JPS60215063A - Fiber-reactive monoazo compound - Google Patents

Abstract

NEW MATERIAL:Monoazo compounds of formula I (wherein R is OH, amino; X is H, methyl, methoxy, sulfo group; m is 0, 1, 2). EXAMPLE:A compound of formula II. USE:Dyes which dye cellulosic fibers clear yellow with excellent fastness to chlorine, light and perspiration. PREPARATION:2-Aminonaphthalenesulfonic acid of formula III (wherein m is as defined above) is diazotized and then coupled with a pyrazolone derivative of formula IV (wherein R is as defined above) at a neutral to alkaline pH to obtain a monoazo compd. of formula V (wherein R, m are as defined above). The monoazo compd. is primarily condensed with cyanuric chloride to obtain a dichlorotriazinyl compd. which is then condensed with an aniline compd. of formula VI (wherein X is as defined above) to obtain the dye of formula I .

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for dyeing cellulose fibers in bright yellow.

More specifically, the present invention provides compounds of the following general formula (I) 503HRX (wherein R is a hydroxyl group or an amino group, X is hydrogen, a methyl group, a methoxy group, or a sulfonic acid group, and m is 0, 1 or This is a method for dyeing cellulose-based fiber materials, which is characterized by using a dye represented by (2).

It is known that dyes having a β-sulfatoethylsulfone group can be used as so-called vinylsulfone-type reactive dyes for dyeing textile materials. However, dyeings made with azo-based bright yellow reactive dyes containing a β-sulfatoethyl sulfone group generally have low chlorine fastness, and fading due to chlorine contained in tap water is often a problem. There has been a strong demand for a bright yellow reactive dye with excellent chlorine fastness.

Bright yellow dyes with a monochlorotriazinyl group as another typical reactive group different from the β-sulfatoethyl sulfone group are also known, but these reactive dyes generally require high dyeing temperatures. In addition, it is only used for textile printing because it lacks exhaust dyeing suitability, and furthermore, it has the disadvantage of low acid stability of the dyed product, so it is never sufficient for practical use. I couldn't say it. For this reason, the inventors of the present invention have conducted intensive studies to develop a bright yellow vinyl sulfone type reactive dye with particularly good chlorine fastness. It has been found that monoazo dyes having as radicals β-sulfatoethylsulfone and monohalogenotriazinyl give bright yellow dyeings of excellent chlorine fastness. It has also been found that the dye of the present invention can overcome the drawbacks of reactive dyes having a monochlorotriazinyl group as described above.

In the present invention, the cellulose fibers include natural or regenerated cellulose fibers such as cotton, linen, viscose human silk, and viscose cotton.

In the case of the exhaust method, the dyeing of the present invention is carried out at a relatively low temperature in a dye bath containing Glauber's salt or common salt in the presence of an acid binder such as soda carbonate, tribasic sodium phosphate, or caustic soda. Also,
It can also be dyed using the textile printing method.

The dye of the present invention can be produced, for example, as follows. 2-aminonaphthalenesulfonic acid represented by the general formula (1) (% formula %) (wherein m has the above meaning) is diazotized to form a compound of the general formula (2) (wherein R has the above meaning). A monoazo compound represented by the general formula (W) (wherein R and m have the above-mentioned meanings) is obtained by coupling with a pyrazolone derivative represented by and cyanuric chloride are primarily condensed to obtain a dichlorotriazinyl compound. Then, the aniline compound represented by the general formula (V) (wherein X has the above-mentioned meaning) is secondarily condensed to obtain the dye represented by the general formula (1).

Alternatively, the dye in the general formula can also be obtained by firstly condensing an aniline compound represented by the general formula (V) with cyanuric chloride, and secondarily condensing the monoazo compound represented by the general formula (IV). be able to.

Alternatively, cyanuric chloride, a pyrazolone derivative represented by the general formula (2), and an aniline compound represented by the general formula (V) are condensed in any order to form a compound of the general formula (1) (wherein R and X have the above-mentioned meanings). The dye in the general formula can also be obtained by obtaining a compound represented by the formula (1) and then coupling it with a diazonium salt of 2-aminonaphthalenesulfonic acid represented by the general formula (1).

Alternatively, a β-hydroxyethyl sulfone compound represented by the general formula (■) 502C-OH (in the formula, After carrying out the reaction, the dye of general formula (1) may be obtained by finally esterifying in sulfuric acid.

Examples of the compound of general formula () include the following compounds.

2-aminonaphthalene-1-sulfonic acid, 2-aminonaphthalene-1,5-disulfonic acid, 2-aminonaphthalene-1,7-disulfonic acid, 2-aminonaphthalene-1
,5,7-)disulfonic acid.

Examples of the compound of general formula (V) include the following.

1-aminobenzene-3 or 4-β-sulfatoethylsulfone, l-amino-2-methoxybenzene-5-
β-sulfatoethylsulfone, ■-amino-4-methoxybenzene-8-β-sulfatoethylsulfone, 1-amino-2-sulfobenzene-4-β-sulfatoethylsulfone, l-amino-2 -Sulfobenzene-5-β-sulf-1-toethylsulfone, 1-amino-
2-Methylbenzene-5-β-sulfatoethylsulfone, 1-amino-4-methylbenzene-3-β-sulfatoethylsulfone.

The dye of the present invention thus obtained is particularly excellent in chlorine fastness, light fastness, and sweat/sunlight fastness. In particular, considering that the use of chlorine bleach for household cleaning has recently become widespread, the value of the dye of the present invention, which has excellent chlorine fastness, is high. In addition, its excellent light fastness and sweat/sunlight fastness make it suitable for dyeing external wear such as sportswear.

Furthermore, since the dye of the present invention exhibits a high exhaustion rate, it is possible not only to obtain dyed products with high density, but also to have a small amount of dye remaining in the dye bath, which is advantageous in terms of wastewater treatment. .

Furthermore, the dye of the present invention has excellent wash-off properties, and has the great advantage that unfixed dye can be easily removed.

Furthermore, the present invention has the unique ability to be unaffected by changes in dyeing temperature, alkali agent, amount of inorganic salt added, and bath ratio in exhaust dyeing, and dyeing can be carried out with extremely high reproducibility.

As a dye similar to the present invention, for example, Japanese Patent Publication No. 39-1
No. 8184 describes the yellow reactive dye shown below. However, the chlorine fastness of these dyes is very low at grade 1 according to the ISO method.
Its practical value is small.

On the other hand, the yellow dye of the present invention has a chlorine fastness according to JIS.
The colorfastness to light is 6th grade, and the sweat and sunlight fastness is 4th grade to 4th to 5th grade, both of which are excellent.

Furthermore, the acid stability of the dyed material (the test method is to soak the dyed fabric in 1% acetic acid at 80%
After soaking for 1 minute, 37 parts were treated with 1259/c) at a temperature of 2° C. for 6 hours using a bar spirometer.

Next, the method of the present invention will be explained with reference to examples.

In the text, parts represent parts by weight.

Example 1 0.8 parts of a dye represented by formula (1) (% formula %) is dissolved in 200 parts of water, 20 parts of Glauber's salt are added, 10 parts of cotton are added, and the temperature is raised to 5°C. Then, after 80 minutes had elapsed, 4 parts of soda carbonate was added and dyed at the same temperature for 1 hour. After dyeing, washing with water and soaping yielded a bright yellow dyed product with excellent fastness, especially fastness to chlorine.

The above dye is synthesized, for example, as follows.

9.2 parts of cyanuric chloride is added to a solution in which 0.1 part of a nonionic surfactant is dissolved in 100 parts of water at 0 to 10°C and dispersed. Add 14.0 parts of 1-aminobenzene-3-β-sulfatoethyl sulfone to 150 parts of water at pH 6.
After adding the dissolved solution in 1 hour, the mixture was stirred at 0 to 10''C for 2 hours while adjusting the pH to 2 to 8.

Then 2-aminonaphthalene-1-sulfonic acid 11.1
The diazonium salt of 1-(8'-aminophenyl)-
The monoazo compound obtained by coupling to 7.6 parts of 3-methylpyrazolone was added, and p
Adjust the temperature to H5-6, raise the temperature to 30°C, and raise the temperature to 8°C at the same temperature.
Stir for an hour.

40 parts of sodium chloride was added to this solution to precipitate crystals, which were filtered, washed, and dried at 60°C to obtain dye (1).

Example 2 0.8 parts of a dye represented by the formula (2) (% formula %) is dissolved in 200 parts of water, 20 parts of Glauber's salt is added, 10 parts of cotton are added, and the temperature is raised to 60°C.

Then, after 20 minutes, 3 parts of tribasic sodium phosphate is added.

Dye for 1 hour at that temperature. After dyeing, washing with water and soaping yielded a bright yellow dyed product with excellent fastness, especially fastness to chlorine.

Examples 8 to 6 When dyeing was carried out using the following dyes in the same manner as in Example 1 or 2, bright yellow dyed products with excellent chlorine fastness were obtained.

Claims (1)

[Claims] In the form of a free acid, it has the following general formula (wherein, R is a hydroxyl group or an amino group, X is hydrogen, a methyl group, a methoxy group, or a sulfonic acid group, and m is 0.1 or 2). A monoazo compound represented by