Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2000-12-29
2003-04-22
Gupta, Yogendra N. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S405000, C008S406000, C008S407000, C008S408000, C008S409000, C548S366400
Reexamination Certificate
active
06551360
ABSTRACT:
The invention relates to a composition for the oxidation dyeing of keratin fibres, in particular human hair, containing at least one pyrazoline-3,5-dione 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 colorless or weakly coloured compounds which, when combined with oxidizing products, can give rise to colored compounds and dyes by a process of oxidative condensation.
It is known that the shades obtained with these oxidation bases can be varied by combining them with couplers or color 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 colors 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 allow shades to be obtained in the desired intensity and it must show good resistance to external agents (light, bad weather, washing, 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 pyrazoline-3,5-dione compounds as couplers in the presence of an oxidation base.
This discovery forms the basis of the present invention.
The subject or 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, a least one pyrazoline-3,5-dione compound of formula (I), or one of the addition salts thereof with an acid;
in which:
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-methoxyphenoxy, 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, myristoyloxy); an arylthio radical (such as, for example: phenylthio, 4-carboxyphenylthio, 2-ethoxy-5-tert-butylphenylthio, 2-carboxyphenylthio, 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-cyanophnenylureido 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-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 hydoxyalkyl; a carboxyl; or an alkoxycarboxylic radical; R
1
and R
3
represent a hydrogen atom; a linear or branched C
1
-C
5
alkyl radical; a C
2
-C
4
mono- or polyhydroxyalkyl radical; a C
2
-C
4
aminoalkyl radical; a phenyl radical; a phenyl radical substituted with a halogen atom or a C
1
-C
4
alkyl, C
1
-C
4
alkoxy, nitro, trifluoromethyl, amino or C
1
-C
4
alkylamino radical; a benzyl radical; a benzyl radical substituted with a halogen atom or with a C
1
-C
4
alkyl, C
1
-C
4
alkoxy, methylenedioxy or amino radical; or a radical
in which m and n are integers, which may be identical or different, between 1 and 3 inclusive, X represents an oxygen atom or an NH group, Y represents a hydrogen atom or a methyl radical, and Z represents a methyl radical, a group OR or NRR′ in which R and R′, which may be identical or different, denote a hydrogen atom, a methyl radical or an ethyl radical; an amino radical; a C
1
-C
4
alkylamino; a carboxyl radical; an alkoxycarbonyl radical; an aryloxycarbonyl radical; a 5- or 6-membered heterocycle with at least one nitrogen, sulphur or oxygen atom (such as pyridyl, quinolyl, pyrrolyl, morpholyl, furyl, pyrazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl , imadazolyl , thiadiazolyl); an acyl radical; a sulphonyl group; a phosphonyl group;
it being understood that when R
2
and R
3
simultaneously represent a hydrogen atom, then R
1
is other than a hydrogen atom, a C
1
-C
5
alkyl radical or a phenyl radical;
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, tartrates, tosylates, benzenesulphonates, sulphates, lactates and acetates.
Among the radicals R
2
of formula (I) defined above, the preferred radicals are chosen from the group consisting of:
a hydrogen atom; a C
1
-C
4
alkoxy; phenoxy; phenoxy substituted with a halogen atom, a C
1
-C
4
alkyl, a carboxyl, a trifluoromethyl group; an acyloxy radical; benzyloxy; C
1
-C
4
alkylthio; phenylthio; phenylthio substituted with a halogen atom, a C
1
-C
4
alkyl, a carboxyl, a trifluoromethyl group; a C
1
-C
4
alkylamido; phenylamido; 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 C
1
-C
4
hydroxyalkyl; a carboxyl; a C
1
-C
4
alkoxycarboxylic radical.
Among the radicals R
2
of formula (I) defined above, the radicals more particularly preferred are chosen from the group consisting of:
hydrogen; chlorine or bromine; methoxy or ethoxy; phenoxy; 4-methylhenoxy; acyloxy; benzyloxy; methylthio or ethylthio; phenylthio; 4-methylphenylthio, 2-tert-butylphenylthio; acetamido; phenylacetamido; dimethylamino; diethylamino; ethylmethylamino; (&bgr;-hydroxyethyl)methylamino.
Even more particularly, the preferred radicals R
2
are chosen from the group consisting of: hydrogen; chlorine; ethoxy; phenoxy; benzyloxy; acyloxy; acetamido; dimethylamino.
Among the radicals R
1
and R
3
of formula (I) defined above, the preferred radicals are chosen from the group consisting of: hydrogen; C
1
-C
4
alkyl (such as methyl, ethyl, isopropyl, t-butyl, n-propyl); C
2
-C
4
mono- or polyhydroxyalkyl (such as 2-hydroxyethyl, 3,4-dihydroxybutyl); C
2
-C
4
aminoalkyl (such as 2-aminoethyl); dialkylaminoalkyl (such as 2-(N,N-dimethylamino)ethyl); phenyl; phenyl substituted with a chlorine atom, or a methoxy, nitro, trifluoromethyl, amino, methylamino or methyl radical; benzyl; benzyl substituted with a chlorine, a methoxy or a methyl; alkoxycarbonyl (such as methoxycarbonyl, ethoxycarbonyl); aryloxycarbonyl (such as phenyloxycarbonyl); pyridyl; furyl; thienyl; pyrrolyl; thi
Malle Gerard
Vidal Laurent
Elhilo Eisa
Gupta Yogendra N.
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