WO2016033853A1

WO2016033853A1 - Bright red disperse dye with high alkaline resistance, and use, preparation method and staining method thereof

Info

Publication number: WO2016033853A1
Application number: PCT/CN2014/088567
Authority: WO
Inventors: 王喆; 王淑香
Original assignee: 蓬莱嘉信染料化工股份有限公司
Priority date: 2014-09-03
Filing date: 2014-10-14
Publication date: 2016-03-10
Also published as: CN104262992A; CN104262992B

Abstract

Provided is a bright red disperse dye with high alkaline resistance and the use and preparation method thereof. A bright red disperse dye with high alkaline resistance, the structure thereof is shown in general formula (I), and the bright red disperse dye with high alkaline resistance is one of the general structural formula, wherein R₁ is a hydrogen or a methyl group, R₂ is a C₁-C₄ alkyl or cyanoethyl group and R₃ is a chlorine or a methyl group. The use of the bright red disperse dye with high alkaline resistance is applied to staining of terylene and the blended fabrics thereof. Further provided is a preparation method for the bright red disperse dye, which comprises a diazotization reaction and a coupling reaction; further provided is a staining method for terylene and the blended fabrics thereof and a staining method for cotton-terylene blended fabrics; and the above-mentioned dye has an excellent fastness and dyeing performance, and simplifies the staining process while achieving the energy saving and emission reduction effects.

Description

High alkali-resistant brilliant red disperse dye, application thereof, preparation method and dyeing method

Technical field

The invention relates to the field of chemistry, in particular to a high alkali-resistant brilliant red disperse dye and an application, a preparation method thereof and a dyeing method.

Background technique

The usual disperse dyeing is carried out in a dye bath having a pH of 5-6. Among the known disperse brilliant reds, the basic ones are preferably:

1.C.I. Disperse red 60, its structural formula is:

2. Chinese patent number 2004100212478, its structural formula is:

Among the above dyes, C.I. disperse red 60, which can be dyed in a dye bath having a pH of 4-9. The brilliant red disperse dye shown in the invention patent has a large improvement in alkali resistance and can be dyed in a dye bath of pH=4-11, which satisfies the need for partial alkaline bath dyeing. However, due to advances in textile and printing technology, dyes are required to have higher alkali resistance, which is suitable for higher dyeing process requirements, and achieves pre-dyeing finishing (alkali Reduction, opening, rinsing) and dyeing the same bath one-step method, so as to achieve the purpose of increasing production, energy saving and emission reduction. Therefore, it is especially necessary to explore the development of highly alkali-resistant disperse dyes.

Summary of the invention

It is an object of the present invention to provide a highly alkali-resistant brilliant red disperse dye, an application thereof, a preparation method and a dyeing method to solve the above problems.

The present application provides a highly alkali-resistant brilliant red disperse dye having the following structural formula:

The brilliant red disperse dye is one of the structural formulas; wherein: R ₁ is hydrogen or methyl, R ₂ is a C ₁ -C ₄ alkyl or cyanoethyl group, and R ₃ is chlorine or methyl .

Preferably, the brilliant red disperse dye is a mixture of two or more compounds in the structural formula.

The application also provides an application of the brilliant red disperse dye for the dyeing of polyester and its blended fabric.

Preferably, the brilliant red disperse dye is applied to a process of dyeing polyester and its blended fabric by a fabric pre-finishing and dyeing one-step method using an overbased bath.

Preferably, the brilliant red disperse dye is applied to a process for dyeing a polyester-cotton blend fabric by a medium temperature hot melt thermosetting one-step method.

The present application also provides a method for preparing the brilliant red disperse dye, wherein the method is: diazotization reaction, an appropriate amount of water and sulfuric acid mixed solution, and dropping 6,7 in an ice salt bath condition ( 5)-Dichloro-2-aminobenzothiazole, the reaction to obtain a diazonium salt solution; coupling reaction in water and sulfur Adding one of the coupling materials of the following formula to the acid mixture, and then adding the sulfamic acid to control the reaction temperature below 0 degrees Celsius, adding the diazonium salt solution to obtain the corresponding disperse dye;

The present application also provides a method for dyeing polyester and its blended fabric, using the brilliant red disperse dye, which comprises pre-finishing and dyeing the fabric in a step using a high alkaline bath, comprising the steps of: using the The dye is formulated into a bath, and the fabric is dyed and washed to obtain a dyed fabric.

The present application also provides a method for dyeing a polyester-cotton blend fabric, using the brilliant red disperse dye, the method adopts a medium temperature hot melt thermosetting one-step method, comprising the following steps: using the dye to prepare a pad dyeing solution, The fabric is padded in the pad dyeing liquor, dried, then hot melted and solidified, and washed to obtain a dyed fabric.

The use of a high alkali-resistant brilliant red disperse dye provided by the present application, an application thereof, a preparation method and a dyeing method can bring about at least one of the following beneficial effects: First, the disperse dye provided by the present application has high alkali resistance. Performance, while having excellent color fastness and dyeing properties, provides users with an excellent dye with more choices to improve the use of such dyes. Second, the disperse dye not only has the usual disperse dyes. It can be dyed in a weak acid bath, and can be dyed in a neutral to strong alkaline bath. It has remarkable advantages, and the new dyeing process can achieve energy saving and emission reduction. Third, the application provides the dye. A certain application, applied to the dyeing of polyester and its blended fabrics, especially for the dyeing of highly alkaline baths, fabric finishing (opening, Alkali reduction or scouring) and dyeing synchronous one-bath process; fourth, the present application also provides a new method for preparing the brilliant red disperse dye; fifth, the present application also provides the use of the brilliant red Dyeing method of disperse dyes, good dyeing effect, energy saving and emission reduction.

detailed description

The present invention will be further described in detail below by way of specific examples. It is understood that the specific embodiments described herein are merely illustrative of the application and are not intended to be limiting.

The present application also provides a method for preparing the brilliant red disperse dye, wherein the method is: diazotization reaction, an appropriate amount of water and sulfuric acid mixed solution, and dropping 6,7 in an ice salt bath condition. (5)-Dichloro-2-aminobenzothiazole, reacting to obtain a diazonium salt solution; coupling reaction, adding one of the coupling materials represented by the following formula to a mixture of water and sulfuric acid, and then adding sulfamic acid Controlling the reaction temperature below 0 degrees Celsius, adding the diazonium salt solution, and reacting to obtain the corresponding disperse dye;

Example 1

The dye structure is:

Diazotization

To a stirred 250 ml three-necked flask, 80 ml of water was added, and 140 g of 93% sulfuric acid was added dropwise with stirring. 26.6 g of 40% nitrosylsulfate was added dropwise to an ice-cold bath to -2 ° C, and then 6,7(5)-dichloro-2-aminobenzothiazole was slowly added at this temperature. The reaction was kept for 3 hours until it was coupled.

b. coupling

Add 200 ml of water, 6 g of 93% sulfuric acid and 21 g of N-ethyl-N-(m-benzyl) m-toluidine to a stirred 1000 ml beaker, stir and dissolve, then add 1 g of sulfamic acid. Add crushed ice to below 0 ° C, then add the diazonium compound prepared above, react until the diazo component disappears, stir for 2 hours, filter, wash with water until neutral. The average yield of the original dye was 39.4 g. The maximum absorption wavelength of the dye is λmax = 530 nm.

Example 2

The dye structure is:

a. Diazotization is the same as in Example 1.

b. Coupling:

Add 200 ml of water, 6 g of 93% sulfuric acid and 19.8 g of N-ethyl-N-p-methylbenzylaniline to a stirred 1000 ml beaker, stir and dissolve, then add 1 g of sulfamic acid, add crushed ice. Drop to below 0 ° C, followed by the addition of the above diazo compound. The reaction was allowed to disappear until the diazo component disappeared, and the mixture was further stirred for 2 hours, washed with water until neutral, and dried. The average yield of the original dye was 38.5 g, and λmax = 525 nm.

Example 3

The dye structure is:

a. Diazotization is the same as in Example 1.

b. Coupling:

Add 200 ml of water to a stirred 1000 ml beaker, add 10 g of 10% flat, and slowly add acetic acid (60) containing 22.2 g of N-methyl-N-(p-chlorobenzyl) m-toluidine.毫升) solution, after stirring for 0.5 hours, add 1 gram of sulfamic acid and appropriate amount of crushed ice to cool to below 0 ° C, then add the above diazonium compound to react until the diazo component disappears, stir for 2 hours, filter to wash until neutral dry . The average yield of the original dye was 38 grams. Λmax = 523 nm.

Example 4

Dye structure:

a. Diazotization is the same as in Example 1.

b. Coupling:

Add 200 ml of water, 10 g of 93% sulfuric acid and 21 g of N-butyl-N-benzylaniline to a stirred 1000 ml beaker, stir and dissolve, add 1 g of sulfamic acid and ice to a suitable amount to cool down to Below 0 ° C, the above diazonium compound was added to react until the diazo component disappeared, and the mixture was further stirred for 2 hours, and filtered to wash with water until neutral. The average yield of the original dye was 37.8 g. Λmax = 520 nm.

Example 5-10

The method of diazotization is the same as that of the first embodiment. The even law is basically the same as the examples 1-4, and the dye structure is shown in the following table 1:

Table 1 Different groups corresponding to Examples 5-10

实施例Example	R₁ R ₁	R₂ R ₂	R₃ R ₃	λmaxΛmax
实施例Example	R₁ R ₁	R₂ R ₂	R₃ R ₃	λmaxΛmax	55	HH	CH₃ CH ₃	P-CH₃ P-CH ₃	521521
66	CH₃ CH ₃	C₄H₉ C ₄ H ₉	M-CH₃ M-CH ₃	533533	55	HH	CH₃ CH ₃	P-CH₃ P-CH ₃	521521
66	CH₃ CH ₃	C₄H₉ C ₄ H ₉	M-CH₃ M-CH ₃	533533	77	CH₃ CH ₃	C₂H₅ C ₂ H ₅	P-CH₃ P-CH ₃	535535
88	CH₃ CH ₃	C₄H₉ C ₄ H ₉	P-CLP-CL	530530	77	CH₃ CH ₃	C₂H₅ C ₂ H ₅	P-CH₃ P-CH ₃	535535
88	CH₃ CH ₃	C₄H₉ C ₄ H ₉	P-CLP-CL	530530	99	CH₃ CH ₃	C₄H₉ C ₄ H ₉	P-CH₃ P-CH ₃	539539
1010	CH₃ CH ₃	C₄H₉ C ₄ H ₉	HH	534534	99	CH₃ CH ₃	C₄H₉ C ₄ H ₉	P-CH₃ P-CH ₃	539539

Note: In the table, P represents the alignment and M represents the meta.

Example 11

The dye structure is:

a. Diazotization is the same as in Example 1.

b. Coupling:

Add 200 ml of water, 6 g of 93% sulfuric acid, and 10.5 g of N-ethyl-N-p-methylbenzyl m-toluidine and 9.9 g of N-ethyl-N-pair to a stirred 1000 ml beaker. After stirring and dissolving benzyl aniline, add 1 g of sulfamic acid, then add appropriate amount of crushed ice to cool to below 0 ° C, then add the above diazonium compound to react until the diazo component disappears, stir for 2 hours, filter to wash to neutral, suck The dried filter cake contained 37.4 g of the original dye.

Example 12

10 g of the dye of Example 1 (or mixed dyeing of different examples) was added to 55 ml of water, 6 g of sodium lignosulfonate and 14 g of a diffusing agent MF, and sanded to a degree of diffusion of 4-5 to be quickly dried to obtain a dispersion. Red 200% commercial dye.

Example 13

Take 1.6 g of the dye of Example 7, disperse 5.4 g of the original blue HA-B dye, and disperse 3.0 g of the original HA-2RW dye; add 55 ml of water, 3 g of sodium lignosulfonate and 7 g of dispersant MF, sand to The degree of diffusion was quickly dried in 4-5 grades to prepare a dispersion black 300% HA-B commercial dye (produced).

Note: Disperse Blue HA-B and Disperse Yellow HA-2RW are high alkali-resistant disperse dye products produced by the applicant.

Example 14

Hot melt thermosetting one-step dyeing polyester/cotton blend fabric

The composition of the pad dyeing liquor is shown in Table 2 below:

Table 2 Composition of pad dyeing solution

项目project	加量Add amount
项目project	加量Add amount	分散艳红(实施例)Disperse brilliant red (example)	2.6克2.6 grams
活性艳红K-2BDReactive Brilliant Red K-2BD	1.4克1.4 grams	分散艳红(实施例)Disperse brilliant red (example)	2.6克2.6 grams
活性艳红K-2BDReactive Brilliant Red K-2BD	1.4克1.4 grams	尿素Urea	10克10 grams

碳酸氢钠Sodium bicarbonate	1.6克1.6 g
碳酸氢钠Sodium bicarbonate	1.6克1.6 g	合成胶糊(6％)Synthetic paste (6%)	2.0克2.0 grams
渗透剂JFC(10％)Penetrant JFC (10%)	3.0克3.0 grams	合成胶糊(6％)Synthetic paste (6%)	2.0克2.0 grams
渗透剂JFC(10％)Penetrant JFC (10%)	3.0克3.0 grams	加水至Add water to	200毫升200 ml

65/35 polyester cotton plain cloth in the above-mentioned pad dyeing liquor, dip two rolls at room temperature, dry at 100-105 ° C, then heat-melt at 190 ° C for 60 seconds, then soap, wash and dry The red fabric has a sublimation fastness better than Disperse Red 60 (dye 1).

Example 15

One-step process for fabric finishing and dyeing (alkali reduction dyeing one bath method)

Conventional disperse dyes are not alkali resistant, and alkali reduction finishing and dyeing are carried out in two steps in two baths. The dye of the present invention has a high basicity, an alkali reduction treatment and a dyeing one-step one-step method. For example: the dyeing process of pure polyester not falling pile:

After adding 200 ml of water, 1.2 g of caustic soda and 0.4 g of leveling agent and 0.1 g of commercial dye to the dyeing tank, 5 g of a predetermined type of non-woven fabric was added. After heating to 80 ° C, the temperature was raised to 130 ° C for 1 minute at a rate of 1 ° /min, and the temperature was lowered and washed to obtain a brilliant red fabric, and the effect of not falling down and fabric softening was achieved.

Example 16

Alkaline dyeing of dyes

The dyed fabric is a pure polyester knitted fabric with a dyeing depth of 2%. The dyes of the comparative examples and the examples are dyed at 130 ° C in different concentrations of alkaline (represented by pH and caustic g/liter respectively) in a bath. Dyeing, washing, drying, computer colorimetry. The results are shown in Table 3 below.

Table 3: Color depth and color change of fabric under different alkalinity

Note: Under high alkalinity, the fabric weight is reduced, and the dyeing concentration is deepened. The dye of the invention has stable color and the dyeing intensity is basically unchanged.

The use of the high alkali-resistant brilliant red disperse dye provided by the application is suitable for the alkaline bath dyeing with many advantages, and can realize the pre-finishing of the fabric (alkali reduction, fiber opening, scouring) and dyeing synchronization Bath technology to achieve the purpose of increasing production, energy saving and emission reduction. At the same time, the dye is also suitable for medium-temperature hot-melt heat-solid one-step dyeing of disperse dyes of polyester-cotton blended fabrics and reactive dyes to achieve energy-saving and energy-saving effects.

The above description is only the preferred embodiment of the present invention, and is not intended to limit the present invention, and various modifications and changes can be made to the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and scope of the present invention are intended to be included within the scope of the present invention.

Claims

A highly alkali-resistant brilliant red disperse dye having the following structural formula:

Characterized in that the disperse dye is one of the structural formulas; wherein: R 1 is hydrogen or methyl, R 2 is a C 1 -C 4 alkyl or cyanoethyl group, and R 3 is chlorine or methyl.
The brilliant red disperse dye according to claim 1, wherein the disperse dye is a mixture of two or more compounds in the structural formula.
Use of a brilliant red disperse dye according to claim 1 or 2 for dyeing polyester and its blended fabric.
The application according to claim 3, which is applied to a dyeing process of a high-alkaline bath, fabric pre-finishing and dyeing one-step dyeing of polyester and its blended fabric.
The application according to claim 3 is applied to a medium temperature hot melt thermosetting one-step dyeing polyester-cotton blend fabric.
A method for preparing a brilliant red disperse dye according to claim 1 or 2, wherein the method is: diazotization reaction, an appropriate amount of water and sulfuric acid mixed solution, and dropping 6 under an ice salt bath condition, 7(5)-dichloro-2-aminobenzothiazole, reacting to obtain a diazonium salt solution; coupling reaction, adding one of the coupling materials represented by the following formula to a mixture of water and sulfuric acid, and then adding aminosulfonate Acid, control the reaction temperature below 0 degrees Celsius, adding the diazonium salt solution, the reaction to obtain the corresponding disperse dye;
A method for dyeing polyester and its blended fabric, using the brilliant red disperse dye according to claim 1 or 2, wherein the method comprises pre-finishing and dyeing the fabric in a step by using an overbased bath, comprising the steps of: The bath was prepared using the dye, and the fabric was dyed and washed to obtain a dyed fabric.
A dyeing method for a polyester-cotton blend fabric using the brilliant red disperse dye according to claim 1 or 2, wherein the method adopts a medium temperature hot melt thermosetting one-step method, comprising the steps of: preparing a pad dyeing process using the dye The liquid is padded in the pad dyeing solution, dried, then hot-melted and solidified, and washed to obtain a dyed fabric.