Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-08-16
2004-03-30
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S405000, C008S407000, C008S408000, C008S415000, C008S426000
Reexamination Certificate
active
06712861
ABSTRACT:
The invention relates to a composition for dyeing keratin fibres, and in particular human keratin fibres such as the hair, comprising, in a medium which is suitable for dyeing, at least one suitably selected cationic direct dye and at least one nitrobenzene direct dye, as well as to the dyeing process using this composition.
It is well known to dye keratin fibres, and in particular human hair, with dye compositions containing direct dyes and in particular nitrobenzene direct dyes. However, direct dyes have the drawback, when they are incorporated into dye compositions, of leading to colorations which have insufficient staying power, in particular with regard to shampooing.
The Applicant has now discovered that it is possible to obtain novel dyes capable of leading to intense, unselective colorations which show good resistance to the various attacking factors to which the hair may be subjected, by combining at least one suitably selected cationic direct dye and at least one nitrobenzene direct dye.
This discovery forms the basis of the present invention.
A first subject of the invention is thus a ready-to-use composition for dyeing 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 cationic direct dye chosen from:
a) the compounds of formula (I) below:
in which:
D represents a nitrogen atom or a —CH group,
R
1
and R
2
, which may be identical or different, represent a hydrogen atom; a C
1
-C
4
alkyl radical which can be substituted with a —CN, —OH or —NH
2
radical; or form, with a carbon atom of the benzene ring, an optionally oxygenated or nitrogenous heterocycle which can be substituted with one or more C
1
-C
4
alkyl radicals; a 4′-aminophenyl radical,
R
3
and R′
3
, which may be identical or different, represent a hydrogen or halogen atom chosen from chlorine, bromine, iodine and fluorine, or a cyano, C
1
-C
4
alkoxy or acetyloxy radical,
X
−
represents an anion preferably chosen from chloride, methyl sulphate and acetate,
A represents a group chosen by structures A1 to A19 below:
in which R
4
represents a C
1
-C
4
alkyl radical which can be substituted with a hydroxyl radical and R
5
represents a C
1
-C
4
alkoxy radical, with the proviso that when D represents —CH, when A represents A
4
or A
13
and when R
3
is other than an alkoxy radical, then R
1
and R
2
do not simultaneously denote a hydrogen atom;
b) the compounds of formula (II) below:
in which:
R
6
represents a hydrogen atom or a C
1
-C
4
alkyl radical,
R
7
represents a hydrogen atom, an alkyl radical which can be substituted with a —CN radical or with an amino group, a 4′-aminophenyl radical, or forms, with R
6
, an optionally oxygenated and/or nitrogenous heterocycle which can be substituted with a C
1
-C
4
alkyl radical,
R
8
and R
9
, which may be identical or different, represent a hydrogen atom, a halogen atom such as bromine, chlorine, iodine or 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,
B represents a group chosen by structures B1 to B6 below:
in which R
10
represents a C
1
-C
4
alkyl radical, R
11
and R
12
, which may be identical or different, represent a hydrogen atom or a C
1
-C
4
alkyl radical;
c) the compounds of formulae (III) and (III′) below:
in which:
R
13
represents a hydrogen atom, a C
1
-C
4
alkoxy radical, a halogen atom such as bromine, chlorine, iodine or fluorine or an amino radical,
R
14
represents a hydrogen atom, a C
1
-C
4
alkyl radical, or forms, with a carbon atom of the benzene ring, a heterocycle which is optionally oxygenated and/or substituted with one or more C
1
-C
4
alkyl groups,
R
15
represents a hydrogen or halogen atom such as bromine, chlorine, iodine or fluorine,
R
16
and R
17
, 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 different, represent a nitrogen atom or a —CH group,
m=0 or 1,
it being understood that when R
13
represents an unsubstituted amino group, then D
1
and D
2
simultaneously represent a —CH group and m=0,
X
−
represents an anion preferably chosen from chloride, methyl sulphate and acetate,
E represents a group chosen by structures E1 to E8 below:
in which R′ represents a C
1
-C
4
alkyl radical; when m=0 and when D
1
represents a nitrogen atom, then E can also denote a group of structure E9 below:
in which R′ represents a C
1
-C
4
alkyl radical,
and at least one nitrobenzene direct dye.
The ready-to-use dye composition in accordance with the invention leads to intense, chromatic colorations which show low selectivity and excellent properties of resistance both with respect to atmospheric agents such as light and bad weather and with respect to perspiration and the various treatments to which the hair may be subjected (washing, permanent-waving).
A subject of the invention is also a process for dyeing keratin fibres using this ready-to-use dye composition.
The cationic direct dyes of formulae (I), (II), (III) and (III′) which can be used in the ready-to-use 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.
Among the cationic direct dyes of formula (I) which can be used in the ready-to-use 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 ready-to-use dye compositions in accordance with the invention, mention may be made more particularly of the compounds corresponding to structures (II1) to (II12) below:
Among the cationic direct dyes of formula (III) which can be used in the ready-to-use 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 ready-to-use 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 ready-to-use dye composition, and even more preferably from 0.05 to 5% by weight approximately relative to this weight.
The nitrobenzene direct dye(s) which can be used in the ready-to-use dye composition in accordance with the invention is (are) preferably chosen from the compounds of formula (IV) below:
in which:
R
18
represents an amino radical; an amino radical monosubstituted or disubstituted with a C
1
-C
4
alkyl, C
1
-C
4
monohydroxyalkyl, C
2
-C
4
polyhydroxyalkyl, C
1
-C
4
aminoalkyl, mono(C
1
-C
4
) alkylamino(C
1
-C
4
) alkyl, di(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl or ureido(C
1
-C
4
)alkyl or aryl radical or an aryl radical in which the aryl ring is substituted with one or more hydroxyl, carboxyl, amino or di(C
1
-C
4
)alkylamino radicals,
R
19
represents a hydrogen atom; an amino radical; hydroxyl radical; C
1
-C
4
alkyl radical; C
1
-C
4
alkoxy radical; C
1
-C
4
monohydroxyalkyl radical; C
2
-C
4
polyhydroxyalkyl radical; C
1
-C
4
monohydroxyalkoxy radical; C
2
-C
4
polyhydroxyalkoxy radical; C
1
-C
4
aminoalkoxy radical; an amino radical monosubstituted or disubstituted with a C
1
-C
4
Einsmann Margaret
L'Oreal (S.A.)
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