Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-06-16
2001-01-30
Liott, Caroline D. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S423000, C008S567000, C008S573000
Reexamination Certificate
active
06179882
ABSTRACT:
The invention relates to a composition for the oxidation dyeing of keratin fibres, in particular human hair, containing at least one pyrazolopyrimidinoxo compound as coupler and at least one oxidation base.
It is known to dye keratin fibres, and in particular human hair, with dye compositions containing oxidation dye precursors, in particular ortho- or para-phenylene diamines, ortho- or para-aminophenols, and heterocyclic compounds, which are generally referred to as oxidation bases. Oxidation dye precursors, or oxidation bases, are colourless or weakly coloured compounds which, when combined with oxidizing products, can 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 colour modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as indole compounds.
The variety of molecules used as oxidation bases and couplers allows a wide range of colours to be obtained.
The so-called “permanent” coloration obtained by means of these oxidation dyes must moreover satisfy a certain number of requirements. Thus, it must have no toxicological drawbacks, it must be able to allow shades to be obtained in the desired intensity and it must show good resistance to external agents (light, bad weather, washing, waving, permanent-waving, perspiration, rubbing).
The dyes must also be able to cover grey hair and, lastly, they must be as unselective as possible, i.e. they must allow only the smallest possible colour differences to be obtained along the length of the same keratin fibre, which may, indeed, be differently sensitized (i.e. damaged) between its tip and its root.
The Applicant has now discovered that it is possible to obtain novel, powerful, unselective and particularly resistant dyes, which are capable of giving rise to intense colorations in varied shades, by using pyrazolopyrimidinoxo compounds as couplers in the presence of an oxidation base.
This discovery forms the basis of the present invention.
The subject of the invention is a composition for dyeing keratin fibres, and in particular human keratin fibres such as the hair, characterized in that it comprises, in a medium which is suitable for dyeing.
as coupler, at least one pyrazolopyrimidinoxo compound of formula (I), or one of the addition salts thereof with an acid.
in which:
R
1
represents: a hydrogen atom; a linear or branched C
1
-C
20
alkyl radical optionally substituted with 1 or 2 radicals R chosen from the group consisting of halogen, nitro, cyano, hydroxyl, alkoxy, aryloxy, amino, alkylamino, acylamino, carbomoyl, sulphonamido, sulphamoyl, imido, alkylthio, arylthio, aryl, alkoxycarbonyl, acyl; an aryl radical (such as phenyl or naphthyl) optionally substituted with 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) optionally substituted with 1 or 2 radicals R as defined above;
when R
1
denotes an alkyl radical, an aryl radical or a 5- or 6-membered heterocycle (defined above),
it can be linked to the carbon atom of the ring via an oxygen, nitrogen or sulphur atom (in this case, R
1
becomes XR
1
with X═O, NH, S);
R
1
can also denote 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; a carboxyl radical;
R
2
represents: 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, methoxyethylcarbamoylmethoxy); an aryloxy radical (such as, for example: phenoxy, 4-methoxylphenoxy, 4-nitrophenoxy, 4-cyanophenoxy, 4-methanesulphonamidophenoxy, 4-methanesulphonylphenoxy, 3-methylphenoxy, 1-naphthyloxy); an acyloxy radical (such as, for example: acetoxy, propanoyloxy, benzoyloxy, 2,4-dichlorobenzoyloxy, ethoxyalkyloxy, pyruvyloyloxy, cinnamoyloxy, myristyloxy); an arylthio radical (such as, for example: phenylthio, 4-carboxyphenyltio, 4-methanesulphonylphenylthio); an alkylthio radical (such as, for example: methylthio, ethylthio, propylthio, butylthio, 2-cyanoethylthio, benzylthio, phenethylthio, 2-(diethylamino)ethylthio, ethoxyethylthio, 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, 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 benzimiazolyl 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-pyridyl radical; an alkylamido; an arylamido; a radical NR
III
R
IV
with R
III
and R
IV
, which may be identical or different, representing a C
1
-C
4
alkyl, a hydroxyalkyl; a carboxyl; or an alkoxycarboxylic radical;
R
3
has the same meanings mentioned as those mentioned for the radical R
1
;
Z
a
and Z
b
are different and represent a C═O group or a carbon atom bearing a radical R
4
having the same meanings as those mentioned for the radical R
1
;
and at least one oxidation base.
The addition salts with an acid for the compounds of the invention can be chosen in particular from hydrochlorides, hydrobromides, tertrates, tosylates, benzenesulphonates, sulphates, lactates and acetates.
Among the radicals R
1
of formula (I) defined above, the preferred radicals are chosen from the group consisting of:
a hydrogen atom; a linear or branched C
1
-C
4
alkyl; a phenyl; a phenyl substituted with 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 a C
1
-C
4
alkylamino group; a benzyl radical; a benzyl radical substituted with a halogen atom, a C
1
-C
4
alkoxy, a nitro group, an amino group, a trifluoromethyl group; a C
1
-C
4
alkylamino, a heterocycle chosen from thiophene, furan and pyridine; a trifluoromethyl radical; a radical (CH
2
)
p
—X—(CH
2
)
4
—OR′ where p and q are integers, which may be identical or different, between 1 and 3, R′ represents H or methyl and X denotes an oxygen atom or a group NR″ with R″ denoting hydrogen or methyl; a C
1
-C
4
hydroxylalkyl; a C
1
-C
4
aminoalkyl; a C
1
-C
4
alkylamino; a C
1
-C
4
dialkylamino; a phenyloxycarbonyl; cyano; an arylamino; an alkoxy radical chosen from methoxy, ethoxy, phenoxy; a halogen chosen from chlorine, bromine, fluorine; a carboxyl group; a (C
1
-C
4
) alkoxycarbonyl.
Among the radicals R
1
of formula (I) defined above, the radicals more particularly preferred as chosen from the group consisting of: hydrogen; an alkyl chosen from methyl, ethyl, isopropyl, tert-butyl; a halogen chosen from fluorine and chlorine; phenyl; toluyl; 4-chlorophenyl; 4-methoxyphenyl; 3-methoxyphenyl; 2-methoxyphenyl; benzyl; a heterocycle chosen from pyridyl, furyl and thienyl; trifluoromethyl; hydroxymethyl; aminomethyl; methoxy or ethoxy; methylamino or ethylamino or dimethylamino
Malle G{acute over (e)}rard
Vidal Laurent
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
L'Oreal
Liott Caroline D.
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