WO2000043386A1 - Cationic di-benzene dyeing agents, use for oxidation dyeing of keratin fibres, dyeing compositions and dyeing method - Google Patents
Cationic di-benzene dyeing agents, use for oxidation dyeing of keratin fibres, dyeing compositions and dyeing method Download PDFInfo
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- WO2000043386A1 WO2000043386A1 PCT/FR2000/000094 FR0000094W WO0043386A1 WO 2000043386 A1 WO2000043386 A1 WO 2000043386A1 FR 0000094 W FR0000094 W FR 0000094W WO 0043386 A1 WO0043386 A1 WO 0043386A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/61—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
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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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
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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
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
Definitions
- the subject of the invention is new di-benzenic dyes comprising at least one cationic group Z, Z being chosen from quaternized aliphatic chains, aliphatic chains comprising at least one quaternized saturated cycle, and aliphatic chains comprising at least one unsaturated cycle quaternized, their use as oxidation dye precursors for the oxidation dyeing of keratin fibers, the dye compositions containing them, as well as the oxidation dyeing processes using them.
- oxidation dye precursors in particular paraphenylenediamines, ortho or paraaminophenols, heterocyclic compounds such as diaminopyrazole derivatives, generally called bases.
- bases oxidation dye precursors
- oxidation dye precursors in particular paraphenylenediamines, ortho or paraaminophenols, heterocyclic compounds such as diaminopyrazole derivatives, generally called bases.
- oxidation dye precursors in particular paraphenylenediamines, ortho or paraaminophenols, heterocyclic compounds such as diaminopyrazole derivatives, generally called bases.
- oxidation dye precursors in particular paraphenylenediamines, ortho or paraaminophenols, heterocyclic compounds such as diaminopyrazole derivatives, generally called bases.
- oxidation dye precursors in particular paraphenylenediamines, ortho or paraaminophenols, heterocyclic compounds such as diaminopyrazole derivatives, generally called bases.
- the dyes must also make it possible to cover the 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.
- new cationic di-benzene dyes of formula (I) defined below comprising at least one cationic group Z, Z being chosen from quaternized aliphatic chains, aliphatic chains comprising at least one quaternized saturated ring, and aliphatic chains comprising at least one unsaturated quaternized ring, not only are suitable for use as oxidation dye precursors for the oxidation dyeing of keratin fibers, but also that 'they make it possible to obtain dye compositions leading to powerful colorings, in a wide palette of colors, and having excellent resistance properties to the various treatments which keratin fibers can undergo.
- the first object of the invention is therefore new compounds of the following formula (I), and their addition salts with an acid:
- B is a linking arm which represents an alkyl chain preferably having from 1 to 14 carbon atoms, linear or branched which can be interrupted by one or more Z 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 6 -C 6 alkoxy radicals, and which can carry one or more ketone functions;
- a ReasonA 2 , and A 3 identical or different, represent a group -NR 7 R 8 or a hydroxyl radical; one and only one of the groups A. ,, A 2 and A 3 may also represent a group R 3 as defined below;
- A, A ' 2 and A' 3 identical or different, represent a group -NR ' 7 R' 8 or a hydroxyl radical; one and only one of the groups A ' 1 t A' 2 and A ' 3 can also represent a group R' 3 as defined below;
- R. ,, R, R 2 , R ' 2 , R 3 and R' 3 which may be identical or different, represent one of the two valences of a link arm B, a hydrogen atom; a halogen atom; a group Z as defined below; an alkyl (CC 6 ) carbonyl radical; an aminoalkyl radical (C., - C 6 ) carbonyl; an NZ-aminoalkyl (C r C 6 ) carbonyl radical; an N-(C 1 -C 6 ) aminoalkyl (C 1 -C 6 ) carbonyl radical; an N, N-dialkyl (CC 6 ) aminoalkyl (C r C 6 ) carbonyl radical; an aminoalky radical ⁇ C ! -
- CC 6 a CC 6 monohydroxyalkyl radical; a C 2 -C 6 polyhydroxyalkyl radical; alkoxy (CC 6) C r C 6; a CC 6 trifluoroalkyl radical; a cyano radical; an ORg, SR 6 , OR ' 6 or SR' 6 group ; an amino group protected by an alky ⁇ C ⁇ C ⁇ carbonyl, (C, - C 6 ) carboxy, C ⁇ C ⁇ carbonyl, aminoalkyl (C., - C 6 ) carbonyl radical,
- R 6 and R ' 6 denote one of the two valences of a linking arm B, an alkyl radical in CC 6 ; a monohydroxyalkyl radical in; a C 2 -C 6 polyhydroxyalkyl radical; a group Z as defined below; a CC 6 alkoxy (C 1 -C 6 ) alkyl radical; an aryl radical; a benzyl radical; a CC 6 carboxyalkyl radical; an alkyl radical (CC 6) carboxyalkyl CC 6; a CC 6 cyanoalkyl radical; a CC 6 carbamylalkyl radical; an N-alkyl (C 1 -C 6 ) carbamylalkyl radical in ; a radical ; a CC 6 trifluoroalkyl radical; an aminosulfonylalkyl radical in ; a CC 6 NZ-aminosulfonylalkyl radical; an N-alkyl (
- R 4 , R ' 4 , R 5 , R' 5) R 7 , R ' 7) R 8 and R' 8 represent one of the two valences of a link arm B, an atom hydrogen; a group Z as defined below in which the link arm D does not contain a ketone function directly linked to the nitrogen atom of said amino group; a CC 6 alkyl radical; a CC 6 monohydroxyalkyl radical; a C 2 -C 6 polyhydroxyalkyl radical; alkoxy (CC 6) alkyl, CC 6; an aryl radical; a benzyl radical; a C., - C 6 cyanoalkyl radical; a C 1 -C 6 carbamylalkyl radical; an N-alky radical ⁇ C !
- D is a linking arm which represents an alkyl chain preferably having from 1 to 14 carbon atoms, linear or branched which can be interrupted by one or more heteroatoms such as oxygen, sulfur or nitrogen atoms, and which can be substituted by one or more hydroxyl or alkoxy radicals in and can carry one or more ketone functions;
- the vertices E, G, J, L and M identical or different, represent a carbon, oxygen, sulfur or nitrogen atom;
- n is an integer between 0 and 4 inclusive;
- m is an integer between 0 and 5 inclusive;
- the radicals R which are identical or different, represent one of the two valences of a linking arm B, a second group Z identical to or different from the first group Z, a halogen atom, a radical hydroxyl, an alkyl radical in CC 6 , a monohydroxyalkyl radical in a polyhydroxyalkyl radical in C 2 -C 6 , a nitro radical, a cyano radical, a
- R 9 represents one of the two valences of a connecting arm B, an alkyl radical in C, -C 6 , a monohydroxyalkyl radical in CC 6 , a polyhydroxyalkyl radical in C 2 -C 6 , a cyanoalkyl radical in CC 6 , a trialkyl (CC 6 ) silanealkyl radical in CC 6 , an alkoxy (C 1 -C 6 ) alkyl CC 6 , a carbamylalkyl radical in CC 6 , a benzyl radical, or a second group Z identical to or different from the first group Z;
- R 10 , R and R 12 represent one of the two valences of a linking arm B, an alkyl radical in a monohydroxyalkyl radical in C ⁇ Ce, a polyhydroxyalkyl radical in C 2 -C 6 , an alkoxy (C 1 -C 6 ) alkyl in CC 6 , a cyanoalkyl radical in C r C 6 , an aryl radical, a benzyl radical, an amidoalkyl radical CC 6, a radical trialkyl (CC 6) alkylsilane CC 6 or an aminoalkyl radical in carbamyl, or alkyl (CC 6 ) sulfonyl;
- two of the radicals R 10 , R passerand R 12 can also form together, with the nitrogen atom to which they are attached, a saturated 5 or 6-membered carbon ring or containing one or more heteroatoms such as for example a pyrrolidine ring , a cycle piperidine, a pipe
- one of the radicals R 10 , R 2 and R 12 can also represent a second group Z, identical or different from the first group Z;
- R 13 represents one of the two valences of a linking arm B, a CC 6 alkyl radical; a CC 6 monohydroxyalkyl radical; a C 2 -C 6 polyhydroxyalkyl radical; an aryl radical; a benzyl radical; a C r C 6 aminoalkyl radical, a C 6 aminoalkyl radical the amine of which is protected by an alkyl (C r C 6 ) carbonyl, carbamyl or alkyl (CC 6 ) sulfonyl radical; a CC 6 carboxyalkyl radical; a CC 6 cyanoalkyl radical; a CC 6 carbamylalkyl radical; a CC 6 trifluoroalkyl radical; a CC 6 trialkyl ⁇ -C ⁇ silanealkyle radical; a sulfonamidoalkyl radical in ; a radical in ; an alkyl (C 1 -C 6) sulf ⁇ ny
- CC 6 a C 6 -C 6 carbamylalkyl N-alkyl radical CC 6 ; an N-C 1 -C 6 sulfonamidoalkyl radical CC 6 ;
- - y can only take the value 1: 1) when the vertices E, G, J and L simultaneously represent a carbon atom, and the radical R 9 is carried by the nitrogen atom of the unsaturated cycle; or
- - y can only take the value 1 when at least one of the vertices E, G, J, L and M represents a divalent atom, and the radical R 9 is carried by the nitrogen atom of the unsaturated cycle; - in the cationic groups of formula (IV):
- X represents a monovalent or divalent anion and is preferably chosen from a halogen atom such as chlorine, bromine, fluorine or iodine, a hydroxide, a hydrogenesulfate, or a such as for example a methyl sulphate or an ethyl sulphate;
- the colorings obtained with the oxidation dye composition containing the dye (s) of formula (I) according to the invention are powerful and make it possible to achieve a wide palette of colors. They also have excellent resistance properties with regard to the action of various external agents (light, bad weather, washing, permanent waving, perspiration, friction). These properties are particularly remarkable in particular with regard to the resistance of the colorings obtained with respect to the action of light, washing, permanent waving and perspiration.
- alkyl and alkoxy radicals can be linear or branched.
- cycles of the unsaturated groups Z of formula (II) above mention may in particular be made, by way of example, of the pyrrolic, imidazolic, pyrazolic, oxazolic, thiazolic and thazolic cycles.
- cycles of the unsaturated groups Z of formula (III) above mention may in particular be made, by way of example, of the pyridine, pyrimidine, pyrazine, oxazine and triazine cycles.
- the compounds of formula (I) above are preferably chosen from:
- the acid addition salts of the compounds of formula (I) are preferably chosen from hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates and acetates.
- the compounds of formula (I) in accordance with the invention can be easily obtained, according to methods well known from the state of the art, by reduction of the corresponding cationic di-benzene nitro compounds.
- This reduction step (obtaining a primary aromatic amine) followed or not by salification, is generally, for convenience, the last step of the synthesis.
- halogenoalkyl radicals carried by the intermediate dibenzene compounds can be prepared by methods known from the prior art, in one or more stages, for example by condensation of a dihaloalkyl compound on an amine or a hydroxyl, or by halogenation of a hydroxyalkyl chain.
- the compounds of formula (I) in accordance with the invention can, if necessary, be recovered by methods well known from the state of the art such as crystallization, distillation.
- Another subject of the invention is the use of the compounds of formulas (I) in accordance with the invention as an oxidation dye precursor for the oxidation dyeing of keratin fibers, and in particular human keratin fibers such than hair.
- a subject of the invention is also a composition for the oxidation dyeing of keratin fibers and in particular human keratin fibers such as the hair, characterized in that it comprises, as oxidation dye precursors, in a medium suitable for dyeing, at least one compound of formula (I) according to the invention.
- the compound (s) of formula (I) according to the invention preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight approximately of this weight .
- the medium suitable for dyeing generally consists of water or a mixture of water and at least one organic solvent to dissolve the compounds which are not sufficiently soluble in water.
- organic solvent mention may, for example, be made of lower C 1 -C 4 alkanols, such as ethanol and isopropanol; glycerol; glycols and ethers of glycols such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, monoethyl ether and monomethyl ether of diethylene glycol, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, analogues and mixtures thereof.
- the solvents may be present in proportions preferably of between 1 and 40% by weight approximately relative to the total weight of the dye composition, and even more preferably between 5 and 30% by weight approximately.
- the pH of the dye composition according to the invention is generally between 3 and 12 approximately, and preferably between 5 and 11 approximately. It can be adjusted to the desired value by means of acidifying or basifying agents usually used in dyeing keratin fibers.
- acidifying agents there may be mentioned, by way of example, mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulfonic acids.
- mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulfonic acids.
- 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, sodium or potassium hydroxides and compounds of following formula (V):
- the dye composition according to the invention may also contain, in addition to the compound or compounds of formula (I) defined above, at least one oxidation base which can be chosen from the oxidation bases conventionally used in dyeing d oxidation and among which there may be mentioned paraphenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases.
- paraphenylenediamines mention may more particularly be made, for example, of paraphenylenediamine, paratoluylenediamine, 2,6-dimethyl paraphenylenediamine, 2- ⁇ -hydroxyethyl paraphenylenediamine, 2-n-propyl paraphenylenediamine, 2-isopropyline paraphenyl , N- ( ⁇ -hydroxypropyl) paraphenylenediamine, N, N-bis- ( ⁇ -hydroxyethyl) paraphenylenediamine, 4-amino N- ( ⁇ -methoxyethyl) aniline, the paraphenylenediamines described in French patent application FR 2 630 438, and their addition salts with an acid.
- para-aminophenol there may be mentioned more particularly by way of example, para-aminophenol, 4-amino 3-methyl phenol, 4-amino
- ortho-aminophenols mention may more particularly be made, for example, of 2-amino phenol, 2-amino 5-methyl phenol, 2-amino 6-methyl phenol, 5-acetamido 2-amino phenol , and their addition salts with an acid.
- heterocyclic bases that may be mentioned more particularly by way of example, pyridine derivatives, non-cationic pyrimidine derivatives and pyrazole derivatives.
- 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, 3,4-diamino pyridine, and their addition salts 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 application 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 pyrazolo-pyrimidine derivatives such as those mentioned in patent application FR-A-2 750 048 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,
- pyrazole derivatives mention may more particularly be made of the compounds described in patents DE 3 843 892, DE 4 133 957 and patent applications WO 94/08969, 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 1-
- these oxidation bases preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight approximately of this weight.
- the oxidation dye compositions in accordance with the invention may also contain at least one coupler and / or at least one direct dye, in particular for modifying the nuances or enriching them with reflections.
- the couplers which can be used in the oxidation dye compositions in accordance with the invention can be chosen from the couplers conventionally used in oxidation dyeing and among which there may be mentioned in particular metaphenylenediamines, meta-aminophenols, metadiphenols and heterocyclic couplers such as, for example, indole derivatives, indolinic derivatives, pyridine derivatives and pyrazolones, and their addition salts with an acid.
- couplers are more particularly chosen from 2-methyl 5-amino phenol, 5-N- ( ⁇ -hydroxyethyl) amino 2-methyl phenol, 3-amino phenol, 1, 3-di hydroxy benzene, 1, 3-dihydroxy 2-methyl benzene, 4-chloro 1, 3-dihydroxy benzene, 2,4-diamino l- ( ⁇ -hydroxyethyloxy) benzene, 2-amino 4- ( ⁇ -hydroxyethylamino) 1-methoxy benzene, 1,3-diamino benzene, 1,3-bis- (2,4-diaminophenoxy) propane, sesamol, ⁇ -naphthol, 6-hydroxy indole, 4-hydroxy indole, 4-hydroxy N -methyl indole, 6-hydroxy indoline, 2,6-dihydroxy 4-methyl pyridine, 1-H 3-methyl pyrazole 5-one, 1-phenyl 3-methyl pyrazole 5-one, and their salts addition with an acid.
- these couplers preferably represent from 0.0001 to 10% by weight approximately of the total weight of the dye composition and even more preferably from 0.005 to 5% by weight approximately of this weight.
- addition salts with an acid which can be used in the context of the invention are in particular chosen from hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates and acetates.
- the dye composition according to the invention may also contain various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or mixtures thereof, anionic, cationic polymers , nonionic, amphoteric, zwitterionic or their mixtures, mineral or organic thickening agents, antioxidant agents, penetration agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as for example silicones, film-forming agents, preserving agents, opacifying agents.
- adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or mixtures thereof, anionic, cationic polymers , nonionic, amphoteric, zwitterionic or their mixtures, mineral or organic thickening agents, antioxidant agents, penetration agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such
- the dye composition according to the invention can be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratin fibers, and in particular human hair.
- the invention also relates to a process for dyeing keratin fibers and in particular human keratin fibers such as the hair, using the dye composition as defined above.
- the subject of the invention is also a process for the oxidation dyeing of keratin fibers and in particular human keratin fibers such as the hair using the dye composition as defined above.
- at least one dye composition as defined above is applied to the fibers, for a time sufficient to develop the desired coloration, either in air or using an oxidizing agent.
- the dye composition may optionally contain oxidation catalysts, in order to accelerate the oxidation process.
- the coloring of the fibers can be carried out without the addition of an oxidizing agent, only in contact with the oxygen in the air.
- the dye composition according to the invention contains one or more oxidation bases and / or one or more couplers
- at least one fiber is applied to the fibers.
- dye composition as defined above, the color being revealed at acidic, neutral or alkaline pH using an oxidizing agent which is added just at the time of use to the dye composition or which is present in an applied oxidizing composition simultaneously or sequentially separately.
- the dye composition described above is preferably mixed with an oxidizing composition containing, in an environment suitable for dyeing, at the time of use, at least one oxidizing agent present in an amount sufficient to develop coloring.
- the mixture obtained is then applied to the keratin fibers and left to stand for 3 to 50 minutes approximately, preferably 5 to 30 minutes approximately, after which it is rinsed, washed with shampoo, rinsed again and dried.
- the oxidizing agent present in the oxidizing composition as defined above can be chosen from the oxidizing agents conventionally used for the oxidation dyeing of keratin fibers, and among which mention may be made of hydrogen peroxide, urea peroxide, alkali metal bramates, persalts such as perborates and persulfates and enzymes such as peroxidases, laccases, tyrosynases and oxidoreductases among which may be mentioned in particular pyranose oxidases, glucose oxidases, glycerol oxidases, lactate oxidases, pyruvate oxidases, and uricases.
- the pH of the oxidizing composition containing the oxidizing agent as defined above is such that after mixing with the dye composition, the pH of the resulting composition applied to the keratin fibers preferably varies between 3 and 12 approximately, and again more preferably between 5 and 11. It is adjusted to the desired value by means of acidifying or basifying agents usually used in dyeing keratin fibers and as defined above.
- the oxidizing composition as defined above may also contain various adjuvants conventionally used in compositions for dyeing the hair and as defined above.
- composition which is finally applied to the keratin fibers can be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratin fibers, and in particular human hair. .
- Another object of the invention is a device with several compartments or "kit” for dyeing or any other packaging system with several compartments, a first compartment of which contains the dye composition as defined above and a second compartment of which contains the oxidizing composition. as defined above.
- These devices can be equipped with a means enabling the mixture to be delivered to the hair. desired, such as the devices described in patent FR-2,586,913 in the name of the applicant.
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Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002322998A CA2322998A1 (en) | 1999-01-19 | 2000-01-18 | Cationic di-benzene dyeing agents, use for oxidation dyeing of keratin fibres, dyeing compositions and dyeing method |
EP00900599A EP1064278A1 (en) | 1999-01-19 | 2000-01-18 | Cationic di-benzene dyeing agents, use for oxidation dyeing of keratin fibres, dyeing compositions and dyeing method |
JP2000594802A JP2002535324A (en) | 1999-01-19 | 2000-01-18 | Cationic dibenzene dye, its use for oxidative dyeing of keratin fibers, dyeing composition and dyeing method |
AU30555/00A AU3055500A (en) | 1999-01-19 | 2000-01-18 | Cationic di-benzene dyeing agents, use for oxidation dyeing of keratin fibres, dyeing compositions and dyeing method |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR99/00502 | 1999-01-19 | ||
FR9900502A FR2788519A1 (en) | 1999-01-19 | 1999-01-19 | Cationic di-benzene colorants for use as oxidation-dyes precursors in oxidation-dyeing of keratin fibres, especially hair, contain cationic group including quaternized cycles |
Publications (1)
Publication Number | Publication Date |
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WO2000043386A1 true WO2000043386A1 (en) | 2000-07-27 |
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Application Number | Title | Priority Date | Filing Date |
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PCT/FR2000/000094 WO2000043386A1 (en) | 1999-01-19 | 2000-01-18 | Cationic di-benzene dyeing agents, use for oxidation dyeing of keratin fibres, dyeing compositions and dyeing method |
Country Status (6)
Country | Link |
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EP (1) | EP1064278A1 (en) |
JP (1) | JP2002535324A (en) |
AU (1) | AU3055500A (en) |
CA (1) | CA2322998A1 (en) |
FR (1) | FR2788519A1 (en) |
WO (1) | WO2000043386A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US7179303B2 (en) | 2001-04-27 | 2007-02-20 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Active ingredient combinations for hair-dyeing agents |
Families Citing this family (1)
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FR2893027B1 (en) * | 2005-11-09 | 2010-12-17 | Oreal | COMPOSITION FOR DYING KERATINIC FIBERS COMPRISING AT LEAST ONE CATIONIC 3-AMINO PYAZOLOPYRIDINE DERIVATIVE |
Citations (15)
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DE1135589B (en) * | 1959-09-12 | 1962-08-30 | Basf Ag | Process for the production of azo dyes |
US3100739A (en) * | 1958-02-25 | 1963-08-13 | Therachemie Chem Therapeut | Process for dyeing human hair with water soluble, quaternary ammonium containing dyes |
FR2428437A2 (en) * | 1974-05-16 | 1980-01-11 | Oreal | Hair cosmetics for dyeing, bleaching or permanent waving - contg. quaternised poly:amine-urea polymers |
FR2586913A1 (en) * | 1985-09-10 | 1987-03-13 | Oreal | PROCESS FOR FORMING IN IN SITU A COMPOSITION CONSISTING OF TWO PARTS CONDITIONED SEPARATELY AND DISPENSING ASSEMBLY FOR IMPLEMENTING SAID METHOD |
JPS62167771A (en) * | 1986-01-17 | 1987-07-24 | Mitsubishi Petrochem Co Ltd | Imidazolium salt type polycationic compound and production thereof |
US4975092A (en) * | 1988-05-13 | 1990-12-04 | Clairol Incorporated | Processes for coloring and/or conditioning hair |
EP0544400A2 (en) * | 1991-11-27 | 1993-06-02 | Bristol-Myers Squibb Company | P-Phenylenediamine substituted by a quaternary ammonium group and an electron withdrawing group |
WO1994001077A1 (en) * | 1992-07-03 | 1994-01-20 | Henkel Kommanditgesellschaft Auf Aktien | Hair-treatment agents |
WO1995001772A1 (en) * | 1993-07-05 | 1995-01-19 | Ciba-Geigy Ag | Process for dyeing keratin-containing fibres |
WO1995015144A1 (en) * | 1993-11-30 | 1995-06-08 | Ciba-Geigy Ag | Cationic dyes for keratin-containing fibres |
EP0714954A2 (en) * | 1994-11-03 | 1996-06-05 | Ciba-Geigy Ag | Cationic iminazoleazodyestuffs |
EP0740931A1 (en) * | 1995-05-05 | 1996-11-06 | L'oreal | Compositions for dyeing keratinic fibers containing diaminopyrazoles, process for dyeing, diaminopyrazoles and process for their preparation |
EP0850638A1 (en) * | 1996-12-23 | 1998-07-01 | L'oreal | Oxidative dye composition for keratinic fibres and dyeing process using this composition |
WO1999003834A2 (en) * | 1997-07-16 | 1999-01-28 | L'oreal | Cationic oxidation bases, their use for oxidation dyeing of keratin fibres, dyeing compositions and methods |
WO1999003836A1 (en) * | 1997-07-16 | 1999-01-28 | L'oreal | Novel cationic oxidation bases, their use for oxidation dyeing of keratin fibres, dyeing compositions and dyeing methods |
-
1999
- 1999-01-19 FR FR9900502A patent/FR2788519A1/en not_active Withdrawn
-
2000
- 2000-01-18 JP JP2000594802A patent/JP2002535324A/en active Pending
- 2000-01-18 WO PCT/FR2000/000094 patent/WO2000043386A1/en not_active Application Discontinuation
- 2000-01-18 CA CA002322998A patent/CA2322998A1/en not_active Abandoned
- 2000-01-18 AU AU30555/00A patent/AU3055500A/en not_active Abandoned
- 2000-01-18 EP EP00900599A patent/EP1064278A1/en not_active Ceased
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US3100739A (en) * | 1958-02-25 | 1963-08-13 | Therachemie Chem Therapeut | Process for dyeing human hair with water soluble, quaternary ammonium containing dyes |
DE1135589B (en) * | 1959-09-12 | 1962-08-30 | Basf Ag | Process for the production of azo dyes |
FR2428437A2 (en) * | 1974-05-16 | 1980-01-11 | Oreal | Hair cosmetics for dyeing, bleaching or permanent waving - contg. quaternised poly:amine-urea polymers |
FR2586913A1 (en) * | 1985-09-10 | 1987-03-13 | Oreal | PROCESS FOR FORMING IN IN SITU A COMPOSITION CONSISTING OF TWO PARTS CONDITIONED SEPARATELY AND DISPENSING ASSEMBLY FOR IMPLEMENTING SAID METHOD |
JPS62167771A (en) * | 1986-01-17 | 1987-07-24 | Mitsubishi Petrochem Co Ltd | Imidazolium salt type polycationic compound and production thereof |
US4975092A (en) * | 1988-05-13 | 1990-12-04 | Clairol Incorporated | Processes for coloring and/or conditioning hair |
EP0544400A2 (en) * | 1991-11-27 | 1993-06-02 | Bristol-Myers Squibb Company | P-Phenylenediamine substituted by a quaternary ammonium group and an electron withdrawing group |
WO1994001077A1 (en) * | 1992-07-03 | 1994-01-20 | Henkel Kommanditgesellschaft Auf Aktien | Hair-treatment agents |
WO1995001772A1 (en) * | 1993-07-05 | 1995-01-19 | Ciba-Geigy Ag | Process for dyeing keratin-containing fibres |
WO1995015144A1 (en) * | 1993-11-30 | 1995-06-08 | Ciba-Geigy Ag | Cationic dyes for keratin-containing fibres |
EP0714954A2 (en) * | 1994-11-03 | 1996-06-05 | Ciba-Geigy Ag | Cationic iminazoleazodyestuffs |
EP0740931A1 (en) * | 1995-05-05 | 1996-11-06 | L'oreal | Compositions for dyeing keratinic fibers containing diaminopyrazoles, process for dyeing, diaminopyrazoles and process for their preparation |
EP0850638A1 (en) * | 1996-12-23 | 1998-07-01 | L'oreal | Oxidative dye composition for keratinic fibres and dyeing process using this composition |
WO1999003834A2 (en) * | 1997-07-16 | 1999-01-28 | L'oreal | Cationic oxidation bases, their use for oxidation dyeing of keratin fibres, dyeing compositions and methods |
WO1999003836A1 (en) * | 1997-07-16 | 1999-01-28 | L'oreal | Novel cationic oxidation bases, their use for oxidation dyeing of keratin fibres, dyeing compositions and dyeing methods |
Non-Patent Citations (1)
Title |
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DATABASE WPI Week 198735, Derwent World Patents Index; AN 1987-246090, XP002120222 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7179303B2 (en) | 2001-04-27 | 2007-02-20 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Active ingredient combinations for hair-dyeing agents |
Also Published As
Publication number | Publication date |
---|---|
CA2322998A1 (en) | 2000-07-27 |
JP2002535324A (en) | 2002-10-22 |
AU3055500A (en) | 2000-08-07 |
EP1064278A1 (en) | 2001-01-03 |
FR2788519A1 (en) | 2000-07-21 |
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