Disperse blue dye composition and use thereof

By adopting a dispersed blue dye mixture with a specific chemical structure, the problem of the existing dispersed blue dye 284 dye is extremely poor in alkaline conditions, and good dyeing performance and economical and environmentally friendly production process under alkaline conditions are achieved.

WO2025107148A2PCT designated stage expired Publication Date: 2025-05-30LEPING SAFELY PHARMA
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Patent Information

Application Number
PCT/CN2023/132929
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Filing Date
2023-11-21
Publication Date
2025-05-30

AI Technical Summary

Technical Problem

The existing dispersed blue 284 dye has extremely poor resistance under alkaline conditions, which limits its application range.

Method used

A dispersed blue dye mixture consisting of component A and component B, wherein component A and component B meet the specific chemical structures of formula (I) and formula (II), respectively, and are prepared by specific synthetic methods. The additives are lignin sulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate or naphthalene sulfonic acid formaldehyde condensate.

Benefits of technology

Under alkaline conditions, the color is bright, the uniform dye is good, the lifting power is high, and the production process is low, and the production process is economical and environmentally friendly, which significantly improves the alkali resistance of the dye.

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Description

Combination and application of disperse brilliant blue dye Technical Field

[0001] The present invention relates to the field of printing and dyeing, and in particular to a combination and application of a disperse brilliant blue dye. Background Art

[0002] Disperse Brilliant Blue 284 is a disperse dye with a vibrant color, high absorption coefficient, high dye strength, and a high build-up rate. It is primarily used for dyeing and printing polyester and blended fabrics, and has a wide range of applications. While Disperse Brilliant Blue 284 exhibits excellent performance, its ester tail group results in extremely poor alkali resistance, preventing dyeing under alkaline conditions. This significantly limits its application. Therefore, developing a Disperse Brilliant Blue dye with a vibrant color, excellent performance, and a color shade similar to Disperse Brilliant Blue 284 is an urgent challenge for the dye industry.

[0003] SUMMARY OF THE INVENTION

[0004] The invention provides a disperse brilliant blue dye mixture, which solves the defect of poor alkali resistance of the existing disperse brilliant blue 284 product and maintains the obvious advantages of bright color, good level dyeing property and high lifting power, and is low in price and has an economical and environmentally friendly production process.

[0005] To achieve the above object, the technical solution adopted by the present invention is: a disperse brilliant blue dye mixture, which is composed of a mixture of two parts: dye and auxiliary agent; the dye includes component A and component B,

[0006] The component A is a disperse dye having the structure shown in formula (I),

[0007] The component B is a disperse dye having the structure shown in formula (II),

[0008] in:

[0009] R is selected from any one of methyl, ethyl, 2-methoxyethyl, and 2-ethoxyethyl;

[0010] R and R are selected from any one of ethyl, 2-(2-methoxyethoxy)ethyl, and 2-(2-ethoxyethoxy)ethyl, or a mixture of two thereof;

[0011] The disperse brilliant blue dye combination is characterized in that component A contains at least one of the following structures:

[0012] The disperse brilliant blue dye combination is characterized in that component B contains at least one of the following structures:

[0013] The weight percentage of the pure dye of the following structural formula of the dye part is: The weight percentage of the pure dye of the following structural formula of the dye part is: 40-95% of the component A dye of formula (I) and 1-50% of the component B dye of formula (II).

[0014] The weight ratio of the disperse brilliant blue dye combination and the auxiliary agent to the disperse brilliant blue dye combination is 0.5-6:1.

[0015] The auxiliary agent is selected from any one of lignin sulfonate, alkylnaphthalenesulfonic acid formaldehyde condensate, and naphthalenesulfonic acid formaldehyde condensate, or a mixture of two or more thereof.

[0016] The present invention relates to the use of a combination of disperse brilliant blue dyes in dyeing or printing hydrophobic fiber materials. The design concept and beneficial effects of the present invention are as follows: the mixed dyes conforming to the general chemical structure formula (I) and the general chemical structure formula (II) both contain ether bonds, have good affinity with polyester fibers, good dyeing levelness, and high lift. Furthermore, the ether bonds are relatively stable and not easily hydrolyzed, especially under alkaline conditions, and can be dyed under alkaline conditions.

[0017] The brilliant blue disperse dye composition of the present invention solves the problem of poor alkali resistance of the disperse blue 284 product, maintains the obvious advantages of bright color, good level dyeing property and high lifting power, is low in price, and has an economical and environmentally friendly production process. It is a rare disperse blue dye composition with good performance. DETAILED DESCRIPTION

[0018] The present invention will be further described below with reference to specific embodiments, but the protection scope of the present invention is not limited thereto.

[0019] Example 1:

[0020] Component A, a method for preparing a disperse dye compound, comprises the following steps: dissolving 3-amino-5-nitro-2,1-benzisothiazole, a compound of the structure represented by formula (III), in sulfuric acid, adding nitrosyl sulfuric acid dropwise at 0-10°C, and incubating for 3 hours to obtain a diazo solution; adding water to the compound of the structure represented by formula (IV), dissolving in sulfuric acid while stirring, adding sulfamic acid, cooling to 0-5°C, adding diazo solution, reacting at 0-5°C, filtering after the reaction is complete, washing with water to neutrality, and drying to obtain a compound of the structure represented by formula (I). The molar ratio of formula (III): nitrosyl sulfuric acid: formula (IV) is 1:1.05:1.

[0021] The preparation method of component B, a disperse dye compound, comprises the following steps:

[0022] The compound 2,6-dibromo-p-nitroaniline of formula (V) is dissolved in sulfuric acid, and nitrosylsulfuric acid is added dropwise at 0-10°C. The temperature is maintained for 2-4 hours to obtain a diazo solution. The compound of formula (VI) is added to water, and sulfuric acid is added to dissolve the mixture while stirring. Aminosulfonic acid is added, the temperature is lowered to 0-5°C, and the diazo solution is added. The mixture is reacted at 0-5°C. After the reaction is complete, the mixture is filtered, washed with water until neutral, and dried to obtain the compound of formula (VII). The molar ratio of formula (V): nitrosylsulfuric acid: formula (VI) is 1:1.05:1.

[0023] The dried compound (VII) is dissolved in DMF, and cuprous cyanide is added. The temperature is raised to 80-100°C for cyanidation. After the reaction is complete, methanol is added, cooled, precipitated, filtered, washed with methanol, and dried to obtain the compound of formula (II). The molar ratio of formula (VII) to cuprous cyanide is 1:2.1.

[0024] The R group of component A is CH2CH2O-CH3 to obtain a compound of formula (I-1), and the R1 and R2 groups of component B are CH2CH3 to obtain a compound of formula (II-1). 31 grams of the compound of formula (I-1), 7.5 grams of the compound of formula (II-1), and 161.5 grams of dispersant MF are mixed with 300 grams of water to form a slurry. The solid content of the slurry is preferably controlled to be 35-45%. The mixture is ground and dispersed, and spray-dried to obtain a finished product, which can provide a blue hue to the fabric.

[0025] Embodiment 2~12:

[0026] The method described in Example 1 was followed, except that the weight ratios of component A and component B as shown in Table 1, along with the additives, were used. Water was added and mixed to form a slurry, preferably with a solids content of 35-45%. The slurry was then ground, dispersed, and spray-dried to obtain a finished product. This product provided the fabric with a uniform blue hue with good fastness properties. The additives included methylnaphthalenesulfonic acid formaldehyde condensate (dispersant MF), naphthalenesulfonic acid formaldehyde condensate (diffuser NNO), and sodium lignin sulfonate (lignin NA, 83A).

[0027] Comparative Example 1: The commercially available Disperse Blue 284 product was used as a comparative example, and the depth of the dyed cloth sample was consistent with the depth of the dyed cloth sample of Example 1-12.

[0028] Table 1: Dye ratio

[0029] Performance testing:

[0030] The disperse dyes prepared in Examples 1-12 and the disperse blue 284 disperse dye from Comparative Example 1 were used to treat polyester fabric using a conventional high-temperature, high-pressure dyeing method. During the treatment, the dye depth (owf) was controlled at 1.2%, the bath ratio was 1:40, and the pH of the dye bath was adjusted to 4-5. Dyeing was performed at room temperature, the temperature was raised to 130°C at a rate of 1°C / min, and the dye bath was held at that temperature for 45 minutes. The fabric was then reduced, washed, and dried according to conventional methods. The fabric was then cooled to 70°C and removed. Based on this dyeing method, the dye bath pH was adjusted to 7, 9, and 10, respectively. Using fabric samples dyed at a pH of 4-5 as a standard, the dye uptake at different pH values ​​was tested to determine the pH value for normal dyeing. See Table 2 for details:

[0031] Table 2 Dye uptake rate at different pH values

[0032] Coloring rate of different disperse dyes at pH=7 Coloring rate at pH=9 Coloring rate at pH=10 Example 1 100.1% 99.8% 95.5% Example 2 99.9% 100% 95.6% Example 3 100.7% 100.1% 95.2% Example 4 99.5% 98.9% 94.2% Example 5 100.3% 99.9% 96.1% Example 6 100.2% 100% 96.3% Example 7 99.8% 98.8% 95.4% Example 8 100.5% 100% 96.7% Example 9 100.2% 100.3% 96.1% Example 10 101.3% 100.5% 96.3% Example 11 100.1% 100% 94.8% Example 12 100.8% 100.3% 95.7% Comparative Example 1 67.7% 67.0% 3.2%

[0033] From the coloring rates at different pH values ​​in Table 2, it can be seen that the coloring rate of Comparative Example 1 at pH = 7 is 67.7%, the coloring rate at pH = 9 is 67.0%, and the coloring rate at pH = 10 is only 3.2%. However, the coloring rates of the dyes of Examples 1 to 12 after dyeing at pH = 7 and pH = 9 all reach 98.8% or more, and the coloring rate of the dyes after dyeing at pH = 10 can also reach 94.2% or more. Therefore, the pH range of the dyes of the examples is much higher than that of Comparative Example 1, the pH requirement for dyeing is wider, and the dyeing is more stable during use.

[0034] The above embodiments are intended only to illustrate the technical concepts and features of the present invention. Their purpose is to enable those skilled in the art to understand the contents of the present invention and implement them accordingly. They are not intended to limit the scope of protection of the present invention. Any equivalent changes or modifications made in accordance with the spirit of the present invention are intended to be covered by the scope of protection of the present invention.

Claims

1. A combination of disperse brilliant blue dyes, which is composed of a mixture of two parts: dyes and auxiliaries. The dyes include component A and component B. It is characterized in that: Component A is one or two compounds with the structure shown in formula (I), and component B is one or two compounds with the structure shown in formula (II), where: R is selected from any one of methyl, ethyl, 2-methoxyethyl, and 2-ethoxyethyl; R and R are selected from any one or a combination of two of ethyl, 2-(2-methoxyethoxy)ethyl, and 2-(2-ethoxyethoxy)ethyl.

2. The combination of disperse brilliant blue dyes according to claim 1, It is characterized in that: The said component A contains at least one group of the following structures:

3. The combination of disperse brilliant blue dyes according to claim 1, It is characterized in that: The said component B contains at least one of the following structures:

4. The combination of disperse brilliant blue dyes according to claim 1, characterized in that: the weight percentage content of the pure dye of the following structural formula in the dye part is: 40-95% of component A dye with the structure of formula (I), and 1-50% of component B dye with the structure of formula (II).

3. A combination of disperse brilliant blue dyes, which contains the combination of disperse brilliant blue dyes according to any one of claims 1 to 4 and an auxiliary. The weight ratio of the auxiliary to the combination of disperse brilliant blue dyes is 0.5-6:

1.

4. The combination of disperse brilliant blue dyes according to claim 5, It is characterized in that: The said auxiliary is selected from any one or a mixture of two or more of lignosulfonate, alkylnaphthalene sulfonate formaldehyde condensate, and naphthalene sulfonate formaldehyde condensate.

5. The application of the combination of disperse brilliant blue dyes according to any one of claims 1 to 4 or the combination of disperse brilliant blue dyes according to any one of claims 5 to 6 in the dyeing or printing of hydrophobic fiber materials.