Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2000-11-21
2003-04-08
Gupta, Yogendra N. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S405000, C008S406000, C008S407000, C008S408000, C008S409000, C008S412000, C546S293000, C424S269100, C430S553000
Reexamination Certificate
active
06544298
ABSTRACT:
The subject of the invention is a composition for the oxidation dyeing of keratinous fibres, and in particular human keratinous fibres such as hair, comprising at least one oxidation base and, as coupler, at least one 2-acylaminophenol of formula (I) comprising at least one cationic group Z of formula (II), their use as coupler for the oxidation dyeing of keratinous fibres, oxidation dyeing methods using them, as well as novel cationic 2-acylaminophenols of formula (I′).
It is known to dye keratinous fibres and in particular human hair with dyeing compositions containing oxidation dye precursors, in particular ortho- or 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 and certain heterocyclic compounds.
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.
To obtain red shades, 4-aminophenol is generally used, alone or as a mixture with other bases, and in combination with appropriate couplers, and to obtain blue shades, para-phenylenediamines are normally used. The use of couplers derived from meta-phenylenediamines, in combination with derivatives of para-phenylenediamines, normally leads to blue shades whose fastness is generally poor.
It has already been proposed, in particular in patent FR-A-1,596,879, to use for the oxidation dyeing of keratinous fibres phenolic derivatives substituted at the 2-position with a ureinyl or thioureinyl radical, in combination with derivatives of para-phenylenediamines, in order to obtain shades similar to those obtained with the couplers derived from meta-phenylenediamines. However, the dyeing compositions containing the compounds mentioned in this patent generally lead, on the hair, to colours which are too selective and which lack intensity.
Moreover, it has already been proposed, in particular in patent BE 816,674, to use for the dyeing of keratinous fibres, in combination with derivatives of para-phenylenediamines, phenolic derivatives substituted at the 2-position with an acetyl or urea radical and at the 5-position with a halogen atom, in order to obtain colours ranging from green to green-blue. The fastness to light of the shades obtained on hair using these compositions is generally better than those obtained with dyeing compositions containing one or more meta-phenylenediamines as couplers. However, the fastness to adverse weather conditions and to washing as well as the intensities of the colours obtained are still too weak and constitute, in this respect, major disadvantages for persons skilled in the art.
In addition, there has already been proposed, in particular in patent application EP 0,579,204, to use for dyeing keratinous fibres, noncationic phenolic derivatives substituted at the 2-position with an acylamino, carbamoyl or ureyl radical, and at the 5-position with a C
1
-C
4
alkyl radical, in combination with derivatives of para-phenylenediamine. However, the use of the phenolic derivatives mentioned in this European patent application does not make it possible to obtain a rich palette of colours, and, furthermore, the blue shades generally obtained are not completely satisfactory as regards their resistance to washing and to the action of light.
However, the applicant has now just discovered, completely unexpectedly and surprisingly, that the use, as coupler, of 2-acylaminophenols of formula (I) defined below and comprising at least one cationic group Z of formula (II) as defined below makes it possible to obtain dyeing compositions leading to intense colours in shades ranging from red to blue and exhibiting, furthermore, a remarkable fastness to light, adverse weather conditions, washing, perspiration or alternatively permanent waving.
These discoveries form the basis of the present invention.
The first subject of the invention is therefore a composition for the oxidation dyeing of keratinous fibres, and in particular human keratinous fibres such as hair, characterized in that it contains, in a medium appropriate for dyeing:
at least one oxidation base, and
at least one coupler chosen from the compounds of the following formula (I) and their addition salts with an acid:
in which:
R
1
represents 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 by an oxygen, nitrogen or sulphur atom or by 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 at the 7-position carrying the radical R
1
; the said radical R
1
comprising no peroxide bond or diazo, nitro or nitroso radicals;
R
2
represents 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) and in which one or more carbon atoms may be replaced by an oxygen, nitrogen or sulphur atom or by 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 radical R
2
containing no peroxide bond or diazo, nitro or nitroso radicals; and it being understood that R
2
cannot represent a hydroxyl or thio radical;
the radicals R
1
and R
2
may, in addition, be linked to form a saturated or unsaturated ring comprising from 5 to 7 members, consisting of carbon, nitrogen, oxygen, sulphur and/or of a C═O group, each member being unsubstituted or substituted with one or two radicals R, which are identical or different, R being 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), 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 by an oxygen, nitrogen or sulphur atom or by 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 radical R containing no peroxide bond or diazo, nitro or nitroso radicals;
R
3
, R
4
and R
5
, which are identical or different, represent a hydrogen or halogen atom; a group Z as defined below; a radical comprising from 1 to 20
Saunier Jean-Baptiste
Vidal Laurent
Elhilo Eisa
Finnegan Henderson Farabow Garrett & Dunner
Gupta Yogendra N.
L'Oreal
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