Classifications

• • 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
• • 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
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/37—Esters of carboxylic acids
• • 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
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
  • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
• • 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
  • A61K8/86—Polyethers

Definitions

• Cosmetic composition comprising a fatty acid ester and a copolymer of acrylate (s) or methacrylate (s) and of hydroxyester of acrylate (s) or methacrylate (s) and its use as a hair product .
• the present invention relates to a cosmetic composition
• a cosmetic composition comprising, in a cosmetically acceptable medium, at least one fatty acid ester and at least one copolymer of acrylate (s) or of methacrylate (s) and of acrylate hydroxyester ( s) or methacrylate (s).
• the present invention also relates to a cosmetic hair treatment method using the aforementioned composition, and a use of this cosmetic composition as a hair product, for example as a styling product.
• Hair styling products are usually used to build, structure the hairstyle and give it a lasting hold.
• the corresponding compositions generally comprise one or more film-forming polymers in a cosmetically acceptable medium. These polymers allow the formation of a sheathing film on the hair, thus ensuring the maintenance of the hairstyle.
• the fixing polymer films thus formed have the disadvantage of being relatively friable, which limits in time the holding of the hairstyle, and causes the formation on the hair of unsightly residues.
• a plasticizer such as a glycol. This effectively improves the behavior of the hairstyle over time and limit the formation of residues during the day.
• the non-friability of the polymer films is generally related to the fixing polymer concentration in the styling product (or degree of fixation): if the polymer concentration is decreased fixing for reduce the rigidity of the hairstyle, then the polymer film becomes more friable and the behavior of the hairstyle is less good.
• the present invention makes it possible in particular to prepare hair styling products that provide significantly improved hairstyling durability, including in products with flexible fixation, that is to say with a low concentration of fixing polymer.
• compositions according to the invention have been found to provide a very marked improvement in the cosmetic properties of the hair after disentangling: the hair is much softer and less dry than after the application of a conventional fixing product.
• the subject of the present invention is therefore a cosmetic composition
• a cosmetic composition comprising, in a cosmetically acceptable medium, at least one fatty acid ester, and at least one copolymer of acrylate (s) or of methacrylate (s) and of hydroxyester of acrylate (s) or methacrylate (s), characterized in that the weight ratio between the amount of copolymer (s) of acrylate (s) or methacrylate (s) and acrylate hydroxyester (s) or of methacrylate (s) on the one hand and the amount of ester (s) of fatty acid (s) on the other hand, is between 0.8 and 8.
• Another subject of the invention consists of a cosmetic hair treatment method using a composition according to the invention as described below.
• the subject of the invention is also the use of the composition according to the invention for the cosmetic treatment of the hair, in particular for shaping and / or maintaining the hairstyle.
• the cosmetic composition comprises, in a cosmetically acceptable medium, at least one fatty acid ester and at least one copolymer of acrylate (s) or of methacrylate (s) and of acrylate hydroxy ester (s). ) or methacrylate (s).
• cosmetically acceptable medium is meant a medium compatible with keratin materials and in particular the hair.
• the cosmetically acceptable medium comprises water and / or at least one cosmetically acceptable solvent chosen from C 1 -C 4 lower alcohols, such as ethanol, isopropanol, tert-butanol or n-butanol. -butanol; polyols such as glycol, glycerol, propylene glycol; polyol ethers; C 5 alkanes -
• C 10 C 3 -4 ketones such as acetone and methyl ethyl ketone; C 1 -C 4 alkyl acetates such as methyl acetate, ethyl acetate and butyl acetate; dimethoxyethane, diethoxyethane; and their mixtures.
• composition according to the invention comprises at least one copolymer of acrylate (s) or of methacrylate (s) and of hydroxyester of acrylate (s) or methacrylate (s), that is to say a copolymer obtained by copolymerization of at least two monomers:
• said copolymer is obtained by copolymerization of at least three monomers: at least one first monomer chosen from acrylic acid and methacrylic acid,
• said second monomer comprises at least one C 1 or C 2 alkyl acrylate or methacrylate.
• said second monomer can then be methyl acrylate, ethyl acrylate, methyl methacrylate, ethyl methacrylate, and mixtures of these compounds.
• said third monomer is selected from hydroxyethyl acrylate, hydroxyethyl methacrylate, and mixtures of these compounds.
• the composition according to the invention comprises a mixture of at least two copolymers of acrylate (s) or of methacrylate (s) and of hydroxyester of acrylate (s) or methacrylate (s) as described above.
• It may be a mixture of at least two copolymers with at least two monomers as described above, a mixture of at least two copolymers with at least three monomers as described above, or a mixture of at least one copolymer with at least two monomers and at least one copolymer with at least three monomers as described above.
• the composition according to the invention comprises a mixture of two copolymers of acrylate (s) or of methacrylate (s) and of hydroxyester of acrylate (s) or methacrylate (s). ), each of the copolymers being obtained by copolymerization of at least three monomers as described above, namely: at least one first monomer chosen from acrylic acid and methacrylic acid,
• the composition according to the invention comprises a mixture of two copolymers of acrylate (s) or of methacrylate (s) and of hydroxyester of acrylate (s) or methacrylate (s). ), comprising a first copolymer obtained by copolymerization of at least three monomers as described above: at least one first monomer chosen from acrylic acid and methacrylic acid, - at least one second monomer chosen from acrylates and C1 to C4 alkyl methacrylates, and
• At least one third monomer chosen from C1 to C4 hydroxyalkyl acrylates and methacrylates and a second copolymer obtained by copolymerization of at least two monomers: at least one first monomer chosen from C1-C4 alkyl acrylates and methacrylates, and at least one second monomer chosen from C1-hydroxyalkyl acrylates and methacrylates; at C4; said second copolymer does not contain monomers consisting of unsaturated carboxylic acids.
• composition according to the invention comprises a mixture of at least two copolymers of acrylate (s) or of methacrylate (s) and of hydroxyester of acrylate (s) or methacrylate (s), the two copolymers of this
• the mixture preferably has different glass transition temperatures.
• the glass transition temperature (Tg) is measured by Differential Scanning Calorimetry (DSC) according to ASTM D3418-97.
• One of the two copolymers preferably has a Tg ranging from 35 ° C. to 250 ° C., more preferably from 40 ° C. to 150 ° C. and even more preferentially from 75 ° C. to 100 ° C.
• the second copolymer preferably has a Tg ranging from -20 ° C to 35 ° C, more preferably from 0 ° C to 35 ° C and even more preferably from 15 ° C to 30 ° C.
• the difference of Tg between the two copolymers is preferably greater than or equal to 10 ° C, more preferably greater than or equal to 20 ° C and even more preferably greater than or equal to 30 ° C.
• the copolymer (s) of acrylate (s) or of methacrylate (s) and of hydroxyester of acrylate (s) or of methacrylate (s) usable (s) in the compositions according to the invention can (can) ) be a block copolymer (s), statistical or alternating. Preferably, it is a random copolymer.
• the copolymer of acrylate (s) or of methacrylate (s) and of hydroxyester of acrylate (s) or methacrylate (s) is an anionic copolymer.
• it comprises hard sequences and soft sequences, that is to say sequences with two glass transition temperatures (Tg), one of the Tg being between 15 and 35 ° C, preferably between 20 and 30 ° C, the other Tg being between 90 and 1 10 ° C, preferably between 95 and 105 ° C.
• Tg glass transition temperatures
• the hard sequence comprises at least one monomer chosen from methyl methacrylate, butyl acrylate, hydroxyethyl methacrylate and methacrylic acid, and more advantageously, the hard sequence comprises all these monomers.
• the soft sequence comprises at least one monomer selected from ethyl acrylate, butyl acrylate, hydroxyethyl methacrylate, methacrylic acid and more preferably, the soft sequence comprises all these monomers.
• the molecular weight of this copolymer is between 10,000 g / mol and 200,000 g / mol. Even more preferentially, it is between 20,000 g / mol and 100,000 g / mol.
• the copolymers of acrylate (s) or of methacrylate (s) and of hydroxyester of acrylate (s) or of methacrylate (s) can be in a wide variety of forms, for example in the form of solutions or emulsions in water or any other solvent. They can be synthesized by any known method for preparing a copolymer from its different monomers.
• copolymers and copolymer mixtures that may be used in the compositions according to the invention, mention may be made, inter alia, of the products sold under the name Acudyne by the company Rohm & Haas, such as, for example, and in a nonlimiting manner, the products proposed under the name ACUDYNE DHR, ACUDYNE 258, ACUDYNE 180.
• the composition according to the invention preferably contains at least 0.01% by weight of copolymer (s) of acrylate (s) or of methacrylate (s) and of hydroxyester of acrylate (s) or methacrylate (s) , relative to the total weight of the composition.
• it contains from 0.01% to 20% by weight of copolymer (s) of acrylate (s) or of methacrylate (s) and of hydroxyester of acrylate (s) or methacrylate (s), and even more preferably from 0.1 to 10% by weight, more preferably from 0.5 to 8% by weight, relative to the total weight of the composition.
• composition according to the invention also comprises at least one fatty acid ester, the fatty acid being saturated or unsaturated, linear or branched and preferably comprising from 8 to 30 carbon atoms, more preferably from 12 to 24 carbon atoms. carbon, more preferably from 15 to 18 carbon atoms.
• esters that can be used in the compositions according to the invention include esters of fatty acids and of monoalcohols, esters of fatty acids and of polyols, and mixtures of these two types of esters.
• composition according to the invention may comprise at least one fatty acid and monoalcohol ester, chosen from compounds of formula R 8 COORb in which R a represents the residue of a saturated or unsaturated, linear or branched fatty acid. and including
• Rb represents a hydrocarbon chain linear or branched, saturated or unsaturated, containing from 1 to 30 carbon atoms, preferably from 3 to 22 carbon atoms.
• esters By way of examples of such esters, mention may especially be made of purcellin oil (stearyl octanoate), isopropyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate and isononanoate. isononyl, 2-ethylhexyl palmitate, 2-hexyldecyl laurate, 2-octyldecyl palmitate, 2-octyldodecyl myristate, isostearyl neopentanoate or tridecyl neopentanoate.
• purcellin oil stearyl octanoate
• isopropyl myristate isopropyl palmitate
• butyl stearate hexyl laurate
• isononyl 2-ethylhexyl palmitate, 2-hexyldecyl laurate, 2-octyl
• composition according to the invention may comprise at least one fatty acid and polyol ester, preferably chosen from monoesters, diesters and triesters of fatty acids containing from 8 to 30 carbon atoms and polyols.
• non-polyoxyalkylenated or polyalkylene glycols Preferably, the non-polyoxyalkylenated polyol is chosen from ethylene glycol, propylene glycol and glycerol. Preferably, it contains at least 3 carbon atoms.
• the fatty acid ester is preferably chosen from mono or diesters of fatty acid and of ethylene glycol, mono or diesters of fatty acid and polyethylene glycol, mono or diesters of fatty acid and of propylene. glycol, and mono or diesters of fatty acid and polypropylene glycol, mono, di or triesters of fatty acid and glycerol.
• the ester comprises a polyalkylene glycol group
• this group preferably comprises from 2 to 500 alkylene glycol units. More preferably, such a group comprises from 2 to 250 alkylene glycol units, more preferably from 2 to 200 alkylene glycol units.
• the polyalkylene glycol group is a polyethylene glycol group.
• the composition according to the invention comprises at least one mono or one diester of fatty acid and polyethylene glycol. Even more preferably, the composition according to the invention comprises a polyethylene glycol monostearate or distearate having from 2 to 200 ethylene glycol units.
• the composition according to the invention preferably contains at least 0.05% by weight of ester (s) of fatty acid (s), relative to the total weight of the composition. Preferably, it contains from 0.05 to 20% by weight, more preferably from 0.1 to 10% by weight, and even more preferably from 0.5 to 8% by weight of acid ester (s) ( s) fat, relative to the total weight of the composition.
• the compositions according to the invention may also contain at least one fatty substance different from the fatty acid esters described above.
• the fatty substances that can be used in the present invention are chosen in particular from animal oils, mineral oils, natural or synthetic oils, fatty alcohols, waxes and their mixtures.
• mineral oil mention may be made of paraffin oil and liquid petroleum jelly.
• synthetic oil there may be mentioned squalane, poly ( ⁇ -olefins) such as isododecane or isohexadecane, transesterified vegetable oils and fluorinated oils.
• Preferred fatty alcohols include myristyl, cetyl, stearyl, arachidyl, behenyl and erucyl alcohols.
• a wax within the meaning of the present invention, is a lipophilic compound, solid at room temperature (about 25 ° C.), with a reversible solid / liquid state change, having a melting temperature greater than about 40 ° C. and that can go up to 200 ° C, and having in the solid state an anisotropic crystalline organization.
• the size of the crystals of the wax is such that the crystals diffract and / or diffuse the light, conferring on the composition which comprises them a more or less opaque cloudy appearance.
• waxes that can be used in the present invention, mention may be made of mineral waxes, for example of paraffin, petroleum jelly, lignite or microcrystalline waxes, ceresin or ozokerite; synthetic waxes such as polyethylene waxes, Fischer-Tropsch waxes, and mixtures thereof.
• the fatty substances as described above, when they are present in the composition according to the invention, are preferably present in an amount ranging from 0.1 to 30% by weight, preferably from 1 to 20% by weight. and more preferably from 5 to 15% by weight, based on the total weight of the composition.
• the composition according to the invention may also comprise at least one surfactant chosen from cationic surfactants, anionic surfactants, nonionic surfactants other than esters of fatty acids and (poly) alkylene glycol, or amphoteric or zwitterionic surfactants.
• the composition according to the invention then preferably comprises at least 0.01% by weight of surfactant (s), relative to the total weight of the composition.
• the composition according to the invention contains from 0.01 to 20% by weight of surfactant (s), more preferably from 0.05 to 4% by weight, relative to the total weight of the composition.
• anionic surfactants that can be used in the compositions according to the present invention, mention may be made in particular (nonlimiting list) of the salts (in particular alkaline salts, in particular sodium salts, ammonium salts, amine salts, sodium salts and the like).
• alkylsulfates alkylethersulfates, alkylamidoethersulfates, alkylarylpolyethersulfates, monoglycerides sulfates; alkylsulfonates, alkylphosphates, alkylamidesulfonates, alkylarylsulfonates, ⁇ -olefin-sulfonates, paraffin-sulfonates; alkylsulfosuccinates; alkyl ether sulfosuccinates, alkyl amide sulfosuccinates; alkylsulfosuccinamates; alkylsulfoacetates; alkyl ether phosphates, acylsarcosinates; acylisethionates and N-acyltaurates, the alkyl or acyl radical of all these different compounds preferably comprising alkylsulfates, alkylethersulfates, alkylamido
• anionic surfactants that can still be used, mention may also be made of fatty acid salts such as the oleic, ricinoleic, palmitic and stearic acid salts; coconut oil or hydrogenated coconut oil acids; acyl lactylates whose acyl radical has 8 to 20 carbon atoms.
• weakly anionic surfactants such as acid alkyl D galactoside uronic and salts thereof, polyoxyalkylenated (C 6 - C 24) ether carboxylic acids, polyoxyalkylenated (C 6 -C2 4) aryl ether carboxylic polyoxyalkylenated, polyoxyalkylenated (C 6 -C 24 ) alkyl ether carboxylic acids and their salts, in particular those containing from 2 to
• anionic surfactants it is preferred to use, according to the invention, the salts of alkyl sulphates and alkyl ether sulphates and their mixtures.
• the cationic surfactants that can be used in the compositions of the present invention comprise, for example, primary, secondary or tertiary fatty amine salts, optionally polyoxyalkylenated salts, quaternary ammonium salts, and mixtures thereof.
• radicals R 8 to R 11 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 comprise heteroatoms such as in particular oxygen, nitrogen, sulfur and halogens.
• the aliphatic radicals are for example chosen from alkyl C 1 -30 alkoxy, C 1 -30, polyoxy (C 2 -C 6) alkylamide C 1 -30, (C 1 2-C22) amidoalkyl ( C 2 -C 6) alkyl (Ci2-
• X is an anion selected from the group of halides, phosphates, acetates, lactates, (C 2 -C 6 ) alkyl sulfates, alkyl- or alkylarylsulfonates.
• tetraalkylammonium chlorides such as, for example, dialkyldimethylammonium or alkyltrimethylammonium chlorides in which the alkyl radical has from about 12 to 22, are preferred.
• carbon atoms in particular behenyltrimethylammonium, distearyl dimethylammonium, cetyltrimethylammonium, benzyldimethylstearylammonium chlorides or else palmitylamidopropyltrimethylammonium chloride or stearamidopropyldimethyl (myristylacetate) ammonium chloride sold under the CERAPHYL ® 70 denomination by the company VAN DYK.
• R 12 represents an alkenyl or alkyl radical containing from 8 to 30 carbon atoms, for example derived from tallow fatty acids
• R 13 represents a hydrogen atom, a C 1 -C 4 alkyl radical or an alkenyl radical; or alkyl having from 8 to 30 carbon atoms
• R 14 represents a C 1 -C 4 alkyl radical
• R 15 represents a hydrogen atom, a C 1 -C 4 alkyl radical
• X " is an anion selected from the group of halides, phosphates, acetates, lactates, alkyl sulphates, alkyl or alkylaryl sulphonates
• R 12 and R 13 preferably denote a mixture of alkenyl or alkyl radicals containing from 12 to 21 carbon atoms, for example acid derivatives.
• fatty tallow R 14 denotes a methyl radical
• R 15 denotes a hydrogen atom such a product is for example sold under the name
• R 16 is an aliphatic radical having about 16 to 30 carbon atoms
• R 17 , R 18 , R 1, R 20 and R 21 which are identical or different, are chosen from a hydrogen atom and an alkyl radical containing from 1 to 4 carbon atoms
• X is an anion selected from the group of halides, acetates, phosphates, nitrates and methylsulfates.
• Such diammonium quaternary salts include in particular propane dichloride diammonium;
• R22 is selected from alkyl C 1 -C 6 hydroxyalkyl or dihydroxyalkyl radicals C 1 -C 6 alkyl;
• R 23 is chosen from:
• R 27 hydrocarbon radicals in C 1 -C 22 linear or branched, saturated or unsaturated, - the hydrogen atom
• R 25 is selected from:
• R24, R2 6 and R 28 which are identical or different, are chosen from linear or branched, saturated or unsaturated C 7 -C 21 hydrocarbon radicals; r, s and t, identical or different, are integers ranging from 2 to 6; y is an integer from 1 to 10; x and z, which are identical or different, are integers ranging from 0 to 10;
• X " is a simple or complex anion, organic or inorganic, provided that the sum x + y + z is from 1 to 15, that when x is 0, then R 23 denotes R 27 and that when z is 0, then R 25 denotes R29.
• the alkyl radicals R 22 may be linear or branched and more particularly linear.
• R 22 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.
• R 23 is a hydrocarbon radical R 27 , it may be long and have from 12 to 22 carbon atoms, or short and have from 1 to 3 carbon atoms.
• R 25 is a hydrocarbon radical R 29 , it preferably has 1 to 3 carbon atoms.
• R 24 , R 26 and R 28 which are identical or different, are chosen from linear or branched, saturated or unsaturated C 11 -C 21 hydrocarbon radicals, and more particularly from C 11 -C 11 alkyl and alkenyl radicals. 21 , linear or branched, saturated or unsaturated.
• x and z are 0 or 1.
• y is 1.
• r, s and t which are identical or different, are equal to 2 or 3, and even more particularly are equal to 2.
• the anion is preferably a halide (chloride, bromide or iodide) or an alkyl sulphate more particularly methyl sulphate.
• a halide chloride, bromide or iodide
• an alkyl sulphate more particularly methyl sulphate.
• methanesulphonate, phosphate, nitrate, tosylate an anion derived from an organic acid such as acetate or lactate or any other anion compatible with ammonium with an ester function.
• the anion X - is even more particularly chloride or methylsulfate.
• the ammonium salts of formula (IV) are used more particularly in which: R 22 denotes a methyl or ethyl radical,
• z is 0 or 1;
• r, s and t are equal to 2;
• R 23 is chosen from:
• R 25 is chosen from:
• R 24 , R 26 and R 28 which are identical or different, are chosen from linear or branched, saturated or unsaturated C 13 -C 17 hydrocarbon radicals, and preferably from C 13 -C 17 alkyl and alkenyl radicals; , linear or branched, saturated or unsaturated.
• hydrocarbon radicals are linear.
• the compounds of formula (IV) such as the salts (especially chloride or methylsulfate) of diacyloxyethyl-dimethylammonium, of diacyloxyethyl-hydroxyethyl-methylammonium, of monoacyloxyethyl-dihydroxyethyl-methylammonium, of triacyloxyethyl-methylammonium, of monoacyloxyethyl-hydroxyethyl-dimethylammonium and mixtures thereof.
• the acyl radicals preferably have from 14 to 18 carbon atoms and come more particularly from a vegetable oil such as palm oil or sunflower oil. When the compound contains more than one acyl radical, the latter may be identical or different.
• These products are obtained, for example, by direct esterification of triethanolamine, triisopropanolamine, alkyldiethanolamine or alkyldiisopropanolamine optionally oxyalkylenated on fatty acids or mixtures of fatty acids of plant or animal origin, or by transesterification. of their methyl esters.
• This esterification is followed by quaternization using an alkylating agent such as an alkyl halide (preferably methyl or ethyl), a dialkyl sulphate (preferably methyl or ethyl), the methyl methanesulfonate, methyl para-toluenesulfonate, glycol or glycerol chlorohydrin.
• an alkylating agent such as an alkyl halide (preferably methyl or ethyl), a dialkyl sulphate (preferably methyl or ethyl), the methyl methanesulfonate, methyl para-tolu
• composition according to the invention may contain, for example, a mixture of quaternary ammonium mono-, di- and triester salts with a majority by weight of diester salts.
• acyloxyethyl-dihydroxyethyl-methylammonium methylsulfate a mixture of ammonium salts
• the mixture containing 15 to 30% by weight of acyloxyethyl-dihydroxyethyl-methylammonium methylsulfate, 45 to 60% of diacyloxyethyl-hydroxyethyl-methylammonium methylsulfate and 15 to 30% of triacyloxyethylmethylammonium methylsulfate, the acyl radicals having from 14 to 18 carbon atoms and coming from partially hydrogenated palm oil.
• ammonium salts containing at least one ester function described in US-A-4874554 and US-A-4137180.
• nonionic surfactants that can be used in the compositions of the present invention are compounds that are well known per se (see in particular in this connection "Handbook of Surfactants” by MR PORTER, Blackie & Son editions (Glasgow and London), 1991, pp. 1 16- 178). They are chosen in particular from polyethoxylated, polypropoxylated or polyglycerolated alcohols and fatty alcohols, polyethoxylated, polypropoxylated or polyglycerolated alpha-diols, alkyl (Ci)
• polyethoxylated phenols polypropoxylated or polyglycerolated, the number of ethylene oxide groups or propylene oxide ranging in particular from 2 to 50 and the number of glycerol groups ranging in particular from 2 to 30.
• the condensates of ethylene oxide and propylene oxide on fatty alcohols preferably having from 2 to 30 ethylene oxide units, the polyglycerolated fatty amides comprising on average from 1 to 5 glycerol groups and in particular from 1, 5 to 4, the esters of fatty acids and of ethoxylated sorbitan having from 2 to 30 ethylene oxide units, the fatty acid esters of sucrose, alkylpolyglycosides, derivatives of N- (C 6- 2 4) glucamine, amine oxides such as oxides of alkyl (C 10-14) amines or oxides of N (acyl C 10-14) -aminopropylmorpholine.
• amine derivatives include the products sold under the name Miranol ®, as described in US patents 2,528,378 and US 2,781,354 and classified in the CTFA dictionary, 3rd edition, 1982, under the names
• R a represents an alkyl group derived from an R 8 -COOH acid present in the hydrolysed coconut oil, a heptyl, nonyl or undecyl group,
• Rb represents a beta-hydroxyethyl group, and R 0 represents a carboxymethyl group
• B represents -CH 2 CH 2 OX '
• X ' represents the group -CH 2 CH 2 -COOH or a hydrogen atom
• Y' represents -COOH or the group -CH 2 -CHOH-SO 3 H
• R a ' represents an alkyl group of a R a ' -COOH acid present in coconut oil or in hydrolysed linseed oil, an alkyl group, especially C 17 and its iso form, a C 17 group unsaturated.
• Examples include the cocoamphodiacetate sold by Rhodia under the trade name Miranol ® C2M concentrate.
• compositions according to the invention may also comprise at least one silicone or a silicone derivative, in soluble, dispersed or micro-dispersed form.
• the silicones or silicone derivatives are preferably present in an amount of less than 10% by weight, preferably ranging from 0.01 to 8%, and still more preferably from 0.1 to 5% by weight relative to the total weight of the composition.
• silicone oils such as, for example, linear or cyclic polydimethylsiloxanes.
• compositions according to the invention may also contain at least one additional fixing polymer, different from the copolymer of acrylate (s) or of methacrylate (s) and of hydroxyester of acrylate (s) or of methacrylate (s), to reinforce the holding effect.
• additional fixing polymer may be of anionic, cationic, nonionic or amphoteric, and preferably anionic, nonionic or amphoteric nature.
• the anionic fixing polymers that may be used in the compositions according to the invention are polymers containing groups derived from carboxylic, sulfonic or phosphoric acid and have a number-average molecular mass of between about 500 and 5,000,000.
• the carboxylic groups are provided by unsaturated mono- or di-carboxylic acid monomers, such as those corresponding to the formula:
• n is an integer from 0 to 10
• a 1 denotes a methylene group, optionally connected to the carbon atom of the unsaturated group or to the neighboring methylene group when n is greater than 1, via a heteroatom such as oxygen or sulfur
• R 7 denotes a hydrogen atom, a phenyl or benzyl group
• R 8 denotes a hydrogen atom, a lower alkyl or carboxyl group
• R 9 denotes a hydrogen atom, a lower alkyl group, a -CH 2 -COOH group, phenyl or benzyl group.
• a lower alkyl group preferably denotes a group having 1 to 4 carbon atoms and in particular the methyl and ethyl groups.
• the preferred anionic fixing polymers with carboxylic groups according to the invention are: A) copolymers of acrylic acid and acrylamide;
• lauryl such as the product sold by the company ISP under the name ACRYLIDONE ® LM
• methacrylic acid terpolymers / ethyl acrylate / butyl acrylate terpolymers such as the product sold under the name Luvimer ® 100 P by the company BASF.
• Copolymers derived from crotonic acid such as those comprising in their chain vinyl acetate or propionate units, and optionally other monomers such as allyl or methallyl esters, vinyl ethers or vinyl esters of a saturated carboxylic acid , linear or branched, long hydrocarbon chain, such as those comprising at least 5 carbon atoms, these polymers may optionally be grafted and crosslinked, or another vinyl ester monomer, allyl or methallylique a carboxylic acid ⁇ - or ⁇ - cyclic.
• Such polymers are described, inter alia, in French patents Nos . 1,222,944, 1,580,545, 2,265,782, 2,265,781, 1,564,110 and 2,439,798.
• a commercial product in this class is the resin. 29-30 marketed by the company National Starch.
• copolymers comprising (i) one or more maleic, fumaric and itaconic acids or anhydrides and (ii) at least one monomer chosen from vinyl esters, vinyl ethers, vinyl halides, phenylvinyl derivatives, acrylic acid and its esters, the anhydride functions of these copolymers being optionally monoesterified or monoamidified.
• Such polymers are described in particular in US Patents Nos 2,047,398, 2,723,248, January 13 2102, GB Patent No. 839 805.
• Commercial products include those sold under the Gantrez ® AN or ES by denominations the ISP company.
• copolymers comprising (i) one or more maleic, citraconic and itaconic anhydride units and (ii) one or more monomers chosen from allyl or methallyl esters optionally containing one or more acrylamide, methacrylamide, ⁇ -olefin, acrylic or methacrylic acid groups, acrylic or methacrylic acid or vinylpyrrolidone in their chain, the anhydride functions of these copolymers being optionally monoesterified or monoamidified.
• the polymers comprising the sulphonic groups are polymers comprising vinylsulphonic, styrene-sulphonic, naphthalenesulphonic or acrylamido-alkylsulphonic units.
• polymers may be chosen in particular from: - the salts of polyvinylsulphonic acid having a molecular mass of between about 1,000 and 100,000, as well as copolymers with an unsaturated comonomer such as acrylic or methacrylic acids and their esters, as well as Acrylamide or its derivatives, vinyl ethers and vinylpyrrolidone.
• - salts of polystyrene sulfonic acid such as the sodium salts are sold under the name Flexan ® 130 by National Starch. These compounds are described in patent FR 2 198 719.
• polyacrylamidesulfonic acid salts such as those mentioned in US Pat. No. 4,128,631, and more particularly polyacrylamidoethylpropanesulphonic acid.
• acrylic acid copolymers such as the acrylic acid terpolymers / ethyl acrylate / N-tert-butylacrylamide sold under the name Ultrahold ® STRONG by the company BASF copolymers derived from crotonic acid, such as vinyl acetate / vinyl tert-butylbenzoate / crotonic acid terpolymers and crotonic acid / vinyl acetate / vinyl neododecanoate terpolymers, sold in particular under the name Resin 28-29-30 by the company National Starch, polymers derived from maleic, fumaric, itaconic acids or anhydrides with vinyl esters, vinyl ethers, vinyl halides, phenylvinyl derivatives, acrylic acid and its esters such as methyl vinyl ether copolymer / maleic anhydride monoesterified sold, e.g., under the name GANTREZ
• Luvimer ® MAEX or MAE by the company BASF and the vinyl acetate / crotonic acid copolymers and vinyl acetate / crotonic acid grafted by polyethylene glycol sold under the name Aristoflex ® A by the company BASF.
• the anionic fixing polymers mentioned above are chosen from the methyl vinyl ether / monoesterified maleic anhydride sold under the name Gantrez ® ES 425 by the company ISP, the acrylic acid terpolymers / ethyl acrylate / N-tert-butylacrylamide sold under the name Ultrahold ® STRONG by the company BASF, the copolymers of methacrylic acid and of methyl methacrylate sold under the name Eudragit ® L by the company Rohm Pharma, the vinyl acetate / vinyl tert-butylbenzoate / crotonic acid and crotonic acid / vinyl acetate / neododecanoate terpolymers sold under the name Resin
• amphoteric fixing polymers that may be used in accordance with the invention may be chosen from polymers comprising units B and C statistically distributed in the polymer chain, where B denotes a unit derived from a monomer comprising at least one basic nitrogen atom and C denotes a unit derived from an acidic monomer having one or more carboxylic or sulphonic groups, or B and C may denote groups derived from zwitterionic monomers of carboxybetaines or of sulphobetaines; B and C may also designate a cationic polymer chain comprising primary, secondary, tertiary or quaternary amine groups, in which at least one of the amine groups carries a carboxylic or sulfonic group connected via a hydrocarbon group, or B and C are part of a chain of an ethylene- ⁇ , ⁇ -dicarboxylic-containing polymer, one of which has been reacted with a polyamine having one or more primary or secondary amine groups.
• amphoteric fixing polymers corresponding to the definition given above, which are more particularly preferred, are chosen from the following polymers:
• a monomer derived from a vinyl compound carrying a carboxylic group such as, more particularly, acrylic acid, methacrylic acid, maleic acid, alpha-chloro acrylic acid
• a basic monomer derived from a substituted vinyl compound containing at least one basic atom such as more particularly dialkylaminoalkylmethacrylate and acrylate, dialkylaminoalkylmethacrylamide and acrylamide.
• (2) polymers comprising units derived from: a) at least one monomer chosen from acrylamides or methacrylamides substituted on the nitrogen atom with an alkyl group; b) with at least one acidic comonomer containing one or more several reactive carboxylic groups, and c) at least one basic comonomer such as primary, secondary, tertiary and quaternary amine substituted esters of acrylic and methacrylic acids, and the product of quaternization of dimethylaminoethyl methacrylate with dimethyl or diethyl sulfate.
• N-substituted acrylamides or methacrylamides which are more particularly preferred according to the invention are those compounds whose alkyl groups contain from 2 to 12 carbon atoms, and more particularly N-ethylacrylamide, N-tert-butylacrylamide,
• N-tert-octylacrylamide N-octylacrylamide, N-decylacrylamide, N-dodecylacrylamide and the corresponding methacrylamides.
• the acidic comonomers are chosen more particularly from acrylic, methacrylic, crotonic, itaconic, maleic and fumaric acids as well as alkyl monoesters having 1 to 4 carbon atoms of maleic or fumaric acids or anhydrides.
• Preferred basic comonomers are aminoethyl, butylaminoethyl, N, N'-dimethylaminoethyl methacrylates,
• Octylacrylamide / acrylates / butylaminoethyl-methacrylate copolymer such as the products sold under the name or AMPHOMER® ®
• R 10 represents a divalent group derived from a saturated dicarboxylic acid, an ethylenically double-bonded mono or dicarboxylic aliphatic acid, an ester of a lower alkanol having 1 to 6 carbon atoms of these acids or a group derived from the addition of any of said acids with a bis-primary or bis-secondary amine
• Z denotes a group derived from of a bis-primary, mono- or bis-secondary polyalkylene polyamine and preferably represents: a) in the proportions of 60 to 100 mol%, the group
• the saturated carboxylic acids are preferably chosen from acids having 6 to 10 carbon atoms such as adipic, trimethyl-2,2,4-adipic and trimethyl-2,4,4-adipic acid, terephthalic acids, double acids and the like.
• ethylenic bond such as, for example, acrylic, methacrylic, itaconic acids.
• the alkane sultones used in the acylation are preferably propane or butane sultone, the salts of the acylating agents are preferably the sodium or potassium salts.
• R 11 denotes a polymerizable unsaturated group such as an acrylate, methacrylate, acrylamide or methacrylamide group
• y and z represent an integer of 1 to 3
• R 12 and R 13 represent a hydrogen atom, a methyl group, ethyl or propyl
• R 14 and R 15 represent a hydrogen atom or an alkyl group such that the sum of the carbon atoms in R 14 and R 15 does not exceed 10.
• Polymers comprising such units may also include units derived from non-zwitterionic monomers such as dimethyl- or diethylaminoethyl acrylate or methacrylate or alkyl acrylates or methacrylates, acrylamides or methacrylamides, or vinyl acetate.
• non-zwitterionic monomers such as dimethyl- or diethylaminoethyl acrylate or methacrylate or alkyl acrylates or methacrylates, acrylamides or methacrylamides, or vinyl acetate.
• R 16 represents a group of formula: R 18 R " ⁇ , 19
• R 20 represents a hydrogen atom, a CH 3 O, CH 3 CH 2 O, phenyl group
• R 21 denotes a hydrogen atom or a lower alkyl group such as methyl, ethyl
• R 22 denotes a hydrogen atom, hydrogen or a C 1 -C 6 lower alkyl group such as methyl, ethyl
• R 23 denotes a C 1 -C 6 lower alkyl group such as methyl, ethyl or a group of the formula: -R.24-N (R22) 2, R24 representing a -CH2-CH2- group, -CH2-CH2-CH2-, -CH 2 - CH (CH 3) - , R22 having the meanings mentioned above.
• Amphoteric polymers of the -D-X-D-X type chosen from: a) the polymers obtained by the action of chloroacetic acid or sodium chloroacetate on compounds comprising at least one unit of formula:
• X denotes the symbol E or E ', E or E', which may be the same or different, denotes a divalent group which is a straight or branched chain alkylene group having up to 7 carbon atoms in the unsubstituted or substituted backbone.
• hydroxyl groups and may further comprise oxygen, nitrogen, sulfur, 1 to 3 aromatic and / or heterocyclic rings; the oxygen, nitrogen and sulfur atoms being present in the form of ether, thioether, sulfoxide, sulfone, sulfonium, alkylamine, alkenylamine, hydroxyl groups, benzylamine, amine oxide, quaternary ammonium, amide, imide groups, alcohol, ester and / or urethane.
• E denotes the symbol E or E 'and at least once E';
• E having the meaning indicated above and E 'is a divalent group which is a straight or branched chain alkylene group having up to 7 carbon atoms in the main chain, substituted or unsubstituted by one or more hydroxyl groups and having one or more nitrogen atoms, the nitrogen atom being substituted by an optionally interrupted alkyl chain by an oxygen atom and necessarily comprising one or more carboxyl functions or one or more hydroxyl functional groups and betainized by reaction with chloroacetic acid or sodium chloroacetate.
• (9) (C 1 -C 5 ) alkyl vinyl ether / maleic anhydride copolymers partially modified by semiamidation with an N 5 N-dialkylaminoalkylamine such as N, N-dimethylaminopropylamine or by semi-esterification with an N, N-dialkylaminoalkanol.
• These copolymers may also comprise other vinylic comonomers such as vinylcaprolactam.
• amphoteric fixing polymers mentioned above that are most particularly preferred according to the invention, mention will be made of those of the family (3) such as the copolymers whose CTFA name is Octylacrylamide / acrylates / butylaminoethylmethacrylate copolymer, such as the products sold. under the names AMPHOMER ® , AMPHOMER ® LV 71 or LOVOCRYL ® 47 by NATIONAL
• the nonionic fixing polymers that can be used according to the present invention are chosen, for example, from:
• copolymers of vinyl acetate and of ethylene copolymers of vinyl acetate and of maleic ester, for example of dibutyl maleate;
• copolymers of acrylic esters such as, for example, copolymers of alkyl acrylates and of alkyl methacrylates, such as the products offered by the company ROHM & HAAS under the ® names Primal AC-261 K and EUDRAGIT ® NE 30 D, by BASF under the name 8845, by Hoechst under the name APPRETAN ® 9212;
• MOWILITH ® LDM 6070 offered by the company HOECHST, RHODOPAS ® SD 215 and RHODOPAS ® DS 910 products offered by RHODIA CHIMIE;
• copolymers of styrene, of alkyl methacrylate and of alkyl acrylate
• the alkyl groups of the nonionic polymers mentioned above preferably have from 1 to 6 carbon atoms.
• the nonionic setting polymers with vinyllactam motifs can be those described in US Pat. Nos. 3,770,683, 3,929,735, 4,521,504, 5,156,762 and 5,506,315.
• Homopolymers or copolymers with vinyllactam units comprise units of formula (XI):
• n is independently 3, 4 or 5.
• the number-average molecular weight of the polymers with vinyllactam units is generally greater than about 5,000, preferably between about 10,000 and 1,000,000, more preferably between about 10,000 and 100,000.
• These fixing polymers include polyvinylpyrrolidones such as those marketed under the name Luviskol ® K30 by BASF; polyvinylcaprolactams such as those sold under the name Luviskol ® Plus by BASF; poly (vinylpyrrolidone / vinyl acetate) such as those sold under the name PVPVA® S630L ® by ISP, Luviskol ® VA 73, VA 64, VA 55, VA 37 and VA 28 by the company BASF; terpolymers and poly (vinylpyrrolidone / vinyl acetate / vinyl propionate) such as, for example, those marketed under the name Luviskol ® VAP 343 by BASF.
• polyvinylpyrrolidones such as those marketed under the name Luviskol ® K30 by BASF
• polyvinylcaprolactams such as those sold under the name Luviskol ® Plus by BASF
• poly (vinylpyrrolidone / vinyl acetate) such
• the additional fixing polymers may also be chosen from optionally silicone polyurethanes.
• fixing polymers of the polyurethane type mention may be made of the Luviset Pur and Luviset Si Pur polymers proposed by BASF.
• These additional fixing polymers may also be chosen from silicone grafted with a hydrocarbon backbone and silicone or silicone backbone grafts and hydrocarbon grafts such as the products VS 70 and VS 80 proposed by the company 3M. They may also be chosen from polyesters containing sulphonic groups, such as the AQ resins (AQ55, AQ38, and AQ48) proposed by EASTMAN CHEMICAL.
• composition according to the invention may then contain at least 0.01% by weight of additional fixing polymer, relative to the total weight of the composition. More preferably, the composition according to the invention contains from 0.01 to 20% by weight of additional fixing polymer, more preferably from 0.05 to 15% by weight, even more preferably from 0.1 to 10% by weight. , relative to the total weight of the composition.
• the compositions according to the invention may also contain at least one thickener, chosen from natural or synthetic, anionic, amphoteric, zwitterionic, nonionic or cationic, associative or non-associative polymeric thickeners, and non-polymeric thickeners such as for example an electrolyte or a sugar.
• the composition according to the invention comprises at least one natural or synthetic thickening polymer.
• a thickening polymer may advantageously be chosen from homopolymers of acrylic acid, crosslinked or non-crosslinked, such as, for example, those sold under the name Carbopol by the company Noveon.
• the composition according to the invention preferably contains at least 0.01% by weight of thickening polymer, relative to the total weight of the composition. Preferably, it contains from 0.1 to 10% by weight of thickening polymer, relative to the total weight of the composition.
• compositions in accordance with the invention may be packaged in a jar, in a tube, in a pump bottle or in an aerosol device that is usual in cosmetics.
• the compositions according to the invention may, when they are intended to be packaged in an aerosol-type device, contain at least one propellant, such as a propellant gas.
• the propellant can then be chosen for example from dimethyl ether, C 3 to C 5 alkanes, halogenated hydrocarbons, and mixtures thereof.
• compositions according to the invention may further contain at least one additive chosen from pearlescent agents; opacifying agents; plasticizers; solar filters; the perfumes ; dyes; conservatives ; pH stabilizers; acids; the basics ; polyols (for example glycols); mineral charges; glitter, and any other additive conventionally used in the cosmetic field.
• additives chosen from pearlescent agents; opacifying agents; plasticizers; solar filters; the perfumes ; dyes; conservatives ; pH stabilizers; acids; the basics ; polyols (for example glycols); mineral charges; glitter, and any other additive conventionally used in the cosmetic field.
• additives are present in the composition according to the invention in an amount ranging from 0 to 50% by weight relative to the total weight of the composition.
• compositions according to the invention may be in the form of more or less thickened liquids, gels, creams, pastes or foams. Preferably, they are in the form of gels.
• composition according to the invention may advantageously be used as a hair product. It may in particular be used as a styling product, for example as a styling gel.
• it is used as a non-rinsed styling product, that is to say for shaping and / or maintaining the hairstyle not followed by rinsing.
• the present invention also relates to a cosmetic hair treatment method, for example a hair care method, or a method of shaping and / or maintaining the hairstyle, which consists in applying to the hair an effective amount of a hair. composition as described above, then to perform a possible rinsing after a possible exposure time.
• a cosmetic hair treatment method for example a hair care method, or a method of shaping and / or maintaining the hairstyle, which consists in applying to the hair an effective amount of a hair. composition as described above, then to perform a possible rinsing after a possible exposure time.
• the composition according to the invention is not rinsed.
• the following example is given by way of illustration of the present invention.
• This example illustrates the formulation of a styling gel according to the invention.
• a styling gel has been prepared from the ingredients indicated in the table below:
• This composition provides a very good fixation of the hair, both flexible and durable.
• the fixing polymer film is very friable.
• this composition has been found to provide the hair with excellent cosmetic properties.
• the hair is not dry, and is particularly soft.

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