Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-04-30
2001-05-15
Liott, Caroline D. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S423000, C008S573000
Reexamination Certificate
active
06231623
ABSTRACT:
The invention relates to a composition for the oxidation dyeing of keratinous fibres, especially human hair, which comprises at least one pyrazolo-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 pyrazolo-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 dyeing keratinous fibres, and especially human keratinous fibres such as hair, which is characterized in that it comprises, in a medium appropriate for dyeing:
as coupler, at least one pyrazolo-azole compound of formula (I) or one of its addition salts with an acid:
in which:
R
1
is: a hydrogen atom; a linear or branched C
1
-C
20
alkyl radical which is optionally substituted by one or two 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 one or two 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, triazolyl, oxazolyl, imidazolyl or thiadiazolyl) and being optionally substituted by one or two radicals R as defined above;
when R
1
is an alkyl radical, an aryl radical or a 5- or 6-membered heterocycle (as defined above) it can be attached to the carbon atom of the ring system by way of an oxygen, nitrogen or sulphur atom (in this case R
1
becomes XR
1
where X=O, NH, S);
R
1
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 siloxy radical; an amino radical; an acylamino radical; an acyloxy radical; a carbamoyloxy radical; a sulphonamide radical; an imide radical; a ureido radical; a sulphamoylamino radical; an alkoxycarbonylamino radical; an aryloxycarbonylamino radical; an alkoxycarbonyl radical; an aryloxycarbonyl radical; or a carboxyl radical;
R
2
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-dichorobenzoyloxy, ethoxyalkyloxy, pyruviloyloxy, cinnamoyloxy or myristoyloxy); an arylthio radical (such as, for example: phenylthio, 4-carboxyphenylthio, 2-ethoxy-5-tert-butylphenylthio, 2-carboxyphenylthio or 4-methanesulphonylphenylthio); an alkythio 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 or 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.
Z
a
, Z
b
and Z
c
independently of one another are a nitrogen atom, a carbon atom carrying a radical R
3
or R
4
as defined for the radical R
1
; with the proviso that at least one of the radicals Z
a
, Z
b
and Z
c
is other than a carbon atom; R
3
and R
4
may also together form a substituted or unsubstituted aromatic ring such as phenyl;
and at least one oxidation base.
The acid addition salts of the compounds of the invention can be selected in particular from hydrochlorides, hydrobromides, tartrates, tosylates, benzenesulphonates, sulphates, lactates and acetates.
Among the radicals R
1
of the above-defined formula (I), preference is given to the radicals selected from the group consisting of: a hydrogen atom; a linear or branched C
1
-C
4
alkyl; a phenyl; a phenyl substituted by a halogen atom, a C
1
-C
4
alkyl, a C
1
-C
4
alkoxy, a nitro group, an amino group, a trifluoromethyl group or C
1
-C
4
alkylamino group; a benzyl radical; a benzyl radical substituted by a halogen atom, a C
1
-C
4
alkyl, a C
1
-C
4
alkoxy, a nitro group, an amino group or a trifluoromethyl group; a C
1
-C
4
alkylamino; a heterocycle selected from thiophene, furan and pyridine; a trifluoromethyl radical; a radical (CH
2
)
p
—X—(CH
2
)
q
—OR′ where p and q are identical or different integers from 1 to 3, R′ is H or methyl and X is an oxygen atom or a group NR″ where R″ is hydrogen or methyl; a C
1
-C
4
hydroxyalkyl; a C
1
-C
4
aminoalkyl; a C
1
-C
4
alkylamino; a C
1
-C
4
dialkylamino; an arylamino; an alkoxy radical selected from methoxy, ethoxy and phenoxy; a halogen selected from fluorine, chlorine and bromine; a carboxyl group; a C
1
-C
4
alkoxycarbonyl; a phenyloxycarbonyl; methylthio; ethylthio; phenylthio; methanesulphonyl; and cyano.
Among the radicals R
1
of the above-defined formula (I), particular preference is given to the radicals selected from the group consisting of: hydrogen; an alkyl selected from methyl, ethyl, isopropyl and tert-butyl; a ha
Malle Gerard
Monteil Eric
Vidal Laurent
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
L'Oreal (S.A.)
Liott Caroline D.
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