Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2000-01-19
2002-08-13
Douyon, Lorna M. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S407000, C008S405000, C008S408000, C008S409000, C008S410000, C008S411000, C008S423000, C008S426000
Reexamination Certificate
active
06432146
ABSTRACT:
The present invention relates to dyeing compositions comprising a combination of two specific cationic dyes and not containing a self-oxidizing agent, to the use of the compositions as direct dyes in dyeing applications for keratin fibers, and in particular human keratin fibers such as the hair, to direct dyeing processes using the compositions, and to dyeing devices using the compositions.
Two types of dyeing can be distinguished in the hair field.
The first is permanent dyeing or oxidation dyeing, which uses oxidation dyes that develop their dyeing power in the presence of oxidizing agents.
The second is semi-permanent or temporary dyeing, or direct dyeing, which uses dyes capable of giving the hair's natural color a more or less pronounced color change which may be able to withstand shampooing several times. These dyes are referred to as direct dyes; they can be used with or without an oxidizing agent. In the presence of an oxidizing agent, the dyeing is referred to as lightening; without an oxidizing agent, the dyeing is referred to as conventional direct dyeing rather than lightening dyeing.
The present invention relates to conventional direct dyeing, i.e., dyeing without an oxidizing agent, which is less aggressive towards keratin fibers.
Among the cationic direct dyes available for dyeing keratin fibers, in particular human keratin fibers, the compounds of formulae (I) to (III) defined below are already known. However, these dyes, generally referred to as Arianor dyes, give dyeing results which have properties that are insufficient with regard to the intensity and chromaticity of the shades obtained, the homogeneity of the color distributed along the fiber (the dyeing is then said to be too selective), and the staying power in terms of fastness with respect to the various attacking factors to which the hair may be subjected (e.g., light, bad weather, shampooing).
The inventor has just discovered, entirely surprisingly and unexpectedly, that a combination of at least one cationic dye of formulae (I) to (III) defined below and of at least one cationic dye of formulae (IV) to (VII) defined below is suitable for direct dyeing, and that, in addition, it makes it possible to obtain dye compositions which give relatively unselective and highly chromatic dyeing results that are particularly fast with respect to the various attacking factors to which the hair may be subjected.
This discovery forms the basis of the present invention.
A first subject of the present invention is thus the use, as a direct dye in, or for the manufacture of, direct dyeing compositions for keratin fibers and in particular for human keratin fibers such as the hair, of a combination comprising (i) at least one cationic dye of formulae (I) to (III) defined below, and (ii) at least one cationic dye of formulae (IV) to (VII) defined below, it being understood that the direct dyeing compositions do not contain a self-oxidizing dye:
(i) cationic dye of formulae (I), (II) and (III):
in which:
R
1
represents a hydrogen atom or an amino radical;
R
2
represents a hydrogen atom or a nitro group;
R
3
represents a hydrogen atom, a nitro group or a C
1
-C
4
alkoxy radical;
R
4
represents a C
1
-C
4
alkyl radical;
R
5
represents a hydrogen atom or a para-tri(C
1
-C
4
)alkylammoniophenyl group;
R
6
represents a bromine atom or an NH-para-tri-(C
1
-C
4
)alkylammoniophenyl group; and
X
−
represents an anion preferably chosen from chloride, methylsulphate and acetate.
According to the present invention, the compounds corresponding to the mesomeric forms of structures (I) to (III) can also be used.
As examples of compounds of formula (I), mention may be made of the dyes Basic Brown 16, Basic Red 76, Basic Brown 17 and Basic Red 118.
As an example of compounds of formula (II), mention may be made of the dye Basic Yellow 57.
As an example of compounds of formula (III), mention may be made of the dye Basic Blue 99.
These Color Index names cover the following chemical structures (in the form of their chlorides):
8-((4-aminophenyl)azo)-7-hydroxy-2-trimethylammonionaphthalene,
8-((2-methoxyphenyl)azo)-7-hydroxy-2-trimethylammonionaphthalene,
8-((4-amino nitrophenyl)azo)-7-hydroxy-2-trimethylammonionaphthalene,
8-((4-amino-2-nitrophenyl)azo)-7-hydroxy-2-trimethylammonionaphthalene,
3-((3-methyl-5-hydroxy-1-phenyl-1H-pyrazol-4-yl)azo) trimethylammoniobenzene,
3-((4-amino-6-bromo-5,8-dihydro-1-hydroxy-8-imino-5-oxo-2-naphthyl)amino)trimethylammoniobenzene, and
3-((3,7-dibromo-5,8-dihydro-4-hydroxy-5-imino-8-oxo-1-naphthyl)amino)trimethylammoniobenzene.
The compounds of formulae (I) to (III) are found, alone or in combination, in the products corresponding to the trade names, sold by the company Warner Jenkinson: Arianor Mahogany, Arianor Steel Blue, Arianor Madder Red, Arianor Sienna Brown, Arianor Straw Yellow and Arianor Bordeaux.
(ii) cationic dye of formulae (IV), (V), (VI), (VI′) and (VII) below:
a) compounds of formula (IV):
in which:
D represents a nitrogen atom or a —CH group,
R
7
and R
8
, which may be identical or different, represent a hydrogen atom; a 4′-aminophenyl radical; or a C
1
-C
4
alkyl radical which can be substituted with a —CN, —OH or —NH
2
radical, or which can form, with the nitrogen atom to which it is attached and with a carbon atom of the benzene ring, a heterocycle optionally comprising oxygen or additional nitrogen atoms and which can be substituted with one or more C
1
-C
4
alkyl radicals;
R
9
and R′
9
, which may be identical or different, represent a hydrogen atom, a halogen atom chosen from chlorine, bromine, iodine and fluorine, or a cyano, C
1
-C
4
alkyl, C
1
-C
4
alkoxy or acetyloxy radical;
X
−
represents an anion preferably chosen from chloride, methylsulphate and acetate; and
A represents a group chosen from the structures A1 to A19 below:
in which:
R
10
represents a C
1
-C
4
alkyl radical which can be substituted with a hydroxyl radical; and
R
11
represents a C
1
-C
4
alkoxy radical;
with the provisos that:
(i) when D represents —CH, and A represents A
4
or A
13
, and R
9
is other than an alkoxy radical, then R
7
and R
8
do not simultaneously denote a hydrogen atom; and
(ii) when D represents a nitrogen atom, and A represents A
6
, then R
7
and R
8
do not simultaneously denote a methyl radical.
b) compounds of formula (V):
in which:
R
12
represents a hydrogen atom or a C
1
-C
4
alkyl radical;
R
13
represents a hydrogen atom, an alkyl radical which can be substituted with a —CN radical or with an amino group, or a 4′-aminophenyl radical; or R
13
forms, together with R
12
and the nitrogen atom to which they are attached, a heterocycle optionally comprising oxygen and/or nitrogen, and which can be substituted with a C
1
-C
4
alkyl radical;
R
14
and R
15
, which may be identical or different, represent a hydrogen atom, a halogen atom such as bromine, chlorine, iodine and fluorine, a C
1
-C
4
alkyl or C
1
-C
4
alkoxy radical or a —CN radical;
X
−
represents an anion preferably chosen from chloride, methyl sulphate and acetate; and
B represents a group chosen from the structures B1 to B6 below:
in which:
R
16
represents a C
1
-C
4
alkyl radical; and
R
16
and R
17
, which may be identical or different, represent a hydrogen atom or a C
1
-C
4
alkyl radical;
(c) compounds of formulae (VI) and (VI′):
in which:
R
19
represents a hydrogen atom, a C
1
-C
4
alkoxy radical, a halogen atom such as bromine, chlorine, iodine and fluorine or an amino radical;
R
20
represents a hydrogen atom or a C
1
-C
4
alkyl radical, or forms, with the nitrogen atom to which it is attached and a carbon atom of the benzene ring, a heterocycle optionally containing oxygen and/or substituted with one or more identical or different C
1
-C
4
alkyl groups;
R
21
represents a hydrogen or halogen atom such as bromine, chlorine, iodine or fluorine;
R
22
and R
23
, which may be identical or different, represent a hydrogen atom or a C
1
-C
4
alkyl radical;
D
1
and D
2
, which may be identical or dif
Douyon Lorna M.
Elhilo Eisa
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
L'Oreal (S.A.)
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