Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-05-28
2002-04-16
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S408000, C008S429000, C008S431000, C008S609000, C008S610000, C008S611000, C008S613000, C008S654000, C008S655000, C008S657000, C008S659000
Reexamination Certificate
active
06371994
ABSTRACT:
The invention relates to a dye composition for keratin fibers, in particular for 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 glycerol and/or one specific polyol and/or polyol ether.
The invention also relates to the dyeing processes and devices using the composition.
Two types of coloration can be distinguished in the field of hair treatment.
The first is semi-permanent or temporary dyeing, or direct dyeing, which involves dyes capable of giving the hair's natural color a more or less pronounced color 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 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 dyes known as “oxidation” dyes comprising oxidation dye precursors and couplers.
Oxidation dye precursors, commonly known as “oxidation bases”, are initially colorless or weakly colored compounds 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 modifier compounds commonly known as “couplers”, which are generally present in the dye compositions used in oxidation dyeing.
In order to vary the shades obtained with the said oxidation dyes, or to enrich them with glints, it is known to add direct dyes thereto.
Among the cationic direct dyes available in the field of dyeing keratin fibers, in particular human keratin fibers, 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, e.g., the homogeneity of the color distributed along the fiber (“unison”), in which case it is said that the coloration is too selective, the staying power, in terms of resistance to the various attacking factors to which the hair may be subjected (light, bad weather, shampooing) and the intensity.
After considerable research conducted in this matter, the inventors have now discovered that it is possible to obtain novel compositions for dyeing keratin fibers, which are capable of leading to colorations which can be more resistant to the various attacking factors to which the hair may be subjected, and can be more intense and less selective, by combining at least glycerol and/or one specific polyol and/or polyol ether with at least one cationic direct dye known in the prior art, and of formula (I) 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 formula (I) below, characterized in that it also contains (ii) at least glycerol and/or one specific polyol and/or polyol ether.
(i) The cationic direct dye which can be used according to the present invention is a compound of formula (I) below:
in which:
the symbol A represents a group chosen from structures A
1
to A
3
below:
in which structures A
1
to A
3
,
R
1
is chosen from C
1-C
4
alkyl radicals and a phenyl radical having a substituent chosen from C
1
-C
4
alkyl radicals and halogen atoms chosen from chlorine, bromine, iodine and fluorine;
R
2
is chosen from C
1
-C
4
alkyl radicals and a phenyl radical;
R
3
and R
4
, which may be identical or different, are chosen from C
1
-C
4
alkyl radicals and a phenyl radical or, in the case of structure A
1
, can together form a substituted benzene ring, and in the case of structure A
2
, can together form a benzene ring optionally having at least one substituent chosen from C
1
-C
4
alkyl, C
1
-C
4
alkoxy and NO
2
radicals;
R
3
can also denote a hydrogen atom;
Z is chosen from an oxygen atom, a sulphur atom, and —NR
2
groups;
M is chosen from —CH, —CR, where R is chosen from C
1
-C
4
alkyl radicals, and —N
+
R
5
(X
−
)
r
groups;
K is chosen from —CH, —CR, where R is chosen from C
1
-C
4
alkyl radicals, and —N
+
R
5
(X
−
)
r
groups;
P is chosen from —CH, —CR, where R is chosen from C
1
-C
4
alkyl radicals, and —N
+
R
5
(X
−
)
r
r denotes 0 or 1;
R
5
is chosen from an atom O
−
, C
1
-C
4
alkoxy radicals and C
1
-C
4
alkyl radicals;
R
6
and R
7
, which may be identical or different, are chosen from a hydrogen atom, halogen atoms chosen from chlorine, bromine, iodine and fluorine, C
1
-C
4
alkyl radicals, C
1
-C
4
alkoxy radicals and an —NO
2
radical;
X
31
is an anion, preferably chosen from chloride, iodide, methyl sulphate, ethyl sulphate, acetate and perchlorate;
with the proviso that,
if R
4
is a C
1
-C
4
alkyl radical and Z is a sulphur atom, R
3
is not a hydrogen atom;
if R
5
is O
−
, then r is zero;
if K or P or M is —N
+
—C
1
-C
4
-alkyl X
−
, then R
6
or R
7
is other than a hydrogen atom;
if K is —N
+
R
5
(X
−
)
r
, then M═P and is —CH or —CR;
if M is —N
+
R
5
(X
−
)
r
, then K═P and is —CH or —CR;
if P is —N
+
R
5
(X
−
)
r
, then K═M and is —CH or —CR;
if Z is —NR
2
and R
2
is a C
1
-C
4
alkyl radical, then at least one of the radicals R
1
, R
3
or R
4
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
is chosen from a hydrogen atom, halogen atoms chosen from chlorine, bromine, iodine and fluorine, C
1
-C
4
alkyl radicals, C
1
-C
4
alkoxy radicals, a radical —OH, a radical —NO
2
, —NHR
11
radicals, —NR
12
R
13
radicals, and —NHCO(C
1
-C
4
) alkyl radicals or forms, with R
9
, a 5- or 6-membered ring which may contain at least one hetero atom chosen from nitrogen, oxygen and sulphur;
R
9
is chosen from a hydrogen atom, halogen atoms chosen from chlorine, bromine, iodine and fluorine, C
1
-C
4
alkyl radicals, and C
1
-C
4
alkoxy radicals, or forms, with R
10
or R
11
, a 5- or 6-membered ring which may contain at least one hetero atom chosen from nitrogen, oxygen and sulphur;
R
10
is chosen from a hydrogen atom, an —OH radical, —NHR
11
radicals and —NR
12
R
13
radicals;
R
11
is chosen from a hydrogen atom, C
1
-C
4
alkyl radicals, C
1
-C
4
monohydroxyalkyl radicals, C
2
-C
4
polyhydroxyalkyl radicals and a phenyl radical;
R
12
and R
13
, which may be identical or different, are chosen from C
1
-C
4
alkyl radicals, C
1
-C
4
monohydroxyalkyl radicals and C
2
-C
4
polyhydroxyalkyl radicals; or
(b) a 5- or 6-membered nitrogenous heterocyclic group which can contain at least one other hetero atom and/or at least one carbonyl group and which can have at least one substituent chosen from C
1
-C
4
alkyl, amino and phenyl radicals, and in particular a group of structure B2 below:
in which structure B2,
R
14
and R
15
, which may be identical or different, are chosen from a hydrogen atom and C
1
-C
4
alkyl and phenyl radicals;
Y denotes a —CO— radical or a radical
n=0 or 1, where, when n denotes 1, U denotes 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 use
Cotteret Jean
Lang Gerard
Einsmann Margaret
L'Oreal (S.A.)
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