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WO2002032385A1 - Agents colorants d'oxydation contenant 2-chloro-p-aminophenol - Google Patents

Agents colorants d'oxydation contenant 2-chloro-p-aminophenol Download PDF

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Publication number
WO2002032385A1
WO2002032385A1 PCT/EP2001/011520 EP0111520W WO0232385A1 WO 2002032385 A1 WO2002032385 A1 WO 2002032385A1 EP 0111520 W EP0111520 W EP 0111520W WO 0232385 A1 WO0232385 A1 WO 0232385A1
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WO
WIPO (PCT)
Prior art keywords
bis
radical
aminophenyl
amino
alkyl
Prior art date
Application number
PCT/EP2001/011520
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German (de)
English (en)
Inventor
Horst Höffkes
Doris Oberkobusch
Melanie Moch
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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Filing date
Publication date
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to AU2002210523A priority Critical patent/AU2002210523A1/en
Priority to EP01978399A priority patent/EP1326578A1/fr
Publication of WO2002032385A1 publication Critical patent/WO2002032385A1/fr

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Classifications

    • 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
    • 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
    • A61K8/415—Aminophenols

Definitions

  • the present invention relates to compositions for dyeing keratin fibers which contain 2-chloro-4-aminophenol in combination with 2-core developer components, a process for dyeing keratin fibers with these compositions and the use of this dye combination for dyeing keratin fibers.
  • Coloring agents or tinting agents which contain so-called direct draws as the coloring component are usually used for temporary dyeings. These are dye molecules that attach directly to the hair and do not require an oxidative process to form the color. These dyes include, for example, henna, which is known from antiquity for coloring body and hair. These dyeings are generally sensitive to shampooing, so that a frequently undesirable shift in the shade or even a visible “discoloration" can occur.
  • oxidation dyes are used for permanent, intensive dyeings with appropriate fastness properties.
  • Such colorants usually contain oxidation dye precursors, so-called developer components and coupler components.
  • the developer components form under the influence of oxidizing agents or of atmospheric oxygen with one another or under coupling with one or more Coupler components from the actual dyes.
  • the oxidation coloring agents are characterized by excellent, long-lasting coloring results.
  • Good oxidation dye precursors are primarily intended to meet the following requirements: They have to develop the desired color shades with sufficient intensity and authenticity in the oxidative coupling. They must also have a good ability to draw onto the fiber, with no noticeable differences between stressed and freshly regrown hair, especially with human hair (leveling ability). They should be resistant to light, sweat, heat, friction and the influence of chemical reducing agents, e.g. Perm liquids. After all, if they are used as a hair dye, they should not stain the scalp too much, and above all they should be harmless from a toxicological and dermatological point of view. Furthermore, the coloration obtained should be easily removed from the hair again by bleaching, if it does not correspond to the individual wishes of the individual and should be reversed.
  • a first subject of the present invention is therefore an agent for coloring keratin fibers, contained in a cosmetically acceptable medium
  • keratin fibers are understood to mean furs, wool, feathers and in particular human hair.
  • dinuclear developer components are understood to mean nerobonds which contain at least two aromatic nuclei which carry at least two optionally substituted amino and / or hydroxyl groups which are in the para and / or ortho position to one another.
  • Binuclear developer components of the formula (I) are preferred according to the invention.
  • Z 1 and Z 2 independently represent a hydroxyl or NH radical, optionally substituted by a Ci to C4 alkyl radical, by a Ci to C 4 - / or substituted hydroxyalkyl radical, and by a bridge Y, or the part of a bridging ring system
  • the Nerbrückung Y stands for an alkylene group with 1 to 14 carbon atoms, such as a linear or branched alkylene chain or an alkylene ring which are interrupted or terminated by one or more nitrogen-containing groups and / or one or more heteroatoms such as oxygen, sulfur or nitrogen atoms can and may be substituted by one or more hydroxyl or - to C 8 - alkoxy radicals, or a direct bond
  • R 2 and R 3 independently of one another represent a hydrogen or halogen atom, a Ci to C 4 alkyl radical, a Ci to C 4 monohydroxyalkyl radical, a C 2 to C 4 polyhydroxyalkyl radical, a Cp to C 4 amino
  • R 4 , R 5 , R 6 , R 7 , R 8 and R 9 independently of one another represent a hydrogen atom, a direct bond to the bridging Y or a Ci to C 4 alkyl radical, with the provisos that
  • the compounds of formula (I) contain at least one amino group which carries at least one hydrogen atom.
  • Examples of the C 1 -C 4 -alkyl radicals mentioned as substituents in the compounds according to the invention are the groups methyl, ethyl, propyl, isopropyl and butyl. Ethyl and methyl are preferred alkyl radicals. According to the invention preferred Ci to C 4 -alkoxy radicals, for example, a methoxy or an ethoxy group. Further preferred examples of a C 1 -C 4 -hydroxyalkyl group are a hydroxymethyl, a 2-hydroxyethyl, a 3-hydroxypropyl or a 4-hydroxybutyl group. A 2-hydroxyethyl group is particularly preferred.
  • halogen atoms are F, CI or Br atoms, Cl atoms are very particularly preferred. According to the invention, the other terms used are derived from the definitions given here.
  • nitrogen-containing groups of the formula (I) are especially the amino groups, Ci to C 4 - monoalkylamino, Cj.- -C 4 -dialkylamino, C ⁇ - to C 4 - trialkylammonium, d- to C 4 -Monohydroxyalkylamino phenomenon, imidazolinium and Ammonium.
  • the compound of the formula (I) is selected from N, N'-bis- ( ⁇ -hydroxyethyl) -N, N'-bis- (4 , -aminophenyl) -l, 3-diamino- propan-2-ol, N 5 N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) ethylenediamine, N, N'-bis (4-aminophenyl) tetramethylene diamine, N, N'-bis- ( ⁇ -hydroxyethyl) -N, N'-bis- (4-aminophenyl) tetramethylene diamine, N, N'-bis- (4-methylaminophenyi) tetramethylene diamine, N, N '-bis- (ethyl) -N, N'-bis (4'-amino-3'-methylphenyl) ethylenediamine, bis (2-hydroxy-5
  • N, N'-bis- ( ⁇ -hydroxyethyl) -N, N , -bis- (4'-aminophenyl) -1,3-diamino-propan-2-ol, bis- (2-hydroxy-5- aminophenyl) methane, N, N'-bis (4'-aminopheny ⁇ ) -l, 4-diazacycloheptane and l, 10-bis (2, 5'-diaminophenyl) -l, 4,7,10-tetraoxadecane or one of their physiologically tolerable salts are particularly preferred according to the invention.
  • the color-changing agents according to the invention contain at least one further dye precursor.
  • the present invention is not subject to any restrictions.
  • the agents according to the invention can be used as dye precursors
  • G 1 stands for a hydrogen atom, a Ci to C 4 alkyl radical, a Ci to C 4 monohydroxyalkyl radical, a C 2 to C 4 polyhydroxyalkyl radical, a (Ci to C 4 ) alkoxy- (C ⁇ - bis C 4 ) alkyl radical, a 4'-aminophenyl radical or a Q to C 4 alkyl radical which is substituted by a nitrogen-containing group, a phenyl or a 4'-aminophenyl radical;
  • G 2 represents a hydrogen atom, a Ci to C 4 alkyl radical, a Ci to C - monohydroxyalkyl, a C 2 - to C 4 -Polyhydroxyalkylradikal, a (Ci to C 4) - alkoxy (C ⁇ - to C 4 ) alkyl radical or a Ci to C 4 alkyl radical which is substituted with a nitrogen-containing group;
  • G stands for a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, a Ci to C 4 alkyl radical, a Ci to C 4 -Monohydroxyalkylradikal, a Ci to C -Hydroxyalkoxyradikal, a Ci to C 4 -Acetylaminoalkoxyradikal, a Ci to C 4 - Mesylaminoalkoxyradikal or a Ci to C 4 -Carbamoylaminoalkoxyradikal;
  • a halogen atom such as a chlorine, bromine, iodine or fluorine atom
  • a Ci to C 4 alkyl radical a Ci to C 4 -Monohydroxyalkylradikal, a Ci to C -Hydroxyalkoxyradikal, a Ci to C 4 -Acetylaminoalkoxyradikal, a Ci to C 4 - Mesylaminoal
  • G 4 represents a hydrogen atom, a halogen atom or a Ci to C - alkyl radical or if G 3 and G 4 are in the ortho position to one another, they can together form a bridging ⁇ , ⁇ -alkylenedioxo group, such as, for example, an ethylenedioxy group.
  • C 1 -C 4 -alkyl radicals mentioned as substituents in the compounds according to the invention are the groups methyl, ethyl, propyl, isopropyl and butyl. Ethyl and methyl are preferred alkyl radicals.
  • Ci to bis preferred according to the invention C 4 alkoxy radicals are, for example, a methoxy or an ethoxy group.
  • Further preferred examples of a d- to C 4 -hydroxyalkyl group are a hydroxymethyl, a 2-hydroxyethyl, a 3-hydroxypropyl or a 4-hydroxybutyl group. A 2-hydroxyethyl group is particularly preferred.
  • halogen atoms are F, CI or Br atoms, Cl atoms are very particularly preferred. According to the invention, the other terms used are derived from the definitions given here.
  • nitrogen-containing groups of the formula (III) are especially the amino groups, d- to C 4 - monoalkylamino, d- to C 4 dialkylamino, Ci to C 4 - trialkylammonium groups, Ci to C 4 -Monohydroxyalkylamino phenomenon, imidazolinium and ammonium.
  • Particularly preferred p-phenylenediamines of the formula (II) are selected from p-phenylenediamine, p-toluenediamine, 2-chloro-p-phenylenediamine, 2,3-dimethyl-p-phenylenediamine, 2,6-dimethyl-p-phenylenediamine, 2 , 6-diethyl-p-phenylenediamine, 2,5-dimethyl-p-phenylenediamine, N, N-dimethyl-p-phenylenediamine, N, N-diethyl-p-phenylenediamine, N, N-dipropyl-p-phenylenediamine, 4 - Amino-3-methyl- (N, N-diethyl) - aniline, N, N-bis- (ß-hydroxyethyl) -p-phenylenediamine, 4-N, N-bis- (ß-hydroxyethyl) amino-2- methylaniline, 4-N
  • p-phenylenediamine derivatives of the formula (II) which are very particularly preferred are p-phenylenediamine, p-toluenediamine, 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine and N, N-bis ( ⁇ -hydroxyethyl) -p-phenylenediamine.
  • a p-aminophenol derivative or one of its physiologically tolerable salts as developer component.
  • P-Aminophenol derivatives of the formula (III) are particularly preferred
  • G represents a hydrogen atom, a halogen atom, ad- to C 4 -alkyl radical, ad- to C 4 -monohydroxyalkyl radical, a (Ci to C 4 ) alkoxy- (C ⁇ - to C 4 ) alkyl radical, a Ci - to C 4 -aminoalkyl radical, a hydroxy- (C ⁇ - to C 4 ) - alkylamino radical, a - to C 4 -hydroxyalkoxy radical, a Ci- to C 4 -
  • G 14 represents a hydrogen or halogen atom, a C 1 -C 4 -alkyl radical
  • Aminoalkyl radical or a Ci to C 4 -Cyanoalkylradikal is a Ci to C 4 -Cyanoalkylradikal
  • G 15 stands for hydrogen, a Ci to C 4 alkyl radical, a Ci to C 4 -
  • Monohydroxyalkyl radical a C to C polyhydroxyalkyl radical
  • G 16 represents hydrogen or a halogen atom.
  • Preferred p-aminophenols of the formula (III) are in particular p-aminophenol, N-methyl-p-aminophenol, 4-amino-3-methylphenol, 4-amino-3-ftuorphenol, 2-hydroxymethylamino-4-aminophenol , 4-amino-3-hydroxymethylphenol, 4-amino-2- (2-hydroxyethoxy) phenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4 -Amino-2-aminomethylphenol, 4-amino-2- (ß- hydroxyethyl-aminomethyl) phenol, 4-amino-2-fluorophenol, 2,6-dichloro-4-aminophenol, 4-amino-2 - ((diethylamino) methyl) phenol and their physiologically tolerable salts.
  • Very particularly preferred compounds of the formula (III) are p-aminophenol, 4-amino-3-methylphenol, 4-amino-2-aminomethylphenol and 4-amino-2-
  • the developer component can be selected from o-aminophenol and its derivatives, such as, for example, 2-amino-4-methylphenol or 2-amino-4-chlorophenol.
  • the developer component can be selected from heterocyclic developer components, such as, for example, the pyridine, pyrimidine, pyrazole, pyrazole-pyrimidine derivatives and their physiologically tolerable salts.
  • heterocyclic developer components such as, for example, the pyridine, pyrimidine, pyrazole, pyrazole-pyrimidine derivatives and their physiologically tolerable salts.
  • Preferred pyridine derivatives are, in particular, the compounds described 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 and 3,4-diamino-pyridine.
  • Preferred pyrimidine derivatives are, in particular, the compounds described in German patent DE 2 359 399, Japanese laid-open patent publication JP 02019576 A2 or in laid-open publication WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy- 2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2-dimethylamino-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6- triaminopyrimidine.
  • Preferred pyrazole derivatives are in particular the compounds described in the patents DE 3 843 892, DE 4 133 957 and patent applications WO 94/08969, WO 94/08970, EP-740931 and DE 195 43 988, such as 4,5- Diamino-l-methylpyrazole, 4,5-diamino-1 - ( ⁇ -hydroxyethyl) pyrazole, 3,4-diaminopyrazole, 4,5-diamino-l- (4'-chlorobenzyl) pyrazole, 4,5-diamino -l, 3-dimethylpyrazole, 4,5-diamino-3-methyl-l- phenylpyrazole, 4,5-diamino-l-methyl-3-phenylpyrazole, 4-amino-l, 3-dimethyl-5-hydrazinopyrazole, l-benzyl-4,5-diamino-3-methylpyrazole, 4,5-di
  • Preferred pyrazole-pyrimidine derivatives are in particular the derivatives of pyrazole- [1,5-a] -pyrimidine of the following formula (IV) and its tautomeric forms, provided that there is a tautomeric equilibrium:
  • G 17 , G 18 , G 19 and G 20 independently represent a hydrogen atom, a C 1 -C 4 -alkyl radical, an aryl radical, a C 1 -C 4 -hydroxyalkyl radical, a C 2 -C -polyhydroxyalkyl radical (Ci to C 4 ) alkoxy (C 1 to C 4 ) alkyl radical, ad to C 4 aminoalkyl radical, which can optionally be protected by an acetyl-ureide or sulfonyl radical, a (Ci to C 4 ) alkylamino (Cr to C) alkyl radical, a di - [(C ⁇ - to C 4 ) alkyl] - (C ⁇ - to C 4 ) aminoalkyl radical, the dialkyl radicals optionally having a carbon cycle or a heterocycle form with 5 or 6 chain links, a Ci- to C 4 -hydroxyalkyl or a di- (d- to C 4 ) - [hydroxy
  • pyrazole- [1,5-a] pyrimidine of the formula (IV) above contains a hydroxyl group at one of the positions 2, 5 or 7 of the ring system, there is a tautomeric equilibrium, which is illustrated, for example, in the following scheme:
  • pyrazole [1,5-a] pyrimidines of the above formula (IV) can be prepared as described in the literature by cyclization starting from an aminopyrazole or from hydrazine.
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives are generally used as coupler components.
  • Suitable coupler substances are in particular 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinomino methyl ether, m-phenylenediamine, 1- Phenyl-3-methyl-pyrazolone-5, 2,4-dichloro-3-aminophenol, 1,3-bis- (2 ', 4'-diaminophenoxy) propane, 2-chloro-resorcinol, 4-chloro-resorcinol, 2-chloro-6-methyl-3-aminophenol, 2-amino-3-hydroxypyridine, 2-methylresorcinol, 5-methylresorcinol and
  • Coupler components preferred according to the invention are: m-aminophenol and its derivatives, such as 5-amino-2-methylphenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 2,6-dimethyl-3- aminophenol, 3-trifluoroacetylamino-2-chloro-6-methylphenol, 5-amino-4-chloro-2-methylphenol, 5-amino-4-methoxy-2-methylphenol, 5- (2'-hydroxyethyl) amino-2 methylphenol, 3- (diethylamino) phenol, N-cyclopentyl-3-aminophenol, 1,3-
  • Diaminophenoxyethanol 1, 3-bis- (2,, 4'-diaminophenoxy) -propane, 1-methoxy-2-amino-4- (2'-hydroxyethylamino) benzene, 1, 3-bis (2 ', 4, -diaminophenyl) -propane, 2,6-
  • Resorcinol monomethyl ether 2-methylresorcinol, 5-methylhesorcinol, 2,5-
  • Pyridine derivatives such as 2,6-dihydroxypyridine, 2-amino-3-hydroxypyridine, 2-amino-5-chloro-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxypyridine, 2,6-dihydroxy-4-methylpyridine , 2,6-diaminopyridine, 2,3-diamino
  • Naphthalene derivatives such as 1-naphthol, 2-methyl-1-naphthol, 2-
  • Morpholine derivatives such as 6-hydroxybenzomorpholine and 6-aminobenzomorpholine,
  • Pyrazole derivatives such as, for example, l-phenyl-3-methylpyrazol-5-one,
  • Indole derivatives such as 4-hydroxyindole, 6-hydroxyindole and 7-
  • hydroxyindole - Pyrimidine derivatives, such as 4,6-diaminopyrimidine, 4-amino-2,6-dihydroxypyrimidine, 2,4-diamino-6-hydroxypyrimidine, 2,4,6-trihydroxypyrimidine, 2-amino-4-methylpyrimidine, 2-amino -4-hydroxy-6-methylpyrimidine and 4,6-dihydroxy-2-methylpyrimidine, or
  • Methylenedioxybenzene derivatives such as l-hydroxy-3,4-methylenedioxybenzene, l-amino-3,4-methylenedioxybenzene and l- (2'-hydroxyethyl) - amino-3, 4-methylenedioxybenzene.
  • coupler components are 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 3-aminophenol, 5-amino-2-methylphenol, 2-amino-3-hydroxypyridine, resorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol and 2,5-dimethylresorcinol.
  • the hair colorants according to the invention may contain minor components in minor amounts, provided that these do not adversely affect the coloring result or for other reasons, e.g. B. toxicological, must be excluded.
  • the oxidation dye precursors are preferably present in the agents according to the invention in amounts of 0.01 to 20% by weight, preferably 0.5 to 5% by weight, in each case based on the total agent.
  • Those indoles and indolines which have at least one hydroxyl or amino group, preferably as a substituent on the six-membered ring, are preferably used as precursors of nature-analogous dyes.
  • These groups can carry further substituents, e.g. B. in the form of etherification or esterification of the hydroxy group or an alkylation of the amino group.
  • R 1 stands for hydrogen, a dC 4 alkyl group or a C 1 -C 4 hydroxyalkyl group
  • R 2 ' stands for hydrogen or a -COOH group, where the -COOH group can also be present as a salt with a physiologically compatible cation
  • R 3 represents hydrogen or a C 1 -C 4 alkyl group
  • R 4 represents hydrogen, a C 1 -C 4 -alkyl group or a group -CO-R 6 , in which
  • R 6 ' represents a C 1 -C 4 alkyl group
  • R 5 stands for one of the groups mentioned under R 4 , as well as physiologically tolerable salts of these compounds with an organic or inorganic acid.
  • Particularly preferred derivatives of indoline are 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N- Butyl-5,6-dihydroxyindoline, 5,6-dihydroxyindoline-2-carboxylic acid and 6-hydroxyindoline, 6-aminoindoline and 4-aminoindoline.
  • N-methyl-5,6-dihydroxyindoline N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline and especially that 5,6-Dihydroxyindolin.
  • R 1 represents hydrogen, a dC -alkyl group or a -C-C 4 hydroxyalkyl group
  • R 2 stands for hydrogen or a -COOH group, where the -COOH group can also be present as a salt with a physiologically compatible cation
  • R 3 represents hydrogen or a C 1 -C 4 alkyl group
  • R 4 represents hydrogen, a C 1 -C 4 -alkyl group or a group -CO-R 6 , in which
  • R 6 ' represents a C 1 -C 4 alkyl group
  • R 5 stands for one of the groups mentioned under R 4 , as well as physiologically tolerable salts of these compounds with an organic or inorganic acid.
  • Particularly preferred derivatives of indole are 5,6-dihydroxyindole, N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5, 6-dihydroxyindole, 5,6-dihydroxyindole-2-carboxylic acid, 6-hydroxyindole, 6-aminoindole and 4-aminoindole.
  • N-methyl-5,6-dihydroxyindole N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole and in particular 5.6 -Dihydroxyindol.
  • the indoline and indole derivatives can be used in the colorants used in the process according to the invention both as free bases and in the form of their physiologically tolerable salts with inorganic or organic acids, for.
  • B. the hydrochloride, sulfates and hydrobromides can be used.
  • the indole or indoline derivatives are usually contained in these in amounts of 0.05-10% by weight, preferably 0.2-5% by weight.
  • the agents according to the invention can contain direct dyes for further shading. These are usually selected from nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Preferred direct dyes are those with the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yelow 6, Basic Yellow 57, HC Orange 1, Disperse Orange 3, HC Red 1, HC Red 3, HC Red 13, HC Red BN, Basic Red 76, HC Blue 2, HC Blue 12, Disperse Blue 3, Basic Blue 7, Basic Blue 26, Basic Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Basic Violet 2, Basic Violet 14, Acid Violet 43, Disperse Black 9, Acid Black 52, Basic Brown 16 and Basic Brown 17 known compounds as well as 1,4-bis- (ß-hydroxyethyl) -amino- 2-nitrobenzene, 3 -nitro- 4- (ß-hydroxyethyl) aminophenol, 4-amino-2-nitrodipheny lamin-2 '-carboxylic acid, 6-nitro-l, 2,3,4-tetrahydroquinoxaline, 2-hydroxy-l, 4-naphthoquinone, hy - Droxyethyl-2-nitro-tolui
  • compositions according to the invention in accordance with this embodiment preferably contain the substantive dyes in an amount of 0.01 to 20% by weight, based on the total colorant.
  • preparations according to the invention can also contain naturally occurring dyes such as, for example, henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, rotten tree bark, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • the agents according to the invention preferably contain dye precursors in a suitable aqueous, alcoholic or aqueous-alcoholic carrier.
  • a suitable aqueous, alcoholic or aqueous-alcoholic carrier are, for example, creams, emulsions, gels or also surfactant-containing foaming solutions, such as shampoos, foam aerosols or other preparations which are suitable for use on the hair.
  • surfactant-containing foaming solutions such as shampoos, foam aerosols or other preparations which are suitable for use on the hair.
  • aqueous-alcoholic solutions are understood to mean aqueous solutions containing 3 to 70% by weight of a dC 4 alcohol, in particular ethanol or isopropanol.
  • the agents according to the invention can additionally contain further organic solvents, such as, for example, methoxybutanol, benzyl alcohol, ethyl diglycol or 1,2-propylene glycol. All water-soluble organic solvents are preferred.
  • the actual oxidative coloring of the fibers can basically be done with atmospheric oxygen.
  • a chemical oxidizing agent is preferably used, especially if, in addition to the coloring, a lightening effect on human hair is desired.
  • Persulfates, chlorites and in particular hydrogen peroxide or its adducts with urea, melamine and sodium borate are suitable as oxidizing agents. It is also possible to carry out the oxidation with the aid of enzymes, the enzymes being used both for producing oxidizing per compounds and for enhancing the action of a small amount of oxidizing agents present.
  • the enzymes (enzyme class 1: oxidoreductases) can transfer electrons from suitable developer components (reducing agents) to atmospheric oxygen.
  • Oxidases such as tyrosinase, ascorbate oxidase and laccase are also preferred Glucose oxidase, uricase or pyruvate oxidase. Furthermore, the procedure should be mentioned to increase the effect of small amounts (e.g. 1% and less, based on the total agent) of hydrogen peroxide by peroxidases.
  • the actual hair dye is expediently prepared immediately before use by mixing the preparation of the oxidizing agent with the preparation containing the dye precursors.
  • the resulting ready-to-use hair dye preparation should preferably have a pH in the range from 6 to 12. It is particularly preferred to use the hair dye in a weakly alkaline environment.
  • the application temperatures can range between 15 and 40 ° C. After an exposure time of 5 to 45 minutes, the hair dye is rinsed off from the hair to be colored. Washing with a shampoo is not necessary if a carrier with a high tenside content, e.g. a coloring shampoo was used.
  • the agents according to the invention can furthermore contain all active substances, additives and auxiliary substances known for such preparations.
  • these agents contain at least one surfactant, with both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants being suitable in principle.
  • anionic and zwitterionic, ampholytic, nonionic and cationic surfactants being suitable in principle.
  • Suitable anionic surfactants in preparations according to the invention are all anionic surface-active substances suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms.
  • anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms.
  • the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
  • Sulfosuccinic acid mono- and dialkyl esters with 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid mono-alkyl polyoxyethyl esters with 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, linear alkanesulfonates with 12 to 18 carbon atoms, linear alpha-olefin sulfonates with 12 to 18 carbon atoms, alpha-sulfofatty acid methyl ester of fatty acids with 12 to 18 carbon atoms, - alkyl sulfates and alkyl polyglycol ether sulfates of the formula RO (CH 2 -CH 2 O) x -SO 3 H, in which R is a preferably linear alkyl group with 10 to 18 C atoms and x 0 or 1 to 12,
  • Esters of tartaric acid and citric acid with alcohols which are adducts of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols with 8 to 22 carbon atoms.
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids with 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, and in particular salts of saturated and in particular unsaturated C 8 -C 22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid.
  • Non-ionic surfactants contain z.
  • B a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group.
  • Such connections are, for example Addition products of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide with linear fatty alcohols with 8 to 22 C atoms, with fatty acids with 12 to 22 C atoms and with alkylphenols with 8 to 15 C atoms in the alkyl group , -C 2 -C 22 fatty acid monoesters and diesters of adducts of 1 to 30 moles of ethylene oxide with glycerol,
  • Preferred nonionic surfactants are alkyl polyglycosides of the general formula R'O- (Z) ⁇ . These connections are characterized by the following parameters.
  • the alkyl radical R 1 contains 6 to 22 carbon atoms and can be either linear or branched. Primary linear and methyl-branched aliphatic radicals in the 2-position are preferred. Examples of such alkyl radicals are 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, 1-cetyl and 1-stearyl. 1-Octyl, 1-decyl, 1-lauryl, 1-myristyl are particularly preferred. When using so-called "oxo alcohols" as starting materials, compounds with an odd number of carbon atoms in the alkyl chain predominate.
  • the alkyl polyglycosides which can be used according to the invention can contain, for example, only a certain alkyl radical R 1 .
  • these compounds are made from natural fats and oils or mineral oils.
  • the alkyl radicals R are mixtures corresponding to the starting compounds or corresponding to the respective working up of these compounds.
  • R l consists essentially of C 8 and Cio alkyl groups, essentially from C 2 and C 14 alkyl groups, essentially from C 8 to C 6 alkyl groups or essentially from C 2 - C ⁇ 6 alkyl groups.
  • Any mono- or oligosaccharides can be used as sugar building block Z.
  • Sugar with 5 or 6 carbon atoms and the corresponding oligosaccharides are usually used. Examples of such sugars are glucose, fructose, galactose, arabinose, ribose, xylose, lyxose, allose, old rose, mannose, gulose, idose, talose and sucrose.
  • Preferred sugar units are glucose, fructose, galactose, arabinose and sucrose; Glucose is particularly preferred.
  • alkyl polyglycosides which can be used according to the invention contain an average of 1.1 to 5 sugar units. Alkyl polyglycosides with x values from 1.1 to 1.6 are preferred. Alkyl glycosides in which x is 1.1 to 1.4 are very particularly preferred.
  • the alkyl glycosides can also serve to improve the fixation of fragrance components on the hair.
  • the person skilled in the art will preferably resort to this substance class as a further ingredient of the preparations according to the invention.
  • alkoxylated homologs of the alkyl polyglycosides mentioned can also be used according to the invention. These homologues can contain an average of up to 10 ethylene oxide and / or propylene oxide units per alkyl glycoside unit.
  • zwitterionic surfactants can be used, in particular as co-surfactants.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one -COO (_) - or -SOs ⁇ group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyl-dimethylammonium glycinate, N-acyl-aminopropyl-N, N-dimethylammomumglycinate, for example the cocoacylaminopropyl-dimethylammonium glycinate, and 2-alkyl-3-carboxylmethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group, and also the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyl-dimethylammonium glycinate, N-acyl-aminopropyl-N, N-d
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under the INCI name Cocamidopropyl Betaine.
  • Ampholytic surfactants are also particularly suitable as co-surfactants. Ampholytic surfactants are surface-active compounds which, in addition to a C 8 -C 8 -alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO 3 H group in the molecule and are capable of forming internal salts are.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12 . 18 acyl sarcosine.
  • the cationic surfactants used are, in particular, those of the quaternary ammonium compound, esterquat and amidoamine type.
  • Preferred quaternary ammonium compounds are ammonium halides, especially chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. B. cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride, as well as the compounds known under the INCI names Quaternium-27 and Quaternium-83 compounds imidazolium.
  • the long alkyl chains of the above-mentioned surfactants preferably have 10 to 18 carbon atoms.
  • Esterquats are known substances which contain both at least one ester function and at least one quaternary ammonium group as a structural element.
  • Preferred ester quats are quaternized ester salts of fatty acids with triethanolamine, quaternized ester salts of fatty acids with diethanolalkylamines and quaternized ester salts of fatty acids with 1,2-dihydroxypropyldialkylamines.
  • Such products are sold, for example, under the trademarks Stepantex ® , Dehyquart ® and Armocare ® .
  • alkylamidoamines are usually produced by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines.
  • An inventively particularly suitable compound from this group is that available under the name Tegoamid ® S 18 commercially stearamidopropyl dimethylamine.
  • the quaternized protein hydrolyzates are further cationic surfactants which can be used according to the invention.
  • cationic silicone oils such as, for example, the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethylsilylamodimethicone), Dow Corning 929 emulsion (containing a hydroxylamino-modified silicone, which is also referred to as amodimethicone), SM-2059 (Manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® - Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxanes, Quaternium-80).
  • a suitable cationic surfactant quaternary sugar derivative is the commercial product Glucquat ® 100, according to INCI nomenclature a "lauryl methyl Gluceth-10 Hydroxypropyl Dimonium Chloride”.
  • the compounds with alkyl groups used as surfactant can each be uniform substances. However, it is generally preferred to start from natural vegetable or animal raw materials in the production of these substances, so that substance mixtures with different alkyl chain lengths depending on the respective raw material are obtained.
  • both products can be used with a "normal” homolog distribution as well as those with a narrow homolog distribution can be used.
  • “Normal” homolog distribution is understood to mean mixtures of homologues which are obtained as catalysts when converting fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates.
  • narrow homolog distributions are obtained if, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts. The use of products with a narrow homolog distribution can be preferred.
  • the agents according to the invention can preferably also contain a conditioning active ingredient selected from the group formed by cationic surfactants, cationic polymers, alkylamidoamines, paraffin oils, vegetable oils and synthetic oils.
  • Cationic polymers can be preferred as conditioning agents. These are usually polymers that have a quaternary nitrogen atom, for example in the form of a
  • Preferred cationic polymers are, for example, quaternized cellulose derivatives, such as are available under the names of Celquat ® and Polymer JR ® commercially.
  • the compounds Celquat ® H 100, Celquat ® L 200 and Polymer JR ® 400 are preferred quaternized cellulose derivatives.
  • Merquat ® 100 Poly (dimethyldiallylammonium chloride)
  • Merquat ® 550 dimethyldiallylammonium chloride-acrylamide copolymer
  • Merquat ® 280 dimethyldiallylammonium chloride-acrylic acid copolymer commercially available products copolymers are examples of such cationic polymers.
  • vinylpyrrolidone with quaternized derivatives of dialkylamino acrylate and methacrylate such as vinyl quaternized with diethyl sulfate pyrrolidone-dimethylaminoethyl methacrylate copolymers.
  • Such compounds are commercially available under the names Gafquat ® 734 and Gafquat ® 755.
  • Vinylpyrrolidone methoimidazolinium chloride copolymers such as those sold under the name Luviquat ®, quaternized polyvinyl alcohol and under the designations Polyquaternium 2, Polyquaternium 17, Polyquaternium 18 and
  • Polyquaternium 27 known polymers with quaternary nitrogen atoms in the main polymer chain.
  • Cationic polymers of the first four groups are particularly preferred; polyquaternium-2, polyquaternium-10 and polyquaternium-22 are very particularly preferred.
  • conditioning agents are silicone oils, in particular dialkyl and alkylarylsiloxanes, such as, for example, dimethylpolysiloxane and methylphenylpolysiloxane, and their alkoxylated and quaternized analogs.
  • silicones examples include the products sold by Dow Corning under the names DC 190, DC 200, DC 344, DC 345 and DC 1401 as well as the commercial products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethylsilylamodimethicone), Dow Coming® 929 emulsion (containing a hydroxylamino-modified silicone, which is also referred to as amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® -Quat 3270 and 3272 (manufacturer: Th. Goldschmidt ; diquaternary polydimethylsiloxanes, Quaternium-80).
  • Dow Corning a stabilized trimethylsilylamodimethicone
  • Dow Coming® 929 emulsion containing a hydroxylamino-modified silicone, which is also referred to as amodimethicone
  • SM-2059 manufactured by General Electric
  • Paraffin oils synthetically produced oligomeric alkenes and vegetable oils such as jojoba oil, sunflower oil, orange oil, almond oil, wheat germ oil and peach seed oil can also be used as conditioning agents.
  • suitable hair-conditioning compounds are phospholipids, for example soy lecithin, egg lecithin and cephalins.
  • Other active ingredients, auxiliaries and additives are, for example, nonionic polymers such as, for example, vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and ninylpyrrolidone / vinyl acetate copolymers and polysiloxanes, zwitterionic and amphoteric polymers such as, for example, acrylamidopropyltrimethylammonium chloride and acrylate Octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers,
  • anionic polymers such as polyacrylic acids, crosslinked polyacrylic acids, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and acrylic acid / ethyl acrylate / t-butyl acrylamide ⁇ - terpolymers
  • - Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, for.
  • B. bentonite or fully synthetic hydrocolloids such as e.g. Polyvinyl alcohol,
  • Structurants such as maleic acid and lactic acid, hair-conditioning compounds such as phospholipids, for example soy lecithin,
  • Protein hydrolyzates in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolyzates, their condensation products with fatty acids and quaternized protein hydrolyzates,
  • Solvents and mediators such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerin and diethylene glycol, active substances which improve fiber structure, in particular mono-, di- and oligosaccharides such as, for example, glucose, galactose, fructose, cargo sugar and lactose, quaternized amines such as methyl-1-alkylamidoethyl -2-alkylimidazolinium methosulfate
  • anti-dandruff agents such as piroctone olamine, zinc omadine and climbazol
  • Light stabilizers in particular derivatized benzophenones, cinnamic acid derivatives and triazines,
  • Substances for adjusting the pH such as, for example, customary acids, in particular edible acids and bases,
  • Active ingredients such as allantoin, pyrrolidone carboxylic acids and their salts and bisabolol, vitamins, provitamins and vitamin precursors, in particular those of the groups A, B 3 , B 5 , B 6 , C, E, F and H,
  • Extracts such as the extracts from green tea, oak bark, nettle, witch hazel, hops, chamomile, burdock root, horsetail, white dome, linden flowers, almond, aloe vera, spruce needle, horse chestnut, sandalwood, juniper, coconut, mango, apricot, lime, wheat, Kiwi, melon, orange, grapefruit, sage, rosemary, birch, mallow, cuckoo flower, quendel, yarrow, thyme, lemon balm, hake, coltsfoot, marshmallow, meristem, ginseng and ginger root.
  • - fats and waxes such as walrus, beeswax, montan wax and paraffins, fatty acid alkanolamides,
  • Complexing agents such as EDTA, NTA, ⁇ -alaninediacetic acid and phosphonic acids, swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary phosphates,
  • Opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers pearlescent agents such as ethylene glycol mono- and distearate and PEG-3 distearate, pigments,
  • a second object of the present invention is a process for dyeing keratin fibers, in which an agent according to the invention is applied to the fibers and rinsed off again after an exposure time.
  • a third object of the present invention is the use of a dye combination
  • Ci ö - ⁇ 8 fatty alcohol (INCI name: Cetearyl alcohol) (Cognis) C ⁇ 2 - ⁇ 8 fatty alcohol (INCI name: Coconut alcohol) (Cognis) Cetylstearyl alcohol with approx. 20 EO units (INCI name: Ceteareth -20) (Cognis)
  • the substances Hydrenol ® D, Lorol ® and Eumulgin B2 were melted at 80 ° C, mixed with the 80 ° C hot water containing Texapon ® NSO and Dehyton ® K, and emulsified with vigorous stirring. The emulsion was then cooled with gentle stirring.
  • the coloring cream obtained in this way was mixed in a ratio of 1: 1 with a 6% H 2 O 2 solution and applied to 5 cm long strands of standardized, 80% gray, but not specially pretreated human hair (Kerling) (quantitative ratio of dye mixture: hair amount 4: 1). After a contact time of 30 minutes at 32 ° C., the hair was rinsed, washed out with a customary shampoo and then dried.
  • the coloring results are shown in Table I.

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Abstract

L'invention concerne des agents de coloration de fibres kératiniques, contenant dans un milieu cosmétiquement acceptable les précurseurs de colorants suivants : (A) 2-chloro-4-aminophénol, et (B) au moins un développeur à deux noyaux. Les agents selon l'invention permettent une coloration particulièrement forte avec d'excellentes propriétés de résistance, et se caractérisent par ailleurs par leurs propriétés toxicologiques exceptionnelles.
PCT/EP2001/011520 2000-10-14 2001-10-05 Agents colorants d'oxydation contenant 2-chloro-p-aminophenol WO2002032385A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2002210523A AU2002210523A1 (en) 2000-10-14 2001-10-05 Oxidation colorants comprising 2-chloro-p-aminophenol
EP01978399A EP1326578A1 (fr) 2000-10-14 2001-10-05 Agents colorants d'oxydation contenant 2-chloro-p-aminophenol

Applications Claiming Priority (2)

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DE10051032.9 2000-10-14
DE2000151032 DE10051032A1 (de) 2000-10-14 2000-10-14 Oxidationsfärbemittel mit 2-Chlor-p-aminophenol

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003041671A2 (fr) * 2001-11-17 2003-05-22 Henkel Kommanditgesellschaft Auf Aktien Colorants d'oxydation contenant du bis-(5-amino-2-hydroxyphenyl)-methane

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5443596A (en) * 1991-06-26 1995-08-22 L'oreal Keratinous fiber dyeing compositions and processes utilizing oxidation dye precursors in combination with dimethoxy meta-aminophenol couplers
US5609649A (en) * 1989-11-10 1997-03-11 L'oreal Tinctorial composition for keratinous fibers containing oxidation dye precursors and couplers derived from 4-hydroxyindole, and dyeing method using them
DE29710077U1 (de) * 1997-06-10 1998-10-08 Goldwell GmbH, 64297 Darmstadt Haarfärbemittel
DE19807245C1 (de) * 1998-02-20 1999-02-04 Goldwell Gmbh Haarfärbemittel
FR2767686A1 (fr) * 1997-09-01 1999-03-05 Oreal Composition pour la teinture d'oxydation des fibres keratiniques comprenant du 2-chloro 6-methyl 3-aminophenol et deux bases d'oxydation, et procede de teinture
EP0951900A2 (fr) * 1998-03-03 1999-10-27 Bristol-Myers Squibb Company Compositions de teinture pour cheveux contenant des 2-chloro- et 2,6-dichloro-4-aminophenols et des phenylpyrazolones

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5609649A (en) * 1989-11-10 1997-03-11 L'oreal Tinctorial composition for keratinous fibers containing oxidation dye precursors and couplers derived from 4-hydroxyindole, and dyeing method using them
US5443596A (en) * 1991-06-26 1995-08-22 L'oreal Keratinous fiber dyeing compositions and processes utilizing oxidation dye precursors in combination with dimethoxy meta-aminophenol couplers
DE29710077U1 (de) * 1997-06-10 1998-10-08 Goldwell GmbH, 64297 Darmstadt Haarfärbemittel
FR2767686A1 (fr) * 1997-09-01 1999-03-05 Oreal Composition pour la teinture d'oxydation des fibres keratiniques comprenant du 2-chloro 6-methyl 3-aminophenol et deux bases d'oxydation, et procede de teinture
DE19807245C1 (de) * 1998-02-20 1999-02-04 Goldwell Gmbh Haarfärbemittel
EP0951900A2 (fr) * 1998-03-03 1999-10-27 Bristol-Myers Squibb Company Compositions de teinture pour cheveux contenant des 2-chloro- et 2,6-dichloro-4-aminophenols et des phenylpyrazolones

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003041671A2 (fr) * 2001-11-17 2003-05-22 Henkel Kommanditgesellschaft Auf Aktien Colorants d'oxydation contenant du bis-(5-amino-2-hydroxyphenyl)-methane
WO2003041671A3 (fr) * 2001-11-17 2003-11-13 Henkel Kgaa Colorants d'oxydation contenant du bis-(5-amino-2-hydroxyphenyl)-methane

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