Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2001-11-14
2004-05-11
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S401000, C008S406000, C008S407000, C008S408000, C008S409000, C008S415000, C008S424000, 56
Reexamination Certificate
active
06733540
ABSTRACT:
The invention relates to the field of the oxidation dyeing of keratinous fibres and in particular of human keratinous fibres, such as the hair. The invention relates more particularly to the use of certain 2-(sulphonylamino)phenols in combination with oxidation dye precursors for the oxidation dyeing of fibres.
It is known to dye keratinous fibres and in particular human hair with dyeing compositions comprising oxidation dye precursors, in particular para-phenylenediamines, ortho- or para-aminophenols, or heterocyclic compounds, such as diaminopyrazole derivatives, generally known as oxidation bases. Oxidation dye precursors or oxidation bases are colourless or weakly coloured compounds which, in combination with oxidizing substances, can give rise by an oxidative coupling process to coloured and colouring compounds.
It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or colouring modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols, non-cationic naphthols or certain heterocyclic compounds, such as, for example, indole couplers.
The variety of the molecules employed as oxidation bases and couplers makes it possible to obtain a rich palette of colours.
The <<permanent>> colouring obtained by virtue of these oxidation dyes has, however, to satisfy a certain number of requirements. Thus, it must be without disadvantage toxicologically, it must make it possible to obtain shades in the desired intensity and it must behave well in the face of external agents (light, bad weather, washing, permanent waving, perspiration or rubbing).
The dyes must also make it possible to cover white hair and, finally, be as unselective as possible, that is to say make it possible to obtain the least possible differences in colouring along the same keratinous fibre, this being because the latter can be sensitized (i.e. damaged) to a varying degree between its tip and its root.
Provision has already been made, in particular in Patent Application BE 803 712, for oxidation dyeing compositions comprising nitrated 2-(sulphonylamino)phenols as direct yellow dye or as yellow couplers, in combination with oxidation bases conventionally used in oxidation dyeing, such as, for example, para-phenylenediamine, para-toluylenediamine, para-dimethylaminoaniline, para-amino-phenol or para-diaminoanisole. Such compositions are not, however, always satisfactory, in particular from the viewpoint of the power and the chromaticity of the colourings obtained.
The Applicant Company has now just discovered, in a completely unexpected and surprising way, that it is possible to obtain novel dyes, which dyes are capable of resulting in powerful colourings in shades varying from red to blue which are particularly chromatic and bright, which are not very selective and which exhibit excellent properties of resistance to the various attacks which keratinous fibres may be subjected to, by combining at least one oxidation base and at least one coupler chosen from certain 2-(sulphonylamino) phenols.
A first subject-matter of the invention is therefore a composition for the oxidation dyeing of keratinous fibres and in particular of human keratinous fibres, such as the hair, comprising, in a medium appropriate for the dyeing of the said fibres:
at least one oxidation base;
and at least one coupler chosen from the compounds of following formula (I) and/or their addition salts with an acid:
in which:
R
1
represents a hydrogen atom or a linear or branched radical comprising from 1 to 15 carbon atoms (it being possible for the branching or branchings to form one or more carbonaceous rings comprising from 3 to 7 ring members) which can comprise one or more double bonds and/or one or more triple bonds (the said double bonds optionally resulting in aromatic groups) and one or more carbon atoms of which can be replaced by an oxygen, nitrogen or sulphur atom or by an SO
2
group and the carbon atoms of which can, independently of one another, be substituted by one or more halogen atoms, the said R
1
radical comprising neither peroxide bonds nor diazo, nitro and nitroso radicals;
R
2
represents a hydrogen atom or a linear or branched radical comprising from 1 to 20 carbon atoms (it being possible for the branching or branchings to form one or more carbonaceous rings comprising from 3 to 7 ring members) which can comprise one or more double bonds and/or one or more triple bonds (the said double bonds optionally resulting in aromatic groups) and one or more carbon atoms of which can be replaced by an oxygen, nitrogen or sulphur atom or by an SO
2
group and the carbon atoms of which can, independently of one another, be substituted by one or more halogen atoms, the said R
2
radical comprising neither peroxide bonds nor diazo, nitro and nitroso radicals;
R
3
, R
4
and R
5
, which are identical or different, represent a hydrogen or halogen atom or a linear or branched radical comprising from 1 to 20 carbon atoms (it then being possible for the branching or branchings to form one or more rings comprising from 3 to 7 ring members) which can comprise one or more double bonds and/or one or more triple bonds (the said double bonds optionally resulting in aromatic groups) and one or more carbon atoms of which can be replaced by an oxygen, nitrogen or sulphur atom or by an SO
2
group and the carbon atoms of which can, independently of one another, be substituted by one or more halogen atoms, the said radical comprising neither peroxide bonds nor diazo, nitro and nitroso radicals and it being understood that R
5
cannot represent a hydroxyl, thio or amino radical and it being understood that the R
3
, R
4
and R
5
radicals cannot be connected to the benzene ring of the formula (I) via an —NH—NH— bond;
Y represents a hydrogen or halogen atom; an —OR
6
, —SR
6
or —NH—SO
2
R, group in which R
6
represents a linear or branched C
1
-C
6
alkyl radical (it then being possible for the branching or branchings to form one or more rings comprising from 3 to 6 ring members), optionally substituted by one or more radicals chosen from the group: halogen, hydroxyl, C
1
-C
4
alkoxy, amino or C
1
-C
4
aminoalkyl; a phenyl radical, optionally substituted by 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 or C
1
-C
4
aminoalkyl; or a benzyl radical.
As indicated above, the oxidation dyeing composition comprising the compound or compounds of formula (I) in accordance with the invention makes it possible to obtain powerful colourings in shades varying from red to blue which furthermore exhibit a noteworthy persistence towards the various treatments which keratinous fibres may be subjected to. These properties are particularly noteworthy especially as regards the resistance of the colourings obtained with respect to the action of bad weather, washing, permanent waving and perspiration.
Another subject-matter of the invention is a process for the oxidation dyeing of keratinous fibres employing this dyeing composition.
According to the invention, when it is indicated that one or more of the carbon atoms of the R
1
to R
5
radical or radicals can be replaced by an oxygen, nitrogen or sulphur atom or by an SO
2
group and/or that the said R
1
to R
5
radicals can comprise one or more double bonds and/or one or more triple bonds, this means that it is possible, by way of example, to carry out the following
conversions:
According to the invention, preferably denotes a hydrogen atom or an A
1
, A
2
, A
3
, A
4
or A
5
group as defined is below.
According to the invention, the term <<A group>> is understood to mean a linear or branched C
1
-C
6
hydrocarbonaceous radical which can carry one or two double bonds or one triple bond, which may or may not be substituted by a group chosen from an A
2
group, an A
4
group or an A
5
group, which may or may not be substituted by one or two identical or different groups chosen fr
Saunier Jean-Baptiste
Vidal Laurent
Einsmann Margaret
Elhilo Eisa
L'Oreal
Nixon & Vanderhye P.C.
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