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WO2006108458A1 - Produits servant simultanement a colorer et a eclaircir des fibres keratiniques - Google Patents

Produits servant simultanement a colorer et a eclaircir des fibres keratiniques Download PDF

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Publication number
WO2006108458A1
WO2006108458A1 PCT/EP2006/000666 EP2006000666W WO2006108458A1 WO 2006108458 A1 WO2006108458 A1 WO 2006108458A1 EP 2006000666 W EP2006000666 W EP 2006000666W WO 2006108458 A1 WO2006108458 A1 WO 2006108458A1
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PCT/EP2006/000666
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German (de)
English (en)
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Horst Höffkes
Thomas Mucha
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Henkel Kommanditgesellschaft Auf Aktien
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Publication of WO2006108458A1 publication Critical patent/WO2006108458A1/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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/22—Peroxides; Oxygen; Ozone
    • 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
    • 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
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • 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
    • A61Q5/08—Preparations for bleaching the hair
    • 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 a novel means for the simultaneous dyeing and whitening of keratin fibers, in particular human hair hair dyes based on direct dyes and / or oxidation dye precursors, which compared to conventional hair dyes both a more brilliant coloring and a better lightening of the hair causes ,
  • Coupler and developer components are also referred to as oxidation dye precursors.
  • the developer components are usually primary aromatic amines having a further, in the para or ortho position free or substituted hydroxy or amino group, Diaminopyridinderivate, heterocyclic hydrazones, 4-Aminopyra- zolonderivate and 2,4,5, 6-tetraaminopyrimidine and its derivatives used.
  • m-phenylenediamine derivatives naphthols, resorcinol and resorcinol derivatives, pyrazolones, m-aminophenols and substituted pyridine derivatives are generally used.
  • Suitable coupler substances are in particular ⁇ -naphthol, 1, 5, 2,7- and 1, 7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2,4-diaminophenoxyethanol , 2-amino-4- (2-hydroxyethylamino) -anisole (Lehmann's Blue), 1-phenyl-3-methyl-pyrazol-5-one, 2,4-diol chloro-3-aminophenol, 1, 3-bis- (2,4-diaminophenoxy) -propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5- Methylresorcinol, 3-amino-6-methoxy-2-methylaminopyridine and 3,5-diamino-2,6-d
  • dyeing or tinting agents which contain so-called direct drawers as a coloring component. These are dye molecules that raise directly onto the hair and do not require an oxidative process to form the dye. These dyes include, for example, the henna already known from antiquity for coloring body and hair. These dyeings are generally much more sensitive to shampooing than the oxidative dyeings, so that a much more undesirable change in shade or even a visible "discoloration" occurs much faster.
  • hair dye with oxidation dye precursors Prior to their application to human hair, hair dye with oxidation dye precursors are mixed with dilute aqueous hydrogen peroxide solution. The duration of exposure to the hair to achieve complete coloration is between about 30 and 40 minutes. It is obvious that users of these hair dyes have a need to reduce this exposure time.
  • the disclosed therein agents contain at least one developing agent and at least one coupler substance and at least one ammonium compound selected from the group consisting of ammonium chloride, ammonium sulfate, ammonium carbonate, ammonium bicarbonate and ammonium carbamate, and, after mixing with an oxidizing agent, in the ready-to-use mixture has a pH between 8 and 11.
  • the present invention is in a first embodiment, a means for simultaneous dyeing and whitening of human hair, comprising at least one substantive hair dye and at least one carbonate and / or a carbonate precursor, characterized in that it comprises at least one substantive hair dye from the group
  • Disperse Yellow 241 Disperse Blue 7 (Cl 62500) Disperse Blue 14 (CI 61500) Disperse Blue 26 (CI 63305) Disperse Blue 35 Disperse Blue 55 Disperse Blue 56 (Cl 63285) Disperse Blue 60 (Cl 61104) Disperse Blue 62 Disperse Blue 64 Disperse Blue 72 (CI 60725) Disperse Blue 77 Disperse Blue 79 (CI 11345) Disperse Blue 87 Disperse Blue 94 Disperse Blue 109 Disperse Blue 153 Disperse Blue 180 Disperse Blue 183 Disperse Blue 287 Disperse Blue 326 Disperse Blue 333 Disperse Blue 337 (Cl 11337) Disperse Disperse Blue 367 Disperse Green 9 Disperse Violet 8 (Cl 62030) Disperse Violet 17 (Cl 60712) Disperse Violet 26 (Cl 62025) Disperse Violet 28 (Cl 61102) Disperse Violet 33 (Cl 11218) Disperse Violet
  • Basic Blue 77 Basic Blue 124 Basic Blue 151 contains.
  • compositions according to the invention contain at least one carbonate and / or one carbonate precursor.
  • Carbonates within the meaning of the present application Compounds containing the carbonate group -0-C (O) -O- or ⁇ 0-C (O) -O ⁇ or a carbonate-analogous group with elements of IV.
  • Main group of the Periodic Table (especially -0-Si (O) -O - or "... 0-Si (O) -O ⁇ ) comprise carbonates may therefore be both salts and esters of carbonic acid or of the analogous acids of the elements of the IV main group of the Periodic Table" carbonate precursor "in the sense of the present Registration are substances that can form carbonates under the conditions of use. In this group fall mainly organic carbonic acid derivatives which form carbonates in the hydrolysis, in particular the carbamates.
  • sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate or ammonium carbonate and mixtures thereof can be used as carbonates in the context of the present invention.
  • organic carbonates is preferred.
  • Agents preferred according to the invention are characterized in that the carbonate is selected from carbonic acid mono- and / or diesters, preferably from methyl carbonate, ethyl carbonate, propyl carbonate, their salts and / or mixtures thereof.
  • esters of carbonic acid can be used. Both carbonic acid monoesters and carbonic acid diesters are suitable here. Agents preferred according to the invention comprise at least one carbonic acid monoester of the formula (I)
  • R is a saturated or unsaturated, straight-chain, branched, or cyclic, substituted or unsubstituted hydrocarbon radical, or a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle.
  • R preferably represents a substituted or unsubstituted, straight-chain or branched alkyl, alkenyl or alkynyl radical, preference being given to hydroxy, amino, nitro, sulfonic acid groups or halogens as substituents.
  • Further preferred radicals R are phenyl and benzyl radicals and further substituted representatives. More preferably, R is a C 1-6 alkyl group.
  • C r C 6 -alkyl groups are the groups methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl and hexyl.
  • radical R in formula (I) is selected from methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, terf-butyl as well as hydroxymethyl and hydroxyethyl radicals.
  • the acidic carbon atom of the carbonic monoester may also be present in neutralized form, i. it is also possible according to the invention to use salts of carbonic acid monoesters.
  • agents according to the invention are preferred which comprise the carbonic acid monoester carbonic acid monoamide in completely or partially neutralized form, preferably in the form of its alkali metal, ammonium, alkaline earth metal or aluminum salt and in particular in the form of its sodium salt.
  • Carbonic acid diesters according to the invention can be used as further preferred esters of carbonic acid.
  • Agents preferred according to the invention therefore contain at least one carbonic acid diester of the formula (II)
  • R and R ' are each, independently of one another, preferably a substituted or unsubstituted, straight-chain or branched alkyl, alkenyl or alkynyl radical, preference being given to hydroxy, amino, nitro, sulfonic acid groups or halogens as substituents , Further preferred radicals R and R 'are phenyl and benzyl radicals and further substituted representatives. Particularly preferably R or R 'is a C 1-6 alkyl group.
  • C 1 -C 6 -alkyl groups are the groups methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl and hexyl.
  • Particularly preferred agents according to the invention are characterized in that the radical R and R ' in formula (II) are each independently selected from methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl , tert-butyl and hydroxymethyl and hydroxyethyl radicals.
  • compositions according to the invention may also contain esters of orthocarbonic acid.
  • esters of carbonic acid can therefore be used according to the invention Orthokohlenklareester.
  • Agents preferred according to the invention therefore contain at least one carbonic diester of the formula (III)
  • R, R ', R "and R'” each independently represent a saturated or unsaturated, straight-chain, branched, or cyclic, substituted or unsubstituted hydrocarbon radical, or a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle.
  • R, R ', R “and R'” each independently of one another preferably represent a substituted or unsubstituted, straight-chain or branched alkyl, alkenyl or alkynyl radical, preference being given to hydroxy, amino, nitro, as substituents. , Sulfonic acid groups or halogens in question.
  • Further preferred radicals R, R ', R “and R'” are phenyl and benzyl radicals and further substituted representatives. Particularly preferably R or R 'is a C 1-6 alkyl group.
  • C r C 6 -alkyl groups are the groups methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl and hexyl.
  • Particularly preferred agents according to the invention are characterized in that the radicals R, R ', R "and R"' in formula (III) are each independently selected from methyl, ethyl, n-propyl, iso-propyl, n Butyl, iso-butyl, terf-butyl and Hydroxymethyl and hydroxyethyl residues.
  • Particularly preferred representatives are tetramethyl and tetraethyl orthocarbonate.
  • cyclic carbonic acid esters are referred to as 1, 3-dioxolan-2-ones and can be described by the following structure:
  • 3-dioxolan-2-ones are each bound in the 4- and 5-position two H atoms. It is possible and preferred within the scope of the present invention to use also derivatives of this basic structure, ie 1, 3-dioxolan-2-ones substituted in 4- or 4- and 5-position. There are no limits to the structural diversity, so that mono-, di-, tri- and tetra-substituted 1, 3-dioxolan-2-ones are suitable for use in the context of the present invention.
  • Agents preferred according to the invention are therefore characterized in that they contain at least one carboxylic ester from the group of substituted or unsubstituted 1,3-dioxolan-2-ones
  • R is a substituted or unsubstituted alkyl, alkenyl or alkylaryl radical.
  • Preferred radicals R are methyl, ethyl, n-propyl, isopropyl and hydroxymethyl and hydroxyethyl radicals.
  • agents according to the invention are therefore characterized in that they contain at least one monosubstituted 1-substituted 3-dioxolan-2-one derivative of the following formula (IV)
  • R is a substituted or unsubstituted alkyl, alkenyl or alkylaryl radical, wherein in further preferred agents of the invention the radical R in formula (III) is selected from methyl, ethyl, n-propyl, iso-propyl - As well as hydroxymethyl and hydroxyethyl radicals.
  • Ethylene carbonate is a colorless crystalline compound that melts at 39 ° C and boils at 238 ° C.
  • the readily soluble in water, alcohols and organic solvents ethylene carbonate can be prepared by large-scale synthesis of ethylene oxide and liquid CO 2 .
  • Propylene carbonate is a water-bright, easily mobile liquid, with a density of 1, 2057 like '3 , the melting point is -49 ° C, the boiling point at 242 0 C.
  • propylene carbonate is industrially by reaction of propylene oxide and CO 2 at 200 0 C. and 80 bar accessible.
  • Glycerol carbonate is accessible by transesterification of ethylene carbonate or dimethyl carbonate with glycerol, as by-products of ethylene glycol or methanol incurred. Another synthetic route is based on glycidol (2,3-epoxy-1-propanol), which is converted under pressure in the presence of catalysts with CO 2 to glycerol carbonate. Glycerol is a clear, mobile liquid with a density of 1, 398 gcm -3, boiling at 125-130 0 C (0.15 mbar).
  • glycerol carbonate for example, in amounts of 1, 0 to 15.0 wt .-%, preferably from 2.0 to 13.5 wt .-% and in particular from 3.5 to 11, 5 wt .-%, each based on the agent is used.
  • salts of carbonic acid monoesters or "carbonate precursors" which can form carbonates under the conditions of use can also be used according to the invention.
  • agents according to the invention are particularly preferred in which the carbonate is selected from carbonate monoester salts and / or carbonic acid monoamides and / or their salts, silyl carbonates and / or silyl carbamates and mixtures thereof.
  • Carbon monoxide salts preferred according to the invention satisfy the abovementioned formula (I), the acidic hydrogen being exchanged for a physiologically compatible cation, preferably Na + , K + , NH 4 + , etc.
  • compositions according to the invention may also contain carbonic acid monoamides as carbonate precursors.
  • preferred agents according to the invention are characterized in that they contain at least one carbonic acid monoamide of the formula (IV)
  • R is a saturated or unsaturated, straight-chain, branched, or cyclic, substituted or unsubstituted hydrocarbon radical, or a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle and X is H or a physiologically compatible cation.
  • R preferably represents a substituted or unsubstituted, straight-chain or branched alkyl, alkenyl or alkynyl radical, preference being given to hydroxy, amino, nitro, sulfonic acid groups or halogens as substituents come.
  • Further preferred radicals R are phenyl and benzyl radicals and further substituted representatives.
  • R is particularly preferably -6 alkyl group is a C.
  • C r C 6 -alkyl groups are the groups methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl and hexyl.
  • radical R in formula (IV) is selected from methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, fe / ⁇ f Butyl and hydroxymethyl and hydroxyethyl radicals.
  • the acidic H atom of the carbonic acid monoester or monoamide may also be in neutralized form, i.
  • agents according to the invention are preferred which contain the carbonic acid monoester or the carbonic acid monoamide in completely or partially neutralized form, preferably in the form of its alkali metal, ammonium, alkaline earth metal or aluminum salt and in particular in the form of its sodium salt.
  • a compound which contains, instead of carbon, another element of main group IV of the periodic table can also be used as the carbonate or carbonate precursor.
  • the silyl carbonates and / or silyl carbamates should be mentioned as preferred. These substances are described in detail below.
  • Agents preferred according to the invention are characterized in that they contain at least one silyl carbonate of the formula (V)
  • radicals R 1 , R 2 and R 3 are independently of one another a hydrogen atom, a saturated or unsaturated, straight-chain, branched or cyclic, substituted or unsubstituted hydrocarbon radical or for a Trialkylsilyl group, preferably a trimethylsilyl group or a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle or a halogen, a substituted or unsubstituted hydroxy, oxo, amino, imino groups and the radical R 4 is a chemical bond to Si - atom or to one of the radicals R 1 , R 2 or R 3 , a hydrogen atom, a saturated or unsaturated, straight-chain, branched or cyclic, substituted or unsubstituted hydrocarbon radical or for a substituted or unsubstituted SiIyI or Aluminylrios or for a substituted or unsubstituted aryl group or
  • Preferred radicals R 1 , R 2 and R 3 in the abovementioned formula (V) are substituted or unsubstituted, straight-chain or branched alkyl radicals.
  • the alkyl radicals having 1 to 5 carbon atoms and the hydroxyalkyl radicals are preferred, so that preferred agents according to the invention are characterized in that the radicals R 1 , R 2 and R 3 in formula (I) are selected from methyl, ethyl, n Propyl, iso-propyl, n-butyl, iso-butyl, ferf-butyl, hydroxymethyl and hydroxyethyl radicals.
  • Preferred radicals R 4 in the abovementioned formula (V) are hydrogen, substituted or unsubstituted, straight-chain or branched alkyl radicals and trialkylsilyl radicals. Among them, preferred are hydrogen, methyl, ethyl, tert-butyl and trimethylsilyl radicals.
  • silyl carbonates of the general formula (V) are reproduced with respect to their radicals R 1 , R 2 , R 3 and R 4 in the following Table 1:
  • agents according to the invention are preferred which comprise at least one silyl carbonate in completely or partially neutralized form, preferably in the form of its alkali metal, ammonium, alkaline earth metal or aluminum salt and in particular in the form of its sodium salt.
  • compositions of the invention may contain silyl carbamates.
  • Agents preferred according to the invention are characterized in that they contain a silyl carbamate of the formula (VI)
  • radicals R 1 , R 2 and R 3 independently of one another represent a hydrogen atom, a saturated or unsaturated, straight-chain, branched or cyclic, substituted or unsubstituted hydrocarbon radical or for a trialkylsilyl group, preferably a trimethylsilyl group or a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle or a halogen, a substituted or unsubstituted hydroxy, oxo, amino groups and the radicals R 4 and R 5 independently of one another for a chemical bond to the Si atom or to a the radicals R 1 , R 2 or R 3 , a hydrogen atom, a saturated or unsaturated, straight-chain, branched or cyclic, substituted or unsubstituted hydrocarbon radical or for a substituted or unsubstituted SiIyI or Aluminylolitute
  • Preferred radicals R 1 , R 2 and R 3 in the abovementioned formula (VI) are substituted or unsubstituted, straight-chain or branched alkyl radicals.
  • the alkyl radicals having 1 to 5 carbon atoms and the hydroxyalkyl radicals are preferred, so that preferred agents according to the invention are characterized in that the radicals R 1 , R 2 and R 3 in formula (VI) are selected from methyl, ethyl, n Propyl, iso-propyl, n-butyl, iso-butyl, fe / f-butyl and hydroxymethyl and hydroxyethyl radicals.
  • Preferred radicals R 4 and R 5 in the abovementioned formula (VI) are hydrogen, substituted or unsubstituted, straight-chain or branched alkyl radicals and trialkylsilyl radicals. Among them, preferred are hydrogen, methyl, ethyl, tert-butyl and trimethylsilyl radicals.
  • silyl carbamates of the general formula (VI) are reproduced with respect to their radicals R 1 , R 2 , R 3 and R 4 in the following Table 2:
  • the carbonate (s) in amounts of 0.5 to 15 wt .-%, preferably from 1 to 12 wt .-%, especially preferably from 2 to 9 wt .-% and in particular from 3 to 7 wt .-%, each based on the total agent included.
  • the direct dyes mentioned are preferably used in specific amounts.
  • agents according to the invention are preferred, the substantive (s) Dye (s) from the above list in amounts of 0.01 to 10 wt.%, Preferably from 0.05 to 8 wt.%, Particularly preferably from 0.1 to 5 wt.% And in particular from 0.5 to 3.5% by weight, based in each case on the total agent,
  • the agents according to the invention may contain further dyes and / or dye precursors.
  • Compositions according to the invention which additionally comprise at least one oxidation-type dye precursor of the developer type and / or optionally at least one coupler-type oxidation dye precursor are preferred.
  • the present invention is not subject to any restrictions.
  • the agents according to the invention can be used as further dye precursors - oxidation dye precursors of the developer and / or coupler type, and
  • Precursors of natural analog dyes such as indole and indoline derivatives, and mixtures of representatives of these groups.
  • the agent further contains at least one developer component.
  • the developer components are usually primary aromatic amines having a further, in the para or ortho position, free or substituted hydroxy or amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazole derivatives and 2,4,5,6-tetraaminopyrimidine and its derivatives used ,
  • p-phenylenediamine derivatives of the formula (E1) it may be preferred according to the invention to use as the developer component a p-phenylenediamine derivative or one of its physiologically acceptable salts. Particular preference is given to p-phenylenediamine derivatives of the formula (E1)
  • G 1 is a hydrogen atom, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -
  • Monohydroxyalkyl radical a C 2 - to C 4 -polyhydroxyalkyl radical, a (C 1 - to C 4 ) -
  • G 2 is a hydrogen atom, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -
  • Monohydroxyalkyl radical a C 2 - to C 4 -polyhydroxyalkyl radical, a (C 1 - to C 4 ) -
  • G 3 represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or
  • Fluorine atom a C 1 - to C 4 -alkyl radical, a d- to C 4 monohydroxyalkyl radical, a
  • G 4 represents a hydrogen atom, a halogen atom or a C 1 - to C 4 -alkyl radical or when G 3 and G 4 are ortho to each other, they may together form a bridging ⁇ , ⁇ -alkylenedioxy group, such as, for example, an ethylenedioxy group.
  • Examples of the C 1 - to C 4 -alkyl radicals mentioned as substituents in the compounds according to the invention are the groups methyl, ethyl, propyl, isopropyl and buty). Ethyl and methyl are preferred alkyl radicals.
  • Preferred Cr to C 4 -alkoxy radicals according to the invention are, for example, a methoxy or an ethoxy group.
  • a C 1 to C 4 hydroxyalkyl group there may be mentioned a hydroxymethyl, a 2-hydroxyethyl, a 3-hydroxypropyl or a 4-hydroxybutyl group. A 2-hydroxyethyl group is particularly preferred.
  • a particularly preferred C 2 to C 4 polyhydroxyalkyl group is the 1, 2-dihydroxyethyl group.
  • halogen atoms are according to the invention F, Cl or Br atoms, Cl atoms are very particularly preferred.
  • the other terms used are derived according to the invention from the definitions given here.
  • nitrogen-containing groups of the formula (E1) are in particular the amino groups, C 1 to C 4 monoalkylamino groups, C 1 to C 4 dialkylamino groups, C 1 to C 4 trialkylammonium groups, C 1 to C 4 monohydroxyalkylamino groups, Imidazolinium and ammonium.
  • Particularly preferred p-phenylenediamines of the formula (E1) are selected from p-phenylenediamine, p-toluenediamine, 2-chloro-p-phenylenediamine, 2,3-dimethyl-p-phenylenediamine, 2,6-dimethyl-p-phenylenediamine, 2 , 6-diethyl-p-phenylenediamine, 2,5-dimethyl-p-phenylenediamine, N, N-dimethyl-p-phenylenediamine, N, N-diethyl-p-phenylenediamine, N, N-dipropyl-p-phenylenediamine, 4-amino 3-methyl- (N, N-diethyl) -aniline, N, N-bis ( ⁇ -hydroxyethyl) -p-phenylenediamine, 4-N, N-bis ( ⁇ -hydroxyethyl) amino-2-methylaniline, 4-N, N-bis- ( ⁇
  • Very particularly preferred p-phenylenediamine derivatives of the formula (E1) according to the invention are p-phenylenediamine, p-toluenediamine, 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine, 2- ( ⁇ , ⁇ -dihydroxyethyl) -p-phenylenediamine and N, N bis (.beta.-hydroxyethyl) -p-phenylenediamine.
  • developer component compounds which contain at least two aromatic nuclei which are substituted by amino and / or hydroxyl groups.
  • binuclear developer components which can be used in the compositions according to the invention, mention may be made in particular of the compounds which correspond to the following formula (E2) and their physiologically tolerated salts:
  • Z 1 and Z 2 independently of one another represent a hydroxyl or NH 2 radical which is optionally substituted by a C 1 - to C 4 -alkyl radical, by a C 1 - to C 4 -hydroxyalkyl radical and / or by a bridge Y.
  • the bridge Y is 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 may be interrupted or terminated and may optionally be substituted by one or more hydroxyl or C 1 - to C 8 alkoxy radicals, or a direct bond
  • G 5 and G 6 are each independently a hydrogen or halogen atom , a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -monohydroxyalkyl radical, a C 2 - to C 4 -hydroxyalkyl radical, a C 1 - to C 4 -aminoalkyl radical or a direct compound for 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 C 1 to C 4 alkyl radical, with the provisos that
  • the compounds of formula (E2) contain at least one amino group which carries at least one hydrogen atom.
  • Preferred binuclear developer components of the formula (E2) are in particular: N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1,3-diamino-propan-2-ol, N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) ethylenediamine, N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'-bis - (ß-hydroxyethyl) -N, N'-bis (4-aminophenyl) - tetramethylenediamine, N, N'-bis (4-methyl-aminophenyl) -tetramethy endiamin, N 1 N'-diethyl-N,!
  • N'-bis (4'-amino-3'-methylphenyl) ethylenediamine bis (2-hydroxy-5-aminophenyl) methane, 1, 3-bis (2,5-diaminophenoxy) -propane-2 -ol, N, N'-bis (4'-aminophenyl) -1, 4-diazacycloheptane, N, N'-bis (2-hydroxy-5-aminobenzyl) -piperazine, N- (4'-Aminophenyl) -p-phenylenediamine and 1, 10-bis (2 ', 5'-diaminophenyl) -1, 4, 7, 10-tetraoxadecane and their physiologically acceptable salts.
  • Very particularly preferred binuclear developer components of the formula (E2) are N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1,3-diamino-propan-2-ol, Bis (2-hydroxy-5-aminophenyl) methane, 1, 3-bis (2,5-diaminophenoxy) -propan-2-ol, N, N'-bis (4'-aminophenyl) -1, 4-diazacycloheptane and 1, 10-bis- (2 ', 5'-diaminophenyl) -1, 4, 7, 10-tetraoxadecane or one of their physiologically acceptable salts.
  • p-aminophenol derivatives of the formula (E3) it may be preferred according to the invention to use as the developer component a p-aminophenol derivative or one of its physiologically tolerable salts. Particular preference is given to p-aminophenol derivatives of the formula (E3)
  • G 13 represents a hydrogen atom, a halogen atom, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -monohydroxyalkyl radical, a C 2 - to C 4 -polyhydroxyalkyl radical, a (C 1 - to C 4 ) - Alkoxy (C r to C 4 ) alkyl, a C 1 - to C 4 -Aminoalkylrest, a hydroxy (C r to C 4 ) alkylamino, a C 1 - to C 4 -hydroxyalkoxy, a C 1 - C 4 hydroxyalkyl aminoalkyl (C Crbis 4) or (di-C r to C 4 alkylamino) - alkyl - (C 1 to C 4), and
  • G 14 is a hydrogen or halogen atom, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -monohydroxyalkyl radical, a C 2 - to C 4 -polyhydroxyalkyl radical, a (C 1 - to C 4 ) - Alkoxy (C r to C 4 ) -alkyl radical, a C 1 - to C 4 -aminoalkyl radical or a C 1 - to C 4 -cyanoalkyl radical,
  • G 15 is hydrogen, C 1 - to C 4 alkyl, C 1 - to C 4 - monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a phenyl radical or a benzyl radical, and
  • G 16 is hydrogen or a halogen atom.
  • the substituents used in formula (E3) are defined according to the invention analogously to the above statements.
  • Preferred p-aminophenols of the formula (E3) are, in particular, p-aminophenol, N-methyl-p-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 2-hydroxymethylamino-4-aminophenol, 4 -Amino-3-hydroxymethylphenol, 4-amino-2- (D-hydroxyethoxy) -phenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, A-amino-2-methoxymethyl-phenol, 4-amino 2-aminomethylphenol, 4-amino-2- ( ⁇ -hydroxyethyl-aminomethyl) phenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) phenol, 4-amino-2-fluorophenol, 4-amino-2 chlorophenol, 4-amino-2,6-dichlorophenol, 4-amino-2- (diethylaminomethyl) phenol and their physiologically acceptable salts.
  • Very particularly preferred compounds of the formula (E3) are p-aminophenol, A-amino-3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) phenol and 4-amino 2- (diethylaminomethyl) -phenol.
  • the developer component may be selected from o-aminophenol and its derivatives such as 2-amino-4-methylphenol, 2-amino-5-methylphenol or 2-amino-4-chlorophenol.
  • the developer component may be selected from heterocyclic developer components such as the pyridine, pyrimidine, pyrazole, pyrazole pyrimidine derivatives and their physiologically acceptable salts.
  • Preferred pyridine derivatives are in particular the compounds 2,5-diamino-pyridine, 2- (4'-methoxyphenyl) amino-3-amino-pyridine, 2,3-diamino-6-methoxypyridine, 2- ( ⁇ -methoxyethyl ) amino-3-amino-6-methoxy-pyridine and 3,4-diamino-pyridine.
  • Preferred pyrimidine derivatives are in particular 2,4,5,6-tetraaminopyrimidine, A-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2-dimethylamino-4,5,6- triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triaminopyrimidine.
  • Preferred pyrazole derivatives are, in particular, 4,5-diamino-i-methylpyrazole, 4,5-diamino-1- ( ⁇ -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-phenylpyrazole, 4-amino-1, 3 dimethyl-5-hydrazinopyrazole, 1-benzyl-4,5-diamino-3-methylpyrazole, 4,5-diamino-3-tert-butyl-1-methylpyrazole, 4,5-diamino-1-tert-butyl 3-methylpyrazole, 4,5-diamino-1- ( ⁇ -hydroxyethyl) -3
  • Triaminopyrazole 1-methyl-3,4,5-triaminopyrazole, 3,5-diamino-1-methyl-4-methylaminopyrazole and 3,5-diamino-4- ( ⁇ -hydroxyethyl) amino-1-methylpyrazole.
  • Preferred pyrazole-pyrimidine derivatives are, in particular, the derivatives of pyrazolo [1,5-a] pyrimidine of the following formula (E4) and their tautomeric forms, provided that a tautomeric equilibrium exists:
  • G 17 , G 18 , G 19 and G 20 independently of one another represent a hydrogen atom, a C 1 - to C 4 -alkyl radical, an aryl radical, a C 1 - to C 4 -hydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl a (C 1 - to C 4) alkoxy -, alkyl (Ci to C4) a C 1 - to C 4 -aminoalkyl radical, which may be optionally protected by an acetyl ureide or a sulfonyl radical a (C 1 - to C 4) alkylamino (Cr to C 4) - alkyl group, a di - aminoalkyl (C r to C 4), wherein the dialkyl - [(C r to C 4) alkyl] - residues optionally form a carbocycle or a heterocycle with 5 or 6 chain links, a C 1 - to C 4 hydroxyalky
  • the pyrazolo [1, 5-a] -pyrimidines of the above formula (E4) can be prepared as described in the literature by cyclization from an aminopyrazole or from hydrazine.
  • the agents according to the invention contain at least one coupler component.
  • coupler components m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives are generally used.
  • Suitable coupler substances are in particular 1-naphthol, 1, 5, 2,7- and 1, 7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinomonomethylether, m-phenylenediamine, 1-phenyl 3-methyl-pyrazolone-5, 2,4-dichloro-3-aminophenol, 1, 3-bis (2 ', 4'-diaminophenoxy) -propane, 2-chloro-resorcinol, 4-chloro-resorcinol, 2 Chloro-6-methyl-3-aminophenol, 2-amino-3-hydroxypyridine, 2-methylresorcinol, 5-methylresorcinol and 2-methyl-4-
  • Preferred coupler components according to the invention are m-aminophenol and its derivatives, such as, for example, 5-amino-2-methylphenol, 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, N-cyclopentyl-3-aminophenol, 1,3-dihydroxy-5- (methylamino) benzene, 3-ethylamino-4-methylphenol and 2,4- dichloro-3-aminophenol, o-aminophenol and its derivatives,
  • Di- or trihydroxybenzene derivatives such as, for example, resorcinol, resorcinomonomethyl ether, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol, 2-chlororesorcinol, 4-chlororesorcinol, pyrogallol and 1,2,4-trihydroxybenzene,
  • Pyridine derivatives such as 2,6-dihydroxypyridine, 2-amino-3-hydroxypyridine, 2-amino-5-chloro-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxypyridine, 2,6-dihydroxy-3, 4-dimethylpyridine, 2,6-dihydroxy-4-methylpyridine, 2,6-diaminopyridine, 2,3-diamino-6-methoxypyridine and 3,5-diamino-2,6-dimethoxypyridine,
  • Naphthalene derivatives such as, for example, 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 1-phenyl-3-methylpyrazol-5-one, indole derivatives such as 4-hydroxyindole, 6-hydroxyindole and 7-hydroxyindole, pyrimidine derivatives such as 4,6-diaminopyrimidine, 4-amino-2,6-dihydroxypyrimidine , 2,4-diamino-6-hydroxypyrimidine, 2,4,6-trihydroxypyrimidine, 2-amino-4-methylpyrimidine, 2-amino-4-hydroxy-6-methylpyrimidine and 4,6-dihydroxy-2-methylpyrimidine, or
  • coupler components according to the invention are 1-naphthol, 1, 5, 2,7- and 1, 7-dihydroxynaphthalene, 3-aminophenol, 5-amino-2-methylphenol, 2-amino-3 hydroxypyridine, resorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methyl resorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol and 2,6-dihydroxy-3,4-dimethylpyridine.
  • indoles and indolines which have at least one hydroxy or amino group, preferably as a substituent on the six-membered ring.
  • These groups may carry further substituents, e.g. Example in the form of etherification or esterification of the hydroxy group or alkylation of the amino group.
  • the agents contain at least one indole and / or indoline derivative.
  • Particularly suitable precursors of naturally-analogous hair dyes are derivatives of 5,6-dihydroxyindoline of the formula (IIIa),
  • R 1 is hydrogen, a C r C 4 -alkyl group or a C r C 4 -hydroxy-alkyl group
  • R 2 is hydrogen or a -COOH group, wherein the -COOH group may also be present as a salt with a physiologically compatible cation
  • R 3 is hydrogen or a C r C 4 alkyl group
  • R 4 is hydrogen, a C 1 -C 4 -alkyl group or a group -CO-R 6 , in which R 6 is a C r C 4 -alkyl group, and R 5 is one of the groups mentioned under R 4 , as well as physiologically acceptable 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 5, 6-Dihydroxyindolin.
  • R 1 is hydrogen, a C r C 4 -alkyl group or a C r C 4 -hydroxyalkyl group
  • R 2 is hydrogen or a -COOH group, wherein the -COOH group may also be present as a salt with a physiologically compatible cation,
  • R 3 is hydrogen or a C 1 -C 4 -alkyl group
  • R 4 is hydrogen, a C r C 4 -alkyl group or a group -CO-R 6 , in which R 6 is a C 1 -C 4 -alkyl group, and
  • R 5 is one of the groups mentioned under R 4 , as well as physiologically acceptable 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 especially the 5,6 -Dihydroxyindol.
  • the indoline and indole derivatives can be used in the agents used in the process according to the invention both as free bases and in the form of their physiologically acceptable salts with inorganic or organic acids, eg.
  • the indole or indoline derivatives are usually contained therein in amounts of 0.05-10% by weight, preferably 0.2-5% by weight.
  • the indoline or indole derivative in hair dyes in combination with at least one amino acid or an oligopeptide.
  • the amino acid is advantageously an ⁇ -amino acid;
  • Very particularly preferred ⁇ -amino acids are arginine, ornithine, lysine, serine and histidine, in particular arginine.
  • Preferred agents according to the invention are characterized in that they contain at least one dye precursor from the groups of the aromatic and heteroaromatic diamines, aminophenols, naphthols, polyphenols CH-acidic coupler components and their derivatives in amounts of from 0.01 to 25% by weight, preferably 0.5 to 10 wt.%, In particular from 1 to 5 wt .-%, each based on the total agent included.
  • compositions according to the invention may contain further substantive dyes.
  • Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Preferred substantive dyes are those having the international designations or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, Acid Yellow 1, Acid Yellow 10, Acid Yellow 23, Acid Yellow 36, HC Orange Disperse Orange 3, Acid Orange 7, HC Red 1, HC Red 3, HC Red 10, HC Red 11, HC Red 13, Acid Red 33, Acid Red 52, HC Red BN, Pigment Red 57: 1, HC Blue 2, HC Blue 12, Disperse Blue 3, Acid Blue 7, Acid Green 50, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Acid Violet 43, Disperse Black 9, Acid Black 1, and Acid Black 52 known compounds as well as 1 , 4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1,4-bis- ( ⁇ -hydroxyethyl) amino-2-nitrobenzene, 3-islitro-4- ( ⁇ -hydroxyethyl) aminophenol, 2- 2'-hydroxyethyl) amino-4,6-dinitrophenol, 1- (2'-hydroxyethyl) amino-4-
  • Corresponding agents according to the invention which are characterized in that they contain at least one substantive dye from the group of cationic (basic) dyes, preferably Basic Blue 6, CI-No. 51, 175; Basic Blue 7, CI- No. 42.595; Basic Blue 9, Cl-No. 52.015; Basic Blue 26, Cl-No. 44.045; Basic Blue 41, Cl-No. 11, 154; Basic Blue 99, Cl-No. 56.059; Basic Brown 4, Cl-No. 21, 010; Basic Brown 16, Cl-No. 12.250; Basic Brown 17, Cl-No. 12,251; Basic Green 1, Cl-No. 42.040; Basic Orange 31; Basic Red 2, Cl-No. 50.240; Basic Red 22, Cl-No.
  • Basic Blue 6 cationic (basic) dyes
  • dyes some representatives are particularly preferred, for which reason further preferred agents according to the invention, characterized in that they comprise at least one direct drawler selected from Basic Blue 7, Basic Blue 99, Basic Violet 14, Basic Brown 16, Basic Brown 17, Basic Orange 31, Basic Red 46, Basic Red 51, Basic Red 76, Basic Yellow 57, Basic Yellow 87, Acid Black 1, Acid Blue 7, Acid Violet 43, Acid Red 23, Acid Red 52, Acid Orange 7, Acid Yellow Disperse Blue 1, Disperse Blue 3, Disperse Violet 1, Disperse Violet 4, HC Orange 1, HC Red 1, HC Red 1, Acid Yellow 10, Acid Yellow 36, Food Green 3, Pigment Red 57-1, Disperse Black 9, Disperse Blue 1 3, HC Red 13, HC Yellow 2, HC Yellow 4, Na-Pikramat, 1, 4-bis (2 '-hydroxyethyl) amino-2-nitro-p-phenylenediamine, HC Yellow 5, HC Blue 2, HC Blue 12, 4-amino-3-nitrophenol, HC Yellow 6, HC Yellow 12, 2-nitro-1- (2 'hydroxyethyl)
  • agents according to the invention may contain a cationic substantive dye. Particularly preferred are
  • aromatic systems substituted with a quaternary nitrogen group such as Basic Yellow 57, Basic Red 76, Basic Blue 99, Basic Brown 16 and Basic Brown 17, as well as
  • Preferred cationic substantive dyes of group (c) are in particular the following compounds:
  • the compounds of the formulas (DZ1), (DZ3) and (DZ5) which are also known by the names Basic Yellow 87, Basic Orange 31 and Basic Red 51, are very particularly preferred cationic substantive dyes of group (c).
  • the cationic direct dyes, which are sold under the trademark Arianor ® are, according to the invention also very particularly preferred cationic direct dyes.
  • the agents according to the invention according to this embodiment contain the remaining, i. not directly in the above list substantive dyes preferably in an amount of 0.01 to 20 wt .-%, based on the total agent.
  • preparations of the invention may also naturally occurring dyes such as henna red, henna neutral, henna black, chamomile, sandalwood, black tea, buckthorn bark, sage, bluewood, madder root, Catechu, Sedre and alkano root are included.
  • the agents according to the invention contain nonionic surfactants.
  • Such surfactants having an HLB of 5.0 and greater are preferred.
  • HLB value For the definition of the HLB value, explicit reference is made to the statements in Hugo Janistyn, Handbuch der Kosmetika und Riechstoffe, III. Volume: The personal care products, 2nd edition, Dr. med. Alfred Hüthig Verlag Heidelberg, 1973, pages 68-78 and Hugo Janistyn, Paperback of modern perfumery and cosmetics, 4th edition, Scientific Publishing Company m.b.H. Stuttgart, 1974, pages 466-474, as well as the original works cited therein.
  • nonionic surfactants are because of the ease of processing substances that are commercially available as solids or liquids in pure form.
  • the definition of purity in this context does not refer to chemically pure compounds. Rather, especially when it comes to natural-based products, mixtures of different homologs can be used, for example, with different alkyl chain lengths, such as those obtained with products based on natural fats and oils. Even with alkoxylated products, mixtures of different degrees of alkoxylation are usually present.
  • purity in this context refers rather to the fact that the selected substances should preferably be free from solvents, adjuvants and other impurities.
  • Preferred nonionic surfactants are
  • fatty alkyl groups having 8 to 22, in particular 10 to 16, carbon atoms in the fatty alkyl group and 1 to 30, in particular 1 to 15, ethylene oxide and / or propylene oxide units.
  • Preferred fatty alkyl groups are, for example, lauryl, myristyl, cetyl, but also stearyl, isostearyl and oleyl groups.
  • Particularly preferred compounds of this class are, for example, lauryl alcohol with 2 to 4 ethylene oxide units, oleyl and cetyl alcohol with 5 to 10 ethylene oxide, cetyl alcohol and stearyl alcohol and mixtures thereof with 10 to 30 ethylene oxide units and the commercial product Aethoxal ® B (Henkel), a Lauryl alcohol with 5 ethylene oxide and 3 propylene oxide units.
  • Aethoxal ® B (Henkel)
  • Lauryl alcohol with 5 ethylene oxide and 3 propylene oxide units
  • the alkoxy group has no OH group at the end but is "closed” in the form of an ether, in particular a C 1 -C 4 -alkyl ether.
  • An example of such a compound is the commercially available product ® Dehypon LT 054, a C-8 12-1 Fettalkoholol + 4.5 ethylene oxide-butyl ether.
  • - alkoxylated fatty acids having 8 to 22, in particular 10 to 16, carbon atoms in the fatty acid group and 1 to 30, in particular 1 to 15, ethylene oxide and / or propylene oxide units.
  • Preferred fatty acids are, for example, lauric, myristic, palmitic, stearic, isostearic and oleic acids.
  • - alkoxylated, preferably propoxylated and especially ethoxylated, mono-, di- and triglycerides examples are glycerol monolaurate + 20 ethylene oxide and glycerol monostearate + 20 ethylene oxide.
  • Polyglycerol esters and alkoxylated polyglycerol esters are for example poly (3) glycerindiisostearat (commercial product: Lame form ® TGI (Henkel)) and poly (2) glycerinpolyhydroxy- stearate (commercial product: Dehymuls ® PGPH (Henkel)).
  • Sorbitan fatty acid esters and alkoxylated sorbitan fatty acid esters such as sorbitan monolaurate and sorbitan monolaurate + 20 ethylene oxide (EO).
  • EO ethylene oxide
  • - Alkylphenols and Alkylphenolalkoxylate having 6 to 21, in particular 6 to 15, carbon atoms in the alkyl chain and 0 to 30 ethylene oxide and / or propylene oxide units.
  • Preferred representatives of this class are, for example, nonylphenol + 4 EO, nonylphenol + 9 EO, octylphenol + 3 EO and octylphenol + 8 EO.
  • nonionic surfactants are the alkoxylated fatty alcohols, the alkoxylated fatty acids and the alkylphenols and alkylphenol alkoxylates.
  • Agents according to the invention which contain non-ionic surface-active substances in amounts of 1 to 5% by weight have proved to be particularly advantageous.
  • compositions according to the invention may contain all known in such preparations active ingredients, additives and excipients.
  • the agents contain at least one surfactant, wherein in principle both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable.
  • anionic surfactants may be very particularly preferred.
  • Preferred anionic surfactants are alkyl sulfates, ether carboxylic acid salts having 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule such as C 12 H 25 - (C 2 H 4 O) S -CH 2 -COONa and in particular salts of saturated and especially unsaturated C8-C22 carboxylic acids such as oleic acid, stearic acid, isostearic acid and palmitic acid.
  • anionic surfactants should preferably be present in solid, in particular powder form. Very particular preference is given to solid soaps, especially sodium stearate, at room temperature. These are preferably present in amounts of from 5 to 20% by weight, in particular from 10 to 15% by weight.
  • nonionic surfactants are C 8 -C 22 -alkyl mono- and oligoglycosides and their ethoxylated analogs.
  • the nonethoxylated compounds have been found to be particularly suitable.
  • the cationic surfactants which can be used in the agents according to the invention are, in particular, quaternary ammonium compounds. Preference is given to ammonium halides such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, eg.
  • cetyltrimethylammonium chloride stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride.
  • Further cationic surfactants which can be used according to the invention are the quaternized protein hydrolysates.
  • Alkylamidoamines in particular fatty acid amidoamines, such as the stearylamidopropyldimethylamine obtainable under the name Tego Amid® S 18, are distinguished not only by a good conditioning action but also by their good biodegradability.
  • esterquats such as the Distearoylethylhydroxyethylammoniurnmethosulfat available in a blend with Cetearylalkohle under the name Dehyquart® ® F 75 miles.
  • the compounds containing alkyl groups used as surfactants may each be uniform substances. However, it is generally preferred to use native vegetable or animal raw materials in the production of these substances, so that substance mixtures having different alkyl chain lengths depending on the respective raw material are obtained.
  • compositions according to the invention may comprise at least one ammonium compound from the group consisting of ammonium chloride, ammonium carbonate, ammonium bicarbonate, ammonium sulfate and / or
  • Ammonium carbamate in an amount of 0.5 to 10, preferably 1 to 5 wt .-%, based on the total composition of the composition.
  • the agents according to the invention may contain further active ingredients, auxiliaries and additives, such as - Nonionic polymers such as vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes, cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyldiallylammonium chloride polymers, acrylamide-dimethyldiallyl ammonium chloride copolymers, dimethylaminoethyl methacrylate quaternized with diethyl sulfate Vinylpyrrolidone copolymers, vinylpyrrolidone-imidazolinium methochloride copolymers and quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers such as, for example, acrylamidopropyltrimethylammonium chloride / acrylate copo
  • Thickeners such as agar-agar, guar gum, alginates, xanthan gum, gum arabicum, karaya gum, locust bean gum, linseed gums, dextrans, celulose derivatives, e.g. For example, methyl cellulose, hydroxyalkyl cellulose and carboxymethylcellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such. Bentonite or fully synthetic hydrocolloids such as e.g. Polyvinyl alcohol, structurants such as maleic acid and lactic acid, hair conditioning compounds such as phospholipids, for example soya lecithin, egg lecithin and cephalins,
  • Protein hydrolysates in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolysates, their condensation products with fatty acids and quaternized protein hydrolysates, perfume oils, dimethyl isosorbide and cyclodextrins,
  • Solvents and mediators such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol,
  • fiber-structure-improving active substances in particular mono-, di- and oligosaccharides such as, for example, glucose, galactose, fructose, fructose and lactose,
  • quaternized amines such as methyl-1-alkylamidoethyl-2-alkylimidazolinium methanesulfate defoamers such as silicones,
  • 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 substances such as allantoin, pyrrolidonecarboxylic acids and their salts, and also bisabolol, vitamins, provitamins and vitamin precursors, in particular those of groups A, B 3 , B 5 , B 6 , C, E, F and H,
  • Plant extracts such as extracts of green tea, oak bark, stinging nettle, witch hazel, hops, chamomile, burdock root, horsetail, hawthorn, lime blossom, almond, aloe vera, spruce needle, horse chestnut, sandalwood, juniper, coconut, mango, apricot, lime, wheat, kiwi , Melon, orange, grapefruit, sage, rosemary, birch, mallow, meadowfoam, quenelle, yarrow, thyme, lemon balm, toadstool, coltsfoot, marshmallow, meristem, ginseng and ginger root ,. Cholesterol, ⁇
  • Bodying agents such as sugar esters, polyol esters or polyol alkyl ethers, fats and waxes such as spermaceti, beeswax, montan wax and paraffins, fatty acid alkanolamides,
  • - swelling and penetrating substances such as glycerol, propylene glycol monoethyl ether, carbonates, bicarbonates, guanidines, ureas and primary, secondary and tertiary phosphates,
  • Opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers, pearlescing agents such as ethylene glycol mono- and distearate and PEG-3-distearate,
  • Stabilizers for hydrogen peroxide and other oxidizing agents propellants such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and air,
  • compositions according to the invention may contain the ingredients in a suitable aqueous, alcoholic or aqueous-alcoholic carrier.
  • a suitable aqueous, alcoholic or aqueous-alcoholic carrier are, for example, creams, emulsions, gels or 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 of the present invention are aqueous solutions containing, to understand 3 to 70 wt .-% of a C r C 4 -alcohol, in particular ethanol or isopropanol in a sense.
  • the compositions of the invention may additionally contain other organic solvents, such as methoxybutanol, benzyl alcohol, ethyl diglycol or 1, 2-propylene glycol. Preference is given to all water-soluble organic solvents.
  • Preferred agents according to the invention are characterized in that they additionally contain a nonaqueous solvent, with particularly preferred agents according to the invention the solvent in a concentration of 0.1 to 30 weight percent, preferably in a concentration of 1 to 20 weight percent, most preferably in a concentration of 2 - 10 weight percent, each based on the agent included.
  • the solvent is selected from ethanol, n-propanol, isoropanol, n-butanol, propylene glycol, n-butylene glycol, glycerol, diethylene glycol monoethyl ether, diethylene glycol mono-n-butyl ether, phenoxyethanol and benzyl alcohol and their mixtures.
  • compositions according to the invention may contain further ingredients.
  • use of certain metal ions or complexes may be preferred to obtain intense colorations.
  • Agents according to the invention which additionally contain Cu, Fe, Mn, Ru ions or complexes of these ions are preferred here.
  • Preferred agents according to the invention comprise from 0.0001 to 2.5% by weight, preferably from 0.001 to 1% by weight, based on the total composition of the composition, of at least one compound from the group consisting of copper chloride (CuCl 2 ), copper sulfate (CuSO 4 ), Iron (II) sulfate, manganese (II) sulfate, manganese (II) chloride, cobalt (II) chloride, cerium sulfate, cerium chloride, vanadium sulfate, potassium iodide, sodium iodide, lithium chloride, potassium dichromate, magnesium acetate, calcium chloride, calcium nitrate, barium nitrate, manganese dioxide ( MnO 2 ) and / or hydroquinone.
  • CuCl 2 copper chloride
  • CuSO 4 copper sulfate
  • Iron (II) sulfate Iron
  • manganese (II) sulfate manganese
  • the pH of the compositions according to the invention can be adjusted within a wide range by suitable ingredients such as acidifying agent or alkalizing agent.
  • suitable ingredients such as acidifying agent or alkalizing agent.
  • Preferred agents according to the invention are characterized in that the pH of the composition is 6 to 11, preferably 7.5 to 10 and particularly preferably 8 to 9.
  • Oxidative dyeing of the fibers can in principle be carried out with atmospheric oxygen in the presence of oxidation dye precursors.
  • a chemical oxidizing agent is used, especially if, in addition to the coloring, a lightening effect on human hair is desired. This lightening effect may be desired regardless of the staining method.
  • the presence of oxidation dye precursors is not a mandatory requirement for the use of oxidizing agents in the compositions according to the invention.
  • Suitable oxidizing agents are persulfates, chlorites and in particular hydrogen peroxide or its addition products of urea, melamine and sodium borate.
  • the oxidation colorant can also be applied to the hair together with a catalyst which promotes the oxidation of the dye precursors, e.g. by atmospheric oxygen, activated.
  • catalysts are e.g. Metal ions, iodides, quinones or certain enzymes.
  • Suitable metal ions are, for example, Zn 2+ , Cu 2+ , Fe 2+ , Fe 3+ , Mn 2+ , Mn 4+ , Li + , Mg 2+ , Ca 2+ and Al 3+ . Particularly suitable are Zn 2+ , Cu 2+ and Mn 2+ .
  • the metal ions can in principle be used in the form of any physiologically acceptable salt or in the form of a complex compound.
  • Preferred salts are the acetates, sulfates, halides, lactates and tartrates.
  • Suitable enzymes include peroxidases, which can significantly enhance the effect of small amounts of hydrogen peroxide.
  • enzymes suitable according to the invention which directly oxidize the oxidation dye precursors with the aid of atmospheric oxygen, such as, for example, the laccases, or generate small amounts of hydrogen peroxide in situ and thus biocatalytically activate the oxidation of the dye precursors.
  • catalysts for the oxidation of the dye precursors are the so-called 2-electron oxidoreductases in combination with the specific substrates, eg
  • Lactate oxidase and lactic acid and their salts Lactate oxidase and lactic acid and their salts
  • the actual colorant is conveniently prepared immediately prior to use by mixing the preparation of the oxidizing agent with the preparation containing the compounds of formula I and optionally dye precursors.
  • the resulting ready-to-use hair dye preparation should preferably have a pH in the range of 6 to 12. Particularly preferred is the use of the hair dye in a weakly alkaline medium.
  • the application temperatures can be in a range between 15 and 40 0 C.
  • the hair dye is removed by rinsing of the hair to be dyed. The washing with a shampoo is omitted if a strong surfactant-containing carrier, such as a dyeing shampoo was used.
  • an agent according to the invention may optionally be applied to the hair with additional dye precursors but also without prior mixing with the oxidation component. After an exposure time of 20 to 30 minutes, the oxidation component is then applied, if appropriate after an intermediate rinse. After another The reaction time of 10 to 20 minutes is then rinsed and, if desired, post-sonicated.
  • the corresponding agent is adjusted to a pH of about 4 to 7.
  • an air oxidation is initially desired, wherein the applied agent preferably has a pH of 7 to 10.
  • the use of acidified peroxydisulfate solutions may be preferred as the oxidizing agent.
  • a second object of the present invention is a process for the simultaneous dyeing and whitening of human hair comprising adding to an aqueous-based composition containing hydrogen peroxide an agent comprising at least one substantive hair dye and at least one carbonate and / or carbonate precursor homogeneous composition is mixed, and this is applied to the hair, characterized in that at least one direct-acting dye contained in the medium is selected from
  • Disperse Red 338 Disperse Red 54 Disperse Red 258 Disperse Orange 66 Disperse Yellow 241 Disperse Biue 7 (Cl 62500) Disperse Blue 14 (Cl 61500) Disperse Blue 26 (Cl 63305) Disperse Blue 35 Disperse Blue 55 Disperse Blue 56 (Cl 63285) Disperse Blue 60 Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue Disperse Blue 337 Disperse Blue 369 Disperse Blue 34 Disperse Blue 36 Disperse Blue 9 Disperse Violet 8 (Cl 62030) Disperse Violet 17 (Cl 60712) Disperse
  • the aqueous-based composition contains from 1 to 20% by weight, preferably from 2 to 10% by weight and in particular from 3 to 6% by weight of hydrogen peroxide, calculated as 100% H 2 O 2 .
  • Another object of the present invention is therefore a process for the simultaneous dyeing and whitening of human hair, comprising an aqueous-based composition containing hydrogen peroxide with an agent containing at least one substantive hair dye and an agent containing at least one carbonate and / or a Carbonate precursor mixed into a homogeneous composition, and this is applied to the hair.
  • Another object of the present invention is the use of substantive dyes from the group
  • Basic Blue 124 Basic Blue 151 in carbonate and / or carbonate precursor-containing agents for the simultaneous dyeing and whitening of hair.
  • the mutated mutandis applies to the preferred agents.
  • Ci 2- i8 coconut fatty alcohol 3.0% by weight
  • Formulations 1 to 10 were mixed in a weight ratio of 1: 1 with a hydrogen peroxide-containing emulsion of the following composition:
  • Formulations 1 to 10 were dyed in a liquor ratio of 4: 1 for 30 minutes on natural white or dark blond hair strands (codes: Kerling natural white or Kerlinggnablond 7/0). After the exposure time, the hair is rinsed, washed with a conventional shampoo and then dried.

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Abstract

L'invention concerne des produits servant simultanément à colorer et à éclaircir des cheveux d'être humain. Ces produits contiennent un colorant capillaire spécifique montant directement sur la fibre, et au moins un carbonate et/ou un précurseur de carbonate.
PCT/EP2006/000666 2005-03-21 2006-01-26 Produits servant simultanement a colorer et a eclaircir des fibres keratiniques WO2006108458A1 (fr)

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DE200510013488 DE102005013488A1 (de) 2005-03-21 2005-03-21 Mittel zum gleichzeitigen Färben und Aufhellen von keratinhaltigen Fasern

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Cited By (15)

* Cited by examiner, † Cited by third party
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EP2196184A1 (fr) * 2008-12-11 2010-06-16 Henkel AG & Co. KGaA Agent de teinture capillaire avec indicateur de couleur
WO2010097338A3 (fr) * 2009-02-25 2010-11-11 Basf Se Composition de coloration capillaire
WO2010097339A3 (fr) * 2009-02-25 2010-11-11 Basf Se Composition de coloration capillaire
CN101983999A (zh) * 2010-07-30 2011-03-09 江苏亚邦染料股份有限公司 一种复配型直接印花分散蓝染料
EP2468248A1 (fr) * 2010-12-27 2012-06-27 KPSS-Kao Professional Salon Services GmbH Utilisation de colorants pour colorer des fibres en kératine et compositions comportant les colorants
US8444710B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a m-aminophenol and derivatives thereof
US8444709B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a 2-aminophenol and derivatives thereof
US8444714B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-Hexy1/Hepty1-4,5-diaminopyrazole and a benzene-1,3-diol and derivatives thereof
US8444711B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a benzene-1,3-diamine and derivatives thereof
US8444712B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a benzo[1,3]dioxol-5-ylamine and derivatives thereof
US8444713B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a naphthalen-1-ol and derivatives thereof
US8460397B2 (en) 2011-02-22 2013-06-11 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a pyridine and derivatives thereof
CN103525124A (zh) * 2013-10-23 2014-01-22 江苏德旺化工工业有限公司 一种分散黑染料
WO2018180515A1 (fr) * 2017-03-29 2018-10-04 株式会社マンダム Composition de coloration capillaire
EP2793817B1 (fr) 2011-12-23 2020-09-23 Kao Germany GmbH Composition décolorante et colorante pour les cheveux

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JP7105155B2 (ja) * 2017-09-20 2022-07-22 花王株式会社 粉末状染毛剤組成物
DE102017222516A1 (de) 2017-12-12 2019-06-13 Henkel Ag & Co. Kgaa Blondiermittel und Verfahren zur schonenden oxidativen Haaraufhellung

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DE4331136C1 (de) * 1993-09-14 1994-08-25 Goldwell Ag Mittel zum gleichzeitigen Färben und Aufhellen von menschlichen Haaren
WO2000030596A1 (fr) * 1998-11-20 2000-06-02 Hans Schwarzkopf Gmbh & Co. Kg Solvants pour milieux pulverulents
WO2005123019A1 (fr) * 2004-06-22 2005-12-29 Henkel Kommmanditgesellschaft Auf Aktien Agents effectuant en meme temps la coloration et l'eclaircissement des fibres keratiniques

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EP0435012A1 (fr) * 1989-11-30 1991-07-03 Sunstar Kabushiki Kaisha Composition pour la teinture des cheveux en deux parties
DE4331136C1 (de) * 1993-09-14 1994-08-25 Goldwell Ag Mittel zum gleichzeitigen Färben und Aufhellen von menschlichen Haaren
WO2000030596A1 (fr) * 1998-11-20 2000-06-02 Hans Schwarzkopf Gmbh & Co. Kg Solvants pour milieux pulverulents
WO2005123019A1 (fr) * 2004-06-22 2005-12-29 Henkel Kommmanditgesellschaft Auf Aktien Agents effectuant en meme temps la coloration et l'eclaircissement des fibres keratiniques

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2196184A1 (fr) * 2008-12-11 2010-06-16 Henkel AG & Co. KGaA Agent de teinture capillaire avec indicateur de couleur
US8268014B2 (en) 2009-02-25 2012-09-18 BASF SE Ludwigshafen Hair dyeing composition
JP2012518614A (ja) * 2009-02-25 2012-08-16 ビーエーエスエフ ソシエタス・ヨーロピア 毛髪染色用組成物
JP2015017109A (ja) * 2009-02-25 2015-01-29 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 毛髪染色用組成物
KR101322111B1 (ko) 2009-02-25 2013-10-29 바스프 에스이 모발 염색 조성물
CN102333515A (zh) * 2009-02-25 2012-01-25 巴斯夫欧洲公司 毛发染色组合物
US8257448B2 (en) 2009-02-25 2012-09-04 Basf Se Hair dyeing composition
JP2012518615A (ja) * 2009-02-25 2012-08-16 ビーエーエスエフ ソシエタス・ヨーロピア 毛髪染色用組成物
JP2015017108A (ja) * 2009-02-25 2015-01-29 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 毛髪染色用組成物
WO2010097339A3 (fr) * 2009-02-25 2010-11-11 Basf Se Composition de coloration capillaire
KR101364872B1 (ko) 2009-02-25 2014-02-21 바스프 에스이 모발 염색 조성물
CN102333516A (zh) * 2009-02-25 2012-01-25 巴斯夫欧洲公司 毛发染色组合物
EP3459520A1 (fr) * 2009-02-25 2019-03-27 Basf Se Composition de teinture capillaire
CN107753305A (zh) * 2009-02-25 2018-03-06 巴斯夫欧洲公司 毛发染色组合物
WO2010097338A3 (fr) * 2009-02-25 2010-11-11 Basf Se Composition de coloration capillaire
JP2017075157A (ja) * 2009-02-25 2017-04-20 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 毛髪染色用組成物
CN101983999A (zh) * 2010-07-30 2011-03-09 江苏亚邦染料股份有限公司 一种复配型直接印花分散蓝染料
EP2468248A1 (fr) * 2010-12-27 2012-06-27 KPSS-Kao Professional Salon Services GmbH Utilisation de colorants pour colorer des fibres en kératine et compositions comportant les colorants
WO2012089645A3 (fr) * 2010-12-27 2012-11-22 Kao Germany Gmbh Utilisation de colorants pour la coloration de fibres kératiniques et compositions comprenant les colorants
US8579993B2 (en) 2010-12-27 2013-11-12 Kao Germany Gmbh Use of dyestuffs for dyeing keratin fibers and compositions comprising the dyestuffs
US8444714B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-Hexy1/Hepty1-4,5-diaminopyrazole and a benzene-1,3-diol and derivatives thereof
US8460397B2 (en) 2011-02-22 2013-06-11 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a pyridine and derivatives thereof
US8444713B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a naphthalen-1-ol and derivatives thereof
US8444712B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a benzo[1,3]dioxol-5-ylamine and derivatives thereof
US8444711B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a benzene-1,3-diamine and derivatives thereof
US8444709B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a 2-aminophenol and derivatives thereof
US8444710B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a m-aminophenol and derivatives thereof
EP2793817B1 (fr) 2011-12-23 2020-09-23 Kao Germany GmbH Composition décolorante et colorante pour les cheveux
CN103525124A (zh) * 2013-10-23 2014-01-22 江苏德旺化工工业有限公司 一种分散黑染料
WO2018180515A1 (fr) * 2017-03-29 2018-10-04 株式会社マンダム Composition de coloration capillaire
JPWO2018180515A1 (ja) * 2017-03-29 2019-11-07 株式会社マンダム 染毛料組成物

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