Cationic ortho-phenylenediamines, their use for the...

Details Cationic ortho-phenylenediamines, their use for the... Cationic ortho-phenylenediamines, their use for the...

1999-09-01

2002-01-22

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S408000, C008S409000, C008S416000, C008S423000, C008S426000, C008S655000, C564S282000, C548S300100, C548S335500, C548S346100, C546S329000

Reexamination Certificate

active

06340371

ABSTRACT:

The invention relates to monobenzenic ortho-phenylenediamines comprising at least one cationic group Z, to their use for the oxidation dyeing of keratin fibres, to dye compositions containing them, and to oxidation dyeing processes using them. Z is chosen from aliphatic chains containing at least one quaternized unsaturated ring.
It is known practice to dye keratin fibres, and in particular human hair, with dye compositions containing 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 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.
Oxidation dyes, by which so-called “permanent” coloration can be obtained, should have no toxicological drawbacks, should allow shades of the desired strength to be obtained, and should have good resistance to external agents (e.g., light, bad weather, washing, permanent-waving, perspiration and friction).
The dyes should also allow white hairs to be covered, and they should be as unselective as possible, i.e. they should 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.
The inventors have discovered, surprisingly and unexpectedly, that a novel family of monobenzenic ortho-phenylenediamines of formula (I), defined below, can be suitable for use as oxidation bases or as couplers or as self-oxidizing compounds for oxidation dyeing, and can also allow dye compositions to be obtained which can lead to strong colorations, in a wide range of shades, and which can have excellent properties of resistance to the various treatments to which keratin fibres may be subjected. These compositions can also be readily synthesized.
The monobenzenic ortho-phenylenediamines of formula (I) comprise at least one cationic group Z, wherein Z is chosen from aliphatic chains containing at least one quaternized unsaturated ring.
These discoveries form the basis of the present invention.
A subject of the invention is thus an ortho-phenylenediamine of formula (I) below, or an acid addition salt thereof:
in which:
R
1
, R
2
, and R
3
, which may be identical or different, are radicals chosen from a hydrogen atom; halogens; Z groups; (C
1
-C
6
)alkylcarbonyls; amino(C
1
-C
6
)alkylcarbonyls; N—Z-amino(C
1
-C
6
)alkylcarbonyls; N—(C
1
-C
6
)alkylamino(C
1
-C
6
)alkylcarbonyls; N,N-di(C
1
-C
6
)alkylamino(C
1
-C
6
)alkylcarbonyls; amino(C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyls; N—Z-amino(C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyls; N—(C
1
-C
6
)alkylamino(C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyls; N,N-di(C
1
-C
6
)alkylamino(C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyls; carboxyl; (C
1
-C
6
)alkylcarboxyls; (C
1
-C
6
)alkylsulphonyls; aminosulphonyls; N—Z-aminosulphonyls; (C
1
-C
6
)N-alkylaminosulphonyls; N,N-di(C
1
-C
6
)alkylaminosulphonyls; (C
1
-C
6
)aminosulphonylalkyls; (C
1
-C
6
)N—Z-aminosulphonylalkyls; N—(C
1
-C
6
)alkylaminosulphonyl(C
1
-C
6
)alkyls; N,N-di(C
1
-C
6
)alkylaminosulphonyl(C
1
-C
6
)alkyls; carbamyl; N—(C
1
-C
6
)alkylcarbamyls; N,N-di(C
1
-C
6
)alkylcarbamyls; carbamyl(C
1
-C
6
)alkyls; N—(C
1
-C
6
)alkylcarbamyl(C
1
-C
6
)alkyls; N,N-di(C
1
-C
6
)alkylcarbamyl(C
1
-C
6
)alkyls; (C
1
-C
6
)alkyls; (C
1
-C
6
)monohydroxyalkyls; (C
2
-C
6
)polyhydroxyalkyls; (C
1
-C
6
)alkoxy(C
1
-C
6
)alkyls; (C
1
-C
6
)trifluoroalkyls; a cyano group; OR
6
and SR
6
groups; amino groups protected with a radical chosen from (C
1
-C
6
)alkylcarbonyls, (C
1
-C
6
)alkylcarboxyls, trifluoro(C
1
-C
6
)alkylcarbonyls, amino(C
1
-C
6
)alkylcarbonyls, N—Z-amino(C
1
-C
6
)alkylcarbonyls, N—(C
1
-C
6
)alkylamino(C
1
-C
6
)alkylcarbonyls, N,N-di(C
1
-C
6
)alkylamino (C
1
-C
6
)alkylcarbonyls, (C
1
-C
6
)alkylcarboxyls, carbamyl, N—(C
1
-C
6
)alkylcarbamyls, N,N-di(C
1
-C
6
)alkylcarbamyls, (C
1
-C
6
)alkylsulphonyls, aminosulphonyls, N—Z-aminosulphonyls, (C
1
-C
6
)N-alkylaminosulphonyls, N,N-di(C
1
-C
6
)alkylaminosulphonyls, thiocarbamyl radicals, formyl radicals, and Z groups, wherein the linker arm B of the Z groups comprises a ketone function directly attached to the nitrogen atom of the amino group; and (C
1
-C
6
)aminoalkyls in which the amine is substituted with one or two identical or different radicals chosen from (C
1
-C
6
)alkyls, (C
1
-C
6
)monohydroxyalkyls, (C
2
-C
6
)polyhydroxyalkyls, (C
1
-C
6
)alkylcarbonyls, carbamyl, N—(C
1
-C
6
)alkyl-carbamyls, N,N-di(C
1
-C
6
)alkylcarbamyls, (C
1
-C
6
)alkylsulphonyls, formyls, trifluoro(C
1
-C
6
)alkylcarbonyls, (C
1
-C
6
)alkylcarboxyls, thiocarbamyl, and Z groups;
R
6
is a radical chosen from (C
1
-C
6
)alkyls; (C
1
-C
6
)monohydroxyalkyls; (C
2
-C
6
)polyhydroxyalkyls; Z groups; (C
1
-C
6
)alkoxy(C
1
-C
6
)alkyl; aryls; benzyl; carboxy(C
1
-C
6
)alkyls; (C
1
-C
6
)alkylcarboxy(C
1
-C
6
)alkyls; cyano(C
1
-C
6
)alkyls; carbamyl(C
1
-C
6
)alkyls; N—(C
1
-C
6
)alkylcarbamyl(C
1
-C
6
)alkyls; N,N-di(C
1
-C
6
)alkylcarbamyl(C
1
-C
6
)alkyls; (C
1
-C
6
)trifluoroalkyls; (C
1
-C
6
)aminosulphonylalkyls; (C
1
-C
6
)N—Z-aminosulphonylalkyls; N—(C
1
-C
6
)alkylaminosulphonyl(C
1
-C
6
)alkyls; N,N-di(C
1
-C
6
)alkylaminosulphonyl(C
1
-C
6
)alkyls; (C
1
-C
6
)alkylsulphinyl(C
1
-C
6
)alkyls; (C
1
-C
6
)alkylsulphonyl(C
1
-C
6
)alkyls; (C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyls; (C
1
-C
6
)aminoalkyls; (C
1
-C
6
)aminoalkyls in which the amine is substituted with one or two identical or different radicals chosen from (C
1
-C
6
)alkyls, (C
1
-C
6
)monohydroxyalkyls, (C
2
-C
6
)polyhydroxyalkyls, (C
1
-C
6
)alkylcarbonyls, formyls, trifluoro-(C
1
-C
6
)alkylcarbonyls, (C
1
-C
6
)alkylcarboxyls, carbamyl, N—(C
1
-C
6
)alkylcarbamyls, N,N-di-(C
1
-C
6
)alkylcarbamyls, thiocarbamyl, (C
1
-C
6
)alkylsulphonyls, and Z groups;
R
4
, R′
4
, R
5
and R′
5
, which may be identical or different, are radicals chosen from a hydrogen atom; Z groups; (C
1
-C
6
)alkyls; (C
1
-C
6
)monohydroxyalkyls; (C
2
-C
6
)polyhydroxyalkyls; (C
1
-C
6
)alkoxy(C
1
-C
6
)alkyls; aryls; benzyl; cyano(C
1
-C
6
)alkyls; carbamyl(C
1
-C
6
)alkyls; N—(C
1
-C
6
)alkylcarbamyl(C
1
-C
6
)alkyls; N,N-di(C
1
-C
6
)alkylcarbamyl(C
1
-C
6
)alkyls; thiocarbamyl(C
1
-C
6
)alkyls; (C
1
-C
6
)trifluoroalkyls; (C
1
-C
6
)sulphoalkyls; (C
1
-C
6
)alkylcarboxy(C
1
-C
6
)alkyls; (C
1
-C
6
)alkylsulphinyl(C
1
-C
6
)alkyls; (C
1
-C
6
)aminosulphonylalkyls; (C
1
-C
6
)N—Z-aminosulphonylalkyls; N—(C
1
-C
6
)alkylaminosulphonyl(C
1
-C
6
)alkyls; N,N-di(C
1
-C
6
)alkylaminosulphonyl(C
1
-C
6
)alkyls; (C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyls; (C
1
-C
6
)aminoalkyls; (C
1
-C
6
)aminoalkyls in which the amine is substituted with one or two identical or different radicals chosen from (C
1
-C
6
)alkyls, (C
1
-C
6
)monohydroxyalkyls, (C
2
-C
6
)polyhydroxyalkyls, (C
1
-C
6
)alkylcarbonyls, carbamyl, N—(C
1
-C
6
)alkylcarbamyls, N,N-di(C
1
-C
6
)alkylcarbamyls, (C
1
-C
6
)alkylsulphonyls, formyl, trifluoro(C
1
-C
6
)alkylcarbonyls, (C
1
-C
6
)alkylcarboxyls, thiocarbamyl, and Z groups;
Z is chosen from 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 chosen from linear and branched alkyl chains, optionally interrupted by at least one hetero atom, such as oxygen, sulphur, and nitrogen atoms, and optionally substituted with at least one radical chosen from a hydroxyl group and (C
1
-C
6
)alkoxys, and which can op

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