EP1237528A1 - Eine zusammensetzung zur entfärbung oder dauerhaften verförmung von keratinischen fasern, die ein verdickungspolymer mit einer aminoplastether hauptkette enthält - Google Patents

Eine zusammensetzung zur entfärbung oder dauerhaften verförmung von keratinischen fasern, die ein verdickungspolymer mit einer aminoplastether hauptkette enthält

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Publication number
EP1237528A1
EP1237528A1 EP00979710A EP00979710A EP1237528A1 EP 1237528 A1 EP1237528 A1 EP 1237528A1 EP 00979710 A EP00979710 A EP 00979710A EP 00979710 A EP00979710 A EP 00979710A EP 1237528 A1 EP1237528 A1 EP 1237528A1
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EP
European Patent Office
Prior art keywords
composition
composition according
aminoplast
polymer
chosen
Prior art date
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Application number
EP00979710A
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English (en)
French (fr)
Inventor
Frédéric Legrand
Delphine Allard
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LOreal SA
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LOreal SA
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Publication of EP1237528A1 publication Critical patent/EP1237528A1/de
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365Hydroxycarboxylic acids; Ketocarboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/447Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67Vitamins
    • A61K8/676Ascorbic acid, i.e. vitamin C
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/731Cellulose; Quaternized cellulose derivatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86Polyethers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/04Preparations for permanent waving or straightening the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/08Preparations for bleaching the hair

Definitions

  • the present invention relates to a composition for bleaching or permanently deforming keratin fibers and in particular human keratin fibers such as the hair, comprising at least one reducing agent and at least one thickening polymer with an aminoplast-ether skeleton.
  • bleaching compositions containing one or more oxidizing agents It is known to bleach keratin fibers and in particular human hair, with bleaching compositions containing one or more oxidizing agents.
  • oxidizing agents conventionally used, mention may be made of hydrogen peroxide or of compounds capable of producing hydrogen peroxide by hydrolysis, such as urea peroxide or persalts such as perborates, percarbonates and persulfates, hydrogen peroxide and persulfates being particularly preferred.
  • reducing agents preferably used in the context of permanent deformation of the hair are thiols such as thioglycolic acid, its salts and esters, thiolactic acid and its salts, cysteine or cysteamine, and sulfites.
  • compositions intended for bleaching the hair using reducing agents are mainly in the form of ready-to-use compositions consisting of anhydrous products (powders or creams) containing the reducing agent (s) which are mixed at the time. use with an aqueous composition optionally containing a pH agent.
  • the bleaching compositions are also in the form of aqueous ready-to-use compositions containing the reducing agent (s) at the appropriate pH.
  • the reducing compositions for the permanent deformation of the hair are generally in the form of aqueous compositions ready for use or in the form of anhydrous powdery or liquid compositions which are mixed at the time of use with an aqueous composition at the appropriate pH.
  • the Applicant has found that the thickening systems mentioned above did not make it possible to obtain sufficiently powerful and homogeneous discolourations or permanent deformations. Furthermore, it also found that the compositions for bleaching or permanent deformation of the hair, ready to use, containing the reducing agent or agents, and in addition the thickening systems of the prior art did not allow a sufficiently precise application. without drips or drops in viscosity over time.
  • compositions for bleaching or permanent deformation of the hair containing at least one reducing agent ready to use, which do not flow and therefore remain well located at the point of application, and which also make it possible to obtain permanent and powerful and homogeneous discolourations or deformations, if an effective amount of a polymer with an aminoplast-ether skeleton is introduced into the composition.
  • the present invention thus relates to a ready-to-use composition for bleaching or permanent deformation of keratin fibers, in particular human keratin fibers, such as the hair, comprising, in a medium suitable for bleaching or permanent deformation , at least one reducing agent, which is characterized in that it also contains at least one polymer with an aminoplast-ether backbone.
  • ready-to-use composition is meant, within the meaning of the invention, the composition intended to be applied as it is to keratin fibers, ie it can be stored as it is before use or result from extemporaneous mixture of two or more compositions.
  • the polymer with an aminoplast-ether skeleton may be present in one or more or in all of the mixed compositions.
  • the polymer with an aminoplast-ether backbone can be present in an anhydrous composition in the form of preferably powdery powder or cream and / or in one or more aqueous compositions.
  • the polymer or polymers with an aminoplast-ether skeleton are present in at least one aqueous composition which is mixed with moment of use with a composition either aqueous or anhydrous in the form of powder or cream and containing at least one reducing agent.
  • a composition either aqueous or anhydrous in the form of powder or cream and containing at least one reducing agent.
  • Another preferred form of the invention is a unique composition containing the reducing agent (s) and the polymer (s) with an aminoplast-ether skeleton.
  • Another object targeted by the present invention is an anhydrous composition containing at least one reducing agent and at least one polymer with an aminoplast-ether skeleton, said composition being intended to be diluted before application to the fibers.
  • the invention also relates to a bleaching process or a process for permanent deformation of keratin fibers, and in particular of human keratin fibers such as the hair using the bleaching or permanent deformation composition ready for use as described according to invention, the application of said composition can be followed, in the case of permanent deformation, by the application, optionally after rinsing, of an oxidizing composition.
  • the invention also relates to bleaching devices or "Kits" for packaging containing such a ready-to-use composition.
  • a device with two compartments comprises a first compartment containing at least one powder or an anhydrous cream or an aqueous composition, and the second compartment an aqueous composition, at least one of the two compartments containing at least one reducing agent and the at least one of the two compartments containing at least one polymer with an aminoplast-ether skeleton.
  • aminoplast-ether is understood within the meaning of the present invention, any product resulting from the condensation of an aldehyde with an amine or an amide.
  • aminoplast-ether is also meant in the sense of the present invention, any structural unit formed of an aminoplast residue and a divalent hydrocarbon residue linked to the aminoplast residue by an ether bond.
  • polymers with an aminoplast-ether skeleton used according to the invention are preferably chosen from those containing at least one unit of structure (I) below:
  • -AMP is an aminoplast residue with alkylene units
  • -R denotes a hydrogen atom, a C1C4 alkyl radical or an acyl radical
  • -RO1 is a divalent alkyleneoxy residue
  • -p denotes a positive integer, the OR group or groups being linked to the alkylene units of the AMP residue.
  • the polymers with an aminoplast-ether skeleton are chosen from those containing at least one unit of structure (II) as follows:
  • - RO2 is a hydrophobic group different from RO linked to AMP via a heteroatom and comprising at least two carbon atoms, and, -q is a positive integer.
  • the polymers of the invention have the following formulas (III) and (III) bis:
  • R3 identical or different, represent a terminal group which can denote a hydrogen atom, a group RO-j H, a group RO2H, a group AMP (OR) p or any monofunctional group such as alkyl, cycloalkyl, aryl, aralkyl, alkylaryl , alkyloxyalkyle, aryloxyalkyle, cycloalkoxyalkyle, a being a number greater than 1 and preferably greater than 2.
  • aminoplast residues carrying their OR groups integrated into the polymers of the invention can be chosen without limitation from the following structures (IV) to (XV):
  • R1 denotes C1C4 alkyl
  • y is a number at least equal to 2
  • x denotes 0 or 1.
  • aminoplast residue (s) carrying their OR groups are chosen from those of structure (XVI) below:
  • R, p, and x have the same meanings as before.
  • the divalent alkyleneoxy residues are preferably those corresponding to the diols of general formula (XVII) below: HO- (ZO) y- (Z1 (Z2O) w) t- (Z'O) y'-Z3OH (XVII), y and y 'being numbers ranging from 0 to 1000, t and w being numbers ranging from 0 to 10,
  • Z, Z ', Z2 and Z3 are C2C4 alkylene radicals and preferably radicals
  • Z4 -CH2-CH (Z4) - and -CH2-CH (Z4) -CH2-, Z1 being a linear or cyclic radical, branched or not, aromatic or not, comprising or not one or more heteroatoms and having from 1 to 40 carbon atoms,
  • Z4 denoting a hydrogen atom or a C1C4 alkyl radical or a C1C3 acyl radical, it being understood that at least one of the radicals Z4 of the radicals Z, Z ', Z2 and Z3 is different from acyl.
  • Z4 denotes a hydrogen atom or a methyl radical.
  • polymers with an aminoplast-ether skeleton of formula (I) mention may in particular be made of the products PURE-THIX L [PEG-180 / Octoxynol-40 / TMMG Copolymer (INCI name)], PURE-THIX M [PEG-180 / Laureth-50 / TMMG Copolymer (INCI name)], and PURE-THIX HH [Polyether-1 (INCI name)] sold by the company SUD-CHEMIE.
  • the polymers with an aminoplast-ether skeleton are preferably used in an amount which can vary from approximately 0.01 to 10% by weight of the total weight of the discoloration or permanent deformation composition ready for use. More preferably, this amount varies from about 0.1 to 5% by weight.
  • the reducing agents which can be used according to the invention are preferably chosen from thiols such as cysteine, thioglycolic acid, thiolactic acid, their salts and their esters, cysteamine and its salts or sulphites.
  • thiols such as cysteine, thioglycolic acid, thiolactic acid, their salts and their esters, cysteamine and its salts or sulphites.
  • reducers are used in said ready-to-use compositions in concentrations of between 0.1 and 30% approximately, preferably between 0.5 and 20% by weight, by adding to the total weight of the composition.
  • compositions according to the invention may also contain, at least one cationic or amphoteric substantive polymer.
  • cationic polymer designates any polymer containing cationic groups and / or groups which can be ionized into cationic groups.
  • the cationic polymers which can be used in accordance with the present invention can be chosen from all those already known per se as improving the cosmetic properties of the hair, namely in particular those described in patent application EP-A-337 354 and in French patents FR- 2,270,846, 2,383,660, 2,598,611, 2,470,596 and 2,519,863.
  • the preferred cationic polymers are chosen from those which contain units comprising primary, secondary, tertiary and / or quaternary amine groups which can either be part of the main polymer chain or be carried by a lateral substituent directly connected thereto.
  • the cationic polymers used generally have a number average molecular mass of between 500 and 5.10 ° approximately, and preferably between 10 3 and 3.10 6 approximately.
  • cationic polymers mention may more particularly be made of polymers of the polyamine, polyaminoamide and quaternary polyammonium type. These are known products. They are described in particular in French patents 2,505,348 or 2,542,997. Among the said polymers, there may be mentioned:
  • R3 identical or different, denote a hydrogen atom or a CH3 radical
  • A identical or different, represent an alkyl group, linear or branched, from 1 to 6 carbon atoms, preferably 2 or 3 carbon atoms or a hydroxyalkyl group from 1 to 4 carbon atoms;
  • R-1 and R2 identical or different, represent hydrogen or an alkyl group having from 1 to 6 carbon atoms and 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 polymers of family (1) can also contain one or more units deriving from comonomers which can be chosen from the family of acrylamides, methacrylamides, diacetones, acrylamides, acrylamides and methacrylamides substituted on nitrogen by lower alkyls (C1-C4) , acrylic or methacrylic acids or their esters, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, vinyl esters.
  • comonomers can be chosen from the family of acrylamides, methacrylamides, diacetones, acrylamides, acrylamides and methacrylamides substituted on nitrogen by lower alkyls (C1-C4) , acrylic or methacrylic acids or their esters, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, vinyl esters.
  • Cationic cellulose derivatives such as cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer, and described in particular in US Pat. No. 4,131,576, such as hydroxyalkyl celluloses, such as hydroxymethyl- , hydroxyethyl- or hydroxypropyl celluloses grafted in particular with a methacryloylethyl salt trimethylammonium, methacryimidopropyl trimethylammonium, dimethyl-diallylammonium.
  • cationic polysaccharides described more particularly in US patents 3,589,578 and 4,031,307 such as guar gums containing cationic trialkylammonium groups.
  • Guar gums modified with a salt (eg chloride) of 2,3-epoxypropyl trimethylammonium are used, for example.
  • Such products are marketed in particular under the trade names of JAGUAR C13 S, JAGUAR C 15, JAGUAR C 17 or JAGUAR C162 by the company MEYHALL.
  • 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-halide of alkyl or also with an oligomer resulting from the reaction of a bifunctional compound reactive with a bis-halohydrin, a bis-azetidinium, a bis-haloacyldiamine, an alkyl bis-halide, d 'an epilhalohydrin, a diepoxide or a bis-unsaturated derivative; the crosslinking agent being used in proportions ranging from 0.025 to 0.35 mol per amino group of the polyaminoamide; these polyaminoamides
  • Polyaminoamide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids followed by alkylation by bifunctional agents Mention may be made, for example, of the adipic acid-diacoylaminohydroxyalkoyldialoylene triamine polymers in which the alkyl radical contains from 1 to 4 carbon atoms and preferably denotes methyl, ethyl, propyl. Such polymers are described in particular in French patent 1,583,363.
  • adipic acid / dimethylaminohydroxypropyl / diethylene triamine polymers sold under the name "Cartaretine F, F4 or F8" by the company Sandoz.
  • the molar ratio between the polyalkylene polylamine and the dicarboxylic acid being between 0.8: 1 and 1.4: 1; the resulting polyaminoamide being reacted with epichlorohydrin in a molar ratio of epichlorohydrin relative to the secondary amine group of the polyaminoamide of between 0.5: 1 and 1.8: 1.
  • Such polymers are described in particular in the patents American 3,227,615 and 2,961,347.
  • Polymers of this type are in particular sold under the name "Hercosett 57” by the company Hercules Inc. or else under the name of "PD 170” or “Delsette 101” by the company Hercules in the case of the adipic acid copolymer / epoxypropyl / diethylenetriamine.
  • Rg denotes a hydrogen atom or a methyl radical
  • R 7 and R 8 independently of one another, denote an alkyl group having from 1 to 22 carbon atoms, a hydroxyalkyl group in which the alkyl group preferably has 1 to 5 carbon atoms, a lower amidoalkyl group (C-1-C4), or R7 and Rs can denote, jointly with the nitrogen atom to which they are attached, heterocyclic groups, such as piperidinyl or morpholinyl
  • R7 and Rs independently of one another, preferably denote an alkyl group having from 1 to 4 carbon atoms
  • Y " is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, sulfate, phosphate.
  • R 1 1, R12 and R 13 represent a C 1 alkyl radical -
  • A1 and B1 represent polymethylenic groups containing 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 atoms of oxygen, sulfur 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
  • R " ⁇ o and R-12 can form with the two nitrogen atoms to which they are attached a piperazine ring; in addition if A1 denotes a linear or branched, saturated or unsaturated alkylene or hydroxyalkylene radical, B1 can also denote a group - (CH2) n-CO-D-OC- (CH2) n- in which D denotes: a) a residue of glycol of formula: -OZO-, where Z denotes a linear or branched hydrocarbon radical or a group corresponding to one of the following formulas:
  • X " is an anion such as chloride or bromide.
  • These polymers have a number average molecular weight generally between 1000 and 100,000.
  • Quaternary polyammonium polymers consisting of units of formula (IX): CH, CH,
  • D may be zero or may represent a group - (CH2) r - CO in which r denotes a number equal to 4 or 7, and
  • X is an anion derived from a mineral or organic acid.
  • cationic polymers comprising units of formula (IX) are described in particular in patent application EP-A-122 324 and can be prepared according to the methods described in US patents No. 4,157,388, 4,390,689, 4,702,906 , 4,719,282.
  • the polymer with units of formula (IX) in which p is equal to 3 is preferred, D denotes the value zero, X denotes a chlorine atom, the molecular mass measured by NMR of Carbon 13, (NMR 1 3 C) being approximately 25500.
  • -C4) trialkyl (C ⁇ - C4) ammonium salts such as the polymers obtained by homopolymerization of dimethylaminoethylmethacrylate quaternized with methyl chloride, or by copolymerization of acrylamide with dimethylaminoethyl methacrylate quaternized by methyl chloride, homo or copolymerization being followed by crosslinking with an olefinically unsaturated compound, in particular methylene bis acrylamide.
  • This dispersion is marketed under the name of
  • SALCARE® SC 92 by the company ALLIED COLLOIDS. It is also possible to use a crosslinked homopolymer of methacryloyloxyethyl trimethylammonium chloride containing approximately 50% by weight of the homopolymer in mineral oil or in a liquid ester. These dispersions are marketed under the names of "SALCARE® SC 95” and “SALCARE® SC 96" by the company ALLIED COLLOIDS.
  • cationic polymers which can be used in the context of the invention are polyalkyleneimines, in particular polyethyleneimines, polymers containing vinylpyridine or vinylpyridinium units, polyamine and epichlorohydrin condensates, quaternary polyureylenes and chitin derivatives.
  • cationic polymers capable of being used in the context of the present invention, it is preferred to use the polymers of families (1), (9), (10) (11) and (14) and even more preferably the polymers of formulas (W) and (U) below:
  • CH 3 C 2 H 5 and in particular those whose molecular weight, determined by gel permeation chromatography, is approximately 1200.
  • the concentration of cationic polymer in the compositions according to the present invention can vary from 0.01 to 10% by weight relative to the total weight of the composition, preferably from 0.05 to 5% and even more preferably from 0.1 to 3%.
  • amphoteric polymers which can be used in accordance with the present invention can be chosen from polymers comprising distributed K and M units statistically in the polymer chain, where K denotes a unit deriving from a monomer comprising at least one basic nitrogen atom and M denotes a unit deriving from an acid monomer comprising one or more carboxylic or sulphonic groups, or else K and M may denote groups derived from zwitterionic monomers of carboxybetaines or sulfobetaines; K and M can also denote a cationic polymer chain comprising primary, secondary, tertiary or quaternary amine groups, in which at least one of the amine groups carries a carboxylic or sulphonic group linked via a hydrocarbon radical, or although K and M form part of a chain of a polymer with an ⁇ , ⁇ -dicarboxylic ethylene unit, one of the carboxyl groups of which has been reacted with a polyamine comprising one or more primary or
  • amphoteric polymers corresponding to the definition given above which are more particularly preferred are chosen from the following polymers:
  • the vinyl compound can also be a dialkyldiallylammonium salt such as dimethyldiallylammonium chloride.
  • the copolymers of acrylic acid and of the latter monomer are offered under the names MERQUAT 280, MERQUAT 295 and MERQUAT PLUS 3330 by the company CALGON.
  • the N-substituted acrylamides or methacrylamides more particularly preferred according to the invention are the groups in which the alkyl radicals contain from 2 to 12 carbon atoms and more particularly N-ethylacrylamide, N-tertiobutyl-acrylamide, N-tertiooctyl-acrylamide , N-octylacrylamide, N-decylacrylamide, N-dodecylacrylamide and the corresponding methacrylamides.
  • the acid comonomers are chosen more particularly from acrylic, methacrylic, crotonic, itaconic, maleic, fumaric acids as well as alkyl monoesters having 1 to 4 carbon atoms of maleic or fumaric acids or anhydrides.
  • the preferred basic comonomers are aminoethyl, butyl aminoethyl, N, N'-dimethylaminoethyl, N-tert-butylaminoethyl methacrylates.
  • Copolymers are particularly used, the name CTFA (4th Ed., 1991) being Octylacrylamide / acrylates / butylaminoethylmethacrylate copolymer such as the products sold under the name AMPHOMER or LOVOCRYL 47 by the company NATIONAL STARCH.
  • R-jg represents a divalent radical derived from a saturated dicarboxylic acid, from a mono or dicarboxylic acid with ethylene double bond, from an ester of a lower alkanol having 1 to 6 carbon atoms of these acids or of a radical derived from the addition of any one of said acids with an amin e bis-primary or bis-secondary
  • Z denotes a radical of a polyamine polyaikylène bis-primary, mono- or bis-secondary and preferably represents: a) in proportions of 60 to 100 mol%, the radical
  • N - ⁇ / c) in the proportions of 0 ⁇ to 20 mol% the radical -NH- (CH2) 6-NH- deriving from hexamethylenediamine, these polyaminoamines being crosslinked by addition of a bifunctional crosslinking agent chosen from epihalohydrins , diepoxides, dianhydrides, bis unsaturated derivatives, using 0.025 to 0.35 mole of crosslinking agent by amino group of the polyaminoamide and alkylated by the action of acrylic acid, chloracetic acid or a sultone alkane or of their salts.
  • a bifunctional crosslinking agent chosen from epihalohydrins , diepoxides, dianhydrides, bis unsaturated derivatives
  • the saturated carboxylic acids are preferably chosen from acids having 6 to 10 carbon atoms such as adipic, trimethyl-2,2,4-adipic acid and trimethyl-2,4,4-adipic, terephthalic acid, ethylenic double bond such as for example acrylic, methacrylic, itaconic acids.
  • the alkane sultones used in the alkylation are preferably propane or butane sultone, the salts of the alkylating agents are preferably the sodium or potassium salts.
  • R20 denotes a polymerizable unsaturated group such as an acrylate, methacrylate, acrylamide or methacrylamide group
  • y and z represent an integer from 1 to 3
  • R21 and R22 represent a hydrogen, methyl, ethyl or propyl atom
  • R23 and R24 represent a hydrogen atom or an alkyl radical such that the sum of the carbon atoms in R23 and R24 does not exceed 10.
  • the polymers comprising such units may also contain units derived from non-zwitterionic monomers such as dimethyl or diethylaminoethyl acrylate or methacrylate or alkyl acrylates or methacrylates, acrylamides or methacrylamides or vinyl acetate.
  • the copolymer of methyl methacrylate / methyl dimethyl-carboxymethylammonio-ethyl methacrylate such as the product sold under the name DIAFORMER Z301 by the company SANDOZ.
  • R 25 represents a radical of formula: R 27 R 28
  • R 27 and R 28 each represent a hydrogen atom, as well as the salts formed by these compounds with bases or acids.
  • R29 represents a hydrogen atom, a CH3O radical, CH3CH2O, phenyl
  • R30 denotes hydrogen or a lower alkyl radical such as methyl, ethyl
  • R31 denotes hydrogen or a lower alkyl radical such as methyl, ethyl
  • R32 denotes a lower alkyl radical such as methyl, ethyl or a radical corresponding to the formula: -R33 "N (31) 2>
  • R 33 representing a group -CH 2 -CH 2 -, -CH 2 -CH 2 -CH 2 -, -CH 2 -CH (CH 3 ) -, R 31 having the meanings mentioned above, as well as the higher homologs of these radicals and containing up to 6 carbon atoms.
  • E or E ' denote a bivalent radical which is a straight or branched chain alkylene radical containing up to 7 carbon atoms in the main chain unsubstituted or substituted by hydroxyl groups and which may also contain 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, alkenylamine groups, hydroxyl groups, benzylamine, amine oxide, quaternary ammonium, amide, imide, alcohol, ester and / or urethane;
  • E denotes the symbol E or E 'and at least once E';
  • E having the meaning indicated above and E 'is a 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 comprising a or more nitrogen atoms, the nitrogen atom being substituted by an alkyl chain optionally interrupted by an oxygen atom and necessarily having one or more carboxyl functions or one or more hydroxyl functions and betainized by reaction with chloracetic acid or sodium chloracetate.
  • These copolymers can also contain other vinyl comonomers such as vinylcaprolactam.
  • amphoteric polymers which are particularly preferred according to the invention are those of the family (1).
  • the amphoteric polymer (s) can represent from 0.01% to 10% by weight, preferably from 0.05% to 5% by weight, and even more preferably from 0.1% to 3% by weight , of the total weight of the composition.
  • compositions of the invention preferably comprise one or more surfactants.
  • the surfactant (s) can be chosen either, alone or as a mixture, from anionic, amphoteric, nonionic, zwitterionic and cationic surfactants.
  • surfactants which are suitable for carrying out the present invention are in particular the following:
  • Anionic surfactant (s) By way of example of anionic surfactants which can be used, alone or as mixtures, in the context of the present invention, there may be mentioned in particular (non-limiting list) the salts (in particular alkaline salts, in particular sodium salts, ammonium salts, amin e s salts, amino alcohol salts or magnesium salts) of the following compounds: alkyl sulphates, alkyl ether sulphates, alkylamido, alkylarylpolyether sulphates, monoglyceride sulphates; alkylsulfonates, alkylphosphates, alkylamidesulfonates, alkylarylsulfonates, ⁇ -olefin-sulfonates, paraffin-sulfonates; (C 6 -C 24 ) alkyl sulfosuccinates, (C 6 -C 2 ) alkyl ethersulfosuccinates, (C 6
  • alkyl esters (C 6 -C 2 ) carboxylic polyglycosides such as the alkylglucoside citrates, the alkylpolyglycoside tartrate and the alkylpolyglycoside sulfosuccinates.
  • anionic surfactants which can still be used, mention may also be made of the salts of fatty acids such as the salts of oleic, ricinoleic, palmitic, stearic acids, coconut oil or hydrogenated coconut oil acids; acyl lactylates whose acyl radical contains 8 to 20 carbon atoms.
  • alkyl D galactoside uronic acids and their salts the polyoxyalkylenated (C 6 -C 2 ) alkyl ether carboxylic acids, the polyoxyalkylenated (C 6 -C 24 ) aryl ether carboxylic acids, the alkyl (C 6 -C 2 ) polyoxyalkylenated carboxylic amido ether and their salts, in particular those comprising from 2 to 50 alkylene oxide groups, in particular ethylene groups, and their mixtures.
  • Non-ionic surfactants are also well known compounds per se (see in particular in this regard "Handbook of Surfactants” by MR PORTER, Blackie & Son editions (Glasgow and London), 1991, pp 116-178) and their nature is not, in the context of the present invention, critical. So, they can in particular be chosen from (nonlimiting list) alcohols, alpha-diols, polyethoxylated, polypropoxylated alkylphenols, having a fatty chain comprising for example 8 to 18 carbon atoms, the number of ethylene oxide or oxide groups propylene which can range in particular from 2 to 50.
  • Amphoteric or zwitterionic surfactants may in particular be (non-limiting list) derivatives of aliphatic secondary or tertiary amines, in which the aliphatic radical is a chain linear or branched having 8 to 18 carbon atoms and containing at least one water-soluble anionic group (for example carboxylate, sulfonate, sulfate, phosphate or phosphonate); mention may also be made of (C8-C20) alkyl betaines, sulfobetaines, (C8-C20) alkyl amidoalkyl (C1-C5) betaines or (Cs-C20) amidoalkyl (C-
  • B represents -CH2CH2OX '
  • C represents - (CH2) Z -Y'
  • z 1 or 2
  • X 'de notes the group -CH2CH2-COOH or a hydrogen atom
  • Y' denotes -COOH or the radical -CH 2 - CHOH - SO3H
  • R34 'de notes an alkyl radical of an acid R37 -COOH present in coconut oil or in hydrolysed linseed oil, an alkyl radical, especially in C7, Cg, C ⁇
  • cationic surfactants that may be mentioned in particular (nonlimiting list): the salts of primary, secondary or tertiary fatty amines, optionally polyoxyalkylenated; quaternary ammonium salts such as chlorides or bromides of tetraalkylammonium, alkylamidoalkyltrialkylammonium, trialkylbenzylammonium, trialkylhydroxyalkylammonium or alkylpyridinium; imidazoline derivatives; or amine oxides of a cationic nature.
  • the amounts of surfactants present in the ready-to-use composition according to the invention can vary from 0.01 to 30% and preferably from 0.1 to 20% of the total weight of the composition.
  • compositions according to the invention may also contain other rheology adjusting agents such as cellulosic thickeners (hydroxyethylcellulose, hydroxypropylcellulose, carboxymethylcellulose, etc.), guar gum and its derivatives (hydroxypropylguar, etc.), microbial origin (xanthan gum, scleroglucan gum, etc.), synthetic thickeners such as crosslinked homopoiymers of acrylic acid or acrylamidopropanesulfonic acid and ionic or nonionic associative polymers such as the polymers sold under the names PEMULEN TR1 or TR2 by the company GOODRICH, SALCARE SC90 by the company ALLIED COLLOIDS, ACULYN 22, 28, 33, 44, or 46 by the company ROHM & HAAS and ELFACOS T210 and T212 by the company AKZO.
  • cellulosic thickeners hydroxyethylcellulose, hydroxypropylcellulose, carboxymethylcellulose, etc.
  • These additional thickeners can represent from 0.05 to 10% by weight of the total weight of the composition.
  • the pH of the ready-to-use composition is generally between approximately
  • the pH of the ready-to-use compositions of the invention intended for bleaching is between approximately 1, 5 and 10, and even more preferably between approximately 1, 5 and 7. More preferably, the pH of the compositions of the ready-to-use invention intended for permanent deformation is between approximately 6 and 12 and even more preferably between approximately 7 and 11.
  • This pH can be adjusted to the desired value by means of acidifying or basifying agents well known in the state of the art in discoloration or in permanent deformation of keratin fibers.
  • basifying agents there may be mentioned, by way of example, ammonia, alkali or ammonium carbonates, alkanolamines such as mono-, di- and triethanolamines and their derivatives, oxyethylenated and / or oxypropylenated hydroxyalkylamines and ethylenediamines, sodium or potassium hydroxides and the compounds of formula (XIX) below:
  • R is a propylene residue optionally substituted by a hydroxyl group or a C ⁇ -C 4 alkyl radical
  • R 38 , R 3 g, R40 and R 41 identical or different, represent a hydrogen atom, a C ⁇ -C 4 alkyl or CC 4 hydroxyalkyl radical.
  • the acidifying agents are conventionally, for example, mineral or organic acids such as hydrochloric acid, orthophosphoric acid, carboxylic acids such as tartaric acid, citric acid, lactic acid, or acids sulfonic.
  • the basifying or acidifying agents may represent approximately 0.01 to 30% by weight of the total weight of the discoloration or permanent deformation composition.
  • compositions of the invention can also contain sequestering agents such as for example ethylenediamine tetraacetic acid (EDTA).
  • sequestering agents such as for example ethylenediamine tetraacetic acid (EDTA).
  • compositions containing the reducing agent and the polymer with an aminoplast-ether skeleton are in anhydrous form (powder or cream), they contain the main agents and additives mentioned above in the form of essentially anhydrous solids or liquids. They can also contain mineral or organic fillers such as silica or clays. They can also contain binders such as vinylpyrrolidone, oils or waxes, polyalkylene glycols or derivatives of polyalkylene glycols. They can also contain lubricants such as polyol stearates or alkali or alkaline earth metal sterates, as well as coloring or matifying agents such as titanium oxides.
  • the medium containing the reducing agent when it is an aqueous medium, it may optionally contain cosmetically acceptable organic solvents, including more particularly alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol, and phenylethyl alcohol, or glycols or glycol ethers such as, for example, monomethyl, monoethyl and monobutyl ethers of ethylene glycol, propylene glycol or its ethers such as, for example, propylene glycol monomethyl ether, butylene glycol, dipropylene glycol as well as the diethylene glycol alkyl ethers such as, for example, the monoethyl ether or the monobutyl ether of diethylene glycol, in concentrations of between approximately 0.5 and 20% and, preferably, between approximately 2 and 10% by weight relative to the total weight of the composition.
  • cosmetically acceptable organic solvents including more particularly alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol, and phen
  • the bleaching or permanent deformation composition according to the invention may also contain an effective amount of other agents, also previously known in bleaching or in permanent deformation of keratin fibers, such as various usual adjuvants such as volatile or non-volatile silicones, cyclic or linear or branched, organomodified (in particular by amino groups) or not organomodified, preservatives, ceramides, waxes or oils, vegetable, mineral or synthetic, acids and in particular AHAs etc.
  • agents also previously known in bleaching or in permanent deformation of keratin fibers
  • various usual adjuvants such as volatile or non-volatile silicones, cyclic or linear or branched, organomodified (in particular by amino groups) or not organomodified, preservatives, ceramides, waxes or oils, vegetable, mineral or synthetic, acids and in particular AHAs etc.
  • the bleaching process according to the invention consists in applying the ready-to-use reducing composition to the dry or wet keratin fibers, and to leaving it to act for a pause time varying, preferably, from 1 to 60 minutes approximately, and more preferably from 10 to 45 minutes approximately, to rinse the fibers, then optionally to wash them in shampoo, then to rinse them again, and to dry them.
  • the permanent deformation method according to the invention consists in applying the reducing composition ready for use to the dry or wet keratin fibers, to leaving it to act for a pause time varying, preferably, from 1 to 60 minutes. approximately, and more preferably from 10 to 45 minutes approximately, optionally rinsing the fibers, then applying an oxidizing composition and leaving to act for a pause time of between 1 and 20 minutes and preferably between 1 and 10 minutes, then optionally at wash them in shampoo, then rinse again, and dry them.
  • Mechanical means for tensioning the keratin fibers can be used before, during or after application of the reducing composition and removed before or after rinsing the oxidizing composition.
  • the above bleaching composition allowed for regular bleaching of artificially dyed hair with an oxidation dye.
  • the above permanent deformation composition was applied for 15 minutes to wet hair previously wound on styling rollers, then rinsed thoroughly with water.
  • An 8-volume hydrogen peroxide and .pH 3 solution was then applied for 5 minutes, then rinsed again, the rollers were removed and dried.
  • the hair presented a beautiful homogeneous crimp.

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EP00979710A 1999-12-08 2000-11-10 Eine zusammensetzung zur entfärbung oder dauerhaften verförmung von keratinischen fasern, die ein verdickungspolymer mit einer aminoplastether hauptkette enthält Withdrawn EP1237528A1 (de)

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FR9915485 1999-12-08
FR9915485A FR2802093B1 (fr) 1999-12-08 1999-12-08 Composition pour la decoloration ou la deformation permanente des fibres keratiniques comprenant un polymere epaississant a squelette aminoplaste-ether
PCT/FR2000/003144 WO2001041722A1 (fr) 1999-12-08 2000-11-10 Composition pour la decoloration ou la deformation permanente de s fibres keratiniques comprenant un polymere epaissis a squelette aminoplaste-ether

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FR2802093B1 (fr) 2002-01-18
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US6984250B1 (en) 2006-01-10
WO2001041722A1 (fr) 2001-06-14
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