JPH10306222A - Disperse dye for new synthetic fiber - Google Patents

Abstract

(57) [Problem] To provide a blue monoazo disperse dye useful for dyeing a new synthetic fiber such as a fine denier polyester fiber material. SOLUTION: A monoazo disperse dye for a new synthetic fiber represented by the following formula (I). Embedded image (Wherein, R1 represents hydrogen, alkyl, R2 represents hydrogen, alkoxy, R3 represents phenyl or alkyl, A and B represent alkylene, and X represents —OCO— or —COO—).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a new synthetic fiber disperse dye and a method for dyeing or printing a new synthetic fiber using the same, and more particularly to a new synthetic fiber material such as fine denier polyester fiber and different shrinkage blended polyester fiber material. The present invention relates to a thiophene-based monoazo disperse dye for synthetic fibers, and a method for dyeing or printing the above-mentioned new synthetic fibers using the disperse dye.

[0002]

2. Description of the Related Art For example, JP-A-58-157863 discloses that
The following formula (1)

[0003]

Embedded image

[0004] A blue-based monoazo disperse dye represented by On the other hand, in recent years, attention has been paid to a synthetic fiber having a new texture, texture, or functionality, which has not been provided by conventional synthetic fibers, that is, a new synthetic fiber. The new synthetic fiber is made of ultra-fine yarn (usually called fine denier), irregularly shaped yarn,
It is a fiber material composed of a different shrinkage blended yarn and a multi-phase hybrid yarn.

[0005]

Although the above-mentioned new synthetic fibers have excellent properties, they have different problems from conventional synthetic fibers in terms of coloring and various processing techniques. For example, even if a new synthetic fiber is dyed using a known blue monoazo disperse dye represented by the above formula (1), it cannot be dyed in a dark color, or the dyed material has insufficient fastness. There is.

[0006]

Means for Solving the Problems The present inventor has solved the above problems and has developed a disperse dye which can dye the new synthetic fiber in a deep blue color and has various fastnesses of the dyed material which are practically sufficient. As a result of intensive studies, a specific thiophene-based monoazo dispersion obtained by a coupling reaction between a diazotized product of 2-amino-3-cyano-5-nitrothiophene and an N-alkyl (or alkoxyalkyl) -aniline derivative has been provided. The inventors have found that dyes achieve this purpose and completed the present invention. That is, the present invention provides a compound represented by the general formula (I):

[0007]

Embedded image

(Wherein R ₁ is a hydrogen atom, a chlorine atom, an alkyl group having 1 to 4 carbon atoms, an alkylcarbonylamino group having 2 to 5 carbon atoms, a phenylsulfonylamino group or an alkylsulfonylamino group having 1 to 4 carbon atoms) R ₂ represents a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms, R ₃ represents a phenyl group or an alkyl group having 1 to 6 carbon atoms, and A and B each independently represent 1 And X represents a group represented by —OCO— or —COO—.) A disperse dye for a new synthetic fiber, and a dyeing of the new synthetic fiber using the disperse dye. Or a printing method is provided.

In the general formula (I), R ₁ is a hydrogen atom, a chlorine atom, an alkyl group having 1 to 4 carbon atoms, an alkylcarbonylamino group having 2 to 5 carbon atoms, a phenylsulfonylamino group or a Represents an alkylsulfonylamino group, wherein the alkyl herein may be linear,
Moreover, it may be branched. Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group,
Examples of the i-butyl group and the like are alkylcarbonylamino groups having 2 to 5 carbon atoms, such as acetylamino group and propionylamino group. Examples of the alkylcasulfonylamino group having 1 to 4 carbon atoms are methylsulfonylamino group and ethyl. Examples include a sulfonylamino group and an n-butylsulfonylamino group.

In the general formula (I), R ₂ represents a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms, and the alkoxy group may be linear or branched. Examples of the alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group and a t-butyloxy group.

In the general formula (I), R ₃ represents a phenyl group or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be linear or branched. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group,
c-butyl group, n-pentyl group, n-hexyl group and the like.

In the general formula (I), A and B each independently represent
It represents an alkylene group having 1 to 4 carbon atoms, and the alkylene group may be linear or branched. Examples of the alkylene group include a methylene group, an ethylene group, an n-propylene group, an i-propylene group, and an n-butylene group. Among these, a linear alkylene group is preferable, and an ethylene group is particularly preferable.

The disperse dye represented by the formula (I) is known, for example, from EP-A-727464 and JP-A-5-105817, and can be produced according to the methods described in these documents.

The new synthetic fiber materials to which the new synthetic fiber disperse dye of the present invention can be applied include polyethylene terephthalate, polybutylene terephthalate, terephthalic acid and 1,4-bis-
Fiber material of polyester such as polycondensate with (hydroxymethyl) cyclohexane; blended or mixed fabric of polyamide fiber such as nylon and fiber material of the above polyester; or natural fiber such as wood brocade, silk, wool And a fiber material of the above-mentioned polyester. The form of these materials may be any of yarn, woven fabric, knitted fabric and the like.

[0015] When the new synthetic fiber is in the form of a yarn, for example, 1
Ultra-fine fibers of less than denier (called fine denier fibers. In particular, ultra-fine fibers of less than 0.3 denier are sometimes called ultra-micro fibers.)
It is composed of yarns, irregular cross-section yarns, different shrinkage blended yarns, multi-phase hybrid yarns and the like. These yarns may be in the form of filaments, or may be variously processed or modified yarns such as matte yarns containing titanium dioxide or the like.

The disperse dye for new synthetic fibers of the present invention may be used alone or as a mixture of two or more. or,
The disperse dye of the present invention may be mixed with a known disperse dye such as an azobenzene-based or anthraquinone-based dye to adjust the hue.

Further, such a single disperse dye or a disperse dye as a mixture may optionally contain a dispersant,
It can also be used as a composition together with known auxiliaries usually mixed with disperse dyes, such as extenders, pH adjusters, dispersing leveling agents, builders, dyeing auxiliaries, solvents, resin binders and the like.

When the disperse dye of the present invention is used for coloring a new synthetic fiber, the dyeing bath may be prepared by using a dispersion obtained after the treatment by a known fine particle dispersing method, or may be performed after the above treatment. After drying the resulting dispersion, a dye bath may be prepared using the obtained powder. Fine particles / dispersion of the disperse dye of the present invention is usually carried out using a pulverizer such as a sand mill together with a formalin condensate of naphthalenesulfonic acid or a ligninsulfonic acid-based dispersant.

The preparation of the dyeing bath is carried out by using a single disperse dye as described above or a disperse dye as a mixture, a known auxiliary mixed with the disperse dye, and water or o-phenylphenol.
It may be carried out by mixing a carrier such as an aromatic organic compound such as methylnaphthalene, or a composition obtained by mixing a disperse dye and a known auxiliary agent with a carrier such as water or an aromatic organic compound. It may be carried out after dilution.

When the disperse dye for a new synthetic fiber of the present invention is applied to a new synthetic fiber material, the disperse dye represented by the general formula (I) of the present invention alone or the disperse dye represented by the general formula (I) of the present invention may be used. A mixture, or a mixture of these and a known azobenzene-based or anthraquinone-based disperse dye, is dispersed in an aqueous medium as a carrier to prepare a dyeing bath. Adjusting agent, in the presence of an auxiliary agent such as a dispersion leveling agent, by immersing the new synthetic fiber material, 105 ° C. or more, preferably 110 ~ 140 ° C. under pressure, preferably 30
Can be stained for -60 minutes. When the above-mentioned aromatic organic compound such as o-phenylphenol or methylnaphthalene is used as a carrier, dyeing can be performed at a relatively low temperature, for example, at about 100 ° C. Furthermore, it is also possible to perform thermosol dyeing by padding the dye dispersion onto an object to be dyed such as cloth and then steaming or heat-drying at a temperature of 100 ° C. or higher.

Further, the disperse dye represented by the general formula (I) of the present invention alone, a mixture of the disperse dye represented by the general formula (I) of the present invention, or a known azobenzene type
A mixture of a disperse dye such as anthraquinone is used as a dye dispersion, and this dispersion is kneaded with a known appropriate paste, and a printing paste obtained is printed on an object to be printed such as a cloth, and then steaming or dry heat treatment is performed for printing. You can also. Furthermore, it is also possible to carry out printing by an ink jet method.

[0022]

The present invention will be described in more detail with reference to the following examples. In the examples, parts and% indicate parts by weight and% by weight, respectively.

Example 1 (a) Production Example of Disperse Dye A diazo solution obtained by diazotizing 2-amino-3-cyano-5-nitrothiophene with nitrosylsulfuric acid in a conventional manner was cooled, and cooled to an equivalent amount of 3-ethylsulfonylamino. The mixture was added dropwise to a methanol solution of -N-ethyl-N- (2-benzoyloxyethyl) aniline with stirring. After dropping,
The reaction mixture was cooled, and the precipitated crystals were separated by filtration and washed with methanol to obtain the following formula (2)

[0024]

Embedded image

A disperse dye represented by the following formula was obtained.

(B) Preparation of dye bath A mixture of 300 parts of the disperse dye represented by the above formula (2), 600 parts of water and 300 parts of a formalin condensate of sodium naphthalenesulfonate is pulverized by a sand mill, and then ligninsulfonic acid. 350 parts were added and dispersed. The obtained dispersion was spray-dried. The dried disperse dye contained a total of 65% of an anionic dispersant and 5% of water. 5 parts of this dye was dispersed in 1000 parts of water, and then the pH was adjusted to 5 by adding acetic acid and sodium acetate.

(C) Dyeing Example 100 parts of a fine denier polyester fiber material (Toray Co., Ltd. Toraysee) is immersed in the dyeing bath obtained in the above (b) at a rate of 1 ° C./min. The temperature was raised to ° C. 130 ℃
The fiber material obtained by dyeing with caustic soda 3 for 60 minutes
, 3 parts of hydrosulfite, 3 parts of a betaine-type amphoteric surfactant and 3,000 parts of water, subjected to a reduction washing treatment at 85 ° C for 10 minutes, washed with water, and dried. Uniform and dense blue dyeings were obtained with good reproducibility.

Comparative Example 1 Same as (c) of Example 1 except that a blue monoazo disperse dye represented by the above formula (1) was used instead of the disperse dye represented by the above formula (2). And stained.

The fastnesses of the dyed products obtained in Example 1 and Comparative Example 1 were measured. The results are shown in Table 1.

[0030]

【table 1】

In Table 1 above, the sublimation fastness was determined according to JIS L0.
It was measured by the 879 method. Similarly, washing fastness is AATC
C Measured by the IIA method.

Example 2 Instead of the disperse dye represented by the above formula (2), the following formula (3)

[0033]

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A dye bath was prepared and dyed in the same manner as in Example 1 except that the disperse dye represented by the formula (1) was used, and a uniform and deep blue dyed product was obtained with good reproducibility. Further, the obtained dyed product had excellent fastness to sublimation and fastness to washing.

Example 3 The procedure of Example 1 was repeated, except that a different-shrinkage blended polyester fiber material (Cirlook Syldeux, manufactured by Toray Industries, Inc.) was used instead of the fine denier polyester fiber material (Toray, manufactured by Toray Industries, Inc.). Preparation and dyeing of the dye bath in the same way,
Uniform and dense blue dyeings were obtained with good reproducibility.
Further, the obtained dyed product had excellent fastness to sublimation and fastness to washing.

Example 4 An equivalent mixture 300 of disperse dyes of the formulas (2) and (3) was used instead of 300 parts of the disperse dye of the formula (2).
A dye bath was prepared and dyed in the same manner as in Example 1 except for using the part, and a uniform and deep blue dyed product was obtained with good reproducibility. Further, the obtained dyed product had excellent fastness to sublimation and fastness to washing.

Examples 5-40 Except that each of the disperse dyes shown in Tables 2 and 3 represented by the following general formula (II) was used instead of the disperse dye represented by the above formula (2), Preparation and dyeing of the dyeing bath were carried out in the same manner as in Example 1, and uniform and dense blue dyeings were obtained with good reproducibility. Further, the obtained dyed products were excellent in fastness to sublimation and fastness to washing.

[0038]

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(Wherein R4, R5 and R6 represent the groups described in the second, third and fourth columns in the numbers of the examples in Tables 2 and 3, respectively). And Ph in Table 3 represents phenyl.

[0040]

[Table 2]

[0041]

[Table 3]

Example 41 Each of the disperse dyes described in Tables 2 and 3 was used, and
Preparation of a dye bath in the same manner as in Example 1 except that a different shrinkage-blend polyester fiber material [Shilux Sildue manufactured by Toray Co., Ltd.] is used instead of the fine denier polyester fiber material [Toray Co., Ltd. Toraysee]. And dyeing,
Uniform and dense blue dyeings were obtained with good reproducibility.
Further, the obtained dyed product had excellent fastness to sublimation and fastness to washing.

[0043]

The new synthetic fiber disperse dye of the present invention is suitably used for coloring fine denier polyester fiber materials and the like. Further, according to the dyeing or printing method of the present invention, a blue dyed material having a dark color and excellent in various fastnesses can be obtained.

Claims (4)

[Claims] [Claim 1] General formula (I) (Wherein, R ₁ is a hydrogen atom, a chlorine atom, an alkyl group having 1 to 4 carbon atoms, an alkylcarbonylamino group having 2 to 5 carbon atoms,
Represents a phenylsulfonylamino group or an alkylsulfonylamino group having 1 to 4 carbon atoms, R ₂ represents a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms, and R ₃ represents a phenyl group or an alkyl group having 1 to 6 carbon atoms. A and B each independently represent an alkylene group having 1 to 4 carbon atoms, and X is -OC
Represents an O- group or a -COO- group. ) New synthetic fiber disperse dye. 2. A method for dyeing or printing a new synthetic fiber, comprising using the disperse dye according to claim 1. 3. The method according to claim 2, wherein the new synthetic fiber is a fine denier polyester fiber material. 4. The method according to claim 2, wherein the new synthetic fiber is a different shrinkage blended polyester fiber material.