JPH10316878A - Disperse dye composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a disperse dye composition capable of dyeing in various colors such as brown, gray and beige in high reproducibility, having improved washing fastness and suitable for the dyeing of polyester fiber, etc., by including respectively specific thiophene azo compound, pyridone azo compound, etc. SOLUTION: This disperse dye composition contains (A) a thiophene azo compound of the formula I [X1 is H, a halogen, a (substituted)alkyl, etc.; Y1 is H, a halogen, a (substituted)aryl, etc.; Z1 is H, a halogen, cyano, etc.; R1 is H, a halogen or an alkoxy; R2 and R3 are each H, a (substituted)alkyl, etc.] and (B) a pyridone azo compound of the formula II [X2 is H, a halogen, etc.; Y2 is H, an alkoxy, etc.; R4 is H, a (sbstituted)alkyl, etc.] and/or (C) a benzothiazole azo compound of the formula III (Y3 is a halogen, an alkoxy, etc.; (m) is 1 or 2; R5 is H, an alkyl, etc.; R6 and R7 are each a hydroxyalkyl, etc.). The content of the component A is preferably 0.5-99.5 wt.% based on the total weight of the composition. The composition is preferably used for the dyeing of a hydrophobic material such as polyester fiber having a fineness of <=1 de.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a disperse dye composition containing a thiophenazo compound and a heterocyclic compound, and a method for coloring a hydrophobic material such as a polyester fiber material using the same.

[0002]

2. Description of the Related Art Conventionally, as a disperse dye for three primary colors,
A disperse dye composition containing a heterocyclic yellow disperse dye and / or a heterocyclic red disperse dye and a thiophenazo blue disperse dye is used. In addition,
JP-A-8-84120 discloses the following formula:

[0003]

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[0004] A thiophenazo-based blue disperse dye is disclosed.

[0005]

However, for the three primary colors obtained by blending the above-mentioned known thiophenazo blue disperse dye with a heterocyclic yellow dye and / or a heterocyclic red dye. When dyeing is performed using the disperse dye composition, there is a problem that the washing fastness of the obtained dyed product becomes extremely poor and troubles such as uneven dyeing often occur. In particular, when the dye concentration between the three primary color dyes is significantly different, variation occurs between the dyeing batches, resulting in a hue difference between the obtained dyed materials, or a dyed material having a spotted dye. There was a problem that it could be obtained.

[0006]

Means for Solving the Problems The present inventors have intensively studied to solve these problems, and as a result, a disperse dye composition containing a specific thiophene azo compound and a heterocyclic compound. It has been found that coloring of a hydrophobic material by using the method described above can provide a dyed product having good reproducibility and excellent washing fastness and levelness, thereby completing the present invention.

That is, the present invention provides the following formula (I)

[0008]

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(Wherein X1 is a hydrogen atom, a halogen atom,
Cyano group, nitro group, optionally substituted alkyl group, optionally substituted aryl group, formyl group, optionally substituted alkylcarbonyl group, optionally substituted arylcarbonyl group, substituted An optionally substituted alkyloxycarbonyl group, an optionally substituted carbamoyl group, an optionally substituted alkylsulfonyl group or an optionally substituted arylsulfonyl group, Y1 represents a hydrogen atom, a halogen atom, a cyano group, Nitro group, optionally substituted alkyl group, optionally substituted aryl group, optionally substituted hydroxyl group, optionally substituted mercapto group, formyl group, optionally substituted alkylcarbonyl group An optionally substituted arylcarbonyl group, an optionally substituted alkyloxy Carbonyl group or SO2K (where, K is an alkyl group, an alkenyl group, an aryl group, a chlorine atom, a bromine atom,. An optionally substituted hydroxyl group or an optionally substituted amino group) represents, Z
1 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxy group, an optionally substituted alkylcarbonyl group An optionally substituted arylcarbonyl group, an optionally substituted alkyloxycarbonyl group, an optionally substituted aryloxycarbonyl group, an optionally substituted carbamoyl group, an optionally substituted alkylsulfonyl R1 represents a hydrogen atom, a halogen atom or an alkoxy group; R2 and R3 independently of one another are a hydrogen atom, an optionally substituted alkyl group, a substituted or unsubstituted arylsulfonyl group; An optionally substituted cycloalkyl group, an optionally substituted alkenyl group or tet It represents a tetrahydrofurfuryl group, R2
And R3 together with the nitrogen atom to which they are attached may form a morpholino group. A) a monoazo compound represented by the general formula (II):

[0010]

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Wherein X2 represents a hydrogen atom, a halogen atom, a cyano group or a nitro group, and Y2 is a hydrogen atom, a halogen atom, an alkoxy group, a phenylsulfonyloxy group, an optionally substituted aminosulfonyloxy group. ,
Optionally substituted aminosulfonyl group, alkoxyalkoxyalkoxycarbonyl group, optionally substituted aminocarbonyl group, nitro group, 5-membered ring or 6
Represents an alkoxycarbonyl group which may be substituted by a cycloalkyl containing one oxygen atom in the member ring, or a phenoxyalkoxycarbonyl group, wherein R4 is a hydrogen atom,
Represents an alkyl group which may be substituted, or an aryl group which may be substituted. And / or the general formula (III)

[0012]

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(Wherein Y3 represents a halogen atom, an alkoxy group, an alkylsulfonyl group or a nitro group;
Is 1 or 2 when Y3 is a halogen atom, and is 1 when Y3 is an alkoxy group, an alkylsulfonyl group or a nitro group. R5 is a hydrogen atom,
Represents an alkyl group, a phenylcarbonylamino group or an alkylcarbonylamino group, and R6 and R7 independently represent a hydroxyalkyl group, an alkyl group, an alkylcarbonyloxyalkyl group or a cyanoalkyl group. The present invention provides a disperse dye composition comprising a benzothiazole azo compound represented by the formula (1), and a method for coloring a hydrophobic material using the disperse dye composition. Hereinafter, the present invention will be described in detail.

[0014]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The definitions of the symbols in the above formulas will be described below. X1, Y1, K, Z1, R
1, R2, R3, Y2, R4, Y3, R5, R6 and R
7, alkyl group, alkylcarbonyl group, alkyloxycarbonyl group, alkylsulfonyl group, alkenyl group, alkoxy group, alkoxyalkoxyalkoxycarbonyl group, aminocarbonyl group, phenoxyalkoxycarbonyl group, alkylcarbonylamino group, hydroxyalkyl Group, alkylcarbonyloxyalkyl group and cyanoalkyl group, alkyl,
Both alkenyl and alkoxy may be straight-chain or branched. Furthermore, Y
The alkyl group which is a substituent of the aminosulfonyloxy group and the aminosulfonyl group represented by 2 may be linear or branched.

In the above formula (I), X1 represents a hydrogen atom, a halogen atom (a chlorine atom, a bromine atom or the like), a cyano group, a nitro group, an optionally substituted alkyl group, an optionally substituted aryl group. , A formyl group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkyloxycarbonyl group, an optionally substituted carbamoyl group, an optionally substituted Represents an alkylsulfonyl group or an arylsulfonyl group which may be substituted, and examples of the substituent of the alkyl group include a substituted or unsubstituted aryl group such as phenyl and tolyl, a halogen atom (a chlorine atom, a bromine atom and the like). ) Or an alkoxy group having 1 to 4 carbon atoms. Examples of the substituent of the aryl group include an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a halogen atom (a chlorine atom,
Bromine atom). Examples of the substituent of the alkylcarbonyl group include an alkoxy group having 1 to 4 carbon atoms and a halogen atom (eg, a chlorine atom or a bromine atom). Examples of the substituent of the arylcarbonyl group include an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a halogen atom (such as a chlorine atom or a bromine atom). Examples of the substituent of the alkyloxycarbonyl group include a halogen atom (a chlorine atom, a bromine atom and the like). Examples of the substituent of the carbamoyl group include an alkyl group having 1 to 4 carbon atoms. Examples of the substituent of the alkylsulfonyl group include, for example,
Examples thereof include an alkoxy group having 1 to 4 carbon atoms. Examples of the substituent of the arylsulfonyl group include, for example, C1 to C1.
Examples thereof include four alkoxy groups, an alkyl group having 1 to 4 carbon atoms, and a halogen atom (eg, a chlorine atom or a bromine atom).

X1 represents a hydrogen atom, chlorine atom, bromine atom, cyano group, nitro group, formyl group, C1-4 alkylcarbonyl group, C1-4 alkyloxycarbonyl group, carbamoyl group, C1-4 alkylsulfonyl group,
A phenylsulfonyl group is preferable, and further a cyano group,
Nitro and formyl groups are particularly preferred. Y1 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted hydroxyl group, an optionally substituted mercapto group, formyl Group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkyloxycarbonyl group or SO2K (where K is an alkyl group, an alkenyl group, an aryl group, Atom, bromine atom, an optionally substituted hydroxyl group or an optionally substituted amino group), wherein an alkyl group, an aryl group, an alkylcarbonyl group, an arylcarbonyl group and an alkyloxycarbonyl group As a substituent of
Examples of the same substituents as the alkyl group substituent, the aryl group substituent, the alkylcarbonyl group substituent, the arylcarbonyl group substituent, and the alkyloxycarbonyl group described above for X1 can be given. Also,
Examples of the substituent of the hydroxyl group and the amino group represented by K include, for example, an alkyl group having 1 to 4 carbon atoms. As Y1, a hydrogen atom, a chlorine atom, a bromine atom, a C1-4 alkyl group, a phenyl group, a C1-4 alkylcarbonyl group, a C1-4 alkoxycarbonyl group, and a benzoyl group are preferable, and a hydrogen atom and a methyl group are particularly preferable. preferable.

Z1 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxy group, or an optionally substituted Alkylcarbonyl group, optionally substituted arylcarbonyl group, optionally substituted alkyloxycarbonyl group, optionally substituted aryloxycarbonyl group, optionally substituted carbamoyl group, optionally substituted A good alkylsulfonyl group or an optionally substituted arylsulfonyl group, wherein the substituents of the alkyl group, the aryl group, the alkylcarbonyl group, the arylcarbonyl group and the alkyloxycarbonyl group are each the above-mentioned X1 In the examples, the substituent of the alkyl group, the substituent of the aryl group, Substituents Le carbonyl group, those similar to the substituents of the substituents and alkyloxycarbonyl group arylcarbonyl group, respectively, thereof. Examples of the substituent of the aryloxycarbonyl group include an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, and a halogen atom (eg, a chlorine atom or a bromine atom).
Examples of the substituent of the alkoxy group include a halogen atom (eg, a chlorine atom and a bromine atom). Z1 represents a hydrogen atom, a cyano group, a nitro group,
C1-4 alkylcarbonyl group, benzoyl group, C1-
A 4 alkoxycarbonyl group and a phenoxycarbonyl group are preferable, and a cyano group, a nitro group, a C1-4 alkylcarbonyl group, and a C1-4 alkoxycarbonyl group are particularly preferable.

R1 represents a hydrogen atom, a halogen atom or an alkoxy group, preferably a hydrogen atom, a C1-4 alkoxy group, and particularly preferably a hydrogen atom.

R2 and R3 each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group or a tetrahydrofurfuryl group. , R2
And R3 together with the nitrogen atom to which they are attached may form a morpholino group. Here, examples of the substituent of the alkyl group and the alkenyl group include an alkoxy group having 1 to 6 carbon atoms, a cyano group, a phenyl group, a phenoxy group, a halogen atom such as a chlorine atom and a bromine atom, a hydroxy group, a benzyloxy group. C1-4 alkoxycarbonyl group, C1-4 alkoxycarbonyloxy group, C2
-5 alkanoyloxy group, benzoyloxy group, phenoxycarbonyloxy group, C2-5 alkanoyl group,
And a C1-4 alkoxy C1-4 alkoxycarbonyl group and a C1-4 alkoxy C1-4 alkoxy group. The cycloalkyl group preferably has 5 or 6 carbon atoms, and examples of the substituent include a halogen atom such as a chlorine atom and a bromine atom. Preferred R2 and R3 are each independently a halogen atom such as a chlorine atom or a bromine atom, a cyano group, or a C1 to C1 atom.
6, alkoxy, hydroxy, phenoxy, phenyl, benzyloxy, C1-4 alkoxycarbonyl, C1-4 alkoxycarbonyloxy, C2
-5 alkanoyloxy group, benzoyloxy group, phenoxycarbonyloxy group, C2-5 alkanoyl group,
A C1-6 alkyl group optionally substituted by one or two substituents selected from the group consisting of a C1-4 alkoxy C1-4 alkoxycarbonyl group and a C1-4 alkoxy C1-4 alkoxy group, a hydrogen atom, Examples thereof include an allyl group and a tetrahydrofurfuryl group. Among the above-mentioned optionally substituted C1-6 alkyl groups,
Unsubstituted ones include, for example, methyl group, ethyl group, n-
Examples include a propyl group, an i-propyl group, an n-butyl group, an i-butyl group, an n-pentyl group, an i-pentyl group, and an n-hexyl group. Among the above-mentioned alkyl groups, those substituted with one substituent selected from the group described above include, for example, 3-chloro (or bromo) propyl group and 2-chloro (or bromo) ethyl group. A chloro (or bromo) substituted alkyl group; a cyano substituted alkyl group such as a 2-cyanoethyl group; a C1-4 such as a 2- [methoxy (or ethoxy)] ethyl group or a 3- [methoxy (or ethoxy)] propyl group. Alkoxy-substituted alkyl groups; hydroxy-substituted alkyl groups such as 2-hydroxyethyl group, 2- (or 3-) hydroxypropyl group and 4-hydroxybutyl group; phenoxy groups such as 2-phenoxyethyl group, phenethyl group and benzyl group Substituted alkyl group or phenyl substituted alkyl group; 2-acetoxyethyl group, 4-acetoxybutyl group, 2-p Propionyloxy oxyethyl groups, such as 2-benzoyloxy ethyl C2-
5-alkanoyloxy-substituted alkyl group or benzoyloxy-substituted alkyl group; alkoxy (C1--) such as 2- [methoxy (or ethoxy)] carbonylethyl group
4) a carbonyl-substituted alkyl group; an alkoxy (C) such as a 2- [methoxy (or ethoxy)] carbonyloxyethyl group or a 2-phenoxycarbonyloxyethyl group;
1-4) carbonyloxy-substituted alkyl group or phenoxycarbonyloxy-substituted alkyl group; alkanoyl-substituted alkyl group such as 2-acetylethyl group and 2-propionylethyl group; 2- (2-methoxyethoxy) ethyl group, 2- ( 2-ethoxyethoxy) ethyl group, 2- (2
Alkoxy (C1) such as -butoxyethoxy) ethyl group
-4) an alkoxy (C1-4) substituted alkyl group; and 2
And alkoxy (C1-4) alkoxy (C1-4) carbonyl-substituted alkyl groups such as-(2-methoxyethoxycarbonyl) ethyl group. Further, among the above-mentioned alkyl groups, those substituted with two substituents selected from the aforementioned groups include, for example, a 3-phenoxy-2-hydroxypropyl group, a 3-methoxy-2-hydroxypropyl group, 3-butoxy-2-hydroxypropyl group, 3-methoxy-2-acetoxypropyl group, 3
-Ethoxy-2-acetoxypropyl group.

The thiophenazo compound represented by the formula (I) is, for example, a compound represented by the formula (IV)

[0021]

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(Wherein X1, Y1 and Z1 have the same meanings as described above), and diazotizes the 2-aminothiophenes by a conventional method.

[0023]

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(Wherein, R1, R2 and R3 have the same meanings as described above), and can be produced by coupling with a 3-aminophenol.

The 2-aminothiophenes represented by the above formula (IV) are known compounds, for example, JP-A-48-81851, JP-B-55-18710, JP-A-1-153668 and JP-A-6-153668. It can be produced by the method described in JP-A-25220. Further, the 3-aminophenols represented by the formula (V) are, for example, represented by the formula (VI)

[0026]

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(Wherein, R1 has the same meaning as described above.)
A compound represented by the formula: (VII) R2-Xa (VII) (wherein, R2 has the same meaning as described above. Xa represents a nucleophilic group such as a chlorine atom, a bromine atom, an iodine atom, a tosyloxy group, and a benzenesulfonyloxy group. A group which is eliminated or substituted by the reaction), and a compound represented by the formula (VI
II) R3-Xb (VIII) (wherein, R3 has the same meaning as described above. Xb is eliminated / substituted by a nucleophilic reaction such as a chlorine atom, a bromine atom, an iodine atom, a tosyloxy group and a benzenesulfonyloxy group). Can be produced by reacting a compound represented by the formula:

X2 in the formula (II) represents a hydrogen atom, a halogen atom, a cyano group or a nitro group, preferably a hydrogen atom, a nitro group or a cyano group. Also, Y
2 is a hydrogen atom, a halogen atom, an alkoxy group, a phenylsulfonyloxy group, an optionally substituted aminosulfonyloxy group, an optionally substituted aminosulfonyl group, an alkoxyalkoxyalkoxycarbonyl group, or an optionally substituted An aminocarbonyl group, a nitro group, an alkoxycarbonyl group optionally substituted with a cycloalkyl containing one oxygen atom in a 5- or 6-membered ring, or a phenoxyalkoxycarbonyl group, Examples of the substituent of the aminosulfonyloxy group and the aminosulfonyl group include an alkyl group having 1 to 8 carbon atoms, and a substituted or unsubstituted aryl group such as phenyl or tolyl. Y2 is preferably a chlorine atom, a methoxy group, an optionally substituted aminosulfonyloxy group, or a methoxyethoxyethoxycarbonyl group.

R4 represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group, and the alkyl group preferably has 1 to 10 carbon atoms. Further, as a substituent of the alkyl group, for example,
A halogen atom (a chlorine atom, a bromine atom, etc.), a hydroxyl group, a cyano group, an alkoxy group having 1 to 4 carbon atoms, a C1-4 alkoxy C1-4 alkoxy group, a C1-4 alkylcarbonyloxy group, a C1-4 alkoxycarbonyl group, and C1-
And 4 alkoxycarbonyloxy groups. Furthermore, examples of the substituent of the aryl group include a C1-4 alkyl group, a C1-4 alkoxy group, and a halogen atom (a bromine atom, a chlorine atom, etc.). As R4,
Preferred are a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group and a phenyl group. The pyridone azo compound represented by the formula (II) is disclosed in
It is a known compound described in, for example, JP-A-18549.

In the above formula (III), Y3 represents a halogen atom, an alkoxy group, an alkylsulfonyl group or a nitro group.
It has 8 carbon atoms, preferably the alkylsulfonyl group has 1-4 carbon atoms. As Y3, a chlorine atom, a nitro group, a methoxy group or a methylsulfonyl group is preferable. R5 represents a hydrogen atom, an alkyl group, a phenylcarbonylamino group or an alkylcarbonylamino group, and preferably, the alkyl group has 1 to 8 carbon atoms. The alkylcarbonylamino group has 2 to 5 carbon atoms. R5 is preferably a hydrogen atom, a methyl group, an acetylamino group, or a phenylcarbonylamino group.

R6 and R7 independently represent a hydroxyalkyl group, an alkyl group, an alkylcarbonyloxyalkyl group or a cyanoalkyl group, wherein the alkyl of these groups preferably has 1 to 8 carbon atoms. Have R6 and R7 each independently represent an ethyl group, a cyanoethyl group, a hydroxyethyl group,
An n-hexyl group and a methylcarbonyloxyethyl group are preferred. The benzothiazole azo compound represented by the formula (III) is a known compound described in JP-B-44-8117 and the like.

In the composition of the present invention, the thiophenazo compound represented by the formula (I) is a blue-based disperse dye,
The pyridone azo compound represented by the formula (II) is a yellow disperse dye, and the benzothiazole azo compound represented by the formula (III) is a red disperse dye. The disperse dye composition of the present invention is used in the form of a dispersion obtained by dispersing each compound, or a dried powder or granule. Dispersion of each compound represented by the formulas (I), (II) and (III) can be carried out, for example, in a sand mill by using an anionic system such as naphthalenesulfonic acid formalin condensate, ligninsulfonic acid, cresol-shaferic acid formalin condensate, etc. It can be carried out in an appropriate amount of an aqueous medium using a dispersant or a dispersant selected from various dispersants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, and other nonionic dispersants. The obtained dispersion can be used as a liquid or as a powder or granules after drying.

The composition of the present invention contains at least one thiophenazo compound represented by the above formula (I),
Pyridoneazo compounds represented by I) and a compound of formula (III)
And at least one selected from benzothiazole azo compounds represented by the formula: Specifically, one or more compounds in the thiophenazo compound group, one or more compounds in the pyridone azo compound group and / or one or more compound in the benzothiazole azo compound group,
Appropriate amount, can be blended according to the desired hue,
The preferred content of the compound of the formula (I) is 0.5 to 99.5% by weight based on the total weight of the compound of the formula (II) and / or the compound of the formula (III) and the compound of the formula (I). It is. The compounding of these compounds may be performed at the stage of dispersing each compound, may be performed after each compound is dispersed, or may be performed in a dyeing bath at the stage of dyeing. Further, the composition of the present invention may be added with a compound other than the compound represented by each of the above formulas for the purpose of adjusting the hue, and further, a dispersant, a bulking agent, a pH adjuster, a dispersion leveling agent, It may contain a dyeing aid, a solvent or a resin binder.
The composition of the present invention is useful as a disperse dye for coloring such as dyeing of hydrophobic fiber materials such as polyester, triacetate, diacetate, polyamide and polycarbonate. Dyeing, for example, a dye bath in which the composition of the present invention is dispersed in an aqueous medium, if necessary, after adding a pH adjuster, a dispersion leveling agent, and the like, a hydrophobic material such as a hydrophobic polyester fiber. Is carried out under pressure at 100 ° C. or higher, preferably 105-140 ° C. for 30-60 minutes. This dyeing time can be shortened or extended depending on the state of dyeing. Dyeing can also be performed at a relatively high temperature, for example, in the boiling state of water, in the presence of a carrier such as o-phenylphenol, trichlorobenzene, or methylnaphthalene. Furthermore, after padding the dye dispersion onto a cloth,
A so-called thermosol dyeing method in which steaming or dry heat treatment is performed at a temperature of 100 ° C. or more is also applicable. On the other hand, in the case of printing, the dye dispersion can be kneaded with an appropriate paste, padded onto a cloth, and then subjected to steaming or thermosol treatment for dyeing. Printing can also be performed by an inkjet method. Alternatively, a solvent dyeing method using an organic solvent such as trichlorethylene or perchlorethylene as a dyeing medium can be applied. Examples of the hydrophobic fiber material include polyester fiber, triacetate fiber, diacetate fiber, and polyamide fiber material. As the blended or interwoven product, a blended interwoven product of the above fibers and / or a cellulose fiber, wool, And blended and woven products with natural fibers such as silk. The disperse dye composition of the present invention is particularly useful for dyeing or printing polyester fiber materials.
Further, the disperse dye composition of the present invention is also useful for dyeing or printing new synthetic fibers. As the new synthetic fiber, polyester fiber material is preferable, and among the polyester fiber material,
For example, a polyester fiber such as a polycondensate of polyethylene terephthalate, polybutylene terephthalate, terephthalic acid and the like and 1,4-bis (hydroxymethyl) cyclohexane is used. For example, an ultrafine fiber yarn (fine denier, 1 denier or less) is used. 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. In addition, when the disperse dye composition of the present invention is used, a new material hydrophobic fiber material such as a polyester fiber spun at high speed, particularly spun at a speed of 6000 m / min or more, can be relatively easily darkened. In addition, it is possible to dye uniformly and to obtain a dyed product having similarly excellent fastnesses. In using these hydrophobic fiber materials for dyeing or printing, the form is not particularly limited, and may be in the form of a thread or in the form of a fiber,
Further, it may be in the form of a nonwoven fabric.

[0034]

EFFECT OF THE INVENTION By using the composition of the present invention, for example, in coloring a hydrophobic fiber material, it is possible to easily and reproduce a coloring material excellent in levelness of various hues such as brown, gray and beige. Can be obtained sexually. In particular, when dyeing with three primary colors, excellent leveling dyeing is obtained, and excellent dye reproducibility is obtained. Furthermore, the dyeings obtained have excellent washing fastness.

[0035]

The present invention will be described in more detail with reference to the following examples. In addition, in the text, parts represent parts by weight.

Example 1 The following formula (1)

[0037]

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

[0039]

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11.8 parts of a pyridone azo compound represented by the following formula (3)

[0041]

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Benzothiazole azo compound represented by the formula 4.
5 parts of the mixture was atomized with 75 parts of a formalin condensate of naphthalenesulfonic acid to obtain a disperse dye composition.
1500 parts of a brown dye bath containing 1.7 parts of this disperse dye composition and 1.5 parts of SUMIPON TF (a dyeing aid manufactured by Sumitomo Chemical Co., Ltd.) were prepared. To this dyeing bath, 1.2 parts of acetic acid and 4.8 parts of sodium acetate were added, and 100 parts of Tetron tropical (a polyester fiber woven fabric manufactured by Toray Industries, Inc.) cloth was added.
The temperature is increased at a rate of 1 ° C./min from 130 ° C. to 130 ° C., and staining is performed at 130 ° C. for 60 minutes. After the dyeing, the dyed product was cooled to 90 ° C. or lower and the dyeing object in the dyeing bath was taken out, washed with water, reduced / washed, washed with water and dried to obtain a dyed product. The obtained dyed product was spotless and uniform, and the compatibility of each compound was excellent. Further, the obtained dyed product had an excellent fastness, and in particular, a washing fastness was extremely excellent.

Comparative Example 1 Instead of the compound of the formula (1) in Example 1, the following formula (4)

[0044]

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A disperse dye composition was obtained in the same manner as in Example 1 except for using the above. Using this, dyeing was performed in the same manner as in Example 1 to obtain a brown dyed product. The resulting dyed product was turbulent on the entire surface, and the compatibility of the three primary colors was poor. The color fastness of the obtained dyed product was poor, and particularly the wash fastness was remarkably poor.

Example 2 The following formula (5)

[0047]

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The thiophenazo compound represented by the formula
Part, the following formula (6)

[0049]

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2.1 parts of a pyridoneazo compound represented by the following formula (7)

[0051]

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Benzothiazole azo compound 1 represented by
2.7 parts of the mixture was pulverized with 77.2 parts of a ligninsulfonic acid-based dispersant to obtain a disperse dye composition. 1500 parts of a gray dye bath containing 0.4 part of this disperse dye composition and 1.5 parts of Sumipon TF (a dyeing aid manufactured by Sumitomo Chemical Co., Ltd.) was prepared,
When the same dyeing was carried out as in Example 1, the obtained dyed product was uniform without spots, and the compatibility of each compound was excellent. Further, the obtained dyed product had an excellent fastness, and in particular, a washing fastness was extremely excellent.

Example 3 The thiophene azo compound represented by the formula (5)
And the following formula (8)

[0054]

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A mixture of 10.0 parts of the pyridone azo compound represented by the formula was atomized with 85.0 parts of a ligninsulfonic acid-based dispersant to obtain a disperse dye composition. 1.0 part of this disperse dye composition and Sumipon TF (a dyeing assistant manufactured by Sumitomo Chemical Co., Ltd.) 1.
Example 1 1500 parts of a green dye bath containing 5 parts were prepared.
As a result, the obtained dyed product was uniform without spots, and the compatibility of each compound was excellent.
Also, the resulting dyed material has excellent fastness,
In particular, the washing fastness was extremely excellent.

Example 4 The thiophene monoazo compound represented by the formula (5)
0 parts, and the following formula (9)

[0057]

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Benzothiazole azo compound 1 represented by
0.0 parts of the mixture was pulverized with 85.0 parts of a ligninsulfonic acid-based dispersant to obtain a disperse dye composition. 1500 parts of a violet dye bath containing 1.0 part of this disperse dye composition and 1.5 parts of Sumipon TF (a dyeing aid manufactured by Sumitomo Chemical Co., Ltd.) were prepared, and dyed in the same manner as in Example 1. The dyed product was uniform without spots, and the compatibility of each compound was excellent. Further, the obtained dyed product had an excellent fastness, and in particular, a washing fastness was extremely excellent.

Examples 5-15 Compounds that can be used in place of the compound of formula (1) in Example 1 are shown in Tables 1 and 2 below, and compounds that can be used in place of the compound of formula (2) are shown below. Shown in Tables 3 and 4 of
Table 5 shows compounds that can be used in place of the compound of the formula (3). Dye preparations were prepared from these compounds as shown in Tables 6 and 7, and dyed in the same manner as in Example 1. The obtained dyed products were all uniform without any unevenness, and the compatibility of each compound was excellent. In addition, each of the obtained dyed products had excellent fastness, and in particular, was extremely excellent in washing fastness. Ph in Tables 1, 2, 4, and 5 represents a phenyl group.

[0060]

[Table 1]

[0061]

[Table 2]

[0062]

[Table 3]

[0063]

[Table 4]

[0064]

[Table 5]

[0065]

[Table 6]

[0066]

[Table 7]

Examples 16 to 30 Examples 1 to 15 were carried out in the same manner as in Examples 1 to 15, 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. As a result, each of the obtained dyed products was uniform without spots, and the compatibility of each compound was excellent. Further, each of the obtained dyed products had excellent fastness, and particularly, fastness to washing was extremely excellent.

Example 31 To a dyebath containing 1.2 parts of a powder obtained by drying the dispersion obtained in Example 1, 10 parts of a cross-woven cloth of polyester fibers having a fiber diameter of 2 denier and 0.01 denier was added. 130-13 under pressure
Staining was performed at 5 ° C. for 60 minutes. Subsequently, the dyed product was treated at 85 ° C. with a treatment liquid consisting of 3 parts of caustic soda, 3 parts of hydrosulfite, 3 parts of a betaine-type amphoteric surfactant and 3000 parts of water.
For 10 minutes, washed with water and dried to obtain a dyed product having the same color and the same density between different deniers. The obtained dyed product was spotless and uniform, and the compatibility of each compound was excellent. Further, the obtained dyed product had an excellent fastness, and in particular, a washing fastness was extremely excellent.

Example 32 A dyeing test was carried out in the same manner as in Example 2 except that a high-speed spun polyester woven fabric was used instead of the tetron tropical cloth. The obtained dyed product was spotless and uniform, and the compatibility of each compound was excellent. Further, the obtained dyed product had an excellent fastness, and in particular, a washing fastness was extremely excellent.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI C07D 409/12 307 C07D 409/12 307

Claims (5)

[Claims] (1) The following formula (I): (In the formula, X1 represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, an optionally substituted alkyl group, an optionally substituted aryl group, a formyl group, an optionally substituted alkylcarbonyl group, Represents an optionally substituted arylcarbonyl group, an optionally substituted alkyloxycarbonyl group, an optionally substituted carbamoyl group, an optionally substituted alkylsulfonyl group or an optionally substituted arylsulfonyl group. ,
Y1 represents a hydrogen atom, a halogen atom, a cyano group, a nitro group,
An optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted hydroxyl group, an optionally substituted mercapto group, a formyl group, an optionally substituted alkylcarbonyl group, Optionally substituted arylcarbonyl group, optionally substituted alkyloxycarbonyl group or SO2K (where K is an alkyl group, alkenyl group, aryl group, chlorine atom, bromine atom, optionally substituted hydroxyl group or substituted Z1 is a hydrogen atom,
Halogen atom, cyano group, nitro group, alkyl group which may be substituted, aryl group which may be substituted, alkoxy group which may be substituted, alkylcarbonyl group which may be substituted, An optionally substituted arylcarbonyl group, an optionally substituted alkyloxycarbonyl group, an optionally substituted aryloxycarbonyl group, an optionally substituted carbamoyl group, an optionally substituted alkylsulfonyl group or an optionally substituted Represents an arylsulfonyl group which may be substituted, R1 represents a hydrogen atom, a halogen atom or an alkoxy group;
R2 and R3 each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group or a tetrahydrofurfuryl group; R3, together with the nitrogen atom to which they are attached, may form a morpholino group. ) And a thiophenazo compound represented by the general formula (II): (Wherein, X2 represents a hydrogen atom, a halogen atom, a cyano group or a nitro group, and Y2 represents a hydrogen atom, an alkoxy group, a halogen atom, a phenylsulfonyloxy group, an aminosulfonyloxy group which may be substituted, Optionally substituted with an aminosulfonyl group, an alkoxyalkoxyalkoxycarbonyl group, an optionally substituted aminocarbonyl group, a nitro group, a cycloalkyl containing one oxygen atom in a 5- or 6-membered ring. R4 represents a hydrogen atom, an alkyl group which may be substituted, or an aryl group which may be substituted), and / or a pyridoneazo compound represented by the formula:
Or the general formula (III): (Wherein Y3 represents a halogen atom, an alkoxy group, an alkylsulfonyl group or a nitro group, m is 1 or 2 when Y3 is a halogen atom, and Y3 is an alkoxy group, an alkylsulfonyl group or a nitro group. In some cases, it is 1. R5 represents a hydrogen atom, an alkyl group, a phenylcarbonylamino group or an alkylcarbonylamino group, and R6 and R7 each independently represent a hydroxyalkyl group, an alkyl group, an alkylcarbonyloxyalkyl group or a cyano group. A benzothiazole azo compound represented by the following formula (1): 2. A method for coloring a hydrophobic material, comprising using the composition according to claim 1. 3. The coloring method according to claim 2, wherein the hydrophobic material is a new synthetic fiber. 4. The method according to claim 2, wherein the hydrophobic material comprises polyester fibers of 1 denier or less. 5. The method according to claim 2, wherein the hydrophobic material comprises polyester fibers spun at a speed of at least 6000 m / min.