Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1998-12-03
2001-06-19
Liott, Caroline D. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C423S567100, C423S573100
Reexamination Certificate
active
06248137
ABSTRACT:
The invention relates to novel compositions for the oxidation dyeing of keratinous fibers, comprising at least one 3-aminopyrazolo[1,5-a]-pyrimidine as an oxidation base, the method of dyeing which employs this composition, novel 3-amino-pyrazolo[1,5-a]pyrimidines, and the process for their preparation.
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 and 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 lightly colored compounds which, when combined with oxidizing products, are able to give rise to colored compounds and dyes by a process of oxidative condensation. These compounds have the common feature of possessing one amino group and one hydroxyl group or two amino groups, which give them their oxidation-base character.
It is also known that the shades obtained with these oxidation bases can 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 diversity of 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. Hence 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, inclement weather, washing, permanent-waving, perspiration and friction).
The dyes should also allow white hairs to be covered and, finally, they should be as unselective as possible - in other words, they should allow the smallest possible differences in coloration to be produced over the entire length of a single keratinous fiber, which may vary in condition of sensitization or damage from its tip to its root.
Patent application DE 4 029 324 proposes the use of certain 2-hydroxypyrazolo[1,5-a]pyrimidines, which may be substituted by C
1
-C
4
alkyl radicals in positions 4, 5 and/or 6, as couplers for the oxidation dyeing of keratinous fibers.
Patent application DE 4 133 957 also proposes the use of certain pyrazolo-[1,5-a]pyrimidine derivatives, belonging to the class of the tetrahydropyrazolo[1,5-a]pyrimidines, as oxidation dye precursors for the oxidation dyeing of keratinous fibers.
The inventors have now made the unexpected and surprising discovery that a new class of 3-aminopyrazolo[1,5-a]pyrimidines of formula (I) defined below, some of which are themselves novel, are suitable for use as an oxidation base. These compounds contain only a single amino group that makes it possible to obtain dyeing compositions which lead to colorations which are strong and have good resistance to external agents (light, inclement weather, washing, permanent-waving, perspiration and friction). Finally, these compounds can be easy to synthesize.
These discoveries form the basis of the present invention.
The invention therefore provides a composition for the oxidation dyeing of keratinous fibers, and in particular human keratinous fibers such as hair, that comprises, in a medium suitable for dyeing, at least one 3-aminopyrazolo[1,5-a]pyrimidine chosen from compounds of formula (I) below and acid and base addition salts thereof, as oxidation base:
in which
R
1
, R
2
, R
3
and R
4
are identical or different and represent a hydrogen atom, a halogen atom, a C
1
-C
4
alkyl radical, a C
1
-C
4
trifluoroalkyl radical, a C
1
-C
4
alkoxy radical, an aryl radical, a C
1
-C
4
monohydroxyalkyl radical, a C
2
-C
4
polyhydroxyalkyl radical, a C
1
-C
4
(C
1
-C
4
alkoxy)alkyl radical, a C
1
-C
4
aminoalkyl radical, a C
1
-C
4
(C
1
-C
4
alkyl)aminoalkyl radical, a C
1
-C
4
di(C
1
-C
4
alkyl)aminoalkyl radical, a C
1
-C
4
monohydroxy (C
1
-C
4
alkyl)aminoalkyl radical or a C
1
-C
4
di[hydroxy(C
1
-C
4
alkyl)]aminoalkyl radical.
Among the 3-aminopyrazolo[1,5-a]pyrimidines of formula (I) which can be used as an oxidation base in the compositions in accordance with the invention generally preferred 3-aminopyrazolo[1,5-a]pyrimidines are:
pyrazolo[1,5-a]pyrimidin-3-ylamine;
5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylamine;
5,6,7-trimethylpyrazolo[1,5-a]pyrimidin-3-ylamine;
7-methylpyrazolo[1,5-a]pyrimidin-3-ylamine;
5,6,7-trimethylpyrazolo[1,5-a]pyrimidin-3-ylamine;
7-methylpyrazolo[1,5-a]pyrimidin-3-ylamine;
5-methylpyrazolo[1,5-a]pyrimidin-3-ylamine;
7-methoxy-5-methylpyrazolo[1,5-a]pyrimidin-3 -ylamine;
2,5,6,7-tetramethylpyrazolo[1,5-a]pyrimidin-3-ylamine;
2-methoxy-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylamine;
5,7-di-tert-butylpyrazolo[1,5-a]pyrimidin-3-ylamine;
5,7-di-trifluoromethylpyrazolo[1,5-a]pyrimidin-3-ylamine;
2,6-dimethylpyrazolo[1,5-a]pyrimidin-3-ylamine;
2-chloro-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylamine;
7-methyl-2-tert-butyl-5-trifluoromethylpyrazolo-[1,5-a]pyrimidin-3-ylamine; and the acid or base addition salts thereof.
Among the 3-aminopyrazolo[1,5-a]pyrimidines of formula (I) which can be used as an oxidation base in the compositions in accordance with the invention particularly preferred 3-aminopyrazolo [1,5-a]pyrimidines are:
pyrazolo[1,5-a]pyrimidin-3-ylamine;
5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylamine;
5,6,7-trimethylpyrazolo[1,5-a]pyrimidin-3-ylamine;
2,5,6,7-tetramethylpyrazolo[1,5-a]pyrimidin-3-ylamine;
2-methoxy 5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylamine;
5,7-di-trifluoromethylpyrazolo[1,5-a]pyrimidin-3-ylamine;
7-methylpyrazolo[1,5-a]pyrimidin-3-ylamine;
5-methylpyrazolo[1,5-a]pyrimidin-3-ylamine; and the acid or base addition salts thereof.
The great majority of the 3-aminopyrazolo[1,5-a]pyrimidines of formula (I) are compounds which are known in the pharmaceutical field and are described, in particular, in patent applications EP-A-0 433 854 and EP-A-0 433 855.
The 3-aminopyrazolo[1,5-a]pyrimidine or -pyrimidines of formula (I) above makes or make up preferably from 0.0005 to 12% by weight approximately relative to the total weight of the dyeing composition and, more preferably, from 0.005 to 6% by weight, approximately, of the total weight.
A medium (or vehicle) suitable for dyeing is, for example, water, water/alcohol mixtures, and a mixture of water and at least one organic solvent to dissolve any compounds which are not sufficiently water soluble. Preferred organic solvents are, for example, C
1
-C
4
lower alkanols, such as ethanol and isopropanol; glycerol; glycols and glycol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether and diethylene glycol monoethyl and monomethyl ether, and aromatic alcohols such as benzyl alcohol or phenoxyethanol, similar products and mixtures thereof.
The solvents can be present in proportions preferably ranging from 1 to 40% by weight approximately relative to the total weight of the dyeing composition, and even more preferably from 5 to 30% by weight approximately.
The pH of the dyeing composition in accordance with the invention generally ranges from 3 to 12, approximately, and preferably approximately from 5 to 11. It can be adjusted to the desired value by means of acidifying or basifying agents commonly used in the dyeing of keratinous fibers, or by using conventional buffer systems.
Preferred acidifying agents include, for example, mineral acids or organic acids, such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid and lactic acid, and sulphonic acids.
Preferred basifying agents
Fadli Aziz
Lagrange Alain
Terranova Eric
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
L'Oreal (S.A.)
Liott Caroline D.
LandOfFree
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