Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
  • A61K8/89—Polysiloxanes
  • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
  • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/08—Processes
  • C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
  • C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
  • C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
  • C08G18/0866—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being an aqueous medium
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/61—Polysiloxanes
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
  • C08G77/458—Block-or graft-polymers containing polysiloxane sequences containing polyurethane sequences
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J3/00—Processes of treating or compounding macromolecular substances
  • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
  • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
  • C08J3/07—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media from polymer solutions
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/54—Silicon-containing compounds
  • C08K5/541—Silicon-containing compounds containing oxygen
  • C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
  • C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
  • C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
  • C08J2375/02—Polyureas
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
  • C08J2383/04—Polysiloxanes
  • C08J2383/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen

Definitions

• the present invention relates to aqueous dispersions of silicone copolymers, which are especially nonionic and hydrogen-bond donors, to cosmetic compositions comprising them, and to their use in particular for cosmetically treating the hair.
• the shaping of hair is generally achieved by depositing a film-forming polymer on the surface of the fibre, via the use of a styling product. It is important for this polymer to have good affinity for the fibre and good styling properties, while at the same time maintaining a pleasant cosmetic feel, especially good softness and absence of tack.
• this shaping mode presents a few problems, especially in terms of resistance over time: specifically, the polymer may become brittle under the styling stresses; problems of water resistance: the shaping may be eliminated by washing with water or in the presence of surfactants; or alternatively problems in terms of a laden feel or a coarse and/or unnatural feel.
• compositions with a low content of volatile organic compounds are most particularly sought.
• the shaping of hair may also be performed via a chemical treatment of the fibre, such as permanent waving.
• the shaping of the hair has improved durability when compared with shaping by means of a styling product.
• this gain in durability is achieved by means of a chemical treatment that generally intimately modifies the hair proteins and is liable to lead to more or less substantial degradation of the physicochemical properties of the fibre, especially its intrinsic softness, hydrophilicity and/or mechanical strength.
• One of the aims of the present invention is thus to propose a means for achieving long-lasting and non-degrading shaping of the fibre, especially by virtue of the presence of a polymer dispersion, while otherwise affording, especially by virtue of the presence of the silane, good resistance of the latex deposit (aqueous polymer dispersion), in particular shampoo resistance, which will be reflected by better resistance of the shaping of the hair.
• aqueous dispersion of nonionic silicone copolymer furthermore comprising a silane can provide such long-lasting shaping that is non-degrading to the fibre and resistant.
• compositions comprising nonionic silicone polymers can be difficult. Specifically, if the silicone polymer does not bear any hydrophilic grafts and/or if high concentrations of surfactants are not introduced into the formulation, precipitation of the silicone occurs, making its formulation impossible.
• the addition of high concentrations of surfactants is not always desirable either.
• the surfactant not removed may give rise to a change in the mechanical properties of the deposits, especially plasticization, or the appearance of a laden feel (greasy, transferring onto the fingers) in particular in the field of haircare.
• document US 2005/137 327 describes the synthesis of aqueous dispersions of polyorgano-siloxane/polyurea via a process that consists in dispersing an organopolysiloxane ending with amine groups in an acidic aqueous solution preferably comprising a surfactant, in adding a diisocyanate and then in adding a base so as to regain a neutral pH and bring about polycondensation of the amino organopolysiloxane with the diisocyanate, in order finally to obtain a polyorganosiloxane/polyurea copolymer in dispersion.
• Patent FR 2 708 199 describes the synthesis of aqueous dispersions of anionic or cationic polyurethanes/polyureas. According to the described process, it is necessary to introduce a sufficiently large quantity of ionic groups to enable dispersion of the polymer in water.
• the polymer dispersion is generally prepared using monomers, which are synthesized either directly in the required solvent, or in another solvent, the synthesis then being followed in the latter case by a step of changing the solvent.
• the aim of the present invention is, in particular, to propose a novel process for preparing aqueous dispersions of silicone copolymers, the said dispersion being prepared from the already-formed polymer.
• the process according to the invention allows the introduction, into the dispersion, of silane, this being a compound that is difficult to incorporate into an aqueous polymer dispersion.
• its introduction generally brings about virtually instantaneous precipitation of the polymer in aqueous medium.
• One subject of the present invention is thus an aqueous dispersion of polysiloxane/polyurea copolymer derived from the reaction between:
• Another subject of the invention is a cosmetic composition comprising the said dispersion.
• Another subject of the invention is a cosmetic treatment process, especially for making up, caring for, cleansing, colouring or shaping keratin materials, especially bodily or facial skin, the lips, the nails, the hair and/or the eyelashes, comprising the application to the said materials of a cosmetic composition as defined above.
• Another subject of the invention is a kit in two or more parts, comprising at least one such cosmetic composition.
• silicone copolymer dispersions according to the invention can contain a large amount of water, which allows the easy introduction of hydrophilic compounds into the compositions. These hydrophilic compounds may prove to be advantageous in terms of affording novel cosmetic properties.
• compositions comprising these dispersions are entirely different from those of the prior art.
• these compositions make it possible to obtain individualized hairs, whose coating is resistant to external mechanical stresses, such as being handled, massaged or combed.
• compositions according to the invention do not require the use of large amounts of solvents of VOC type, for example ethanol, or of the type such as alkanes or isododecane, for example, or alternatively of silicone type, for example D5 or D6; this allows greater latitude of formulation.
• VOC type for example ethanol
• silicone type for example D5 or D6
• silicone copolymers used in the context of the invention are nonionic silicones, which are hydrogen-bond donors; they are especially described in patent application US 2005/137 327.
• At least one additional nonionic unit bearing at least two reactive functions containing labile hydrogen.
• the polymer of formula (I), bearing at its ends reactive units containing labile hydrogen, is of the formula:
• radicals R1 that are suitable for use in the context of the invention, mention may be made more particularly of C1-C20 alkyl radicals, and especially methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl and octadecyl radicals; C3-C7 cycloalkyl radicals, in particular the cyclohexyl radical; aryl radicals, especially phenyl and naphthyl; arylalkyl radicals, especially benzyl and phenylethyl, and also tolyl and xylyl radicals.
• C1-C20 alkyl radicals and especially methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl and octadec
• Y is chosen from the alkylene radicals of formula —(CH 2 ) a ,— in which a represents an integer between 1 and 10; it being understood that these radicals are substituted with at least one reactive function containing labile hydrogen, especially located at the end of the chain.
• silicones that will preferentially be chosen are those of formula:
• Mw average molecular weight
• polyethers especially from polyethers, polyesters, polyolefins, polycarbonates, polyamides, polyimides and polypeptides.
• polyethers especially from polyethers, polyesters, polyolefins, polycarbonates, polyamides, polyimides and polypeptides.
• the diisocyanate may be represented by the general formula (II):
• R is a linear, branched and/or cyclic, saturated or unsaturated, or even aromatic, C1-20 divalent alkylene group, which may be unsubstituted or substituted with one or more heteroatoms (in particular O, N, S or P).
• R may be chosen from the radicals of formulae:
• b is an integer between 0 and 3
• c is an integer between 1 and 20.
• the diisocyanate will preferentially be chosen from 1,6-hexamethylene diisocyanate, 1,4-tetramethylene diisocyanate, 4,4′-methylenedicyclohexyl diisocyanate, 4,4′-methylenediphenyl diisocyanate, 2,4-toluene diisocyanate, 2,5-toluene diisocyanate, 2,6-toluene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, m-xylylene diisocyanate, tetramethyl-m-xylylene diisocyanate, naphthalene diisocyanate, butane diisocyanate, hexyl diisocyanate and isophorone diisocyanate. Needless to say, these diisocyanates may be used alone or in the form of a mixture of two or more diisocyanates.
• the additional nonionic unit may be represented by formula (III):
• the copolymer is a nonionic polysiloxane/polyurea copolymer, i.e. it does not contain any ionized or ionizable groups.
• block copolymer means a copolymer formed from at least two blocks that are different from each of the polymers constituting the copolymer in the backbone of the copolymer.
• the copolymer of the invention contains at least one siloxane block and at least one polyurea block in the copolymer backbone.
• the copolymer of the invention may comprise, in addition to the polysiloxane/polyurea, other blocks of different units. Mention will be made in particular of polysiloxane/polyurea/polyurethane block terpolymers.
• the copolymer contains a weight amount of polysiloxane of greater than 5%.
• the amount of polysiloxane is predominant in the copolymer, preferably greater than 90% by weight relative to the total weight of the copolymer.
• the copolymer contains solely one or more siloxane blocks and one or more polyurea blocks.
• the copolymer may correspond to the general formula (IV):
• R represents a monovalent C1-C16 hydrocarbon-based radical, for example methyl, ethyl, vinyl and phenyl.
• R is an unsubstituted alkyl radical.
• X represents a C2-C10 alkylene radical.
• the alkylene radical X is not interrupted.
• the group A in all the units (b) and (c), when they are present, represents NH.
• all the groups A represent an NH radical.
• Z represents an oxygen atom or an NH radical.
• Y represents a C3-C13 hydrocarbon-based radical, which is preferably unsubstituted.
• Y represents a linear or cyclic aralkylene or alkylene radical.
• D represents an alkylene radical containing at least 2 and in particular at least 4 carbon atoms, and not more than 12 carbon atoms.
• D represents a polyoxyalkylene radical, in particular a polyoxyethylene or polyoxypropylene radical containing at least 20 and in particular at least 100 carbon atoms, and not more than 600 and in particular not more than 200 carbon atoms.
• n represents a number equal to at least 3 and in particular at least 25, and preferably not more than 800, in particular not more than 400 and particularly preferably not more than 250.
• a represents a number greater than 50.
• b When b is other than 0, b preferably represents a number not greater than 50 and in particular not greater than 25.
• c represents a number not greater than 10 and in particular not greater than 5.
• copolymers of the invention may be obtained according to the polymerization processes described in patent application US 2004/0 254 325 or patent application WO 03/014 194.
• the copolymer may thus be obtained via a two-step process, such that:
• W representing a hydrogen atom, a substituted or unsubstituted hydrocarbon-based radical, preferably containing from 1 to 20 carbon atoms, or a radical R 2 Si—X—NH 2 ;
• organosilicon compound of general formula (3) is reacted with an organosilicon compound of general formula (3):
• silazanes of general formula (2) or (2′) and reagents containing silanol groups in liquid molar proportions are used.
• chain extenders which are chosen from diamines, hydroxy compounds blocked with an isocyanate, dihydroxy compounds or mixtures thereof, may be used during the second step.
• the chain extenders have the general formula (6):
• the chain extender of general formula (6) may also be reacted before the reaction in the second step, with the diisocyanate of general formula (5). Where appropriate, water may be used as chain extender.
• diisocyanates of general formula (5) to be used are aliphatic compounds such as isophorone diisocyanate, 1,6-hexamethylene diisocyanate, 1,4-tetramethylene diisocyanate and 4,4′-methylene-dicyclohexyl diisocyanate or aromatic compounds, for instance 4,4′-methylenediphenyl diisocyanate, 2,4-toluene diisocyanate, 2,5-toluene diisocyanate, 2,6-toluene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, m-xylylene diisocyanate, tetramethyl-m-xylylene diisocyanate, or mixtures of these isocyanates.
• aliphatic compounds such as isophorone diisocyanate, 1,6-hexamethylene diisocyanate, 1,4-tetramethylene diisocyanate and 4,4
• An example of a commercially available compound is a diisocyanate of the Desmodur® series (H, I, M, T or W) from Bayer AG, Germany.
• Aliphatic diisocyanates, in which Y is an alkylene radical, are preferred since they lead to materials that have improved UV stabilities.
• the alkylenes containing ⁇ , ⁇ -OH end groups of general formula (6) are preferably polyalkylenes or polyoxyalkylenes. They are preferably essentially free of contaminations of mono- or trifunctional polyoxyalkylenes or polyoxyalkylenes of higher functionality.
• Polyetherpolyols, polytetramethylene-diols, polyesterpolyols or polycaprolactonediols, but also polyalkylenes containing ⁇ , ⁇ -OH end groups based on poly(vinyl acetate), poly(vinyl acetate)-ethylene copolymers, poly(vinyl chloride) copolymers or polyisobutyldiols may be used here.
• polyoxyalkyls and particularly preferably polypropylene glycols are used.
• Such compounds are commercially available as base materials, inter alia, for polyurethane foams and for uses as coating, with molecular masses Mn of up to 10 000.
• Examples are the polyetherpolyols and polyesterpolyols Baycoll® from Bayer AG, Germany or the polyetherpolyols Acclaim® from Lyondell Inc., USA.
• ⁇ , ⁇ -Alkylenediol monomers for instance ethylene glycol, propanediol, butanediol or hexanediol, may also be used.
• the term “dihydroxylated compounds” also means bishydroxyalkyl silicones, such as those sold, for example, by the company Goldschmidt under the names Tegomer H—Si 2111, 2311 and 2711.
• the preparation of the copolymers described above of general formula (I) may be performed in solution, but also in solid form, in continuous or batch mode.
• a solvent having a high solubility parameter is chosen, for instance dimethylacetamide. THF may also be used. According to one particular embodiment, the synthesis of the copolymer is performed without solvent.
• the synthesis is preferably performed in the absence of moisture and under a protective gas, usually nitrogen or argon.
• the reaction is preferably performed in the presence of a catalyst.
• the catalysts that are suitable for the preparation are dialkyltin compounds, for instance dibutyltin dilaurate or dibutyltin diacetate, or tertiary amines, for instance N,N-dimethylcyclo-hexanamine, 2-dimethylaminoethanol or 4-dimethylaminopyridine.
• the copolymer that is useful in the present invention does not contain any polyurethane.
• copolymers examples include the dimethylpolysiloxane/urea copolymer, of INCI name polyureadimethicone.
• Belsil UD-60 Wacker SLM TPSE 60 or Geniomer 60
• Belsil UD-80 Wacker SLM TPSE 80 or Geniomer 80
• Wacker Belsil UD-140 Wacker SLM TPSE 180 or Geniomer 180
• Wacker Belsil UD-200 sold by the company Wacker.
• the copolymers according to the invention have a number-average molecular mass (Mn) of between 1000 and 5 000 000, especially between 2000 and 1 000 000 and more preferentially between 2000 and 100 000 g/mol.
• Mn number-average molecular mass
• cosmetic oils or solvents used to dissolve the polymer may be evaporated off via any technique considered appropriate by a person skilled in the art, such as evaporation under vacuum.
• An aqueous dispersion of silicone copolymer that is stable over time (absence of macroscopic phase separation after 5 days at room temperature) may thus be obtained, the said dispersion also comprising a silane.
• any liquid compound (at 20-25° C., 1 atm.) that is insoluble in water and solubilizing for the copolymer.
• insoluble in water refers to a compound whose solubility in water (at 25° C., 1 atm.) is less than 1% by weight.
• the term “solubilizing for the copolymer” refers to a compound that enables the dissolution of at least 1% by weight of polymer (at 25° C., 1 atm.).
• At least one solvent compound with a boiling point of less than 150° C., at 1 atm., and/or a solvent compound that can form an azeotrope with water is used.
• silicone oils mention may be made of polydimethylsiloxanes, polymethylphenyl-siloxanes, silicones comprising polyoxyalkylene blocks or grafts, in particular polyoxyalkylene or copoly(oxyethylene/oxypropylene) such as dimethicone copolyols, silicones bearing both hydrocarbon-based hydrophobic groups (for example C 2 -C 30 alkyl groups) and polyoxyethylene or copoly(oxyethylene/oxypropylene) blocks or grafts such as alkyldimethicone copolyols, silicones bearing fluoro or perfluoro groups, such as perfluoroalkyl polydimethylsiloxanes and perfluoroalkyl polymethylphenylsiloxanes, and mixtures thereof. These silicone oils may optionally comprise alkyl or alkoxy groups at the end of the silicone chain or pendent thereon.
• Mention may also be made of linear or cyclic silicones, in particular comprising from 2 to 7 silicon atoms. Mention may be made especially of octamethylcyclotetrasiloxane, decamethylcyclopenta-siloxane, hexadecamethylcyclopentasiloxane, hepta-methylhexyltrisiloxane and heptamethyloctyltrisiloxane, and mixtures thereof.
• a solvent of linear or branched C5-C20 alcohol type is used, alone or as a mixture with a C5-C20 alkane, a cyclic volatile silicone oil and/or a C4-C20 ester, which are themselves alone or as a mixture.
• the surfactants that may be used may be anionic, cationic, amphoteric or nonionic; a mixture of surfactants may be used.
• the surfactants are cationic or anionic, preferentially cationic.
• anionic surfactants which may be used alone or as mixtures: salts, in particular alkali metal salts such as sodium salts, ammonium salts, amine salts, amino alcohol salts or alkaline-earth metal salts, for example magnesium salts, of the following compounds: alkyl sulfates, alkyl ether sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, alkyl sulfonates, alkyl phosphates, alkylamide sulfonates, alkylaryl sulfonates, ⁇ -olefin sulfonates, paraffin sulfonates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkylamide sulfosuccinates, alkyl sulfoacetates, acyl
• esters of C 6 -C 24 alkyl and of polyglycoside-carboxylic acids such as alkyl glucoside citrates, polyalkyl glycoside tartrates and polyalkyl glycoside sulfosuccinates; alkyl sulfosuccinamates, acyl isethionates and N-acyltaurates, the alkyl or acyl group of all these compounds containing from 12 to 20 carbon atoms.
• anionic surfactants that may also be used, mention may also be made of acyl lactylates in which the acyl group contains from 8 to 20 carbon atoms.
• alkyl-D-galactosideuronic acids and salts thereof mention may also be made of alkyl-D-galactosideuronic acids and salts thereof, and also polyoxyalkylenated (C 6 -C 24 alkyl)ethercarboxylic acids, polyoxyalkylenated (C 6 -C 24 alkyl) (C 6 -C 24 aryl)ethercarboxylic acids and polyoxyalkylenated (C 6 -C 24 alkyl)amidoethercarboxylic acids and salts thereof, in particular those comprising from 2 to 50 ethylene oxide groups, and mixtures thereof.
• polyoxyalkylenated (C 6 -C 24 alkyl)ethercarboxylic acids polyoxyalkylenated (C 6 -C 24 alkyl) (C 6 -C 24 aryl)ethercarboxylic acids and polyoxyalkylenated (C 6 -C 24 alkyl)amidoethercarboxylic acids and salts thereof, in particular those comprising
• the salts in particular of sodium, of magnesium or of ammonium, of alkyl sulfates; of alkyl ether sulfates, for instance sodium lauryl ether sulfate, preferably containing 2 or 3 mol of ethylene oxide; of alkyl ether carboxylates; and mixtures thereof, the alkyl groups generally containing from 6 to 24 carbon atoms and preferably from 8 to 16 carbon atoms.
• nonionic surfactants that may be used in the composition according to the invention, mention may be made of polyethoxylated, polypropoxylated or polyglycerolated fatty acids, (C 1 -C 20 )alkylphenols, ⁇ -diols or alcohols, having a fatty chain containing, for example, 8 to 18 carbon atoms, it being possible for the number of ethylene oxide or propylene oxide groups to range in particular from 2 to 50 and for the number of glycerol groups to range in particular from 2 to 30.
• amphoteric surfactants mention may be made of aliphatic secondary or tertiary amine derivatives, in which the aliphatic group is a linear or branched chain containing 8 to 22 carbon atoms and containing at least one water-soluble anionic group, such as, for example, a carboxylate, sulfonate, sulfate, phosphate or phosphonate group; mention may also be made of (C 8 -C 20 )alkylbetaines, sulfobetaines, (C 8 -C 20 ) alkylamido (C 6 -C 8 ) alkylbetaines or (C 8 -C 20 ) alkyl-amido(C 6 -C 8 )alkylsulfobetaines; and mixtures thereof.
• aliphatic secondary or tertiary amine derivatives in which the aliphatic group is a linear or branched chain containing 8 to 22 carbon atoms and containing at least one water
• amine derivatives that may be mentioned are the products sold under the name Miranol®, as described in patents U.S. Pat. No. 2,528,378 and U.S. Pat. No. 2,781,354 and classified in the CTFA dictionary, 3rd edition, 1982, under the names Amphocarboxyglycinate and amphocarboxypropionate, having the respective structures (2) and (3):
• R 2 represents an alkyl group derived from an acid R 2 —COOH present in hydrolysed coconut oil, or a heptyl, nonyl or undecyl group,
• R 3 represents a ⁇ -hydroxyethyl group
• R 4 represents a carboxymethyl group
• X′ represents the —CH 2 CH 2 —COOH group or a hydrogen atom
• Y′ represents —COOH or the —CH 2 —CHOH—SO 3 H group
• R 2 represents the alkyl group of an acid R 9 —COOH present in coconut oil or in hydrolysed linseed oil, an alkyl group, especially a C 17 group and its iso form, or an unsaturated C 17 group.
• cocoamphodiacetate sold under the trade name Miranol® C2M Concentrate by the company Rhodia.
• amphoteric surfactants that are preferably used are (C 8 -C 20 ) alkylbetaines, (C 8 -C 20 )alkyl-amido(C 6 -C 9 )alkylbetaines and alkylamphodiacetates, and mixtures thereof.
• cationic surfactants mention may be made of:
• alkylpyridinium salts ammonium salts of imidazoline, diquaternary ammonium salts, and ammonium salts containing at least one ester function;
• radicals R1 to R4 which may be identical or different, represent a linear or branched aliphatic radical containing from 1 to 30 carbon atoms, or an aromatic radical such as aryl or alkylaryl; the aliphatic radicals may optionally comprise heteroatoms (O, N, S or halogens).
• the aliphatic radicals are chosen, for example, from C12-C22 alkyl, alkoxy, C2-C6 polyoxyalkylene, alkylamide, (C12-C22)alkylamido(C2-C6)alkyl, (C12-C22)alkylacetate and hydroxyalkyl radicals, containing from about 1 to 30 carbon atoms.
• X ⁇ is an anion chosen from the group of halides, phosphates, acetates, lactates, C2-C6 alkyl sulfates and alkyl- or alkylaryl-sulfonates.
• R5 and R6 preferably denote a mixture of alkenyl or alkyl radicals containing from 12 to 21 carbon atoms, such as, for example, fatty acid derivatives of tallow, R7 denotes methyl and R8 denotes hydrogen.
• a product is, for example, Quaternium-27 (CTFA 1997) or Quaternium-83 (CTFA 1997), which are sold under the names Rewoquat® W75, W90, W75PG and W75HPG by the company Witco,
• the alkyl radicals R15 may be linear or branched, and more particularly linear.
• R15 denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl radical, and more particularly a methyl or ethyl radical.
• the sum x+y+z is from 1 to 10.
• R16 is a hydrocarbon-based radical R20, it may contain from 12 to 22 carbon atoms, or contain from 1 to 3 carbon atoms.
• R18 is a hydrocarbon-based radical R22, it preferably contains 1 to 3 carbon atoms.
• R17, R19 and R21 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C11-C21 hydrocarbon-based radicals, and more particularly from linear or branched, saturated or unsaturated C11-C21 alkyl and alkenyl radicals.
• x and z which may be identical or different, are 0 or 1.
• y is equal to 1.
• r, n and p which may be identical or different, are equal to 2 or 3 and even more particularly equal to 2.
• the anion X ⁇ is preferably a halide (chloride, bromide or iodide) or a C1-C4 alkyl sulfate, more particularly methyl sulfate.
• the anion X ⁇ may also represent methanesulfonate, phosphate, nitrate, tosylate, an anion derived from an organic acid (such as acetate or lactate), or any other anion that is compatible with the ammonium containing an ester function.
• the surfactants may be, for example, the salts (chloride or methyl sulfate) of diacyloxyethyl-dimethylammonium, of diacyloxyethylhydroxyethyl-dimethylammonium, of monoacyloxyethylhydroxyethyl-dimethylammonium, of triacyloxyethylmethylammonium, of monoacyloxyethylhydroxyethyldimethylammonium, and mixtures thereof.
• the acyl radicals preferably contain 14 to 18 carbon atoms and are more particularly derived from a plant oil, for instance palm oil or sunflower oil. When the compound contains several acyl radicals, these radicals may be identical or different.
• Such compounds are sold, for example, under the names Dehyquart® by the company Cognis, Stepanquat® by the company Stepan, Noxamium® by the company Ceca, and Rewoquat® WE 18 by the company Rewo-Goldschmidt.
• quaternary ammonium salts and in particular behenyltrimethylammonium chloride, dipalmitoylethyl hydroxyethyl methyl ammonium methosulfate, cetyltrimethylammonium chloride, quaternium-83, behenylamidopropyl-2,3-dihydroxypropyldimethylammonium chloride and palmitylamidopropyltrimethylammonium chloride.
• the silane present in the aqueous dispersion is of structure:
• Examples that may be mentioned include N-(3-acryloxy-2-hydroxypropyl)-3-aminopropyltriethoxysilane, 4-aminobutyltriethoxysilane, 3-aminopropylmethyl-diethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropyltris(methoxyethoxyethoxy)silane, bis(methyl-diethoxysilylpropyl)amine, bis[3-(triethoxysilyl)-propyl]urea, 3-(2,4-dinitrophenylamino)propyltriethoxy-silane, hydroxymethyltriethoxysilane, mercapto-methylmethyldiethoxysilane, 3-mercaptopropyl-triethoxysilane, o-(methacryloxyethyl)-N-(triethoxy-silylpropyl)urethane, N-(3-methacryloxy-2-
• the silane may serve to promote the attachment of the copolymer to the keratin support.
• the silane alone or as a mixture, may be present in a proportion of from 0.5% to 30% by weight, especially 1% to 25% by weight or even 2% to 20% by weight, relative to the weight of the dispersion.
• ingredients may be present in the aqueous dispersion of silicone copolymer according to the invention; these ingredients may be introduced into the aqueous phase or the organic phase, during the preparation of the dispersion.
• cationic, anionic and/or nonionic silicones bearing hydrophilic or hydrophobic grafts plasticizers; spreading agents or coalescers; solid fatty substances such as fatty alcohols, fatty acids or plant or mineral waxes; conditioning agents, especially of cationic polymer type including polyamines; anionic (neutralized or non-neutralized), cationic or nonionic polymers and especially styling polymers; pH agents, bases or acids; organic or mineral pigments or colorants; sunscreens, fragrances, peptizers, preserving agents, amino acids or vitamins; and thickeners
• a process for preparing the aqueous dispersions of polysiloxane/polyurea comprises the following steps:
• the copolymer is present in a proportion of from 2% to 60% by weight, especially 5% to 40% by weight or even 8% to 25% by weight, in the organic phase.
• the surfactant(s) are present in a proportion of from 0.01% to 15% by weight, especially 0.05% to 10% by weight or even 0.1% to 6% by weight, in the aqueous phase.
• the surfactant represents 0.01% to 15% by weight, especially 0.05% to 10% by weight or even 0.1% to 5% by weight relative to the weight of the organic phase comprising the copolymer.
• aqueous phase comprising the surfactants Preferably, 0.5 to 50 parts by weight and in particular 0.8 to 20 parts of aqueous phase comprising the surfactants are added, especially 1 to 12 parts, or even 2 to 8 parts, per 1 part of organic phase comprising the copolymer.
• the emulsification is performed at a temperature from 15 to 100° C., especially 18 to 50° C., or even 20-30° C., at a speed of between 50 and 30 000 rpm and especially 200 to 10 000 rpm, via any means known to those skilled in the art, especially with an homogenizer, in particular of the Ultra-Turrax type.
• all or part of the organic phase may then be evaporated, via any technique considered adequate by a person skilled in the art, such as evaporation under reduced pressure (under vacuum).
• aqueous dispersion of polysiloxane/polyurea copolymer whose solids content may be between 0.1% and 50% by weight, especially 0.5% to 40% by weight, or even 1% to 30% by weight and better still 2% to 25% by weight.
• the dispersion according to the invention may comprise solvent compounds and/or an organic phase, which may represent 0.05% to 80% by weight and especially 1% to 70% by weight of the said dispersion.
• This organic phase may also be absent (less than 0.05%, or even 0%).
• the dispersion may also comprise surfactants, which may represent 0.05% to 10% by weight, especially 0.01% to 8% by weight or even 0.1% to 5% by weight of the said dispersion. These surfactants may also be absent (less than 0.05%, or even 0%).
• aqueous dispersion according to the invention finds a quite particular application in the field of cosmetics, especially in the field of haircare.
• the amount of polymer present in the compositions obviously depends on the type of composition and on the desired properties; it may range between 0.01% and 30% by weight, preferably between 0.1% and 20% by weight, especially between 0.5% and 10% by weight, or even between 1% and 5% by weight of polymer solids relative to the weight of the cosmetic composition.
• compositions according to the invention may be in any galenical form conventionally used for topical application, and especially in the form of an aqueous, alcoholic or aqueous-alcoholic solution or suspension; an oily solution or suspension; a solution or dispersion of the lotion or serum type; an emulsion of liquid or semi-liquid consistency of the milk or cream type, obtained by dispersing a fatty phase in an aqueous phase (O/W) or, conversely, (W/O); an aqueous or anhydrous gel, an ointment, a loose or compact powder to be used in this form or to be incorporated into an excipient, or any other cosmetic form.
• O/W aqueous phase
• W/O aqueous or anhydrous gel, an ointment, a loose or compact powder to be used in this form or to be incorporated into an excipient, or any other cosmetic form.
• compositions may be packaged, especially in pump bottles or in aerosol containers, so as to apply the composition in vaporized form or in the form of a mousse.
• packaging forms are indicated, for example, when it is desired to obtain a spray or a mousse for treating the hair.
• the compositions in accordance with the invention may also be in the form of creams, gels, emulsions, lotions or waxes.
• the composition according to the invention is packaged in the form of an aerosol in order to obtain a lacquer or a mousse, it comprises at least one propellant.
• compositions according to the invention comprise a cosmetically acceptable medium, i.e. a medium that is compatible with keratin materials, especially facial or bodily skin, the lips, the hair, the eyelashes, the eyebrows and the nails.
• a cosmetically acceptable medium i.e. a medium that is compatible with keratin materials, especially facial or bodily skin, the lips, the hair, the eyelashes, the eyebrows and the nails.
• the ingredients of the cosmetically acceptable medium may be present in usual amounts, which may be readily determined by a person skilled in the art, and which may be, for each ingredient, between 0.01% and 80% by weight.
• nonionic, cationic, anionic or amphoteric surfactants hydrophilic solvents (alcohols) or hydrophobic solvents (alkanes); cationic, anionic or nonionic silicones bearing hydrophilic or hydrophobic grafts, which may or may not be phenylated; plasticizers, for example of polyol type; spreading agents or coalescers; silanes, especially those having the structure described above; liquid or solid fatty substances such as fatty alcohols, fatty acids, plant or mineral oils and plant or mineral waxes; conditioning agents such as cationic polymers including polyamines; polymers, especially styling polymers, which are in particular anionic (neutralized or non-neutralized), cationic or nonionic; pH agents (bases or acids); organic or mineral pigments or colorants; fillers such as nacres, TiO 2 , resins and clays; sunscreens; fragrances; peptizers; preserving
• the cosmetic composition according to the invention may be in the form of a product for caring for, cleansing and/or making up bodily or facial skin, the lips, the eyebrows, the eyelashes, the nails and the hair, an antisun or self-tanning product, a body hygiene product, or a haircare product, especially for caring for, cleansing, styling, shaping or colouring the hair.
• the composition especially finds a particularly advantageous use in the field of haircare, especially for holding the hairstyle or shaping the hair, or for the care, cosmetic treatment or cleansing of the hair.
• the haircare compositions are preferably shampoos, hair conditioners, styling or care gels, care lotions or creams, conditioners, hairsetting lotions, blow-drying lotions, hair styling and fixing compositions such as lacquers or sprays; hair restructuring lotions; lotions or gels for preventing hair loss, antiparasitic shampoos, antidandruff lotions or shampoos, and anti-seborrhoea treating shampoos.
• the lotions may be packaged in various forms, especially in vaporizers, in pump bottles or in aerosol containers so as to apply the composition in vaporized form or in the form of a mousse.
• the composition may also be in the form of a hair colouring product, especially an oxidation dye or direct dye, optionally in the form of colouring shampoos; in the form of a permanent-waving, relaxing or bleaching composition, or alternatively in the form of a rinse-out composition, to be applied before or after dyeing, bleaching, permanent-waving or relaxing the hair, or alternatively between the two steps of a permanent-waving or relaxing operation.
• a hair colouring product especially an oxidation dye or direct dye, optionally in the form of colouring shampoos
• a permanent-waving, relaxing or bleaching composition or alternatively in the form of a rinse-out composition, to be applied before or after dyeing, bleaching, permanent-waving or relaxing the hair, or alternatively between the two steps of a permanent-waving or relaxing operation.
• composition according to the invention may also be in the form of a care composition, especially a moisturizer, for bodily or facial skin, the lips and/or the integuments, especially a care product for cosmetically treating the skin and especially for moisturizing it, making it smooth, depigmenting it, nourishing it, protecting it against sunlight, or giving it a specific cosmetic treatment.
• a care composition especially a moisturizer, for bodily or facial skin, the lips and/or the integuments, especially a care product for cosmetically treating the skin and especially for moisturizing it, making it smooth, depigmenting it, nourishing it, protecting it against sunlight, or giving it a specific cosmetic treatment.
• a lipcare base for lipsticks, an antisun or artificial tanning composition, a facial care composition (a day, night, anti-ageing or moisturizing composition); a matting composition; a skin cleansing composition, for example a makeup-removing product or a bath or shower gel, or a cleansing bar or soap; a body hygiene composition, especially a deodorant or antiperspirant product, or alternatively a hair-removing composition or an aftershave gel or lotion.
• a makeup product for bodily or facial skin for bodily or facial skin, the lips, the eyelashes, the nails or the hair; in particular a foundation, a blusher, a makeup rouge, an eyeshadow, a concealer product, an eyeliner, a mascara, a lipstick, a lip gloss, a lip pencil; a nail varnish, a nailcare product; a temporary tattoo product for bodily skin.
• composition according to the invention finds an advantageous application in holding the hairstyle or shaping the hair, or alternatively in caring for, cosmetically treating or cleansing the hair.
• One subject of the invention is thus a cosmetic treatment process, especially for making up, caring for, cleansing, colouring or shaping keratin materials, especially bodily or facial skin, the lips, the nails, the hair and/or the eyelashes, comprising the application to the said materials of a cosmetic composition comprising at least one compound according to the invention.
• it is a cosmetic treatment process for conditioning the hair, in particular to give it or improve its suppleness, disentangling, smoothing, combability and manageability.
• the application of the composition may optionally be followed by a heat treatment step.
• composition may also be in the form of a kit in two or more parts.
• These parts may be intended for mixing together at the time of use or alternatively for application successively to the keratin substrate to be treated, in particular the hair.
• These successive application steps may or may not be interrupted by a step of manual drying, for example with a towel, or by means of an appliance, for instance a hairdryer.
• composition comprising the dispersion according to the invention is used in leave-in mode.
• the composition comprising the dispersion according to the invention is used in combination with a heating appliance for shaping the hair, such as a curling iron, a waving iron, a crimping iron, a straightening iron or heated curlers.
• a heating appliance for shaping the hair such as a curling iron, a waving iron, a crimping iron, a straightening iron or heated curlers.
• the temperature of the heating appliance used is preferably between 60° C. and 200° C.
• the composition according to the invention may be applied to wet or dry hair, a step optionally followed by partial or total drying of the hair, optionally followed by the application of a heating tool, which may be a hairdryer or a tool for simultaneously applying a mechanical constraint and heating (straightening iron, waving iron, crimping iron or curling iron, using or not using steam).
• a heating tool which may be a hairdryer or a tool for simultaneously applying a mechanical constraint and heating (straightening iron, waving iron, crimping iron or curling iron, using or not using steam).
• the temperature of the tool is preferably between 60° C. and 200° C.
• a polysiloxane/polyurea copolymer (Belsil UD80) and aminopropyltriethoxysilane (APTES) are dissolved in hexanol. This solution is added to an aqueous solution of cationic surfactant (cetyltrimethylammonium chloride) diluted in water and stirred with an Ultra-Turrax blender at 13 000 rpm. The mixture is homogenized for 30 minutes and the hexanol is then removed on a rotary evaporator. An opaque white aqueous dispersion is thus obtained, the composition of which is given below.
• cationic surfactant cetyltrimethylammonium chloride
• compositions are prepared (weight %):
• composition 1 compo- composition 1 composition 2 composition 3 sition 4 Dispersion 48% — — — — (1) Dispersion — 53% — — (2) Dispersion — — 52% — (3) Dispersion — — — 76.5% (4) lactic qs pH 10 qs pH 10 qs pH 10 qs pH 10 acid deionized qs 100% qs 100% qs 100% qs 100% water
• composition 1 g is deposited on a lock of 2.7 g of natural hair. After drying, shaping is performed using a heating tool such as a curling iron, applied for 30 seconds, with the thermostat set for a temperature of between 140 and 180° C. After cooling, the lock is suspended in ambient medium. The shape setting and its hold over time are evaluated, at T 0 and after 6 shampoo washes.
• a heating tool such as a curling iron
• the resistance of the coating to shampooing is evaluated in the following manner: 1 g of Ultra Doux shampoo from Garnier is deposited on the prewetted lock; the lock is massaged from the root to the end in passes; the lock is then rinsed in water for 10 seconds. The operation is repeated six times in a row. After drying, the iron is reapplied and the lock is again suspended for evaluation of the shape.
• the comparative composition only contains water.

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