Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2002-09-26
2004-11-30
Kopec, Mark (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S406000, C008S407000, C008S437000, C008S441000, C008S451000, C008S463000, C008S568000, C008S570000, C008S572000, C008S573000, C008S574000, C132S202000, C132S208000
Reexamination Certificate
active
06824570
ABSTRACT:
The present invention relates to a dye composition for dyeing human keratin fibres, such as hair, comprising at least one monocationic monoazo dye. The present invention also relates to the processes for dyeing human keratin fibres, such as hair, using such a composition. The present invention further relates to novel monocationic monoazo compounds.
It is a known practice to dye human keratin fibres, such as hair, with dye compositions containing oxidation dye precursors, generally referred to as oxidation bases, such as ortho- or para-phenylenediamines, ortho- or para-aminophenols, and heterocyclic compounds. These oxidation bases are generally colourless or weakly coloured compounds that, when combined with oxidizing agents, may give rise to coloured compounds 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. These couplers or colour modifiers may be chosen, for example, from aromatic meta-diamines, meta-aminophenols, meta-diphenols, and certain heterocyclic compounds such as indole compounds.
The variety of molecules used as oxidation bases and couplers can allow for a wide range of colours to be obtained.
This oxidation dyeing process comprises applying to the keratin fibres, oxidation bases or a mixture of oxidation bases and couplers, with an oxidizing agent, for example, aqueous hydrogen peroxide; leaving the mixture to stand on the fibres; and then rinsing the fibres. The colorations which result from the oxidation dyeing process can be permanent, strong, and resistant to external agents, such as light, bad weather, washing, perspiration, and rubbing. The oxidation dyeing process, which is generally applied at basic pH, makes it possible to obtain dyeing and simultaneously lightening of the fibre, making it possible to obtain a final coloration that is lighter than the original colour. Additionally, the lightening of the fibre can have the advantageous effect of giving rise to a uniform colour in the case of grey hair, and, in the case of naturally pigmented hair, of bringing the colour out, i.e., of making it more visible.
It is also a known practice to dye human keratin fibres by direct dyeing. The process conventionally used in direct dyeing comprises applying to the keratin fibres direct dyes, which are coloured, and colouring molecules having an affinity for the fibres, leaving the dyes to stand on the fibres, and then rinsing the fibres.
It is also a known practice, for example, to use nitrobenzene, anthraquinone or nitropyridine direct dyes, azo, xanthene, acridine or azine dyes or triarylmethane dyes.
The resulting colorations from the direct dyes can be chromatic colorations that can, however, be temporary or semi-permanent. The nature of the interactions that bind the direct dyes to the keratin fibre, and their desorption from the surface and/or from the core of the fibre, can be responsible for their weak dyeing capacity, and for their poor resistance to washing or to perspiration. These direct dyes can also be sensitive to light due to the poor resistance of the chromophore to photochemical attacks that lead, over time, to a dulling of the coloration of the hair. Additionally, their sensitivity to light is dependent on whether they are distributed uniformly or in aggregates in the keratin fibre.
Another known practice is to use direct dyes in combination with oxidizing agents. However, the direct dyes can be sensitive to the action of oxidizing agents such as aqueous hydrogen peroxide, and reducing agents such as sodium bisulphite, which generally makes them difficult to use in lightening direct dye compositions based on aqueous hydrogen peroxide and on a basifying agent, or in oxidation dyeing compositions in combination with precursors such as oxidation bases or couplers.
For example, in patent applications FR-1 584 965 and JP-062 711 435, it has been proposed to dye the hair with dye compositions based on direct nitro dyes, and/or on dispersed azo dyes, and on ammoniacal aqueous hydrogen peroxide, by applying to the hair a mixture of said dyes and of said oxidant, prepared just before use. The colorations obtained by this approach, however, can prove to be insufficiently durable, and disappear with shampooing, thus allowing lightening of the hair fibre to appear. By changing over time, such a coloration becomes unaesthetic.
In patent applications JP-53 95693 and JP-55 022638, it has also been proposed to dye the hair with compositions based on cationic direct dyes of the oxazine type and of ammoniacal aqueous hydrogen peroxide, by applying to the hair, in a first step, ammoniacal aqueous hydrogen peroxide, and in a second step, a composition based on the oxazine direct dye. This coloration can be unsatisfactory, due to the fact that it requires a process in which the product needs to be left to stand on the hair for a long time in the two successive steps. If, moreover, an extemporaneous mixture of the oxazine direct dye with ammoniacal aqueous hydrogen peroxide is applied to the hair, then no coloration can be obtained or, at the very least, a virtually nonexistent coloration of the hair fibre can be obtained.
More recently, patent application FR 2 741 798 described dye compositions containing direct dyes comprising at least one quarternized nitrogen atom of the azo or azomethine type, wherein said compositions need to be mixed extemporaneously at basic pH with an oxidizing composition. These compositions make it possible to obtain colorations with homogeneous, durable, and brilliant glints. However, they may not dye keratin fibres with as much strength as oxidation dyeing compositions.
There is therefore a need for chromatic direct dyes which can dye human keratin fibres as strongly as oxidation dyes, and/or can be as stable as oxidation dyes when exposed to light, bad weather, washing, and perspiration. Additionally, there is a need for chromatic direct dyes that can be sufficiently stable in the presence of oxidizing and reducing agents to be able to obtain simultaneously a lightening of the fibre either by using direct lightening compositions comprising them, or by using oxidation dye compositions based on oxidation dye precursors comprising them. There is also a need for direct dyes which can dye human keratin fibres in a wide range of colours, such as chromatic colours, as well as the “fundamental” shades such as blacks and browns.
The present invention therefore relates to a composition for dyeing human keratin fibres, such as hair, comprising, in a cosmetically acceptable medium, at least one monocationic monoazo dye of formula (I) below:
W
1
—W
2
—N═N—W
3
Formula (I)
wherein:
W
1
is chosen from 5-, 6-, 7- and 8-membered heterocycles of formula (II) below:
W
2
is chosen from divalent, aromatic, and carbon-based pyridines and pyridazines of formula (III) below:
W
3
is chosen from cationic heteroaromatic radicals of formula (IV) below:
wherein in formulae (II), (III) and (IV):
n=0, 1, 2 or 3, provided that when n is greater than or equal to 2, then the R
4
radicals may be identical or different,
X
1
is chosen from a nitrogen atom and CR
7
radicals,
X
2
is chosen from a nitrogen atom and CR
8
radicals,
Z
1
is chosen from CHR
2
radicals, oxygen and sulphur atoms, and NR
14
radicals,
Z
2
is chosen from oxygen and sulphur atoms, and NR
15
radicals,
R
0
, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, R
11
and R
12
, which may be identical or different, are each chosen from a hydrogen atom, linear and branched C
1
-C
10
hydrocarbon-based chains, possibly forming at least one carbon-based ring comprising from 3 to 6 members, and being saturated or unsaturated, wherein at least one carbon atom of the hydrocarbon-based chains may be replaced with an entity chosen from oxygen, nitrogen, and sulphur atoms, and an SO
2
group, and wherein the carbon atoms may be, independently of one another, substituted, for example, with at least one halogen atom; R
0
, R
1
, R
2
, R
3
, R
4
,
Fadli Aziz
Vidal Laurent
Elhilo Eisa
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
Kopec Mark
L'Oreal (S.A.)
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