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WO2003030841A1 - Procede de coloration de fibres keratiniques - Google Patents

Procede de coloration de fibres keratiniques Download PDF

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Publication number
WO2003030841A1
WO2003030841A1 PCT/EP2002/010732 EP0210732W WO03030841A1 WO 2003030841 A1 WO2003030841 A1 WO 2003030841A1 EP 0210732 W EP0210732 W EP 0210732W WO 03030841 A1 WO03030841 A1 WO 03030841A1
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WIPO (PCT)
Prior art keywords
amino
acid
methyl
hydroxy
group
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German (de)
English (en)
Inventor
Doris Oberkobusch
Hinrich Möller
Horst Höffkes
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Priority to EP02777202A priority Critical patent/EP1434552A1/fr
Publication of WO2003030841A1 publication Critical patent/WO2003030841A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • 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
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • 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 invention relates to a process for dyeing keratin-containing fibers, in particular human hair, in which the fibers are first treated with an oxidizing agent and then with a reactive coloring component.
  • keratin fibers e.g. B. hair, wool or fur
  • direct dyes or oxidation dyes which are formed by oxidative coupling of one or more developer components with one another or with one or more coupler components
  • Coupler and developer components are also referred to as oxidation dye precursors.
  • the object of the present invention is to provide a process for dyeing keratin-containing fibers, by means of which it is possible to apply fashionably intensive colorations to the fibers which show good wash resistance and do not cause strain on the fibers in the actual dyeing step.
  • the invention relates to a process for dyeing keratin-containing fibers, in particular human hair, in which the fibers are first treated with an agent 1 containing an oxidizing agent and then an agent 2 containing A. at least one compound A with the formula I,
  • AR stands for benzene, naphthalene, pyridine, furan, quinoline, isoquinoline, quinolizine, pyrimidine, pyrrole, thiophene, indole, indan, imidazole, benzimidazole, benzothiazole, indazole, benzoxazole, quinoxaline, quinazoline, cinnoline, acenaphthene, fluorene, biphenyl Diphenylmethane, benzophenone, diphenyl ether, azobenzene, diphenylamine, stilbene and their partially or fully hydrogenated derivatives,
  • R 1 , R 2 and R 3 independently of one another represent a hydrogen atom, a halogen atom, a C ⁇ alkyl, C ⁇ alkoxy, C ⁇ acyl, C ⁇ hydroxyalkoxy, a hydroxy or nitro group or an amino, C ⁇ -acylamino, ammonio or a 1-imidazoli (ni) o group, which can be substituted by C ⁇ alkyl or C ⁇ hydroxyalkyl groups, and also two of the radicals R 1 , R 2 and R 3 one to AR fused-on saturated or unsaturated, optionally substituted 5-, 6- or 7-ring, which in turn can carry an aromatic, optionally substituted ring, the system AR, depending on the size of the ring, can carry further substituents that have the same May have meaning like R 1 , R 2 and R 3 and • X stands for a group N ⁇ N + Y " , where Y " stands for a halide, nitrate, 0.5
  • G represents a direct bond, a CrC ⁇ alkylene group, a C 2 -C 4 alkenylene group or a C -C 6 dialkenylene group,
  • R 6 and R 7 independently of one another represent a hydrogen atom, a CrC 4 alkyl group, or together with the group -C (O) -GC (O) - form an optionally substituted ring, which in turn forms a condensed one may carry an optionally substituted aromatic ring, where the groups R 6 and R 7 together form a CrC 4 alkenylene group, a C -C 6 dialkenylene group or a CC 4 alkylene group,
  • the fibers are treated with an oxidizing agent in a manner known per se.
  • H 2 O 2 , H 2 O 2 releasing compounds or combinations thereof are preferably used as oxidizing agents, in particular for human hair, these compounds also being able to be applied to an inert carrier.
  • H 2 O 2 can e.g. B. in combination with Na, K, NH - peroxodisulfate or the corresponding peroxodiphosphonates, especially in an alkaline environment.
  • the pH is preferably in the range from pH 6 to 11, particularly preferably in the range from pH 8.5 to pH 10.5.
  • the oxidizing agent preparation can also compounds such.
  • B. Magnesium peroxide can be added.
  • H 2 O can be in the oxidizing agents in free form or bound, e.g. B. be used as sodium carbonate peroxyhydrate, urea peroxide or melamine perhydrate.
  • the oxidizing agents are generally used in an amount of 0.01 to 6% by weight, based on the application solution.
  • the compounds with the formulas I and II and component B used in the second step are to a large extent known from the literature or commercially available or can be prepared by known synthetic processes.
  • Suitable diazonium salts with the formula I are 4-diazo-phenylamine sulfate (Variamin blue salt ® RT), 4-diazo-4'-methoxydiphenylamine chloride (Variamine blue salt ® B), 4-diazo-3,2'-dimethylazobenzenesulfate (real garnet salt ® GBC), 2-methoxy-4-nitrobenzene diazonium naphthalene-1,5-disulfonate (Echtrotsalz ® B), 4-diazo-2,5-dimethoxy-4'-nitroazobenzene chloride-zinc chloride double salt (real black salt ® K), 2,5-dimethoxy-4 - benzolyaminophenyldiazonium chloride (Real Blue Salt ® RR), 2-methoxy-4-nitrobenzene-diazonium-1,5-naphthalenedisulfonate, 4-chloro-2-nitrobenzene diazonium chlor
  • Preferred onium aldehydes are, for example, the benzenesulfonates, p-toluenesulfonates, methanesulfonates, perchlorates, sulfates, chlorides, bromides, iodides and / or tetrachlorozincates of 4-formyl-1-methylpyridinium, 3-formyl-1-methylpyridinium, 2-formyl- 1-methylpyridinium, 4-formyl-1-ethylpyridinium, 2-formyl-1-ethylpyridinium, 4-formyl-1-benzylpyridinium, 2-formyl-1-benzylpyridinium, 4-formyl-1,2-dimethylpyridinium, 4-formyl- 1,3-dimethylpyridinium, 4-formyl-1-methylquininoin, 2-formyl-1-methylquininoinium, 4- (2-formylvinyl) -1-methylquinol
  • isatin derivatives are isatin, isatin-5-sulfonic acid, isatin-4-carboxylic acid and isatin-5-carboxylic acid, N-substituted isatin derivatives, such as N-hydroxymethyl-isatin, N-hydroxyethyl-isatin N- (2'-hydroxypropyl ) isatin, N- (3'-hydroxypropyl) isatin, N- (2 ', 3'-dihydroxypropyl) isatin, N- (2'-sulfoethyl) isatin, N- (3'-sulfopropyl) isatin , N-allylisatin, N- vinylisatin, N-benzylisatin, N- (4'-methoxybenzyl) isatin, N- (4'-carboxybenzyl) isatin, N- (4'-sulfobenzyl) isatin, N- (2nd '-Dimethylaminoethyl
  • Carbazolaldehydes or carbazole ketones especially 9-methyl-3-carbazolaldehyde, 9-ethyl-3-carbazolaldehyde, 3-acetylcarbazole, 3,6-diacetyl-9-ethylcarbazole, 3-acetyl-9-methylcarbazole, 1, 4-dimethyl-3 -carbazolaldehyde, 1, 4,9-trimethyl-3-carbazolaldehyde, 4-trimethylammoniobenzaldehyde, 4-benzyldimethylammoniobenzaldehyde, 4-trimethylammoniozimtaldehyde, 4-trimethylammonionaphthaldehyde, 2-methoxy-4-trimethylammonobaldehyde (4'-acetylphenyl) trimethylammonium, 4- (N, N-diethyl) -N-methylammonio) benzaldehyde, N- (4'-benzoylphenyl)
  • Indanone derivatives such as. B. 1,2-indandione, 2-oximo-1-indanone, indan-1,2,3-trione-2-oxime, 5-methoxy-indan-1, 2,3-thon-2-oxime, 2- Nitro-1,3-indanedione, quaternized azafluorenones, such as the trifluoromethanesulfonates, benzenesulfonates, p-toluenesulfonates, methanesulfonates, perchlorates, sulfates, chlorides, bromides, iodides, tetrachlorozincates, hexafluorophosphates tetrafluoroborates [1-methyl-5-indeno 1,2-b] pyridinium- (4'-methyl-4'-azonio-9'-fluorenone), 1-ethyl-5-oxo-indeno [1, 2-b] pyridinium, 1-benzy
  • Carbonyl compounds according to formula II which are preferably used according to the invention are glutacondialdehyde, fumaraldehyde, glyoxal, malondialdehyde, amber dialdehyde, mucondialdehyde, 1, 2-naphthoquinone, 4-sulfonic acid-1,2-naphthoquinone, 1,2-benzoquinone, 1,4-benzoquinone, 2, 3-dimethoxy-5-methyl-1,4-benzoquinone (juglone), 1,4-naphthoquinone, spinulosin, atromentin, aurentioglyocladin, 5-hydroxy-1, 4-naphthoquinone, 2,5-dihydroxy-6-methylbenzoquinone, 2 Hydroxy-3-methyl-6-methoxy-1,4-benzoquinone, 2,5-dihydroxy-3,6-diphenyl-1,4-benzoquinone, 2,5-dihydroxy-6
  • the compounds of component B are, on the one hand, compounds which, on their own, only give weakly colored keratin-containing fibers and only give brilliant colors together with the compounds of the formulas I and / or II. On the other hand, there are also compounds that are already used as oxidation dye precursors or direct pullers.
  • Suitable compounds with primary or secondary amino group as component B are e.g. B. primary and secondary aromatic amines such as N, N-dimethyl-p-phenylenediamine, N, N-diethyl-p-phenylenediamine, N- (2-hydroxyethyl) -N-ethyl-p-phenylenediamine, N, N-bis- (2-hydroxyethyl) -p-phenylene diamine, N- (2-methoxyethyl) -p-phenylene diamine, 2,3-dichloro-p-phenylene diamine, 2,4-dichloro-p-phenylene diamine, 2,5-dichloro-p- phenylenediamine, 2-chloro-p-phenylenediamine, 2,5-dihydroxy-4-morpholinoaniline, 2-aminophenol, 3-aminophenol, 4-aminophenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-amino
  • R 8 represents a hydroxyl or an amino group which can be substituted by C 1-4 alkyl, C 1-4 hydroxyalkyl, C 1-4 alkoxy or C 1-4 alkoxy-C 1-4 alkyl groups,
  • R 9 , R 10 , R 11 , R 12 and R 13 independently of one another represent a hydrogen atom, a hydroxy or an amino group which can be substituted by C ⁇ alkyl, C ⁇ hydroxyalkyl, C ⁇ alkoxy, C ⁇ aminoalkyl or C ⁇ alkoxy-C ⁇ alkyl groups can be substituted,
  • Z stands for a direct bond, a saturated or unsaturated carbon chain with 1 to 4 carbon atoms optionally substituted by hydroxyl groups, a carbonyl, sulfonyl or imino group, an oxygen or sulfur atom, or a group with the formula IV
  • Z 4 denotes a direct bond, a CH 2 or CHOH group
  • Z 2 and Z 3 independently of one another for an oxygen atom, an NR 14 group, in which R 14 is hydrogen, a C 1-4 alkyl or a hydroxyC 1-4 alkyl group, both groups together with the rest of the molecule also being a 5-, Can form 6 or 7 ring means the group O- (CH 2 ) p -NH or NH- (CH 2 ) p '-O, where p and p' are 2 or 3, and
  • O is a number from 1 to 4,
  • 4,4'-diaminostilbene and its hydrochloride 4,4'-diaminostilbene-2,2'-disulfonic acid mono- or di-Na salt, 4-amino-4'-dimethylaminostilbene and its hydrochloride, 4, 4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl isulfide, 4,4'- Diaminodiphenyl sulfoxide, 4,4'-diaminodiphenylamine, 4,4'-diaminodiphenylamine-2-sulfonic acid, 4,4'-diaminobenzophenone, 4,4'-diaminodiphenyl ether, 3,3 ', 4,4'-tetraaminodiphenyl, S.S ' ⁇ ' - tetraamino-benzophenone, 1,3-bis (2,4-diaminophenoxy) propane, 1,8-bis (2,4-
  • the abovementioned compounds can be used both in free form and in the form of their physiologically tolerable salts, in particular as salts of inorganic acids, such as hydrochloric or sulfuric acid.
  • Suitable nitrogen-containing heterocyclic compounds are e.g. B. 2-aminopyridine, 3-aminopyridine, 4-aminopyridine, 2-amino-3-hydroxy-pyridine, 2,6-diamino-pyridine. 2,5-diamino-pyridine, 2- (aminoethylamino) -5-aminopyridine, 2,3-diamino-pyridine, 2-dimethylamino-5-amino-pyridine, 2-methylamino-3-amino-6-methoxy- pyridine, 2,3-diamino-6-methoxy-pyridine, 2,6-dimethoxy-3,5-diamino-pyridine, 2,4,5-triamino-pyridine, 2,6-dihydroxy-3,4- dimethylpyridine, N- [2- (2,4-diaminophenyl) aminoethyl] -N- (5-amino-2-pyridyl) amine, N- [2- (4-
  • the hydroxypyrimidines disclosed in DE-U 1-299 08 573 can also be used as heterocyclic compounds.
  • the aforementioned compounds can be used both in free form and in the form of their physiologically salts in question, e.g. B. as salts of inorganic acids such as hydrochloric or sulfuric acid.
  • Suitable aromatic hydroxy compounds are e.g. B. 2-methylresorcinol, 4-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol, resorcinol, 3-methoxyphenol, pyrocatechol, hydroquinone, pyrogallol, phloroglucinol, hydroxyhydroquinone, 2-methoxyphenol, 3-methoxyphenol, 4-methoxyphenol, 3- Dimethylaminophenol, 2- (2-hydroxyethyl) phenol, 3,4-methylenedioxyphenol, 2,4-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 2,4-dihydroxyphenylacetic acid, 3,4-dihydroxyphenylacetic acid, gallic acid, 2 , 4,6-trihydroxybenzoic acid, 2,4,6-trihydroxyacetophenone, 2-chlororesorcinol, 4-chlororesorcinol, 1-naphthol, 1, 5-dihydroxynaphthalene,
  • Preferred amino acids are all naturally occurring and synthetic ⁇ -amino acids, e.g. obtained by hydrolysis from vegetable or animal proteins, e.g. Collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein accessible amino acids. Both acidic and alkaline amino acids can be used. Preferred amino acids are arginine, histidine, tyrosine, phenylalanine, DOPA (dihydroxyphenylalanine), omithin, proline, lysine and tryptophan. But also other amino acids, e.g. 6-aminocaproic acid and ⁇ -alanine can be used.
  • Component B can also be a CH-acidic compound.
  • CH-acidic compounds Those compounds which carry a hydrogen atom bonded to an aliphatic carbon atom are generally regarded as CH-acidic, activation of the corresponding carbon-hydrogen bond being effected on account of electron-withdrawing substituents.
  • the CH-acidic compounds are preferably selected from compounds according to one of the formulas C1 to C21:
  • M 5 is a group -COM 7 or COOM 7 , in which M 7 represents a hydrogen atom or a d-Ce-alkyl group, or a cyano group, a substituted or unsubstituted aryl group or an aryl-CrC ⁇ alkyl group, a substituted or unsubstituted, is saturated or unsaturated heterocycle,
  • M 6 is a substituted or unsubstituted CrC ⁇ alkyl group, an acetyloxy group, a C 3 -C 6 cycloalkyl group, a substituted or unsubstituted aryl group or aryl-dC ⁇ alkyl group, a substituted or unsubstituted aminoaryl group, a substituted or unsubstituted, saturated or unsaturated heterocycle is
  • M 8 is a group -COM 10 or COOM 10 , where M 10 represents a hydrogen atom or a C 6 -C 6 -alkyl group, or a cyano group, a substituted or unsubstituted aryl group or aryl-CrC-alkyl group, a substituted or unsubstituted, is saturated or unsaturated heterocycle,
  • M 9 is a substituted or unsubstituted aryl group or aryl-C 1 -C 4 -alkyl group, is a substituted or unsubstituted aminoaryl group, a substituted or unsubstituted, saturated or unsaturated heterocycle,
  • M 11 and M 12 independently of one another for a substituted or unsubstituted CC 6 alkyl group, an acetyloxy group, a C 3 -C 6 cycloalkyl group, a substituted or unsubstituted aryl group or aryl-CrC-alkyl group, a substituted or unsubstituted aminoaryl group, a substituted one or unsubstituted, saturated or unsaturated heterocycle,
  • M 13 is a hydrogen atom or a substituted or unsubstituted C 1 -C 6 -alkyl group
  • M 14 and M 15 independently of one another represent a dC 6 alkyl group, a C 2 -C 6 alkenyl group, a C 3 -C 6 cycloalkyl group, an aryl-C 1 -C 4 -alkyl group, a substituted or unsubstituted aryl group, or a bicyclic bonded via the residues M 14 or M 15 ,
  • X stands for an oxygen or a sulfur atom
  • M is a substituted or unsubstituted CC 6 alkyl group or substituted or unsubstituted aryl group
  • M 7 is a hydrogen atom, a substituted or unsubstituted CC 6 alkyl group or a substituted or unsubstituted aryl group,
  • M 18 is a hydrogen atom, a cyano group, a substituted or unsubstituted d-Ce alkyl group, a group COOM 19 , in which M 19 is a hydrogen atom or a substituted or unsubstituted dC 6 alkyl group,
  • A stands for an oxygen atom, a sulfur atom, a sulfonyl group or a G Grruuppppee NNMM 2200aa ,, wwoorriinn MM 2200aa eeiinn Waasssseerrstoffatom, a substituted or unsubstituted d-Ce alkylene group
  • M and M 21 independently of one another represent a hydrogen, a chlorine, a bromine atom, a hydroxy group, a nitro group, a dC 6 alkyl group, a C Ce alkoxy, a carboxamide, a sulfonamide, a carboxyl, a -CC -acyl, a cyano group or an amino group -NM 22 M 23 , in which M 22 and M 23 independently represent a hydrogen atom or a dC 6 -alkyl group,
  • a ' represents an oxygen atom, a sulfur atom or a group NM 25 , in which M 25 represents a hydrogen atom or a substituted or unsubstituted dC 6 alkyl group,
  • M 24 stands for a hydrogen, a chlorine, a bromine atom, a hydroxyl group, a nitro group, a C Ce alkyl, a dC 6 alkoxy, a carboxamide, a sulfonamide, a carboxyl, a dC 4 -Acyl, a cyano group or an amino group -NM 26 M 27 , in which M 26 and M 27 independently of one another represent hydrogen and a CrCe alkyl group
  • M 28 is a hydrogen atom, a hydroxy group, a substituted or unsubstituted d-C ⁇ -alkyl group or a substituted or unsubstituted aryl or dC 6 -alkylaryl group;
  • M 29 represents a hydrogen atom or a C 1 -C 8 alkyl group Indanedione derivatives with the formula C12
  • M 30 is a hydrogen, a chlorine, a bromine atom, a nitro, a dC 6 -alkyl, a d-Ce-alkoxy, a carboxamide, a sulfonamide or a cyano group,
  • Z represents an oxygen atom or a group NM f -32, where M «32
  • Z ' represents a sulfur atom or a group NM 33 , where M 33 is
  • M 31 represents a hydrogen atom, a dC 6 alkyl group or a C r C 4 carboxyalkyl group
  • M and M independently of one another represent a hydrogen, a chlorine, a bromine atom, a hydroxyl group, a nitro group, a CC 6 alkyl, a CC 6 alkoxy, a carboxamide, a sulfonamide, a carboxyl, a C r C 4 -acyl, a cyano group or an amino group -NM 36 M 37 , in which M 36 and M 37 independently represent hydrogen or a dC 6 -alkyl group,
  • M and M independently of one another represent a hydrogen, a chlorine, a bromine atom, a hydroxyl group, a nitro group, a CC 6 alkyl, a dC 6 alkoxy, a carboxamide, a sulfonamide, a carboxyl, a dd-acyl, a cyano group or an amino group -NM 41 M 42 , in which M 41 and M 42 independently of one another represent a hydrogen atom or a dC 6 -alkyl group, M 40 represents a hydrogen atom or a dC 6 -alkyl group,
  • M and M «44 independently of one another represent a hydrogen, a chlorine, a bromine atom, a hydroxyl group, a nitro group, a CC 6 -alkyl, a C -, - C 6 -alkoxy-, a carboxamide-, one Sulfonamide, a carboxyl, a dd-acyl, a cyano group or an amino group -NM 45 M 46 , in which M 45 and M 46 independently represent a hydrogen atom or a dC 6 alkyl group Compounds with the formula C17
  • D 1 is a fused aromatic or heteroaromatic ring
  • D 2 is a carbonyl group or a methylene group CD'D ", in which D 1 or D 11 each have a substituent with a Hammett constant between 0.4 and 2.0 or both substituents in total a Hammett constant between 0, 4 and 2.0;
  • M 49 and M 50 independently of one another are a hydrogen atom or a substituted or unsubstituted CC 6 alkyl group
  • E 1 represents an oxygen, a sulfur atom or a group NH
  • E 2 represents a group NH or an oxygen atom
  • E 3 represents an amino group or a hydroxy group
  • M 51 and M 52 independently of one another represent a hydrogen atom, a halogen atom, a hydroxyl group, a dC -hydroxyalkyl group, a dC 6 - aminoalkyl group, a dd-dialkylamino-dd-alkyl group, a linear or branched dC 6 alkyl group, a C 2 -C 6 alkenyl group, an optionally substituted aryl group, a sulfonic acid group, a carboxyl group, a formyl group, a nitro group, a cyano group or a group -NM 54 M 55 , where M 54 and M 55 independently represent a hydrogen atom, a dC 6 -Alkyl group, a C 2 -C 6 alkenyl group, an aryl-dC 4 -alkyl group or a dC 4 -hydroxyalkyl group, where M 51 and M 52 together can form a fused-on 5- or
  • Y stands for an oxygen atom, a sulfur atom, an optionally substituted methylene group or a group NM 60 , where M 60 can stand for the same groups which are defined under M 55 ,
  • a " stands for a chloride, bromide, iodide, hexafluorophosphate, tetrachlorozincate, tetrafluoroborate, trifluoromethyl sulfonate, methyl sulfonate or p-toluenesulfonate,
  • M 51 , M 52 , M 53 and A are selected from the groups defined under Compound C19.
  • CH-acidic compounds also include enamines which arise from quaternized N-heterocycles with an CH-acidic alkyl group conjugated to the quaternary nitrogen by alkaline treatment.
  • suitable enamines are compounds with the general formula C22
  • M 61 stands for an aromatic radical, in particular for a 5-membered or 6-membered aryl residue, preferably a phenyl residue, or one optionally substituted with a dC 4 -alkyl, dC 4 -hydroxyalkyl, hydroxy, methoxy or halogen group 5-membered or 6-membered, fused, aliphatic or aromatic, carbocyclic or heterocyclic ring, preferably a phenyl residue, a quinoline or pyridyl residue,
  • M 62 stands for a hydrogen atom, a linear or branched dC 8 -alkyl, a linear or branched dC 8 -hydroxyalkyl or a dC 8 -alkoxyalkyl group, where an oxygen atom can sit between the carbon atoms of the alkyl chain
  • M 63 stands for a linear or branched CC 8 -alkyl group, a -C 6 -alkoxy-d- C 6 -alkyl group, a d-Cs-alkylamino-d-Ce-alkyl group, a dC 6 -alkyl mercapto-d- Ce-alkyl group, a d-Ce-alkoxy-d-C ⁇ -alkylene group, a CC 6 -alkylamino-d-Ce-alkylene group, a d-Ce-alkylmercapto-d-Ce-alkylene group, a straight-chain or
  • the compounds with the formulas C1, C2 and C3 are preferably selected from malonic acid, malonic acid esters and their derivatives and acetoacetic acid, acetoacetic acid esters and their derivatives.
  • Examples of compounds with the formula C4 are pyrazol-5-one, 3-methyl-pyrazol-5-one, 1-phenyl-3-methyl-pyrazol-5-one, 1- ( ⁇ -cyanoethyl) -3-methyl- pyrazol-5-one, 1,3-dimethyl-pyrazol-5-one, 1- ( ⁇ -acetoxyethyl) -3-methyl-pyrazol-5-one, 1- (2'-chlorophenyl) -3-methyl-pyrazole -5-one, 1-phenyl-3-carbomethoxy-pyrazol-5-one, 1- (3'-aminophenyl-pyrazol-5-one, 1 - (4'-aminophenyl) pyrazol-5-one, 3- Methyl-pyrazol-5-one-1-carboxamides, 1-phenyl-pyrazol-5-one-3-carboxamides, amino-pyrazole, 1-phenyl-5-amino-pyrazole, 1-benzyl-5-amino-pyr
  • the barbituric acid derivatives with the formula C6 are preferably selected from barbituric acid, thiobarbituric acid, di-N-ethylthiobarbituric acid, di-N-
  • Methylthiobarbituric acid di-n-butyl barbituric acid, di-isobutyl barbituric acid, di-N-amyl barbituric acid, di-iso-amyl barbituric acid, di-n-hexyl barbituric acid, di-benzyl barbituric acid, di- ß-phenylethyl barbituric acid, di-cyclohexyl barbituric acid, di-phenyl barbituric acid, di-p-tolyl barbituric acid, di-p-methoxybenzyl barbituric acid, N-methyl-N'-n-butyl-barbituric acid, N-methyl-N'-benzyl-barbituric acid, N-methy1-N'-ß -phenylethyl-barbituric acid, N-methyl-N'- ⁇ -phenylpropyl-barbituric acid, N-methyl-N'- ⁇ -phen
  • 2,6-Dihydroxy-3-cyano-4-methyl-pyridine 2,6-Dihydroxy-3-cyano-4-methyl-pyridine, cyanopyridones, aminonitropyridones and aminocyano-pyridones, in particular N-methyl-3-cyano-4-methyl, may be mentioned as preferred examples of the pyridine derivatives having the formula C7 -6-hydroxy-pyridone-2, N-ethyl-3-cyano-4-methyl-6-hydroxy-pyridone-2, N- ⁇ -methoxyethyl-3-cyano-4-methyl-6-hydroxy-pyridine-2 -on, N- ⁇ -hydroxyethyl-3-cyano-4-methyl-6-hydroxy-pyridin-2-one, N-butyl-3-cyano-4-methyl-6-hydroxy-pyridin-2-one and N -Phenyl-3-cyano-4-methyl-6-hydroxy-pyridin-2-one.
  • the compounds with the formula C8 can be selected from 6-hydroxybenzofuran (2H) -one and 3-indoxy acetate.
  • the compounds having the formula C9 can be selected from indol-2-one, 1,3-dihydro-indol-2-one, 3H-benzofuran-2-one, 1-methyl-1,3-dihydro-indol-2- on, 5-methoxy-3H-benzofuran-2-one, 5-nitro-1, 3-dihydro-indol-2-one, 1-methyl-5-nitro-1, 3-dihydro-indol-2-one, 6-methoxy-1,3-dihydro-indol-2-one, 5-chloro-1,3-dihydro-indol-2-one, 5,6-difluoro-1,3-dihydro-indol-2-one, 6-hydroxy-5-methoxy-1,3-dihydro-indol-2-one, 5,6-dimethoxy-1,3-dihydro-indol-2-one and 6-trifluoromethyl-1,3-dihydro-indole-
  • Examples of compounds having the formula C10 are imidazo [1.2-a] pyridin-2-one and 6-bromo-imidazo [1.2-a)] pyridin-2-one.
  • the compounds with the formula C11 are preferably selected from the derivatives in which in the formula C11 the radicals M 28 and M 29 stand for a hydrogen atom, such as 2,4-dihydroxyquinoline.
  • a suitable example of an indanedione derivative with the formula C12 is 1,3-indanedione.
  • the compounds with the formula C13 are preferably selected from rhodanine, rhodanine-3-acetic acid and 4-imino-4,5-dihydro-thiazol-2-ylamine.
  • 1,2-Diphenyldioxopyrazole can be mentioned as the preferred compound with the formula C14.
  • the compounds having the formula C15 are preferably selected from 2-phenyl-3,5-dihydro-imidazol-4-one and 3-methyl-2-p-toloyl-3,5-dihydro-imidazol-4-one.
  • a preferred example of a compound having the formula C16 is phenyldihydrobutyrolactone.
  • the compounds having the formula C17 are preferably selected from 1,1-dioxo-1,2-dihydro-11,6-benzo [b] -thiophen-3-one, 1-dicyanomethylene indane, 1,3-
  • hydroxypyrimidine derivatives with the formula C18 are 2,4-diamino-6-hydroxy-pyrimidine, 2,6-diamino-4-hydroxypyrimidine, 4-amino-2,6-dihydroxypyrimidine, 4-amino-6-hydroxy-2- sulfanylpyrimidine, 2-amino-4,6-dihydroxypyrimidine, 4,6-dihydroxy-1-mercaptopyrimidine and 2,4,6-trihydroxypyrimidine, with 2,4-diamino-6-hydroxypyhmidine being particularly preferred.
  • Preferred compounds with the formula C19, C20 or C21 are 1,2-dimethylnaphtho [1,2-d] thiazolium p-toluenesulfonate, 2,3-dimethyl-benzothiazolium iodide, 2,3-dimethyl-benzothiazolium p-toluenesulfonate, 1-ethyl-2-methyl-naphtho [1,2-d] thiazolium p-toluenesulfonate, 1,2,3,3-tetramethyl-3-H-indolium iodide, 1,2,3,3-
  • Preferred enamines having the formula C22 are those in which the radicals M 61 and M 63 form a cyclic compound together with the nitrogen atom and the carbon atom of the basic enamine structure, the 1,3,3-trimethyl-2-methylene-indoline, the 1- (2-Hydroxyethyl) -3,3-dimethyl-2-methylene indoline and 3-ethyl-2-methylenebenzothiazoline are particularly preferred.
  • the oligopeptides can be naturally occurring or synthetic oligopeptides, but also the oligopeptides contained in polypeptide or protein hydrolyzates, provided that they have sufficient water solubility for use in the colorants according to the invention.
  • Examples include glutathione or the oligopeptides contained in the hydrolyzates of collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein. Use together with compounds having a primary or secondary amino group or with aromatic hydroxy compounds is preferred.
  • quaternary ammonium salts are tetramethyl, tetraethyl, tetrapropyl, tetrabutyl, benzyltrimethylammonium chloride, bromide, iodide, hydrogen sulfate, 0.5 sulfate and the quaternized hydroxyethyl cellulose derivatives (INCI name: Polyquaternium 10).
  • the compounds of component B are particularly preferably selected from the group consisting of N- (2-hydroxyethyl) -N-ethyl-p-phenylenediamine, 2-chloro-p-phenylenediamine, N, N-bis- (2-hydroxyethyl) ) -p-phenylenediamine, 2-aminophenol, 3-aminophenol, 4-aminophenol, 2-amino-6-chloro-4-nitrophenol, p-phenylenediamine, 2- (2,5-diaminophenyl) ethanol, 2,5- Diaminotoluene, 3,4-methylenedioxyaniline, 2-amino-4- (2-hydroxyethylamino) anisole, 2- (2,4-diaminophenoxy) ethanol, 3-amino-2,4-dichlorophenol, 2-methyl-5- aminophenol, 3-methyl-4-aminophenol, 2-methyl-5- (2-hydroxyoxyamino) phenol, 2-methyl-5-amino-4
  • Very particularly preferred compounds of component B according to the invention are N, N-bis (2-hydroxyethyl) p-phenylenediamine, 2,5-diaminotoluene, 2- (2,5-diaminophenyl) ethanol, 2-aminophenol, 3-aminophenol, 4-aminophenol, 2-aminomethyl-4-aminophenol, 2- (diethylaminomethyl) -4-aminophenol, 1-hydroxy-2-amino-5-methyl-benzene, 2,4-diaminophenoxyethanol, 3-amino-2,4- dichlorophenol, 2-methyl-5-aminophenol, 2-methyl-5- (2-hydroxyethylamino) phenol, 6-methyl-3-amino-2-chlorophenol, 2-methyl-5-amino-4-chlorophenol, 3, 4-methylenedioxyaniline, 3,4-diaminobenzoic acid, 3,5-diamino-2-methoxy-1-methylbenzene, 2-amino-4-
  • Components A and B are preferably used in an amount of 0.03 to 65 mmol, in particular 1 to 40 mmol, based on 100 g of the finished coloring agent (agent 2) used.
  • Color intensifiers can be used in addition to the compounds used as component B in the process according to the invention in order to obtain further and more intensive colorations.
  • the color enhancers are preferably selected from the group consisting of piperidine, piperidine-2-carboxylic acid, piperidine-3-carboxylic acid, piperidine-4-carboxylic acid, pyridine, 2-hydroxypyridine, 3-hydroxypyridine, 4-hydroxypyridine, imidazole, 1- Methyl imidazole, arginine, histidine, pyrrolidine, proline, Pyrrolidone, pyrrolidone-5-carboxylic acid, pyrazole, 1,2,4-triazole, piperazine, methoxybutanol, propylene carbonate, ethylene carbonate, their derivatives and their physiologically tolerable salts.
  • the aforementioned color enhancers can be used in an amount of 0.03 to 65 mmol, in particular 1 to 40 mmol, in each case based on 100 g of the entire colorant (agent 2). If one of the compounds defined as a color enhancer is used both as a color enhancer and as component B, the amounts of these compounds can exceed the respective upper limits of 65 mmol or 40 mmol. In this embodiment, the upper limits are preferably 130 mmol, in particular 80 mmol.
  • colorants in all colorants (agent 2), several different compounds with the formulas I and II and component B can also be used; several different color enhancers can also be used together.
  • customary direct dyes e.g. B. from the group of nitrophenylenediamines, nitroaminophenols, anthraquinones or indophenols, such as. B.
  • the substantive dyes are preferably added in an amount of 0.01 to 20% by weight, based on the components used.
  • the preparations used according to the invention can also contain naturally occurring dyes, such as those contained in henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, rotten tree bark, sage, blue hoot, madder root, catechu, sedre and alkanna root ,
  • naturally occurring dyes such as those contained in henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, rotten tree bark, sage, blue hoot, madder root, catechu, sedre and alkanna root .
  • the compounds according to the invention with the formulas I and II or the optional color enhancers and substantive dyes each represent uniform compounds. Rather, in the colorants used according to the invention (agent 2), due to the production process for the individual dyes, further components may be present in minor amounts, provided that these do not adversely affect the dyeing result or for other reasons, e.g. B. toxicological, must be excluded.
  • the colorants (agent 2) used according to the invention produce intensive colorations even at physiologically tolerable temperatures of below 45 ° C. They are therefore particularly suitable for dyeing human hair.
  • the colorants (agent 2) can usually be incorporated into an aqueous cosmetic carrier.
  • Suitable water-containing cosmetic carriers are e.g. B. creams, emulsions, gels or surfactant-containing foaming solutions such.
  • the agents 1 and / or agents 2 used according to the invention can contain all active ingredients, additives and auxiliaries known in such preparations.
  • the agents contain at least one surfactant, and in principle both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable.
  • anionic surfactants in preparations used 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.
  • the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
  • suitable anionic surfactants are, in each case in the form of the sodium, potassium and ammonium as well as the mono-, di- and trialkanolammonium salts with 2 or 3 carbon atoms in the alkanol group,
  • Ether carboxylic acids of the formula R-0- (CH 2 -CH 2 0) 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 Carbon atoms in the acyl group, acyl taurides with 10 to 18 carbon atoms in the acyl group, acyl isethionates with 10 to 18 carbon atoms in the acyl group,
  • Mono and dialkyl sulfosuccinic acid with 8 to 18 carbon atoms in the alkyl group and mono-alkyl polyoxyethyl sulfosuccinate with 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, linear alkane sulfonates 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 R-0 (CH 2 -CH 2 0) x -S0 3 H, in which R is a preferably linear alkyl group 10 to 18 carbon atoms and x 0 or 1 to 12,
  • esters of tartaric acid and citric acid with alcohols which are adducts of about 2 to 15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols with 8 to 22 carbon atoms.
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids with 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, and in particular salts of saturated and in particular unsaturated C 8 -C 22 carboxylic acids, such as oleic acid, stearic acid , Isostearic acid and palmitic acid.
  • Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one -COO H or -SOa ⁇ group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyl dimethylammonium glycinate, N-AcyI-aminopropyl-N, N-dimethylammonium glycinate, for example coconut acylaminopropyl dimethylammonium glycinate, and -AlkyI-3-carboxymethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under
  • Ampholytic surfactants are understood to mean those surface-active compounds which, in addition to a C 8 . 18 -alkyl or -acyl group in the molecule contain at least one free amino group and at least one -COOH or -SO 3 H group and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12 . 18 - acyl sarcosine.
  • Nonionic surfactants contain z as a hydrophilic group.
  • B a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group.
  • Such connections are, for example
  • Examples of the cationic surfactants which can be used in the hair treatment compositions according to the invention are, in particular, quaternary ammonium compounds.
  • Ammonium halides such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, for.
  • 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).
  • alkylamidoamines especially fatty acid amidoamines such as the stearylamidopropyldimethylamine available under the name Tego Amid ® S 18, are notable for their good biodegradability.
  • quaternary Esterharmen so-called “esterquats”, such as those sold under the trademark Stepantex ® methylhydroxyalkyldialkoyloxyalkylammonium.
  • An example of a suitable cationic surfactant quaternary sugar derivative is the commercial product Glucquat ® 100, according to CTFA nomenclature a "lauryl methyl Gluceth-10 Hydroxypropyl Dimonium Chloride".
  • the compounds with alkyl groups used as surfactants 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, hydrotaicites, 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.
  • nonionic polymers such as, for example, vinylpyrrolidone-inylacrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes
  • cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary acrylic groups, dimethyl dimethyldiallyl ammonium chloride copolymers, dimethylaminoethyl methacrylate-vinylpyrrolidone copolymers quaternized with diethyl sulfate, vinylpyrrolidone
  • 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, hydroxyalkylceilulose and carboxy-methyl cellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such as. B. bentonite or fully synthetic hydrocolloids such.
  • Structurants such as glucose and maleic acid, hair-conditioning compounds such as phospholipids, for example soy lecithin, egg lecithin and cephalins, and silicone oils,
  • Protein hydrolyzates in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolyzates, their condensation products with fatty acids and quaternized protein hydrolyzates, perfume oils, dimethyl isosorbide and cyclodextrins,
  • Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerin and diethylene glycol,
  • Anti-dandruff agents such as piroctone olamine and zinc omadine, other substances for adjusting the pH value,
  • Active ingredients such as panthenol, pantothenic acid, allantoin, pyrrolidone carboxylic acids and their salts, plant extracts and vitamins, cholesterol, light stabilizers,
  • Consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers, fats and waxes such as walrus, beeswax, montan wax, paraffins, fatty alcohols and fatty acid esters, fatty acid alkanolamides,
  • Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary phosphates, imidazoles, tannins, pyrrole, opacifiers such as latex,
  • Pearlescent agents such as ethylene glycol mono- and distearate, blowing agents such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and air and Antioxidants.
  • the constituents of the water-containing carrier are used for the production of agents suitable for the process according to the invention in amounts customary for this purpose; z.
  • emulsifiers are used in concentrations of 0.5 to 30% by weight and thickeners in concentrations of 0.1 to 25% by weight of the entire preparation.
  • Suitable metal salts are e.g. B. formates, carbonates, halides, sulfates, butyrates, valerates, capronates, acetates, lactates, glycolates, tartrates, citrates, gluconates, propionates, phosphates and phosphonates of alkali metals, such as potassium, sodium or lithium, alkaline earth metals, such as magnesium, calcium, Strontium or barium, or of aluminum, manganese, iron, cobalt, copper or zinc, with sodium acetate, lithium bromide, calcium bromide, calcium gluconate, zinc chloride, zinc sulfate, magnesium chloride, magnesium sulfate, ammonium carbonate, chloride and acetate being preferred.
  • These salts are preferably present in an amount of 0.03 to 65 mmol, in particular from 1 to 40 mmol, based on 100
  • the pH of the ready-to-use coloring preparations is usually between 2 and 12, preferably between 4 and 10.
  • Components A and optionally component B and the color enhancers optionally used can either be stored separately or together, either in a liquid to pasty preparation (aqueous or anhydrous) or as a dry powder. In the case of separate storage, the components are only intimately mixed with one another immediately before use. In dry storage, a defined amount of warm (30 to 80 ° C) water is usually added before use and a homogeneous mixture is produced. Examples
  • ⁇ E [( ⁇ L) 2 + ( ⁇ a) 2 + ( ⁇ b) 2 ] 1 ' 2
  • the tresses were washed 6 x with the shampoo poly ® cure Aloe & Mango Balsam Shampoo (Schwarzkopf Henkel) and then measured again colorimetrically.
  • the strand of hair before shampooing was used as the standard for determining the ⁇ E value (see Table 2).
  • Dehyton ® KN N-Dimethyl-N- (C 8 -d 8 -kokosamidopropyl) ammonium acetobetaine (approx. 30% active substance; INCI name: Aqua (Water), Cocamidopropyl Betaine) (COGNIS)

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Abstract

Procédé de coloration de fibres kératiniques, en particulier de cheveux humains, selon lequel les fibres sont d'abord traitées avec un oxydant, puis (A) au moins un composé diazo et / ou carbonyle de formule I et / ou II et éventuellement (B) au moins un composé en tant que constituant B, choisi dans un groupe constitué par (a) des composés à groupe amino ou hydroxy primaire ou secondaire, choisis parmi des amines aromatiques primaires ou secondaires, des composés hétérocycliques azotés et des composés hydroxy aromatiques, (b) des acides aminés, (c) des oligopeptides constitués de 2 à 9 acides aminés, (d) des composés acides CH, (e) des composés d'ammonium quaternaire, ainsi, éventuellement, que des constituants cosmétiques classiques, sont appliqués sur les fibres kératiniques, laissés quelque temps, habituellement env. 30 minutes, sur les fibres pour déployer leur action, puis rincés ou éliminés à l'aide d'un shampooing. On obtient ainsi des colorations résistant au lavage qui n'endommagent pas les fibres pendant l'étape de coloration et n'entraînent pas non plus une sensibilisation du cuir chevelu.
PCT/EP2002/010732 2001-10-04 2002-09-25 Procede de coloration de fibres keratiniques Ceased WO2003030841A1 (fr)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1433468A1 (fr) * 2002-12-23 2004-06-30 Henkel Kommanditgesellschaft auf Aktien Imines des sels du N-methylquinoline utilisés pour la teinture des fibres keratiniques
WO2004058200A1 (fr) * 2002-12-23 2004-07-15 Henkel Kommanditgesellschaft Auf Aktien Agent pour colorer des fibres keratiniques
US7504401B2 (en) 2003-08-29 2009-03-17 Locus Pharmaceuticals, Inc. Anti-cancer agents and uses thereof
US7709468B2 (en) 2005-09-02 2010-05-04 Abbott Laboratories Imidazo based heterocycles
WO2010129665A3 (fr) * 2009-05-05 2011-04-07 Cambria Pharmaceuticals, Inc. Pyrimidine-2,4,6-triones destinée à être utilisée pour le traitement d'une sclérose latérale amyotrophe

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007047685A1 (de) 2007-10-04 2008-07-31 Henkel Ag & Co. Kgaa Aufhellmittel mit kationischen Acylpyridiniumderivaten, Imidazolderivaten und Wasserstoffperoxid
DE102008022710A1 (de) 2008-05-07 2009-11-12 Henkel Ag & Co. Kgaa Aufhellmittel mit kationischen Acylpyridiniumderivaten, Co-Bleichaktivatoren und Wasserstoffperoxid
DE102008046433A1 (de) * 2008-09-09 2010-03-11 Henkel Ag & Co. Kgaa Aufhellmittel mit 2-Acylpyridinium-Derivaten
DE102008061133A1 (de) 2008-12-11 2010-06-17 Henkel Ag & Co. Kgaa Verstärkte Aufhellung bei gleichzeitiger Haarkräftigung
EP2246098A1 (fr) * 2009-04-27 2010-11-03 KPSS-Kao Professional Salon Services GmbH Composition de coloration
DE102009026817A1 (de) * 2009-06-08 2010-12-09 Henkel Ag & Co. Kgaa Nachbehandlung zur Farbfixierung
DE102009029043A1 (de) 2009-08-31 2011-03-03 Henkel Ag & Co. Kgaa Intensive, schonende Färbemittel
DE102009045629A1 (de) 2009-10-13 2011-04-14 Henkel Ag & Co. Kgaa Aufhellmittel mit kationischen Acylpyridiniumderivaten und bestimmten Ammonium-Verbindungen
DE102009045631A1 (de) 2009-10-13 2011-04-14 Henkel Ag & Co. Kgaa Aufhellmittel mit kationischen Acylpyridiniumderivaten und bestimmten Aminosäuren
FR3117823B1 (fr) * 2020-12-18 2023-11-17 Oreal Procédé de coloration capillaire mettant en oeuvre des dérivés particuliers de résorcinol, compositions associées et nouveaux composés

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000015184A1 (fr) * 1998-09-15 2000-03-23 Henkel Kommanditgesellschaft Auf Aktien Procede de coloration de fibres contenant de la keratine a l'aide de sels de diazonium stables
WO2001026616A1 (fr) * 1999-10-12 2001-04-19 Henkel Kommanditgesellschaft Auf Aktien Procede de coloration des cheveux

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000015184A1 (fr) * 1998-09-15 2000-03-23 Henkel Kommanditgesellschaft Auf Aktien Procede de coloration de fibres contenant de la keratine a l'aide de sels de diazonium stables
WO2001026616A1 (fr) * 1999-10-12 2001-04-19 Henkel Kommanditgesellschaft Auf Aktien Procede de coloration des cheveux

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1433468A1 (fr) * 2002-12-23 2004-06-30 Henkel Kommanditgesellschaft auf Aktien Imines des sels du N-methylquinoline utilisés pour la teinture des fibres keratiniques
WO2004058200A1 (fr) * 2002-12-23 2004-07-15 Henkel Kommanditgesellschaft Auf Aktien Agent pour colorer des fibres keratiniques
US7504401B2 (en) 2003-08-29 2009-03-17 Locus Pharmaceuticals, Inc. Anti-cancer agents and uses thereof
US7709468B2 (en) 2005-09-02 2010-05-04 Abbott Laboratories Imidazo based heterocycles
WO2010129665A3 (fr) * 2009-05-05 2011-04-07 Cambria Pharmaceuticals, Inc. Pyrimidine-2,4,6-triones destinée à être utilisée pour le traitement d'une sclérose latérale amyotrophe
US9499494B2 (en) 2009-05-05 2016-11-22 Northwestern University Pyrimidine-2,4,6-triones for use in the treatment of amyotrophic lateral sclerosis
EP3144299A1 (fr) * 2009-05-05 2017-03-22 Cambria Pharmaceuticals, Inc. Pyrimidine-2, 4, 6-triones a utiliser dans le traitement de sclerose laterale amyotrophique

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DE10148845A1 (de) 2003-04-10
EP1434552A1 (fr) 2004-07-07

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