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Diacid monomer containing diphenylamine-fluorene, preparation method and application in preparation of polyamide

A technology of diacid monomer and diphenylamine is applied in the field of preparing polyamides with electrochromic properties, which can solve the problem of less polyamide varieties, and achieve the effects of preventing accumulation, weakening interaction force and maintaining thermal properties.

Active Publication Date: 2018-04-13
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, there are fewer varieties of polyamides with multiple functions. Therefore, it is necessary to design and synthesize new diacid monomers containing triphenylamine units, and to prepare polyamides from them.

Method used

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  • Diacid monomer containing diphenylamine-fluorene, preparation method and application in preparation of polyamide
  • Diacid monomer containing diphenylamine-fluorene, preparation method and application in preparation of polyamide
  • Diacid monomer containing diphenylamine-fluorene, preparation method and application in preparation of polyamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Preparation of N,N-bis(4-carboxyphenyl)-9,9-dimethylfluorene

[0038] The first step reaction: add 10.0g (48mmol) of 2-amino-9,9-dimethylfluorene, 11.6g (96mmol) of p-fluorobenzonitrile, 14.6g ( 96mmol) of cesium fluoride, add 100mL of dimethyl sulfoxide as a solvent, and react for 18h at 170°C under stirring and nitrogen protection. After cooling, discharge the material into ice water, wash the crude product twice with water, and recrystallize with glacial acetic acid to obtain 13.2 g of dark yellow N,N-bis(4-cyanophenyl)-9,9-dimethylfluorene crystals , yield 67%.

[0039]The second step reaction: Add 8 g of N,N-bis(4-cyanophenyl)-9,9-dimethylfluorene prepared in the first step into a 100mL three-necked flask equipped with a magnetic stirrer and a condenser powder, 16.0g potassium hydroxide, add 20mL ethanol and 20mL water as solvent, heat to reflux, continue to reflux and stir for 72h. After cooling, adjust the pH close to 3 with concentrated hydrochlori...

Embodiment 2

[0042] Example 2: Preparation of N,N-bis(4-carboxyphenyl)-9,9-diphenylfluorene

[0043] The first step reaction: add 15.0g (45mmol) of 2-amino-9,9-diphenylfluorene, 10.9g (90mmol) of p-fluorobenzonitrile, 13.7g ( 90mmol) of cesium fluoride, add 120mL of dimethyl sulfoxide as a solvent, and react for 26h at 170°C under stirring and nitrogen protection. After cooling, discharge the material into ice water, wash the crude product twice with water, and recrystallize with glacial acetic acid to obtain 15.2 g of dark yellow N,N-bis(4-cyanophenyl)-9,9-diphenylfluorene powder , yield 63%.

[0044] The second step reaction: Add 10 g of N,N-bis(4-cyanophenyl)-9,9-diphenylfluorene prepared in the first step into a 100mL three-necked flask equipped with a magnetic stirrer and a condenser Powder, 15.7g potassium hydroxide, add 25mL ethanol and 15mL water as solvent, heat to reflux, continue to reflux and stir for 72h. After cooling, use concentrated hydrochloric acid (6mol / L) to adjust ...

Embodiment 3

[0046] Example 3: Preparation of N,N-bis(4-carboxyphenyl)-9,9-dihexylfluorene

[0047] The first step reaction: add 15.0g (43mmol) of 2-amino-9,9-dihexylfluorene, 10.4g (86mmol) of p-fluorobenzonitrile, 13.1g (86mmol) in a 250mL three-necked flask equipped with mechanical stirring ) of cesium fluoride, add 120 mL of dimethyl sulfoxide as a solvent, and react for 26 hours at 170° C. under stirring and nitrogen protection. After cooling, discharge the material into ice water, wash the crude product twice with water, and recrystallize from glacial acetic acid to obtain 14.4 g of dark yellow N,N-bis(4-cyanophenyl)-9,9-dihexylfluorene powder. Yield 61%.

[0048] The second step reaction: Add 10 g of N,N-bis(4-cyanophenyl)-9,9-dihexylfluorene powder prepared in the first step into a 100mL three-necked flask equipped with a magnetic stirrer and a condenser 15.0g potassium hydroxide, add 25mL ethanol and 15mL water as a solvent, heat to reflux, continue to reflux and stir for 72h. ...

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Abstract

The invention belongs to the technical field of organic compounds, and relates to a diacid monomer containing a diphenylamine-fluorene structure, a preparation method and application thereof for preparing polyamide with the electrochromism performance. The synthetic method comprises the two steps that 2-aminofluorene with a substituent group at the bit 9 and p-fluorobenzonitrile are subjected to a nucleophilic substitution reaction under the effect of cesium fluoride to obtain a nitroamiline compound containing the diphenylamine-fluorene structure; then, under the effect of potassium hydroxide, basic hydrolysis is performed to obtain the diacid monomer containing the diphenylamine-fluorene structure. The diacid monomer and various diamine monomers are subjected to a reaction to obtain polyamide with the electrochromism performance. Due to the specific structure of the diacid monomer, the obtained polymer has the good solubility and unique photoelectric property; the diacid monomer and the polyamide prepared by the diacid monomer have the huge application prospect in the fields such as electrochromism.

Description

technical field [0001] The invention belongs to the technical field of organic compounds, and in particular relates to a class of diacid monomers containing a diphenylamine-fluorene structure, a preparation method and an application thereof in preparing polyamides with electrochromic properties. Background technique [0002] Aromatic polyamides have excellent physical and chemical properties. However, due to its rigid framework and strong interactions between molecular chains, it has the property of refractory and insoluble, which limits its application range. Introducing bulky non-coplanar groups into the main chain of polyamide can effectively prevent the accumulation of molecular chains and increase the free volume, thereby increasing the solubility and film-forming properties of the polymer. [0003] Introducing a propeller-shaped triphenylamine group into the polyamide main chain can increase the solubility and film-forming properties of the polymer without losing ther...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C229/60C07C227/18C08G69/32
CPCC07C227/18C07C229/60C07C253/30C08G69/32C08G2261/54C07C255/58
Inventor 陈春海孟诗瑶孙宁伟赵晓刚冯非王大明
Owner JILIN UNIV
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