Aromatic diamine monomer containing di-tert-butyl structure and preparation method and application of aromatic diamine monomer

An aromatic diamine and tert-butyl technology, which is applied in the field of aromatic diamine monomer and its preparation, can solve the problems of poor dissolving film-forming property and low gas permeability of commercial polyimide, and achieve convenient product separation and synthesis. Effect of simple method, good film formation and gas separation performance

Active Publication Date: 2015-02-18
CHANGZHOU UNIV
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  • 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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  • Aromatic diamine monomer containing di-tert-butyl structure and preparation method and application of aromatic diamine monomer

Examples

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 an aromatic diamine monomer containing a di-tert-butyl structure. A preparation method of the aromatic diamine monomer comprises the following steps: a bisphenol compound 9,9-di(3-tert-butyl-4-hydroxyphenyl)fluorine and parachloronitrobenzene react under an alkaline condition to obtain a dinitro compound 9,9-di(3-tert-butyl-4-(4-nitrophenoxy)phenyl)fluorine; then the dinitro compound is subjected to catalytic reduction in an organic solvent to obtain the aromatic diamine monomer 9,9-di(3-tert-butyl-4-(4-amidophenoxy)phenyl)fluorine. The aromatic diamine monomer can be applied to preparation of soluble polyetherimide, and the prepared polyetherimide has a favourable film-forming property, a high thermal property and an excellent gas separation property.

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 Applications(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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