Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-11-19
2002-05-21
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S408000, C008S409000, C008S411000, C008S416000
Reexamination Certificate
active
06391063
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 substituted meta-phenylenediamine 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 oxidation bases, one or more 2,6-diaminotoluene derivatives as coupler, and optionally one or more additional couplers chosen from the couplers conventionally used in the field of oxidation dyeing, have already been proposed, in particular in patent applications FR-A-2,681,860 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 substituted meta-phenylenediamine 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 a second coupler chosen from the substituted meta-phenylenediamines 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
1
-C
4
monohydroxyalkyl radical or a C
2
-C
4
polyhydroxyalkyl radical;
R
2
and R
3
, which may be identical or different, represent a hydrogen atom, a C
1
-C
4
alkyl radical or a C
1
-C
4
hydroxyalkoxy radical;
R
4
represents a C
1
-C
4
alkoxy radical, a C
1
-C
4
aminoalkoxy radical, a C
1
-C
4
monohydroxyalkoxy radical, a C
2
-C
4
polyhydroxyalkoxy radical or a 2,4-diaminophenoxyalkoxy radical;
it being understood that when R
1
, R
2
and R
3
simultaneously represent a hydrogen atom, then R
4
is other than a methoxy radical.
The dye composition in accordance with the invention gives intense, highly chromatic colorations which have excellent properties of resistance 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. These properties are particularly noteworthy especially as regards the resistance of the colorations towards the action of permanent-waving.
A subject of the invention is also a process for the oxidation dyeing keratin fibres using this dye composition.
Among the substituted meta-phenylenediamines of formula (I) above which may be mentioned more particularly are 2,4-diaminophenoxyethanol, 2,4-diamino-1-ethoxybenzene, 2-amino-4-N-(&bgr;-hydroxyethyl)aminoanisole, 3,5-diamino-1-ethyl-2-methoxybenzene, 3,5-diamino-2-methoxy-1-methylbenzene, 1,3-bis(2,4-diaminophenoxy)propane, bis-(2,4-diaminophenoxy)methane, 1-(&bgr;-aminoethyloxy)-2,4-diaminobenzene, 2-amino-1-(&bgr;-hydroxyethyloxy)-4-methylaminobenzene, 2,4-diamino-1-ethoxy-5-methylbenzene, 2,4-diamino-5-(&bgr;-hydroxyethyloxy)-1-methylbenzene, 2,4-diamino-1-(&bgr;,&ggr;-dihydroxy-propyloxy)benzene and 2-amino-4-N-(&bgr;-hydroxyethyl)-amino-1-methoxybenzene and the addition salts thereof with an acid.
The nature of the oxidation base(s) used in the ready-to-use dye composition is not critical. They can be chosen in particular from para-phenylenediamines, double bases, para-aminophenols, ortho-aminophenols and heterocyclic oxidation bases.
Among the para-phenylenediamines which can be used as oxidation base in the dye compositions in accordance with the invention, mention may be made in particular of the compounds of formula (II) below, and the addition salts thereof with an acid:
in which:
R
5
represents a hydrogen atom, a C
1
-C
4
alkyl radical, a C
1
-C
4
monohydroxyalkyl radical, a C
2
-C
4
polyhydroxyalkyl radical, a (C
1
-C
4
)alkoxy(C
1
-C
4
)alkyl radical or a C
1
-C
4
alkyl radical substituted with a nitrogenous, phenyl or 4′-aminophenyl group;
R
6
represents a hydrogen atom, a C
1
-C
4
alkyl radical, a C
1
-C
4
monohydroxyalkyl radical, a C
2
-C
4
polyhydroxyalkyl radical, a (C
1
-C
4
)alkoxy(C
1
-C
4
)alkyl radical or a C
1
-C
4
alkyl radical substituted with a nitrogenous group;
R
7
represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, a C
1
-C
4
alkyl radical, a C
1
-C
4
monohydroxyalkyl radical, a C
1
-C
4
hydroxyalkoxy radical, a C
1
-C
4
acetylaminoalkoxy radical, a C
1
-C
4
mesylaminoalkoxy radical or a C
1
-C
4
carbamoylaminoalkoxy radical,
R
8
represents a hydrogen or halogen atom or a C
1
-C
4
alkyl radical.
Among the nitrogenous groups of formula (II) above which may be mentioned in particular are amino, mono(C
1
-C
4
)alkylamino, di(C
1
-C
4
)alkylamino, tri(C
1
-C
4
)alkylamino, monohydroxy(C
1
-C
4
)alkylamino, imidazolinium and ammonium radicals.
Among the para-phenylenediamines of formula (II) above, mention may be made more particularly of para-phenylenediamine, para-tolylenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para-phenylenediamine, N,N-diethyl-para-phenylenediamine, N,N-dipropyl-para-phenylenediamine, 4-amino-N,N-diethyl-3-methylaniline, N,N-bis(&bgr;-hydroxyethyl)-para-phenylene-diamine, 4-N,N-bis(&bgr;-hydroxyethyl)amino-2-methylaniline, 4-N,N-bis(&bgr;-hydroxyethyl)amino-2-chloroaniline, 2-&bgr;-hydroxyethyl-para-phenylenediamine, 2-fluoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-(&bgr;-hydroxypropyl)-para-phenylenediamine, 2-hydroxymethyl-para-phenylenediamine, N,N-dimethyl-3-methyl-
Einsmann Margaret
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
L'Oreal
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