JPS5839186B2 - 4,4'- diaminobenzanilidecara - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel sulfonated triazo dyes suitable for direct dyeing of cotton and other cellulose fibers such as flax, regenerated cellulose fibers, hemp, jute.

The object of this patent application is the formula An object of the present invention is to provide a water-soluble triaz dye having the following properties.

This direct dye exhibits application properties similar to conventional direct dyes, such as those of the benzidine series, but without any toxicological risks involved during the process of producing it.

In fact, benzidine, which is used to make direct dyes, is a dangerous compound because of its carcinogenic properties, and its use and production therefore require strict standards of integrity.

This dye gives a brownish-yellow staining to cellulose fibers.

The dye of general formula (1) can be prepared according to the same method as used for conventional direct dyes, i.e. by adding a suitable amount of dye and
The dyeing is generally applied at temperatures from 56 to 100 DEG C. from a water bath containing ~20 parts (with respect to fiber weight) of anhydrous Na2SO4 or NaCl.

The following examples are provided to illustrate the invention, but not to limit it.

Unless otherwise specified, "7 parts" is by weight.

Example 150 parts of water and 10.5 parts of 200Be' hydrochloric acid 32.
Cool 18.9 parts of 2-amino-phenol-4-sulfonic acid suspended in 14 wt. H (J') by using 100 parts of water;

Diazotization was carried out in 30 minutes at 0-5<0>C by dropwise addition of a solution of 7 parts of NaNo2 in 30 parts of H2O.

After 60 minutes of stirring, excess nitrous acid was removed with sulfamic acid.

11.6 parts of resolmin were dissolved in 70 parts of water and 13.3 parts of 36° Be'NaOH (30.30% by weight NaCH).

The diazo compound was added to the resulting solution at a temperature of 0 to 5°C with 150 parts of water, and 26.5 parts of 36°Be'NaOH.
The mixture was poured over a period of about 1 hour while maintaining the pH value at about 9 with (30.30% by weight NaOH).

Stirring was carried out for 1 hour to complete the coupling reaction, and then 26 parts of copper sulfate pentahydrate were dissolved in 80 parts of H2O.
After mixing the solution dissolved at 0° C., 8 parts of St-IJium acetate 3H20 were added thereto.

The whole was kept at 35-40℃ for 3 hours, and the pH value was 5-5.
．． It was 5.

It was salted with 45 parts of rock salt (parts/volume) and the resulting precipitate was passed under vacuum and squeezed securely.

The cake thus obtained was treated in 150 parts of water at 40°C and 15 parts of Na2CO3 were mixed with 70 parts of H2O.
It was solubilized by adding a solution dissolved in it to the cake at a pH value of about 9.

The temperature was brought to 0-5°C and the pH value was adjusted to 1 with 200 parts of water.
0 parts of Na COs (20% solution (parts/volume) kept at about 9-9.5, was added the tetrazo prepared as described below).

The tetrazo compound was produced as follows.

After cooling with 150 parts of ice, 22.7 parts of 4,4' diaminobenzanilide suspended in 50 parts of water and 52 parts of 200Be (32.14 parts by weight HCl) are mixed with 1
Tetrazotization was carried out by feeding a solution of 2 parts NaNO2 in 60 parts H2O at 0-5<0>C over 30 minutes.

After 60 minutes of stirring, excess nitrous acid was removed with sulfamic acid.

The coupling reaction was completed in about 3 hours.

10.9 parts of m-aminophenol was mixed with ioO parts of H2O at 40°C and 1.5 parts of 36°Be'NaOH (30,
A solution dissolved in 30 wt% Na0H) was added to the diazo-diazo.

It was stirred overnight.

The temperature is 10-15°C, and the pH value is 11.3 parts of 36°Be'NaOH (30,30% by weight NaOH)
was maintained between 9 and 9.5 by the addition of .

The next morning, it was salted with 25 parts of rock salt (parts/volume) and heated at 70-80°C for 1 hour.

It was passed under vacuum and carefully squeezed.

The obtained product could be applied for dyeing and printing cellulose fibers after drying at 70-80°C.

It thus gave a brownish-yellow color and exhibited excellent stability to moisture and light.

When the produced dye was measured in an aqueous solution at pH 9, λmax in visible light was 459 mμ.

Claims (1)

[Claims] coupling 12-aminophenol-4-sulfonic acid with resorcin in an aqueous alkaline medium after diazotization and then reacting with an aqueous solution of copper sulfate pentahydrate, and the product thus obtained then being coupled with a resorcin in an aqueous alkaline medium; of the formula ( 1) A novel method for producing a water-soluble triazo dye.