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N-substituted polybenzimidazole amide compound and preparation method thereof

A technology of benzimidazole and compound, which is applied in the field of N-substituted polybenzimidazole amide compound and its preparation, can solve the problems of affecting heat resistance level and lowering stability, and achieves the effect of low preparation cost and simple operation process

Inactive Publication Date: 2012-07-25
LASER FUSION RES CENT CHINA ACAD OF ENG PHYSICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the currently synthesized polybenzimidazole amide materials, whether they contain benzimidazole groups in the main chain or contain benzimidazole groups in the branch chains, all have N-H bonds. The stability of the product is reduced, which in turn affects its heat resistance level

Method used

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  • N-substituted polybenzimidazole amide compound and preparation method thereof
  • N-substituted polybenzimidazole amide compound and preparation method thereof
  • N-substituted polybenzimidazole amide compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1 The polycondensation synthesis of N-substituted polybenzimidazole amide compound

[0029] (1) In a 25mL three-necked flask, add 0.01mol terephthalic acid, 0.022mol o-phenylenediamine, 8mL polyphosphoric acid, 2 Under the protection of , the reaction was stirred at 200°C for 6h. After the solution is cooled, pour it into 100mL of cold distilled water, add dropwise 15% NaOH solution, neutralize to pH=8, and generate a large amount of precipitate. Suction filtration, washing with water, and drying gave solid crude product. The crude product was dissolved in absolute ethanol for recrystallization, activated carbon decolorization and vacuum drying at 60°C to obtain the bis(benzimidazole) intermediate- .

[0030]

[0031] (2) In a 50mL three-necked flask, add 0.01mol p-phenylenediamine, 0.05mol 4-fluorobenzoyl chloride, 20mL triethylamine, in N 2 Under the protection of , the reaction was stirred overnight in an ice-water bath. Then the mixed solution wa...

Embodiment 2

[0037] Embodiment 2 The polycondensation synthesis of N-substituted polybenzimidazole amide compound

[0038] ⑴In a 25mL three-necked flask, add 0.01mol 4'4dicarboxylic acid diphenyl ether, 0.022mol o-phenylenediamine, 8mL polyphosphoric acid, in N 2 Under the protection of , the reaction was stirred at 200°C for 6h. After the solution is cooled, pour it into 100mL of cold distilled water, add dropwise 15% NaOH solution, neutralize to pH=8, and generate a large amount of green precipitate. Suction filtration, washing with water, and drying gave solid crude product. The crude product was dissolved in absolute ethanol for recrystallization, decolorized by activated carbon and vacuum dried at 60°C to obtain bis(benzimidazole) compound- .

[0039]

[0040] (2) In a 50mL three-necked flask, add 0.01mol 4'4-diaminodiphenyl ether, 0.05mol 4-fluorobenzoyl chloride, 20mL triethylamine, 2 Under the protection of , the reaction was stirred overnight in an ice-water bath. Then t...

Embodiment 3

[0043] Embodiment 3 The polycondensation synthesis of N-substituted polybenzimidazole amide compound

[0044] (1) In a 25mL three-necked flask, add 0.01mol 4'4 diphenyl sulfone dicarboxylate, 0.022mol o-phenylenediamine, 8mL polyphosphoric acid, in N 2 Under the protection of , the reaction was stirred at 200°C for 6h. After the solution is cooled, pour it into 100mL of cold distilled water, add dropwise 15% NaOH solution, neutralize to pH=8, and generate a large amount of green precipitate. Suction filtration, washing with water, and drying gave solid crude product. The crude product was dissolved in absolute ethanol for recrystallization, decolorized by activated carbon and vacuum dried at 60°C to obtain bis(benzimidazole) compound- .

[0045]

[0046] (2) In a 50mL three-necked flask, add 0.01mol 1,4-bis(4-aminophenoxy)benzene, 0.05mol 4-fluorobenzoyl chloride, 20mL triethylamine, in N 2 Under the protection of , the reaction was stirred overnight in an ice-water b...

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Abstract

The invention discloses an N-substituted polybenzimidazole amide compound and a preparation method thereof. The preparation method disclosed by the invention comprises the following steps that: (1) bis(benzimidazole) compounds with different structures are obtained in the catalysis of a polyphosphoric acid system based on aromatic dicarboxylic acids with different structures and o-phenylenediamine (the molar ratio is 1:2.2) as monomers; (2) difluorinated amido compounds with different structures are obtained in the catalysis of triethylamine based on aromatic diamines with different structures and 4-fluorobenzoyl chloride (the molar ratio is 1:5) as the monomers; and (3) the N-substituted polybenzimidazole amide compound is obtained by taking bis(benzimidazole) intermediate and the difluorinated amido compound (the molar ratio is 1:1) as the monomers, sulfolane as a solvent, chlorobenzene as a dewatering agent and calcium carbonate as a fluorinion removing agent in the catalysis of anhydrous potassium carbonate. The preparation method disclosed by the invention is simple in synthesis process and low in cost, and the compound disclosed by the invention is high in yield.

Description

technical field [0001] The invention relates to an N-substituted polybenzimidazole amide compound and a preparation method thereof. Background technique [0002] Since its inception, polybenzimidazole (PBI) has become an irreplaceable special material in high-tech fields such as aerospace and other harsh environments, and has been widely used abroad. In my country, although many research institutions are conducting research in this area, the key process technology has not been broken through, and engineering application products have not yet been released. At the same time, the synthesized polybenzimidazole has extremely poor solubility, which hinders the application and development of polybenzimidazole. [0003] Polyamide (PA) is widely used because of its excellent mechanical properties and good electrical properties, as well as its wear resistance, oil resistance, solvent resistance, self-lubrication, corrosion resistance and good processing performance. Its biggest dis...

Claims

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Application Information

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IPC IPC(8): C08G73/18
Inventor 张林徐业伟常冠军
Owner LASER FUSION RES CENT CHINA ACAD OF ENG PHYSICS
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