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

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

1999-06-07

2003-10-28

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S409000, C008S410000, C008S416000, C008S423000, C008S426000, C008S513000, C008S655000, C564S290000, C564S282000, C564S287000, C548S314400, C548S335500, C548S346100, C548S300100, C548S356100, C548S375100

Reexamination Certificate

active

06638321

ABSTRACT:

The invention relates to novel monobenzene oxidation bases containing at least one cationic group Z, Z being chosen from aliphatic chains containing at least one quaternized unsaturated ring, to their use 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.
It has already been proposed, in particular in U.S. Pat. No. 5,139,532, to use certain cationic para-phenylenediamine derivatives, i.e. more precisely, para-phenylenediamines in which one of the amino groups is monosubstituted with a quaternized aliphatic chain, for the oxidation dyeing of keratin fibres in strong shades which are redder than those usually obtained using standard para-phenylenediamines, i.e. compounds containing no cationic groups. However, the use of the para-phenylenediamines described in that prior patent does not make it possible to obtain a wide range of colours and, furthermore, the colorations obtained are not always entirely satisfactory from the point of view of their resistance with respect to the various forms of attack to which the hair may be subjected (action of light, perspiration, shampoo, etc.).
Now, the Applicant has just discovered, entirely surprisingly and unexpectedly, that certain novel monobenzene oxidation bases of formula (I) defined below, containing at least one cationic group Z, Z being chosen from aliphatic chains containing 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 colours, and which have excellent properties of resistance to the various treatments to which keratin fibres may be subjected. Lastly, these compositions prove to be readily synthesizable.
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:
R
1
, R
2
and R
3
, which may be identical or different, represent a hydrogen atom; a halogen atom; a group Z; 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
C
6
)alkylcarbonyl(C
1
-C
6
)alkyl radical; an N—(C
1
-C
1
)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; an (C
1
-C
6
)alkylcarboxyl radical; a C
1
-C
6
alkylsulphonyl radical; an aminosulphonyl radical; an N—Z-amino-sulphonyl 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-amino-sulphonylalkyl 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
--
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
-
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
2
-C
6
trifluoroalkyl radical; a cyano radical; a group OR
6
or SR
6
; 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
16
)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
)alkylamino-sulphonyl, thiocarbamyl or formyl radical, or with a group Z; or 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, 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 with a group Z;
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)alkylaminosulphonyl(C
1
-C
6
)alkyl radical; an N,N-di(C
11
-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
1
)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 the group Z;
A represents a group —NR
4
R
5
or a hydroxyl radical;
R
4
and R
5
, 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
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
trifluoroal

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