CN116004032A - A kind of red dye compound and its synthesis method and application - Google Patents

Abstract

The application relates to the field of textile printing and dyeing, and particularly discloses a red dye compound, and a synthesis method and application thereof. The red dye compound is a compound represented by a general formula (I);

wherein R is ₁ Selected from the group consisting of

Or (b)

M is selected from H or alkali metal cations; x is selected from Br, cl or F. The synthesis process of the red dye compound involves diazotization reaction, condensation reaction I, coupling reaction and condensation reaction II. The red dye compound can be used for dyeing cellulose fibers, wool and blended fabrics containing cellulose fibers or wool, and particularly can be applied to one-bath one-step method dyeing of the blended fabrics containing cellulose fibers or wool, and the dyeing effect and the dyeing fastness are very excellent.

Description

A red dye compound and its synthesis method and application

Technical Field

The present invention relates to the field of textile printing and dyeing, and more specifically, to a red dye compound and a synthesis method and application thereof.

Background Art

Reactive dyes, also known as reactive dyes, contain active groups in their molecules that can react with hydroxyl groups in cellulose and amino groups in protein fibers. When dyeing, they form covalent bonds with fibers to generate "dye-fiber" compounds, which have the characteristics of bright colors, good dyeing uniformity, simple dyeing method, high dyeing fastness, complete color spectrum and low cost.

In recent years, blended fabrics made of two or more fibers have been deeply loved by people because they have the characteristics of different types of fibers at the same time. In the field of textile printing and dyeing, there are two processes for dyeing blended fabrics: two-bath method and one-bath method. The two-bath method is to dye the different components in the blended fabric separately. The process is complicated, the process time is long, and the production efficiency is low. Therefore, in the future, production is more inclined to use the one-bath method to dye the blended fibers. However, the currently commonly used reactive dyes, such as C.I. Reactive Red 195, one of the three primary colors, have poor dyeing effects and dyeing fastness when used in one-bath one-step dyeing, and there is still room for improvement.

Summary of the invention

In order to improve the dyeing effect and dyeing fastness of red reactive dyes when used in one-bath one-step dyeing, the present application provides a red dye compound and a synthesis method and application thereof.

In a first aspect, the present application provides a red dye compound, using the following technical solution:

A red dye compound, wherein the active dye compound is a compound represented by general formula (I);

或Wherein, R ₁ is selected from

or

M is selected from H or an alkali metal cation;

X is selected from Br, Cl or F.

By adopting the above technical scheme, compared with existing reactive dyes, such as C.I. Reactive Red 195, the red dye compound of the present application has better dyeing enhancement and dyeing fastness, and the red dye compound has good compatibility with other dyes. It can not only be used to dye single fiber products alone, but also can be compounded with other reactive dyes for dyeing fabrics. In addition, the red dye compound can also be compounded with disperse dyes known in the art and used in blended fiber coloring, and has a wide range of applicability.

Preferably, in the general formula (I), -SO ₂ CH ₂ CH ₂ OSO ₃ M is at the meta-position or para-position relative to -NH-R.

Preferably, the compound represented by the general formula (I) is a compound of formula (I-1), formula (I-2) or formula (I-3);

In a second aspect, the present application provides a method for synthesizing the red dye compound in the first aspect, using the following technical solution:

A method for synthesizing a red dye compound comprises the following steps:

Diazotization reaction: diazotizing the compound represented by general formula (II) or general formula (III) to obtain a diazonium salt;

Wherein, M is selected from H or an alkali metal cation;

Condensation reaction I: subjecting the compounds represented by general formula (IV) and general formula (V) to a condensation reaction to obtain a condensate;

Wherein, M is selected from H or an alkali metal cation;

X is selected from Br, Cl or F;

Coupling reaction: coupling the diazonium salt obtained by the diazotization reaction with the condensation product obtained by the condensation reaction I to obtain a coupled compound; condensation reaction II: condensing the coupled compound obtained by the coupling reaction with the compound represented by the general formula (VI) to obtain a red dye compound;

Wherein, M is selected from H or an alkali metal cation;

-SO ₂ CH ₂ CH ₂ OSO ₃ M is in the meta or para position of -NH ₂ .

By adopting the above technical scheme, the synthesis process of the present application involves a diazotization reaction, two condensation reactions and a coupling reaction. The reaction conditions are easy to control and implement, and a red dye compound can be stably prepared.

Preferably, in the condensation reaction I, the feed ratio of the compound represented by the general formula (IV) to the compound represented by the general formula (V) is 1 mol:(1.05-1.1) mol.

Preferably, in the condensation reaction I, the reaction temperature is 0-5°C and the reaction time is 3-4h.

Preferably, in the coupling reaction, the reaction temperature is 0-5°C and the reaction time is 2-3h.

Preferably, in the condensation reaction II, the feed ratio of the coupler to the compound represented by the general formula (VI) is 1 mol:(1-1.05) mol.

Preferably, in the condensation reaction II, the reaction temperature is 10-20°C and the reaction time is 4-5h.

In a third aspect, the present application provides the use of the red dye compound in the first aspect, which can be used in dyeing cellulose fibers, dyeing wool, and dyeing blended fabrics containing cellulose fibers or wool.

When used for dyeing cellulose fibers or wool, the red dye compound can be compounded with other reactive dyes known in the art according to actual needs;

When used for dyeing blended fabrics containing cellulose fiber or wool, the red dye compound can be used together with disperse dyes known in the art according to actual needs, and dyeing can be carried out using a two-bath process or a one-bath process, and conventional dyeing auxiliaries in the art can also be added.

In summary, this application has at least the following beneficial effects:

The red dye compound of the present application has bright color, good level dyeing property, excellent dyeing effect and dyeing fastness, and good compatibility with other dyes. It can be applied to cellulose fiber dyeing, wool dyeing, and dyeing of blended fabrics containing cellulose fiber or wool, and can be applied to one-bath dyeing and two-bath dyeing. A large number of dyeing experiments have shown that the red dye compound of the present application has a very broad application prospect.

BRIEF DESCRIPTION OF THE DRAWINGS

Fig. 1 is a dyeing process diagram of tests 1-1 to 1-5 in the performance test of the present application;

FIG. 2 is a dyeing process diagram of experiments 2-1 to 2-5 in the performance test of the present application.

DETAILED DESCRIPTION

The present application is further described in detail below in conjunction with the accompanying drawings and embodiments.

The raw materials used in the examples of the present application are all commercially available.

Examples of Red Dye Compounds

Example 1

A red dye compound, the structure of which is shown in the following formula (I-1):

The preparation method of the red dye compound represented by the above formula (I-1) comprises the following specific steps:

(1) Diazotization reaction:

In a 1000mL three-necked flask, add 303g of a 15% solution of the compound of formula (III-1) (0.1mol), then add 30.8g of a 30% hydrochloric acid solution (0.25mol), and dropwise add 23g of a 30% sodium nitrite solution (0.1mol) while stirring. Control the temperature to 5°C and react for 2h to obtain a diazonium salt.

(2) Condensation reaction I:

In a 500mL three-necked flask, add 100mL of water, add 19.3g of the compound of formula (V-1) (0.105mol) while stirring to make a slurry, and then dropwise add 242g of a 15% mass concentration of the compound of formula (IV-1) (0.1mol) to carry out a condensation reaction, control the temperature to 5°C, react for 3h, and obtain a condensate;

(3) Coupling reaction:

The diazonium salt obtained by the diazotization reaction is coupled with the condensation product obtained by the condensation reaction I, the temperature is controlled at 5°C, the pH is 6.0-6.5, and the reaction is carried out for 2 hours to obtain a coupled product;

(4) Condensation reaction II:

30.3 g of the compound of formula (VI-1) (0.1 mol) was added to the couple (about 0.1 mol), the temperature was controlled at 20°C, pH = 6.0-6.5, and the reaction was carried out for 4 hours to obtain 120.5 g of a red dye compound with a purity of 95.3% and a yield of 96.9%.

The obtained red dye compound was subjected to elemental analysis, and the analysis results are shown in the following table:

Furthermore, infrared spectroscopy analysis revealed that the obtained red dye compound was the compound represented by formula (I-1).

Example 2

A red dye compound, the structure of which is shown in the following formula (I-1):

The preparation method of the red dye compound represented by the above formula (I-1) comprises the following specific steps:

(1) Diazotization reaction: same as in Example 1;

(2) Condensation reaction I:

In a 500mL three-necked flask, add 100mL of water, add 20.1g of the compound of formula (V-1) (0.11mol) while stirring to make a slurry, then dropwise add 242g of a 15% mass concentration of the compound of formula (IV-1) (0.1mol) to carry out a condensation reaction, control the temperature to 5°C, react for 3h, and obtain a condensate;

(3) Coupling reaction: the same as in Example 1;

(4) Condensation reaction II: The same as in Example 1, after the reaction, 122.3 g of red dye compound was obtained with a purity of 95.5% and a yield of 98.4%.

The obtained red dye compound was subjected to elemental analysis, and the analysis result was basically consistent with that in Example 1. Furthermore, infrared spectroscopy analysis showed that the obtained red dye compound was the compound represented by formula (I-1).

Example 3

A red dye compound, the structure of which is shown in the following formula (I-1):

The preparation method of the red dye compound represented by the above formula (I-1) comprises the following specific steps:

(1) Diazotization reaction: same as in Example 1;

(2) Condensation reaction I:

In a 500mL three-necked flask, add 100mL of water, add 19.3g of the compound of formula (V-1) (0.105mol) while stirring to make a slurry, and then dropwise add 242g of a 15% mass concentration of the compound of formula (IV-1) (0.1mol) solution to carry out a condensation reaction, control the temperature to 0°C, react for 4h, and obtain a condensate;

(3) Coupling reaction: the same as in Example 1;

(4) Condensation reaction II: The same as in Example 1, after the reaction, 119.8 g of red dye compound was obtained with a purity of 94.9% and a yield of 96.4%.

The obtained red dye compound was subjected to elemental analysis, and the analysis result was basically consistent with that in Example 1. Furthermore, infrared spectroscopy analysis showed that the obtained red dye compound was the compound represented by formula (I-1).

Example 4

A red dye compound, the structure of which is shown in the following formula (I-1):

The preparation method of the red dye compound represented by the above formula (I-1) comprises the following specific steps:

(1) Diazotization reaction: same as in Example 1;

(2) Condensation reaction I: the same as in Example 1;

(3) Coupling reaction:

The diazonium salt obtained by the diazotization reaction is coupled with the condensation product obtained by the condensation reaction I, the temperature is controlled at 0°C, pH = 6.0-6.5, and the reaction is carried out for 3 hours to obtain a coupled product;

(4) Condensation reaction II: The same as in Example 1, after the reaction, 120.8 g of red dye compound was obtained with a purity of 95.1% and a yield of 97.2%.

The obtained red dye compound was subjected to elemental analysis, and the analysis result was basically consistent with that in Example 1. Furthermore, infrared spectroscopy analysis showed that the obtained red dye compound was the compound represented by formula (I-1).

Example 5

A red dye compound, the structure of which is shown in the following formula (I-1):

The preparation method of the red dye compound represented by the above formula (I-1) comprises the following specific steps:

(1) Diazotization reaction: same as in Example 1;

(2) Condensation reaction I: the same as in Example 1;

(3) Coupling reaction:

The diazonium salt obtained by the diazotization reaction is coupled with the condensation product obtained by the condensation reaction I, the temperature is controlled at 10°C, pH = 6.0-6.5, and the reaction is carried out for 4 hours to obtain a coupled product;

(4) Condensation reaction II: The same as in Example 1, after the reaction, 115.6 g of red dye compound was obtained with a purity of 92.7% and a yield of 93.0%.

The obtained red dye compound was subjected to elemental analysis, and the analysis result was basically consistent with that in Example 1. Furthermore, infrared spectroscopy analysis showed that the obtained red dye compound was the compound represented by formula (I-1).

Example 6

A red dye compound, the structure of which is shown in the following formula (I-1):

The preparation method of the red dye compound represented by the above formula (I-1) comprises the following specific steps:

(1) Diazotization reaction: same as in Example 1;

(2) Condensation reaction I: the same as in Example 1;

(3) Coupling reaction: the same as in Example 1;

(4) Condensation reaction II:

31.8 g of the compound of formula (VI-1) (0.105 mol) was added to the couple (about 0.1 mol), the temperature was controlled at 20°C, pH = 6.0-6.5, and the reaction was carried out for 4 hours to obtain 120.3 g of a red dye compound with a purity of 95.5% and a yield of 96.8%.

The obtained red dye compound was subjected to elemental analysis, and the analysis result was basically consistent with that in Example 1. Furthermore, infrared spectroscopy analysis showed that the obtained red dye compound was the compound represented by formula (I-1).

Example 7

A red dye compound, the structure of which is shown in the following formula (I-1):

The preparation method of the red dye compound represented by the above formula (I-1) comprises the following specific steps:

(1) Diazotization reaction: same as in Example 1;

(2) Condensation reaction I: the same as in Example 1;

(3) Coupling reaction: the same as in Example 1;

(4) Condensation reaction II:

30.3 g of the compound of formula (VI-1) (0.1 mol) was added to the couple (about 0.1 mol), the temperature was controlled at 10°C, pH = 6.0-6.5, and the reaction was carried out for 5 hours to obtain 120.6 g of a red dye compound with a purity of 95.7% and a yield of 97.0%.

The obtained red dye compound was subjected to elemental analysis, and the analysis result was basically consistent with that in Example 1. Furthermore, infrared spectroscopy analysis showed that the obtained red dye compound was the compound represented by formula (I-1).

Example 8

A red dye compound, the structure of which is shown in the following formula (I-1):

The preparation method of the red dye compound represented by the above formula (I-1) comprises the following specific steps:

(1) Diazotization reaction: same as in Example 1;

(2) Condensation reaction I: the same as in Example 1;

(3) Coupling reaction: the same as in Example 1;

(4) Condensation reaction II:

30.3 g of the compound of formula (VI-1) (0.1 mol) was added to the couple (about 0.1 mol), the temperature was controlled at 30°C, pH = 6.0-6.5, and the reaction was carried out for 3 hours to obtain 116.6 g of a red dye compound with a purity of 92.2% and a yield of 93.8%.

The obtained red dye compound was subjected to elemental analysis, and the analysis result was basically consistent with that in Example 1. Furthermore, infrared spectroscopy analysis showed that the obtained red dye compound was the compound represented by formula (I-1).

Example 9

A red dye compound, the structure of which is shown in the following formula (I-2):

The preparation method of the red dye compound represented by the above formula (I-2) comprises the following specific steps:

(1) Diazotization reaction:

In a 1000mL three-necked flask, add 270g of a 15% solution of the compound of formula (III-2) (0.1mol), then add 30.8g of a 30% hydrochloric acid solution (0.25mol), and dropwise add 23g of a 30% sodium nitrite solution (0.1mol) while stirring. Control the temperature to 5°C and react for 2h to obtain a diazonium salt.

(2) Condensation reaction I:

In a 500mL three-necked flask, add 100mL of water, add 19.3g of the compound of formula (V-1) (0.105mol) while stirring to make a slurry, and then dropwise add 242g of a 15% mass concentration of the compound of formula (IV-1) (0.1mol) to carry out a condensation reaction, control the temperature to 5°C, react for 3h, and obtain a condensate;

(3) Coupling reaction:

The diazonium salt obtained by the diazotization reaction is coupled with the condensation product obtained by the condensation reaction I, the temperature is controlled at 5°C, the pH is 6.0-6.5, and the reaction is carried out for 2 hours to obtain a coupled product;

(4) Condensation reaction II:

30.3 g of the compound of formula (VI-1) (0.10 mol) was added to the couple (about 0.1 mol), the temperature was controlled at 20°C, pH = 6.0-6.5, and the reaction was carried out for 4 hours to obtain 116.2 g of a red dye compound with a purity of 96.1% and a yield of 97.4%.

The obtained red dye compound was subjected to elemental analysis, and the analysis results are shown in the following table:

Furthermore, infrared spectroscopy analysis revealed that the obtained red dye compound was the compound represented by formula (I-2).

Example 10

A red dye compound, the structure of which is shown in the following formula (I-3):

The preparation method of the red dye compound represented by the above formula (I-3) comprises the following specific steps:

(1) Diazotization reaction:

In a 1000mL three-necked flask, add 270g of a 15% solution of the compound of formula (III-3) (0.1mol), then add 30.8g of a 30% hydrochloric acid solution (0.25mol), and dropwise add 23g of a 30% sodium nitrite solution (0.1mol) while stirring. Control the temperature to 5°C and react for 2h to obtain a diazonium salt.

(2) Condensation reaction I:

In a 500mL three-necked flask, add 100mL of water, add 19.3g of the compound of formula (V-1) (0.105mol) while stirring to make a slurry, and then dropwise add 242g of a 15% mass concentration of the compound of formula (IV-1) (0.1mol) to carry out a condensation reaction, control the temperature to 5°C, react for 3h, and obtain a condensate;

(3) Coupling reaction:

The diazonium salt obtained by the diazotization reaction is coupled with the condensation product obtained by the condensation reaction I, the temperature is controlled at 5°C, the pH is 6.0-6.5, and the reaction is carried out for 2 hours to obtain a coupled product;

(4) Condensation reaction II:

30.3 g of the compound of formula (VI-1) (0.10 mol) was added to the couple (about 0.1 mol), the temperature was controlled at 20°C, pH = 6.0-6.5, and the reaction was carried out for 4 hours to obtain 115.2 g of a red dye compound with a purity of 95.6% and a yield of 96.6%.

The obtained red dye compound was subjected to elemental analysis, and the analysis results are shown in the following table:

Furthermore, infrared spectroscopy analysis revealed that the obtained red dye compound was the compound represented by formula (I-3).

Comparative Example

Comparative Example 1

A red reactive dye is commercially available as C.I. Reactive Red 195.

Performance testing

(1) Dyeing performance test of pure cotton fabric

Test 1-1: Lifting force test

Provide dye bath compositions of 1% (o.w.f), 3% (o.w.f), 5% (o.w.f), 6% (o.w.f), 7% (o.w.f), 8% (o.w.f), 10% (o.w.f), and 12% (o.w.f) in Examples 1, 9, 10 and Comparative Example 1, respectively. Dye the pure cotton knitted fabric according to the dyeing process shown in FIG. 1 to obtain a sample to be tested.

The color depth value (Integ value) of the test sample is measured in accordance with the provisions of GB/T 6688-1986. The measurement results are expressed to one decimal place and are recorded in the following table.

Test 1-2: Water fastness test A dye bath composition of 3% (o.w.f.) was provided in Examples 1, 9, 10 and Comparative Example 1. A pure cotton knitted fabric was dyed according to the dyeing process shown in FIG1 to obtain a sample to be tested.

Prepare two cups of 2g/L laundry detergent solutions at 70℃ and 90℃ respectively, put the samples to be tested into the above laundry detergent solutions respectively, cool naturally for 10 minutes, stir twice during the period, compare the chromaticity of the residual solution and the untreated solution, and rate and record according to the AATCC gray sample card. The test results are recorded in the table below.

Test 1-3: Water fastness test

The dye bath composition of Examples 1, 9, 10 and Comparative Example 1 was provided in an amount of 3% (o.w.f.). The pure cotton knitted fabric was dyed according to the dyeing process shown in FIG1 to obtain a sample to be tested.

The water fastness test was carried out on the test samples according to the method in ISO 105-E01-2013, and the test results were recorded in the following table.

Test 1-4: Color fastness to rubbing

The dye bath composition of Examples 1, 9, 10 and Comparative Example 1 was provided in an amount of 3% (o.w.f.). The pure cotton knitted fabric was dyed according to the dyeing process shown in FIG1 to obtain a sample to be tested.

The color fastness to rubbing was tested on the test samples according to the method in ISO 105-X12-2016, and the test results were recorded in the following table.

Test 1-5: Color fastness to perspiration test

The dye bath composition of Examples 1, 9, 10 and Comparative Example 1 was provided in an amount of 3% (o.w.f.). The pure cotton knitted fabric was dyed according to the dyeing process shown in FIG1 to obtain a sample to be tested.

The color fastness to perspiration of the test samples was tested according to the method in ISO 105-E04-2013, and the test results were recorded in the following table.

In summary, from the test data of experiments 1-1 to 1-5, it can be seen that the red dye compounds of Examples 1, 9, and 10 have better dyeing enhancement and various color fastnesses than Comparative Example 1 (C.I. Reactive Red 195). This shows that the red dye compound of the present application has very excellent dyeing effect and color fastness, and can be applied to cellulose fiber dyeing and wool dyeing. A large number of dyeing experiments have shown that the red dye compound of the present application has a very broad application prospect.

(2) Dyeing performance test of polyester-cotton blended fabric

Test 2-1: Lifting force test

The reactive dyes in Examples 1, 9, 10 and Comparative Example 1 were mixed with disperse red FBL at 55wt%:45wt%, and dyeing auxiliaries accounting for 10wt% of the total amount of the dye were added, and 1% (o.w.f), 3% (o.w.f), 5% (o.w.f), 6% (o.w.f), 7% (o.w.f), 8% (o.w.f), 10% (o.w.f), 12% (o.w.f) of dye bath compositions were provided respectively. Referring to FIG2, a polyester-cotton blended fabric was dyed at 40°C, with a bath ratio of 1:10, and kept warm for 10min, then heated to 60°C at a heating rate of 1°C/min for 30min, then heated to 130°C at a heating rate of 1°C/min for continued heat dyeing for 30min, and then the fabric was washed, soaped, and washed to obtain a sample to be tested.

The color depth value (Integ value) of the test sample is measured in accordance with the provisions of GB/T 6688-1986. The measurement results are expressed to one decimal place and are recorded in the following table.

Test 2-2: Water fastness test

The reactive dyes in Examples 1, 9, 10 and Comparative Example 1 were mixed with disperse red FBL at 55 wt%:45 wt%, and dyeing auxiliaries accounting for 10 wt% of the total amount of the dye were added, and a dye bath composition of 3% (o.w.f) was provided. Referring to FIG2, the polyester-cotton blended fabric was dyed at 40°C, with a bath ratio of 1:10, and kept warm for 10 minutes, then heated to 60°C at a heating rate of 1°C/min for 30 minutes, then heated to 130°C at a heating rate of 1°C/min for 30 minutes, and then the fabric was washed, soaped, and washed to obtain a sample to be tested.

Prepare two cups of 2g/L laundry detergent solutions at 70℃ and 90℃ respectively, put the dyed samples into the above laundry detergent solutions respectively, cool naturally for 10 minutes, stir twice during the period, compare the chromaticity of the residual solution and the untreated solution, and rate and record according to the AATCC gray sample card. The test results are recorded in the table below.

Test 2-3: Water fastness test

The reactive dyes in Examples 1, 9, 10 and Comparative Example 1 were mixed with disperse red FBL at 55 wt%:45 wt%, and dyeing auxiliaries accounting for 10 wt% of the total amount of the dye were added, and a 3% (o.w.f) dye bath composition was provided. Referring to FIG2, the polyester-cotton blended fabric was dyed at 40°C, with a bath ratio of 1:10, and kept warm for 10 minutes, then heated to 60°C at a heating rate of 1°C/min for 30 minutes, then heated to 130°C at a heating rate of 1°C/min for 30 minutes, and then the fabric was washed, soaped, and washed to obtain a sample to be tested.

The water fastness test was carried out on the test samples according to the method in ISO 105-E01-2013, and the test results were recorded in the following table.

Test 2-4: Color fastness to rubbing test

The reactive dyes in Examples 1, 9, 10 and Comparative Example 1 were mixed with disperse red FBL at 55 wt%:45 wt%, and dyeing auxiliaries accounting for 10 wt% of the total amount of the dye were added, and a dye bath composition of 3% (o.w.f) was provided. Referring to FIG2, the polyester-cotton blended fabric was dyed at 40°C, with a bath ratio of 1:10, and kept warm for 10 minutes, then heated to 60°C at a heating rate of 1°C/min for 30 minutes, then heated to 130°C at a heating rate of 1°C/min for 30 minutes, and then the fabric was washed, soaped, and washed to obtain a sample to be tested.

The color fastness to rubbing was tested on the test samples according to the method in ISO 105-X12-2016, and the test results were recorded in the following table.

Test 2-5: Color fastness to perspiration test

The reactive dyes in Examples 1, 9, 10 and Comparative Example 1 were mixed with disperse red FBL at 55 wt%:45 wt%, and dyeing auxiliaries accounting for 10 wt% of the total amount of the dye were added, and a dye bath composition of 3% (o.w.f) was provided. Referring to FIG2, the polyester-cotton blended fabric was dyed at 40°C, with a bath ratio of 1:10, and kept warm for 10 minutes, then heated to 60°C at a heating rate of 1°C/min for 30 minutes, then heated to 130°C at a heating rate of 1°C/min for 30 minutes, and then the fabric was washed, soaped, and washed to obtain a sample to be tested.

The color fastness to perspiration of the test samples was tested according to the method in ISO 105-E04-2013, and the test results were recorded in the following table.

In summary, from the test data of experiments 2-1 to 2-5, it can be seen that the red dye compounds of Examples 1, 9, and 10 can be used to dye polyester-cotton blended fabrics in a one-bath one-step process, and the dyeing effect and dyeing fastness are very excellent. Therefore, the red dye compounds of the present application have a very broad application prospect.

This specific embodiment is merely an explanation of the present application and is not a limitation of the present application. After reading this specification, those skilled in the art may make modifications to the present embodiment without any creative contribution as needed. However, as long as it is within the scope of the claims of the present application, it shall be protected by the patent law.

Claims (10)

1. The red dye compound is characterized in that the reactive dye compound is a compound represented by a general formula (I);

wherein R is ₁ Selected from the group consisting of

M is selected from H or alkali metal cations;

x is selected from Br, cl or F.

2. The red dye compound according to claim 1, wherein in the general formula (I), -SO ₂ CH ₂ CH ₂ OSO ₃ M is in the meta or para position of-NH-R.

3. The red dye compound according to claim 1, wherein the compound represented by the general formula (i) is a compound of the formula (i-1), the formula (i-2) or the formula (i-3);

4. a method for synthesizing a red dye compound according to any one of claims 1 to 3, comprising the steps of: diazotization reaction: diazotizing a compound represented by a general formula (II) or a general formula (III) to obtain diazonium salt;

wherein M is selected from H or an alkali metal cation;

condensation reaction I: carrying out condensation reaction on the compounds shown in the general formula (IV) and the general formula (V) to obtain a condensate;

wherein M is selected from H or an alkali metal cation;

x is selected from Br, cl or F;

coupling reaction: coupling diazonium salt obtained by diazotization reaction with condensate obtained by condensation reaction I to obtain a coupling compound;

condensation reaction II: condensing the coupling compound obtained by the coupling reaction with a compound represented by a general formula (VI) to obtain a red dye compound;

wherein M is selected from H or an alkali metal cation;

-SO ₂ CH ₂ CH ₂ OSO ₃ m is at-NH ₂ Meta or para of (a).

5. The method for synthesizing a red dye compound according to claim 4, wherein the ratio of the compound represented by the general formula (IV) to the compound represented by the general formula (V) in the condensation reaction I is 1mol (1.05 to 1.1 mol).

6. The method for synthesizing a red dye compound according to claim 4 or 5, wherein in the condensation reaction I, the reaction temperature is 0-5 ℃ and the reaction time is 3-4h.

7. The method for synthesizing a red dye compound according to claim 4, wherein in the coupling reaction, the reaction temperature is 0-5 ℃ and the reaction time is 2-3h.

8. The method for synthesizing a red dye compound according to claim 4, wherein the ratio of the coupling compound to the compound represented by the general formula (VI) in the condensation reaction II is 1mol (1 to 1.05 mol).

9. The method for synthesizing a red dye compound according to claim 4 or 8, wherein in the condensation reaction II, the reaction temperature is 10-20 ℃ and the reaction time is 4-5h.

10. Use of a red dye compound according to any one of claims 1 to 3 for dyeing cellulose fibres, wool, blends containing cellulose fibres or wool.

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