Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-05-28
2002-08-20
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S407000, C008S429000, C008S431000, C008S609000, C008S610000, C008S611000, C008S613000, C008S654000, C008S655000, C008S657000, C008S659000
Reexamination Certificate
active
06436153
ABSTRACT:
The invention relates to a direct dye composition for keratin fibres, in particular for human keratin fibres such as the hair, comprising, in a medium which is suitable for dyeing and which is free of oxidases or oxidoreductases, at least one cationic direct dye of given formula and at least one specific polyol and/or polyol ether.
Subjects of the invention are also the dyeing processes and devices using the said composition.
In the hair sector, semi-permanent or temporary dyeing, or direct dyeing, involves dyes capable of giving the hair's natural colour a more or less pronounced change which may withstand shampooing several times. These dyes are known as direct dyes; they can be used with or without an oxidizing agent. In the presence of an oxidizing agent, the aim is to obtain a lightening coloration. The lightening coloration is carried out by applying to the hair the mixture, prepared at the time of use, of a direct dye and an oxidizing agent, and in particular makes it possible to obtain, by lightening the melanin in the hair, an advantageous effect such as a uniform colour in the case of grey hair, or to bring out the colour in the case of naturally pigmented hair.
Among the cationic direct dyes available in the field of dyeing keratin fibres, in particular human keratin fibres, compounds which are already known are those whose structure is developed in the text which follows; nevertheless, these dyes lead to colorations which have properties that are still insufficient as regards the staying power, in terms of resistance to the various attacking factors to which the hair may be subjected (light, bad weather, shampooing).
After considerable research conducted in this matter, the Applicant has now discovered that it is possible to obtain novel compositions for the direct dyeing of keratin fibres, which are capable of leading to colorations which can be particularly resistant to the various attacking factors to which the hair may be subjected, by combining at least one specific polyol and/or polyol ether with at least one cationic direct dye known in the prior art, and of formulae respectively defined below.
This discovery forms the basis of the present invention.
A first subject of the present invention is thus a composition for the direct dyeing of keratin fibres, and in particular human keratin fibres such as the hair, containing, in a medium which is suitable for dyeing, (i) at least one cationic direct dye whose structure corresponds to the following formulae, characterized in that it also contains (ii) at least one specific polyol and/or polyol ether.
(i) The cationic direct dye which can be used according to the present invention is a compound chosen from those of formulae (I), (II), (III) and (III′) below:
a) the compounds of formula (I) below:
in which formula (I):
D is chosen from a nitrogen atom and a —CH group,
R
1
and R
2
, which may be identical or different, are chosen from a hydrogen atom, C
1
-C
4
alkyl radicals optionally having a substituent chosen from —CN, —OH, and —NH
2
radicals, and a 4′-aminophenyl radical; or form, with a carbon atom of the benzene ring, a nitrogenous heterocycle, optionally oxygenated and optionally having at least one substituent chosen from C
1
-C
4
alkyl radicals,
R
3
and R′
3
, which may be identical or different, are chosen from a hydrogen atom, halogen atoms chosen from chlorine, bromine, iodine and fluorine, and cyano, C
1
-C
4
alkoxy, C
1
-C
4
alkyl, and acetyloxy radicals,
X
−
is an anion, preferably chosen from chloride, methyl sulphate, and acetate,
A is a group chosen from structures A
1
to A
18
below:
in which R
4
is chosen from C
1
-C
4
alkyl radicals which can be substituted with a hydroxyl radical and R
5
is chosen from C
1
-C
4
alkoxy radicals, with the proviso that when D is —CH, when A is A
4
or A
13
and when R
3
is other than an alkoxy radical, then R
1
and R
2
are not simultaneously a hydrogen atom;
b) the compounds of formula (II) below:
in which formula (II):
R
6
is chosen from a hydrogen atom and C
1
-C
4
alkyl radicals,
R
7
is chosen from a hydrogen atom, alkyl radicals having a substituent chosen from —CN and amino radicals, and a 4′-aminophenyl radical, or forms, with R
6
, a nitrogenous heterocycle optionally oxygenated and optionally having a substituent chosen from C
1
-C
4
alkyl radicals,
R
8
and R
9
, which may be identical or different, are chosen from a hydrogen atom, halogen atoms, such as bromine, chlorine, or fluorine, and C
1
-C
4
alkyl, C
1
-C
4
alkoxy, and —CN radicals,
X
−
is an anion,
B is a group chosen from structures B1 to B6 below:
in which R
10
is chosen from C
1
-C
4
alkyl radicals, and R
11
and R
12
, which may be identical or different, are chosen from a hydrogen atom and C
1
-C
4
alkyl radicals;
c) the compounds of formulae (III) and (III′) below:
in which formulae (III) and (III′):
R
13
is chosen from a hydrogen atom, C
1
-C
4
alkoxy radicals, halogen atoms, such as bromine, chlorine, iodine and fluorine, and unsubstituted and substituted amino radicals,
R
14
is chosen from a hydrogen atom, and C
1
-C
4
alkyl radicals or forms, with a carbon atom of the benzene ring, a heterocycle which is optionally oxygenated and optionally has a substituent chosen from C
1
-C
4
alkyl radicals,
R
15
is chosen from a hydrogen atom and halogen atoms, such as bromine, chlorine, iodine and fluorine,
R
16
and R
17
, which may be identical or different, are chosen from a hydrogen atom and C
1
-C
4
alkyl radicals,
D
1
and D
2
, which may be identical or different, are chosen from a nitrogen atom and a —CH group,
m is 0 or 1,
it being understood that when R
13
is an unsubstituted amino radical, then D
1
and D
2
are simultaneously a —CH group and m is 0,
X
−
is an anion,
E is a group chosen from structures E1 to E8 below:
in which R′ is chosen from C
1
-C
4
alkyl radicals;
when m is 0 and when D
1
is a nitrogen atom, then E can also be a group of structure E9 below:
in which R′ is chosen from C
1
-C
4
alkyl radicals.
The cationic direct dyes of formulae (I), (II), (III) and (III′) which can be used in the dye compositions in accordance with the invention are known compounds and are described, for example, in patent applications WO 95/01772, WO 95/15144 and EP-A-0,714,954 (the disclosures of which are specifically incorporated by reference herein).
Among the cationic direct dyes of formula (I) which can be used in the dye compositions in accordance with the invention, mention may be made more particularly of the compounds corresponding to structures (I1) to (I52) below:
Among the compounds of structures (I1) to (I52) described above, the compounds most particularly preferred are those corresponding to structures (I1), (I2), (I14) and (I31).
Among the cationic direct dyes of formula (II) which can be used in the dye compositions in accordance with the invention, mention may be made more particularly of the compounds corresponding to structures (II1) to (II9) below:
Among the cationic direct dyes of formula (III) which can be used in the dye compositions in accordance with the invention, mention may be made more particularly of the compounds corresponding to structures (III1) to (III18) below:
Among the specific compounds of structures (III1) to (III18) described above, the compounds most particularly preferred are those corresponding to structures (III4), (III5) and (III13).
Among the cationic direct dyes of formula (III′) which can be used in the dye compositions in accordance with the invention, mention may be made more particularly of the compounds corresponding to structures (III′1) to (III′3) below:
The cationic direct dye(s) used according to the invention preferably represent(s) from 0.001 to 10% by weight approximately relative to the total weight of the dye composition, and even more preferably from 0.005 to 5% by weight approximately relative to this weight.
(ii) For the purposes of the invention, the term “polyol” denotes a compound of linear
Einsmann Margaret
L'Oreal (S.A.)
LandOfFree
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