TW201843244A - Chromic blue azo dye as well as preparation method and application thereof - Google Patents

Abstract

The invention discloses a chromic blue azo dye as well as a preparation method and application thereof. The structural formula is as shown in formula (I). The chromic blue azo dye in the invention is applied to polyester fiber dyeing or printing. The chromic blue azo dye is selected from at least one compound of structural general formula (I) to prepare and obtain a disperse dye composition, and the disperse dye composition can be applied to polyester fiber dyeing or printing. During dyeing, the washing fastness, rubbing fastness, perspiration fastness, light fastness and degree of dyeing are excellent, and the disperse dye composition in the invention is high in strength, bright in color and good in dyeing property, particularly has excellent washing fastness, is stable in color and luster, is unlikely to fade and is relatively low in cost.

Description

Brilliant blue azo dye and preparation method and application thereof

The invention belongs to the technical field of dyes, and particularly relates to a brilliant blue azo dye and a preparation method and application thereof.

After entering the 21st century, competition in the world's textile market is becoming increasingly fierce. Southeast Asian economies have become synonymous with low cost and high growth, and textile industry businesses in Europe and the United States have also accelerated their transfer to Asia. In order to adapt to the fierce competition in the textile market, it has become a common goal for textile companies to continuously reduce the production cost of textiles, continuously improve the quality of products, and reduce the environmental load.

Disperse dyes have low solubility in water, very fine particles, and are dispersed in the dyeing solution. They are non-ionic dyes. They are mainly used for dyeing polyester, and their dyeing fastness is high.

Azo dyes (organic compounds with aryl groups at both ends of the azo group) are the most widely used class of synthetic dyes in the printing and dyeing process of textiles and garments. They are used for the dyeing and printing of a variety of natural and synthetic fibers. , Rubber and other colors. Azo dyes have a variety of colors, such as red, yellow, green, blue, etc. However, the existing blue azo dyes have problems such as poor washing fastness and are easily migrated out of the fabric fiber under high temperature conditions, which seriously affects Dye fastness to fabrics.

The technical problem to be solved by the present invention is to provide a brilliant blue azo dye with good dyeing fastness.

In order to solve the above technical problems, the technical solution of the present invention is:

A brilliant blue azo dye, the structural formula is shown in formula (I): (I);

Wherein R ₁ represents H, CH ₃ O or C ₂ H ₅ O;

R ₂ represents C ₁ ~ C ₄ alkyl;

R ₃ represents a C ₁ to C ₄ alkyl group.

Preferably, R ₁ represents CH ₃ O.

Preferably, R ₂ represents an ethyl group.

Preferably, R ₃ represents a methyl group.

Preferably, the following steps are included:

1) 6-bromo-2,4-dinitroaniline is diazotized with nitrosylsulfuric acid, then coupled with the coupling component, filtered, washed and dried to obtain the structural formula shown in formula (1): (1),

Wherein R ₁ represents H, CH ₃ O or C ₂ H ₅ O; R ₂ represents C ₁ ~ C ₄ alkyl; R ₃ represents C ₁ ~ C ₄ alkyl;

The coupling component is a structural formula shown by formula (2): (2),

Wherein R ₁ represents H, CH ₃ O or C ₂ H ₅ O, R ₂ represents C ₁ ~ C ₄ alkyl, and R ₃ represents C ₁ ~ C ₄ alkyl;

2) Cyanide the formula (1) in dimethylacetamide with a zinc salt and a copper salt, and filter out the crude product;

3) Detoxify the crude product with acidic ferric chloride in water and wash with water to obtain a brilliant blue azo dye.

The present invention also provides a disperse dye containing the above-mentioned brilliant blue azo dye, wherein the brilliant blue azo dye is selected from at least one compound of the general formula (I).

It should be noted that due to the particularity of the dye industry, it is difficult and unnecessary for each component to be made into a pure product, and it usually contains a small amount of water and a small amount of physical impurities. The existence of this part of water and physical impurities is in the present invention. Within the tolerance range.

The dye composition of the present invention can be obtained by conventional preparation methods in the industry, for example, after mixing the components in a preset ratio, the additives (including dispersants, water or other wetting agents, etc.) The presence of the disperse dye composition is obtained by micronizing with a pulverizing device such as a sand mill or a grinder in the presence of the disperse dye composition. Alternatively, each component may be first subjected to a sand mill in the presence of an auxiliary agent, water or other wetting agent The pulverization device such as a grinder or the like performs micronization, and then mixes according to a preset ratio to obtain the dispersed black dye mixture.

The invention also provides the application of the above-mentioned brilliant blue azo dye in polyester fiber dyeing or printing.

The invention also provides the application of the above-mentioned disperse dye composition in polyester fiber dyeing or printing.

The invention also provides a polyester fiber material which is dyed or printed by using the above-mentioned brilliant blue azo dye.

The invention also provides a polyester fiber material for dyeing or printing by using the disperse dye.

Compared with the prior art, the beneficial effects of the present invention are:

When dyeing according to the present invention, the washing fastness, the rubbing fastness, the sweat fastness, the sun fastness and the coloring rate are all excellent. The disperse dye composition of the present invention has high dyeing strength, bright color, and dyeing performance. Good, especially with excellent washing fastness, stable color, not easy to fade, and low cost.

Example 1

A brilliant blue azo dye of this embodiment has a structural formula as follows:

Where R ₁ represents H;

R ₂ represents methyl;

R ₃ represents ethyl.

The method for preparing the brilliant blue azo dye is as follows:

1) Add a certain amount of sulfuric acid and nitrosylsulfuric acid to the diazo kettle, control the temperature between 20 and 25 degrees, slowly add 6-bromo-2,4-dinitroaniline, and complete the heat preservation after 20 to 25 degrees After 4 hours of reaction, the end point was tested with ice water, and it was reserved after passing.

2) Add water, sulfuric acid and sulfamic acid to the coupling bucket, and then slowly add the coupling component (3-N, N-dipropanyloxymethyl-ethylanilide) to dissolve, and completely cool with ice to about 0 ° C. Slowly add the prepared diazonium salt to the coupling reaction. After the diazonium salt is added, continue stirring until the diazonium salt disappears as the end point. Heat the steam to 55 ~ 60 degrees for 1 hour with heat preservation and crystallize. Filter and wash at 50 degrees with hot water. Filter cake to neutral, unloading and drying to obtain the following structural formula: ,

Wherein R ₁ represents H; R ₂ represents methyl; R ₃ represents ethyl.

3) Add dimethylacetamide to the cyanide kettle, add the above structural formula to 90-95 degrees to dissolve, lower the temperature to about 80 degrees, add zinc and copper salts, keep the temperature at 85-90 degrees and react for 1 hour, take a sample After the test, the temperature is reduced to 20-40 degrees after passing the test. Water is added slowly and the crude product is filtered.

4) Add water to the detoxification kettle, add the crude product, beat until homogeneous, add acidic ferric chloride solution, heat to 60-65 degrees for 2 hours, and filter to wash to obtain the above-mentioned brilliant blue azo dye.

Example 2

A brilliant blue azo dye of this embodiment has a structural formula as follows:

Wherein R ₁ represents CH ₃ O;

R ₂ represents ethyl;

R ₃ represents a methyl group.

The method for preparing the brilliant blue azo dye refers to Example 1, and the difference lies in that the coupling components are different.

Example 3

A brilliant blue azo dye of this embodiment has a structural formula as follows:

Wherein R ₁ represents C ₂ H ₅ O;

R ₂ represents butyl;

R ₃ represents ethyl.

The method for preparing the brilliant blue azo dye refers to Example 1, and the difference lies in that the coupling components are different.

Example 4

A brilliant blue azo dye of this embodiment has a structural formula as follows:

Wherein R ₁ represents CH ₃ O;

R ₂ represents ethyl;

R ₃ represents propyl.

The method for preparing the brilliant blue azo dye refers to Example 1, and the difference lies in that the coupling components are different.

Example 5

A brilliant blue azo dye of this embodiment has a structural formula as follows:

Wherein R ₁ represents C ₂ H ₅ O;

R ₂ represents methyl;

R ₃ represents butyl.

The method for preparing the brilliant blue azo dye refers to Example 1, and the difference lies in that the coupling components are different.

Detection example 1

Take 1.0g of each of the dispersed black dye mixtures prepared in Examples 1 to 5 and disperse them in 500mL of water to obtain a dispersion. Then, draw 20mL of the dispersion and mix with 60mL of water to obtain a dye solution. Adjust the pH of the dye bath to 5 with acetic acid. When it reaches 70 ° C, 4g of polyester fiber is put in for dyeing, and the temperature of the dyeing bath is raised from 70 ° C to 130 ° C within 30 minutes, and the temperature is kept at 130 ° C for 30 minutes, and then cooled to 90 ° C, and samples are taken. Observe the color of the sample cloth, and use the international standards GB / T3921-1997, GB / T3920-1997, GB / T3922-1997, GB / T8427-1998 to test the fastness to washing, fastness to rubbing, and fastness to perspiration. Degree and fastness to sunlight, GB / T9337-2009 method is used to determine the dyeing rate. The test results are shown in Table 1. Table 1

It can be seen from Table 1 that the various fastness properties of the dye compositions prepared in Examples 1 to 5 are relatively good. Among them, when R ₁ represents CH ₃ O, R ₂ represents ethyl, and R ₃ represents methyl, the prepared The bright blue azo dyes have the best dyeing fastness, washing fastness and coloring rate.

Example 6

This embodiment is a disperse dye. The brilliant blue azo dye shown in Example 1, the brilliant blue azo dye shown in Example 2, and the brilliant blue azo dye shown in Example 3 are used according to a mass ratio of 1. : 2: 2 ratio.

Example 7

A disperse dye in this embodiment is obtained by mixing the brilliant blue azo dye shown in Example 2 and the brilliant blue azo dye shown in Example 3 in a mass ratio of 2: 3.

Example 8

A disperse dye in this embodiment is obtained by mixing the brilliant blue azo dye shown in Example 3 and the brilliant blue azo dye shown in Example 4 in a mass ratio of 3: 1.

Example 9

A disperse dye in this embodiment is obtained by mixing the brilliant blue azo dye shown in Example 1 and the brilliant blue azo dye shown in Example 5 at a mass ratio of 1: 3.

Example 10

A disperse dye in this embodiment includes the brilliant blue azo dye shown in Example 1, the brilliant blue azo dye shown in Example 2, the brilliant blue azo dye shown in Example 3, and The brilliant blue azo dye shown and the brilliant blue azo dye shown in Example 5 are mixed at a ratio of 1: 2: 4: 3: 1 by mass.

Detection example 2

Take 1.0g of the disperse dyes prepared in Examples 6 to 10, use the same method as in Test Example 1 to dye the polyester fiber cloth with the disperse dye composition, and test the wash fastness and rub fastness of the sample cloth. Degree, fastness to perspiration, fastness to sunlight, and coloring rate. The test results are shown in Table 2. Table 2

It can be seen from Table 2 that the fastness properties of the disperse dyes prepared in Examples 6 to 10 are relatively good; among them, the dye composition prepared in Example 6 has the best dyeing fastness, washing fastness, and coloring rate.

Claims (10)

A brilliant blue azo dye, wherein the structural formula is shown by formula (I) (I); wherein R ₁ represents H, CH ₃ O or C ₂ H ₅ O; R ₂ represents C ₁ to C ₄ alkyl; R ₃ represents C ₁ to C ₄ alkyl. The brilliant blue azo dye according to claim 1, wherein R ₁ represents CH ₃ O. The brilliant blue azo dye according to claim 1, wherein R ₂ represents an ethyl group. The brilliant blue azo dye according to claim 1, wherein R ₃ represents a methyl group. A method for preparing a brilliant blue azo dye according to claim 1, comprising the following steps: 1) 6-bromo-2,4-dinitroaniline is diazotized with nitrosylsulfuric acid, and then combined with a coupling group The coupling reaction is performed separately, filtered, washed, and dried to obtain the structural formula shown in formula (1): (1), wherein R ₁ represents H, CH ₃ O, or C ₂ H ₅ O; R ₂ represents C ₁ to C ₄ alkyl; R ₃ represents C ₁ to C ₄ alkyl; and the coupling component is (2 The structural formula shown in the following formula: (2), wherein R ₁ represents H, CH ₃ O, or C ₂ H ₅ O, R ₂ represents C ₁ to C ₄ alkyl, and R ₃ represents C ₁ to C ₄ alkyl; 2) Formula (1) in The dimethylacetamide is subjected to a cyanidation reaction with a zinc salt and a copper salt, and the crude product is filtered; 3) The crude product is detoxified with acidic ferric chloride in water, and washed with water to obtain a brilliant blue azo dye. A disperse dye containing the brilliant blue azo dye according to any one of claims 1 to 4, wherein the brilliant blue azo dye is selected from at least one compound of the general formula (I). An application of the brilliant blue azo dye according to any one of claims 1 to 4 in the dyeing or printing of polyester fibers. An application of the disperse dye composition according to claim 6 in the dyeing or printing of polyester fibers. A polyester fiber material that is dyed or printed using the brilliant blue azo dyes according to any one of claims 1 to 4. A polyester fiber material for dyeing or printing using a disperse dye as described in claim 6.