A fatty alcohol dimer may also be the product of hydrogenation, for example catalytic hydrogenation, of a fatty acid dimer, which is itself obtained by dimerization of at least one unsaturated fatty acid, especially of Cs to C34, especially of C12 to C22, in particular of C16 to C20 and more particularly of C18. A fatty alcohol dimer may range from C16 to Cβs, especially from C24 to C44, in particular from C32 to C40 and more particularly may be of C36.
According to one particular embodiment, a fatty alcohol dimer may be a diol dimer that can be the product of hydrogenation of dilinoleic diacid. It may be in a saturated form.
A fatty alcohol dimer may be, for example, a dilinoleol dimer.
As an example of a diol that may be suitable for use in the invention, mention may be made especially of diglycerol.
This compound is a glycerol dimer resulting from the condensation of two molecules of glycerol, with the loss of a water molecule.
The term "diglycerol" denotes any isomer combination that can result from such a condensation, for instance linear isomers, branched isomers and, where appropriate, cyclic isomers resulting from an intramolecular dehydration of a diglycerol molecule.
The diglycerol may be obtained via any process known to those skilled in the art and especially those described in patent EP 0 750 848.
As examples of acid molecules that can interact with one or more hydroxyl functions of the polyol, not employed in the ester bond with the dimerdilinoleic acid, mention may be made, in a non-limiting manner, of molecules derived from isostearic acid, behenic acid, phytosteric acid, stearic acid or cetylic acid.
An ester that is suitable for use in the present invention may be obtained by reacting a polyol or an ester thereof with a dimerdilinoleic acid, in a molar ratio of about 1.0:0.2-1.0.
An ester that may be suitable for use in the present invention may especially be obtained by reacting a dimerdilinoleic acid with a dilinoleol and, where appropriate, at least one additional monoalcohol chosen especially from behenol, isostearol, phytosterol, stearol and cetol, and mixtures thereof.
Thus, an ester used in the context of the present invention may be used in the form of a mixture of various esters, for example.
An ester that is suitable for the invention may be obtained, for example, by reacting a glycerol, an isostearic acid and a dimerdilinoleic acid, especially, in a molar ratio of 1.0:0.2-1.0:0.5-0.9.
As examples of esters of dimerdilinoleic acid and of polyol(s) or an ester thereof suitable for the invention, mention may be made of the esters described in patent applications JP 2004-256515 and JP 2005-179377.
An ester of dilinoleic acid and of polyol(s) or an ester thereof suitable for use in the present invention may have a molecular weight ranging from about 2000 to about 25 000 g/mol, in particular from about 4000 to about 20 000 g/mol, in particular from about 7000 to about 15 000 g/mol and more particularly from about 8000 to about
10 000 g/mol.
According to one embodiment, an ester in accordance with the invention may comprise an alternating sequence of dimerdilinoleate residue(s) and of residue (s) related to the said polyol(s), and especially to the said diol(s), the said polyols or diols being, for example, as defined above.
Thus, in such a configuration, each of the two ends of the said sequence may bear, respectively, a unit OR' and OR" with R' and R" representing, independently of each other, a hydrogen atom or OR' and OR" representing, independently of each other, a C2 to C36, especially Cs to C24, in particular C12 to C20 and more particularly C16 to C18 hydrocarbon-based monoalcohol residue.
According to one embodiment, R' and R" may both represent a hydrogen atom.
According to one embodiment, OR' and OR" may both represent an identical or different hydrocarbon-based monoalcohol residue.
As examples of hydrocarbon-based monoalcohol residues OR' and OR" that may be suitable for the invention, mention may be made of fatty alcohol residues.
According to one embodiment, an ester of dimer dilinoleic acid and of polyol(s) or an ester thereof that may be suitable for use in the present invention may have the general formula (I) below:
R3-OCO-Ri(-COO-R2-OCO-Ri)n-COO-R3 (I)
in which:
- CORiCO represents a dimerdilinoleate residue,
- OR2O represents a fatty alcohol dimer residue, may range from C16 to C68, especially from C24 to C44, in particular from C32 to C40 and more particularly may be of C36. - OR-3 represents a monoalcohol residue may range from 4 to 40 carbon atoms, in particular from 6 to 36 carbon atoms, in particular from 8 to 32, in particular from 16 to 28, and more particularly from 18 to 24 carbon atoms, and
- n is an integer ranging from 1 to 15, in particular from 2 to 10 and more particularly from 5 to 7.
According to one embodiment, OR2O may represent a dimerdilinoleyl residue. Moreover, OR3 may represent a hydrocarbon-based monoalcohol residue chosen, for example, from behenyl, isostearyl and phytosteryl residues, and mixtures thereof.
According to another embodiment, the ester of dimerdilinoleic acid and of polyol(s) or an ester thereof that may be suitable for use in the invention may, especially, have the general formula (II) below:
HO-R? 2 -(-O— C -R' , C— 0-R2 )- OH
in which:
- n is an integer ranging from 1 to 15, especially from 2 to 10 and in particular from
5 to 7
- OCR' 1 CO represents a dimerdilinoleate residue,
- OR'2O represents a diglyceryl residue of general formula (III) below:
Figure imgf000010_0001
in which:
R'3 represents H or OR'3 represents a fatty acid residue that may range from Cs to C34, especially from C12 to C22, in particular of C16 to C2o and more particularly may be C18..
According to one embodiment, the fatty acid residue represented by OR3 may be an isostearyl residue.
The viscosity of an ester of dimerdilinoleic acid and of polyol(s) or an ester thereof, according to the invention, may be measured according to any process known to those skilled in the art, and especially according to the conventional process described hereinbelow.
The viscosity may be measured using a cone/plate or parallel plate viscometer of Ares type (TA-Instrument) operating in kinetic sweep mode over a shear range of about 1-1000 s"1 to induce a flow tension at about 1000 Pa.
The cone/plate or parallel plates may consist of a material selected from the group constituted of stainless steel, acrylic resins or polyphenylene sulfide (PPS resin).
The cone/plate diameter may be 25 mm (cone angle 0.10 radiants).
The measurement is performed at about 25°C.
Before any measurement, the stability of the sample is checked by means of the dynamic sweep period test, which makes it possible to determine if the sample is stable per se.
The shear viscosity is determined using the ETA value in the plateau region according to the flow.
The dynamic sweep period is determined at a frequency of 1.0 Hz over a period of 600 seconds.
The measurements at constant sweep rate are performed with a rate ranging from 1.0 to 1000 s"1 and in particular from 1.0 to 100 s"1.
The viscosity of an ester of dimerdilinoleic acid and of polyol or an ester thereof suitable for use in the invention may range from about 20 000 mPa.s to about 150 000 mPa.s, especially from about 40 000 mPa.s to about lOO OOO mPa.s and in particular from about 60 000 mPa.s to about 80 000 mPa.s.
An ester that is suitable for the invention may be chosen especially from the esters having the following INCI nomenclature: polyglyceryl-2 isostearate dimerdilinoleate copolymer, bis-behenyl/isostearyl/phytosteryl dimerdilinoleyl dimerdilinoleate, and mixtures thereof.
Such compounds may be obtained, for example, under the reference Hailucent ISDA (Kokyu Alcohol) and Plandool-G (Nippon Fine Chemical Company Ltd).
An ester of dimerdilinoleic acid and of polyol(s) or an ester thereof suitable for use in the invention may be advantageously present in the cosmetic compositions according to the invention in an amount sufficient to give these compositions improved cosmetic properties, especially in terms of mean gloss staying power. The ester may be present in a content ranging from about 5% to about 90% by weight, in particular from about 15% to about 80% by weight and more particularly from about 20% to about 50% by weight relative to the total weight of the composition. SEMI-CRYSTALLINE POLYMER
The compositions according to the invention may also advantageously comprise at least one semi-crystalline polymer.
For the purposes of the invention, the term "polymer" means a compound comprising at least 2 repeating units, especially at least 3 repeating units, and in particular at least 10 repeating units.
For the purposes of the invention, the term "semi-crystalline polymer" means a polymer comprising a crystallizable portion and an amorphous portion in the backbone and having a first-order reversible temperature of phase change, in particular of melting
(solid-liquid transition). The crystallizable portion may be either a side chain (or pendent chain) or a block in the backbone.
When the crystallizable portion of the semi-crystalline polymer is a block of the polymer backbone, this crystallizable block is of different chemical nature from that of the amorphous blocks.
In this case, the semi-crystalline polymer may be a block copolymer, for example of the diblock, triblock or multiblock type.
When the crystallizable portion is a pendent chain on the backbone, the semi- crystalline polymer may be a homopolymer or a copolymer.
The crystallizable blocks or chains of the semi-crystalline polymers may represent at least 30% and better still at least 40% of the total weight of each polymer.
The terms "organic compound" and "of organic structure" mean a compound comprising carbon atoms and hydrogen atoms and possibly hetero atoms, for instance S, O, N or P, alone or in combination.
The semi-crystalline polymer(s) according to the invention preferably has (have) a melting point higher than the temperature of the keratin support intended to receive the said composition, in particular the skin or the lips.
The melting point of a semi-crystalline polymer that is suitable for the invention may be, for example, less than about 500C. The melting point of a semi-crystalline polymer that is suitable for the invention may especially be greater than or equal to about 25°C and less than about 45°C. In particular, the melting point of the semi-crystalline polymer may be greater than or equal to about 35°C and less than about 400C.
The melting point values correspond to the melting point measured using a differential scanning calorimeter (D. S. C.) such as the calorimeter sold under the name DSC 30 by the company Mettler, with a temperature rise of 5 or 100C per minute. The melting point under consideration is the point corresponding to the temperature of the most endothermic peak in the thermogram.
According to the invention, the semi-crystalline polymers may be soluble in a fatty phase, especially to at least 1% by weight, at a temperature above their melting point.
The semi- crystalline polymers of the invention containing crystallizable blocks may be block or multiblock copolymers. They may be obtained via polymerization of a monomer containing reactive double bonds (or ethylenic bonds) or via poly condensation.
When the polymers of the invention are polymers containing crystallizable side chains, these polymers may advantageously be in random form.
A semi-crystalline polymer that may be suitable for use in the present invention may be selected from the group constituted of a polymer comprising a) a hydrocarbon-based or silicone polymer backbone and b) at least one crystallizable organic side chain and/or a crystallizable organic block forming part of the polymer backbone of the said polymer, the said polymer having a number-average molecular mass of greater than 2000.
The semi-crystalline polymers of the invention may be of synthetic origin. The semi-crystalline polymers that may be used in the invention may in particular be selected from the group constituted of:
- block copolymers of polyolefϊns of controlled crystallization, whose monomers are described in EP-A-O 951 897,
- poly condensates, especially of aliphatic or aromatic or aliphatic/aromatic polyester type, - homopolymers or copolymers bearing at least one crystallizable side chain and homopolymers or copolymers bearing at least one crystallizable block in the backbone, for instance those described in document US-A-5 156 911,
- homopolymers or copolymers bearing at least one crystallizable side chain, in particular bearing fluoro group(s), such as those described in document
WO-A-01/19333,
- copolymers comprising carboxylate groups and polydimethylsiloxane groups,
- and mixtures thereof.
A) Semi-crystalline polymers containing crystallizable side chains
Mention may be made in particular of those defined in documents US-A- 5 156 911 and WO-A-01/19333.
They are homopolymers or copolymers comprising from 50% to 100% by weight of units resulting from the polymerization of one or more monomers bearing a crystallizable hydrophobic side chain.
These homopolymers or copolymers may be of any nature, provided that they meet the conditions mentioned hereinbelow with, in particular, the characteristic of being soluble or dispersible in the fatty phase, by heating above their melting point mp. They can result:
- from the polymerization, especially the free-radical polymerization, of one or more monomers containing reactive or ethylenic double bond(s) with respect to a polymerization, namely a vinyl, (meth)acrylic or allylic group,
- from the poly condensation of one or more monomers bearing co-reactive groups (carboxylic acid, sulfonic acid, alcohol, amine or isocyanate), such as, for example, polyesters, polyurethanes, polyethers, polyureas or polyamides.
In general, the crystallizable units (chains or blocks) of semi-crystalline polymers according to the invention are derived from monomer(s) containing crystallizable block(s) or chain(s), used for manufacturing semi- crystalline polymers. These polymers are chosen especially from homopolymers and copolymers resulting from the polymerization of at least one monomer containing crystallizable chain(s) that may be represented by the formula: — M—
C
with M representing an atom of the polymer backbone,
S representing a spacer, and
C representing a crystallizable group.
The crystallizable chains "-S-C" may be aliphatic or aromatic, and optionally fluorinated or perfluorinated.
"S" especially represents a group (CH2)n or (CH2CH2O)n or (CH2O), which may be linear or branched or cyclic, with n being an integer ranging from 0 to 22.
Preferably, "S" is a linear group.
Preferably, "S" and "C" are different.
When the crystallizable chains are hydrocarbon-based aliphatic chains, they may comprise hydrocarbon-based alkyl chains containing at least 11 carbon atoms and not more than 40 carbon atoms and better still not more than 24 carbon atoms. They may especially be aliphatic chains or alkyl chains containing at least 12 carbon atoms, and they may be, in particular Cw-C24, in particular Ci6-C22, alkyl chains. When they are fluoroalkyl or perfluoroalkyl chains, they may contain at least 11 carbon atoms, at least 6 of which carbon atoms are fluorinated.
As examples of semi-crystalline homopolymers or copolymers containing crystallizable chain(s), mention may be made of those resulting from the polymerization of one or more of the following monomers: (meth)acrylates of saturated alkyls with the alkyl group being Ci4-C24, perfluoroalkyl (meth)acrylates with a C11-C15 perfluoroalkyl group, N-alkyl(meth)acrylamides with the alkyl group being Ci4 to C24 with or without a fluorine atom, vinyl esters containing alkyl or perfluoroalkyl chains with the alkyl group being Ci4 to C24 (with at least 6 fluorine atoms per perfluoroalkyl chain), vinyl ethers containing alkyl or perfluoroalkyl chains with the alkyl group being Ci4 to C24 and at least 6 fluorine atoms per perfluoroalkyl chain, Ci4 to C24 α-olefms such as, for example, octadecene, para-alkylstyrenes with an alkyl group containing from 12 to 24 carbon atoms, and mixtures thereof. When the polymers result from a polycondensation, the hydrocarbon-based and/or fluorinated crystallizable chains as defined above may be borne by a monomer that may be a diacid, a diol, a diamine or a diisocyanate.
When the polymers that are the subject of the invention are copolymers, they additionally contain from 0 to 50% of groups Y or Z resulting from the copolymerization: α) of Y which is a polar or non-polar monomer or a mixture of the two:
When Y is a polar monomer, it is either a monomer bearing polyoxyalkylenated groups (especially oxyethylenated and/or oxypropylenated groups), a hydroxyalkyl (meth)acrylate, for instance hydroxyethyl acrylate, (meth)acrylamide, an N-alkyl(meth)acrylamide, an N,N-dialkyl(meth)acrylamide such as, for example, N,N-diisopropylacrylamide or N-vinylpyrrolidone (NVP), N- vinylcapro lactam, a monomer bearing at least one carboxylic acid group, for instance (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid or fumaric acid, or bearing a carboxylic acid anhydride group, for instance maleic anhydride, and mixtures thereof.
When Y is a non-polar monomer, it may be an ester of the linear, branched or cyclic alkyl (meth)acrylate type, a vinyl ester, an alkyl vinyl ether, an α-olefm, styrene or styrene substituted with a Ci to C10 alkyl group, for instance α-methylstyrene, or a macromonomer of the polyorganosiloxane type containing vinyl unsaturation.
For the purposes of the invention, the term "alkyl" means a saturated group especially of Cs to C24, except where otherwise mentioned. β) of Z which is a polar monomer or a mixture of polar monomers. In this case, Z has the same definition as the "polar Y" defined above.
Preferably, the semi-crystalline polymers containing a crystallizable side chain are alkyl (meth)acrylate or alkyl(meth)acrylamide homopolymers with an alkyl group as defined above, and especially of Ci4-C24, especially of Ci6-C2O, copolymers of these monomers with a hydrophilic monomer preferably of different nature from (meth)acrylic acid, for instance N-vinylpyrrolidone or hydroxyethyl (meth)acrylate, and mixtures thereof.
Advantageously, the semi-crystalline polymer(s) containing a crystallizable side chain has (have) a weight-average molecular mass Mp ranging from 5000 to 1 000 000 g/mol, preferably from 10 000 to 800 000 g/mol, preferentially from 15 000 to 500 000 g/mol and more preferably from 100 000 to 200 000 g/mol.
As a particular example of a semi-crystalline polymer that may be used in a composition according to the invention, mention may be made of the Intelimer products
®
from the company Landec described in the brochure "Intelimer polymers", Landec IP22
(Rev. 4-97). These polymers are in solid form at room temperature (25°C). They bear crystallizable side chains and correspond to the above general formula.
For example, the Intelimer product IPA 13-1 from the company Landec is chosen, which is a polystearyl acrylate with a molecular weight of about 145 000 and a melting point of 49°C.
The semi-crystalline polymers may especially be those described in Examples 3, 4, 5, 7 and 9 of patent US-A-5 156 911, containing a -COOH group, resulting from the copolymerization of acrylic acid and of a Cs to Ci6 alkyl (meth)acrylate with a melting point ranging from 200C to 35°C, and more particularly from the copolymerization:
- of acrylic acid, of hexadecyl acrylate and of isodecyl acrylate in a 1/16/3 ratio,
- of acrylic acid and of pentadecyl acrylate in a 1/19 ratio,
- of acrylic acid, of hexadecyl acrylate and of ethyl acrylate in a 2.5/76.5/20 ratio,
- of acrylic acid, of hexadecyl acrylate and of methyl acrylate in a 5/85/10 ratio,
- of acrylic acid and of octadecyl (meth)acrylate in a 2.5/97.5 ratio.
It is also possible to use the polymer Structure "O" from National Starch, such as that described in document US-A-5 736 125 with a melting point of 44°C.
The semi-crystalline polymers may especially be semi- crystalline polymers with crystallizable pendent chains comprising fluoro groups, as described in Examples 1, 4, 6, 7 and 8 of document WO-A-01/19333.
It is also possible to use the semi-crystalline polymers obtained by copolymerization of stearyl acrylate and of acrylic acid or of NVP, as described in document US-A-5 519 063 or EP-A-055 0745. It is also possible to use the semi-crystalline polymers obtained by copolymerization of behenyl acrylate and of acrylic acid or of NVP, such as those described in documents US-A-5 519 063 and EP-A-550 745. B) Polymers bearing at least one crystallizable block in the backbone
This may also be a case of polymers that are soluble or dispersible in the fatty phase by heating above their melting point mp. These polymers are especially block copolymers consisting of at least two blocks of different chemical nature, one of which is crystallizable.
The polymer bearing at least one crystallizable block in the backbone may be selected from the group constituted of block copolymers of olefin or of cycloolefϊn containing a crystallizable chain, for instance those derived from the block polymerization of:
- cyclobutene, cyclohexene, cyclooctene, norbornene (i.e. bicyclo(2,2,l)-2- heptene), 5-methylnorbornene, 5-ethylnorbornene, 5,6-dimethylnorbornene, 5,5,6-tri- methylnorbornene, 5-ethylidenenorbornene, 5-phenylnorbornene, 5-benzylnorbornene, 5-vinylnorbornene, l,4,5,8-dimethano-l,2,3,4,4a,5,8a-octahydronaphthalene, dicyclopentadiene, or mixtures thereof,
- with ethylene, propylene, 1-butene, 3-methyl-l-butene, 1-hexene, 4-methyl- 1-pentene, 1-octene, 1-decene or 1-eicosene, or mixtures thereof,
- and in particular copoly(ethylene/norbornene) blocks and (ethylene/propylene/ethylidene-norbornene) block terpolymers.
Those resulting from the block copolymerization of at least 2 C2-Ci6, and better still C4-C12, α-olefms such as those mentioned above and in particular block bipolymers of ethylene and of 1-octene may also be used.
The polymer bearing at least one crystallizable block in the backbone may be selected from the group constituted of copolymers containing at least one crystallizable block, the rest of the copolymer being amorphous at room temperature. These copolymers may also contain two crystallizable blocks of different chemical nature.
The preferred copolymers are those that simultaneously contain, at room temperature, a crystallizable block and an amorphous block that are both hydrophobic and lipophilic, sequentially distributed. Mention may be made, for example, of polymers containing one of the crystallizable blocks and one of the amorphous blocks below:
- block that is crystallizable by nature, of polyester type, for instance poly(alkylene terephthalate), or of polyolefϊn type, for instance polyethylenes or polypropylenes,
- amorphous and lipophilic block, for instance amorphous polyolefms or copoly(olefϊn)s such as poly(isobutylene), hydrogenated polybutadiene or hydrogenated poly(isoprene).
As examples of such copolymers containing a crystallizable block and an amorphous block, mention may be made of:
α) poly(ε-caprolactone)-b-poly(butadiene) block copolymers, preferably used hydrogenated, such as those described in the article "Melting behaviour of poly(-caprolactone)-block-polybutadiene copolymers" from S. Nojima, Macromolecules, 32, 3727-3734 (1999),
β) the hydrogenated block or multiblock poly(butylene terephthalate)-b- poly(isoprene) block copolymers cited in the article "Study of morphological and mechanical properties of PP/PBT" by B. Boutevin et al, Polymer Bulletin, 34, 117-123 (1995),
γ) the poly(ethylene)-b-copoly(ethylene/propylene) block copolymers cited in the articles "Morphology of semi-crystalline block copolymers of ethylene-(ethylene-alt- propylene)" by P. Rangarajan et al., Macromolecules, 26, 4640-4645 (1993) and "Polymer aggregates with crystalline cores: the system poly(ethylene)-poly(ethylene-propylene)" by
P. Richter et al., Macromolecules, 30, 1053-1068 (1997),
δ) the poly(ethylene)-b-poly(ethylethylene) block copolymers cited in the general article "Crystallization in block copolymers" by LW. Hamley, Advances in Polymer Science, Vol. 148, 113-137 (1999).
C) Poly condensates of aliphatic or aromatic or aliphatic/ aromatic polyester type
The polyester poly condensates may be selected from the group constituted of aliphatic polyesters. Their molecular mass is, for example, greater than or equal to about 200 g/mol and less than or equal to about 15 000 g/mol, and more particularly greater than or equal to about 1000 g/mol and less than or equal to 10 000 g/mol, in particular greater than or equal to about 2000 g/mol and less than or equal to about 5000 g/mol.
The polyester polycondensates are in particular selected from the group constituted of polycapro lactones. In particular, the polycapro lactones may be selected from the group constituted of ε-capro lactone homopolymers. The homopolymerization may be initiated with a diol, especially a diol containing from 2 to 10 atoms, such as diethylene glycol, 1,4-butanediol or neopentyl glycol.
Polycapro lactones may be used for example, especially those sold under the name CAP A® 240 (melting point of 68°C and molecular weight of 4000 g/mol), 223 (melting point of 48°C and molecular weight of 2000 g/mol), 222 (melting point of 48°C and molecular weight of 2000 g/mol), 217 (melting point of 44°C and molecular weight of 1250 g/mol), 2125 (melting point of 45°C and molecular weight of 1250) g/mol, 212 (melting point of 45°C and molecular weight of 1000 g/mol), 210 (melting point of 38°C and molecular weight of 1000 g/mol), 205 (melting point of 39°C and molecular weight of 830 g/mol) by the company Solvay, or PCL-300 and PCL-700 by the company Union Carbide.
The CAPA 2125 whose melting point is between 35 and 45°C and whose weight-average molecular mass is equal to 1250 g/mol may be used in particular. D) Copolymer comprising carboxylate groups and poly dimethylsiloxane groups
In the present patent application, the expression "copolymer comprising carboxylate groups and poly dimethylsiloxane groups" means a copolymer obtained from the polymerization of (a) one or more carboxylic (acid or ester) monomers, with (b) one or more poly dimethylsiloxane (PDMS) chains comprising at least one polymerizable radical.
Among the "carboxylic monomers" that are suitable for use in the invention, mention may be made of carboxylic acid monomers and carboxylic acid ester monomers.
Thus, the monomer (a) may be chosen, for example, from acrylic acid, methacrylic acid, maleic acid, fumaric acid, itaconic acid, crotonic acid, esters thereof and mixtures of these monomers. Esters that may be mentioned include the following monomers methyl, ethyl, stearyl, butyl or 2-ethylhexyl acrylate, methacrylate, maleate, fumarate, itaconate and/or crotonate, and mixtures thereof. According to one embodiment of the invention, the monomers in ester form may be selected from the group constituted of linear or branched, preferably C1-C24 and better still C1-C22 alkyl acrylates and methacrylates, the alkyl radical being selected from the group constituted of methyl, ethyl, stearyl, butyl and 2-ethylhexyl radicals, and mixtures thereof.
According to one embodiment of the invention, the copolymer may comprise as carboxylate groups at least one group selected from the group constituted of acrylic acid and methacrylic acid, and methyl, ethyl, stearyl, butyl or 2-ethylhexyl acrylate or methacrylate, and mixtures thereof.
In the present patent application, the term "polydimethylsiloxanes" (also known as organopolysiloxanes and abbreviated as PDMS) denotes, in accordance with what is generally accepted, any organosilicon polymer or oligomer of linear structure, of variable molecular weight, obtained by polymerization and/or poly condensation of suitably functionalized silanes, and consisting essentially of a repetition of main units in which the silicon atoms are linked together via oxygen atoms (siloxane bond≡Si-O-Si≡), comprising trimethyl radicals directly linked via a carbon atom to the said silicon atoms.
The PDMS chains that may be used to obtain the copolymer used according to the invention comprise at least one polymerizable radical group, preferably located on at least one of the ends of the chain, i.e. the PDMS may contain, for example, a polymerizable radical group on the two ends of the chain or one polymerizable radical group on one end of the chain and one trimethylsilyl end group on the other end of the chain. The polymerizable radical group may especially be an acrylic or methacrylic group, in particular a group CH2 = CR1-CO-O-R2, in which Ri represents a hydrogen or a methyl group and R2 represents -CH2-, -(CH2)n- with n = 3, 5, 8 or 10, -CH2-CH(CHs)-CH2-, -CH2-CH2-O-CH2-CH2-, -CH2-CH2-O-CH2-CH2-CH(CHS)-CH2-, -CH2-CH2-O-CH2 CH2- 0-CH2-CH2-CH2-.
The copolymers that may be used in the composition of the invention may be obtained according to the usual methods of polymerization and grafting, for example by free-radical polymerization (a) of a PDMS comprising at least one polymerizable radical group (for example on one of the ends of the chain or on both ends) and (b) of at least one carboxylic monomer, as described, for example, in documents US-A-5 061 481 and US- A-5 219 560. The copolymers obtained may have a molecular weight ranging from about 3000 g/mol to about 200 000 g/mol and especially from about 5000 g/mol to about 100 000 g/mol.
A copolymer that may be used in a composition of the invention may be in its native form or in dispersed form in a solvent such as lower alcohols containing from 2 to 8 carbon atoms, for instance isopropyl alcohol, or oils, for instance volatile silicone oils (for example cyclopentasiloxane).
As copolymers that may be used in a composition of the invention, mention may be made, for example, of copolymers of acrylic acid and of stearyl acrylate containing polydimethylsiloxane grafts, copolymers of stearyl methacrylate containing polydimethylsiloxane grafts, copolymers of acrylic acid and of stearyl methacrylate containing polydimethylsiloxane grafts, copolymers of methyl methacrylate, butyl methacrylate, 2-ethylhexyl acrylate and stearyl methacrylate containing polydimethylsiloxane grafts. As a copolymer that may be used in the composition of the invention, mention may also be made of the copolymers sold by the company Shin-Etsu under the names KP-561 (CTFA name: acrylates/dimethicone), KP-541 in which the copolymer is dispersed at 60% by weight in isopropyl alcohol (CTFA name: acrylates/dimethicone and isopropyl alcohol), KP-545 in which the copolymer is dispersed at 30% in cyclopentasiloxane (CTFA name: acrylates/dimethicone and cyclopentasiloxane).
According to one particular embodiment of the invention, a copolymer of acrylate and of dimethicone, such as KP-561, may be used; this copolymer is not dispersed in a solvent, but is in waxy form, its melting point being about 300C.
In the last two cases, the crystallizable side chain(s) or block(s) are hydrophobic.
The semi-crystalline polymers of the composition of the invention may or may not be partially crosslinked provided that the degree of crosslinking does not interfere with their dissolution or dispersion in the fatty phase by heating above their melting point. This may then be a case of chemical crosslinking, by reaction with a multifunctional monomer during polymerization. It may also be a case of physical crosslinking, which may then be due either to the establishment of bonds of hydrogen or dipolar type between groups borne by the polymer, for instance dipolar interactions between carboxylate ionomers, these interactions being in small amount and borne by the polymer backbone; or to a phase separation between the crystallizable blocks and the amorphous blocks, borne by the polymer.
Preferably, the semi-crystalline polymers of the composition according to the invention are not crosslinked.
In practice, the total amount of semi-crystalline polymer(s) may represent from about 1% to about 8%, in particular from about 2% to about 6% and more particularly from about 3% to about 6% by weight relative to the total weight of the composition. In particular, it may represent from about 4% to about 5% by weight relative to the total weight of the composition.
When introduced in sufficient amount, and in combination with an ester of dimerdilinoleic acid and of polyol(s), or an ester thereof as defined above, the semi- crystalline polymer especially has the advantage of being able to afford an improvement in the gloss staying power, or even also in the colour staying power, to the cosmetic compositions according to the invention.
According to one embodiment, the ester of dimerdilinoleic acid and of polyol(s), or an ester thereof, and the semi-crystalline polymer are present, in the compositions according to the invention, in a weight ratio that may range from about 15:1 to about 2:1, in particular from about 10:1 to about 4:1 and more particularly from about 8:1 to about 6:1.
PHYSIOLOGICALLY ACCEPTABLE MEDIUM
The term "physiologically acceptable medium" is intended to denote a medium that is particularly suitable for the application of a composition according to the invention to the skin and/or the lips. The physiologically acceptable medium is generally suited to the nature of the support onto which the composition is to be applied, and to the aspect in which the composition is intended to be conditioned.
The physiologically acceptable medium may comprise an aqueous and/or water-soluble phase and/or a fatty phase.
According to one particular embodiment, the aqueous phase or the fatty phase may form the continuous phase of the composition. This aqueous phase may, where appropriate, be thickened, gelled or structured by also incorporating therein a conventional aqueous gelling agent especially of mineral origin, for instance clay, and/or of organic origin, for instance an aqueous gelling polymer.
According to another particular embodiment, a composition in accordance with the invention may be in the form of a suspension, a dispersion, a solution, a gel or an emulsion, especially an oil-in-water (O/W) or water-in-oil (W/O) emulsion, or a multiple emulsion (W/O/W, polyol/O/W or 0/W/O), or in the form of a cream, a stick, a paste, a mousse, a dispersion of vesicles, especially of ionic or nonionic lipids, a two-phase or multi-phase lotion or a powder.
For the purposes of the present invention, the emulsions contain a lipophilic phase and a hydrophilic phase, the latter phase not systematically being water.
Thus, the cosmetic compositions in accordance with the invention may be in the form of an anhydrous emulsion.
In particular, the composition may have, for example, a continuous fatty phase, which may contain less than 10% by weight of water, especially less than 5% by weight of water or even less than 1% by weight of water relative to the total weight of the composition.
In particular, a cosmetic composition according to the invention may be anhydrous, i.e. may contain less than 5%, in particular less than 3%, in particular less than 2% and more particularly less than 1% by weight of water relative to the total weight of the composition. This composition may then especially be in the form of oily gels, oily liquids, pastes or sticks or alternatively in the form of a vesicular dispersion containing ionic and/or nonionic liquids. FATTY PHASE
A cosmetic composition in accordance with the present invention may comprise at least one fatty phase, for example a liquid fatty phase, selected from the group constituted of volatile and non-volatile oils, and a fatty substance that is solid at room temperature (20-250C) and atmospheric pressure, and mixtures thereof.
A composition according to the invention may comprise at least one liquid fatty phase selected from the group constituted of volatile oils and non- volatile oils, and mixtures thereof. The term "oil" means any fatty substance that is in liquid form at room temperature (20-250C) and at atmospheric pressure. The liquid fatty phase may also contain, in addition to oils, other compounds dissolved in the oils, such as gelling agents and/or structuring agents.
The oil(s) may be present in a proportion of from 0.1% to 99% by weight, in particular from at least 1% to 90% by weight, more particularly from 5% to 70% by weight, especially from 10% to 60% by weight or even from 20% to 50% by weight relative to the total weight of the cosmetic composition according to the invention.
The liquid fatty phase that may be suitable for preparing a cosmetic composition according to the invention may be selected from the group constituted of volatile or non-volatile, silicone or non-silicone oils, and mixtures thereof.
The volatile or non-volatile oils may be hydrocarbon-based oils especially of animal or plant origin, synthetic oils, silicone oils or fluoro oils, or mixtures thereof.
For the purposes of the present invention, the term "silicone oil" means an oil comprising at least one silicon atom, and especially at least one Si-O group.
The term "hydrocarbon-based oil" means an oil mainly containing hydrogen and carbon atoms, and possibly oxygen, nitrogen, sulfur and/or phosphorus atoms.
Volatile oils
For the purposes of the present invention, the term "volatile oil" means an oil
(or non-aqueous medium) capable of evaporating on contact with the skin in less than one hour, at room temperature and at atmospheric pressure. The volatile oil is a volatile cosmetic oil, which is liquid at room temperature, especially having a non-zero vapour pressure, at room temperature and atmospheric pressure, in particular having a vapour pressure ranging from 0.13 Pa to 40 000 Pa (10~3 to 300 mmHg), preferably ranging from 1.3 Pa to 13 000 Pa (0.01 to 100 mmHg) and preferably ranging from 1.3 Pa to 1300 Pa (0.01 to 10 mmHg).
The volatile hydrocarbon-based oils may be selected from the group constituted of hydrocarbon-based oils containing from 8 to 16 carbon atoms, and especially branched Cs-Ci6 alkanes (also known as isoparaffins), for instance isododecane (also known as 2,2,4,4, 6-pentamethylheptane), isodecane, isohexadecane and, for example, the oils sold under the trade names Isopar® or Permethyl®. Volatile oils that may also be used include volatile silicones, for instance volatile linear or cyclic silicone oils, especially those with a viscosity < 8 centistokes
(8 x 10~6 m2/s), and especially containing from 2 to 10 silicon atoms and in particular from
2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups containing from 1 to 10 carbon atoms. As a volatile silicone oil that may be used in the invention, mention may be made especially of dimethicones with a viscosity of 5 and
6 cSt, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclo- hexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldi- siloxane, octamethyltrisiloxane, decamethyltetrasiloxane and dodecamethylpentasiloxane, and mixtures thereof.
Volatile fluoro oils such as nonafluoromethoxybutane or perfluoromethyl- cyclopentane, and mixtures thereof, may also be used.
It is also possible to use a mixture of the oils mentioned above. Non-volatile oils
The fatty phase of the cosmetic compositions according to the present invention may also comprise at least one non-volatile oil, especially an oil of high molar mass.
For the purposes of the present invention, the term "non-volatile oil" means an oil with a vapour pressure of less than 0.13 Pa and especially oils of high molar mass.
The non- volatile oils may be chosen especially from non- volatile hydrocarbon-based oils, which may be fluorinated, and/or non-volatile silicone oils.
The term "oil of high molar mass" means oils with a molar mass ranging from about 650 to about 10 000 g/mol, in particular from about 750 to about 7500 g/mol, and more particularly ranging from about 1000 to about 5000 g/mol.
As oils of high molar mass that may be used in the present invention, mention may especially be made of oils selected from the group constituted of:
- lipophilic polymers,
- linear fatty acid esters with a total carbon number ranging from 35 to 70, - hydroxylated esters,
- aromatic esters,
- esters Of C24-C2S branched fatty alcohols or fatty acids, - silicone oils,
- oils of plant origin,
- and mixtures thereof.
For example, an oil of high molar mass may be selected from the group constituted of:
a) lipophilic polymers such as:
- polybutylenes such as Indopol H-IOO (of molar mass or MM = 965 g/mol), Indopol H-300 (MM = 1340 g/mol) and Indopol H- 1500 (MM = 2160 g/mol) sold or manufactured by the company Amoco,
- polyisobutylenes, for example hydrogenated polyisobutylenes, such as
Panalane H-300 E sold or manufactured by the company Amoco (MM = 1340 g/mol), Viseal 20000 sold or manufactured by the company Synteal (MM = 6000 g/mol) and Rewopal PIB 1000 sold or manufactured by the company Witco (MM = 1000 g/mol),
- polydecenes and hydrogenated polydecenes such as: Puresyn 10 (MM = 723 g/mol) and Puresyn 150 (MM = 9200 g/mol) sold or manufactured by the company Mobil Chemicals,
- vinylpyrrolidone copolymers such as: the vinylpyrrolidone/1-hexadecene copolymer Antaron V-216 sold or manufactured by the company ISP (MM = 7300 g/mol) and polyvinylpyrrolidone (PVP) copolymers such as the copolymers of a C2 to C30 such as a C3 to C22 alkene and combinations thereof, may be used. As examples of PVP copolymers that may be used in the invention, mention may be made of PVP/vinyl laurate, PVP/vinyl stearate, butylated polyvinylpyrrolidone, PVP/hexadecene, PVP/triacontene or PVP/acrylic acid/lauryl methacrylate copolymer,
b) esters such as:
- linear fatty acid esters with a total carbon number ranging from 35 to 70, for instance pentaerythrityl tetrapelargonate (MM = 697 g/mol),
- hydroxylated esters such as polyglyceryl-2 triisostearate (MM = 965 g/mol),
- aromatic esters such as tridecyl trimellitate (MM = 757 g/mol), - esters of C24-C28 branched fatty alcohols or fatty acids, such as those described in patent application EP-A-O 955 039 and pentaerythritol esters, and especially triisoarachidyl citrate (MM = 1033.76 g/mol), pentaerythrityl tetraisononanoate (MM = 697 g/mol), glyceryl triisostearate (MM = 891 g/mol), glyceryl tris(2-decyl)tetradecanoate (MM = 1143 g/mol), pentaerythrityl tetraisostearate (MM = 1202 g/mol), polyglyceryl-2 tetraisostearate (MM = 1232 g/mol) or alternatively pentaerythrityl tetrakis(2-decyl)tetradecanoate (MM = 1538 g/mol),
- diol dimer esters and polyesters, such as esters of diol dimer and of fatty acid, and esters of diol dimer and of diacid, sold by the company Nippon Fine Chemical and described in the patent application FR 03 02809 filed on 6 March 2003, the content of which is incorporated into the present patent application by reference,
- silicone oils such as phenyl silicones, for instance Belsil PDM 1000 from the company Wacker (MM = 9000 g/mol),
- oils of plant origin such as sesame oil (MM820 g/mol),
- and mixtures thereof.
The esters of diol dimer and of monocarboxylic acid may be obtained from a monocarboxylic acid containing from 4 to 34 carbon atoms and especially from 10 to 32 carbon atoms, these acids being linear or branched, and saturated or unsaturated.
As illustrations of the monocarboxylic acids that are suitable for the invention, mention may be made especially of fatty acids.
The esters of diol dimer and of dicarboxylic acid may be obtained from a diacid dimer derived in particular from the dimerization of an unsaturated fatty acid especially of Cs to C34, especially of C12 to C22, in particular of C16 to C20 and more particularly of Ci 8.
According to one particular variant, it may more particularly be the diacid dimer from which the diol dimer to be esterified is also derived.
The diol dimer esters may be obtained from a diol dimer produced by catalytic hydrogenation of a diacid dimer as described above, for example hydrogenated dilinoleic diacid.
Illustrations of esters of a diol dimer that may especially be mentioned include the esters of dilinoleic diacids and of dilinoleyl diol dimers sold by the company Nippon Fine Chemical under the trade names Lusplan DD-DA5® and DD-D A7®.
An oil of high molar mass may be chosen especially from polybutylenes, polyisobutylenes, hydrogenated polyisobutylenes, polydecenes, hydrogenated polydecenes, vinylpyrrolidone copolymers such as PVP/hexadecene copolymer, pentaerythrityl tetrapelargonate, polyglyceryl-2 triisostearate, tridecyl trimellitate, triisoarachidyl citrate, pentaerythrityl tetraisononanoate, glyceryl triisostearate, glyceryl tris(2-decyl)tetradecanoate, pentaerythrityl tetraisostearate, polyglyceryl-2 tetraisostearate, pentaerythrityl tetrakis(2-decyl)tetradecanoate, phenyl silicones, sesame oil and oils of ester of acid dimer and of alcohol dimer, and mixtures thereof.
As non-volatile hydrocarbon-based oils that are also suitable for use in the invention, mention may be made especially of:
- hydrocarbon-based oils of animal origin,
- hydrocarbon-based oils of plant origin such as phytostearyl esters, such as phytostearyl oleate, phytostearyl isostearate and lauroyl/octyldodecyl/phytostearyl glutamate, for example sold under the name Eldew PS203 by Ajinomoto, triglycerides consisting of fatty acid esters of glycerol, the fatty acids of which may have chain lengths ranging from C4 to C24, these chains possibly being linear or branched, and saturated or unsaturated; these oils are especially heptanoic or octanoic triglycerides, wheatgerm oil, sunflower oil, grapeseed oil, corn oil, apricot oil, castor oil, shea oil, avocado oil, olive oil, soybean oil, sweet almond oil, palm oil, rapeseed oil, cotton seed oil, hazelnut oil, macadamia oil, jojoba oil, alfalfa oil, poppy oil, pumpkin oil, marrow oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passion flower oil or musk rose oil; shea butter; or alternatively caprylic/capric acid triglycerides, for instance those sold by the company Stearineries Dubois or those sold under the names Miglyol 810®, 812® and 818® by the company Dynamit Nobel,
- oils of mineral or synthetic origin, for instance:
• synthetic ethers containing from 10 to 40 carbon atoms;
• linear or branched hydrocarbons of mineral or synthetic origin such as petroleum jelly, polydecenes, hydrogenated polyisobutene such as
Parleam, and squalane, and mixtures thereof, and in particular hydrogenated polyisobutene,
• synthetic esters, for instance oils of formula RiCOOR2 in which Ri represents a linear or branched fatty acid residue containing from 1 to 40 carbon atoms and R2 represents a hydrocarbon-based chain that is especially branched, containing from 1 to 40 carbon atoms provided that Ri + R2 > 10. The esters may be chosen especially from fatty acid esters, for example:
• cetostearyl octanoate, isopropyl alcohol esters, such as isopropyl myristate or isopropyl palmitate, ethyl palmitate, 2-ethylhexyl palmitate, isopropyl stearate or isostearate, isostearyl isostearate, octyl stearate, hydroxylated esters, for instance isostearyl lactate, octyl hydroxystearate, diisopropyl adipate, heptanoates, and especially isostearyl heptanoate, alcohol or polyalcohol octanoates, decanoates or ricinoleates, for instance propylene glycol dioctanoate, cetyl octanoate, tridecyl octanoate, 2-ethylhexyl A- diheptanoate and palmitate, alkyl benzoate, polyethylene glycol diheptanoate, propylene glycol 2-diethylhexanoate, and mixtures thereof,
C12 to C15 alcohol benzoates, hexyl laurate, neopentanoic acid esters, for instance isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate and octyldodecyl neopentanoate, isononanoic acid esters, for instance isononyl isononanoate, isotridecyl isononanoate and octyl isononanoate, and hydroxylated esters, for instance isostearyl lactate and diisostearyl malate;
• polyol esters and pentaerythritol esters, for instance dipentaerythrityl tetrahydroxystearate/tetraisostearate;
• esters of diol dimers and of diacid dimers, such as Lusplan DD-D A5® and Lusplan DD-DA7®, sold by the company Nippon Fine Chemical and described in patent application FR 03/02809 filed on March 2003, the content of which is incorporated in the present application by reference;
• fatty alcohols that are liquid at room temperature, with a branched and/or unsaturated carbon-based chain containing from 12 to 26 carbon atoms, for instance 2-octyldodecanol, isostearyl alcohol, oleyl alcohol, 2-hexyl- decanol, 2-butyloctanol and 2-undecylpentadecanol;
• higher fatty acids such as oleic acid, linoleic acid or linolenic acid, and mixtures thereof; and
• dialkyl carbonates, the two alkyl chains possibly being identical or different, such as dicaprylyl carbonate sold under the name Cetiol CC® by
Cognis;
• non-volatile silicone oils, for instance non-volatile polydimethylsiloxanes (PDMS), polydimethylsiloxanes comprising alkyl or alkoxy groups that are pendent and/or at the end of a silicone chain, these groups each containing from 2 to 24 carbon atoms, phenyl silicones, for instance phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyl- trisiloxanes and 2-phenylethyl trimethylsiloxysilicates, and dimethicones or phenyltrimethicones with a viscosity of less than or equal to 100 cSt, and mixtures thereof;
• and mixtures thereof.
The non- volatile oils may be present in a composition according to the invention in a content ranging from 5% to 90% by weight, especially from 25% to 80% by weight and in particular from 40% to 70% by weight relative to the total weight of the composition.
An oil of high molar mass that may be used in a composition according to the invention may be present in a proportion of from 5% to 40%, preferably from 10% to 30% and better still from 15% to 20% of the total weight of the composition.
Solid fatty substances
The compositions according to the invention may also comprise at least one solid fatty phase selected from the group constituted of waxes and pasty fatty substances, and mixtures thereof.
The wax is solid at room temperature (25°C), with a reversible solid/liquid change of state, having a melting point of greater than 300C, which may be up to 2000C, a hardness of greater than 0.5 MPa and having in the solid state an anisotropic crystal organization.
It may be a hydrocarbon-based wax, a fluoro wax and/or a silicone wax and may be of animal, plant, mineral or synthetic origin.
It may be chosen, for example, from beeswax, carnauba wax, candelilla wax, paraffin waxes, hydrogenated castor oil, synthetic waxes, for instance polyethylene waxes (preferably with a molecular weight of between 400 and 600) or Fischer-Tropsch waxes, silicone waxes, for instance alkyl or alkoxy dimethicones containing from 16 to 45 carbon atoms, ceresins or ozokerites, for instance isoparaffϊns with a melting point of less than 400C, such as EMW-0003 sold by the company Nippon Seirou, α-olefϊn oligomers, such as the polymers Performa V® 825, 103 and 260 sold by the company New Phase Technologies; ethylene-propylene copolymers, such as Performalene® EP 700, and microcrystalline waxes with a melting point of greater than 85°C, such as Hi-Mic® 1070, 1080, 1090 and 3080, sold by Nippon Seirou, and mixtures thereof.
According to one particular embodiment, the wax(es) used in the cosmetic compositions in accordance with the present invention may be present in a content ranging from about 5% to about 30%, in particular from about 5% to about 25%, in particular from about 10% to about 20% and more particularly from about 10% to about 15% by weight relative to the total weight of the composition.
The cosmetic compositions in accordance with the present invention may also comprise at least one pasty compound.
For the purposes of the present invention, the term "pasty compound" means a fatty compound with a reversible solid/liquid change of state, and comprising at a temperature of 23°C a liquid fraction and a solid fraction. The term "pasty substance" also means polyvinyl laurate.
For the purposes of the invention, the pasty compound advantageously has a hardness at 200C ranging from 0.001 to 0.5 MPa and preferably from 0.002 to 0.4 MPa.
Among the pasty compounds that may be used in the composition according to the invention, mention may be made of lanolins and lanolin derivatives, for instance acetylated lanolins, oxypropylenated lanolins or isopropyl lanolate, and mixtures thereof.
Esters of fatty acids or of fatty alcohols may also be used, especially those containing from
20 to 65 carbon atoms, for instance triisostearyl or cetyl citrate; arachidyl propionate; polyvinyl laurate; cholesterol esters, for instance triglycerides of plant origin such as hydrogenated plant oils, viscous polyesters and mixtures thereof. Triglycerides of plant origin that may be used include hydrogenated castor oil derivatives, such as Thixinr® from
Rheox.
Mention may also be made of polyesters resulting from the esterification of a carboxylic acid and of an aliphatic hydroxycarboxylic acid ester. For example, Risocast® DA-L (ester derived from the esterification reaction of hydrogenated castor oil with dilinoleic acid in proportions of 2 to 1) and Risocast® DA-H (ester resulting from the esterification of hydrogenated castor oil with isostearic acid in proportions of 4 to 3) sold by the Japanese company Kokyu Alcohol Kogyo.
As pasty compounds that are advantageously suitable for formulating the cosmetic compositions in accordance with the present invention, mention may be made of hydrogenated cocoglycerides.
Mention may also be made of pasty silicone compounds such as high molecular weight polydimethylsiloxanes (PDMS) and in particular those containing pendent chains of the alkyl or alkoxy type containing from 8 to 24 carbon atoms, and having a melting point of 20-550C, for instance stearyl dimethicones, especially those sold by the company Dow Corning under the trade names DC2503® and DC25514®, and mixtures thereof.
GELLING AGENT
A composition according to the invention may also contain at least one gelling agent.
Such a gelling agent may be used to gel the liquid fatty phase and/or the aqueous phase of the composition.
The fatty-phase gelling agent may increase the viscosity of the liquid fatty phase and may lead to a solid or flowable composition, during its introduction into the said liquid fatty phase.
The fatty-phase gelling agent may be selected from the group constituted of gelling agents in polymer form and gelling agents in mineral form.
In one embodiment, the fatty-phase gelling agent is insoluble in an aqueous phase or in water.
According to one embodiment, the fatty-phase gelling agent may be selected from the group constituted of crosslinked elastomeric polyorganosiloxanes of three- dimensional structure, silicone gums, amino silicone polymers, silicone polyamides, non- silicone polyamides, polyurethanes, (meth)acrylic and/or vinyl polymers, copolymers such as polystyrene-silicone or poly ethylene-silicone, copolymers comprising a silicone block and another block or graft that is polyvinyl or poly(meth)acrylic, polymers or copolymers resulting from the polymerization or copolymerization of an ethylenic monomer, a modified clay and a fumed silica, and a mixture thereof. For example, the fatty-phase gelling agent may be selected from the group constituted of the group consisting of:
a) crosslinked elastomeric polyorganosiloxanes of three-dimensional structure, such as the MQ silicone resins, and polyalkylsesquioxanes, in particular polymethylsesquioxanes and resins crosslinked via hydrosilylation. These silicone resins may bear hydrophilic groups, such as polyoxyethylene or copoly(oxyethylene/ oxypropylene).
As polyorganosiloxanes that may be used in the invention, mention may be made of the crosslinked elastomeric polyorganosiloxanes described in patent application EP-A-O 295 886, the disclosure of which is incorporated into the present text by reference.
As examples of polyorganosiloxanes that may be used according to the invention, mention may be made of those sold or manufactured under the names KSG6 from Shin-Etsu, Trefil E-505C or Trefil E-506C from Dow Corning, Gransil from Grant
Industries (SR-CYC, SR DMFlO, SR-DC556) or those sold in the form of preconstituted gels (KSGl 5, KSG 17, KSG 16, KSGl 8 and KSG21 from Shin-Etsu, and Gransil SR
5CYC gel, Gransil SR DMF 10 gel, Gransil SR DC556 gel, SF 1204 and JK 113 from
General Electric). A mixture of these commercial products may also be used,
b) silicone gums, such as the product sold or manufactured under the name SE30 by the company General Electric, the product sold or manufactured under the name AK 500 000 by the company Wacker, the product sold or manufactured under the name Q2-1401 by the company Dow Corning, the product sold or manufactured under the name Q2-1403 by the company Dow Corning, and the product sold or manufactured under the name 761 by the company Rhόne-Poulenc (Rhodia Chimie),
c) amino silicone polymers containing triazinyl groups or pyrimidinyl groups linked to the amino groups of amino silicones, such as described in patent application EP 0 751 170, the disclosure of which is incorporated into the present text by reference,
d) silicone polyamides,
e) non- silicone polyamides, the ends of which bear ester or triamide functions, such as the compounds described in patents and patent applications
US 5 783 657, US 6 268 466, WO 01/95871, WO 00/40216, US 2002/0035237 and EP 1 068 856, the disclosure of which is incorporated into the present text by reference, f) polyurethanes, such as the compounds described in patent applications DE 100 22 247 and FR 2 814 365, the disclosure of which is incorporated into the present text by reference,
g) (meth)acrylic and/or vinyl polymers bearing side groups that can create mutual hydrogen interactions, such as the compounds described in patent application
WO 93/01797, the disclosure of which is incorporated into the present text by reference, h) copolymers such as polystyrene-silicone or poly ethylene-silicone, described in patents US 6 225 390, US 6 160 054, US 6 174 968 and US 6 225 390, the disclosures of which are incorporated into the present text by reference,
i) copolymers comprising a silicone block and another block or graft that is polyvinylic or poly(meth)acrylic, such as those described in patents US 5 468 477 and
US 5 725 882, the disclosures of which are incorporated into the present text by reference, j) polymers or copolymers resulting from the polymerization or copolymerization of an ethylenic monomer comprising one or more ethylenic bonds, which are preferably conjugated (or dienes),
k) polymers or copolymers resulting from the polymerization or copolymerization of an ethylenic monomer, such as those sold or manufactured under the name "Luvitol HSB" by BASF or those sold or manufactured under the brand name "Kraton" by Shell Chemical Co. or Gelled Permethyl 99A by Penreco, or those sold by the company Penreco under the name Versagel®.
As ethylenic gelling agents that may be used in the composition of the invention, examples that may be mentioned include Kraton G1650 (SEBS), Kraton G1651 (SEBS), Kraton G1652 (SEBS), Kraton G1657X (SEBS), Kraton G1701X (SEP), Kraton G1702X (SEP), Kraton G1726X (SEB), Kraton D-1101 (SBS), Kraton D-1102 (SBS), Kraton D-1107 (SIS), Gelled Permethyl 99A-750, Gelled Permethyl 99A-753-58, Gelled Permethyl 99A-753-59, Versagel 5970 and Versagel 5960 (mixture of butylene/ethylene/styrene triblock copolymer and of ethylene/propylene/styrene star copolymer in isododecane) from Penreco, and OS 129880, OS 129881 and OS 84383 from Lubrizol (styrene-methacrylate copolymer),
1) and mixtures thereof.
In another embodiment, the liquid fatty-phase gelling agent may be in mineral form. A mineral gelling agent that is suitable for the invention may or may not be used in combination with a gelling agent as defined above, and may be selected from the group constituted of:
a) a modified clay, for instance hectorites modified with an ammonium chloride of a C10 to C22 fatty acid, for instance the products sold or manufactured under the names Bentone 34 by the company Rheox, Claytone XL, Claytone 34 and Claytone 40 sold or manufactured by the company Southern Clay, benzalkonium quaternium-18 bentonites, sold or manufactured under the names Claytone HT, Claytone GR and Claytone PS by the company Southern Clay, clays modified with stearyldimethylbenzoylammonium chloride, for instance the products sold or manufactured under the names Claytone APA and Claytone AF by the company Southern Clay, and Baragel 24 sold or manufactured by the company Rheox.
b) a fumed silica.
The fumed silica may have a particle size that may be nanometric or micrometric, for example ranging from about 5 nm to 200 nm.
Fumed silicas may be obtained by high-temperature hydrolysis of a volatile silicon compound in an oxyhydric flame, producing a finely divided silica. This process allows the production of hydrophilic silicas having a large number of silanol groups at their surface. The silanol groups may be replaced, for example, with hydrophobic groups: this then gives a hydrophobic silica. The hydrophobic groups may be:
- trimethylsiloxyl groups, which are obtained especially by treating fumed silica in the presence of hexamethyldisilazane. Silicas thus treated are known as "silica silylate" according to the CTFA (6th edition, 1995). They are sold or manufactured, for example, under the references "Aerosil R812®" by the company Degussa, and "Cab-O-Sil TS-530®" by the company Cabot;
- dimethylsilyloxyl or polydimethylsiloxane groups, which are obtained in particular by treating fumed silica in the presence of polydimethyldisiloxane or dimethyldichlorosilane. Silicas thus treated are known as "silica dimethyl silylate" according to the CTFA (6th edition, 1995). They are sold or manufactured, for example, under the references "Aerosil R972®" and "Aerosil R974®" by the company Degussa, and "Cab-O-Sil TS-610®" and "Cab-O-Sil TS-720®" by the company Cabot; - groups derived from the reaction of fumed silica with silane alkylates or siloxanes. These treated silicas are, for example, the products sold or manufactured under the reference "Aerosil R805®" by the company Degussa;
c) and mixtures thereof.
A liquid fatty-phase gelling agent may be used, for example, in concentrations ranging from 1% to 30%, preferably from 5% to 20% and better still from 10% to 15% by weight relative to the total weight of the composition. The composition according to the invention may also comprise, where appropriate, a hydrophilic or water-soluble gelling agent.
Hydrophilic or water-soluble gelling agents that may be mentioned include:
- homopolymers or copolymers of acrylic or methacrylic acid or the salts and esters thereof, and in particular the products sold under the names "Versicol F" or "Versicol K" by the company Allied Colloid, "Ultrahold 8" by the company Ciba-Geigy, and the polyacrylic acids of Synthalen K type;
- copolymers of acrylic acid and of acrylamide sold in the form of the sodium salt thereof under the names "Reten" by the company Hercules, sodium polymethacrylate sold under the name "Darvan No. 7" by the company Vanderbilt, and the sodium salts of polyhydroxycarboxylic acids sold under the name "Hydagen F" by the company Henkel;
- polyacrylic acid/alkyl acrylate copolymers of the Pemulen type;
- AMPS (polyacrylamidomethylpropanesulfonic acid partially neutralized with ammonia and highly crosslinked) sold by the company Clariant;
- AMPS/acrylamide copolymers of the Sepigel or Simulgel type, sold by the company SEPPIC, and
- AMPS/polyoxyethylenated alkyl methacrylate copolymers (crosslinked or non-crosslinked), and mixtures thereof.
As other examples of water-soluble gelling polymers, mention may be made of:
- proteins, for instance proteins of plant origin, such as wheat or soybean proteins; proteins of animal origin such as keratins, for example keratin hydro lysates and sulfonic keratins; - anionic, cationic, amphoteric or nonionic chitin or chitosan polymers;
- cellulose polymers such as hydroxyethylcellulose, hydroxypropylcellulose, methylcellulose, ethylhydroxyethylcellulose and carboxymethylcellulose, and also quaternized cellulose derivatives;
- vinyl polymers, for instance polyvinylpyrrolidones, copolymers of methyl vinyl ether and of malic anhydride, the copolymer of vinyl acetate and of crotonic acid, copolymers of vinylpyrrolidone and of vinyl acetate; copolymers of vinylpyrrolidone and of capro lactam; polyvinyl alcohol;
- associative polyurethanes such as the C16-OE120-C16 polymer from the company Servo Delden (sold under the name Ser Ad FXI lOO, which is a molecule containing urethane functions and having a weight-average molecular weight of 1300 g/mol), OE being an oxyethylene unit, Rheolate 205 containing urea functions, sold by the company Rheox, or Rheolate 208 or 204 (these polymers being sold in pure form) or DW 1206B from Rohm & Haas, containing a C20 alkyl chain and a urethane bond, sold at a solids content of 20% in water. It is also possible to use solutions or dispersions of these associative polyurethanes, especially in water or in aqueous-alcoholic medium. Examples of such polymers that may be mentioned include Ser Ad FXlOlO, Ser Ad FXl 035 and Ser Ad 1070 from the company Servo Delden, and Rheolate 255, Rheolate 278 and Rheolate 244 sold by the company Rheox. It is also possible to use the product DW 1206F and DW 1206 J, and also Acrysol RM 184 or Acrysol 44 from the company Rohm & Haas, or Borchigel LW 44 from the company Borchers;
- optionally modified polymers of natural origin, such as:
- gum arabics, guar gum, xanthan derivatives and karaya gum;
- alginates and carrageenans;
- glycoaminoglycans, and hyaluronic acid and its derivatives;
- shellac resin, sandarac gum, dammar resins, elemi gums and copal resins;
- deoxyribonucleic acid;
- mucopolysaccharides such as hyaluronic acid and chondroitin sulfates,
- and mixtures thereof. DYESTUFF
A cosmetic composition according to the invention may also comprise at least one dyestuff.
Such a dyestuff may be chosen, for example, from a water-soluble or water- insoluble, liposoluble or non-liposoluble, organic or mineral dyestuff, for example of the type such as pigments or nacres, conventionally used in cosmetic compositions.
The term "pigments" should be understood as meaning white or coloured, mineral or organic particles that are insoluble in an aqueous solution, which are intended to colour and/or opacify the resulting film.
The pigments may be present in a proportion of from 0.5% to 30% by weight, especially from 5% to 25% by weight and in particular from 10% to 20% by weight relative to the total weight of the cosmetic composition.
As mineral pigments that may be used in the invention, mention may be made of titanium oxide, zirconium oxide or cerium oxide, and also zinc oxide, iron oxide or chromium oxide, ferric blue, manganese violet, ultramarine blue and chromium hydrate.
It may also be a pigment having a structure that may be, for example, of sericite/brown iron oxide/titanium dioxide/silica type. Such a pigment is sold, for example, under the reference Coverleaf® NS or JS by the company Chemicals and Catalysts, and has a contrast ratio in the region of 30.
The dyestuff may also comprise a pigment having a structure that may be, for example, of silica microsphere type containing iron oxide. An example of a pigment having this structure is the product sold by the company Miyoshi under the reference
PC BALL® PC-LL-100 P, this pigment consisting of silica microspheres containing yellow iron oxide.
Among the organic pigments that may be used in the invention, mention may be made of carbon black, pigments of D&C type, lakes based on cochineal carmine or on barium, strontium, calcium or aluminium, or alternatively the diketopyrrolopyrroles (DPP) described in documents EP-A-542669, EP-A-787730, EP-A-787731 and WO-A- 96/08537.
The term "nacres" should be understood as meaning coloured particles of any form, which may or may not be iridescent, especially produced by certain molluscs in their shell, or alternatively synthesized, and which have a colour effect via optical interference.
The nacres may be selected from the group constituted of nacreous pigments such as titanium mica coated with an iron oxide, mica coated with bismuth oxychloride, titanium mica coated with chromium oxide, titanium mica coated with an organic dye and also nacreous pigments based on bismuth oxychloride. They may also be mica particles at the surface of which are superposed at least two successive layers of metal oxides and/or of organic dyestuffs.
Examples of nacres that may also be mentioned include natural mica coated with titanium oxide, with iron oxide, with natural pigment or with bismuth oxychloride.
Among the commercially available nacres that may be mentioned are the nacres Timica®, Flamenco® and Duochrome® (on mica base) sold by the company Engelhard, the Timiron® nacres sold by the company Merck, the Prestige® nacres on mica base sold by the company Eckart and the Sunshine® nacres on synthetic mica base sold by the company Sun Chemical.
The nacres may more particularly have a yellow, pink, red, bronze, orange, brown and/or coppery colour or glint.
As illustrations of nacres that may be used in the context of the present invention, mention may be made in particular of gold-coloured nacres sold especially by the company Engelhard under the name Brilliant gold 212G (Timica), Gold 222C (Cloisonne), Sparkle gold (Timica), Gold 4504 (Chromalite) and Monarch gold 233X (Cloisonne); the bronze nacres sold especially by the company Merck under the names Bronze fine (17384) (Colorona) and Bronze (17353) (Colorona) and by the company Engelhard under the name Super bronze (Cloisonne); the orange nacres sold especially by the company Engelhard under the names Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by the company Merck under the names Passion orange (Colorona) and Matte orange (17449) (Microna); the brown-tinted nacres sold especially by the company Engelhard under the names Nu-antique copper 340XB (Cloisonne) and Brown CL4509 (Chromalite); the nacres with a copper glint sold especially by the company Engelhard under the name Copper 340A (Timica); the nacres with a red glint sold especially by the company Merck under the name Sienna fine (17386) (Colorona); the nacres with a yellow glint sold especially by the company Engelhard under the name Yellow (4502) (Chromalite); the red-tinted nacres with a golden glint sold especially by the company Engelhard under the name Sunstone GO 12 (Gemtone); the pink nacres sold especially by the company Engelhard under the name Tan opale G005 (Gemtone); the black nacres with a golden glint sold especially by the company Engelhard under the name Nu antique bronze 240 AB (Timica); the blue nacres sold especially by the company Merck under the name Matte blue (17433) (Microna); the white nacres with a silvery glint sold especially by the company Merck under the name Xirona Silver; and the golden-green pinkish- orange nacres sold especially by the company Merck under the name Indian summer (Xirona), and mixtures thereof.
The cosmetic composition according to the invention may also comprise at least one water-soluble or liposoluble dye in a content ranging from 0.5% to 30% by weight and especially ranging from 5% to 25% by weight relative to the total weight of the cosmetic composition.
The liposoluble dyes are, for example, Sudan Red, DC Red 17, DC Green 6, β-carotene, soybean oil, Sudan Brown, DC Yellow 11, DC Violet 2, DC Orange 5 and quinoline yellow. The water-soluble dyes are, for example, beetroot juice or methylene blue.
The cosmetic composition according to the invention may also contain at least one material with a specific optical effect.
This effect is different from a simple conventional hue effect, i.e. a unified and stabilized effect as produced by standard dyestuffs, for instance monochromatic pigments.
For the purposes of the invention, the term "stabilized" means lacking the effect of variability of the colour with the angle of observation or in response to a temperature change.
For example, this material may be selected from the group constituted of particles with a metallic glint, gonio chromatic colouring agents, diffracting pigments, thermochromic agents, optical brighteners, and also fibres, especially interference fibres.
Needless to say, these various materials may be combined so as to afford the simultaneous manifestation of two effects, or even of a novel effect in accordance with the invention.
The particles with a metallic glint that may be used in the invention are in particular selected from the group constituted of:
particles of at least one metal and/or of at least one metal derivative, particles comprising a monomaterial or multimaterial organic or mineral substrate, at least partially coated with at least one layer with a metallic glint comprising at least one metal and/or at least one metal derivative, and
mixtures of the said particles.
Among the metals that may be present in the said particles, mention may be made, for example, of Ag, Au, Cu, Al, Ni, Sn, Mg, Cr, Mo, Ti, Zr, Pt, Va, Rb, W, Zn, Ge, Te and Se and mixtures or alloys thereof. Ag, Au, Cu, Al, Zn, Ni, Mo and Cr, and mixtures or alloys thereof (for example bronzes and brasses) are preferred metals.
The term "metal derivatives" is intended to denote compounds derived from metals, especially oxides, fluorides, chlorides and sulfides.
Illustrations of these particles that may be mentioned include aluminium particles, such as those sold under the names Starbrite 1200 EAC® by the company Siberline and Metalure® by the company Eckart.
Mention may also be made of metal powders of copper or of alloy mixtures such as the references 2844 sold by the company Radium Bronze, metallic pigments, for instance aluminium or bronze, such as those sold under the names Rotosafe® 700 from the company Eckart, silica-coated aluminium particles sold under the name Visionaire Bright
Silver ® from the company Eckart, and metal alloy particles, for instance the silica-coated bronze (alloy of copper and zinc) powders sold under the name Visionaire Bright Natural Gold ® from the company Eckart.
They may also be particles comprising a glass substrate, for instance those sold by the company Nippon Sheet Glass under the name Microglass Metashine®.
The goniochromatic colouring agent may be chosen, for example, from interference multilayer structures and liquid-crystal colouring agents.
Examples of symmetrical interference multilayer structures that may be used in compositions produced in accordance with the invention are, for example, the following structures: AlZSiO2ZAlZSiO2ZAl, pigments having this structure being sold by the company Dupont de Nemours; CrZMgF2/ Al/MgF2/Cr, pigments having this structure being sold under the name Chromaflair® by the company Flex; MoS2ZSiO2ZAlZSiO2ZMoS2; Fe2O3ZSiO2ZAlZSiO2ZFe2O3 and Fe2O3ZSiO2ZFe2O3ZSiO2ZFe2O3, pigments having these structures being sold under the name Sicopearl® by the company BASF; MoS2ZSiO2Zmica oxideZSiO2ZMoS2; Fe2O3ZSiO2Zmica oxideZSiO2ZFe2O3 ; TiO2ZSiO2ZTiO2 and Ti(VAl2O3ZTiO2; SnO/TiO2/SiO2/TiO2/SnO; Fe2O3ZSiO2ZFe2O3;
Sn0ZmicaZTi02ZSi02ZTi02ZmicaZSn0, pigments having these structures being sold under the name Xirona® by the company Merck (Darmstadt). By way of example, these pigments may be the pigments of silicaZtitanium oxideZtin oxide structure sold under the name Xirona Magic® by the company Merck, the pigments of silicaZbrown iron oxide structure sold under the name Xirona Indian Summer® by the company Merck and the pigments of silicaZtitanium oxideZmicaZtin oxide structure sold under the name Xirona Caribbean Blue® by the company Merck. Mention may also be made of Infinite Colors® pigments from the company Shiseido. Depending on the thickness and the nature of the various coats, different effects are obtained. Thus, with the structure Fe2O3ZSiO2ZAlZ SiO2ZFe2O3, the colour changes from green-golden to red-grey for SiO2 layers of from 320 to 350 nm; from red to golden for SiO2 layers of from 380 to 400 nm; from violet to green for SiO2 layers of from 410 to 420 nm; from copper to red for SiO2 layers of from 430 to 440 nm.
Examples of pigments with a polymeric multilayer structure that may be mentioned include those sold by the company 3M under the name Color Glitter®.
Examples of liquid-crystal goniochromatic particles that may be used include those sold by the company Chenix and also the product sold under the name Helicone® HC by the company Wacker.
According to one embodiment, a composition according to the invention may comprise not more than 30% by weight of dyestuff relative to the total weight of the composition.
FILLERS
The cosmetic compositions in accordance with the invention may also comprise at least one filler, of organic or mineral nature, which especially makes it possible to give them improved stability with regard to exudation.
The term "filler" should be understood as meaning colourless or white solid particles of any form, which are in an insoluble form and dispersed in the medium of the composition. Being of mineral or organic nature they make it possible to impart body or rigidity to the composition, andZor softness, a matt effect and uniformity to the makeup.
The fillers used in the compositions according to the present invention may be of lamellar, globular or spherical form, fibres or in any other form intermediate between these defined forms.
The fillers according to the invention may or may not be surface-coated, and in particular they may be surface-treated with silicones, amino acids, fluoro derivatives or any other substance that promotes the dispersion and compatibility of the filler in the composition.
For the purposes of the present invention, the terms "mineral fillers" and "inorganic fillers" are used interchangeably.
Among the mineral fillers that may be used in the compositions according to the invention, mention may be made of talc, mica, silica, trimethyl siloxysilicate, kaolin, bentone, precipitated calcium carbonate, magnesium carbonate, magnesium hydrogen carbonate, hydroxyapatite, boron nitride, hollow silica microspheres (Silica Beads from Maprecos), glass or ceramic microcapsules, silica-based fillers, for instance Aerosil 200 or Aerosil 300; Sunsphere L-31 and Sunsphere H-31 sold by Asahi Glass; Chemicelen sold by Asahi Chemical; composites of silica and of titanium dioxide, for instance the TSG series sold by Nippon Sheet Glass, and mixtures thereof.
Among the organic fillers that may be used in the compositions according to the invention, mention may be made of polyamide powders (Nylon® Orgasol from Atochem), poly-β-alanine powder and polyethylene powder, polytetrafluoroethylene powders (Teflon®), lauroyllysine, starch, tetrafluoroethylene polymer powders, hollow polymer microspheres such as Expancel® (Nobel Industrie), precipitated calcium carbonate, magnesium carbonate, magnesium hydrogen carbonate, metal soaps derived from organic carboxylic acids containing from 8 to 22 carbon atoms and preferably from 12 to 18 carbon atoms, for example zinc stearate, magnesium stearate or lithium stearate, zinc laurate or magnesium myristate, Polypore® L 200 (Chemdal Corporation), silicone resin microbeads (for example Tospearl® from Toshiba), polyurethane powders, in particular powders of crosslinked polyurethane comprising a copolymer, the said copolymer comprising trimethylol hexyllactone. In particular, it may be a polymer of hexamethylene diisocyanate/trimethylol hexyllactone. Such particles are especially commercially available, for example, under the name Plastic Powder D-400® or Plastic Powder D-800® from the company Toshiki, and mixtures thereof.
A filler may be present in a cosmetic composition in accordance with the invention in a proportion of from 0.5% to 40% by weight and preferably from 5% to 30% by weight of filler relative to the total weight of the composition.
A filler that is suitable for the invention may be, for example, a filler whose mean particle size is less than 100 μm and especially between 1 and 50 μm, for example between 4 and 20 μm.
ADDITIVES
The cosmetic compositions according to the invention may, furthermore, also comprise any additive usually used in the field under consideration, selected from the group constituted of film- forming agents and, where appropriate, auxiliary film- forming agents, gums, antioxidants, surfactants, essential oils, preserving agents, fragrances, neutralizers, moisturizers, antiseptics, vitamins such as vitamin B3 or E and derivatives thereof, and anti-UV agents, and mixtures thereof.
One subject of the present invention is the use of at least one ester of dimerdilinoleic acid and of polyol(s), or an ester thereof, in accordance with the invention, in combination with at least one semi-crystalline polymer, for the preparation of a cosmetic composition for caring for and/or making up the skin and/or the lips, which shows improved gloss staying power, or even also improved colourfastness. According to one embodiment, the semi-crystalline polymer used in the use in accordance with the invention may be as defined above.
According to one of its aspects, a subject of the present invention is a synthetic support comprising at least one coat of a composition in accordance with the invention.
A composition in accordance with the invention may be prepared in the usual manner for those skilled in the art. It may thus be in cast form, for example in the form of a stick or wand, in the form of a soft paste in a heating bag or in the form of dishes that may be used by direct contact or with a sponge.
For example, it may constitute a cast foundation, a cast makeup rouge or eyeshadow, which is especially coloured, a lipstick, a lip gloss or a concealer product.
A composition in accordance with the invention may be obtained by heating the various constituents to the melting point of the highest-melting waxes, followed by pouring the molten mixture into a mould (dish or finger stall). It may also be obtained by extrusion, as described in patent application EP-A-O 667 146.
The present invention also relates to a process for making up and/or caring for the skin and/or the lips, comprising at least one step that consists in applying a composition in accordance with the invention to at least part of a support.
The cosmetic composition according to the invention may especially be in the form of a lip makeup and/or care composition, in particular a lipstick, a lip balm or a gloss.
For the purposes of the present invention, and unless otherwise indicated, the term "one" should be understood as meaning "at least one".
The composition example below is given as a non-limiting illustration of the invention.
EXAMPLE 1
Lipstick
Figure imgf000046_0001
Figure imgf000047_0001
Procedure
An oily phase is prepared by mixing together the oils and the polyglyceryl-2 isostearate/dimerdilinoleate copolymer (Hailucent ISDA) for the composition according to the invention, with heating (about 95°C).
The oily phase thus prepared is stirred at about 95°C and the fillers are added to the mixture.
The waxes, the pigments in the form of a pigmentary paste, prepared by mixing the dyestuffs with the polyglyceryl triisostearate and the isononyl isononanoate, the simethicone and the bis-behenyl/isostearyl/phytosteryl dimerdilinoleyl dimerdilinoleate are then added to the mixture.
The mixture thus obtained is then poured into a lipstick mould and is left to cool until a solid composition is obtained.
The mean gloss and the mean gloss staying power of composition 1 are measured according to the protocol described previously.
The results obtained are summarized in the table below.
Figure imgf000047_0002

Claims

1. Cosmetic composition for caring for and/or making up the skin and/or the lips, comprising at least one ester of dimerdilinoleic acid and of polyol(s), or an ester thereof, the viscosity of which, measured at about 25°C, is greater than or equal to about 20 000 mPa.s, and which has a gloss staying power of greater than or equal to about 7.
2. Anhydrous cosmetic composition for caring for and/or making up the skin and/or the lips, comprising at least one ester of dimerdilinoleic acid and of polyol(s), or an ester thereof, the viscosity of which, measured at about 25°C, is greater than or equal to about 20 000 mPa.s, and at least one semi-crystalline polymer.
3. Composition according to claim 1 or 2, in which the said ester has a molecular weight ranging from about 2000 to about 25 000 g/mol, in particular from about 4000 to about 20 000 g/mol, in particular from about 7000 to about 15 000 g/mol and more particularly from about 8000 g/mol to about 10 000 g/mol.
4. Composition according to any one of the preceding claims, in which the polyol is a diol.
5. Composition according to the preceding claim, in which the said ester comprises an alternating sequence of dimerdilinoleate residue(s) and of residue(s) related to the said diol(s).
6. Composition according to claim 4 or 5, in which the diol is selected from the group constituted of a fatty alcohol dimer, a monoglycerol or polyglyceryl, a C2-4 monoalkylene or polyalkylene glycol, 1 ,4-butanediol and pentaerythritol.
7. Composition according to claim 6, in which the fatty alcohol dimer is the product of hydrogenation of a fatty acid dimer obtained by dimerization of a Cs to C34, especially C12 to C22, in particular C16 to C20 and more particularly C18 unsaturated fatty acid.
8. Composition according to any one of claims 5 to 7, in which each of the two ends of the said sequence bears, respectively, a residue OR' and OR" with R' and R" representing, independently of each other, a hydrogen atom or OR' and OR", representing, independently of each other, a C2 to C36 hydrocarbon-based monoalcohol residue.
9. Composition according to claim 8, in which R' and R" both represent a hydrogen atom.
10. Composition according to claim 8, in which OR' and OR" both represent an identical or different hydrocarbon-based monoalcohol residue.
11. Cosmetic composition for caring for and/or making up the skin and/or the lips, comprising at least one ester of general formula (I) below:
R3-OCO-Ri(-COO-R2-OCO-Ri)n-COO-R3 (I) in which:
- OCRiCO represents a dimerdilinoleate residue,
- OR2O represents a fatty alcohol dimer residue,
- OR3 represents a hydrocarbon-based monoalcohol residue, and
- n is an integer ranging from 1 to 15,
and having a gloss staying power of greater than or equal to 7.
12. Composition according to any one of claims 1 to 8 and 10, comprising an ester as defined according to claim 11.
13. Composition according to claim 11 or 12, in which OR2O represents a dimer dilino ley 1 residue.
14. Composition according to any one of claims 11 to 13, in which OR3 represents a hydrocarbon-based monoalcohol residue selected from the group constituted of behenyl, isostearyl and phytosteryl residues, and mixtures thereof.
15. Cosmetic composition for caring for and/or making up the skin and/or the lips, comprising at least one ester of general formula (II) below:
Figure imgf000049_0001
in which:
- n is an integer ranging from 1 to 15,
- OCR' i CO represents a dimerdilinoleate residue,
- OR'2O represents a diglyceryl residue of general formula (III) below:
Figure imgf000049_0002
in which: R53 represents H or OR'3 represents a fatty acid residue, and having a gloss staying power of greater than or equal to 7.
16. Composition according to any one of claims 1 to 9, comprising an ester as defined according to claim 15.
17. Composition according to claim 15 or 16, in which the fatty acid residue featured by OR'3 is an isostearyl residue.
18. Composition according to any one of the preceding claims, in which the said ester is selected from the group constituted of the esters of the following INCI nomenclature: polyglyceryl-2 isostearate/dimerdilinoleate copolymer, bis- behenyl/isostearyl/phytosteryl dimerdilinoleyl dimerdilinoleate, and mixtures thereof.
19. Composition according to any one of the preceding claims, characterized in that it comprises from 5% to 90%, in particular from 15% to 80% and more particularly from 20% to 50% by weight of the said ester relative to the total weight of the composition.
20. Composition according to any one of claims 1 or 3 to 19, also comprising a semi-crystalline polymer.
21. Composition according to claim 2 or 20, in which the said semi- crystalline polymer has a melting point of less than about 500C.
22. Composition according to any one of claims 2 to 21, in which the said semi-crystalline polymer is a polymer comprising a) a hydrocarbon-based or silicone polymer backbone and b) at least one crystallizable organic side chain and/or one crystallizable organic block forming part of the polymer backbone of the said polymer, the said polymer having a number-average molecular mass of greater than or equal to about 2000.
23. Composition according to any one of claims 2 to 22, in which the said semi-crystalline polymer is selected from the group constituted of copolymers resulting from the polymerization (a) of one or more carboxylic monomer(s) with (b) one or more polydimethylsiloxane chain(s) comprising at least one polymerizable radical.
24. Composition according to the preceding claim, in which the monomer is selected from the group constituted of acrylic acid, methacrylic acid, maleic acid, fumaric acid, itaconic acid, crotonic acid, and esters thereof, such as methyl, ethyl, stearyl, butyl or 2-ethylhexyl acrylate or methacrylate, and mixtures thereof.
25. Composition according to any one of claims 2 to 24, in which the semi- crystalline polymer is a copolymer of acrylate and of dimethicone.
26. Composition according to any one of claims 2 to 25, in which the ester and the semi- crystalline polymer are present in a weight ratio ranging from about 15:1 to about 2:1, in particular from about 10:1 to about 4:1 and more particularly from about 8:1 to about 6:1.
27. Composition according to any one of claims 1 and 3 to 26, characterized in that it is anhydrous.
28. Composition according to any one of the preceding claims, also comprising at least one liquid fatty phase selected from the group constituted of volatile oils and non- volatile oils, and mixtures thereof.
29. Composition according to the preceding claim, comprising at least one oil of molar mass ranging from about 650 to about 10 000 g/mol, in particular from about 750 to about 7500 g/mol and more particularly ranging from about 1000 to about 5000 g/mol.
30. Composition according to claim 28 or 29, in which the said oil is selected from the group constituted of:
- lipophilic polymers,
- linear fatty acid esters with a total carbon number ranging from 35 to 70,
- hydroxylated esters,
- aromatic esters,
- esters Of C24-C2S branched fatty alcohols or fatty acids,
- silicone oils,
- oils of plant origin,
- and mixtures thereof.
31. Composition according to claim 29 or 30, in which the said oil is selected from the group constituted of polybutylenes, hydrogenated polyisobutylenes, polydecenes, hydrogenated polydecenes, vinylpyrrolidone copolymers, such as PVP/hexadecene copolymer, pentaerythrityl tetrapelargonate, polyglyceryl-2 triisostearate, tridecyl trimellitate, triisoarachidyl citrate, pentaerythrityl tetraisononanoate, glyceryl triisostearate, glyceryl tris(2-decyl)tetradecanoate, pentaerythrityl tetraisostearate, polyglyceryl-2 tetraisostearate, pentaerythrityl tetrakis(2-decyl)tetradecanoate, phenyl silicones, sesame oil and oils of an ester of an acid dimer and of alcohol, and mixtures thereof.
32. Composition according to any one of the preceding claims, also comprising at least one gelling agent.
33. Composition according to the preceding claim, in which the said gelling agent is selected from the group constituted of crosslinked elastomeric polyorganosiloxanes of three-dimensional structure, silicone gums, amino silicone polymers, silicone polyamides, non-silicone polyamides, polyurethanes, (meth)acrylic and/or vinyl polymers, copolymers such as polystyrene-silicone or poly ethylene-silicone, copolymers comprising a silicone block and another block or graft that is polyvinyl or poly(meth)acrylic, polymers or copolymers resulting from the polymerization or copolymerization of an ethylenic monomer, a modified clay and a fumed silica, and a mixture thereof.
34. Composition according to any one of the preceding claims, further comprising at least one dyestuff.
35. Composition according to any one of the preceding claims, characterized in that it is a lip makeup and/or care composition.
36. Use of at least one ester of dimerdilinoleic acid and of polyol(s), or an ester thereof, the viscosity of which, measured at 25°C, is greater than or equal to 20 000 mPa.s, or as defined in claim 11 or 15, in combination with at least one semi- crystalline polymer, for the preparation of a cosmetic composition for caring for and/or making up the skin and/or the lips, which has improved gloss staying power.
37. Use according to the preceding claim, in which the said ester is as defined according to any one of claims 3 to 19.
38. Use according to claim 36 or 37, in which the semi-crystalline polymer is as defined according to any one of claims 21 to 25.
39. Process for making up and/or caring for the skin and/or the lips, comprising at least one step that consists in applying, to at least part of a support, a composition as defined according to any one of claims 1 to 35.
PCT/IB2006/054663 2005-12-08 2006-12-07 Cosmetic composition comprising an ester of dimerdilinoleic acid and of polyol(s) and a semi-crystalline polymer WO2007066309A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN200680045929.XA CN101355985B (en) 2005-12-08 2006-12-07 Cosmetic composition comprising an ester of dimerdilinoleic acid and of polyol(s) and a semi-crystalline polymer
JP2008543985A JP5840339B2 (en) 2005-12-08 2006-12-07 Cosmetic composition comprising an ester of dimer linoleic acid and a polyol and a semi-crystalline polymer

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR0553799A FR2894472B1 (en) 2005-12-08 2005-12-08 COSMETIC COMPOSITION COMPRISING A DIMERDILINOLEIC ACID ESTER AND POLYOL (S) AND A SEMI-CRYSTALLINE POLYMER
FR0553799 2005-12-08
US75428405P 2005-12-29 2005-12-29
US60/754,284 2005-12-29

Publications (2)

Publication Number Publication Date
WO2007066309A2 true WO2007066309A2 (en) 2007-06-14
WO2007066309A3 WO2007066309A3 (en) 2007-08-16

Family

ID=37993097

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2006/054663 WO2007066309A2 (en) 2005-12-08 2006-12-07 Cosmetic composition comprising an ester of dimerdilinoleic acid and of polyol(s) and a semi-crystalline polymer

Country Status (2)

Country Link
JP (1) JP5840339B2 (en)
WO (1) WO2007066309A2 (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009149227A1 (en) * 2008-06-06 2009-12-10 Lubrizol Advanced Materials, Inc. Ester compounds for use in personal care products
WO2012004896A1 (en) * 2010-07-05 2012-01-12 L'oreal Powdery cosmetic composition
US20140004060A1 (en) * 2012-06-28 2014-01-02 Johnson & Johnson Consumer Companies, Inc. Ultraviolet radiation absorbing polymers
US8734765B2 (en) 2008-06-02 2014-05-27 L'oreal Compositions based on polyester in an oily phase and uses thereof
US8932573B2 (en) 2013-03-22 2015-01-13 L'oreal Mascara compositions comprising a semicrystalline polymer, a silicone elastomer, and a hydrophilic gelling agent
US9737470B2 (en) 2012-06-28 2017-08-22 Johnson & Johnson Consumer Inc. Sunscreen compositions containing an ultraviolet radiation-absorbing polymer
US9758618B2 (en) 2012-06-28 2017-09-12 Johnson & Johnson Consumer Inc. Ultraviolet radiation absorbing polyethers
WO2018119762A1 (en) * 2016-12-28 2018-07-05 L'oreal Solid anhydrous composition for caring for and/or making up keratin materials
US10596087B2 (en) 2016-10-05 2020-03-24 Johnson & Johnson Consumer Inc. Ultraviolet radiation absorbing polymer composition
US10874603B2 (en) 2014-05-12 2020-12-29 Johnson & Johnson Consumer Inc. Sunscreen compositions containing a UV-absorbing polyglycerol and a non-UV-absorbing polyglycerol
WO2023060376A1 (en) * 2021-10-11 2023-04-20 L'oreal Petrolatum substitute and cosmetic composition comprsing the same

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2726678C (en) * 2008-06-23 2014-05-27 Elc Management Llc Compositions for forming long wear cosmetic products
KR102645442B1 (en) * 2018-12-04 2024-03-11 (주)아모레퍼시픽 Oil in water type composition having high gloss

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2795309A1 (en) * 1999-06-28 2000-12-29 Nippon Fine Chemical Co Novel ester of dimer diol with 4-34 carbon mono- or di-carboxylic acid is used as oily substance or in cosmetic or external agent
FR2824264A1 (en) * 2001-05-04 2002-11-08 Oreal Composition useful as a cosmetic make-up product comprises an oil phase thickened with a low-melting semi-crystalline polymer
EP1454612A1 (en) * 2003-03-06 2004-09-08 L'oreal Cosmetic composition comprising an ester and pasty component
EP1604637A2 (en) * 2004-06-08 2005-12-14 L'oreal Cosmetic composition containing a semicrystalline polymer and a dispersion of polymer particles in a fatty phase
EP1604636A2 (en) * 2004-06-08 2005-12-14 L'oreal Cosmetic composition containing a non-polar wax and a dispersion of polymer particles in a fatty phase
EP1604638A2 (en) * 2004-06-08 2005-12-14 L'oreal Cosmetic composition containing a semicrystalline polymer and a diol dimer ester

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002275020A (en) * 2001-03-22 2002-09-25 Nippon Fine Chem Co Ltd Oil agent, and cosmetic and external agent containing the same
JP4331584B2 (en) * 2003-02-04 2009-09-16 日本精化株式会社 Oily base and cosmetics and skin external preparations containing the same
JP4589050B2 (en) * 2003-12-22 2010-12-01 日本精化株式会社 Diesters and oils, and cosmetics and skin external preparations
JP2005179377A (en) * 2005-03-10 2005-07-07 Kokyu Alcohol Kogyo Co Ltd Cosmetic

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2795309A1 (en) * 1999-06-28 2000-12-29 Nippon Fine Chemical Co Novel ester of dimer diol with 4-34 carbon mono- or di-carboxylic acid is used as oily substance or in cosmetic or external agent
FR2824264A1 (en) * 2001-05-04 2002-11-08 Oreal Composition useful as a cosmetic make-up product comprises an oil phase thickened with a low-melting semi-crystalline polymer
EP1454612A1 (en) * 2003-03-06 2004-09-08 L'oreal Cosmetic composition comprising an ester and pasty component
EP1604637A2 (en) * 2004-06-08 2005-12-14 L'oreal Cosmetic composition containing a semicrystalline polymer and a dispersion of polymer particles in a fatty phase
EP1604636A2 (en) * 2004-06-08 2005-12-14 L'oreal Cosmetic composition containing a non-polar wax and a dispersion of polymer particles in a fatty phase
EP1604638A2 (en) * 2004-06-08 2005-12-14 L'oreal Cosmetic composition containing a semicrystalline polymer and a diol dimer ester

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
"Composition useful as cosmetics such as cleansing gel, contains esterified substance of alcohol and dimer acid having specified melting point" DERWENT, 12 August 2003 (2003-08-12), XP002399564 *
"Oil-based base for use in cosmetics and skin external preparation, contains ester, which esterified oligomer ester of dimer acid/diol and alcohol/carboxylic acid with monovalent alcohol and/or monovalent carboxylic acid" DERWENT, 16 September 2004 (2004-09-16), XP002399103 *
"Oil-based makeup cosmetic such as foundation and lip gloss, comprises di (phytosteryl-isostearyl-cetyl-stearyl-behe nyl) dimer dilinoleic acid and a hydrophilic polymeric processed pigment" DERWENT, 30 September 2004 (2004-09-30), XP002399110 *
"Oil-based makeup cosmetics such as foundation, lip gloss, etc, comprises di (phytosteryl-isostearyl-cetyl-stearyl-behe nyl) dimer dilinoleic acid and N-acylation lysine processed pigment" DERWENT, 30 September 2004 (2004-09-30), XP002399109 *
"Oily cosmetics using gelling agent, dimeric linoleic acid derivative and oily substance" DERWENT, 9 May 2002 (2002-05-09), XP002399105 *
"Oily cosmetics using polydimer dilinoleic acid derivative and wax" DERWENT, 30 September 2002 (2002-09-30), XP002399111 *
DATABASE WPI Week 200565 Derwent Publications Ltd., London, GB; AN 2005-632594 XP002402694 & JP 2005 179377 A (KOKYU ALCOHOL KOGYO CO LTD) 7 July 2005 (2005-07-07) *

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104622714A (en) * 2008-06-02 2015-05-20 欧莱雅公司 Compositions based on polyester in an oily phase and uses thereof
US9549892B2 (en) 2008-06-02 2017-01-24 L'oreal Compositions based on polyester in an oily phase and uses thereof
US8734765B2 (en) 2008-06-02 2014-05-27 L'oreal Compositions based on polyester in an oily phase and uses thereof
JP2011522826A (en) * 2008-06-06 2011-08-04 ルブリゾル アドバンスド マテリアルズ, インコーポレイテッド Ester compounds for use in personal care products
CN102088949B (en) * 2008-06-06 2013-05-01 路博润高级材料公司 Ester compounds for use in personal care products
US8895040B2 (en) 2008-06-06 2014-11-25 Lubrizol Advanced Materials, Inc. Ester compounds for use in personal care products
WO2009149227A1 (en) * 2008-06-06 2009-12-10 Lubrizol Advanced Materials, Inc. Ester compounds for use in personal care products
WO2012004896A1 (en) * 2010-07-05 2012-01-12 L'oreal Powdery cosmetic composition
US9469725B2 (en) * 2012-06-28 2016-10-18 Johnson & Johnson Consumer Inc. Ultraviolet radiation absorbing polymers
US9758618B2 (en) 2012-06-28 2017-09-12 Johnson & Johnson Consumer Inc. Ultraviolet radiation absorbing polyethers
US10278910B2 (en) 2012-06-28 2019-05-07 Johnson & Johnson Consumer Inc. Sunscreen compositions containing an ultraviolet radiation-absorbing polymer
US20140004060A1 (en) * 2012-06-28 2014-01-02 Johnson & Johnson Consumer Companies, Inc. Ultraviolet radiation absorbing polymers
US9737470B2 (en) 2012-06-28 2017-08-22 Johnson & Johnson Consumer Inc. Sunscreen compositions containing an ultraviolet radiation-absorbing polymer
US9737471B2 (en) 2012-06-28 2017-08-22 Johnson & Johnson Consumer Inc. Sunscreen compositions containing an ultraviolet radiation-absorbing polymer
CN104411366B (en) * 2012-06-28 2017-09-08 强生消费者公司 Ultraviolet radiation absorption polymer
CN104411366A (en) * 2012-06-28 2015-03-11 强生消费者公司 Ultraviolet radiation absorbing polymers
US8932573B2 (en) 2013-03-22 2015-01-13 L'oreal Mascara compositions comprising a semicrystalline polymer, a silicone elastomer, and a hydrophilic gelling agent
US10874603B2 (en) 2014-05-12 2020-12-29 Johnson & Johnson Consumer Inc. Sunscreen compositions containing a UV-absorbing polyglycerol and a non-UV-absorbing polyglycerol
US10596087B2 (en) 2016-10-05 2020-03-24 Johnson & Johnson Consumer Inc. Ultraviolet radiation absorbing polymer composition
US10874597B2 (en) 2016-10-05 2020-12-29 Johnson & Johnson Consumer Inc. Ultraviolet radiation absorbing polymer composition
WO2018119762A1 (en) * 2016-12-28 2018-07-05 L'oreal Solid anhydrous composition for caring for and/or making up keratin materials
WO2023060376A1 (en) * 2021-10-11 2023-04-20 L'oreal Petrolatum substitute and cosmetic composition comprsing the same

Also Published As

Publication number Publication date
WO2007066309A3 (en) 2007-08-16
JP2009518385A (en) 2009-05-07
JP5840339B2 (en) 2016-01-06

Similar Documents

Publication Publication Date Title
JP5840339B2 (en) Cosmetic composition comprising an ester of dimer linoleic acid and a polyol and a semi-crystalline polymer
US20070134181A1 (en) Cosmetic composition comprising an ester of dimerdilinoleic acid and of polyol(s) and a silicone surfactant
KR102109997B1 (en) Liquid cosmetic composition comprising an oil, hydrophobic silica aerogel particles and a wax with a melting point of greater than 60℃
US20070134192A1 (en) Two-coat cosmetic product comprising an ester of dimerdilinoleic acid and of polyol(s)
US10071045B2 (en) Cosmetic composition comprising a hydrocarbonated-based resin, a hydrocarbon-based block copolymer, a non volatile dimethicone oil and a non volatile hydrocarbonated oil
US20090010868A1 (en) Composition combining a silicone polymer and a tackifying resin
EP2293772B1 (en) Compositions based on polyester in an oily phase and uses thereof
KR102109996B1 (en) Cosmetic composition comprising an oil, hydrophobic silica aerogel particles and a hydrocarbon-based resin
CN104394834A (en) Cosmetic composition comprising an oil, hydrophobic silica aerogel particles, and a hydrocarbon-based block copolymer preferably obtained from at least one styrene monomer
WO2013190130A1 (en) Anhydrous cosmetic composition comprising an oil, hydrophobic silica aerogel particles, a hydrophilic active agent and at least one surfactant
KR102097976B1 (en) Cosmetic composition comprising a hydrocarbonated-based resin, a hydrocarbon-based block copolymer, a non volatile phenyl dimethicone oil and a non volatile hydrocarbonated oil
KR102109998B1 (en) Cosmetic composition comprising an oil, hydrophobic silica aerogel particles and a semi-crystalline polymer
US20100028394A1 (en) Cosmetic composition for making up and/or caring for the lips
US20070190001A1 (en) Cosmetic composition comprising an ester of polyol(s) and of fatty diacid dimer and a polyamide
EP2863867A2 (en) Liquid cosmetic composition comprising an oil, hydrophobic silica aerogel particles and a block ethylenic copolymer
CN101355985B (en) Cosmetic composition comprising an ester of dimerdilinoleic acid and of polyol(s) and a semi-crystalline polymer
WO2009147088A1 (en) Compositions containing a polyester and a colorant and uses thereof
EP1795232A2 (en) Bilayered cosmetic product comprising an ester of dimerdilinoleic acid and polyol

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200680045929.X

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2008543985

Country of ref document: JP

NENP Non-entry into the national phase in:

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 06832145

Country of ref document: EP

Kind code of ref document: A2