JPS60158264A - Dis-azo reactive dye - Google Patents

Abstract

NEW MATERIAL:Dis-azo compounds of formula I wherein R is CH3, C2H5 ; the ring A is a benzene ring, or a naphthalene ring ; m is 0-3 ; the sulfo group attached to the naphthalene ring B is bonded to the naphthalene ring B at position 6 or 7 against the azo group attached to the ring A. EXAMPLE:Compound of formula II. USE:Vinylsulfone type reactive dyes which dye cellulosic fibers dense brown with good fastness. PREPARATION:A monoazo compd. of formula III (wherein A, m naphthalene ring B are as defined above) is diazotized and then coupled with an alkylaniline of formula IV (wherein R is as defined above). The resulting org. compd., 3- aminophenyl-beta-sulfatoethylsulfone and cyanuric chloride are condensed together to produce the compd. of formula I .

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a disazo-reactive dye for cellulosic fibers. More particularly, the present invention relates to vinyl sulfone-type reactive dyes that dye cellulosic fibers, particularly natural or regenerated cellulose fibers, in a fast, deep brown color.

(In the formula, R represents a methyl group or an ethyl group, ring A represents a benzene ring or a naphthalene ring, m is O-3, and the sulfonic acid group bonded to the naphthalene ring B is attached to the ring A. It is a disazo-reactive dye for cellulose fibers, which is bonded to the 6 or 7 position with respect to the azo group bonded to it.The dye expressed by the general formula (i) of the present invention can be obtained, for example, as follows. be able to.

General formula (II) (wherein, the substitution positions of Alm and the sulfonic acid group on naphthalene ring B are the same as the substitution positions of A, m and the sulfonic acid group on naphthalene ring B in general formula (I) r-. ) is diazotized into a monoazo compound represented by the general formula (11
11 (wherein R is the same as R in general formula (I)), an organic dye obtained by coupling with an alkylaniline represented by It can be produced by condensation with cyanuric chloride in the following order.

The compound represented by the general formula (n) is a compound represented by the general formula (It/) (
In the formula, A and m are the same as A and m in general formula (I). ) by diazotizing the amine represented by the general formula (V) (wherein,
The substitution position of the sulfonic acid group on the naphthalene ring B is the 6th or 7th position with respect to the amino group. ) can be produced by coupling with naphthylamine sulfonic acid.

The following types of amines represented by general formula (IV) can be used in the present invention.

Aniline, aniline-2-sulfonic acid, aniline-3-
Sulfonic acid, aniline-4-sulfonic acid, aniline-2
, 5-disulfonic acid, aniline-3,5-disulfonic acid, aniline-2,4-disulfonic acid, ninaphthylamine-4-sulfonic acid, 2-naphthylamine-48-disulfonic acid, 2-naphthylamine-6,8-disulfonic acid acid, 2-naphthylamine-5,7-disulfonic acid, 1-naphthylamine-5-sulfonic acid, 1-naphthylamine-
6-sulfonic acid, 1-naphthylamine-7-sulfonic acid, 2-naphthylamine-5-sulfonic acid, 2-naphthylamine-6-sulfonic acid, 2-naphthylamine-7-sulfonic acid, 2-naphthylamine-8-sulfonic acid, 1-
naphthylamine-3,6-disulfonic acid, 2-naphthylamine-1,5-disulfonic acid, 2-naphthylamine-
1,6-disulfonic acid, 2-naphthylamine-6,8-
Disulfonic acid, 2-naphthylamine-3,6,8-)disulfonic acid, 2-naphthylamine-4,6,8-)disulfonic acid, 1-naphthylamine-2,5,7-)disulfonic acid, etc. also have the general formula ( The naphthylamine sulfonic acid represented by Vl includes 1-naphthylamine-6-sulfonic acid, 1-naphthylamine-7-sulfonic acid, and mixtures thereof.

Further, as the alkylaniline represented by the general formula (II) used as the secondary coupling component, m-toluidine, m-toluidine,
- Ethylaniline is an example, but disazo dyes obtained by using O-alkylaniline instead of these m-alkylanilines cannot be used in the dyes of the present invention because their chlorine bleach fastness is only about 4th grade and is inferior. .

Examples of cellulosic fibers that can be dyed with the disazo reactive dye of the present invention include natural fibers such as cotton and hemp, regenerated fibers such as viscose rayon, or blends of cellulose fibers and synthetic fibers such as polyester fibers and polyacrylonitrile fibers. can be mentioned.

To dye cellulose fibers using the monoazo reactive dye of the present invention, any conventional method can be used in the presence of an acid binder such as sodium bicarbonate or soda carbonate. For example, in the case of dyeing by dip dyeing, dyeing can be carried out by a conventional method at a temperature of 40 to 60° C. in the presence of an inorganic salt such as common salt or mirabilite salt and an acid binder.

Furthermore, when dyeing by a textile printing method, it can be dyed by a commonly used method, such as a method using sodium alginate, urea, a reduction inhibitor, or an acid binder.
Various conventional dyeing methods used for vinyl sulfone reactive dyes, such as the pad patch method and the pad steam method, can also be applied.

The dye of the present invention has a very high dyeing rate and is also advantageous in terms of waste water treatment after dyeing. In addition, various fastnesses are also very good, and in particular, the chlorine fastness, which has become a problem in recent years, is extremely excellent at grade 5, and has high practical value.

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

Example 1 2-Naphthylamine-3,6,8-) Lysulfonic acid disodium salt 10.711, ice water 100g and hydrochloric acid 5.211
1, and 35% sodium nitrite aqueous solution 5. ．． 1# from 0 to
Diazotization is carried out by addition at 5°C. After quenching with excess nitrous and sulfamic acid, 5.6 g of 1-naphthylamine-6-sulfonic acid was added and the pH was brought to 4-5 using 15% aqueous sodium carbonate solution. After the diazo compound disappears,
7.8 g of 35% hydrochloric acid was added at 0 to 5°C, and 5.1 g of 35% nitrous acid aqueous solution was added again to diazotize the mixture at the same temperature.

After erasing with excess nitrous sulfamic acid, m-)
Approximately 30 g of an acidic aqueous solution of 2.7 g of Luidine was added, and 1
The pn was adjusted to 4 to 5 with a 5% aqueous sodium carbonate solution, and coupling was carried out until the diazo compound disappeared.

On the other hand, 4.6g of cyanuric chloride and 20mJ of acetone! It was added to 50Ii of ice water and suspended at 0 to 5°C. child,
The coupling liquid was added to the suspension, and a 15% aqueous sodium carbonate solution was added at 0 to 5°C to maintain the pH at 5 to 6. After about 2 hours, no hydrochloric acid was produced, so 7.0 g of 3-aminophenyl-β-sulfatoethyl sulfone was added, and 1
Adjust the pH to 5 to 6 with a 5% aqueous sodium carbonate solution, and then adjust the pH to <pH 5.
The temperature was raised to 40°C while maintaining the temperature at ~6. After keeping the pH at 5-6 at 40°C for about 3 hours, salting out with potassium chloride,
After filtration and drying, a brown dye 30.29 of the following formula was obtained in free acid form.

Dissolve 0.3 g of this dye in 200 g of water and add 201 g of mirabilite.
Cotton cloth 1011 was immersed in a dye bath prepared by adding and dissolving 1, and the temperature was raised to 50° C. over 30 minutes.

Next, 4.5 liters of sodium carbonate was added and dyed at 50° C. for 1 hour, followed by washing with water and soaping to obtain a dyed product with a high concentration of brown and excellent fastness to chlorine, light, perspiration and sunlight. Chlorine bleaching fastness of this product (weak test, JISL 0856)
) was grade 5.

(Left below) Examples 2 to 4 A dye represented by the general formula below was synthesized using a method similar to Example 1, and cotton fabric was dyed. As a result, a brown dyed product with good light fastness and chlorine fastness was obtained. I got it. The results are shown in Table-1.

Table 1

Claims (1)

[Claims] 1. General formula (I) (wherein, R represents a methyl group or an ethyl group, and ring A
represents a benzene ring or a naphthalene ring, and m is 0 to
3, and the sulfonic acid group bonded to the naphthalene ring B is an azo bonded to the ring.