Hair dye composition

Details Hair dye composition Hair dye composition

2001-06-26

2003-09-23

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S406000, C008S451000, C008S455000, C008S568000, C008S573000, C008S655000, C008S657000, C008S659000

Reexamination Certificate

active

06623531

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a hair dye composition having markedly high dyeing power, can strongly impart the hair with an extremely vivid color ranging from yellow, red, blue to green, has less color fade over time and undergoes a small change in the color tone of the dye even after storage.
BACKGROUND ART
Hair dyes can be classified by the dye to be used therefor, or whether they have bleaching action of melanin or not. Typical examples include a two-part permanent hair dye composed of a first part containing an alkali agent, an oxidation dye and a direct dye such as nitro dye and a second part containing an oxidizing agent; and one-part semi-permanent hair dye containing an organic acid or an alkali agent, and a direct dye such as acid dye, basic dye or nitro dye.
The above-described permanent hair dye is however accompanied with the drawbacks that color tone imparted by an oxidation dye is not so vivid and the color of the hair dyed with a vivid-color producing nitro dye ordinarily employed as a direct dye markedly fades over time and becomes dull soon even if the color tone rightly after dyeing is very vivid (Japanese Patent Application Laid-Open (Kokai) No. Hei 6-271435).
Recently, hair dyes containing as a direct dye a so-called cationic dye having a cation group contained in their conjugate system have been reported (Japanese Language Laid-Open Publication (PCT) No. Hei 8-507545, 8-501322 or 10-502946, or Japanese Patent Application Laid-Open (Kokai) No. Hei 10-194942). They have been found to involve drawbacks that intended dyeing effects are not available owing to decomposition of them caused by mixing, upon hair dyeing, with hydrogen peroxide ordinarily employed as an oxidizing agent; and that when a cation group is contained in an azo-based (—N═N—) conjugated system, they are unstable to an alkali agent or a reducing agent essentially contained in a permanent hair dye.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide a hair dye composition which has high hair dyeing power, less color fade over time, and excellent storage stability to permit only a small change in color tone of the dye after storage.
The present inventors have found that when the below-described compounds known as photosensitizing dye or sensitizing dye [Journal of Synthetic Organic Chemistry, Japan, 32(12), 971-988 (1974), etc.] are used as a hair dye, the resulting dye composition can strongly impart the hair with a vivid color ranging from yellow, red, blue to green without decomposing the dye upon hair drying, exhibits excellent light resistance, washing resistance, perspiration resistance, friction resistance and heat resistance, and undergoes a small change in the color tone of the dye after storage as compared with that rightly after preparation because the dye exists in the composition stably.
In one aspect of the present invention, there is thus provided a hair dye composition comprising, as a direct dye, a compound represented by the following formula (I), (II), (III) or (IV):
wherein, m stands for 0, 1 or 2, n stands for 1 or 2,
m units of R
1
and n units of R
4
each independently represents a hydrogen atom, a C
1-4
alkyl group or a halogen atom, m units of R
2
each independently represents a hydrogen atom, a C
1-4
alkyl group or an aryl group, with the proviso that at m=2, two R
2
s, taken together with the adjacent ═C—CH═C—, may form a carbocyclic structure or an oxygen-containing heterocyclic structure, n units of R
3
each independently represents a hydrogen atom or a C
1-4
alkyl group, n units of R
5
each independently represents a hydrogen atom or a C
1-4
alkyl group, or is bonded, via a group —CO—O—, to a ring B
5
to form a lactone ring, R
6
represents a hydrogen atom or a C
1-4
alkyl group,
A
1
represents the below-described formula (1), (2) or (3), A
2
represents the below-described formula (4), A
3
represents the below-described formula (5), (6), (7), (8) or (9), A
4
and Z
1
each independently represents the below-described formula (10), (11), (12), (13), (14), (15) or (16), Z
2
represents the below-described formula (17), Z
3
represents the below-described formula (18), (19), (20) or (21):
 (in which, a broken line means presence or absence of &pgr; bonding, D
1
represents an oxygen atom, a sulfur atom or a group NR
25
, D
2
represents an oxygen atom, a sulfur atom, a group NR
26
or a group CR
27
R
28
, D
3
represents a nitrogen atom or a group CR
29
, D
4
represents an oxygen atom, a sulfur atom or a group NR
30
, R
7
, R
8
, R
9
, R
14
and R
25
each independently represents a C
1-6
alkyl group which may have a substituent, R
10
, R
11
, R
13
, R
15
, R
16
, R
21
, R
22
, R
27
, R
28
and R
29
each independently represents a hydrogen atom or a C
1-6
alkyl group, R
12
and R
26
each independently represents a hydrogen atom or a C
1-6
alkyl group which may have a substituent, R
17
and R
18
each independently represents a hydrogen atom, a C
1-6
alkyl group which may have a substituent or an aryl group which may have a substituent, or R
17
and R
18
, taken together with the adjacent nitrogen atom, form a nitrogen-containing heterocycle or one or both of R
17
and R
18
is (are) bonded to the ring B
5
to form a nitrogen-containing heterocycle, R
19
and R
23
each independently represents an aryl group which may have a substituent, R
20
represents a C
1-6
alkyl group, R
24
and R
30
each independently represents a hydrogen atom, a C
1-6
alkyl group which may have a substituent, or an aryl group which may have a substituent, Y
1
and Y
2
each independently represents an oxygen atom or a sulfur atom, rings B
1
, B
2
, B
3
and B
4
each independently has a ring structure which may have, as a substituent, a halogen atom, an aryl group or a C
1-4
alkyl group or may further be cyclocondensed with a benzene ring, B
5
has a ring structure which may have, as a substituent, a halogen atom, an aryl group or a C
1-4
alkyl group, may be condensed with a benzene ring, or may be bonded to R
17
or R
18
to have a ring structure which may be cyclocondensed with a nitrogen-containing heterocycle), and
X
−
represents an anion, with the proviso that X
−
does not exist when R
7
, R
8
, R
9
and R
25
each has a sulfonium group as a substituent.
In another aspect of the present invention, there is also provided a method for dyeing the hair with the above-described hair dye composition.
BEST MODE FOR CARRYING OUT THE INVENTION
In the formulas (I) to (IV), m is preferably 0 or 1 and n is preferably 1 from the viewpoint of stability in the hair dye composition.
Examples of the C
1-4
alkyl group represented by R
1
or R
4
include methyl, ethyl and butyl groups, those of the halogen atom include chlorine, bromine and fluorine atoms. As each of R
1
and R
4
, a hydrogen atom is most preferred.
Examples of the C
1-4
alkyl group represented by R
2
include methyl, ethyl and butyl groups, those of the aryl group include phenyl group. Examples of the carbocyclic structure which may be formed at m=2 by two R
2
s when they are taken together with the adjacent ═C—CH═C— include cyclohexene ring and cyclopentene ring. As the oxygen-containing heterocyclic structure, 4H-pyrane ring can be mentioned as an example. These rings may be substituted by an alkyl group. As R
2
, hydrogen atom and C
1-4
alkyl groups are preferred, of which the hydrogen atom, methyl group and ethyl group are particularly preferred.
Examples of the C
1-4
alkyl group represented by R
3
or R
6
include methyl, ethyl and butyl groups. As each of R
3
and R
6
, hydrogen atom is most preferred.
Examples of the C
1-4
alkyl group represented by R
5
include methyl, ethyl and butyl groups, while those of the lactone ring which may be formed by bonding of R
5
to the ring B
5
via —CO—O— include coumalin ring (including ring B
5
). As R
5
, hydrogen atom is most preferred.
As examples of the substituents for the groups (1) to (21) represented by each of A
1
to A
4
and Z
1
to Z
3
, th

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