Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1998-12-16
2002-04-30
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S406000, C008S407000, C008S408000, C008S423000, C008S573000
Reexamination Certificate
active
06379397
ABSTRACT:
The invention relates to a composition for the oxidation dyeing of keratinous fibers, and in particular of human keratinous fibers such as human hair, comprising at least one pyrazoloazole compound as an oxidation base, the method of dyeing which employs this composition, and novel pyrazoloazoles.
It is well known to dye keratinous fibers, and in particular human hair, using dyeing compositions comprising oxidation dye precursors, such as ortho- or para-phenylenediamines, ortho- or para-aminophenols, and heterocyclic compounds, which are generally referred to as oxidation bases. The oxidation dye precursors, or oxidation bases, are colorless or lightly colored compounds which, when combined with oxidizing products, can give rise, by an oxidative coupling process, to colored and coloring compounds.
It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or coloring modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds, such as indole compounds.
The diversity of the molecules employed as oxidation bases and couplers makes it possible to obtain a wide range of colors.
The “permanent” coloration obtained by these oxidation dyes should optimally meet certain conditions. Thus, it should have no toxicological effects, should allow shades of the desired intensity to be obtained, and should have good resistance to external agents (light, bad weather, washing, permanent waving, perspiration or rubbing).
The dyes should also allow white hairs to be covered and, finally, they should be as unselective as possible, that is to say, they should allow the smallest possible differences in coloration to be produced over the entire length of a single keratinous fibre, which may vary in condition of sensitization or damage from its tip to its root. They should also exhibit good chemical stability in the formulations and a good toxicological profile.
The inventors have discovered that it is possible to obtain powerful novel dyes which are not very selective, are particularly resistant to various external agents which keratinous fibers can be subjected to, and which are capable of generating intense colorings in varied shades by using, as oxidation base, pyrazoloazole compounds of formula (I) defined below.
This discovery is the basis of the present invention.
The first aspect of the invention is thus a composition for the oxidation dyeing of keratinous fibers, and in particular human keratinous fibers such as hair, comprising, in a medium suitable for dyeing:
as oxidation base, at least one pyrazoloazole compound of formula (I) or at least one acid addition salt thereof:
in which:
R
1
represents: a hydrogen atom; a linear or branched C
1
-C
20
alkyl radical, optionally substituted by 1 or 2 radicals R chosen from a halogen atom, a nitro radical, a cyano radical, a hydroxyl radical, an alkoxy radical, an aryloxy radical, an amino radical, an alkylamino radical, an acylamino radical, a carbamoyl radical, a sulphonamido radical, a sulphamoyl radical, an imido radical, an alkylthio radical, an arylthio radical, an aryl radical, such as phenyl or naphthyl, a (C
1
-C
4
)alkoxy-carbonyl radical and an acyl radical; an aryl radical (such as phenyl or naphthyl), optionally substituted by 1 or 2 radicals R as defined above; a 5- or 6-membered heterocycle containing at least one nitrogen, oxygen or sulphur atom (such as pyridyl, quinolyl, pyrrolyl, morpholyl, furanyl, tetrahydrofuranyl, pyrazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, imidazolyl or thiadiazolyl), wherein said heterocycle is optionally substituted by 1 or 2 radicals R as defined above;
when R
1
denotes a C
1
-C
4
alkyl radical, an aryl radical or a 5- or 6-membered heterocycle (as defined above), it can be connected to the carbon atom of the pyrazole via an oxygen, nitrogen or sulphur atom (in this case, R
1
becomes XR
1
with X=O, NH or S);
R
1
can, additionally, 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; a (C
1
-C
4
)alkoxy-carbonylamino radical; an aryloxycarbonylamino radical; a (C
1
-C
4
)alkoxy-carbonyl radical; an aryloxycarbonyl radical; a carboxyl radical; or a hydroxyl radical; R
2
denotes a hydrogen atom; a C
1
-C
4
alkyl radical; a C
1
-C
4
monohydroxyalkyl radical; a C
2
-C
4
polyhydroxyalkyl radical; a C
1
-C
4
aminoalkyl radical; a (CH
2
)
p
—X— (CH
2
)
q
OR′ radical in which p and q are identical or different integers ranging from 1 to 3, R′ represents a hydrogen atom or a methyl radical, and X denotes an oxygen atom or an NR″ group in which R″ represents a hydrogen atom or a methyl radical; a (C
1
-C
4
)alkoxy(C
2
-C
4
)alkyl radical; or a di(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radical; and
Z
a
, Z
b
, and Z
c
represent, independently of one another, a nitrogen atom or a carbon atom carrying an R
3
or R
4
radical, where R
3
and R
4
have the same meanings as those indicated above for the R
1
radical, with the proviso that at least one of the Z
a
, Z
b
, and Z
c
radicals is other than a carbon atom; R
3
and R
4
can also together form a substituted or unsubstituted aromatic ring, such as a phenyl ring.
Preferred R
1
radicals of the compounds of formula (I) defined above are chosen from a hydrogen atom; a linear or branched C
1
-C
4
alkyl radical; a phenyl ring; a phenyl ring substituted by a halogen atom, a C
1
-C
4
alkyl radical, a C
1
-C
4
alkoxy radical, a nitro radical, an amino radical, a trifluoromethyl radical or a C
1
-C
4
alkylamino radical; a benzyl radical; a benzyl radical substituted by a halogen atom, a C
1
-C
4
alkyl radical, a C
1
-C
4
alkoxy radical, a nitro radical, an amino radical, a trifluoromethyl radical or a C
1
-C
4
alkylamino radical; a heterocycle chosen from the thiophene, furan or pyridine rings; a trifluoromethyl radical; a (CH
2
)
p
—X—(CH
2
)
q
—OR′ radical in which p and q are identical or different integers ranging from 1 to 3, where R′ represents a hydrogen atom or a methyl radical and X denotes an oxygen atom or an NR″ radical in which R″ denotes a hydrogen atom or a methyl radical; a C
1
-C
4
hydroxyalkyl radical; a C
1
-C
4
aminoalkyl radical; a C
1
-C
4
alkylamino radical; a di(C
1
-C
4
)alkylamino radical; an arylamino radical; an alkoxy radical chosen from methoxy, ethoxy and phenoxy; a halogen atom chosen from bromine, chlorine and fluorine; a carboxyl group; a C
1
-C
4
alkoxycarbonyl radical; a phenyloxycarbonyl radical; a methylthio radical; an ethylthio radical; a phenylthio radical; a methanesulphonyl radical; a cyano radical; an amino radical; or a hydroxyl radical.
More preferred R
1
radicals of the compounds of formula (I) defined above are chosen from a hydrogen atom; an alkyl radical chosen from the methyl, ethyl, isopropyl and tert-butyl radicals; a halogen atom chosen from chlorine and fluorine; a phenyl radical; a toluyl radical; a 4-chlorophenyl radical; a 4-methoxyphenyl radical; a 3-methoxyphenyl radical; a 2-methoxyphenyl radical; a benzyl radical; a heterocycle chosen from the pyridyl, furyl and thienyl rings; a trifluoromethyl radical, a hydroxymethyl radical; an aminomethyl radical; a methoxy radical; an ethoxy radical; a methylamino radical; an ethylamino radical; a dimethylamino radical; a carboxyl radical; a methoxycarbonyl radical; an ethoxycarbonyl radical and a cyano radical.
More particularly preferred R
1
radicals are chosen from: a hydrogen atom; a chlorine atom; a methyl radical; an ethyl radical; a phenyl radical; a toluyl radical; a 4-chlorophenyl radical; a 4-methoxyphenyl radical; a benzyl radical; a trifluoromethyl radical; a methoxy radical; an ethoxy radical; a car
Maubru Mireille
Vidal Laurent
Einsmann Margaret
L'Oreal (S.A.)
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