CN104292885B - A kind of Disperse green dye composition, dye preparations and application thereof - Google Patents

Abstract

A disperse green dye composition, dye product and application thereof, the disperse green dye composition is composed of a blue component A and a yellow component B, and the blue component A is selected from formula (I) One or more of the dyes, the yellow component B is selected from one or more of the dyes shown in formula (II), based on the blue component A and yellow component B, blue The mass percentage of the color component A is 50-90%, and the mass percentage of the yellow component B is 10-50%. The dye product mainly contains the disperse green dye composition and auxiliary agents, which are applied to the dyeing of hydrophobic fiber materials, especially polyester/ammonia blended fabrics, with good dyeing effect and excellent color fastness, and can be used very well Improve the quality of fabrics.

Description

A kind of disperse green dye composition, dye product and application thereof

(1) Technical field

The present invention relates to a kind of dyestuff composition, dyestuff product and application thereof, especially relate to a kind of disperse green dyestuff composition, the dyestuff product made from this composition and this dyestuff product on hydrophobic fiber material especially polyester/ammonia blended Application in fabric dyeing.

(2) Background technology

In recent years, fabrics containing spandex elastic fibers are very popular in the world. Because these products are soft to the touch, comfortable to wear, and can show the beauty of the human body, they are used more and more. Spandex is very elastic. General products do not use 100% polyurethane. They are often made of composite yarn, that is, spandex is used as the core, and other fibers are used as the cortex to make core-spun elastic fabrics. Polyester/spandex blended fabrics are common. Due to the special structure of spandex, its performance is quite different from that of polyester fiber. Disperse dyes are easy to dye spandex, but they are also prone to desorption during washing, which reduces the fastness of this type of product, especially the color fastness to washing. Spend. In addition, the common disperse green dyes currently on the market are mainly disperse green 9, or a blend of disperse red 3B, disperse blue 2BLN and disperse yellow. However, the fastness of such conventional dyes on polyester is acceptable. Fastnesses on blended fabrics are not satisfactory and cannot meet today's demand for high-end dyes.

(3) Contents of the invention

The purpose of the present invention is to solve the problem of poor color fastness of existing conventional disperse green dyes, to provide a high-fastness disperse green dye composition, a dye product made from the composition and the dye product on hydrophobic fiber materials Especially in the dyeing of polyester/ammonia blended fabrics, when the dye products made of the high-fastness disperse green dye composition are applied to the dyeing of polyester/ammonia blended fabrics, the dyeing effect is good, the color fastness is excellent, and it can be used very well. Improve the quality of fabrics.

The technical solution adopted by the present invention to solve its technical problems is:

A disperse green dye composition, consisting of blue component A and yellow component B, said blue component A being selected from one or more of the dyes shown in formula (I), said yellow Component B is selected from one or more of the dyes shown in formula (II), based on the blue component A and yellow component B, the mass percentage of blue component A is 50-90 %, the mass percentage of yellow component B is 10-50%;

In the above formula (I), R ₁ is NO ₂ or CN; R ₂ is H or C ₁ -C ₄ alkoxy; R ₃ is C ₁ -C ₄ alkyl; R ₄ is C ₁ -C ₄ Alkyl or benzyl, preferably methyl, ethyl or benzyl;

In the above formula (II), R ₅ is C ₁ -C ₄ alkyl or -CH ₂ NHCOCH ₃ , preferably methyl or ethyl; R ₆ is H, R ₇ is -OSO ₂ -Ph or -OSO ₂ -N(CH ₃ ) ₂ ; or R ₆ is C ₁ to C ₄ alkyl or C ₁ to C ₄ alkoxy, R ₇ is NO ₂ ;

Ph represents phenyl.

As a further preference, the disperse green dye composition of the present invention consists of 60-80% blue component A and 20-40% yellow component B in mass fraction.

The blue component A is preferably one or more of the following formulas (I-1) to (I-10):

The component B is preferably selected from one or more of the following formulas (II-1) to (II-10):

Disperse green dye composition of the present invention, more preferably forms as follows:

Component A is selected from at least one of formulas (I-1) to (I-2);

Component B is selected from at least one of formulas (II-1) to (II-2);

Based on the above component A and component B, the mass percentage of component A is 50-90%, and the mass percentage of component B is 10-50%.

When the disperse green dye composition of the present invention is sold as a commodity or applied to the coloring of textile materials, it is usually necessary to add auxiliary agents for post-treatment. Therefore, the present invention also provides a disperse green dye product, which mainly contains the disperse green dye composition and an auxiliary agent, and the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-5:1. Described auxiliary agent is commonly used dispersant, diffusion agent and other surfactants etc. when compounding disperse dyes, preferred auxiliary agent includes one of the following or its mixture: naphthalenesulfonic acid formaldehyde condensate, lignosulfonate, Alkylnaphthalenesulfonic acid formaldehyde condensate (such as methylnaphthalenesulfonic acid formaldehyde condensate (dispersant MF)), naphthalenesulfonic acid formaldehyde condensate (diffusion agent NNO), benzylnaphthalenesulfonic acid formaldehyde condensate (diffusion agent CNF) , Sodium lignosulfonate (Lignin 85A, Lignin 83A), etc.

The present invention specifically recommends that the disperse green dye product is composed of a disperse green dye composition and an auxiliary agent in a weight ratio of 1:0.2 to 5, wherein the disperse green dye composition is composed of blue component A and yellow component B, blue The color component A is selected from one or more of the formulas (I-1) to (I-10); the yellow component B is selected from one or more of the formulas (II-1) to (II-10). species; based on the blue component A and the yellow component B, the mass percentage of the blue component A is 50-90%, and the mass percentage of the yellow component B is 10-50%.

The preparation method of disperse green dye product of the present invention is as follows:

After mixing the dye monomer compounds represented by the blue component A and the yellow component B according to the above-mentioned ratio, in the presence of additives, water or other wetting agents, use a pulverizer such as a sand mill or a grinder. Micronization; In addition, the dye monomer compounds represented by component A and component B can also be micronized with a pulverizer such as a sand mill or a grinder in the presence of auxiliary agents, water or other wetting agents. Mix in the ratios above. The disperse green dye composition of the present invention can be liquid after grinding with a sand mill or grinder, and can be powder or granular after spray drying. This is a preparation method well known to those skilled in the art.

The former dye shown in the formula (I) of the present invention can be prepared by the usual diazotization and coupling reaction methods in the industry, typically as:

(1) Diazotize the compound of formula (Ⅲ) with nitrosyl sulfuric acid or sodium nitrite under acidic conditions, and control the temperature at 0-5°C; (2) add water, concentrated sulfuric acid and formula (IV) Stir and beat the compound; (3) Add the diazonium salt into the coupling reaction pot, control the temperature at 0-5°C, stir to the end of the reaction, filter, and wash until neutral to obtain the disperse dye monomer compound. The compounds of formula (Ⅲ) and formula (Ⅳ) can be prepared by conventional methods in the industry, or commercially available products;

In the above formula (III) and formula (IV), the definitions of R ₁ , R ₂ , R ₃ and R ₄ are the same as those in (I).

For those of ordinary skill in the art in the industry, the compounds of formula (III) and formula (IV) are known, or are easily prepared from known compounds by known methods, and can also be prepared according to the methods introduced in patents CN1208057A and US5550217A preparation.

The primary dye represented by formula (II) of the present invention can be prepared according to the methods introduced in patents JP61019664, JP11158402, DE2708418, or commercially available products.

The invention also provides the application of the disperse green dye product in the dyeing of hydrophobic fiber materials, especially in the dyeing of polyester/spandex blended fabrics.

The disperse green dye product made from the disperse green dye composition of the present invention is used for dyeing hydrophobic fiber materials, especially polyester/spandex blended fabrics, has good lifting power and good dye uptake, and can be dyed on polyester/spandex fabrics The washing fastness, rubbing fastness, sublimation fastness and other fastness are excellent, especially the washing fastness is outstanding.

(4) Specific implementation methods

The present invention will be further described below in conjunction with specific examples, but the protection scope of the present invention is not limited thereto.

The preparation of embodiment 1 formula (I-1) dyestuff

Put 36g of reducing substance (2-amino-4-acetamidoanisole), 300g of ethanol, 181g of ethyl bromopropionate into a 500ml container, heat up and reflux for 10h, cool down, add 200g of water at the same time, keep stirring at 0～5℃ After 12h, the crystallization was filtered to obtain the intermediate product a ₁ .

Put 101.3g of benzyl chloride, 11.6g of soda ash, product a ₁ (28g), and 100g of DMF into a 250ml container, raise the temperature to 80°C, put in 5g of KI, and keep warm for 12h. Cool down to 40°C, add 100 g of water, crystallize and filter to obtain a crude product. Put it back into a 250ml beaker, add 100g of methanol, keep stirring at 10°C for 15h, crystallize and filter to obtain the raw material compound represented by formula (III-1), that is, the coupling component.

Diazotization: Add 80g of concentrated sulfuric acid to a 250ml container, add 35g of 40% nitrosyl sulfuric acid, cool down to 0-5°C, control 3-4h to add 0.1mol 2,4-dinitro-6-bromoaniline, add After incubation for 3 hours, the diazo component was obtained.

Coupling: Put 1000g of water, 60g of concentrated sulfuric acid, and 0.1mol of coupling component (Ⅲ-1) into a 2L container, and beat for half an hour. Add the above-mentioned diazo component dropwise into the beating liquid of the coupling component within 20 minutes. Control the temperature at 0-5°C and fully react for 5-6 hours. After the end point is reached, the temperature of the material is raised to 75°C, kept for 3 hours, filtered with suction, washed until neutral, and dried to obtain the dye intermediate b ₁ .

Cyanidation: Add DMF100g to a 250ml container, add 10g cuprous cyanide, heat up to 100°C, put in dye intermediate b ₁ (63.3g), keep it warm for 4h, cool down to 30°C, filter with suction to get crude dye, Throw the dye back into a 250ml flask, add 100g of water and 100g of ammonia water, stir at 20-30°C for 15 hours, and filter with suction to obtain the finished dye (I-1).

Example 2

According to the preparation method described in Example 1, component A of formulas (I-2) to (I-10) can be prepared by changing the corresponding conventional raw material components.

Embodiment 3-20

According to the measurement data shown in the following table 1, the original dyes and auxiliary agents of the disperse dyes shown in the formulas (I) and (II) are fully mixed with water, ground and dispersed with a sand mill, and then dried to obtain disperse green dye products .

Table 1 Unit: (gram)

Comparative example 1～7

Examples 3, 5, and 7 disclosed in CN103540168A are respectively used as comparative examples 1-3;

The embodiment 5 disclosed in CN103468024A is used as comparative example 4;

The embodiment 5 disclosed in CN102964873A is used as comparative example 5;

Examples 2 and 18 disclosed in CN101974255A are respectively used as comparative examples 6-7.

Dyeing Example 21:

The dyes of Examples 1-20 and Comparative Examples 1-7 were subjected to high-temperature and high-pressure dyeing at dyeing concentrations of 1.5% (C), 3% (2C), and 6% (4C) respectively according to the method in GB/T2397, and evaluated Its lifting performance, the results are shown in Table 2 below.

Dyeing Example 22:

Take by weighing 2 grams of the disperse dyes prepared in Examples 1-4 and disperse them in 500 milliliters of water, mix them with 60 milliliters of water after drawing 20 milliliters, adjust the pH to 4.5 with acetic acid, put 2 grams of polyester/ammonia fabrics, and heat up to 60 °C, continue to increase the temperature to 130 °C with a gradient of about 1 °C/min, and keep it for 45 minutes for dyeing. Then cool down to about 80°C, wash with hot water for 10 minutes, and dry. It can provide uniform green color to the fabric with good fastness properties.

The national standard GB/T3921, GB/T3920-, GB/T5718 were used to measure its washing fastness, rubbing fastness and sublimation color fastness respectively. The test results are shown in the following table 2:

Table 2 Units: Grade

The test results show that: when the commercial dyes made from the disperse green dye composition provided by the present invention are applied to the dyeing of polyester/spandex blended fabrics, compared with the dyed polyester/spandex blended fabrics of comparative examples, the improvement in performance and color fastness Significantly improved.

Claims (11)

1. a Disperse green dye composition, it is characterized in that: described Disperse green dye composition is made up of blue color component A and yellow color component B, described blue color component A is selected from one or more in the dyestuff shown in formula I, described yellow color component B is selected from one or more in the dyestuff shown in formula II, based on described blue color component A and yellow color component B, the weight/mass percentage composition of blue color component A is the weight/mass percentage composition of 50-90%, yellow color component B is 10-50%；

In above-mentioned formula I, R₁For NO₂Or CN；R₂For H or C₁～C₄Alkoxyl；R₃For C₁～C₄Alkyl；R₄For C₁～C₄Alkyl or benzyl；

In above-mentioned formula II, R₅For C₁～C₄Alkyl or-CH₂NHCOCH₃；R₆For H, R₇For-OSO₂-Ph or-OSO₂-N(CH₃)₂；Or R₆For C₁～C₄Alkyl or C₁～C₄Alkoxyl, R₇For NO₂；

Ph represents phenyl.

2. Disperse green dye composition as claimed in claim 1, it is characterised in that: R₄For methyl, ethyl or benzyl；R₅For methyl or ethyl.

3. Disperse green dye composition as claimed in claim 1, it is characterised in that: described blue color component A is selected from one or more in following formula (I-1)～(I-10):

4. Disperse green dye composition as claimed in claim 1, it is characterised in that: described component B is selected from one or more in following formula (II-1)～(II-10):

5. Disperse green dye composition as claimed in claim 3, it is characterised in that: described component B is selected from one or more in following formula (II-1)～(II-10):

6. the Disperse green dye composition as described in one of Claims 1 to 5, it is characterised in that: described Disperse green dye composition is made up of the blue color component A that weight/mass percentage composition is 60-80% and the yellow color component B that weight/mass percentage composition is 20-40%.

7. Disperse green dye goods, the weight ratio mainly containing the Disperse green dye composition described in claim 1 and auxiliary agent, auxiliary agent and disperse dye composition is 0.2～5:1.

8. Disperse green dye goods as claimed in claim 7, it is characterised in that: described auxiliary agent is selected from following a kind of or arbitrarily several mixture: lignosulfonates, alkyl naphthalene sulfonic acid formaldehyde condensation products, naphthalene sulfonic acid-formaldehyde condensation product, benzyl naphthalene sulfonic formaldehyde condensation compound.

9. Disperse green dye goods as claimed in claim 8, it is characterized in that: described Disperse green dye goods are made up of the Disperse green dye composition that weight ratio is 1:0.2～5 and auxiliary agent, wherein Disperse green dye composition is made up of blue color component A and yellow color component B, and blue color component A is selected from one or more in formula (I-1)～(I-10)；Yellow color component B is selected from one or more in formula (II-1)～(II-10)；Weight/mass percentage composition based on blue color component A and yellow color component B, blue color component A is 50～90%, and the weight/mass percentage composition of yellow color component B is 10～50%；

10. the Disperse green dye goods as claimed in claim 7 application in hydrophobic fiber material dyes.

11. apply as claimed in claim 10, it is characterised in that: described hydrophobic fiber material is for washing/ammonia blend fabric.