JPH1053718A - Disperse dye composition and method for coloring hydrophobic material using the same - Google Patents

Abstract

(57) [Problem] To provide a novel disperse dye composition containing a thiophenazo compound, an anthraquinone compound and the like, and a method for coloring a hydrophobic material using the same. SOLUTION: General formula (I) (Wherein, R ₁ represents a hydrogen atom or a halogen atom;
₂ represents a lower alkyl group which may be substituted or a phenyl group which may be substituted; R ₃ represents a hydrogen atom or a lower alkoxy group; R ₄ and R ₅ each independently represent a hydrogen atom Or an alkyl group which may be substituted. ) And a thiophenazo compound represented by the general formula (II) And / or an anthraquinone compound represented by the general formula (I
II) A disperse dye composition comprising a quinone compound represented by the formula:

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a disperse dye composition containing a thiophenazo compound.

[0002]

2. Description of the Related Art Conventionally, as a disperse dye for dyeing or printing a hydrophobic fiber material, a disperse dye composition comprising an anthraquinone compound added to a specific thiophenazo compound having a carboxamide group (JP-A-6-41461). No.)
And a disperse dye composition containing a quinone compound (see
No. 5-263002) is also known.

[0003]

However, when a hydrophobic fiber material, for example, a polyester fiber material is dyed by using such a conventional disperse dye composition, the dyed material obtained has a uniform dyeing property and a high dyeing property. There was a problem that the build-up property enabling dyeing up to the concentration range, and furthermore, the wet fastness, particularly the washing fastness, were not sufficiently satisfactory. On the other hand, in recent years, polyester fiber materials called new synthetic fibers have been developed by various fiber manufacturers as sensible materials with a new texture unique to synthetic fibers that are not found in natural fibers, and they have become established in the market. Even if the new synthetic fiber is dyed with the conventional disperse dye composition, there is a problem that a dyed product which can sufficiently satisfy leveling property, build-up property and wet fastness, particularly washing fastness, cannot be obtained. Was. For this reason, not only when dyeing polyester fiber materials, but also when dyeing new synthetic fibers, disperse dyes that have excellent leveling properties and build-up properties, and that give dyeings with good wet fastness. Development was desired.

[0004]

Means for Solving the Problems The present inventors have made intensive studies to solve the above problems, and as a result, have found that they contain a specific thiophenazo compound having a sulfoamide group and an anthraquinone compound and / or a quinone compound. By dyeing using the disperse dye composition thus obtained, not only when dyeing a polyester fiber material, but also when dyeing a new synthetic fiber, excellent leveling properties, excellent build-up properties,
It has been found that a dyed product having good wet fastness such as washing fastness can be obtained, and the present invention has been completed.

That is, the present invention provides a compound represented by the general formula (I)

[0006]

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(Wherein R ₁ represents a hydrogen atom or a halogen atom, R ₂ represents an optionally substituted lower alkyl group or an optionally substituted phenyl group,
₃ represents a hydrogen atom or a lower alkoxy group, R _4, R
₅ represents a hydrogen atom or an optionally substituted alkyl group independently of each other. A thiophenazo compound represented by the general formula (II):

[0008]

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(Wherein, R ₆ represents an amino group which may be substituted, R ₇ represents a hydroxyl group or an amino group which may be substituted, and R ₈ and R ₉ each independently represent A hydroxyl group, an amino group or a nitro group which may be substituted, R ₁₀ represents a hydrogen atom, a halogen atom or a phenyl group which may be substituted, and n represents that R ₁₀ is a hydrogen atom
When R ₁₀ is a halogen atom, it represents 1 or 2, and when R ₁₀ is an optionally substituted phenyl group, it represents 1. ) Anthraquinone compound,
And / or general formula (III)

[0010]

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(Wherein X represents an oxygen atom or an imino group, and R ₁₁ represents a lower alkyl group which may be substituted) and a disperse dye composition comprising a quinone compound represented by the formula: It is intended to provide a method for coloring a hydrophobic material using the same.

[0012]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.
The thiophenazo compound used in the present invention is represented by the general formula (I), wherein R ₁ represents a hydrogen atom or a halogen atom such as a bromine atom or a chlorine atom, and R ₂ represents It represents a lower alkyl group which may be substituted or a phenyl group which may be substituted.

The lower alkyl group which may be substituted in R ₂ includes, for example, hydroxy, C 1 -C 4
And an alkoxy group, an alkyl group having 1 to 4 carbon atoms which may be substituted with a halogen atom or the like.

Specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, methoxyethyl, ethoxyethyl, hydroxyethyl, chloroethyl and the like.

The phenyl group which may be substituted in R ₂ includes, in addition to phenyl, one or two groups selected from the group consisting of hydroxy, an alkoxy group having 1 to 4 carbon atoms and a halogen atom. Substituted phenyl and the like can be mentioned, and specific examples thereof include, for example, phenyl,
Examples include p-methylphenyl, p-hydroxyphenyl, p-methoxyphenyl, o-ethoxyphenyl, p-chlorophenyl and the like.

R ₂ is preferably an unsubstituted lower alkyl group or an unsubstituted phenyl group, of which methyl, phenyl and the like are particularly preferred.

In formula (I), R ₃ represents a hydrogen atom or a lower alkoxy group. Examples of the lower alkoxy group include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, Isobutoxy, se
Examples thereof include alkoxy groups having 1 to 4 carbon atoms such as c-butoxy.

Further, in the general formula (I), R_Four, R_FiveAre each other
Independently represents a hydrogen atom or an optionally substituted alkyl group
Represents As such an optionally substituted alkyl group
Is an alkyl group having 1 to 6 carbon atoms and a substituent
For example, hydroxy, alkoxy having 1 to 6 carbon atoms, shea
No, phenyl, phenoxy, benzyloxy, phenoxy
Cicarbonyl, phenoxycarbonyloxy, benzoi
Luoxy, alkyl carbonyl, alkoxy carbonyl
, Alkoxycarbonyloxy, tetrahydrofurf
Ryloxycarbonyl, allyl, general formula -OW¹-O
-W^Two, -O-CO-W^Two, -CO-OW ¹-OW
^Two(Where W¹Is methylene, ethylene, propylene, etc.
Represents lower alkylene having 1 to 4 carbon atoms;^TwoIs
Chill, ethyl, n-propyl, isopropyl, n-butyl
, Isobutyl, sec-butyl, etc. with 1 to 4 carbon atoms
Represents an alkyl group or a phenyl group. )
Having, for example, an alkyl having 1 to 6 carbon atoms.
Wear.

R_Four, R_FiveMay be substituted
Specific examples of the alkyl group include, for example, methyl and ethyl.
, N-propyl, isopropyl, n-butyl, isobu
Chill, sec-butyl, n-pentyl, isopentyl, n-
Hexyl, hydroxyethyl, hydroxypropyl,
Toxiethyl, ethoxypropyl, cyanoethyl,
Nilethyl, phenylpropyl, phenoxyethyl,
Benzyloxyethyl, phenoxycarbonylethyl,
Phenoxycarbonyloxyethyl, benzoyloxy
Ethyl, methylcarbonylethyl, ethylcarbonyl
Tyl, propylcarbonylethyl, methoxycarbonyl
Ethyl, ethoxycarbonylethyl, methoxycarbonyl
Ruoxyethyl, ethoxycarbonyloxyethyl, t
Trahydrofurfuryloxycarbonylethyl, tetra
Hydrofurfuryloxycarbonylpropyl, vinyl ether
Chill, -C_TwoH_FourOC_TwoH_FourOCH_Three, -C_TwoH_FourOC
_TwoH _FourOC_TwoH_Five, -C_ThreeH₆OC_TwoH_FourOCH_Three, −
C_ThreeH₆OC_TwoH_FourOC_TwoH _Five, -C_TwoH_FourOCOCH
_Three, -C_TwoH_FourOCOC_TwoH_Five, -C_TwoH_FourCOOC _Two
H_FourOCH_Three, -C_TwoH_FourCOOC_TwoH_FourOC_TwoH_Five,
-C_TwoH_FourOC_TwoH_FourOC₆H_Five, -C_TwoH_FourOC_TwoH
_FourOC₆H_FiveAnd the like.

R ₄ and R ₅ are preferably an unsubstituted alkyl group and the other is an substituted alkyl group.

The anthraquinone compound used in the present invention is represented by the general formula (II):
R ₆ represents an amino group which may be substituted. Examples of such a substituent include a phenyl group which may be substituted with a substituent selected from the group consisting of alkyl having 1 to 4 carbon atoms, hydroxyalkyl, and a halogen atom;
O—W ⁴ —O—W ⁵ (wherein W ⁴ represents alkylene having 1 to 4 carbon atoms such as methylene, ethylene and propylene, and W ⁵ represents methyl, ethyl, n-propyl, isopropyl, n Represents a lower alkyl group having 1 to 4 carbon atoms such as -butyl, isobutyl, sec-butyl, etc.), and an alkyl group having 1 to 4 carbon atoms which may be substituted.

Here, specific examples of the phenyl group which may be substituted with a substituent selected from the group consisting of alkyl having 1 to 4 carbon atoms, hydroxyalkyl and halogen atom include, for example, phenyl, m-methyl Phenyl, p-hydroxyethylphenyl, m-hydroxyethylphenyl, p-hydroxypropylphenyl, p-chlorophenyl, p-bromophenyl, m-chlorophenyl, m-
Bromophenyl and the like can be mentioned.

In addition, the general formula -CO-OW^Four-OW
^Five(Where W^FourAnd W^FiveHas the meaning described above. )so
An alkyl group having 1 to 4 carbon atoms which may be substituted
Examples of the body include, for example, methyl, ethyl, n-propyl
, Isopropyl, n-butyl, isobutyl, sec-butyl
, N-pentyl, -C_TwoH_FourCOOC_TwoH_FourOC
H_Three, -C_ThreeH₆COOC_TwoH_FourOCH_Three, -C_TwoH_Four
COOC_TwoH_FourOC_TwoH_Five, -C _ThreeH₆COOC_TwoH_Four
OC_TwoH_Five, -C_TwoH_FourCOOC_ThreeH₆OCH_ThreeEtc.
I can do it.

Specific examples of R ₆ include, for example, amino,
Phenylamino, m-methylphenylamino, p-hydroxyethylphenylamino, m-hydroxyethylphenylamino, p-hydroxypropylphenylamino, p-chlorophenylamino, p-bromophenylamino, m-chlorophenylamino, m-bromophenyl amino,

[0025] methylamino, ethylamino, n- propylamino, isopropylamino, n- butylamino, isobutylamino, sec- butylamino, n- _{pentylamino, -NHC 2 H 4 COOC 2 H} 4 OCH 3, -NHC
_{3 H 6 COOC 2 H 4 OCH} 3, -NHC 2 H 4 COO
_{C 2 H 4 OC 2 H 5} , -NHC 3 H 6 COOC 2 H 4 O
C ₂ H _5, and the like can be given _{-NHC 2 H 4 COOC 3 H 6} OCH 3.

R ₆ is preferably amino, methylamino, phenylamino, p-chlorophenylamino, p-
Hydroxyethyl phenylamino, m- hydroxyethyl phenylamino, hydroxymethyl amino, isobutylamino, sec- butylamino, -NHC ₂ H ₄ COOC
_{2 H 4 OCH 3, -NHC 3} H 6 COOC 2 H 4 OCH
₃

In the formula of the anthraquinone compound (II), R
₇ represents a hydroxyl group or an amino group which may be substituted.

Specific examples of the optionally substituted amino group for R ₇ include the same optionally substituted amino groups as those described above for R ₆ . Phenylamino. R
₇ is preferably a hydroxyl group, amino, or phenylamino.

In the formula of the anthraquinone compound (II), R
₈, R₉Are independently of each other a hydroxyl group, even if
Represents a good amino or nitro group, but such substituted
As the amino group which may be present, a group represented by the general formula -W⁶-CO-O
-W⁷-OW⁸(Where W ⁶, W⁷Are independent of each other
With 1 to 4 carbon atoms such as methylene, ethylene and propylene
Lower alkylene;⁸Is methyl, ethyl,
n-propyl, isopropyl, n-butyl, isobuty
And lower alkyl groups having 1 to 4 carbon atoms such as
Represent. )).
And specific examples thereof include amino, -NHC_TwoH
_FourCOOC_TwoH_FourOCH_Three, -NHC_ThreeH₆COOC_Two
H_FourOCH_Three, -NHC_TwoH_FourCOOC_TwoH_FourOC_TwoH
_Five, -NHC _ThreeH₆COOC_TwoH_FourOC_TwoH_Five, -NH
C_TwoH_FourCOOC_ThreeH₆OCH_ThreeEtc.
You. R₇Is preferably a hydroxyl group, nitro, amino,-
NHC_TwoH_FourCOOC_TwoH _FourOCH_ThreeIt is.

Further, in the formula of the anthraquinone compound (II),
R_TenIs a halogen atom such as a hydrogen atom, chlorine atom, bromine atom, etc.
And a phenyl group which may be substituted,
Is R _TenIs a hydrogen atom, represents 2;_TenIs haloge
R 1 represents 1 or 2,_TenIs replaced
And represents 1 when it is a phenyl group which may be substituted.

In the optionally substituted phenyl group for R ₁₀ , examples of the substituent include a hydroxyl group, an alkoxy having 1 to 6 carbon atoms, a general formula -O-CO-W ⁹ ,-
During ^{O-CO-O-W 10} ( wherein, W ^9, W ¹⁰ are methyl, ethyl, n- propyl, isopropyl, n- butyl, isobutyl, alkyl group having 1 to 4 carbon atoms such as sec- butyl,
Or a phenyl group. ) And the like.

Specific examples of the optionally substituted phenyl group for R ₁₀ include, for example, phenyl, m-hydroxyphenyl, p-hydroxyphenyl, m-methoxyphenyl, p-methoxyphenyl, p-ethoxyphenyl, p-ethoxyphenyl -Propoxyphenyl, m-methylcarbonyloxyphenyl, p-methylcarbonyloxyphenyl,
p-ethylcarbonyloxyphenyl, p-propylcarbonyloxyphenyl, m-propylcarbonyloxyphenyl, m-methoxycarbonyloxyphenyl,
Examples include p-methoxycarbonyloxyphenyl, p-ethoxycarbonyloxyphenyl, p-propoxycarbonyloxyphenyl, m-propoxycarbonyloxyphenyl, benzoyloxyphenyl and the like.

R ₁₀ is preferably a hydrogen atom, p-
Hydroxyphenyl, p-methoxyphenyl, p-ethoxyphenyl, p-methylcarbonyloxyphenyl,
p-ethylcarbonyloxyphenyl, p-methoxycarbonyloxyphenyl, p-ethoxycarbonyloxyphenyl and benzoyloxyphenyl.

The anthraquinone compound used in the present invention is not particularly limited as long as it is represented by the general formula (II). Preferred compounds are those wherein R ₇ is a hydroxyl group, amino or phenylamino, and R ₉ is , A hydroxyl group or a nitro group.

The quinone compound used in the present invention is represented by the following general formula (III).
Represents an oxygen atom or an imino group, and R ₁₁ represents an optionally substituted lower alkyl group. Examples of such an alkyl group include an alkyl group having 1 to 5 carbon atoms.
~ 6 alkoxy, general formula -OW ¹ -OW ³ ,-
CO—O—W ³ (where W ¹ is methylene, ethylene,
Propylene, alkylene having 1 to 4 carbon atoms such as butylene, and W ³ represents lower alkyl having 1 to 4 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, and sec-butyl. . ) And the like.

R₁₁Optionally substituted lower represented by
Specific examples of the alkyl group include methyl, ethyl, n-pro
Pill, isopropyl, n-butyl, sec-butyl, n-pliers
Methoxyethyl, ethoxyethyl, propoxyethyl
, Butoxyethyl, pentoxyethyl, hexoxy
Chill, methoxypropyl, ethoxypropyl, propoxy
Cypropyl, butoxypropyl, pentoxypropyl,
Hexoxypropyl, -C_TwoH_FourOC_TwoH_FourOCH_Three,
-C_ThreeH₆OC_TwoH_FourOCH_Three, -C_TwoH_FourOC_TwoH_Four
OC_TwoH_Five, -C_ThreeH₆OC_TwoH_FourOC_TwoH_Five, -C_Two
H_FourCOOCH _Three, -C_TwoH_FourCOOC_TwoH_FiveEtc.
Can be

R ₁₁ is preferably alkyl having 2 to 4 carbon atoms which may be substituted by alkoxy having 2 to 6 carbon atoms.

The thiophenazo compound (I), anthraquinone compound (II) and quinone compound (I) used in the present invention
The production method of II) is not particularly limited. For example, the thiophenazo compound (I) is represented by the following general formula (IV)

[0039]

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(Wherein R ₁ has the same meaning as described above), which is diazotized by a conventional method.
Then, this is represented by the following general formula (V)

[0041]

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Wherein R ₂ , R ₃ , R ₄ and R ₅ have the same meaning as described above;
It can be obtained by coupling in a conventional manner. Further, the anthraquinone compound (II) is described in, for example, a known method such as the method described in JP-B-32-9089, and the quinone compound (III) is described in, for example, JP-B-41-3711. Can be obtained in accordance with known methods such as the method described above.

The disperse dye composition of the present invention comprises at least one thiophenazo compound (I) and at least one anthraquinone compound (II) and / or a quinone compound (III).
Species containing two or more thiophenazo compounds (I), two or more anthraquinone compounds (II),
A compound containing two or more quinone compounds (III) may be used.

Further, as long as the effects of the present invention are not impaired, even if the composition further contains other disperse dyes,
It may contain a dispersant such as an anionic dispersant or a nonionic dispersant, an extender, a pH adjuster, a dispersion leveling agent, a builder, an organic solvent, and an auxiliary agent such as a resin binder.

Specific examples of the anionic dispersant include formalin condensates of naphthalene sulfonic acids, lignin sulfonic acids, and formalin condensates of cresol-scheffer acid, and nonionic dispersants. Examples of the agent include polyoxyethylene alkyl ethers and polyoxyethylene alkyl phenyl ethers.

The content ratio of each compound in the disperse dye composition of the present invention is not particularly limited, but the preferable content ratio is thiophenazo compound (I), thiophenazo compound (I), anthraquinone compound (II) and quinone. Compound (I
1) to 99% by weight based on the total weight of (II). In particular, a compound containing 20 to 80% by weight of the thiophenazo compound (I) based on the total weight of the thiophenazo compound (I), the anthraquinone compound (II) and the quinone compound (III) is particularly preferable.

In the present invention, the thiophene compound (I)
And an anthraquinone compound (II) and / or a quinone compound
The method of mixing (III) is not particularly limited, either. For example, when used as a disperse dye, it may be mixed before dyeing or may be mixed at the time of dyeing. As the former method, for example, after previously mixing each compound and, if necessary, the above dispersant, etc., a method of dispersing in an aqueous medium or the like, and adding the above dispersant, etc., as necessary The respective compounds may be separately dispersed and then mixed, and the like.Examples of the latter method include, for example, adding a dispersant or the like as necessary and separately dispersing. A method of adding each compound to a dye bath can be used.

The form of the disperse dye composition of the present invention is not particularly limited, and may be in the form of a powder, a granule, or a liquid.

The disperse dye composition of the present invention can be used, for example, as a disperse dye for dyeing or printing a hydrophobic fiber material. Here, as the hydrophobic fiber material, specifically, other than polyester-based fibers, triacetate-based fibers, diacetate-based fibers, polyamide-based fibers, polycarbonate-based fibers, and the like, blended products and interwoven products thereof, and cellulose-based fibers Fibers, natural fibers such as wool and silk, and blended and woven products thereof can also be exemplified.

The disperse dye composition of the present invention is particularly useful for dyeing or printing polyester fiber materials, and is also useful for dyeing or printing new synthetic fibers.

The new synthetic fibers include, among polyester fiber materials, for example, polycondensates of polyethylene terephthalate, polybutylene terephthalate, terephthalic acid and the like with 1,4-bis (hydroxymethyl) cyclohexane. Made of polyester fiber, for example, ultra-fine fiber yarn of 1 denier or less (fine denier,
Ultra microfiber, etc.), irregular cross-section yarn, different shrinkage blended yarn, and the like. They may be composed of mixed or interwoven fabrics of extra-fine fiber yarns and yarns of normal thickness, or may be blended or interwoven products with fibers other than the new synthetic fiber. Good.

When these hydrophobic materials are used for dyeing or printing, the form is not particularly limited, and may be in the form of yarn or fiber.
Further, it may be in the form of a nonwoven fabric.

In the method of coloring the hydrophobic material of the present invention, the disperse dye composition of the present invention may be used, and other conditions are not particularly limited. Examples of the method include a hydrophobic fiber material such as polyester. When dyeing the system fiber material, the auxiliary agent such as a pH adjuster is added to a dye bath in which the disperse dye composition of the present invention is dispersed in an aqueous medium, if necessary, and the polyester fiber material is immersed. 100 ° C. or more under pressure, preferably 105 to 14
A method of dyeing at about 0 ° C. for about 30 to 60 minutes can be used.

Further, a method of dyeing at around 95 to 100 ° C. in the presence of a carrier such as O-phenylphenol or methyl naphthalene, or a method of padding a dyeing bath with a hydrophobic fiber material and steaming at 100 ° C. or higher. A method of performing heat-sensitive treatment can also be used.

In printing, there may be mentioned a method in which the disperse dye composition of the present invention is kneaded together with a sizing agent, printed on a hydrophobic fiber material or the like, dried, steamed and subjected to heat treatment. .

The disperse dye composition of the present invention is used not only as a disperse dye for dyeing or printing a hydrophobic fiber material as described above, but also as a dye for ink jet, a dye for sublimation transfer type thermal recording and the like. Can be used.

[0057]

EFFECTS OF THE INVENTION By using the disperse dye composition of the present invention, for example, in dyeing a hydrophobic fiber material, a dyed material having excellent leveling properties and build-up properties and good wet fastness such as washing fastness. Is obtained.

[0058]

EXAMPLES The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples.
In the examples, parts and% indicate parts by weight and% by weight, respectively.

Example 1 The following formula (1)

[0060]

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0.7 parts of a thiophenazo compound represented by the following formula:
The following equation (2)

[0062]

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0.3 parts of an anthraquinone compound represented by the following formula:
And 3 parts of a formalin condensate of naphthalenesulfonic acid,
It was dispersed in 6 parts of water to obtain a disperse dye composition. 20 parts of the obtained disperse dye composition, 1.2 parts of acetic acid and sodium acetate 4.
Add 8 parts to the dye bath, set the bath ratio to 1:30, and add Tetron Tropical (a polyester fiber fabric manufactured by Toray Industries, Inc.).
When 100 parts were immersed and dyed at about 130 ° C. for about 60 minutes according to a conventional method, the obtained dyed product was a uniform blue dyeing product without spots, and the washing fastness was good. Further, when the obtained disperse dye composition was similarly dyed using 30 parts, the obtained dyed product was remarkably dark blue in comparison with the dyed product when dyed using 20 parts of the disperse dye composition. It was a dyed product, and it was found that the build-up property of the present disperse dye composition was good.

Example 2 In Example 1, instead of using 0.3 parts of the anthraquinone compound represented by the formula (2), the following formula (3) was used.

[0065]

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A disperse dye composition was obtained by dispersing in water according to Example 1 except that 0.3 part of the quinone compound represented by the following formula was used. Using the obtained disperse dye composition, dyeing was carried out in the same manner as in Example 1, and the obtained dyed product was a uniform blue dyed product without spots, and the washing fastness was also good. The build-up properties were also good.

Comparative Example 1 Instead of using 0.7 parts of the thiophenazo compound represented by the formula (1) in Example 1, the following formula (4) was used.

[0068]

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A disperse dye composition was obtained by dispersing in water according to Example 1, except that 0.7 part of a thiophenazo compound having a carboxamide group represented by the following formula was used. Using the obtained disperse dye composition, dyeing was carried out in the same manner as in Example 1, and the obtained dyed product had poor leveling properties, in which spots were observed, and extremely poor washing fastness. The blue color of the dyed product obtained by dyeing using 30 parts of the disperse dye composition is almost not different from the blue color of the dyed product obtained by dyeing using 20 parts, and the build-up property is improved. Was found to be bad.

Comparative Example 2 In Example 2, instead of using 0.7 parts of the thiophene compound represented by the formula (1), a thiophene compound having a carboxamide group represented by the formula (4) was used instead of 0.7 part.
A dispersion dye composition was obtained by dispersing in water in accordance with Example 2, except for using parts. Using the obtained disperse dye composition, dyeing was carried out in the same manner as in Example 1, and the obtained dyed product had poor leveling properties, in which spots were observed, and extremely poor washing fastness. The disperse dye composition 30
The darkness of the blue color of the dyed product obtained by dyeing using 20 parts was almost not different from the blue color of the dyed product obtained by dyeing using 20 parts, indicating that the build-up property was poor. Was.

Comparative Example 3 To 1.0 part of the anthraquinone compound represented by the above formula (2), 3 parts of a formalin condensate of naphthalenesulfonic acid was added and dispersed in 6 parts of water to obtain a disperse dye composition. When the obtained disperse dye composition was dyed in the same manner as in Example 1, the obtained dyed product was extremely poor in washing fastness and poor in build-up property.

Comparative Example 4 To 1.0 part of the quinone compound represented by the above formula (3), 3 parts of a formalin condensate of naphthalenesulfonic acid was added and dispersed in 6 parts of water to obtain a disperse dye composition. Using the obtained disperse dye composition, dyeing was carried out in the same manner as in Example 1, and the resulting dyed product had poor leveling properties with spots, poor washing fastness, and The build-up property was also poor.

Example 3 In Example 1, instead of using 0.7 part of the thiophenazo compound represented by the formula (1), the following formula (5) was used.

[0074]

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In place of using 0.7 part of the thiophenazo compound represented by the formula and 0.3 part of the anthraquinone compound represented by the formula (2), the following formula (6) is used.

[0076]

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A disperse dye composition was obtained by dispersing in water according to Example 1, except that 0.3 part of the anthraquinone compound represented by the following formula was used. Using the obtained disperse dye composition, dyeing was carried out in the same manner as in Example 1, and the obtained dyed product was a uniform blue dyed product without spots, and the washing fastness was also good. The build-up properties were also good.

Example 4 Instead of using 0.3 part of the anthraquinone compound represented by the formula (6) in Example 3, the following formula (7) was used.

[0079]

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A disperse dye composition was obtained by dispersing in water according to Example 3, except that 0.3 part of the quinone compound represented by the following formula was used. Using the obtained disperse dye composition, dyeing was carried out in the same manner as in Example 1, and the obtained dyed product was a uniform blue dyed product without spots, and the washing fastness was also good. The build-up properties were also good.

Example 5 Examples 1 to 4 were repeated except that 100 parts of a new synthetic fiber Toraysee (microfiber polyester fiber woven fabric manufactured by Toray Industries, Inc.) was used instead of using tetron tropical. When dyed according to the method, the obtained dyed product was a uniform blue dyed product without spots, and also had good washing fastness. The build-up properties were also good.

Comparative Example 5 The procedure of Example 5 was repeated, except that the disperse dye compositions obtained in Comparative Examples 1 to 4 were used instead of the disperse dye compositions obtained in Examples 1 to 4. When the new synthetic fiber Toraysee was dyed according to, the obtained dyed product was extremely poor in washing fastness.

Examples 6 to 23 In Example 3, instead of using the thiophenazo compound represented by the formula (5) and the anthraquinone compound represented by the formula (6), the thiophenazo compounds (8) to (23) and the anthraquinone compounds (24) to (37) shown in Table 2 or the quinone compounds (38) to (38) shown in Table 3
A disperse dye composition was obtained in the same manner as in Example 3 except that (41) was used in the combination and use amount shown in Table 4, and dyed in the same manner as in Example 3. All were uniform blue dyeings without spots, and also had good washing fastness. In addition, the build-up properties were all good.

[0084]

[Table 1]

[0085]

[Table 2]

[0086]

[Table 3]

[0087]

[Table 4]

Example 24 In Example 1, the amount of the thiophenazo compound represented by the formula (1) was changed to 0.95 part, and the amount of the anthraquinone compound represented by the formula (2) was changed to 0.05 part. When a disperse dye composition was obtained in accordance with Example 1 and dyed in the same manner as in Example 1, the resulting dyed product was a uniform blue dyeing product having no spots, and the washing fastness was good. Was.
The build-up properties were also good.

Example 25 In Example 1, instead of using 0.7 part of the thiophenazo compound represented by the formula (1) and 0.3 part of the anthraquinone compound represented by the formula (2), a thiophenazo compound represented by the formula (5) was used. A disperse dye composition was obtained in the same manner as in Example 1, except that 0.8 parts, 0.1 part of the anthraquinone compound represented by the formula (2) and 0.1 part of the quinone compound represented by the formula (3) were used. When the obtained disperse dye composition was dyed in the same manner as in Example 1, the obtained dyed product was a uniform blue dyed product without spots, and the washing fastness was good. The build-up properties were also good.

Claims (5)

[Claims] 1. A compound of the general formula (I) (Wherein, R ₁ represents a hydrogen atom or a halogen atom;
₂ represents a lower alkyl group which may be substituted or a phenyl group which may be substituted; R ₃ represents a hydrogen atom or a lower alkoxy group; R ₄ and R ₅ each independently represent a hydrogen atom Or an alkyl group which may be substituted. ) And a thiophenazo compound represented by the general formula (II): (Wherein, R ₆ represents an optionally substituted amino group, R ₇ represents a hydroxyl group or an optionally substituted amino group, and R ₈ and R ₉ each independently represent a hydroxyl group, a substituted R ₁₀ represents an amino group or a nitro group which may be
A hydrogen atom, a halogen atom or a phenyl group which may be substituted, n represents 2 when R ₁₀ is a hydrogen atom, and represents 1 or 2 when R ₁₀ is a halogen atom;
_{When 1} is an optionally substituted phenyl group, it represents 1. And / or an anthraquinone compound represented by the general formula (III): (Wherein, X represents an oxygen atom or an imino group, and R ₁₁ is
Represents a lower alkyl group which may be substituted. A disperse dye composition comprising a quinone compound represented by the formula (1): 2. The thiophenazo compound represented by the general formula (I) is added to the total weight of the thiophenazo compound represented by the general formula (I), the anthraquinone compound represented by the general formula (II) and the quinone compound (III). The disperse dye composition according to claim 1, which is contained in an amount of 1 to 99% by weight. 3. The thiophenazo compound represented by the general formula (I) is added to the total weight of the thiophenazo compound represented by the general formula (I), the anthraquinone compound represented by the general formula (II) and the quinone compound (III). The disperse dye composition according to any one of claims 1 to 2, which is contained in an amount of 20 to 80% by weight. 4. A method for coloring a hydrophobic material, comprising using the disperse dye composition according to claim 1. 5. The coloring method according to claim 4, wherein the hydrophobic material is a new synthetic fiber.