Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2000-01-05
2004-09-28
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S407000, C008S423000, C008S426000
Reexamination Certificate
active
06797013
ABSTRACT:
The invention relates to a composition for the oxidation dyeing of keratin fibres, and in particular human keratin fibres such as the hair, comprising, in a medium which is suitable for dyeing, at least one heterocyclic oxidation base and at least one 3-aminopyridine derivative as direct dye, as well as to the dyeing process using this composition.
It is known practice to dye keratin fibres, and in particular human hair, with dye compositions containing oxidation dye precursors, in particular ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic bases, which are generally referred to as oxidation bases. Oxidation dye precursors, or oxidation bases, are colourless or weakly coloured compounds which, when combined with oxidizing products, can give rise to coloured 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 colour 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 regards the oxidation bases and couplers allows a wide range of colours to be obtained.
It is also known that, in order to vary the shades obtained even more and to give them glints, it is possible to use, in combination with the oxidation dye precursors and couplers, direct dyes, i.e. coloured substances which provide a coloration in the absence of an oxidizing agent.
The great majority of these direct dyes belong to the family of nitrobenzene compounds and have the drawback, when they are incorporated into dye compositions, of leading to colorations that are not sufficiently fast, in particular with respect to shampoos.
The so-called “permanent” coloration obtained by means of these oxidation dyes must moreover satisfy a certain number of requirements. Thus, it must be able to give shades of the desired intensity and it must be able to withstand external agents (light, bad weather, washing, permanent-waving, perspiration and rubbing).
The dyes must also make it possible to cover white hair, and, finally, they must be as unselective as possible, i.e. they must give the smallest possible differences in colour all the way along the same keratin fibre, which may indeed be differently sensitized (i.e. damaged) between its tip and its root.
Compositions for the oxidation dyeing of keratin fibres containing a combination of a benzenic oxidation base and a direct dye of the 3-aminopyridine family have already been proposed, in particular in patent application FR-A-2,285,851. However, the colorations obtained using such compositions are not entirely satisfactory, in particular from the point of view of their chromaticity and their fastness.
The Applicant has now discovered that it is possible to obtain novel dyes which are capable of giving intense and chromatic colorations, which show little selectivity and which satisfactorily withstand the various attacking factors to which the fibres may be subjected, by combining at least one heterocyclic oxidation base and at least one suitably selected 3-aminopyridine derivative as direct dye.
This discovery forms the basis of the present invention.
A first subject of the invention is thus a composition for the oxidation dyeing of keratin fibres, and in particular of human keratin fibres such as the hair, characterized in that it comprises, in a medium which is suitable for dyeing:
at least one heterocyclic oxidation base and
as direct dye, at least one 3-aminopyridine derivative chosen from the compounds of formula (I) below:
in which:
B represents a group of formula (Ia) or (Ib) below:
R represents a C
1
-C
4
alkyl radical;
R
1
represents a hydrogen or halogen atom such as chlorine, bromine or fluorine, or a C
1
-C
4
alkyl or C
1
-C
4
alkoxy radical;
R
2
represents a hydrogen atom or a C
1
-C
4
alkyl or C
1
-C
4
alkoxy radical;
R
4
represents a hydrogen or halogen atom such as chlorine, bromine or fluorine, or a C
1
-C
4
alkyl, nitro, amino or (C
1
-C
4
)acylamino radical;
R
3
represents a hydrogen atom or else R
4
and R
3
together form a 6-membered unsaturated ring bearing a hydroxyl substituent chelated with one of the nitrogen atoms of the azo double bond;
A represents a residue —NR
5
R
6
in which R
5
represents a hydrogen atom or a C
1
-C
4
alkyl, C
1
-C
4
monohydroxyalkyl or C
2
-C
4
polyhydroxyalkyl radical; R
6
represents a hydrogen atom, a C
1
-C
4
alkyl, C
1
-C
4
monohydroxyalkyl or C
2
-C
4
polyhydroxyalkyl radical, a phenyl ring or a —CH
2
—SO
3
Na radical;
X
−
represents a monovalent or divalent anion and is preferably chosen from a halogen atom such as chlorine, bromine, fluorine or iodine, a hydroxide, a hydrogen sulphate or a (C
1
-C
6
)alkyl sulphate such as, for example, a methyl sulphate or an ethyl sulphate.
The dye composition in accordance with the invention gives intense, chromatic colorations which show little selectivity and excellent properties of resistance both with respect to atmospheric agents such as light and bad weather, and with respect to perspiration and the various treatments to which the hair may be subjected. These properties are particularly noteworthy as regards the chromaticity.
A subject of the invention is also a process for the oxidation dyeing of keratin fibres using this dye composition.
The heterocyclic oxidation base(s) is(are) preferably chosen from pyridine derivatives, pyrimidine derivatives and pyrazole derivatives, and the addition salts thereof with an acid.
Among the pyridine derivatives, mention may be made more particularly of the compounds described, for example, in GB patents 1,026,978 and 1,153,196, such as 2,5-diaminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine, 2,3-diamino-6-methoxypyridine, 2-(&bgr;-methoxyethyl)amino-3-amino-6-methoxypyridine and 3,4-diaminopyridine, and the addition salts thereof with an acid.
Among the pyrimidine derivatives, mention may be made more particularly of the compounds described, for example, in German patent DE 2,359,399 or Japanese patents JP 88-169,571 and JP 91-333,495, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, and the addition salts thereof with an acid, and also pyrazolopyrimidine derivatives, such as pyrazolo[1,5-a]pyrimidine-3,7-diamine, 2-methyl-pyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,5-dimethyl-pyrazolo[1,5-a]pyrimidine-3,7-diamine, pyrazolo-[1,5-a]pyrimidine-3,5-diamine, 2,7-dimethylpyrazolo-[1,5-a]pyrimidine-3,5-diamine, 3-aminopyrazolo[1,5-a]-pyrimidin-7-ol, 3-amino-5-methylpyrazolo[1,5-a]-pyrimidin-7-ol, 3-aminopyrazolo[1,5-a]pyrimidin-5-ol, 2-(3-aminopyrazolo[1,5-a]pyrimidin-7-ylamino)ethanol, 3-amino-7-&bgr;-hydroxyethylamino-5-methylpyrazolo[1,5-a]-pyrimidine, 2-(7-aminopyrazolo[1,5-a]pyrimidin-3-ylamino)ethanol, 2-[(3-aminopyrazolo[1,5-a]pyrimidin-7-yl)-(2-hydroxyethyl)amino]ethanol, 2-[(7-amino-pyrazolo[1,5-a]pyrimidin-3-yl)-(2-hydroxyethyl)-amino]ethanol, 5,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine and 2,5, N7,N7-tetramethylpyrazolo[1,5-a]-pyrimidine-3,7-diamine, and the addition salts thereof and the tautomeric forms thereof, when a tautomeric equilibrium exists.
Among the pyrazole derivatives, mention may be made more particularly of the compounds described in patents or patent applications DE 3,843,892, DE 4,133,957, DE 4,234,886, DE 4,234, 887, FR 2,733,749, FR 2,735,685, WO 94/08969 and WO 94/08970, such as 4,5-diaminopyrazole, 4,5-diamino-1-methylpyrazole, 1-benzyl-4,5-diaminopyrazole, 3,4-diaminopyrazole, 1-benzyl-4,5-diamino-3-methylpyrazole, 4-amino-1,3-dimethyl-5-hydrazinopyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-3-methyl-1-tert-butylpyrazole, 4,5-diamino-1-methyl-3-tert-butylpyrazole, 4,5-diamino-1-ethyl-3-methylpyrazole, 4,5-diamino-1-ethyl-3-(4′
Cotteret Jean
Lang Gerard
Maubru Mireille
Einsmann Margaret
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
L'Oreal (S.A.)
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