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Aromatic diamine monomer containing hexamethyl structure and preparation method thereof

A technology for aromatic diamine and diamine monomer, applied in the field of preparation of aromatic diamine monomer, can solve problems such as limited number of methyl groups, reduce the force and direction of conjugate type, high reaction yield, and simple synthesis route Effect

Inactive Publication Date: 2020-05-15
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Purpose: In order to solve the problem of the limited number of methyl groups in the polymethyl structure aromatic diamine monomer in the prior art, the present invention provides a hexamethyl structure aromatic diamine monomer and its preparation method

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  • Aromatic diamine monomer containing hexamethyl structure and preparation method thereof
  • Aromatic diamine monomer containing hexamethyl structure and preparation method thereof
  • Aromatic diamine monomer containing hexamethyl structure and preparation method thereof

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Effect test

Embodiment 1

[0022] Under nitrogen protection, 27.24g (0.2mol) of 2,4,6-trimethylphenol and 20.41g (0.1mol) of 1,5-difluoro-2, 4-Dinitrobenzene, further adding 200ml of N,N-dimethylformamide as solvent and 82g of potassium carbonate as catalyst, the system was stirred at room temperature for half an hour and then heated to 120°C for 6 hours to complete the reaction. Sedimentation, suction filtration, drying and further recrystallization to obtain the intermediate dinitro compound 4,6-bis-(2,4,6-trimethyl)phenoxy-1,3-dinitrobenzene, 1 H NMR spectrum such as figure 1 As shown, the yield is 91%, where the yield is obtained from the ratio of the mass of the intermediate compound actually obtained to the mass of the intermediate compound obtained theoretically.

[0023] Add 21.82g (0.05mol) intermediate dinitro compound 4,6-bis-(2,4,6-trimethyl)phenoxy-1,3-dinitro to a three-necked flask equipped with mechanical stirring Benzene, respectively add 410ml ethanol, 20.02g (0.4mol) of hydrazine hy...

Embodiment 2

[0027] Under nitrogen protection, 27.24g (0.2mol) of 2,4,6-trimethylphenol and 20.41g (0.1mol) of 1,5-difluoro-2, 4-Dinitrobenzene, further adding 110ml of N,N-dimethylacetamide as solvent and 28g of potassium carbonate as catalyst, the system was stirred at room temperature for half an hour and then heated to 60°C for 12 hours to complete the reaction. Sedimentation, suction filtration, drying and further recrystallization to obtain the intermediate dinitro compound 4,6-bis-(2,4,6-trimethyl)phenoxy-1,3-dinitrobenzene, the yield is 91%.

[0028] Add 21.82g (0.05mol) intermediate dinitro compound 4,6-bis-(2,4,6-trimethyl)phenoxy-1,3-dinitro to a three-necked flask equipped with mechanical stirring Benzene, add the hydrazine hydrate reductant of 280ml ethanol, 10.01g (0.2mol) and the Pd / C catalyst of 1.1g 5% respectively, under reflux reaction 4h, after finishing the reaction, obtain crude product through hot filtration, cooling, further weight The aromatic diamine 4,6-bis-(2,...

Embodiment 3

[0030] Under nitrogen protection, 27.24g (0.2mol) of 2,4,6-trimethylphenol and 20.41g (0.1mol) of 1,5-difluoro-2, 4-Dinitrobenzene, further add 185ml of N-methylpyrrolidone as a solvent and 28g of sodium carbonate as a catalyst, stir the system at room temperature for half an hour, then heat up to 60°C and react for 6h to end the reaction. Settling and suction filtration , drying and further recrystallization to obtain the intermediate dinitro compound 4,6-bis-(2,4,6-trimethyl)phenoxy-1,3-dinitrobenzene with a yield of 91%.

[0031] Add 21.82g (0.05mol) intermediate dinitro compound 4,6-bis-(2,4,6-trimethyl)phenoxy-1,3-dinitro to a three-necked flask equipped with mechanical stirring Benzene, add the hydrazine hydrate reductant of 350ml ethanol, 15.02g (0.3mol) and the Pd / C catalyst of 1.1g 10% respectively, under reflux reaction 4h, after finishing the reaction, obtain crude product through hot filtration, cooling, further weight The aromatic diamine 4,6-bis-(2,4,6-trimethyl...

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Abstract

The invention discloses an aromatic diamine monomer containing a hexamethyl structure, the aromatic diamine monomer is specifically 4,6-bis-(2,4,6-trimethyl)phenoxy-1,3-diaminobenzene, and six methylgroups contained in the aromatic diamine monomer are all located on a side group benzene ring; the diamine monomer can be applied to preparation of a high-performance polyimide film material, and canfurther improve the potential application value of the prepared polyimide film material in dissolving film-forming property, optical transparency and gas separation property. The preparation method comprises the following steps: firstly, carrying out reactions between 2,4,6-trimethyl phenol and 1,5-difluoro-2,4-dinitrobenzene under stirring according to a mole ratio of 2:1 for 6 to 12 hours at a temperature of 60 to 120 DEG C under the action of an alkaline catalyst so as to obtain an intermediate 4,6-bis-(2,4,6-trimethyl)phenoxy-1,3-dinitrobenzene; and then performing a redox reaction to reduce the intermediate dinitro compound to obtain a corresponding aromatic diamine monomer 4,6-bis-(2,4,6-trimethyl)phenoxy-1,3-diaminobenzene containing a hexamethyl structure. The method is simple in synthetic route, high in yield, and the product is easy to purify and stable at a room temperature.

Description

technical field [0001] The invention relates to an aromatic diamine monomer containing a hexamethyl structure and a preparation method thereof, belonging to the technical field of preparation of aromatic diamine monomers. Background technique [0002] Since its industrial application in the 1950s, polyimide has attracted more and more attention from researchers due to its excellent comprehensive properties, and is known as a "problem-solving expert" and the most potential special polymer in the 21st century. material. However, affected by the molecular structure characteristics of polymers, conventional polyimides are usually refractory and difficult to directly process into films. At the same time, polyimide film materials mostly have dark color, poor optical transparency and low gas permeability, which cannot meet the development needs of modern high-tech fields. Therefore, based on molecular design, it is of great academic research and practical application value to fur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/02C07C217/90C07C201/12C07C205/38C08G73/10
CPCC07C213/02C07C201/12C08G73/10C07C217/90C07C205/38
Inventor 汪称意蒋彩荣张晓静王俊儒赵晓燕
Owner CHANGZHOU UNIV