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Difunctional compound containing hindered phenol and crown ether structures, synthetic method and application thereof

A synthesis method and technology of hindered phenols, applied in the direction of organic chemistry, etc., can solve the problem of reducing the antioxidant effect

Active Publication Date: 2016-07-06
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, hindered phenolic antioxidants and amphiphilic antistatic agents are widely used in polyolefin products. The hindered phenolic antioxidants are relatively uniformly dispersed in the resin to play an antioxidative role, but after the resin is molded, only the surface and the air Contact therefore only a small number of hindered phenolic molecules act as an antioxidant, thus greatly reducing the antioxidant effect

Method used

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  • Difunctional compound containing hindered phenol and crown ether structures, synthetic method and application thereof
  • Difunctional compound containing hindered phenol and crown ether structures, synthetic method and application thereof
  • Difunctional compound containing hindered phenol and crown ether structures, synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0113] Under nitrogen protection, 220g of 2,6-di-tert-butyl-p-cresol and 150g of dimethyl sulfate were dissolved in 2.5L of dry chloroform. The reaction solution was heated to 60° C. under stirring in a 5 L three-necked flask, and the reaction continued for 1.5 hours. The reaction solution was cooled to 25°C and extracted four times with 1LO.5 mol / L potassium carbonate solution, and the organic layer was dried with anhydrous magnesium sulfate for 24 hours. The anhydrous magnesium sulfate desiccant in the solution was removed by filtration, and the solvent was distilled off under reduced pressure to obtain 215.3 g of 2,6-di-tert-butyl-p-methylanisole, with a yield of 92%.

[0114] Under nitrogen protection, 215.3g of 2,6-di-tert-butyl-p-methylanisole was added into a 5L three-necked flask containing 3L of carbon tetrachloride. Then add 161g of N-bromosuccinimide and 2g of azobisisobutyronitrile, heat the reaction solution to 77°C for 3 hours and stop heating, cool the reaction...

Embodiment 2

[0125] Under nitrogen protection, 220g of 2,6-di-tert-butyl-p-cresol and 150g of dimethyl sulfate were dissolved in 2.5L of dry chloroform. The reaction solution was heated to 60° C. under stirring in a 5 L three-necked flask, and the reaction continued for 1.5 hours. The reaction solution was cooled to 25°C and extracted four times with 1LO.5 mol / L potassium carbonate solution, and the organic layer was dried with anhydrous magnesium sulfate for 24 hours. The anhydrous magnesium sulfate desiccant in the solution was removed by filtration, and the solvent was evaporated under pressure to obtain 215.3 g of 2,6-di-tert-butyl-p-methylanisole, with a yield of 92%.

[0126] Under nitrogen protection, 215.3g of 2,6-di-tert-butyl-p-methylanisole was added into a 5L three-necked flask containing 3L of carbon tetrachloride. Then add 161g of N-bromosuccinimide and 2g of azobisisobutyronitrile, heat the reaction solution to 77°C for 3 hours and stop heating, cool the reaction solution t...

Embodiment 3

[0137] Under nitrogen protection, 220g of 2,6-di-tert-butyl-p-cresol and 150g of dimethyl sulfate were dissolved in 2.5L of dry chloroform. The reaction solution was heated to 60° C. under stirring in a 5 L three-necked flask, and the reaction continued for 1.5 hours. The reaction solution was cooled to 25°C and extracted four times with 1LO.5 mol / L potassium carbonate solution, and the organic layer was dried with anhydrous magnesium sulfate for 24 hours. The anhydrous magnesium sulfate desiccant in the solution was removed by filtration, and the solvent was distilled off under reduced pressure to obtain 215.3 g of 2,6-di-tert-butyl-p-methylanisole, with a yield of 92%.

[0138] Under nitrogen protection, 215.3g of 2,6-di-tert-butyl-p-methylanisole was added into a 5L three-necked flask containing 3L of carbon tetrachloride. Then add 161g of N-bromosuccinimide and 2g of azobisisobutyronitrile, heat the reaction solution to 77°C for 3 hours and stop heating, cool the reaction...

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Abstract

A compound containing both anti-static and anti-oxidizing functional groups is composed of a hindered phenol unit, a crown ether unit, and a straight chain segment unit. The content of effective functional groups in unit mass of the compound and the compatibility of the compound with resin are regulated by controlling the length of the straight chain segment unit. Through migration of the crown ether group, the hindered phenol unit is migrated to a surface layer of resin, so that oxidization in air can be eliminated more effectively. The hindered phenol unit has a large space structure, so that the crown ether structure is prevented from falling off from the surface of the resin, thereby increasing anti-static time of the compound. The compound can be used as an anti-static and anti-oxidizing agent for polypropylene or polyethylene.

Description

technical field [0001] The present invention relates to an anti-oxidation and antistatic bifunctional compound and its synthesis method, especially to a compound containing both hindered phenol groups and crown ether structure hydrophilic groups in its molecule and its synthesis method. The present invention also relates to the compound Application in polyolefin resin. Background technique [0002] Hindered phenolic compounds can compete with polymers for peroxy radicals formed in auto-oxidation, and through the transfer of hydrogen atoms, form carboxylic acids and a stable antioxidant radical, which has the ability to capture active free radicals. ability to terminate the second kinetic chain of the polymer chain oxidation reaction. Hindered phenolic antioxidants are usually produced by transesterification under alkaline conditions. Such as: US4716244, US5481023, US5563291, US6878843, US2003166962 describe using lithium amide, lithium acetate, sodium acetate, magnesium ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D273/08C08L23/00C08L23/12C08K5/35
Inventor 李广全李丽段宏义吴建刘义刘敏杨柳陈旭邓守军李朋朋张鹏魏福庆张华强樊洁慕雪梅
Owner PETROCHINA CO LTD