WO2020002522A1 - Procédé de mise en forme des cheveux comprenant une étape d'application d'une composition comprenant une lactone, une étape de mise en forme et une longue durée pendant laquelle le produit est laissé sur les cheveux - Google Patents

Procédé de mise en forme des cheveux comprenant une étape d'application d'une composition comprenant une lactone, une étape de mise en forme et une longue durée pendant laquelle le produit est laissé sur les cheveux Download PDF

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Publication number
WO2020002522A1
WO2020002522A1 PCT/EP2019/067201 EP2019067201W WO2020002522A1 WO 2020002522 A1 WO2020002522 A1 WO 2020002522A1 EP 2019067201 W EP2019067201 W EP 2019067201W WO 2020002522 A1 WO2020002522 A1 WO 2020002522A1
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WIPO (PCT)
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alkyl
formula
chosen
hydroxyl
hydrogen atom
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PCT/EP2019/067201
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English (en)
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Stéphanie COULOMBEL
Manon Chaumontet
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L'oreal
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Publication of WO2020002522A1 publication Critical patent/WO2020002522A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61Q5/04—Preparations for permanent waving or straightening the hair

Definitions

  • the present invention relates to a process for shaping the hair which comprises a step of applying a composition comprising a compound of lactone type, a step of placing under mechanical tension and a long leave-on time.
  • Styling products are normally used to construct and structure the hairstyle and to give it hold. They are usually in the form of lotions, gels, mousses, creams or sprays. These compositions generally comprise one or more film-forming polymers, or“fixing polymers” , which allow the formation of a coating film on the hair and thus ensure the hold of the hairstyle and/or the formation of micro-bonds between the individual hairs, thus ensuring the fixing of the hairstyle.
  • compositions are generally applied to wet hair, which is shaped before performing blow drying or drying.
  • the head of hair thus made rigid, has a dry and rough feel which is unliked by consumers.
  • the process sought must also make it possible to care for the hair while at the same time giving it a pleasant cosmetic feel, in particular a smooth and soft feel.
  • the applicant has discovered that applying a composition comprising a compound of lactone type and placing the hair under tension for a long leave-on time, namely for at least four hours made it possible to achieve the objectives set out above; in particular, to obtain a styling process which is easy to carry out and capable of shaping the hairstyle while at the same time preserving a natural and non-rigid appearance, and also a smooth and soft feel.
  • a subject of the present invention is in particular a process for shaping the hair, in which:
  • composition comprising one or more compound(s) of formula (I) below is applied to the hair, preferably wet hair,
  • composition and the tensioning means are left on the hair for at least four hours, then
  • the process for shaping the hair according to the invention is simple to use and it makes it possible to easily shape the hair without any risk of damaging the hair, since it does not require heating means or sulfur-containing reducing agents such as those conventionally used in permanent reshaping.
  • keratin fibres denotes human keratin fibres and more particularly the hair.
  • the process according to the invention comprises a step of applying a composition comprising one or more compound(s) of formula (I) below:
  • R 2 , R 3 , R 4 , R 5 and R 6 which may be identical or different, represent:
  • R' and R which may be identical or different, represent a hydrogen atom or a (Ci-C 6 )alkyl or hydroxy(Ci-C 6 )alkyl group,
  • R 7 representing a hydrogen atom or a (Ci-C 6 )alkyl group
  • U', Y" and Y" ⁇ which may be identical or different, represent an oxygen or sulfur atom
  • said alkyl, alkenyl or alkoxy groups being optionally substituted with one or more groups chosen from hydroxyl and -(0)t-C(0)-Rs with t being equal to 0 or 1
  • Re represents a) a hydrogen atom, b) a hydroxyl group, c) (Ci-C 6 )alkyl, d) (Ci-C 6 )alkoxy, e) (di)(Ci-C 6 )(alkyl)amino, f) (di)hydroxy(Ci-C 6 )alkylamino;
  • n represents an integer between 0 and 6 inclusive, particularly between 0 and 4 inclusive, more particularly between 0 and 3 inclusive, preferably n is 1 or 2, and more preferentially n is 2; it being understood that:
  • the contiguous groups C(Rs)-R 6 may be identical or different;
  • the compound(s) of formula (I) are such that n is 1 or 2, and preferably of formula (la):
  • R 1 , R 2 , R 3 , R 4 , R 5 and R6, which may be identical or different, represent:
  • amino -NR'R R' and R" which may be identical or different, representing a hydrogen atom or a (Ci-C 6 )alkyl or hydroxy(Ci-C 6 )alkyl group;
  • R 7 representing a hydrogen atom or a (Ci-C 6 )alkyl group
  • p and q which may be identical or different, are to 0 or 1
  • the compound of lactone type is chosen from polyhydroxylated lactones derived from sugar.
  • the compound of lactone type is chosen from gluconolactone, ribonolactone, galactonolactone, glucoheptonolactone, glucuronolactone, galacturonolactone, glucarolactone and galactarolactone.
  • the compound(s) of formula (I) are such that n is 2, and preferably of formula (I’a):
  • R1, R 2 , R 3 , R 4 , R 5 and R 6 which may be identical or different, are as defined above, and in particular represent:
  • alkyl groups being optionally substituted with one or more groups chosen from hydroxyl and -(0) t -C(0)-R 8 with t being equal to 0 or 1
  • Re represents a) a hydrogen atom, b) a hydroxyl group, c) (Ci-C 6 )alkyl, d) (Ci-C 6 )alkoxy, e) (di)(Ci- C 6 )(alkyl)amino, f) (di)hydroxy(Ci-C 6 )alkylamino;
  • the compound of lactone type is chosen from those of formula (I’a), and also the organic or mineral acid or base salts thereof, the optical isomers thereof, the geometric isomers thereof, the tautomers thereof and the solvates thereof such as the hydrates, and the hydrolysis products thereof, in which R 5 is an alkyl group, in particular a methyl group, substituted with a hydroxyl, R'5, R3 and R1 are hydroxyl groups and R6, R'6, R4 and R2 are hydrogen atoms .
  • the compound of formula (I) is chosen from gluconolactones, in particular D-gluconolactone.
  • composition used in the process of the invention preferably comprises one or more compound(s) of formula (I) ranging from 0.1 % to 20%, preferably from 0.5% to 15%, more preferably from 1 % to 10%, relative to the total weight of the composition.
  • composition used in the process according to the invention may also comprise at least one conditioning agent.
  • conditioning agent is intended to mean any compound that is capable of producing a conditioning effect on keratin fibres when the composition comprising same is applied to the fibres.
  • the conditioning effect may be constituted of any improvement of a cosmetic nature in the condition and/or appearance of keratin fibres, for instance, in a non-limiting manner, a visual and/or tactile sensory improvement, reinforcement of the keratin fibres, improvement of their ease of disentangling, styling or shaping, provision of sheen or provision of resistance to frizziness.
  • the conditioning agents may advantageously be chosen, alone or as a mixture, from:
  • organosilicon compounds and especially silicones and silanes
  • non-silicone liquid fatty substances and especially hydroxylated or non- hydroxylated liquid fatty acids; liquid fatty alcohols; mineral, plant or animal oils; liquid fatty esters; liquid hydrocarbons; and
  • non-silicone solid fatty substances and especially solid fatty alcohols; solid fatty esters; ceramides; animal, plant or mineral waxes other than ceramides.
  • the cationic surfactant(s) that may be used as conditioning agents in the composition of the process of the invention especially comprise optionally polyoxyalkylenated primary, secondary or tertiary fatty amine salts, quaternary ammonium salts, and mixtures thereof.
  • quaternary ammonium salts examples include:
  • ⁇ Re to R11 which may be identical or different, represent a linear or branched aliphatic group comprising from 1 to 30 carbon atoms, or an aromatic group such as aryl or alkylaryl, it being understood that at least one of the groups Re to Rn comprises from 8 to 30 carbon atoms and preferably from 12 to 24 carbon atoms; and ⁇ X represents an organic or mineral anionic counterion, such as that chosen from halides, acetates, phosphates, nitrates, (Ci-C 4 )alkyl sulfates, (Ci-C 4 )alkyl- and (Ci-C 4 )alkylarylsulfonates, in particular methyl sulfate and ethyl sulfate.
  • the aliphatic groups of Re to Rn may also comprise heteroatoms in particular such as oxygen, nitrogen, sulfur and halogens.
  • the aliphatic groups of Rs to Rn are chosen, for example, from C1-C30 alkyl, C1- C30 alkoxy, polyoxy(C2-C6)alkylene, C1-C30 alkylamide, (Ci2-C22)alkylamido(C2-C6)alkyl, (Ci2-C22)alkyl acetate, and C1-C30 hydroxyalkyl groups;
  • X is an anionic counterion chosen from halides, phosphates, acetates, lactates, (Ci-C 4 )alkyl sulfates, and (C1- C 4 )alkyl or (Ci-C 4 )alkylaryl sulfonates.
  • tetraalkylammonium chlorides for instance dialkyldimethylammonium or alkyltrimethylammonium chlorides in which the alkyl group contains approximately from 12 to 22 carbon atoms, in particular behenyltrimethylammonium chloride, distearyldimethylammonium chloride, cetyltrimethylammonium chloride, benzyldimethylstearylammonium chloride, or else, secondly, distearoylethylhydroxyethylmethylammonium methosulfate, dipalmitoylethylhydroxyethylammonium methosulfate or distearoylethylhydroxyethylammonium methosulfate, or else, lastly, palmitylamidopropyltrimethylammonium chloride or stearamidopropyldimethyl(myristyl acetate)ammonium chlor
  • R12 represents an alkenyl or alkyl group comprising from 8 to 30 carbon atoms, for example fatty acid derivatives of tallow;
  • R13 represents a hydrogen atom, a C1-C4 alkyl group or an alkenyl or alkyl group comprising from 8 to 30 carbon atoms;
  • R M represents a Ci-C 4 alkyl group
  • R15 represents a hydrogen atom or a Ci-C 4 alkyl group
  • ⁇ X represents an organic or mineral anionic counterion, such as that chosen from halides, phosphates, acetates, lactates, (Ci-C 4 )alkyl sulfates, (Ci-C 4 )alkyl or (Ci- C 4 )alkylaryl sulfonates.
  • R 12 and R 13 denote a mixture of alkenyl or alkyl groups including from 12 to 21 carbon atoms, for example derived from tallow fatty acids, RM denotes a methyl group and R 15 denotes a hydrogen atom.
  • a product is sold, for example, under the name Rewoquat® W 75 by the company Rewo;
  • ⁇ Ri 6 denotes an alkyl group comprising approximately from 16 to 30 carbon atoms, which is optionally hydroxylated and/or interrupted with one or more oxygen atoms;
  • R 17 is chosen from hydrogen, an alkyl group comprising from 1 to 4 carbon atoms or a group -(CH 2 )3-N + (Ri 6 a)(Ri7a)(Ri8a), X ;
  • Ri6a, Ri7a, Ri8a, R18, R19, R20 and R21 which may be identical or different, are chosen from hydrogen and an alkyl group comprising from 1 to 4 carbon atoms;
  • ⁇ X which may be identical or different, represents an organic or mineral anionic counterion, such as that chosen from halides, acetates, phosphates, nitrates, alkyl(Ci-C 4 ) sulfates, alkyl(Ci-C 4 )- or alkyl(Ci-C 4 )aryl-sulfonates, in particular methyl sulfate and ethyl sulfate.
  • organic or mineral anionic counterion such as that chosen from halides, acetates, phosphates, nitrates, alkyl(Ci-C 4 ) sulfates, alkyl(Ci-C 4 )- or alkyl(Ci-C 4 )aryl-sulfonates, in particular methyl sulfate and ethyl sulfate.
  • Such compounds are, for example, Finquat CT-P, made available by the company Finetex (Quaternium 89), and Finquat CT, made available by the company Finetex (Quaternium 75);
  • ⁇ R 22 is chosen from C 1 -C 6 alkyl groups and C 1 -C 6 hydroxyalkyl or dihydroxyalkyl groups;
  • ⁇ R 23 is chosen from:
  • ⁇ R 25 is chosen from:
  • R 24 , R 26 and R 28 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C 7 -C 21 hydrocarbon-based groups;
  • ⁇ r, s and t which may be identical or different, are integers ranging from 2 to 6,
  • ⁇ y is an integer ranging from 1 to 10,
  • ⁇ x and z which may be identical or different, are integers ranging from 0 to 10;
  • ⁇ X represents an organic or mineral anionic counterion
  • R 23 denotes R 27
  • R 25 denotes a linear or branched, saturated or unsaturated C1-C6 hydrocarbon-based radical R29.
  • the alkyl groups R 22 may be linear or branched, and more particularly linear.
  • R 22 denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl group, and more particularly a methyl or ethyl group.
  • the sum x + y + z is from 1 to 10.
  • R 23 is a hydrocarbon-based group R 27 , it may be long and contain from 12 to 22 carbon atoms, or may be short and contain from 1 to 3 carbon atoms.
  • R 25 is a hydrocarbon-based group R 29 , it preferably contains 1 to 3 carbon atoms.
  • R 24 , R 26 and R 28 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C 11 -C 21 hydrocarbon-based groups, and more particularly from linear or branched, saturated or unsaturated C11-C21 alkyl and alkenyl groups.
  • x and z which may be identical or different, are equal to 0 or 1 .
  • y is equal to 1.
  • r, s and t which may be identical or different, are equal to 2 or 3, and even more particularly are equal to 2.
  • the anionic counterion X is preferably a halide, such as chloride, bromide or iodide; a (Ci-C 4 )alkyl sulfate or a (Ci-C 4 )alkyl- or (Ci-C 4 )alkylarylsulfonate.
  • a halide such as chloride, bromide or iodide
  • a (Ci-C 4 )alkyl sulfate or a (Ci-C 4 )alkyl- or (Ci-C 4 )alkylarylsulfonate e.g., a halide, such as chloride, bromide or iodide
  • a (Ci-C 4 )alkyl sulfate or a (Ci-C 4 )alkyl- or (Ci-C 4 )alkylarylsulfonate e.g., a halide, such as chloride,
  • the anionic counterion X is even more particularly chloride, methyl sulfate or ethyl sulfate.
  • R22 denotes a methyl or ethyl group
  • - R 25 is chosen from:
  • R 24 , R 26 and R 28 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C 13 -C 17 hydrocarbon-based groups, and preferably from linear or branched, saturated or unsaturated C 13 -C 17 alkyl and alkenyl groups.
  • hydrocarbon-based radicals are linear.
  • acyl groups preferably contain from 14 to 18 carbon atoms and are derived more particularly from a plant oil such as palm oil or sunflower oil. When the compound contains several acyl groups, these groups may be identical or different.
  • This esterification is followed by a quaternization by means of an alkylating agent such as an alkyl halide, preferably methyl or ethyl halide, a dialkyl sulfate, preferably dimethyl or diethyl sulfate, methyl methanesulfonate, methyl para-toluenesulfonate, glycol chlorohydrin or glycerol chlorohydrin.
  • an alkylating agent such as an alkyl halide, preferably methyl or ethyl halide, a dialkyl sulfate, preferably dimethyl or diethyl sulfate, methyl methanesulfonate, methyl para-toluenesulfonate, glycol chlorohydrin or glycerol chlorohydrin.
  • Such compounds are sold, for example, under the names Dehyquart® by the company Henkel, Stepanquat® by the company Stepan, Noxamium® by the company Ceca or Rewoquat® WE 18 by the company Rewo-Witco.
  • the composition may contain, for example, a mixture of quaternary ammonium monoester, diester and triester salts with a weight majority of diester salts.
  • ammonium salts containing at least one ester function that are described in patents US-A-4 874 554 and US-A-4 137 180.
  • Use may be made of behenoylhydroxypropyltrimethylammonium chloride sold by KAO under the name Quatarmin BTC 131.
  • the ammonium salts containing at least one ester function contain two ester functions.
  • cationic surfactants that may be present in the composition, it is more particularly preferred to choose cetyltrimethylammonium, behenyltrimethylammonium and dipalmitoylethylhydroxyethylmethylammonium salts, and mixtures thereof, and more particularly behenyltrimethylammonium chloride, cetyltrimethylammonium chloride, and dipalmitoylethylhydroxyethylammonium methosulfate, and mixtures thereof.
  • the cationic surfactants may be present in a total amount ranging from 0.01 % to 10% by weight, preferably from 0.1 % to 5% by weight and better still from 0.2% to 3% by weight, relative to the total weight of the composition.
  • composition used in the process according to the invention can comprise, as conditioning agent, one or more polymers chosen from amphoteric polymers, cationic polymers, and also mixtures thereof.
  • cationic polymer means any polymer comprising cationic groups and/or groups that can be ionized into cationic groups and not comprising any anionic groups and/or groups that can be ionized into anionic groups.
  • the cationic polymer is hydrophilic or amphiphilic.
  • the preferred cationic polymers are chosen from those that contain units comprising primary, secondary, tertiary and/or quaternary amine groups that may either form part of the main polymer chain or may be borne by a side substituent directly connected thereto.
  • the cationic polymers that may be used preferably have a weight-average molar mass (Mw) of between 500 and 5x10 6 approximately and preferably between 10 3 and 3x10 6 approximately.
  • cationic polymers mention may be made more particularly of:
  • - R3 which may be identical or different, denote a hydrogen atom or a CH 3 radical
  • - A which may be identical or different, represent a linear or branched divalent alkyl group of 1 to 6 carbon atoms, preferably 2 or 3 carbon atoms, or a hydroxyalkyl group of 1 to 4 carbon atoms;
  • R4, R5 and R6, which may be identical or different, represent an alkyl group containing from 1 to 18 carbon atoms or a benzyl radical, preferably an alkyl group containing from 1 to 6 carbon atoms;
  • R1 and R2 which may be identical or different, represent a hydrogen atom or an alkyl group containing from 1 to 6 carbon atoms, preferably methyl or ethyl;
  • - X denotes an anion derived from a mineral or organic acid, such as a methosulfate anion or a halide such as chloride or bromide.
  • the copolymers of family (1 ) may also contain one or more units derived from comonomers that may be chosen from the family of acrylamides, methacrylamides, diacetone acrylamides, acrylamides and methacrylamides substituted on the nitrogen with lower (C1-C4) alkyls, acrylic or methacrylic acids, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, and vinyl esters.
  • - vinylpyrrolidone/quaternized dimethylaminopropylmethacrylamide copolymers such as the product sold under the name Gafquat HS 100 by the company ISP, - preferably crosslinked polymers of methacryloyloxy(C1 -C4)alkyltri(C1 - C4)alkylammonium salts, such as the polymers obtained by homopolymerization of dimethylaminoethyl methacrylate quaternized with methyl chloride, or by copolymerization of acrylamide with dimethylaminoethyl methacrylate quaternized with methyl chloride, the homopolymerization or copolymerization being followed by crosslinking with an olefinically unsaturated compound, in particular methylenebisacrylamide.
  • an olefinically unsaturated compound in particular methylenebisacrylamide.
  • Use may be made more particularly of a crosslinked acrylamide/methacryloyloxyethyltrimethylammonium chloride copolymer (20/80 by weight) in the form of a dispersion comprising 50% by weight of said copolymer in mineral oil.
  • This dispersion is sold under the name Salcare® SC 92 by the company Ciba.
  • Use may also be made of a crosslinked methacryloyloxyethyltrimethylammonium chloride homopolymer comprising approximately 50% by weight of the homopolymer in mineral oil or in a liquid ester. These dispersions are sold under the names Salcare® SC 95 and Salcare® SC 96 by the company Ciba.
  • cationic polysaccharides especially cationic galactomannan gums and celluloses.
  • cationic polysaccharides mention may be made more particularly of cellulose ether derivatives comprising quaternary ammonium groups, cationic cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer and cationic galactomannan gums.
  • cellulose ether derivatives comprising quaternary ammonium groups are in particular described in FR 1 492 597, and mention may be made of the polymers sold under the name Ucare Polymer JR (JR 400 LT, JR 125 and JR 30M) or LR (LR 400 and LR 30M) by the company Amerchol. These polymers are also defined in the CTFA dictionary as quaternary ammoniums of hydroxyethylcellulose that have reacted with an epoxide substituted with a trimethylammonium group.
  • cationic cellulose copolymers or cellulose derivatives grafted with a water- soluble quaternary ammonium monomer are described in particular in patent US 4 131 576, and mention may be made of hydroxyalkyl celluloses, for instance hydroxymethyl, hydroxyethyl or hydroxypropyl celluloses grafted, in particular, with a methacryloylethyltrimethylammonium, methacrylamidopropyltrimethylammonium or dimethyldiallylammonium salt.
  • the commercial products corresponding to this definition are more particularly the products sold under the names Celquat L 200 and Celquat H 100 by the company National Starch.
  • guar gums comprising cationic trialkylammonium groups.
  • Use is made, for example, of guar gums modified with a 2,3-epoxypropyltrimethylammonium salt (for example, a chloride).
  • a 2,3-epoxypropyltrimethylammonium salt for example, a chloride.
  • Such products are in particular sold under the names Jaguar C13 S, Jaguar C 15, Jaguar C 17 and Jaguar C162 by the company Rhodia.
  • polymers constituted of piperazinyl units and of divalent alkylene or hydroxyalkylene radicals containing linear or branched chains, optionally interrupted with oxygen, sulfur or nitrogen atoms or with aromatic or heterocyclic rings, and also the oxidation and/or quaternization products of these polymers.
  • water-soluble polyaminoamides prepared in particular by polycondensation of an acidic compound with a polyamine; these polyaminoamides can be crosslinked with an epihalohydrin, a diepoxide, a dianhydride, an unsaturated dianhydride, a bis- unsaturated derivative, a bis-halohydrin, a bis-azetidinium, a bis-haloacyldiamine, a bis- alkyl halide or alternatively with an oligomer resulting from the reaction of a difunctional compound which is reactive with a bis-halohydrin, a bis-azetidinium, a bis- haloacyldiamine, a bis-alkyl halide, an epihalohydrin, a diepoxide or a bis-unsaturated derivative; the crosslinking agent being used in proportions ranging from 0.025 to 0.35 mol per amine group of the polyaminoamide; these polyaminoamide
  • polyaminoamide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids followed by alkylation with difunctional agents Mention may be made, for example, of adipic acid/dialkylaminohydroxyalkyldialkylenetriamine polymers in which the alkyl radical comprises from 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl.
  • alkyl radical comprises from 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl.
  • these derivatives mention may be made more particularly of the adipic acid/dimethylaminohydroxypropyl/diethylenetriamine polymers sold under the name Cartaretine F, F4 or F8 by the company Sandoz.
  • Polymers of this type are sold in particular under the name Hercosett 57 by the company Hercules Inc. or else under the name PD 170 or Delsette 101 by the company Hercules in the case of the adipic acid/epoxypropyl/diethylenetriamine copolymer.
  • cyclopolymers of alkyldiallylamine or of dialkyldiallylammonium such as the homopolymers or copolymers containing, as main constituent of the chain, units corresponding to formula (I) or (II) below:
  • R12 denotes a hydrogen atom or a methyl radical
  • R10 and R1 1 independently of each other, denote an alkyl group containing from 1 to 6 carbon atoms, a hydroxyalkyl group in which the alkyl group contains 1 to 5 carbon atoms, a C1 -C4 amidoalkyl group; or alternatively R10 and R1 1 may denote, together with the nitrogen atom to which they are attached, heterocyclic groups such as piperidinyl or morpholinyl; R10 and R1 1 , independently of each other, preferably denote an alkyl group containing from 1 to 4 carbon atoms;
  • - Y is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, sulfate or phosphate.
  • R13, R14, R15 and R16 which may be identical or different, represent aliphatic, alicyclic or arylaliphatic radicals comprising from 1 to 20 carbon atoms, or lower hydroxyalkylaliphatic radicals, or else R13, R14, R15 and R16, together or separately, constitute, with the nitrogen atoms to which they are attached, heterocycles optionally comprising a second non-nitrogen heteroatom, or else R13, R14, R15 and R16 represent a linear or branched C1 -C6 alkyl radical substituted with a nitrile, ester, acyl, amide or - CO-0-R17-D or -CO-NH-R17-D group in which R17 is an alkylene and D is a quaternary ammonium group;
  • A1 and B1 represent divalent polymethylene groups comprising from 2 to 20 carbon atoms, which may be linear or branched, saturated or unsaturated, and which may contain, linked to or intercalated in the main chain, one or more aromatic rings or one or more oxygen or sulfur atoms or sulfoxide, sulfone, disulfide, amino, alkylamino, hydroxyl, quaternary ammonium, ureido, amide or ester groups, and
  • - X denotes an anion derived from a mineral or organic acid
  • A1 , R13 and R15 can form, with the two nitrogen atoms to which they are attached, a piperazine ring;
  • A1 denotes a linear or branched, saturated or unsaturated alkylene or hydroxyalkylene radical
  • B1 may also denote a group (CH2)n-CO-D-OC-(CH2)n- in which D denotes:
  • a glycol residue of formula -0-Z-0- in which Z denotes a linear or branched hydrocarbon-based radical, or a group corresponding to one of the following formulae: -(CH2-CH2-0)x-CH2-CH2- and -[CH2-CH(CH3)-0]y-CH2-CH(CH3)-, in which x and y denote an integer from 1 to 4, representing a defined and unique degree of polymerization or any number from 1 to 4 representing an average degree of polymerization;
  • a bis-secondary diamine residue such as a piperazine derivative
  • X is an anion, such as chloride or bromide.
  • Mn number-average molar mass
  • R1 , R2, R3 and R4 which may be identical or different, denote an alkyl or hydroxyalkyl radical containing from 1 to 4 carbon atoms approximately, n and p are integers ranging from 2 to 20 approximately, and X- is an anion derived from a mineral or organic acid.
  • R19, R20 and R21 which may be identical or different, represent a hydrogen atom or a methyl, ethyl, propyl, b-hydroxyethyl, b-hydroxypropyl or - CH CH (OCH CH ) p OH radical, in which p is equal to 0 or to an integer between 1 and 6, with the proviso that Rie, R19, R20 and R21 do not simultaneously represent a hydrogen atom,
  • - r and s which may be identical or different, are integers between 1 and 6,
  • X- denotes an anion such as a halide
  • - A denotes a dihalide radical or preferably represents -CH2-CH2-0-CH2-CH2-. Examples that may be mentioned include the products Mirapol® A 15, Mirapol®
  • polyamines such as Polyquart® H sold by Cognis, referred to under the name Polyethylene glycol (15) tallow polyamine in the CTFA dictionary.
  • these polymers may especially be chosen from homopolymers or copolymers comprising one or more units derived from vinylamine and optionally one or more units derived from vinylformamide.
  • these cationic polymers are chosen from polymers comprising, in their structure, from 5 mol% to 100 mol% of units corresponding to the formula (A) and from 0 mol% to 95 mol% of units corresponding to the formula (B), preferentially from 10 mol% to 100 mol% of units corresponding to the formula (A) and from 0 mol% to 90 mol% of units corresponding to the formula (B).
  • These polymers may be obtained, for example, by partial hydrolysis of polyvinylformamide. This hydrolysis may take place in acidic or basic medium.
  • the weight-average molecular weight of said polymer measured by light scattering, may range from 1000 to 3 000 000 g/mol, preferably from 10 000 to 1 000 000 and more particularly from 100 000 to 500 000 g/mol.
  • the cationic charge density of these polymers may range from 2 meq/g to 20 meq/g, preferably from 2.5 to 15 and more particularly from 3.5 to 10 meq/g.
  • the polymers comprising units of formula (A) and optionally units of formula (B) are sold in particular under the name Lupamin by the company BASF, for instance, in a non-limiting way, the products provided under the names Lupamin 9095, Lupamin 5095, Lupamin 1095, Lupamin 9030 (or Luviquat 9030) and Lupamin 9010.
  • the cationic polymers are chosen from those of families (1 ), (2), (7), (10) and (12) mentioned above, and more preferably from those of family (1 ).
  • the ones that may preferably be used are cationic polysaccharides, in particular cationic celluloses and cationic galactomannan gums, and in particular quaternary cellulose ether derivatives such as the products sold under the name JR 400 by the company Amerchol, cationic cyclopolymers, in particular dimethyldiallylammonium salt (for example chloride) homopolymers or copolymers, sold under the names Merquat 100, Merquat 550 and Merquat S by the company Nalco, and homologues thereof of low weight-average molecular weights, quaternary polymers of vinylpyrrolidone and of vinylimidazole, optionally crosslinked homopolymers or copolymers of methacryloyloxy(C1 - C4)alkyltri(C1 -C4)alkylammonium salts, and mixtures thereof.
  • the cationic polymer(s) are chosen from:
  • alkyldiallylamine or dialkyldiallylammonium cyclopolymers alkyldiallylamine or dialkyldiallylammonium cyclopolymers
  • the cationic polymer(s) are chosen from 2-methacryloyloxyethyltrimethylammonium chloride homopolymers or copolymers, dimethyldiallylammonium chloride homopolymers, and mixtures thereof.
  • amphoteric polymers as conditioning agent.
  • amphoteric polymer means any polymer comprising cationic groups and/or groups that can be ionized into cationic groups and also anionic groups and/or groups that can be ionized into anionic groups.
  • amphoteric polymers may preferably be chosen from amphoteric polymers comprising the repetition of:
  • the units derived from a (meth)acrylamide-type monomer (i) are units of structure (la) below:
  • Ri denotes H or CH3 and R2 is chosen from an amino, dimethylamino, tert-butylamino, dodecylamino and -NH-CH2OH radical.
  • said amphoteric polymer comprises the repetition of only one unit of formula (la).
  • the unit derived from a monomer of (meth)acrylamide type of formula (la) in which R1 denotes H and R2 is an amino radical (NH2) is particularly preferred. It corresponds to the acrylamide monomer per se.
  • the units resulting from a (meth)acrylamido-alkyl-trialkylammonium- type monomer (ii) are units of structure (I la) below:
  • R 3 denotes H or CH 3 ,
  • R 4 denotes a group (CH2)k with k being an integer ranging from 1 to 6 and preferably from 2 to 4;
  • R5 , R 6 and R7 which may be identical or different, each denote an alkyl group containing from 1 to 4 carbon atoms;
  • - Y is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, sulfate or phosphate.
  • said amphoteric polymer comprises the repetition of only one unit of formula (I la).
  • the ones that are preferred are those derived from the methacrylamidopropyltrimethylammonium chloride monomer, for which R 3 denotes a methyl radical, k is equal to 3, R5, R 6 and R7 denote a methyl radical, and Y denotes a chloride anion.
  • the units derived from a (meth)acrylic acid-type monomer (iii) are units of formula (Ilia):
  • Re denotes H or CH3 and Rg denotes a hydroxyl radical or an -NH- C(CH 3 )2-CH2-S0 3 H radical.
  • the preferred units of formula (Ilia) correspond to the acrylic acid, methacrylic acid and 2-acrylamido-2-methylpropanesulfonic acid monomers.
  • the unit derived from a monomer of (meth)acrylic acid type of formula (Ilia) is that derived from acrylic acid, for which R 3 denotes a hydrogen atom and Rg denotes a hydroxyl radical.
  • the (meth)acrylic acid-type acidic monomer(s) may be non-neutralized or partially or totally neutralized with an organic or mineral base.
  • said amphoteric polymer comprises the repetition of only one unit of formula (Ilia).
  • the amphoteric polymer(s) of this type comprise at least 30 mol% of units derived from a monomer of (meth)acrylamide type (i). Preferably, they comprise from 30 mol% to 70 mol% and more preferably from 40 mol% to 60 mol% of units derived from a (meth)acrylamide-type monomer.
  • the content of units derived from a monomer of (meth)acrylamidoalkyltrialkylammonium type (ii) may advantageously be from 10 mol% to 60 mol% and preferentially from 20 mol% to 55 mol%.
  • the content of units derived from an acidic monomer of (meth)acrylic acid type (iii) may advantageously be from 1 mol% to 20 mol% and preferentially from 5 mol% to 15 mol%.
  • amphoteric polymer of this type comprises:
  • Amphoteric polymers of this type may also comprise additional units, other than the units derived from a (meth)acrylamide-type monomer, a (meth)acrylamidoalkyltrialkylammonium-type monomer and a (meth)acrylic acid-type monomer such as described above.
  • said amphoteric polymers are constituted solely of units derived from monomers of (meth)acrylamide type (i), of (meth)acrylamidoalkyltrialkylammonium type (ii) and of (meth)acrylic acid type (iii).
  • amphoteric polymers examples include acrylamide/methacrylamidopropyltrimethylammonium chloride/acrylic acid terpolymers. Such polymers are listed in the CTFA dictionary, 10th edition 2004, under the name Polyquaternium 53. Corresponding products are in particular sold under the names Merquat 2003 and Merquat 2003 PR by the company Nalco.
  • amphoteric polymer As another type of amphoteric polymer that may be used, mention may also be made of copolymers based on (meth)acrylic acid and on a dialkyldiallylammonium salt, and optionally on acrylamide or one of its derivatives, such as copolymers of (meth)acrylic acid and of dimethyldiallylammonium chloride.
  • copolymers based on (meth)acrylic acid and on a dialkyldiallylammonium salt and optionally on acrylamide or one of its derivatives, such as copolymers of (meth)acrylic acid and of dimethyldiallylammonium chloride.
  • An example that may be mentioned is Merquat 280 sold by the company Nalco.
  • the composition comprises one or more cationic and/or amphoteric polymers, it comprises them in a total amount ranging from 0.01 % to 5% by weight, especially from 0.05% to 3% by weight and preferentially from 0.1 % to 2.5% by weight, relative to the total weight of the composition.
  • composition used in the process according to the invention may comprise, as conditioning agent, one or more organosilicon compounds, chosen especially from silicones and silanes, and also mixtures thereof.
  • organicsilicon compound means any organic compound comprising in its structure at least one silicon atom.
  • the silicones that may be used according to the invention may be soluble or insoluble in the composition; they may be in the form of oils, waxes, resins or gums; they may be volatile or non-volatile.
  • the silicones may be organopolysiloxanes, which are especially insoluble in the composition of the invention.
  • Organopolysiloxanes are especially described in Walter Noll’s Chemistry and Technology of Silicones (1968), Academic Press.
  • the volatile silicones are more particularly chosen from those with a boiling point of between 60°C and 260°C. Mention may be made of:
  • cyclic volatile silicones comprising from 3 to 7 and preferably 4 to 5 silicon atoms, such as:
  • Volatile Silicone FZ 3109 sold by the company Union Carbide;
  • cyclic silicones with silicon-derived organic compounds such as the mixture of octamethylcyclotetrasiloxane and of tetratrimethylsilylpentaerythritol (50/50) and the mixture of octamethylcyclotetrasiloxane and of 1 ,T-oxy(2,2,2',2',3,3'- hexatrimethylsilyloxy)bisneopentane;
  • linear volatile silicones containing 2 to 9 silicon atoms which generally have a viscosity of less than or equal to 5 x10 6 m 2 /s at 25°C, such as:
  • non-volatile silicones mention may be made of, alone or as a mixture, polydialkylsiloxanes, polydiarylsiloxanes, polyalkylarylsiloxanes, silicone gums and resins, and also organopolysiloxanes which are silicones as defined above, comprising in their structure one or more organofunctional groups attached by means of a hydrocarbon-based group (also called organomodified silicones).
  • organomodified silicones mention may be made of polyorganosiloxanes comprising:
  • C6-C24 alkyl groups such as dimethicone copolyols and especially those sold by the company Dow Corning under the name DC 1248 or the oils Silwet ® L 722, L 7500, L 77 and L 71 1 by the company Union Carbide; or (Ci2)alkylmethicone copolyols and especially those sold by the company Dow Corning under the name Q2-5200;
  • hydroxylated groups for instance polyorganosiloxanes containing a hydroxyalkyl function
  • amino silicone denotes any silicone including at least one primary, secondary or tertiary amine or a quaternary ammonium group.
  • the weight-average molecular masses of these amino silicones may be measured by gel permeation chromatography (GPC) at ambient temperature (25°C), as polystyrene equivalent.
  • the columns used are m styragel columns.
  • the eluent is THF and the flow rate is 1 ml/min. 200 mI of a 0.5% by weight solution of silicone in THF are injected. Detection is performed by refractometry and UV-metry.
  • amino silicone(s) that may be used in the context of the invention are chosen from:
  • - G which may be identical or different, denotes a hydrogen atom or a phenyl, OH, Ci-Cs alkyl, for example methyl, or Ci-Cs alkoxy, for example methoxy, group,
  • - a which may be identical or different, denotes 0 or an integer from 1 to 3, in particular 0,
  • - b denotes 0 or 1 , in particular 1 , - m and n are numbers such that the sum (n + m) ranges from 1 to 2000 and in particular from 50 to 150, n possibly denoting a number from 0 to 1999 and in particular from 49 to 149, and m possibly denoting a number from 1 to 2000 and in particular from 1 to 10;
  • - R' which may be identical or different, denotes a monovalent radical of formula -
  • C q H 2q L in which q is a number ranging from 2 to 8 and L is an optionally quaternized amino group chosen from the following groups: -NR"-Q-N(R")2, -N(R")2, -N + (R")3 A , N + H(R") 2 A-, N + H 2 (R") A-, -NR"-Q-N + (R")H 2 A-, -NR"-Q-N + (R") 2 H A and NR"-Q-N + (R”) 3 A , in which R”, which may be identical or different, denotes hydrogen, phenyl, benzyl, or a saturated monovalent hydrocarbon-based radical, for example a C1-C20 alkyl radical; Q denotes a linear or branched group of formula C r H2 r , r being an integer ranging from 2 to 6, preferably from 2 to 4; and A represents a cosmetically acceptable anion, in particular a halide such as fluoride,
  • the amino silicones that may be used according to the invention are chosen from the amino silicones of formula (VII). Even more preferably, the amino silicones of formula (VII) are chosen from the amino silicones corresponding to formulae (VIII), (IX), (X), (XI) and/or (XII) below.
  • amino silicones corresponding to formula (VII) are chosen from the silicones known as "trimethylsilyl amodimethicone", corresponding to formula (VIII):
  • n and m are numbers such that the sum (n + m) ranges from 1 to 2000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to 1999 and notably from 49 to 149, and for m to denote a number from 1 to 2000 and notably from 1 to 10.
  • amino silicones corresponding to formula (VII) are chosen from the silicones of formula (IX) below:
  • n + m and n are numbers such that the sum (n + m) ranges from 1 to 1000 and in particular from 50 to 250 and more particularly from 100 to 200; it being possible for n to denote a number from 0 to 999 and in particular from 49 to 249 and more particularly from 125 to 175, and for m to denote a number from 1 to 1000 and in particular from 1 to 10, and more particularly from 1 to 5;
  • R 2 and R 3 which may be identical or different, represent a hydroxyl or C1-C4 alkoxy radical, at least one of the radicals R 1 to R 3 denoting an alkoxy radical.
  • the alkoxy radical is a methoxy radical.
  • the hydroxy/alkoxy mole ratio preferably ranges from 0.2:1 to 0.4:1 and preferably from 0.25:1 to 0.35:1 and more particularly equals 0.3:1.
  • the weight-average molecular mass (Mw) of these silicones preferably ranges from 2000 to 1 000 000 g/mol and more particularly from 3500 to 200 000 g/mol.
  • amino silicones corresponding to formula (VII) are chosen from the silicones of formula (X) below:
  • - p and q are numbers such that the sum (p + q) ranges from 1 to 1000, in particular from 50 to 350 and more particularly from 150 to 250; it being possible for p to denote a number from 0 to 999 and in particular from 49 to 349 and more particularly from 159 to 239, and for q to denote a number from 1 to 1000, in particular from 1 to 10 and more particularly from 1 to 5;
  • Ri and R 2 which are different, represent a hydroxyl or C1-C4 alkoxy radical, at least one of the radicals Ri or R 2 denoting an alkoxy radical.
  • the alkoxy radical is a methoxy radical.
  • the hydroxy/a I koxy mole ratio generally ranges from 1 :0.8 to 1 :1.1 and preferably from 1 :0.9 to 1 :1 and more particularly equals 1 :0.95.
  • the weight-average molecular mass (Mw) of the silicone preferably ranges from 2000 to 200 000 g/mol, more preferentially from 5000 to 100 000 g/mol and in particular from 10 000 to 50 000 g/mol.
  • the commercial products comprising silicones of structure (IX) or (X) may include in their composition one or more other amino silicones of which the structure is different from formula (IX) or (X).
  • a product containing amino silicones of structure (IX) is sold by the company Wacker under the name Belsil® ADM 652.
  • a product containing amino silicones of structure (X) is sold by Wacker under the name Fluid WR 1300®.
  • Another product containing amino silicones of structure (X) is sold by Wacker under the name Belsil ADM LOG 1®.
  • the oil-in-water emulsion may comprise one or more surfactants.
  • the surfactants may be of any nature but are preferably cationic and/or non-ionic.
  • the number-average size of the silicone particles in the emulsion generally ranges from 3 nm to 500 nanometres.
  • use is made of microemulsions of which the mean particle size ranges from 5 nm to 60 nm (limits included) and more particularly from 10 nm to 50 nm (limits included).
  • use may be made according to the invention of the amino silicone microemulsions of formula (X) sold under the names Finish CT 96 E® or SLM 28020® by the company Wacker.
  • amino silicones corresponding to formula (VII) are chosen from the silicones of formula (XI) below:
  • n + m and n are numbers such that the sum (n + m) ranges from 1 to 2000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to 1999 and notably from 49 to 149, and for m to denote a number from 1 to 2000 and notably from 1 to 10;
  • A denotes a linear or branched alkylene radical containing from 4 to 8 carbon atoms and preferably 4 carbon atoms. This radical is preferably linear.
  • the weight-average molecular mass (Mw) of these amino silicones preferably ranges from 2000 to 1 000 000 g/mol and more particularly from 3500 to 200 000 g/mol.
  • a silicone corresponding to this formula is sold, for example, under the name Xiameter MEM 8299 Emulsion by the company Dow Corning.
  • amino silicones corresponding to formula (VII) are chosen from the silicones of formula (XII) below:
  • n + m and n are numbers such that the sum (n + m) ranges from 1 to 2000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to 1999 and notably from 49 to 149, and for m to denote a number from 1 to 2000 and notably from 1 to 10;
  • A denotes a linear or branched alkylene radical containing from 4 to 8 carbon atoms and preferably 4 carbon atoms. This radical is preferably branched.
  • the weight-average molecular mass (Mw) of these amino silicones preferably ranges from 500 to 1 000 000 g/mol and more particularly from 1000 to 200 000 g/mol.
  • a silicone corresponding to this formula is sold, for example, under the name DC2- 8566 Amino Fluid by Dow Corning. c) the amino silicones corresponding to formula (XIII):
  • R5 represents a monovalent hydrocarbon-based radical containing from 1 to 18 carbon atoms, and in particular a C1-C18 alkyl or C2-C18 alkenyl, for example methyl, radical;
  • R 6 represents a divalent hydrocarbon-based radical, in particular a C1-C18 alkylene radical or a divalent C1-C18, for example C-i-Cs, alkyleneoxy radical linked to the Si via an SiC bond;
  • - Q is an anion such as a halide, especially chloride, ion or an organic acid salt, especially acetate;
  • - r represents a mean statistical value ranging from 2 to 20 and in particular from 2 to 8;
  • - s represents a mean statistical value ranging from 20 to 200 and in particular from
  • R 7 which may be identical or different, represent a monovalent hydrocarbon- based radical containing from 1 to 18 carbon atoms, and in particular a C1-C18 alkyl radical, a C2-C18 alkenyl radical or a ring comprising 5 or 6 carbon atoms, for example methyl;
  • R 6 represents a divalent hydrocarbon-based radical, notably a C1-C18 alkylene radical or a divalent C1-C18, for example C-i-Cs, alkyleneoxy radical linked to the Si via an SiC bond;
  • - Re which may be identical or different, represent a hydrogen atom, a monovalent hydrocarbon-based radical having from 1 to 18 carbon atoms, and in particular a C1-C18 alkyl radical, a C2-C18 alkenyl radical or a radical -R6-N HCOR7;
  • - X is an anion such as a halide, especially chloride, ion or an organic acid salt, especially acetate;
  • - r represents a mean statistical value ranging from 2 to 200 and in particular from
  • R1 , R2, R 3 and R 4 which may be identical or different, denote a C1-C4 alkyl radical or a phenyl group,
  • R5 denotes a C1-C4 alkyl radical or a hydroxyl group
  • - n is an integer ranging from 1 to 5
  • - m is an integer ranging from 1 to 5
  • - x is chosen such that the amine number ranges from 0.01 to 1 meq/g; f) multiblock polyoxyalkylenated amino silicones, of the type (AB) n , A being a polysiloxane block and B being a polyoxyalkylene block comprising at least one amine group.
  • Said silicones are preferably constituted of repeating units of the following general formulae: [-(SiMe 2 0) x SiMe 2 -R-N(R")-R'-0(C 2 H 4 0) a (C 3 H 6 0) b -R'-N(H)-R-] or alternatively
  • - a is an integer greater than or equal to 1 , preferably ranging from 5 to 200 and more particularly ranging from 10 to 100;
  • - b is an integer between 0 and 200, preferably ranging from 4 to 100 and more particularly between 5 and 30;
  • - x is an integer ranging from 1 to 10 000 and more particularly from 10 to 5000;
  • - R" is a hydrogen atom or a methyl
  • R which may be identical or different, represent a linear or branched divalent C2- C12 hydrocarbon-based radical, optionally comprising one or more heteroatoms such as oxygen; preferably, R denotes an ethylene radical, a linear or branched propylene radical, a linear or branched butylene radical or a radical CH2CH2CH20CH2CH(0H)CH2-; preferentially, R denotes a radical CH2CH2CH20CH2CH(0H)CH2-;
  • R’ which may be identical or different, represent a linear or branched divalent C2- C12 hydrocarbon-based radical, optionally comprising one or more heteroatoms such as oxygen; preferably, R’ denotes an ethylene radical, a linear or branched propylene radical, a linear or branched butylene radical or a radical -CH2CH2CH20CH2CH(0H)CH2-; preferentially, R’ denotes -CH(CH3)-CH2-.
  • the siloxane blocks preferably represent 50 mol% and 95 mol% of the total weight of the silicone, more particularly from 70 mol% to 85 mol%.
  • the amine content is preferably between 0.02 and 0.5 meq/g of copolymer in a 30% solution in dipropylene glycol, more particularly between 0.05 and 0.2.
  • the weight-average molecular mass (Mw) of the silicone is preferably between 5000 and 1 000 000 g/mol and more particularly between 10 000 and 200 000 g/mol.
  • the amino silicone(s) are chosen from the amino silicones of formulae (VIII), (IX), (X), (XI) and (XII) above, and better still from the amino silicones of formulae (IX), (X) or (XI).
  • the silanes are preferably chosen from the compounds of formula (I) and/or oligomers thereof:
  • R2 and R3 which may be identical or different, represent a linear or branched alkyl group comprising from 1 to 6 carbon atoms,
  • - y denotes an integer ranging from 0 to 3
  • - z denotes an integer ranging from 0 to 3
  • - x denotes an integer ranging from 0 to 2
  • oligomer means the polymerization products of the compounds of formula (I) comprising from 2 to 10 silicon atoms.
  • R2 represents an alkyl group comprising from 1 to 4 carbon atoms, better still a linear alkyl group comprising from 1 to 4 carbon atoms, and preferably the ethyl group.
  • z ranges from 1 to 3.
  • y 0.
  • R1 represents an alkyl group, and even more preferentially a linear alkyl group, comprising from 7 to 18 carbon atoms and more particularly from 7 to 12 carbon atoms or a C1 -C6 and preferably C2-C4 aminoalkyl group. More particularly, R1 represents an octyl group.
  • the composition comprises octyltriethoxysilane (OTES).
  • R1 preferably represents a C1 -C6, preferably C2-C4, aminoalkyl group.
  • the composition comprises g-aminopropyltriethoxysilane (APTES).
  • the composition may comprise, as silane, at least one compound chosen from octyltriethoxysilane, dodecyltriethoxysilane, octadecyltriethoxysilane, hexadecyltriethoxysilane and y-aminopropyltriethoxysilane; more particularly chosen from octyltriethoxysilane (OTES) and g-aminopropyltriethoxysilane (APTES).
  • OTES octyltriethoxysilane
  • APTES g-aminopropyltriethoxysilane
  • the silanes may also be chosen from the compounds of formula (III) below, and/or hydrolysis products thereof and/or oligomers thereof:
  • R 4 and Rs each represent, independently of each other, a Ci- 6 , better still Ci -4 , alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl, preferably methyl, ethyl or n-propyl,
  • n 1 to 3
  • n 1 to 3
  • the oligomers of the compounds of formula (III) are water-soluble.
  • alkylalkoxysilanes that are particularly preferred, mention may be made especially of methyltriethoxysilane (MTES), methyltripropoxysilane, oligomers thereof and hydrolysis products thereof.
  • MTES methyltriethoxysilane
  • oligomers thereof oligomers thereof and hydrolysis products thereof.
  • the silanes used in the composition of the invention may be partially or totally neutralized in order to improve their water solubility.
  • the neutralizer may be chosen from organic or mineral acids, such as citric acid, tartaric acid, lactic acid or hydrochloric acid.
  • the optionally neutralized silanes according to the invention are water- soluble and especially soluble at a concentration of 2%, better still at a concentration of 5% and even better still at a concentration of 10% by weight in water at a temperature of 25°C ⁇ 5°C and at atmospheric pressure (1 atm).
  • the term“soluble” is intended to mean the formation of a single macroscopic phase.
  • the siliceous compounds are chosen from amino silicones.
  • the composition used in the process according to the invention comprises one or more organosilicon compounds, it comprises them in a total amount ranging from 0.1 % to 15% by weight, preferentially from 0.5% to 10% by weight and better still from 1 % to 5% by weight, relative to the total weight of the composition.
  • the composition used in the process according to the invention comprises one or more amino silicones, it comprises them in a total amount ranging from 0.1 % to 15% by weight, preferentially from 0.5% to 10% by weight and better still from 1 % to 5% by weight, relative to the total weight of the composition.
  • fatty substance means an organic compound that is insoluble in water at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg or 1.013x10 5 Pa) (solubility of less than 5%, preferably of less than 1 % and even more preferentially of less than 0.1% by weight).
  • the non-silicone fatty substances i.e. the fatty substances not comprising any silicon atoms in their structure
  • non- silicone fatty substances are generally soluble in organic solvents under the same temperature and pressure conditions, for instance chloroform, dichloromethane, carbon tetrachloride, ethanol, benzene, toluene, tetrahydrofuran (THF), liquid petroleum jelly or decamethylcyclopentasiloxane.
  • non-silicone fatty substances of the invention do not contain any salified carboxylic acid groups.
  • non-silicone fatty substances of the invention are not (poly)oxyalkylenated or (poly)glycerolated ethers.
  • liquid fatty substance or “oil” is intended to mean a “fatty substance” that is liquid at ambient temperature (25°C) and at atmospheric pressure (760 mmHg or 1.013x10 s Pa).
  • solid fatty substance is intended to mean a "fatty substance” that is solid at ambient temperature (25°C) and at atmospheric pressure (760 mmHg or 1.013x10 s Pa).
  • composition used in the process according to the invention may comprise, as conditioning agent, one or more non-silicone liquid fatty substances.
  • these substances may be chosen notably from liquid fatty alcohols; mineral, plant or animal oils; liquid fatty esters; liquid hydrocarbons, and mixtures thereof.
  • the liquid fatty alcohols may be linear or branched; they preferably comprise 8 to
  • the saturated liquid fatty alcohols are preferably branched. They may optionally comprise in their structure at least one aromatic or non-aromatic ring. Preferably, they are acyclic. More particularly, the saturated liquid fatty alcohols are chosen from octyldodecanol, isostearyl alcohol, 2-hexyldecanol, and also palmityl, myristyl, stearyl and lauryl alcohols, and mixtures thereof.
  • the unsaturated liquid fatty alcohols contain in their structure at least one double or triple bond, and preferably one or more double bonds. When several double bonds are present, there are preferably 2 or 3 of them, and they may be conjugated or unconjugated.
  • the unsaturated liquid fatty alcohols are chosen from oleyl alcohol, linoleyl alcohol, linolenyl alcohol and undecylenyl alcohol, and mixtures thereof.
  • oils of plant origin of sweet almond oil, avocado oil, castor oil, olive oil, jojoba oil, sunflower oil, wheatgerm oil, sesame oil, groundnut oil, grapeseed oil, soybean oil, rapeseed oil, safflower oil, coconut oil, corn oil, hazelnut oil, shea butter, palm oil, apricot kernel oil, beauty-leaf oil, evening primrose oil or camelina oil; as oil of animal origin, perhydrosqualene; as oils of mineral origin, liquid paraffin and liquid petroleum jelly; and mixtures thereof.
  • the liquid fatty esters may be esters of monoalcohols or of polyols with monoacids or polyacids, at least one of the alcohols and/or acids including at least one chain of more than 7 carbon atoms.
  • the liquid fatty ester according to the invention is chosen from esters of a fatty acid and of a monoalcohol.
  • at least one of the alcohols and/or acids is branched.
  • isopropyl myristate isopropyl palmitate, isononyl or isostearyl isononanoate
  • 2-ethylhexyl palmitate 2- hexyldecyl laurate
  • 2-octyldecyl palmitate 2-octyldodecyl myristate
  • purcellin oil stearyl octanoate
  • isopropyl lanolate and mixtures thereof.
  • liquid hydrocarbon means a hydrocarbon composed solely of carbon and hydrogen atoms, which is liquid at 25°C and 1 atm, which is notably of mineral or plant origin, preferably of plant origin.
  • liquid hydrocarbon that may be used in the composition according to the invention, mention may be made of:
  • hydrocarbons especially of mineral, animal or synthetic origin with more than 16 carbon atoms, such as volatile or non-volatile liquid paraffins, petroleum jelly, liquid petroleum jelly, polydecenes, hydrogenated polyisobutene such as the product sold under the brand name Parleam® by the company NOF Corporation, and squalane.
  • the composition comprises one or more non-silicone liquid fatty substances
  • it comprises them in a total amount ranging from 0.1 % to 15% by weight, preferably from 0.5% to 10% by weight and even better still from 1 % to 5% by weight, relative to the total weight of the composition.
  • Non-silicone solid fatty substances preferably from 0.5% to 10% by weight and even better still from 1 % to 5% by weight, relative to the total weight of the composition.
  • composition used in the process according to the invention may comprise, as conditioning agent, one or more non-silicone solid fatty substances.
  • These substances may be chosen notably from solid fatty alcohols; solid fatty esters, ceramides; animal, plant or mineral waxes other than ceramides; and mixtures thereof.
  • the solid fatty alcohols that may be used are preferably chosen from saturated or unsaturated, linear or branched, preferably linear and saturated, (mono)alcohols including from 8 to 30 carbon atoms and notably 10 to 24 carbon atoms. Mention may be made, for example, of cetyl alcohol, stearyl alcohol and the mixture thereof (cetylstearyl alcohol).
  • the solid fatty esters that may be used are preferably chosen from esters derived from C9-C26 monocarboxylic acids and from C9-C26 alcohols. Mention may be made of octyldodecyl behenate, isocetyl behenate, cetyl lactate, stearyl octanoate, octyl octanoate, cetyl octanoate, decyl oleate, myristyl stearate, octyl palmitate, octyl pelargonate, octyl stearate, alkyl myristates such as cetyl myristate, myristyl myristate or stearyl myristate, and hexyl stearate.
  • Esters of C4-C22 dicarboxylic or tricarboxylic acids and of C1-C22 alcohols and esters of mono-, di- or tricarboxylic acids and of C2-C26 di-, tri-, tetra- or pentahydroxy alcohols may also be used. Mention may be made notably of diethyl sebacate, diisopropyl sebacate, diisopropyl adipate, di-n-propyl adipate, dioctyl adipate and dioctyl maleate.
  • C9-C26 alkyl palmitates notably myristyl, cetyl or stearyl palmitates
  • C9-C26 alkyl myristates such as cetyl myristate, stearyl myristate and myristyl myristate or mixtures of myristyl palmitate and myristyl stearate.
  • ceramides, or ceramide analogues such as glycoceramides, that may be used in the composition according to the invention are known per se; mention may in particular be made of ceramides of classes I, II, III and V according to the Dawning classification; they are molecules which may correspond to the formula below: FLCHOH— CH— CH 9 OR 9
  • - Ri denotes a linear or branched, saturated or unsaturated alkyl group, derived from C14-C30 fatty acids, it being possible for this group to be substituted with a hydroxyl group in the alpha position, or a hydroxyl group in the omega position esterified with a saturated or unsaturated C16-C30 fatty acid;
  • R2 denotes a hydrogen atom, a (glycosyl)n group, a (galactosyl)m group or a sulfogalactosyl group, in which n is an integer ranging from 1 to 4 and m is an integer ranging from 1 to 8;
  • R 3 denotes a C 15 -C 26 hydrocarbon-based group, which is saturated or unsaturated in the alpha position, this group possibly being substituted with one or more C1-C14 alkyl groups;
  • R3 may also denote a C15-C26 alpha-hydroxyalkyl group, the hydroxyl group optionally being esterified with a C16-C30 alpha-hydroxy acid.
  • the ceramides more particularly preferred are the compounds for which R1 denotes a saturated or unsaturated alkyl derived from C16-C22 fatty acids; R2 denotes a hydrogen atom and R3 denotes a saturated linear C15 group.
  • R1 denotes a saturated or unsaturated alkyl radical derived from C12-C22 fatty acids
  • R2 denotes a galactosyl or sulfogalactosyl radical
  • 2-N- linoleoylaminooctadecane-1 ,3-diol 2-N-oleoylaminooctadecane-1 ,3-diol
  • a wax is a lipophilic compound, which is solid at ambient temperature (25°C), with a reversible solid/liquid change of state, having a melting point greater than about 40°C, which may be up to 200°C, and having in the solid state anisotropic crystal organization.
  • the size of the wax crystals is such that the crystals diffract and/or scatter light, giving the composition that comprises them a more or less opaque cloudy appearance.
  • waxes other than the ceramides above, that can be used in the present invention, mention may be made of waxes of animal origin, such as beeswaxes or modified beeswaxes (cera bellina), spermaceti, lanolin wax and lanolin derivatives; plant waxes such as carnauba wax, candelilla wax, esparto wax, ouricury wax, Japan wax, cocoa butter, cork-fibre wax, sugarcane wax, olive-tree wax, rice wax, hydrogenated jojoba wax, absolute waxes of flowers; mineral waxes, for example paraffin wax, petroleum jelly wax, lignite wax, microcrystalline waxes, ozokerites, and mixtures thereof.
  • beeswaxes or modified beeswaxes (cera bellina) spermaceti, lanolin wax and lanolin derivatives
  • plant waxes such as carnauba wax, candelilla wax, esparto wax, ouri
  • the non-silicone solid fatty substances may be chosen from solid fatty alcohols and solid fatty esters.
  • the composition comprises one or more solid fatty substances, it comprises them in a total amount ranging from 0.1 % to 15% by weight, preferably from 0.5% to 10% by weight and even better still from 1 % to 5% by weight, relative to the total weight of the composition.
  • the conditioning agent(s) are chosen from:
  • organosilicon compounds and especially silicones and silanes and preferably amino silicones
  • non-silicone liquid fatty substances and especially hydroxylated or non- hydroxylated liquid fatty acids; liquid fatty alcohols; mineral or plant oils; liquid fatty esters; liquid hydrocarbons;
  • non-silicone solid fatty substances and especially solid fatty alcohols; solid fatty esters; ceramides; animal, plant or mineral waxes other than ceramides; and mixtures of these compounds.
  • the conditioning agent(s) are chosen from cationic surfactants, cationic polymers, amino silicones, liquid fatty alcohols, solid fatty alcohols, liquid fatty esters and solid fatty esters, and mixtures thereof.
  • the composition does not comprise any fixing polymer.
  • fixing polymer is intended to mean any polymer that is capable, by application to the hair, of giving a shape to the head of hair or of holding an already acquired shape, it being possible for the fixing polymers to be anionic, cationic, amphoteric or non-ionic fixing polymers.
  • the composition comprises one or more fixing polymers, then it preferably comprises less than 3% by weight thereof relative to the total weight of the composition, preferably less than 2% by weight relative to the total weight of the composition.
  • composition used in the process according to the invention may also comprise an organic acid and/or a sugar and/or a sugar derivative.
  • the organic acid(s) may be chosen from monocarboxylic acids, dicarboxylic acids and tricarboxylic acids, in particular from glycolic acid, lactic acid, succinic acid, glutaric acid, itaconic acid, maleic acid and citric acid, preferably from maleic acid and citric acid, and preferably is citric acid.
  • the sugar(s) and/or sugar derivative(s) may be chosen from erythrose, trehalose, lactulose and maltose, preferably in their D form, pectin, D-glucosamine hydrochloride, preferably from trehalose and pectin.
  • composition applied in the process according to the present invention is preferably aqueous.
  • the water content is preferably greater than or equal to 10% by weight, more preferentially greater than or equal to 20% by weight, and even better still greater than or equal to 30% by weight relative to the total weight of the composition.
  • the water content present in the composition of the invention ranges from 30% to 98% by weight, preferably from 50% to 95% by weight and more preferentially from 65% to 95% by weight, relative to the total weight of the composition.
  • composition according to the present invention may optionally comprise one or more organic solvents, or mixtures thereof.
  • organic solvents examples include linear or branched C 2 to C 4 alkanols, such as ethanol and isopropanol; glycerol; polyols and polyol ethers, for instance 2-butoxyethanol, propylene glycol, hexylene glycol, dipropylene glycol, propylene glycol monomethyl ether, diethylene glycol monomethyl ether and monoethyl ether, and also aromatic alcohols or ethers, such as benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • alkanols such as ethanol and isopropanol
  • glycerol examples include 2-butoxyethanol, propylene glycol, hexylene glycol, dipropylene glycol, propylene glycol monomethyl ether, diethylene glycol monomethyl ether and monoethyl ether, and also aromatic alcohols or ethers, such as benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • the pH of the composition is preferably greater than or equal to 2, preferably greater than or equal to 3 and preferably ranges from 2 to 8, better still from 3 to 5.
  • the basifying agent may be chosen from mineral or organic or hybrid alkaline agents, or mixtures thereof.
  • the mineral alkaline agent(s) are preferably chosen from aqueous ammonia, alkaline carbonates or bicarbonates such as sodium or potassium carbonates and sodium or potassium bicarbonates, sodium hydroxide or potassium hydroxide, or mixtures thereof.
  • the organic alkaline agent(s) are preferably chosen from organic amines with a pKb at 25°C of less than 12, preferably less than 10 and even more advantageously less than 6. It should be noted that this is the pKb corresponding to the function of highest basicity.
  • Hybrid compounds that may be mentioned include the salts of the amines mentioned previously with acids such as carbonic acid or hydrochloric acid.
  • the organic alkaline agent(s) are chosen, for example, from amine derivatives such as alkanolamines, oxyethylenated and/or oxypropylenated ethylenediamines, and amines such as 1 ,3-diaminopropane, 1 ,3-diamino-2-propanol, spermine or spermidine.
  • amine derivatives such as alkanolamines, oxyethylenated and/or oxypropylenated ethylenediamines
  • amines such as 1 ,3-diaminopropane, 1 ,3-diamino-2-propanol, spermine or spermidine.
  • alkanolamine is intended to mean an organic amine comprising a primary, secondary or tertiary amine function, and one or more linear or branched C-i-Cs alkyl groups bearing one or more hydroxyl radicals.
  • Sodium hydroxide is in particular suitable for the implementation of the invention.
  • the acidifying agent may be chosen from mineral acids, for instance hydrochloric acid or phosphoric acid.
  • the composition according to the invention comprises neither hair- dyeing agent, nor sulfur-containing or phosphorus-containing reducing agent for permanent reshaping.
  • reducing agent is intended to mean an agent that is capable of reducing the disulfide bonds of the hair, such as compounds chosen from thiols, alkaline sulfites, hydrides and phosphines.
  • the term "hair-dyeing agent” is intended to mean a direct dye, an oxidation dye precursor (oxidation base and coupler) or any other compound which gives colour to the keratin fibres, usually used for colouring human keratin fibres, or alternatively, if it does comprise any, the total amount thereof does not exceed 0.005% by weight relative to the weight of the composition. Specifically, at such a content, only the composition would be dyed, i.e. no dyeing effect would be observed on the keratin fibres.
  • oxidation dye precursors, oxidation bases and couplers are colourless or sparingly coloured compounds, which, via a condensation reaction in the presence of an oxidizing agent, give a coloured species.
  • direct dyes these compounds are coloured and have a certain affinity for keratin fibres.
  • the composition may also comprise at least one usual cosmetic ingredient, in particular chosen from surfactants other than the cationic surfactants described above and in particular from non-ionic surfactants; polymeric or non-polymeric thickeners, and most particularly polysaccharide thickeners and/or associative polymers, sunscreens; antidandruff agents; antioxidants; chelating agents; nacreous agents and opacifiers; plasticizers or coalescence agents; fillers; emulsifiers; fragrances; crosslinking agents.
  • the composition can, of course, comprise several cosmetic ingredients appearing in the above list.
  • the usual cosmetic ingredients may be present in usual amounts, which can be readily determined by those skilled in the art and which may be, for each ingredient, between 0.01 % and 80% by weight. Those skilled in the art will take care to select the ingredients included in the composition, and also the amounts thereof, so that they do not harm the properties of the composition of the present invention.
  • composition that is of use in the process of the invention may be in any of the conventionally used galenical forms, in particular in the form of a gel or a cream.
  • the application of the composition as described above can be carried out on dry hair or on wet hair.
  • the composition is applied to wet hair. More preferably, the wet hair has been predried before the application of the composition, that is to say it has been wiped with a towel for example, or optionally partially dried using a hairdryer.
  • the process according to the invention also comprises a step of placing the hair under mechanical tension using a tensioning means.
  • the step of placing the hair under mechanical tension can be carried out before or after the application of the composition to the hair.
  • the step of placing the hair under mechanical tension is carried out after the application of the composition to the hair.
  • the step of placing under mechanical tension can be carried out with a mechanical tensioning means chosen from rollers, head bands, elastics, buns, strips for braiding with or around the hair braiding, headscarves.
  • a mechanical tensioning means chosen from rollers, head bands, elastics, buns, strips for braiding with or around the hair braiding, headscarves.
  • the mechanical tensioning means can be made of flexible or rigid material, for example of woven or nonwoven textile material, of plastic, or foam.
  • the tensioning means may be variable in shape, for example spherical, toric, tubular, elongated, flat.
  • the mechanical tensioning means most suitable for the desired effect will be chosen.
  • the composition is left on the hair subjected to a mechanical stress for at least four hours, preferably at least six hours, more preferentially for at least eight hours, better still between eight hours and ten hours. It is for example possible to apply the composition and to place the hair under mechanical tension before going to bed and to leave this on overnight, in particular while sleeping.
  • the step of placing the hair under tension using a tensioning means is carried out without applying heat using a heating means.
  • the process according to the invention does not comprise a step of rinsing the hair after the step of removing the tensioning means.
  • the process for shaping the hair according to the invention does not comprise any step in which a composition comprising a reducing agent and/or a colouring agent as defined above are applied.
  • compositions were prepared. The concentrations are expressed as weight percentages of active material in the final composition.
  • compositions C and T1 to T3 were applied, in a proportion of 0.4 g of composition per lock, to locks of straight natural Caucasian hair of 2.7 g, 27 cm long, prewashed with a shampoo, rinsed and predried using a towel.
  • the locks thus treated were rolled around a spiral roller and left to dry for 8 hours in a chamber at 37°C.
  • the locks obtained are then photographed at TO and after 4 hours (T4h) and the length of each lock was measured.
  • the relaxation after 4 h corresponds to the difference in length between the lock at TO and the lock after 4 h.
  • composition C makes it possible to improve the hold of the hairstyle after 4 hours compared with an identical process in which a conventional fixing polymer is used, this being with an identical feel. It is also noted that, at equal lock relaxation, the composition according to the invention makes it possible to improve the feel of the hair compared with an identical process in which a conventional fixing polymer is used.
  • composition was prepared. The concentrations are expressed as weight percentages of active material in the final composition.
  • compositions A1 was applied, in a proportion of 0.4 g of composition per lock, to locks of straight natural Caucasian hair of 2.7 g, 27 cm long, prewashed with a shampoo, rinsed and predried using a towel.
  • the locks thus treated were rolled around a spiral roller (diameter 16 mm) and left to dry for 3 hours or 7 hours in a chamber at 37°C (in order to simulate scalp temperature).
  • Each lock was then suspended vertically in front of graph paper and they were photographed at TO. The length of each lock was measured.
  • composition A1 with a tensioning means during more than 4 hours makes it possible to improve the fixing power compared with an identical composition but with tensioning means during less the 4 hours.

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Abstract

La présente invention concerne un procédé de mise en forme des cheveux, dans lequel : - une composition comprenant un ou plusieurs composés(s) de type lactone est appliquée sur les cheveux, de préférence sur des cheveux humides, - les cheveux sont mis sous tension à l'aide d'un moyen de mise sous tension, - la composition et les moyens de mise sous tension sont laissés sur les cheveux pendant au moins quatre heures, puis - le moyen de mise sous tension est retiré.
PCT/EP2019/067201 2018-06-29 2019-06-27 Procédé de mise en forme des cheveux comprenant une étape d'application d'une composition comprenant une lactone, une étape de mise en forme et une longue durée pendant laquelle le produit est laissé sur les cheveux WO2020002522A1 (fr)

Applications Claiming Priority (2)

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FR1856040 2018-06-29
FR1856040A FR3083104B1 (fr) 2018-06-29 2018-06-29 Procede de mise en forme des cheveux comprenant une etape d’application d’une composition comprenant une lactone, une etape de mise en forme et un long temps de pause

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US3589578A (en) 1968-01-20 1971-06-29 Monforts Fa A Tension-relieving device for stretchable sheet material
FR2077143A5 (fr) 1970-01-30 1971-10-15 Gaf Corp
US4031307A (en) 1976-05-03 1977-06-21 Celanese Corporation Cationic polygalactomannan compositions
US4131576A (en) 1977-12-15 1978-12-26 National Starch And Chemical Corporation Process for the preparation of graft copolymers of a water soluble monomer and polysaccharide employing a two-phase reaction system
FR2393573A1 (fr) 1977-06-10 1979-01-05 Gaf Corp Preparations capillaires contenant un copolymere de vinylpyrrolidone
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US4874554A (en) 1986-07-10 1989-10-17 Henkel Kommanditgesellschaft Auf Aktien Quaternary ammonium compounds
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US3589578A (en) 1968-01-20 1971-06-29 Monforts Fa A Tension-relieving device for stretchable sheet material
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US4031307A (en) 1976-05-03 1977-06-21 Celanese Corporation Cationic polygalactomannan compositions
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FR2393573A1 (fr) 1977-06-10 1979-01-05 Gaf Corp Preparations capillaires contenant un copolymere de vinylpyrrolidone
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US4874554A (en) 1986-07-10 1989-10-17 Henkel Kommanditgesellschaft Auf Aktien Quaternary ammonium compounds
US4957732A (en) 1988-12-29 1990-09-18 L'oreal Shaving composition for the skin based on polyorgano-siloxanes containing an acyloxyalkyl group and process for use
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