Cationic compounds, their use for the oxidation dyeing of...

Details Cationic compounds, their use for the oxidation dyeing of... Cationic compounds, their use for the oxidation dyeing of...

1999-09-01

2002-04-30

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S416000, C008S426000, C008S654000, C008S423000, C008S655000, C564S282000, C564S290000, C548S314400, C548S335500, C548S346100

Reexamination Certificate

active

06379398

ABSTRACT:

The invention relates to dibenzenic ortho-phenylenediamines 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 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 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, must satisfy a certain number of requirements. Oxidation dyes 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 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 dibenzenic ortho-phenylenediamines 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 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 be readily synthesized.
These discoveries form the basis of the present invention.
A subject of the invention is thus ortho-phenylenediamines of formula (I) below, and the acid addition salts thereof:
in which:
B is a linker arm chosen from linear and branched alkyl chains, which can be optionally interrupted with at least one group chosen from Z groups and hetero atoms such as oxygen, sulphur, and nitrogen, and which can be optionally substituted with at least one substituent chosen from hydroxyls and (C
1
-C
6
) alkoxys, and which can optionally bear at least one ketone function; in an embodiment of the invention, the alkyl chains comprise from 1 to 14 carbon atoms;
R
1
, R
2
, R
3
, R′
1
, R′
2
and R′
3
, which may be identical or different, can be the point of attachment of a linker arm B, i.e., they represent one of the two valencies of linker arm B; otherwise, they are 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; cyano; 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-alkylaminosulphonyl, N,N-di(C
1
-C
6
)alkylaminosulphonyls, thiocarbamyl, formyl, and Z groups in which the linker arm B comprises a ketone function directly attached to the nitrogen atom of the amino group;
R
6
can be the point of attachment of a linker arm B, i.e., it can be one of the two valencies of a linker arm; otherwise 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
)alkyls; 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, formyl, 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
5
, R
7
, R
8
, R′
4
, R′
5
, R′
7
and R′
8
, which may be identical or different, can be the point of attachment of a linker arm B, i.e, they can represent one of the two valencies of a linker arm B; otherwise they are 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, c

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