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Diamine monomer with carbazole structure and polyimide synthesized by diamine monomer

A technology of diamine monomer and polyimide, applied in the field of polyimide, can solve problems such as single variety, and achieve the effect of easy operation, good application prospect and great application value

Inactive Publication Date: 2018-10-26
NANXIONG MATERIAL PRODION BASE OF CHINESE ACADEMY OF SCI GUANGZHOU CHEM +4
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, at present, its variety is still relatively single, and its thermal stability needs to be further improved, so it is necessary to carry out research on the design and synthesis of new functional diamine monomers

Method used

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  • Diamine monomer with carbazole structure and polyimide synthesized by diamine monomer
  • Diamine monomer with carbazole structure and polyimide synthesized by diamine monomer
  • Diamine monomer with carbazole structure and polyimide synthesized by diamine monomer

Examples

Experimental program
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Effect test

Embodiment 1

[0035] This example provides a synthesis method of 3,6-bis(4-aminophenyl)-9-phenylcarbazole and polyimide (1) 3,6-bis(4-aminophenyl)-9 -Synthesis of phenylcarbazole:

[0036] Dissolve 4.01g (10mmol) of 3,6-dibromo-9-phenylcarbazole and 3.47g (20mmol) of 4-aminophenylboronic acid hydrochloride into 30mL THF, then add 2mol / L K 2 CO 3 Solution 37.5mL, Aliquat 336 (phase transfer catalyst) 15 drops, under the protection of nitrogen, stir at room temperature for half an hour, then add tetrakis (triphenylphosphine) palladium catalyst to the system, react at 75°C for 24 hours. The reaction was detected by TLC. After the reaction was completed, the system was spin-dried, put on a silica gel column, and eluted with petroleum ether: ethyl acetate = 1:1 to obtain the product with a yield of 65%. product 1 H NMR and 13 C NMR spectrum as figure 1 As shown, it can be seen from the figure that the product synthesized by the reaction is 3,6-bis(4-aminophenyl)-9-phenylcarbazole of the pre...

Embodiment 2

[0041] This example provides a synthesis method of 3,6-bis(4-aminophenyl)-9-phenylcarbazole and polyimide (1) 3,6-bis(4-aminophenyl)-9 -Synthesis of phenylcarbazole:

[0042] Dissolve 8.02g (20mmol) of 3,6-dibromo-9-phenylcarbazole and 6.94g (40mmol) of 4-aminophenylboronic acid hydrochloride into 70mL THF, then add 2mol / L K 2 CO 3 Solution 75mL, Aliquat336 (phase transfer catalyst) 20 drops, under the protection of nitrogen, stir at room temperature for half an hour, then add tetrakis (triphenylphosphine) palladium catalyst to the system, react at 75°C for 24 hours. The reaction was detected by TLC. After the reaction was completed, the system was spin-dried, put on a silica gel column, and eluted with petroleum ether: ethyl acetate = 1:1 to obtain the product with a yield of 68%. 1 H NMR and 13 The characteristic peaks of the C NMR spectrum are the same as the characteristic peaks of the product detected in step (1) of Example 1, confirming that the product is 3,6-bis(4-a...

Embodiment 3

[0048] This example provides a synthesis method of 3,6-bis(4-aminophenyl)-9-phenylcarbazole and polyimide (1) 3,6-bis(4-aminophenyl)-9 -Synthesis of phenylcarbazole:

[0049] 16.04g (40mmol) of 3,6-dibromo-9-phenylcarbazole and 13.88g (80mmol) of 4-aminophenylboronic acid hydrochloride were dissolved in 150mL THF, followed by adding 2mol / L K 2 CO 3 Solution 180mL, Aliquat 336 (phase transfer catalyst) 40 drops, under the protection of nitrogen, stir at room temperature for half an hour, then add tetrakis (triphenylphosphine) palladium catalyst to the system, react at 85°C for 24 hours. The reaction was detected by TLC. After the reaction was completed, the system was spin-dried, put on a silica gel column, and eluted with petroleum ether: ethyl acetate = 1:1 to obtain the product with a yield of 70%. 1 H NMR and 13 The characteristic peaks of the C NMR spectrum are the same as the characteristic peaks of the product detected in step (1) of Example 1, confirming that the pro...

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Abstract

The invention belongs to the technical field of organic polymer materials, and discloses a diamine monomer with a carbazole structure and polyimide synthesized by the diamine monomer. The diamine monomer with the carbazole structure is prepared by 3,6-dibromo-9-phenyloxazole and 4-aminobenzeneboronic acid hydrochloride through a one-step reaction, the monomer and aromatic dianhydride are subjectedto a ring-opening reaction to obtain polyamide acid, and polyimide is obtained through a heating ring formation method. A method for synthesizing polyimide adopts mild reactions and is easy to operate and provides possibility for industrialization. The prepared polyimide material shows excellent performance, particularly has significantly-improved thermal stability, and has great potential application value and good application prospects in the fields of aerospace, electrical engineering, microelectronics and the like.

Description

technical field [0001] The invention belongs to the technical field of organic polymer materials, in particular to a diamine monomer containing a carbazole structure and a polyimide synthesized therefrom. Background technique [0002] Polyimide is a type of polymer material with the highest heat resistance. Due to its excellent comprehensive performance, it is widely used in various fields such as aviation, aerospace, electrical, machinery, chemical industry, and microelectronics. In the 1960s, all countries listed the research, development and utilization of polyimide as one of the most promising engineering plastics in the 21st century. Polyimide, because of its outstanding characteristics in performance and synthesis, whether it is used as a structural material or as a functional material, its huge application prospects have been fully recognized. [0003] Aromatic polyimide has an aromatic ring as the molecular backbone, which makes it exhibit excellent comprehensive pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C08G73/10
CPCC07D209/86C08G73/1067
Inventor 吕满庚张世恒胡卓荣王善吴昆
Owner NANXIONG MATERIAL PRODION BASE OF CHINESE ACADEMY OF SCI GUANGZHOU CHEM
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