Compositions for dyeing keratin fibers, containing...

Details Compositions for dyeing keratin fibers, containing... Compositions for dyeing keratin fibers, containing...

1999-07-19

2002-05-14

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

C008S407000, C008S408000, C008S410000, C008S411000, C008S412000, C008S423000

Reexamination Certificate

active

06387136

ABSTRACT:

The invention relates to novel compositions for the oxidation dyeing of keratin fibers, comprising at least one oxidation base and at least one 3-aminopyrazoline derivative suitably selected as coupler, to the dyeing process using this composition and an oxidizing agent, as well as to the corresponding dyeing kit.
It is known practice 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. Oxidation dye precursors, or oxidation bases, are colorless or weakly colored compounds which, when combined with oxidizing products, can 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 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.
The variety of compounds used with regards to the oxidation bases and the couplers can produce a wide range of colors.
The so-called “permanent” coloration obtained by means of these oxidation dyes preferably satisfies a certain number of requirements. Thus, it should have no toxicological drawbacks, it should be able to give shades of the desired intensity and it should be able to withstand external agents (light, bad weather, washing, permanent-waving, perspiration, rubbing).
The dyes should also be able to cover white hair and, lastly, they should be as unselective as possible, i.e. they should give the smallest possible color differences along the same length of keratin fiber, which may in fact be differently sensitized (i.e. damaged) between its tip and its root.
It has already been proposed, in particular in patent application FR-A-2,018,056, the disclosure of which is incorporated by reference herein, to use certain 3-aminopyrazolines as oxidation bases, i.e., more precisely, 1-(4′-aminophenyl)-3-aminopyrazolines or 1-(4′-hydroxyphenyl)-3-aminopyrazolines, for the oxidation dyeing of keratin fibers.
The inventors have discovered, entirely surprisingly and unexpectedly, that the use of certain 3-aminopyrazolines of formula (I) defined below, is not only suitable for use as couplers for oxidation dyeing, but that they can also give particularly intense colorations, especially when they are combined with heterocyclic oxidation bases. Moreover, they make it possible to obtain dye compositions giving colorations which show good resistance to the various attacking factors to which the hair may be subjected. Lastly, these compounds prove to be easily synthesized.
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 of human keratin fibers such as the hair, characterized in that it comprises, in a medium which is suitable for dyeing:
at least one oxidation base, and
at least one coupler chosen from 3-aminopyrazolines of formula (I) below and the acid addition salts thereof:
 in which:
R
1
and R
2
, which may be identical or different, are chosen from a hydrogen atom; halogen atoms; C
1
-C
4
alkyl radicals; C
1
-C
4
monohydroxyalkyl radicals; C
1
-C
4
polyhydroxyalkyl radicals; (C
1
-C
4
)alkoxy(C
1
-C
4
)alkyl radicals; radicals OR
5
in which R
5
is chosen from a hydrogen atom, C
1
-C
4
alkyl radicals, aryl radicals, C
1
-C
4
monohydroxyalkyl radicals, C
2
-C
4
polyhydroxyalkyl radicals and (C
1
-C
4
)alkoxy(C
1
-C
4
)alkyl radicals;
R
3
and R
4
, which may be identical or different, are chosen from a hydrogen atom, halogen atoms; C
1
-C
4
alkyl radicals; C
1
-C
4
monohydroxyalkyl radicals; C
2
-C
4
polyhydroxyalkyl radicals; (C
1
-C
4
)alkoxy(C
1
-C
4
)alkyl radicals; C
1
-C
4
aminoalkyl radicals; C
1
-C
4
aminoalkyl radicals in which the amine is protected with a protecting group chosen from acetyl, amido, and sulphonyl radicals; (C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radicals; di[(C
1
-C
4
)alkyl]amino(C
1
-C
4
)alkyl radicals (it being possible for the dialkyls to form a 5- or 6-membered ring with the nitrogen atom to which they are bound, said ring being able to contain an additional heterocyclic atom); and mono[hydroxy(C
1
-C
4
)alkyl]amino(C
1
-C
4
)alkyl and di[hydroxy(C
1
-C
4
)alkyl]amino(C
1
-C
4
)alkyl radicals.
As mentioned above, the colorations obtained with the oxidation dye composition in accordance with the invention can be intense, most particularly when the compounds of formula (I) are used in combination with at least one heterocyclic oxidation base. The oxidation dye compositions in accordance with the invention furthermore make it possible to achieve shades in a very wide range of colors, which also can show excellent properties of resistance with respect to the action of the various external agents (light, bad weather, washing, permanent-waving, perspiration, rubbing).
In formula (I) above, the halogen atoms are chosen from bromine, chlorine, iodine and fluorine and the alkyl and alkoxy radicals can be linear or branched.
Among the 3-aminopyrazolines of formula (I) above which can be used as couplers in the dye compositions in accordance with the invention, mention may be made in particular of:
3-amino-1-phenylpyrazoline,
3-amino-1-phenyl-4-methylpyrazoline,
3-amino-1-phenyl-5-methylpyrazoline,
3-amino-1-phenyl-5-ethylpyrazoline,
3-amino-1-phenyl-5-n-propylpyrazoline,
3-amino-1-phenyl-5-isopropylpyrazoline,
3-amino-1-(2′-bromophenyl)pyrazoline,
3-amino-1-(3′-bromophenyl)pyrazoline,
3-amino-1-(4′-bromophenyl)pyrazoline,
3-amino-1-(2′-chlorophenyl)pyrazoline,
3-amino-1-(2′,4′-dichlorophenyl)pyrazoline,
3-amino-5-methyl-1-(2′,4′-dichlorophenyl)-pyrazoline,
3-amino-1-(3′-chlorophenyl)pyrazoline,
3-amino-1-(2′,5′-dichlorophenyl)pyrazoline,
3-amino-1-(2′,6′-dichlorophenyl)pyrazoline,
3-amino-1-(3′,4′-dichlorophenyl)pyrazoline,
3-amino-1-(3′,4′-dichlorophenyl)-4-methyl-pyrazoline,
3-amino-1-(3′,4′-dichlorophenyl)-5-methyl-pyrazoline,
3-amino-1-(3′,4′-dichlorophenyl)-5-ethyl-pyrazoline,
3-amino-1-(3′,5′-dichlorophenyl)pyrazoline,
3-amino-1-(3′-chloro-4′-methylphenyl)pyrazoline,
3-amino-5-methyl-1-(3′-chloro-4′-methylphenyl)-pyrazoline,
3-amino-1-(4′-amino-3′-chlorophenyl)pyrazoline,
3-amino-1-(4′-chlorophenyl)pyrazoline,
3-amino-1-(4′-chlorophenyl)-4-methylpyrazoline,
3-amino-1-(4′-chlorophenyl)-5-methylpyrazoline,
3-amino-1-(4′-chlorophenyl)-5-ethylpyrazoline,
3-amino-1-(4′-chlorophenyl)-5-n-propylpyrazoline,
3-amino-1-(4′-chlorophenyl)-4-n-butylpyrazoline,
3-amino-1-(4′-chlorophenyl)-5-n-butylpyrazoline,
3-amino-1-(2′-fluorophenyl)pyrazoline,
3-amino-1-(3′-fluorophenyl)pyrazoline,
3-amino-1-(4′-fluorophenyl)pyrazoline,
3-amino-1-(4′-fluorophenyl)-5-fluoropyrazoline,
3-amino-1-(4′-fluorophenyl)-4-methylpyrazoline,
3-amino-1-(4′-fluorophenyl)-5-methylpyrazoline,
3-amino-1-(4′-fluorophenyl)-5-ethylpyrazoline,
3-amino-1-(4′-fluorophenyl)-5-n-butylpyrazoline,
3-amino-5-methyl-1-(4′-fluorophenyl)pyrazoline,
3-amino-5-ethyl-1-(4′-fluorophenyl)pyrazoline,
3-amino-1-(4′-iodophenyl)pyrazoline,
3-amino-1-(2′-methylphenyl)pyrazoline,
3-amino-1-(3′-methylphenyl)pyrazoline,
3-amino-1-(4′-methylphenyl)pyrazoline,
3-amino-1-(4′-tert-butylphenyl)pyrazoline,
3-amino-1-(2′-methoxyphenyl)pyrazoline,
3-amino-1-(3′-methoxyphenyl)pyrazoline,
3-amino-1-(4′-methoxyphenyl)pyrazoline,
3-amino-1-(2′-ethoxyphenyl)pyrazoline,
3-amino-1-(3′-ethoxyphenyl)pyrazoline,
3-amino-1-(4′-ethoxyphenyl)pyrazoline,
3-amino-1-(4′,3′-dimethoxyphenyl)pyrazoline, and

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