WO2002026201A2 - Colorants d'oxydation contenant 2-amino-5-methylphenol - Google Patents

Colorants d'oxydation contenant 2-amino-5-methylphenol Download PDF

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Publication number
WO2002026201A2
WO2002026201A2 PCT/EP2001/010851 EP0110851W WO0226201A2 WO 2002026201 A2 WO2002026201 A2 WO 2002026201A2 EP 0110851 W EP0110851 W EP 0110851W WO 0226201 A2 WO0226201 A2 WO 0226201A2
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Prior art keywords
amino
aminophenol
methylphenol
group
radical
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PCT/EP2001/010851
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German (de)
English (en)
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WO2002026201A3 (fr
Inventor
Horst Höffkes
Doris Oberkobusch
Udo Erkens
Bernd Meinigke
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Henkel Kommanditgesellschaft Auf Aktien
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Priority to AU9557501A priority Critical patent/AU9557501A/xx
Publication of WO2002026201A2 publication Critical patent/WO2002026201A2/fr
Publication of WO2002026201A3 publication Critical patent/WO2002026201A3/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • 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
    • 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

Definitions

  • the present invention relates to agents for dyeing keratin fibers, the 2-amino-5-methylphenol in combination mi. Contain p-aminophenol derivatives and special coupler components, a process for dyeing keratin fibers with these agents 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 the actual dyes under the influence of oxidizing agents or atmospheric oxygen with one another or under coupling with one or more coupler components.
  • 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, whereby there must be no noticeable differences between stressed and fit, regrown hair, especially with human hair (leveling ability).
  • a first object 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.
  • p-aminophenol derivatives of the formula (I) are preferably used as component (B)
  • R 1 represents a hydrogen atom, a halogen atom, a C 1 -C 4 -monohydroxyalkyl radical, a (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl radical, a C 1 -C 4 -aminoalkyl radical hydroxy (Cr to C4) -alkylaminoradikal, a Ci to C 4 - Hydroxyalkoxyradikal, a Ci to C 4 hydroxyalkyl (C ⁇ -to C4) -aminoalkyl radical, or a (di-Ci to C 4 alkylamino ) - (C ⁇ - to C 4 ) -alkyl radical, and
  • R 2 stands for a hydrogen or halogen atom, a d- to C -alky radical, a Ci- to C -monohydroxyalkyl radical, a C- to C -polyhydroxyalkyl radical, a (Ci- to C 4 ) -alkoxy- (C ⁇ - to C 4) alkyl radical, a radical Ci to C -Aminoalky .radikal or a Ci to C 4 -Cyanoalky,
  • R 3 represents hydrogen, a - to C 4 -alkyl radical, a Ci to C 4 - monohydroxyalkyl radical, a C 2 - to C 4 -polyhydroxyalkyl radical, a phenyl radical or a benzyl radical, and
  • R 4 represents hydrogen or a halogen atom.
  • Preferred p-aminophenol derivatives are p-aminophenol, N-methyl-p-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 2-hydroxymethylamino-4-amino-phenol, 4-amino -3-hydroxymethylphenol, 4-amino-2- (2-hydroxyethoxy) phenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2 - (ß-hydroxyethyl-aminomethyl) phenol, 4-amino-2-fluorophenol, 4-amino-2-chlorophenol, 2,6-DicUor-4 - ⁇ rninophenol, 2,6-dibromo-4-aminophenol, 4- Amino-2 - ((diethylamino) methyl) phenol and their physiologically compatible salts.
  • Particularly preferred p-aminophenol derivatives are p-aminophenol, 4-amino-3-methylphenol and 4-amino-2 - ((diethylamino) methyl) phenol.
  • m-aminophenol derivatives of the formula (II) are preferably used as component (cl)
  • R 5 and R 6 independently represent hydrogen, a trifluoroacetyl
  • Monohydroxyalkyl group a C ⁇ polyhydroxyalkyl group or a C 1 . 4 -
  • R 7 , R 8 and R 9 independently of one another represent hydrogen, a CM-alkyl group, a C M -alkoxy group, a C M -monohydroxyalkyl group, a C ⁇ -
  • m-aminophenol derivatives of the formula (II) are m-aminophenol, N-cyclopentyl-3-aminophenol, 5-amino-2-methylphenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol , 2,6-dimethy 1-3 -aminophenol, 3-trifluoroacetylammo-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, 3-ethylamino-4-methylphenol and 2,4-dichloro-3-aminophenol and their physiologically tolerable salts.
  • Preferred m-aminophenol derivatives of the formula (II) are N-cyclopentyl-3-aminophenol, 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, 3-ethylamino-4-methylphenol and 2,4-dichloro-3-aminophenol and their physiologically tolerable salts.
  • Particularly preferred m-aminophenol derivatives of the formula (II) are 3-aminophenol, 5-amino-2-methylphenol and 2-chloro-6-methyl-3-aminophenol.
  • a very particularly preferred m-aminophenol derivative is 2-chloro-6-methyl-3-aminophenol.
  • 5- (2'-Hydroxyethyl) - u- ⁇ ino-2-methylphenol is also a very particularly preferred m-aminophenol derivative.
  • the agent according to the invention additionally contains at least one pyridine derivative (c2) and / or a direct dye for further shading, if the agent according to the invention is 5-amino as the m-aminophenol derivative (cl) Contains -2-methylphenol.
  • pyridine derivatives of the formula (III) are preferably used as component (c2)
  • R 10 , R n , R 12 , R 13 and R 14 independently of one another represent hydrogen, a Ci
  • R 13 can also represent a halogen atom, in particular a chlorine atom, with the proviso that at least two of the radicals R 10 , R 11 , R 12 , R 13 and R 14 represent a hydroxyl group or an optionally substituted amino group.
  • Preferred pyridine derivatives of the formula (III) are 2,6-dihydroxypyridine, 2-amino-3-hydroxypyridine, 2-amino-5-chloro-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxypyridine, 2,6- Dihydroxy-3,4-dimethylpyridine, 2,6-dihydroxy-4-methylpyridine, 2,6-diaminopyridine, 2,3-diamino-6-methoxypyridine and 3,5-diamino-2,6-dimethoxypyridine and their physiologically acceptable salts ,
  • a particularly preferred pyridine derivative of the formula (III) is 2-amino-3-hydroxypyridine.
  • Examples of the C 1 -C 4 -alkyl radicals mentioned as substituents in the compounds of the formulas (I), (II) and (III) according to the invention are the groups methyl, ethyl, propyl, isopropyl and butyl. Ethyl and methyl are preferred alkyl radicals.
  • Q to C 4 alkoxy radicals preferred according to the invention are, for example, a methoxy or an ethoxy group.
  • a hydroxymethyl, a 2-hydroxyethyl, a 3-hydroxypropyl or a 4-hydroxybutyl group can be mentioned as preferred examples of a C 1 to C 4 hydroxyalkyl group.
  • a 2-hydroxyethyl group is particularly preferred.
  • Examples of halogen atoms according to the invention are F, Cl or Br atoms, Cl atoms are very particularly preferred. According to the invention, the other terms used are derived from the definitions given here.
  • 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 with regard to the dye precursors which can be used in the agents according to the invention.
  • 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 to C 4 polyhydroxyalkyl radical, a (Ci to C 4 ) alkoxy (C ⁇ - to C) 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 stands for a hydrogen atom, a Ci to C 4 alkyl radical, a Ci to C 4 monohydroxyalkyl radical, a C 2 to C polyhydroxyalkyl radical, a (Ci to C 4 alkoxy (C ⁇ to C) - alkyl radical or a Cj to C alkyl radical which is substituted with a nitrogen-containing group;
  • G 3 represents a hydrogen atom, a halogen atom, such as a chlorine, bromine, iodine or fluorine atom, a C 1 -C 4 -alkyl radical, a C 1 -C 4 -monohydroxyalkyl radical, a C 1 -C 4 -hydroxyalkoxy radical, a C. to C -Acetylaminoalkoxyradikal, a Ci to C - Mesylaminoalkoxyradikal or a Ci to C 4 -Carbamoylaminoalkoxyradikal;
  • G 4 represents a hydrogen atom, a halogen atom or a Ci 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.
  • the groups methyl, ethyl, propyl, isopropyl and butyl are examples of the C 1 -C 4 -alkyl radicals mentioned as substituents in the novel compounds.
  • Ethyl and methyl are preferred alkyl radicals.
  • preferred Ci to C 4 -alkoxy radicals 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.
  • Examples of halogen atoms according to the invention are F, Cl or Br atoms, Cl atoms are very particularly preferred.
  • nitrogen-containing groups of formula (IN) are especially the amino groups, Ci to C - monoalkylamino, Ci to C 4 dialkylamino, Ci to C 4 - trialkylammonium, d- to C 4 -Monohydroxyalkylamino phenomenon, imidazolinium and ammonium.
  • Particularly preferred p-phenylenediamines of the formula (IN) 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-phenylene diamine, 2,5-dimethyl-p-phenylene diamine, ⁇ , ⁇ -dimethyl-p-phenylene diamine, N, N-diethyl-p-phenylene diamine, N, N-dipropy 1-p-phenylene diamine , 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-bis- (ß-hydroxy
  • p-phenylenediamine derivatives of the formula (IV) which are particularly preferred are p-phenylenediamine, p-toluenediamine, 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine and N, N-bis ( ⁇ -hydroxyethyl) -p-phenylenediamine ,
  • developer component compounds which contain at least two aromatic nuclei which are substituted with amino and / or hydroxyl groups.
  • Z 1 and Z 2 independently of one another represent a hydroxyl or NH radical, which is optionally replaced by a C 1 -C 4 -alkyl radical, by a C 1 -C 4 - Hydroxyalkyl radical and / or is substituted by a bridging Y or is optionally part of a bridging ring system
  • the bridging Y stands for an alkylene group having 1 to 14 carbon atoms, such as a linear or branched alkylene chain or an alkylene ring, which is one or more nitrogen-containing groups and / or one or more heteroatoms such as oxygen, sulfur or nitrogen atoms can be interrupted or terminated and possibly substituted by one or more hydroxyl or Ci to C 8 alkoxy radicals, or a direct bond
  • the bridging Y stands for an alkylene group having 1 to 14 carbon atoms, such as a linear or branched alkylene chain or an alkylene ring, which is one or more nitrogen-containing groups and / or one or
  • G 5 and G 6 independently of one another represent a hydrogen or halogen atom, a Ci to C 4 alkyl radical, a Ci to C monohydroxyalkyl radical, a C 2 to C 4 polyhydroxyalkyl radical, a Ci to C 4 -A ⁇ inoalky .radikal 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 bridge Y or a Ci to C 4 alkyl radical, with the provisos that the compounds of the formula ( V) contain only one bridge Y per molecule and the compounds of the formula (V) contain at least one amino group which carries at least one hydrogen atom.
  • Preferred dinuclear developer components of the formula (V) are in particular: ⁇ , ⁇ '-bis- (ß-hydroxyethyl) - ⁇ , ⁇ l -bis- (4'-aminophenyl) - 1, 3-diamino-propan-2-ol, N, N'- bis (ß-hydroxyethyl) -N, N'-bis (4'-aminophenyl) ethylenediamine, N, N'-bis- (4-
  • Aminophenyl) tetramethylene diamine N, N'-bis (ß-hydroxyethyl) -N, N'-bis (4-aminophenyl) tetramethylene diamine, N, N'-bis (4-methylaminophenyl) tetramethylene diamine, N, N I -bis- (ethyl) -N, N'-bis (4 , amino, 3 , methylphenyl) ethylenediamine, 1,8-bis (2 ', 5'-diaminophenoxy) -3, 5-dioxaoctane, bis (2-hydroxy-5-aminophenyl) methane, 1,4-bis (4 l -aminophenyl) diaza-cycloheptane, N, N'-bis- (2- hydroxy-5-aminobenzyl) piperazine, N- (4'-aminophenyl) -p-phenylenediamine and 1,10-bis (2 '
  • Very particularly preferred dinuclear developer components of the formula (V) 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) -l, 4-diazacycloheptane and l, 10-bis (2 ', 5'-diaminophenyl) - l, 4,7,10-tetraoxadecane or one of its physiologically acceptable salts.
  • 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 the patents GB 1 026 978 and GB 1 153 196, such as 2,5-diamino-pyridine, 2- (4-methoxyphenyl) amino-3 --- mino-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-tri-minopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2-dimethyl-mino-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 - (ß-hydroxyethyl) pyrazole, 3, 4-diaminopyrazole, 4,5-diamino-1 - (4'-chlorobenzyl) pyrazole, 4,5-diamino-1, 3-dimethylpyrazole, 4.5 -Diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenyl-pyrazole, 4- amino-1,3-dimethyl 1-5 - hydrazinopyrazole, l-benzyl-4,5- diamino-3-methylpyrazole, 4,5-diamino-3-tert-
  • Preferred pyrazole-pyrimidine derivatives are in particular the derivatives of pyrazole- [1,5-a] -pyrimidine of the following formula (VI) and its tautomeric forms, provided that there is a tautomeric equilibrium:
  • G 17 , G 18 , G 19 and G 20 independently of one another represent a hydrogen atom, a C 1 -C 4 -alkyl radical, an aryl radical, a C 1 -C 4 -hydroxyalkyl radical, a C 2 - bis
  • C -polyhydroxyalkyl radical is a (Ci to C) alkoxy (Ci to C) alkyl radical, a Ci to C aminoalkyl radical which can optionally be protected by an acetyl ureide or sulfonyl radical, a (Ci to C 4 ) -alkylamino- (C ⁇ - to C) -alkyl radical, a di - [(C ⁇ - to C) alkyl] - (C ⁇ - to C) - ⁇ minoalkylradikal, where the dialkyl radicals optionally a carbon cycle or one Form a heterocycle with 5 or 6 chain links, a Ci- to C -hydroxyalkyl or a di- (C ⁇ - to C) - [hydroxyalkyl] - (C ⁇ - to C 4 ) - aminoalkyl radical, the X radicals are each independently a hydrogen atom, a Q- to C 4 alkyl radical, an aryl radical, a Ci to C
  • pyrazole- [1,5-a] pyrimidines of the above formula (VI) 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.
  • Coupler components preferred according to the invention are:
  • o-aminophenol and its derivatives m-diaminobenzene and its derivatives such as, for example, 2,4-diaminophenoxyethanol, 1, 3-bis (2 ', 4 l -diaminophenoxy) propane, 1-methoxy-2-amino-4- (2'-hydroxyemyl-imino) benzene, 1,3-bis- (2 ⁇ 4'-di-minophenyl) propane, 2,6- Bis- (2'-hydroxyethylamino) -l-methylbenzene and l-amino-3-bis- (2'-hydroxyethyl) aminobenzene, o-diaminobenzene and their derivatives such as 3,4-diaminobenzoic acid and 2,3-diamino- l-methylbenzene,
  • Resorcinol monomethyl ether 2-methylresorcinol, 5-methylresorcinol, 2,5-
  • Naphthalene derivatives such as 1-naphthol, 2-methyl-1-naphthol, 2-hydroxymethyl-1-naphthol, 2-hydroxyethyl-1-naphthol, 1, 5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 2,7-dihydroxynaphthalene and 2,3-dihydroxynaphthalene,
  • 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-
  • - 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-memylpyrimidine and 4,6-dihydroxy-2-memylpyrimidine, or
  • 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, resorcinol, 4-chlororesorcinol, 2-methylresorcinol, 5-methylresorcinol and 2,5-dimethylresorcinol.
  • the O-ddationsf ⁇ rbstoffvo ⁇ rodukte or the substantive dyes each represent uniform Neritatien. Rather, in the invented hair colorants according to the invention, due to the manufacturing process for the individual dyes, may also 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, each 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 -CC alkyl group or a -C-hydroxy-alkyl 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 -CC 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 C 1 -C 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 -CC 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 present in these in amounts of 0.05-10% by weight, preferably 0.2-
  • the agents according to the invention can contain direct dyes for further shading. These are usually selected from nitrophenylenediamines, nitro-tminophenols, azo dyes, anthraquinones or indo- phenols.
  • 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 -Ni1xo- 4- (ß-hydroxyemyl) --- minophenol, 4-amino-2-nitrodiphenylamine-2'-carboxylic acid, 6-nitro-l, 2,3,4-tetrahydroquinoxaline, 2-hydroxy-l, 4-naphthoquinone, Hy - Droxyethyl-2-nitro
  • 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.
  • 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 products 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 C 1 -C 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.
  • 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 their 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 preferred, but also 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 products.
  • the resulting ready-to-use hair color 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, pholytic, nonionic and cationic surfactants are suitable.
  • anionic and zwitterionic, pholytic, nonionic and cationic surfactants are suitable.
  • 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 alkyl group with 10 to 22 C atoms and x 0 or 1 to 16, acyl sarcosides with 10 to 18 C- Atoms in the acyl group, acyl taurides with 10 to 18 C atoms in the acyl group, acyl isethionates with 10 to 18 C atoms in the acyl group,
  • 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 2 -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. 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 . Usually, however, these compounds are made from natural fats and oils or mineral oils. In this case, 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 2 - and -C-alkyl groups, essentially from C 8 - to C 6 -alkyl groups or essentially from C 2 - to Ci 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.
  • 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 -SO 3 H group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-Al 1N, N-dime yl-mmomum-glycinate, for example the cocoalkyl-dimethylammonium-glycinate, N-acyl-aminopropyl-N, N-dimethyla ⁇ -monium glycinate, for example the coco-acylaminopropyl dimethyl ammonium 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.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under the ESO name Cocamidopropyl Betaine.
  • Ampholytic surfactants are also particularly suitable as co-surfactants.
  • Ampholytic surfactants are understood to mean those 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-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkylaminopropionic acid and -All ⁇ - ylaminoacetic acids each having about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Ci 2 - ⁇ 8 -acylsarcosine.
  • the cationic surfactants used are, in particular, those of the quaternary ammonium compound, esterquat and amidoamine type.
  • Preferred quaternary ammonium compounds are ammonium halides, in particular chlorides and bromides, such as Allsylmemyl-immoniumchloride, Dialkyldimethyl- -immoniumchloride and Trialkylmethyl --- nmoniumchloride, e.g. B.
  • cetyltrimethylammonium chloride ste-uyltrimethylunmonium chloride, diste-iryldimemylainmonium chloride, lauryldimethylammonium chloride, lau-yldimemylben-ylammonium chloride and tricetyl-methylammonium chloride, as well as those known under the INCI names quatemium-27 and quatidium-27 and quatidiumium.
  • the long alkyl chains of the above-mentioned surfactants preferably have 10 to 18 carbon atoms.
  • Ester quats are known substances which contain both at least one ester function and at least one quaternary ammonium group as 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 ® .
  • the products Armocare ® VGH-70, an N, N-bis (2-palmitoyloxyethyl) dime ylammonium chloride, and Dehyquart ® F-75 and Dehyquart ® AU-35 are examples of such esterquats.
  • 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 Trimethylsilylamodimethicone
  • Dow Corning 929 emulsion containing a hydroxylamino-modified silicone, which is also referred to as amodimethicone
  • SM-2059 manufactured by General Electric
  • SLM-55067 manufactured by SLM-55067
  • Abil ® - Quat 3270 and 3272 manufactured by Dow Corning 929 emulsion
  • 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 homologs which are obtained as catalysts from the reaction of 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 (dimemyldi-dlylammoniumchlorid)
  • Merquat ® 550 dimethyldi-dlyl-immoniumchlorid-acrylamide copolymer
  • Merquat ® 280 Dimyldiallylammoniumchlorid-acrylic acid copolymer commercially available products are examples of such cationic polymers, copolymers of vinylpyrrolidone with quaternized derivatives of dialkylaminoacrylate and methacrylate, such as, for example, vinylpyrrolidone-dimethylaminomethacrylate copolymers quaternized with diethyl.
  • Gafquat ® 734 and Gafquat ® 75yrrolidon -Methoimidazolinium chloride copolymers are commercially available under the names Gafquat ® 734 and Gafquat ® 75yrrolidon -Methoimidazolinium chloride copolymers,
  • Polyquaternium 27 known polymers with quaternary nitrogen atoms in the main polymer chain.
  • Cationic polymers of the first four grappes are particularly preferred; polyquaternium-2, polyquaternium-10 and polyquaternium-22 are very particularly preferred.
  • Silicone oils in particular diaikyl- and alkylarylsiloxanes, such as, for example, dimethylpolysiloxane and methylphenylpolysiloxane, and their alkoxylated and quaternized analogs are also suitable as conditioning agents.
  • silicones examples include those from Dow Corning under the names DC 190, DC 200; DC 344, DC 345 and DC 1401 and the commercial products Q2- 7224 (manufacturer: Dow Corning; a stabilized trimethylsilylamodimethicone), Dow Corning ® 929 emulsion (containing a hydroxylamino-modified silicone, which is also known as amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® -Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxanes, Quaternium-80).
  • 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 vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidor / vinyl acetate copolymers and polysiloxanes,
  • - zwitterionic and amphoteric polymers such as, for example, acrylamidopropyltrimylammonium chloride / acrylate copolymers and octylacylamide / methyl methacrylate / tert-butylaminoethyl ac-7late / 2-hydroxypropyl methacrylate copolymers, anionic polymers such as, for example, polyacrylic acids, crosslinked polyacrylic acids, Vinyl acetate / crotonic acid copolymers, vinyl pyrrolidor / vinyl acrylate copolymers, vinyl acetate butyl maleate / isobomylacrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and acrylic acid / ethyl acrylate / tert-butyl acrylamide polymers,
  • anionic polymers such as, for example, polyacrylic acids, crosslinked polyacrylic acids, Vinyl acetate /
  • Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose loose derivatives, e.g. As methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such as. B. bentonite or fully synthetic hydrocolloids such as polyvinyl alcohol,
  • Structurants such as maleic acid and lactic acid, hair-conditioning compounds such as phospholipids, for example soy lecithin, egg lecithin and cephalins,
  • Protein hydrolyzates in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolysates, their condensation products with fatty acids and quaternized protein hydrolyzates, perfume oils, dimethyl isosorbide and cyclodextrins,
  • Solvents and intermediates such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerin and diethylene glycol, active substances that improve fiber structure, in particular mono-, di- and oligosaccharides such as glucose, galactose, fructose, cargo sugar and lactose, quaternized amines such as methyl yl all - yl - midoemyl-2-alkylimidazolinium methosulfate defoamers such as silicones, dyes for coloring the agent,
  • Anti-dandruff agents such as piroctone olamine, zinc omadine and climbazole, 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 as well as bisabolol, vitamins, provitamins and vitamin precursors, in particular those of grappa A, B 3 , B 5 , B 6 , C, E, F and H,
  • Plant 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, squirrel, coltsfoot, marshmallow, meristem, ginseng and ginger root.
  • - cholesterol cholesterol
  • 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,
  • Propellants such as propane-butane mixtures, N 2 O, dimethyl ether, CO and air,
  • 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
  • Ci6- ⁇ 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)
  • N, N-Dimethyl-N- (C 8 . ⁇ 8 coconut midopropyl) - ammonium acetobetaine (approx. 30% active substance; INCI name: Aqua (Water), Cocamidopropyl Betaine) (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. After that the emulsion was under 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, natural white, not specially pretreated human hair (Kerling) (quantitative ratio of dye mixture: hair amount 5: 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 according to the German Color Atlas are shown in Table II.

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Abstract

L'invention concerne des moyens de coloration de fibres kératiniques contenant, dans un agent cosmétiquement acceptable, les demi-produits colorants suivants: (A) 2-amino-5-méthylphénol et (B) au moins un dérivé p-aminophénol et (C) au moins un composant d'accouplement, choisi parmi (c1) les dérivés m-aminophénol et (c2) les dérivés de la pyridine. Les produits selon l'invention permettent des colorations oranges particulièrement intenses avec d'excellentes propriétés de résistance et caractérisées par leurs exceptionnelles propriétés toxicologiques.
PCT/EP2001/010851 2000-09-29 2001-09-20 Colorants d'oxydation contenant 2-amino-5-methylphenol WO2002026201A2 (fr)

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DE2000148733 DE10048733A1 (de) 2000-09-29 2000-09-29 Oxidationsfärbemittel mit 2-Amino-5-methylphenol

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
KR101780512B1 (ko) * 2011-09-30 2017-10-10 가부시키가이샤 미르본 산화염모제용 제1제 및 산화염모제

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US5645610A (en) * 1994-06-18 1997-07-08 Balzer; Wolfgang R. Substituted 2-alkylamino-4-amino-1-alkylbenzene compounds and oxidation hair dye compositions based on said compounds
DE19961274C1 (de) * 1999-12-18 2001-02-15 Wella Ag Neue 1,4-Diaminobenzol-Derivate und diese Verbindungen enthaltende Färbemittel für keratinische Fasern, insbesondere Haarfärbemittel
EP1120105A2 (fr) * 2000-01-27 2001-08-01 Bristol-Myers Squibb Company (Diamino-2,5 phényl)éthanol-1 et son utilisation en coloration capillaire
DE10032134C1 (de) * 2000-07-01 2001-12-13 Wella Ag 2-Hydroxy-5-amino-biphenyl-Derivate sowie diese Verbindungen enthaltende Oxidationshaarfärbemittel

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Publication number Priority date Publication date Assignee Title
US5645610A (en) * 1994-06-18 1997-07-08 Balzer; Wolfgang R. Substituted 2-alkylamino-4-amino-1-alkylbenzene compounds and oxidation hair dye compositions based on said compounds
DE19961274C1 (de) * 1999-12-18 2001-02-15 Wella Ag Neue 1,4-Diaminobenzol-Derivate und diese Verbindungen enthaltende Färbemittel für keratinische Fasern, insbesondere Haarfärbemittel
EP1120105A2 (fr) * 2000-01-27 2001-08-01 Bristol-Myers Squibb Company (Diamino-2,5 phényl)éthanol-1 et son utilisation en coloration capillaire
DE10032134C1 (de) * 2000-07-01 2001-12-13 Wella Ag 2-Hydroxy-5-amino-biphenyl-Derivate sowie diese Verbindungen enthaltende Oxidationshaarfärbemittel

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101780512B1 (ko) * 2011-09-30 2017-10-10 가부시키가이샤 미르본 산화염모제용 제1제 및 산화염모제
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

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