Phosphonic acid functionalized polybenzimidazole as well as preparation method and application thereof

A technology of benzimidazole and functionalization, which is applied in the field of high-temperature proton exchange membranes, can solve the problems of low proton conductivity of proton exchange membranes, the inability to realize accurate and high-efficiency, and difficult control of atmosphere conditions, and achieve excellent proton conductivity. , good dissolution and film-forming properties, good thermal stability and mechanical properties

Active Publication Date: 2022-05-13
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this technology, the method of modifying polybenzimidazole with phosphoric acid vapor in a closed environment is used to prepare phosphoric acid-modified polybenzimidazole proton exchange membranes. The anhydrous phosphoric acid vapor atmosphere used in step 2 is difficult to control. The equipment requirements are high, and at the same time, the grafting on the polymer main chain cannot be realized accurately and efficiently, and the proton conductivity of the obtained proton exchange membrane is not high

Method used

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  • Phosphonic acid functionalized polybenzimidazole as well as preparation method and application thereof
  • Phosphonic acid functionalized polybenzimidazole as well as preparation method and application thereof
  • Phosphonic acid functionalized polybenzimidazole as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Such as figure 1 As shown, in a dry 1000ml three-necked flask, 28.4g (0.1mol) 2-methyl-[1,1'-biphenyl]-4,4'-dicarboxylic acid dimethyl ester, 17.8g (0.1mol ) N-bromosuccinimide and 0.82g (0.05mol) of azobisisobutyronitrile were dissolved in 400mL of carbon tetrachloride, and the temperature was raised to 83°C under nitrogen protection and refluxed for 3h. After the reaction was complete, the solvent was removed by a rotary evaporator at 45°C, the yellow crude product was recrystallized twice with isopropanol, and dried under vacuum at 45°C to obtain a white powder, which was 2-(bromomethyl)-[1, Dimethyl 1'-biphenyl]-4,4'-dicarboxylate. Yield: 63%.

[0045] In a dry 500ml three-necked flask, 20.1g (0.055mol) 2-(bromomethyl)-[1,1'-biphenyl]-4,4'-dicarboxylic acid dimethyl ester, 6.6g (0.03mol ) zinc bromide and 30 g (0.181 mol) of triethyl phosphite were dissolved in 240 ml of 1,4-dioxane, and the temperature was raised to 103° C. for 8 hours under nitrogen protection....

Embodiment 2

[0048] In a dry 1000ml three-necked flask, 28.4g (0.1mol) dimethyl-[1,1'-biphenyl]-4,4'-dicarboxylate, 17.8g (0.1mol) N- Bromosuccinimide and 0.82g (0.05mol) of azobisisobutyronitrile were dissolved in 300mL of carbon tetrachloride, and the temperature was raised to 75°C under nitrogen protection and refluxed for 2h. After the reaction was complete, the solvent was removed by a rotary evaporator at 45°C, the yellow crude product was recrystallized twice with isopropanol, and dried under vacuum at 45°C to obtain a white powder, which was 2-(bromomethyl)-[1, Dimethyl 1'-biphenyl]-4,4'-dicarboxylate. Yield: 59%.

[0049] In a dry 500ml three-necked flask, 20.1g (0.055mol) 2-(bromomethyl)-[1,1'-biphenyl]-4,4'-dicarboxylic acid dimethyl ester and 30g (0.181mol) Triethyl phosphite was dissolved in 240ml of 1,4-dioxane, and the temperature was raised to 103°C for 8 hours under the protection of nitrogen. When the reaction was complete, the solvent was removed by a rotary evaporato...

Embodiment 3

[0052] In a dry 250ml three-necked flask, 14.2g (0.05mol) of 2-methyl-[1,1'-biphenyl]-4,4'-dicarboxylic acid dimethyl ester, 13.4g (0.075mol) of N-bromo Substituted succinimide and 0.49g (0.03mol) of azobisisobutyronitrile were dissolved in 180mL of carbon tetrachloride, and the temperature was raised to 75°C under nitrogen protection and refluxed for 6h. After the reaction was complete, the solvent was removed by a rotary evaporator at 50°C, the yellow crude product was recrystallized twice with isopropanol, and dried under vacuum at 45°C to obtain a white powder, which was 2-(bromomethyl)-[1, Dimethyl 1'-biphenyl]-4,4'-dicarboxylate. Yield: 55%.

[0053] In a dry 500ml three-necked flask, 9.08 (0.025mol) 2-(bromomethyl)-[1,1'-biphenyl]-4,4'-dicarboxylic acid dimethyl ester and 10g (0.06mol) Triethyl phosphate was dissolved in 150ml of 1,4-dioxane, and heated to 103°C under nitrogen protection to reflux for 12h. When the reaction was complete, the solvent was removed by a ...

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Abstract

The invention discloses phosphonic acid functionalized polybenzimidazole as well as a preparation method and application thereof, and belongs to the technical field of high-temperature proton exchange membranes. The preparation method comprises the following steps: adding 2-((diethoxyphosphoryl) methyl)-[1, 1 '-biphenyl]-4, 4'-dicarboxylic acid, aromatic dicarboxylic acid and 3, 3 '-diaminobenzidine into a mixture of polyphosphoric acid and phosphorus pentoxide without dissolved oxygen, reacting at 120-170 DEG C for 5-20 hours, heating to 190-210 DEG C, and reacting; pouring the reaction liquid into deionized water, separating out a solid, soaking the obtained solid in a baking soda aqueous solution, stirring, and washing; soaking a product obtained by washing in concentrated hydrochloric acid, and washing to be neutral; and drying. The introduction of a methyl phosphonic acid side group reduces the close packing degree of a polybenzimidazole main chain, increases the free volume of the polymer, and is beneficial to improving the doping amount of phosphoric acid. Phosphonic acid groups and phosphoric acid molecules can form hydrogen-bond interaction, so that the proton conductivity is improved.

Description

technical field [0001] The invention relates to the technical field of high-temperature proton exchange membranes, in particular to a phosphonic acid functionalized polybenzimidazole, a preparation method thereof and an application in high-temperature proton exchange membranes. Background technique [0002] Proton exchange membrane fuel cell (PEMFC) is an efficient and clean electrochemical device that can realize the direct conversion of chemical energy to electrical energy. It has broad application prospects in the fields of electric vehicles and stationary power supplies. The proton exchange membrane is one of the key components in PEMFC, which determines the performance and life of the fuel cell to a certain extent. The Nafion proton exchange membrane invented by DuPont is now widely used in PEMFC. However, the proton conductivity of the membrane is heavily dependent on the ambient humidity, which requires low temperature and high humidity working conditions, which brin...

Claims

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Application Information

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IPC IPC(8): C08G73/18H01M8/103H01M8/1086
CPCC08G73/18H01M8/103H01M8/1086Y02E60/50
Inventor 彭晓宏何跃明
Owner SOUTH CHINA UNIV OF TECH
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