KR19980072440A - Mono-Azo Disperse Dyes for Polyester Fibers - Google Patents

Abstract

It relates to the yellow type monoazo dispersion dye for polyester fiber represented by the following general formula (I),

In the above formula;

R is a C ₁ to C ₄ alkyl group;

X is 3-methoxy butoxy group, 2-phenylethyl amino group, 3- (3-methoxy propyloxy) phoroxy oxy group, N- (2-pyrrolidino) ethoxy group, 4-ethoxy benzene amino group, 2 -Pyridyl amino group, 3-methoxy-3-methyl butoxy group, 5-ethoxy carbonyl pentyl amino group or 3-chloro-4-methyl benzene amino group.

Description

Mono-Azo Disperse Dyes for Polyester Fibers

It is an object of the present invention to provide a yellow monoazo dye, ie a monoazo dye for polyester fibers represented by the following general formula (I).

In the above formula;

R represents an alkali group of C ₁ to C ₄ ;

X is 3-methoxy butoxy group, 2-phenylethyl amino group, 3- (3-methoxy propyloxy, propyl oxy group, N- (2-pyrrolidino) ethoxy group, 4-ethoxybenzene amino group, 2- A pyridyl amino group, 3-methoxy-3-methyl butoxy group, 5-ethoxy carbonyl pentyl amino group, and 3-chloro-4-methyl benzene amino group are shown.

The yellow monoazo dispersion dye of the general formula (I) according to the present invention diazotizes the aniline derivative represented by the following formula (II) by a generally known method;

In the above formula;

X is the same as defined in general formula (I).

It is produced by coupling with a pyridone compound represented by the following general formula (II).

In the above formula;

R is a C ₁ to C ₄ alkyl group.

As a specific example of the aniline compound represented by general formula (II) which can be used as a diazo component in the manufacturing method of the disperse dye (I) which concerns on this invention;

4- (3-methoxy butoxy carbonyl) benzeneamino, 4- (2-phenylethyl amino carbonyl) benzene amino, 4- [3- (3-methoxy propyloxy) propyloxy carbonyl] benzene amino;

4- [N- (2-pyrrolidino) -ethoxy carbonyl] benzeneamino;

4- (4-ethoxy benzeneamino carbonyl) benzeneamino;

4- (2-pyridylamino carbonyl) benzeneamino;

4- (3-methoxy-3-methylbutoxycarbonyl) benzeneamino;

4- (5-ethoxy carbonyl pentylamino carbonyl) benzeneamino;

4-[(3-chloro-4-methyl) benzeneaminocarbonyl] benzeneamino.

The pyridone compound represented by the general formula (III) used as a coupler component is, for example, ethylaceto acetate, methylcyano acetate, and alkylamine of C ₁ to C ₄ for 15 hours in the temperature range of 80 ℃ to 100 ℃ It is prepared by refluxing.

The method for preparing the dye compound (I) according to the present invention can be carried out by diazotization and coupling reaction according to a known method, for example, 4- (3-methoxy butoxycarbonyl) benzeneamino and The same aniline is added to a sulfuric acid solution in which nitrous acid is dissolved or dissolved in an aqueous hydrochloric acid solution, followed by diazotization by adding nitrous acid aqueous solution, followed by acetic acid containing 3-cyano-4-methyl-6-hydroxypyridone derivative. It can couple | couple and couple | pour into alkyl aqueous solution, such as sodium, sodium carbonate, or caustic sodium. In addition to the basic, the coupling reaction can be carried out in a neutral or acidic aqueous solution.

Fibers which can be dyed with the monoazo yellow dispersant of the present invention include polyester fibers made of polyethylene terephthalate or a condensate of terephthalic acid with 1,4-bis- (hydroxy methyl) cyclohexane, or cotton, silk or wool. And blended products and blended materials of natural fibers such as polyester fiber described above.

In order to dye the polyester fiber using the disperse dye of the present invention, the dye represented by the general formula (I) may be used as an anionic dispersant such as sodium salt of naphthalene sulfonic acid and formaldehyde condensate or lignin sulfonic acid as water and a dispersant. In the presence of a paste or pulverized using a grinder such as a ball mill, sand grinder or sand mill, or a dry powder prepared by spray dryer to prepare a dyeing bath or soda alginate, etc. When performed, very good dyeing results can be obtained.

For example, in the case of dip dyeing, a well-known dyeing treatment method such as high temperature dyeing, carrier dyeing and thermosol dyeing can be used to dye polyester fibers or blends thereof with excellent color fastness. By adding acidic materials such as formic acid, acetic acid, phosphoric acid or ammonium sulfate, much better dyeing results can be obtained. In addition, when the dyes of the general formula (I) according to the present invention are used in combination with dyes of the same system or other yellow dyes of the same system, or when the dyes of the present invention of the formula (I) are used in combination, This results in very improved results.

Although this invention is demonstrated in detail based on an Example, the technical scope of this invention is not limited to this.

Example 1

33.45 g (0.15 mol) of 4- (3-methoxybutoxy carbonyl) benzeneamine was dissolved in a mixed solution of 35 mL of concentrated hydrochloric acid and 300 mL of water, and cooled to 0 to 5 DEG C, followed by 11.4 g of acetic acid. Was dissolved in 75 ml of water dropwise. The reaction was stirred at 0-5 ° C. for 2 hours, and 0.1 g of sulfamic acid was added thereto to prepare a diazo solution.

And 24.6 g (0.15 mol) of 1-methyl-3-cyano-4-methyl-6-hydroxy-2-pyridone, 43 g of sodium acetate, and 6 g of caustic soda in 1,000 ml of water. A diazo solution at 5 ° C. was added dropwise for 30 minutes and stirred for 2 hours. The resulting dye was filtered, washed and dried to give 55.2 g of yellow crystals of the azo compound represented by the following formula (IV).

The maximum absorption wavelength (λ max) in the acetone solution of this compound (IV) was 428 nm.

0.5 g of the dye obtained in Example 1 was added 1 g of naphthalene sulfonic acid formaldehyde condensate as a dispersant and 2 g of lignin sulfonic acid sodium salt to 1000 ml of melted water, pulverized with sand mill, suspended in 2.9 L of water, and then polyester in this dyeing bath. 50 g of the fiber was added and dyed at 130 ° C. for 60 minutes, followed by soaping, washing with water, and drying to obtain a bright yellow-yellow dyeing cloth. The light fastness, wash fastness and pH stability of this dyed cloth were good.

Example 2

33.5 g (0.15 mol) of 4- (3-methoxy butoxycarbonyl) benzeneamine in Example 1 was charged to 40.05 g (0.15 mol) of 4-[(3-methoxypropyloxy) propyloxycarbonyl] benzeneamine. Except for replacing, the same procedure as in Example 1 was carried out to obtain 56.3 g of yellow crystals of the azo compound represented by the following structural formula (V).

The maximum absorption wavelength (λ max) in the acetone solution of this compound (V) was 428 nm.

0.5 g of the dye obtained in Example 2 was dyed in the same manner as in Example 1 to obtain a bright yellow-yellow polyester dyed cloth having good daylight fastness, sublimation fastness and pH stability.

Example 3

1-butyl-3-cyano-4-methyl-6-hydroxy-2- instead of 24.6 g of 1-methyl-3-cyano-4-methyl-6-hydroxy-2-pyridone of Example 1 54.9 g of yellow crystals of the azo compound of the following structural formula (VI) were obtained in the same manner as in Example 1 except that 30.9 g (0.15 mol) of pyridone was used.

The maximum absorption wavelength (λ max) in the acetone solution of this compound (VI) was 429 nm.

0.5 g of the dye obtained in Example 3 was dyed in the same manner as in Example 1 to obtain a bright yellow-yellow polyester dyed cloth having good daylight fastness, sublimation fastness and pH stability.

Example 4-19

Dye of Structural Formula (I)

Wherein the definition of R and X is shown in Table 1 below, 33.45g of 4- (3-methoxy butoxycarbonyl) benzeneamine of Example 1 and 1-methyl-3-cyano-4-methyl 4-substituted kybornyl benzeneamine (0.15 mol) and 1-alkyl-3-cyano-4-methyl-6-hydroxy-2-pyridone instead of 24.6 g of 6-hydroxy-2-pyridone A yellow polyester dyed cloth was obtained in the same manner as in Example 1 except that (0.15 mol) was used, with good daylight fastness, sublimation fastness and pH stability.

[Table 1]

The present invention relates to a yellow monoazo dispersion dye for polyester fibers, and more particularly to the present invention, the polyester fiber is dyed to a yellowish yellow color, so that the overall fastness, particularly the light fastness, sublimation fastness and washing fastness, and temperature stability at the time of dyeing And a dispersion dye having excellent pH stability.

Claims (2)

Monoazo dispersion dye for polyester fiber represented by the following general formula (I) In the above formula; R is a C ₁ to C ₄ alkyl group; X is 3-methoxy butoxy group, 2-phenylethyl amino group, 3- (3-methoxy propyloxy) propyl oxy group, N- (2-pyrrolidino) ethoxy group, 4-ethoxy benzene amino group, 2- A pyridyl amino group, 3-methoxy-3-methyl butoxy group, 5-ethoxy carbonyl pentyl amino group, or 3-chloro-4-methyl benzene amino group is shown. A method of dyeing or printing polyester fibers or blended fibers thereof using the disperse dyes of formula (I) as defined in claim 1.