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A kind of aromatic diamine monomer containing bis-tert-butyl structure and its preparation method and application

A technology of tert-butyl and structural formula, applied in the field of aromatic diamine monomer and its preparation, can solve the problems of low gas permeability, poor dissolving and film-forming property of commercial polyimide, etc., and achieves simple synthesis method and convenient product separation. , the effect of good film formation and gas separation performance

Active Publication Date: 2018-03-02
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The patent of this invention aims to solve the shortcomings of commercialized polyimide, such as poor dissolution and film formation, low gas permeability, etc., and provides an aromatic diamine monomer containing a bis-tert-butyl structure, its preparation method and synthesis of polyether Application in imide; the polyetherimide prepared by the aromatic diamine monomer not only has good solubility and film formation, but also has high gas permeability, and is expected to be applied to a new generation of high-performance polyimide gas Separation membrane field

Method used

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  • A kind of aromatic diamine monomer containing bis-tert-butyl structure and its preparation method and application
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  • A kind of aromatic diamine monomer containing bis-tert-butyl structure and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0030] (1) Add 46.262g (0.1mol) of 9,9-bis(3-tert-butyl-4-hydroxyphenyl)fluorene to a 500ml dry three-necked flask equipped with nitrogen protection, condenser and water separator , 31.51g (0.2mol) of p-chloronitrobenzene, 27.642g (0.2mol) of potassium carbonate, 165ml of N,N-dimethylformamide and 20ml of toluene, after azeotropic dehydration at 150°C for 1 hour, the toluene was distilled off, After continuing to stir and react for 6 hours, cool it and pour it into an ice-water bath, a large amount of solid precipitates out, and is filtered and dried. The crude product is recrystallized with N,N-dimethylformamide to obtain a white crystalline powder which is the intermediate dinitro compound 9. 9-bis[3-tert-butyl-4-(4-nitrophenoxy)phenyl]fluorene, the yield was 82% (as 9,9-bis(3-tert-butyl-4-hydroxyphenyl ) conversion meter of fluorene);

[0031] The melting point of the above-mentioned 9,9-bis[3-tert-butyl-4-(4-nitrophenoxy)phenyl]fluorene is 254~255°C (obtained by DSC test,...

Embodiment 2

[0035](1) Add 46.262g (0.1mol) of 9,9-bis(3-tert-butyl-4-hydroxyphenyl)fluorene to a 500ml dry three-necked flask equipped with nitrogen protection, condenser and water separator , 36.237g (0.23mol) of p-chloronitrobenzene, 41.463g (0.3mol) of potassium carbonate, 260ml of N,N-dimethylformamide and 78ml of toluene, after azeotropic dehydration at 130°C for 3 hours, the toluene was distilled off, After continuing to stir and react for 10 h, cool it and pour it into an ice-water bath, a large amount of solid precipitates out, and is filtered and dried. The crude product is recrystallized with N,N-dimethylacetamide to obtain a white crystalline powder which is the intermediate dinitro compound 9. 9-bis[3-tert-butyl-4-(4-nitrophenoxy)phenyl]fluorene, the yield was 81% (as 9,9-bis(3-tert-butyl-4-hydroxyphenyl ) fluorene conversion meter).

[0036] (2) In a 500ml three-necked flask, add 35.24g (0.05mol) of the dinitro compound 9,9-bis[3-tert-butyl-4-(4-nitrophenoxy) obtained in ste...

Embodiment 3

[0039] In a dry 50ml three-necked round-bottomed flask with nitrogen, add 9,9-bis[3-tert-butyl-4-(4-aminophenoxy)phenyl]fluorene and 3mmol obtained in Example 1 3mmol aromatic dianhydride monomer (take diphenyl ether tetra-acid dianhydride as an example), then add 12ml m-cresol and 0.78g isoquinoline respectively, raise the temperature of the reaction system to 180°C and stir for 20h, then finish the reaction and cool to After room temperature, pour the polymer solution into methanol to obtain a fibrous polyimide polymer.

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Abstract

The invention provides a kind of aromatic diamine monomer containing bis-tert-butyl structure, and its preparation method is: at first by bisphenol compound 9,9-bis(3-tert-butyl-4-hydroxyphenyl) fluorene and p-chloro Nitrobenzene reacts under basic condition, obtains dinitro compound 9,9 bis[3-tert-butyl-4-(4-nitrophenoxy) phenyl] fluorene; Then dinitro compound is in Carry out catalytic reduction in an organic solvent to obtain the aromatic diamine monomer 9,9-bis[3-tert-butyl-4-(4-aminophenoxy)phenyl]fluorene. The bis-tert-butyl-containing aromatic diamine monomer can be applied to the preparation of soluble polyetherimide, and the prepared polyetherimide has good film-forming properties, high thermal performance and excellent gas separation performance.

Description

technical field [0001] The invention belongs to the field of aromatic diamine compounds and their preparation and application, and in particular relates to an aromatic diamine monomer containing a bis-tert-butyl structure and its preparation method and application. Background technique [0002] Polymer membrane separation technology is a green chemical separation technology that has developed rapidly in recent years. It has important application value in some fields related to environmental protection and energy, such as nitrogen and oxygen separation, carbon dioxide enrichment, natural gas dehumidification, and hydrogen recovery. As a key component of membrane separation technology, the performance of polymer membrane materials directly affects the separation efficiency and performance of the entire separation equipment. Polyimide has been used in the field of polymer membrane separation due to its excellent thermal properties, mechanical properties, and easy design of mole...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/90C07C213/02C08G73/10
Inventor 汪称意徐常赵晓燕李坚任强
Owner CHANGZHOU UNIV
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