Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-11-19
2002-05-28
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S408000, C008S410000, C008S423000
Reexamination Certificate
active
06395042
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 oxidation base, 1,3-bis(&bgr;-hydroxyethyl)amino-2-methylbenzene and/or at least one of the addition salts thereof with an acid as first coupler, and at least one selected heterocyclic coupler as second coupler, 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 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 allows a wide range of colours 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 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, rubbing).
The dyes must also be able to cover white hair and, lastly, they must be as unselective as possible, i.e. they must give the smallest possible coloration differences along the same length of keratin fibre, which may in fact be differently sensitized (i.e. damaged) between its tip and its root.
Compositions for the oxidation dyeing of keratin fibres containing one or more oxygen bases, one or more 2,6-diaminotoluene derivatives as second coupler, and optionally one or more additional couplers chosen from the couplers conventionally used in the field of oxidation dyeing, such as resorcinol and derivatives thereof, naphthalene derivatives or pyridine derivatives, have already been proposed, in particular in patent applications DE-A-4,132,615 and DE-A-19,637,371. However, although the colorations obtained using such compositions are highly chromatic, they are not entirely satisfactory, in particular as regards their fastness with respect to the various treatments and natural attacking factors to which keratin fibres may be subjected.
The Applicant has now discovered that it is possible to obtain novel dyes which are capable of giving intense and highly chromatic colorations, and which show good resistance to the various attacking factors to which the fibres may be subjected, by combining at least one oxidation base, 1,3-bis(&bgr;-hydroxyethyl)amino-2-methylbenzene and/or at least one of the addition salts thereof with an acid as first coupler, and at least one suitably selected heterocyclic coupler as second coupler.
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 human keratin fibres such as the hair, characterized in that it comprises, in a medium which is suitable for dyeing:
at least one oxidation base,
1,3-bis(&bgr;-hydroxyethyl)amino-2-methylbenzene and/or at least one of the addition salts thereof with an acid, as first coupler; and
at least one heterocyclic coupler, as second coupler;
it being understood that when the dye composition contains a pyrimidine oxidation base and/or 2-&bgr;-hydroxyethyl-para-phenylenediamine and/or one of the addition salts thereof with an acid, then the heterocyclic coupler is other than a pyridine coupler.
The dye composition in accordance with the invention gives intense, highly chromatic colorations which show excellent resistance properties with respect both to atmospheric agents such as light and bad weather, and to perspiration and the various treatments to which the hair may be subjected.
A subject of the invention is also a process for the oxidation dyeing of keratin fibres using this dye composition.
Among the heterocyclic couplers which can be used as second couplers in the dye composition according to the invention, mention may be made in particular of indole derivatives, indoline derivatives, benzimidazole derivatives, benzomorpholine derivatives, sesamol derivatives, pyrazoloazole derivatives, pyrroloazole derivatives, imidazoloazole derivatives, pyrazolopyrimidine derivatives, pyrazoline-3,5-dione derivatives, pyrrolo[3,2-d]oxazole derivatives, pyrazolo[3,4-d]thiazole derivatives, thiazoloazole S-oxide derivatives, thiazoloazole S,S-dioxide derivatives and pyridine derivatives, and the addition salts thereof with an acid.
Among the indole derivatives which can be used as heterocyclic couplers in the dye composition in accordance with the invention, mention may be made more particularly of the compounds of formula (I) below, and the addition salts thereof with an acid:
in which:
R
1
represents a hydrogen atom, a C
1
-C
4
alkyl radical, a C
2
-C
4
mono- or polyhydroxyalkyl radical or a C
1
-C
4
aminoalkyl radical in which the amine is mono- or disubstituted with a C
1
-C
4
alkyl group;
R
2
represents a hydrogen atom or a C
1
-C
4
alkyl radical;
R
3
represents a hydrogen atom or a C
1
-C
4
alkyl or hydroxyl radical;
X represents a hydroxyl radical or a radical NHR
4
in which R
4
represents a hydrogen atom or a C
1
-C
4
alkyl or C
1
-C
4
hydroxyalkyl radical.
Among the indole derivatives of formula (I) above, mention may be made more particularly of 4-hydroxyindole, 6-hydroxyindole, 7-aminoindole, 6-aminoindole, 7-hydroxyindole, 7-ethyl-6-(&bgr;-hydroxyethyl)aminoindole, 4-aminoindole, 6-hydroxy-1-methylindole, 5,6-dihydroxyindole, 4-hydroxy-1-N-methylindole, 4-hydroxy-2-methylindole, 4-hydroxy-5-methylindole, 4-hydroxy-1-N-(&bgr;-hydroxyethyl)indole, 4-hydroxy-1 -N-(&bgr;-hydroxypropyl) indole, 1-N-(&bgr;,&ggr;-dihydroxypropyl)-4-hydroxyindole, 4-hydroxy-1-N-(&bgr;-hydroxyethyl)-5-methylindole and 1-N-(g-dimethylaminopropyl)4-hydroxyindole, and the addition salts thereof with an acid.
Among the indoline derivatives which can be used as heterocyclic couplers in the dye composition in accordance with the invention, mention may be made in particular of 4-hydroxyindoline, 6-hydroxyindoline, 6-aminoindoline and 5,6-dihydroxyindoline, and the addition salts thereof with an acid.
Among the benzimidazole derivatives which can be used as heterocyclic couplers in the dye composition in accordance with the invention, mention may be made more particularly of the compounds of formula (II) below, and the addition salts thereof with an acid:
in which:
R
5
represents a hydrogen atom or a C
1
-C
4
alkyl radical, R
6
represents a hydrogen atom or a C
1
-C
4
alkyl or phenyl radical, R
7
represents a hydroxyl, amino or methoxy radical,
R
8
represents a hydrogen atom or a hydroxyl, methoxy or C
1
-C
4
alkyl radical;
with the proviso that:
when R
7
denotes an amino radical, then it occupies position 4,
when R
7
occupies position 4, then R
8
occupies position 7,
when R
7
occupies position 5, then R
8
occupies position 6.
Among the benzimidazole derivatives of formula (II) above, mention may be made more particularly of 4-hydroxybenzimidazole, 4-aminobenzimidazole, 4-hydroxy-7-methylbenzimidazole, 4-hydroxy-2-methylbenzimidazole, 1-butyl-4-hydroxybenzimidazole, 4-amino-2-methylbenzimidazole, 5,6-dihydroxybenzimidazole, 5-hydroxy-6-methoxy-benzimidazole, 4,7-dihydroxybenzimidazole, 4,7-dihydroxy-1-methylbenzimidazole, 4,7-dimethoxybenzimidazole, 5,6-dihydroxy-1-methylbenzimidazole, 5,6-dihydroxy-2-methylbenzimidazole and 5,6-dimethoxybenzimidazole, and the addition salts thereof with an acid.
Among the benzomorpholine derivatives whic
Einsmann Margaret
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
L'Oreal
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