Substituted anilino-benzothiazole-2-thioketone compound as well as preparation method and application thereof

A benzothiazole and compound technology, applied in the field of organic synthesis, can solve problems such as easy migration

Pending Publication Date: 2020-05-15
江苏方圆芳纶研究院有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Aiming at the problem of easy migration of rubber anti-aging agents in the prior art, the purpose of the present invention is to provide a compound ...

Method used

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  • Substituted anilino-benzothiazole-2-thioketone compound as well as preparation method and application thereof
  • Substituted anilino-benzothiazole-2-thioketone compound as well as preparation method and application thereof
  • Substituted anilino-benzothiazole-2-thioketone compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1 (preparation of 4-aminodiphenylamine)

[0073] In a 700ml steel autoclave, under a nitrogen atmosphere, 110g (1.0mol) of hydroquinone, 108g of pulverized γ-alumina catalyst and 186g (2.0mol) of aniline were added to the autoclave, and the reaction temperature was 270°C, pressure 2MPa, reaction time 4 hours. The obtained reaction product was extracted with dichloromethane, and the extracted filtrate was subjected to vacuum distillation to obtain 157.3 g of 4-hydroxydiphenylamine with a yield of 85%.

[0074] In a 700ml steel autoclave, under a nitrogen atmosphere, 44.4g (0.24mol) of 4-hydroxydiphenylamine, 88g of γ-alumina catalyst and 120g (7.0mol) of ammonia were added to the autoclave, the reaction temperature The temperature is 350°C, the pressure is 3.5 MPa, and the reaction time is 2 hours. The obtained reaction product was extracted with dimethylformamide, and then the extracted filtrate was distilled under reduced pressure to obtain 36.21 g of 4-am...

Embodiment 2

[0075] Embodiment 2 (preparation of 4-amino-2'-methyl-diphenylamine)

[0076] In a 700ml steel autoclave, under a nitrogen atmosphere, 110g (1.0mol) of hydroquinone, 108g of pulverized γ-alumina catalyst and 214g (2.0mol) of o-toluidine were added to the autoclave, and the reaction The temperature is 270° C., the pressure is 0.6 MPa, and the reaction time is 3 hours. The obtained reaction product was extracted with dichloromethane, and the extracted filtrate was distilled under reduced pressure to obtain 163.2 g of 4-hydroxy-2'-methyldiphenylamine with a yield of 82%.

[0077] In a 700ml steel autoclave, under a nitrogen atmosphere, 47.8g (0.24mol) of 4-hydroxy-2'-methyldiphenylamine, 88g of gamma-alumina catalyst and 85g (5.0mol) of ammonia were added In the autoclave, the reaction temperature is 350° C., the pressure is 27 MPa, and the reaction time is 2 hours. The obtained reaction product was extracted with dimethylformamide, and then the extracted filtrate was distilled...

Embodiment 3

[0078] Embodiment 3 (preparation of 4-amino-3'-methyl-diphenylamine)

[0079] In a 700ml steel autoclave, under a nitrogen atmosphere, 110g (1.0mol) of hydroquinone, 108g of crushed γ-alumina catalyst and 214g (2.0mol) of m-toluidine were added to the autoclave, and the reaction The temperature is 270° C., the pressure is 2 MPa, and the reaction time is 3 hours. The obtained reaction product was extracted with dichloromethane, and the extracted filtrate was distilled under reduced pressure to obtain 165.2 g of 4-hydroxy-3'-methyldiphenylamine with a yield of 83%.

[0080] In a 700ml steel autoclave, under a nitrogen atmosphere, 47.8g (0.24mol) of 4-hydroxy-3'-methyldiphenylamine, 88g of γ-alumina catalyst and 85g (5.0mol) of ammonia were added In the autoclave, the reaction temperature is 350° C., the pressure is 26 MPa, and the reaction time is 2 hours. The obtained reaction product was extracted with dimethylformamide, and then the extracted filtrate was distilled under re...

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Abstract

The invention discloses a substituted anilino-benzothiazole-2-thioketone compound and a preparation method thereof. In addition, the invention also relates to an application of the compound in rubberproducts. The substituted anilino-benzothiazole-2-thioketone compound disclosed by the invention not only can promote rubber vulcanization, but also can prolong the service life of the rubber products.

Description

[0001] field of invention [0002] The invention relates to the field of organic synthesis, in particular to a substituted anilino-benzothiazole-2-thione compound, a preparation method thereof and an application in the production of rubber products. Background technique [0003] Rubber additives are mainly anti-aging agents and accelerators, in addition to a wide variety of other processing aids. They are an indispensable and important part of the rubber industry, and play an important role in improving rubber properties, reducing production costs, and extending product life. [0004] Rubber accelerator refers to the rubber vulcanization accelerator, which plays a very important role in the rubber vulcanization process. Rubber vulcanization is mainly carried out with sulfur, but the reaction between sulfur and rubber is relatively slow, so vulcanization accelerators came into being. Adding the accelerator to the rubber compound can promote the activation of the vulcanizing a...

Claims

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Application Information

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IPC IPC(8): C07D277/70C08L7/00C08K13/04C08K5/47
CPCC07D277/70C08K5/47C08K13/04C08L2201/08C08L7/00
Inventor 王农跃瞿雄伟沙艳松陈莉杨文学闻国强
Owner 江苏方圆芳纶研究院有限公司
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