WO2018225529A1 - Composition for keratin fibers - Google Patents

Composition for keratin fibers Download PDF

Info

Publication number
WO2018225529A1
WO2018225529A1 PCT/JP2018/020086 JP2018020086W WO2018225529A1 WO 2018225529 A1 WO2018225529 A1 WO 2018225529A1 JP 2018020086 W JP2018020086 W JP 2018020086W WO 2018225529 A1 WO2018225529 A1 WO 2018225529A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
weight
keratin fibers
composition according
vinylpyrrolidone
Prior art date
Application number
PCT/JP2018/020086
Other languages
French (fr)
Inventor
Harumi Mori
Takuya Hara
Amer Alkahwaji
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
Application filed by L'oreal filed Critical L'oreal
Publication of WO2018225529A1 publication Critical patent/WO2018225529A1/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
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362Polycarboxylic acids
    • 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
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/08Preparations for bleaching the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair

Definitions

  • the present invention relates to a composition to be applied onto keratin fibers such typically used in dyeing or bleaching the keratin fibers, as well as the uses thereof.
  • the dyed or bleached keratin fibers tend to lose their volume because the roots of the dyed or bleached keratin fibers tend to bend, and it becomes difficult to lift up the keratin fibers.
  • the loss of volume in dyed or bleached keratin fibers is not preferable because hair styling tends to be not easy.
  • the side of the roots can be more visible.
  • the difference in color between the dyed or bleached part of the keratin fibers and the newly grown undyed or unbleached part of the keratin fibers tends to be more distinct. This is not preferable either from the viewpoint of uniform appearance of dyed or bleached keratin fibers from the root to the tip of the keratin fibers.
  • undyed keratin fibers are white or gray hair, for example, the loss of volume of dyed keratin fibers may cause the appearance of looking old.
  • the loss of volume of dyed or bleached keratin fibers tends to be worse, when the dyed or bleached keratin fibers are washed by, for example, shampooing.
  • An objective of the present invention is to provide a composition for keratin fibers which can prevent or reduce the loss of volume of keratin fibers when the keratin fibers are colored and/or when the colored keratin fibers are washed.
  • composition for use in coloring or bleaching keratin fibers, preferably hair comprising:
  • the (b) cationic polymer may have a unit derived from vinylpyrrolidone.
  • the (b) cationic polymer may be selected from:
  • copolymers comprising vinylpyrrolidone units and dimethylaminoethyl methacrylate units
  • copolymers comprising vinylpyrrolidone units and methylvinylimidazolium units.
  • copolymers comprising vinylpyrrolidone units and dimethylaminoethyl methacrylate units may be chosen from:
  • the amount of the (a) malonic acid may range from 0.1% to 20% by weight, preferably from 0.5% to 15% by weight, and more preferably from 1% to 10% by weight, relative to the total weight of the composition.
  • the amount of the (b) cationic polymer may range from 0.5% to 30% by weight, preferably from 1%) to 20%) by weight, and more preferably from 1.5% to 15% by weight, relative to the total weight of the composition.
  • the composition according to the present invention may further comprise propylene glycol.
  • the amount of the propylene glycol may range from 0.01 to 30% by weight, preferably from 0.1 to 25% by weight, and more preferably from 1 to 20% by weight relative to the total weight of the composition.
  • composition according to the present invention may further comprise at least one oxidizing agent.
  • the oxidizing agent may be hydrogen peroxide.
  • the amount of the oxidizing agent may range from 0.01% to 30% by weight, preferably from 0.1%) to 20%) by weight, and more preferably from 1% to 10% by weight, relative to the total weight of the composition.
  • the present invention also relates to a ready-to-use cosmetic composition for keratin fibers, preferably hair, comprising:
  • a first composition comprising at least one oxidizing agent
  • the present invention also relates to a kit for keratin fibers, preferably hair, comprising: a first compartment comprising the composition according to the present invention, further comprising at least one oxidizing agent, and
  • a second compartment comprising a second composition comprising at least one alkaline agent.
  • the present invention also relates to a kit for keratin fibers, preferably hair, comprising: a first compartment comprising a first composition comprising at least one oxidizing agent,
  • a second compartment comprising a second composition comprising at least one alkaline agent
  • a third compartment comprising the composition according to the present invention.
  • the present invention also relates to a cosmetic process for keratin fibers, preferably hair, comprising the steps of:
  • a first composition comprising at least one oxidizing agent
  • a second composition comprising at least one alkaline agent to prepare a ready-to-use cosmetic composition
  • Fig. 1 shows a side view in order to show how to determine the vertical angle between a plate and the tips of a hair fiber in the evaluation of volumizing effects of the compositions according to Examples 1-5 and Comparative Examples 1-10.
  • a combination of malonic acid and at least one cationic polymer can impart a volumizing effect and long lastingness to keratin fibers, when it is used in coloring or bleaching compositions for keratin fibers, thus completing the present invention.
  • the present invention relates to a composition for use in coloring or bleaching keratin fibers, preferably hair, comprising:
  • the above composition according to the present invention can prevent or reduce the loss of volume of keratin fibers when the keratin fibers are colored by, for example, dyeing or bleaching, and/or when the colored keratin fibers are washed by, for example, shampooing.
  • "Keratin fibers” here mean fibers which include at least one keratin substance. It is preferable that at least a part of the surface of the keratin fibers be formed by keratin substances. Examples of keratin fibers include hair, eyebrows, eyelashes, and the like. It is preferable that the present invention is used for hair.
  • the above composition for keratin fibers according to the present invention can be used as a conditioning or a booster composition in coloring keratin fibers for the purpose of preventing or reducing the loss of volume of keratin fibers.
  • composition according to the present invention can be used in combination with another composition including oxidizing agent(s). If the composition according to the present invention, which further comprises oxidizing agent(s), is used in combination with another composition including oxidation dye(s), it is possible to dye the keratin fibers. Alternatively, if the composition according to the present invention, which further comprises oxidizing agent(s), is used alone, it is possible to bleach the keratin fibers due to the action of the oxidizing agent.
  • composition for keratin fibers according to the present invention be mixed with other compositions including each of at least one oxidizing agent and at least one alkaline agent, and the mixture thus obtained is used to color keratin fibers.
  • another composition including at least one alkaline agent includes oxidation base(s) and coupler(s)
  • the keratin fibers can be dyed in a variety of colors.
  • composition for use in coloring or bleaching keratin fibers according to the present invention can prevent or reduce the loss of volume of keratin fibers when the keratin fibers are colored by, for example, dyeing or bleaching, and/or when the colored keratin fibers are washed by, for example, shampooing.
  • composition for use in coloring or bleaching keratin fibers, preferably hair, according to the present invention comprises:
  • composition according to the present invention comprises (a) malonic acid.
  • Malonic acid can be represented by the general formula below:
  • the (a) malonic acid may be present in a content of 0.1% by weight or more, preferably 0.5% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition.
  • the (a) malonic acid may be present in a content of 20% by weight or less, preferably 15% by weight or less, and more preferably 10% by weight or less, relative to the total weight of the composition.
  • the (a) malonic acid may be present in a content ranging from 0.1% to 20% by weight, preferably from 0.5% to 15% by weight, and more preferably from 1% to 10% by weight, relative to the total weight of the composition.
  • composition according to the present invention comprises (b) at least one cationic polymer.
  • Two or more (b) cationic polymers may be used in combination.
  • a single type of cationic polymer or a combination of different types of cationic polymers may be used.
  • cationic polymer denotes any polymer containing cationic groups and/or groups that may be ionized into cationic groups.
  • Such polymers may be chosen from those already known per se as improving the cosmetic properties of the hair, i.e., especially those described in patent application EP-A-337 354 and in French patents FR-2 270 846, 2 383 660, 2 598 611, 2 470 596 and 2 519 863.
  • cationic polymers that may be mentioned more particularly are polymers of the polyamine, polyamino amide and polyquaternary ammonium type.
  • Acationic polymer has a positive charge density.
  • the charge density of the cationic polymer may be from 0.1 meq/g to 20 meq/g, preferably from 1 to 15 meq/g, and more preferably from 4 to 10 meq/g.
  • the molecular weight of the cationic polymer be 1,000 or more, preferably 10,000 or more, more preferably 100,000 or more, and even more preferably 1,000,000 or more.
  • the cationic polymer may have at least one positively chargeable and/or positively charged moiety selected from the group consisting of a secondary or tertiary amino group, a quaternary ammonium group, a guanidine group, a biguanide group, an imidazole group, an imino group, a pyridyl group, and an amino group.
  • the cationic polymer may be a homopolymer or a copolymer.
  • copolymer is understood to mean both copolymers obtained from two kinds of monomers and those obtained from more than two kinds of monomers, such as terpolymers obtained from three kinds of monomers.
  • the cationic polymer may be selected from natural and synthetic cationic polymers.
  • Non-limiting examples of the cationic polymers are as follows.
  • Ri and R 2 which may be identical or different, are chosen from hydrogen and alkyl groups comprising from 1 to 6 carbon atoms, for instance, methyl and ethyl groups;
  • R 3 which may be identical or different, is chosen from hydrogen and CH 3 ;
  • the symbols A which may be identical or different, are chosen from linear or branched alkyl groups comprising from 1 to 6 carbon atoms, for example, from 2 to 3 carbon atoms and hydroxyalkyl groups comprising from 1 to 4 carbon atoms;
  • R 4 , R 5 , and R 6 which may be identical or different, are chosen from alkyl groups comprising from 1 to 18 carbon atoms and benzyl groups, and in at least one embodiment, alkyl groups comprising from 1 to 6 carbon atoms; and
  • X is an anion derived from an inorganic or organic acid, such as methosulphate anions and halides, for instance chloride and bromide.
  • the copolymers of family (1) may also comprise at least one unit derived from comonomers which may be chosen from acrylamides, methacrylamides, diacetone acrylamides, acrylamides and methacrylamides substituted on the nitrogen atom with (C1-C4) lower alkyl groups, groups derived from acrylic or methacrylic acids and esters thereof, vinyllactams such as vinylpyrrolidone and vinylcaprolactam, and vinyl esters.
  • comonomers which may be chosen from acrylamides, methacrylamides, diacetone acrylamides, acrylamides and methacrylamides substituted on the nitrogen atom with (C1-C4) lower alkyl groups, groups derived from acrylic or methacrylic acids and esters thereof, vinyllactams such as vinylpyrrolidone and vinylcaprolactam, and vinyl esters.
  • Examples of copolymers of family (1) include, but are not limited to:
  • copolymers of acrylamide and of dimethylaminoethyl methacrylate quaternized with dimethyl sulphate or with a dimethyl halide
  • copolymers of acrylamide and of methacryloyloxyethyltrimethylammonium methosulphate quatemized or nonquatemized vinylpyrrolidone/dialkylaminoalkyl acrylate or methacrylate copolymers, described, for example, in French Patent Nos. 2 077 143 and 2 393 573, dimethylaminoethyl methacrylate/vinylcaprolactam/vinylpyrrolidone terpolymers, vinylpyrrolidone/methacrylamidopropyldimethylamine copolymers, quatemized vinylpyrrolidone/dimethylaminopropylmethacrylamide copolymers, and
  • crosslinked methacryloyloxy(C 1 -C 4 )alkyltri(Ci-C4)alkylammonium salt polymers such as the polymers obtained by homopolymerization of dimethylaminoethyl methacrylate quatemized with methyl chloride, or by copolymerization of acrylamide with dimethylaminoethyl methacrylate quatemized with methyl chloride, the homopolymerization or copolymerization being followed by crosslinking with a compound containing olefinic unsaturation, for example, methylenebisacrylamide.
  • copolymers of family (1) have a unit derived from vinylpyrrolidone. More preferably, copolymers of family (1) have at least one pendent ring structure derived from the vinylpyrrolidone. On the other hand, it is preferable that the copolymers of family (1) comprise no ring structure in the backbone of the polymer.
  • copolymers of family (1) having vinylpyrrolidone units can be selected from:
  • vinylpyrrolidone/dimethylaminoethyl methacrylate copolymers quatemized with diethyl sulphate for example, vinylpyrrolidone/dimethylaminoethyl methacrylate copolymer quatemized with diethyl sulphate, sold under the trade names Gafquat 734, 755, 755S and 755L by the company I.S.P.,
  • vinylpyrrolidone/dimethylaminoethyl methacrylate/hydrophilic polyurethane copolymers for example, vinylpyrrolidone/dimethylaminoethyl methacrylate/hydrophilic polyurethane copolymer, sold under the trade name Pecogel GC-310 by the company U.C.I.B., or under the trade names Aquamere CI 031 and C1511 by the company Blagden Chemicals,
  • vinylpyrrolidone/dimethylaminoethyl methacrylate/vinylcaprolactam copolymers for example, vinylpyrrolidone/dimethylaminoethyl methacrylate/vinylcaprolactam copolymer sold under the trade name Gaffix VC713 by the company I.S.P;
  • vinylpyrrolidone/methacrylamidopropyltrimethylammonium copolymers for example, vinylyrrolidone/MAPTAC copolymer sold under the trade names Gafquat ACP1011 and Gafquat HS100 by the company I.S.P,
  • the copolymers comprising vinylpyrrolidone units and methylvinylimidazolium units, for example: - vinylpyrrolidone/methylvinylimidazolium chloride copolymers; for example, vinylpyrrolidone/methylvinylimidazolium chloride copolymer sold under the trade names Luviquat FC370, FC550, FC905 and HM552 by the company BASF,
  • vinylpyrrolidone/methylvinylimidazolium chloride/vinylimidazole copolymers for example, vinylpyrrolidone/methylvinylimidazolium chloride/vinylimidazole copolymer sold under the trade name Luviquat 8155 by the company BASF,
  • vinylpyrrolidone/methylvinylimidazolium methosulphate copolymers for example, vinylpyrrolidone/methylvinylimidazolium methosulphate copolymer sold under the trade name Luviquat MS370 by the company BASF.
  • the copolymers of family (1) be chosen from the copolymer comprising vinylpyrrolidone units and dimethylaminoethyl methacrylate units, more preferably chosen from vinylpyrrolidone/dimethylaminoethyl methacrylate copolymers quaternized with diethyl sulphate, and even more preferably Polyquaternium-11.
  • Cationic cellulose derivatives such as cellulose ether derivatives comprising quaternary ammonium groups described, for example, in French Patent No. 1 492 597, such as the polymers sold under the names "JR" (JR 400, JR 125, and JR 30M) or "LR” (LR 400 and LR 30M) by the company Union Carbide Corporation. These polymers are also defined in the CTFA dictionary as quaternary ammoniums of hydroxyethylcellulose that have reacted with an epoxide substituted with a trimethylammonium group.
  • the cationic cellulose derivatives be quaternized hydroxyethyl celluloses modified with at least one quaternary ammonium group comprising at least one fatty chain, such as alkyl, arylalkyl or alkylaryl groups comprising at least 8 carbon atoms, or mixtures thereof.
  • the alkyl radicals borne by the quaternary ammonium group may preferably contain from 8 to 30 carbon atoms, especially from 10 to 30 carbon atoms.
  • the aryl radicals preferably denote phenyl, benzyl, naphthyl or anthryl groups.
  • the cationic cellulose derivatives may comprise at least one quaternary ammonium group including at least one Cs-C 30 hydrocarbon group.
  • Examples of quaternized alkylhydroxyethylcelluloses containing C 8 -C 30 fatty chains that may be mentioned include the products Quatrisoft LM 200, Quatrisoft LM-X 529-18-A, Quatrisoft LM-X 529-18B (CI 2 alkyl) and Quatrisoft LM-X 529-8 (CI 8 alkyl) or Softcat Polymer SL100, Softcat SX-1300X, Softcat SX-1300H, Softcat SL-5, Softcat SL-30, Softcat SL-60 , Softcat SK-MH, Softcat SX-400X, Softcat SX-400H, SoftCat SK-L, Softcat SK-M, and Softcat SK-H, sold by the company Amerchol and the products Crodacel QM, Crodacel, QL (C 12 alkyl) and Crodacel QS (C 18 alkyl) sold by the company Croda.
  • Quatrisoft LM 200 Quatrisoft LM-X 5
  • the products corresponding to INCI name Polyquaternium-67 are preferred.
  • the cationic cellulose derivatives could also be chosen among cationic cellulose ether(s), comprising from 4 000 to 10 000 anhydroglucose units, said anhydroglucose units being substituted with at least:
  • R4 and R 5 represent, independently of one another, a methyl or ethyl group
  • R 6 represents a linear or branched C 8 -C 24 alkyl group or an aralkyl group in which the linear or branched alkyl part is C 8 -C 24 ,
  • R9 represents a divalent group which allows the attachment to the anhydroglucose group and which is chosen from -(B) q -CH 2 -CHOH-CH 2 - and -CH 2 CH 2 -,
  • n' being an integer ranging from 1 to 100
  • X 2 " represents an anion
  • R 1 , R 2 and R 3 represent, independently of one another, a methyl or ethyl group
  • R 8 represents a divalent group which allows the attachment to the anhydroglucose group and which is chosen from -(A) p -CH 2 -CHOH-CH 2 - and -CH 2 CH 2 -,
  • n an integer ranging from 1 to 100
  • Xf represents an anion.
  • the substituent (i) of formula [R 4 R 5 R6R9N + ](X 2 " ) is present at an average of from 0.0003 to 0.08 mol, per mole of anhydroglucose units.
  • the cationic cellulose ethers that can be used in the compositions according to the present invention are preferably hydroxyethyl celluloses or hydroxypropyl celluloses.
  • the cationic cellulose ethers that can be used in the compositions according to the present invention preferably comprise more than 4500, advantageously more than 5000, and more preferably more than 6000 anhydroglucose units.
  • the cationic cellulose ethers that can be used in the compositions according to the present invention preferably comprise up to 9000, and preferably up to 8000 anhydroglucose units.
  • the cationic cellulose ethers that can be used in the compositions according to the present invention are formed from at least one unit (IV) and at least one of the following units (I), (II) and (III): with the proviso that:
  • the total number of units (I)+(II)+(III)+(IV) is between 4000 and 10 000;
  • n and n' independently of one another, range from 0 to 5;
  • Ri, R 2 , R 3 , R 4 and R 5 represent, independently of one another, a methyl or ethyl group
  • R 6 represents a linear or branched C 8 -C 24 , preferably Ci 0 -C 24 , more preferably Ci 2 -C 24 and better still Ci 2 -C 15 , alkyl group or an aralkyl group in which the linear or branched alkyl part is C8-C24;
  • Xi " and X 2 " represent anions preferably chosen, independently of one another, from phosphate, nitrate, sulphate and halide (CI “ , Br “ , F “ , ⁇ ) ions.
  • the cationic cellulose ethers that can be used in the compositions according to the present invention are formed from at least one unit (IV) and at least one of the units (I), (II) or (III) above, in which R 6 is a linear dodecyl group.
  • the cationic cellulose ethers that are particularly preferred are the polymers of SL-60 and SL- 100 type.
  • Cationic cellulose derivatives such as cellulose copolymers and cellulose derivatives grafted with a water-soluble monomer of quaternary ammonium, and described, for example, in U.S. Pat. No. 4,131,576, such as hydroxyalkylcelluloses, for instance, hydroxymethyl-, hydroxyethyl-, and hydroxypropylcelluloses grafted, for example, with a salt chosen from methacryloylethyltrimethylammonium, methacrylamidopropyltrimethylammonium, and dimethyldiallylammonium salts.
  • Non-cellulose-based cationic polysaccharides described in U.S. Pat. Nos. 3,589,578 and 4,031,307 such as guar gums comprising cationic trialkylammonium groups, cationic hyaluronic acid, and dextran hydroxypropyl trimonium chloride.
  • Guar gums modified with a salt, for example the chloride, of 2,3-epoxypropyltrimethylammonium (guar hydroxypropyltrimonium chloride) may also be used.
  • Such products are sold, for instance, under the trade names JAGUAR® C13 S, JAGUAR® C15, JAGUAR® C17, and JAGUAR® C162 by the company MEYHALL.
  • Polymers comprising piperazinyl units and divalent alkylene or hydroxyalkylene groups comprising straight or branched chains, optionally interrupted with at least one entity chosen from oxygen, sulphur, nitrogen, aromatic rings, and heterocyclic rings, and also the oxidation and/or quaternization products of these polymers.
  • Such polymers are described, for example, in French Patent Nos. 2 162 025 and 2 280 361.
  • Water-soluble polyamino amides prepared, for example, by polycondensation of an acidic compound with a polyamine; these polyamino amides possibly being crosslinked with an entity chosen from epihalohydrins; diepoxides; dianhydrides; unsaturated dianhydrides; bisunsaturated derivatives; bishalohydrins; bisazetidiniums; bishaloacyidiamines; bisalkyl halides; oligomers resulting from the reaction of a difunctional compound which is reactive with an entity chosen from bishalohydrins, bisazetidiniums, bishaloacyldiamines, bisalkyl halides, epihalohydrins, diepoxides, and bisunsaturated derivatives; the crosslinking agent being used in an amount ranging from 0.025 to 0.35 mol per amine group of the polyamino amide; these polyamino amides optionally being alkylated or, if they comprise at least one
  • difunctional agents for example, adipic acid/dialkylaminohydroxyalkyldialkylenetriamine polymers in which the alkyl group comprises from 1 to 4 carbon atoms, such as methyl, ethyl, and propyl groups, and the alkylene group comprises from 1 to 4 carbon atoms, such as an ethylene group.
  • adipic acid/dialkylaminohydroxyalkyldialkylenetriamine polymers in which the alkyl group comprises from 1 to 4 carbon atoms, such as methyl,
  • the molar ratio of the polyalkylene polyamine to the dicarboxylic acid may range from 0.8:1 to 1.4: 1 ; the polyamino amide resulting therefrom being reacted with epichlorohydrin in a molar ratio of epichlorohydrin relative to the secondary amine group of the polyamino amide ranging from 0.5:1 to 1.8:1.
  • Such polymers are described, for example, in U.S. Pat. Nos. 3,227,615 and 2,961,347.
  • Ri2 is chosen from hydrogen and methyl groups
  • R 10 and Rn which may be identical or different, are chosen from alkyl groups comprising from 1 to 6 carbon atoms, hydroxyalkyl groups in which the alkyl group comprises, for example, from 1 to 5 carbon atoms, and lower (Ci-C 4 )amidoalkyl groups, or Rio and Rn may form, together with the nitrogen atom to which they are attached, heterocyclic groups such as piperidinyl and morpholinyl; and
  • Y' is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulphate, bisulphite, sulphate, and phosphate.
  • Rio and Rn which may be identical or different, are chosen from alkyl groups comprising from 1 to 4 carbon atoms.
  • polymers include, but are not limited to, (co)polydiallyldialkyl ammonium chloride such as the dimethyldiallylammonium chloride homopolymer (INCI: Polyquaternium-6) sold under the name "MERQUAT® 100" by the company CALGON (and its homologues of low weight-average molecular mass) and the copolymers of diallyldimethylammonium chloride and of acrylamide (INCI: Polyquaternium-7) sold under the name "MERQUAT® 550".
  • (co)polydiallyldialkyl ammonium chloride such as the dimethyldiallylammonium chloride homopolymer (INCI: Polyquaternium-6) sold under the name "MERQUAT® 100" by the company CALGON (and its homologues of low weight-average molecular mass) and the copolymers of diallyldimethylam
  • Ri3, Ri4, Ri5, and R 16 which may be identical or different, are chosen from aliphatic, alicyclic, and arylaliphatic groups comprising from 1 to 20 carbon atoms and lower hydroxyalkyl aliphatic groups, or alternatively Ri 3 , Ri 4 , R 15 , and Ri 6 may form, together or separately, with the nitrogen atoms to which they are attached, heterocycles optionally comprising a second heteroatom other than nitrogen, or alternatively Ri 3 , Ri 4 , Ris, and Ri 6 , which may be identical or different, are chosen from linear or branched Ci-C 6 alkyl groups substituted with at least one group chosen from nitrile groups, ester groups, acyl groups, amide groups, -CO-O-Rn-E groups, and -CO-NH-R17-E groups, wherein Rn is an alkylene group and E is a quaternary ammonium group;
  • Ai and Bi which may be identical or different, are chosen from polymethylene groups comprising from 2 to 20 carbon atoms, which may be linear or branched, saturated or unsaturated, and which may comprise, linked or intercalated in the main chain, at least one entity chosen from aromatic rings, oxygen, sulphur, sulphoxide groups, sulphone groups, disulphide groups, amino groups, alkylamino groups, hydroxyl groups, quaternary ammonium groups, ureido groups, amide groups, and ester groups, and
  • X " is an anion derived from an inorganic or organic acid; Ai, Rn, and R 15 may form, together with the two nitrogen atoms to which they are attached, a piperazine ring;
  • Bi may be chosen from: -(CH 2 ) n -CO-E'-OC-(CH 2 )n- wherein E' is chosen from:
  • x and y which may be identical or different, are chosen from integers ranging from 1 to 4, which represent a defined and unique degree of polymerization, and numbers ranging from 1 to 4, which represent an average degree of polymerization;
  • X " is an anion such as chloride or bromide.
  • Polymers of this type are described, for example, in French Patent Nos. 2 320 330; 2 270 846; 2 316 271; 2 336 434; and 2 413 907 and U.S. Pat. Nos. 2,273,780; 2,375,853; 2,388,614; 2,454,547; 3,206,462; 2,261,002; 2,271,378; 3,874,870; 4,001,432; 3,929,990; 3,966,904; 4,005,193; 4,025,617; 4,025,627; 4,025,653; 4,026,945; and 4,027,020.
  • Non-limiting examples of such polymers include those comprising at least one repeating unit of formula (VII):
  • Ri 3 , Ri 4 , Ris, and Ri 6 which may be identical or different, are chosen from alkyl and hydroxyalkyl groups comprising from 1 to 4 carbon atoms, n and p, which may be identical or different, are integers ranging from 2 to 20, and X " is an anion derived from an inorganic or organic acid.
  • Ri8, Ri9, R20, and R 2 i which may be identical or different, are chosen from hydrogen, methyl groups, ethyl groups, propyl groups, ⁇ -hydroxyethyl groups, ⁇ -hydroxypropyl groups, -CH 2 CH 2 (OCH 2 CH 2 ) p OH groups, wherein p is chosen from integers ranging from 0 to 6, with the proviso that R 18 , R19, R20, and R 2 i are not simultaneously hydrogen,
  • r and s which may be identical or different, are chosen from integers ranging from 1 to 6
  • q is chosen from integers ranging from 0 to 34
  • X " is an anion such as a halide
  • A is chosen from radicals of dihalides and -CH 2 -CH 2 -0-CH 2 -CH 2 -.
  • Quaternary polymers of vinylpyrrolidone and of vinylimidazole include, but are not limited to, cationic proteins and cationic protein hydrolysates, polyalkyleneimines, such as polyethyleneimines, polymers comprising units chosen from vinylpyridine and vinylpyridinium units, condensates of polyamines and of epichlorohydrin, quaternary polyureylenes, and chitin derivatives.
  • the at least one cationic polymer is chosen from cellulose ether derivatives comprising quaternary ammonium groups, such as the product sold under the name "JR 400" by the company UNION CARBIDE CORPORATION, cationic cyclopolymers, for instance, the homo-polymers and copolymers of dimethyldiallylammonium chloride sold under the names MERQUAT® 100, MERQUAT® 550, and MERQUAT® S by the company CALGON, guar gums modified with a 2,3-epoxypropyltrimethylammonium salt, and quaternary polymers of vinylpyrrolidone and of vinylimidazole. (13) Polyamines
  • (co)polyamines which may be homopolymers or copolymers, with a plurality of amino groups.
  • the amino group may be a primary, secondary, tertiary or quaternary amino group.
  • the amino group may be present in a polymer backbone or a pendent group, if present, of the (co)polyamines.
  • (co)polyamines examples include chitosan, (co)polyallylamines, (co)polyvinylamines, (co)polyanilines, (co)polyvinylimidazoles,
  • (co)polydimethylaminoethylenemethacrylates (co)polyvinylpyridines such as (co)poly-l-methyl-2-vinylpyridines, (co)polyimines such as (co) polyethyleneimines, (co)polypyridines such as (co)poly(quaternary pyridines), (co)polybiguanides such as (co)polyaminopropyl biguanides, (co)polylysines, (co)polyornithines, (co)polyarginines, (co)polyhistidines, aminodextrans, aminocelluloses, amino(co)polyvinylacetals, and salts thereof.
  • polylysine As the (co)polyamines, it is preferable to use (co)polylysines.
  • Polylysine is well known. Polylysine can be a natural homopolymer of L-lysine that can be produced by bacterial fermentation. For example, polylysine can be ⁇ -Poly-L-lysine, typically used as a natural preservative in food products. Polylysine is a polyelectrolyte which is soluble in polar solvents such as water, propylene glycol and glycerol. Polylysine is commercially available in various forms, such as poly D-lysine and poly L-lysine. Polylysine can be in salt and/or solution form.
  • cationic polyaminoacids which may be cationic homopolymers or copolymers, with a plurality of amino groups and carboxyl groups.
  • the amino group may be a primary, secondary, tertiary or quaternary amino group.
  • the amino group may be present in a polymer backbone or a pendent group, if present, of the cationic polyaminoacids.
  • the carboxyl group may be present in a pendent group, if present, of the cationic polyaminoacids.
  • cationic polyaminoacids mention may be made of cationized collagen, cationized gelatin, steardimonium hydroxypropyl hydrolyzed wheat protein, cocodimonium hydroxypropyl hydrolyzed wheat protein, hydroxypropyltrimonium hydrolyzed conchiolin protein, steardimonium hydroxypropyl hydrolyzed soy protein, hydroxypropyltrimonium hydrolyzed soy protein, cocodimonium hydroxypropyl hydrolyzed soy protein, and the like.
  • the cationic polymer be selected from the group consisting of cyclopolymers of alkyldiallylamine and cyclopolymers of dialkyldiallylammonium such as (co)polydiallyldialkyl ammonium chloride, (co)polyamines such as (co)polylysines, cationic (co)polyaminoacids such as cationized collagen, and salts thereof.
  • the (b) cationic polymer be a polyquaternium polymer or a polymeric quaternary ammonium salt.
  • Polymeric quaternary ammonium salts are cationic polymers comprising at least one quaternized nitrogen atom. Mention may in particular be made, as polymeric quaternary ammonium salts, of the Polyquaternium products (CTFA name), which contribute mainly to the quality of foam and feeling of the skin after use, in particular the feeling of the skin after use.
  • CTFA name Polyquaternium products
  • These polymers can preferably be chosen from the following polymers:
  • Polyquaternium-5 such as the product Merquat 5 sold by Nalco;
  • Polyquaternium-6 such as the product Salcare SC 30 sold by BASF and the product Merquat 100 sold by Nalco;
  • Polyquaternium-7 such as the products Merquat S, Merquat 2200, Merquat 7SPR, and Merquat 550 sold by Nalco and the product Salcare SC 10 sold by BASF;
  • Polyquaternium- 11 such as the products Gafquat 755, Gafquat 755N and Gafquat 734 sold by ISP;
  • Polyquaternium- 16 such as the products Luviquat FC905, Luviquat FC370, Luviquat HM552 and Luviquat FC550 sold by BASF;
  • Polyquaternium-28 such as the product Styleze CC10 sold by ISP;
  • Polyquaternium-44 such as the product Luviquat Care sold by BASF;
  • Polyquaternium-46 such as the product Luviquat Hold sold by BASF.
  • Polyquaternium-47 such as the product Merquat 2001 sold by Nalco.
  • the (b) cationic polymer can be selected from the copolymers of families (1), (2), and (9), and any combinations thereof.
  • the (b) cationic polymer comprises at least the copolymers of family (1).
  • the (b) cationic polymer comprises the copolymers of families (2) and/or (9) in addition to the copolymers of family (1).
  • the (b) cationic polymer comprises Polyquaternium-11.
  • the (b) cationic polymer may be present in a content of 0.5% by weight or more, preferably 1% by weight or more, and more preferably 1.5% by weight or more, relative to the total weight of the composition.
  • the (b) cationic polymer may be present in a content of 30% by weight or less, preferably 20% by weight or less, and more preferably 15% by weight or less, ' relative to the total weight of the composition.
  • the (b) cationic polymer may be present in a content ranging from 0.5% to 30% by weight, preferably from 1% to 20% by weight, and more preferably from 1.5% to 15% by weight, relative to the total weight of the composition.
  • the pH of the composition according to the present invention may be adjusted to the desired value using acidifying or basifying agents commonly used in the technical field of coloring keratin fibers.
  • the pH of the composition according to the present invention may be preferably from 1 to 6, more preferably from 2 to 5, and even more preferably from 2 to 4, and most preferably from 2 to 3.
  • acidifying agents mention may be made, by way of example, of mineral or organic acids such as hydrochloric acid, ortho-phosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, and lactic acid, and sulfonic acids.
  • mineral or organic acids such as hydrochloric acid, ortho-phosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, and lactic acid, and sulfonic acids.
  • basifying agents mention may be made, by way of example, of sodium hydroxide, ammonium hydroxide, alkali metal carbonates, alkanolamines such as mono-, di- and triethanolamines and also their derivatives, sodium or potassium hydroxide and compounds of the formula below:
  • W denotes an alkylene such as propylene optionally substituted by a hydroxyl or a Ci-C 4 alkyl radical
  • a , Rb, Rc and a independently denote a hydrogen atom, an alkyl radical or a d-C 4 hydroxyalkyl radical, which may be exemplified by 1,3-propanediamine and
  • Sodium or potassium hydroxide may also be preferable.
  • the acidifying or basifying agent may be used in an amount ranging from 0.001 to 15%) by weight, preferably from 0.01 to 10%) by weight, and more preferably from 0.1 to 5% by weight, relative to the total weight of the composition.
  • the composition according to the present invention may preferably comprise propylene glycol.
  • the use of propylene glycol may be preferable since it can improve the volumizing effect of keratin fibers of the present invention.
  • the amount of the propylene glycol included in the composition according to the present invention is not limited, but may be from 0.01 to 30% by weight, preferably from 0.1 to 25% by weight, and more preferably from 1 to 20% by weight relative to the total weight of the composition according to the present invention.
  • composition according to the present invention may comprise at least one oxidizing agent.
  • the oxidizing agent may be chosen from hydrogen peroxide, peroxygenated salts, and compounds capable of producing hydrogen peroxide by hydrolysis.
  • the oxidizing agent can be chosen from aqueous hydrogen peroxide solution, urea peroxide, alkali metal bromates and ferricyanides and persalts such as perborates and persulphates.
  • At least one oxidase enzyme chosen, for example, from laccases, peroxidases and 2-electron oxidoreductases such as uricase may also be used as the oxidizing agent, where appropriate in the presence of the respective donor or co-factor thereof.
  • the oxidizing agent is hydrogen peroxide, such as an aqueous hydrogen peroxide solution.
  • the hydrogen peroxide concentration may range from 0.15 wt% to 12 wt% such as from 0.6 wt% to 9 wt% relative to the total weight of the (c) oxidizing agent.
  • the concentration of compounds capable of forming hydrogen peroxide by hydrolysis may range from 0.1 wt% to 25 wt% relative to the total weight of the oxidizing agent.
  • the aqueous solution may comprise at least one hydrogen peroxide stabilizer, which may be chosen, for example, from alkali metal and alkaline-earth metal pyrophosphates, alkali metal and alkaline-earth metal stannates, phenacetin and salts of acids and of oxyquinoline, for example, oxyquinoline sulphate.
  • at least one stannate optionally in combination with at least one pyrophosphate is used.
  • concentration of the hydrogen peroxide stabilizer may range from 0.0001 wt% to 5 wt% such as from 0.01 wt% to 2 wt% relative to the total weight of the (c) oxidizing agent.
  • the amount of the oxidizing agent in the composition according to the present invention may range from 0.01% to 30% by weight, preferably from 0.1% to 20% by weight, and more preferably from 1% to 10% by weight, relative to the total weight of the composition.
  • the composition according to the present invention may comprise water.
  • the amount of water in the composition according to the present invention may range from 50% to 99% by weight, preferably from 60% to 95% by weight, and more preferably from 70 to 90% by weight, relative to the total weight of the composition.
  • composition according to the present invention may also contain various adjuvants conventionally used in compositions for coloring keratin fibers such as hair, such as oils, anionic, non-ionic, cationic, amphoteric or zwitterionic surfactants, or mixtures thereof, antioxidants, thickening agents, sequestering agents, fragrances, dispersing agents, conditioning agents, film-forming agents, ceramides, preservatives, for example, phenoxy ethanol, and opacifying agents.
  • adjuvants conventionally used in compositions for coloring keratin fibers such as hair such as oils, anionic, non-ionic, cationic, amphoteric or zwitterionic surfactants, or mixtures thereof, antioxidants, thickening agents, sequestering agents, fragrances, dispersing agents, conditioning agents, film-forming agents, ceramides, preservatives, for example, phenoxy ethanol, and opacifying agents.
  • the amount of the adjuvants included in the composition according to the present invention is not limited, but may be from 0.01 to 30% by weight relative to the total weight of the composition according to the present invention.
  • the form of the composition according to the present invention is not particularly limited, as long as it is water-based, and may take various forms such as an emulsion (O/W or W/O form), an aqueous gel, an aqueous solution, or the like. It is preferable that the composition according to the present invention be in the form of a water-based solution.
  • the composition according to the present invention can be used as a conditioning or a booster composition for use in coloring keratin fibers, for example by dyeing or bleaching the keratin fibers.
  • the composition according to the present invention can be a cosmetic composition used in combination with compositions for coloring for keratin fibers, such as a composition including at least one oxidizing agent, a composition including at least one alkaline agent, or a combination thereof.
  • composition according to the present invention including the combination of the (a) malonic acid and the (b) cationic polymer can be used in combination with another composition including at least one oxidizing agent.
  • composition including at least one oxidizing agent is referred to as first composition.
  • the oxidizing agent(s) which can be used in the first composition is (are) the same as explained above.
  • the first composition may comprise the oxidizing agent(s) in an amount of 0.01% to 30% by weight, preferably 0.1% to 20% by weight, and more preferably 1% to 10% by weight, relative to the total weight of the composition.
  • composition Including Alkaline Agent The composition according to the present invention further including the oxidizing agent(s) can be used in combination with another composition including at least one alkaline agent.
  • composition including at least one alkaline agent is referred to as second composition.
  • the second composition comprises at least one alkaline agent.
  • a single type of alkaline agent may be used, or two or more different types of alkaline agents may be used in combination.
  • alkaline agents mention may be made of any inorganic or organic basic agents which are commonly used in cosmetic products such as ammonia; alkanolamines such as mono-, di- and tri-ethanolamine, isopropanolamine; sodium and potassium hydroxides; urea, guanidine and their derivatives; basic amino acids such as lysine or arginine; and diamines such as those described in the structure below:
  • R / R £ wherein R denotes an alkylene such as propylene optionally substituted by a hydroxyl or a C 1 -C 4 alkyl radical, and R3, R 4 , R5 and R 6 independently denote a hydrogen atom, an alkyl radical or a Ci-C 4 hydroxyalkyl radical, which may be exemplified by 1 ,3-propanediamine and derivatives thereof. Arginine and monoethanolamine are preferred.
  • the alkaline agent may be used in an amount ranging from 0.001 to 15% by weight, preferably from 0.01 to 10% by weight, and more preferably from 0.1 to 5% by weight, relative to the total weight of the composition.
  • the second composition may comprise at least one oxidation dye.
  • a single type of oxidation dye may be used, or two or more different types of oxidation dyes may be used in
  • the oxidation dye can be selected from oxidation bases, oxidation couplers, and the acid addition salts thereof.
  • the oxidation base can be selected from those conventionally known in oxidation dyeing, preferably from the group consisting of ortho- and para-phenylenediamines, double bases, ortho- and para-aminophenols, heterocyclic bases and the acid addition salts thereof.
  • Ri represents a hydrogen atom, a d-C 4 alkyl radical, a monohydroxy(C!-C 4 alkyl) radical, a polyhydroxy-(C 2 -C4 alkyl) radical, a (C 1 -C 4 )alkoxy(C 1 -C 4 )alkyl radical, a d-C 4 alkylradical substituted with a nitrogen-containing group, a phenyl radical or a 4'-aminophenyl radical;
  • R 2 represents a hydrogen atom, a C1-C4 alkyl radical, a monohydroxy(Ci-C 4 alkyl) radical, a polyhydroxy(C 2 -C 4 alkyl) radical, a (C 1 -C 4 )alkoxy(C 1 -C 4 )alkyl radical or a Ci-C 4 alkyl radical substituted with a nitrogen-containing group;
  • Ri and R 2 may also form with the nitrogen atom carrying them a 5- or 6-membered nitrogen-containing heterocycle optionally substituted with one or more alkyl, hydroxyl or ureido groups;
  • R 3 represents a hydrogen atom, a halogen atom such as a chlorine atom, a Ci-C 4 alkyl radical, a sulpho radical, a carboxyl radical, a monohydroxy(C!-C 4 alkyl) radical, a hydroxy(Ci-C 4 alkoxy) radical, an acetylamino(C!-C 4 alkoxy) radical, a mesylamino(Ci-C 4 alkoxy) radical or a carbamoylamino(d-C 4 alkoxy) radical; and
  • a halogen atom such as a chlorine atom, a Ci-C 4 alkyl radical, a sulpho radical, a carboxyl radical, a monohydroxy(C!-C 4 alkyl) radical, a hydroxy(Ci-C 4 alkoxy) radical, an acetylamino(C!-C 4 alkoxy) radical, a mesylamino(Ci-C 4 alk
  • R 4 represents a hydrogen or halogen atom or a C1-C4 alkyl radical.
  • nitrogen-containing groups of formula (I) above there may be mentioned in particular the amino, mono(Ci-C4)alkylamino, (Ci -C 4 )dialkylamino, (Ci-C 4 )trialkylamino, monohydroxy(Ci-C 4 )alkylamino, di(monohydroxy(Ci-C 4 )alkyl)amino, imidazolinium and ammonium radicals.
  • para-phenylenediamines of formula (I) above there may be mentioned more particularly para-phenylenediamine, para-tolylenediamine, 2-chloro-paraphenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine,
  • N-( -hydroxypropyl)-paraphenylenediamine 2-hydroxymethyl-para-phenylenediamine, N,N-dimethyl-3-methylpara-phenylenediamine,
  • N-(4'-aminophenyl)-para-phenylenediamine N-phenyl-para-phenylenediamine
  • para-phenylenediamines of formula (I) above there are most particularly preferred para-phenylenediamine, para-tolylenediamine, 2-isopropyl-paraphenylenediamine, 2- -hydroxyethyl-para-phenylenediamine, 2-P-hydroxyethyloxy-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine,
  • double bases is understood to mean compounds containing at least two aromatic rings on which amino and/or hydroxyl groups are carried.
  • double bases which can be used as oxidation bases in the dyeing compositions in accordance with the present invention, there may be mentioned in particular compounds corresponding to the following formula (II), and their addition salts with an acid:
  • - Zi and Z 2 which are identical or different, represent a hydroxyl or -NH 2 radical which may be substituted with a Ci-C 4 alkyl radical or with a linking arm Y;
  • the linking arm Y represents a linear or branched alkylene chain comprising from 1 to 14 carbon atoms, which may be interrupted by or which may end with one or more
  • nitrogen-containing groups and/or one or more heteroatoms such as oxygen, sulphur or nitrogen atoms, and optionally substituted with one or more hydroxyl or Ci-C 6 alkoxy radicals;
  • R.5 and R 6 represent a hydrogen or halogen atom, a C1-C4 alkyl radical, a
  • Ri 3 represents a hydrogen atom, or a halogen atom such as fluorine, a Ci-C 4 alkyl, monohydroxy(Ci-C 4 alkyl), (Ci-C4)alkoxy(C 1 -C 4 )-alkyl, amino(Ci-C4 alkyl) or
  • - Ri4 represents a hydrogen atom, or a halogen atom such as fluorine, a Ci-C 4 alkyl, monohydroxy(G-C 4 alkyl), polyhydroxy(C 2 -C 4 alkyl), amino(Ci-C 4 alkyl), cyano(Ci-C 4 alkyl) or (C 1 -C 4 )alkoxy(Ci-C 4 )alkyl radical.
  • para-aminophenols of formula (III) above there may be mentioned more particularly para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol,
  • heterocyclic bases which can be used as oxidation bases in the dyeing compositions in accordance with the present invention, there may be mentioned more particularly pyridine derivatives, pyrimidine derivatives, pyrazole derivatives, and their addition salts with an acid.
  • pyrimidine derivatives there may be mentioned more particularly the compounds described, for example, in Patents DE 2 359 399; JP 88-169571 ; and JP 91-10659 or patent application WO 96/15765, such as 2,4,5, 6-tetraaminopyrimidine,
  • heterocyclic bases which can be used as oxidation bases, there may be mentioned more particularly diaminopyrazolopyrazolones and especially
  • the oxidation dye may be an oxidation coupler which can be selected from those
  • heterocyclic couplers may be selected from the group consisting of indole derivatives, indoline derivatives, sesamol and its derivatives, pyridine derivatives, pyrazolotriazole derivatives, pyrazolones, indazoles, benzimidazoles, benzothiazoles, benzoxazoles,
  • 1,3-benzodioxoles, quinolines and their addition salts with an acid are more particularly chosen from 2,4-diamino-l-(P-hydroxyethyloxy)benzene, 2-methyl-5-aminophenol, 5-N-( -hydroxyethyl)amino-2-methylphenol, 3-aminophenol, 2-chloro-3-amino-6-methylphenol, 1 ,3-dihydroxybenzene, 1 ,3-dihydroxy-2-methylbenzene,
  • the addition acid salts of the oxidation bases and couplers are chosen in particular from hydrochlorides, hydrobromides, sulphates, tartrates, lactates and acetates.
  • the second composition may comprise an oxidation dye or dyes in an amount of 0.0001 to 20 wt%, preferably 0.0005 to 15 wt%, and more preferably 0.005 to 10 wt%, relative to the total weight of the composition.
  • the first and second compositions may also contain various adjuvants conventionally used in compositions for coloring keratin fibers such as hair, such as oils, anionic, non-ionic, cationic, amphoteric or zwitterionic surfactants, or mixtures thereof, anionic, non-ionic, cationic, amphoteric or zwitterionic polymers, or mixtures thereof, antioxidants, neutralizers, thickening agents, sequestering agents, stabilizers, pH adjusting agents, fragrances, dispersing agents, conditioning agents, film-forming agents, ceramides, preservatives and opacifying agents.
  • the first and second compositions may comprise water.
  • the amount of water in the first and second compositions may range from 50% to 99% by weight, preferably from 60% to 95% by weight, and more preferably from 70 to 90% by weight, relative to the total weight of the composition.
  • the form of the first and second compositions is not particularly limited, as long as it is water-based, and may take various forms such as an emulsion (O/W or W/O form), an aqueous gel, an aqueous solution, or the like. It is preferable that the first and second compositions be in the form of a water-based solution.
  • composition according to the present invention can be prepared by mixing the ingredients (a) and (b), as essential ingredients, and optional ingredient(s), if necessary, as explained above.
  • the composition according to the present invention can be mixed with the first composition for its use.
  • the first composition can be prepared by mixing oxidizing agent(s), as essential ingredient(s), and optional ingredient(s), if necessary, as explained above.
  • the mixing ratio of the composition according to the present invention and the first composition is not limited.
  • the mixing ratio may be 1 :50 to 1 : 1, preferably 1 :40 to 1 :2, and more preferably 1 :30 to 1 :5, as weight ratio.
  • the composition according to the present invention can be mixed with the first and second compositions for its use.
  • the second composition can be prepared by mixing the alkaline agent(s), as essential ingredient(s), and optional ingredient(s), if necessary, as explained above.
  • the mixing ratio of the composition according to the present invention, the first composition, and the second composition is not limited.
  • the mixing ratio may be 1 :50:50 to 1 : 1 :1, preferably 1 :40:40 to 1 :2:2, and more preferably 1 :30:30 to 1 :5:5, as weight ratio.
  • the method and means to mix the above essential and optional ingredients are not limited. Any conventional method and means can be used to mix the above essential and optional ingredients to prepare the first or second composition.
  • the present invention also relates to a ready-to-use cosmetic composition for keratin fibers, preferably hair, comprising:
  • the first composition comprising at least one oxidizing agent
  • the second composition comprising at least one alkaline agent.
  • the ready-to-use composition according to the present invention can be applied, as it is, to keratin fibers such as hair, for coloring the keratin fibers by, for example, dyeing or bleaching the keratin fibers.
  • the ready-to-use composition according to the present invention can be prepared by mixing the composition according to the present invention, the first composition, and the second composition.
  • the mixing ratio of the composition according to the present invention, the first composition, and the second composition is not limited.
  • the mixing ratio may be 1 :50:50 to 1 :1 : 1, preferably 1 :40:40 to 1 :2:2, and more preferably 1 :30:30 to 1 :5:5, as weight ratio.
  • the (a) malonic acid may be present in the ready-to-use composition according to the present invention in an amount of 0.005% by weight or more, preferably 0.025% by weight or more, and more preferably 0.05% by weight or more, relative to the total weight of the composition.
  • the (a) malonic acid may be present in the ready-to-use composition according to the present invention in an amount of 1% by weight or less, preferably 0.75% by weight or less, and more preferably 0.5% by weight or less, relative to the total weight of the composition.
  • the amount of the (a) malonic acid in the ready-to-use composition according to the present invention may range from 0.005% to 1% by weight, preferably from 0.025% to 0.75% by weight, and more preferably from 0.05% to 0.5% by weight, relative to the total weight of the composition.
  • the (b) cationic polymer may be present in the ready-to-use composition according to the present invention in an amount of 0.025% by weight or more, preferably 0.05% by weight or more, and more preferably 0.075% by weight or more, relative to the total weight of the composition.
  • the (b) cationic polymer may be present in the ready-to-use composition according to the present invention in an amount of 1.5% by weight or less, preferably 1% by weight or less, and more preferably 0.75% by weight or less, relative to the total weight of the composition.
  • the amount of the (b) cationic polymer present in the ready-to-use composition may range from 0.025% to 1.5% by weight, preferably from 0.05% to 1% by weight, and more preferably from 0.075% to 0.75% by weight, relative to the total weight of the composition.
  • the present invention also relates to a kit for keratin fibers, preferably hair, comprising: a first compartment comprising the first composition comprising at least one oxidizing agent, a second compartment comprising the second composition comprising at least one alkaline agent, and
  • a third compartment comprising the composition according to the present invention. It is possible to use the kit by, for example, dispensing or discharging the first composition from the first compartment, while dispensing or discharging the second composition from the second compartment and/or dispensing or discharging the composition according to the present invention from the third compartment, followed by treating keratin fibers such as hair with the mixture of the first and second compositions and the composition according to the present invention.
  • the composition according to the present invention can be mixed with at least one oxidizing agent before it is charged in a compartment of the kit. Therefore, the present invention also relates to a kit for keratin fibers, preferably hair, comprising:
  • a first compartment comprising the composition according to the present invention pre-mixed with at least one oxidizing agent
  • a second compartment comprising the second composition comprising at least one alkaline agent.
  • the present invention also relates to a cosmetic process for keratin fibers, preferably hair, comprising the steps of:
  • the first composition comprising at least one oxidizing agent
  • the second composition comprising at least one alkaline agent to prepare the ready-to-use cosmetic composition
  • the cosmetic process according to the present invention comprise a step of washing, with or without drying, keratin fibers before and/or after the step of applying the ready-to-use cosmetic composition onto the keratin fibers.
  • the step of applying the ready-to-use cosmetic composition onto the keratin fibers can be performed by a conventional applicator such as a brush, or even by the hands.
  • the keratin fibers to which the ready-to-use cosmetic composition has been applied can be left for an appropriate time which is required to treat the keratin fibers.
  • the time length for the treatment is not limited, but it may be from 1 minute to 1 hour, preferably 1 minute to 30 minutes, and more preferably 1 minute to 15 minutes.
  • the time for dyeing the keratin fibers may be from 1 to 20 minutes, preferably 5 to 15 minutes.
  • the keratin fibers may be treated at room temperature.
  • the keratin fibers can be heated at 25°C to 65°C, preferably 30°C to 60°C, more preferably 35°C to 55°C, and even more preferably 40°C to 50°C, before and/or during and/or after the step of applying the ready-to-use cosmetic composition onto the keratin fibers.
  • the present invention may also relate to a use of a combination of:
  • compositions for coloring or bleaching keratin fibers preferably in a composition for coloring keratin fibers comprising at least one oxidizing agent to prevent or reduce the loss of volume of keratin fibers when the keratin fibers are colored with the above composition for keratin fibers, with or without another composition including at least one alkaline agent, and/or when the colored keratin fibers are washed.
  • the above coloring is preferably for cosmetic purposes for the keratin fibers, for example, dyeing or bleaching the keratin fibers, preferably hair.
  • Example ⁇ Example 1
  • Comparative Examples 1 to 3 Comparative Examples 1 to 3
  • Table 1 The numerical values for the amounts of the ingredients are all based on "% by weight" as active raw materials.
  • Polyquaternium-11 was purchased from the company I.S.P. (Ashland).
  • Three hair swatches (1 g, 20 cm) were prepared for each experiment. 4 g of the mixture obtained as above was applied onto 1 g of hair swatch for each sample. The swatch was then left for 30 minutes at room temperature, followed by shampooing and rinsing with tap water. The swatch was hung downwardly and dried at 25 °C under relative humidity of 30-50% over night. The dried swatch was cut such that the length between the root of the swatch and the cut point (tip of the swatch) was 15 cm. The root of the swatch was fixed on a plate. On the other hand, the tip of the swatch was held and oriented upwardly, and the tip of the swatch was then released such that the tip of the swatch could point downwardly. The vertical angle between the plate and the tip of the hair fiber was measured (cf. Fig. 1). The average value of the three swatches was determined for the vertical angle with regard to the hair fibers in the swatch.
  • the measured vertical angle was evaluated in accordance with the evaluation criteria shown below.
  • the swatch used in the evaluation of the above "Volumizing Effects” was shampooed five times.
  • the swatch was hung downwardly and dried overnight at 25 °C under relative humidity of 30-50%.
  • the root of the swatch was fixed on a plate.
  • the tip of the swatch was held and oriented upwardly, and the tip of the swatch was then released such that the tip of the swatch could point downwardly.
  • the vertical angle between the plate and the tip of the hair fiber was measured (cf. Fig. 1).
  • the average value of the three swatches was determined for the vertical angle with regard to the hair fibers in the swatch.
  • the measured vertical angle was evaluated in accordance with the evaluation criteria shown below.
  • Example 1 it can be recognized from the comparisons of Example 1 and Comparative Examples 1 to 3, shown in Table 1 , that, when a composition for keratin fibers such as hair contains malonic acid and a cationic polymer such as polyquaternium- 11, the composition can improve both volumizing and long-lasting effects.
  • the composition according to Comparative Example 1, which does not include malonic acid showed good long lasting effects but did not show good volumizing effects.
  • Comparative Example 2 which includes citric acid instead of malonic acid, did not show good volumizing effects and showed inferior long lasting effects.
  • composition according to the present invention can be very preferable for use to impart hair volumizing effects and long lasting effects to colored keratin fibers.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

The present invention relates to a composition for use in coloring or bleaching keratin fibers, preferably hair, comprising (a) malonic acid and (b) at least one cationic polymer. The present invention can prevent or reduce the loss of volume of keratin fibers when the keratin fibers are colored by, for example, dyeing or bleaching, and when the colored keratin fibers are washed by, for example, shampooing.

Description

DESCRIPTION
COMPOSITION FOR KERATIN FIBERS
TECHNICAL FIELD
The present invention relates to a composition to be applied onto keratin fibers such typically used in dyeing or bleaching the keratin fibers, as well as the uses thereof.
BACKGROUND ART
It is known practice to add various conditioners to hair dye compositions in order to give the hair at least one of the following cosmetic properties-ease of disentangling, good feeling, smoothness, sheen, and volume.
However, there still exists a demand for a conditioning agent used in coloring or bleaching keratin fibers, which can prevent or reduce the loss of volume of keratin fibers when the keratin fibers are colored and/or when the colored keratin fibers are washed.
DISCLOSURE OF INVENTION
Especially, in some cases, the dyed or bleached keratin fibers tend to lose their volume because the roots of the dyed or bleached keratin fibers tend to bend, and it becomes difficult to lift up the keratin fibers. The loss of volume in dyed or bleached keratin fibers is not preferable because hair styling tends to be not easy.
Also, when the roots of the dyed or bleached keratin fibers bend, the side of the roots can be more visible. Thus, the difference in color between the dyed or bleached part of the keratin fibers and the newly grown undyed or unbleached part of the keratin fibers tends to be more distinct. This is not preferable either from the viewpoint of uniform appearance of dyed or bleached keratin fibers from the root to the tip of the keratin fibers. In addition, if undyed keratin fibers are white or gray hair, for example, the loss of volume of dyed keratin fibers may cause the appearance of looking old.
Furthermore, the loss of volume of dyed or bleached keratin fibers tends to be worse, when the dyed or bleached keratin fibers are washed by, for example, shampooing.
Thus, it is preferable to prevent or reduce the loss of volume of keratin fibers when the keratin fibers are colored by, for example, dyeing or bleaching and/or when the colored keratin fibers are washed by, for example, shampooing.
An objective of the present invention is to provide a composition for keratin fibers which can prevent or reduce the loss of volume of keratin fibers when the keratin fibers are colored and/or when the colored keratin fibers are washed.
The above objective can be achieved by a composition for use in coloring or bleaching keratin fibers, preferably hair, comprising:
(a) malonic acid; and
(b) at least one cationic polymer. The (b) cationic polymer may have a unit derived from vinylpyrrolidone.
The (b) cationic polymer may be selected from:
copolymers comprising vinylpyrrolidone units and dimethylaminoethyl methacrylate units,
copolymers comprising vinylpyrrolidone units,
ethacrylamidopropyltrimethylammonium units, and
copolymers comprising vinylpyrrolidone units and methylvinylimidazolium units.
The copolymers comprising vinylpyrrolidone units and dimethylaminoethyl methacrylate units may be chosen from:
vinylpyrrolidone/dimethylaminoethyl methacrylate copolymers;
vinylpyrrolidone/dimethylaminoethyl methacrylate copolymers quaternized with diethyl sulphate;
vinylpyrrolidone/dimethylaminoethyl methacrylate/hydrophilic polyurethane copolymers;
quaternized or non-quaternized vinylpyrrolidone/dimethylaminoethyl
methacrylate/C8-Ci6 olefin copolymers; and
vinylpyrrolidone/dimethylaminoethyl methacrylate/vinylcaprolactam copolymers.
The amount of the (a) malonic acid may range from 0.1% to 20% by weight, preferably from 0.5% to 15% by weight, and more preferably from 1% to 10% by weight, relative to the total weight of the composition.
The amount of the (b) cationic polymer may range from 0.5% to 30% by weight, preferably from 1%) to 20%) by weight, and more preferably from 1.5% to 15% by weight, relative to the total weight of the composition. The composition according to the present invention may further comprise propylene glycol.
The amount of the propylene glycol may range from 0.01 to 30% by weight, preferably from 0.1 to 25% by weight, and more preferably from 1 to 20% by weight relative to the total weight of the composition.
The composition according to the present invention may further comprise at least one oxidizing agent.
The oxidizing agent may be hydrogen peroxide.
The amount of the oxidizing agent may range from 0.01% to 30% by weight, preferably from 0.1%) to 20%) by weight, and more preferably from 1% to 10% by weight, relative to the total weight of the composition. The present invention also relates to a ready-to-use cosmetic composition for keratin fibers, preferably hair, comprising:
the composition according to the present invention,
a first composition comprising at least one oxidizing agent, and
a second composition comprising at least one alkaline agent. The present invention also relates to a kit for keratin fibers, preferably hair, comprising: a first compartment comprising the composition according to the present invention, further comprising at least one oxidizing agent, and
a second compartment comprising a second composition comprising at least one alkaline agent.
The present invention also relates to a kit for keratin fibers, preferably hair, comprising: a first compartment comprising a first composition comprising at least one oxidizing agent,
a second compartment comprising a second composition comprising at least one alkaline agent, and
a third compartment comprising the composition according to the present invention.
The present invention also relates to a cosmetic process for keratin fibers, preferably hair, comprising the steps of:
(1) mixing:
the composition according to the present invention,
a first composition comprising at least one oxidizing agent, and
a second composition comprising at least one alkaline agent to prepare a ready-to-use cosmetic composition, and
(2) applying the ready-to-use cosmetic composition to the keratin fibers.
BRIEF DESCRIPTION OF DRAWINGS Fig. 1 shows a side view in order to show how to determine the vertical angle between a plate and the tips of a hair fiber in the evaluation of volumizing effects of the compositions according to Examples 1-5 and Comparative Examples 1-10.
BEST MODE FOR CARRYING OUT THE INVENTION
After diligent research, the inventors have discovered that a combination of malonic acid and at least one cationic polymer can impart a volumizing effect and long lastingness to keratin fibers, when it is used in coloring or bleaching compositions for keratin fibers, thus completing the present invention.
Thus, the present invention relates to a composition for use in coloring or bleaching keratin fibers, preferably hair, comprising:
(a) malonic acid; and
(b) at least one cationic polymer.
The above composition according to the present invention can prevent or reduce the loss of volume of keratin fibers when the keratin fibers are colored by, for example, dyeing or bleaching, and/or when the colored keratin fibers are washed by, for example, shampooing. "Keratin fibers" here mean fibers which include at least one keratin substance. It is preferable that at least a part of the surface of the keratin fibers be formed by keratin substances. Examples of keratin fibers include hair, eyebrows, eyelashes, and the like. It is preferable that the present invention is used for hair. The above composition for keratin fibers according to the present invention can be used as a conditioning or a booster composition in coloring keratin fibers for the purpose of preventing or reducing the loss of volume of keratin fibers.
The composition according to the present invention can be used in combination with another composition including oxidizing agent(s). If the composition according to the present invention, which further comprises oxidizing agent(s), is used in combination with another composition including oxidation dye(s), it is possible to dye the keratin fibers. Alternatively, if the composition according to the present invention, which further comprises oxidizing agent(s), is used alone, it is possible to bleach the keratin fibers due to the action of the oxidizing agent.
It is preferable that the composition for keratin fibers according to the present invention be mixed with other compositions including each of at least one oxidizing agent and at least one alkaline agent, and the mixture thus obtained is used to color keratin fibers. In addition, if another composition including at least one alkaline agent includes oxidation base(s) and coupler(s), the keratin fibers can be dyed in a variety of colors.
The composition for use in coloring or bleaching keratin fibers according to the present invention can prevent or reduce the loss of volume of keratin fibers when the keratin fibers are colored by, for example, dyeing or bleaching, and/or when the colored keratin fibers are washed by, for example, shampooing.
Hereafter, the present invention will be described in a detailed manner. [Composition]
The composition for use in coloring or bleaching keratin fibers, preferably hair, according to the present invention comprises:
(a) malonic acid; and
(b) at least one cationic polymer.
(Malonic Acid)
The composition according to the present invention comprises (a) malonic acid.
Malonic acid can be represented by the general formula below:
Figure imgf000005_0001
The inventor surprisingly found that the combination of malonic acid and cationic polymer can provide a superior hair volumizing effect as well as long lasting performance in hair coloring and/or bleaching compared to other combinations using another dicarboxylic acid instead of malonic acid. The (a) malonic acid may be present in a content of 0.1% by weight or more, preferably 0.5% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition. The (a) malonic acid may be present in a content of 20% by weight or less, preferably 15% by weight or less, and more preferably 10% by weight or less, relative to the total weight of the composition.
The (a) malonic acid may be present in a content ranging from 0.1% to 20% by weight, preferably from 0.5% to 15% by weight, and more preferably from 1% to 10% by weight, relative to the total weight of the composition.
(Cationic Polymer)
The composition according to the present invention comprises (b) at least one cationic polymer. Two or more (b) cationic polymers may be used in combination. Thus, a single type of cationic polymer or a combination of different types of cationic polymers may be used.
It should be noted that, for the purposes of the present invention, the term "cationic polymer" denotes any polymer containing cationic groups and/or groups that may be ionized into cationic groups.
Such polymers may be chosen from those already known per se as improving the cosmetic properties of the hair, i.e., especially those described in patent application EP-A-337 354 and in French patents FR-2 270 846, 2 383 660, 2 598 611, 2 470 596 and 2 519 863.
Among the (b) cationic polymers that may be mentioned more particularly are polymers of the polyamine, polyamino amide and polyquaternary ammonium type. Acationic polymer has a positive charge density. The charge density of the cationic polymer may be from 0.1 meq/g to 20 meq/g, preferably from 1 to 15 meq/g, and more preferably from 4 to 10 meq/g.
It may be preferable that the molecular weight of the cationic polymer be 1,000 or more, preferably 10,000 or more, more preferably 100,000 or more, and even more preferably 1,000,000 or more.
The cationic polymer may have at least one positively chargeable and/or positively charged moiety selected from the group consisting of a secondary or tertiary amino group, a quaternary ammonium group, a guanidine group, a biguanide group, an imidazole group, an imino group, a pyridyl group, and an amino group. The term (primary) "amino group" here means a of -NH2 group.
The cationic polymer may be a homopolymer or a copolymer. The term "copolymer" is understood to mean both copolymers obtained from two kinds of monomers and those obtained from more than two kinds of monomers, such as terpolymers obtained from three kinds of monomers.
The cationic polymer may be selected from natural and synthetic cationic polymers. Non-limiting examples of the cationic polymers are as follows.
(1) Homopolymers and copolymers derived from acrylic or methacrylic esters and amides and comprising at least one unit chosen from units of the following formulas:
Figure imgf000007_0001
wherein:
Ri and R2, which may be identical or different, are chosen from hydrogen and alkyl groups comprising from 1 to 6 carbon atoms, for instance, methyl and ethyl groups;
R3, which may be identical or different, is chosen from hydrogen and CH3;
the symbols A, which may be identical or different, are chosen from linear or branched alkyl groups comprising from 1 to 6 carbon atoms, for example, from 2 to 3 carbon atoms and hydroxyalkyl groups comprising from 1 to 4 carbon atoms;
R4, R5, and R6, which may be identical or different, are chosen from alkyl groups comprising from 1 to 18 carbon atoms and benzyl groups, and in at least one embodiment, alkyl groups comprising from 1 to 6 carbon atoms; and
X is an anion derived from an inorganic or organic acid, such as methosulphate anions and halides, for instance chloride and bromide.
The copolymers of family (1) may also comprise at least one unit derived from comonomers which may be chosen from acrylamides, methacrylamides, diacetone acrylamides, acrylamides and methacrylamides substituted on the nitrogen atom with (C1-C4) lower alkyl groups, groups derived from acrylic or methacrylic acids and esters thereof, vinyllactams such as vinylpyrrolidone and vinylcaprolactam, and vinyl esters. Examples of copolymers of family (1) include, but are not limited to:
copolymers of acrylamide and of dimethylaminoethyl methacrylate quaternized with dimethyl sulphate or with a dimethyl halide,
copolymers of acrylamide and of methacryloyloxyethyltrimethylammonium chloride described, for example, in European Patent Application No. 0 080 976,
copolymers of acrylamide and of methacryloyloxyethyltrimethylammonium methosulphate, quatemized or nonquatemized vinylpyrrolidone/dialkylaminoalkyl acrylate or methacrylate copolymers, described, for example, in French Patent Nos. 2 077 143 and 2 393 573, dimethylaminoethyl methacrylate/vinylcaprolactam/vinylpyrrolidone terpolymers, vinylpyrrolidone/methacrylamidopropyldimethylamine copolymers, quatemized vinylpyrrolidone/dimethylaminopropylmethacrylamide copolymers, and
crosslinked methacryloyloxy(C1-C4)alkyltri(Ci-C4)alkylammonium salt polymers such as the polymers obtained by homopolymerization of dimethylaminoethyl methacrylate quatemized with methyl chloride, or by copolymerization of acrylamide with dimethylaminoethyl methacrylate quatemized with methyl chloride, the homopolymerization or copolymerization being followed by crosslinking with a compound containing olefinic unsaturation, for example, methylenebisacrylamide.
Preferably, copolymers of family (1) have a unit derived from vinylpyrrolidone. More preferably, copolymers of family (1) have at least one pendent ring structure derived from the vinylpyrrolidone. On the other hand, it is preferable that the copolymers of family (1) comprise no ring structure in the backbone of the polymer.
The copolymers of family (1) having vinylpyrrolidone units can be selected from:
(i) the copolymers comprising vinylpyrrolidone units and dimethylaminoethyl methacrylate units, for example:
- vinylpyrrolidone/dimethylaminoethyl methacrylate copolymers; for example, vinylpyrrolidone/dimethylaminoethyl methacrylate copolymer (20/80 by weight) sold under the trade name Copolymer 845 by the company I.S.P.,
vinylpyrrolidone/dimethylaminoethyl methacrylate copolymers quatemized with diethyl sulphate; for example, vinylpyrrolidone/dimethylaminoethyl methacrylate copolymer quatemized with diethyl sulphate, sold under the trade names Gafquat 734, 755, 755S and 755L by the company I.S.P.,
- vinylpyrrolidone/dimethylaminoethyl methacrylate/hydrophilic polyurethane copolymers; for example, vinylpyrrolidone/dimethylaminoethyl methacrylate/hydrophilic polyurethane copolymer, sold under the trade name Pecogel GC-310 by the company U.C.I.B., or under the trade names Aquamere CI 031 and C1511 by the company Blagden Chemicals,
- vinylpyrrolidone/dimethylaminoethyl methacrylate/C -Ci6 olefin copolymers, quatemized or non-quatemized; for example, vinylpyrrolidone/dimethylaminoethyl methacrylate/C8-Ci6 olefin copolymer sold under the trade names Ganex ACP1050 to 1057, 1062-1069 and 1079-1086 by the company I.S.P.,
and
- vinylpyrrolidone/dimethylaminoethyl methacrylate/vinylcaprolactam copolymers; for example, vinylpyrrolidone/dimethylaminoethyl methacrylate/vinylcaprolactam copolymer sold under the trade name Gaffix VC713 by the company I.S.P;
(ii) the copolymers comprising vinylpyrrolidone units and methacrylamidopropyltrimethylammonium (MAPTAC) units, for example:
- vinylpyrrolidone/methacrylamidopropyltrimethylammonium copolymers; for example, vinylyrrolidone/MAPTAC copolymer sold under the trade names Gafquat ACP1011 and Gafquat HS100 by the company I.S.P,
and
- vinylpyrrolidone/methacrylamidopropyltrimethylammonium/vinylcaprolactam
terpolymers; for example, vinylpyrrolidone/MAPTAC/vinylcaprolactam terpolymer sold under the trade names Polymer ACP 1059, 1060 and 1156 by the company I.S.P.; and
(iii) the copolymers comprising vinylpyrrolidone units and methylvinylimidazolium units, for example: - vinylpyrrolidone/methylvinylimidazolium chloride copolymers; for example, vinylpyrrolidone/methylvinylimidazolium chloride copolymer sold under the trade names Luviquat FC370, FC550, FC905 and HM552 by the company BASF,
- vinylpyrrolidone/methylvinylimidazolium chloride/vinylimidazole copolymers; for example, vinylpyrrolidone/methylvinylimidazolium chloride/vinylimidazole copolymer sold under the trade name Luviquat 8155 by the company BASF,
and
- vinylpyrrolidone/methylvinylimidazolium methosulphate copolymers; for example, vinylpyrrolidone/methylvinylimidazolium methosulphate copolymer sold under the trade name Luviquat MS370 by the company BASF.
It may be preferable that the copolymers of family (1) be chosen from the copolymer comprising vinylpyrrolidone units and dimethylaminoethyl methacrylate units, more preferably chosen from vinylpyrrolidone/dimethylaminoethyl methacrylate copolymers quaternized with diethyl sulphate, and even more preferably Polyquaternium-11.
(2) Cationic cellulose derivatives such as cellulose ether derivatives comprising quaternary ammonium groups described, for example, in French Patent No. 1 492 597, such as the polymers sold under the names "JR" (JR 400, JR 125, and JR 30M) or "LR" (LR 400 and LR 30M) by the company Union Carbide Corporation. These polymers are also defined in the CTFA dictionary as quaternary ammoniums of hydroxyethylcellulose that have reacted with an epoxide substituted with a trimethylammonium group.
It may be preferable that the cationic cellulose derivatives be quaternized hydroxyethyl celluloses modified with at least one quaternary ammonium group comprising at least one fatty chain, such as alkyl, arylalkyl or alkylaryl groups comprising at least 8 carbon atoms, or mixtures thereof. The alkyl radicals borne by the quaternary ammonium group may preferably contain from 8 to 30 carbon atoms, especially from 10 to 30 carbon atoms. The aryl radicals preferably denote phenyl, benzyl, naphthyl or anthryl groups.
More preferably, the cationic cellulose derivatives may comprise at least one quaternary ammonium group including at least one Cs-C30 hydrocarbon group.
Examples of quaternized alkylhydroxyethylcelluloses containing C8-C30 fatty chains that may be mentioned include the products Quatrisoft LM 200, Quatrisoft LM-X 529-18-A, Quatrisoft LM-X 529-18B (CI 2 alkyl) and Quatrisoft LM-X 529-8 (CI 8 alkyl) or Softcat Polymer SL100, Softcat SX-1300X, Softcat SX-1300H, Softcat SL-5, Softcat SL-30, Softcat SL-60 , Softcat SK-MH, Softcat SX-400X, Softcat SX-400H, SoftCat SK-L, Softcat SK-M, and Softcat SK-H, sold by the company Amerchol and the products Crodacel QM, Crodacel, QL (C 12 alkyl) and Crodacel QS (C 18 alkyl) sold by the company Croda.
Among these quaternized alkylhydroxyethylcelluloses the products corresponding to INCI name Polyquaternium-67 are preferred. From another view point, the cationic cellulose derivatives could also be chosen among cationic cellulose ether(s), comprising from 4 000 to 10 000 anhydroglucose units, said anhydroglucose units being substituted with at least:
(i) one substituent of formula [R4R5R6R9N+](X2-) in which
R4 and R5 represent, independently of one another, a methyl or ethyl group,
R6 represents a linear or branched C8-C24 alkyl group or an aralkyl group in which the linear or branched alkyl part is C8-C24,
R9 represents a divalent group which allows the attachment to the anhydroglucose group and which is chosen from -(B)q-CH2-CHOH-CH2- and -CH2CH2-,
q denoting 0 or 1,
B denoting a divalent group -(CH2CH20)n'-s
n' being an integer ranging from 1 to 100,
X2 " represents an anion; and
(ii) one substituent of formula
[R1R2R3R8N+](Xf) in which:
R1, R2 and R3 represent, independently of one another, a methyl or ethyl group,
R8 represents a divalent group which allows the attachment to the anhydroglucose group and which is chosen from -(A)p-CH2-CHOH-CH2- and -CH2CH2-,
p denoting 0 or 1,
A denoting a divalent group -(CH2CH20)n-,
n being an integer ranging from 1 to 100, and
Xf represents an anion. Preferably, the substituent (i) of formula [R4R5R6R9N+](X2 ") is present at an average of from 0.0003 to 0.08 mol, per mole of anhydroglucose units.
The cationic cellulose ethers that can be used in the compositions according to the present invention are preferably hydroxyethyl celluloses or hydroxypropyl celluloses. The cationic cellulose ethers that can be used in the compositions according to the present invention preferably comprise more than 4500, advantageously more than 5000, and more preferably more than 6000 anhydroglucose units.
Preferably, the cationic cellulose ethers that can be used in the compositions according to the present invention preferably comprise up to 9000, and preferably up to 8000 anhydroglucose units.
These cationic cellulose ethers and the process for the preparation thereof are described in application WO 2005/000903.
According to a preferred variant, the cationic cellulose ethers that can be used in the compositions according to the present invention are formed from at least one unit (IV) and at least one of the following units (I), (II) and (III):
Figure imgf000011_0001
with the proviso that:
the total number of units (I)+(II)+(III)+(IV) is between 4000 and 10 000;
the [(III)+(IV)]/[(I)+(II)+(III)+(IV)] ratio ranges from 0.0003 to 0.8;
the [(II)+(IV)]/[(I)+(II)+(III)+(IV)] ratio ranges from 0.02 to 0.9;
the integers n and n', independently of one another, range from 0 to 5;
Ri, R2, R3, R4 and R5 represent, independently of one another, a methyl or ethyl group;
R6 represents a linear or branched C8-C24, preferably Ci0-C24, more preferably Ci2-C24 and better still Ci2-C15, alkyl group or an aralkyl group in which the linear or branched alkyl part is C8-C24;
Xi" and X2 " represent anions preferably chosen, independently of one another, from phosphate, nitrate, sulphate and halide (CI", Br", F", Γ) ions.
According to a particular variant, the cationic cellulose ethers that can be used in the compositions according to the present invention are formed from at least one unit (IV) and at least one of the units (I), (II) or (III) above, in which R6 is a linear dodecyl group.
Among the cationic cellulose ethers that can be used in the compositions of the present invention, mention may be made of the polymers of Softcat SL-5, SL-30, SL-60 and SL-100 type (INCI: Polyquaternium-67) sold by the company Amerchol. The cationic cellulose ethers that are particularly preferred are the polymers of SL-60 and SL- 100 type.
(3) Cationic cellulose derivatives such as cellulose copolymers and cellulose derivatives grafted with a water-soluble monomer of quaternary ammonium, and described, for example, in U.S. Pat. No. 4,131,576, such as hydroxyalkylcelluloses, for instance, hydroxymethyl-, hydroxyethyl-, and hydroxypropylcelluloses grafted, for example, with a salt chosen from methacryloylethyltrimethylammonium, methacrylamidopropyltrimethylammonium, and dimethyldiallylammonium salts.
Commercial products corresponding to these polymers include, for example, the products sold under the name "Celquat® L 200" and "Celquat® H 100" by the company National Starch.
(4) Non-cellulose-based cationic polysaccharides described in U.S. Pat. Nos. 3,589,578 and 4,031,307, such as guar gums comprising cationic trialkylammonium groups, cationic hyaluronic acid, and dextran hydroxypropyl trimonium chloride. Guar gums modified with a salt, for example the chloride, of 2,3-epoxypropyltrimethylammonium (guar hydroxypropyltrimonium chloride) may also be used.
Such products are sold, for instance, under the trade names JAGUAR® C13 S, JAGUAR® C15, JAGUAR® C17, and JAGUAR® C162 by the company MEYHALL.
(5) Polymers comprising piperazinyl units and divalent alkylene or hydroxyalkylene groups comprising straight or branched chains, optionally interrupted with at least one entity chosen from oxygen, sulphur, nitrogen, aromatic rings, and heterocyclic rings, and also the oxidation and/or quaternization products of these polymers. Such polymers are described, for example, in French Patent Nos. 2 162 025 and 2 280 361.
(6) Water-soluble polyamino amides prepared, for example, by polycondensation of an acidic compound with a polyamine; these polyamino amides possibly being crosslinked with an entity chosen from epihalohydrins; diepoxides; dianhydrides; unsaturated dianhydrides; bisunsaturated derivatives; bishalohydrins; bisazetidiniums; bishaloacyidiamines; bisalkyl halides; oligomers resulting from the reaction of a difunctional compound which is reactive with an entity chosen from bishalohydrins, bisazetidiniums, bishaloacyldiamines, bisalkyl halides, epihalohydrins, diepoxides, and bisunsaturated derivatives; the crosslinking agent being used in an amount ranging from 0.025 to 0.35 mol per amine group of the polyamino amide; these polyamino amides optionally being alkylated or, if they comprise at least one tertiary amine function, they may be quaternized. Such polymers are described, for example, in French Patent Nos. 2 252 840 and 2 368 508.
(7) Polyamino amide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids, followed by alkylation with difunctional agents, for example, adipic acid/dialkylaminohydroxyalkyldialkylenetriamine polymers in which the alkyl group comprises from 1 to 4 carbon atoms, such as methyl, ethyl, and propyl groups, and the alkylene group comprises from 1 to 4 carbon atoms, such as an ethylene group. Such polymers are described, for instance, in French Patent No. 1 583 363. In at least one embodiment, these derivatives may be chosen from adipic acid/dimethylaminohydroxypropyldiethylenetriamine polymers .
(8) Polymers obtained by reaction of a polyalkylene polyamine comprising two primary amine groups and at least one secondary amine group, with a dicarboxylic acid chosen from diglycolic acid and saturated aliphatic dicarboxylic acids comprising from 3 to 8 carbon atoms. The molar ratio of the polyalkylene polyamine to the dicarboxylic acid may range from 0.8:1 to 1.4: 1 ; the polyamino amide resulting therefrom being reacted with epichlorohydrin in a molar ratio of epichlorohydrin relative to the secondary amine group of the polyamino amide ranging from 0.5:1 to 1.8:1. Such polymers are described, for example, in U.S. Pat. Nos. 3,227,615 and 2,961,347.
(9) Cyclopolymers of alkyldiallylamine and cyclopolymers of dialkyldiallyl-ammonium, such as homopolymers and copolymers comprising, as the main constituent of the chain, at least one unit chosen from units of formulas (Va) and (Vb):
Figure imgf000013_0001
(C¾)/-— CRji C(RJ2)— C¾—
N
I
R<* (Vb)
wherein:
k and t, which may be identical or different, are equal to 0 or 1, the sum k+t being equal to 1 ; Ri2 is chosen from hydrogen and methyl groups;
R10 and Rn, which may be identical or different, are chosen from alkyl groups comprising from 1 to 6 carbon atoms, hydroxyalkyl groups in which the alkyl group comprises, for example, from 1 to 5 carbon atoms, and lower (Ci-C4)amidoalkyl groups, or Rio and Rn may form, together with the nitrogen atom to which they are attached, heterocyclic groups such as piperidinyl and morpholinyl; and
Y' is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulphate, bisulphite, sulphate, and phosphate. These polymers are described, for example, in French Patent No. 2 080 759 and in its Certificate of Addition 2 190 406.
In one embodiment, Rio and Rn, which may be identical or different, are chosen from alkyl groups comprising from 1 to 4 carbon atoms. Examples of such polymers include, but are not limited to, (co)polydiallyldialkyl ammonium chloride such as the dimethyldiallylammonium chloride homopolymer (INCI: Polyquaternium-6) sold under the name "MERQUAT® 100" by the company CALGON (and its homologues of low weight-average molecular mass) and the copolymers of diallyldimethylammonium chloride and of acrylamide (INCI: Polyquaternium-7) sold under the name "MERQUAT® 550".
(10) Quaternary diammonium polymers comprising at least one repeating unit of formula (VI):
Figure imgf000014_0001
wherein:
Ri3, Ri4, Ri5, and R16, which may be identical or different, are chosen from aliphatic, alicyclic, and arylaliphatic groups comprising from 1 to 20 carbon atoms and lower hydroxyalkyl aliphatic groups, or alternatively Ri3, Ri4, R15, and Ri6 may form, together or separately, with the nitrogen atoms to which they are attached, heterocycles optionally comprising a second heteroatom other than nitrogen, or alternatively Ri3, Ri4, Ris, and Ri6, which may be identical or different, are chosen from linear or branched Ci-C6 alkyl groups substituted with at least one group chosen from nitrile groups, ester groups, acyl groups, amide groups, -CO-O-Rn-E groups, and -CO-NH-R17-E groups, wherein Rn is an alkylene group and E is a quaternary ammonium group;
Ai and Bi, which may be identical or different, are chosen from polymethylene groups comprising from 2 to 20 carbon atoms, which may be linear or branched, saturated or unsaturated, and which may comprise, linked or intercalated in the main chain, at least one entity chosen from aromatic rings, oxygen, sulphur, sulphoxide groups, sulphone groups, disulphide groups, amino groups, alkylamino groups, hydroxyl groups, quaternary ammonium groups, ureido groups, amide groups, and ester groups, and
X" is an anion derived from an inorganic or organic acid; Ai, Rn, and R15 may form, together with the two nitrogen atoms to which they are attached, a piperazine ring;
if Ai is chosen from linear or branched, saturated or unsaturated alkylene or hydroxyalkylene groups, Bi may be chosen from: -(CH2)n-CO-E'-OC-(CH2)n- wherein E' is chosen from:
a) glycol residues of formula -0-Z-0-, wherein Z is chosen from linear or branched hydrocarbon-based groups and groups of the following formulas:
-(CH2-CH2-0)x-CH2-CH2- -[CH2-CH(CH3)-0]y-CH2-CH(CH3)- wherein x and y, which may be identical or different, are chosen from integers ranging from 1 to 4, which represent a defined and unique degree of polymerization, and numbers ranging from 1 to 4, which represent an average degree of polymerization;
b) bis-secondary diamine residue such as piperazine derivatives;
c) bis-primary diamine residues of formula -NH-Y-NH-, wherein Y is chosen from linear or branched hydrocarbon-based groups and the divalent group -CH2-CH2-S-S-CH2-CH2-; and d) ureylene groups of formula -NH-CO-NH-.
In at least one embodiment, X" is an anion such as chloride or bromide. Polymers of this type are described, for example, in French Patent Nos. 2 320 330; 2 270 846; 2 316 271; 2 336 434; and 2 413 907 and U.S. Pat. Nos. 2,273,780; 2,375,853; 2,388,614; 2,454,547; 3,206,462; 2,261,002; 2,271,378; 3,874,870; 4,001,432; 3,929,990; 3,966,904; 4,005,193; 4,025,617; 4,025,627; 4,025,653; 4,026,945; and 4,027,020. Non-limiting examples of such polymers include those comprising at least one repeating unit of formula (VII):
Figure imgf000015_0001
wherein Ri3, Ri4, Ris, and Ri6, which may be identical or different, are chosen from alkyl and hydroxyalkyl groups comprising from 1 to 4 carbon atoms, n and p, which may be identical or different, are integers ranging from 2 to 20, and X" is an anion derived from an inorganic or organic acid.
One particularly preferred compound of formula VII) is that for which R10, Ri i Ri2 and R13 represent a methyl group, n=3, p=6 and X=C1, which is called Hexadimethrine chloride according to the INCI(CTFA) nomenclature.
(11) Polyquaternary ammonium polymers comprising units of formula (VIII):
R IS
— +-(C¾J,- H-CO— (C¾)4-CO-NH— (C¾)s-N+-A—
x- I I
19 X- ½
(VIII) wherein:
Ri8, Ri9, R20, and R2i, which may be identical or different, are chosen from hydrogen, methyl groups, ethyl groups, propyl groups, β-hydroxyethyl groups, β-hydroxypropyl groups, -CH2CH2(OCH2CH2)pOH groups, wherein p is chosen from integers ranging from 0 to 6, with the proviso that R18, R19, R20, and R2i are not simultaneously hydrogen,
r and s, which may be identical or different, are chosen from integers ranging from 1 to 6, q is chosen from integers ranging from 0 to 34,
X" is an anion such as a halide, and
A is chosen from radicals of dihalides and -CH2-CH2-0-CH2-CH2-.
Such compounds are described, for instance, in European Patent Application No. 0 122 324.
(12) Quaternary polymers of vinylpyrrolidone and of vinylimidazole. Other examples of suitable cationic polymers include, but are not limited to, cationic proteins and cationic protein hydrolysates, polyalkyleneimines, such as polyethyleneimines, polymers comprising units chosen from vinylpyridine and vinylpyridinium units, condensates of polyamines and of epichlorohydrin, quaternary polyureylenes, and chitin derivatives.
According to one embodiment of the present invention, the at least one cationic polymer is chosen from cellulose ether derivatives comprising quaternary ammonium groups, such as the product sold under the name "JR 400" by the company UNION CARBIDE CORPORATION, cationic cyclopolymers, for instance, the homo-polymers and copolymers of dimethyldiallylammonium chloride sold under the names MERQUAT® 100, MERQUAT® 550, and MERQUAT® S by the company CALGON, guar gums modified with a 2,3-epoxypropyltrimethylammonium salt, and quaternary polymers of vinylpyrrolidone and of vinylimidazole. (13) Polyamines
As the cationic polymer, it is also possible to use (co)polyamines, which may be homopolymers or copolymers, with a plurality of amino groups. The amino group may be a primary, secondary, tertiary or quaternary amino group. The amino group may be present in a polymer backbone or a pendent group, if present, of the (co)polyamines.
As examples of the (co)polyamines, mention may be made of chitosan, (co)polyallylamines, (co)polyvinylamines, (co)polyanilines, (co)polyvinylimidazoles,
(co)polydimethylaminoethylenemethacrylates, (co)polyvinylpyridines such as (co)poly-l-methyl-2-vinylpyridines, (co)polyimines such as (co) polyethyleneimines, (co)polypyridines such as (co)poly(quaternary pyridines), (co)polybiguanides such as (co)polyaminopropyl biguanides, (co)polylysines, (co)polyornithines, (co)polyarginines, (co)polyhistidines, aminodextrans, aminocelluloses, amino(co)polyvinylacetals, and salts thereof.
As the (co)polyamines, it is preferable to use (co)polylysines. Polylysine is well known. Polylysine can be a natural homopolymer of L-lysine that can be produced by bacterial fermentation. For example, polylysine can be ε-Poly-L-lysine, typically used as a natural preservative in food products. Polylysine is a polyelectrolyte which is soluble in polar solvents such as water, propylene glycol and glycerol. Polylysine is commercially available in various forms, such as poly D-lysine and poly L-lysine. Polylysine can be in salt and/or solution form.
(14) Cationic Polyaminoacids
As the cationic polymer, it may be possible to use cationic polyaminoacids, which may be cationic homopolymers or copolymers, with a plurality of amino groups and carboxyl groups. The amino group may be a primary, secondary, tertiary or quaternary amino group. The amino group may be present in a polymer backbone or a pendent group, if present, of the cationic polyaminoacids. The carboxyl group may be present in a pendent group, if present, of the cationic polyaminoacids.
As examples of the cationic polyaminoacids, mention may be made of cationized collagen, cationized gelatin, steardimonium hydroxypropyl hydrolyzed wheat protein, cocodimonium hydroxypropyl hydrolyzed wheat protein, hydroxypropyltrimonium hydrolyzed conchiolin protein, steardimonium hydroxypropyl hydrolyzed soy protein, hydroxypropyltrimonium hydrolyzed soy protein, cocodimonium hydroxypropyl hydrolyzed soy protein, and the like.
It may be preferable that the cationic polymer be selected from the group consisting of cyclopolymers of alkyldiallylamine and cyclopolymers of dialkyldiallylammonium such as (co)polydiallyldialkyl ammonium chloride, (co)polyamines such as (co)polylysines, cationic (co)polyaminoacids such as cationized collagen, and salts thereof.
It is preferable that the (b) cationic polymer be a polyquaternium polymer or a polymeric quaternary ammonium salt.
Polymeric quaternary ammonium salts are cationic polymers comprising at least one quaternized nitrogen atom. Mention may in particular be made, as polymeric quaternary ammonium salts, of the Polyquaternium products (CTFA name), which contribute mainly to the quality of foam and feeling of the skin after use, in particular the feeling of the skin after use. These polymers can preferably be chosen from the following polymers:
Polyquaternium-5, such as the product Merquat 5 sold by Nalco;
Polyquaternium-6, such as the product Salcare SC 30 sold by BASF and the product Merquat 100 sold by Nalco;
Polyquaternium-7, such as the products Merquat S, Merquat 2200, Merquat 7SPR, and Merquat 550 sold by Nalco and the product Salcare SC 10 sold by BASF;
Polyquaternium- 10, such as the product Polymer JR400 sold by Amerchol;
Polyquaternium- 11 , such as the products Gafquat 755, Gafquat 755N and Gafquat 734 sold by ISP;
Polyquaternium- 15, such as the product Rohagit KF 720 F sold by Rohm;
Polyquaternium- 16, such as the products Luviquat FC905, Luviquat FC370, Luviquat HM552 and Luviquat FC550 sold by BASF;
Polyquaternium-28, such as the product Styleze CC10 sold by ISP;
Polyquaternium-44, such as the product Luviquat Care sold by BASF;
Polyquaternium-46, such as the product Luviquat Hold sold by BASF; and
Polyquaternium-47, such as the product Merquat 2001 sold by Nalco.
Preferably, the (b) cationic polymer can be selected from the copolymers of families (1), (2), and (9), and any combinations thereof. In particular, the (b) cationic polymer comprises at least the copolymers of family (1). Especially, the (b) cationic polymer comprises the copolymers of families (2) and/or (9) in addition to the copolymers of family (1). In particular, the (b) cationic polymer comprises Polyquaternium-11.
The (b) cationic polymer may be present in a content of 0.5% by weight or more, preferably 1% by weight or more, and more preferably 1.5% by weight or more, relative to the total weight of the composition. The (b) cationic polymer may be present in a content of 30% by weight or less, preferably 20% by weight or less, and more preferably 15% by weight or less, ' relative to the total weight of the composition. The (b) cationic polymer may be present in a content ranging from 0.5% to 30% by weight, preferably from 1% to 20% by weight, and more preferably from 1.5% to 15% by weight, relative to the total weight of the composition.
(pH and Optional Ingredients)
The pH of the composition according to the present invention may be adjusted to the desired value using acidifying or basifying agents commonly used in the technical field of coloring keratin fibers. The pH of the composition according to the present invention may be preferably from 1 to 6, more preferably from 2 to 5, and even more preferably from 2 to 4, and most preferably from 2 to 3.
Among the acidifying agents, mention may be made, by way of example, of mineral or organic acids such as hydrochloric acid, ortho-phosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, and lactic acid, and sulfonic acids.
Among the basifying agents, mention may be made, by way of example, of sodium hydroxide, ammonium hydroxide, alkali metal carbonates, alkanolamines such as mono-, di- and triethanolamines and also their derivatives, sodium or potassium hydroxide and compounds of the formula below:
Figure imgf000018_0001
d wherein
W denotes an alkylene such as propylene optionally substituted by a hydroxyl or a Ci-C4 alkyl radical, and a, Rb, Rc and a independently denote a hydrogen atom, an alkyl radical or a d-C4 hydroxyalkyl radical, which may be exemplified by 1,3-propanediamine and
derivatives thereof. Sodium or potassium hydroxide may also be preferable.
The acidifying or basifying agent may be used in an amount ranging from 0.001 to 15%) by weight, preferably from 0.01 to 10%) by weight, and more preferably from 0.1 to 5% by weight, relative to the total weight of the composition.
The composition according to the present invention may preferably comprise propylene glycol. The use of propylene glycol may be preferable since it can improve the volumizing effect of keratin fibers of the present invention. The amount of the propylene glycol included in the composition according to the present invention is not limited, but may be from 0.01 to 30% by weight, preferably from 0.1 to 25% by weight, and more preferably from 1 to 20% by weight relative to the total weight of the composition according to the present invention.
The composition according to the present invention may comprise at least one oxidizing agent.
The oxidizing agent may be chosen from hydrogen peroxide, peroxygenated salts, and compounds capable of producing hydrogen peroxide by hydrolysis. For example, the oxidizing agent can be chosen from aqueous hydrogen peroxide solution, urea peroxide, alkali metal bromates and ferricyanides and persalts such as perborates and persulphates. At least one oxidase enzyme chosen, for example, from laccases, peroxidases and 2-electron oxidoreductases such as uricase may also be used as the oxidizing agent, where appropriate in the presence of the respective donor or co-factor thereof.
In one embodiment, the oxidizing agent is hydrogen peroxide, such as an aqueous hydrogen peroxide solution. The hydrogen peroxide concentration may range from 0.15 wt% to 12 wt% such as from 0.6 wt% to 9 wt% relative to the total weight of the (c) oxidizing agent. The concentration of compounds capable of forming hydrogen peroxide by hydrolysis may range from 0.1 wt% to 25 wt% relative to the total weight of the oxidizing agent. In one embodiment, when the oxidizing agent is an aqueous hydrogen peroxide solution, the aqueous solution may comprise at least one hydrogen peroxide stabilizer, which may be chosen, for example, from alkali metal and alkaline-earth metal pyrophosphates, alkali metal and alkaline-earth metal stannates, phenacetin and salts of acids and of oxyquinoline, for example, oxyquinoline sulphate. In another embodiment, at least one stannate optionally in combination with at least one pyrophosphate is used.
It is also possible to use salicylic acid and its salts, pyridinedicarboxylic acid and its salts, paracetamol. In the oxidizing agent in the form of an aqueous hydrogen peroxide solution, the
concentration of the hydrogen peroxide stabilizer may range from 0.0001 wt% to 5 wt% such as from 0.01 wt% to 2 wt% relative to the total weight of the (c) oxidizing agent.
The amount of the oxidizing agent in the composition according to the present invention may range from 0.01% to 30% by weight, preferably from 0.1% to 20% by weight, and more preferably from 1% to 10% by weight, relative to the total weight of the composition.
The composition according to the present invention may comprise water. The amount of water in the composition according to the present invention may range from 50% to 99% by weight, preferably from 60% to 95% by weight, and more preferably from 70 to 90% by weight, relative to the total weight of the composition.
The composition according to the present invention may also contain various adjuvants conventionally used in compositions for coloring keratin fibers such as hair, such as oils, anionic, non-ionic, cationic, amphoteric or zwitterionic surfactants, or mixtures thereof, antioxidants, thickening agents, sequestering agents, fragrances, dispersing agents, conditioning agents, film-forming agents, ceramides, preservatives, for example, phenoxy ethanol, and opacifying agents.
The amount of the adjuvants included in the composition according to the present invention is not limited, but may be from 0.01 to 30% by weight relative to the total weight of the composition according to the present invention. The form of the composition according to the present invention is not particularly limited, as long as it is water-based, and may take various forms such as an emulsion (O/W or W/O form), an aqueous gel, an aqueous solution, or the like. It is preferable that the composition according to the present invention be in the form of a water-based solution. The composition according to the present invention can be used as a conditioning or a booster composition for use in coloring keratin fibers, for example by dyeing or bleaching the keratin fibers. Thus, the composition according to the present invention can be a cosmetic composition used in combination with compositions for coloring for keratin fibers, such as a composition including at least one oxidizing agent, a composition including at least one alkaline agent, or a combination thereof.
[Composition Including Oxidizing Agent]
The composition according to the present invention including the combination of the (a) malonic acid and the (b) cationic polymer can be used in combination with another composition including at least one oxidizing agent.
Hereafter, the composition including at least one oxidizing agent is referred to as first composition.
The oxidizing agent(s) which can be used in the first composition is (are) the same as explained above.
The first composition may comprise the oxidizing agent(s) in an amount of 0.01% to 30% by weight, preferably 0.1% to 20% by weight, and more preferably 1% to 10% by weight, relative to the total weight of the composition.
[Composition Including Alkaline Agent] The composition according to the present invention further including the oxidizing agent(s) can be used in combination with another composition including at least one alkaline agent.
Hereafter, the composition including at least one alkaline agent is referred to as second composition.
(Alkaline Agent)
The second composition comprises at least one alkaline agent. A single type of alkaline agent may be used, or two or more different types of alkaline agents may be used in combination. As the alkaline agents, mention may be made of any inorganic or organic basic agents which are commonly used in cosmetic products such as ammonia; alkanolamines such as mono-, di- and tri-ethanolamine, isopropanolamine; sodium and potassium hydroxides; urea, guanidine and their derivatives; basic amino acids such as lysine or arginine; and diamines such as those described in the structure below:
Rc
N-R-N
R / R£ wherein R denotes an alkylene such as propylene optionally substituted by a hydroxyl or a C1-C4 alkyl radical, and R3, R4, R5 and R6 independently denote a hydrogen atom, an alkyl radical or a Ci-C4 hydroxyalkyl radical, which may be exemplified by 1 ,3-propanediamine and derivatives thereof. Arginine and monoethanolamine are preferred. The alkaline agent may be used in an amount ranging from 0.001 to 15% by weight, preferably from 0.01 to 10% by weight, and more preferably from 0.1 to 5% by weight, relative to the total weight of the composition.
(Oxidation Dye)
The second composition may comprise at least one oxidation dye. A single type of oxidation dye may be used, or two or more different types of oxidation dyes may be used in
combination. The oxidation dye can be selected from oxidation bases, oxidation couplers, and the acid addition salts thereof.
The oxidation base can be selected from those conventionally known in oxidation dyeing, preferably from the group consisting of ortho- and para-phenylenediamines, double bases, ortho- and para-aminophenols, heterocyclic bases and the acid addition salts thereof.
There may be mentioned in particular:
- (I) the para-phenylenediamines of the following formula (I) and their addition salts with an acid:
Figure imgf000021_0001
in which:
Ri represents a hydrogen atom, a d-C4 alkyl radical, a monohydroxy(C!-C4 alkyl) radical, a polyhydroxy-(C2-C4 alkyl) radical, a (C1-C4)alkoxy(C1-C4)alkyl radical, a d-C4 alkylradical substituted with a nitrogen-containing group, a phenyl radical or a 4'-aminophenyl radical; R2 represents a hydrogen atom, a C1-C4 alkyl radical, a monohydroxy(Ci-C4 alkyl) radical, a polyhydroxy(C2-C4 alkyl) radical, a (C1-C4)alkoxy(C1-C4)alkyl radical or a Ci-C4 alkyl radical substituted with a nitrogen-containing group;
Ri and R2 may also form with the nitrogen atom carrying them a 5- or 6-membered nitrogen-containing heterocycle optionally substituted with one or more alkyl, hydroxyl or ureido groups;
R3 represents a hydrogen atom, a halogen atom such as a chlorine atom, a Ci-C4 alkyl radical, a sulpho radical, a carboxyl radical, a monohydroxy(C!-C4 alkyl) radical, a hydroxy(Ci-C4 alkoxy) radical, an acetylamino(C!-C4 alkoxy) radical, a mesylamino(Ci-C4 alkoxy) radical or a carbamoylamino(d-C4 alkoxy) radical; and
R4 represents a hydrogen or halogen atom or a C1-C4 alkyl radical.
Among the nitrogen-containing groups of formula (I) above, there may be mentioned in particular the amino, mono(Ci-C4)alkylamino, (Ci -C4)dialkylamino, (Ci-C4)trialkylamino, monohydroxy(Ci-C4)alkylamino, di(monohydroxy(Ci-C4)alkyl)amino, imidazolinium and ammonium radicals.
Among the para-phenylenediamines of formula (I) above, there may be mentioned more particularly para-phenylenediamine, para-tolylenediamine, 2-chloro-paraphenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine,
2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para-phenylenediamine,
Ν,Ν-dimethylpara-phenylenediamine, N,N-diethyl-para-phenylenediamine,
Ν,Ν-dipropyl-paraphenylenediamine, 4-amino-N,N-diethyl-3-methylaniline,
N,N-bis(P-hydroxyethyl)-paraphenylenediamine,
4-N,N-bis(P-hydroxyethyl)amino-2-methylaniline,
4-N,N-bis(P-hydroxyethyl)amino-2-chloroaniline, 2-P-hydroxyethyl-para-phenylenediamine, 2-fluoro-paraphenylenediamine, 2-isopropyl-para-phenylenediamine,
N-( -hydroxypropyl)-paraphenylenediamine, 2-hydroxymethyl-para-phenylenediamine, N,N-dimethyl-3-methylpara-phenylenediamine,
N,N-(ethyl- -hydroxyethyl)-para-phenylenediamine,
N-( ,y-dihydroxypropyl)-para-phenylenediamine,
N-(4'-aminophenyl)-para-phenylenediamine, N-phenyl-para-phenylenediamine,
2-P-hydroxyethyloxy-para-phenylenediamine,
2-P-acetylamino-ethyloxy-para-phenylenediamine,
N-( -methoxyethyl)-para-phenylenediamine,
2-methyl- 1 -Ν-β-hydroxyethyl-para-phenylenediamine,
N-(4-aminophenyl)-3 -hydroxy-pyrrolidine,
2-[{2-[(4-Aminophenyl)amino]ethyl}(2-hydroxyethyl)amino]-ethanol, and their addition salts with an acid.
Among the para-phenylenediamines of formula (I) above, there are most particularly preferred para-phenylenediamine, para-tolylenediamine, 2-isopropyl-paraphenylenediamine, 2- -hydroxyethyl-para-phenylenediamine, 2-P-hydroxyethyloxy-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine,
2,3-dimethyl-para-phenylenediamine, N,N-bis(P-hydroxyethyl)-para-phenylenediamine, 2-chloro-para-phenylenediamine, and their addition salts with an acid.
- (II) According to the present invention, the term "double bases" is understood to mean compounds containing at least two aromatic rings on which amino and/or hydroxyl groups are carried.
Among the double bases which can be used as oxidation bases in the dyeing compositions in accordance with the present invention, there may be mentioned in particular compounds corresponding to the following formula (II), and their addition salts with an acid:
Figure imgf000023_0001
in which:
- Zi and Z2, which are identical or different, represent a hydroxyl or -NH2 radical which may be substituted with a Ci-C4 alkyl radical or with a linking arm Y;
- the linking arm Y represents a linear or branched alkylene chain comprising from 1 to 14 carbon atoms, which may be interrupted by or which may end with one or more
nitrogen-containing groups and/or one or more heteroatoms such as oxygen, sulphur or nitrogen atoms, and optionally substituted with one or more hydroxyl or Ci-C6 alkoxy radicals;
- R.5 and R6 represent a hydrogen or halogen atom, a C1-C4 alkyl radical, a
monohydroxy(C!-C4 alkyl) radical, a polyhydroxy(C2-C4 alkyl) radical, an amino(C1-C4 alkyl) radical or a linking arm Y;
- R.7, Rs, Rs>, Rio, Rii and Ri2, which are identical or different, represent a hydrogen atom, a linking arm Y or a C1-C4 alkyl radical; it being understood that the compounds of formula (II) contain only one linking arm Y per molecule, Among the nitrogen-containing groups of formula (II) above, there may be mentioned in particular the amino, mono(Ci-C4)alkylamino, (Ci-C4)dialkylamino, (Ci-C4)trialkylamino, monohydroxy(C1-C4)alkylamino, imidazolinium and ammonium radicals.
Among the double bases of formulae (II) above, there may be mentioned more particularly N,N'-bis(P-hydroxyethyl)-N,N'-bis(4'-aminophenyl)-l,3-diaminopropanol,
N,N'-bis( -hydroxyethyl)-N,N'-bis(4'-aminophenyl)ethylenediamine,
N,N'-bis(4-aminophenyl)-tetramethylenediamine,
N,N'-bis(P-hydroxyethyl)-N,N'-bis(4-aminophenyl)tetramethylenediamine,
N,N'-bis(4-methylaminophenyl)tetramethylenediamine,
N,N'-bis(ethyl)-N,N'-bis(4'-amino-3'-methylphenyl)ethylene-diamine,
l,8-bis(2,5-diaminophenoxy)-3,5-dioxaoctane, and their addition salts with an acid.
Among these double bases of formula (II),
N,N'-bis(P-hydroxyethyl)-N,N'-bis(4'-aminophenyl)-l,3-diaminopropanol,
1 ,8-bis(2,5-diaminophenoxy)-3,5-dioxaoctane or one of their addition salts with an acid are particularly preferred.
- (HI) The para-aminophenols corresponding to the following formula (III), and their addition salts with an acid:
Figure imgf000024_0001
in which:
- Ri3 represents a hydrogen atom, or a halogen atom such as fluorine, a Ci-C4 alkyl, monohydroxy(Ci-C4 alkyl), (Ci-C4)alkoxy(C1-C4)-alkyl, amino(Ci-C4 alkyl) or
hydroxy(Ci-C4)alkylamino-(Ci-C4 alkyl) radical,
- Ri4 represents a hydrogen atom, or a halogen atom such as fluorine, a Ci-C4 alkyl, monohydroxy(G-C4 alkyl), polyhydroxy(C2-C4 alkyl), amino(Ci-C4 alkyl), cyano(Ci-C4 alkyl) or (C1-C4)alkoxy(Ci-C4)alkyl radical.
Among the para-aminophenols of formula (III) above, there may be mentioned more particularly para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol,
4-amino-3 -hydro xymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol,
4- amino-2-( -hydroxyethylaminomethyl)phenol, and their addition salts with an acid.
- (IV) The ortho-aminophenols which can be used as oxidation bases in the context of the present invention are chosen in particular from 2-aminophenol,
2- amino- 1 -hydroxy-5-methylbenzene, 2-amino- 1 -hydroxy-6-methylbenzene,
5- acetamido-2-aminophenol, and their addition salts with acid.
-(V) Among the heterocyclic bases which can be used as oxidation bases in the dyeing compositions in accordance with the present invention, there may be mentioned more particularly pyridine derivatives, pyrimidine derivatives, pyrazole derivatives, and their addition salts with an acid.
Among the pyridine derivatives, there may be mentioned more particularly the compounds described for example in Patents GB 1,026,978 and GB 1,153,196, such as
2,5-diaminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine,
2.3- diamino-6-methoxypyridine, 2-(P-methoxyethyl)amino-3-amino-6-methoxypyridine,
3.4- diaminopyridine, and their addition salts with an acid. Among the pyrimidine derivatives, there may be mentioned more particularly the compounds described, for example, in Patents DE 2 359 399; JP 88-169571 ; and JP 91-10659 or patent application WO 96/15765, such as 2,4,5, 6-tetraaminopyrimidine,
4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine,
2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triamino-pyrimidine, and the pyrazolopyrimidine derivatives such as those mentioned in patent application FR-A-2 750 048 and among which there may be mentioned pyrazolo[l,5-a]-pyrimidine-3,7-diamine;
2,5 -dimethyl-pyrazolo [ 1 ,5 -a] -pyrimidine-3 ,7-diamine;
pyrazolo[l,5-a]pyrimidine-3,5-diamine; 2,7-dimethylpyrazolo[l,5-a]pyrimidine-3,5-diamine;
3- aminopyrazolo[l ,5-a]pyrimidin-7-ol; 3-amino-pyrazolo[l ,5-a]pyrimidin-5-ol;
2-(3-amino-pyrazolo-[l ,5-a]pyrimidin-7-ylamino)ethanol, 2-(7-aminopyrazolo[l,5-a]pyrimidin-3-ylamino)ethanol,
2- [(3 -amino-pyrazolo [ 1 ,5 -a]pyrimidin-7-yl)-(2-hydroxy-ethyl)amino] -ethanol,
2- [(7-arninopyrazolo[l,5-a]-pyrimidin-3-yl)-(2-hydroxyethyl)amino]ethanol,
5,6-dimetliylpyrazolo-[l,5-a]pyrimidine-3,7-diamine,
2,6-dimethylpyrazolo-[l,5-a]pyrimidine-3,7-diamine,
2,5 ,N7,N7-tetramethyl-pyrazolo [ 1 ,5 -a]pyrimidine-3 ,7-diamine,
3- amino-5-methyl-7-imidazolylpropyl-aminopyrazolo[l,5-a]-pyrimidine, their addition salts and their tautomeric forms when a tautomeric equilibrium exists, and their addition salts with an acid.
Among the pyrazole derivatives, there may be mentioned more particularly the compounds described in Patents DE 3 843 892, and DE 4 133 957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988 such as 4,5-diamino-l-methylpyrazole,
3.4- diaminopyrazole, 4,5-diamino- 1 -(4' -chlorobenzyl)-pyrazole,
4,5-diamino- 1 ,3-dimethylpyrazole, 4,5-diamino-3-methyl- 1 -phenylpyrazole,
4.5- diamino-l-methyl-3-phenylpyrazole, 4-amino-l,3-dimethyl-5-hydrazino-pyrazole, 1 -benzyl-4,5-diamino-3-methyl-pyrazole, 4,5-diamino-3-tert-butyl- 1 -methylpyrazole,
4,5-diamino-l-tertbutyl-3-methylpyrazole, 4,5-diamino-l-(P-hydroxyethyl)-3-methylpyrazole, 4,5-diamino- l-(p-hydroxyethyl)pyrazole, 4,5-diamino-l-ethyl-3-methylpyrazole,
4,5-diamino-l-ethyl-3-(4'-methoxyphenyl)pyrazole,
4,5-diamino- 1 -ethyl-3 -hydroxy-methylpyrazole,
4,5-diamino-3-hydroxymethyl- 1 -methylpyrazole,
4,5-diamino-3-hydroxymethyl- 1 -isopropyl-pyrazole,
4,5-diamino-3 -methyl- 1 -isopropyl-pyrazole,
4-amino-5-(2'-aminoethyl)amino-l,3-dimethylpyrazole, 3,4,5-triaminopyrazole,
1 -methyl-3,4,5-triamino-pyrazole, 3,5-diamino- 1 -methyl-4-methylaminopyrazole,
3,5-diamino-4-( -hydroxy-ethyl)amino-l-methylpyrazole, and their addition salts with an acid. Among the heterocyclic bases which can be used as oxidation bases, there may be mentioned more particularly diaminopyrazolopyrazolones and especially
2,3-diamino-6,7-dihydro-lH5H-[pyrazolol,2,a]pyrazol-l-one and the addition salts of these diaminopyrazolopyrazolones with an acid. The oxidation dye may be an oxidation coupler which can be selected from those
conventionally known in oxidation dyeing, preferably from the group consisting of
meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthols, heterocyclic couplers and the acid addition salts thereof. The heterocyclic couplers may be selected from the group consisting of indole derivatives, indoline derivatives, sesamol and its derivatives, pyridine derivatives, pyrazolotriazole derivatives, pyrazolones, indazoles, benzimidazoles, benzothiazoles, benzoxazoles,
1,3-benzodioxoles, quinolines and their addition salts with an acid. These couplers are more particularly chosen from 2,4-diamino-l-(P-hydroxyethyloxy)benzene, 2-methyl-5-aminophenol, 5-N-( -hydroxyethyl)amino-2-methylphenol, 3-aminophenol, 2-chloro-3-amino-6-methylphenol, 1 ,3-dihydroxybenzene, 1 ,3-dihydroxy-2-methylbenzene,
4- chloro-l,3-dihydroxybenzene, 2-amino-4-(P-hydroxyethylamino)-l-methoxybenzene, 1 ,3-diaminobenzene, 2-methyl-5-hydroxyethylaminophenol, 4-amino-2-hydroxytoluene, l,3-bis(2,4-diaminophenoxy)-propane, sesamol, 1 -amino-2-methoxy-4,5-methylene-dioxybenzene, α-naphthol, 6-hydroxyindole,
4-hydroxyindole, 4-hydroxy-N-methylindole, 6-hydroxy-indoline,
2,6-dihydroxy-4-methylpyridine, 1 -H-3-methylpyrazol-5-one,
1 -phenyl-3-methylpyrazol-5-one, 2-amino-3 -hydro xypyridine,
3,6-dimethyl-pyrazolo[3,2-c]-l,2,4-triazole, 2,6-dimethylpyrazolo[l,5-b]-l,2,4-triazole and their addition salts with an acid.
In general, the addition acid salts of the oxidation bases and couplers are chosen in particular from hydrochlorides, hydrobromides, sulphates, tartrates, lactates and acetates.
The second composition may comprise an oxidation dye or dyes in an amount of 0.0001 to 20 wt%, preferably 0.0005 to 15 wt%, and more preferably 0.005 to 10 wt%, relative to the total weight of the composition. (Optional Ingredients)
The first and second compositions may also contain various adjuvants conventionally used in compositions for coloring keratin fibers such as hair, such as oils, anionic, non-ionic, cationic, amphoteric or zwitterionic surfactants, or mixtures thereof, anionic, non-ionic, cationic, amphoteric or zwitterionic polymers, or mixtures thereof, antioxidants, neutralizers, thickening agents, sequestering agents, stabilizers, pH adjusting agents, fragrances, dispersing agents, conditioning agents, film-forming agents, ceramides, preservatives and opacifying agents. The first and second compositions may comprise water.
The amount of water in the first and second compositions may range from 50% to 99% by weight, preferably from 60% to 95% by weight, and more preferably from 70 to 90% by weight, relative to the total weight of the composition.
The form of the first and second compositions is not particularly limited, as long as it is water-based, and may take various forms such as an emulsion (O/W or W/O form), an aqueous gel, an aqueous solution, or the like. It is preferable that the first and second compositions be in the form of a water-based solution.
[Preparation]
The composition according to the present invention can be prepared by mixing the ingredients (a) and (b), as essential ingredients, and optional ingredient(s), if necessary, as explained above.
If the composition according to the present invention is used in combination with the first composition, the composition according to the present invention can be mixed with the first composition for its use. The first composition can be prepared by mixing oxidizing agent(s), as essential ingredient(s), and optional ingredient(s), if necessary, as explained above. The mixing ratio of the composition according to the present invention and the first composition is not limited. The mixing ratio may be 1 :50 to 1 : 1, preferably 1 :40 to 1 :2, and more preferably 1 :30 to 1 :5, as weight ratio.
If the composition according to the present invention is used in combination with the first and second compositions, the composition according to the present invention can be mixed with the first and second compositions for its use. The second composition can be prepared by mixing the alkaline agent(s), as essential ingredient(s), and optional ingredient(s), if necessary, as explained above. The mixing ratio of the composition according to the present invention, the first composition, and the second composition is not limited. The mixing ratio may be 1 :50:50 to 1 : 1 :1, preferably 1 :40:40 to 1 :2:2, and more preferably 1 :30:30 to 1 :5:5, as weight ratio.
The method and means to mix the above essential and optional ingredients are not limited. Any conventional method and means can be used to mix the above essential and optional ingredients to prepare the first or second composition.
[Ready-To-Use Composition] The present invention also relates to a ready-to-use cosmetic composition for keratin fibers, preferably hair, comprising:
the composition according to the present invention,
the first composition comprising at least one oxidizing agent, and
the second composition comprising at least one alkaline agent.
The ready-to-use composition according to the present invention can be applied, as it is, to keratin fibers such as hair, for coloring the keratin fibers by, for example, dyeing or bleaching the keratin fibers. The ready-to-use composition according to the present invention can be prepared by mixing the composition according to the present invention, the first composition, and the second composition. The mixing ratio of the composition according to the present invention, the first composition, and the second composition is not limited. The mixing ratio may be 1 :50:50 to 1 :1 : 1, preferably 1 :40:40 to 1 :2:2, and more preferably 1 :30:30 to 1 :5:5, as weight ratio.
The (a) malonic acid may be present in the ready-to-use composition according to the present invention in an amount of 0.005% by weight or more, preferably 0.025% by weight or more, and more preferably 0.05% by weight or more, relative to the total weight of the composition. The (a) malonic acid may be present in the ready-to-use composition according to the present invention in an amount of 1% by weight or less, preferably 0.75% by weight or less, and more preferably 0.5% by weight or less, relative to the total weight of the composition.
The amount of the (a) malonic acid in the ready-to-use composition according to the present invention may range from 0.005% to 1% by weight, preferably from 0.025% to 0.75% by weight, and more preferably from 0.05% to 0.5% by weight, relative to the total weight of the composition.
The (b) cationic polymer may be present in the ready-to-use composition according to the present invention in an amount of 0.025% by weight or more, preferably 0.05% by weight or more, and more preferably 0.075% by weight or more, relative to the total weight of the composition. The (b) cationic polymer may be present in the ready-to-use composition according to the present invention in an amount of 1.5% by weight or less, preferably 1% by weight or less, and more preferably 0.75% by weight or less, relative to the total weight of the composition.
The amount of the (b) cationic polymer present in the ready-to-use composition may range from 0.025% to 1.5% by weight, preferably from 0.05% to 1% by weight, and more preferably from 0.075% to 0.75% by weight, relative to the total weight of the composition.
[Kit and Process]
The present invention also relates to a kit for keratin fibers, preferably hair, comprising: a first compartment comprising the first composition comprising at least one oxidizing agent, a second compartment comprising the second composition comprising at least one alkaline agent, and
a third compartment comprising the composition according to the present invention. It is possible to use the kit by, for example, dispensing or discharging the first composition from the first compartment, while dispensing or discharging the second composition from the second compartment and/or dispensing or discharging the composition according to the present invention from the third compartment, followed by treating keratin fibers such as hair with the mixture of the first and second compositions and the composition according to the present invention.
In another embodiment, the composition according to the present invention can be mixed with at least one oxidizing agent before it is charged in a compartment of the kit. Therefore, the present invention also relates to a kit for keratin fibers, preferably hair, comprising:
a first compartment comprising the composition according to the present invention pre-mixed with at least one oxidizing agent, and
a second compartment comprising the second composition comprising at least one alkaline agent.
The present invention also relates to a cosmetic process for keratin fibers, preferably hair, comprising the steps of:
(1) mixing:
the composition according to the present invention,
the first composition comprising at least one oxidizing agent, and
the second composition comprising at least one alkaline agent to prepare the ready-to-use cosmetic composition, and
(2) applying the ready-to-use cosmetic composition to the keratin fibers.
It may be preferable that the cosmetic process according to the present invention comprise a step of washing, with or without drying, keratin fibers before and/or after the step of applying the ready-to-use cosmetic composition onto the keratin fibers. The step of applying the ready-to-use cosmetic composition onto the keratin fibers can be performed by a conventional applicator such as a brush, or even by the hands.
The keratin fibers to which the ready-to-use cosmetic composition has been applied can be left for an appropriate time which is required to treat the keratin fibers. The time length for the treatment is not limited, but it may be from 1 minute to 1 hour, preferably 1 minute to 30 minutes, and more preferably 1 minute to 15 minutes. For example, the time for dyeing the keratin fibers may be from 1 to 20 minutes, preferably 5 to 15 minutes.
The keratin fibers may be treated at room temperature. Alternatively, the keratin fibers can be heated at 25°C to 65°C, preferably 30°C to 60°C, more preferably 35°C to 55°C, and even more preferably 40°C to 50°C, before and/or during and/or after the step of applying the ready-to-use cosmetic composition onto the keratin fibers.
The present invention may also relate to a use of a combination of:
(a) malonic acid; and
(b) at least one cationic polymer
in a composition for coloring or bleaching keratin fibers, preferably in a composition for coloring keratin fibers comprising at least one oxidizing agent to prevent or reduce the loss of volume of keratin fibers when the keratin fibers are colored with the above composition for keratin fibers, with or without another composition including at least one alkaline agent, and/or when the colored keratin fibers are washed.
The above coloring is preferably for cosmetic purposes for the keratin fibers, for example, dyeing or bleaching the keratin fibers, preferably hair.
EXAMPLES
The present invention will be described in a more detailed manner by way of examples. However, these examples should not be construed as limiting the scope of the present invention.
Example 1 and Comparative Examples 1 to 3
[Preparation]
Each of the compositions according to Example Γ (Ex. 1) and Comparative Examples 1 to 3 (Comp. Ex. 1 to Comp. Ex. 3) was prepared by mixing the ingredients shown in Table 1. The numerical values for the amounts of the ingredients are all based on "% by weight" as active raw materials. Polyquaternium-11 was purchased from the company I.S.P. (Ashland).
[Evaluations] (Volumizing Effects) 0.6 g of each of the compositions according to Example 1 and Comparative Examples 1 to 3 was mixed with 6 g of Composition A and 6g of Composition B with the following formulations. Therefore the weight ratio of each of the compositions according to Example 1 and Comparative Examples 1 to 3 : Composition A : Composition B was 1 : 10: 10. Composition A
Figure imgf000030_0001
Three hair swatches (1 g, 20 cm) were prepared for each experiment. 4 g of the mixture obtained as above was applied onto 1 g of hair swatch for each sample. The swatch was then left for 30 minutes at room temperature, followed by shampooing and rinsing with tap water. The swatch was hung downwardly and dried at 25 °C under relative humidity of 30-50% over night. The dried swatch was cut such that the length between the root of the swatch and the cut point (tip of the swatch) was 15 cm. The root of the swatch was fixed on a plate. On the other hand, the tip of the swatch was held and oriented upwardly, and the tip of the swatch was then released such that the tip of the swatch could point downwardly. The vertical angle between the plate and the tip of the hair fiber was measured (cf. Fig. 1). The average value of the three swatches was determined for the vertical angle with regard to the hair fibers in the swatch.
The larger the vertical angle is, the better the volumizing effect is. The measured vertical angle was evaluated in accordance with the evaluation criteria shown below.
Good: over 80° Fair: 77-80°
Poor: less than 77°
The results are shown in Table 1.
(Long Lasting Effects)
The swatch used in the evaluation of the above "Volumizing Effects" was shampooed five times. The swatch was hung downwardly and dried overnight at 25 °C under relative humidity of 30-50%. The root of the swatch was fixed on a plate. On the other hand, the tip of the swatch was held and oriented upwardly, and the tip of the swatch was then released such that the tip of the swatch could point downwardly. The vertical angle between the plate and the tip of the hair fiber was measured (cf. Fig. 1). The average value of the three swatches was determined for the vertical angle with regard to the hair fibers in the swatch.
The larger the vertical angle is, the better the long lasting effect is. The measured vertical angle was evaluated in accordance with the evaluation criteria shown below.
Good: over 80°
Fair: 77-80°
Poor: less than 77°
The results are shown in Table 1.
Table 1
Figure imgf000031_0001
It can be recognized from the comparisons of Example 1 and Comparative Examples 1 to 3, shown in Table 1 , that, when a composition for keratin fibers such as hair contains malonic acid and a cationic polymer such as polyquaternium- 11, the composition can improve both volumizing and long-lasting effects. On the other hand, the composition according to Comparative Example 1, which does not include malonic acid, showed good long lasting effects but did not show good volumizing effects. The composition according to
Comparative Example 2, which includes citric acid instead of malonic acid, did not show good volumizing effects and showed inferior long lasting effects. Similarly, the composition according to Comparative Example 3, which does not include any cationic polymer, did not show good volumizing effects and showed inferior long lasting effects.
Therefore, it can be concluded that the composition according to the present invention can be very preferable for use to impart hair volumizing effects and long lasting effects to colored keratin fibers.

Claims

A composition for use in coloring or bleaching keratin fibers, preferably hair, comprising:
(a) malonic acid; and
(b) at least one cationic polymer.
The composition according to Claim 1, wherein the (b) cationic polymer has a unit derived from vinylpyrrolidone.
3. The composition according to Claim 2, wherein the (b) cationic polymer is selected from
copolymers comprising vinylpyrrolidone units and dimethylaminoethyl methacrylate units,
copolymers comprising vinylpyrrolidone units and
ethacrylamidopropyltrimethylammonium units, and
copolymers comprising vinylpyrrolidone units and methylvinylimidazolium units. 4. The composition according to Claim 3, wherein the copolymers comprising
vinylpyrrolidone units and dimethylaminoethyl methacrylate units are chosen from: vinylpyrrolidone/dimethylaminoethyl methacrylate copolymers;
vinylpyrrolidone/dimethylaminoethyl methacrylate copolymers quaternized with diethyl sulphate;
vinylpyrrolidone/ dimethylaminoethyl methacrylate/hydrophilic polyurethane copolymers;
quaternized or non-quaternized vinylpyrrolidone/dimethylaminoethyl methacrylate/C8-Ci6 olefin copolymers; and
vinylpyrrolidone/dimethylaminoethyl methacrylate/vinylcaprolactam copolymers.
Figure imgf000033_0001
The composition according to any one of Claims 1 to 4, wherein the amount of the
(a) malonic acid ranges from 0.1% to 20% by weight, preferably from 0.5% to 15% by weight, and more preferably from 1% to 10% by weight, relative to the total weight of the composition.
Figure imgf000033_0002
The composition according to any one of Claims 1 to 5, wherein the amount of the
(b) cationic polymer ranges from 0.5% to 30% by weight, preferably from 1% to 20% by weight, and more preferably from 1.5% to 15% by weight, relative to the total weight of the composition.
The composition according to any one of Claims 1 to 6, further comprising propylene glycol.
The composition according to Claim 7, wherein the amount of the propylene glycol ranges from 0.01 to 30% by weight, preferably from 0.1 to 25% by weight, and more preferably from 1 to 20% by weight relative to the total weight of the composition.
The composition according to any one of Claims 1 to 8, comprising at least one oxidizing agent.
10. The composition according to Claim 9, wherein the oxidizing agent is hydrogen peroxide.
11. The composition according to Claim 9 or 10, wherein the amount of the oxidizing agent ranges from 0.01% to 30% by weight, preferably from 0.1% to 20% by weight, and more preferably from 1% to 10% by weight, relative to the total weight of the composition.
12. A ready-to-use cosmetic composition for keratin fibers, preferably hair, comprising: the composition according to any one of Claims 1 to 8,
a first composition comprising at least one oxidizing agent, and
a second composition comprising at least one alkaline agent.
13. A kit for keratin fibers, preferably hair, comprising:
a first compartment comprising the composition according to any one of Claims 9 to 11 , and
a second compartment comprising a second composition comprising at least one alkaline agent.
14. A kit for keratin fibers, preferably hair, comprising:
a first compartment comprising a first composition comprising at least one oxidizing agent,
a second compartment comprising a second composition comprising at least one alkaline agent, and
a third compartment comprising the composition according to any one of Claims 1 to 8.
15. A cosmetic process for keratin fibers, preferably hair, comprising the steps of:
(1) mixing:
the composition according to any one of Claims 1 to 8,
a first composition comprising at least one oxidizing agent, and
a second composition comprising at least one alkaline agent to prepare a ready-to-use cosmetic composition, and
(2) applying the ready-to-use cosmetic composition to the keratin fibers.
PCT/JP2018/020086 2017-06-09 2018-05-18 Composition for keratin fibers WO2018225529A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2017-114156 2017-06-09
JP2017114156A JP2018203699A (en) 2017-06-09 2017-06-09 Composition for keratin fibers

Publications (1)

Publication Number Publication Date
WO2018225529A1 true WO2018225529A1 (en) 2018-12-13

Family

ID=62705629

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2018/020086 WO2018225529A1 (en) 2017-06-09 2018-05-18 Composition for keratin fibers

Country Status (2)

Country Link
JP (1) JP2018203699A (en)
WO (1) WO2018225529A1 (en)

Citations (60)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2261002A (en) 1941-06-17 1941-10-28 Du Pont Organic nitrogen compounds
US2271378A (en) 1939-08-30 1942-01-27 Du Pont Pest control
US2273780A (en) 1939-12-30 1942-02-17 Du Pont Wax acryalte ester blends
US2375853A (en) 1942-10-07 1945-05-15 Du Pont Diamine derivatives
US2388614A (en) 1942-05-05 1945-11-06 Du Pont Disinfectant compositions
US2454547A (en) 1946-10-15 1948-11-23 Rohm & Haas Polymeric quaternary ammonium salts
US2961347A (en) 1957-11-13 1960-11-22 Hercules Powder Co Ltd Process for preventing shrinkage and felting of wool
US3206462A (en) 1962-10-31 1965-09-14 Dow Chemical Co Quaternary poly(oxyalkylene)alkylbis(diethylenetriamine) compounds
US3227615A (en) 1962-05-29 1966-01-04 Hercules Powder Co Ltd Process and composition for the permanent waving of hair
GB1026978A (en) 1962-03-30 1966-04-20 Schwarzkopf Verwaltung G M B H Method of dyeing hair
FR1492597A (en) 1965-09-14 1967-08-18 Union Carbide Corp New cellulose ethers containing quaternary nitrogen
GB1153196A (en) 1965-07-07 1969-05-29 Schwarzkopf Verwaltung G M B H Method of Dyeing Hair
FR1583363A (en) 1967-09-28 1969-10-24
US3589578A (en) 1968-01-20 1971-06-29 Monforts Fa A Tension-relieving device for stretchable sheet material
FR2077143A5 (en) 1970-01-30 1971-10-15 Gaf Corp
FR2080759A1 (en) 1970-02-25 1971-11-19 Gillette Co
FR2162025A1 (en) 1971-11-29 1973-07-13 Oreal
FR2190406A2 (en) 1972-06-29 1974-02-01 Gillette Co
US3874870A (en) 1973-12-18 1975-04-01 Mill Master Onyx Corp Microbiocidal polymeric quarternary ammonium compounds
DE2359399A1 (en) 1973-11-29 1975-06-12 Henkel & Cie Gmbh Tetraaminopyrimidines as developers in oxidation hair dyes - esp. used with meta aminophenol couplers for blue shading dyes
FR2252840A1 (en) 1973-11-30 1975-06-27 Oreal
FR2270846A1 (en) 1974-05-16 1975-12-12 Oreal
US3929990A (en) 1973-12-18 1975-12-30 Millmaster Onyx Corp Microbiocidal polymeric quaternary ammonium compounds
FR2280361A2 (en) 1974-08-02 1976-02-27 Oreal HAIR TREATMENT AND CONDITIONING COMPOSITIONS
US3966904A (en) 1974-10-03 1976-06-29 Millmaster Onyx Corporation Quaternary ammonium co-polymers for controlling the proliferation of bacteria
US4001432A (en) 1974-10-29 1977-01-04 Millmaster Onyx Corporation Method of inhibiting the growth of bacteria by the application thereto of capped polymers
US4005193A (en) 1974-08-07 1977-01-25 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
FR2316271A1 (en) 1975-07-04 1977-01-28 Oreal NEW QUATERNIZED POLYMERS, THEIR PREPARATION PROCESS, AND THEIR APPLICATION
FR2320330A1 (en) 1974-01-25 1977-03-04 Calgon Corp COMPOSITION OF FUNCTIONAL IONEN POLYMERS AND THEIR USE
US4025617A (en) 1974-10-03 1977-05-24 Millmaster Onyx Corporation Anti-microbial quaternary ammonium co-polymers
US4025627A (en) 1973-12-18 1977-05-24 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
US4025653A (en) 1975-04-07 1977-05-24 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
US4026945A (en) 1974-10-03 1977-05-31 Millmaster Onyx Corporation Anti-microbial quaternary ammonium co-polymers
US4027020A (en) 1974-10-29 1977-05-31 Millmaster Onyx Corporation Randomly terminated capped polymers
US4031307A (en) 1976-05-03 1977-06-21 Celanese Corporation Cationic polygalactomannan compositions
FR2336434A1 (en) 1975-12-23 1977-07-22 Ciba Geigy Ag QUATERNARY POLYMERIC AMMONIUM SALTS, THEIR PREPARATION PROCESS AND THEIR USE
FR2368508A2 (en) 1977-03-02 1978-05-19 Oreal HAIR CONDITIONING COMPOSITION
FR2383660A1 (en) 1977-03-15 1978-10-13 Oreal COMPOSITION AND PROCESS FOR TREATMENT OF KERATINIC MATERIALS WITH CATIONIC AND ANIONIC POLYMERS
US4131576A (en) 1977-12-15 1978-12-26 National Starch And Chemical Corporation Process for the preparation of graft copolymers of a water soluble monomer and polysaccharide employing a two-phase reaction system
FR2393573A1 (en) 1977-06-10 1979-01-05 Gaf Corp HAIR PREPARATIONS CONTAINING A VINYLPYRROLIDONE COPOLYMER
FR2413907A1 (en) 1977-09-20 1979-08-03 Oreal COSMETIC COMPOSITIONS BASED ON QUATERNARY POLYAMMONIUM POLYMERS
FR2470596A1 (en) 1979-11-28 1981-06-12 Oreal COMPOSITION FOR THE TREATMENT OF KERATIN FIBERS BASED ON AMPHOTERIC POLYMERS AND CATIONIC POLYMERS
EP0080976A1 (en) 1981-11-30 1983-06-08 Ciba-Geigy Ag Mixtures of quaternary polymeric acrylic ammonium salts, quaternary mono- or oligomeric ammonium salts and surfactants, their preparation and their use in cosmetic compositions
FR2519863A1 (en) 1982-01-15 1983-07-22 Oreal COSMETIC COMPOSITION FOR THE TREATMENT OF KERATIN FIBERS AND METHOD FOR THE TREATMENT THEREOF
EP0122324A1 (en) 1983-04-15 1984-10-24 Miranol Inc. Polyquaternary ammonium compounds and cosmetic compositions containing them
FR2598611A1 (en) 1986-05-16 1987-11-20 Oreal COSMETIC COMPOSITIONS CONTAINING A CATIONIC POLYMER AND AN ANIONIC POLYMER AS A THICKENING AGENT
EP0337354A1 (en) 1988-04-12 1989-10-18 Kao Corporation Low-irritation detergent composition
DE3843892A1 (en) 1988-12-24 1990-06-28 Wella Ag OXIDATION HAIR AGENTS CONTAINING DIAMINOPYRAZOL DERIVATIVES AND NEW DIAMINOPYRAZOLE DERIVATIVES
DE4133957A1 (en) 1991-10-14 1993-04-15 Wella Ag HAIR DYE CONTAINING AMINOPYRAZOLE DERIVATIVES AND NEW PYRAZOLE DERIVATIVES
WO1994008970A1 (en) 1992-10-16 1994-04-28 Wella Aktiengesellschaft Oxidation hair dye containing 4,5-diaminopyrazole derivatives and novel 4,5-diaminopyrazole derivatives and process for their production
WO1994008969A1 (en) 1992-10-16 1994-04-28 Wella Aktiengesellschaft Process for producing 4,5-diamino pyrazole derivatives, their use for colouring hair and novel pyrazole derivatives
WO1996015765A1 (en) 1994-11-17 1996-05-30 Henkel Kommanditgesellschaft Auf Aktien Oxidation dyes
FR2733749A1 (en) 1995-05-05 1996-11-08 Oreal COMPOSITIONS FOR DYEING KERATINIC FIBERS CONTAINING DIAMINO PYRAZOLES, DYEING PROCESS, NOVEL DIAMINO PYRAZOLES, AND PREPARATION METHOD THEREOF
DE19543988A1 (en) 1995-11-25 1997-05-28 Wella Ag Oxidative hair dye composition
FR2750048A1 (en) 1996-06-21 1997-12-26 Oreal KERATIN FIBER DYEING COMPOSITIONS CONTAINING PYRAZOLO- (1,5-A) -PYRIMIDINE DERIVATIVES, DYEING PROCESS, NOVEL PYRAZOLO- (1,5-A) -PYRIMIDINE DERIVATIVES AND PROCESS FOR PREPARING THE SAME
WO2005000903A1 (en) 2003-06-17 2005-01-06 Union Carbide Chemicals & Plastics Technology Corporation Cellulose ethers
JP2005145890A (en) * 2003-11-17 2005-06-09 Kao Corp Composition for photobleaching hair
US20060115440A1 (en) * 2004-09-07 2006-06-01 Arata Andrew B Silver dihydrogen citrate compositions
WO2017091797A1 (en) * 2015-11-24 2017-06-01 L'oreal Compositions for treating the hair
WO2018081399A1 (en) * 2016-10-31 2018-05-03 L'oreal Compositions for chemically treated hair

Patent Citations (60)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2271378A (en) 1939-08-30 1942-01-27 Du Pont Pest control
US2273780A (en) 1939-12-30 1942-02-17 Du Pont Wax acryalte ester blends
US2261002A (en) 1941-06-17 1941-10-28 Du Pont Organic nitrogen compounds
US2388614A (en) 1942-05-05 1945-11-06 Du Pont Disinfectant compositions
US2375853A (en) 1942-10-07 1945-05-15 Du Pont Diamine derivatives
US2454547A (en) 1946-10-15 1948-11-23 Rohm & Haas Polymeric quaternary ammonium salts
US2961347A (en) 1957-11-13 1960-11-22 Hercules Powder Co Ltd Process for preventing shrinkage and felting of wool
GB1026978A (en) 1962-03-30 1966-04-20 Schwarzkopf Verwaltung G M B H Method of dyeing hair
US3227615A (en) 1962-05-29 1966-01-04 Hercules Powder Co Ltd Process and composition for the permanent waving of hair
US3206462A (en) 1962-10-31 1965-09-14 Dow Chemical Co Quaternary poly(oxyalkylene)alkylbis(diethylenetriamine) compounds
GB1153196A (en) 1965-07-07 1969-05-29 Schwarzkopf Verwaltung G M B H Method of Dyeing Hair
FR1492597A (en) 1965-09-14 1967-08-18 Union Carbide Corp New cellulose ethers containing quaternary nitrogen
FR1583363A (en) 1967-09-28 1969-10-24
US3589578A (en) 1968-01-20 1971-06-29 Monforts Fa A Tension-relieving device for stretchable sheet material
FR2077143A5 (en) 1970-01-30 1971-10-15 Gaf Corp
FR2080759A1 (en) 1970-02-25 1971-11-19 Gillette Co
FR2162025A1 (en) 1971-11-29 1973-07-13 Oreal
FR2190406A2 (en) 1972-06-29 1974-02-01 Gillette Co
DE2359399A1 (en) 1973-11-29 1975-06-12 Henkel & Cie Gmbh Tetraaminopyrimidines as developers in oxidation hair dyes - esp. used with meta aminophenol couplers for blue shading dyes
FR2252840A1 (en) 1973-11-30 1975-06-27 Oreal
US3874870A (en) 1973-12-18 1975-04-01 Mill Master Onyx Corp Microbiocidal polymeric quarternary ammonium compounds
US3929990A (en) 1973-12-18 1975-12-30 Millmaster Onyx Corp Microbiocidal polymeric quaternary ammonium compounds
US4025627A (en) 1973-12-18 1977-05-24 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
FR2320330A1 (en) 1974-01-25 1977-03-04 Calgon Corp COMPOSITION OF FUNCTIONAL IONEN POLYMERS AND THEIR USE
FR2270846A1 (en) 1974-05-16 1975-12-12 Oreal
FR2280361A2 (en) 1974-08-02 1976-02-27 Oreal HAIR TREATMENT AND CONDITIONING COMPOSITIONS
US4005193A (en) 1974-08-07 1977-01-25 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
US4025617A (en) 1974-10-03 1977-05-24 Millmaster Onyx Corporation Anti-microbial quaternary ammonium co-polymers
US3966904A (en) 1974-10-03 1976-06-29 Millmaster Onyx Corporation Quaternary ammonium co-polymers for controlling the proliferation of bacteria
US4026945A (en) 1974-10-03 1977-05-31 Millmaster Onyx Corporation Anti-microbial quaternary ammonium co-polymers
US4001432A (en) 1974-10-29 1977-01-04 Millmaster Onyx Corporation Method of inhibiting the growth of bacteria by the application thereto of capped polymers
US4027020A (en) 1974-10-29 1977-05-31 Millmaster Onyx Corporation Randomly terminated capped polymers
US4025653A (en) 1975-04-07 1977-05-24 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
FR2316271A1 (en) 1975-07-04 1977-01-28 Oreal NEW QUATERNIZED POLYMERS, THEIR PREPARATION PROCESS, AND THEIR APPLICATION
FR2336434A1 (en) 1975-12-23 1977-07-22 Ciba Geigy Ag QUATERNARY POLYMERIC AMMONIUM SALTS, THEIR PREPARATION PROCESS AND THEIR USE
US4031307A (en) 1976-05-03 1977-06-21 Celanese Corporation Cationic polygalactomannan compositions
FR2368508A2 (en) 1977-03-02 1978-05-19 Oreal HAIR CONDITIONING COMPOSITION
FR2383660A1 (en) 1977-03-15 1978-10-13 Oreal COMPOSITION AND PROCESS FOR TREATMENT OF KERATINIC MATERIALS WITH CATIONIC AND ANIONIC POLYMERS
FR2393573A1 (en) 1977-06-10 1979-01-05 Gaf Corp HAIR PREPARATIONS CONTAINING A VINYLPYRROLIDONE COPOLYMER
FR2413907A1 (en) 1977-09-20 1979-08-03 Oreal COSMETIC COMPOSITIONS BASED ON QUATERNARY POLYAMMONIUM POLYMERS
US4131576A (en) 1977-12-15 1978-12-26 National Starch And Chemical Corporation Process for the preparation of graft copolymers of a water soluble monomer and polysaccharide employing a two-phase reaction system
FR2470596A1 (en) 1979-11-28 1981-06-12 Oreal COMPOSITION FOR THE TREATMENT OF KERATIN FIBERS BASED ON AMPHOTERIC POLYMERS AND CATIONIC POLYMERS
EP0080976A1 (en) 1981-11-30 1983-06-08 Ciba-Geigy Ag Mixtures of quaternary polymeric acrylic ammonium salts, quaternary mono- or oligomeric ammonium salts and surfactants, their preparation and their use in cosmetic compositions
FR2519863A1 (en) 1982-01-15 1983-07-22 Oreal COSMETIC COMPOSITION FOR THE TREATMENT OF KERATIN FIBERS AND METHOD FOR THE TREATMENT THEREOF
EP0122324A1 (en) 1983-04-15 1984-10-24 Miranol Inc. Polyquaternary ammonium compounds and cosmetic compositions containing them
FR2598611A1 (en) 1986-05-16 1987-11-20 Oreal COSMETIC COMPOSITIONS CONTAINING A CATIONIC POLYMER AND AN ANIONIC POLYMER AS A THICKENING AGENT
EP0337354A1 (en) 1988-04-12 1989-10-18 Kao Corporation Low-irritation detergent composition
DE3843892A1 (en) 1988-12-24 1990-06-28 Wella Ag OXIDATION HAIR AGENTS CONTAINING DIAMINOPYRAZOL DERIVATIVES AND NEW DIAMINOPYRAZOLE DERIVATIVES
DE4133957A1 (en) 1991-10-14 1993-04-15 Wella Ag HAIR DYE CONTAINING AMINOPYRAZOLE DERIVATIVES AND NEW PYRAZOLE DERIVATIVES
WO1994008970A1 (en) 1992-10-16 1994-04-28 Wella Aktiengesellschaft Oxidation hair dye containing 4,5-diaminopyrazole derivatives and novel 4,5-diaminopyrazole derivatives and process for their production
WO1994008969A1 (en) 1992-10-16 1994-04-28 Wella Aktiengesellschaft Process for producing 4,5-diamino pyrazole derivatives, their use for colouring hair and novel pyrazole derivatives
WO1996015765A1 (en) 1994-11-17 1996-05-30 Henkel Kommanditgesellschaft Auf Aktien Oxidation dyes
FR2733749A1 (en) 1995-05-05 1996-11-08 Oreal COMPOSITIONS FOR DYEING KERATINIC FIBERS CONTAINING DIAMINO PYRAZOLES, DYEING PROCESS, NOVEL DIAMINO PYRAZOLES, AND PREPARATION METHOD THEREOF
DE19543988A1 (en) 1995-11-25 1997-05-28 Wella Ag Oxidative hair dye composition
FR2750048A1 (en) 1996-06-21 1997-12-26 Oreal KERATIN FIBER DYEING COMPOSITIONS CONTAINING PYRAZOLO- (1,5-A) -PYRIMIDINE DERIVATIVES, DYEING PROCESS, NOVEL PYRAZOLO- (1,5-A) -PYRIMIDINE DERIVATIVES AND PROCESS FOR PREPARING THE SAME
WO2005000903A1 (en) 2003-06-17 2005-01-06 Union Carbide Chemicals & Plastics Technology Corporation Cellulose ethers
JP2005145890A (en) * 2003-11-17 2005-06-09 Kao Corp Composition for photobleaching hair
US20060115440A1 (en) * 2004-09-07 2006-06-01 Arata Andrew B Silver dihydrogen citrate compositions
WO2017091797A1 (en) * 2015-11-24 2017-06-01 L'oreal Compositions for treating the hair
WO2018081399A1 (en) * 2016-10-31 2018-05-03 L'oreal Compositions for chemically treated hair

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE GNPD [online] MINTEL; "Chamomile Hair Lightening Spray", XP002783666, Database accession no. 1614565 *

Also Published As

Publication number Publication date
JP2018203699A (en) 2018-12-27

Similar Documents

Publication Publication Date Title
JP6914632B2 (en) Composition for keratin fibers
JP3297056B2 (en) Dyeing method of keratin fiber using oxidation dye precursor and powder direct dye
JP3814536B2 (en) Composition for oxidation dyeing of keratin fibers containing a thickening polymer having an ether resin skeleton
US20030084516A9 (en) Compositions for oxidation dyeing keratinous fibers comprising at least one oxidation precursor, and at least one direct dye, and dyeing methods
US20040205901A1 (en) Oxidation dyeing composition for keratin fibres comprising a cationic poly(vinyllactam)
MXPA03000155A (en) Composition for the oxidative dyeing of keratin fibres containing an oxyalkylenated carboxylic acid ether, an associative polymer and an unsaturated fatty acid.
MXPA04006060A (en) Dyeing composition for keratinous fibers comprising an oxyethylene rapeseed fatty acid amide.
FR2812810A1 (en) COMPOSITION FOR KERATIN FIBER OXIDATION DYE COMPRISING A CATIONIC AMPHIPHILIC POLYMER, OXYALKYLENE OR POLYGLYCEROL FATTY ALCOHOL AND A HYDROXYL SOLVENT
US7959687B2 (en) Hair dyeing process comprising a post-treatment using at least one organic silicon compound
JP2001206829A (en) Composition for oxidation dye for keratin fiber, comprising oxyalkylenated nonionic surfactant having hlb exceeding 5 and fatty alcohol having carbon atoms more than 20
JP4065196B2 (en) Composition for oxidation dyeing of keratin fibers containing cationic associative polyurethane
JP2005512950A (en) Composition for dyeing human keratin fibers comprising an oxidative dye and a dicationic compound
CN112312972A (en) Hair colouring composition comprising an oxidation dye, a scleroglucan gum and a cationic polymer
MXPA03000163A (en) Composition for the oxidative dyeing of keratin fibres.
EP1754466B1 (en) Oxidative dye composition for keratinic fibers comprising a fatty alcohol, an oxidative dye, an associative polymer, a fatty acid ester and/or a metallic oxide
MXPA03000156A (en) Composition useful for the oxidation dyeing of keratin fibres, containing a polyoxyalkylenated carboxylic acid ether, a mono-or polyglycerolated surfactant and an unsaturated fatty alcohol.
US20040133995A1 (en) Oxidation dyeing composition for keratin fibers comprising a cationic poly(vinyllactam) and at least one C10-C14 fatty acid, methods and devices for oxidation dyeing
US20040133993A1 (en) Oxidation dyeing composition for keratin fibers comprising a cationic poly(vinyllactam) and at least one oxidation dye in the form of a sulphate ion
ES2374566T3 (en) COMPOSITION OF OXIDATION DYEING FOR KERATIN FIBERS THAT INCLUDE AN OXIDATION COLOR, AN ASSOCIATIVE POLYMER, A NON-IONIC CELLULOSE COMPOUND THAT DOES NOT CONTAIN THE FAT CHAIN OF C8-C30 AND A CATIONIC POLYMER OF SUPERIOR DENSITY 1 CONTAINS THE FAT CHAIN OF C8-C30.
US20020026675A1 (en) Compositions for oxidation dyeing keratinous fibers comprising at least one 1-(4-aminophenyl)pyrrolidine and at least one thickening polymer comprising at least one sugar unit, and dyeing methods
US7323015B2 (en) Oxidation dyeing composition for keratin fibers comprising a cationic poly(vinyllactam) and at least One C10-C14 fatty alcohol, methods and devices for oxidation dyeing
JP2013537165A (en) Cosmetic composition for keratin fibers
WO2018225529A1 (en) Composition for keratin fibers
JP2001220331A (en) Dye composition for keratinous fiber comprising nonionic compound
FR2923389A1 (en) KERATIN FIBER OXIDATION DYEING COMPOSITION COMPRISING HYDROPHOBIC SUBSTITUTE CELLULOSE (S), OXIDATION DYE AND CATIONIC POLYMER

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18733352

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18733352

Country of ref document: EP

Kind code of ref document: A1