Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-03-25
2001-05-29
Liott, Caroline D. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S423000, C008S573000, C008S574000
Reexamination Certificate
active
06238440
ABSTRACT:
The invention relates to a composition for the dyeing of keratinous fibres, especially human hair, which comprises at least one pyrrolo-azole compound as coupler and at least one oxidation base.
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, 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, are able to 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 selected in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds, such as indole compounds.
The variety of molecules employed as oxidation bases and couplers makes it possible to obtain a wide range of colours.
The “permanent” coloration obtained by means of these oxidation dyes is required, moreover, to meet a certain 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 in fact be sensitized (i.e. damaged) differently between its tip and its root.
The Applicant has now discovered that it is possible to obtain new, powerful dyes, of low selectivity and particularly high resistance, which are capable of giving rise to intense colorations in various shades, using pyrrolo-azole compounds as couplers in the presence of an oxidation base.
It is this discovery which forms the basis of the present invention.
The invention provides a composition for the dyeing of keratinous fibres and, in particular, of human keratinous fibres, such as hair, which is characterized in that it comprises, in a medium appropriate for dyeing:
as coupler, at least one pyrrolo-azole compound corresponding to one of the following formulae (I) and (II), or one of its addition salts with an acid:
in which:
R
1
is: a hydrogen atom; a halogen atom such as bromine, chlorine or fluorine; an acetylamido group; an alkoxy radical (such as, for example: methoxy, ethoxy, propyloxy, benzyloxy, methoxyethoxy, phenoxyethoxy, 2-cyanoethoxy, phenethyloxy, p-chlorobenzyloxy or methoxyethylcarbamoylmethoxy); an aryloxy radical (such as, for example: phenoxy, 4-methoxyphenoxy, 4-nitrophenoxy, 4-cyanophenoxy, 4-methanesulphonamidophenoxy, 4-methanesulphonylphenoxy, 3-methylphenoxy or 1-naphthyloxy); an acyloxy radical (such as, for example: acetoxy, propanoyloxy, benzoyloxy, 2,4-dichlorobenzoyloxy, ethoxyalkyloxy, pyruvyloyloxy, cinnamoyloxy or myristoyloxy); an arylthio radical (such as, for example: phenylthio, 4-carboxyphenylthio, 2-ethoxy-5-tert-butylphenylthio, 2-carboxyphenylthio or 4-methanesulphonylphenylthio); an alkylthio radical (such as, for example: methylthio, ethylthio, propylthio, butylthio, 2-cyanoethylthio, benzylthio, phenethylthio, 2-(diethylamino)ethylthio, ethoxyethylthio or phenoxyethylthio); a heteroarylthio radical (such as, for example: 5-phenyl-2,3,4,5-tetrazolylthio, 2-benzothiazolylthio); a heteroaryloxy radical (such as, for example: 5-phenyl-2,3,4,5-tetrazolyloxy or 2-benzothiazolyloxy); a thiocyano radical; an N,N-diethylthiocarbonylthio radical; a dodecyloxythiocarbonylthio radical; a benzenesulphonamido radical; an N-ethyltoluenesulphonamido radical; a pentafluorobutanamido radical; a 2,3,4,5,6-pentafluorobenzamido radical; a p-cyanophenylureido radical; an N,N-diethylsulphamoylamino radical; a pyrazolyl radical; an imidazolyl radical; a triazolyl radical; a tetrazolyl radical; a benzimidazolyl radical; a 1-benzyl-5-ethoxy-3-hydantoinyl radical; a 1-benzyl-3-hydantoinyl radical; 5,5-dimethyl-2,4-dioxo-3-oxazolidinyl; a 2-oxy-1,2-dihydro-1-pyridinyl radical; an alkylamido; an arylamido; a radical NR
III
R
IV
where R
III
and R
IV
are identical or different and are a C
1
-C
4
alkyl; a hydroxyalkyl; a carboxyl; or an alkoxycarboxyl radical;
R
2
and R
3
are independently of one another a hydrogen atom; a halogen atom (such as bromine, chlorine or fluorine); a linear or branched C
1
-C
5
alkyl radical which is optionally substituted by one or two halogen, hydroxyl, alkoxy, aryloxy, amino, alkylamino, acyl or acylamino radicals; a C
1
-C
4
alkoxy radical; a C
1
-C
4
alkylthio radical; an arylthio radical; a benzylthio radical; an acyl radical (such as acetyl, 3-phenylpropanoyl, benzoyl or 4-dodecyloxybenzoyl); an acylamino radical; an acyloxy radical (such as acetoxy); a carbamoyl radical (such as carbamoyl, N-ethylcarbamoyl, N-phenylcarbamoyl, N,N-dibutylcarbamoyl or N-(2-dodecyloxyethyl)carbamoyl); a phenyl radical which is optionally substituted by one or two halogen, nitro, sulphonyl, C
1
-C
4
alkoxy, C
1
-C
4
alkyl, C
1
-C
3
trifluoroalkyl, amino or alkylamino groups; an alkoxycarbonyl radical (such as methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl, tert-butyloxycarbonyl, isobutyloxycarbonyl, butylcarbamoylethoxycarbonyl or perfluorohexylethoxycarbonyl); an aryloxycarbonyl radical (such as phenoxycarbonyl or 2,5-diamylphenoxycarbonyl); a cyano radical; a nitro radical; a dialkylphosphono radical (such as dimethylphosphono); a diarylphosphono radical (such as diphenylphosphono); a dialkoxyphospholyl radical (such as dimethoxyphospholyl); a dialkylphosphinyl radical (such as dimethylphosphinyl); a diarylphosphinyl radical (such as diphenylphosphinyl); an alkylsulphinyl radical (such as 3-phenoxypropylsulphinyl); an arylsulphinyl radical (such as 3-phenoxypropylsulphinyl); an arylsulphonyl radical (such as benzenesulphonyl or toluenesulphonyl); an alkylsulphonyl radical (methanesulphonyl, octanesulphonyl); a sulphonyloxy radical (such as methanesulphonyloxy or toluenesulphonyloxy); an acylthio radical (such as acetylthio or benzoylthio); a sulphamoyl radical (such as N-ethylsulphamoyl, N,N-diisopropylsulphamoyl or N,N-diethylsulphamoyl); a thiocyanate radical; or a thiocarbonyl radical (such as methylthiocarbonyl or phenylthiocarbonyl);
Z
a
, Z
b
and Z
c
are independently of one another a nitrogen atom or a carbon atom carrying a radical R
4
, R
5
, R
6
or R
7
;
R
4
, R
6
and R
7
are identical or different and are a hydrogen atom; a linear or branched C
1
-C
20
alkyl radical which is optionally substituted by 1 or 2 radicals R selected from the group consisting of halogen, nitro, cyano, hydroxyl, alkoxy, aryloxy, amino, alkylamino, acylamino, carbamoyl, sulphonamido, sulphamoyl, imido, alkylthio, arylthio, aryl, alkoxycarbonyl and acyl; an aryl radical (such as phenyl or naphthyl) which is optionally substituted by 1 or 2 radicals R as defined above; a 5- or 6-membered heterocycle having at least one nitrogen, oxygen or sulphur atom (such as pyridyl, quinolyl, pyrrolyl, morpholyl, furyl, tetrahydrofuryl, pyrazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, imidazolyl or thiadiazolyl) and being optionally substituted by 1 or 2 radicals R as defined above;
when R
4
, R
6
and R
7
are an alkyl radical, an aryl radical or a 5- or 6-membered heterocycle (defined above), the radical or heterocycle may be attached to the carbon atom of the ring system via an oxygen, nitrogen or sulphur atom (in this case, R
4
, R
6
and R
7
become XR
4
, XR
6
or XR
7
where X=O, NH, S);
R
4
, R
6
and R
7
may also be a halogen atom (such as bromine, chlorine or fluorine); an acyl radical; a sulphonyl radical; a sulphinyl radical; a phosphonyl radical; a carbamoyl radical; a sulphamoyl radical; a cyano radical; a silo
Malle Gerard
Vidal Laurent
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
L'Oreal (S.A.)
Liott Caroline D.
LandOfFree
Keratin fibre dye compositions containing pyrrolo-azole... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Keratin fibre dye compositions containing pyrrolo-azole..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Keratin fibre dye compositions containing pyrrolo-azole... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2490490