Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2001-10-18
2003-11-11
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, C008S416000, C008S423000, C548S371400, C548S371700, C548S372500
Reexamination Certificate
active
06645258
ABSTRACT:
The invention relates to novel compositions for the oxidation dyeing of keratin fibers, which compositions comprise at least one 3-substituted 4,5-diaminopyrazole as oxidation base, to the dyeing process using this composition, to novel 3-substituted 4,5-diaminopyrazoles and to a process for their preparation.
It is known to dye keratin fibers, and in particular human hair, with dye compositions containing oxidation dye precursors, in particular ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds such as diaminopyrazole derivatives, which are generally referred to as oxidation bases. The oxidation dye precursors, or oxidation bases, are colorless or weakly colored compounds which, when combined with oxidizing products, may give rise to colored compounds and dyes by a process of oxidative condensation.
It is also known that the shades obtained with these oxidation bases may be varied by combining them with couplers or coloration modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds.
The variety of molecules used as oxidation bases and couplers makes it possible to obtain a wide range of colors.
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 and it must allow shades of the desired strength to be obtained and have good resistance to external agents (light, inclement weather, washing, permanent-waving, perspiration and friction).
The dyes must also allow white hairs to be covered and, lastly, they must be as unselective as possible, i.e., they must allow the smallest possible differences in coloration to be produced over the entire length of the same keratin fiber, which may indeed be differently sensitized (i.e. damaged) between its tip and its root.
In order to obtain red shades, para-aminophenol is usually used, alone or as a mixture with other bases, and in combination with suitable couplers, and in order to obtain blue shades, para-phenylenediamines are generally used.
European Patent Application EP-A-375,977 in particular has already proposed to use certain diaminopyrazole derivatives, namely, more precisely, 3,4- or 4,5-diaminopyrazoles, for the oxidation dyeing of keratin fibers in red shades. However, the use of the diaminopyrazoles described in EP-A-375,977 do not make it possible to obtain a wide range of colors and, furthermore, the process for the preparation of these compounds is long and expensive.
Now, the inventors have discovered, entirely unexpectedly and surprisingly, that the use of certain 3-substituted 4,5-diaminopyrazoles of formula (I) defined below for the part which is novel per se, is not only suitable for use as oxidation dye precursors but also make it possible to obtain dye compositions leading to strong colorations, in shades ranging from red to blue. Lastly, these compounds prove to be readily synthesizable.
These discoveries form the basis of the present invention.
A first subject of the invention is thus a composition for the oxidation dyeing of keratin fibers, and in particular human keratin fibers such as the hair, characterized in that it comprises, in a medium which is suitable for dyeing, at least one 3-substituted 4,5-diaminopyrazole of formula (I) below as oxidation base and/or at least one of the addition salts thereof with an acid:
in which:
R
1
, R
2
, R
3
, R
4
and R
5
which may be identical or different, represent a hydrogen atom; a linear or branched C
1
-C
6
alkyl radical; a C
2
-C
4
hydroxyalkyl 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, from 1 to 3 inclusive, X represents an oxygen atom or the 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, it being understood that when R
2
represents a hydrogen atom, R
3
may then also represent an amino or C
1
-C
4
alkylamino radical,
R
6
represents a linear or branched C
1
-C
6
alkyl radical; a C
1
-C
4
hydroxyalkyl radical; a C
1
-C
4
aminoalkyl radical; a C
1
-C
4
dialkylamino (C
1
-C
4
) alkyl radical; a C
1
-C
4
alkylamino (C
1
-C
4
) alkyl radical; a C
1
-C
4
hydroxyalkylamino (C
1
-C
4
) alkyl radical; a C
1
-C
4
alkoxymethyl radical; a phenyl radical; a phenyl radical substituted with a halogen atom or with 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, nitro, trifluoromethyl, amino or C
1
-C
4
alkylamino radical; a heterocycle chosen from thiophene, furan and pyridine, or alternatively a radical —(CH
2
)
p
—O—(CH
2
)
q
—OR″, in which p and q are integers, which may be identical or different, from 1 to 3 inclusive and R″ represents a hydrogen atom or a methyl radical,
it being understood that, in the above formula (I):
at least one of the radicals R
2
, R
3
, R
4
and R
5
represents a hydrogen atom,
when R
2
, or respectively R
4
, represents a substituted or unsubstituted phenyl radical or a benzyl radical or a radical
R
3
, or respectively R
5
, cannot then represent any of these three radicals,
when R
4
and R
5
simultaneously represent a hydrogen atom, R
1
can then form, with R
2
and R
3
, a hexahydropyrimidine or tetrahydroimidazole heterocycle optionally substituted with a C
1
-C
4
alkyl or 1,2,4-tetrazole radical,
when R
2
, R
3
, R
4
and R
5
represent a hydrogen atom or a C
1
-C
6
alkyl radical, R
1
or R
6
may then also represent a 2-, 3- or 4-pyridyl, 2- or 3-thienyl or 2- or 3-furyl heterocyclic residue optionally substituted with a methyl radical or alternatively a cyclohexyl radical.
As indicated above, the colorations obtained with the oxidation dye composition in accordance with the invention are strong and make it possible to achieve shades ranging from red to blue. One of the essential characteristics of the oxidation bases in accordance with the invention, in particular relative to those described in the abovementioned document EP-A 375,977, lies in the presence of a substituent radical R
6
on the pyrazole ring.
In general, the addition salts with an acid which can be used in the context of the dye compositions of the invention (oxidation bases and couplers) are chosen in particular from the hydrochlorides, hydrobromides, sulphates, tartrates, lactates and acetates.
Among the 3-substituted 4,5-diaminopyrazoles of formula (I) which can be used as oxidation base in the compositions in accordance with the invention, mention may be made, in particular, of:
1-benzyl-4,5-diamino-3-methylpyrazole,
4,5-diamino-1-(&bgr;-hydroxyethyl)-3-(4′-methoxyphenyl)-pyrazole,
4,5-diamino-1-(&bgr;-hydroxyethyl)-3-(4′-methylphenyl)-pyrazole,
4,5-diamino-1-(&bgr;-hydroxyethyl)-3-(3′-methylphenyl)-pyrazole,
4,5-diamino-3-methyl-1-isopropylpyrazole,
4,5-diamino-3-(4′-methoxyphenyl)-1-isopropyl-pyrazole,
4,5-diamino-1-ethyl-3-methylpyrazole,
4,5-diamino-1-ethyl-3-(4′-methoxyphenyl)pyrazole,
4,5-diamino-3-hydroxymethyl-1-methylpyrazole,
4,5-diamino-1-ethyl-3-hydroxymethylpyrazole,
4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole,
4,5-diamino-3-hydroxymethyl-1-tert-butylpyrazole,
4,5-diamino-3-hydroxymethyl-1-phenylpyrazole,
4,5-diamino-3-hydroxymethyl-1-(2′-methoxyphenyl)-pyrazole,
4,5-diamino-3-hydroxymethyl-1-(3′-methoxyphenyl)-pyrazole,
4,5-diamino-3-hydroxymethyl-1-(4′-methoxyphenyl)-pyrazole,
1-benzyl-4,5-di
Burande Agnes
Hocquaux Michel
Malle Gerard
Vidal Laurent
Elhilo Eisa
Gupta Yogendra N.
L'Oreal (S.A.)
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