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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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the triphenylamine cation is unstabl

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

Example Embodiment

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

[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 to react at 110 °C for 5 h under stirring and nitrogen protection. After cooling, the material was discharged into ice water. The crude product was washed with water 3 times. After drying, ethanol was recrystallized to obtain a yellow 4- Nitrophenylpiperidine powder 16.7g, the yield is 46%;

[0042] The second step reaction: add 15.0g 4-nitrophenylpiperidine powder obtained in the first step reaction, 2.0g mass fraction of 10% Pd to a 500mL three-necked flask equipped with a magnetic stirring bar, a thermometer and a condenser tube / C, add 180 mL of ethanol as a solvent, and stir to obtain a suspension. Then, it was heated to reflux, and 45....

Example Embodiment

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

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

[0049] The second step of reaction: add 10.0g of 4-nitrobenzene tetrahydropyrrole powder obtained in the first step reaction, 1.5g of 10% Pd / C, 150 mL of ethanol was added as a solvent, and the mixture was stirred to obtain a suspension. After that, it was heated to reflux, and 32.0 g of hydrazine hydrate with a mass fraction o...

Example Embodiment

[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 The N,N-dimethylformamide was used as a solvent to react at 120 °C for 12 h under stirring and nitrogen protection. After cooling, the material was discharged into ice water. The crude product was washed three times with water, dried and recrystallized from ethanol to obtain 11.3 g of yellow 4-nitrobenzenetetrahydropyrrole powder with a yield of 51%;

[0055] The second step reaction: add 10.0g of 4-nitrobenzene-4-methylpiperidine powder obtained in the first step reaction, 1.5g mass fraction to a 500mL three-necked flask equipped with a magnetic stirring bar, a thermometer and a condenser tube. To 10% Pd / C, add 150 mL of ethanol as a solvent, and stir to obtain a suspensi...

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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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