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Preparation method of thermosensitive color developer containing sulfonylurea structure

A technology of sulfonylurea and color developer, applied in the field of preparation of heat-sensitive color developer, can solve the problems of destroying the chemical structure of the color developer, deterioration of by-products, etc.

Active Publication Date: 2017-06-20
康爱特维迅(蓬莱)化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The chemical properties of the sulfonylurea group are very active, which makes the heat-sensitive chromogenic agent containing the sulfonylurea structure very easy to react with non-inert solvents, such as methanol, ethanol, acetonitrile, DMF, water, etc. Destroy the chemical structure of the developer, produce by-products and cause deterioration

Method used

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  • Preparation method of thermosensitive color developer containing sulfonylurea structure
  • Preparation method of thermosensitive color developer containing sulfonylurea structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Esterification reaction

[0037] Add 200ml of acetone into a 500ml four-neck glass flask, add 56.6g of MAP under stirring, stir at room temperature to completely dissolve, add 30g of caustic soda, cool to 17°C and stir for 2 hours to basically dissolve caustic soda, then add 99.2g of PTSC, and use 0.5 After adding PTSC, continue to react for 2 hours. Add 200ml of water, recover acetone by distillation under normal pressure until the gas phase temperature is 100°C, replenish 200ml of water, reduce to room temperature, suction filter, wash with water until neutral, dry the wet filter cake to obtain 123.1g of 3-aminophenyl p-toluenesulfonate, and collect The rate is 90.1%.

[0038] Addition reaction

[0039] Add 300ml of acetone into a 500ml four-neck glass flask, add 60g of 3-aminophenyl p-toluenesulfonate under stirring, and add 54.0g of PTSI dropwise for 2 hours. Continue to react for 1 hour after adding PTSI, filter, wash the filter cake with 100ml of acetone, dry t...

Embodiment 2

[0043] Esterification reaction

[0044]Add 200ml of acetone into a 500ml four-necked glass flask, add 56.6g of MAP under stirring, stir at room temperature to completely dissolve, add 45g of caustic soda, cool down to 23°C and stir for 2 hours to basically dissolve the caustic soda, add 99.2g of PTSC for 0.5 hours . After the addition of PTSC, the reaction was continued for 2 hours. Add 200ml of water, recover acetone by normal pressure distillation until the gas phase temperature is 100°C, replenish 200ml of water, reduce to room temperature, suction filter, wash with water until neutral, dry the wet filter cake to obtain 128.2g of 3-aminophenyl p-toluenesulfonate, and collect The rate is 93.9%.

[0045] Addition reaction

[0046] Add 780ml of toluene to a 1000ml four-necked glass flask, add 60g of 3-aminophenyl p-toluenesulfonate under stirring, heat up to 60°C, add 5g of activated carbon, stir for 0.5 hours, filter, and wash the filtrate (toluene layer) with hot water un...

Embodiment 3

[0049] The impact of acid-binding agent on reaction in embodiment 3 esterification

[0050] Operation steps: Add 200ml of acetone into a 500ml four-neck glass flask, add 56.6g of MAP under stirring, stir at room temperature to completely dissolve, add 30g of acid-binding agent, cool down to 17°C and stir for 2 hours to basically dissolve the acid-binding agent, then add PTSC 99.2g, it takes 0.5 hours, and the reaction is continued for 2 hours after the addition of PTSC. Add 200ml of water, recover acetone by normal pressure distillation until the gas phase temperature is 100°C, make up 200ml of water, reduce to room temperature, suction filter, wash with water until neutral, dry the wet filter cake to obtain 3-aminophenyl p-toluenesulfonate, calculate the yield .

[0051] Acid-binding agent added to the group: (1) potassium hydroxide; (2) sodium hydroxide; (3) sodium carbonate; (4) sodium bicarbonate.

[0052] See Table 1 for the yield of 3-aminophenyl p-toluenesulfonate.

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Abstract

The invention discloses a preparation method of thermosensitive color developer containing a sulfonylurea structure. The preparation method comprises the following steps: (1) esterification: m-aminophenol and p-toluenesulfonyl chloride react under alkaline conditions to obtain 3-amino phenyl p-toluenesulfonate; (2) addition: the obtained 3-amino phenyl p-toluenesulfonate reacts with p-toluenesulfonyl isocyanate (PTSI) to obtain a crude product of the thermosensitive color developer containing the sulfonylurea structure; and (3) refining: the crude product obtained in the step (2) is dissolved into an alkaline solution and acidification and organic solvent treatment are carried out to obtain the thermosensitive color developer containing the sulfonylurea structure.

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 heat-sensitive color developer containing a sulfonylurea structure. Background technique [0002] The function of the heat-sensitive color developer is to release hydrogen ions (H+) when heated and melted to make the color base of the heat-sensitive color coupler develop color. Commonly used heat-sensitive color developers include bisphenol A, bisphenol S and 4-hydroxy-4 '-isopropoxydiphenyl sulfone, etc. These color developers are synthesized from phenol, and the phenolic hydroxyl group provides hydrogen ions (H+) to produce color development. After color development, its image stability is poor, and the image will become blurred when left for a long time, and the scope of use is limited; there are also controversies in terms of carcinogenicity, and a heat-sensitive chromogenic agent with a new structure is needed to replace t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/36C07C311/60
Inventor 林淑美高景庆任志惠王毅
Owner 康爱特维迅(蓬莱)化学有限公司
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