JPS59161463A - Monoazo compound and its preparation - Google Patents

Abstract

NEW MATERIAL:The compound of formula I (R is methyl or amino; X1 and X2 are H, Cl, methyl, methoxy, carboxy or sulfonic acid group) as free acid. EXAMPLE:The compound of formula II. USE:A dye for dyeing cellulosic fiber material in yellow color. It has excellent fastness to chlorine, light, and sweat and sunlight. PREPARATION:2-Aminonaphthalene-3,6,8-trisulfonic acid is diazotized, and coupled with the m-phenylenediamine compound of formula III to obtain the amino- monoazo compound of formula IV, which is condensed with cyanuric chloride and the aniline compound of formula V or VI. When the aniline compound is formula VI, the product is converted to sulfuric acid ester.

Description

[Detailed description of the invention] The present invention is a monoazo compound and a method for producing the same.

Regarding. More specifically, the present invention relates to a monoazo compound suitable for dyeing fiber materials, particularly cellulose fiber materials, yellow, and a method for producing the same.

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

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 cannot be used at high temperatures compared to the general dyeing temperature. In addition, it is only used for printing with a lack of exhaustion dyeing suitability, and it is not suitable for practical use even though it has the disadvantage of low acid stability of the dyed product. The inventors of the present invention have developed a special code and a chlorine-resistant product.
As a result of extensive research in search of a vinyl sulfone-type reactive dye with a degree (7) of yellow color, a specific σ) monoazo compound having a β-sulfatoethyl sulfone group and a monochlorotriazinyl group as a reactive group was found. It has been found that it gives yellow dyeings of excellent chlorine fastness. It has also been found that such a specific compound can overcome the drawbacks of reactive dyes having a monochlorotriazinyl group as described above.

That is, in the form of a free acid, the following general formula (I)C [ [wherein, 几 represents a methyl group or an amino group, and X1 and X2 each represent hydrogen, chlorine, a methyl group, a methoxy group, a carboxy group, or a sulfonic acid group] . ] The monoazo compound represented by these and 2-aminonaphthalene-8,6,8-1 lysulfonic acid are diazotized to give the general formula (yam) [wherein R has the above meaning. ] The m-phenylenediamine compound represented by the formula (1) is coupled with the general formula (1) [wherein has the above-mentioned meaning. ] An aminomonoazo compound represented by the formula (FF) or (V) is obtained, together with cyanuric chloride and the general formula (ff) or (V)
X2 has the meaning given above. ] The aniline compound represented by formula (I) is condensed in any order, and when the aniline compound represented by general formula (V) is used, the monoazo compound represented by general formula (I) is then esterified with sulfuric acid. A method of making a compound is provided.

The monoazo compound represented by the general formula (I) has excellent dye properties and is suitable for dyeing fiber materials, especially natural or regenerated cellulose fiber materials such as cotton, linen, viscose human silk, and viscose cotton, and is suitable for dyeing various natural or regenerated cellulose fiber materials. It is possible to provide a yellow dyeing with excellent fastness, especially fastness to chlorine.

The monoazo compound represented by the general formula (I) can be produced by the method described below.

2-Aminonaphthalene-8,6,8-)risulfonic acid is diazotized according to a conventional method, and this is coupled with an m-phenylenediamine compound represented by the general formula (1) according to a conventional method to obtain the general formula (I ) is obtained.

This is primarily condensed with cyanuric chloride to obtain a dichlorotriazinyl compound, and then an aniline compound represented by general formula (ff) is condensed secondarily to obtain a monoazo compound represented by general formula (1). be able to.

Alternatively, the monoazo compound of general formula (1) can also be obtained by firstly condensing an aniline compound represented by general formula (fV) with cyanuric chloride, and then secondarily condensing the monoazo compound of general formula (I). be able to.

Alternatively, the β-hydroxyethyl sulfone compound represented by the general formula (V) can be used in place of the aniline compound of the general formula (■), and the same reaction can be carried out, followed by esterification in sulfuric acid according to a conventional method. According to the general formula (1)
It may also be used as a monoazo compound.

In either case, the above condensation reaction can be carried out according to a known method for de-denogenide condensation.

In the monoazo compound produced by the above method, the sulfatoethylsulfonyl group can be easily changed by the action of an alkali to form a monoazo compound having a vinylsulfonyl group.

The monoazo compound of the present invention thus obtained is useful for yellow dyeing of natural or regenerated cellulose fibers such as cotton, linen, viscose human silk, and viscose cotton.

In the case of the exhaust method, dyeing is carried out at a specific absorption temperature in a dye bath containing mirabilite or common salt in the presence of an acid binder such as sodium carbonate, tribasic sodium phosphate, or caustic soda. It can also be dyed using a textile printing method. At this time, by addition of an acid binder, the sulfatoethylsulfonyl group becomes a vinylsulfonyl group, which undergoes an addition reaction with the cellulose fibers to effect dyeing.

By such a dyeing method, the monoazo compound of the present invention provides a yellow dyed product particularly excellent in chlorine fastness, light fastness, and sweat/sunlight fastness.

In particular, considering that the use of chlorine bleach in laundry in general households has recently become widespread, the value of the monoazo compound of the present invention, which provides dyed products with excellent chlorine fastness, is high. In addition, its excellent light fastness, sweat fastness and sunlight fastness make it suitable for dyeing external wear such as sportswear.

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

Furthermore, the monoazo compound of the present invention has excellent level dyeing properties, can be applied over a wide range of dyeing temperatures, and is less affected by the amount of inorganic salt added and the bath ratio, so it also has the characteristics of good dyeing reproducibility.

As a dye similar to the present invention, for example, Japanese Patent Publication No. 89-
Publication No. 2684 describes, for example, a monochlorotriazine type yellow reactive dye shown below in the form of a free acid. However, these dyes require high temperatures for dyeing and are not suitable for exhaustion, so they have the disadvantage that they do not produce a high density for dyeing.

Another disadvantage is that the resulting dyed product has low acid stability and is susceptible to changes over time.

Further, Japanese Patent Publication No. 89-18184 describes the following yellow reactive dyes. However, the chlorine fastness of these dyes is very low, being 1st class according to the ISO method, and their practical value is small.

On the other hand, the monoazo compound of the present invention has an excellent chlorine fastness of 8th grade to 8th to 4th grade according to the I80 method. In addition, the light fastness is 6th grade, and the sweat and sunlight fastness is 4th to 5th grade, both of which are excellent. Furthermore, the acid stability of the dyed product (test method is after soaking the dyed fabric in 1% acetic acid for 80 minutes) <-87 parts using a spirometer and treating at 125 f/d for 6 hours at a temperature of 2°C) is 4 -5th grade to 5th grade, which is good.

Next, the present invention will be explained by examples. In the text, parts represent parts by weight.

Example 1 2-aminonaphthalene-8,6,8-) in 100 parts of water
Add 8.5 parts of lysulfonic acid disodium salt, adjust the PL to 8 with caustic soda solution and dissolve. After adding 1.4 parts of sodium nitrite to this solution, cool to 0-5°C and then dissolve. Inject 6.1 parts of concentrated hydrochloric acid and stir for 30 minutes at the same temperature.After removing excess nitrous acid, m-
Add 8.8 parts of acetylaminoaniline dissolved in 80 wtl of water at 0-5°C.

Next, the pH of this solution is adjusted to 8 to 5 to complete the coupling, and then the pH is raised to 8 to dissolve the product, and 40 parts of sodium chloride is added to reprecipitate the crystals.

After suction filtration and washing, it was redissolved in 100 parts of water.
pl (adjust to 6-7. Add cyanuric chloride 8 to this solution.
．． Add 3 parts and stir at 20-25°C for 5 hours while adjusting the pH to 5-6 using 20% aqueous sodium carbonate solution.

Next, after adding 5.6 parts of 1-aminobenzene-8-β-hydroxyethylsulfone sulfate, the temperature was raised to 40°C while adjusting the pH to 5 to 6 using a 20% aqueous sodium carbonate solution. Stir for 5 hours. 25 parts of sodium chloride was added to this solution to precipitate crystals, which were suction filtered, washed, and dried at 60°C to obtain a monoazo compound of the following formula (1).

Formula (1) (λmax 4 Q Q nm in an aqueous solvent, the same applies hereinafter) Perform diazo and coupling in the same manner as above to obtain the aminomonoazo compound [general Nishu] shown in the table below. The aniline compounds shown [general formula α] were condensed in the same manner as above to obtain respective monoazo compounds.

Example 2 A monoazo compound represented by the following formula (6) was obtained in the same manner as in Example 1 except that 8-aminophenyl urea was used in place of m-acetylaminoaniline in Example 1.

Formula (6) % Formula %) Coupling to shea was carried out in the same manner as in Example 1 to obtain the aminoazo compound [general formula (Ill)] shown in the table below, and this and the aniline compound [general formula (Ill)] shown in the table below. ] were similarly condensed to obtain the respective monoazo compounds.

Reference Example 1 0.8 parts of the monoazo compound represented by formula (1) 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 40°C. After 30 minutes, 4 parts of soda carbonate was added and dyed at the same temperature for 1 hour. After dyeing, washing and soaping were performed to obtain a yellow dyed product with excellent chlorine fastness.

In addition, the monoazo compounds (2), (8), (4),
When dyeing was carried out in the same manner as above using (5), yellow dyed products with excellent chlorine fastness were obtained.

Also, when a monoazo compound represented by formula (1) in which the sulfatoethylsulfonyl group is a vinylsulfonyl group was dyed in the same manner as above, a similar dyed product was obtained. I was massaged.

Reference Example 2 0.3 parts of a monoazo compound represented by formula (6) was added to 200
of water, add 20 parts of Glauber's salt, add 10 parts of cotton, raise the temperature to 50°C, and after 20 minutes add 4 parts of soda carbonate. Dye for 1 hour at that temperature. After dyeing, wash with water,
After soaping, a yellow dyeing with excellent chlorine fastness was obtained.

(10), a yellow dyed product with excellent chlorine fastness was obtained.

Further, when a monoazo compound represented by formula (6) in which the sulfatoethylsulfonyl group is a vinylsulfonyl group was dyed in the same manner as above, a similar dyed product was obtained.

Claims (1)

[Claims] 1) In the form of a free acid, the following general formula [wherein is a methyl group or an amino group, Xl. X2 each represents hydrogen, chlorine, methyl group, methoxy group, carboxy group or sulfonic acid group. ] A monoazo compound represented by 2) 2-aminonaphthalene-8,6,8-trisulfonic acid is diazotized to give the general formula 1) % formula % [wherein R represents a methyl group or an amino group]. ] It is made to couple with the m-phenylenediamine compound shown by General formula (1) [In formula, 几 has the above-mentioned meaning. ] An aminomonoazo compound represented by the formula (IT) or (MA) [wherein, Xl,
X2 each represents hydrogen, chlorine, methyl group, methoxy group, carboxy group or sulfonic acid group. ] The aniline compound represented by is condensed in any order, to □11
□□□□ When a compound of general formula (1) is used, it is then converted into a sulfuric acid ester in the form of a free acid, where R, X and X2 have the above meanings. ] A method for producing a monoazo compound represented by.