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Preparation method of azoxy and azo distyrylbenzene dye

A technology of azo oxide and stilbene, which is applied in the field of dyes, can solve the problems of economical and environmental protection that are difficult to meet production requirements, affect product yield, and complicated processing steps, and achieve easy implementation, good cellulose affinity, The effect of stable storage

Active Publication Date: 2019-10-25
洛阳美伦色彩科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the disadvantage of this method is that lipophilic amines containing more carbon atoms cannot be separated well, while lipophilic amines containing less carbon atoms (≤C 12 ) lipophilic amines are easily lost with the electrolyte in the waste liquid to an unusable level
Therefore, this method economy and environmental protection all are difficult to reach production requirement
[0009] US3953419 discloses the preparation method of dyes Direct Yellow 11 and Direct Orange 15. The method uses 4-nitrotoluene-2-sulfonic acid as raw material, water as reaction solvent, and condensation in the presence of tetramethylammonium hydroxide. The suspension of yellow 11 dye was obtained, but because the suspension was obtained, it needed to be filtered. Not only the processing steps were complicated, which affected the product yield, but also the obtained product had to be further configured into a solution before it could be used, which brought great challenges to the use of dyes. big inconvenience

Method used

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  • Preparation method of azoxy and azo distyrylbenzene dye
  • Preparation method of azoxy and azo distyrylbenzene dye
  • Preparation method of azoxy and azo distyrylbenzene dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The preparation method of dye Direct Yellow 11 is as follows:

[0037] Slowly add 11.9 parts of 4-nitrotoluene-2-sulfonic acid to 44 parts of 25% tetramethylammonium hydroxide aqueous solution (40°C), and stir to form a blue-purple solution. At 70°C, the reaction was stirred for 5h. After the reaction, a reddish-brown transparent solution was formed, and 4.7 parts of 30% hydrochloric acid was added to the solution to adjust the pH to 8 to obtain a yellow solution with a maximum absorption wavelength of 414 nm.

[0038] Dye structural formula I, as shown in the figure below:

[0039] (I)

[0040] Among them, X represents the group N ⊕ (CH 3 ) 4 .

Embodiment 2

[0042] The preparation method of dye Direct Yellow 11 is as follows:

[0043] Slowly add 4-nitrotoluene-2-sulfonic acid to 15% tetramethylammonium hydroxide aqueous solution, the molar ratio of 4-nitrotoluene-2-sulfonic acid to tetramethylammonium hydroxide is 1:2, Stir to form a blue-violet solution. At 65°C, the reaction was stirred for 8h. After the reaction, a reddish-brown transparent solution was formed, and hydrochloric acid was added to the solution to adjust the pH to 7 to obtain a yellow solution with a maximum absorption wavelength of 410 nm.

[0044] Structure is with embodiment 1.

Embodiment 3

[0046] The preparation method of dye Direct Yellow 11 is as follows:

[0047]Slowly add 4-nitrotoluene-2-sulfonic acid to 30% tetramethylammonium hydroxide aqueous solution (40°C), the molar ratio of 4-nitrotoluene-2-sulfonic acid to tetramethylammonium hydroxide 1:5, stirring to form a blue-purple solution. The reaction was stirred at 85 °C for 4 h. After the reaction, a reddish-brown transparent solution was formed, and hydrochloric acid was added to the solution to adjust the pH to 9 to obtain a yellow solution with a maximum absorption wavelength of 416 nm.

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Abstract

The invention provides a preparation method of azoxy and azo distyrylbenzene dye. The preparation method includes the following steps that 4-nitrotoluene-2-sulfonate is taken as a raw material, wateris taken as a reaction solvent, in the presence of tetramethylammonium hydroxide, dye direct yellow 11 is obtained through the condensation reaction, and then dye direct orange 15 can be obtained through reduction. According to the preparation method of the azoxy and azo distyrylbenzene dye, filtering operation is not needed, process steps are simple, operability is high, a concentrated aqueous solution of the dye is prepared, the concentrated aqueous solution can be stably stored and basically does not contain an organic solvent and an inorganic salt, is suitable for industrial production, and the problems of the production, storage and use of the dye in the prior art are solved.

Description

technical field [0001] The invention relates to the field of dyes, in particular to a method for preparing azo oxide and azo-stilbene dyes. Background technique [0002] As the paper dyeing process matures, the market demand for high-fast direct dye products is increasing. However, there are still some problems with direct dyes on the market, such as poor affinity with cellulose, light fastness and acid and alkali resistance, complex dye preparation process, poor stability, and easy formation of gel, crystallization or agglomeration in long-term storage , making direct dyes difficult or impossible to use. [0003] It is known that 4-nitrotoluene-2-sulfonic acid self-condenses to prepare azo-stilbene yellow dyes. These dyes are direct dyes especially used for dyeing paper, the most important and commercially valuable of which is the direct dye Direct Yellow 11 (abbreviated DY11) -- a yellow direct dye with a reddish tinge. [0004] It is known that 4-nitrotoluene-2-sulfoni...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B56/08
CPCC09B56/08
Inventor 于克兢
Owner 洛阳美伦色彩科技有限公司
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