MXPA98002962A - Composition for the treatment of keratinic fibers, covering at least one fixed polymer and at least one compound of type ceramid and procedure - Google Patents

Composition for the treatment of keratinic fibers, covering at least one fixed polymer and at least one compound of type ceramid and procedure

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Publication number
MXPA98002962A
MXPA98002962A MXPA/A/1998/002962A MX9802962A MXPA98002962A MX PA98002962 A MXPA98002962 A MX PA98002962A MX 9802962 A MX9802962 A MX 9802962A MX PA98002962 A MXPA98002962 A MX PA98002962A
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Mexico
Prior art keywords
copolymers
radical
acid
composition according
vinyl
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MXPA/A/1998/002962A
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Spanish (es)
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MX202859B (en
MX9802962A (en
Inventor
Dubief Claude
Cretois Isabelle
Braidavalerio Damarys
Dupuis Christine
Original Assignee
L'oreal
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Priority claimed from FR9512448A external-priority patent/FR2740034B1/en
Application filed by L'oreal filed Critical L'oreal
Publication of MX9802962A publication Critical patent/MX9802962A/en
Publication of MXPA98002962A publication Critical patent/MXPA98002962A/en
Publication of MX202859B publication Critical patent/MX202859B/en

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Abstract

The present invention relates to a composition cosmetically for the treatment of keratin fibers, in particular human hair, comprising at least one anionic, nonionic, amphoteric or zwitterionic fixing polymer and at least one ceramide-type compound as well as the process of treatment with the help of this composition

Description

POMPOSTPT? M FOR THE TREATMENT OF AS FTRRAS QUERAT NICAS-OVE COMPRISES AT LEAST ONE POLYMER FT ftNTB AND AT LEAST ONE COMPOSITE OF TTPO CERAMTDA AND PROCEDURES DESCRIPTION OF THE INVENTION The present invention relates to a cosmetic composition for the treatment of keratin fibers such as hair, comprising at least one fixing polymer and at least one. compound of the ceramide type as well as the non-therapeutic treatment method with the aid of this composition. Maintenance or hair shaping compositions containing styling polymers (fixative polymers) in their formulation generally have the disadvantage of making it difficult to disentangle, re-styling or brushing the hair, in particular during a brush marking. During the brush marking, the hair is damaged by the heat of the dryer and the brush passes through the hair to shape the hair.
REF: 27113 Numerous hairs break like this during a brush marking. Therefore, compositions are sought to protect the hair from this break during these attacks. The production of silicone derivatives in association with fixing polymers is known in the preparation of cosmetic compositions for the maintenance of combing. It has been observed that these silicone derivatives improve the detangling, softness and brilliance properties of the treated hair with the help of these. compositions However, on the one hand, the silicone derivatives are not favorable for the styling properties of the compositions containing fixative polymers and, on the other hand, the protective effect with respect to the breakage of the hair is still not satisfactory. However, the applicant has surprisingly discovered that by using compositions containing a fixing polymer in association with ceramide-type compounds, a very good protection effect was obtained with respect to the breakage of the hair, in particular during a brush marking presenting excellent styling properties.
The combing properties are of the same level or even superior to those of a composition that only contains the fixing polymer. In particular, the fixing power, the behavior with time and the volume of hair are very good. This discovery forms the basis of the present invention. The subject of the invention is therefore a non-detergent cosmetic composition, intended for the treatment of keratinous fibers such as hair, characterized in that it contains in a cosmetically acceptable medium at least one fixing polymer and at least one compound of the ceramide type, said polymeric compositions containing vinylpyrrolidone and / or cationic polymer comprising primary, secondary, tertiary or quaternary ammonium groups in the main chain and having a viscosity of 1% by weight of active material in water less than 15 mPa.s. The subject of the invention is also the use of the composition defined above to protect the hair during brush marking.
These compositions also make it possible to improve the cosmetic properties, in particular the softness and the straightening of the hair. By the fixing power of the composition, the behavior of the latter is designated in providing the hair with a cohesion such that the initial conformation of the hairstyle is maintained. By "fixing polymer" is meant any polymer which has the function of temporarily fixing the shape of the hairstyle. The term "non-detergent" means that the composition does not allow to remove from a solid medium, such as, for example, the hair, the dirt adhering to it by its dispersion or solution. In particular, the compositions according to the invention comprise less than 4% by weight relative to the total weight of the composition of anionic or amphoteric detergent surfactants. By vinylpyrrolidone polymer, polymers containing at least one vinylpyrrolidone monomer are designated. According to the present invention, it is understood, by compound of ceramide type, ceramides and / or glycoceramides and / or pseudoceramides and / or neoceramides, natural or synthetic.
Ceramide-type compounds are described, for example, in patent applications DE 4,424,530 DE 4,424,533; DE4, 402,929; DE4, 420, 736; WO95 / 23807 WO94 / 07844; EP-A-0, 64 ß, 572; 095 / lßßß5; FR-2,673,179 EP-A-0, 227, 994 and WO94 / 07844; WO94 / 24097; WO94 / 10131 whose teachings are included herein by way of reference. The ceramide-type compounds which can be used according to the present invention preferably correspond to the general formula (I): in which: - Ri designates: - either a hydrocarbon radical, linear or branched, saturated or unsaturated, of C5-C5, this radial being able to be replaced by one or more hydroxyl groups optionally esterified by an acid R7COOH, being R- a hydrocarbon radical, saturated or unsaturated, linear or branched, optionally mono or polyhydroxylated, of C? -C; ^, the hydroxyl (s) of the radical R being capable of being esterified by a saturated or unsaturated fatty acid, linear or branched, optionally mono or polyhydroxylated, of d-C35; - either a radical R "- (NR-CO) -R ', R designates a hydrogen atom or a hydrocarbon radical C? -C or monohydric or polyhydric, preferably monohydroxylated, R' and R" are hydrocarbon radicals whose sum of the carbon atoms is between 9 and 30, where R 'is a divalent radical; or else a radical Rβ-0-CO- (CH;) p, Rs denotes a hydrocarbon radical of C 1 -C-., p is an integer ranging from 1 to 12; R_ designates a hydrogen atom or a radical (glycosyl) r, (galactosyl) m, sulfo-galactosyl, a radical fos for ilet ilamine or fos foriletilamium, in which n is an integer ranging from 1 to 4 and m is an integer that varies from 1 to 8; R designates a hydrogen atom or a C1-C33 hydrocarbon radical, saturated or unsaturated, hydroxylated or not, the hydroxyl (s) being capable of being esterified by a mineral acid or an acid R7COOH, having R- the same meanings as above, the or the hydroxyls are etherified by a radical (glycosyl) r, (galactosyl) m, sul-fogalactosyl, fos-forylethylamine or phosphorylethylammonium, where R3 can also be substituted by one or more C rad-C? alkyl radicals.; Preferably, R3 designates an α-hydroxyalkyl radical of C15-C-6, the hydroxyl group optionally being esterified by an α-hydroxy acid of c 1 r, -C 30; R4 denotes a hydrogen atom, a methyl, ethyl radical, a C3-C50 hydrocarbon radical, saturated or unsaturated, linear or branched, optionally hydroxylated or a radical -CH; -CHOH-CH2-. 0-R6 in which R ,. designates a hydrocarbon radical of Cι-Cβ or a radical R ^ -O-CO- (CH_) F, R8 denotes a hydrocarbon radical of C?-C _, p is an integer ranging from 1 to 12; R; designates a hydrogen atom or a hydrocarbon radical of C? -C or saturated or unsaturated, linear or branched, optionally mono or polyhydroxy, the hydroxyl (s) being capable of being esterified by a radical (glycosyl), (galactosyl), sul ilo, fos forilet ilamine or phosphorylethylammonium fogalactos, with the proviso that when R3 and Rt designate hydrogen or when R3 designates hydrogen and Rr designates methyl then R4 does not designate a hydrogen atom, a methyl or ethyl radical. Among the compounds of formula (I), ceramides and / or glycoceramides whose structure is described by DOWNING in Journal of Lipid Research Vol. 35, 2060-2068, 1994, or those described in French patent application FR-2,673,179 are preferred. , whose teachings are included here for reference. The compounds of the ceramide type which are more particularly preferred according to the invention are the compounds of formula (I) for which Ri denotes a saturated or unsaturated alkyl derived from fatty acids of C? -C__ eventually hydroxylated; R_ designates a hydrogen atom; and Ri designates a linear radical of Cn-i? optionally hydroxylated and preferably Cp -; .. Such compounds are for example: - N-linoleoyldihydrosphingosine, - N-oleoi ldihydroes fingosine, - N-palmi toildihydroes phytosine, - N-es tearoidihydroes f ingosine, - N-behenoyldihydrosphingosine, - N-2-hydroxypallitoyldihydrosphingosine, - N-es tearoi 1 phytoes fingos ina, - N-palmitamidohexadecanediol, or the mixtures of these compounds. It is also possible to use specific mixtures such as, for example, mixtures of ceramide (s) 2 and ceramide (s) 5 according to the DOWNING classification. It is also possible to use the compounds of formula (I) for which Ri denotes a saturated or unsaturated alkyl radical derived from fatty acids; R denotes a galactosyl radical. or sulfogalactosyl; and R3 designates a saturated or unsaturated C?-C: 2 hydrocarbon radical, and preferably a -CH = CH- (CH_) -CH 3 group. By way of example, mention may be made of the product constituted by a mixture of glycoceramides, sold under the trade name GLYCOCER by the company WAITAKI INTERNATIONAL BIOSCIENCES. It is also possible to use the compounds of formula (I) described in patent applications EP-A-0227994 and WO94 / 07844. Such compounds are for example QUESTAMIDE H (bis- (N-hydroxy et i 1-N-cet i 1) malonamide) sold by the company QUEST, N- (2-hydroxyethyl i) -N- (3-cet) iloxy-2-hydroxypropyl 1) cetyl acid amide. It is also possible to use the N-docosanoyl-N-met i 1-D-glucamine described in the patent application WO94 / 24097. The concentration of ceramide-type compounds can vary between 0.0001% and 20% by weight approximately relative to the total weight of the composition, and preferably between 0.001 and 10% approximately and even more preferably between 0.005 and 3% by weight. According to the invention, any known per se removable polymer with shampoo selected from anionic, amphoteric, zwitter ionic, nonionic polymers and mixtures thereof can be used. The fixing polymers can be used in solubilized form or in the form of latex or pseudolatex (aqueous dispersion of insoluble solid polymer particles). Thus, the anionic fixing polymers generally used are polymers which include carboxylic, sulfonic or phosphoric acid derivative groups and have a molecular weight of between about 500 and 5,000,000.
These carboxylic groups are provided by unsaturated mono or dicarboxylic carboxylic monomers such as those which correspond to the formula: wherein n is an integer from 0 to 10, A designates a methylene group, optionally attached to the carbon atom of the unsaturated group or to the next methylene group when n is greater than 1 by mediating a heteroatom such as oxygen or sulfur , RT denotes a hydrogen atom, a phenyl or benzyl group, R * denotes a hydrogen atom, a lower alkyl or carboxyl group, R ^ denotes a hydrogen atom, a lower alkyl group, a -CH_-COOH group, or a phenyl or benzyl group. In the aforementioned formula a lower alkyl radical preferably designates a group having from 1 to 4 carbon atoms and in particular, methyl and ethyl. The anionic polymers with preferred carboxylic groups according to the invention are: A) the homo- or copolymers of acrylic or methacrylic acid or their salts and in particular the products sold under the names VERSICOL E or K by the company ALLIED COLLOID, ULTRAHOLD, by BASF society. The acrylic acid and acrylamide copolymers sold in the form of their sodium salt under the names RETEN 421, 423 or 425 by the company HERCULES, the sodium salts of the polyhydroxycarboxylic acids; B) copolymers of acrylic or methacrylic acids with a monoether monomer such as ethylene, styrene, vinyl esters, esters of acrylic or methacrylic acid, optionally grafted onto a polyalkylene glycol. such as polyethylene glycol and eventually crosslinked. Such polymers are described in particular in French Patent 1,222,944 and German Application 2,330,956, copolymers of this type include in their chain an optionally N-alkylated and / or hydroxyalkylated acrylamide type such as those described in particular in the Luxembourg patent applications 75370 and 75371 or proposals under the name QUADRAMER by the AMERICAN CYANAMID Company. Mention may also be made of the copolymers of acrylic acid and C 1 -C 4 alkyl methacrylate and the copolymer of methacrylic acid and ethyl acrylate sold under the name LUVIMER MAEX by the company BASF. C) copolymers derived from crotonic acid such as those which include in their chain vinyl acetate or propionate and optionally other monomers such as allyl or metalyl esters, vinyl ether or vinyl ester of a linear or branched saturated carboxylic acid of long hydrocarbon chain such as those which include at least 5 carbon atoms, these polymers possibly being grafted and crosslinked or else, a vinyl, allyl or metalyl ester of an α- or β-cyclic carboxylic acid. Such polymers are described inter alia in French patents 1,222,944, 1,580,545, 2,265,782, 2,265,782, 2,265,781, 1,564,110 and 2,439,798. The commercial products that fall into this class are resins 28-29-30, 26-13-14 and 28-13-10 sold by the company NATIONAL STARCH; D) polymers derived from maleic, fumaric, itaconic acids or anhydrides with vinyl esters, vinyl ethers, vinyl halides, phenyl vinyl derivatives, acrylic acid and their esters; these polymers can be esterified. Such polymers are described in particular in U.S. Patent Nos. 2,047,398, 2,723,248, 2,102,113, the Great Britain Patent 839,805 and particularly sold under the names GANTREZ AB or ES by the ISP Company. Polymers that also fall into this class are the copolymers of maleic, citraconic and itaconic anhydrides and of an allyl or methallyl ester optionally including an acrylamide group, methacrylamide, an α-olefin, acrylic or methacrylic esters, acrylic or methacrylic acids in their chain, the anhydride functions are mono- or ternal. monoamidi f ican. These polymers are described, for example, in French Patents 2,350,384 and 2,357,241, of the applicant. E) Polyacrylamides including carboxylate groups. The polymers comprising the sulfonic groups are polymers including vinyl sulfonic, styrene sulfonic, naphthalene sulphonic or acrylamido alkylsulfonic motifs. These polymers can be selected in particular from: - the salts of polyvinyl sulphonic acid with a molecular weight 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, sodium salts with a molecular weight of approximately 500,000 and approximately 100,000 sold respectively under the names Flexan 500 and Flexan 130 by National Starch. These compounds are described in patent FR 2,198,719. - the salts of polyacrylamide sulphonic acids, those mentioned in US Pat. No. 4,128,631 and more particularly the polyacrylamidoethepropropane sulfonic acid sold under the name COSMEDIA POLYMER HSP 1180 by Henkel. According to the invention, the anionic polymers are preferably chosen from acrylic acid copolymers such as the terpolymer acrylic acid / ethyl acrylate / N-tert-butyl acrylamide expired under the name ULTRAHOLD STRONG by the company BASF, the derived copolymers of crotonic acid such as the terpolymers vinyl acetate / vinyl tert-butylbenzoate / crotonic acid and the terpolymers crotonic acid / vinyl acetate / vinyl neododecanoate sold under the name Resin 28-29-30 by the company NATIONAL STARCH, the polymers derivatives of acids or of anhydrides maleic, fumaric, itaconic with vinyl esters, vinyl ethers, vinyl halides, fenilvinyl derivatives, acrylic acid and their esters such as the methyl vinyl ether / maleic esterified anhydride copolymer sold under the name GANTREZ ES 425 by the ISP society, the copolymers of methacrylic acid and methyl methacrylate or sold under the name EUDRAGIT L by the company ROHM PHARMA, the copolymer of methacrylic acid and acrylate of. ethyl sold under the name LUVIMER MAEX by the company BASF and the copolymer vinyl acetate / crotonic acid expired under the name LUVISET CA 66 by the company BASF and the terpolymer vinyl acetate / crotonic acid / polyethylene glycol under the name ARISTOFLEX A by the Company BASF. The most particularly preferred anionic polymers are chosen from the monovinyl ether / maleic esterified monohydric anhydride copolymer sold under the name GANTREZ ES 425 by the Company ISP, the terpolymer acrylic acid / ethyl acrylate / N-tert-butylacrylamide expired under the designation ULTRAHOLD STRONG by the company BASF, the copolymers of methacrylic acid and methyl methacrylate sold under the name EUDRAGIT L by the company ROHM PHARMA, the terpolymers vinyl acetate / tert-butylbenzoate vinyl / crotonic acid and the terpolymers crotonic acid / acetate vinyl / neododecanoate sold under the name Resine 28-29-30 by the company NATIONAL STARCH, the copolymer of methacrylic acid and ethyl acrylate sold under the name LUVIMER MAEX by the company BASF, the terpolymer of vinylpyrrolidone / acrylic acid / methacrylate of. lauril sold under the name ACRYLIDONE LM by the ISP Company. The amphoteric or zwitterionic polymers which can be used according to the invention can be chosen from polymers including motifs B and C statistically distributed in the polymer chain where B denotes a moiety derived from a monomer comprising at least one basic nitrogen atom and C designates a motif that is derived from an acidic monomer that includes one or more carboxylic or sulphonic groups, or B and C may designate a group derived from zwitterionic monomers of carboxy betaines or sulfo betaines; B and C can also designate a cationic polymer chain including primary, secondary, tertiary or quaternary amine groups, in which at least one of the amine groups carries a carboxylic or sulphonic group attached via a hydrocarbon radical or B and C they form part of a chain of a polymer of ethylene α, β-dicarboxylic motif of which one of the carboxylic groups has been reacted with a polyamine which includes one or several primary amine groups. or secondary The amphoteric fixing polymers that meet the above given definition are more particularly preferred among the following polymers: 1) The polymers resulting from the copolymerization of a monomer derived from a vinyl compound bearing a carboxylic group such as more particularly acrylic acid, methacrylic acid, maleic acid, facloracrylic acid, and a basic monomer derived from a substituted vinyl compound containing at least one basic atom such as, more particularly, the dialkyl, laminoalkyl, acrylate, dialkyl, laminoalkyl, lmetacri, and Acrylamide Such compounds are described in American Patent No. 3, 836, 537. 2) Polymers that include motifs that are derived: a) from at least one monomer selected from acrylamides or methacrylamides substituted on nitrogen by an alkyl radical, ) of at least one acid comonomer containing one or more reactive carboxylic groups, and c) at least one such basic comonomer. as esters with primary, secondary, tertiary and quaternary amine substituents of the acrylic and methacrylic acids and the quaternization product of dimethylaminoethyl methacrylate with dimethyl or diethyl sulfate. The N-substituted acrylamides or methacrylamides more particularly preferred according to the invention are those groups whose alkyl radicals contain from 2 to 12 carbon atoms and more particularly N-ethylacrylamide, N-tert-butylacrylamide, N-tert-octylacrylamide, N-octylacrylamide, N-decylacrylamide, N-dodecyl acrylamide as well as the corresponding methacrylamides.
Acid comonomers are chosen more particularly from acrylic, methacrylic, crotonic, itaconic, maleic, fumaric acids as well as alkyl monoesters having from 1 to 4 carbon atoms of maleic or fumaric acids or anhydrides. Preferred basic comonomers are aminoethyl, butyl aminoethyl, N, N'-dimethylaminoethyl, N-tert-butylaminoethyl methacrylates. Particularly used are copolymers whose CTFA designation (4th Ed., 1991) is. Octyl acrylamide / acrylates / butylaminoethyl methacrylate copolymer such as the products sold under the name AMPHOMER or LOVOCRYL 47 by the company NATIONAL STARCH. (3) Crosslinked and partially or totally alkylated polyaminoamides which are derived from polyaminoamides of the general formula: wherein Ri represents a divalent radical derived from a saturated dicarboxylic acid, from an aliphatic mono- or dicarboxylic acid of ethylenic double bond, from an ester of a lower alkanol having from 1 to 6 carbon atoms of these acids or from a radical which is derived from the addition of one of any of said acids with a bis-primary or bis-secondary amine, and Z denotes a radical of a bis-primary, mono- or bis-secondary polyalkylene-polyamine and preferably represents : a) in the proportions of 60 to 100 mol%, the radical • NH- £ (CH2)? - (IV) - r where x = 2 and p = 2 or 3, or x = 3 and p = 2, this radical being derived from diethylenetriamine, from rietylentetraamine or from dipropylenetriamine; b) in the proportions of 0 to 40 mol% the radical (IV) indicated above, in which x = 2 and p = l and which is derived from ethylenediamine, or the radical derived from piperazine: ./ Y \ / c) in the proportions of 0 to 20 moles 1 the radical -NH- (CH;), - NH- which is derived from hexa-met ilendiamine, these polyaminoamines being crosslinked by addition of a bifunctional crosslinking agent selected from epihalohydrins, diepoxides, dianhydrides, bis-unsaturated derivatives, by means of 0.025 to 0.35 moles of crosslinking agent per amine group of the pliaminoamide and alkylated by the action of acrylic acid, chloroacetic acid or an alkanesul tone or its salts. Saturated carboxylic acids are preferably chosen from acids having from 6 to 10 carbon atoms such as adipic acid, 2, 2, 4-trimethoprim and 2,4,4-trimethyl-adipic acid, terephthalic acids. double ethylenic bond such as acrylic, methacrylic, itaconic acids. The alkanesulones used in alkylation are preferably propane or butanesulon, the salts of the alkylating agents are preferably the sodium or potassium salts. (4) Polymers that include zwitterionic motifs of the formula: wherein Ru designates a polymerizable unsaturated group such as an acrylate, methacrylate, acrylamide or methacrylamide group, and Z represents an integer from 1 to 3, R? and R13 represent a hydrogen atom, methyl, ethyl or propyl, R? and R represent a hydrogen atom or an alkyl radical such that the sum of the carbon atoms in R14 and R1 does not exceed 10. The polymers comprising such units may also comprise motifs derived from non-zwitterionic monomers such as acrylate. or the dimethyl or diethylaminoethyl methacrylate or the alkyl acrylates or methacrylates, the acrylamides or methacrylamides or the vinyl acetate. By way of example, mention may be made of the copolymer of methyl methacrylate / dimethylcarboxy, methylammonium and methyl methacrylate, such as the product sold under the name DIAFORMER Z301 by the company SANDOZ. (5) Polymers derived from chitosan comprising monomeric motifs that respond to the following formulas: the pattern D being present in portions comprised between 0 and 30. The pattern E is proportions comprised between 5 and 50% and the motif F in proportions comprised between 30 and 90%, it being understood that in this motif F, R? fi represents a radical of formula: ^ 18 R19 R-C- (O) -C wherein if q = 0, Ri7, R? "and Ri ?, identical or different, each represents a hydrogen atom, a methyl, hydroxyl, acetoxy or amino moiety, a monoalkylamine moiety or a dialkylamine moiety optionally interrupted by one (several nitrogen atoms and / or optionally substituted by one or more amine, hydroxyl, carboxyl, alkylthio, sulphonic groups, an alkylthio radical whose alkyl group carries an amino moiety, at least one of the radicals Rp, R? R? 5 in this case a hydrogen atom, or if q = l, Ri7, Ria and Ri? Each represent a hydrogen atom, as well as the salts formed by these compounds with bases or acids. (6) Derived polymers of the N-carboxyalkylation of chitosan such as N-carboxymethylchucoune or the N-carboxybutylkyntane sold under the name "EVALSAN" by the company JAN DEKKER. (7) Polymers corresponding to the general formula (VI) are described in the French patent 1, 400, 366: wherein R_ represents a hydrogen atom, a radical CH30, CH3CH_0, phenyl, R? designates hydrogen or a lower alkyl radical such as methyl, ethyl, R denotes hydrogen or a lower alkyl radical such as methyl, ethyl, R33 designates a lower alkyl radical such as methyl, ethyl or a radical corresponding to the formula: -R24 -N (R;:) _, R representing a group -CH_-CH-, -CH_-CH3-CH_-, -CH -CH (CH3) -, R having the meanings mentioned above, as well as the higher homologs of these radicals and containing up to 6 carbon atoms. (8) Amphoteric polymers of the type -D-X-D-X selected from: (a) polymers obtained by the action of chloroacetic acid or sodium chloroacetate on the compounds that include at least one motif of the formula: -D-X-D-X-D-: vn where D designates a radical \ / and X designates the symbol E or Et, E or E 'identical or different, denote a bivalent radical which is a straight or branched chain alkylene radical including up to 7 carbon atoms in the main chain unsubstituted or substituted by hydroxyl groups and which may further include oxygen, nitrogen, sulfur atoms, 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, alkene sheet, hydroxyl, benzylamine, amine oxide, quaternary ammonium, amide, imide, alcohol, ester groups and / or urethane; b) Polymers of the formula: -D-X-D-X-; vn where D designates a radical \ / and X designates the symbol E or E 'and at least once E'; having E the meaning indicated above and E 'is a bivalent radical which is a straight or branched chain alkylene radical having up to 7 carbon atoms in the main chain, substituted or not by one or more hydroxyl radicals and including "one or more nitrogen atoms, the nitrogen atom being substituted by an alkyl chain optionally interrupted by an oxygen atom and which necessarily includes one or more carboxyl functions or a or various hydroxyl functions and betainized by reaction with chloroacetic acid or chloroacetate soda (9) alkyl (C1-C5) vinyl ether / -anhydro maleic copolymers partially modified by semiamidification with an N, N-dialkylamino-alkylamine such as N, N-dimethylaminopropylamine or by semi-esterification with an N, N-dialkanolamine These copolymers can also include other vinyl comonomers such as vinylcaprolactam Particularly preferred amphoteric polymers according to the invention are those of family (3) such as copolymers whose CTFA name is octylacrylamide / acrylates / -butylaminoethylmethacrylate copolymer such as the products sold under the name AMPHOMER or LOVOCRYL 47 by the company NATIONAL STARCH. The nonionic fixing polymers which can be used according to the present invention are selected, for example from: - the poly ß alanines described more particularly in French Patent No. 2508795; - the polyalkyloxazolines such as the polyethyloxazolines proposed by the Company DOW CHEMICAL under the names PEOX 50,000, PEOX 200,000 and PEOX 500,000; - the vinyl acetate homopolymers such as the product proposed under the name of APPRETAN EM by the Company HOECHST or the product proposed under the name of RHODOPAS A 012 by the Company RHONE POULENC; the copolymers of vinyl acetate and acrylic ester such as the product proposed under the name RHODOPAS AD 310 of RHONE POULENC; - vinyl acetate and ethylene copolymers such as the proposed product under the name of APPRETAN TV by the HOECHST Society; copolymers of vinyl acetate and of maleic ester for example of dibutyl maleate such as the product proposed under the name of APPRETAN MB EXTRA by the Company HOECHST; - the vinyl chloride homopolymers such as, the products proposed under the names of GEON 460X45, GEON 460x46 and GEON 577 by the GOODRICH Company; - polyethylene waxes such as the products proposed under the names AQUACER 513 and AQUACER 533 by the BYK CERA Company; polyethylene / polytetraf luoroethylene waxes such as the products proposed under the names DREWAX D-3750 by the company DREW AMEROID and WAX DISPERSION WD-1077 by the R.T.
NEWEY; the polyethylene and maleic anhydride copolymers; the homopolymers of alkyl acrylates and the homopolymers of alkyl methacrylates such as the product proposed under the name MICROPEARL RQ 750 by the company MATSUMOTO or the product proposed under the name LUHYDRAN A 848 S by the company BASF; copolymers of acrylic esters such as for example the copolymers of alkyl acrylates and alkyl methacrylates such as the products proposed by the company ROHM & HAAS under the names PRIMAL ACZ 61 k AND EUDRAGIT IN 30 D, _ by the company BASF under the names ACRONAL 601, LUHYDRAW LR 8833 or 8845, by the Company HOECHST under the names APPRETAN N 9213 or N9212; - the copolymers of acrylonitrile and of a nonionic monomer selected for example between butadiene and alkyl (meth) acrylates; the products proposed under the names NIPOL LX 531 B by the company NIPPON ZEON or those proposed under the name CJ 0601 B by the company ROHM & HAAS; styrene homopolymers such as the product RHODOPAS 5051 proposed by the Company RHONE POULENC; - copolymers of styrene and of alkyl (meth) acrylate such as the products MOWILITH LDM 6911, MOWILITH DM 611 and MOWILITH LDM 6070 proposed by the Company HOECHST, the products RHODOPAS SD 215 and RHODOPAS SD 910 proposed by the company RHONE POULENC, the URAMUL SC 70 product proposed by the DSM Company; copolymers of styrene, alkyl methacrylate and alkyl acrylate such as the product DAITISOL SPA proposed by the company WACKHERR; the copolymers of styrene and of butadiene such as the products RHODOPAS SB 153 and RHODOPAS SB 012 proposed by the company RHONE POULENC; - styrene, butadiene and vinylpyridine copolymers such as GOODRITE SB products VINYLPYRIDINE 2528X10 and GOODRITE SB VINYLPYRIDINE 2508 proposed by the GOODRICH Company; polyurethanes such as the products proposed under the names ACRYSOL RM 1020 or ACRYSOL RM 2020 by the company ROHM & HAAS, URAFLEX XP 401 UZ, URAFLEX XP 402 UZ products by the DSM RESINS Company; - the alkyl acrylate and urethane copolymers such as the product 8538-33 by the company NATIONAL STARCH; - the polyamides such as the product ESTAPOR LO 11 proposed by the company RHONE POULENC. The alkyl radicals of the nonionic polymers preferably have from 1 to 6 carbon atoms. According to the present invention, the fixing polymers are preferably anionic polymers. The fixing polymer (s) are, for example, present in concentrations comprised between 0.01 and 20% by weight relative to the total weight of the composition, preferably between 0.1 and 15% by weight and more particularly from 0.5 to 10% by weight. The cosmetically or dermatologically acceptable medium is preferably constituted by water or a mixture of water and cosmetically acceptable solvents such as monoalcohols, polyalcohols, glycol ethers or fatty acid esters, which can be used alone or as a mixture. Mention may be made more particularly of lower alcohols such as ethanol, isopropanol, polyalcohols such as diethylene glycol, glycol ethers, glycol alkyl ethers or diethylene glycol. The composition of the invention can also contain at least one additive selected from thickeners, fatty acid esters, esters of fatty acids and glycerol, silicones, perfumes, preservatives, sunscreens, proteins, vitamins. , polymers, vegetable, animal, mineral or synthetic oils and any other additive classically used in the cosmetic field. Preferably, the composition contains a silicone such as an oil, a resin, a wax or a silicone gum. The compositions according to the invention can also contain one or more surfactants. The nature and concentration of these surfactants are chosen by the person skilled in the art in order not to confer a detergent character on the composition. Preferably, the composition contains less than 4% by weight of anionic and / or amphoteric and / or zwitterionic detergent surfactants. These additives are present in the composition according to the invention in proportions that can range between 0 and 20? by weight in relation to the total weight of the composition. The precise amount of each additive is a function of its nature and is easily determined by the person skilled in the art. Of course, the person skilled in the art will take care in choosing the optional compound (s) to be added to the composition according to the invention in such a way that the advantageous properties intrinsically related to the composition according to the invention are not substantially altered by the addition considered. . In particular, the compositions according to the invention preferably comprise less than 10% by weight relative to the total weight of the composition of fatty substances such as waxes, oils, paraffin, fatty acid esters of Cs-C3p . Thus, the keratin fibers treated with the compositions according to the invention do not have a touch, nor a fatty aspect and the fixing power of the composition is not diminished. Preferably, the composition according to the invention does not contain or substantially cationic surfactant. The compositions according to the invention can be in the form of gel, milk, cream, dispersion, more or less thick lotion or foam.
The compositions according to the invention are used more particularly as non-rinsed products, particularly for the maintenance of styling, shaping or combing of the hair. They are more particularly marking lotions, lotions for brush marking, fixing compositions (lacquers) and styling. The lotions can be conditioned in various forms, particularly in vaporizers, pump bottles or aerosol containers for the purpose of ensuring an application of the composition in vaporized form or in the form of a foam. Such forms of conditioning are indicated, for example, when it is desired to obtain a spray, a lacquer or a foam for fixing or treating the hair. When the composition according to the invention is packaged in the form of an aerosol in order to obtain a lacquer or an aerosol foam, it comprises at least one propellant which can be chosen from volatile hydrocarbons such as n-butane, propane, isobutane, pentane, a chlorinated and / or fluorinated hydrocarbon and their mixtures. It is also possible to use carbon dioxide, nitrous oxide, dimethyl ether, nitrogen, compressed air and mixtures thereof as the propellant. The subject of the invention is also a non-therapeutic process for treating keratinous fibers such as human hair, which consists in applying a composition to them as defined above. The invention will now be illustrated more fully with the help of the fwing examples which will not be considered as limiting to the described embodiments. (In what fws MA means Active Matter).
EXAMPLE 1 A brush marking lotion with the fwing composition was prepared: - N-oleoyldihydroesf ingosine (ceramide) 0.02 g - Copolymer methyl vinyl ether / maleic esterified monohydric anhydride sold by the ISP Company under the name GANTREZ ES 425 (fixing polymer) 1 g MA - Ethanol 50 g - Water csp 100 g The composition was prepared at the time of use by mixing a part A containing the cetamide and 10 g of ethanol and a part B containing the polymer, water and the rest of ethanol. The composition was applied to the washed and drained hair, and then brush marking was carried out. The dry hair is smooth and soft and has good combing properties. The hair resists well to the mark. Brush it.
EXAMPLE 2 A brush marking lotion with the fwing composition was prepared: - N-oleoidihydrosphingosine (ceramide) 0.02 g - Copolymer of methacryloyl ether and 1 N, N-dimethylcarboximet ilbetaine and butyl methacrylate sold in 30% solution of MA in ethanol under the name of DIAFORMER Z301 by the company SANDOZ 1 g MA - Ethanol 50 g - Demineralized water csp 100 g The composition was prepared and applied in the same way as in Example 1. The dry hair is smooth and smooth and has good combing properties. The hair resists well to the marked with brush.
EXAMPLE 3 A brush marking lotion with the fwing composition was prepared: - N-oilyldihydrogens f ingosine (ceramide) 0.02 9 - Copolymer methyl vinyl ether / mono esterified maleic anhydride expired by the ISP Company under the name GANTREZ ES 425 1 g MA - Hydroxyethylcellulose and diallyl chloride ammonium copolymer sold under the trade name CELQUAT L200 by the company NATIONAL STARCH 0.5 g - Ethanol 50 g - Demineralized water csp 100 g The composition was prepared and applied in the same manner as in Example 1. The dry hair is smooth and smooth and has good combing properties. The hair resists well to the marked with brush.
EXAMPLE 4 A brush marking lotion with the fwing composition was prepared: - N-oleoidihydrosphingosine (ceramide) 0.02 g - Terpolymer vinyl acetate / crotonic acid / pi liet ilenglicol under the name ARISTOFLEX A by the company BASF 1 g MA - Amodimet icona sold under the name DC 929 by the company DOW CORNING at 35% of MA 0.5 g MA - Ethanol 17.2 g - Demineralized water csp 100 g The composition was prepared and applied in the same manner as in Example 1. The dry hair is smooth and smooth and has good combing properties. The hair resists well to the marked with brush.
COMPARATIVE ESSAYS Four compositions A, 2A, 3A and 4A were prepared with respectively the same composition as those of Examples 1, 2, 3 and 4 with the exception of the ceramide which was deleted.
The mass of hair recovered was compared with a brush-on-wig marking for each pair of compositions. The higher the mass of broken hair, the less the composition protects the hair. Each half wig was previously washed with 6 ml of standard shampoo. After rinsing and draining with a sponge napkin, 2.4 ml of the first product was applied on a half wig with the help of a pipette. A brush marking was carried out. Then, 2.4 ml of the second, product was applied on the second half wig and brush marking was carried out. The brush marking was done by an experienced hairdresser with the help of a Centauro 3940 brush and a Mega-sprint bi-turbo 1500 hair dryer (regulation 2 and 2). After each brush marking, the hair remaining in the brush was recovered and weighed and the hair mass was compared for each of the compositions tested. The results are indicated in the table given below: For each pair of compositions (1.1A), (2.2A), (3.3A), (4.4A), it is observed that the mass of hair recovered in the brush after marking has clearly decreased for the compositions according to the invention 1, 2, 3 and 4 containing the ceramide. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention. Having described the invention as above, property is claimed as contained in the following:

Claims (21)

1. Non-detergent cosmetic composition, intended for the treatment of keratin fibers such as hair, characterized in that it contains in a cosmetically acceptable medium at least one anionic, nonionic, zwitterionic or amphoteric fixing polymer, and at least one ceramide-type compound, said vinylpyrrolidone polymer and / or cationic polymer compositions comprising primary, secondary, tertiary or quaternary ammonium groups in a main chain and said cationic polymer having viscosity of 1% by weight of active material not containing said compositions in water less than 15 mPa.s.
2. Composition according to claim 1, characterized in that the compound of the ceramide type corresponds to the general formula (I): wherein: R: designates: - either a hydrocarbon radical, linear or branched, saturated or unsaturated, of C5-C5-J, this radial being able to be replaced by one or several hydroxyl groups optionally esterified by an acid RcCOOH, where R7 is a hydrocarbon radical, saturated or unsaturated, linear or branched, optionally mono- or polyhydroxylated, of C? -C35, the hydroxyl (s) of the radical R being capable of being esterified by a saturated or unsaturated fatty acid, linear or branched, optionally mono- or polyhydroxylated, of C? -C3S; - either a radical R "- (NR-CO) -R ', R designates a hydrogen atom or a hydrocarbon radical C? -C_? mono or polyhydroxy, preferably monohydroxy, R and R" are hydrocarbon radicals whose sum of the carbon atoms is between 9 and 30, where R 'is a divalent radical; or a radical Ra-0-CO- (CH.) μ, R "denotes a hydrocarbon radical of C? -C _,., p is an integer ranging from 1 to 12; R_ designates a hydrogen atom or a radical (glycosyl) r / (galactosyl) p, sulfo-galactosyl, a radical fos for i let ilamine or fos forilet ilamonium, in which n is an integer ranging from 1 to 4 and m is an integer that varies from 1 to 8; R3 designates a hydrogen atom or a hydrocarbon radical of C? -C33, saturated or unsaturated, hydroxylated or not, the hydroxyl (s) being capable of being esterified by a mineral acid or an acid R7COOH, R7 having the same meanings as above, the or the hydroxyls are etherified by a radical (glycosyl) n, (galactosyl), sulfogalactosyl, fos-forylethylamine or phosphoryl-ammonium, where R3 can also be substituted by one or several C1-C14alkyl radicals; R 4 denotes a hydrogen atom, a methyl, ethyl radical, a C 3 -C 2 hydrocarbon radical, saturated or unsaturated, linear or branched, optionally hydroxylated or a radical -CH-CH 0 H -CH-0-R 6 in which R denotes a hydrocarbon radical of C 1 -C 6 or a radical R 4 -O-CO- (CH:),:, R 1 designates a hydrocarbon radical of C 1 -C 1, p is an integer ranging from 1 to 12; R5 denotes a hydrogen atom or a C1-C33 hydrocarbon radical saturated or unsaturated, linear or branched, optionally mono or polyhydroxylated, the hydroxyl (s) being able to be esterified by a radical (glycosyl) n, (galactosyl) m, sul fogalactosi , phosphoryl ilamine or phosphorylethyl ammonium, with the proviso that when R and R5 designate hydrogen or when R3 designates hydrogen and R5 designates methyl then R4 does not designate a hydrogen atom, a methyl or ethyl radical.
3. Composition according to any of the preceding claims, characterized in that the compound of ceramide type is chosen from the group consisting of: - N-linoleoyl dihydrosphingosine, - N-oleoidihydroes fingosine, - N-palmi toildihydroes fingos ina, - la N-stearoyldihydrosphingosine, - N-behenoyldihydroes phytosine, - N-2-hydroxyipalmi toildihydroesf ingosine, - N-stearoyl phytosphingosine, - N-palmitamidohexadecanediol, or mixtures of these compounds.
4. Composition according to any of claims 1 or 2, characterized in that the compound of ceramide type is chosen from bis- (N-hydroxyethyl N-cet il) malonamide, N- (2-hydroxyethyl) -N- (3- cet i loxi-2-hydroxypropyl 1) cetyl acid amide) and N-docosanoyl N-methyl-D-glucamine.
5. Composition according to one of the preceding claims, characterized in that the anionic fixing polymer is chosen from: - polymers including carboxylic units derived from unsaturated mono or dicarboxylic carboxylic monomers of the formula: wherein n is an integer from 0 to 10, A designates a methylene group, optionally attached to the carbon atom of the unsaturated group or to the next methylene group when n is greater than 1 by mediating a heteroatom such as oxygen or sulfur , R- designates a hydrogen atom, a phenyl or benzyl group, R, denotes a hydrogen atom, a lower alkyl or carboxyl group, R3 designates a hydrogen atom, a lower alkyl group, a -CH.-COOH group, or a phenyl or benzyl group; - polymers comprising motifs derived from sulfonic acid, such as vinyl sulphonic, styrenesulfonic, acrylamido alkylsulfonic motifs.
6. Composition according to claim 5, characterized in that the anionic fixing polymer is chosen from: A) the homo- or copolymers of acrylic or methacrylic acid or their salts, the copolymers of acrylic acid and of acrylamide or its salts, the sodium salts of polyhydroxycarboxylic acids; B) copolymers of acrylic or methacrylic acids with a monoether monomer such as ethylene, styrene, vinyl esters, esters of acrylic or methacrylic acid, optionally grafted onto a polyalkylene glycol such as polyethylene glycol and optionally crosslinked; such copolymers including an optionally N-alkylated and / or hydroxyalkyl acrylamide, the copolymers of acrylic acid and C1-C alkyl methacrylate; C) copolymers derived from crotonic acid such as those which include vinyl acetate or propionate in their chain and optionally other monomers such as allyl or metalyl esters, vinyl ether or vinyl ester of a linear or branched saturated carboxylic acid of long hydrocarbon chain such as those that include at least 5 carbon atoms, these polymers may eventually be grafted and crosslinked D) polymers derived from maleic, fumaric, itaconic acids or anhydrides with vinyl esters, vinyl ethers, vinyl halides, phenylvinyl derivatives, acrylic acid and their esters; copolymers of maleic, citraconic and itaconic anhydrides and of an allyl or methallyl ester optionally including an acrylamide group, methacrylamide, an α-olefin, acrylic or methacrylic esters, acrylic or methacrylic acids in their chain, the anhydride functions are monoes teri f ican or monoamidi f ican; E) polyacrylamides including carboxylate groups.
7. Composition according to claim 6, characterized in that the anionic fixing polymer is chosen from: acrylic acid copolymers such as the terpolymer acrylic acid / ethyl acrylate / N-tert-butylacrylamide; - copolymers derived from crotonic acid such as the terpolymers vinyl acetate / tert-butyl benzoate / crotonic acid and the terpolymers crotonic acid / vinyl acetate / vinyl neododecanoate; polymers derived from acids or from maleic, fumaric, itaconic anhydrides with vinyl esters, vinyl ethers, vinyl halides, phenyl vinyl derivatives, acrylic acid and their esters such as methyl vinyl ether / maleic esterified mono anhydride copolymers; the copolymers of methacrylic acid and methyl methacrylate; - the copolymer of methacrylic acid and ethyl acrylate; - the vinyl acetate / crotonic acid copolymer; - the vinyl acetate / crotonic acid / polyethylene glycol terpolymer.
8. Composition according to any of claims 1 to 4, characterized in that the amphoteric fixing polymer is chosen from among the polymers including derived motifs: a) from at least one monomer selected from acrylamides or methacrylamides substituted on nitrogen by a radical alkyl, b) of at least one acid comonomer containing one or more reactive carboxylic groups, and c) at least one basic comonomer such as esters with primary, secondary, tertiary and quaternary amine substituents of the acrylic and methacrylic acids and the quaternization product of dimethylaminoethyl methacrylate with sulfate, dimethyl or diethyl.
9. Composition according to claim 8, characterized in that the amphoteric fixing polymer is chosen from copolymers whose CTFA name is octyl acrylamide / acrylates / -but i laminoet i lmetacri lato copolymer.
10. Composition according to any of claims 1 to 4, characterized in that the nonionic fixing polymer is chosen from: - the poly ß alanines; - polyalkyloxazolines; - vinyl acetate homopolymers; the copolymers of vinyl acetate and of acrylic ester; - the vinyl acetate and ethylene copolymers; - copolymers of vinyl acetate and maleic ester; - vinyl chloride homopolymers; - polyethylene waxes; - polyethylene / poly tetrafluoroethylene waxes; - polyethylene and maleic anhydride copolymers; the homopolymers of alkyl acrylates and the homopolymers of alkyl methacrylates; copolymers of acrylic esters, such as, for example, copolymers of alkyl acrylates and alkyl methacrylates; - the copolymers of acrylonitrile and of a nonionic monomer selected for example between butadiene and alkyl (meth) acrylates; - styrene homopolymers; - the copolymers of styrene and of alkyl (meth) acrylate; copolymers of styrene, alkyl methacrylate and alkyl acrylate; - styrene and butadiene copolymers; styrene, butadiene and vinylpyridine copolymers; the alkyl acrylate and urethane copolymers.
11. Composition according to any of the preceding claims, characterized in that the ceramide-type compound or compounds are present in concentrations ranging between 0.0001 and 20% by weight with respect to the total weight of the composition and preferably from 0.001 to 10% in weight and more preferably between 0.005 and 3% by weight.
12. Composition according to any of the preceding claims, characterized in that the fixing polymer or polymers are used in an amount ranging between 0.01 and 20% by weight with respect to the total weight of the composition, preferably from 0.1 to 15% by weight and more particularly from 0.5 to 10% by weight.
13. Composition according to any of the preceding claims, characterized in that it also contains at least one additive selected from the group consisting of thickeners, fatty acid esters, esters of fatty acids and glycerol, silicones, surfactants, perfumes , preservatives, sunscreens, proteins, vitamins, polymers, vegetable, animal, mineral or synthetic oils and any other additive classically used in the cosmetic field.
14. Composition according to any one of the preceding claims, characterized in that the cosmetically acceptable medium is constituted by water or a mixture of water and by at least one cosmetically acceptable solvent. fen.
Composition according to claim 14, characterized in that the cosmetically acceptable solvents are chosen from the group consisting of monoalcohols, polyalcohols, glycol ethers, fatty acid esters and their mixtures.
16. Composition according to any of the preceding claims, characterized in that it is in the form of gel, milk, cream, dispersion, more or less thick lotion or foam.
17. Composition according to any of the preceding claims, characterized in that it is a product for combing, maintaining the styling and shaping.
18. Composition according to any of the preceding claims, characterized in that it is provided in the form of a vaporizer, a pump bottle or in an aerosol container with a view to obtaining a spray, a lacquer or a foam.
19. Composition according to any one of the preceding claims, characterized in that the fixing polymer is solubilized in the cosmetically acceptable medium or is used in the form of an aqueous dispersion of insoluble solid particles.
20. Non-therapeutic process for the treatment of keratin materials, in particular of the hair, characterized in that it consists of applying a composition according to any of the preceding claims on said materials.
21. Use of a composition according to any of claims 1 to 19, to protect the hair during marking by brush.
MX9802962A 1995-10-23 1996-10-22 Keratin fibre treatment composition including at least one setting polymer and at least one ceramide-type compound, and methods MX202859B (en)

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FR95/12448 1995-10-23
FR9512448A FR2740034B1 (en) 1995-10-23 1995-10-23 COMPOSITION FOR THE TREATMENT OF KERATINIC MATERIALS COMPRISING AT LEAST ONE FIXING POLYMER AND AT LEAST ONE CERAMID-LIKE COMPOUND AND METHODS
FR9512448 1995-10-23
PCT/FR1996/001652 WO1997015274A1 (en) 1995-10-23 1996-10-22 Keratin fibre treatment composition including at least one setting polymer and at least one ceramide-type compound, and methods

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JP4173944B2 (en) 2000-06-29 2008-10-29 株式会社紀文フードケミファ Glycosphingolipid
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FR2853832B1 (en) * 2003-04-16 2006-08-11 Oreal HAIR TREATMENT PROCESS AND USE OF THE METHOD FOR THE SMOOTHING OF HAIR
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EP2571493A1 (en) * 2010-05-21 2013-03-27 Basf Se Preparations of biologically active substances with enlarged surface area based on amphiphilic copolymers
FR2991875B1 (en) * 2012-06-15 2015-10-02 Oreal COMPOSITION COMPRISING A DYARBOXYLIC PYRIDINE ACID ESTER AND A FIXING POLYMER, METHOD AND USE
KR101586694B1 (en) 2014-05-20 2016-01-19 주식회사 에스에프에이 Cassette transfer system
CN104523540A (en) * 2014-12-01 2015-04-22 唯美度科技(北京)有限公司 Hair conditioner having hair restoration function and preparation method thereof
US10143644B2 (en) * 2015-08-31 2018-12-04 L'oreal Composition comprising an anionic-ampholytic polymer association
WO2022020332A1 (en) 2020-07-21 2022-01-27 Chembeau LLC Diester cosmetic formulations and uses thereof
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