Dye with high lifting power as well as preparation method and application thereof

Abstract

The invention discloses a high-lifting-power dye and a preparation method and application thereof, and belongs to the field of dyes, the high-lifting-power dye comprises a mixture of three compounds shown in the formula (I), in the formula (I), R1 respectively represents C1-4 alkyl groups; d is independently selected from H, Cl, Br and CN, and R3 and R4 are independently selected from H, Cl, Br and CN. The coupling component is prepared by using N-methylaniline, p-chlorobenzyl chloride, o-chlorobenzyl chloride and m-chlorobenzyl chloride which can be purchased on the market as raw materials, and the dye prepared by using the coupling component has higher lifting power and strength.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of dyes, more particularly, to a high build-up dye, a preparation method and application thereof. BACKGROUND

[0002] As non-ionic dyes, disperse dyes are widely used in the dyeing process of synthetic fibers such as polyester, and are dyed in a dispersed state at the initial stage of dyeing. In the dyeing process, disperse dyes are uniformly dispersed in the dyeing solution in the form of fine particles, and the coloring of polyester fibers is achieved through high-temperature and high-pressure, hot melting or carrier dyeing. The dyeing performance is affected by factors such as solubility, dispersion stability and chemical stability, among which the build-up is a key indicator to measure the dyeing depth performance, which refers to the characteristic that the color depth of the fabric can be increased synchronously with the increase of the amount of dye.

[0003] In the hue matching of disperse black dyes, orange and red dyes play an important role, not only affecting the final color, but also directly affecting the final performance of black dyes. Dyes with high build-up can increase the dyeing depth in proportion to the amount of dye, which is suitable for deep and dark colors (such as black and navy blue); while dyes with poor build-up have poor dyeing depth, and the color does not deepen with the increase of the amount of dye after reaching a certain depth. For example, in the preparation of disperse black dyes, if dyes with insufficient build-up are selected, excessive addition is required to make up for the dyeing depth, which will increase the cost and reduce the color fastness.

[0004] Traditional disperse dyes have significant defects: first, some functional groups such as ester groups and amide groups in the molecules of some dyes are prone to hydrolysis under alkaline conditions; second, some dyes based on azo structure also have stability problems under alkaline conditions, which leads to incomplete alkali-resistant color spectrum, especially the lack of red and orange varieties with high build-up, limiting the application of disperse dyes in polyester alkaline short process. In addition, although the existing technology attempts to develop alkali-resistant disperse dyes, the effect is still not ideal.

[0005] For example, a dye compound, a preparation method and application thereof are disclosed in Chinese Patent No. CN202410831475.9, filed on June 25, 2024, which provides an alkali-resistant dye, but it has the core defects of insufficient dyeing intensity and poor build-up. This limitation requires excessive use of dyes in deep dyeing processes, which significantly increases production costs and may affect the color fastness performance of the fabric due to dye residue.

[0006] To solve the above problems, it is urgent to develop a new type of dye with high alkali resistance and high build-up, as well as a preparation method thereof. The new dye has high alkali resistance and high build-up, and the intensity of the dye can also be guaranteed. SUMMARY

[0007] In view of the problems in the prior art, a first object of the present application is to provide a dye with high build-up and a preparation method thereof, which uses commercially available compounds such as those shown in formula (II), p-chlorobenzyl chloride, o-chlorobenzyl chloride and m-chlorobenzyl chloride as raw materials to prepare a coupling component; the dye prepared using the coupling component has high build-up, alkali resistance and strength. A second object of the present application is to provide an application of the dye with high build-up.

[0008] To solve the above problems, the present application adopts the following technical solutions.

[0009] A dye with high build-up, comprising a mixture of three compounds shown in formula (I) in which R2 is respectively;

[0010] Formula (I)

[0011] in which R1 represents C 1-4 alkyl respectively;

[0012] D is independently selected from in which R3 and R4 are independently selected from H, Cl, Br and CN.

[0013] Further, R1 is independently selected from Me and Et;

[0014] D is independently selected from

[0015] Further, the dye with high build-up is preferably:

[0016] Formula (I-1) in which R2 in formula (I-1) is respectively, and the molar ratio of the compounds is 1:1:1);

[0017] Formula (I-2) in which R2 in formula (I-2) is respectively, and the molar ratio of the compounds is 1:1:3);

[0018] Formula (I-3) in which R2 in formula (I-3) is respectively, and the molar ratio of the compounds is 3:1:1);

[0019] Formula (I-4) in which R2 in formula (I-4) is respectively, and the molar ratio of the compounds is 1:3:1);

[0020] Formula (I-5) (Wherein, R2 in Formula (I-5) respectively is The molar ratio of the compound of Formula (I-5) is 1:1:1);

[0021] Formula (I-6) (Wherein, R2 in Formula (I-6) respectively is The molar ratio of the compound of Formula (I-6) is 1:1:1);

[0022] Formula (I-7) (Wherein, R2 in Formula (I-7) respectively is The molar ratio of the compound of Formula (I-7) is 1:1:1);

[0023] Formula (I-8) (Wherein, R2 in Formula (I-8) respectively is The molar ratio of the compound of Formula (I-8) is 1:1:1);

[0024] Formula (I-9) (Wherein, R2 in Formula (I-9) respectively is The molar ratio of the compound of Formula (I-9) is 1:1:1) or Formula (I-10) (Wherein, R2 in Formula (I-10) respectively is The molar ratio of the compound of Formula (I-10) is 1:1:1).

[0025] Further, in the mixture, R2 in Formula (I) respectively is The molar ratio of the compound of Formula (I) is (1 / 3)-3:(1 / 3)-3:1; preferably 1:1:1.

[0026] The present application also provides a preparation method of the above-mentioned dye with high lifting force, and the equation is as follows:

[0027]

[0028] Coupling component + diazonium salt → target dye:

[0029] Wherein, R1 respectively represents C 1-4 alkyl;

[0030] The preparation steps are as follows:

[0031] S1: preparation of coupling component: adding p-chloro-chlorobenzyl, o-chloro-chlorobenzyl and m-chloro-chlorobenzyl in sequence to the compound as shown in Formula (II), and reacting for 12-24h to obtain the coupling component;

[0032] S2: adding diazonium salt to the coupling component obtained in S1 step, and obtaining the target dye after reaction.

[0033] Further, the molar ratio of the compound of formula (II), p-chlorobenzyl chloride, o-chlorobenzyl chloride and m-chlorobenzyl chloride is 1:0.2-0.7:0.2-0.7:0.2-0.7, preferably 1:0.2-0.6:0.2-0.6:0.2-0.6; the molar ratio of diazonium salt and coupling component is 1:1-1.1.

[0034] Further, the reaction temperature of S1 step is 90-110℃, and the reaction time is 12-24h; the reaction temperature of S2 step is -5-20℃, and the reaction time is 1-6h.

[0035] Further, the diazonium salt is prepared by reacting diazo component with nitrosyl sulfuric acid in sulfuric acid at 0-30℃, and the diazo component is one of 2,6-dibromo-4-nitroaniline, 2-cyano-4-nitroaniline, 2-cyano-6-chloro-4-nitroaniline, 2-cyano-6-bromo-4-nitroaniline, 2-amino-6-nitrobenzothiazole and 3-amino-5-nitrobenzisothiazole.

[0036] The application further provides the use of the above-mentioned high-build dye in dyeing.

[0037] A disperse orange dye, comprising the above-mentioned high-build dye.

[0038] A disperse red dye, comprising the above-mentioned high-build dye.

[0039] A disperse black dye, comprising the above-mentioned high-build dye.

[0040] Compared with the prior art, the application has the following advantages:

[0041] The preparation method provided by the application uses commercially available N-methylaniline, p-chlorobenzyl chloride, o-chlorobenzyl chloride and m-chlorobenzyl chloride as raw materials to prepare the coupling component. The dye prepared using the coupling component not only has excellent build, but also exhibits high dyeing strength. DETAILED DESCRIPTION

[0042] Example 1:

[0043] Preparation of the coupling component:

[0044] Step one: 200g of water, 94g of N-methylaniline, 55g of soda ash, 52g of p-chlorobenzyl chloride, 52g of o-chlorobenzyl chloride and 52g of m-chlorobenzyl chloride are mixed, heated to 100-105℃, and reacted for 16 hours, then cooled and separated, and 100g of glacial acetic acid is added to the oil layer to dissolve it, to obtain the coupling component;

[0045] Step two: add 120 g sulfuric acid, 132 g nitrosyl sulfuric acid with 40% mass concentration into a flask, control 20-30°C to uniformly add 119 g 2,6-dibromo-p-nitroaniline, and keep the reaction for 3 hours to obtain a diazonium salt.

[0046] Step three: add 50 g water, 100 g ice, 50 g sulfuric acid, 1 g Pingpingka O, and 2 g sulfamic acid into a beaker, add 0.5 batches of the coupling component, and beat and dissolve for 30 minutes, then add all the diazonium salt obtained in step two at 0°C, and keep the reaction for 3 hours, and then filter and wash to obtain 214 g orange disperse dye with a yield of 93.4%.

[0047] Example 2:

[0048] The difference between this example and Example 1 is that: in step one, 200 g water, 94 g N-methylaniline, 55 g soda ash, 93 g p-chlorobenzyl chloride, 31 g o-chlorobenzyl chloride, and 31 g m-chlorobenzyl chloride are mixed to prepare the coupling component, and the other reaction conditions are consistent with those of Example 1. The yield of orange disperse dye is 94.6%.

[0049] Example 3:

[0050] The difference between this example and Example 1 is that: in step one, 200 g water, 94 g N-methylaniline, 55 g soda ash, 31 g p-chlorobenzyl chloride, 93 g o-chlorobenzyl chloride, and 31 g m-chlorobenzyl chloride are mixed to prepare the coupling component, and the other reaction conditions are consistent with those of Example 1. The yield of orange disperse dye is 94.1%.

[0051] Example 4:

[0052] The difference between this example and Example 1 is that: in step one, 200 g water, 94 g N-methylaniline, 55 g soda ash, 31 g p-chlorobenzyl chloride, 31 g o-chlorobenzyl chloride, and 93 g m-chlorobenzyl chloride are mixed to prepare the coupling component, and the other reaction conditions are consistent with those of Example 1. The yield of orange disperse dye is 92.1%.

[0053] Example 5:

[0054] Preparation of:

[0055] Step one: mix 200 g water, 94 g N-methylaniline, 55 g soda ash, 52 g p-chlorobenzyl chloride, 52 g o-chlorobenzyl chloride, and 52 g m-chlorobenzyl chloride, and then heat to 100-105°C, keep the reaction for 16 hours, cool and separate the layers, and then add 100 g glacial acetic acid to the oil layer to dissolve, to obtain the coupling component;

[0056] Step two: add 160 g sulfuric acid, 130 g nitrosyl sulfuric acid with 40% mass concentration into the flask, control the temperature at 10-20℃, add 65.2 g 2-cyano-p-nitroaniline uniformly, and keep the reaction for 3 hours.

[0057] Step three: add 50 g water, 100 g ice, 50 g sulfuric acid, 1 g peregal O, and 2 g sulfamic acid into the beaker, add 0.5 batches of coupling component 1, and beat to dissolve for 30 minutes, add ice to control the temperature at 0℃, add all the diazonium salt obtained in step two, and keep the reaction for 3 hours, and then filter and wash to obtain 160 g red disperse dye with a yield of 90.9%.

[0058] Test example 1:

[0059] The orange dyes involved in example 1 and existing orange dyes are respectively subjected to fastness tests, and the test method is as follows:

[0060] The orange dyes involved in example 1 and existing disperse orange dyes are respectively subjected to fastness tests, and the test method is as follows:

[0061] Table 1 is the test result of fastness properties

[0062]

[0063]

[0064] From the content of table 1, it can be seen that the water washing fastness, water immersion fastness, acid sweat fastness and alkali sweat fastness of the disperse orange dye of example 1 are not lower than those of the existing disperse orange dye, and in some test methods, the disperse orange dye involved in example 1 is better than the existing disperse orange dye; for example, according to the ISO-105-C06 C2S standard test of water washing fastness, the existing disperse orange dye has an acetic acid staining rating of 3-4, while the disperse orange dye of the application has an acetic acid staining rating of 4-5, which shows that the water washing fastness (ISO-105-C06 C2S) of the disperse orange dye prepared by the application is better than that of the existing disperse orange dye; in addition, the disperse orange dye involved in the application has a nylon and acetic acid staining rating of 4-5 and 5 respectively in the test of water immersion fastness, while the existing disperse orange dye has a nylon and acetic acid staining rating of 4 and 4-5 respectively, which is obviously lower than that of the disperse orange dye involved in the application, which shows that the water immersion fastness of the disperse orange dye of the application is more excellent, and the comprehensive performance is better.

[0065] The most prominent difference is that the pH range of the existing dispersed orange dye is 3.5-5; the pH range of the dispersed orange dye involved in the present application is 3.5-8, which shows that the dispersed orange dye of the embodiment not only maintains the stability of the traditional dye under acidic conditions, but also significantly widens the pH range to alkaline environment (pH 8), while having excellent pH stability.

[0066] Test Example 2:

[0067] The fastness test was carried out on the red dye involved in Example 5 and the existing red dye, respectively, and the test method was as follows:

[0068] The polyester was dyed with the red dye involved in the above Example 5 and the existing dispersed red dye at a concentration of 5% by the conventional dyeing method, and adjusted to the same depth, the pH range was tested, and the water washing fastness was tested by ISO-105-C06 C2S, AATCC-61-2A, ADIDAS-AD three standard methods, the water immersion fastness was tested by ISO-105-E01, the acid and alkali sweat fastness was tested by ISO-105-E04, and the rubbing fastness (dry) and rubbing fastness (wet) was tested by ISO-105-X12.

[0069] Table 2 is a fastness property test table

[0070]

[0071]

[0072] As can be seen from the content of Table 2, the water washing fastness, water immersion fastness, acid sweat fastness and alkali sweat fastness performance of the dispersed red dye involved in the present application are not lower than those of the existing dispersed red dye, and in some test methods, the dispersed red dye involved in Example 5 is better than the existing dispersed red dye; for example, according to the ISO-105-C06 C2S standard test of water washing fastness, the polyester staining and acetic acid staining ratings of the existing dispersed red dye are 3 and 3-4 respectively; while the polyester staining and acetic acid staining ratings of the dispersed red dye involved in Example 5 are 3-4 and 4 respectively; which shows that the water washing fastness (ISO-105-C06 C2S) of the dispersed red dye involved in Example 5 is better than that of the existing dispersed red dye; in addition, the nylon and acetic acid staining ratings of the dispersed red dye involved in Example 5 are 4-5 and 5 respectively when testing the water immersion fastness, while the nylon and acetic acid staining ratings of the existing dispersed red dye are 4 and 4-5 respectively, which is significantly lower than that of the dispersed red dye involved in Example 5, which shows that the water immersion fastness of the dispersed red dye of the present application is more excellent, and the comprehensive performance is better.

[0073] The most prominent difference is that the pH range of the existing disperse red dye is 3.5-5, while the pH range of the disperse red dye involved in Example 5 is 3.5-8, which shows that the disperse red dye of Example 5 not only maintains the stability of the traditional dye under acidic conditions, but also significantly widens the pH range to alkaline environment (pH 8) while maintaining excellent pH stability.

[0074] In summary, the fastness performance test results of the disperse dyes prepared in the present application all reach or even exceed the level of similar dyes, while significantly widening the pH range of the dyes and enhancing the flexibility of actual application.

[0075] Test Example 3:

[0076] The build-up of the high build disperse dyes involved in Example 1 and Example 5 and the existing corresponding dyeing dyes were tested respectively, and the test method was as follows:

[0077] Determine 1 / 1 standard depth (C) according to GB / T 4841.1-2006, and use the high temperature and high pressure dyeing method in GB / T 2394-2024 as the benchmark to dye C, 2C and 4C three concentration samples; use GB / T 250-2008 to evaluate the color change of gray sample card to compare the color difference level of C and 4C and 2C and 4C dyeing samples. (Rating standard: excellent: C and 4C dyeing sample color change ≤2 levels, and 2C and 4C dyeing sample color change <3 levels; good: C and 4C dyeing sample color change ≤2 levels, and 2C and 4C dyeing sample color change ≥3 levels; general: C and 4C dyeing sample color change >2 levels; poor: cannot reach 1 / 1 standard depth within the specified concentration.)

[0078] The color depth change was evaluated to determine the build-up level. The evaluation results are as follows:

[0079] Table 3 Build-up determination results

[0080]

[0081] From the content of Table 3, it can be seen that the disperse orange dye involved in Example 1 and the disperse red dye involved in Example 5 meet the color change of C and 4C dyeing samples ≤ 2 levels, and the color change of 2C and 4C dyeing samples < 3 levels, and the final evaluation is "excellent"; while the existing corresponding disperse dyes only meet the color change of C and 4C dyeing samples ≤ 2 levels, and the color change of 2C and 4C dyeing samples ≥ 3 levels, and the final evaluation is "good". This shows that the building-up property of the disperse orange dye involved in Example 1 and the disperse red dye involved in Example 5 is better than that of the existing disperse orange dye and disperse red dye. In addition, the color change rating of the disperse orange dye involved in Example 1 and the disperse red dye involved in Example 5 in the 2C-4C high concentration interval is 2 levels, while the color change rating of the existing disperse orange dye and the existing disperse red dye in the 2C-4C high concentration interval is 3 levels. This shows that the color depth of the dye of the present application grows more stably at high concentration, the dyeing uniformity is better, and the color depth does not stagnate due to the increase of concentration, which indirectly reflects that the dyeing stability at high concentration is better than that of the existing dye.

Claims

1. A high lift dye, characterized by: a mixture of compounds as shown in formula (I) wherein R2 is selected from the group consisting of a mixture of compounds as shown in formula (I) wherein R2 is selected from the group consisting of Formula (I) wherein R1represents independently for each occurrence C 1-4 alkyl; D are each independently selected from wherein R3and R4are each independently selected from H, CI, Br, and CN.

2. A high lift dye according to claim 1, characterized in that: said R1 is independently selected from Me and Et; D is independently selected from 3. The high lift dye according to claim 1, characterized in that: In the mixture, R2as shown in formula (I) is The molar ratio of the compounds of formula (I) is (1 / 3)-3 : (1 / 3)-3 :

1.

4. A process for the preparation of a high lift dye according to any one of claims 1 to 3, characterized in that: The preparation equation is shown as follows: wherein R1represents independently C 1-4 alkyl; The preparation procedure is shown as follows: S1: preparing the coupling component: adding p-chlorobenzyl chloride, o-chlorobenzyl chloride and m-chlorobenzyl chloride into the compound shown as formula (II) in sequence, and reacting to obtain the coupling component; S2: adding diazonium salt into the coupling component obtained in step S1, and reacting to obtain the target dye.

5. A process for the preparation of a high-lift dye according to claim 4, characterized in that: The molar ratio of the compound shown as formula (II), p-chlorobenzyl chloride, o-chlorobenzyl chloride and m-chlorobenzyl chloride is 1:0.2-0.7:0.2-0.7:0.2-0.7; and the molar ratio of diazonium salt and the coupling component is 1:1-1.

1.

6. A process for the preparation of a dye having high build according to claim 3, characterized in that: The reaction temperature of step S1 is 90-110℃, and the reaction time is 12-24h; and the reaction temperature of step S2 is-5-20℃, and the reaction time is 1-6h.

7. A process for the preparation of a high-lift dye according to claim 4, characterized in that: The diazonium salt is prepared by reacting diazo component with nitrosyl sulfuric acid in sulfuric acid at 0-30℃, wherein the diazo component is one of 2,6-dibromo-4-nitroaniline, 2-cyano-4-nitroaniline, 2-cyano-6-chloro-4-nitroaniline, 2-cyano-6-bromo-4-nitroaniline, 2-amino-6-nitrobenzothiazole and 3-amino-5-nitrobenzoisothiazole.

8. Use of a dye with high lifting force according to any one of claims 1-3 in dyeing.

9. A disperse black dye, characterized by: A dye with high lifting force according to any one of claims 1-3. A dye with high lifting force according to any one of claims 1-3.

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