JPS60155269A - Isothiazole azo dye - Google Patents

Abstract

NEW MATERIAL:Isothiazole azo compounds of formula I , wherein Y1, Y2 are each H, halogen, lower alkyl, lower alkoxy, nitro; n is 1-3; X is H, halogen, lower alkyl, lower alkoxy or a group of formula II or III; R1 is H, (substd.) alkyl, cycloalkyl, alkenyl; R2, R3, R4 are each H, lower alkyl; R5 is H, lower alkyl, (lower alkyl-or lower alkoxy-substd.) phenyl. EXAMPLE:Compound of formula IV. USE:Dyes which dye hydrophobic synthetic fibers such as polyester clear yellowish red to purple with excellent fastness to light. PREPARATION:A compd. of formula V (wherein Y1, Y2, n are as defined above) is diazotized and then coupled with a compd. of formula VI (wherein X, R1, R2, R3, R4 are as defined above) to obtain the compd. of formula I .

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an isothiazole azo dye suitable for dyeing hydrophobic fibers.

More specifically, the present invention relates to the general formula (I) (wherein, Yl and Y2 are hydrogen atoms,) 10 gene atoms, lower alkyl group, lower alkoxy group or nitro group, n is 1
~B, X are hydrogen atoms, halogen atoms, lower alkyl groups,
Lower alkoxy group, -NHCOR, or -NH30
2R5, R1 is a hydrogen atom, an optionally substituted alkyl group, a cycloalkyl group, an alkenyl group, R2, Ra.

R4 each represents a hydrogen atom or a lower alkyl group. However, R5 represents a hydrogen atom, a lower alkyl group, a phenyl group which may be substituted with a lower alkyl group or a lower alkoxy group. ) is an isothiazole azo dye represented by

In the present invention, examples of substituents for the alkyl group which may be substituted in R1 include chlorine, bromine, hydroxyl group, cyano group, -0R6, -CO2R6, -0C0R6
, -〇CO2R6, -〇502R6, -NH5O2R6
, -NHR6, -0CONHR6, where R2 represents the above meaning, R6 is an alkyl group, cycloalkyl group, alkenyl group, aralkyl group or phenyl group (lower alkyl group, lower alkoxy group, halogen atom, lower alkanoylamino group) , a cyano group, or a lower alkoxycarbonyl group). R
7 represents a lower alkyl group, an optionally substituted phenyl group, a benzothiazolyl group or a benzoxacylyl group. R8 represents a lower alkyl group, a lower alkoxy group, a halogen atom, a lower alkanoylamino group, a cyano group, or a lower alkoxycarbonyl group.

m represents an integer of 1 or more.

The compound of the general formula is obtained by diazotizing the compound represented by the general formula CTI) (wherein Yl, Y2.n represent the above-mentioned meanings), and converting it into the general formula (m)9 with 1 (wherein, X, R1, R2, R8, R4 represent the above meanings).

The compound of general formula (I) thus obtained dyes polyester in a vivid color tone ranging from yellowish red to purple, and has various fastness properties such as water fastness, sublimation fastness, light fastness, and washing fastness. Provides dyed products with excellent strength and particularly light fastness.

Moreover, the dye bath stability, dyeing property, and build-up property are good.

The obtained compound is dispersed according to a conventional method for use as a dye. For example, in a sand mill, naphthalene sulfonic acid formalin condensate, lignin sulfonic acid, Fragile chloride.

Dispersion selected as desired from various dispersants such as anionic dispersants such as Schefferic acid formalin condensate, polyoxyethylene alkylphenyl ethers, holoxyethylene alkylphenyl ethers, and other nonionic dispersants. It may be treated with a suitable amount of water, and it may be processed as a liquid or as a powder or granules by drying.

Synthetic fibers to which the dyeing method of the present invention can be applied include synthetic polyamide fibers, polyester J fibers, and other so-called hydrophobic synthetic fibers, and semi-synthetic fibers such as G or triacetate, and these may be used alone or in combination. It also refers to various forms of fiber materials mixed with other natural fibers. Among these, it is particularly suitable for polyester J fibers and mixed products of polyester fibers and natural or regenerated cellulose fibers.

Dyeing methods in the present invention include dip dyeing, continuous dyeing, textile printing, and transfer printing.In addition, in textile printing, the present invention can be used as a background dye for alkaline resist discharge printing in addition to ordinary direct printing. This will be explained in more detail.

In the examples, parts refer to parts by weight unless otherwise specified, and color tones refer to those on polyester fibers.

Example 1 21.5 parts of a compound represented by the following formula (na) was mixed with glacial acetic acid/brobionoic acid (
3:1) dissolved in 150 parts and 70 parts of 85% sulfuric acid,
Gradually add 82 parts of 48% nitrosyl sulfuric acid at 5°C,
Stir at ~5°C for 4 hours. On the other hand, N-ethyl-2,2゜4-trimethyl-1,2,8,4, 20 parts of tetrahydroquinoline, 330 parts of water, 085 parts of concentrated hydrochloric acid, 1.7 parts of diisobutylnaphthalene-1-sulfonic acid mixture, and ethanol. Dissolve in 100 parts of the mixture and add about 4 parts of ice to this.
The above diazo solution is gradually added at 0-5° C. while adding 0.00 parts. After the reaction is completed, the precipitated solid is filtered, washed to neutrality, and then dried. 38 parts of the dye of the following formula (1) are obtained.

2H5 Color tone: bluish red λmax 540 nm (dimethylformamide) Example 2 100 parts of ethanol, N-β-phenoxyethyl-2
, 25 parts of 2,4-trimethyl-1,2°8.4-tetrahydroquinoline, 800 parts of water, 85 parts of concentrated hydrochloric acid, and 1.7 parts of diisobutylnaphthalene-1-sulfonic acid mixture, and about 400 parts of ice. The same diazo solution as in Example 1 is gradually added at 0 to 5°C while adding .Then, the same treatment as in Example 1 is carried out.

42 parts of compound (2) of the following formula are obtained. 2maX:
588 nm (dimethylformamide) Two bluish red color Example 3 N-n-butyl-2,2,4-)limethyl'-7-acetylamino-1,2,8,4-tetrahydroquinoline 2
Dissolve 4 parts in 150 parts of dimethylformamide, and add 80 parts of water.
0 parts, 8.5 parts of concentrated hydrochloric acid and 1 part of hydiisobutylnaphthalene
- Add to the mixture consisting of zit'i parts of the sulfonic acid mixture. A diazo solution similar to that in Example 1 is gradually added at 0-5° C. while adding about 400 parts of ice.

The same processing as in Example 1 is performed. Compound (8) of the following formula is 3
You can get 8 copies.

λmax: 548 nm (dimethylformamide) Color tone: Purple Example 4 Using the compound (1) obtained in Example 1, staining was performed by the following operation.

a) Preparation of dispersion Total: 100 parts (Note 1) Naphthalene sulfonic acid formalin condensate The above mixture was treated in a sand mill for 4 hours to obtain a dispersion.

b) Dyeing 8 parts of the dispersion obtained in a) are placed in a dyeing pot along with 3000 parts of water and adjusted to pH 5 using acetic acid. Next, 100 parts of polyester fabric was added to this, and dyeing was carried out at 130°C for 60 minutes. After finishing dyeing, wash and rinse using the usual method. To obtain a vivid bluish-red dyed product with excellent color fastness.

Example 5 Using the compound (2) obtained in Example 2, a dispersion is prepared according to a) of Example 5. Using this dispersion, prepare a printing paste with the following composition (printing paste composition) Tartaric acid 0.8 parts Sodium chlorate 0.2 parts Water Total balance 100 parts (Note 2) Half emulsion source fflAMi kerosene oil
70 parts water 25 parts Bi7yoa KM-g (Note 8) 5 parts Total ioo parts (Note 3) Shin-Nakamura Chemical Co., Ltd.: Emulsifier 80 parts of an emulsion obtained by mixing the above in a high-speed mixer and Maybrogum NP 12% paste (Grinara) company product) 7
Mix with 0 parts and perform hand printing. The fabric is then dried and subjected to superheated steam treatment at 175°C for 7 minutes. Thereafter, washing and drying are performed using a conventional method. A robust and vivid bluish-red printed fabric is obtained.

Example 6 Using a dispersion of the compound of Example 8 prepared according to the method of Example 4, dyeing is carried out using 100 parts of polyester cloth and 100 parts of cotton cloth instead of 100 parts of the polyester cloth of Example 4.

After dyeing, the temperature of the dye bath is cooled to 60°C, 6 parts of sodium carbonate is added to the bath, and the temperature is kept at 60°C for 1 hour.Then, the dyed fabric is taken out and washed with boiling water and water. Polyester fabrics are dyed in bright and strong bluish-red colors, whereas cotton fabrics are dyed with virtually no staining.

Example 7 The compounds shown in the table below are obtained in the same manner as in Examples 1 to 8. The color tone is polyester delicate 1.

Claims (1)

[Claims] General formula (I) 1 (wherein, Yl and Y2 are hydrogen atoms, halogen atoms, lower alkyl group, lower alkoxy group or nitro group, n
is 1 to B, X is 2 hydrogen atoms, halogen atom, lower alkyl group, lower alkoxy group, -NHCOR5, or -N
H5O□R,, R1 is a hydrogen atom, an optionally substituted alkyl group, a cycloalkyl group, an alkenyl group, R2,
Ra. R4 each represents a hydrogen atom or a lower alkyl group. However, R5 represents a hydrogen atom, a lower alkyl group, a phenyl group which may be substituted with a lower alkyl group or a lower alkoxy group. ) isothiazole azo dye.