Cationic couplers and their use for oxidation dyeing

Details Cationic couplers and their use for oxidation dyeing Cationic couplers and their use for oxidation dyeing

2000-11-22

2003-08-12

Delcotto, Gregory (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S406000, C008S409000, C008S410000, C008S421000, C008S424000, C430S378000, C430S547000, C430S566000, C430S567000

Reexamination Certificate

active

06605124

ABSTRACT:

The invention relates to novel compounds derived from naphth-1-ol which can be represented by formula (I) and comprising at least one cationic group Z of formula (II), their use as coupler for the oxidation dyeing of keratinous fibres, compositions for the oxidation dyeing of keratinous fibres, and in particular human keratinous fibres such as hair, containing them in combination with at least one oxidation base, as well as the oxidation dyeing methods using them.
It is known to dye keratinous fibres and in particular human hair with dyeing compositions containing oxidation dye precursors, in particular para-phenylenediamines, ortho- or para-aminophenols, heterocyclic compounds such as diaminopyrazole derivatives, generally called oxidation bases. Oxidation dye precursors, or oxidation bases, are colourless or weakly coloured compounds which, combined with oxidizing products, can give rise, through a process of oxidative condensation, to coloured or colouring compounds.
It is also known that it is possible to vary the shades obtained with these oxidation bases by combining them with couplers or colour modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols, noncationic naphthols or alternatively certain heterocyclic compounds such as for example indolic couplers.
The variety of molecules used in oxidation bases and couplers allows a rich palette of colours to be obtained.
The so-called “permanent” colour obtained using these oxidation dyes must moreover satisfy a number of requirements. Thus, it must be without drawbacks from the toxicological point of view, it must make it possible to obtain shades in the desired intensity and exhibit good resistance towards external agents (light, adverse weather conditions, washing, permanent waving, perspiration, rubbing).
The dyes must also make it possible to cover grey hair and must finally be the least selective possible, that is to say make it possible to obtain the smallest possible differences in colour right along the same keratinous fibre, which may indeed be differently sensitized (i.e. damaged) between its tip and its root.
However, the applicant has now just discovered, completely unexpectedly and surprisingly, that the use, as coupler, of novel compounds of the 2-acylaminonaphth-1-ol, 2-amidonaphth-1-ol and 2-sulphonylaminonaphth-1-ol type, comprising at least one cationic group Z of formula (II) as defined below, and which can be represented by formula (I) as defined below, makes it possible to obtain dyeing compositions leading to intense colours, in shades ranging from red to blue and exhibiting, furthermore, remarkable fastness to light, adverse weather conditions, washing, perspiration or permanent waving.
These discoveries form the basis of the present invention.
The first subject of the invention is therefore a compound of the following formula (I), as well as its addition salts with an acid:
in which:
R
1
represents a group chosen from —NR
4
(C═O)R
5
, —NR
6
SO
2
R
7
and —(C═O)NR
6
R
8
, the radicals R
4
, R
5
, R
6
, R
7
and R
8
being as defined below;
R
2
and R
3
, which are identical or different, represent a hydrogen atom; a halogen atom; a group Z as defined below; a radical comprising from 1 to 20 carbon atoms, linear or branched (it being possible for the branch(es) to form one or more carbon-containing rings comprising from 3 to 7 members), which may contain one or more double bonds and/or one or more triple bonds (the said double bonds possibly leading to aromatic groups), in which one or more carbon atoms may be replaced with an oxygen, nitrogen or sulphur atom or with an SO
2
group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms;
it being understood that:
the said radicals R
2
and R
3
cannot be linked to the benzene ring of formula (I) by an —NH—NH— bond; and that R
2
and R
3
do not contain a peroxide bond or diazo, nitro and nitroso radicals;
that R
2
and R
3
cannot represent a hydroxyl radical or a thio radical;
that R
2
and R
3
cannot represent, simultaneously, an amino, alkylamino, acylamino or sulphonylamino radical;
Y represents a hydrogen or halogen atom; a group —OR
9
, —SR
9
, or —NH—SO
2
R
9
in which R
9
represents a C
1
-C
6
alkyl radical, linear or branched (it being possible for the branch(es) to then form one or more rings comprising from 3 to 6 members), unsubstituted or substituted with one or more radicals chosen from the group consisting of a halogen atom, a hydroxyl, C
1
-C
4
alkoxy, amino and amino(C
1
-C
4
alkyl) radical; a phenyl radical, unsubstituted or substituted with one or two radicals chosen from the group consisting of a C
1
-C
4
alkyl, trifluoromethyl, carboxyl, C
1
-C
4
alkoxycarbonyl, halogen, hydroxyl, C
1
-C
4
alkoxy, amino and amino(C
1
-C
4
alkyl) radical; or a benzyl radical;
R
4
, R
6
and R
8
, which are identical or different, represent a hydrogen atom; a group Z as defined below; a radical comprising from 1 to 15 carbon atoms, linear or branched (it being possible for the branch(es) to form one or more carbon-containing rings comprising from 3 to 7 members), which may contain one or more double bonds and/or one or more triple bonds (the said double bonds possibly leading to aromatic groups), in which one or more carbon atoms may be replaced with an oxygen, nitrogen or sulphur atom or with an SO
2
group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms;
it being understood that the said SO
2
group is not directly linked to the nitrogen atom carrying the radical R
4
or R
6
;
it being understood that the group —(C═O)— is not directly linked to the nitrogen atom carrying the radical R
6
;
it being understood that the said radicals R
4
, R
6
and R
8
do not contain a peroxide bond or diazo, nitro and nitroso radicals;
it being understood that the radicals R
4
, R
6
and R
8
cannot represent a hydroxyl radical, a thio radical, an amino radical, an alkoxy radical, an alkylthio radical;
R
5
and R
7
, which are identical or different, represent a hydrogen atom; a group Z as defined below; a radical comprising from 1 to 20 carbon atoms, linear or branched (it being possible for the branch(es) to form one or more carbon-containing rings comprising from 3 to 7 members), which may contain one or more double bonds and/or one or more triple bonds (the said double bonds possibly leading to aromatic groups), in which one or more carbon atoms may be replaced with an oxygen, nitrogen or sulphur atom or with an SO
2
group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms;
it being understood that the said radicals R
5
and R
7
do not contain peroxide bonds or diazo, nitro and nitroso radicals;
it being understood that R
5
cannot represent a hydroxyl radical or a thio radical;
it being understood that R
7
cannot represent a thio radical;
it, being understood that the radicals R
4
and R
5
on the one hand, and the radicals R
6
and R
8
on the other hand, can, in addition, be linked to form, independently of each other, a saturated or unsaturated ring comprising from 5 to 7 members, consisting of carbon, nitrogen and/or acyl, each member being unsubstituted or substituted with 1 or 2 radicals R, which are identical or different, R being a C
1
-C
8
alkyl radical, linear or branched (it being possible for the branch(es) to then form one or more rings comprising from 3 to 7 members), which may contain one or more double bonds and/or one or more triple bonds (the said double bonds possibly leading to aromatic groups), and in which one or more carbon atoms may be replaced with an oxygen, nitrogen or sulphur atom or with an SO
2
group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms; the said ring containing no peroxide bonds or diazo, nitro and nitroso radicals;
Z is a cationic group represented by the following formula (II):
 in which:
n

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