AU750093B2 - Cosmetic composition comprising at least one silicone/ acrylate copolymer and at least one grafted silicone polymer - Google Patents
Cosmetic composition comprising at least one silicone/ acrylate copolymer and at least one grafted silicone polymer Download PDFInfo
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- AU750093B2 AU750093B2 AU56487/00A AU5648700A AU750093B2 AU 750093 B2 AU750093 B2 AU 750093B2 AU 56487/00 A AU56487/00 A AU 56487/00A AU 5648700 A AU5648700 A AU 5648700A AU 750093 B2 AU750093 B2 AU 750093B2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
- A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/895—Polysiloxanes containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
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Abstract
Cosmetic comprises silicone/acrylate copolymer A, obtained by radical polymerization of ethylenically unsaturated monomer (a) in presence of silicone derivative (b) comprising oxyalkylene groups, and grafted silicone polymer B with polysiloxane skeleton grafted with organic non-silicone monomers. Independent claims are also included for 1) process of maintaining or setting a hair style involving application of composition as claimed; 2) the use of composition as claimed for making cosmetic product for use on hair; and 3) use of composition as claimed for cosmetic treatment of skin, nails, lips, hair, eyebrows and eyelashes.
Description
AUSTRALIA
Patents Act 1990 COMPLETE SPECIFICATION STANDARD PATENT
L'OREAL
Title: COSMETIC COMPOSITION COMPRISING AT LEAST ONE SILICONE/ACRYLATE COPOLYMER AND AT LEAST ONE GRAFTED SILICONE POLYMER Applicant Invention The following statement is a full description of this invention, including the best method of performing it known to me/us: iA COSMETIC COMPOSITION COMPRISING AT LEAST ONE SILICONE/ACRYLATE COPOLYMER AND AT LEAST ONE GRAFTED SILICONE POLYMER The invention relates to a cosmetic composition comprising at least one specific silicone/acrylate copolymer and at least one grafted silicone polymer, containing a polysiloxane skeleton grafted with non-silicone organic monomers. The 10 invention also relates to a cosmetic process, in :°oeeo .particular a process for fixing and/or holding the hairstyle by using the said composition, as well as to the use of this composition for the manufacture of a cosmetic formulation intended in particular for holding and/or shaping the hairstyle.
Among hair products, in particular those intended for shaping and/or holding the hairstyle which are most widely available on the cosmetics market, there may be distinguished the spray compositions essentially consisting of a solution, usually an alcoholic or aqueous solution, and one or more materials.
When the compositions are intended for fixing and/or holding the hairstyle, these materials are generally polymeric resins, whose function is to form welds between the hairs, and these are also known as fixing materials, mixed with various cosmetic adjuvants. These compositions are generally packaged either in a suitable aerosol container placed under pressure with the aid of a propellant, or in a pumpdispenser bottle.
Hair gels and hair mousses which are generally applied to wet hair before blow-drying or setting the hair are also known. A drying or blowdrying operation is then carried out in order to shape and fix the hairstyle. These gels or mousses can also contain polymeric resins.
However, these hair compositions often have the drawback of adversely affecting the cosmetic properties of the hair. Thus, the hair may become S* coarse and difficult to disentangle, it may lose its pleasant feel and appearance or it may lack body.
Styling compositions are thus sought which afford good cosmetic properties, in particular in terms of "disentangling, softness and feel.
In addition, these hair compositions also have the major drawback of giving rise to a powdering S 20 effect. For the purposes of the present invention, the term "powdering" means the aptitude of the material obtained, on drying the hair composition, to form a powder once it has been applied to the hair. Needless to say, the powder falls on the user's shoulders or clothing, or it attaches to the comb or the brush, and this is a detrimental effect.
There is thus a need to find cosmetic compositions, in particular for styling, which do not have the set of drawbacks mentioned above, and which in particular fix the hairstyle well, while at the same time affording good cosmetic properties, and do so without the powdering effect.
The Applicant has discovered, surprisingly and unexpectedly, that when specific silicone/acrylate copolymers are combined with certain specific polymers, it is possible to obtain cosmetic compositions which satisfy the requirements expressed above.
10 One subject of the invention is a cosmetic :eooeo composition comprising, in a cosmetically acceptable medium, at least one silicone/acrylate copolymer and at least one grafted silicone polymer, containing a polysiloxane skeleton grafted with non-silicone organic monomers, the silicone/acrylate copolymer being obtained by radical-mediated polymerization of at least one ethylenically unsaturated monomer in the o* presence of at least one silicone derivative (b) *...comprising oxyalkylene groups.
20 Another subject of the invention relates to a cosmetic hair process, in particular a process for fixing and/or holding the hairstyle using the said composition.
Yet another subject of the invention relates to the use of this composition for the manufacture of a cosmetic hair formulation which is intended in particular for holding and/or shaping the hairstyle.
The silicone/acrylate copolymers particularly targeted by the present invention are those described in International patent application WO 99/04750. In particular, the copolymer sold by BASF under the name Luviflex Silk is preferred. This polymer is a grafted copolymer of tert-butyl acrylate/methacrylic acid and silicone copolyol.
Preferably, the monomer corresponds to formula (Ia):
X-C-CR
7
=CHR
6 (Ia) 0 in which: 15 X is chosen from the group comprising OH, OM, OR NH 2
NHR
8 and N(R )2; M is a cation chosen from Na', Mg"
NH
4 alkylammonium, dialkylammonium, trialkylammonium d k and tetraalkylammonium; the radicals R 8 may be identical or different and are chosen from the group comprising hydrogen, linear or branched C 1 to C 40 alkyl groups, mono- or polyhydroxylated C 1 to C 40 alkyl groups, optionally substituted with one or more alkoxy, amino or carboxyl groups, hydroxylated polyethers, and N,N-dimethylaminoethyl, 2-hydroxyethyl, 2-methoxyethyl, 2-ethoxyethyl, hydroxypropyl, methoxypropyl and ethoxypropyl groups;
R
7 and R 6 are chosen, independently of each other, from the group comprising hydrogen, linear or branched C 1 to C 8 alkyl groups, methoxy, ethoxy, 2-hydroxyethoxy, 2-methoxyethoxy and 2-ethoxyethyl groups, and CN, COOH and COOM groups.
In particular, the monomers of formula (Ia) are acrylic acid and its salts, esters or amides.
The esters may be derivatives of linear Ci to C 40 alkyls, of branched C 3 to C 40 alkyls or of C 3 to C 40 carboxylic alcohols, of polyfunctional alcohols containing 2 to 8 hydroxyls, such as ethylene glycol, hexylene glycol, glycerol and 1,2,6-hexanetriol, of amino alcohols or of alcohol ethers such as methoxymethanol and ethoxyethanol, or polyalkylene glycols.
The monomers of formula (Ia) may also be chosen from N,N-dialkylaminoalkyl acrylates and methacrylates and N-dialkylaminoalkyl-acrylamides and -methacrylamides, the amide group possibly being unsubstituted, N-alkyl- or N-alkylamino-monosubstituted or N,N-dialkylamino-disubstituted, the alkyl or alkylamino groups being derived from linear C 1 to C 40 or branched C 3 to C 40 carboxylic units.
The monomers of formula (Ia) which can be used may also be substituted compounds derived from acrylic acid or its salts, esters or amides. Mention may be made, for example, of methacrylic acid, ethacrylic acid and 3-cyanoacrylic acid.
Other monomers which are particularly suitable are Ci to C40 vinyl and allyl esters, linear C3 to C 40 carboxylic acids or C3 to C40 carboxycyclic acids, vinyl or allyl haldides, vinyllactams, preferably vinylpyrrolidone and vinylcaprolactam, heterocyclic compounds substituted with vinyl or allyl groups, preferably vinylpyridine, vinyloxazoline and allylpyridine, N-vinylimidazoles, diallylamines, vinylidene chloride, carbon-based unsaturated compounds, such as styrene or isoprene, and acrylic or S* methacrylic acid derivatives quaternized with epichlorohydrin.
Other monomers which may finally be mentioned are N-vinylimidazoles, diallylamines, 15 vinylidene chloride, carbon-based unsaturated compounds such as styrene and isoprene, and acrylic or methacrylic acid derivatives quaternized with epichlorohydrin.
Monomers which are most particularly 20 preferred are acrylic, methacrylic and ethacrylic acid; methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, 2-thylhexyl and decyl acrylate; methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, 2-ethylhexyl and decyl methacrylate; methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, 2-ethylhexyl and decyl ethacrylate; 2,3-ihydroxypropyl acrylate; 2,3-dihydroxypropyl methacrylate; 2-dihydroxyethyl acrylate; hydroxypropyl acrylate; 2-hydroxyethyl methacrylate; 2-hydroxyethyl ethacrylate; 2-methoxyethyl acrylate; 2-ethoxyethyl methacrylate; 2-ethoxyethyl ethacrylate; hydroxypropyl methacrylate; glyceryl monoacrylate; glyceryl monomethacrylate; polyalkylene glycol (meth)acrylates, unsaturated sulphonic acids, acrylamide, methacrylamide, ethacrylamide, N,N-dimethylacrylamide, N-ethylacrylamide, N-ethylmethacrylamide, 1-vinylimidazole, N,N-dimethylaminoethyl (meth)acrylate, maleic acid, fumaric acid, maleic anhydride and its monoesters, crotonic acid, itaconic acid, vinyl ethers, vinylformamide, vinylamine, vinylpyridine, vinylimidazole, vinylfuran, styrene, styryl sulphonate and allyl alcohol, and mixtures thereof.
The monomer can also contain silicon or 9 15 fluorine atoms or alternatively thio groups. The monomers can be neutralized if they contain acid groups, this being carried out before or after the polymerization, and partially or totally, so as to adjust the solubility or the degree of dispersion in 20 water to the desired level. Agents serving for the neutralization which may be used are mineral bases, such as sodium carbonate, and organic bases such as amino alcohols, for instance alkanolamines such as methanolamine, 2-amino-2-methyl-l-propanol or triethanolamine, and diamines such as lysine.
The monomers can also be quaternized when they contain a basic nitrogen atom. If they contain at 8 least two ethylenic double bonds, the monomers can be partially crosslinked.
The silicone derivatives are in particular the compounds known under the INCI name of dimethicone copolyols or silicone surfactants. Mention may be made of those sold under the brand names Abil® by Goldschmidt, Alkasil® by Rh6ne-Poulenc, silicone Polyol Copolymer® by Genesee, Besil® by Wacker, Silwet® by OSI or Dow Corning 190® by Dow Corning.
Among the preferred monomers are those Swhich have the formula I below:
S
IX
1 2
S
in which formula R is chosen from CH 3 and the group
R
3 is chosen from hydrogen, CH and the group R 2
R
4 is chosen from hydrogen, CH 3 and the groups I R 1 R1 Oc.c
R
6 is an organic C 1 to C 40 group which can contain amino, carboxyl or sulphonated groups, and if c=0, R 6 is the anion of an inorganic acid; 5 the radicals R 1 may be identical or different and are 4.
chosen from C 1 to C 20 aliphatic hydrocarbons, C 3 to C 20 aliphatic or cycloaliphatic hydrocarbons, and the groups R 5 corresponding to the formula below: [lacuna] a Among the preferred silicone derivatives (b) are those which have the formula I below: 9.4. R3. R2 R1 Jx -y in which formula
R
2 is chosen from CH 3 and the group IR4 .a
R
3 is chosen from CH 3 and the group R 2
R
4 is chosen from hydrogen, CH 3 and the groups L-oJ-- Si-CH3
PA
.*p c R6 is a C 1 to C 40 organic group which can contain amino, carboxyl or sulphonate groups, and if c=0, R 6 is the anion of an inorganic acid; the radicals R 1 may be identical or different and are chosen from C 1 to C 20 aliphatic hydrocarbons, C 3 to C 20 aliphatic or cycloaliphatic hydrocarbons, and the groups R 5 corresponding to the formula below: (C2 (I.a LO b- o S
R
n is an integer between 1 and 6, x and y are integers chosen such that the molecular weight of the polysiloxane is between 300 and 30,000, a and b are integers between 0 and 50, and 11 c is 0 or 1.
R
1 is preferably chosen from methyl, ethyl, propyl, butyl, isobutyl, pentyl, isopentyl, hexyl, octyl, decyl, dodecyl and octadecyl groups, cycloaliphatic radicals, in particular cyclohexyl groups, aromatic groups, in particular phenyl or naphthyl groups, and mixtures of aromatic and aliphatic radicals, such as benzyl and phenylethyl, and also tolyl and xylyl.
The preferred radicals R 4 are those having the formula -(CO)c-R 6
R
6 being an alkyl, cycloalkyl or aryl containing 1 to 4 carbon atoms which can contain additional groups such as NH2, COOH and/or SO 3
H.
The preferred radicals R 6 are those for which c=0, which are phosphates or sulphates.
The silicone derivatives which are particularly preferred are those having the general 0* formula below: t I 5
OH
x y .Ha The relative proportion of derivative in the copolymer is generally from 0.1% to 50% and preferably from 1% to 20% by weight.
The preferred copolymers are the watersoluble silicone/acrylate copolymers or those whose dispersibility in water is such that, in a water/ethanol mixture dosed at 50/50 by volume, they are soluble in a proportion of greater than 0.1 g/l and preferably greater than 0.2 g/l.
The composition advantageously comprises, as a relative percentage by weight of the composition, from 0.1% to 20% of grafted silicone polymer, containing a polysiloxane skeleton grafted with nonsilicone organic monomers, and preferably from 0.2% to The composition advantageously comprises, as a relative percentage by weight, between 0.1% and of silicone/acrylate copolymer, and more preferably between 0.5% and 10% of this copolymer.
o In the following text, in accordance with what is generally accepted, the term silicone polymer is understood to denote any organosilicon polymer or e 20 oligomer having a linear or cyclic, branched or crosslinked structure of variable molecular weight, obtained by polymerization and/or polycondensation of suitably functionalized silanes, and consisting essentially of a repetition of main units in which the silicon atoms are linked together by oxygen atoms (siloxane bonding optionally substituted hydrocarbon radicals being linked directly via a carbon atom to the said silicon atoms. The most common 13 hydrocarbon radicals are alkyl radicals, especially Ci-Cio alkyl radicals, and in particular methyl, fluoroalkyl radicals, aryl radicals and in particular phenyl, and alkenyl radicals and in particular vinyl; other types of radicals which can be linked, either directly or via a hydrocarbon radical, to the siloxane chain are, especially, hydrogen, halogens and in particular chlorine, bromine or fluorine, thiols, alkoxy radicals, polyoxyalkylene (or polyether) radicals and in particular polyoxyethylene and/or polyoxypropylene, hydroxyl or hydroxyalkyl radicals, substituted or unsubstituted amine groups, amide groups, acyloxy radicals or acyloxyalkyl radicals, hydroxyalkylamino radicals or aminoalkyl radicals, quaternary ammonium groups, amphoteric or betaine groups, anionic groups such as carboxylates, thioglycolates, sulphosuccinates, thiosulphates, phosphates and sulphates, needless to say this list not being limiting in any way (so-called "organomodified" silicones).
According to the present invention, the silicone polymer(s) which must be used is (are) that (those) which comprise(s) a main silicone chain (or polysiloxane on which is grafted, inside the said chain as well as, optionally, on at least one of its ends, at least one organic group containing no silicone.
These silicone polymers can be existing commercial products or can be obtained according to any means known to those skilled in the art, in particular by reaction between a starting silicone which is correctly functionalized on one or more of these silicon atoms, and (ii) a non-silicone organic compound which is itself correctly functionalized with a function which is capable of reacting with the functional group(s) borne by the said silicone, forming a covalent bond; a classic example of such a reaction is the hydrosilylation reaction between =Si-H groups and vinyl groups CH 2 or alternatively the reaction between thio functional groups -SH with these same vinyl groups.
Examples of silicone polymers which are suitable for carrying out the present invention, as well as their specific mode of preparation, are described in particular in patent applications EP-A-0,582,152, WO 93/23009 and WO 95/03776, the teachings of which are included in their entirety in the present description by way of non-limiting references.
According to a particularly preferred embodiment of the present invention, the silicone polymer which is used comprises the result of the radical copolymerization between, on the one hand, at least one non-silicone anionic organic monomer having ethylenic unsaturation and/or a non-silicone hydrophobic organic monomer having ethylenic unsaturation, and, on the other hand, a silicone having in its chain at least one functional group capable of reacting with the said ethylenic unsaturations of the said non-silicone monomers, forming a covalent bond, in particular thio functional groups.
According to the present invention, the said anionic monomers containing ethylenic unsaturation are preferably chosen, alone or as a mixture, from linear or branched, unsaturated carboxylic acids, optionally partially or totally neutralized in the form of a salt, it being possible for this (these) carboxylic acid(s) to be, more particularly, acrylic acid, methacrylic acid, maleic acid, maleic anhydride, itaconic acid, fumaric acid and crotonic acid. The suitable salts are, in particular, alkali metal salts, alkaline-earth metal salts and ammonium salts. It will likewise be noted that, in the final grafted silicone polymer, the organic group of anionic nature which comprises the 20 result of the radical (homo)polymerization of at least one anionic monomer of unsaturated carboxylic acid type can, after reaction, be post-neutralized with a base (sodium hydroxide, aqueous ammonia, etc.) in order to bring it into the form of a salt.
According to the present invention, the hydrophobic monomers containing ethylenic unsaturation are preferably chosen, alone or as a mixture, from acrylic acid esters of alkanols and/or methacrylic acid esters of alkanols. The alkanols are preferably Cl-C 18 and more particularly C 1
-C
12 The preferred monomers are chosen from the group consisting of isooctyl (meth)acrylate, isononyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, isopentyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, methyl (meth)acrylate, tert-butyl (meth)acrylate, tridecyl (meth)acrylate and stearyl (meth)acrylate, or mixtures thereof.
One family of grafted silicone polymers which is particularly suitable for carrying out the present invention consists of silicone polymers containing in their structure the unit of formula below: GI GI
G
*I
(G
2
)-S-G
3
(G
2
S-G
4
(I)
in which the radicals G 1 which may be identical or different, represent hydrogen or a C 1
-C
0 i alkyl radical or alternatively a phenyl radical; the radicals G 2 which may be identical or different, represent a Ci-Clo alkylene group; G 3 represents a polymer residue resulting from the (homo)polymerization of at least one anionic monomer containing ethylenic unsaturation; G 4 represents a polymer residue resulting from the (homo)polymerization of at least one hydrophobic monomer containing ethylenic unsaturation; m and n are equal to 0 or 1; a is an integer ranging from 0 to b is an integer which may be between 10 and 350, c is an integer ranging from 0 to 50; with the proviso that one of the parameters a and c is other than 0.
Preferably, the unit of formula above has at least one, and even more preferably all, of the following characteristics: the radicals GL denote an alkyl radical, preferably the methyl radical; n is non-zero and the radicals G 2 represent a divalent CI-C 3 radical, preferably a propylene radical;
G
3 represents a polymeric radical resulting .from the (homo)polymerization of at least one monomer of the carboxylic acid type containing ethylenic unsaturation, preferably acrylic acid and/or methacrylic acid;
G
4 represents a polymeric radical resulting from the (homo)polymerization of at least one monomer of the Ci-Clo alkyl (meth)acrylate type, preferably of the isobutyl or methyl (meth)acrylate type.
Examples of silicone polymers corresponding to formula are, in particular, polydimethylsiloxanes (PDMS) on which are grafted, via a thiopropylene-type connecting chain, mixed polymer units of the poly(meth)acrylic acid type and of the polymethyl (meth)acrylate type.
Other examples of silicone polymers corresponding to formula are, in particular, polydimethylsiloxanes (PDMS) on which are grafted, via a thiopropylene-type connecting chain, polymer units of the polyisobutyl (meth)acrylate type.
Preferably, the number-average molecular mass of the silicone polymers of the invention, ranges approximately from 10,000 to 1,000,000 and even more preferably approximately from 10,000 to 100,000.
The cosmetically acceptable medium preferably consists of water or one or more cosmetically acceptable solvents such as alcohols or water/solvent(s) mixtures, the solvents preferably being C 1
-C
4 alcohols.
Among these alcohols which may be mentioned are ethanol and isopropanol. Ethanol is particularly preferred.
The composition of the invention can also contain at least one additive chosen from anionic, cationic, nonionic and amphoteric surfactants, fragrances, screening agents, preserving agents, proteins, vitamins, polymers other than those of the invention, plant, mineral or synthetic oils and any other additive conventionally used in cosmetic compositions.
Needless to say, a person skilled in the art will take care to select the optional compound(s) to be added to the composition according to the invention such that the advantageous properties intrinsically associated with the composition in accordance with the 19 invention are not, or are not substantially, adversely affected by the addition envisaged.
These compositions may be packaged in various forms, in particular in pump-dispenser bottles or in aerosol containers, in order to ensure application of the composition in vaporized form or in the form of a mousse. Such packaging forms are indicated, for example, when it is desired to obtain a spray, a lacquer or a mousse for fixing or treating hair. The compositions in accordance with the invention can also be in the form of creams, gels, emulsions, lotions or waxes.
~When the composition according to the invention is packaged in aerosol form in order to obtain a lacquer or a mousse, it comprises at least one propellant which may be chosen from volatile ro hydrocarbons such as n-butane, propane, isobutane and pentane, a halogenated hydrocarbon and mixtures p. thereof. Carbon dioxide, nitrous oxide, dimethyl ether (DME), nitrogen or compressed air can also be used as propellant. Mixtures of propellants can also be used.
Dimethyl ether is preferably used.
The propellant is advantageously present in a concentration of between 5% and 90% by weight relative to the total weight of the composition in the aerosol device, and more particularly at a concentration of between 10% and The compositions in accordance with the invention can be applied to the skin, the nails, the lips, the hair, the eyebrows and the eyelashes.
The compositions in accordance with the invention are particularly suitable for dry or wet hair, as styling products.
The invention will be illustrated more fully with the aid of the non-limiting examples which follow.
All the percentages are relative percentages 10 by weight with respect to the total weight of the composition, and a.m. means active material.
EXAMPLE:
The composition below is prepared in a pump-dispenser bottle.
Luviflex Silk (BASF)* 4% Polysilicone 8 (VS80 sold by the company 3M) 2% AMP qs pH 7 Water 14% Ethanol qs 100 g silicone/acrylate copolymer (t-butyl acrylate/methacrylic acid/PDMS polyether) 704 This composition is sprayed onto European natural chestnut hair. After drying, the hair is held well and has a cosmetic feel.
It is to be understood that, if any prior art publication is referred to herein, such reference does not constitute an admission that the publication forms a part of the common general knowledge in the art, in Australia or any other country.
For the purposes of this specification it will be clearly understood that the word "comprising" means "including but not limited to", and that the word "comprises" has a corresponding meaning.
Claims (23)
1. Cosmetic composition comprising, in a cosmetically acceptable medium, at least one silicone/acrylate copolymer and at least one grafted silicone polymer, containing a polysiloxane skeleton grafted with non-silicone organic monomers, the silicone/acrylate copolymer being obtained by radical- mediated polymerization of at least one ethylenically 10 unsaturated monomer in the presence of at least one silicone derivative comprising oxyalkylene groups. Composition according to Claim 1, characterized in that the monomer corresponds to formula (Ia): X-C-CR 7 =CHR 6 (Ia) 0 in which: 20 X is chosen from the group comprising OH, OM, OR NH 2 NHR and N(R )2; M is a cation chosen from Na', K Mg", NH", alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium; the radicals R 8 may be identical or different and are chosen from the group comprising hydrogen, linear or branched C 1 to C 40 alkyl groups, mono- or polyhydroxylated Ci to C 40 alkyl groups, optionally substituted with one or more alkoxy, amino i* 22 or carboxyl groups, hydroxylated polyethers, and N,N-dimethylaminoethyl, 2-hydroxyethyl, 2-methoxyethyl,
2-ethoxyethyl, hydroxypropyl, methoxypropyl and ethoxypropyl groups; R 7 and R 6 are chosen, independently of each other, from the group comprising hydrogen, linear or branched C 1 to Cs alkyl groups, methoxy, ethoxy, 2-hydroxyethoxy, 2-methoxyethoxy and 2-ethoxyethyl groups, and CN, COOH and COOM groups. 10 3. Cosmetic hair composition according to Claim 1, characterized in that the silicone derivative corresponds to the formula below: -t a in which formula 15 R 2 is chosen from CH 3 and the group R is chosen from CH 3 and the group R R 4 is chosen from hydrogen, CH 3 and the groups R 1 H 1 C c R 6 is an organic C 1 to C 40 group which can contain amino, carboxyl or sulphonate groups, and if c=0, R 6 is the anion of an inorganic acid; 5 the radicals R 1 may be identical or different and are chosen from C 1 to C 20 aliphatic hydrocarbons, C 3 to C 20 aliphatic or cycloaliphatic hydrocarbons, and the groups R 5 corresponding to the formula below: n is an integer between 1 and 6, x and y are integers chosen such that the molecular weight of the polysiloxane is between 300 and 30,000, a and b are integers between 0 and 50, and c is 0 or 1.
4. Composition according to Claim 1, characterized in that the monomer is chosen from C 1 to C 40 vinyl and allyl esters, linear C 3 to C 40 carboxylic acids or C 3 to C 40 carboxycyclic acids, vinyl or allyl haldides, vinyllactams, preferably vinylpyrrolidone and vinylcaprolactam, heterocyclic compounds substituted with vinyl or allyl groups, preferably vinylpyridine, vinyloxazoline and allylpyridine, N-vinylimidazoles, diallylamines, vinylidene chloride, carbon-based unsaturated compounds, such as styrene or isoprene, and acrylic or methacrylic acid derivatives quaternized with epichlorohydrin.
5. Composition according to Claim 1, characterized in that the monomer is chosen from the group comprising acrylic, methacrylic and ethacrylic acid; methyl, ethyl, propyl, n-butyl, 0..0 isobutyl, t-butyl, 2-ethylhexyl and decyl acrylate; methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, 2-ethylhexyl and decyl methacrylate; methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, 2-ethylhexyl and decyl ethacrylate; 2,3-dihydroxypropyl acrylate; 2,3-dihydroxypropyl methacrylate; 2-dihydroxyethyl acrylate; hydroxypropyl acrylate; 2-hydroxyethyl methacrylate; 2-hydroxyethyl ethacrylate; 2-methoxyethyl acrylate; 2-ethoxyethyl methacrylate; 2-ethoxyethyl ethacrylate; hydroxypropyl methacrylate; glyceryl monoacrylate; glyceryl monomethacrylate; polyalkylene glycol (meth)acrylates, unsaturated sulphonic acids, acrylamide, methacrylaide, ethacrylamide, N,N-dimethylacrylamide, N-ethyl- acrylamide, N-ethylmethacrylamide, 1-vinylimidazole, 25 N,N-dimethylaminoethyl (meth)acrylate, maleic acid, fumaric acid, maleic anhydride and it monoesters, crotonic acid, itaconic acid, vinyl ethers, vinylformamide, vinylamine, vinylpyridine, vinylimidazole, vinylfuran, styrene, styryl sulphonate and allyl alcohol, and mixtures thereof.
6. Composition according to any one of the preceding claims, characterized in that the silicone derivatives are chosen from dimethicone copolyols and silicone surfactants.
7. Composition according to any one of the preceding claims, characterized in that it comprises, as a relative percentage by weight, from 0.1% to 20% of silicone/acrylate copolymer. S8. Composition according to claim 7, characterized in that it comprises, as a relative percentage by weight, 20 from 0.5% to 10% of silicone/acrylate copolymer.
9. Composition according to any one of the preceding claims, characterized in that the grafted silicone polymer comprises a main polysiloxane chain on which is grafted, inside the said chain as well as, optionally, on at least one of its ends, at least one organic group containing no silicone. Composition according to any one of the preceding claims, characterized in that the grafted silicone polymer can be obtained by radical-mediated copolymerization between, on the one hand, at least one non-silicone anionic organic monomer having ethylenic unsaturation and/or a non-silicone hydrophobic organic monomer having ethylenic unsaturation, and, on the other hand, a polysiloxane having in its chain at least one ^functional group capable of reacting with the said \\melbfiles\home$\shonal\Keep\SPECI\56487-00. SPEI .doc 10/05/02 26 ethylenic unsaturations of the said non-silicone monomers.
11. Composition according to Claim 10, characterized in that the anionic organic monomer containing ethylenic unsaturation is chosen, alone or in the form of a mixture of monomers, from linear or branched unsaturated carboxylic acids.
12. Composition according to Claim 10, characterized in that the anionic organic monomer containing ethylenic unsaturation is chosen, alone or in the form of a mixture of monomers, from acrylic acid, methacrylic acid, maleic acid, maleic anhydride, itaconic acid, fumaric acid and crotonic acid, or alkali metal, alkaline-earth metal or ammonium salts thereof, or mixtures thereof.
13. Composition according to Claim 10, characterized in that the hydrophobic organic monomer containing ethylenic unsaturation is chosen, alone or as a mixture of 20 monomers, from acrylic acid esters of alkanols and/or methacrylic acid esters of alkanols, the alkanol preferably being Ci-C 18
14. Composition according to Claim 10, characterized in that the hydrophobic organic monomer containing ethylenic unsaturation is chosen, alone or as a mixture of monomers, from the group consisting of isooctyl (meth)acrylate, isononyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, isopentyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, methyl (meth)acrylate, tert-butyl (meth)acrylate, tridecyl (meth)acrylate and stearyl (meth)acrylate.
15. Composition according to any one of the preceding claims, characterized in that the grafted S silicone polymer comprises, on the main silicone chain, at \\melbfiles\home$\shonal\Keep\SPECI\56487-00.1 SPECI.doc 10/05/02 27 least one organic group of anionic nature obtained by radical-mediated (homo)polymerization of at least one anionic monomer of unsaturated carboxylic acid type, partially or totally neutralized in the form of a salt.
16. Composition according to any one of Claims 1 to characterized in that the grafted silicone polymer is chosen from silicone polymers containing in their structure the unit of formula below: GI G 1 (-Si (G2)-S-G G, (G 2 in which the radicals G 1 which may be identical or different, represent hydrogen or a Ci-CIo alkyl radical or alternatively a phenyl radical; the radicals G 2 which may be identical or different, represent a Ci-C 10 alkylene group; G 3 represents a polymer residue resulting from the 20 (homo)polymerization of at least one anionic monomer containing ethylenic unsaturation; G 4 represents a polymer residue resulting from the (homo)polymerization of at least one hydrophobic monomer containing ethylenic unsaturation; m and n are equal to 0 or 1; a is an integer ranging from 0 to 50; b is an integer which may be between and 350, c is an integer ranging from 0 to 50; with the proviso that one of the parameters a and c is other than 0.
17. Composition according to Claim 16, characterized in that the unit of formula has at least one of the following characteristics: the radicals Gi denote a Ci-Clo alkyl radical; n is non-zero and the radicals G 2 represent a divalent C 1 -C 3 radical; ST G 3 represents a polymeric radical resulting \\melb_files\homeS\shonal\Keep\SPECI\56 487 -00.1 SPECI.doc 10/05/02 OFF 28 from the (homo)polymerization of at least one monomer of the carboxylic acid type containing ethylenic unsaturation; G 4 represents a polymeric radical resulting from the (homo)polymerization of at least one monomer of the Ci-Cio alkyl (meth)acrylate type.
18. Composition according to Claim 16 or 17, characterized in that the unit of formula (I) simultaneously has the following characteristics: the radicals Gi denote a methyl radical; n is non-zero and the radicals G 2 represent a propylene radical; S G 3 represents a polymeric radical resulting from the (homo)polymerization of at least acrylic acid and/or methacrylic acid; .G 4 represents a polymeric radical resulting from the (homo)polymerization of at least one monomer of the isobutyl or methyl (meth)acrylate type.
19. Composition according to any one of the preceding claims, characterized in that the number-average molecular mass of the grafted silicone polymer ranges .i approximately from 10,000 to 1,000,000. Composition according to claim 19, characterized in that the number-average molecular mass of the grafted silicone polymer ranges from 10,000 to 100,000.
21. Composition according to any one of the preceding claims, characterized in that it comprises, as a relative percentage by weight, from 0.1% to 20% of grafted silicone polymer.
22. Composition according to claim 21, characterized in that it comprises, as a relative percentage by weight, A^1<i from 0.2% to 10% of the grafted silicone polymer. \\melb-files\hames\shonal\Keep\SP ECI\56 4 8 7 0 0 1 SPECI.doc 10/05/02 29
23. Composition according to any one of the preceding claims, characterized in that it also contains at least one additive chosen from anionic, cationic, nonionic and amphoteric surfactants, fragrances, preserving agents, screening agents, proteins, vitamins, polymers other than those of the invention, and plant, mineral or synthetic oils.
24. Process for holding or shaping the hairstyle, characterized in that it uses a composition in accordance with any one of Claims 1 to 23. Use of a composition according to any one of Claims 1 to 23, for the manufacture of a cosmetic product.
26. Use of a composition according to claim 25, for the manufacture of a hair product.
27. Use of a composition according to any one of Claims 1 to 23, for the skin, the nails, the lips, the hair, the eyebrows and the eyelashes.
28. Cosmetic compositions or use or processes involving them, substantially as hereinbefore described 25 with reference to the accompanying example. Dated this 1 0 th day of May 2002 L'OREAL By their Patent Attorneys GRIFFITH HACK Fellows Institute of Patent and Trade Mark Attorneys of Australia \\melb-files\home$\sonal\Keep\SPECI\64 8 7 0 1 SPECI.doc 10/05/02
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9911596A FR2798844B1 (en) | 1999-09-16 | 1999-09-16 | COSMETIC COMPOSITION COMPRISING AT LEAST ONE SILICONE / ACRYLATE COPOLYMER AND AT LEAST ONE GRAFTED SILICONE POLYMER |
FR9911596 | 1999-09-16 |
Publications (2)
Publication Number | Publication Date |
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AU5648700A AU5648700A (en) | 2001-03-22 |
AU750093B2 true AU750093B2 (en) | 2002-07-11 |
Family
ID=9549922
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU56487/00A Ceased AU750093B2 (en) | 1999-09-16 | 2000-09-05 | Cosmetic composition comprising at least one silicone/ acrylate copolymer and at least one grafted silicone polymer |
Country Status (13)
Country | Link |
---|---|
EP (1) | EP1084698B1 (en) |
JP (2) | JP2001114655A (en) |
KR (1) | KR100364307B1 (en) |
CN (1) | CN1293028A (en) |
AT (1) | ATE244550T1 (en) |
AU (1) | AU750093B2 (en) |
BR (1) | BR0004351A (en) |
CA (1) | CA2319959A1 (en) |
DE (1) | DE60003763T2 (en) |
ES (1) | ES2202018T3 (en) |
FR (1) | FR2798844B1 (en) |
PL (1) | PL342564A1 (en) |
RU (1) | RU2197221C2 (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
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FR2825630B1 (en) * | 2001-06-11 | 2003-09-19 | Oreal | COSMETIC AND / OR DERMATOLOGICAL COMPOSITION IN THE FORM OF A WATER IN OIL EMULSION STABILIZED BY A (CO) POLYMER OF SULFONIC 2-ACRYLAMIDO-2-METHYLPROPANE WITH HYDROPHOBIC GRAFTS |
JP6224557B2 (en) * | 2014-09-04 | 2017-11-01 | 信越化学工業株式会社 | Film-forming composition and cosmetic |
US9988590B1 (en) * | 2017-11-10 | 2018-06-05 | Afton Chemical Corporation | Polydialkylsiloxane poly (meth)acrylate brush polymers for lubricant additive application |
JP6850268B2 (en) * | 2018-02-09 | 2021-03-31 | 信越化学工業株式会社 | (Meta) Acrylic Silicone Graft Copolymer and Its Manufacturing Method |
TW202023523A (en) * | 2018-10-11 | 2020-07-01 | 美商陶氏全球科技責任有限公司 | Color cosmetic formulation |
CN110437944A (en) * | 2019-08-15 | 2019-11-12 | 广州立白企业集团有限公司 | A kind of dedicated purificant of automatic dish-washing machine with resistive connection film and spotting performance |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US5166276A (en) * | 1989-07-12 | 1992-11-24 | Mitsubishi Petrochemical Company Ltd. | Polymer for hair-care products |
FR2735689B1 (en) * | 1995-06-21 | 1997-08-01 | Oreal | COMPOSITION COMPRISING A DISPERSION OF POLYMER PARTICLES IN A NON-AQUEOUS MEDIUM |
FR2740037B1 (en) * | 1995-10-18 | 1997-12-05 | Rhone Poulenc Chimie | COSMETIC COMPOSITIONS FOR HAIR AND SKIN BASED ON FUNCTIONALIZED POLYORGANOSILOXANES |
JP4099310B2 (en) * | 1997-07-23 | 2008-06-11 | ビーエーエスエフ ソシエタス・ヨーロピア | Use of polysiloxane-containing polymers for cosmetic formulations |
-
1999
- 1999-09-16 FR FR9911596A patent/FR2798844B1/en not_active Expired - Fee Related
-
2000
- 2000-08-28 EP EP00402377A patent/EP1084698B1/en not_active Revoked
- 2000-08-28 ES ES00402377T patent/ES2202018T3/en not_active Expired - Lifetime
- 2000-08-28 DE DE60003763T patent/DE60003763T2/en not_active Expired - Fee Related
- 2000-08-28 AT AT00402377T patent/ATE244550T1/en not_active IP Right Cessation
- 2000-09-05 AU AU56487/00A patent/AU750093B2/en not_active Ceased
- 2000-09-12 JP JP2000277134A patent/JP2001114655A/en active Pending
- 2000-09-15 CA CA002319959A patent/CA2319959A1/en not_active Abandoned
- 2000-09-15 RU RU2000123753/04A patent/RU2197221C2/en not_active IP Right Cessation
- 2000-09-15 BR BR0004351-6A patent/BR0004351A/en not_active IP Right Cessation
- 2000-09-15 PL PL00342564A patent/PL342564A1/en not_active Application Discontinuation
- 2000-09-15 CN CN00128741A patent/CN1293028A/en active Pending
- 2000-09-16 KR KR1020000054438A patent/KR100364307B1/en not_active IP Right Cessation
-
2004
- 2004-08-02 JP JP2004226152A patent/JP2004307517A/en not_active Withdrawn
Also Published As
Publication number | Publication date |
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CA2319959A1 (en) | 2001-03-16 |
KR20010030416A (en) | 2001-04-16 |
FR2798844A1 (en) | 2001-03-30 |
EP1084698B1 (en) | 2003-07-09 |
EP1084698A1 (en) | 2001-03-21 |
JP2004307517A (en) | 2004-11-04 |
DE60003763T2 (en) | 2004-04-15 |
BR0004351A (en) | 2001-04-10 |
PL342564A1 (en) | 2001-03-26 |
ATE244550T1 (en) | 2003-07-15 |
RU2197221C2 (en) | 2003-01-27 |
FR2798844B1 (en) | 2001-11-30 |
JP2001114655A (en) | 2001-04-24 |
CN1293028A (en) | 2001-05-02 |
KR100364307B1 (en) | 2002-12-12 |
ES2202018T3 (en) | 2004-04-01 |
AU5648700A (en) | 2001-03-22 |
DE60003763D1 (en) | 2003-08-14 |
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