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Diamine monomer containing diphenylamine-fluorene, preparation method and application of same in polyimide preparation

A polyimide and dimethyl fluorene diamine technology, which is applied in the field of polyimide preparation, can solve the problems of single polyimide species, and achieve the effects of improving solubility, large application prospects, and improving stability

Active Publication Date: 2015-11-25
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the polyimide species containing triphenylamine groups is relatively single at present, and polyimides with multiple functions are rarely reported. Therefore, designing and synthesizing new diamine monomers and preparing polyimides from them imine becomes necessary

Method used

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  • Diamine monomer containing diphenylamine-fluorene, preparation method and application of same in polyimide preparation
  • Diamine monomer containing diphenylamine-fluorene, preparation method and application of same in polyimide preparation
  • Diamine monomer containing diphenylamine-fluorene, preparation method and application of same in polyimide preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Preparation of N,N-bis(4-aminophenyl)-9,9-dimethylfluorene

[0031] Step 1: Add 12g (57mmol) of 2-amino-9,9-dimethylfluorene, 12.2g (114mmol) of p-fluoronitrobenzene, 13g (114mmol) of fluorine to a 250mL three-necked flask equipped with mechanical stirring Cesium chloride, add 100mL dimethyl sulfoxide as a solvent, react at 160°C for 20h, discharge in ethanol, and recrystallize with glacial acetic acid to obtain yellow N,N-bis(4-nitrophenyl)-9,9- Dimethylfluorene 21.2g, yield rate is 80%;

[0032] The second step reaction: add 20g of N,N-bis(4-nitrophenyl)-9,9-dimethyl prepared in the first step to a 500mL three-necked flask equipped with a magnet, a thermometer and a condenser Base fluorene, 2g of Pd / C with a mass fraction of 10%, add 200mL of ethanol as a solvent, and stir evenly to obtain a suspension. After heating to reflux, slowly dropwise add N,N-bis(4-nitrophenyl)-9,9-dimethylfluorene with a molar ratio of 20:1 and 85% hydrated solution to the suspe...

Embodiment 2

[0033] Example 2: Preparation of polyimide by polymerization of N,N-bis(4-aminophenyl)-9,9-dimethylfluorene and pyromellitic anhydride

[0034]Feed nitrogen into the three-necked flask equipped with magneton, nitrogen gas inlet and outlet, and thermometer, add 0.3912g (1mmol) N,N-bis(4-aminophenyl)-9,9-bis Add 8mL of DMAc solvent to dissolve methylfluorene, slowly add 0.2181g (1mmol) pyromellitic anhydride, stir at room temperature for 6h, add 2mL pyridine and 4mL acetic anhydride, heat to 100°C and continue the reaction for 1.5h, after the reaction is completed, cool to room temperature , discharged into ethanol to obtain a dark yellow powder, reflux washed with ethanol three times, and dried in a vacuum oven at 100° C. to obtain a pyromellitic anhydride polyimide with a mass of 0.5913 g.

Embodiment 3

[0035] Example 3: Preparation of polyimide by polymerization of N,N-bis(4-aminophenyl)-9,9-dimethylfluorene and 3,3',4,4'-biphenyltetracarboxylic anhydride

[0036] Feed nitrogen into the three-necked flask equipped with magneton, nitrogen gas inlet and outlet, and thermometer, add 0.3912g (1mmol) N,N-bis(4-aminophenyl)-9,9-bis Add 10mL of DMAc solvent to dissolve methylfluorene, slowly add 0.2942g (1mmol) 3,3',4,4'-biphenyltetracarboxylic anhydride, stir at room temperature for 6h, add 2mL pyridine and 4mL acetic anhydride, heat to 100°C Continue the reaction for 1.5h, cool to room temperature after the reaction is complete, discharge the material into ethanol to obtain a dark yellow powder, reflux wash with ethanol three times, and dry in a vacuum oven at 100°C to obtain biphenyltetracarboxylic anhydride polyimide with a mass of 0.6431g .

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Abstract

The invention discloses diamine monomer containing diphenylamine-fluorene, a preparation method and the application of same in polyimide preparation and belongs to the technical field of organic compound preparation. The monomer is N, N-dual (4-aminophenyl)-9, 9-dimethyl fluorene. A synthetic method comprise the following two steps that 1, under the action of cesium fluoride, 2 amino-9, 9-dimethyl fluorene and p-fluoronitrobenzene are subjected to nucleophilic substitution, and the N, N-dual (4-aminophenyl)-9, 9-dimethyl fluorene is obtained; then Pd / C serves as a catalyst and hydrazine hydrate serves as a reducing agent, and the N, N-dual (4-aminophenyl)-9, 9-dimethyl fluorene is obtained. According to the application, the N, N-dual (4-aminophenyl)-9, 9-dimethyl fluorene diamine monomer is involved into reaction with various dianhydride, and polyimide is obtained through the preparation. According to the diamine monomer containing the diphenylamine-fluorene, the preparation method and the application of same in polyimide preparation, by means of the structure peculiar to the diamine monomer, obtained polymer has good solubleness, and the unique photoelectric property is achieved; the diamine monomer and the polyimide obtained with the diamine monomer have vast application prospect in such fields as electroluminescence, cavity transmission and electrochromism.

Description

technical field [0001] The invention belongs to the technical field of organic compounds, and in particular relates to a diamine monomer containing a diphenylamine-fluorene structure, a preparation method and its application in preparing polyimide. Background technique [0002] Polyimide is widely used in high-tech fields such as aerospace, electronics and military because of its excellent performance. However, its application is greatly limited due to its refractory and insoluble properties. The introduction of bulky units such as hexafluoroisopropane and triphenylamine can effectively prevent the accumulation of molecular chains and increase the free volume, thereby improving the solubility of polyimide. [0003] In recent years, the research group of Professor Liu Guisheng from Taiwan has carried out a series of studies on polyimides containing triphenylamine groups (YenHJ, LiouGS, Polymer Chemistry, 2012, 3(2):255-264.), the introduction of triphenylamine groups The gro...

Claims

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Application Information

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IPC IPC(8): C07C211/61C07C209/36C08G73/10C09K9/02
Inventor 赵晓刚孙宁伟冯非王大明陈春海
Owner JILIN UNIV
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