WO2002100366A2 - Composition de teinture des fibres keratiniques humaines avec des colorants d'oxydation et des composes dicationiques - Google Patents
Composition de teinture des fibres keratiniques humaines avec des colorants d'oxydation et des composes dicationiques Download PDFInfo
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- WO2002100366A2 WO2002100366A2 PCT/FR2002/001964 FR0201964W WO02100366A2 WO 2002100366 A2 WO2002100366 A2 WO 2002100366A2 FR 0201964 W FR0201964 W FR 0201964W WO 02100366 A2 WO02100366 A2 WO 02100366A2
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- 0 **(N)N*(*)N Chemical compound **(N)N*(*)N 0.000 description 5
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4966—Triazines or their condensed derivatives
Definitions
- the invention relates to a dye composition for human keratin fibers and more particularly the hair, comprising, in a medium suitable for dyeing, at least one oxidation dye, and in addition at least one dicationic compound.
- oxidation bases in particular ortho- or para-phenylenediamines, ortho - or para-aminophenols, and heterocyclic bases.
- the oxidation dye precursors are initially little or no colored compounds which develop their dyeing power within the hair in the presence of oxidizing agents, leading to the formation of colored compounds.
- the formation of these colored compounds results either from an oxidative condensation of the "oxidation bases” on themselves, or from an oxidative condensation of the "oxidation bases” on color-modifying compounds, or “couplers” , which are generally present in the dye compositions used in oxidation dyeing and are represented more particularly by metaphenylenediamines, meta-aminophenols and metadiphenols, and certain heterocyclic compounds.
- the dyes must also make it possible to cover white hair, and finally be the least selective possible, that is to say allow to obtain the smallest possible color differences throughout the same keratin fiber, which can be in differently sensitized effect (ie damaged) between its tip and its root.
- direct dyes are generally added to them, most often chosen from benzene nitro direct dyes, azo direct dyes, quinone direct dyes and in particular anthraquinone dyes, azine direct dyes , triarylmethanics, indoamines or natural direct dyes.
- Oxidation dyes however, have the disadvantage, when incorporated into dye compositions, of leading to nuances which are not very chromatic.
- Chromaticity is defined by the value c * in the colorimetric notation system L *, a *, b *, of the International Commission on Lighting (OLE.). This value is equal to the square root of the sum a ⁇ + b ⁇ (+ a is red, -a is green, + b is yellow, -b is blue). The shade becomes more luminous the larger the value of c *.
- the cationic dyes described in the present invention have never been proposed for use in cosmetics.
- the present invention thus has for first object, a dye composition for human keratin fibers and more particularly hair, comprising, in a medium suitable for dyeing, at least one oxidation dye, characterized in that it comprises in in addition to at least one dicationic compound chosen from those of formulas (I), (II), or (III), described below.
- Another subject of the invention relates to a ready-to-use composition for dyeing human keratin fibers, and in particular hair, which contains at least one oxidation dye, at least one dicationic compound of formulas (I) , (II), or (III), and an oxidizing agent.
- 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 of the extemporaneous mixture of two or more compositions.
- the invention also relates to a process for the oxidation dyeing of human keratin fibers and in particular of the hair, consisting in applying to the fibers at least one composition A containing, in a medium suitable for dyeing, at least one oxidation dye. and at least one dicationic compound of formulas (I), (II), or (III), the color being revealed at alkaline, neutral or acidic pH, using a composition B containing at least one oxidizing agent, which is mixed just at the time of use with composition A or which is applied sequentially without intermediate rinsing.
- a subject of the invention is also a device for the oxidation dyeing of human keratin fibers and in particular of the hair, or dye "kit", which comprises a first compartment containing, in a medium suitable for dyeing, at least one oxidation dye and at least one dicationic compound of formulas (I), (II), or (III), and a second compartment containing an oxidizing agent.
- This device can be equipped with a means enabling the desired mixture to be delivered to the hair, such as the devices described in patent FR-2,586,913 in the name of the applicant.
- Dicationic direct dye The direct dicationic dyes according to the present invention are chosen from those of formulas (I), (II), or (III), below:
- -Z denotes an aliphatic or aromatic radical
- -Z- denotes an alkyl radical
- -R ⁇ l and R2 independently of one another, denote a hydrogen atom, or a radical (C ⁇ -C4) alkyl, or (C -] - C4) alkyl substituted by one or more atoms of halogen, a hydroxyl, carboxyl, cyano radical, a (C "
- -X is a bridging radical chosen from: -CO-; -CO-CH 2 -CH 2 -CO-; -CO-CO-; 1,4-dicarbonylphenyl; -CH2-CH2-; or a triazine of formulas (b) or (c) below:
- Y and Y1 independently of each other, denote a halogen atom, or a hydroxyl, or amino, or monoalkylamino, or dialkylamino, or 1-piperidino, or morpholino, or 1-piperazino radical, the piperazino radical being unsubstituted, or substituted on the nitrogen atom not attached to the triazine ring by a (C-
- -Z denotes an alkylene radical (C2-Cs) or forms, with the two adjacent nitrogen atoms and the radicals R-
- radical of formula (a), -R3 and R4 independently of one another, denote a hydrogen atom, or a (C-
- R5 and R ⁇ independently of one another, denote a hydrogen atom, a (C-
- -R-1 and R2 independently of one another, denote hydrogen, (C-
- -Z denotes a linear, branched or cyclic C2-C8 alkyl radical, optionally substituted by hydroxy, alkoxy, halogen, the chain of said radical being optionally interrupted by an -O- or -NR-j- group; a 1,4-phenyl radical, a 1,4-naphthyl radical optionally substituted by an alkyl, alkoxy, halogen; Z can be formed with R-
- -Z preferably denotes an unsubstituted phenyl radical, a phenyl or naphthyl radical substituted by 1 or 2 methyl or methoxy radicals, a piperazine radical by bond with R-
- -Z1 denotes a linear or branched or cyclic C2-C8 alkyl radical, optionally substituted by hydroxy, alkoxy, halogen, the chain of said radical being optionally interrupted by a group -O- or -NR ⁇
- -X 'and Y' independently of each other, denote hydrogen, halogen, (C -] - C4) alkyl, (C ⁇ -C4) alkoxy, (C ⁇
- R'1 denotes hydrogen, a substituted alkyl or aryl radical, an unsubstituted alkyl or aryl radical, or the same designation as R'2
- -B denotes a linear or branched alkylene radical
- -R'6 denotes hydrogen or substituted or unsubstituted alkyl
- -R'7 and R's, independently of one another denote substituted or unsubstituted alkyl
- R'3 denotes hydrogen, halogen, (C-
- -Z denotes a bridging radical chosen from the radicals of formulas
- R'g denotes, hydrogen, (C2-C4) unsubstituted or substituted alkylene, the alkylene radical being linear or branched and capable of be interrupted by one or more groups chosen from: -NR'9-, -O-, -S-.
- B denotes ethylene, n-propylene, isopropylene or n-butylene
- K denotes a coupling compound chosen from those of formula (f), (g) or (h) below
- the dyes of formula (I), (II), or (III), according to the present invention are known as such, and described and prepared in US Pat. Nos. 5,674,299 or US Pat. No. 5,708,151, the content of which is an integral part of the present invention. They are generally present in the dye composition in proportions of between approximately 0.01 and 40%, preferably between approximately 0.1 and 20% by weight, relative to the total weight of the composition.
- oxidation dyes which can be used according to the invention are chosen from oxidation bases and / or couplers.
- the compositions according to the invention contain at least one oxidation base.
- the oxidation bases which can be used in the context of the present invention are chosen from those conventionally known in oxidation dyeing, and among which mention may be made of ortho- and para-phenylenediamines, double bases, ortho- and para- aminophenols, the following heterocyclic bases and their addition salts with an acid. We can notably cite:
- Ri represents a hydrogen atom, an alkyl radical in CC 4 , monohydroxyalkyle in
- C r -C 4 polyhydroxyalkyl, C 2 -C 4 aIcoxy (CrC 4) alkyl (CC 4), C r C 4 alkyl substituted with a nitrogenous, phenyl or 4'-aminophenyl;
- R 2 represents a hydrogen atom, a CC 4 alkyl radical, a monohydroxyalkyl radical
- Ri and R 2 can also form, with the nitrogen atom which carries them, a 5 or 6-membered nitrogen heterocycle optionally substituted by one or more alkyl, hydroxy or ureido groups;
- R 3 represents a hydrogen atom, a halogen atom such as a chlorine atom, a CC 4 alkyl radical, sulfo, carboxy, monohydroxyalkyl in CC or hydroxyalkoxy in CC, acetylaminoalkoxy in CC 4 , mesylaminoalkoxy in CC 4 or carbamoylaminoalkoxy in CC,
- R 4 represents a hydrogen or halogen atom or a C 1 -C 4 alkyl radical.
- nitrogen groups of formula (V) above there may be mentioned in particular the amino, monoaIkyl (C r C 4 ) amino, dialkyl (C r C 4 ) amino, trialkyl (CC 4 ) amino, monohydroxyalkyl (CrC) radicals ) amino, imidazolinium and ammonium.
- paraphenylenediamines of formula (V) above there may be mentioned more particularly paraphenylenediamine, paratoluylenediamine, 2-chloro-paraphenylenediamine, 2,3-dimethyl-paraphenylenediamine, 2,6-dimethyl-paraphenylenediamine, 2 , 6-diethyl-paraphenylenediamine, 2,5-dimethyl-paraphenylenediamine, N, N-dimethyl-paraphenylenediamine, N, N-diethyl-paraphenylenediamine, N, N-dipropyl-paraphenylenediamine, 4-amino-N, N-diethyl-3-methyl-aniline, N, N-bis- ( ⁇ -hydroxyethyl) -paraphenylenediamine, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino-2-methyl-aniline, 4- N, N-bis- ( ⁇ -hydroxyethyl) -
- para-phenylenediamines of formula (V) above very particularly preferred are para-phenylenediamine, paratoluylenediamine, 2-isopropyl-para-phenylenediamine, 2- ⁇ -hydroxyethyl-para-phenylenediamine,
- - Z ⁇ and Z 2 identical or different, represent a hydroxyl radical or -NH 2 which can be substituted by an alkyl radical in CC 4 or by a link arm Y;
- the link arm Y represents an alkylene chain comprising from 1 to 14 carbon atoms, linear or branched which can be interrupted or terminated by one or more nitrogen groups and / or by one or more heteroatoms such as oxygen atoms, sulfur or nitrogen, and optionally substituted by one or more hydroxyl or C C6 alkoxy radicals;
- R 5 and R 6 represent a hydrogen or halogen atom, a C 1 -C 4 alkyl radical, CC 4 monohydroxyalkyl, C 2 -C 4 polyhydroxyalkyl, CC aminoalkyl or a linking arm Y;
- R 7 , R 8 , R 9 , Rio, R11 and R 12 identical or different, represent a hydrogen atom, a linker Y or a CC 4 alkyl radical; it being understood that the compounds of formula (VI) have only one linker arm Y per molecule.
- nitrogen groups of formula (VI) above there may be mentioned in particular the amino, monoalkyl (CC 4 ) amino, dialkyl (CC 4 ) amino, trialky ⁇ CC ⁇ amino, monohydroxyalkyl (CrC) amino, imidazolinium and ammonium.
- N, N'-bis- ( ⁇ -hydroxyethyl) -N, N'-bis- (4'-aminophenyl) -1, 3-diamino-propanol, 1, 8 -bis- (2,5-diaminophenoxy) -3,5-dioxaoctane or one of their addition salts with an acid are particularly preferred.
- R 13 represents a hydrogen atom, a halogen atom such as fluorine, an alkyl radical in CC 4 , monohydroxyalkyl in CC 4 , alkoxy (C r C 4 ) alkyl (CC 4 ) or aminoalkyl in CC 4 , or hydroxyalkyl (CC 4) aminoalkyl CC 4.
- R 14 represents a hydrogen atom or a halogen atom such as fluorine, an alkyl radical in CrC 4 , monohydroxyalkyle in CC, polyhydroxyalkyle in C 2 -C 4 , aminoalkyle in
- para-aminophenols of formula (VII) mention may more particularly be made of para-aminophenol, 4-amino-3-methyl-phenol, 4-amino-3-fluoro-phenol, 4-amino -3-hydroxymethyl-phenol, 4-amino-2-methyl-phenol, 4-amino-2-hydroxymethyl-phenol, 4-amino-2-methoxymethyl-phenol, 4-amino-2-aminomethyl-phenol , 4-amino-2- ( ⁇ -hydroxyethyl-aminomethyl) -phenol, and their addition salts with an acid.
- para-aminophenol 4-amino-3-methyl-phenol, 4-amino-3-fluoro-phenol, 4-amino -3-hydroxymethyl-phenol, 4-amino-2-methyl-phenol, 4-amino-2-hydroxymethyl-phenol, 4-amino-2-methoxymethyl-phenol, 4-amino-2-aminomethyl-phenol , 4-amino-2- ( ⁇ -hydroxyethyl-aminomethyl) -
- the ortho-aminophenols which can be used as oxidation bases in the context of the present invention, are in particular chosen from 2-amino-phenol, 2-amino-1- hydroxy-5-methyl-benzene, 2-amino-1-hydroxy-6-methyl-benzene, 5-acetamido-2-amino-phenol, and their addition salts with an acid.
- heterocyclic bases which can be used as oxidation bases in the dye compositions in accordance with the invention, mention may more particularly be made of pyridine derivatives, pyrimidine derivatives, pyrazole derivatives, and their addition salts with an acid.
- pyridine derivatives mention may more particularly be made of the compounds described for example in patents GB 1,026,978 and GB 1,153,196, such as 2,5-diamino-pyridine, 2- (4-methoxyphenyl) amino-3- amino-pyridine, 2,3-diamino-6-methoxy-pyridine, 2- ( ⁇ -methoxyethyl) amino-3-amino-6-methoxy pyridine, there 3,4-diamino-pyridine, and their salts addition with an acid.
- 2,5-diamino-pyridine 2- (4-methoxyphenyl) amino-3- amino-pyridine
- 2,3-diamino-6-methoxy-pyridine 2,3-diamino-6-methoxy-pyridine
- 2- ( ⁇ -methoxyethyl) amino-3-amino-6-methoxy pyridine there 3,4-diamino-pyridine, and their salts addition with an acid.
- pyrimidine derivatives mention may be made more particularly of the compounds described for example in German patents DE 2,359,399 or Japanese patents JP 88-169 571 and JP 91-10659 or patent applications WO 96/15765, such as 2,4, 5,6-tetra-aminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2, 5,6-triaminopyrimidine, and pyrazolopyrimidine derivatives such as those mentioned in patent application FR-A-2750 048 and among which mention may be made of pyrazolo- [1,5-a] -pyrimidine-3,7-diamine ; 2,5-dimethyl-pyrazolo- [1,5-a] -pyrimidine-3,7-diamine; pyrazolo- [1,5-a] -pyrimidine-3,5-d
- WO 94/08970, FR-A-2 733 749 and DE 195 43 988 such as 4,5-diamino-1 -methyl- pyrazole, 3,4-diamino-pyrazole, 4,5-diamino-1- (4'-chlorobenzyl) -pyrazole, 4,5-diamino 1, 3-dimethyl-pyrazole, 4,5-diamino- 3-methyl-1-phenyl-pyrazole, 4,5-diamino 1-methyl-3-phenyl-pyrazole, 4-amino-1,3-dimethyl-5-hydrazino-pyrazole, 1-benzyl-4, 5-diamino-3-methyl-pyrazole, 4,5-diamino-3-tert-butyl-1-methyl-pyrazole, 4,5-diamino-1-tert-butyl-3-methyl-pyrazole, 4 , 5-diamino-1- ( ⁇ -hydroxyethyl)
- the oxidation bases preferably represent from 0.0005 to 12% by weight approximately of the total weight of the composition and even more preferably from 0.005 to 8% by weight approximately of this weight.
- the couplers which can be used in the dyeing process according to the invention are those conventionally used in oxidation dyeing compositions, that is to say the meta-aminophenols, the meta-phenylenediamines, the metadiphenols, the naphthols and the couplers heterocyclic derivatives such as, for example, indole derivatives, indoline derivatives, sesamol and its derivatives, pyridine derivatives, pyrazolotriazole derivatives, pyrazolones, indazoles, benzimidazoles, benzothiazoles, benzoxazoles, 1,3-benzodioxoles, quinolines and their addition salts with an acid.
- couplers are more particularly chosen from 2,4-diamino l- ( ⁇ -hydroxyethyloxy) -benzene, 2-methyl-5-amino-phenol, 5-N- ( ⁇ -hydroxyethyl) amino-2-methyl- phenol, 3-amino-phenol, 1,3-dihydroxy-benzene, 1,3-dihydroxy-2-methyl-benzene, 4-chloro 1,3-dihydroxy-benzene, 2-amino 4- ( ⁇ -hydroxyethylamino) -1-methoxy-benzene, 1,3-diamino-benzene, 1, 3-bis- (2,4-diaminophenoxy) -propane, sesamol, 1-amino-2-methoxy- 4,5-methylenedioxy benzene, ⁇ -naphthol, 6-hydroxy-indole, 4-hydroxy-indole, 4-hydroxy-N-methyl indole, 6-hydroxy-indoline, 2,6-dihydroxy -4-
- these couplers preferably represent from 0.0001 to 10% by weight approximately of the total weight of the composition, and even more preferably from 0.005 to 5% by weight approximately.
- addition salts with an acid of the oxidation bases and couplers are in particular chosen from hydrochlorides, hydrobromides, sulfates and tartrates, lactates and acetates.
- the medium of the composition suitable for dyeing is preferably an aqueous medium consisting of water and may advantageously 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, the 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, monoethyl ether or diethylene glycol monobutyl ether.
- the solvents can then be present in concentrations ranging from approximately 0.5 to 20% and, preferably, from approximately 2 to 10% by weight relative to the total weight of the composition:
- the dye composition may also contain an effective amount of other agents, which are moreover previously known in oxidation dyeing, such as various usual adjuvants such as surfactants well known in the art and of anionic type, cationic, non-ionic, amphoteric, zwitterionic or mixtures thereof, thickening agents, antioxidants, perfumes, dispersing agents, conditioning agents including in particular cationic or amphoteric polymers, opacifying agents, sequestering agents such that EDTA and etidronic acid, UV filters, waxes, silicones, volatile or not, cyclic or linear or branched, organomodified (in particular by amino groups) or not, preservatives, ceramides, pseudoceramides, vegetable, mineral or synthetic oils, vitamins or provitamins such as panthenol, non-ionic, anionic associative polymers, a mphoteric or cationic.
- agents which are moreover previously known in oxidation dyeing, such as various usual adjuvants
- Associative polymers are water-soluble polymers capable, in a medium aqueous, to associate reversibly with each other or with other molecules.
- hydrophilic zones and hydrophobic zones characterized by at least one fatty chain.
- Associative polymers of anionic type One can cite among them:
- R denotes H or CHè
- B denotes the ethyleneoxy radical
- n is zero or denotes an integer ranging from 1 to 100
- R denotes a hydrocarbon radical chosen from the radicals alkyl, arylalkyl, aryl, alkylaryl, cycloalkyl, comprising from 8 to 30 carbon atoms, preferably 10 to 24, and more particularly still from 12 to 18 carbon atoms.
- a unit of formula (I) more particularly preferred is a unit in which R ′ denotes H, n is equal to 10, and R denotes a stearyl radical (C 18 ).
- Anionic associative polymers of this type are described and prepared, according to an emulsion polymerization process, in patent EP-0 216479.
- anionic associative polymers the polymers formed from 20 to 20 are particularly preferred according to the invention.
- acrylic acid and / or methacrylic acid from 5 to 60% by weight of lower alkyl (meth) acrylates, from 2 to 50% by weight of fatty chain allyl ether of formula (I), and from 0 to 1% by weight of a crosslinking agent which is a well-known polyethylene unsaturated copolymerizable monomer, such as diallyl phthalate, allyl (meth) acrylate, divinylbenzene, dimethacrylate of ( poly) ethylene glycol, and methylene-bis-acrylamide.
- a crosslinking agent which is a well-known polyethylene unsaturated copolymerizable monomer, such as diallyl phthalate, allyl (meth) acrylate, divinylbenzene, dimethacrylate of ( poly) ethylene glycol, and methylene-bis-acrylamide.
- crosslinked terpolymers of methacrylic acid, ethyl acrylate, polyethylene glycol (10 EO) stearyl alcohol ether (Steareth 10), in particular those sold by the company ALLIED COLLOIDS under the names SALCARE SC 80 and SALCARE SC90 which are 30% aqueous emulsions of a crosslinked terpolymer of methacrylic acid, ethyl acrylate and steareth-10-allyl ether (40/50/10).
- these polymers are chosen from those in which the hydrophilic unit of olefinic unsaturated carboxylic acid type corresponds to the monomer of formula (II) below:
- R 2 denotes H or CH 3 or C 2 H 5 (that is to say acrylate, methacrylate or ethacrylate units) and preferably H (acrylate units) or CH 3 (methacrylate units), R 3 denoting a C 10 -C 30 , and preferably C 12 -C 22, alkyl radical.
- (C 10 -C 30 ) alkyl esters of unsaturated carboxylic acids according to the invention include, for example, lauryl acrylate, stearyl acrylate, decyl acrylate, isodecyl acrylate , dodecyl acrylate, and the corresponding methacrylates, lauryl methacrylate, stearyl methacrylate, decyl methacrylate, isodecyl methacrylate, and dodecyl methacrylate.
- Anionic polymers of this type are for example described and prepared, according to patents US-3,915,921 and 4,509,949.
- anionic associative polymers use will be made more particularly of polymers formed from a mixture of monomers comprising:
- crosslinking agent which is a well-known polyethylene copolymerizable unsaturated monomer, such as diallyl phthalate, allyl (meth) acrylate, divinylbenzene, (poly) ethylene glycol dimethacrylate, and methylene-bis- acrylamide.
- a crosslinking agent which is a well-known polyethylene copolymerizable unsaturated monomer, such as diallyl phthalate, allyl (meth) acrylate, divinylbenzene, (poly) ethylene glycol dimethacrylate, and methylene-bis- acrylamide.
- anionic associative polymers use will be made more particularly of those consisting of 95 to 60% by weight of acrylic acid (hydrophilic unit), 4 to 40% by weight of C 10 -C 30 alkyl acrylate (unit hydrophobic), and 0 to 6% by weight of crosslinking polymerizable monomer, or else those consisting of 98 to 96% by weight of acrylic acid
- a nonionic mono-urethane which is the reaction product of a monohydric surfactant with a monoethylenically unsaturated monoisocyanate, such as those described in the patent application EP-A-0173109 and more particularly that described in Example 3, namely, a methacrylic acid / methyl acrylate / dimethyl metaisopropenyl benzyl isocyanate ethoxylated behenyl alcohol isocyanate (40OE) terpolymer in 25% aqueous dispersion.
- a monohydric surfactant with a monoethylenically unsaturated monoisocyanate
- a methacrylic acid / methyl acrylate / dimethyl metaisopropenyl benzyl isocyanate ethoxylated behenyl alcohol isocyanate (40OE) terpolymer in 25% aqueous dispersion.
- the copolymers comprising, among their monomers, an ⁇ , ⁇ -monoethylenically unsaturated carboxylic acid and an ⁇ , ⁇ -monoethylenically unsaturated carboxylic acid ester and of an oxyalkylenated fatty alcohol.
- these compounds also comprise, as monomer, an ester of ⁇ , ⁇ -monoethylenically unsaturated carboxylic acid and of C1C4 alcohol.
- ACULYN 22 sold by the company ROHM and HAAS, which is a methacrylic acid / ethyl acrylate / oxyalkylenated stearyl methacrylate terpolymer.
- Cationic type associative polymers According to the present invention, they are preferably chosen from quaternized cellulose derivatives and polyacrylates with non-cyclic amino side groups.
- the quaternized cellulose derivatives are, in particular, - the quaternized celluloses modified by groups comprising at least one fatty chain, such as the alkyl, arylalkyl or alkylaryl groups containing at least 8 carbon atoms, or mixtures thereof,
- - quaternized hydroxyethylcelluloses modified by groups comprising at least one fatty chain, such as alkyl, arylalkyl, alkylaryl groups containing at least 8 carbon atoms, or mixtures thereof.
- the alkyl radicals carried by the above quaternized celluloses or hydroxyethylcelluloses preferably contain from 8 to 30 carbon atoms.
- the aryl radicals preferably denote the phenyl, benzyl, naphthyl or anthryl groups.
- quaternized C 8 -C 30 fatty chain alkyl hydroxyethyl celluloses examples include the products QUATRISOFT LM 200, QUATRISOFT LM-X 529-18-A, QUATRISOFT LM-X 529-18B (C 12 alkyl) and QUATRISOFT LM-X 529-8 (C 8 alkyl) sold by the company AMERCHOL and the products CRODACEL QM, CRODACEL QL (C 12 alkyl) and CRODACEL QS (C18 alkyl) sold by the company CRODA.
- They are preferably chosen from those comprising at least one non-cyclic cationic unit. More particularly still, those prepared from or comprising 1 to 20 mol% of monomer comprising a fatty chain, and preferably 1.5 to 15 mol% and more particularly still 1.5 to 6 mol%, are preferred, relative to the number total moles of monomers.
- amphoteric associative polymers preferred according to the invention comprise, or are prepared by copolymerizing: 1) at least one monomer of formula (la) or (Ib):
- R j and R 2 identical or different, represent a hydrogen atom or a methyl radical
- Z represents an NH group or an oxygen atom
- n is an integer from 2 to 5
- R 6 - -CH CR 7 COOH (II) in which, RQ and R7, identical or different, represent a hydrogen atom or a methyl radical;
- R 6 - CH CR 7 - COXR 8 (III) in which RQ and R7, identical or different, represent a hydrogen atom or a methyl radical, X denotes an atom oxygen or nitrogen and RQ denotes a linear or branched alkyl radical having from 1 to 30 carbon atoms; at least one of the monomers of formula (Ia), (Ib) or (III) comprising at least one fatty chain.
- the monomers of formula (la) and (Ib) of the present invention are preferably chosen from the group consisting of:
- these monomers being optionally quaternized, for example by a halide C1-C4 alkyl or C1-C4 dialkyl sulfate.
- the monomer of formula (la) is chosen from acrylamide-propyl trimethyl ammonium chloride and methacrylamidopropyl trimethyl ammonium chloride.
- the monomers of formula (II) of the present invention are preferably chosen from the group consisting of acrylic acid, methacrylic acid, crotonic acid and 2-methyl crotonic acid. More particularly, the monomer of formula (II) is acrylic acid.
- the monomers of formula (III) of the present invention are preferably chosen from the group consisting of Cj 2 -C 22 and more particularly C-15-C1 s- alkyl acrylates or methacrylates.
- the monomers constituting the fatty chain amphoteric polymers of the invention are preferably already neutralized and / or quaternized.
- the ratio of the number of cationic charges / anionic charges is preferably equal to approximately 1.
- amphoteric associative polymers according to the invention preferably comprise from 1 to 10 mol% of the monomer comprising a fatty chain (monomer of formula (la), (Ib) or (III)), and preferably from 1.5 to 6 moles %.
- the weight average molecular weights of the amphoteric associative polymers according to the invention can vary from 500 to 50,000,000 and are preferably between 10,000 and 5,000,000.
- amphoteric associative polymers according to the invention can also contain other monomers such as nonionic monomers and in particular such as C1-C4 alkyl acrylates or methacrylates.
- Amphoteric associative polymers are for example described and prepared in patent application WO9844012.
- the acrylic acid / (meth) acrylamidopropyl trimethyl ammonium chloride / stearyl methacrylate terpolymers are preferred.
- celluloses modified by groups comprising at least one fatty chain as an example, we can cite:
- alkyl groups modified by groups comprising at least one fatty chain such as alkyl, arylalkyl, alkylaryl groups, or their mixtures, and in which the alkyl groups are preferably C 8 -C 22 , such as the product NATROSOL PLUS GRADE 330 CS (C 16 alkyls) sold by the company AQUALON, or the product BERMOCOLL EHM 100 sold by the company BEROL NOBEL,
- polyalkylene glycol ether groups of alkyl phenol such as the product AMERCELL POLYMER HM-1500 (polyethylene glycol (15) nonyl phenol ether) sold by the company AMERCHOL.
- hydroxypropylguars modified by groups comprising at least one fatty chain such as the product ESAFLOR HM 22 (C 22 alkyl chain) sold by the company LAMBERTI, the products RE210-18 (C 14 alkyl chain) and RE205 -1 (C 20 alkyl chain) sold by the company RHONE POULENC.
- copolymers of CC 6 alkyl methacrylates or acrylates and of amphiphilic monomers comprising at least one fatty chain such as for example the methyl acrylate / oxyethylenated stearyl acrylate sold by the company GOLDSCHMIDT under the name ANTIL 208.
- copolymers of hydrophilic methacrylates or acrylates and hydrophobic monomers comprising at least one fatty chain such as for example the polyethylene glycol methacrylate / lauryl methacrylate copolymer.
- polyether polyurethanes comprising in their chain, both hydrophilic sequences of a nature most often polyoxyethylenated and hydrophobic sequences which can be aliphatic sequences alone and / or cycloaliphatic and / or aromatic sequences.
- polymers with an aminoplast ether skeleton having at least one fatty chain such as the PURE THIX compounds offered by the company SUD-CHEMIE.
- the polyether polyurethanes comprise at least two lipophilic hydrocarbon chains, having from 6 to 30 carbon atoms, separated by a hydrophilic block, the hydrocarbon chains being able to be pendant chains or chains at the end of hydrophilic block.
- the polymer may comprise a hydrocarbon chain at one end or at both ends of a hydrophilic block.
- the polyether polyurethanes can be multiblock in particular in the form of a triblock.
- the hydrophobic blocks can be at each end of the chain (for example: triblock copolymer with hydrophilic central block) or distributed both at the ends and in the chain (multiblock copolymer for example).
- nonionic fatty chain polyurethane polyethers can be triblock copolymers whose hydrophilic block is a polyoxyethylenated chain comprising from 50 to 1000 oxyethylenated groups.
- Non-ionic polyether polyurethanes have a urethane bond between the hydrophilic blocks, hence the origin of the name.
- non-ionic polyether polyurethanes with a fatty chain which can be used in the invention, it is also possible to use Rheolate 205 with urea function sold by the company RHEOX or Rheolates 208, 204 or 212, as well as Acrysol RM 184. Mention may also be made of the product ELFACOS T210 with a C 12-14 alkyl chain and the product ELFACOS T212 with a C 18 alkyl chain from AKZO. • The product DW 1206B from ROHM & HAAS with a C 2 o alkyl chain and a urethane bond, available at 20% dry matter in water, can also be used.
- solutions or dispersions of these polymers are Rheolate 255, Rheolate 278 and Rheolate 244 sold by the company RHEOX.
- Rheolate 255, Rheolate 278 and Rheolate 244 sold by the company RHEOX.
- polyether polyurethanes which can be used according to the invention are in particular those described in the article by G. Fonnum, J. Bakke and Fk. Hansen - Colloid Polym. Sci 271, 380.389 (1993J.
- a polyether polyurethane capable of being obtained by polycondensation of at least three compounds comprising (i) at least one polyethylene glycol comprising from 150 to 180 moles of ethylene oxide, ( ii) stearyl alcohol or decyl alcohol and (iii) at least one diisocyanate.
- Aculyn 46 is a polycondensate of
- ACULYN 44 is a polycondensate of polyethylene glycol with 150 or 180 moles of ethylene oxide, decyl alcohol and methylene bis (4-cyclohexylisocyanate) (SMDI), at 35% by weight in a mixture of propylene glycol (39 %) and water (26%)].
- the associative polymers of nonionic, anionic, cationic or amphoteric type are preferably used in an amount which can vary from approximately 0.1 to 10% by weight of the total weight of the coloring composition. More preferably, this amount varies from about 0.5 to 5% by weight, and even more particularly from about 1 to 3% by weight.
- 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 6 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.
- 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;
- R4, R5, R ⁇ > identical or different, represent an alkyl group having from 1 to 18 carbon atoms or a benzyl radical and preferably an alkyl group having from 1 to 6 carbon atoms;
- Ri and R2, identical or different, represent hydrogen or an alkyl group having
- 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 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.
- 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 vis-a '-vis a bis-halohydrin, a bis-azetidinium, a bis-haloacyldiamine, a bis-alkyl halide, 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 polyamin
- adipic acid / dimethylaminohydroxypropyl / diethylene triamine polymers sold under the name "Cartaretine F, F4 or F8" by the company Sandoz.
- Rg denotes a hydrogen atom or a methyl radical
- R7 and RQ 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 atoms.
- R7 and R8 may denote, jointly with the nitrogen atom to which they are attached, heterocyclic groups, such as piperidinyl or morpholinyl; R7 and RQ 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. These polymers are described in particular in French patent 2,080,759 and in its certificate of addition 2,190,406.
- R14 is alkylene and D is a quaternary ammonium group
- 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;
- A1, R10 and R12 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 - (CH 2 ) n-CO-D-OC- (CH 2 ) n- in which n is between 1 and 100 and preferably between 1 and 50, and D denotes: a) a glycol residue of formula: -OZO-, where Z denotes a linear or branched hydrocarbon radical or a group corresponding to one of the following formulas:
- x and y denote an integer from 1 to 4, representing a defined and unique degree of polymerization or any number of 1 to 4 representing an average degree of polymerization; b) a bis-secondary diamine residue such as a piperazine derivative; c) a bis-primary diamine residue of formula: -NH-Y-NH-, where Y denotes a linear or branched hydrocarbon radical, or else the bivalent radical
- X " is an anion such as chloride or bromide.
- These polymers have a number average molecular weight generally between 1000 and 100,000.
- 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, ( 3 C NMR) being approximately 25500.
- a crosslinked acrylamide / methacryloyloxyethyltrimethylammonium chloride copolymer (20/80 by weight) can more particularly be used in the form of a dispersion containing 50% by weight of said copolymer in mineral oil.
- This dispersion is marketed under the name of "SALCARE® SC 92" by the company ALLIED COLLOIDS.
- 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), (6), (7) (8) and (11) and even more preferably the polymers with recurring units 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 composition 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 K and M units distributed statistically in the polymer chain, where K denotes a unit derived 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 deriving from zwitterionic monomers of carboxybetaines or of sulphobetaines;
- 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 secondary amine groups.
- amphoteric polymers corresponding to the definition given above which are more particularly preferred are chosen from the following polymers:
- the substituted vinyl compound containing at least one basic atom 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.
- Polymers comprising units derived from: a) at least one monomer chosen from acrylamides or methacrylamides substituted on nitrogen with an alkyl radical, b) at least one acidic comonomer containing one or more reactive carboxylic groups, and c) at least one basic comonomer such as esters with primary, secondary, tertiary and quaternary amino substituents of acrylic and methacrylic acids and the product of quaternization of dimethylaminoethyl methacrylate with dimethyl or diethyl sulfate.
- the N-substituted acrylamides or methacrylamides which are more particularly preferred according to the invention are groups whose 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 ⁇ g 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 a primary bis or secondary bis amino
- 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
- the saturated carboxylic acids are preferably chosen from acids having 6 to
- adipic acid such as adipic acid, trimethyl-2,2,4-adipic and trimethyl-2,4,4-adipic, terephthalic, acids with ethylenic double bond like 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. 40
- R 25 represents a radical of formula:
- R29 represents a hydrogen atom, a CH3O radical, CH3CH2O, phenyl
- R30 denotes hydrogen or a lower alkyl radical such as methyl, ethyl
- R3I 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 (R3i) 2, R33 representing a group -CH 2 -CH 2 -, -CH 2 -CH 2 -CH 2- , -CH 2 -CH (CH3) -, R31 having the meanings mentioned above, as well as the higher homologs of these radicals and containing up to 6 carbon atoms,
- r is such that the molecular weight is between 500 and 6,000,000 and preferably between 1,000 and 1,000,000.
- Amphoteric polymers of the -DXDX- type chosen from: a) the polymers obtained by the action of chloracetic acid or sodium chloroacetate on the compounds comprising at least one unit of formula: -DXDXD- (XVII) where D denotes a radical
- ⁇ / and X denotes the symbol E or E ', E or E', which are identical or different, denote a bivalent radical which is an alkylene radical with a straight or branched chain 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; b) polymers of formula:
- 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, whether or not substituted 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.
- N, N-dimethylaminopropylamine or by semiesterification with an N, N-dialcanolamine is N, N-dimethylaminopropylamine or by semiesterification with an N, N-dialcanolamine.
- 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 which can be chosen indifferently, alone or in mixtures, from anionic, amphoteric, nonionic, zwitterionic and cationic surfactants.
- surfactants which are suitable for carrying out the present invention are in particular the following:
- anionic surfactants which can be used, alone or as mixtures, in the context of the present invention, mention may be made in particular (non-limiting list) of the salts (in particular alkali salts, in particular sodium salts, ammonium salts, amine salts, amino alcohol salts or magnesium salts) of the following compounds: alkyl sulfates, alkyl ether sulfates, alkylamidoethersulfates, alkylaryl polyethersulfates, monoglycerides sulfates; alkylsulfonates, alkylphosphates, alkylamidesulfonates, alkylarylsulfonates, ⁇ -olefin-sulfonates, paraffin-sulfonates; (C 6 -C 24 ) alkyl sulfosuccinates, (C 6 - C 2 ) alkyl ethersulfosuccinates, (C 6 -C 24 ) alkyl
- alkyl esters C 6 -C 24 of carboxylic polyglycosides such as alkylglucoside citrates, alkylpolyglycoside tartrate and alkylpolyglycoside sulfosuccinates., Alkylsulfosuccinamates; acylisethionates and N-acyltaurates, the alkyl or acyl radical of all these different compounds preferably containing from 12 to 20 carbon atoms, and the aryl radical preferably denoting a phenyl or benzyl group.
- carboxylic polyglycosides such as alkylglucoside citrates, alkylpolyglycoside tartrate and alkylpolyglycoside sulfosuccinates., Alkylsulfosuccinamates; acylisethionates and N-acyltaurates, the alkyl or acyl radical of all these different compounds preferably containing from
- 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 polyoxyalkylenated (C 6 -C 24 ) alkyl ether carboxylic acids, polyoxyalkylenated (C 6 -C 24 ) aryl ether carboxylic acids, alkyl (C 6 -C 24 ) amido ether carboxylic polyoxyalkylenated and their salts, in particular those comprising from 2 to 50 alkylene oxide groups, in particular ethylene, 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. Thus, 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 groups or propylene oxide which can range in particular from 2 to 50.
- copolymers of ethylene oxide and of propylene, condensates of ethylene oxide and of propylene on fatty alcohols polyethoxylated fatty amides preferably having from 2 to 30 moles of ethylene oxide, polyglycerolated fatty amides comprising on average 1 to 5 glycerol groups and in particular 1, 5 to 4; polyethoxylated fatty amines preferably having 2 to 30 moles of ethylene oxide; esters of oxyethylenated sorbitan fatty acids having from 2 to 30 moles of ethylene oxide; sucrose fatty acid esters, polyethylene glycol fatty acid esters, alkylpolyglycosides, N-alkyl glucamine derivatives, amine oxides such as alkyl oxides (C-JQ - C-14) amines or N-acylaminopropylmorpholine oxides.
- the alkylpolyglycosides constitute nonionic surfactants
- 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 the (C8-C20) alkyl betaines, the sulfobetaines, the (C8-C20) alkyl amidoalkyl (C- j -Cg) betaines or the (C8-C20) amidoalkyl (O1-C6) sulfobetaines alkyls.
- 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,
- B represents -CH 2 CH2 ⁇ X '
- 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
- R2 'de notes an alkyl radical of an acid Rg -COOH present in coconut oil or in hydrolysed linseed oil, an alkyl radical, especially in C7, Cg, C- j ⁇
- 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, of alkylamidoaikyltrialkylammonium, of trialkylbenzylammonium, of trialkylhydroxyalkyl-ammonium or alkylpyridinium; imidazoline derivatives; or amine oxides of a cationic nature.
- the amounts of surfactants present in the composition according to the invention can vary from 0.01 to 40% and preferably from 0.5 to 30% of the total weight of the composition.
- Said composition can also contain reducing or antioxidant agents. These can be chosen in particular from sodium sulfite, thioglycolic acid, thiolactic acid, sodium bisulfite, dehydroascorbic acid, hydroquinone, 2-methyl-hydroquinone, terbutyl- hydroquinone and homogentisic acid, and they are then usually present in amounts ranging from about 0.05 to . 3% by weight relative to the total weight of the composition.
- reducing or antioxidant agents can be chosen in particular from sodium sulfite, thioglycolic acid, thiolactic acid, sodium bisulfite, dehydroascorbic acid, hydroquinone, 2-methyl-hydroquinone, terbutyl- hydroquinone and homogentisic acid, and they are then usually present in amounts ranging from about 0.05 to . 3% by weight relative to the total weight of the composition.
- the oxidizing agent is preferably chosen from hydrogen peroxide, urea peroxide, bramates or ferricyanides of alkali metals, persalts such as perborates and persulfates .
- the use of hydrogen peroxide is particularly preferred.
- This oxidizing agent advantageously consists of a solution of hydrogen peroxide, the titer of which can vary, more particularly, from approximately 1 to 40 volumes, and even more preferably from approximately 5 to 40.
- oxidoreductipn enzymes such as laccases, peroxidases and oxidoreductases with 2 electrons (such as uricase), where appropriate in the presence of their respective donor or cofactor.
- the pH of the composition is generally between the values 2 and 12. It is preferably between 3 and 11, and more particularly between 7 and 10. It can be adjusted to the value desired by means of acidifying or basifying agents or buffers well known in the state of the art in dyeing keratin fibers. More preferably when the composition contains an oxidizing agent for lightening the fibers, the pH of the ready-to-use mixture is greater than 7 and even more preferably greater than 8.
- basifying agents there may be mentioned, by way of example, ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines as well as their derivatives, hydroxyalkylamines and ethylenediamines oxyethylenated and / or oxypropylenes, sodium or potassium hydroxides and the compounds of formula (XIX) below:
- R is a propylene residue optionally substituted by a hydroxyl group or a CC alkyl radical
- R 38 , R 39 , R o and R 4 ⁇ identical or different, represent a hydrogen atom, an alkyl radical in C r C 4 or hydroxyalkyl in dC.
- 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.
- buffers mention may be made of those sold by the company MERCK under the brand TITRISOL, such as the phosphate buffer (KH 2 P ⁇ 4 at 0.026 mole / l, Na2HP ⁇ 4 at 0.041 mole / l), and the borate buffer (H3BO3 at 0 , 05 mole / l, KCI at 0.05 mole / l, NaOH at 0.022 mole / l).
- the dyeing process according to the invention is carried out at ambient temperature, and consists in applying the ready-to-use dye composition according to the invention (produced by extemporaneous mixing at the time of use of the dye composition and the oxidizing composition) on dry or wet keratin fibers, and leaving it to act for a pause time varying from 5 seconds to approximately 60 minutes, more preferably from 10 seconds to approximately 5 minutes, and more particularly from 30 seconds to approximately 2 minutes , rinse the fibers, then optionally wash them with shampoo, then rinse them again, and dry them.
- the method according to the invention has the advantage of requiring only very short application times, of the order of 10 seconds to 5 minutes and more particularly from 30 seconds to 2 minutes.
- compositions of Examples 1 and 2 were applied, on the one hand to locks of natural gray hair containing 90% white hairs, on the other hand to locks of permanent gray hair containing 90% white hairs, for 35 minutes at room temperature (20 ° C).
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Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/480,380 US7172631B2 (en) | 2001-06-12 | 2002-06-07 | Dyeing composition for human keratinous fibers with oxidation dyes and dicationic compounds |
JP2003503190A JP2005512950A (ja) | 2001-06-12 | 2002-06-07 | 酸化染料およびジカチオン化合物を含むヒトのケラチン繊維を染色するための組成物 |
DE60229643T DE60229643D1 (de) | 2001-06-12 | 2002-06-07 | Zusammensetzung zur färbung von menschlichen keratd dikationische verbindungen |
EP02747518A EP1416908B1 (fr) | 2001-06-12 | 2002-06-07 | Composition de teinture des fibres keratiniques humaines avec des colorants d'oxydation et des composes dicationiques |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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FR0107680A FR2825623B1 (fr) | 2001-06-12 | 2001-06-12 | Composition de teinture des fibres keratiniques humaines avec des colorants d'oxydation et des composes dicationiques |
FR01/07680 | 2001-06-12 |
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WO2002100366A2 true WO2002100366A2 (fr) | 2002-12-19 |
WO2002100366A3 WO2002100366A3 (fr) | 2004-02-19 |
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PCT/FR2002/001964 WO2002100366A2 (fr) | 2001-06-12 | 2002-06-07 | Composition de teinture des fibres keratiniques humaines avec des colorants d'oxydation et des composes dicationiques |
Country Status (7)
Country | Link |
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US (1) | US7172631B2 (fr) |
EP (1) | EP1416908B1 (fr) |
JP (1) | JP2005512950A (fr) |
AT (1) | ATE412451T1 (fr) |
DE (1) | DE60229643D1 (fr) |
FR (1) | FR2825623B1 (fr) |
WO (1) | WO2002100366A2 (fr) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2872163A1 (fr) * | 2004-06-23 | 2005-12-30 | Oreal | Composes diazoiques cationiques particuliers, compositions les comprenant a titre de colorant direct, procede de coloration de fibres keratiniques et dispositif |
FR2872161A1 (fr) * | 2004-06-23 | 2005-12-30 | Oreal | Composes diazoiques cationiques particuliers, compositions les comprenant a titre de colorant direct, procede de coloration de fibres keratiniques et disposirif |
FR2872162A1 (fr) * | 2004-06-23 | 2005-12-30 | Oreal | Composes diazoiques cationiques particuliers, compositions les comprenant a titre de colorant direct, procede de coloration de fibres keratiniques et dispositif |
FR2872160A1 (fr) * | 2004-06-23 | 2005-12-30 | Oreal | Composes diazoiques cationiques, compositions les comprenant a titre de colorant direct, procede de coloration de fibres keratiniques et dispositif |
WO2006056489A2 (fr) * | 2004-11-26 | 2006-06-01 | L'oreal | Composes polyazo cationiques dissymetriques particuliers, compositions comprenant ces composes utilises comme colorant direct, processus de coloration de fibres de keratine et dispositif a cet effet |
FR2879196A1 (fr) * | 2004-12-15 | 2006-06-16 | Oreal | Composes diaz0iques symetriques a groupements 2-imidazolium et bras de liaison non cationique, compositions les comprenant, procede de coloration et dispositif |
US7247713B2 (en) | 2004-12-15 | 2007-07-24 | L'oreal, S.A. | Symmetrical diazo compounds containing 2-pyridinium groups and cationic or non-cationic linker, compositions comprising them, method of coloring, and device |
US7282069B2 (en) | 2004-06-23 | 2007-10-16 | L'oreal S.A. | Cationic diazo compounds, compositions comprising them as direct dye, process for dyeing keratin fibers and device therefor |
US7285138B2 (en) | 2004-06-23 | 2007-10-23 | L'oreal, S.A. | Cationic diazo compound, compositions comprising at least one cationic diazo compound as a direct dye, a process for dyeing keratin fibers and device therefore |
US7288122B2 (en) | 2004-06-23 | 2007-10-30 | L'oreal S.A. | Cationic diazo compounds, compositions comprising them as direct dye, process for dyeing keratin fibers and device therefor |
US7288639B2 (en) | 2004-12-15 | 2007-10-30 | L'oreal S.A. | Dyssymmetrical diazo compounds having at least one 4-pyridinium unit and a cationic or non-cationic linker, compositions comprising them, method of coloring, and device |
US7396368B2 (en) | 2004-12-15 | 2008-07-08 | L'oreal S.A. | Symmetrical diazo compounds comprising 4-pyridinium groups and a cationic or non-cationic linker, compositions comprising them, method for coloring, and device |
US7438728B2 (en) | 2004-12-15 | 2008-10-21 | L'oreal S.A. | Dissymmetrical diazo compounds comprising 2-pyridinium group and a cationic or non-cationic linker, compositions comprising them, method for coloring, and device |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7410506B2 (en) | 2004-10-14 | 2008-08-12 | L'oreal S.A. | Dicationic bis-hydrazone compound, dye composition comprising at least one such compound, implementation process therefor and uses thereof |
FR2876690B1 (fr) * | 2004-10-14 | 2007-04-06 | Oreal | Compose bis-hydrazone dicationique, composition tinctoriale comprenant au moins un tel compose, procede de mise en oeuvre et utilisations |
FR2879199B1 (fr) * | 2004-12-15 | 2007-02-02 | Oreal | Composes diazoiques symetriques a groupements 2-imidazolium et bras de liaison cationique, compositions les comprenant, procede de coloration et dispositif |
US20090062517A2 (en) * | 2004-12-15 | 2009-03-05 | L'oreal S.A. | Dissymmetrical Diazo Compounds Containing Having at Least One 2-imidazolium Unit and a Cationic or Non-cationic Linker, Compositions Comprising Them, Method of Coloring, and Device |
DE102005015329A1 (de) * | 2005-04-01 | 2006-10-19 | Henkel Kgaa | Mittel zum Färben von keratinhaltigen Fasern |
FR2920781B1 (fr) * | 2007-09-11 | 2009-11-20 | Oreal | Composes azoiques cationiques thiol/disulfures, compositions les comprenant, procede de coloration de fibres keratiniques et dispositif. |
DE102014223935A1 (de) | 2014-11-25 | 2016-05-25 | Henkel Ag & Co. Kgaa | Mittel zum Färben von keratinischen Fasern, enthaltend mindestens einen dimeren, dikationischen Azofarbstoff und mindestens ein anionisches und/oder kationisches Tensid |
DE102014223939A1 (de) | 2014-11-25 | 2016-05-25 | Henkel Ag & Co. Kgaa | Mittel zum Färben von keratinischen Fasern, enthaltend mindestens einen dimeren, dikationischen Azofarbstoff und mindestens ein anionisches Tensid |
DE102014223938A1 (de) | 2014-11-25 | 2016-05-25 | Henkel Ag & Co. Kgaa | Mittel zum Färben von keratinischen Fasern, enthaltend mindestens einen dimeren, dikationischen Azofarbstoff und mindestens ein nichtionisches Tensid |
DE102014223936A1 (de) * | 2014-11-25 | 2016-05-25 | Henkel Ag & Co. Kgaa | Mittel zum Färben von keratinischen Fasern, enthaltend mindestens einen dimeren, dikationischen Azofarbstoff mit speziellem Substitutionsmuster |
DE102014223937A1 (de) | 2014-11-25 | 2016-05-25 | Henkel Ag & Co. Kgaa | Mittel zur Farbveränderung von keratinischen Fasern, enthaltend mindestens einen dimeren, ringvergbrückten Azofarbstoff |
US11596612B1 (en) | 2022-03-08 | 2023-03-07 | PTC Innovations, LLC | Topical anesthetics |
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- 2001-06-12 FR FR0107680A patent/FR2825623B1/fr not_active Expired - Fee Related
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- 2002-06-07 JP JP2003503190A patent/JP2005512950A/ja not_active Withdrawn
- 2002-06-07 WO PCT/FR2002/001964 patent/WO2002100366A2/fr active Application Filing
- 2002-06-07 US US10/480,380 patent/US7172631B2/en not_active Expired - Fee Related
- 2002-06-07 EP EP02747518A patent/EP1416908B1/fr not_active Expired - Lifetime
- 2002-06-07 AT AT02747518T patent/ATE412451T1/de not_active IP Right Cessation
- 2002-06-07 DE DE60229643T patent/DE60229643D1/de not_active Expired - Lifetime
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US3578386A (en) * | 1967-02-22 | 1971-05-11 | Oreal | Dyeing human hair with benzothiazole azo compounds |
EP0318294A2 (fr) * | 1987-11-24 | 1989-05-31 | Nippon Chemical Works Co., Ltd | Colorants cationiques dimères et trimères |
DE4128490A1 (de) * | 1991-08-28 | 1993-03-04 | Bitterfeld Wolfen Chemie | Neue kationische thiazolazofarbstoffe |
EP0696619A1 (fr) * | 1994-07-15 | 1996-02-14 | Ciba-Geigy Ag | Procédé pour colorer du papier |
US5708151A (en) * | 1994-11-03 | 1998-01-13 | Ciba Specialty Chemicals Corporation | Cationic imidazole azo dyes |
DE19802940A1 (de) * | 1998-01-27 | 1999-08-05 | Wella Ag | Neue kationische Farbstoffe, Verfahren zu deren Herstellung und diese Farbstoffe enthaltende Färbemittel für Keratinfasern |
FR2779054A1 (fr) * | 1998-05-26 | 1999-12-03 | Oreal | Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition |
EP1022016A2 (fr) * | 1999-01-19 | 2000-07-26 | L'oreal | Utilisation de composés phényl-azo-benzéniques cationiques en teinture des fibres kératiniques, compositions tinctoriales et procédés de teinture |
EP1133975A2 (fr) * | 2000-03-17 | 2001-09-19 | Kao Corporation | Teinture de cheveux |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7282069B2 (en) | 2004-06-23 | 2007-10-16 | L'oreal S.A. | Cationic diazo compounds, compositions comprising them as direct dye, process for dyeing keratin fibers and device therefor |
US7285138B2 (en) | 2004-06-23 | 2007-10-23 | L'oreal, S.A. | Cationic diazo compound, compositions comprising at least one cationic diazo compound as a direct dye, a process for dyeing keratin fibers and device therefore |
US7288122B2 (en) | 2004-06-23 | 2007-10-30 | L'oreal S.A. | Cationic diazo compounds, compositions comprising them as direct dye, process for dyeing keratin fibers and device therefor |
FR2872160A1 (fr) * | 2004-06-23 | 2005-12-30 | Oreal | Composes diazoiques cationiques, compositions les comprenant a titre de colorant direct, procede de coloration de fibres keratiniques et dispositif |
EP1619221A1 (fr) * | 2004-06-23 | 2006-01-25 | L'oreal | Composés diazoiques cationiques particuliers compositions les comprenant à titre de colorant direct procédé de coloration de fibres kératiniques et dispositif |
EP1619220A1 (fr) * | 2004-06-23 | 2006-01-25 | L'Oreal-D.I.P.I. | Composes diazoiques cationiques particuliers, compositions les comprenant à titre de colorant direct, procédé de coloration de fibres kératiniques et dispositif |
EP1634926A1 (fr) * | 2004-06-23 | 2006-03-15 | L'oreal | Composés diazoiques cationiques particuliers, compositions les comprenant à titre de colorant direct, procédé de coloration de fibres kératiniques et dispositif |
EP1637566A1 (fr) * | 2004-06-23 | 2006-03-22 | L'oreal | Composés diazoiques cationiques, compositions les comprenant à titre de colorant direct, procédé de coloration de fibres kératiniques et dispositif |
FR2872161A1 (fr) * | 2004-06-23 | 2005-12-30 | Oreal | Composes diazoiques cationiques particuliers, compositions les comprenant a titre de colorant direct, procede de coloration de fibres keratiniques et disposirif |
FR2872163A1 (fr) * | 2004-06-23 | 2005-12-30 | Oreal | Composes diazoiques cationiques particuliers, compositions les comprenant a titre de colorant direct, procede de coloration de fibres keratiniques et dispositif |
FR2872162A1 (fr) * | 2004-06-23 | 2005-12-30 | Oreal | Composes diazoiques cationiques particuliers, compositions les comprenant a titre de colorant direct, procede de coloration de fibres keratiniques et dispositif |
US7208586B2 (en) | 2004-06-23 | 2007-04-24 | L'oreal S.A. | Cationic diazo compounds, compositions comprising them as direct dye, process for dyeing keratin fibers and device therefor |
FR2878527A1 (fr) * | 2004-11-26 | 2006-06-02 | Oreal | Composes polyazoiques cationiques dissymetriques particuliers, compositions les comprenant a titre de colorant direct, procede de coloration de fibres keratiniques et dispositif |
WO2006056489A3 (fr) * | 2004-11-26 | 2006-10-19 | Oreal | Composes polyazo cationiques dissymetriques particuliers, compositions comprenant ces composes utilises comme colorant direct, processus de coloration de fibres de keratine et dispositif a cet effet |
WO2006056489A2 (fr) * | 2004-11-26 | 2006-06-01 | L'oreal | Composes polyazo cationiques dissymetriques particuliers, compositions comprenant ces composes utilises comme colorant direct, processus de coloration de fibres de keratine et dispositif a cet effet |
US7438728B2 (en) | 2004-12-15 | 2008-10-21 | L'oreal S.A. | Dissymmetrical diazo compounds comprising 2-pyridinium group and a cationic or non-cationic linker, compositions comprising them, method for coloring, and device |
US7247713B2 (en) | 2004-12-15 | 2007-07-24 | L'oreal, S.A. | Symmetrical diazo compounds containing 2-pyridinium groups and cationic or non-cationic linker, compositions comprising them, method of coloring, and device |
FR2879196A1 (fr) * | 2004-12-15 | 2006-06-16 | Oreal | Composes diaz0iques symetriques a groupements 2-imidazolium et bras de liaison non cationique, compositions les comprenant, procede de coloration et dispositif |
US7288639B2 (en) | 2004-12-15 | 2007-10-30 | L'oreal S.A. | Dyssymmetrical diazo compounds having at least one 4-pyridinium unit and a cationic or non-cationic linker, compositions comprising them, method of coloring, and device |
US7351267B2 (en) | 2004-12-15 | 2008-04-01 | L'oreal S.A. | Symmetrical diazo compounds comprising 2-imidazolium groups and a non-cationic linke, compositions comprising them, method of coloring, and device |
US7396368B2 (en) | 2004-12-15 | 2008-07-08 | L'oreal S.A. | Symmetrical diazo compounds comprising 4-pyridinium groups and a cationic or non-cationic linker, compositions comprising them, method for coloring, and device |
KR100851260B1 (ko) * | 2004-12-15 | 2008-08-08 | 로레알 | 2-이미다졸륨기 및 비-양이온성 링커를 함유한 대칭 디아조화합물, 이를 함유하는 조성물, 착색 방법 및 장치 |
EP1671955A1 (fr) * | 2004-12-15 | 2006-06-21 | L'oreal | Composés diazoiques symetriques à groupements 2-imidazolium et bras de liaison non cationique, compositions les comprenant, procédé de coloration et dispositif |
Also Published As
Publication number | Publication date |
---|---|
EP1416908B1 (fr) | 2008-10-29 |
WO2002100366A3 (fr) | 2004-02-19 |
US20040244124A1 (en) | 2004-12-09 |
FR2825623A1 (fr) | 2002-12-13 |
JP2005512950A (ja) | 2005-05-12 |
EP1416908A2 (fr) | 2004-05-12 |
DE60229643D1 (de) | 2008-12-11 |
US7172631B2 (en) | 2007-02-06 |
FR2825623B1 (fr) | 2005-04-08 |
ATE412451T1 (de) | 2008-11-15 |
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