JPH08291258A - Monoazo compound, and dyeing or printing hydrophobic fiber using the same - Google Patents

Abstract

PURPOSE: To obtain a new monoazo compound having a deep color and clear hue and excellent buildup property, various fastness such as light fastness, and suitable for blue dyeing of hydrophobic fiber materials such as polyester fiber material, etc. CONSTITUTION: The objective compound is expressed by formula I [R1 is H, Cl, a 1-5C alkyl or a (chloro)alkylcarbonylamino; R2 and R3 are each a 1-5C alkyl, a 1-5C alkoxy, phenyl, an aralkyl, a phenoxy or an arylalkyloxy, and when R1 is H, the total C-number of the 1-5C alkyl and the 1-5C alkoxy is >=5], for instance, 2- 4-[N,N-bis(2-methoxycarbonyloxyethyl)amino]-2- methylphenyl}azo-3-cyano-5-nitrothiophene. The compound of formula I is obtained by diazotizing 2-amino-3-cyano-5-nitrothiophene by a normal method and coupling the diazatized compound with a compound of formula II.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a monoazo compound which gives a vivid blue dyeing product which is excellent in various properties such as fastness to light when used as a dye.

[0002]

2. Description of the Related Art In recent years, new synthetic fibers, microfibers, and the like have been developed that are inexpensive and that are compatible with the upsizing of consumers. However, CI currently on the market
Anthraquinone-based disperse dyes such as Disperse Bull-56 have good light fastness and are vivid blue disperse dyes, but because of their low molar extinction coefficient, they are suitable for the above-mentioned new synthetic fibers and microfibers. On the other hand, there is a problem in that sufficient build-up properties cannot be exhibited (that is, dark colors cannot be dyed). On the other hand, CI dispersible-16 with excellent build-up
The monoazo disperse dyes such as No. 5 have the problems that the hue is unclear and the light fastness is inferior as compared with the anthraquinone disperse dyes.

[0003]

Under these circumstances, the build-up property is excellent, the sharpness is good, and the light fastness is good.
It is strongly desired to develop a blue disperse dye that is well balanced between the two.

[0004]

DISCLOSURE OF THE INVENTION The inventors of the present invention have been able to dye or print a hydrophobic material, especially polyester fiber, in a bright blue phase at a high concentration, and to have various fastnesses, especially light fastness. As a result of diligent studies to find a compound capable of providing a compound, it was found that a compound having a specific substituent at the para position of the azo group of a monoazo compound is effective, and the present invention has been completed.

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

[0006]

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(In the formula, R ₁ is hydrogen atom, chlorine atom, C ₁
To C ₅ alkyl group, alkylcarbonylamino group or chloroalkylcarbonylamino group, R ₂ and R ₃ are each independently a C _{1 to} C ₅ alkyl group, C ₁ to
It represents a C ₅ alkoxy group, a phenyl group, an aralkyl group, a phenoxy group or an arylalkyloxy group. However, when R ₁ is hydrogen atom, the total number of carbon atoms of the alkoxy group of C ₁ -C alkyl and C ₁ -C _{5 5} represented by R ₂ and R ₃ is 5 or more. And a method for dyeing or printing hydrophobic fibers using the compound.

The C ₁ -C ₅ alkyl group represented by R ₁ includes straight or branched ones, and a methyl group is particularly preferable. Examples of the alkylcarbonylamino group and chloroalkylcarbonylamino group represented by R ₁ include an acetylamino group, a propionylamino group and a chloroacetylamino group, and among them, an acetylamino group and a propionylamino group are particularly preferable.

The C ₁ -C ₅ alkyl group and C ₁ -C ₅ alkoxy group represented by R ₂ and R ₃ include ethyl group, isopropyl group, propyl group, n-butyl group, isobutyl group, pentyl group. A group, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group and the like are preferable, and an ethyl group, an ethoxy group, a propyl group and a propoxy group are particularly preferable. R ₂
Examples of the aralkyl group and arylalkyloxy group represented by R ₃ include a benzyl group, a phenethyl group, a benzyloxy group and a phenethyloxy group.

Among the monoazo compounds represented by the above formula (I), it is particularly preferable that R ₁ is a hydrogen atom or a methyl group, and R ₂ and R ₃ are C ₂ -C ₅ alkyl groups. or compounds is an alkoxy group of C ₁ -C _5. The monoazo compound represented by the formula (I) is
For example, formula (II)

[0011]

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The amines represented by the formula (1) are diazotized by a conventional method, and the diazo compound obtained is then represented by the following formula (III):

[0013]

[Chemical 4]

It can be produced by coupling with an aniline represented by the formula (wherein R ₁ , R ₂ and R ₃ have the above-mentioned meanings).

The dyeing or printing method using the monoazo compound of the present invention is useful for hydrophobic fiber materials, particularly polyester fiber materials. In particular, it is possible to dye hydrophobic fibers to a sufficiently dark color by dipping such as exhaust dyeing method. Useful for dyeing. Also, as the fiber diameter generally becomes smaller, for example,
Although it becomes difficult to dye ultrafine fibers such as microfibers in a dark color, it is possible to obtain a dark dye relatively easily when the monoazo compound of the present invention is used.

For example, the monoazo compound of the present invention is pulverized into fine particles in an aqueous medium together with a suitable dispersant such as a condensate of naphthalene sulfonic acid and formaldehyde or lignin sulfonic acid by a conventional method to give a dye. A dispersion is obtained. This dye dispersion may be used as it is or in the form of powder by spray drying or the like. Dyeing, particularly dip dyeing, is carried out by adding a pH to a dyeing bath in which the monoazo compound of the present invention is dispersed in an aqueous medium, if necessary.
After adding a regulator, a dispersion leveling agent, etc., the hydrophobic fiber material is dipped, for example, in the case of polyester fiber, under pressure,
It can be carried out usually in a temperature range of 105 ° C or higher, preferably 110 to 140 ° C. In the presence of a carrier such as o-phenylphenol or methylnaphthalene,
It is also possible to dye at relatively high temperatures, for example boiling water. Furthermore, after padding the dye dispersion on the cloth, 1
A dyeing method of steaming or dry heat treatment at a temperature of 00 ° C. or higher is also applicable. On the other hand, printing can be carried out by kneading a dye dispersion together with an appropriate sizing agent, printing and drying this on a cloth, and then performing steaming or dry heat treatment.

When the monoazo compound represented by formula (I) of the present invention is applied to dyeing or printing, other dyes may of course be used in combination for dyeing, and various dyes may be used in the step of preparing a dye dispersion. A compounding agent may be added.

[0018]

The monoazo compound of the present invention is useful as a disperse dye. Further, according to the method of the present invention, having a dark and clear hue, and also excellent in various fastnesses such as light fastness and sublimation fastness, for example, of a hydrophobic fiber material such as a polyester fiber material. A blue dyeing is obtained.

[0019]

EXAMPLES Next, the present invention will be described more specifically by way of examples, but the present invention is not limited to the following examples. In the examples, parts are parts by weight, and% is% by weight.

Example 1 2-Amino-3-cyano-5-nitrothiophene 1.6
9 parts, 2 parts of propionic acid, and 8 parts of acetic acid were cooled to 10 degrees or less, 2.95 parts of 43% nitrosyl sulfuric acid was added dropwise at 10 degrees or less, and this mixture was stirred at about 5 degrees. The obtained diazo solution was added dropwise to a solution of 3.73 parts of N, N-bis (2-methoxycarbonyloxyethyl) -m-toluidine and 70 parts of methanol at 10 degrees or less. This solution was stirred for 1 hour, the precipitated crystals were filtered off, washed with methanol, and

[0021]

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The compound of formula (1) was obtained in high yield and high purity. A DMF (dimethylformamide) solution of this compound exhibited a blue color. (Λmax = 613nm)

Example 2 1.0 part of the compound obtained in Example 1 was atomized and dispersed in an aqueous medium together with naphthalenesulfonic acid and 3.0 parts of formaldehyde condensate. 10 parts of Tetoron jersey (polyester cloth, product of Teijin Ltd.) was dipped in a dyeing bath containing 0.6 part of powder obtained by drying the dye dispersion, and the mixture was applied under pressure 1
Dyeing was performed at 30 to 135 ° C. for 60 minutes. Then, the dyed product is treated with a treatment liquid consisting of 3 parts of caseisoda, 3 parts of hydrosulfite, 3 parts of betaine type amphoteric surfactant and water at 85 ° C
After 10 minutes of reduction cleaning treatment, washing with water and drying, a bright blue dyed product was obtained, and its light resistance and sublimation fastness were excellent. The obtained dyed product was subjected to soft antistatic processing according to the following method. In a pad tank, Sumitex Softener LK-1 (Sumitomo Chemical Co., Ltd. softening agent) 10 parts / l and Sumistad F-1 (Sumitomo Chemical Co., Ltd. antistatic agent) 5 parts / l A pad solution having a composition of was prepared and after soaking this dyed product, a weight increase rate of 8
Evenly squeezed to 0%. After soaking the dyed product in the liquid again and squeezing it in the same manner, intermediate drying is performed at 80 ° C. for 2 minutes, and then 17
Heat setting was performed at 0 ° C. for 1 minute. When various fastnesses after the post-processing thus obtained were measured, extremely excellent results were obtained.

Example 3 To 1.3 parts of the compound obtained in Example 1 was added 3.7 parts of ligninsulfonic acid, and the mixture was atomized and dispersed. To this, 35 parts of warm water and 60 parts of a half emulsion paste having the following composition were added. And were mixed to prepare a printing paste. 0 / W emulsion 300 parts Maypro gum NP 12% paste 694 parts Sodium chlorate 4 parts Tartaric acid 2 parts ─────────────────────────── ────── Total 1000 parts Tetron tropical (polyester cloth, manufactured by Teijin Ltd.) is printed with this printing paste, and after drying, it is heated at normal pressure at high temperature.
It was fixed by steaming at 170 ° C. for 7 minutes with a marker, followed by reduction cleaning treatment, water washing, softening, and antistatic processing in this order according to the method described in Example 2. The blue dyed product thus obtained was excellent in light fastness and sublimation fastness.

Comparative Example 1

[0026]

[Chemical 6]

A compound represented by the formula (JP-A-48-8412)
Dyeing evaluation was carried out in accordance with Examples 2 and 3 except that the disperse dye described in JP-A No. 0) was used. The obtained dyed product having an unclear hue had a light fastness of grade 3, and the dyeing property was also unsatisfactory. The light fastness was measured according to JIS L0842 using carbon arc as a light source.

Examples 4 to 28 Instead of N, N-bis (2-methoxycarbonyloxyethyl) -m-toluidine used in Example 1, substitution of R ₁ , R ₂ and R ₃ shown in the following table. Formulas with groups (II
The corresponding monoazo compound was obtained in the same manner by using the anilines represented by I).

[0029]

[Table 1]

[0030]

[Table 2]

[0031]

[Table 3]

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Kazushi Yokokawa 3-1,98 Kasugadeka, Konohana-ku, Osaka-shi, Osaka Sumitomo Chemical Co., Ltd.

Claims (2)

[Claims] 1. The following formula (I): (In the formula, R ₁ represents a hydrogen atom, a chlorine atom, a C _{1 to} C ₅ alkyl group, an alkylcarbonylamino group or a chloroalkylcarbonylamino group, and R ₂ and R ₃ are each independently a C _{1 to} C ₅ It represents an alkyl group, a C ₁ -C ₅ alkoxy group, a phenyl group, an aralkyl group, a phenoxy group or an arylalkyloxy group, provided that when R ₁ is a hydrogen atom, it is represented by R ₂ and R _3. C ₁ ~ C
The total number of carbon atoms of ₅ alkoxy group of the alkyl group and C ₁ -C ₅ a is 5 or more. ) The monoazo compound shown by. 2. A method for dyeing or printing a hydrophobic fiber using the monoazo compound according to claim 1.