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A class of polyimide containing four major substituent side groups and twisted non-coplanar structure and preparation method thereof

A polyimide, non-coplanar technology, which is applied in the field of polyimide and its preparation containing four major substituted side groups and twisted non-coplanar structures, can solve the problem of low gas separation performance and polyimide composition Difficult membrane and other problems, to achieve good thermal stability and gas separation performance, simple synthesis route, improve the effect of film formation performance and gas separation performance

Active Publication Date: 2017-01-18
常州亚安新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to improve the existing commercial polyimide film-forming difficulties, low gas separation performance, and inability to meet the development needs of modern high-efficiency gas separation equipment. Polyimide with non-coplanar structure and its preparation method; multiple large substituted side groups and highly twisted non-coplanar structure are simultaneously introduced into the molecular structure unit of polyimide, which effectively improves the film-forming performance of the polymer and gas separation performance

Method used

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  • A class of polyimide containing four major substituent side groups and twisted non-coplanar structure and preparation method thereof
  • A class of polyimide containing four major substituent side groups and twisted non-coplanar structure and preparation method thereof
  • A class of polyimide containing four major substituent side groups and twisted non-coplanar structure and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Add 28.492g (0.05mol) of 2,2'-bis(3,5-dibromo-4-fluorophenyl) to a 1000ml three-necked flask equipped with mechanical stirring, condensing device and nitrogen protection Sulfone and 37.986g (0.20mol) of 4-trifluoromethylphenylboronic acid, 2.311g (0.002mol) of tetrakis (triphenylphosphine) palladium, 42.396g (0.40mol) of sodium carbonate, 170g of water, 85ml of toluene and 85ml of ethylene glycol dimethyl ether, stirred at room temperature (25°C) for 10 minutes, then heated to reflux, reacted for 8 hours, evaporated the organic solvent, and filtered the crude product, washed with water and dried, and used N,N- Further recrystallization of dimethylformamide gave the intermediate bisfluoro compound 2,2'-bis[3,5-bis(4-trifluoromethylphenyl)-4-fluorophenyl]sulfone as a white powder, producing The rate was 81% (calculated based on the conversion rate of 2,2'-bis(3,5-dibromo-4-fluorophenyl)sulfone).

[0031] The melting point of the 2,2'-bis[3,5-bis(4-trifluoromethylphen...

Embodiment 2

[0037] In a dry 50ml three-necked round-bottomed flask with nitrogen, add 3.0266g (3mmol) of 2,2'-bis[3,5-bis(4-trifluoromethylphenyl)-4 obtained in Example 1 -(4-aminophenoxy)phenyl]sulfone and 0.8827 (3mmol) aromatic dianhydride monomer (taking biphenyltetralic acid dianhydride as an example), then add 23.5g N-methylpyrrolidone, room temperature (25°C) After stirring and reacting for 12 hours, the temperature was further raised to 180° C., and after stirring and reacting with water for 20 hours through a nitrogen stream, the reaction solution was poured into ethanol to obtain a fibrous polyimide polymer with a yield of 98% (with 2, Conversion rate calculation of 2'-bis[3,5-bis(4-trifluoromethylphenyl)-4-(4-aminophenoxy)phenyl]sulfone).

[0038] FT-IR(KBr)ν / cm -1 :3067,1782,1724,1387,1329,1178,1129. 1 HNMR (CDCl 3 ,400MHz)δ:8.04(s,4H),7.26(s,16H),6.27(d,4H),6.20(d,4H),3.31(s,4H). image 3 , Figure 4 shown.

Embodiment 3

[0040] In a dry 50ml three-necked round-bottomed flask with nitrogen, add 3.0266g (3mmol) of 2,2'-bis[3,5-bis(4-trifluoromethylphenyl)-4 obtained in Example 1 -(4-aminophenoxy)phenyl]sulfone and 0.930 (3mmol) aromatic dianhydride monomer (taking diphenyl ether tetra-acid dianhydride as an example), then add 35.1g N-methylpyrrolidone, room temperature (25 ℃ ) after stirring and reacting for 24 hours, further warming up to 200° C., and stirring and reacting with water for 8 hours through nitrogen flow, the reaction solution was poured into ethanol to obtain a fibrous polyimide polymer with a yield of 98% (with 2 , 2'-bis[3,5-bis(4-trifluoromethylphenyl)-4-(4-aminophenoxy)phenyl]sulfone conversion calculation).

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Abstract

The invention provides a polyimide high-performance polymer containing four substituent pendant groups and a distorted non-coplanar structure synchronously. The polymer is excellent in dissolving film-forming property, high in thermal stability and good in gas separating property. The preparation process comprises the following steps: under protection of nitrogen, dissolving an aromatic diamine monomer containing the four substituent pendant groups and the distorted non-coplanar structure synchronously and an anhydride monomer at an equal molar ratio in an N-methyl pyrrolidinone solution, stirring to take a reaction for 12-24 hours at the room temperature, further raising the temperature to 180-200 DEG C, feeding water with nitrogen flow, stirring and keeping the reaction for 8-20 hours, then pouring the reaction solution to ethanol, and obtaining the fibrous polyimide polymer.

Description

technical field [0001] The invention belongs to the field of polyimides containing large substituted side group structures and the preparation thereof, in particular to a class of polyimides simultaneously containing four large substituted side groups and distorted non-coplanar structures and a preparation method thereof. Background technique [0002] Polyimide is an important class of high-temperature-resistant polymers. Due to its excellent thermal and mechanical properties, it can be used as a self-supporting membrane in the field of gas separation, including nitrogen and oxygen separation, carbon dioxide enrichment, natural gas dehumidification, hydrogen recovery, etc. separation process. Due to the regular structure of molecular chains and strong intermolecular interactions, commercial polyimide usually exhibits shortcomings such as refractory, insoluble, and low gas permeability, which cannot meet the development needs of modern high-efficiency gas separation equipment...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/10C07C315/04C07C317/22
Inventor 汪称意徐常陈文涛赵晓燕李坚任强
Owner 常州亚安新材料有限公司
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