US20020136699A1 - Cosmetic composition for treating keratin substances, comprising at least one grafted silicone polymer and at least one aqueous dispersion of insoluble particles of nonionic or cationic polymer - Google Patents

Cosmetic composition for treating keratin substances, comprising at least one grafted silicone polymer and at least one aqueous dispersion of insoluble particles of nonionic or cationic polymer Download PDF

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US20020136699A1
US20020136699A1 US10/092,530 US9253002A US2002136699A1 US 20020136699 A1 US20020136699 A1 US 20020136699A1 US 9253002 A US9253002 A US 9253002A US 2002136699 A1 US2002136699 A1 US 2002136699A1
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Claude Dubief
Christine Dupuis
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LOreal SA
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LOreal SA
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/896Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/899Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing sulfur, e.g. sodium PG-propyldimethicone thiosulfate copolyol
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/046Aerosols; Foams
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8105Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • A61K8/8117Homopolymers or copolymers of aromatic olefines, e.g. polystyrene; Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8135Compositions 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 an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid; Compositions of derivatives of such polymers, e.g. vinyl esters (polyvinylacetate)
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54Polymers characterized by specific structures/properties
    • A61K2800/542Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5424Polymers characterized by specific structures/properties characterized by the charge anionic
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54Polymers characterized by specific structures/properties
    • A61K2800/542Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5426Polymers characterized by specific structures/properties characterized by the charge cationic

Definitions

  • the present invention relates to a cosmetic or dermatological composition for treating keratin substances, in particular the hair, comprising at least one grafted silicone polymer with a polysiloxane skeleton-grafted with non-silicone organic monomers, and at least one aqueous dispersion of insoluble particles of nonionic or cationic polymer.
  • Polymers with a polysiloxane skeleton grafted with non-silicone organic monomers are also known in the prior art. They are preferably chosen from those described in patent applications EP-A-0,582,152 and WO 93/23009. They are used in particular in hair compositions for their styling properties.
  • compositions for washing and/or caring for and/or treating the hair containing styling polymers of this type in their formulation generally have the drawback of having a fixing power which is still insufficient.
  • compositions are thus still sought which do not have the drawbacks described above.
  • compositions have good fixing power and good cosmetic properties such as disentangling and styling or brushing of the hair after application, the softness, the feel and the smoothness of the hair.
  • composition according to the invention is thus essentially characterized in that it comprises, in a cosmetically or dermatologically acceptable medium, at least one grafted silicone polymer with a polysiloxane skeleton grafted with non-silicone organic monomers and at least one dispersion of insoluble particles of nonionic or cationic polymer.
  • silicone polymer is understood to denote any organosilicon polymer or oligomer having a linear or cyclic, branched or crosslinked structure of variable molecular weight, obtained by polymerization and/or polycondensation of suitably functionalized silanes, and consisting essentially of a repetition of main units in which the silicon atoms are linked together by oxygen atoms (siloxane bonding ⁇ Si—O—Si ⁇ ), optionally substituted hydrocarbon radicals being linked directly via a carbon atom to the said silicon atoms.
  • hydrocarbon radicals are alkyl radicals, especially C 1 -C 10 alkyl radicals, and in particular methyl, fluoroalkyl radicals, aryl radicals and in particular phenyl, and alkenyl radicals and in particular vinyl; other types of radicals which can be linked, either directly or via a hydrocarbon radical, to the siloxane chain are, especially, hydrogen, halogens and in particular chlorine, bromine or fluorine, thiols, alkoxy radicals, polyoxyalkylene (or polyether) radicals and in particular polyoxyethylene and/or polyoxypropylene, hydroxyl or hydroxyalkyl radicals, substituted or unsubstituted amine groups, amide groups, acyloxy radicals or acyloxyalkyl radicals, hydroxyalkylamino or aminoalkyl radicals, quaternary ammonium groups, amphoteric or betaine groups, anionic groups such as carboxylates, thioglycolates, sulfon
  • the grafted silicone polymer(s) which is (are) to be used is (are) that (those) which comprise(s) a main silicone (or polysiloxane ( ⁇ Si—O—) n ) chain on which is grafted, inside the said chain as well as, optionally, on at least one of its ends, at least one organic group containing no silicone.
  • These silicone polymers can be existing commercial products or alternatively can be obtained according to any means known to those skilled in the art, in particular by reaction between (i) a starting silicone which is correctly functionalized on one or more of these silicon atoms, and (ii) a non-silicone organic compound which is itself correctly functionalized with a function which is capable of reacting with the functional group(s) borne by the said silicone, forming a covalent bond; a classic example of such a reaction is the hydrosilylation reaction between ⁇ Si—H groups and vinyl groups CH 2 ⁇ CH—, or alternatively the reaction between thio functional groups —SH with these same vinyl groups.
  • silicone polymers which are suitable for carrying out the present invention, as well as their specific mode of preparation, are described in particular in patent applications EP-A-0,582,152, WO 93/23009 and WO 95/03776, the teachings of which are included in their entirety in the present description by way of non-limiting references.
  • the silicone polymer used comprises the result of the radical copolymerization between, on the one hand, at least one non-silicone anionic organic monomer having ethylenic unsaturation and/or a non-silicone hydrophobic organic monomer having ethylenic unsaturation, and, on the other hand, a silicone having in its chain at least one functional group capable of reacting with the said ethylenic unsaturations of the said non-silicone monomers, forming a covalent bond, in particular thio functional groups.
  • the said anionic monomers containing ethylenic unsaturation are preferably chosen, alone or as a mixture, from linear or branched, unsaturated carboxyllc acids, optionally partially or totally neutralized in the form of a salt, it being possible for this (these) carboxylic acid(s) to be, more particularly, acrylic acid, methacrylic acid, maleic acid, maleic anhydride, itaconic acid, fumaric acid and crotonic acid.
  • the suitable salts are, in particular, alkali metal salts, alkaline-earth metal salts and ammonium salts.
  • the organic group of anionic nature which comprises the result of the radical (homo)polymerization of at least one anionic monomer of unsaturated carboxylic acid type can, after reaction, be post-neutralized with a base (sodium hydroxide, aqueous ammonia, etc) in order to bring it into the form of a salt.
  • a base sodium hydroxide, aqueous ammonia, etc
  • the hydrophobic monomers containing ethylenic unsaturation are preferably chosen, alone or as a mixture, from acrylic acid esters of alkanols and/or methacrylic acid esters of alkanols.
  • the alkanols are preferably C 1 -C 18 and more particularly C 1 -C 12 .
  • the preferred monomers are chosen from the group consisting of isooctyl (meth)acrylate, isononyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, isopentyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, methyl (meth)acrylate, tert-butyl (meth)acrylate, tridecyl (meth)acrylate and stearyl (meth)acryiate, or mixtures thereof.
  • One family of grafted silicone polymers which is particularly suitable for carrying out the present invention consists of silicone polymers containing in their structure the unit of formula (I) below:
  • radicals G 1 which may be identical or different, represent hydrogen or a C 1 -C 10 alkyl radical or alternatively a phenyl radical; the radicals G 2 , which may be identical or different, represent a C 1 -C 10 alkylene group;
  • G 3 represents a polymer residue resulting from the (homo)polymerization of at least one anionic monomer containing ethylenic unsaturation;
  • G 4 represents a polymer residue resulting from the (homo)polymerization of at least one hydrophobic monomer containing ethylenic unsaturation;
  • m and n are equal to 0 or 1;
  • a is an integer ranging from 0 to 50;
  • b is an integer which may be between 10 and 350,
  • c is an integer ranging from 0 to 50; with the proviso that one of the parameters a and c is other than 0.
  • the unit of formula (I) above has at least one, and even more preferably all, of the following characteristics:
  • radicals G 1 denote an alkyl radical, preferably the methyl radical
  • n is non-zero and the radicals G 2 represent a divalent C 1 -C 3 radical, preferably a propylene radical;
  • G 3 represents a polymeric radical resulting from the (homo)polymerization of at least one monomer of the carboxylic acid type containing ethylenic unsaturation, preferably acrylic acid and/or methacrylic acid;
  • G 4 represents a polymeric radical resulting from the (homo)polymerization of at least one monomer of the C 1 -C 10 alkyl (meth)acrylate type, preferably of the isobutyl or methyl (meth)acrylate type.
  • silicone polymers corresponding to formula (I) are, in particular, polydimethylsiloxanes (PDMS) on which are grafted, via a thiopropylene-type connecting chain, mixed polymer units of the poly(meth)acrylic acid type and of the polymethyl (meth)acrylate type.
  • PDMS polydimethylsiloxanes
  • silicone polymers corresponding to formula (I) are, in particular, polydimethylsiloxanes (PDMS) on which are grafted, via a thiopropylene-type connecting chain, polymer units of the polyisobutyl (meth)acrylate type.
  • PDMS polydimethylsiloxanes
  • the number-average molecular mass of the silicone polymers of the invention ranges approximately from 10,000 to 1,000,000 and even more preferably approximately from 10,000 to 100,000.
  • the grafted silicone polymers in accordance with the invention are preferably used in an amount ranging from 0.01 to 20% by weight relative to the total weight of the composition. More preferably, this amount ranges from 0.1 to 15% by weight and even more particularly from 0.5 to 10% by weight.
  • aqueous dispersions of insoluble particles of nonionic or cationic polymer which can be used according to the invention are generally obtained by suspension or emulsion polymerization or copolymerization of monomers according to processes that are well known in the prior art (such dispersions are also known as “latices”).
  • Aqueous polymer dispersions can also be obtained by dissolving the said polymer in a water-miscible organic solvent, after which water is added and lastly the organic solvent is evaporated off. This type of preparation is described, for example, in French patent application No. 2,697,160.
  • the average diameter of the insoluble polymer particles is generally less than 500 nm and preferably less than 250 nm.
  • the glass transition temperature is generally between ⁇ 30° C. and 90° C. and preferably between 10 and 35° C.
  • the polymer of the aqueous dispersion comprises at least one monomer chosen, for example, from styrene, butadiene, ethylene, tetrafluoroethylene, propylene, vinyltoluene, vinyl propionate, vinyl alcohol, acrylonitrile, chloroprene, vinyl chloride, vinyl acetate, urethanes, isoprene, isobutene and esters or amides of acrylic, methacrylic, maleic, crotonic or itaconic acid, vinyl ethers, vinylpyrrolidone, vinylimidazole, trimethylammonioethyl (meth)acrylate and mixtures thereof.
  • monomer chosen, for example, from styrene, butadiene, ethylene, tetrafluoroethylene, propylene, vinyltoluene, vinyl propionate, vinyl alcohol, acrylonitrile, chloroprene, vinyl chloride, vinyl acetate, urethanes, iso
  • aqueous dispersions which can be used according to the invention can come from the condensation of ionic or nonionic monomers giving nonionic or cationic polymers, such as, for example, polyesters, polyamides, polyurethanes or polyethers.
  • nonionic polymers in the aqueous dispersions which can be used according to the present invention are chosen, for example, from the following compounds:
  • vinyl acetate homopolymers such as the product sold under the name Appretan EM by the company Hoechst or the product sold under the name Rhodopas A 012 by the company Rhone-Poulenc;
  • copolymers of vinyl acetate and of acrylic ester such as the product sold under the name Rhodopas AD 310 by Rhône-Poulenc;
  • copolymers of vinyl acetate and of ethylene such as the product sold under the name Appretan TV by the company Hoechst;
  • copolymers of vinyl acetate and of maleic ester for example of dibutyl maleate, such as the product sold under the name Appretan MB Extra by the company Hoechst;
  • vinyl chloride homopolymers such as the products sold under the names Geon 460 ⁇ 45, Geon 460 ⁇ 46 and Geon 577 by the company Goodrich;
  • polyethylene waxes such as the products sold under the names Aquacer 513 and Aquacer 533 by the company Byk Cera;
  • polyethylene/polytetrafluoroethylene waxes such as the products sold under the names Drewax D-3750 by the company Drew Ameroid and Wax Dispersion WD-1077 by the company R.T. Newey;
  • copolymers of polyethylene and of maleic anhydride [0040] copolymers of polyethylene and of maleic anhydride
  • alkyl acrylate homopolymers and alkyl methacrylate homopolymers such as the product sold under the name Micropearl RQ 750 by the company Matsumoto or the product sold under the name Luhydran A 848 S by the company BASF;
  • copolymers of acrylic esters such as, for example, copolymers of alkyl acrylates and of alkyl methacrylates, such as the products sold by the company Rohm & Haas under the names Primal ACZ 61 k and Eudragit NE 30 D, by the company BASF under the names Acronal 601, Luhydraw LR 8833 or 8845, and by the company Hoechst under the names Appretan N 9213 or N9212;
  • copolymers of acrylonitrile and of a nonionic monomer chosen, for example, from butadiene and alkyl (meth)acrylates mention may be made of the products sold under the names Nipol LX 531 B by the company Nippon Zeon or those sold under the name CJ 0601 B by the company Rohm & Haas;
  • styrene homopolymers such as the product Rhodopas 5051 sold by the company Rhône-Poulenc;
  • copolymers of styrene and of alkyl (meth)acrylate such as the products Mowilith LDM 6911, Mowilith DM 611 and Mowilith LDM 6070 sold by the company Hoechst, the products Rhodopas SD 215 and Rhodopas DS 910 sold by the company Rhone-Poulenc and the product Uramul SC 70 sold by the company DSM;
  • copolymers of styrene, of alkyl methacrylate and of alkyl acrylate such as the product Daitisol SPA sold by the company Wacker;
  • copolymers of styrene and of butadiene such as the products Rhodopas SB 153 and Rhodopas SB 012 sold by the company Rhône-Poulenc;
  • copolymers of styrene, of butadiene and of vinylpyridine such as the products Goodrite SB Vinylpyridine 2528 ⁇ 10 and Goodrite SB Vinylpyridine 2508 sold by the company Goodrich;
  • copolymers of styrene and of vinylpyrrolidone such as the products Antara 450 and Cloud 285 sold by the company ISP;
  • polyurethanes such as the products sold under the names Acrysol RM 1020 or Acrysol RM 2020 by the company Rohm & Haas and the products Uraflex XP 401 UZ and Uraflex XP 402 UZ by the company DSM Resins;
  • copolymers of alkyl acrylate and of urethane such as the product 8538-33 from the company National Starch;
  • polyamides such as the product Estapor LO 11 sold by the company Rhône-Poulenc.
  • the dispersions of insoluble particles of cationic polymer comprise, for example, the following polymers:
  • copolymers of alkyl methacrylate, of alkyl acrylate and of trimethylammonioethyl (meth)acrylate such as the product Eudragit RL 30 D sold by the company Rohm Pharma.
  • aqueous dispersions of insoluble polymer particles which are particularly preferred in the context of the invention are aqueous dispersions of insoluble particles of nonionic polymer.
  • the weight concentration of the insoluble polymer particles in the compositions according to the invention is preferably between 0.1 and 50% by weight relative to the total weight of the composition, and preferablybetween 1 and 30%.
  • the cosmetically or dermatologically acceptable medium preferably consists of water or a mixture of water and cosmetically acceptable solvents such as monoalcohols, polyalcohols, glycol ethers or fatty acid esters, which can be used alone or as a mixture.
  • lower alcohols such as ethanol and isopropanol
  • polyalcohols such as diethylene glycol, glycol ethers, glycol alkyl ethers or diethylene glycol alkyl ethers.
  • the grafted silicone polymers according to the invention can be dissolved in the said cosmetically acceptable medium or used in the form of an aqueous dispersion of insoluble particles.
  • composition of the invention can also contain at least one additive chosen from thickeners, fatty acid esters, fatty acid esters of glycerol, volatile silicones, surfactants, fragrances, preserving agents, sunscreens, proteins, vitamins, polymers, plant, animal, mineral or synthetic oils or any other additive conventionally used in the cosmetics field.
  • at least one additive chosen from thickeners, fatty acid esters, fatty acid esters of glycerol, volatile silicones, surfactants, fragrances, preserving agents, sunscreens, proteins, vitamins, polymers, plant, animal, mineral or synthetic oils or any other additive conventionally used in the cosmetics field.
  • additives are present in the composition according to the invention in proportions which can range from 0 to 20% by weight relative to the total weight of the composition.
  • the precise amount of each additive depends on its nature and is determined easily by those skilled in the art.
  • compositions according to the invention can be in the form of a gel, a milk, a cream, a relatively thickened lotion or a mousse.
  • compositions of the invention are used as rinse-out products or as leave-in products in particular to wash, care for, condition, maintain the style of or shape keratin substances such as the hair.
  • compositions are more particularly styling products such as hairsetting lotions, blow-drying lotions, fixing compositions (lacquers) and styling compositions.
  • the lotions can be packaged in various forms, in particular in vaporizers, pump-dispenser bottles or in aerosol containers in order to ensure application of the composition in vaporized form or in the form of a mousse.
  • Such packaging forms are indicated, for example, when it is desired to obtain a spray, a lacquer or a mousse for fixing or treating the hair.
  • compositions can also be shampoos, rinse-out or leave-in compositions, to be applied before or after shampooing, dyeing, bleaching, permanent-waving or straightening the hair.
  • composition according to the invention when packaged in aerosol form in order to obtain a lacquer or an aerosol mousse, it comprises at least one propellant which can be chosen from volatile hydrocarbons such as n-butane, propane, isobutane, pentane, a chloro and/or fluoro hydrocarbon, and mixtures thereof. Carbon dioxide, nitrous oxide, dimethyl ether, nitrogen or air, which is compressed, and mixtures thereof, can also be used as propellant.
  • propellant can be chosen from volatile hydrocarbons such as n-butane, propane, isobutane, pentane, a chloro and/or fluoro hydrocarbon, and mixtures thereof.
  • Carbon dioxide, nitrous oxide, dimethyl ether, nitrogen or air, which is compressed, and mixtures thereof can also be used as propellant.
  • Another subject of the invention is a process for treating keratin substances such as the hair, which consists in applying a composition as defined above to the hair and then optionally in rinsing with water.
  • AM means active material
  • Grafted silicone polymer of formula (I) 3 g of polymethyl/methylsiloxane structure containing 3-propylthio polymethacrylic acid groups and 3-propylthio polymethyl methacrylate groups Vinyl acetate homopolymer as an aqueous 4 g AM dispersion containing 50% AM, sold under the name Appretan EM by the company Hoechst
  • composition is pressurized as an aerosol.
  • This composition was applied to dried hair, the hair then having a good feel, good maintenance and good hold over time.
  • composition is easily removed on shampooing.
  • Grafted silicone polymer of formula (I) 4 g of polymethyl/methylsiloxane structure containing 3-propylthio polymethacrylic acid groups and 3-propylthio polymethyl methacrylate groups
  • Copolymer of styrene and of butadiene as 2 g AM an aqueous dispersion containing 50% AM, sold under the name Rhodopas SB 012 by the company Rhône-Poulenc
  • composition is pressurized as an aerosol.
  • This composition was applied to dried hair, the hair then having a good feel, good maintenance and good hold over time.
  • composition is easily removed on shampooing.

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Abstract

The present invention relates to a cosmetic or dermatological composition for the treatment of keratinous materials, particularly hair, comprising in a cosmetically or dermatalogically exceptable medium at least a grafted silicone polymer with a polysiloxanic skeleton grafted by organic non silicone monomers and at least an aqueous dispersions of insoluble particles of non ionic or cationic polymer. The compositions of the invention are used particularly as rinsed products or as non rinsed products particularly for hair washing, hair care, hair conditioning, hair dressing or hair setting.

Description

  • The present invention relates to a cosmetic or dermatological composition for treating keratin substances, in particular the hair, comprising at least one grafted silicone polymer with a polysiloxane skeleton-grafted with non-silicone organic monomers, and at least one aqueous dispersion of insoluble particles of nonionic or cationic polymer. [0001]
  • It has been proposed to use aqueous dispersions of insoluble polymer particles in compositions for maintaining the hairstyle. However, is the results obtained hitherto are still not satisfactory. The reason for this is that the fixing power is still not sufficient, the drying time is long and the cosmetic properties are still not satisfactory. Furthermore, the polymer is difficult to remove from the hair during washing with a shampoo. [0002]
  • Polymers with a polysiloxane skeleton grafted with non-silicone organic monomers are also known in the prior art. They are preferably chosen from those described in patent applications EP-A-0,582,152 and WO 93/23009. They are used in particular in hair compositions for their styling properties. [0003]
  • Compositions for washing and/or caring for and/or treating the hair containing styling polymers of this type in their formulation generally have the drawback of having a fixing power which is still insufficient. [0004]
  • The expression fixing power of the composition will be understood to denote the ability of this composition to give the hair cohesion such that the initial shape of the hairstyle is retained. [0005]
  • Compositions are thus still sought which do not have the drawbacks described above. [0006]
  • The Applicant has discovered, surprisingly, that by combining at least one silicone polymer having a polysiloxane skeleton grafted with non-silicone organic monomers with at least one dispersion of insoluble particles of nonionic or cationic polymer, the abovementioned drawbacks are overcome. [0007]
  • These compositions have good fixing power and good cosmetic properties such as disentangling and styling or brushing of the hair after application, the softness, the feel and the smoothness of the hair. [0008]
  • The composition according to the invention is thus essentially characterized in that it comprises, in a cosmetically or dermatologically acceptable medium, at least one grafted silicone polymer with a polysiloxane skeleton grafted with non-silicone organic monomers and at least one dispersion of insoluble particles of nonionic or cationic polymer. [0009]
  • In the following text, in accordance with what is generally accepted, the term silicone polymer is understood to denote any organosilicon polymer or oligomer having a linear or cyclic, branched or crosslinked structure of variable molecular weight, obtained by polymerization and/or polycondensation of suitably functionalized silanes, and consisting essentially of a repetition of main units in which the silicon atoms are linked together by oxygen atoms (siloxane bonding ≡Si—O—Si≡), optionally substituted hydrocarbon radicals being linked directly via a carbon atom to the said silicon atoms. The most common hydrocarbon radicals are alkyl radicals, especially C[0010] 1-C10 alkyl radicals, and in particular methyl, fluoroalkyl radicals, aryl radicals and in particular phenyl, and alkenyl radicals and in particular vinyl; other types of radicals which can be linked, either directly or via a hydrocarbon radical, to the siloxane chain are, especially, hydrogen, halogens and in particular chlorine, bromine or fluorine, thiols, alkoxy radicals, polyoxyalkylene (or polyether) radicals and in particular polyoxyethylene and/or polyoxypropylene, hydroxyl or hydroxyalkyl radicals, substituted or unsubstituted amine groups, amide groups, acyloxy radicals or acyloxyalkyl radicals, hydroxyalkylamino or aminoalkyl radicals, quaternary ammonium groups, amphoteric or betaine groups, anionic groups such as carboxylates, thioglycolates, sulphosuccinates, thiosulphates, phosphates and sulphates, needless to say this list not being limiting in any way (so-called “organomodified” silicones).
  • According to the present invention, the grafted silicone polymer(s) which is (are) to be used is (are) that (those) which comprise(s) a main silicone (or polysiloxane (≡Si—O—)[0011] n) chain on which is grafted, inside the said chain as well as, optionally, on at least one of its ends, at least one organic group containing no silicone.
  • These silicone polymers can be existing commercial products or alternatively can be obtained according to any means known to those skilled in the art, in particular by reaction between (i) a starting silicone which is correctly functionalized on one or more of these silicon atoms, and (ii) a non-silicone organic compound which is itself correctly functionalized with a function which is capable of reacting with the functional group(s) borne by the said silicone, forming a covalent bond; a classic example of such a reaction is the hydrosilylation reaction between ≡Si—H groups and vinyl groups CH[0012] 2═CH—, or alternatively the reaction between thio functional groups —SH with these same vinyl groups.
  • Examples of silicone polymers which are suitable for carrying out the present invention, as well as their specific mode of preparation, are described in particular in patent applications EP-A-0,582,152, WO 93/23009 and WO 95/03776, the teachings of which are included in their entirety in the present description by way of non-limiting references. [0013]
  • According to a particularly preferred embodiment of the present invention, the silicone polymer used comprises the result of the radical copolymerization between, on the one hand, at least one non-silicone anionic organic monomer having ethylenic unsaturation and/or a non-silicone hydrophobic organic monomer having ethylenic unsaturation, and, on the other hand, a silicone having in its chain at least one functional group capable of reacting with the said ethylenic unsaturations of the said non-silicone monomers, forming a covalent bond, in particular thio functional groups. [0014]
  • According to the present invention, the said anionic monomers containing ethylenic unsaturation are preferably chosen, alone or as a mixture, from linear or branched, unsaturated carboxyllc acids, optionally partially or totally neutralized in the form of a salt, it being possible for this (these) carboxylic acid(s) to be, more particularly, acrylic acid, methacrylic acid, maleic acid, maleic anhydride, itaconic acid, fumaric acid and crotonic acid. The suitable salts are, in particular, alkali metal salts, alkaline-earth metal salts and ammonium salts. It will likewise be noted that, in the final grafted silicone polymer, the organic group of anionic nature which comprises the result of the radical (homo)polymerization of at least one anionic monomer of unsaturated carboxylic acid type can, after reaction, be post-neutralized with a base (sodium hydroxide, aqueous ammonia, etc) in order to bring it into the form of a salt. [0015]
  • According to the present invention, the hydrophobic monomers containing ethylenic unsaturation are preferably chosen, alone or as a mixture, from acrylic acid esters of alkanols and/or methacrylic acid esters of alkanols. The alkanols are preferably C[0016] 1-C18 and more particularly C1-C12. The preferred monomers are chosen from the group consisting of isooctyl (meth)acrylate, isononyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, isopentyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, methyl (meth)acrylate, tert-butyl (meth)acrylate, tridecyl (meth)acrylate and stearyl (meth)acryiate, or mixtures thereof.
  • One family of grafted silicone polymers which is particularly suitable for carrying out the present invention consists of silicone polymers containing in their structure the unit of formula (I) below: [0017]
    Figure US20020136699A1-20020926-C00001
  • in which the radicals G[0018] 1, which may be identical or different, represent hydrogen or a C1-C10 alkyl radical or alternatively a phenyl radical; the radicals G2, which may be identical or different, represent a C1-C10 alkylene group; G3 represents a polymer residue resulting from the (homo)polymerization of at least one anionic monomer containing ethylenic unsaturation; G4 represents a polymer residue resulting from the (homo)polymerization of at least one hydrophobic monomer containing ethylenic unsaturation; m and n are equal to 0 or 1; a is an integer ranging from 0 to 50; b is an integer which may be between 10 and 350, c is an integer ranging from 0 to 50; with the proviso that one of the parameters a and c is other than 0.
  • Preferably, the unit of formula (I) above has at least one, and even more preferably all, of the following characteristics: [0019]
  • the radicals G[0020] 1 denote an alkyl radical, preferably the methyl radical;
  • n is non-zero and the radicals G[0021] 2 represent a divalent C1-C3 radical, preferably a propylene radical;
  • G[0022] 3 represents a polymeric radical resulting from the (homo)polymerization of at least one monomer of the carboxylic acid type containing ethylenic unsaturation, preferably acrylic acid and/or methacrylic acid;
  • G[0023] 4 represents a polymeric radical resulting from the (homo)polymerization of at least one monomer of the C1-C10 alkyl (meth)acrylate type, preferably of the isobutyl or methyl (meth)acrylate type.
  • Examples of silicone polymers corresponding to formula (I) are, in particular, polydimethylsiloxanes (PDMS) on which are grafted, via a thiopropylene-type connecting chain, mixed polymer units of the poly(meth)acrylic acid type and of the polymethyl (meth)acrylate type. [0024]
  • Other examples of silicone polymers corresponding to formula (I) are, in particular, polydimethylsiloxanes (PDMS) on which are grafted, via a thiopropylene-type connecting chain, polymer units of the polyisobutyl (meth)acrylate type. [0025]
  • Preferably, the number-average molecular mass of the silicone polymers of the invention, ranges approximately from 10,000 to 1,000,000 and even more preferably approximately from 10,000 to 100,000. [0026]
  • The grafted silicone polymers in accordance with the invention are preferably used in an amount ranging from 0.01 to 20% by weight relative to the total weight of the composition. More preferably, this amount ranges from 0.1 to 15% by weight and even more particularly from 0.5 to 10% by weight. [0027]
  • The aqueous dispersions of insoluble particles of nonionic or cationic polymer which can be used according to the invention are generally obtained by suspension or emulsion polymerization or copolymerization of monomers according to processes that are well known in the prior art (such dispersions are also known as “latices”). Aqueous polymer dispersions can also be obtained by dissolving the said polymer in a water-miscible organic solvent, after which water is added and lastly the organic solvent is evaporated off. This type of preparation is described, for example, in French patent application No. 2,697,160. [0028]
  • The average diameter of the insoluble polymer particles is generally less than 500 nm and preferably less than 250 nm. The glass transition temperature is generally between −30° C. and 90° C. and preferably between 10 and 35° C. [0029]
  • The polymer of the aqueous dispersion comprises at least one monomer chosen, for example, from styrene, butadiene, ethylene, tetrafluoroethylene, propylene, vinyltoluene, vinyl propionate, vinyl alcohol, acrylonitrile, chloroprene, vinyl chloride, vinyl acetate, urethanes, isoprene, isobutene and esters or amides of acrylic, methacrylic, maleic, crotonic or itaconic acid, vinyl ethers, vinylpyrrolidone, vinylimidazole, trimethylammonioethyl (meth)acrylate and mixtures thereof. [0030]
  • The aqueous dispersions which can be used according to the invention can come from the condensation of ionic or nonionic monomers giving nonionic or cationic polymers, such as, for example, polyesters, polyamides, polyurethanes or polyethers. [0031]
  • The nonionic polymers in the aqueous dispersions which can be used according to the present invention are chosen, for example, from the following compounds: [0032]
  • vinyl acetate homopolymers such as the product sold under the name Appretan EM by the company Hoechst or the product sold under the name Rhodopas A 012 by the company Rhone-Poulenc; [0033]
  • copolymers of vinyl acetate and of acrylic ester, such as the product sold under the name Rhodopas AD 310 by Rhône-Poulenc; [0034]
  • copolymers of vinyl acetate and of ethylene, such as the product sold under the name Appretan TV by the company Hoechst; [0035]
  • copolymers of vinyl acetate and of maleic ester, for example of dibutyl maleate, such as the product sold under the name Appretan MB Extra by the company Hoechst; [0036]
  • vinyl chloride homopolymers, such as the products sold under the names Geon 460×45, Geon 460×46 and Geon 577 by the company Goodrich; [0037]
  • polyethylene waxes, such as the products sold under the names Aquacer 513 and Aquacer 533 by the company Byk Cera; [0038]
  • polyethylene/polytetrafluoroethylene waxes, such as the products sold under the names Drewax D-3750 by the company Drew Ameroid and Wax Dispersion WD-1077 by the company R.T. Newey; [0039]
  • copolymers of polyethylene and of maleic anhydride; [0040]
  • alkyl acrylate homopolymers and alkyl methacrylate homopolymers, such as the product sold under the name Micropearl RQ 750 by the company Matsumoto or the product sold under the name Luhydran A 848 S by the company BASF; [0041]
  • copolymers of acrylic esters such as, for example, copolymers of alkyl acrylates and of alkyl methacrylates, such as the products sold by the company Rohm & Haas under the names Primal ACZ 61 k and Eudragit NE 30 D, by the company BASF under the names Acronal 601, Luhydraw LR 8833 or 8845, and by the company Hoechst under the names Appretan N 9213 or N9212; [0042]
  • copolymers of acrylonitrile and of a nonionic monomer chosen, for example, from butadiene and alkyl (meth)acrylates; mention may be made of the products sold under the names Nipol LX 531 B by the company Nippon Zeon or those sold under the name CJ 0601 B by the company Rohm & Haas; [0043]
  • styrene homopolymers such as the product Rhodopas 5051 sold by the company Rhône-Poulenc; [0044]
  • copolymers of styrene and of alkyl (meth)acrylate, such as the products Mowilith LDM 6911, Mowilith DM 611 and Mowilith LDM 6070 sold by the company Hoechst, the products Rhodopas SD 215 and Rhodopas DS 910 sold by the company Rhone-Poulenc and the product Uramul SC 70 sold by the company DSM; [0045]
  • copolymers of styrene, of alkyl methacrylate and of alkyl acrylate, such as the product Daitisol SPA sold by the company Wacker; [0046]
  • copolymers of styrene and of butadiene, such as the products Rhodopas SB 153 and Rhodopas SB 012 sold by the company Rhône-Poulenc; [0047]
  • copolymers of styrene, of butadiene and of vinylpyridine, such as the products Goodrite SB Vinylpyridine 2528×10 and Goodrite SB Vinylpyridine 2508 sold by the company Goodrich; [0048]
  • copolymers of styrene and of vinylpyrrolidone, such as the products Antara 450 and Cloud 285 sold by the company ISP; [0049]
  • polyurethanes, such as the products sold under the names Acrysol RM 1020 or Acrysol RM 2020 by the company Rohm & Haas and the products Uraflex XP 401 UZ and Uraflex XP 402 UZ by the company DSM Resins; [0050]
  • copolymers of alkyl acrylate and of urethane, such as the product 8538-33 from the company National Starch; [0051]
  • polyamides, such as the product Estapor LO 11 sold by the company Rhône-Poulenc. [0052]
  • The dispersions of insoluble particles of cationic polymer comprise, for example, the following polymers: [0053]
  • copolymers of acrylamide and of trimethylammonioethyl (meth)acrylate; [0054]
  • copolymers of alkyl methacrylate, of alkyl acrylate and of trimethylammonioethyl (meth)acrylate, such as the product Eudragit RL 30 D sold by the company Rohm Pharma. [0055]
  • The aqueous dispersions of insoluble polymer particles which are particularly preferred in the context of the invention are aqueous dispersions of insoluble particles of nonionic polymer. [0056]
  • The weight concentration of the insoluble polymer particles in the compositions according to the invention is preferably between 0.1 and 50% by weight relative to the total weight of the composition, and preferablybetween 1 and 30%. [0057]
  • The cosmetically or dermatologically acceptable medium preferably consists of water or a mixture of water and cosmetically acceptable solvents such as monoalcohols, polyalcohols, glycol ethers or fatty acid esters, which can be used alone or as a mixture. [0058]
  • Mention may be made more particularly of lower alcohols such as ethanol and isopropanol, polyalcohols such as diethylene glycol, glycol ethers, glycol alkyl ethers or diethylene glycol alkyl ethers. [0059]
  • The grafted silicone polymers according to the invention can be dissolved in the said cosmetically acceptable medium or used in the form of an aqueous dispersion of insoluble particles. [0060]
  • The composition of the invention can also contain at least one additive chosen from thickeners, fatty acid esters, fatty acid esters of glycerol, volatile silicones, surfactants, fragrances, preserving agents, sunscreens, proteins, vitamins, polymers, plant, animal, mineral or synthetic oils or any other additive conventionally used in the cosmetics field. [0061]
  • These additives are present in the composition according to the invention in proportions which can range from 0 to 20% by weight relative to the total weight of the composition. The precise amount of each additive depends on its nature and is determined easily by those skilled in the art. [0062]
  • Needless to say, a person skilled in the art will take care to select the optional compound(s) to be added to the composition according to the invention such that the advantageous properties intrinsically associated with the composition in accordance with the invention are not, or are not substantially, adversely affected by the addition envisaged. [0063]
  • The compositions according to the invention can be in the form of a gel, a milk, a cream, a relatively thickened lotion or a mousse. [0064]
  • The compositions of the invention are used as rinse-out products or as leave-in products in particular to wash, care for, condition, maintain the style of or shape keratin substances such as the hair. [0065]
  • These compositions are more particularly styling products such as hairsetting lotions, blow-drying lotions, fixing compositions (lacquers) and styling compositions. The lotions can be packaged in various forms, in particular in vaporizers, pump-dispenser bottles or in aerosol containers in order to ensure application of the composition in vaporized form or in the form of a mousse. Such packaging forms are indicated, for example, when it is desired to obtain a spray, a lacquer or a mousse for fixing or treating the hair. [0066]
  • The compositions can also be shampoos, rinse-out or leave-in compositions, to be applied before or after shampooing, dyeing, bleaching, permanent-waving or straightening the hair. [0067]
  • When the composition according to the invention is packaged in aerosol form in order to obtain a lacquer or an aerosol mousse, it comprises at least one propellant which can be chosen from volatile hydrocarbons such as n-butane, propane, isobutane, pentane, a chloro and/or fluoro hydrocarbon, and mixtures thereof. Carbon dioxide, nitrous oxide, dimethyl ether, nitrogen or air, which is compressed, and mixtures thereof, can also be used as propellant. [0068]
  • Another subject of the invention is a process for treating keratin substances such as the hair, which consists in applying a composition as defined above to the hair and then optionally in rinsing with water. [0069]
  • The invention will now be illustrated more fully with the aid of the examples which follow, which should not be considered as limiting it to the embodiments described. In the text which follows, AM means active material. [0070]
  • EXAMPLE 1 Styling Aerosol Spray
  • [0071]
    Grafted silicone polymer of formula (I) 3 g
    of polymethyl/methylsiloxane structure
    containing 3-propylthio polymethacrylic
    acid groups and 3-propylthio polymethyl
    methacrylate groups
    Vinyl acetate homopolymer as an aqueous 4 g AM
    dispersion containing 50% AM, sold under
    the name Appretan EM by the company Hoechst
  • Aminomethylpropanol, qs 100% neutralization of the grafted silicone polymer [0072]
    Dimethyl ether 30 g
    Water qs 100 g
  • The composition is pressurized as an aerosol. [0073]
  • This composition was applied to dried hair, the hair then having a good feel, good maintenance and good hold over time. [0074]
  • The composition is easily removed on shampooing. [0075]
  • EXAMPLE 2 Styling Aerosol Spray
  • [0076]
    Grafted silicone polymer of formula (I) 4 g
    of polymethyl/methylsiloxane structure
    containing 3-propylthio polymethacrylic
    acid groups and 3-propylthio polymethyl
    methacrylate groups
    Copolymer of styrene and of butadiene as 2 g AM
    an aqueous dispersion containing 50% AM,
    sold under the name Rhodopas SB 012 by the
    company Rhône-Poulenc
  • Aminomethylpropanol, qs 100% neutralization of the grafted silicone polymer [0077]
    Dimethyl ether 30 g
    Water qs 100 g
  • The composition is pressurized as an aerosol. [0078]
  • This composition was applied to dried hair, the hair then having a good feel, good maintenance and good hold over time. [0079]
  • The composition is easily removed on shampooing. [0080]

Claims (29)

1. Cosmetic or dermatological composition intended for treating keratin substances, characterized in that it comprises, in a cosmetically or dermatologically acceptable medium, at least one grafted silicone polymer with a polysiloxane skeleton grafted with non-silicone organic monomers and at least one aqueous-dispersion of insoluble particles of nonionic or cationic polymer.
2. Composition according to claim 1, characterized in that the grafted silicone polymer comprises a main polysiloxane chain on which is grafted, inside the said chain as well as, optionally, on at least one of its ends, at least one organic group containing no silicone.
3. Composition according to claim 1 or 2, characterized in that the grafted silicone polymer can be obtained by radical copolymerization between, on the one hand, at least one non-silicone anionic organic monomer having ethylenic unsaturation and/or a non-silicone hydrophobic organic monomer having ethylenic unsaturation, and, on the other hand, a polysiloxane having in its chain at least one, and preferably several, functional groups capable of reacting with the said ethylenic unsaturations of the said non-silicone monomers.
4. Composition according to claim 3, characterized in that the anionic organic monomer containing ethylenic unsaturation is chosen, alone or in the form of a monomer mixture, from linear or branched unsaturated carboxylic acids.
5. Composition according to claim 4, characterized in that the anionic organic monomer containing ethylenic unsaturation is chosen, alone or in the form of a monomer mixture, from acrylic acid, methacrylic acid, maleic acid, maleic anhydride, itaconic acid, fumaric acid and crotonic acid or alkali metal, alkaline-earth metal or ammonium salts thereof, or mixtures thereof.
6. Composition according to claim 3, characterized in that the hydrophobic organic monomer containing ethylenic unsaturation is chosen, alone or as a monomer mixture, from acrylic acid esters of an alkanol and/or methacrylic acid esters of an alkanol, the alkanol preferably being C1-C18.
7. Composition according to claim 6, characterized in that the hydrophobic organic monomer containing ethylenic unsaturation is chosen, alone or as a monomer mixture, from the group consisting of isooctyl (meth)acrylate, isononyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, isopentyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, methyl (meth)acrylate, tert-butyl (meth)acrylate, tridecyl (meth)acrylate and stearyl (meth)acrylate.
8. Composition according to any one of claims 1 to 7, characterized in that the grafted silicone polymer comprises, on the main silicone chain, at least one organic group of anionic nature obtained by radical (homo) polymerization of at least one anionic monomer of unsaturated carboxylic acid type, partially or totally neutralized in the form of a salt.
9. Composition according to any one of claims 1 to 8, characterized in that the grafted silicone polymer is chosen from silicone polymers containing in their structure the unit of formula (I) below:
Figure US20020136699A1-20020926-C00002
in which the radicals G1, which may be identical or different, represent hydrogen or a C1-C10 alkyl radical or alternatively a phenyl radical; the radicals G2, which may be identical or different, represent a C1-C10 alkylene group; G3 represents a polymer residue resulting from the (homo)polymerization of at least one anionic monomer containing ethylenic unsaturation; G4 represents a polymer residue resulting from the (homo)polymerization of at least one hydrophobic monomer containing ethylenic unsaturation; m and n are equal to 0 or 1; a is an integer ranging from 0 to 50; b is an integer which may be between 10 and 350, c is an integer ranging from 0 to 50; with the proviso that one of the parameters a and c is other than 0.
10. Composition according to claim 9, characterized in that the unit of formula (I) has at least one of the following characteristics:
the radicals G1 denote a C1-C10 alkyl radical;
n is non-zero and the radicals G2 represent a divalent C1-C3 radical;
G3 represents a polymeric radical resulting from the (homo)polymerization of at least one monomer of the carboxylic acid type containing ethylenic unsaturation;
G4 represents a polymeric radical resulting from the (homo)polymerization of at least one monomer of the C1-C10 alkyl (meth)acrylate type.
11. Composition according to claim 9 or 10, characterized in that the unit of formula (I) simultaneously has the following characteristics:
the radicals G1 denote a methyl radical;
n is non-zero and the radicals G2 represent a propylene radical;
G3 represents a polymeric radical resulting from the (homo)polymerization of at least acrylic acid and/or methacrylic acid;
G4 represents a polymeric radical resulting from the (homo)polymerization of at least methyl (meth)acrylate.
12. Composition according to any one of claims 1 to 11, characterized in that the number-average molecular mass of the grafted silicone polymer ranges approximately from 10,000 to 1,000,000, and even more preferably approximately from 10,000 to 100,000.
13. Composition according to any one of the preceding claims, characterized in that the grafted silicone polymer(s) is (are) present in concentrations ranging from 0.01 to 20% by weight relative to the total weight of the composition, preferably from 0.1 to 15% by weight and more particularly from 0.5 to 10% by weight.
14. Composition according to any one of the preceding claims, characterized in that the polymer of the aqueous dispersion comprises at least one monomer chosen from styrene, butadiene, ethylene, propylene, vinyltoluene, vinyl propionate, vinyl alcohol, acrylonicrile, chloroprene, vinyl acetate, urethanes, isoprene, isobutene and esters or amides of acrylic, methacrylic, maleic, crotonic or itaconic acid, vinyl ether, vinylpyrrolidone, vinylimidazole, trimethylammonioethyl (meth)acrylate and mixtures thereof.
15. Composition according to any one of the preceding claims, characterized in that the nonionic polymer of the aqueous dispersion is chosen from polyesters, polyamides, polyurethanes and polyethers.
16. Composition according to any one of the preceding claims, characterized in that the nonionic polymer of the aqueous dispersion is chosen from:
vinyl acetate homopolymers;
copolymers of vinyl acetate and of acrylic ester;
copolymers of vinyl acetate and of ethylene;
copolymers of vinyl acetate and of maleic ester;
vinyl chloride homopolymers;
polyethylene waxes;
polyethylene/polytetrafluoroethylene waxes;
copolymers of polyethylene and of maleic anhydride;
alkyl acrylate homopolymers and alkyl methacrylate homopolymers;
copolymers of acrylic esters such as, for example, copolymers of alkyl acrylates and of alkyl methacrylates;
copolymers of acrylonitrile and of a nonionic monomer chosen, for example, from butadiene and alkyl (meth)acrylates;
styrene homopolymers;
copolymers of styrene and of alkyl (meth)acrylate;
copolymers of styrene, of alkyl methacrylate and of alkyl acrylate;
copolymers of styrene and of butadiene;
copolymers of styrene, of butadiene and of vinylpyridine;
copolymers of styrene and of vinylpyrrolidone;
copolymers of alkyl acrylate and of urethane.
17. Composition according to any one of claims 1 to 14, characterized in that the cationic polymer of the aqueous dispersion is chosen from:
copolymers of acrylamide and of trimethylammonioethyl (meth) acrylate;
copolymers of alkyl methacrylate, of alkyl acrylate and of trimethylammonioethyl (meth)acrylate.
18. Composition according to any one of the preceding claims, characterized in that the weight concentration of the insoluble polymer particles is between 0.1 and 50% relative to the total weight of the composition.
19. Composition according to any one of the preceding claims, characterized in that the weight concentration of the insoluble polymer particles is between 1 and 30% relative to the total weight of the composition.
20. Composition according to any one of the preceding claims, characterized in that it also contains at least one additive chosen from the group consisting of thickeners, fatty acid esters, fatty acid esters of glycerol, silicones, surfactants, fragrances, preserving agents, sunscreens, proteins, vitamins, polymers, plant, animal, mineral or synthetic oils or any other additive conventionally used in the cosmetics field.
21. Composition according to any one of the preceding claims, characterized in that the cosmetically or dermatologically acceptable medium consists of water or a mixture of water and at least one cosmetically acceptable solvent.
22. Composition according to claim 21, characterized in that the cosmetically acceptable solvents are chosen from the group consisting of monoalcohols, polyalcohols, glycol ethers, fatty acid esters and mixtures thereof.
23. Composition according to any one of the preceding claims, characterized in that the keratin substance is the hair.
24. Composition according to any one of the preceding claims, characterized in that it is in the form of a gel, a milk, a cream, a more or less thickened lotion or a mousse.
25. Composition according to any one of claims 1 to 24, characterized in that it is a styling product.
26. Composition according to any one of claims 1 to 25, characterized in that it is a hair product chosen from the group consisting of shampoos; rinse-out or leave-in hair products to be applied before or after shampooing, dyeing, bleaching, permanent-waving or straightening the hair.
27. Composition according to any one of claims 1 to 26, characterized in that it is packaged in the form of a vaporizer, a pump-dispenser bottle or in an aerosol container in order to obtain a spray, a lacquer or a mousse.
28. Composition according to any one of the preceding claims, characterized in that the grafted silicone polymer is dissolved in the cosmetically or dermatologically acceptable medium or is used in the form of an aqueous dispersion of insoluble particles.
29. Non-therapeutic process for treating keratin substances, in particular the hair, characterized in that it consists in applying a composition as defined according to any one of claims 1 to 28 to the said substances and then optionally in rinsing with water.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011008540A3 (en) * 2009-06-29 2011-06-30 L'oreal S.A Refreshing cream foundation in gel form

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3679569B2 (en) * 1997-09-24 2005-08-03 花王株式会社 Aqueous hair tonic composition for hair and scalp treatment
FR2774903B1 (en) 1998-02-13 2000-04-07 Oreal COSMETIC COMPOSITION CONTAINING AN AQUEOUS DISPERSION OF INSOLUBLE PARTICLES OF POLYMERIC MATERIAL, USE AND METHOD
DE19949517A1 (en) * 1999-10-14 2001-04-19 Henkel Kgaa Firming hair cleansers
JP2001322916A (en) * 2000-05-17 2001-11-20 Kanebo Ltd Second agent composition for permanent wave
US7959198B2 (en) * 2002-05-16 2011-06-14 Labor Saving Systems, Ltd. Magnetic line retrieval system and method
DE60335798D1 (en) * 2002-05-20 2011-03-03 Danisco Us Inc SYNTHESIS OF INORGANIC STRUCTURES USING TEMPLATES AND CATALYSIS BY SELF-ASSOCIATED REPEAT PROTEIN POLYMERS
US7297678B2 (en) * 2003-03-12 2007-11-20 Genencor International, Inc. Use of repeat sequence protein polymers in personal care compositions
US20050142094A1 (en) * 2003-03-12 2005-06-30 Manoj Kumar Use of repeat sequence protein polymers in personal care compositions
JP4850709B2 (en) * 2003-05-14 2012-01-11 ダニスコ・ユーエス・インコーポレーテッド Controlled release of active agent using repetitive sequence protein polymer
US20040234609A1 (en) * 2003-05-14 2004-11-25 Collier Katherine D. Repeat sequence protein polymer active agent congjugates, methods and uses
US7128412B2 (en) 2003-10-03 2006-10-31 Xerox Corporation Printing processes employing intermediate transfer with molten intermediate transfer materials
US20050074260A1 (en) * 2003-10-03 2005-04-07 Xerox Corporation Printing apparatus and processes employing intermediate transfer with molten intermediate transfer materials
US7833541B2 (en) * 2006-05-01 2010-11-16 Momentive Performance Materials Inc. Cosmetic compositions utilizing acrylate cross linked silicone copolymer networks
BRPI0808221A2 (en) * 2007-03-21 2014-07-08 Dow Global Technologies Inc "WATERY HAIR CARE COMPOSITION, USE OF A HAIR CARE COMPOSITION AND METHOD TO SUPPLY HAIR OIL FORMATION BETWEEN WASHING"
MX2023000870A (en) 2020-07-21 2023-05-19 Chembeau LLC Diester cosmetic formulations and uses thereof.

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4744978A (en) * 1985-10-24 1988-05-17 Dow Corning Corporation Hair treating composition containing cationic organic polymer and carboxyfunctional silicone
US5632998A (en) * 1996-03-15 1997-05-27 The Procter & Gamble Company Personal care compositions containing hydrophobic graft copolymer and hydrophobic, volatile solvent

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU85303A1 (en) * 1984-04-13 1985-11-27 Oreal HAIR COMPOSITION AND METHOD FOR TREATING HAIR
US4728571A (en) 1985-07-19 1988-03-01 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer release coating sheets and adhesive tapes
US4693935A (en) 1986-05-19 1987-09-15 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer pressure sensitive adhesive composition and sheet materials coated therewith
US5061481A (en) 1989-03-20 1991-10-29 Kobayashi Kose Co., Ltd. Cosmetic composition having acryl-silicone graft copolymer
US5166276A (en) 1989-07-12 1992-11-24 Mitsubishi Petrochemical Company Ltd. Polymer for hair-care products
EP0878184A3 (en) 1989-08-07 1998-12-16 The Procter & Gamble Company Hair conditioning and styling compositions
US4972037A (en) 1989-08-07 1990-11-20 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer topical binder composition with novel fluorochemical comonomer and method of coating therewith
DK0412707T3 (en) 1989-08-07 1994-06-13 Procter & Gamble Hair conditioners and hair conditioners
JPH0525025A (en) 1991-07-22 1993-02-02 Kao Corp Hair-care cosmetics
AU674289B2 (en) 1991-08-19 1996-12-19 Procter & Gamble Company, The Hair spray compositions
SK19294A3 (en) 1991-08-19 1994-12-07 Procter & Gamble Hair-styling aerosol compositions with contains of ionic polymers
EP0639969B1 (en) 1992-05-12 1996-06-26 Minnesota Mining And Manufacturing Company Polymers in cosmetics and personal care products
US5468477A (en) * 1992-05-12 1995-11-21 Minnesota Mining And Manufacturing Company Vinyl-silicone polymers in cosmetics and personal care products
WO1993023446A2 (en) 1992-05-15 1993-11-25 The Procter & Gamble Company Adhesive agent containing polysiloxane-grafted polymer, and cosmetic compositions thereof
EP0582152B1 (en) 1992-07-28 2003-04-16 Mitsubishi Chemical Corporation A hair cosmetic composition
US5660820A (en) * 1992-10-28 1997-08-26 L'oreal Hair-setting composition
FR2697160B1 (en) 1992-10-28 1994-11-25 Oreal Aqueous cosmetic composition for fixing the hair based on a pseudo-latex.
FR2702653B1 (en) * 1993-03-16 1995-05-24 Oreal Use in cosmetics or in topical application of an aqueous dispersion based on non-volatile organopolysiloxanes and a crosslinked polymer of methacryloyloxyethyl trimethylammonium chloride.
GB9312629D0 (en) 1993-06-18 1993-08-04 Procter & Gamble Hair cosmetic compositions
US5476901A (en) 1993-06-24 1995-12-19 The Procter & Gamble Company Siloxane modified polyolefin copolymers
ES2126144T3 (en) 1993-08-27 1999-03-16 Procter & Gamble TOPICAL COMPOSITION FOR PERSONAL CARE CONTAINING AN ADHESIVE POLYMER GRAFTED WITH POLYSILOXANE AND A DRYING ADJUSTMENT.
FR2709955B1 (en) 1993-09-15 1995-10-20 Oreal Cosmetic compositions containing a linear polysiloxane-polyoxyalkylene block copolymer and an amphoteric polymer, and their uses.
US5441728A (en) 1994-06-22 1995-08-15 Chesebrough-Pond's Usa Co., A Division Of Conopco, Inc. Hairspray compositions

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4744978A (en) * 1985-10-24 1988-05-17 Dow Corning Corporation Hair treating composition containing cationic organic polymer and carboxyfunctional silicone
US5632998A (en) * 1996-03-15 1997-05-27 The Procter & Gamble Company Personal care compositions containing hydrophobic graft copolymer and hydrophobic, volatile solvent

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011008540A3 (en) * 2009-06-29 2011-06-30 L'oreal S.A Refreshing cream foundation in gel form
US8663667B2 (en) 2009-06-29 2014-03-04 L'oreal Refreshing cream foundation in gel form

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US6368606B1 (en) 2002-04-09
PL326298A1 (en) 1998-09-14
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FR2740033B1 (en) 1998-01-23
WO1997014400A1 (en) 1997-04-24
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CA2232424A1 (en) 1997-04-24
JPH11500449A (en) 1999-01-12
US20020028218A1 (en) 2002-03-07
EP0855903B1 (en) 2002-08-14
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PL186531B1 (en) 2004-01-30
ATE222090T1 (en) 2002-08-15

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