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Diamine monomer with triphenylamine structure containing p-substituted cyclic amine, preparation method and application of diamine monomer

A technology of diamine monomers and cyclic amines, which is applied in the field of preparing polyamides with electrochromic properties, can solve problems such as instability of triphenylamine cations and coupling reactions, and achieve improved solubility, improved stability, and weakened The effect of interaction force

Inactive Publication Date: 2016-04-20
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the triphenylamine cation is unstable and prone to tail-to-tail coupling reactions

Method used

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  • Diamine monomer with triphenylamine structure containing p-substituted cyclic amine, preparation method and application of diamine monomer
  • Diamine monomer with triphenylamine structure containing p-substituted cyclic amine, preparation method and application of diamine monomer
  • Diamine monomer with triphenylamine structure containing p-substituted cyclic amine, preparation method and application of diamine monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1: Preparation of N,N-bis(4-aminophenyl)-4-piperidine aniline

[0041] The first step reaction: add 15.0g (176mmol) piperidine, 24.9g (176mmol) p-fluoronitrobenzene, 24.5g (176mmol) potassium carbonate in a 500mL three-necked flask equipped with mechanical stirring, add 250mL of N, N -Dimethylformamide was used as a solvent, stirred and reacted at 110°C for 5 hours under the protection of nitrogen. After cooling, the material was discharged in ice water, and the crude product was washed with water for 3 times. After drying, ethanol recrystallized to obtain yellow 4- Nitrophenyl piperidine powder 16.7g, productive rate is 46%;

[0042] The second step reaction: add 15.0 g of 4-nitrophenylpiperidine powder prepared in the first step reaction and 2.0 g of Pd with a mass fraction of 10% to a 500 mL three-necked flask equipped with a magnetic stirrer, a thermometer and a condenser tube. / C, add 180mL ethanol as a solvent, stir to obtain a suspension. After heating ...

Embodiment 2

[0047] Example 2: Preparation of N,N-bis(4-aminophenyl)-4-tetrahydropyrrole aniline

[0048] The first step reaction: add 10.0g (141mmol) tetrahydropyrrole, 21.9g (155mmol) p-fluoronitrobenzene, 21.5g (155mmol) potassium carbonate in a 250mL three-necked flask equipped with mechanical stirring, add 100mL of N, N-dimethylformamide was used as a solvent, stirred and reacted at 100°C for 8 hours under the protection of nitrogen. After cooling, the material was discharged in ice water. The crude product was washed 3 times with water, dried, and recrystallized from ethanol to obtain yellow 4 - 13.4g of nitrobenzene tetrahydropyrrole powder, the productive rate is 49%;

[0049] Second-step reaction: Add 10.0 g of 4-nitrobenzenetetrahydropyrrole powder prepared in the first step reaction, 1.5 g of 10% of Pd / C, add 150mL ethanol as a solvent, stir evenly to obtain a suspension. After that, it was heated to reflux, and 32.0 g of hydrazine hydrate with a mass fraction of 80% was slowl...

Embodiment 3

[0053] Example 3: Preparation of N,N-bis(4-aminophenyl)-4-(4-methylpiperidine)aniline

[0054] The first step reaction: add 10.0g (101mmol) 4-methylpiperidine, 14.9g (106mmol) p-fluoronitrobenzene, 14.6g (106mmol) potassium carbonate in a 250mL three-necked flask equipped with mechanical stirring, add 100mL N,N-dimethylformamide was used as a solvent, under stirring and nitrogen protection, reacted at 120°C for 12h, after cooling, the material was discharged in ice water, the crude product was washed 3 times with water, after drying, recrystallized from ethanol to obtain Yellow 4-nitrophenyltetrahydropyrrole powder 11.3g, yield rate is 51%;

[0055] The second step reaction: add 10.0 g of 4-nitrobenzene-4-methylpiperidine powder prepared in the first step reaction, 1.5 g mass fraction For 10% Pd / C, add 150mL ethanol as a solvent, stir evenly to obtain a suspension. After that, it was heated to reflux, and 30.0 g of hydrazine hydrate solution with a mass fraction of 80% was s...

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Abstract

The invention provides a diamine monomer with a triphenylamine structure containing p-substituted cyclic amine, a preparation method and application of the diamine monomer in preparing polyamide, and belongs to the technical field of organic compound preparation. The synthetic method comprises the following four steps: performing a nucleophilic substitution reaction on a cyclic amine compound and p-fluoronitrobenzene under the action of potassium carbonate to obtain a mononitrate compound containing a cyclic amine structure; then, taking Pd / C as a catalyst and hydrazine hydrate as a reducing agent to obtain a monoamino compound containing a cyclic amine structure; then, performing a nucleophilic substitution reaction on the monoamino compound and p-fluoronitrobenzene under the action of cesium fluoride to obtain a dinitro monomer with a triphenylamine structure containing p-substituted cyclic amine; finally, taking Pd / C as a catalyst and hydrazine hydrate as a reducing agent to obtain the diamine monomer with the triphenylamine structure containing p-substituted cyclic amine. The diamine monomer can react with various diacid to prepare the polyamide with the electrochromic performance.

Description

technical field [0001] The invention belongs to the technical field of organic compounds, and in particular relates to a diamine monomer with a triphenylamine structure containing para-substituted cyclic amines, a preparation method and an application thereof in preparing polyamides with electrochromic properties. Background technique [0002] Aromatic polyamides have excellent thermal, mechanical, electrical properties and excellent chemical resistance. However, their rigid frameworks and strong interchain interactions lead to high glass transition temperatures and limited solubility, which limit their applications. A common method to overcome this shortcoming is to introduce large non-coplanar groups to reduce the close packing of molecular chains and increase the free volume to improve the solubility of polyamides. [0003] The introduction of propeller-shaped triphenylamine units in polyamides can make polyamides have excellent solubility and film-forming properties wit...

Claims

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Application Information

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IPC IPC(8): C07D295/135C07D211/14C08G69/32C08G69/26
CPCC07D295/135C07D211/14C08G69/26C08G69/32
Inventor 陈春海孟诗瑶孙宁伟冯非王大明赵晓刚
Owner JILIN UNIV
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