WO2003041671A2 - Oxidationsfärbemittel mit bis-(5-amino-2-hydroxyphenyl)-methan und/oder 4-amino-2-{4-[5'-amino-2'-hydroxyphenyl)-methyl-] piperazinyl)-methyl}-phenol-tetrahydrochloride - Google Patents
Oxidationsfärbemittel mit bis-(5-amino-2-hydroxyphenyl)-methan und/oder 4-amino-2-{4-[5'-amino-2'-hydroxyphenyl)-methyl-] piperazinyl)-methyl}-phenol-tetrahydrochloride Download PDFInfo
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- WO2003041671A2 WO2003041671A2 PCT/EP2002/012558 EP0212558W WO03041671A2 WO 2003041671 A2 WO2003041671 A2 WO 2003041671A2 EP 0212558 W EP0212558 W EP 0212558W WO 03041671 A2 WO03041671 A2 WO 03041671A2
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- amino
- methylphenol
- methyl
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- hydroxyethyl
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- 0 *C(C(*)N(*)c1c2)c1cc(O*)c2OS Chemical compound *C(C(*)N(*)c1c2)c1cc(O*)c2OS 0.000 description 1
Classifications
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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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/415—Aminophenols
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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
-
- 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
- A61K8/4953—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 containing pyrimidine ring derivatives, e.g. minoxidil
Definitions
- the present invention relates to agents for dyeing keratin fibers, the bis (5-amino-2-hydroxyphenyl) methane and / or 4-amino-2- ⁇ (4- [(5 '- amino-2' -hydroxyphenyl) - methyl] piperazinyl) methyl ⁇ phenol-etrahydrochloride in combination with at least one further, special dye precursor.
- 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 colorations are generally sensitive to shampooing, so that a frequently undesirable shift in nuances 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 the actual dyes under the influence of oxidizing agents or of atmospheric oxygen with one another or under coupling with one or more coupler components.
- the oxidation colorants are characterized by excellent, long-lasting coloring results.
- Good oxidation dye precursors should primarily fulfill the following requirements: They must have the desired color shades in the oxidative coupling train sufficient intensity and authenticity. They must also have a good ability to draw onto the fiber, whereby there must be no noticeable differences between stressed and freshly regrown hair, especially with human hair (leveling ability). They should be resistant to light, heat, sweat, friction and the influence of chemical reducing agents, e.g. B. perm fluids. 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.
- colorants which contain bis- (5-amino-2-hydroxyphenyl) methane in combination with at least one further special dye precursor ,
- a first subject of the present invention is therefore an agent for dyeing keratin fibers, in particular human hair, containing, in a medium suitable for dyeing, a combination of a) bis (5-amino-2-hydroxyphenyl) methane and / or as dye precursors 4-amino-2 - ⁇ (4- [5'-amino-2'-hydroxyphenyl) methyl] piperazinyl) methyl ⁇ phenol tetrahydrochloride and b) at least one further dye precursor selected from p-toluenediamine, 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine, 4-amino-3-methylphenol, 4-amino-2,6-dichlorophenol, 4-amino-2,6-dibromophenol, 4-amino-3-fluorophenol, 4-amino-2-aminomethylphenol, 4-amino-2 - ((diethylamino) methyl) phenol, 2-amino-4-methylphenol,
- keratin fibers are understood to mean furs, wool, feathers and in particular human hair.
- physiologically tolerable salts of the compounds according to the invention are the hydrochlorides, hydrobromides, the sulfates, the phosphates, the acetates, the propionates, the citrates and the lactates.
- the color-changing agents according to the invention can 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
- Primary aromatic amines with a further free or substituted hydroxy group in the para or ortho position are usually used as developer components. or amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazole derivatives and 2,4,5,6-tetraaminopyrimidine and its derivatives.
- G 1 stands for a hydrogen atom, a Ci to C 4 alkyl radical, a C ⁇ to C 4 monohydroxyalkyl radical, a C 2 to C 4 polyhydroxyalkyl radical, a (C ⁇ to C 4 ) alkoxy (Cj - to C 4 ) alkyl radical, a 4'-aminophenyl radical or a Ci to C - 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 (- C) - alkoxy- (C - to C) alkyl radical or a C ⁇ - to C 4 alkyl radical substituted with a nitrogenous group;
- G 3 represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, a Cj to C 4 alkyl radical, a Ci to C 4 monohydroxyalkyl radical, a Cj to C 4 hydroxyalkoxy radical Cj to C 4 acetylaminoalkoxy radical, a Cp to C 4 mesylaminoalkoxy radical or a Ci to C 4 carbamoylaminoalkoxy radical;
- G 4 represents a hydrogen atom, a halogen atom or a Cj to C 4 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.
- 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.
- Ci to C 4 alkoxy radicals preferred according to the invention are, for example, a methoxy or an ethoxy group.
- Further preferred examples of a C 1 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 (I) are in particular the amino groups, C ⁇ - to C 4 - monoalkylamino groups, C ⁇ - to C 4 -dialkylamino groups, Cj - to C 4 - trialkylammonium groups, C ⁇ - to C 4 -monohydroxyalkylamino groups, imidazolinium and ammonium.
- Particularly preferred p-phenylenediamines of the formula (I) 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, N-
- p-phenylenediamine derivatives of the formula (I) which are particularly preferred are p-phenylenediamine, p-toluenediamine, 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine and N, N-bis- ( ⁇ -hydroxyethyl) -p-phenylenediamine. It can further be preferred according to the invention to use as developer component compounds which contain at least two aromatic nuclei which are substituted with amino and / or hydroxyl groups.
- binuclear developer components which can be used in the coloring compositions according to the invention, one can name in particular the compounds which correspond to the following formula (II) and their physiologically tolerable salts:
- - Z 1 and Z 2 independently represent a hydroxyl or NH 2 radical, which is optionally substituted by a C ⁇ - substituted hydroxyalkyl radical and / or by a bridge Y -, -C 4 alkyl radical by a CJ-4 to C or which is optionally part of a bridging ring system,
- the bridge 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 is interrupted or terminated by one or more nitrogen-containing groups and / or one or more heteroatoms such as oxygen, sulfur or nitrogen atoms may be and may be substituted by one or more hydroxyl or Ci to C 8 alkoxy radicals, or a direct bond,
- G 5 and G 6 are each independently a hydrogen or halogen atom, a Ci to C 4 alkyl radical, a Ci to C 4 -Monohydroxyalkylradikal, a C 2 - to C 4 - Polyhydroxyalkylradikal, a CJ-4 to C -Aminoalkyl radical or a direct connection to the bridging Y, G 7 , G 8 , G 9 , G 10 , G 11 and G 12 independently of one another represent a hydrogen atom, a direct bond to the bridging Y or a Cj to C 4 alkyl radical, with the provisos that the compounds of the formula ( II) contain only one bridge Y per molecule and the compounds of the formula (II) contain at least one amino group which carries at least one hydrogen atom.
- Preferred dinuclear developer components of the formula (II) are in particular: N, N'- bis (ß-hyckoxyemyl) -N, N'-bis- (4'-ammophenyl) -l, 3-diamino-propan-2-ol, N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) ethylenediamine, N, N'-bis (4-aminophenyl) tetramethylene diamine, N, N , -bis - (ß-Hydroxyethyl) -N, N , -bis- (4-aminophenyl) -tetramethyl-endiamine, N, N'-bis- (4-methyl-aminophenyl) -tetramethylene-diamine, N, N'-bis- (ethyl ) -N, N'- bis- (4'-amino-3'-methylphen
- Very particularly preferred dinuclear developer components of the formula (II) are 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'-aminophenyl) - 1,4-diazacycloheptane and l, 10-bis (2 ', 5'-diaminophenyl) - l, 4,7,10-tetraoxadecane or one of its physiologically acceptable salts.
- P-Aminophenol derivatives of the formula (III) are particularly preferred in which:
- G 13 represents a hydrogen atom, a halogen atom, a C 1 -C 4 -alkyl radical, a C 1 -C to Gp monohydroxyalkyl radical, a (C 1 -C 4 ) -alkoxy- (d- to C 4 ) -alkyl radical, a Cp to C 4 -aminoalkyl radical, a hydroxy (C ⁇ - to C 4) - alkylamino radical, a Cp to C 4 -Hydroxyalkoxyradikal, a Cp to C 4 hydroxyalkyl (cpuntil C4) -aminoalkyl radical, or a (di-Cp to C 4 - Alkylamino) - (Cp to C 4 ) - alkyl radical, and
- G 14 represents a hydrogen or halogen atom, a Cp to C 4 alkyl radical, a Cp to C 4 monohydroxyalkyl radical, a C 2 to C 4 polyhydroxyalkyl radical, a (Cp to C 4 ) alkoxy (Cp to C 4 ) -alkyl radical, a Cp to C 4 aminoalkyl radical or a Cp to C 4 cyanoalkyl radical,
- G 15 represents hydrogen, a Cp to C 4 alkyl radical, a Cp to C 4 monohydroxyalkyl radical, a C 2 to C 4 polyhydroxyalkyl radical, a phenyl radical or a benzyl radical, and
- - 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-fluorophenol, 4-amino-2,6-dichlorophenol , 4-amino-2,6-dibromophenol, 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-fiuorophenol , 4-amino-2-chl ⁇ henol, 2,6-dichloro-4-aminophenol, 4-amino-2- ((diethylamino) methyl)
- Very particularly preferred compounds of the formula (III) are p-aminophenol, 4-amino-3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2 - ((diethylamino) methyl) phenol and 4-amino-2,6 -dichlorphenol.
- 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- (ß-
- 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-
- 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-1 - (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-
- 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 Cp to C 4 alkyl radical, an aryl radical, a Cp to C 4 hydroxyalkyl radical, a C 2 to C 4 polyhydroxyalkyl radical ( Cp to C 4 ) alkoxy- (Cp to C 4 ) -alkyl radical, a Cp to C 4 -aminoalkyl radical which can optionally be protected by an acetyl-ureide or sulfonyl radical, a (Cp to C) -alkylamino- (Cp to C) alkyl radical, a di - [(Cp to C 4 ) alkyl] - (Cp to C 4 ) aminoalkyl radical, the dialkyl radicals optionally forming a carbon cycle or a heterocycle with 5 or 6 chain links Cp to C 4 hydroxyalkyl or a di (Cp to C 4 ) - [hydroxyalkyl] - (
- - n has the value 0 or 1, with the proviso that
- n has the value 0, and the groups NG 17 G 18 and NG 19 G 20 occupy positions (2,3); (5,6); (6,7); (3.5) or (3.7);
- pyrazole- [1,5-a] pyrimidine of the formula (IV) above contains a hydroxy 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 formula (IV) above 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.
- Preferred coupler components according to the invention are m-aminophenol and its derivatives such as 5-amino-2-methylphenol, N-
- Ethylamino-4-methylphenol and 2,4-dichloro-3-aminophenol, o-aminophenol and its derivatives, m-diaminobenzene and its derivatives such as, for example, 2,4-diaminophenoxyethanol, 1,3-bis- (2 ', 4'- diaminophenoxy) propane, 1-
- Resorcinol monomethyl ether 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol,
- Naphthalene derivatives such as 1-naphthol, 2-methyl-1-naphthol, 2-
- Mo ⁇ holinderivate 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-
- Pyrimidine derivatives such as 4,6-diaminopyrimidine, 4-amino-2,6-dihydroxypyrimidine, 2,4-diamino-6-hydroxypyrimidine, 2,4,6-trihydroxypyrimidine, 2-
- Methylenedioxybenzene derivatives such as l-hydroxy-3,4-methylenedioxybenzene, l-amino-3,4-methylenedioxybenzene and l- (2'-hydroxyethyl) - amino-3, 4-methylenedioxybenzene.
- Particularly preferred further 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, 2,5-dimethylresorcinol, 2,6-dihydroxy-3,4-dimethylpyridine and 3-amino-2-methylamino-6 -methoxypyridin.
- the hair colorants according to the invention may also contain further components in minor amounts be, as far as 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 represents hydrogen, a CpC 4 alkyl group or a CpC 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 CpC alkyl group
- R 4 represents hydrogen, a CpC 4 alkyl group or a group -CO-R 6 , in which
- R 6 represents a CpC 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 CpC alkyl group or a CpC 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 CpC 4 alkyl group
- R 4 represents hydrogen, a CpC 4 alkyl group or a group -CO-R 6 , in which
- R 6 represents a CpC 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.
- 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 substantive dyes are those with the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 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
- the agents 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, sapwood, sage, blue wood, madder root, catechu, sedre and alkanna root.
- naturally occurring dyes such as, for example, henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, sapwood, 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, aerosols or other preparations which are suitable for use on the hair.
- surfactant-containing foaming solutions such as shampoos, 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 CpC 4 alcohol, in particular ethanol or isopropanol.
- the agents according to the invention can additionally contain other organic solvents, such as 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. However, a chemical oxidizing agent is preferably used, especially when a lightening effect on human hair is desired in addition to the coloring.
- Persulfates, chlorites and in particular hydrogen peroxide or its adducts with urea, melamine and sodium borate are suitable as oxidizing agents. But you can also apply the oxidation dye together with a catalyst on the hair, which the oxidation of the dye precursors, for. B. activated.
- catalysts are e.g. B. transition metal compounds, iodides, quinones or certain enzymes.
- Suitable enzymes are e.g. B. peroxidases, which can significantly increase the effect of small amounts of hydrogen peroxide.
- enzymes are suitable according to the invention which directly oxidize the oxidation dye precursors with the help of atmospheric oxygen, such as the laccases, or generate small amounts of hydrogen peroxide in situ and thus activate the oxidation of the dye precursors biocatalytically.
- catalysts for the oxidation of the dye precursors are the so-called 2-electron oxidoreductases in combination with the substrates specific for them, e.g. B.
- Pyranose oxidase and e.g. B. D-glucose or galactose,
- Lactate oxidase and lactic acid and their salts Lactate oxidase and lactic acid and their salts
- 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 applied Rinse removed from the hair to be dyed. Washing with a shampoo is not necessary if a carrier with a high tenside content, such as a coloring shampoo, has been 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, in principle both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable. In many cases, however, it has proven advantageous to select the surfactants from anionic, zwitterionic or nonionic surfactants.
- 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.
- anionic surfactants are, in each case in the form of the sodium, potassium and ammonium and the mono-, di- and trialkanolammonium salts with 2 or 3 carbon atoms in the alkanol group, linear fatty acids with 10 to 22 carbon atoms (soaps )
- Ether carboxylic acids of the formula RO- (CH 2 -CH 2 O) x -CH 2 -COOH, in which R is a linear one
- Alkyl group with 10 to 22 carbon atoms and x 0 or 1 to 16,
- Atoms in the alkyl group and 1 to 6 oxyethyl groups linear alkanesulfonates with 12 to 18 C atoms, linear alpha-olefin sulfonates with 12 to 18 C atoms,
- Esters of tartaric acid and citric acid with alcohols the addition products of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols with 8 to 22
- 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
- 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. Such alkyl radicals are, for example, 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 1 consists essentially of C 8 - and Cio-alkyl groups, essentially from C 12 - and C 14 -alkyl groups, essentially from C 8 - to C 6 -alkyl groups or essentially from Cj 2 - C 16 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.
- 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.
- the 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 wear.
- Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the coconut alkyl dimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example the coconut acylaminopropyl dimethylammonium glycinate, and 2-alkyl-3-carboxylmethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
- 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.
- ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkylsarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid each with about 8 to 18 C. Atoms in the alkyl group.
- Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 1 2 - 1 8 - acyl isarcosine.
- 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.
- 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.
- a compound from this group of substances which is particularly suitable according to the invention is stearamidopropyldimethylamine, which is commercially available under the name Tegoamid S 18.
- 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 with a "normal” homolog distribution and those with a narrowed homolog distribution can be used.
- “Normal” homolog distribution is understood to mean mixtures of homologues which are obtained as catalysts when fatty alcohol and alkylene oxide are reacted 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.
- polymeric dimethyldiallylammonium salts and their copolymers with acrylic acid and esters and amides of acrylic acid and methacrylic acid The under the names Merquat ® 100 (poly (dimethyldiallylammonium chloride)),
- Merquat ® 550 (dimethyldiallylammonium chloride-acrylamide copolymer) and Merquat ® 280 (dimethyldiallylammonium chloride-acrylic acid copolymer) are examples of such cationic polymers.
- Such compounds are available under the names Gafquat ® 734 and Gafquat ® 755 commercially.
- Vinylpyrrolidone-Me oimidazoliniumchlorid-copolymers as they are offered under the name Luviquat ® , quaternized polyvinyl alcohol and those under the names 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.
- Silicone oils in particular dialkyl and alkylarylsiloxanes, such as, for example, dimethylpolysiloxane and, are also suitable as conditioning agents Methylphenylpolysiloxane, as well as their alkoxylated and quaternized analogues.
- 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 Corning® 929 emulsion (containing a hydroxyl-amino-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 Corning® 929 emulsion containing a hydroxyl-amino-modified silicone, which is also referred to as amodimethicone
- 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.
- hair-conditioning compounds are phospholipids, for example soy lecithin, egg lecithin and cephalins.
- auxiliaries and additives are, for example, nonionic polymers such as, for example, vinyl pyrrolidone / vinyl acrylate copolymers,
- Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans,
- Cellulose derivatives e.g. B. methyl cellulose, hydroxyalkyl cellulose and
- Structurants such as maleic acid and lactic acid, hair-conditioning compounds such as phospholipids, for example soy lecithin,
- Protein hydrolyzates especially elastin, collagen, keratin, milk protein,
- Solvents and intermediates such as ethanol, isopropanol, ethylene glycol,
- Propylene glycol, glycerin and diethylene glycol, active ingredients that improve fiber structure in particular mono-, di- and oligosaccharides such as glucose, galactose, fructose, fructose and lactose, quaternized amines such as methyl l-alkylamidoethyl-2-alkylimidazolinium methosulfate
- Anti-dandruff agents such as piroctone olamine, zinc omadine and climbazole,
- Light stabilizers in particular derivatized benzophenones, cinnamic acid derivatives and
- Substances for adjusting the pH such as 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 especially those of groups A, B 3 ,
- Plant extracts such as the extracts from green tea, oak bark, nettle,
- Consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers,
- Fats and waxes such as walrus, beeswax, montan wax and paraffins, fatty acid,
- 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,
- Cetylstearyl alcohol with approx. 20 mol EO (INCI name: Ceteareth-20) (Cognis)
- the oxidative development of the color was carried out with 3% hydrogen peroxide solution as the oxidation solution.
- 100 g of the emulsion were mixed with 50 g of hydrogen peroxide solution (3%) and mixed.
- the coloring cream was applied to approx. 5 cm long strands of standardized, 90% gray, but not specially pretreated human hair and left there for 30 minutes at 32 ° C. After the dyeing process was completed, the hair was rinsed, washed with a conventional shampoo and then dried.
- Polymer JR® 400 (Polyquaternium 10) 6 0.4
- Polymer JR® 400 (Polyquaternium 10) 6 0.4
- Guarhydroxypropyltrimethylammoniumchlorid INCI name: guar hydroxypropyltrimonium chloride; (Cognis) poly [N-3- (dimethylammonium) propyl] -N '- [3-ethyleneoxyethylene dimethylammonium) propyl] urea dichloride; INCI name:
- Dimethyldiallylammonium chloride-acrylamide copolymer (8-9% active ingredient); INCI name: Polyquaternium-7 (Chemviron)
- Dimethyldiallylammonium chloride-acrylic acid copolymer (35% active substance); INCI name: Polyquaternium-22 (Chemviron) Vinylpyrrolidone-methacrylamidopropyltrimemylammonium chloride copolymer (19-21% active ingredient); INCI name: Polyquaternium-28 (General Anilin Firm Co ⁇ .) 4-Hexyl-5 (6) -carboxy-2-cyclohexen-1-octanoic acid, potassium salt; (Westvaco Chemicals)
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Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02779546A EP1443888A2 (de) | 2001-11-17 | 2002-11-11 | Oxidationsfärbemittel mit bis-(5-amino-2-hydroxyphenyl)-methan und/oder 4-amino-2- 4-[5'-amino-2'-hydroxyphenyl)-methyl-]piperazinyl)-methyl -phenol-tetrahydrochlorid |
AU2002342899A AU2002342899A1 (en) | 2001-11-17 | 2002-11-11 | Oxidation colouring agent with bis (5-amino-2-hydroxyphenyl)-methane and/or 4-amino-2-{(4-(5'-amino-2'-hydroxy-phenyl)-methyl-) piperazinyl)-methyl}-phenol tetrahydrochloride |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
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DE10156667A DE10156667A1 (de) | 2001-11-17 | 2001-11-17 | Oxidationsfärbemittel auf der Basis zweikerniger Entwicklerkomponenten |
DE10156667.0 | 2001-11-17 | ||
DE2001156881 DE10156881A1 (de) | 2001-11-20 | 2001-11-20 | Oxidationsfärbemittel auf der Basis zweikerniger Entwicklerkomponenten |
DE10156881.9 | 2001-11-20 | ||
DE20118982.8 | 2001-11-21 | ||
DE20118982U DE20118982U1 (de) | 2001-11-21 | 2001-11-21 | Oxidationsfärbemittel mit Bis-(5-amino-2-hydroxyphenyl)-methan |
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WO2003041671A2 true WO2003041671A2 (de) | 2003-05-22 |
WO2003041671A3 WO2003041671A3 (de) | 2003-11-13 |
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EP (1) | EP1443888A2 (de) |
AU (1) | AU2002342899A1 (de) |
WO (1) | WO2003041671A2 (de) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2865397A1 (fr) * | 2004-01-28 | 2005-07-29 | Oreal | Composition de teinture des fibres keratiniques contenant une alcool oxydase et un colorant direct quinonique, procede mettant en oeuvre cette composition |
EP1559412A1 (de) * | 2004-01-28 | 2005-08-03 | L'oreal | Keratinfaserfärbemittel enthaltend eine Alkohol-Oxydase und eine kationische Entwicklerkomponente |
US8608810B2 (en) | 2012-03-27 | 2013-12-17 | The Procter & Gamble Company | Hair colorant compositions comprising 3-amino-2,6-dimethylphenol and 1,4-phenylenediamine-type developers, methods, and kits comprising the compositions |
US8617256B2 (en) | 2012-03-27 | 2013-12-31 | The Procter & Gamble Company | Hair colorant compositions comprising 3-amino-2,6-dimethylphenol and 4-aminophenol-type developers, methods, and kits comprising the compositions |
EP1897532B2 (de) † | 2006-09-11 | 2014-11-05 | Kao Germany GmbH | Haarfärbemittel |
WO2021163777A1 (pt) * | 2020-02-19 | 2021-08-26 | Gloss Express Do Brasil Comercio De Produtos De Beleza Ltda - Epp | Composição cosmética para fibras queratínicas e métodos de aplicação da dita composição |
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DE19916031A1 (de) * | 1999-04-09 | 2000-10-19 | Henkel Kgaa | Färbemittel und Verwendung |
DE19916030A1 (de) * | 1999-04-09 | 2000-10-19 | Henkel Kgaa | Färbemittel und Verwendung |
WO2001008645A1 (de) * | 1999-08-03 | 2001-02-08 | Henkel Kommanditgesellschaft Auf Aktien | Neue entwickler-kuppler-kombinationen |
WO2001041714A2 (de) * | 1999-12-09 | 2001-06-14 | Henkel Kommanditgesellschaft Auf Aktien | Neue farbstoffkombination |
WO2001041717A2 (de) * | 1999-12-09 | 2001-06-14 | Henkel Kommanditgesellschaft Auf Aktien | Neue farbstoffkombination |
WO2001097766A2 (de) * | 2000-06-23 | 2001-12-27 | Henkel Kommanditgesellschaft Auf Aktien | Oxidationshaarfärbemittel |
WO2002032385A1 (de) * | 2000-10-14 | 2002-04-25 | Henkel Kommanditgesellschaft Auf Aktien | Oxidationsfärbemittel mit 2-chlor-p-aminophenol |
-
2002
- 2002-11-11 EP EP02779546A patent/EP1443888A2/de not_active Ceased
- 2002-11-11 AU AU2002342899A patent/AU2002342899A1/en not_active Abandoned
- 2002-11-11 WO PCT/EP2002/012558 patent/WO2003041671A2/de not_active Application Discontinuation
Patent Citations (7)
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DE19916031A1 (de) * | 1999-04-09 | 2000-10-19 | Henkel Kgaa | Färbemittel und Verwendung |
DE19916030A1 (de) * | 1999-04-09 | 2000-10-19 | Henkel Kgaa | Färbemittel und Verwendung |
WO2001008645A1 (de) * | 1999-08-03 | 2001-02-08 | Henkel Kommanditgesellschaft Auf Aktien | Neue entwickler-kuppler-kombinationen |
WO2001041714A2 (de) * | 1999-12-09 | 2001-06-14 | Henkel Kommanditgesellschaft Auf Aktien | Neue farbstoffkombination |
WO2001041717A2 (de) * | 1999-12-09 | 2001-06-14 | Henkel Kommanditgesellschaft Auf Aktien | Neue farbstoffkombination |
WO2001097766A2 (de) * | 2000-06-23 | 2001-12-27 | Henkel Kommanditgesellschaft Auf Aktien | Oxidationshaarfärbemittel |
WO2002032385A1 (de) * | 2000-10-14 | 2002-04-25 | Henkel Kommanditgesellschaft Auf Aktien | Oxidationsfärbemittel mit 2-chlor-p-aminophenol |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2865397A1 (fr) * | 2004-01-28 | 2005-07-29 | Oreal | Composition de teinture des fibres keratiniques contenant une alcool oxydase et un colorant direct quinonique, procede mettant en oeuvre cette composition |
EP1559412A1 (de) * | 2004-01-28 | 2005-08-03 | L'oreal | Keratinfaserfärbemittel enthaltend eine Alkohol-Oxydase und eine kationische Entwicklerkomponente |
EP1559411A1 (de) * | 2004-01-28 | 2005-08-03 | L'oreal | Zusammensetzung zur Färbung von keratinischen Fasern enthaltend eine Akoholoxidase und ein Chinonfarbstoff, und das Verfahren zur Verwendung der Zusammensetzung |
EP1897532B2 (de) † | 2006-09-11 | 2014-11-05 | Kao Germany GmbH | Haarfärbemittel |
US8608810B2 (en) | 2012-03-27 | 2013-12-17 | The Procter & Gamble Company | Hair colorant compositions comprising 3-amino-2,6-dimethylphenol and 1,4-phenylenediamine-type developers, methods, and kits comprising the compositions |
US8617256B2 (en) | 2012-03-27 | 2013-12-31 | The Procter & Gamble Company | Hair colorant compositions comprising 3-amino-2,6-dimethylphenol and 4-aminophenol-type developers, methods, and kits comprising the compositions |
WO2021163777A1 (pt) * | 2020-02-19 | 2021-08-26 | Gloss Express Do Brasil Comercio De Produtos De Beleza Ltda - Epp | Composição cosmética para fibras queratínicas e métodos de aplicação da dita composição |
Also Published As
Publication number | Publication date |
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WO2003041671A3 (de) | 2003-11-13 |
AU2002342899A1 (en) | 2003-05-26 |
EP1443888A2 (de) | 2004-08-11 |
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