Cationic oxidation bases, their use of dyeing keratin...

Details Cationic oxidation bases, their use of dyeing keratin... Cationic oxidation bases, their use of dyeing keratin...

2001-08-30

2003-12-09

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

C008S406000, C008S409000, C008S411000, C008S412000, C008S423000, C008S572000, C008S573000, C548S371400, C548S371700, C548S372500

Reexamination Certificate

active

06660046

ABSTRACT:

The invention relates to novel pyrazole derivatives containing at least one cationic group Z, Z being chosen from quaternized aliphatic chains, aliphatic chains containing at least one quaternized saturated ring and aliphatic chains containing at least one quaternized unsaturated ring, to their use as oxidation base for the oxidation dyeing of keratin fibres, to dye compositions containing them and to oxidation dyeing processes using them.
It is known practice to dye keratin fibres, and in particular human hair, with dye compositions containing oxidation dye precursors, in particular ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds such as diaminopyrazole derivatives, which are generally referred to as oxidation bases. The oxidation dye precursors, or oxidation bases, are colourless or weakly coloured compounds which, when combined with oxidizing products, can give rise to coloured compounds and dyes by a process of oxidative condensation.
It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or coloration modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds.
The variety of molecules used as oxidation bases and couplers makes it possible to obtain a wide range of colours.
The so-called “permanent” coloration obtained by means of these oxidation dyes must moreover satisfy a certain number of requirements. Thus, it must have no toxicological drawbacks and it must allow shades of the desired strength to be obtained and have good resistance to external agents (light, bad weather, washing, permanent-waving, perspiration and friction).
The dyes must also allow white hairs to be covered, and, lastly, they must be as unselective as possible, i.e. they must allow the smallest possible differences in coloration to be produced over the entire length of the same keratin fibre, which may indeed be differently sensitized (i.e. damaged) between its tip and its root.
Now, the Applicant has just discovered, entirely surprisingly and unexpectedly, that novel pyrazole derivatives of formula (I) defined below, containing at least one cationic group Z, Z being chosen from quaternized aliphatic chains, aliphatic chains containing at least one quaternized saturated ring and aliphatic chains containing at least one quaternized unsaturated ring, are not only suitable for use as oxidation base, but also allow dye compositions to be obtained which lead to strong colorations, in a wide range of colours, and which have excellent properties of resistance to the various treatments to which keratin fibres may be subjected.
These discoveries form the basis of the present invention.
A first subject of the invention is thus novel compounds of formula (I) below, the addition salts thereof with an acid or with a base, and the possible tautomeric forms thereof:
in which:
R
1
represents a hydrogen atom; a group Z as defined below; a C
1
-C
6
alkyl radical; a C
1
-C
6
trifluoroalkyl radical; a C
1
-C
6
monohydroxyalkyl radical; a C
2
-C
6
polyhydroxyalkyl radical; an aryl(C
1
-C
6
)alkyl radical in which the aryl radical may be in particular a phenyl radical or a 5- or 6-membered aromatic heterocycle such as, for example, a pyridyl ring, an imidazolyl ring, a furyl ring or an oxazolyl ring; a (C
1
-C
6
)alkoxy(C
1
-C
6
)alkyl radical; a (C
1
-C
6
)alkylthio(C
1
-C
6
)alkyl radical; an amino(C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyl radical; an N—Z-amino(C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyl radical; an N—(C
1
-C
6
)alkylamino(C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyl radical; an N,N-di(C
1
-C
6
)alkylamino(C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyl radical; a C
1
-C
6
aminosulphonylalkyl radical; a C
1
-C
6
N—Z-aminosulphonylalkyl radical; an N—(C
1
-C
6
)alkylaminosulphonyl(C
1
-C
6
)alkyl radical; an N,N-di(C
1
-C
6
)alkylaminosulphonyl(C
1
-C
6
)alkyl radical;
R
2
and R
3
, which may be identical or different, represent a group —NHR
4
; a hydroxyl radical; a halogen atom; a nitro radical; a cyano radical; a carboxyl radical; a C
1
-C
6
alkylcarboxyl radical; a carboxyaryl radical; a carbamyl radical; an N—(C
1
-C
6
)alkylcarbamyl radical; an N,N-di(C
1
-C
6
)alkylcarbamyl radical; an N-arylcarbamyl radical; a C
1
-C
6
alkoxy radical; an aryloxy radical; a C
1
-C
6
thioalkyl radical; a thioaryl radical or one of the meanings given above for R
1
; it being understood that at least one of the radicals R
2
and R
3
represents a group —NHR
4
or a hydroxyl radical;
R
4
represents a hydrogen atom; a group Z as defined below; a C
1
-C
6
alkyl radical; a C
1
-C
6
monohydroxyalkyl radical; a C
2
-C
6
polyhydroxyalkyl radical; a (C
1
-C
6
)alkoxy(C
1
-C
6
)alkyl radical; an aryl radical; a benzyl radical; a cyano(C
1
-C
6
)alkyl radical; a carbamyl(C
1
-C
6
)alkyl radical; an N—(C
1
-C
6
)alkylcarbamyl(C
1
-C
6
)alkyl radical; an N,N-di(C
1
-C
6
)alkylcarbamyl(C
1
-C
6
)alkyl radical; a thiocarbamyl(C
1
-C
6
)alkyl radical; a C
1
-C
6
trifluoroalkyl radical; a C
1
-C
6
sulphoalkyl radical; a (C
1
-C
6
)alkylcarboxy(C
1
-C
6
)alkyl radical; a (C
1
-C
6
)alkylsulphinyl(C
1
-C
6
)alkyl radical; a C
1
-C
6
aminosulphonylalkyl radical; a C
1
-C
6
N—Z-aminosulphonylalkyl radical; an N—(C
1
-C
6
)alkylaminosulphonyl(C
1
-C
6
)alkyl radical; an N,N-di(C
1
-C
6
)alkylaminosulphonyl(C
1
-C
6
)alkyl radical; a C
1
-C
6
aminoalkyl radical; a C
1
-C
6
aminoalkyl radical in which the amine is substituted with one or two radicals, which may be identical or different, chosen from C
1
-C
6
alkyl, C
1
-C
6
monohydroxyalkyl, C
2
-C
6
polyhydroxyalkyl, (C
1
-C
6
)alkylcarbonyl, C
1
-C
6
alkylsulphonyl, formyl and trifluoro(C
1
-C
6
)alkylcarbonyl radicals or with a group Z; the amine of the C
1
-C
6
aminoalkyl radical may also be substituted with two radicals forming, together with the nitrogen atom of the said amine, a saturated or unsaturated 5- or 6-membered ring which may contain one or more hetero atoms chosen from nitrogen, oxygen and sulphur, such as, for example, a piperidine, morpholine, imidazole or oxazole ring;
Z is chosen from the unsaturated cationic groups of formulae (II) and (III) below, and the saturated cationic groups of formula (IV) below:
 in which:
D is a linker arm which represents a linear or branched alkyl chain preferably containing from 1 to 14 carbon atoms, which can be interrupted by one or more hetero atoms such as oxygen, sulphur or nitrogen atoms, and which can be substituted with one or more hydroxyl or C
1
-C
6
alkoxy radicals, and which can bear one or more ketone functions;
the ring members E, G, J, L and M, which may be identical or different, represent a carbon, oxygen, sulphur or nitrogen atom;
n is an integer between 0 and 4 inclusive;
m is an integer between 0 and 5 inclusive;
the radicals R, which may be identical or different, represent a second group Z, which is identical to or different from the first group Z, a halogen atom, a hydroxyl radical, a C
1
-C
6
alkyl radical, a C
1
-C
6
monohydroxyalkyl radical, a C
2
-C
6
polyhydroxyalkyl radical, a nitro radical, a cyano radical, a cyano(C
1
-C
6
)alkyl radical, a C
1
-C
6
alkoxy radical, a tri(C
1
-C
6
)alkylsilane(C
1
-C
6
)alkyl radical, an amido radical, an aldehydo radical, a carboxyl radical, a (C
1
-C
6
)alkylcarbonyl radical, a thio radical, a C
1
-C
6
thioalkyl radical, a C
1
-C
6
alkylthio radical, an amino radical, an amino radical protected with a (C
1
-C
6
)alkylcarbonyl or C
1
-C
6
alkylsulphonyl radical; a group NHR″ or NR″R′″ in which R″ and R′″, which may be identical or different, represent a C
1
-C
6
alkyl radical, a C
1
-C
6
monohydroxyalkyl radical or a C
2
-C
6
polyhydroxyalkyl radical;
R
5
represents a C
1
-C
6
alkyl radical, a C
1
-C
6
monohydroxyalkyl radical, a C
2
-C
6
polyhydroxyalkyl radical, a cyano(C
1
-C
6
)alkyl radical, a tri(C
1
-C
6
)alkylsilane(C
1
-C
6
)alkyl radical, a (C
1
-C
6
)alkoxy(C
1
-C
6
)alkyl radical, a carbamyl(C
1
-C
6
)alk

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