Aromatic diamine monomer simultaneously containing four lateral substituents and having twisted non-coplanar structure and preparation method thereof

An aromatic diamine and non-coplanar technology, which is applied in the field of aromatic diamine monomers and their preparation, can solve difficult problems such as easy purification and separation, simple synthesis route, and improved gas separation performance

Inactive Publication Date: 2015-03-25
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Aromatic diamine monomers containing large substituted side group structures are key monomers for the preparation of polyimide gas sepa

Method used

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  • Aromatic diamine monomer simultaneously containing four lateral substituents and having twisted non-coplanar structure and preparation method thereof
  • Aromatic diamine monomer simultaneously containing four lateral substituents and having twisted non-coplanar structure and preparation method thereof
  • Aromatic diamine monomer simultaneously containing four lateral substituents and having twisted non-coplanar structure and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (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).

[0024] The melting point of the 2,2'-bis[3,5-bis(4-trifluoromethylphen...

Embodiment 2

[0029] (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 41.785g (0.22mol) of 4-trifluoromethylphenylboronic acid, 3.466g (0.003mol) of tetrakis (triphenylphosphine) palladium, 52.995g (0.50mol) of sodium carbonate, 265g of water, 158ml of toluene and 158ml of ethylene glycol dimethyl ether, stirred at room temperature (25°C) for 10 minutes, then heated to reflux, reacted for 16 hours, evaporated the organic solvent, and filtered the crude product, washed with water, 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 82% (calculated based on the conversion rate of 2,2'-bis(3,5-dibromo-4-fluorophenyl)sulfone).

[0030](2) In a 250ml three-neck flask equipped with mechanical stirrin...

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Abstract

The invention provides an aromatic diamine monomer simultaneously containing four lateral substituents and having a twisted non-coplanar structure: 2,2'-di[3,5-di(4-trifluoromethylphenyl)-4-(4-aminophenoxy) phenyl] sulfone. A preparation method comprises: reacting 2,2'-di(3,5-dibromo-4-fluorophenyl) sulfone and 4-trifluoromethylphenyl boracic acid under an alkali condition in the presence of a catalyst to obtain an intermediate difluoride, further reacting the intermediate difluoride and 4-aminophenol under an alkali condition, and purifying a crude product to obtain the aromatic diamine monomer containing big tetra (4-trifluoromethyl) phenyl lateral substituents. The diamine monomer, which simultaneously contains a few big lateral substituents and has a highly twisted non-coplanar structure, can be applied to preparation of high-performance polyimide gas separation membrane materials.

Description

technical field [0001] The invention belongs to the field of aromatic diamine monomers and preparation thereof, in particular to an aromatic diamine monomer containing four major substituted side groups and a distorted non-coplanar structure and a preparation method thereof. Background technique [0002] Polyimide is a kind of high-temperature-resistant polymer containing five-membered imide ring structure. Due to its excellent thermal properties, mechanical properties and electrical properties, it can be used as high-temperature-resistant structural materials, gas separation membrane materials, and microelectronic packaging materials. Wait. When used as a gas separation membrane material, most of the commercialized polyimides have disadvantages such as complicated molding process and low gas separation performance. In order to meet the needs of the development of high-efficiency gas separation equipment, it is of great research value to design and modify the molecular stru...

Claims

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Application Information

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IPC IPC(8): C07C315/04C07C317/22B01D71/64
Inventor 汪称意陈文涛徐常赵晓燕李坚任强
Owner CHANGZHOU UNIV
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