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

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

2001-10-22

2004-08-31

Mruk, Brian P (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S406000, C008S408000, C008S407000, C008S423000, C008S473000, C008S567000, C008S573000, C544S281000, C548S360500

Reexamination Certificate

active

06783557

ABSTRACT:

The invention relates to novel pyrazolo[1,5-a]pyrimidines comprising at least one cationic group Z, Z being selected from quaternized aliphatic chains, aliphatic chains containing at least one quaternized saturated ring and aliphatic chains containing at least one quaternized unsaturated ring, to their use as oxidation base for the oxidation dyeing of keratinous fibres, to the dyeing compositions comprising them, and to the methods of oxidation dyeing which employ them.
It is known to dye keratinous fibres, and especially human hair, with dyeing compositions comprising oxidation dye precursors, especially ortho- or para-phenylenediamines, ortho- or para-aminophenols, and heterocyclic compounds such as diaminopyrazole derivatives, which are referred to generally as oxidation bases. The oxidation dye precursors or oxidation bases are colourless or slightly coloured compounds which, when combined with oxidizing products, have the capacity to give rise to coloured and colouring compounds by virtue of a process of oxidative condensation.
It is also known that the shades obtained with these oxidation bases may be varied by combining them with couplers or coloration modifiers, the latter being selected in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds.
The variety of molecules employed as oxidation bases and couplers makes it possible to obtain a rich palette of colours.
The so-called permanent coloration obtained by virtue of these oxidation dyes is required, moreover, to satisfy acertain number of requirements. Hence it must have no toxicological drawbacks, must allow shades of the desired intensity to be obtained, and must have good resistance to external agents (light, inclement weather, washing, permanent-waving, perspiration and friction).
The dyes must also allow white hair to be covered and, finally, they must be as unselective as possible; in other words, they must allow the smallest possible differences in coloration to be produced over the entire length of a single keratinous fibre, which may indeed be sensitized (i.e. damaged) differently between its tip and its root.
The applicant has now discovered, completely unexpectedly and surprisingly, that new pyrazolo[1,5-a]pyrimidines of formula (I) defined below, comprising at least one cationic group Z, Z being selected from quaternized aliphatic chains, aliphatic chains containing at least one quaternized saturated ring and aliphatic chains containing at least one quaternized unsaturated ring are not only suitable for use as oxidation dye precursors, but also make it possible to obtain dyeing compositions which lead to intense colorations in a wide palette of colours and have excellent properties of resistance to the various treatments which the keratinous fibres may undergo.
It is these discoveries which form the basis of the present invention.
The invention therefore provides, firstly, novel compounds of formula (I) below, and their addition salts 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
alkyl)carbonyl radical; an amino(C
1
-C
6
alkyl)carbonyl radical; an N-Z-amino(C
1
-C
6
alkyl)carbonyl radical; an N-(C
1
-C
6
alkyl)amino(C
1
-C
6
alkyl)carbonyl radical; an N,N-di(C
1
-C
6
alkyl)amino(C
1
-C
6
alkyl)carbonyl radical; an amino(C
1
-C
6
alkyl)carbonyl(C
1
-C
6
alkyl) radical; an N-Z-amino(C
1
-C
6
alkyl)carbonyl(C
1
-C
6
alkyl) radical; an N-(C
1
-C
6
alkyl)amino(C
1
-C
6
alkyl)carbonyl(C
1
-C
6
alkyl) radical; an N,N-di(C
1
-C
6
alkyl)amino(C
1
-C
6
alkyl)carbonyl(C
1
-C
6
alkyl) radical; a carboxyl radical; a (C
1
-C
6
alkyl)carboxyl radical; a (C
1
-C
6
alkyl)sulphonyl radical; an aminosulphonyl radical; an N-Z-aminosulphonyl radical; an N-(C
1
-C
6
alkyl)aminosulphonyl radical; an N,N-di(C
1
-C
6
alkyl)-aminosulphonyl radical; an aminosulphonyl(C
1
-C
6
alkyl) radical; an N-Z-aminosulphonyl(C
1
-C
6
alkyl) radical; an N-(C
1
-C
6
alkyl)aminosulphonyl(C
1
-C
6
alkyl) radical; an N,N-di(C
1
-C
6
alkyl)aminosulphonyl(C
1
-C
6
alkyl) radical; a carbamyl radical; an N-(C
1
-C
6
alkyl)carbamyl radical; an N,N-di(C
1
-C
6
alkyl)carbamyl 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
alkyl)carbamyl(C
1
-C
6
alkyl) radical; a C
1
-C
6
alkyl radical; a hydroxyl radical; a nitro radical; a C
1
-C
6
monohydroxyalkyl radical; a C
2
-C
6
polyhydroxyalkyl radical; a C
1
-C
6
(C
1
-C
6
alkoxy)alkyl radical; a C
1
-C
6
trifluoroalkyl radical; a cyano radical; a group OR
6
or SR
6
; an amino radical; an N-(C
6
-C
6
alkyl)amino radical; an N,N-di(C
1
-C
6
alkyl)amino radical (where the two alkyl substituents may form a 5- or 6-membered ring); an N-hydroxy(C
1
-C
6
alkyl)amino radical; an N,N-bis(hydroxy(C
1
-C
6
alkyl))amino radical; an N-polyhydroxy(C
2
-C
6
alkyl)amino radical; an N,N-bis(polyhydroxy(C
2
-C
6
alkyl))amino radical; an amino(C
1
-C
6
alkyl)amino radical in which the terminal amino group is unsubstituted or substituted by one or two C
1
-C
6
alkyl radicals, where the said alkyl radicals may form a saturated or unsaturated, 5- or 6-membered ring; an amino group protected by a (C
1
-C
6
alkyl)carbonyl, trifluoro(C
1
-C
6
alkyl)carbonyl, amino(C
1
-C
6
alkyl)carbonyl, N-Z-amino(C
1
-C
6
alkyl)-carbonyl, N-(C
1
-C
6
alkyl)amino(C
1
-C
6
alkyl)carbonyl, N,N-di(C
1
-C
6
alkyl)amino(C
1
-C
6
alkyl)carbonyl or formyl radical or by 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
(C
1
-C
6
alkoxy)alkyl radical; an aryl radical; a benzyl radical; a C
1
-C
6
carboxyalkyl radical; a C
1
-C
6
(C
1
-C
6
alkyl)carboxyalkyl radical; a C
1
-C
6
cyanoalkyl radical; a C
1
-C
6
carbamylalkyl radical; a C
1
-C
6
N-(C
1
-C
6
alkyl)carbamylalkyl radical; a C
1
-C
6
N,N-di(C
1
-C
6
alkyl)carbamylalkyl radical; a C
1
-C
6
trifluoroalkyl radical; a C
1
-C
6
aminosulphonylalkyl radical; a C
1
-C
6
N-Z-aminosulphonylalkyl radical; a C
1
-C
6
N-(C
1
-C
6
alkyl)aminosulphonylalkyl radical; a C
1
-C
6
N,N-di(C
1
-C
6
alkyl)aminosulphonylalkyl radical; a C
1
-C
6
(C
1
-C
6
alkyl)sulphinylalkyl radical; a C
1
-C
6
(C
1
-C
6
alkyl)sulphonylalkyl radical; a C
1
-C
6
(C
1
-C
6
alkyl)carbonylalkyl radical; a C
1
-C
6
aminoalkyl radical; a C
1
-C
6
aminoalkyl radical whose amine is substituted by one or two identical or different radicals selected from C
1
-C
6
alkyl, monohydroxy(C
1
-C
6
alkyl), polyhydroxy(C
2
-C
6
alkyl), (C
1
-C
6
alkyl)-carbonyl, formyl, trifluoro(C
1
-C
6
alkyl)carbonyl and (C
1
-C
6
alkyl)sulphonyl radicals or by a group Z;
A represents a group —NR
4
R
5
or a hydroxyl radical;
R
4
and R
5
, which are 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
(C
1
-C
6
alkoxy)alkyl radical; an aryl radical; a benzyl radical; a C
1
-C
6
cyanoalkyl radical; a C
1
-C
6
carbamylalkyl radical; a C
1
-C
6
N-(C
1
-C
6
alkyl)carbamylalkyl radical; a C
1
-C
6
N,N-di(C
1
-C
6
alkyl)carbamylalkyl radical; a C
1
-C
6
thiocarbamylalkyl radical; a C
1
-C
6
trifluoroalkyl radical; a C
1
-C
6
sulphoalkyl radical; a C
1
-C
6
(C
1
-C
6
alkyl)carboxyalkyl radical; a C
1
-C
6
(C
1
-C
6
alkyl)sulphinylalkyl radical; a C
1
-C
6
aminosulphonylalkyl radical; a C
1
-C
6
N-Z-aminosulphonylalkyl radical; a C
1
-C
6
N-(C
1
-C
6
alkyl)-aminosulphonylalkyl radical; a C
1
-C
6
N,N-di(C
1
-C
6
alkyl)aminosulphonylalkyl radical; a C
1
-C
6
(C
1
-C
6
alkyl)carbonylalkyl radical; a C
1
-C
6
aminoalkyl radical; a C
1
-C
6
aminoalkyl radical whose amine is substituted by one or two identical or different radicals selected from C
1
-C
6
alkyl, C
1
-C
6
monohydroxyalkyl, C
2
-C
6
polyhydroxyalkyl, (C
1
-C
6
alkyl)carbonyl, (C
1
-C
6
alkyl)sulphonyl, formyl and trifluoro(C
1
-C
6
alkyl)

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