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Polybenzimidazole material and midbody organic diacid thereof as well as preparation methods thereof

A benzimidazole and organic technology, which is applied in the field of functional polymer material preparation, can solve the problems of oxidative degradation of membranes and needs to be further improved, and achieves the effects of easy availability of raw materials, suitable for large-scale production, and improved solubility.

Active Publication Date: 2010-05-19
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the operation of hydrogen-air PEMFC cells, the oxidation stability of the membrane must be considered, which is due to the H produced during the reaction of the PEMFC cathode electrode. 2 o 2 And -OH or / and -OOH free radicals will erode the molecular chains in the membrane, resulting in oxidative degradation of the membrane
Since the main chain of polybenzimidazole is carbon-carbon bond and carbon-hydrogen bond, its oxidation resistance stability needs to be further improved compared with perfluorosulfonic acid membrane

Method used

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  • Polybenzimidazole material and midbody organic diacid thereof as well as preparation methods thereof
  • Polybenzimidazole material and midbody organic diacid thereof as well as preparation methods thereof
  • Polybenzimidazole material and midbody organic diacid thereof as well as preparation methods thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0048] in N 2 Add 175 parts of p-fluorobromobenzene, 122 parts of 3,5-dimethylphenol, 80 parts of Na2CO3, 800 parts of dimethylformamide and 200 parts of toluene into the three-necked flask under protection, start stirring, and slowly heat to reflux for 5 hours , exclude toluene, heat up to 130 ° C for 10 h, pour the reaction mixture into ethanol / water solution, filter and collect the filtrate and extract it with ether for 3 times, collect the oil phase and concentrate, vacuum distill to obtain 3,5-dimethyl-(4 -fluoro-phenoxy)-benzene. Add 100 parts of 5-(4-fluoro-phenoxy)-1,3-dimethylbenzene, 500 parts of water, and 500 parts of pyridine into a 2L three-necked flask, heat to reflux, slowly add potassium permanganate in portions 100 parts, reflux reaction for 7 days, pour the reactant into excess 10% hydrochloric acid, collect the precipitate by filtration, recrystallize the precipitate with ethanol and dry it in vacuum to obtain 5-(4-fluoro-phenoxy)-resorcinol formic acid. ...

Embodiment 2

[0051] in N 2 Add 225 parts of 4-trifluoromethylbromobenzene, 122 parts of 3,5-dimethylphenol, 80 parts of K2CO3, 1000 parts of dimethylacetamide and 300 parts of toluene into the three-necked flask under protection, start stirring, and heat slowly To reflux for 6 hours, remove toluene, raise the temperature to 140°C for 10 hours, pour the reaction mixture into ethanol / water solution, collect the filtrate by filtration and extract it with ether for 3 times, collect the oil phase and concentrate, then vacuum distill to obtain 3,5-dimethyl yl-(4-trifluoromethyl-phenoxy)-benzene. Add 100 parts of 3,5-dimethyl-(4-trifluoromethyl-phenoxy)-benzene and 500 parts of 50% nitric acid into a 1L autoclave lined with tetrafluoroethylene, and react at 150°C and 5 atm for 3 Hours, after cooling and reducing pressure, the reaction mixture was taken out and the precipitate was collected by filtration. The precipitate was recrystallized with ethanol / water and dried in vacuo to obtain 5-(4-trif...

Embodiment 3

[0054] Add 250 parts of 3,5-trifluoromethylchlorobenzene, 122 parts of 3,5-dimethylphenol, 100 parts of KOH, 1000 parts of dimethyl sulfoxide and 300 parts of toluene into the three-necked flask under the protection of argon, Start stirring, slowly heat to reflux for 5 hours, remove toluene, raise the temperature to 130°C for 12 hours, pour the reaction mixture into ethanol / water solution, collect the filtrate by filtration and extract with chloroform for 3 times, collect the oil phase and concentrate, then vacuum distill to obtain 3 , 5-Dimethyl-(3,5-trifluoromethyl-phenoxy)-benzene. Add 150 parts of 5-(4-fluoro-phenoxy)-1,3-dimethylbenzene, 600 parts of water, and 600 parts of pyridine into a 2L three-necked flask, heat to reflux, slowly add potassium permanganate in portions 120 parts, reflux reaction for 6 days, the reactant was poured into excess 10% hydrochloric acid, the precipitate was collected by filtration, and the precipitate was recrystallized with ethanol / water a...

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Abstract

The invention discloses a polybenzimidazole material and midbody organic diacid thereof as well as preparation methods thereof. The preparation methods comprise the following steps of: condensing fluorine-containing halide and 3,5-dimethyl phenol under the action of basic catalyst to generate fluorine-containing side-chain-substituted m-dimethyl benzene derivatives then oxidizing the obtained fluorine-containing side-substituted m-dimethyl benzene derivatives by potassium permanganate or nitric acid to obtain side-chain fluorine-containing organic diacid monomer and derivatives thereof; and carrying out polycondensation on the side-chain fluorine-containing organic diacid monomer, compound diacid monomer and tetramine monomer in polyphosphoric acid to generate the side-chain fluorine-containing soluble polybenzimidazole material . The prepared polybenzimidazole material has favorable heat resistance performance and solubility performance and can be used as high-temperature proton exchange membranes, separation membranes, sensors, heat resistance materials, composite materials, caking agents and other functional materials for fuel cells.

Description

technical field [0001] The invention belongs to the technical field of preparation of functional polymer materials, and relates to polybenzimidazole materials, intermediate organic diacids and their preparation methods. Background technique [0002] As a high-performance engineering plastic, polybenzimidazole material has excellent heat resistance and stability, mechanical and mechanical properties, acid and alkali resistance, radiation resistance, and can be widely used in aviation, aerospace, electric power, electronics, machinery and other industries. However, because the rigidity of the molecular chain is too strong, it can only be dissolved in a small amount of organic solvents and strong acids, and its application range is limited due to the difficulty in processing and molding. key to wider adoption. [0003] With the development of fuel cell technology in recent years, the application of polybenzimidazole materials in proton exchange membrane fuel cells (PEMFC) has ...

Claims

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Application Information

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IPC IPC(8): C07C65/24C07C51/16C07C51/275C08G73/18D01F6/74C09J179/04H01M8/02H01M2/16B01D71/64B01D69/12H01M8/0202H01M8/1016
CPCY02E60/12Y02E60/50
Inventor 尚玉明谢晓峰王要武王树博王金海王迎姿
Owner TSINGHUA UNIV
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