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Diamine monomer containing tetraphenylethylene-diarylamine structure, preparation method and application of the diamine monomer in polyamide synthesis

A technology of tetraphenylethylene and diamine monomers, applied in the field of polyamides, can solve the problems of dark color, limited use range, poor fluorescence effect, etc., and achieves improved fluorescence effect, improved transmittance, and weakened intermolecular charge transfer. Effect

Active Publication Date: 2019-12-24
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, polyamide materials generally have problems such as deep color and poor fluorescent effect, which limit the scope of use. How to introduce triphenylamine groups into polyamide materials and overcome the problem of poor fluorescent effect is a problem to be solved by the invention

Method used

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  • Diamine monomer containing tetraphenylethylene-diarylamine structure, preparation method and application of the diamine monomer in polyamide synthesis
  • Diamine monomer containing tetraphenylethylene-diarylamine structure, preparation method and application of the diamine monomer in polyamide synthesis
  • Diamine monomer containing tetraphenylethylene-diarylamine structure, preparation method and application of the diamine monomer in polyamide synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: N 1 ,N 1 '-((1,2-cis-diphenylethylene-1,2-)bis(4,1-phenylene)bis(N 1 - Preparation of (4-methoxyphenyl))benzene-1,4-diamine).

[0042] The first step reaction: Add 10-20g of 4-bromobenzophenone and 5-10g of zinc powder into a 1000ml three-necked flask equipped with mechanical stirring, add 500ml of tetrahydrofuran and cool to -78°C, add dropwise 10- 18g of titanium tetrachloride was heated to reflux for 24 hours after returning to room temperature. After the mixture was returned to room temperature, it was quenched with 10% potassium carbonate solution, filtered, and the aqueous layer of the filtrate was extracted three times with ethyl acetate. The organic phases were combined, and the solvent was evaporated. (4-bromophenyl)-1,2-stilbene 12.4g, yield 62%.

[0043] The second step reaction: in a 500m L three-necked flask, add 30-40g p-methoxyaniline, 20-30g p-fluoronitrobenzene, 50-60m L triethylamine and 360m L DMF (DMF is dried with calcium hydride in a...

Embodiment 2

[0047] Example 2: N 1 ,N 1 '-((1,2-diphenylethylene-1,2-)bis(4,1-phenylene)bis(N 1 Polyamide Preparation by Polymerization of -(4-Methoxyphenyl))Benzene-1,4-diamine)Terephthalic Acid

[0048] In the three-necked flask that magneton, nitrogen inlet and outlet, thermometer are housed, add the 0.3~1g N that embodiment 1 makes 1 ,N 1 '-((1,2-diphenylethylene-1,2-)bis(4,1-phenylene)bis(N 1 -(4-methoxyphenyl))benzene-1,4-diamine) and 0.1~0.5g of terephthalic acid, add 2~5mL of N-methylpyrrolidone, add 1~2mL of triphenyl phosphite ester and 0.5-1mL pyridine, add 0.15-0.30g CaCl2, and react at 110°C for 3-5h under nitrogen atmosphere. After the reaction is completed, cool to room temperature, discharge the material into methanol to obtain a light green fibrous product, reflux wash with ethanol for 30 minutes, wash with water reflux once, reflux with ethanol for 30 minutes, and dry in a vacuum oven at 90°C to obtain terephthalic acid polyamide , The yield is 80-90%.

Embodiment 3

[0049] Example 3: N 1 ,N 1 '-((1,2-diphenylethylene-1,2-)bis(4,1-phenylene)bis(N 1 Polymerization of -(4-methoxyphenyl))benzene-1,4-diamine)-4,4'-biphenyldicarboxylic acid to prepare polyamide

[0050] In the three-necked flask that magneton, nitrogen inlet and outlet, thermometer are housed, add the 0.3~1g N that embodiment 1 makes 1 ,N 1 '-((1,2-diphenylethylene-1,2-)bis(4,1-phenylene)bis(N 1 -(4-methoxyphenyl))benzene-1,4-diamine) and 0.1~0.5g of 4,4'-biphenyldicarboxylic acid, add 2~5mL of N-methylpyrrolidone, add 1~ 2mL triphenyl phosphite and 0.5-1mL pyridine, add 0.15-0.30g CaCl2, and react at 110°C for 3-5h under nitrogen atmosphere. After the reaction is completed, cool to room temperature, discharge the material into methanol to obtain a green powder product, reflux with ethanol for 30 minutes, wash with reflux with water once, and reflux with ethanol for 30 minutes, and dry in a vacuum oven at 90°C to obtain, 4'-biphenyldicarboxylic acid type Polyamide, the yi...

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Abstract

The invention discloses a diamine monomer containing a tetraphenylethylene-diarylamine structure, a preparation method and application of the diamine monomer in polyamide synthesis, belonging to the technical field of organic compounds. A polyamide material generally has the problems of dark color, poor fluorescent effect and the like, and the fluorescence effect is weak when a triphenylamine group is directly introduced into the polyamide material, so that a tetraphenylethylene structure and a triphenylamine group are combined together to obtain the diamine monomer containing the tetraphenylethylene-diarylamine structure and introduced into polyamide in the form of the diamine monomer, the twisted structure of the diamine monomer can weaken intermolecular charge transfer and improve the transmittance of polyamide, and the unique aggregation-induced emission phenomenon of the diamine monomer can greatly improve the fluorescence effect.

Description

technical field [0001] The invention belongs to the technical field of organic compounds, and in particular relates to a diamine monomer containing a tetraphenylethylene-bisarylamine structure, a preparation method and its application in the preparation of a multifunctional product with electrochromism, electronically controlled fluorescence, and aggregation-induced luminescence. applications in polyamides. [0002] technical background [0003] Because of its excellent physical and chemical properties and easy processing, polyamide has been widely studied for a long time, especially in the high-tech field, which has great application prospects. Under the action of an external electric field, the triphenylamine group is easy to form a stable cationic free radical, and charge transfer will occur during this process, resulting in a color change. At the same time, the triphenylamine cation can also effectively quench the fluorescence. Therefore, we combined the triphenylamine s...

Claims

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Application Information

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IPC IPC(8): C07C213/08C07C217/84C08G69/26C09K11/06C09K9/02
CPCC07C17/263C07C213/08C07C217/84C08G69/26C09K9/02C09K11/06C09K2211/1425C09K2211/1433C07C25/18
Inventor 于铁琛姚洪岩祝世洋曹光兆狄宜增王洪悦
Owner JILIN UNIV
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