Cationic 2-sulphonylaminophenols, their use as couplers for...

Details Cationic 2-sulphonylaminophenols, their use as couplers for... Cationic 2-sulphonylaminophenols, their use as couplers for...

2000-12-15

2003-03-25

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S406000, C008S407000, C008S408000, C008S415000, C008S421000, C008S424000, C562S039000

Reexamination Certificate

active

06537329

ABSTRACT:

The invention relates to novel cationic 2-sulphonylaminophenols of formula (I) comprising at least one cationic group Z of formula (II), to their use as couplers for the oxidation dyeing of keratin fibres, and in particular of human keratin fibres such as the hair, to oxidation dye compositions containing them in combination with at least one oxidation base, 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-phenylenediamines, 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.
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.
4-Aminophenol is generally used to obtain red shades, alone or as a mixture with other bases, and in combination with suitable couplers, and para-phenylenediamines are usually used to obtain blue shades. The use of meta-phenylenediamine-based couplers, in combination with para-phenylenediamine-based couplers, usually leads to blue shades whose fastness is generally mediocre.
The Applicant has now discovered, entirely surprisingly and unexpectedly, that novel 2-sulphonylaminophenols of formula (I) defined below comprising at least one cationic group Z of formula (II) defined below are not only suitable for use as couplers, but also make it possible to obtain dye compositions which give intense colorations with a wide range of colours, and having excellent properties of resistance with respect to the various treatments to which keratin fibres may be subjected.
These discoveries form the basis of the present invention.
A first subject of the invention is thus novel 2-sulphonylaminophenols of formula (I) below, and the addition salts thereof with an acid:
in which:
R
1
represents a hydrogen atom; a group Z as defined below; a linear or branched radical containing from 1 to 15 carbon atoms (it being possible for the branch(es) to form one or more 3- to 7-membered carbon-based rings) which can contain one or more double bonds and/or one or more triple bonds (the said double bonds optionally leading to aromatic groups), and one or more carbon atoms of which can be replaced with an oxygen, nitrogen or sulphur atom or with an SO
2
group, and the carbon atoms of which can, independently of each other, be substituted with one or more halogen atoms, the said radical R
1
comprising no peroxide linkages or diazo, nitro or nitroso radicals;
R
2
represents a hydrogen atom; a group Z as defined below; a linear or branched radical containing from 1 to 20 carbon atoms (it being possible for the branch(es) to form one or more 3- to 7-membered carbon-based rings) which can contain one or more double bonds and/or one or more triple bonds (the said double bonds optionally leading to aromatic groups), and one or more carbon atoms of which can be replaced with an oxygen, nitrogen or sulphur atom or with an SO
2
group, and the carbon atoms of which can, independently of each other, be substituted with one or more halogen atoms, the said radical R
1
comprising no peroxide linkages or diazo, nitro or nitroso radicals;
R
3
, R
4
and R
5
, which may be identical or different, represent a hydrogen or halogen atom; a group Z as defined below; a linear or branched radical containing from 1 to 20 carbon atoms (it then being possible for the branch(es) to form one or more 3- to 7-membered rings) which can contain one or more double bonds and/or one or more triple bonds (the said double bonds optionally leading to aromatic groups), and one or more carbon atoms of which can be replaced with an oxygen, nitrogen or sulphur atom or with an SO
2
group, and the carbon atoms of which can, independently of each other, be substituted with one or more halogen atoms, the said radical comprising no peroxide linkages or diazo, nitro or nitroso radicals; and it being understood that R
5
cannot represent a hydroxyl, thio or amino radical; and it being understood that the radicals R
3
, R
4
and R
5
cannot be linked to the benzene ring of formula (I) via an —NH—NH— linkage;
Y represents a hydrogen or halogen atom; a group —OR
6
, —SR
6
or —NH—SO
2
R
6
in which R
6
represents a linear or branched C
1
-C
6
alkyl radical (it then being possible for the branch(es) to form one or more 3- to 6-membered rings) optionally substituted with one or more radicals chosen from the group: halogen, hydroxyl, C
1
-C
4
alkoxy, amino, C
1
-C
4
aminoalkyl; a phenyl radical, optionally substituted with one or two radicals chosen from the group: C
1
-C
4
alkyl, trifluoromethyl, carboxyl, (C
1
-C
4
)alkoxycarbonyl, halogen, hydroxyl, C
1
-C
4
alkoxy, amino, C
1
-C
4
aminoalkyl; a benzyl radical;
Z represents a cationic group represented by formula (II) below:
 in which:
B represents a linear or branched C
1
-C
15
alkyl radical (it then being possible for the branch(es) to form one or more 3- to 7-membered rings) which can contain one or more double bonds and/or one or more triple bonds, the said double bonds optionally leading to aromatic groups, and one or more carbon atoms of which can be replaced with an oxygen, nitrogen or sulphur atom or with an SO
2
radical, and one or more carbon atoms of which can, independently of each other, be substituted with one or more halogen atoms or with one or more groups Z, with the exclusion of peroxide linkages and diazo, nitro or nitroso radicals;
D is chosen from the groups of formulae (III) and (IV) below:
 in which:
the radical B is linked to the group D by any of the atoms in the radical D;
n and p can, independently of each other, take the value 0 or 1;
when n=0, then the group (IV) can be linked to the compound of formula (I) directly via the nitrogen of the quaternary ammonium, instead of the radical R
10
;
Z
1
, Z
2
, Z
3
and Z
4
, independently of each other, represent an oxygen atom; a sulphur atom; a nitrogen atom which is unsubstituted or substituted with a radical R
11
; a carbon atom which is unsubstituted or substituted with one or two radicals R
11
, which may be identical or different;
Z
5
represents a nitrogen atom; a carbon atom which is unsubstituted or substituted with a radical R
11
;
Z
6
can take the same meanings as those indicated below for the radical R
11
; it being understood that Z
6
is other than a hydrogen atom;
in addition, the radicals Z
1
or Z
5
can form, with Z
6
, a saturated or unsaturated 5- to 7-membered ring, each ring member being unsubstituted or substituted with one or two radicals R
11
, which may be identical or different;
R
11
represents a hydrogen atom; a group Z; a linear or branched radical containing from 1 to 10 carbon atoms, which can contain one or more double bonds and/or one or mor

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