CA2754962A1 - A 5-hydroxy-quinoline derivative for oxidative dyeing of keratin fibers - Google Patents

Abstract

An oxidative dyeing composition comprising a 5-hydroxy-quinoline derivative of formula (I).
(see formula I)

Description

FIBERS

FIELD OF THE INVENTION
The present invention relates to a composition for the oxidative dyeing of keratin fibers, in particular human keratin fibers, comprising (A) a 5-hydroxy-quinoline derivative as defined in formula (I) hereafter, a physiologically compatible water-soluble salt thereof, or mixtures thereof and (B) an oxidizing agent.
BACKGROUND OF THE INVENTION
The oxidative dyeing process using one or more oxidative hair coloring precursors in combination with one or more oxidizing agent is the most extensively used method to color hair.
Commonly, the oxidative dyeing colorants are marketed as a two components kit.
One component comprises the dye precursors and ammonia and the other is a stabilized solution of hydrogen peroxide. The two components are mixed immediately prior to use and applied to the hair. The dye precursors and peroxide diffuse into the hair where they undergo rapid reaction, which leads to the formation of higher molecular weight coloured materials.
The dyes precursors are divided into two classes: primary intermediates and couplers. The specific combination of these two classes of precursors, their amount and their variety in the hair dyeing composition lead to the achievement of a unique color.
Therefore, it is important to develop and search continuously for new dye precursor candidates in order to achieve new shades or better color results of the already existing shades.
The aim of the invention is to develop a new hair dye composition providing a strong hair color intensity together with color-rich shades, good resistance against shampooing and rubbing.
Indeed, it has surprisingly been found that the oxidative hair dyeing composition comprising at least a 5-hydroxy-quinoline derivative of general formula (I) provides strong hair color intensity together with excellent properties of resistance to the various treatments which keratinous fibers may undergo.
SUMMARY OF THE INVENTION

According to a first aspect, the present invention relates to a composition for the oxidative dyeing of keratin fibers, in particular human keratin fibers comprising (A) a 5-hydroxy-quinoline derivative of the general formula (I) or a physiologically compatible water-soluble salt thereof, or mixtures thereof and (B) an oxidizing agent.

(I) wherein R1 to R7 are as defined hereafter.
According to a second aspect, the present invention relates to a method of dyeing hair comprising the steps of:
(i) providing a tint component comprising (A) a 5-hydroxy-quinoline derivative of formula (I), a physiologically compatible water-soluble salt thereof, or mixtures thereof;
(ii) providing a developer component comprising (B) an oxidizing agent;
(iii) mixing the tint component and the developer component to obtain a composition for the oxidative dyeing of keratin fibers; and (iv) applying said composition for the oxidative dyeing of keratin fibers onto the hair.
According to a third aspect, the present invention relates to a kit comprising: (i) a tint component comprising (A) a 5-hydroxy-quinoline derivative as defined in formula (I), a physiologically compatible water-soluble salt thereof, or mixtures thereof;
(ii) a developer component comprising an (B) oxidizing agent.
DETAILED DESCRIPTION OF THE INVENTION

As used herein, the term "composition for the oxidative dyeing of keratin fibers" means a ready-to-use composition in a suitable carrier medium for dyeing keratin fibers, in particular human hair, comprising oxidative dye precursors (primary intermediates and couplers) and an oxidizing agent. These compositions can typically be the result of a mixture of two compositions namely a tint component comprising the dye precursors and usually an alkalizing agent such as ammonia and a developer component comprising the oxidizing agent.
As used herein, the term "keratin" refers to a scleroprotein found in epidermal tissues and modified into hard structures such as horns, hair, and nails. As used herein, the term "hair" refers to keratinous fibers on a living, e.g. a person, or non-living body, e.g. in a wig, hairpiece, or other aggregation of non-living keratinous fibers. Mammalian, preferably human, hair is preferred.
Notably, hair, wool, fur, and other keratinous fibers are suitable substrates for coloring by the compounds and compositions described herein.

As used herein, the term "dye precursor" refers to compounds that may be used in the composition to act as primary intermediates, couplers, or both, in order to provide the desired color to ketatinous fibers.
It is to be understood that within the scope of this invention, numerous potentially and actually tautomeric compounds are involved. It is to be understood that when this development refers to a particular structure, all of the reasonable additional tautomeric structures are included.
In the art, tautomeric structures are frequently represented by one single structure and the invention follows this general practice.
The present invention relates to a 5-hydroxy-quinoline derivative of general formula (I), a physiologically compatible water-soluble salt thereof, or mixtures thereof:

Ri R5 (I) wherein R1, R2, R3, R4, R5 and R6 are substituents selected independently of each other from the group consisting of:
(a) C-linked substituents selected from the group consisting of-(i) mono- or poly- substituted or unsubstituted, straight or branched, saturated or mono- or poly- unsaturated, alkyl or heteroalkyl systems, (ii) mono- or poly- substituted or unsubstituted, straight or branched, saturated or mono- or poly- unsaturated, aryl systems, and (iii) mono- or poly- substituted or unsubstituted, straight or branched, saturated or mono- or poly- unsaturated, heteroaryl systems, and wherein said systems of (i), (ii) and (iii) comprise from about I to 10 carbon atoms and from about 0 to 5 heteroatoms selected from the group consisting of 0, F, N, P
and Si;
(b) S-linked substituents selected from the group consisting of SA', SO2A', SO3A', SSA', SOA', SO2NA'A2, SNA'A2, and SONA'A2;
(c) 0-linked substituents selected from the group consisting of OA', ONA'A2;
(d) N-linked substituents selected from the group consisting of NA'A2;
(NA'A2A3)+, NA' SA2, NO2; NA' A2;

(e) substituents selected from the group consisting of COOA', CONA', CONA'COA2, C(=NA')NA'A2, CN, and X;

(f) fluoroalkyl substituents selected from the group consisting of mono-, poly-, and per-fluoro alkyl systems comprising from I to 12 carbon atoms and from 0 to 4 heteroatoms; and (g) H;
wherein A', A2, and A3 are selected independently of each other from the group consisting of: H; mono- or poly- substituted or unsubstituted, straight or branched, saturated or mono-or poly- unsaturated, alkyl or heteroalkyl systems; mono- or poly-substituted or unsubstituted, straight or branched, mono-or poly- unsaturated, aryl or heteraryl systems; and substituted or unsubstituted, mono-, poly-, or per-fluoro alkyl systems, or At and A2 together with nitrogen atoms to which they are bound form a ring; wherein said systems comprise from 1 to 10 carbon atoms and from 0 to 5 heteroatoms selected from the group consisting of 0, S, N, P, and Si; and wherein X is a halogen selected from the group consisting of F, Cl, Br, and I; and wherein R7 is a substituent selected independently of each other from the group consisting of:
(h) C-linked substituents selected from the group consisting of:
(i) mono- or poly- substituted or unsubstituted, straight or branched, saturated or mono-or poly- unsaturated, alkyl or heteroalkyl systems, (ii) mono- or poly- substituted or unsubstituted, straight or branched, saturated or mono-or poly- unsaturated, aryl systems, and (iii) mono- or poly- substituted or unsubstituted, straight or branched, saturated or mono-or poly- unsaturated, heteroaryl systems, and wherein said systems of (i), (ii) and (iii) comprise from about 1 to 10 carbon atoms and from about 0 to 5 heteroatoms selected from the group consisting of 0, F, N, P
and Si;
(i) substituents selected from the group consisting of COOA', CONA', CONA'COA2, C(=NA')NA'A2, CN; and (j) H.
Suitable salts of formula (I) are also included such as chlorides, bromides, sulfates, such as hemisulfates, tartrates, lactates, malates and acetates.
In a preferred embodiment, R1, R2, R3, R4, R5 and R6 are selected independently of each other from the group consisting of a H; a halogen atom; an amino substituent, a hydroxyl substituent; a cyano substituent; a C1-C4 alkyl substituent; a trifluoromethyl substituent; an alkylamino substituent; a hydroxyalkylamino substituent; an acetylamido substituent; a carboxyl substituent or its esters; an alkoxy substituent; an alkoxyalkyl substituent;
a carbamoyl substituent; an alkylcarbamoyl substituent; a hydroxyalkylcarbamoyl substituent; an amido substituent; an alkylarnido substituent; an alkylcarbonyl substituent; an alkoxycarbonyl substituent; an aryloxy substituent; an acyloxy substituent; an alkylthio substituent; an arylthio substituent; a heteroarylthio substituent; a heteroaryloxy substituent; a thiocyano substituent; a 3-, 4-, 5-, 6-, or 7- membered heterocycle having at least one nitrogen, oxygen or sulfur atom; an 5 aryl substituent which is optionally substituted; a sulfonyl substituent; a sulfinyl substituent; a phosphonyl substituent; a sulfamoyl substituent; a siloxy substituent; an acyloxy substituent; a carbamoyloxy substituent; a sulphonamide substituent; an imide substituent; a ureido substituent;
a sulfamoylamino substituent; an alkoxycarbonylamino substituent; an aryloxycarbonylamino substituent; an aryloxycarbonyl substituent; and a benzenesulfonamido substituent.
In a preferred embodiment, R7 is selected independently of each other from the group consisting of a H; a Cl-C4 alkyl substituent; an alkylamino substituent; a hydroxyalkylamino substituent; an acetylamido substituent; a carboxyl substituent or its esters;
an alkoxy substituent;
an alkoxyalkyl substituent; a carbamoyl substituent; an alkylcarbamoyl substituent; a hydroxyalkylcarbamoyl substituent; an alkylamido substituent; an alkylcarbonyl substituent; an alkoxycarbonyl substituent.

In a preferred embodiment the 5-hydroxy-quinoline derivative (I) is a compound with formula (1.1):
OH

N
H
(I.1) In order to achieve the desired hair color, the 5-hydroxy-quinoline derivative of formula (I) can be combined with one or more primary intermediate.
The primary intermediate may be a 4,5-diamino pyrazole derivative of the general formula (II) or a physiologically compatible water-soluble salt thereof:

N

(II) wherein R3 has the same definition given above for R1, R2, R3, R4, R5 and R6 and wherein R9, R10, R11, R12 and R13 have the same definition given above for R7 of the 5-hydroxy-quinoline derivative of formula (I).

Rg, R9, R10, R11, R12 and R13 are substituents selected independently of each other from the group consisting of hydrogen, C1-C6 alkyl, C2-C6 hydroxalkyl, C2-C4 alkoxy and mixtures thereof.

In a preferred embodiment the 4,5-diamino pyrazole derivative (II) is a compound of formula (II.1):

NT
N\ NH2 OH
(11.1) The primary intermediate may be a 1,4-diamino-benzene derivative of the general formula (III) or a physiologically compatible water-soluble salt thereof-(III) wherein R14, R15, R16 and R17 have the same definition given above for R1, R2, R3, R4, R5, and R6 of the 5-hydroxy-quinoline derivative of formula (I). Preferably R14, R15, R16 and R17 are selected independently of each other from the group consisting of hydrogen, halogen, hydroxyl, CI-C6 alkyl, C2-C6 hydroxalkyl, C2-C4 alkoxy and mixtures thereof.

The 1,4-diamino-benzene derivative (III) may be a compound of formula (111.1):

(III.1) The 1,4-dialnino-benzene derivative (III) may be a compound of formula (111.2):

(III.2) The 1,4-diamino-benzene derivative (III) may be a compound of formula (111.3):

OH

(111.3) The 1,4-diamino-benzene derivative (III) may be a compound of formula (111.4):

HO,-,~,~ N "-~OH
(111.4) The primary intermediate may be a 4-amino-phenol derivative of the general formula (IV) or a physiologically compatible water-soluble salt thereof:

Res R20 Rig R21 OH
(IV) wherein R18, R19, R20 and R21 have the same definition given above for R1, R2, R3, R4, R5 and R6 of the 5-hydroxy-quinoline derivative of formula (I). Preferably R18, R19, R20 and R21 are selected independently of each other from the group consisting of hydrogen, halogen, hydroxyl, C1-C6 alkyl, C2-C6 hydroxalkyl, C2-C4 alkoxy and mixtures thereof.
The 4-amino-phenol derivative (IV) may be a compound of formula (IV.1):

OH

(IV.!) The 4-amino-phenol derivative (IV) may be a compound of formula (IV.2):

OH

(IV.2) The primary intermediate may be 2,4,5,6-tetraaminopyrimidine or a physiologically compatible water-soluble salts thereof of formula (V):

NYN

(V) Oxidizing Agent The compositions of the invention comprise an oxidizing agent. Typical suitable oxidizing agents for the oxidative dyeing of keratin fibers may be selected from hydrogen peroxide, sodium periodate, urea peroxide, melamine peroxide, perborates, percarbonates, perphosphates, persilicates, persulfates, oxidizing enzymes such as uricases, oxidases, and peroxidases, and mixtures thereof. Hydrogen peroxide, perborates, or percarbonates may be preferred.
Another potential oxidizing agent for use herein is a source of peroxymonocarbonate ions. Preferably, such a source is formed in situ from a source of hydrogen peroxide and a hydrogen carbonate ion source. Such an oxidizing agent has been found to be particularly effective at a pH of up to and including 9.5, preferably from about 7.5 to about 9.5 more preferably about pH 9. Moreover, this system is also particularly effective in combination with a source of ammonia or ammonium ions.
Accordingly, any source of these peroxymonocarbonate ions may be utilized.
Suitable sources for use herein include sodium, potassium, guanidine, arginine, lithium, calcium, magnesium, barium or ammonium salts of carbonate, carbamate and hydrocarbonate ions and mixtures thereof. In particular, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, guanidine carbonate, guanidine hydrogen carbonate, lithium carbonate, calcium carbonate, magnesium carbonate, barium carbonate, ammonium carbonate, ammonium hydrogen carbonate and mixtures thereof may be preferred.
Percarbonate salts may also be utilized to provide both the source of carbonate ions and as an oxidizing agent.
Preferred sources of carbonate ions, carbamate and hydrocarbonate ions are sodium hydrogen carbonate, potassium hydrogen carbonate, ammonium carbonate, ammonium carbamate, and mixtures thereof.

The hair dyeing composition may usually comprise from about 1% to about 15%
by, typically from about 1.5% to about 10% by weight, and more typically from about 2% to about 8% by weight of the oxidizing agent relative to the total weight of the composition.

The oxidizing agent may be provided in a developer component which is mixed to a tint component to obtain the composition of the invention. The developer component may be based on any desired formulation chassis, including any commercial product, for example an oil-in-water emulsion. Typical developer components comprise about 6% or about 9% of the H202 relative to the total weight of the composition. A commercial example is the Welloxon Emulsion with respectively about. 6% and about 9% H202, marketed by Wella and comprising as INCI ingredients: Water, H202, Cetearyl Alcohol, Ceteareth-25, Salicylic Acid, Phosphoric Acid, Disodium Phosphate, Etidronic Acid.

The hair dyeing composition of the invention may be formed as thick liquid, cream, gel, emulsion, foam, aerosol mousse or as a solid form to which water is added to generate the oxidant and form a thickened vehicle suitable for hair coloring. They may comprise in addition to the ingredients indicated above further ingredients in order to further enhance the properties of the composition, including but not limited to: solvents; oxidative dyes, direct dyes; oxidizing agents; radical scavengers; thickeners and or rheology modifiers; chelants; pH
modifiers and buffering agents; carbonate ion sources; peroxymonocarbonate ion sources;
anionic, cationic, nonionic, amphoteric or zwitterionic surfactants, or mixtures thereof;
anionic, cationic, nonionic, amphoteric or zwitterionic polymers, or mixtures thereof; fragrances; enzymes;
dispersing agents; peroxide stabilizing agents; antioxidants; natural ingredients, e.g.
proteins and protein compounds, and plant extracts; conditioning agents including silicones and cationic polymers, ceramides, preserving agents; and opacifiers and pearling agents (such as titanium dioxide and mica). Some adjuvants referred to above, but not specifically described below, which are suitable are listed in the International Cosmetics Ingredient Dictionary and Handbook, (8th ed.; The Cosmetics, Toiletry, and Fragrance Association). Particularly, vol. 2, sections 3 (Chemical Classes) and 4 (Functions) are useful in identifying specific adjuvants to achieve a particular purpose or multipurpose. A few of these ingredients are discussed herein below, whose disclosure is of course non-exhaustive.
Alkalizing agent The composition for the oxidative dyeing of keratin fibers may further comprise, generally in the tint component, an alkalizing agent as known in the art. Any alkalizing agent known in the art may be used such as ammonia, alkanolamines for example monoethanolarnine, diethanolamine, triethanolamine, monopropanolamine, dipropanolamine, tripropanolamine, 2-amino-2-methyl-1,3-propanediol, 2-amino-2-methyl- l-propanol, and 2-amino-2-hydroxymethyl-1,3-propanediol, guanidium salts, alkali metal and ammonium hydroxides such as sodium hydroxide, alkali metal and ammonium carbonates, and mixtures thereof. Typical alkalizing agents are ammonia and/or monoethanolamine.
Typically, the compositions for the oxidative dyeing of keratin fibers comprise from about 0.1% to about 10%, preferably from about 0.5% to about 6%, more preferably from about 5 1% to about 4% by weight of the alkalizing agent relative to the total weight of the composition.
Primary intermediates In addition to the pyrazole compounds of the invention, the hair dyeing compositions of the invention may comprise further primary intermediates. Suitable primary intermediates for use in the compositions described herein include, but are not limited to: toluene-2,5-diamine, p-10 phenylenediamine, N-phenyl-p-phenylenediamine, N,N-bis(2-hydroxyethyl)-p-phenylenediamine, 2-hydroxyethyl-p-phenylenediamine, hydroxypropyl-bis-(N-hydroxyethyl-p-phenylenediamine), 2-methoxymethyl-p-phenylenediamine, 2-(I,2-dihydroxyethyl)-p-phenylenediamine, 2,2'-(2-(4-aminophenylamino)ethylazanediyl)diethanol, 2-(2,5-diamino-4-methoxyphenyl)propane-1,3-diol, 2-(7-amino-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethanol, 2-chloro-p-phenylenediamine, p-aminophenol, p-(methylamino)phenol, 4-amino-m-cresol, 2-methoxy-p-phenylenediamine, 2,2'-methylenebis-4-aminophenol, 2,4,5,6-tetraminopyrimidine, 2,5,6-triamino-4-pyrimidinol, I -hydroxyethyl-4,5-diaminopyrazole sulfate, 4,5-diamino-l-methylpyrazole, 4,5-diamino-l-ethylpyrazole, 4,5-diamino-l-isopropylpyrazole, 4,5-diamino-l-butylpyrazole, 4,5-diamino-l-pentylpyrazole, 4,5-diamino-l-benzylpyrazole, 2,3-diamino-6,7-dihydropyrazolo[1,2-a]pyrazol-1(5H)-one dimethosulfonate, and mixtures thereof.
Typically, the compositions for the oxidative dyeing of keratin fibers comprise from about 0.1% to about 10%, preferably from about 0.3% to about 6%, more preferably from about 0.5% to about 4% by weight of the primary intermediates relative to the total weight of the composition.
Couplers In addition to the pyrazole compounds of the invention, the hair dyeing compositions of the invention may comprise couplers to obtain various shades. Suitable couplers for use in the compositions described herein include, but are not limited to: resorcinol, 4-chlororesorcinol, 2-ch lororesorcinol, 2-methylresorcinol, 4,6-dichlorobenzene-1,3-diol, 2,4-dimethylbenzene-1,3-diol, m-aminophenol, 4-amino-2-hydroxytoluene, 2-methyl-5-hydroxyethylaminophenol, 3-am ino-2,6-dimethylphenol, 3-amino-2,4-dichlorophenol, 5-amino-6-chloro-o-cresol, 5-amino-4-chloro-o-cresol, 6-hydroxybenzomorpholine, 2-amino-5-phenylphenol, 2-amino-5-methylphenol, 2-amino-6-rnethylphenol, 2-amino-5-ethoxyphenol, 5-methyl-2-(methylamino)phenol, 2,4-diaminophenoxyethanol, 2-amino-4-hydroxyethylaminoanisole, 1,3-b1s-(2,4-diam1nophenoxy)-propane, 2,2'-(2-methyl-1,3-phenylene)bis(azanediyl)diethanol, benzene- 1,3 -diani in 2,2'-(4,6-diamino-1,3-phenylene)bis(oxy)diethanol, 3-(pyrrolidin-l-yl)aniline, 1-(3-(dimethylamino)phenyl)urea, 1-(3-aminophenyl)urea, 1-naphthol, 2-methyl-l-naphthol, 1,5-naphthalenediol, 2,7-naphthalenediol or 1-acetoxy-2-methylnaphthalene, 4-chloro-2-methylnaphthalen- l -ol, 4-methoxy-2-methylnaphthalen- I -ol, 2,6-dihydroxy-3,4-dimethylpyridine, 2,6-dimethoxy-3,5-pyridinediamine, 3-amino-2-methylamino-6-methoxypyridine, 2-amino-3-hydroxypyridine, 2,6-diaminopyridine, pyridine-2,6-diol, 5,6-dihydroxyindole, 6-hydroxyindole, 5,6-dihydroxyindoline, 3-methyl-l-phenyl-lH-pyrazol-5(4H)-one, 1,2,4-trihydroxybenzene, 2-(benzo[d][1,3]dioxol-5-ylamino)ethanol (also known as hydroxyethyl-3,4-methylenedioxyaniline), and mixtures thereof.
When the composition is obtained by mixing a tint component and a developer component, additional primary intermediates and couplers may be preferably incorporated in the tint component.
Typically, the compositions for the oxidative dyeing of keratin fibers comprise from about 0.1% to about 10%, preferably from about 0.3% to about 6%, more preferably from about 0.5% to about 4% by weight of the couplers relative to the total weight of the composition.
Direct Dyes The compositions of the present invention may also comprise compatible direct dyes, in an amount sufficient to provide additional coloring, particularly with regard to intensity.
Typically, such an amount will range from about 0.05% to about 4%, by weight of the direct dyes relative to the total weight of the composition. When the composition is obtained by mixing a tint component and a developer component, the direct dyes are usually incorporated in the tint component.

The following direct dyes are commonly used: Acid dyes such as Acid Yellow 1, Acid Orange 3, Acid Black 1, Acid Black 52, Acid Orange 7, Acid Red 33, Acid Yellow 23, Acid Blue 9, Acid Violet 43, HC Blue 16, Acid Blue 62, Acid Blue 25, Acid Red 4, Basic Dyes such as Basic Brown 17, Basic Red 118, Basic Orange 69, Basic Red 76, Basic Brown 16, Basic Yellow 57, Basic Violet 14, Basic Blue 7, Basic Blue 26, Basic Red 2, Basic Blue 99, Basic Yellow 29, Basic Red 51, Basic Orange 31, Basic Yellow 87, 4-(3-(4-amino-9,10-dioxo-9,10-dihydroanthracen-l-ylamino)propyl)-4-methylmorpholin-4-ium-methylsuIfate, (E)-1-(2-(4-(4,5-dimethylthiazol-2-yl)diazenyl)phenyl)(ethyl)amino)ethyl)-3-methyl-1 H-imidazol-3-ium chloride, (E)-4-(2-(4-(dimethylamino)phenyl)diazenyl)-1-methyl-1 H-imidazol-3-ium-3-yl)butane-l-sulfonate, (E)-4-(4-(2-methyl-2-phenylhydrazono)methyl)pyridinium-l-yl)butane-l-sulfonate, N,N-dimethyl-3-(4-(methylamino)-9,10-dioxo-4a,9,9a,10-tetrahydroanthracen-l-ylamino)-N-propylpropan-1-aminium bromide, Disperse Dyes such as Disperse Red 17, Disperse Violet 1, Disperse Red 15, Disperse Violet 1, Disperse Black 9, Disperse Blue 3, Disperse Blue 23, Disperse Blue 377, Nitro Dyes such as 1-(2-(4-nitrophenylamino)ethyl)urea, 2-(4-methyl-2-nitrophenylamino)ethanol, 4-nitrobenzene-1,2-diamine, 2-nitrobenzene-1,4-diamine, Picramic acid, HC Red No. 13, 2,2'-(2-nitro-1,4-phenylene)bis(azanediyl)diethanol, HC
Yellow No. 5, HC
Red No. 7, HC Blue No.2, HC Yellow No. 4, HC Yellow No. 2, HC Orange No. 1, HC
Red No.
1, 2-(4-amino-2-chloro-5-nitrophenylamino)ethanol, HC Red No. 3, 4-amino-3-nitrophenol, 4-(2-hydroxyethylamino)-3-nitrophenol, 2-amino-3-nitrophenol, 2-(3-(methylamino)-4-nitrophenoxy)ethanol, 3-(3-amino-4-nitrophenyl)propane-1,2-diol, HC Yellow No.
11, HC Violet No. 1, HC Orange No. 2, HC Orange No. 3, HC Yellow No. 9, HC Red No. 10, HC
Red No. 11, 2-(2-hydroxyethylamino)-4,6-dinitrophenol, HC Blue No. 12, HC Yellow No. 6, HC
Yellow No.
12, HC Blue No. 10, HC Yellow No. 7, HC Yellow No. 10, HC Blue No. 9, 2-chloro-(ethylamino)-4-nitrophenol, 6-nitropyridine-2,5-diamine, HC Violet No. 2, 2-amino-6-chloro-4-nitrophenol, 4-(3-hydroxypropylamino)-3-nitrophenol, HC Yellow No. 13, 6-nitro-1,2,3,4-tetrahydroquinoxaline, HC Red No. 14, HC Yellow No. 15, HC Yellow No. 14, N2-methyl-6-nitropyridine-2,5-diamine, N1-allyl-2-nitrobenzene-1,4-diamine, HC Red No. 8, HC Green No.1, HC Blue No. 14, and Natural dyes such as Annato, Anthocyanin, Beetroot, Carotene, Capsanthin, Lycopene, Chlorophyll, Henna, Indigo, Cochineal.

Thickeners The hair dyeing compositions of the present invention may comprise a thickener in an amount sufficient to provide the composition with a viscosity so that it can be readily applied to the hair without unduly dripping off the hair and causing mess. Typically, such an amount will be at least 0.05%, preferably at least 0.5%, more preferably at least 1%, by weight of thickener relative to the total weight of the composition. When the composition is obtained by mixing several components, the thickener may be present in any of the components.
Preferred for use herein are salt tolerant thickeners, including but not limited to: xanthan, guar, hydroxypropyl guar, scleroglucan, methyl cellulose, ethyl cellulose (available as AQUACOTE(TM)), hydroxyethyl cellulose (NATROSOL(TM)), carboxymethyl cellulose, hydroxypropyhnethyl cellulose, microcrystalline cellulose, hydroxybutylmethyl cellulose, hydroxypropyl cellulose (available as KLUCEL(TM)), hydroxyethyl ethyl cellulose, cetyl hydroxyethyl cellulose (available as NATROSOL(TM)) Plus 330), N-vinylpyrollidone (available as POVIDONE(TM)), Acrylates/Ceteth-20 Itaconate Copolymer (available as STRUCTURE(TM) 3001), hydroxypropyl starch phosphate (available as STRUCTURE(TM) ZEA), polyethoxylated urethanes or polycarbamyl polyglycol ester (e.g. PEG-150/Decyl/SMDI
copolymer (available as ACULYN(TM) 44), PEG-150/Stearyl/SMDI copolymer available as ACULYN(TM) 46), Acrylates/Beheneth-25 Methacrylate Copolymer (available as ACULYN(TM) 28), AcrylatesNinyl Neodecanoate Crosspolymer (available as ACULYN(TM) 38), Acrylates/Steareth-20 Methacrylate Crosspolymer (available as ACULYN(TM) 88), PEG-150 Distearate (available as ACULYN(TM) 60), trihydroxystearin (available as THIXCIN(TM)), acrylates copolymer (e.g. available as ACULYN(TM) 33) or hydrophobically modified acrylate copolymers (e.g. Acrylates/Steareth-20 Methacrylate Copolymer (available as ACULYN(TM) 22), non-ionic amphophilic polymers comprising at least one fatty chain and at least one hydrophilic unit selected from polyether urethanes comprising at least one fatty chain.
Also preferred for use herein are thickeners based on lamellar gel network systems, comprising at least one surfactant or amphophile having an HLB of 6 or less and a melting point of at least 30 C, preferably selected from fatty alcohols comprising from 14 to 30 carbon atoms, or oxyethylenated fatty alcohols comprising from 16 to 30 carbon atoms and 2 units or less of ethylene oxide, and further comprising at least one ionic or nonionic surfactant, preferably selected from:
anionic surfactants selected from C8-C30 alkyl sulfates, preferably C12-C18 alkyl sulfates, anionic surfactants according to the formula RõXmYM, wherein R is independently selected from alkyl, alkenyl or alkylaryl groups having from 8 to 30 carbon atoms, X is independently selected from polar groups comprising at least one carbon atom and at least one oxygen or nitrogen atom, Y is an anionic group selected from carboxylates, sulfates, sulfonates or phosphates, n and m are independently I or 2, and M is hydrogen or a salt forming cation and mixture thereof, most preferably selected from C8-C30 alkyl ether phosphates having from 1 to 20, preferably 2 to 10 ethylene oxide units (e.g. available as CRODAFOS(TM) CES);
non-ionic surfactant comprising one or more polyethyleneoxide chains, preferably each polyethyleneoxide chain having on average at least 50 ethylene oxide units and most preferably 100 to 200 ethylene oxide units (e.g. available as VOLPO(TM) S200), cationic surfactants selected from quaternary ammonium salts or amido-amines having at least one fatty chain, preferably comprising at least 16 carbon atoms and most preferably at least 20 carbon atoms, and mixture thereof.
Examples of such lamellar gel network systems are disclosed in EP1,832,273 and EP2,103,299.
The composition preferably comprises a mixture of cetearyl alcohol and dicetyl phosphate and ceteth-10 phosphate (e.g. available as CRODAFOS(TM) CES).

Chelants The compositions of the present invention may comprise chelants in an amount sufficient to reduce the amount of metals available to interact with formulation components, particularly oxidizing agents, more particularly peroxides and percarbonates. Typically, such an amount range from at least 0.15%, preferably at least 0.25% by weight of the chelants relative to the total weight of the composition. Suitable chelants for use herein include but are not limited to:
diethylenetriamine-N,N',N"-polyacids, diethylenetriaminepentaacetic acid (DTPA), diethylenetriaminepenta(methylene phosphonic acid) (DTPMP), diamine-N,N'-dipolyacids, monoamine monoamide-N,N'-dipolyacids, N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid, EDDS (ethylenediaminedisuccinic acid), carboxylic acids (preferably aminocarboxylic acids), phosphonic acids (preferably aminophosphonic acids) and polyphosphoric acids (in particular straight polyphosphoric acids), their salts and derivatives.
When the composition is obtained by mixing a tint component and a developer component, the chelants may be incorporated in the tint component or in the developer component or in both. A
chelant is usually present in developer components for stability reason.
pH Modifiers The compositions of the present invention may comprise in addition to the alkalizing agent discussed above a pH modifier and/or buffering agent in an amount that is sufficiently effective to adjust the pH of the composition to fall within a range from about 3 to about 13, preferably from about 8 to about 12, more preferably from about 9 to about 11.
Radical Scavengers According to the present invention, the compositions may comprise a radical scavenger.
As used herein the term radical scavenger refers to a species that can react with a radical, to convert the radical species by a series of fast reactions to an unreactive or less reactive species.
The radical scavenger is also preferably selected such that it is not an identical species as the alkalizing agent and is present in an amount sufficient to reduce the damage to the hair during the coloring /bleaching process. The compositions of the present invention comprise a radical scavenger from about 0.1 % to about 10%, preferably from about I % to about 7%
by weight of the radical scavenger relative to the total weight of the composition Suitable radical scavengers for use herein may be selected from the classes of alkanolamines, amino sugars, amino acids, esters of amino acids and mixtures thereof. Suitable 5 compounds include 3-substituted-pyrazol-5-ones, 3 -carboxy- I H-pyrazol-5 -one, 3-methyl-l-phenyl-pyrazol-5-one, 3-methyl-l-p-tolyl-pyrazol-5-one, 3-methyl-l-(4-sulfophenyl)-pyrazol-5-one, 3-methyl- l -(4-sulfoamidophenyl)-pyrazol-5-one, 3-methyl -l-(3-sulfophenyl)-pyrazol-5-one, 3-methyl-l-(3-sulfoam idophenyl)-pyrazol-5-one, 3-methyl-l-(2-chloro-5-sulfophenyl)-pyrazol-5-one, 3-methyl-1 -(2,5-dichloro-4-sulfophenyl)-pyrazol-5-one, 3-methyl-l-(4-chlorophenyl)-10 pyrazol-5-one, 3 -methyl- I -(4-carboxyphenyl)-pyrazol -5 -one, 3-carboxy-l-phenyl -pyrazol-5-one, 3-carboxy-l-(4-sulfophenyl)-pyrazol-5-one, 1, 3 -d iphenyl-pyrazol-5 -one, methyl pyrazol-5-one-3-carboxylate, 3-amino-l-propanol, 4-amino-l-butanol,5-amino-l-pentanol, 1-amino-2-propanol, 1-amino-2-butanol, 1-amino-2-pentanol, I-amino-3-pentanol, I-amino-4-pentanol, 3-amino-2-methylpropan-1-ol, 1-amino-2-methylpropan-2-ol, 3-aminopropane-1,2-diol, glucosamine, N-15 acetylglucosamine, glycine, arginine, lysine, proline, glutamine, histidine, sarcosine, serine, glutamic acid, tryptophan, or mixtures thereof, or the salts, such as the potassium, sodium, or ammonium salts thereof, or mixtures thereof. In some embodiments, the inventive compositions may comprise glycine, sarcosine, lysine, serine, 2-methoxyethylamine, glucosamine, glutamic acid, morpholine, piperidine, ethylamine, 3-amino-l-propanol, or mixtures thereof.
Method of hair dyeing In order to use the dyeing composition, the tint component and developer components are usually mixed immediately prior to use and a sufficient amount of the mixture is applied to the hair, according to the hair abundance, generally from about 60 to about 250 grams. Upon such preparation the composition is applied to the hair to be dyed and remains in contact with the hair for an amount of time effective to dye the hair. Typically, the hair dye composition is allowed to act on the hair from about 2 to about 60, preferably about 15 to about 45, more preferably about minutes, at a temperature ranging from 15 C to about 50 C. Thereafter, the hair is rinsed with water to remove the composition and dried. If necessary, the hair is washed with a shampoo and rinsed, e.g., with water or a weakly acidic solution, such as a citric acid or tartaric acid 30 solution, and dried. Optionally, a separate conditioning product may also be provided.
The method of dyeing hair with the composition may therefore comprise the steps of-(0 providing a tint component comprising (A) 5-hydroxy-quinoline derivative as defined in formula (I), a physiologically compatible water-soluble salt, or mixtures thereof, (ii) providing a developer component comprising an (B) oxidizing agent;
(iii) mixing the tint component and the developer component to obtain a composition for the oxidative dyeing of keratin fibers according to the composition of the invention;
(iv) applying said composition for the oxidative dyeing of keratin fibers onto the hair.
The method may further comprise waiting a period of time, typically between 2 minutes and 60 minutes, and then rinsing the composition from the hair.
The compositions can be applied on hair via applicator bottle or brush. It can be used on full head or partly on single strands (highlight application) as common highlight applicator foils, caps and special applicators can be used, but also freehand techniques such as balayage, with brush and/or combs can be possible. The composition can also be applied as a mousse via a manual spray, a pressurized container or an aerosol mousse.
The composition may be dispensed as a solid form to which water is added to generate the oxidant and form a thickened vehicle suitable for hair coloring.
The dye combination of the invention may also be used in three components system. See for example disclosed US2010/0223739A2 assigned to L'Oreal. Such a process and kit for lightening or dyeing keratin fibers may comprise the following composition applied to the hair fibers: an aqueous cosmetic composition (A) comprising at least one fatty substance and at least one surfactant; a cosmetic composition (B) comprising at least one alkaline agent and the oxidative dyes of the invention and if present direct dyes and other oxidative dyes, a cosmetic composition (C) comprising at least one oxidizing agent, wherein the amount of the at least one fatty substance in composition (A) is greater than 20% by weight relative to the total weight of composition (A).
Methods of making - Kit The composition, and its tint component and developer component, may be manufactured by conventional processes known in the art for manufacturing oxidative dyeing products, and ad-mixing the ingredients of each component composition in suitable vessels, followed by packaging in appropriate individual containers. The components may be for example packaged in plastic or aluminium bottles.
In particular, the present invention may be provided as a kit comprising different components to be mixed by the consumer or salon stylist to obtain a hair dyeing composition according to the invention. Such a kit may comprise:
(i) a tint component comprising (A) 5-hydroxy-quinoline derivative as defined in formula (1), a physiologically compatible water-soluble salt, or mixtures thereof;

(ii) a developer component comprising an (B) oxidizing agent.
The kit may be presented in a single package comprising separate containers for the tint component, the developer component, and optionally a conditioner, a color refresher or other hair treatment product, instructions for use, gloves. The instructions for use include the steps of the method described above and optionally provide visual cues or pictures for the desired steps of the method. Kits are usually sold in retail products with enough material in each component for preparing a hair dyeing composition for one use.
The composition may be dispensed as a foam using for example manually-actuable, non-aerosol dispenser such as a pump or squeeze foamers, aerosol mousse. See for example EP
613,728 B1, WO 97/013585 Al, EP 1,716,933A1, US 3,709,437, US 3,937,364, US
4,022,351, US 4,147,306, US 4,184,615, US 4,615,467 and FR 2,604,622. One particular example of a squeeze foamer useful herein is able to dispense from an upright or inverted position such as the one discussed in US 6,604,693 assigned to Taplast, and more specifically, at column 2, line 65, through column 4, line 67 of that patent.
The composition may be dispensed as a solid form to which water is added to generate the oxidant and form a thickened vehicle suitable for hair coloring.

EXAMPLES
The following are non-limiting examples of the compositions of the present invention.
The examples are given solely for the purpose of illustration and are not to be construed as limitations of the present invention, as many variations thereof are possible without departing from the spirit and scope of the invention, which would be recognized by one of ordinary skill in the art. In the examples, all concentrations are listed as weight percent, unless otherwise specified.
The 5-hydroxy-quinoline of formula (1.1) can be synthesized following the experimental protocol described by D. Roberts, J.A. Joule in Journal of Organic Chemistry, 62 (1997) pages 568-577.
Example 1: Synthesis of 5-hydroxy-1,2,3,4-tetrahydroquinoline of the formula (1.1) as shown in the following scheme.
OH OH
NiC12/NaBH4 &N) H
(1.1) Examples 2 to 9: flair dyes (1:1 combinations) 1.25 mmol 5-hydroxyquinoline of the formula (1.1) 1.25 mmol primary intermediate substance as in table I
10.0 g lauryl ether sulfate (28 percent aqueous solution) 9.0 g ammonia (22 percent aqueous solution) 7.8 g ethanol 0.3 g ascorbic acid 0.3 g ethylenediaminotetraacetic acid disodium salt hydrate ad 100.0 g water, dernineralized 10 g of the above dye solution were mixed directly prior to application with 10 g of a 6 percent hydrogen peroxide solution. The mixture was then applied to bleached hair. After a contact time of 30 minutes at 40 C, the hair was rinsed with water, washed with a standard commercial shampoo and dried. The resulting colorations are summarized in table 1.
Table 1:

Primary intermediate substance 1.4-diamino- 2,5-Diamino- 2,5-Diamino- 4,5-Diamino-l- 4-Amino-benzene toluene sulfate phenyl-ethanol (2'-hydroxy- phenol (IIL1) (IIL2) sulfate (111.3) ethyl)pyrazole (IV.1) sulfate (11.1) Coupler dark brown dark brown dark brown dark red Brown substance (Example 2) (Example 3) (Example 4) (Example 5) (Example 6) (I.1) Primary intermediate substance 4-Amino-3-methyl- N,N-Bis(2-hydroxyethyl)- 2,4,5,6-Tetraamino-phenol (IV.2) p-phenylenediamine pyrimidine sulfate (V) sulfate (111.4) Coupler Beige dark violet Beige substance (1.1) (Example 7) (Example 8) (Example 9) Example 10: 1 lair colorants (multi-combinations) 0.1 g hydroxy-1,2,3,4-tetrahydroquinoline derivative of the formula (1): 1.1 0.3 g primary intermediate substance (1,4-diaminobenzene) 0.05 g coupler substance (3-aminophenol) 0.20 g coupler substance (1,3-dihydroxybenzene) 10.0 g lauryl ether sulfate (28 percent aqueous solution) 9.0 g ammonia (22 percent aqueous solution) 7.8 g ethanol 0.3 g ascorbic acid 0.3 g ethylenediaminotetraacetic acid disodium salt hydrate ad 100.0 g water, demineralized Directly prior to application 30 g of the above coloring solution were mixed with 30 g of a 6 percent aqueous hydrogen peroxide solution. The mixture was then applied to bleached hair.
After a contact time of 30 minutes at 40 C, the hair was rinsed with water, washed with a standard commercial shampoo and dried. The coloring result is a blonde shade.
Except as otherwise noted, all amounts including part, percentages, and proportions are understood to be modified by the word "about", and amounts are not intended to indicate significant digits. Except as otherwise noted, the articles "a", "an", and "the" mean "one or more".
All percentages, parts and ratios are based upon the total weight of the compositions of the present invention, unless otherwise specified. All such weights as they pertain to listed ingredients are based on the active level and, therefore, do not include solvents or by-products that may be included in commercially available materials, unless otherwise specified. The term "weight percent" may be denoted as "wt. %" herein.
The dimensions and values disclosed herein are not to be understood as being strictly limited to the exact numerical values recited. Instead, unless otherwise specified, each such dimension is intended to mean both the recited value and a functionally equivalent range surrounding that value. For example, a dimension disclosed as "40 mm" is intended to mean "about 40 mm."

Every document cited herein, including any cross referenced or related patent or application is hereby incorporated herein by reference in its entirety unless expressly excluded or otherwise limited. The citation of any document is not an admission that it is prior art with respect to any invention disclosed or claimed herein or that it alone, or in any combination with any other reference or references, teaches, suggests or discloses any such invention. Further, to the extent that any meaning or definition of a term in this document conflicts with any meaning or definition of the same term in a document incorporated by reference, the meaning or definition assigned to that term in this document shall govern.

5 While particular embodiments of the present invention have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this invention.

Claims (18)

1. A composition for the oxidative dyeing of keratin fibers comprising - (A) a 5-hydroxy-quinoline derivative of the general formula (I) or a physiologically compatible water-soluble salt thereof, or mixtures thereof:

wherein R1, R2, R3, R4, R5, R6 are substituents selected independently of each other from the group consisting of:
(a) C-linked substituents selected from the group consisting of:
(1) mono- or poly- substituted or unsubstituted, straight or branched, saturated or mono-or poly- unsaturated, alkyl or heteroalkyl systems, (ii) mono- or poly- substituted or unsubstituted, straight or branched, saturated or mono-or poly- unsaturated, aryl systems, and (iii) mono- or poly- substituted or unsubstituted, straight or branched, saturated or mono-or poly- unsaturated, heteroaryl systems, and wherein said systems of (i), (ii) and (iii) comprise from about 1 to 10 carbon atoms and from about 0 to 5 heteroatoms selected from the group consisting of O, F, N, P
and Si;
(b) S-linked substituents selected from the group consisting of SA1, SO2A1, SO3A1, SSA1, SOA1, SO2NA1A2, SNA1A2, and SONA1A2;
(c) O-linked substituents selected from the group consisting of OA1, ONA1A2;
(d) N-linked substituents selected from the group consisting of NA1A2;
(NA1A2A3)+
NA1 SA2, NO2; NA1 A1 ;
(e) substituents selected from the group consisting of COOA1, CONA1, CONA1COA2, C(=NA1)NA1A2, CN, and X;
(f) fluoroalkyl substituents selected from the group consisting of mono-, poly-, and per-fluoro alkyl systems comprising from 1 to 12 carbon atoms and from 0 to 4 heteroatoms;
and (g) H; and wherein A1, A2, and A3 are selected independently of each other from the group consisting of: H; mono- or poly- substituted or unsubstituted, straight or branched, saturated or mono-or poly- unsaturated, alkyl or heteroalkyl systems; mono- or poly-substituted or unsubstituted, straight or branched, mono-or poly- unsaturated, aryl, or heterocyclic systems; and substituted or unsubstituted, mono-, poly-, or per-fluoro alkyl systems, or Al and A 2 together with nitrogen atoms to which they are bound form a ring;
wherein said systems comprise from 1 to 10 carbon atoms and from 0 to 5 heteroatoms selected from the group consisting of O, S, N, P, and Si; and wherein X is a halogen selected from the group consisting of F, Cl, Br, and 1; and wherein R7 is a substituent selected independently of each other from the group consisting of:
(h) C-linked substituents selected from the group consisting of:
(i) mono- or poly- substituted or unsubstituted, straight or branched, saturated or mono-or poly- unsaturated, alkyl or heteroalkyl systems, (ii) mono- or poly- substituted or unsubstituted, straight or branched, saturated or mono-or poly- unsaturated, aryl systems, and (iii) mono- or poly- substituted or unsubstituted, straight or branched, saturated or mono-or poly- unsaturated, heteroaryl systems, and wherein said systems of (i), (ii) and (iii) comprise from about 1 to 10 carbon atoms and from about 0 to 5 heteroatoms selected from the group consisting of O, F, N, P
and Si;
(i) substituents selected from the group consisting of COOA1, CONA1, CONA1COA2, C(=NA1)NA1A2, CN, and X; and (j) H; and - (B) an oxidizing agent.

2. A composition according to claim 1, wherein said R1, R2, R3, R4, R5 and R6 are substituents selected independently of each other from the group consisting of a hydrogen atom; a halogen atom; an amino substituent; a hydroxyl substituent; a cyano substituent; a C1-C4 alkyl substituent; a trifluoromethyl substituent; an alkylamino substituent; a hydroxyalkylamino substituent; an acetylamido substituent; a carboxyl substituent or its esters; an alkoxy substituent; an alkoxyalkyl substituent; a carbamoyl substituent; an alkylcarbamoyl substituent; a hydroxyalkylcarbainoyl substituent; an amido substituent;
an alkylamido substituent; an alkylcarbonyl substituent; an alkoxycarbonyl substituent; an aryloxy substituent; an acyloxy substituent; an alkylthio substituent; an arylthio substituent; a heteroarylthio substituent; a heteroaryloxy substituent; a thiocyano substituent; a 3-, 4-, 5-, 6-, or 7-membered heterocycle having at least one nitrogen, oxygen or sulfur atom; an aryl substituent which is optionally substituted; a sulfonyl substituent; a sulfinyl substituent; a phosphonyl substituent; a sulfamoyl substituent; a siloxy substituent; an acyloxy substituent; a carbamoyloxy substituent; a sulphonamide substituent; an imide substituent; a ureido substituent; a sulfamoylamino substituent; an alkoxycarbonylamino substituent; an aryloxycarbonylamino substituent; an aryloxycarbonyl substituent; and a benzenesulfonamido substituent.

3. A composition according to claim 1 or 2, wherein said composition further comprises a primary intermediate of formula (II):

4. wherein R8 has the same definition given above for R1, R2, R3, R4, R5 and R6 and wherein R9, R10, R11, R12 and R13 have the same definition given above for R7 of the 5-hydroxy-quinoline derivative of formula (I).

5. A composition according to any of the preceding claims, wherein said composition further comprises a primary intermediate of formula (II):

wherein -R8, R9, R10, R11, R12 and R13 are substituents selected independently of each other from the group consisting of hydrogen, C1-C6 alkyl, C2-C6 hydroxalkyl, C2-C4 alkoxy and mixtures thereof.

6. A composition according to any of the preceding claims, wherein said composition further comprises a primary intermediate of formula (11.1):

7. A composition according to any of the preceding claims, wherein said composition further comprises a primary intermediate of formula (III):

8. wherein R14, R15, R16 and R17 have the same definition given above for R1, R2, R3, R4, R5, and R6 of the 5-hydroxy-quinoline derivative of formula (I).

9. A composition to any of the preceding claims, wherein said composition further comprises a primary intermediate of formula (III):

wherein R14, R15, R16 and R17 are substituents selected independently of each other from the group consisting of hydrogen, halogen, hydroxyl, C1-C6 alkyl, C2-C6 hydroxalkyl, C2-C4 alkoxy and mixtures thereof.

10. A composition according to any of the preceding claims, further comprising fatty alcohols comprising from 14 to 30 carbon atoms, and/or oxyethylenated fatty alcohols comprising from 16 to 30 carbon atoms and 2 units or less of ethylene oxide.

11. A composition according to any of the preceding claims, further comprising at least one ionic or nonionic surfactant selected from:
- anionic surfactants selected from C8-C30 alkyl sulfates, preferably C12-C18 alkyl sulfates;
- anionic surfactants according to the formula R n X m YM, wherein R is independently selected from alkyl, alkenyl or alkylaryl groups having from 8 to 30 carbon atoms, X is independently selected from polar groups comprising at least one carbon atom and at least one oxygen or nitrogen atom, Y is an anionic group selected from carboxylates, sulfates, sulfonates or phosphates, n and m are independently 1 or 2, and M
is hydrogen or a salt forming cation and mixture thereof, most preferably selected from C8-C30 alkyl ether phosphates having from 1 to 20, preferably 2 to 10, ethylene oxide units;

non-ionic surfactant comprising one or more polyethyleneoxide chains, preferably each polyethyleneoxide chain having on average at least 50 ethylene oxide units and most preferably 100 to 200 ethylene oxide units;
cationic surfactants selected from quaternary ammonium salts or amido-amines having at least one fatty chain, preferably comprising at least 16 carbon atoms and most preferably at least 20 carbon atoms; and mixtures thereof.

12. A composition according to any of the preceding claims further comprising a mixture of cetearyl alcohol and dicetyl phosphate and ceteth- 10 phosphate.

13. A composition according to any of the preceding claims further comprising a chelant selected from the group consisting of: diethylenetriamine-N,N',N"-polyacids, diethylenetriaminepentaacetic acid (DTPA), diethylenetriaminepenta(methylene phosphonic acid) (DTPMP), diamine-N,N'-dipolyacids, monoamine monoamide-N,N'-dipolyacids, N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid, EDDS

(ethylenediaminedisuccinic acid), carboxylic acids (preferably aminocarboxylic acids), phosphonic acids (preferably aminophosphonic acids) and polyphosphoric acids (in particular straight polyphosphoric acids), their salts and derivatives.

14. A composition according to any of the preceding claims wherein said oxidizing agent is selected from the group consisting of hydrogen peroxide, sodium periodate, urea peroxide, melamine peroxide, perborates, percarbonates, perphosphates, persilicates, persulfates, oxidizing enzymes such as uricases, oxidases, and peroxidases, a source of peroxymonocarbonate ions and mixtures thereof.

15. A composition according to claim 14 wherein the source of peroxymonocarbonate ions selected from the group consisting of: sodium, potassium, guanidine, arginine, lithium, calcium, magnesium, barium or ammonium salts of carbonate, carbamate and hydrocarbonate ions and mixtures thereof.

16. A composition according to any of the preceding claims, wherein said composition is dispensed as a foam.

17. A method of dyeing hair comprising the steps of.

(i) providing a tint component comprising (A) a 5-hydroxy-quinoline derivative of formula (I) as defined in claim 1, a physiologically compatible water-soluble salt thereof or mixtures thereof;

(ii) providing a developer component comprising (B) an oxidizing agent;
(iii) mixing the tint component and the developer component to obtain a composition for the oxidative dyeing of keratin fibers; and (iv) applying said composition for the oxidative dyeing of keratin fibers onto the hair.

18. An oxidative hair dyeing kit comprising:

(i) a tint component comprising (A) 5-hydroxy-quinoline derivative as defined in formula (I) as defined in claim 1, a physiologically compatible water-soluble salt or mixtures thereof;

(ii) a developer component comprising (B) an oxidizing agent.