JPS59161464A - Monoazo compound and its preparation - Google Patents

Abstract

NEW MATERIAL:The compound of formula I (R is methoxy or ethoxy; X1 and X2 are H, methyl, methoxy, 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, and is suitable for the dyeing of sportswear, etc. PREPARATION:2-Aminonaphthalene-4,8-disulfonic acid is diazotized, and coupled with the toluidine 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 relates to a novel monoazo compound and a method for producing the same.More specifically, the present invention relates to a monoazo compound suitable for dyeing textile materials, particularly cellulose fiber materials, yellow, and a method for producing the same.

It is known that dyes having a β-sulfatoethyl sulfone group can be applied 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 has been a strong demand for a yellow reactive dye with excellent strength.

Yellow dyes with a monochlorotriazinyl group as another typical reactive group different from the β-sulfone and fartoethyl-sulfone groups 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 obtained, so it is never sufficient for practical use. I couldn't say that. For this reason, the present inventors conducted extensive research in search of a yellow vinyl sulfone type reactive dye with particularly excellent chlorine fastness. It has been found that certain monoazo compounds containing a lutriazinyl group give yellow dyeings of excellent chlorine fastness. It has also been found that such specific monoazo compounds can overcome the drawbacks of reactive dyes having a monochlorotriazinyl group as described above.

That is, according to the present invention, the following general formula (
I) (wherein R is a methoxy group or an ethoxy group, Xl, x2
each represents hydrogen, methyl group, methoxy group or sulfonic acid group. ) The monoazo compound represented by
> Ha (In the formula, R has the above meaning.) Coupling with a toluidine compound represented by the general formula (m) (In the formula, R has the above meaning.) obtained, and cyanuric chloride and general formula (IV) or (V) (IV)
When the aniline compound represented by formula (V) (wherein Xr and X2 have the above-mentioned meanings) is condensed in any order and the aniline compound represented by general formula (V) is used, then sulfuric acid ester Provided is a method for producing a monoazo compound represented by the general formula (I), which comprises converting the monoazo compound into a monoazo compound.

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-4,8--,! Sulfonic acid is diazotized according to a conventional method, and this is coupled with a toluidine compound represented by general formula (n) by a conventional method to obtain an aminomonoazo compound represented by general formula (■). This is primarily condensed with cyanuric chloride to obtain a dichlorotriazinyl compound, and then an aniline compound represented by the general formula (blank) is secondarily condensed to obtain a monoazo compound represented by the general formula (I). Can be done.

Alternatively, the monoazo compound of the general formula (I) can be obtained by firstly condensing the aniline compound represented by the general formula (IV) with cyanuric chloride, and then secondarily condensing the aminomonoazo compound of the general formula (III). You can get it.

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

In each case, the above condensation reaction is carried out using the known de/'1 if
It can be carried out according to the method of hydrogenation condensation.

In the monoazo compound produced by the above method, the sulfatoethyl sulfone group can be easily changed by the action of an alkali to form a monoazo compound having a vinyl sulfone 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 relatively low temperature in a dye bath containing mirabilite or common salt in the presence of an acid binder such as soda 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 sulfate ethyl sulfone group becomes a vinyl sulfone group and 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 fastness to sunlight.

In particular, considering that the use of chlorine-based source agents for 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 fastness to light, perspiration and sunlight makes it suitable for dyeing external wear such as sportswear.

In addition, since the monoazo compound of the present invention exhibits a high exhaustion rate, it is possible to obtain dyed products with high density, and it is also advantageous in terms of wastewater treatment because only a small amount of dye remains in the dye bath. 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. 85-1
Publication No. 0628 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 lack exhaustion suitability, so they have the drawback of not producing a high density for dyeing.

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

In addition, Japanese Patent Publication No. 89-18184 describes the yellow reactive dyes shown below, but the chlorine fastness of these dyes is very low at grade 1 according to the 150 method.
Its practical value is small.

In contrast, the yellow dye of the present invention has a chlorine fastness of IS
It has an extremely excellent grade 4 or 4-5 according to the O method, and its light fastness is grade 6-7, and its sweat and sunlight fastness is grade 4 or 4-4.
All of them are excellent as grade 5. In addition, the acid stability of dyed products (
The test method is to immerse the dyed fabric in 1% acetic acid for 80 minutes, and then use a perspirometer to treat 87 parts at 12,517 cd at a temperature of 2°C for 6 hours), which is also good at grades 4-5 to 5.

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

In the text, parts represent parts by weight.

Example 1 A solution containing 6.1 parts of 2-aminonaphthalene-48-disulfonic acid and 4.1 parts of concentrated hydrochloric acid in 100 parts of water was heated at 0 to 10°C.
After cooling to a temperature of 100%, a solution prepared by dissolving 1.4 parts of sodium nitrite in 8.8 parts of water was poured into the solution, and the mixture was stirred at the same temperature for 80 minutes. After removing excess nitrous acid, a solution containing 2.8 parts of concentrated hydrochloric acid and 2.7 parts of 2-methoxy-5-methylaniline in 20 parts of water was added and stirred at 0-10°C for 5 hours. After adjusting the pH of this solution to 8-5 to complete the force/knobbling, increase the pH to 8 to dissolve the product, and add 20 parts of sodium chloride to reprecipitate the crystals. After suction filtration and washing, it is redissolved in 100 parts of water and the pH is adjusted to 6-7. Add 3.8 parts of cyanuric chloride to this solution and
Stir at 0 to 256 C for 5 hours while adjusting the pH to 5 to 6 using a 20% aqueous sodium carbonate solution.

Next, 5.6 parts of 1-aminobenzene-8-β-hydroxyethylsulfone sulfate was added, and the temperature was raised to 40°C while adjusting the pH to 6-6 using a 20% aqueous sodium carbonate solution. Stir at temperature for 5 hours. Add 20 parts of sodium chloride to this solution to precipitate crystals,
After suction filtration, washing, and drying at 60°C, monoazo compounds (1) were obtained. In the same manner, the following monoazo compounds (2) and (8) were obtained.

Example 2 2-methoxy-5-methylaniline 2 in Example 1
．． 2-ethoxy-5-methylaniline instead of 7 parts 8.
The following monoazo compound (4) was obtained in the same manner as in Example 1 using 0 parts.

(λmax 4Q9 nm) Monoazo compounds (5) and (6) of F were obtained in the same manner.

aCO (λmax 4091m) Reference Example 1 0.8 parts of the monoazo compound of formula (1) obtained in Example 1 was dissolved in 200 parts of water, 20 parts of Glauber's salt was added, and 10 parts of cotton
After 20 minutes, add 4 parts of soda and raise the temperature to 50''C.
Add part. Dye for 1 hour at that temperature. After dyeing,
After washing with water and soaping, a highly concentrated yellow dyed product with excellent fastness properties, especially fastness to chlorine, was obtained. The reproducibility of staining was also excellent.

(Chlorine fastness grade 4-5 (ISO method), sweat fastness to sunlight grade 4-5
Grade 5, exhaustion rate 99%, fixation rate 98%) Similarly, formula (2
) and (3), a similar yellow dyed product was obtained.

Further, when a monoazo compound represented by Formula 51 (1) in which the sulfate ethyl sulfone group is a vinyl sulfone group was dyed in the same manner as above, a similar dyed product was obtained.

Reference Example 2 0.8 parts of the monoazo compound of formula (4) obtained in Example 2 was dissolved in 200 parts of water, 20 parts of Glauber's salt was added, and 10 parts of cotton
The mixture was heated to 60°C, and after 20 minutes, 8 parts of tribasic sodium phosphate was added.

Dye for 1 hour at that temperature. After the dyeing was completed, washing and soaping were performed to obtain a yellow dyed product with excellent chlorine fastness and dyeing performance equivalent to that of the dye of formula (1) of Example 1.

In the same manner, a heavy color dyed product similar to Nekoru was obtained by dyeing using the monoazo compounds represented by formulas (5) and (6).

Further, when a monoazo compound represented by formula (4) in which the sulfate ethyl sulfone group is a vinyl sulfone group was dyed in the same manner as above, a similar dyed product was obtained.

Claims (2)

[Claims] (1) In the form of a free acid, the following general formula (wherein R is a methoxy group or an ethoxy group, Xl,
2 each represents hydrogen, a methyl group, a methoxy group or a sulfonic acid group. ) is a monoazo compound represented by (2) 2-aminonaphthalene-4,8-disulfonic acid is diazotized to form a compound of the general formula (II) Ha (wherein R represents a methoxy group or an ethoxy group).
) to obtain an aminomonoazo compound represented by the general formula (m) 0sH (wherein R has the above-mentioned meaning), which is coupled with cyanuric chloride and the general formula (tV) or (v) SO2CH2C
Hs+05OaH5O2G (2C820H(IV)
(V) (wherein Xl and X2 each represent hydrogen, a methyl group, a methoxy group, or a sulfonic acid group) are condensed in any order to form an aniline compound represented by the general formula (V). If you use
A method for producing a monoazo compound represented by general formula (I) 1 (wherein R, Xt, and Xt have the above-mentioned meanings) in the form of a free acid, which is then subjected to sulfuric acid esterification.