WO2006131217A1 - Colorant oxydatif contenant des carbonates et/ou des analogues de carbonates et utilisation - Google Patents

Colorant oxydatif contenant des carbonates et/ou des analogues de carbonates et utilisation Download PDF

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Publication number
WO2006131217A1
WO2006131217A1 PCT/EP2006/005029 EP2006005029W WO2006131217A1 WO 2006131217 A1 WO2006131217 A1 WO 2006131217A1 EP 2006005029 W EP2006005029 W EP 2006005029W WO 2006131217 A1 WO2006131217 A1 WO 2006131217A1
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amino
acid
preferred
carbonate
hair
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PCT/EP2006/005029
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German (de)
English (en)
Inventor
Horst Höffkes
Britta Bossmann
Sabine Kainz
Christa Rohland
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Henkel Kommanditgesellschaft Auf Aktien
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Priority to AU2006254789A priority Critical patent/AU2006254789A1/en
Priority to EP06753892A priority patent/EP1893297A1/fr
Publication of WO2006131217A1 publication Critical patent/WO2006131217A1/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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • 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 agent for dyeing and / or whitening keratin-containing fibers, in particular human hair based on oxidation dye precursors, which has advantages over conventional hair dyes.
  • Coupler and developer components are also referred to as oxidation dye precursors.
  • the developer components are usually primary aromatic amines with a further, located in the para or ortho position free or substituted hydroxy or amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone 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-dichloro-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-methylamino pyridine and 3,5-diamino-2,6-dimethoxypyridine
  • dyeing or tinting agents which contain so-called direct drawers as a coloring component. These are dye molecules that grow directly on the hair and do not require an oxidative process to form the color. 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 nuance shift or even a visible "discoloration" occurs much more quickly.
  • Another undesirable effect that can occur with the application of colorations is the staining of areas of skin near the hair to be dyed.
  • the scalp which is covered by the hair, but also other areas such as forehead, ears and neck, come in the home application of colorations with the application mixture in contact and can be stained with.
  • the agents disclosed therein contain at least one developer and at least one coupler substance and at least one more precisely defined metal salt and at least one ammonium compound selected from the group consisting of ammonium chloride, Ammonium sulfate, ammonium carbonate, ammonium bicarbonate and ammonium carbamate, contains, and has, after mixing with an oxidizing agent, in the ready-mixed a pH between 8 and 11 on.
  • the present invention is in a first embodiment, an oxidation dye for dyeing keratin fibers, in particular human hair, containing at least one coupler component and at least one developer component in an aqueous carrier, characterized in that it comprises at least one carbonate and / or a carbonate precursor in quantities from 0.1 to 2.5 wt .-%, each based on the colorant.
  • the agents according to the invention contain at least one carbonate and / or one carbonate precursor.
  • Carbonates in the context of the present application are compounds which contain the carbonate group -O-C (O) -O- or " O-C (O) -O " or a carbonate-analogous group with elements of main group IV of the Periodic Table (in particular -0-Si (O) -O- or "0-Si (O) - O ') which 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 precursors in the context of the present application are substances which 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 hydrogencarbonate, potassium carbonate, potassium bicarbonate, ammonium carbonate or ammonium bicarbonate and mixtures thereof can be used as carbonates in the context of the present invention.
  • the use of these "inorganic carbonates” is preferred according to the invention.
  • organic carbonates In addition to the "inorganic carbonates” or in their place “organic carbonates” can be used.
  • 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.
  • carbonates according to the invention 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.
  • CVC ⁇ -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, iso-butyl, 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 ' 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 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.
  • R or R ' is a C 1-6 -alkyl group.
  • CrC ⁇ -alkyl groups according to the invention are the groups methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl and hexyl.
  • 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 1 R ' , 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 in question.
  • Further preferred radicals R, R ' , R “ and R '” are phenyl and benzyl radicals and further substituted representatives. Particularly preferred 'is R and R is a C 1- 6 alkyl group.
  • Examples of the inventive 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 radicals R, R ' , R " and R "' in formula (III) are each independently selected from methyl, ethyl, n-propyl, iso-propyl, n Butyl, iso-butyl, te / f-butyl and hydroxymethyl and hydroxyethyl radicals.
  • 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 derivatives of this basic structure, ie 1,3-dioxolan-2-ones substituted in the 4- or 4- and 5-position. There are no limits to the structural diversity, so that mono-, di-, tri- and tetrasubstituted 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-dioxolane-2-ones
  • R is a substituted or unsubstituted alkyl, alkenyl or alkylaryl radical.
  • Preferred radicals R are methyl, ethyl, n-propyl, iso-propyl and hydroxymethyl and hydroxyethyl radicals.
  • agents according to the invention are therefore characterized in that they contain at least one monosubstituted in the 4-position 1, 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 0 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 0 C, the boiling point at 242 0 C.
  • propylene carbonate is industrially by reaction of propylene oxide and CO 2 at 20O 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. Glycerine carbonate is a clear, easily agitated liquid with a density of 1.398, preferably 3 , which boils at 125-13O 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.
  • Further preferred radicals R are phenyl and benzyl radicals and further substituted representatives.
  • R is particularly preferably a C 1-6 -alkyl group.
  • CrC ⁇ -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, tert-butyl as well as hydroxymethyl and hydroxyethyl radicals.
  • the acidic H atom of the carbonic acid monoester or monoamide can also be present in neutralized form, ie according to the invention it is also possible to use salts of carbonic acid monoesters or Be used carbonic monoamides.
  • 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.
  • the carbonate or carbonate precursor used may also be a compound which contains, instead of carbon, another element of main group IV of the periodic table.
  • 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 independently of one another represent a hydrogen atom, a saturated or unsaturated, straight-chain, branched or cyclic, substituted or unsubstituted hydrocarbon radical or 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 the 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 a substituted or unsubstituted SiIyI or alumino group or a substituted or unsubstituted aryl group or a substitute
  • 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, tert-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)
  • R 3 containing, in which the 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 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 a substituted or unsubstituted SiIyI or alumino group or a substituted or unsubstit
  • 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, tert-butyl, 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 .-%, particularly preferably from 2 to 9 wt .-% and in particular from 3 to 7 wt .-%, each based on the total agent.
  • the direct dyes mentioned are preferably used in specific amounts.
  • agents according to the invention are preferred, the substantive dye (s) from the list mentioned above in amounts of from 0.01 to 10% by weight, preferably from 0.05 to 8% by weight, particularly preferably from 0.1 to 5 wt.% And in particular from 0.5 to 3.5 wt.%, Each based on the total agent included.
  • compositions of the invention contain the carbonate (s) in amounts of 0.1 to 2.5 wt .-%, each based on the total agent. Preference is given to amounts of from 0.5 to 2.4 wt .-%, particularly preferably from 1, 0 to 2.3 wt .-% and in particular from 1, 5 to 2.0 wt .-%, each based on the total Medium.
  • ammonium carbonate and / or ammonium bicarbonate in amounts of from 0.4 to 2.4% by weight, particularly preferably from 0.75 to 2.2% by weight and in particular from 1.0 to 2.0% by weight. %, in each case based on the total agent, is particularly preferred according to the invention.
  • the agents according to the invention additionally contain at least one coupler component and at least one developer component in an aqueous carrier.
  • the present invention is not subject to any restrictions.
  • the agents according to the invention can be used as dye precursors
  • 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-amino pyrazole 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 represents a hydrogen atom, a C 1 - to C 4 alkyl, C 1 - to C 4 - monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a (C 1 - to C 4 J-AIkOXy- ( C 1 to C 4 ) alkyl, a 4'-aminophenyl or C 1 to C 4 alkyl substituted with a nitrogen-containing group, a phenyl or a 4'-aminophenyl;
  • G 2 is a hydrogen atom a C 1 - to C 4 alkyl, C 1 - to C 4 - monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a (C 1 - to C 4 J-AIkOXy- (C 1 - to C 4 ) -alkyl radical or a C 1 - to C 4 -alkyl radical which is substituted by a nitrogen-containing group;
  • G 3 represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -monohydroxyalkyl radical, a C 2 - to C 4 Polyhydroxyalkyl, C 1 to C 4 hydroxyalkoxy, C 1 to C 4 acetylaminoalkoxy, C 1 to C 4 mesylaminoalkoxy or C 1 to C 4 carbamoylaminoalkoxy;
  • a halogen atom such as a chlorine, bromine, iodine or fluorine atom
  • a C 1 - to C 4 -alkyl radical such as a chlorine, bromine, iodine or fluorine atom
  • a C 1 - to C 4 -alkyl radical such as a chlorine, bromine, iodine or fluorine atom
  • 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.
  • 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 butyl. Ethyl and methyl are preferred alkyl radicals.
  • C 1 -C 4 -alkoxy radicals preferred according to the invention are, for example, a methoxy or an ethoxy group.
  • a C 1 - to C 4 -hydroxyalkyl group a hydroxymethyl, a 2-hydroxyethyl, a 3-hydroxypropyl or a 4-hydroxybutyl group may be mentioned.
  • 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 especially the amino groups, C 1 - to C 4 monoalkylamino, C 1 - to C 4 dialkylamino, C 1 - to C 4 -Trialkylammonium phenomenon, C 1 - to C 4 - Monohydroxyalkylamino phenomenon, 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 particular 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 -ReSt which is optionally substituted by a C 1 - to C 4 -alkyl radical, by a C 1 - to C 4 -hydroxyalkyl radical and / or is substituted by a bridge Y or which may be part of a bridging ring system
  • 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, of one or more nitrogen-containing groups and / or one or more heteroatoms such as oxygen, sulfur or nitrogen atoms can be interrupted or terminated and may be substituted by one or more hydroxyl or C 1 - to C 8 -alkoxy radicals, or a direct bond
  • 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, of one or more nitrogen-containing groups and / or
  • G 5 and G 6 are each independently a hydrogen or halogen atom, a C 1 - to C 4 alkyl radical, a Ci to C 4 monohydroxyalkyl radical, a C 2 - to C 4 - polyhydroxyalkyl 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 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 the formula (E2) contain only one bridging Y per molecule and the compounds of the 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 - (.beta.-hydroxyethyl) -N, N'-bis (4-aminophenyl) -tetramethylenediamine, N, N'-bis (4-methyl-aminophenyl) -tetramethylenediamine, N.N'-diethyl-N.N ' -bis - ⁇ '- amino-S'-methylphenyO-ethylenediamine, bis (2-hydroxy-5-a
  • 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-tetraoxadecan or one of its physiologically acceptable salts.
  • 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 1 to C 4 ) alkyl, C 1 to C 4 aminoalkyl, hydroxy (C 1 to C 4 ) alkylamino, C 1 to C 4 hydroxyalkoxy, C 1 to (! C 4 to C) C 4 hydroxyalkyl aminoalkyl group or a (di-C 1 - to C ⁇ AlkylaminoHd- to C 4) alkyl, and
  • G 14 represents a hydrogen or halogen atom, a C 1 - to C 4 alkyl, 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, C 2 - to C 4 -polyhydroxyalkyl, phenyl or benzyl, and
  • G 16 is hydrogen or a halogen atom.
  • 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- (2-hydroxyethoxy) -phenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-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- (diethyl-aminomethyl) -phenol and their physiologically
  • Very particularly preferred compounds of the formula (E3) are p-aminophenol, 4-amino-3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) -phenol and A-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-methoxypyridine and 3,4-diamino-pyridine.
  • Preferred pyrimidine derivatives are in particular 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2-dimethylamino-4,5,6- triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triaminopyrimidine.
  • Preferred pyrazole derivatives are in particular 4,5-diamino-1-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.
  • 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 the pyrazolo [1,5-a] pyrimidine of the following formula (E4) and their tautomeric forms, if a tautomeric equilibrium exists: in which:
  • 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 - Polyhydroxyalkylrest a (C 1 - to C 4 J-AIkOXy- (C 1 - to C 4 ) -alkyl radical, a C 1 - to C 4 - aminoalkyl, which may be protected by an acetyl-ureide or a sulfonyl radical can, a (C 1 - to to C 4 ) -alkyl radical, a di-I (C 1 - to C 4 ⁇ aIkVl] - (C 1 - to C 4 ) aminoalkyl radical, wherein the dialkyl radicals optionally form a carbon cycle or a heterocycle having 5 or 6 chain members , a C 1 - to C
  • Group OH occupy the positions (2,3); (5,6); (6,7); (3,5) or (3,7);
  • 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, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-nyl 3-methyl-pyrazolone-5,2,4-dichloro-3-aminophenol, I .S-bis - ⁇ '' - diaminophenoxyJ-propane, 2- Chloro-resorcinol, 4-chloro-resorcinol, 2-chloro-6-methyl-3-aminophenol, 2-amino-3-hydroxypyridine, 2-methylresorcinol, 5-methylres
  • Preferred coupler components according to the invention are m-aminophenol and its derivatives, such as, for example, 5-amino-2-methylphenol, N-
  • Resorcinol monomethyl 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
  • Naphthalene derivatives such as 1-naphthol, 2-methyl-1-naphthol, 2-hydroxymethyl-1-naphthol, 2-hydroxyethyl-1-naphthol, 1, 5-dihydroxynaphthalene, 1, 6-dihydroxynaphthalene, 1, 7
  • Morpholine derivatives such as 6-hydroxybenzomorpholine and 6-aminobenzomorpholine,
  • Indole derivatives such as 4-hydroxyindole, 6-hydroxyindole and 7-hydroxyindole,
  • Pyrimidine derivatives such as 4,6-diaminopyrimidine, 4-amino-2,6-dihydroxypyrimidine,
  • Methylenedioxybenzene derivatives such as 1-hydroxy-3,4-methylenedioxybenzene, 1-
  • 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-methylresorcinol, 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 (Nat-1),
  • R 1 is hydrogen, a C 1 -C 4 -alkyl group or a C 1 -C 4 -hydroxyalkyl group
  • R 2 is hydrogen or a -COOH group, where the -COOH group may also be in the form of a salt with a physiologically compatible cation
  • R 3 is hydrogen or a C 1 -C 4 -alkyl group
  • R 4 is hydrogen, a (VC t -alkyl group or a group -CO-R 6 , in which R 6 is a dC 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.
  • indoline Particularly preferred derivatives of indoline are 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline,
  • Particularly noteworthy within this group are 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 or a dC ⁇ 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 (VC ⁇ alkyl group
  • R 4 is hydrogen, a (-VC-alkyl group or a group -CO-R 6 , in which R 6 is
  • 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. As the hydrochlorides, the sulfates and Hydrobromide used.
  • the indole or indoline derivatives are contained therein usually in amounts of 0.05-10 wt .-%, preferably 0.2-5 wt .-%.
  • the indoline or Indolderivat in hair dyes in combination with at least one amino acid or a Use 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 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 moreover comprise substantive dyes.
  • Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Preferred substantive dyes are those under 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 1, Disperse Orange 3, Acid Orange 7, HC Red 1, HC Red 3, HC Red 10, HC Red
  • 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, CI -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 are characterized in that they comprise at least one direct-puller 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,ticianry and cosmetics, 4th edition,ticianry and cosmetics, 4th edition, psychologistliche Verlagsgesellschaft 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 as solids or liquids in pure Form are available.
  • 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 natural fat and oil based products. Even with alkoxylated products, mixtures of different degrees of alkoxylation are usually present.
  • purity in this context refers rather to the fact that the chosen substances should preferably be free from solvents, stabilizers 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 Ci ⁇ .i ⁇ -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) glycerol diisostearate (commercial product: Lameform ® TGI (Henkel)) and poly (2) glycerinpolyhydroxystearat (commercial product: De hymuls ® PGPH (Henkel)). Sorbitan fatty acid esters and alkoxylated sorbitan fatty acid esters such as sorbitan monolaurate and sorbitan monolaurate + 20 ethylene oxide (EO).
  • poly (3) glycerol diisostearate commercial product: Lameform ® TGI (Henkel)
  • poly (2) glycerinpolyhydroxystearat commercial product: De hymuls ® PGPH (Henkel)
  • Sorbitan fatty acid esters and alkoxylated sorbitan fatty acid esters such as sorbitan monolaurate and sorbitan monolaurate + 20 ethylene oxide (EO).
  • 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) 6 -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.
  • Suitable nonionic surfactants are in particular C 8 -C 22 -alkyl mono- and oligoglycosides and their ethoxylated analogs.
  • the nonethoxylated compounds have been found to be particularly suitable.
  • 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 Distearoylethylhydroxyethylammoniummethosulfat 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 usually preferred to start from the production of these substances from native plant or animal raw materials, so as to obtain substance mixtures with different, depending on the particular raw material alkyl chain lengths.
  • compositions according to the invention may contain 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 from 0.5 to 10, preferably from 1 to 5,% by weight, based on the total composition of the composition ,
  • the agents according to the invention may contain further active ingredients, auxiliaries and additives such as, for example, nonionic polymers such as vinylpyrrolidone / vinylacrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinylacetate copolymers and polysiloxanes, cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyldiallylammonium chloride polymers , Acrylamide-dimethyldiallyl-ammonium chloride copolymers, diethyl sulfate-quaternized dimethylamino-ethylmethacrylate-vinylpyrrolidone copolymers, vinylpyrrolidone-imidazolinium-methochloride copolymers and quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers, for example acrylamidopropyltrimethylammonium chloride / acryl
  • methylcellulose, hydroxyalkylcellulose 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,
  • Structural agents 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
  • Solvents and mediators such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol, fiber-structure-improving agents, especially mono-, di- and oligosaccharides such as glucose, galactose, fructose, fructose and lactose, quaternized amines such as methyl-1-alkylamidoethyl -2-alkylimidazoIinium methosulfate
  • Anti-dandruff agents such as Piroctone Olamine, Zinc Omadine and Climbazole,
  • Light stabilizers in particular derivatized benzophenones, cinnamic acid derivatives and
  • Active ingredients such as allantoin, pyrrolidonecarboxylic acids and their salts, and bisabolol,
  • Vitamins, provitamins and vitamin precursors in particular those of groups A, B 3 , B 5 , B 6 ,
  • 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, Quendel, Yarrow, Thyme, Melissa, Hauhechel, 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,
  • Complexing agents such as EDTA, NTA, ⁇ -alaninediacetic acid and phosphonic acids, swelling and penetrating agents 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, pigments,
  • Stabilizers for hydrogen peroxide and other oxidizing agents blowing agents such as propane-butane mixtures, N 2 O 1 dimethyl ether, CO 2 and air, antioxidants
  • 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 for the purpose of hair coloring such carriers 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 are to be understood as meaning aqueous solutions containing from 3 to 70% by weight of a C 1 -C 4 -alkoxyethane, in particular ethanol or isopropanol.
  • the compositions according to the invention may additionally contain further organic solvents, for example 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 non-aqueous 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 - 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
  • 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.
  • Zn 2+ is particularly suitable here.
  • 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 are e.g. Peroxidases that can significantly increase the effect of small amounts of hydrogen peroxide. Furthermore, such enzymes are 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.
  • Particularly suitable catalysts for the oxidation of the dye precursors are the so-called 2-electron oxidoreductases in combination with the specific substrates, e.g. Pyranose oxidase and e.g. D-glucose or galactose,
  • 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 a further exposure time of 10 to 20 minutes, the product is then rinsed and dried. if desired nachshampooniert.
  • 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.
  • Another object of the present invention is the use of carbonates and / or carbonate precursors in oxidation colorants for dyeing keratin fibers, in particular human hair.
  • a preferred use according to the invention is the use of carbonates and / or carbonate precursors in oxidation colorants for dyeing keratin fibers, in particular human hair
  • agents according to the invention lead by the carbonate (precursor) addition to a better coverage of graying hair.
  • the compositions according to the invention can also be formulated as pure starting colorants, which are applied only to the regrowth of hair. There they lead to improved coverage of the approach. In addition, the unwanted staining of the skin, especially the scalp, is reduced.
  • Another object of the present invention is therefore the use of carbonates and / or carbonate precursors in oxidation colorants for dyeing keratin fibers, in particular human hair
  • the advantages according to the invention are especially evident when the oxidation dye has a certain pH.
  • all uses according to the invention are preferred in which the oxidation dye used has a pH of from 7.8 to 9.0, preferably from 7.9 to 8.7 and in particular from 8.0 to 8.5.
  • mutatis mutandis applies to the means of the invention.
  • the formulations E1, V1, E2, V2 were each in the weight ratio 1: 1 with a developer dispersion of o.g. Mixed composition and used for coloring keratin fibers of several subjects.
  • compositions E according to the invention were distinguished from the respective comparative examples V in the judgment of the test persons by a reduced odor nuisance during dyeing and an improved skin compatibility of the oxidation colorants. In addition, scalp staining was reduced.
  • compositions of the present invention When dyeing on subjects with gray hair, improved coverage of graying hair has been noted for the compositions of the present invention. Also in the hairline staining in other subjects, the agent E according to the invention over the comparison means V were consistently rated as better at covering the hairline.

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Abstract

L'invention concerne des colorants oxydatifs destinés à colorer des fibres kératiniques, notamment des cheveux humains, contenant au moins un composant de couplage et au moins un composant de développement dans un support aqueux, et au moins un carbonate et/ou un précurseur de carbonate dans des quantités de 0,1 à 2,5 % en poids respectivement par rapport au colorant. Les colorants oxydatifs selon l'invention permettent de réduire le dégagement d'odeurs lors de la coloration de fibres kératiniques et/ou d'augmenter la compatibilité dermatologique et/ou d'améliorer la couverture de la racine des cheveux et/ou d'améliorer la couverture de cheveux gris et/ou de réduire la coloration du cuir chevelu lors de la coloration de fibres kératiniques.
PCT/EP2006/005029 2005-06-09 2006-05-26 Colorant oxydatif contenant des carbonates et/ou des analogues de carbonates et utilisation WO2006131217A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2006254789A AU2006254789A1 (en) 2005-06-09 2006-05-26 Oxidation colorants containing carbonates and/or carbonate analogues and use thereof
EP06753892A EP1893297A1 (fr) 2005-06-09 2006-05-26 Colorant oxydatif contenant des carbonates et/ou des analogues de carbonates et utilisation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005026810.2 2005-06-09
DE200510026810 DE102005026810A1 (de) 2005-06-09 2005-06-09 Oxidationsfärbemittel mit Carbonaten und/oder Carbonatanaloga und deren Verwendung

Publications (1)

Publication Number Publication Date
WO2006131217A1 true WO2006131217A1 (fr) 2006-12-14

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/005029 WO2006131217A1 (fr) 2005-06-09 2006-05-26 Colorant oxydatif contenant des carbonates et/ou des analogues de carbonates et utilisation

Country Status (5)

Country Link
EP (1) EP1893297A1 (fr)
AU (1) AU2006254789A1 (fr)
DE (1) DE102005026810A1 (fr)
RU (1) RU2007148736A (fr)
WO (1) WO2006131217A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
WO2001028508A1 (fr) * 1999-10-20 2001-04-26 The Procter & Gamble Company Compositions pour colorants capillaires et procedes
EP1106166A2 (fr) * 1999-12-02 2001-06-13 Kao Corporation Compositions de teinture pour les cheveux
US20040019980A1 (en) * 2002-08-02 2004-02-05 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. One step hair coloring compositions using salts
US20040237218A1 (en) * 2003-06-02 2004-12-02 Marsh Jennifer Mary Hair colouring compositions

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
WO2001028508A1 (fr) * 1999-10-20 2001-04-26 The Procter & Gamble Company Compositions pour colorants capillaires et procedes
EP1106166A2 (fr) * 1999-12-02 2001-06-13 Kao Corporation Compositions de teinture pour les cheveux
US20040019980A1 (en) * 2002-08-02 2004-02-05 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. One step hair coloring compositions using salts
US20040237218A1 (en) * 2003-06-02 2004-12-02 Marsh Jennifer Mary Hair colouring compositions

Also Published As

Publication number Publication date
EP1893297A1 (fr) 2008-03-05
RU2007148736A (ru) 2009-07-20
AU2006254789A1 (en) 2006-12-14
DE102005026810A1 (de) 2006-12-14

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