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Preparation method of high-whiteness thermosensitive color developing agent containing sulfonylurea structure

A technology containing sulfonylurea and high whiteness, which is applied in the field of preparation of heat-sensitive developer, which can solve the problem that the purity of color developer and whiteness affect the quality of thermal paper, the preparation process is cumbersome and complicated, and the heat-sensitive paper is dark. problems, to achieve the effect of preventing poor color, improving the purity of filter cake, and preventing oxidation and discoloration

Pending Publication Date: 2022-03-01
HEBEI JIANXIN CHEM IND CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Since the production process of thermal paper is to directly compound and coat the color developer, color coupler, stabilizer and other functional components on the surface of the paper base, the entire use process does not involve the color developer purification or similar purification process, so the obvious The purity and whiteness of the colorant will directly affect the quality of thermal paper; at the same time, in industrial production, since most of the sulfonylurea color developers are synthesized in a highly polar solvent, the residual solvent will cause the color developer to be separated from the color developer in advance. Chromogenic effect, resulting in dark and gray thermal paper stored for a long time
[0005] The above problems can be solved by decolorizing and recrystallizing the finished chromogenic agent before application, but the purification operation makes the preparation process more complicated and complicated, and the yield is lost. Therefore, while changing and controlling the preparation process, the post-treatment process of the target product should be studied is the best way to solve the problems existing in the application

Method used

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  • Preparation method of high-whiteness thermosensitive color developing agent containing sulfonylurea structure
  • Preparation method of high-whiteness thermosensitive color developing agent containing sulfonylurea structure

Examples

Experimental program
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Effect test

Embodiment 1

[0031] One-step reaction: feed N into reactor 1 2 , add 500L DMAC after air replacement, start stirring, add 272.75kg (2.50kmol) m-aminophenol (MAP), after dissolving at 40°C, slowly add 517.65kg (2.63kmol) p-toluenesulfonyl isocyanate (PTSI), The dropping time is 2.5 hours, and the temperature is kept at 40° C., and the temperature is kept for 2 hours to reach the end point.

[0032] Two-step reaction: p-toluenesulfonyl chloride (PTSC) solution configuration: 524.42kg (2.75kmol) PTSC was dissolved in 525L DMAC.

[0033] Transfer the material in the reactor 1 to N 2 In the reaction kettle 2 of the atmosphere, pump 1196kg (2.99kmol) of 10% NaOH solution in the reaction kettle 2, the system pH=10-11, slowly add the DMAC solution of p-toluenesulfonyl chloride (PTSC) dropwise, and simultaneously add 30 300kg (2.25kmol) of % NaOH was dissolved to ensure that the pH of the system was 10-11, the temperature was between 40-60°C, the dropping time was 1.0h, and the temperature was ke...

Embodiment 2

[0039] One-step reaction: feed N into reactor 1 2, add 750L DMAC after air replacement, start stirring, add 272.75kg (2.50kmol) m-aminophenol (MAP), after dissolving at 30°C, slowly add 542.3kg (2.75kmol) p-toluenesulfonyl isocyanate (PTSI), The dropping time is 3.5 hours, and the temperature is kept at 30° C., and the temperature is kept for 1.5 hours to reach the end point.

[0040] Two-step reaction: p-toluenesulfonyl chloride (PTSC) solution configuration: 572.10kg (3.00kmol) PTSC was dissolved in 720L DMAC.

[0041] Transfer the material in the reactor 1 to N 2 In the reaction kettle 2 of the atmosphere, pump 20% NaOH solution 598kg (2.99kmol) in the reaction kettle 2, the system pH=10-11, slowly add the DMAC solution of p-toluenesulfonyl chloride (PTSC) dropwise, and simultaneously add 20 Dissolve 513.31kg (2.57kmol) of % NaOH, ensure the pH of the system is 10-11, the temperature is between 40-60°C, the dropwise addition time is 1.5h, and keep warm for 1h to reach the...

Embodiment 3

[0047] One-step reaction: feed N into reactor 1 2 , add 1000L DMAC after air replacement, start stirring, add 272.75kg (2.50kmol) m-aminophenol (MAP), after dissolving at 20°C, slowly add 566.95kg (2.88kmol) p-toluenesulfonyl isocyanate (PTSI), The dropping time is 4.0h, and the temperature is kept at 30°C, and the temperature is kept for 1h to reach the end point.

[0048] Two-step reaction: p-toluenesulfonyl chloride (PTSC) solution configuration: 619.78kg (3.25kmol) PTSC was dissolved in 900L DMAC.

[0049] Transfer the material in the reactor 1 to N 2 In the reaction kettle 2 of the atmosphere, pump 15% Na in the reaction kettle 2 2 CO 3 Solution 1060kg (1.5kmol), system pH=10-11, slowly add dropwise the DMAC solution of p-toluenesulfonyl chloride (PTSC), simultaneously dropwise add 40% NaOH to dissolve 280kg (2.80kmol), guarantee system pH=10-11, temperature The temperature is between 40-60°C, the dropping time is 1.5h, and the temperature is kept for 1h to reach the ...

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Abstract

A preparation method of a high-whiteness thermosensitive color developing agent containing a sulfonylurea structure comprises the following steps: dissolving MAP in an organic solvent, slowly dropwise adding PTSI into the organic solvent, and carrying out heat preservation to a reaction endpoint to obtain an intermediate product N-p-toluenesulfonyl-N '-(3-hydroxyphenyl) urea system; adding alkali liquor into the obtained intermediate product system for dissolving, then slowly dropwise adding an organic solution of PTSC, simultaneously dropwise adding the alkali liquor to control the pH value of the system, and carrying out heat preservation reaction to the end point to obtain a product N-p-toluenesulfonyl-N '-(3-p-toluenesulfonyloxyphenyl) urea system; adding an alcohol solvent into the prepared N-p-toluenesulfonyl-N-(3-p-toluenesulfonyloxy phenyl) urea system, neutralizing with acid, and filtering to obtain a filter cake; and carrying out post-treatment and vacuum drying on the filter cake to obtain a final product. According to the preparation method disclosed by the invention, the sulfonylurea color developing agent with high yield, high purity, whiter color and less solvent residue can be obtained, and the process operation is more suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of a heat-sensitive color developer, in particular to a preparation method of a high-whiteness heat-sensitive color developer containing a sulfonylurea structure. Background technique [0002] N-p-toluenesulfonyl-N'-(3-p-toluenesulfonyloxyphenyl) urea is a new type of thermosensitive chromogenic agent, which releases hydrogen ions (H + ) to make the heat-sensitive coupler color base develop color. Compared with the carcinogenic phenolic coupler, which is controversial in terms of carcinogenicity, its photostability is higher, and the image is more suitable for long-term storage. [0003] In recent years, the research on N-p-toluenesulfonyl-N'-(3-p-toluenesulfonyloxyphenyl) urea only focuses on the research on the preparation method, and there is little research on the post-treatment of the target product. [0004] Since the production process of thermal paper is to directly compound and coat the color deve...

Claims

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Application Information

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IPC IPC(8): C07C303/38C07C311/60C07C303/40C07C303/36C07C303/44
CPCC07C303/38C07C303/40C07C303/36C07C303/44C07C311/60Y02P20/55
Inventor 刘佳伟张静朱秀全王成鹏
Owner HEBEI JIANXIN CHEM IND CO LTD
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