Composition for dyeing keratin fibers with a cationic direct...

Details Composition for dyeing keratin fibers with a cationic direct... Composition for dyeing keratin fibers with a cationic direct...

1999-07-08

2003-09-02

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

C008S409000, C008S426000, C008S423000, C008S654000, C008S561000

Reexamination Certificate

active

06613102

ABSTRACT:

The invention relates to a composition for dyeing keratin fibers, in particular human keratin fibers such as the hair, comprising, in a medium which is suitable for dyeing, at least one cationic direct dye of given formula and at least one specific thickening polymer. The invention also relates to the dyeing processes and dyeing devices, i.e., kits, using the composition.
Two types of dyeing may be distinguished in the haircare sector. The first is semi-permanent or temporary dyeing, or direct dyeing, which uses dyes capable of giving the hair a natural coloration, a more or less pronounced color change which may withstand shampooing several times. These dyes are also 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 lightening dyeing. Lightening dyeing is carried out by applying a mixture, prepared at the time of use, of a direct dye and an oxidizing agent to the hair, and makes it possible in particular to obtain, by lightening the melanin in the hair, an advantageous effect such as a unified color in the case of grey hair, or to bring out the color in the case of naturally pigmented hair.
The second is permanent dyeing or oxidation dyeing. This is carried out with so-called “oxidation” dyes comprising oxidation dye precursors and couplers. Oxidation dye precursors, commonly known as “oxidation bases”, are compounds which are initially colorless or weakly colored which develop their dyeing power on the hair in the presence of oxidizing agents added at the time of use, leading to the formation of colored compounds and dyes. The formation of these colored compounds and dyes results either from an oxidative condensation of the “oxidation bases” with themselves or from an oxidative condensation of the oxidation bases with coloration-modifying compounds commonly known as “couplers”, which are generally present in the dye compositions used in oxidation dyeing.
It is known practice to add direct dyes to oxidation dyes in order to vary the shades obtained with the said oxidation dyes or to enrich the shades with glints. Among the cationic direct dyes available in the sector of dyeing keratin fibers, in particular human keratin fibers, the compounds whose structure is developed in the text hereinbelow are already known; nevertheless, these dyes lead to colorations which have characteristics that could still be improved, such as the intensity, the homogeneity of the color distributed along the fiber, in which case the coloration is said to be too selective, and the staying power, in terms of the 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 present inventors have discovered that it is possible to obtain novel compositions for dyeing keratin fibers which are capable of giving more intense and yet unselective colorations which show good resistance to the various attacking factors to which the hair may be subjected, by combining at least one specific thickening polymer with at least one known cationic direct dye of the prior art, which have the respective formulae defined below. This discovery forms the basis of the present invention.
A first subject of the present invention is thus a composition for dyeing keratin fibers, and in particular human keratin fibers such as the hair, containing, in a medium which is suitable for dyeing, (i) at least one cationic direct dye whose structure corresponds to formulae (I) defined below, characterized in that it also contains (ii) at least one specific thickening polymer.
(i) The cationic direct dye which can be used according to the present invention is a compound of formula (I) below:
A—N═N—B  (I)
in which:
the symbol A represents a group chosen from the structures A
1
to A
3
below:
 in which structures A
1
to A
3
,
R
1
denotes a C
1
-C
4
alkyl radical, a phenyl radical which can be substituted with a C
1
-C
4
alkyl radical or a halogen atom chosen from chlorine, bromine, iodine and fluorine;
R
2
denotes a C
1
-C
4
alkyl radical or a phenyl radical;
R
3
and R
4
, which may be identical or different, represent a C
1
-C
4
alkyl radical, a phenyl radical or else, in the case of structure A1, can together form a benzene ring substituted with one or more C
1
-C
4
alkyl, C
1
-C
4
alkoxy or NO
2
radicals and, in the case of structure A2, can together form a benzene ring optionally substituted with one or more C
1
-C
4
alkyl, C
1
-C
4
alkoxy or NO
2
radicals;
R
3
can also denote a hydrogen atom;
Z denotes an oxygen or sulphur atom or a group —NR
2
;
M represents a —CH, —CR (R denoting C
1
-C
4
alkyl) or —N
+
R
5
(X
−
)
r
group;
K represents a —CH, —CR (R denoting C
1
-C
4
alkyl) or —N
+
R
5
(X
−
)
r
group;
P represents a —CH, —CR (R denoting C
1
-C
4
alkyl) or —N
+
R
5
(X
−
)
r
group; r denotes zero or 1;
R
5
represents an atom O
−
, a C
1
-C
4
alkoxy radical or a C
1
-C
4
alkyl radical;
R
6
and R
7
, which may be identical or different, represent a hydrogen atom, a halogen atom chosen from chlorine, bromine, iodine and fluorine, a C
1
-C
4
alkyl or C
1
-C
4
alkoxy radical or an —NO
2
radical;
X
−
represents an anion preferably chosen from chloride, iodide, methyl sulphate, ethyl sulphate, acetate and perchlorate;
with the proviso that,
if R
4
denotes a C
1
-C
4
alkyl radical and Z denotes a sulphur atom, R
3
does not denote a hydrogen atom; if R
5
denotes O
−
, then r denotes zero;
if K or P or M denote C
1
-C
4
—N
+
-alkyl X
−
, then R
6
or R
7
is other than a hydrogen atom;
if K denotes —N
+
R
5
(X
−
)
r
, then M═P═—CH, —CR;
if M denotes —N
+
R
5
(X
−
)
r
, then K═P═—CH, —CR;
if P denotes —N
+
R
5
(X
−
)
r
, then K═M and denote —CH or —CR;
if Z denotes —NR
2
and R
2
denotes a C
1
-C
4
alkyl radical, then at least one of the radicals R
1
, R
3
or R
4
of the group of structure A
2
is other than a C
1
-C
4
alkyl radical;
the symbol B represents:
(a) a group of structure B
1
below:
 in which structure B
1
,
R
8
represents a hydrogen atom, a halogen atom chosen from chlorine, bromine, iodine and fluorine, a C
1
-C
4
alkyl or C
1
-C
4
alkoxy radical, a radical —OH, —NO
2
, —NHR
11
, —NR
12
R
13
, —NHCO (C
1
-C
4
) alkyl, or forms with R
9
a 5- or 6-membered ring which may or may not contain one or more hetero atoms chosen from nitrogen, oxygen and sulphur;
R
9
represents a hydrogen atom, a halogen atom chosen from chlorine, bromine, iodine and fluorine, a C
1
-C
4
alkyl or C
1
-C
4
alkoxy radical or forms, with R
10
or R
11
, a 5- or 6-membered ring which may or may not contain one or more hetero atoms chosen from nitrogen, oxygen and sulphur;
R
10
represents a hydrogen atom, an —OH radical, a radical —NHR
11
or a radical —NR
12
R
13
;
R
11
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 or a phenyl radical;
R
12
and R
13
, which may be identical or different, represent a C
1
-C
4
alkyl radical, a C
1
-C
4
monohydroxyalkyl radical or a C
2
-C
4
polyhydroxyalkyl radical;
(b) a 5- or 6-membered nitrogenous heterocyclic group which can contain other hetero atoms and/or carbonyl groups and which can be substituted with one or more C
1
-C
4
alkyl, amino or phenyl radicals,
and in particular a group of structure B
2
below:
in which structure B
2
,
R
14
and R
15
, which may be identical or different, represent a hydrogen atom, a C
1
-C
4
alkyl radical or a phenyl radical;
Y denotes the —CO— radical or the radical
n=0 or 1, with, when n denotes 1, U denoting a —CO— radical.
In the structures defined above, the C
1
-C
4
alkyl or alkoxy group preferably denotes methyl, ethyl, butyl, methoxy or ethoxy.
The cationic direct dyes of formula (I) which can be used in the dye compositions in accordance with the invention are known compounds and are described, for example

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