Cationic compounds, their use as coupling agents for...

Details Cationic compounds, their use as coupling agents for... Cationic compounds, their use as coupling agents for...

2000-11-13

2002-09-17

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S405000, C008S406000, C008S407000, C008S408000, C008S409000, C008S416000, C008S421000, C008S423000

Reexamination Certificate

active

06451068

ABSTRACT:

The invention relates to novel dibenzenic compounds comprising at least one cationic group Z, Z being chosen from quaternized aliphatic chains, aliphatic chains comprising at least one quaternized saturated ring and aliphatic chains comprising at least one quaternized unsaturated ring, to their use as couplers 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 orthophenylenediamines or para-phenylenediamines, orthoaminophenols 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.
It has already been proposed, in particular in patent application FR-A-2 520 358, to use certain cationic derivatives of meta-phenylenediamines, i.e. more specifically, certain meta-phenylenediamines monosubstituted with a quaternized aliphatic chain, for the oxidation dyeing of keratin fibres in intense shades. However, the use of the meta-phenylenediamines described in that prior patent application does not make it possible to obtain a wide variety of colours and, furthermore, the colorations obtained are not always entirely satisfactory as regards their resistance with respect to the various attacking factors to which the hair may be subjected (the action of light, perspiration, shampooing, etc.).
The Applicant has now discovered, entirely surprisingly and unexpectedly, that dibenzenic compounds of formula (I) defined below comprising at least one cationic group Z, Z being chosen from quaternized aliphatic chains, aliphatic chains comprising at least one quaternized saturated ring, and aliphatic chains comprising at least one quaternized unsaturated ring, are not only suitable for use as a coupler for oxidation dyeing, but also make it possible to obtain dye compositions which give intense colorations, in a very wide range of shades, and which have excellent properties of resistance to the various treatments to which the keratin fibres may be subjected. Finally, these compounds are found to be easy to synthesize.
These discoveries form the basis of the present invention.
A first subject of the invention is thus novel compounds of formula (I) below, and the addition salts thereof with an acid:
in which:
B is a linker arm which represents an alkyl chain preferably containing from 1 to 14 carbon atoms, which is linear or branched and which can be interrupted by one or more hetero atoms such as oxygen, sulphur or nitrogen atoms, and which is optionally substituted with one or more hydroxyl or C
1
-C
6
alkoxy radicals;
R
1
, R
2
, R
3
, R′
1
, R′
2
and R′
3
, which may be identical or different, represent a hydrogen atom; a halogen atom; a group Z; a group —CO—Z; a group —CO—OZ; a (C
1
-C
6
)alkylcarbonyl radical; an amino(C
1
-C
6
)alkylcarbonyl radical; an N—Z-amino(C
1
-C
6
)alkylcarbonyl radical; an N—(C
1
-C
6
)alkylamino(C
1
-C
6
)alkylcarbonyl radical; an N,N-di(C
1
-C
6
)alkylamino(C
1
-C
6
)alkylcarbonyl 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 carboxyl radical; a (C
1
-C
6
)alkylcarboxyl radical; a C
1
-C
6
alkylsulphonyl radical; an aminosulphonyl radical; an N—Z-aminosulphonyl radical; a C
1
-C
6
N-alkylaminosulphonyl radical; an N,N-di(C
1
-C
6
)alkylaminosulphonyl 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 carbamyl radical; an N—(C
1
-C
6
)alkylcarbamyl radical; an N,N-di(C
1
-C
6
)alkylcarbamyl 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 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; a C
1
-C
6
trifluoroalkyl radical; a cyano radical; a group OR
6
or SR
6
; or an amino group protected with a (C
1
-C
6
)alkylcarbonyl, (C
1
-C
6
)alkylcarboxyl, trifluoro(C
1
-C
6
)alkylcarbonyl, amino(C
1
-C
6
)alkylcarbonyl, N—Z-amino(C
1
-C
6
)alkylcarbonyl, N—(C
1
-C
6
)alkylamino(C
1
-C
6
)alkylcarbonyl, N,N-di(C
1
-C
6
)alkylamino(C
1
-C
6
)alkylcarbonyl, (C
1
-C
6
)alkylcarboxyl, carbamyl, N—(C
1
-C
6
)alkylcarbamyl, N,N-di(C
1
-C
6
)alkylcarbamyl, C
1
-C
6
alkylsulphonyl, aminosulphonyl, N—Z-aminosulphonyl, C
1
-C
6
N-alkylaminosulphonyl, N,N-di(C
1
-C
6
)alkylaminosulphonyl, thiocarbamyl or formyl radical, a group —CO—Z or a group —CO—OZ;
R
6
denotes a C
1
-C
6
alkyl radical; a C
1
-C
6
monohydroxyalkyl radical; a C
2
-C
6
polyhydroxyalkyl radical; a group Z; a (C
1
-C
6
)alkoxy(C
1
-C
6
)alkyl radical; an aryl radical; a benzyl radical; a carboxy(C
1
-C
6
)alkyl radical; a (C
1
-C
6
)alkylcarboxy-(C
1
-C
6
)alkyl 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 C
1
-C
6
trifluoroalkyl 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
)alkylsulphinyl(C
1
-C
6
)alkyl radical; a (C
1
-C
6
)alkylsulphonyl(C
1
-C
6
)alkyl radical; a (C
1
-C
6
)alkylcarbonyl(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 identical or different radicals chosen from C
1
-C
6
alkyl, C
1
-C
6
monohydroxyalkyl, C
2
-C
6
polyhydroxyalkyl, (C
1
-C
6
)alkylcarbonyl, formyl, trifluoro-(C
1
-C
6
)alkylcarbonyl, (C
1
-C
6
)alkylcarboxyl, carbamyl, N—(C
1
-C
6
)alkylcarbamyl, N,N-di-(C
1
-C
6
)alkylcarbamyl, thiocarbamyl and C
1
-C
6
alkylsulphonyl radicals, and from the groups Z, —CO—Z and —CO—OZ;
A
1
represents a group —NR
4
R
5
or a hydroxyl radical;
A′
1
represents a group —NR′
4
R′
5
or a hydroxyl radical;
A
2
represents a group —NR
7
R
8
or a hydroxyl radical;
A′
2
represents a group —NR′
7
R′
8
or a hydroxyl radical;
R
4
, R
5
, R
7
, R
8
, R′
4
, R′
5
, R′
7
and R′
8
, which may be identical or different, represent a hydrogen atom; a group Z; a C
1
-C
6
alkyl radical; a C
1
-C
6
monohydroxyalky

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