Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2001-06-25
2003-09-09
Kopec, Mark (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S406000, C008S407000, C008S409000, C008S410000, C008S454000, C008S455000, C546S167000
Reexamination Certificate
active
06616709
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 greenish yellow, yellow, red to blue, 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 cationic 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 having high hair dyeing power, less color fade over time, and excellent storage stability to permit only a smaller change in color tone of the dye after storage.
The present inventors have found that use of the below-described compound—which is known in Japanese Patent Applications Laid-Open (Kokai) Nos. Sho 49-87730, 53-139634, 51-136723 and 55-99955 as a cationic dye for dyeing or printing therewith synthetic resins, synthetic fibers, paper or leather—as a hair dye, the resulting hair dye composition can strongly impart the hair with an extremely vivid color ranging from greenish yellow, yellow, red to blue without decomposing the dye upon hair dyeing, 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 (1):
wherein, ring A represents a benzene ring which may have a substituent or may further be cyclocondensed with another aromatic ring;
B represents an aryl group which may have a substituent or may be coupled with R
2
to form a heterocyclic structure which will be described later, or a heterocyclic group which may have a substituent or may be coupled with R
2
to form a heterocyclic structure which will be described later,
D represents a nitrogen atom or a group CR
4
(in which R
4
represents a hydrogen atom or a C
1-6
alkyl group);
E represents a group NR
5
, CR
6
R
7
or CR
6
═CR
7
(in which R
5
represents a C
1-6
alkyl group which may have a substituent, a C
2-6
alkenyl group which may have a substituent or an aryl group which may have a substituent, or forms, when taken together with R
2
, a ring which will be described later, and R
6
and R
7
each independently represents a hydrogen atom or a C
1-6
alkyl group), an oxygen atom or a sulfur atom;
R
1
represents a C
1-6
alkyl group which may have a substituent, a C
2-6
alkenyl group which may have a substituent or an aryl group which may have a substituent;
R
2
represents a divalent group bonded to B or forms, when taken together with R
3
or R
5
, a ring which will be described later,
R
3
forms, when taken together with R
2
, a ring which will be described later;
n stands for 0 or 1, with the proviso that when n=0, R
2
and R
5
, when taken together with N—C—C, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent, or R
2
is bonded to B, thereby forming a 6- or 7-membered heterocyclic structure which may have a substituent and may contain a hetero atom other than D and when n=1, R
2
and R
3
, when taken together with C═D—N, form a 5- to 7-membered nitrogen-containing heterocyclic structure which may have a substituent, and
X
−
represents an anion.
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 formula (1), examples of the substituent which the ring A may have include alkyl groups, aryl groups, alkoxy groups, amino group, hydroxy group, cyano group, nitro group and halogen atoms, more specifically, methyl group, ethyl group, methoxy group, ethoxy group, chlorine atom and bromine atom. Examples of the aromatic ring with which the ring A may be cyclocondensed include a benzene ring.
Examples of the aryl group represented by B include phenyl, 1-naphthyl and 2-naphthyl groups, while those of the heterocyclic group include 2-benzthiazolyl and 3-indolyl groups, each of which may be substituted with a chlorine atom, bromine atom, nitro group, cyano group, C
1-4
alkyl group, phenyl group, benzyl group, C
1-4
alkoxy group, hydroxy group, phenoxy group, benzyloxy group, C
1-4
alkylsulfonyl group, phenylsulfonyl group, benzylsulfonyl group, aminocarbonyl group, mono- or di-(C
1-4
alkyl)aminocarbonyl group, aminosulfonyl group, C
1-4
alkylcarbonyl group, C
1-4
alkylcarbonylamino group, benzoylamino group, phenylazo group, and a group NR
8
R
9
(in which R
8
and R
9
each independently represents a hydrogen atom, C
1-4
alkyl group, aryl group, aralkyl group, unsubstituted or mono- or di-(C
1-4
alkyl)-substituted amino(C
1-4
alkyl) group, amino(C
1-4
alkyl) group substituted by a group of the formula (1) from which one hydrogen atom has been removed, or (C
1-4
alkoxy) (C
1-4
alkyl)amino group). The number of these substituents is 1 to 3. The cycle-constituting atom may be coupled with the above-exemplified substituent to form another cyclic structure.
Examples of the C
1-6
alkyl group represented by R
4
in the case where D represents a group CR
4
or by R
6
or R
7
in the case where E represents a group CR
6
R
7
or CR
6
═CR
7
include methyl, ethyl, propyl, isopropyl and cyclohexyl groups. Preferred examples of R
4
, R
6
or R
7
include hydrogen atom and methyl groups.
Examples of the C
1-6
alkyl group represented by R
5
in the case where E represents a group NR
5
include methyl, ethyl, propyl, isopropyl and cyclohexyl groups; those of the C
2-6
alkenyl group include ethenyl and propenyl groups; and those of the aryl include phenyl and naphthyl groups, each of which may be substituted with an aryl, alkoxy, amino, hydroxy or cyano group, or a halogen atom.
Examples of the C
1-6
alkyl group represented by R
1
include methyl, ethyl, propyl, isopropyl and cyclohexyl groups, those of the C
2-6
alkenyl group include ethenyl and propenyl groups, and those of the aryl group include phenyl and naphthyl groups, of which the alkyl group is preferred as R
1
. Examples of the group which may be a substituent for them include aryl groups, cyano group, halogen atoms, hydroxy group, C
1-4
alkoxy groups, NR
10
R
11
(in which R
10
and R
11
each independently represents a hydrogen a
Matsunaga Ken-ichi
Miyabe Hajime
Ohashi Yukihiro
Saito Yoshinori
Totoki Shintaro
Elhilo Eisa
Kao Corporation
Kopec Mark
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