N-substituted polybenzimidazole pyridine compound and preparation method thereof

A polybenzimidazole pyridine compound technology, which is applied in the field of N-substituted polybenzimidazole pyridine compounds and its preparation, can solve the problems of affecting heat resistance level and stability reduction, and achieve good solubility, high heat resistance level, The effect of simple operation process

Inactive Publication Date: 2013-12-18
LASER FUSION RES CENT CHINA ACAD OF ENG PHYSICS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the currently synthesized polybenzimidazole pyridine materials have N-H bonds on the benzimidazole ring, and the presence of H atoms reduces the stability of this type of polymer in the air, which in turn affects its heat resistance level.

Method used

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

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preparation example Construction

[0018] The preparation method of N-substituted polybenzimidazole pyridine compound of the present invention, comprises the following steps successively:

[0019] (1) Preparation of 2,6-bis(4-fluorobenzoyl)pyridine compound.

[0020] Under the condition of nitrogen protection, 2,6-bis(diformyl chloride)pyridine and fluorobenzene are used as monomers, and 2,6-bis(4-fluorobenzoyl)pyridine is obtained under the catalysis of anhydrous aluminum chloride The crude product can be purified to obtain 2,6-bis(4-fluorobenzoyl)pyridine compound.

[0021]

[0022] (2) Preparation of N-substituted polybenzimidazole pyridine compounds.

[0023] Under the condition of nitrogen protection, with the 2,6-bis(4-fluorobenzoyl)pyridine compound and bis(benzimidazole) compound prepared above as monomers, add sulfolane, chlorobenzene and calcium carbonate, in anhydrous Under the catalysis of potassium carbonate, an N-substituted polybenzimidazole pyridine compound is obtained.

[0024]

[002...

Embodiment 1

[0034] Example 1 Polycondensation synthesis of N-substituted polybenzimidazole pyridine compounds.

[0035] Include the following steps:

[0036] (1) In an ice-water bath, add 0.05 mol of 2,6-bis(diformyl chloride)pyridine, 0.65 mol of fluorobenzene, and 0.12 mol of anhydrous aluminum chloride powder into a 100 mL single-necked flask, stir for 12 h and then heat up to 95 o C and continue to react for 12 h. After the system temperature was slowly cooled to room temperature, the brown-red solution was slowly poured into deionized water, filtered, and washed with a large amount of deionized water to remove residual hydrogen chloride. Recrystallized twice with dimethylacetamide (DMAc) to give colorless crystals, vacuum 80 o C dried to give 2,6-bis(4-fluorobenzoyl)pyridine.

[0037]

[0038] (2) Nitrogen atmosphere, in a 25mL two-necked flask equipped with a condenser and a water separator, add bis(benzimidazole) intermediate- 0.01mol, 0.01mol of 2,6-bis(4-fluorobenzoyl)p...

Embodiment 2

[0041] Example 2 Polycondensation synthesis of N-substituted polybenzimidazole pyridine compounds.

[0042] Include the following steps:

[0043] (1) Nitrogen atmosphere, add bis(benzimidazole) compound- 0.01mol, 0.01mol of 2,6-bis(4-fluorobenzoyl)pyridine, 0.04mol of anhydrous potassium carbonate, 0.015mol of calcium carbonate, 10mL of sulfolane and 4mL of chlorobenzene. The system was raised from room temperature to 145°C and kept for 2h. Then the temperature was raised from 145°C to 180°C, and the reaction was continued for 4 hours, and the water in the system was removed by the water separator. Subsequently, the temperature was raised to 210° C., and the reaction was carried out for 6 hours. The system was slowly cooled to room temperature, poured into deionized water for precipitation, suction filtered, extracted with methanol, and then vacuum-dried at 100°C for 3 hours to obtain polybenzimidazole pyridine- .

[0044]

[0045] polybenzimidazole pyridine- It ...

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Abstract

The invention provides an N-substituted polybenzimidazole pyridine compound (the general formula is I) and a preparation method thereof. The preparation method sequentially comprises steps of (1) by taking 2, 6-dual (terephthaloyl chloride) pyridine and fluorobenzene as monomers, under the condition of existence of anhydrous aluminum chloride, obtaining a 2,6-dual (4-fluorobenzene formyl) pyridine compound; (2) by taking the 2,6-dual (4-fluorobenzene formyl) pyridine compound and dual (benzimidazole) of different structures as the monomers, sulfolane as the solvent, chlorobenzene as the dewatering agent, calcium carbonate as the fluorinion removing agent, under the condition of catalysis of anhydrous potassium carbonate, preparing the N-substituted polybenzimidazole pyridine compound. The preparation method has a simple synthetic process, and has low cost and high productivity.

Description

technical field [0001] The invention relates to an N-substituted polybenzimidazole pyridine compound and a preparation method thereof. Background technique [0002] Polybenzimidazoles (PBIs) are a class of polymers with benzimidazole groups as repeating units. Since their inception, they have become irreplaceable special materials in cutting-edge technical fields such as machinery, electronics, automobiles and aerospace. However, the solubility of commercialized polybenzimidazoles is extremely poor, which greatly hinders the application and development of polybenzimidazoles. [0003] Pyridine is a class of six-membered heterocyclic molecules containing a nitrogen atom. Pyridine groups are introduced into the polymer system, and the solubility of the polymer in polar solvents can be increased by protonation of the polar N atom on the pyridine ring. At the same time, the structure of the pyridine ring is very similar to that of the benzene ring. The introduction of pyridine s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/18
Inventor 张林徐业伟崔相旺罗炫
Owner LASER FUSION RES CENT CHINA ACAD OF ENG PHYSICS
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