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Benzotriazole compound containing sulfur, and its preparing method

A benzotriazole and benzotriazole technology are applied in the field of sulfur-containing benzotriazole compounds and their preparation, can solve problems such as unreported, and achieve the effect that the preparation method is simple and feasible

Inactive Publication Date: 2008-07-16
GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In summary, although the 5-position of the benzotriazole compound is disclosed by the compound of R-S-group substitution at home and abroad, the compound that the 5-position of the benzotriazole compound is substituted by the R-S-S-group has not yet been published. see the report

Method used

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  • Benzotriazole compound containing sulfur, and its preparing method
  • Benzotriazole compound containing sulfur, and its preparing method
  • Benzotriazole compound containing sulfur, and its preparing method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Put a 250ml four-neck flask on a magnetic stirrer with a heating device, connect a nitrogen inlet tube, install a thermometer and a water separator condenser tube, add 3.2 grams of sodium hydroxide (0.08mol) and 7.25 grams of n-butylsulfide Alcohol (0.08 mol). Stirring was started and the sodium hydroxide was dissolved by slight heating. A further 12.5 ml of toluene was added, the mixture was heated to reflux to drive off the water formed (approximately 1.4 ml), and the toluene was distilled off.

[0029] Then the reaction mixture was cooled to room temperature, the water separator was removed, and the condenser was directly connected to the grinding port of the flask. Then add 30ml of N-methylpyrrolidone (0.31mol), 7.16 grams of 2-(2'-hydroxyl-3', 5'-di-tert-butylphenyl)-5-chlorobenzotriazole (0.02 mol), heated to 186°C, and reacted for 18 hours. The solution was cooled to room temperature. Slowly add 7.5ml of water and 7.5ml of concentrated hydrochloric acid under...

Embodiment 2

[0036] Put a 250ml four-neck flask on a magnetic stirrer with a heating device, connect a nitrogen inlet tube, install a thermometer and a condenser tube, add 7.25 grams of n-butanethiol (0.08mol), and add 2.3 grams of sodium hydride under stirring (0.096 mol).

[0037] Add 30ml N-methylpyrrolidone (0.31mol) and 7.16 grams of 2-(2'-hydroxyl-3', 5'-di-tert-butylphenyl)-5-chlorobenzotriazole ( 0.02mol), heated to 186°C, and reacted for 18 hours. The solution was cooled to room temperature. Slowly add 9.3ml of water and 9.3ml of concentrated hydrochloric acid under stirring, a precipitate precipitates out after cooling, filter, wash the precipitate with petroleum ether, and dry to obtain 5,5'-dithio-bis[2-(2-hydroxy-3, 5-di-tert-butylphenyl)-2H-benzotriazole], the yield was 60%.

[0038] Physicochemical properties, spectral data and UV absorption of 5,5'-dithio-bis[2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole] prepared in this example (measure in chloroform) charact...

Embodiment 3

[0040] Put a 250ml four-neck flask on a magnetic stirrer with a heating device, connect a nitrogen inlet tube, install a thermometer and a condenser tube, add 7.25 grams of n-butanethiol (0.08mol), and add 1.92 grams of sodium hydride under stirring (0.08 mol).

[0041] Add 30ml N-methylpyrrolidone (0.31mol) and 7.16 grams of 2-(2'-hydroxyl-3', 5'-di-tert-butylphenyl)-5-chlorobenzotriazole ( 0.01mol), heated to 186°C, and reacted for 18 hours. The solution was cooled to room temperature. Slowly add 7.5ml of water and 7.5ml of concentrated hydrochloric acid under stirring, a precipitate precipitates out after cooling, filter, wash the precipitate with petroleum ether, and dry to obtain 5,5'-dithio-bis[2-(2-hydroxy-3, 5-di-tert-butylphenyl)-2H-benzotriazole], yield 20%.

[0042] Physicochemical properties, spectral data and UV absorption of 5,5'-dithio-bis[2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole] prepared in this example (measure in chloroform) characteristic ...

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Abstract

This invention discloses new ultraviolet absorbent 5, 5'-disulfo-bi[2- (2-hydroxy group -3,5-bi tert-butyl phenyl group)-2H-benzotriazole] and its preparation method. This compound can be made by ortho butyl sulfhydrate reacting with alkali to synthesize ortho butyl sulfhydrate alkali metal salt, then 5-chlorine-2-(2-hydroxy group-3,5- bi tert-butyl phenyl group)-2H-benzotriazole is made in non proton solvent. The compound is high efficient UVA ultraviolet ray absorbent material, it can protect plastic, pain and human skin from this kind ultraciolet damaging, and its preparation method is simple, reaction intermediate doesn't need separating and purification, its yield can reach 60 percent.

Description

technical field [0001] The invention relates to the field of ultraviolet absorbers, in particular to a sulfur-containing benzotriazole compound and a preparation method thereof. Background technique [0002] Benzotriazole compounds are an important class of ultraviolet light absorbers, which have been widely used in polymer industry, coating industry and cosmetic industry. Now people have synthesized various structures of benzotriazole compounds. Patents EP0323853, US3766205 and US5942626 disclose the synthesis method of sulfur-containing benzotriazole compounds; patent EP0323853 discloses a kind of 5-methyl-sulfur-2-(2-hydroxyl-3 -Second-butyl-5-tert-butylphenyl)-2H-benzotriazole compound; Patent US3766205 discloses 5-mercapto-2-(2-hydroxyl-3,5-di-tert-butylbenzene base)-2H-benzotriazole compound synthesis method; patent US5942626 discloses that the 5-position of the benzene ring in a variety of 2H-benzotriazole compounds is replaced by an alkylthio group, an arylthio gro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/20
Inventor 徐社阳曹德榕陈鸣才
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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