Cationic monobenzenic dyes, their use for the...

Details Cationic monobenzenic dyes, their use for the... Cationic monobenzenic dyes, their use for the...

2000-01-18

2002-05-07

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S405000, C008S406000, C008S408000, C008S409000, C008S410000, C008S412000, C540S001000, C544S003000, C546S001000, C548S125000, C549S013000

Reexamination Certificate

active

06383230

ABSTRACT:

The invention relates to novel monobenzenic dyes comprising at least one cationic group Z, Z 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 oxidation-dye precursors for the oxidation-dyeing of keratin fibers, to dye compositions containing them and to oxidation-dyeing processes using them.
It is a known practice to dye keratin fibers, in particular human hair, with dye compositions comprising oxidation-dye precursors, in particular para-phenylenediamines, ortho-aminophenols 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 colorless 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 such as, for example, indole couplers.
The variety of molecules used as oxidation bases and couplers makes it possible to obtain a wide range of colors. The so-called “permanent” coloration obtained by means of these oxidation dyes must, moreover, satisfy a certain number of requirements. Specifically, the oxidation dyes must have no toxicological drawbacks, 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. 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 fiber, which may indeed be differently sensitized (i.e., damaged) between its tip and its root.
The inventors have discovered, entirely surprisingly and unexpectedly, that novel cationic monobenzenic dyes of formula (I) defined below, comprising at least one cationic group Z, Z 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 oxidation-dye precursors, but also allow dye compositions to be obtained which lead to strong colorations, in a wide range of shades, and which have excellent properties of resistance to the various treatments to which keratin fibers 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, and the acid addition salts thereof:
in which:
A
1
, A
2
and A
3
, which may be identical or different, are chosen from a group —NR
7
R
8
and a hydroxyl radical; one and only one of the groups A
1
, A
2
and A
3
can also represent a group R
3
as defined below;
R
1
, R
2
and R
3
, which may be identical or different, are chosen from a hydrogen atom; a halogen atom; a group Z as defined below; 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
; an amino group protected by 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, or with the group Z defined below in which a linker arm D comprises a ketone function directly attached to the nitrogen atom of the amino group; a
(C
1
-C
6
)aminoalkyl radical in which the alkyl is unsubstituted or substituted with one or more hydroxyl radicals; a (C
1
-C
6
)aminoalkyl radical in which the alkyl is unsubstituted or substituted with one or more hydroxyl radicals and in which the amine is substituted with one or two radicals, which may be identical or different, chosen from alkyl, (C
1
-C
6
)monohydroxyalkyl, (C
2
-C
6
)polyhydroxyalkyl, (C
1
-C
6
)alkylcarbonyl, carbamyl, N-(C
1
-C
6
)alkylcarbamyl, N,N-di(C
1
-C
6
)alkylcarbamyl, (C
1
-C
6
)alkylsulphonyl, formyl, trifluoro(C
1
-C
6
)alkylcarbonyl, (C
1
-C
6
)alkylcarboxyl and thiocarbamyl radicals, or from a group Z as defined below, or which may form, together with the nitrogen atom to which they are attached, a carbonaceous 5- or 6-membered ring or which contains one or more hetero atoms;
R
6
is chosen from a (C
1
-C
6
)alkyl radical; a (C
1
-C
6
)monohydroxyalkyl radical; a
(C
2
-C
6
)polyhydroxyalkyl radical; a group Z as defined below; 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
)alkyl carbamyl(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
) alkylamino-sulphonyl(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 in which the alkyl is unsubstituted or substituted with one or more hydroxyl radicals; a (C
1
-C
6
)aminoalkyl radical in which the alkyl is unsubstituted or substituted with one or more hydroxyl radicals and 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, or from a group Z as defined below; or which may form, together with the nitrogen atom to which they are attached, a carbonaceous 5- or 6-membered ring or which contains one or more hetero atoms;
R
4
, R
5
, R
7
and R
8
, which may be identical or different, are c

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