Qaternized aromatic compound, polyketone with quaternary aromatic groups and methods for preparing quaternized aromatic compound and polyketone with quaternary aromatic groups

A technology of aromatic compounds and aromatic groups, which is applied in the field of polymers and their preparation, can solve problems such as complicated steps and difficulty in introducing quaternary ammonium groups, and achieve the effects of low cost, good mechanical properties and temperature resistance, and easy-to-obtain raw materials

Inactive Publication Date: 2013-04-17
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional polymers containing quaternary ammonium groups usually require chloromethylation of the synthetic polymer backbone, aryl groups on the polymer backbone, and reaction with tertiary ammonium to convert benzyl chloride into quaternary ammonium

Method used

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  • Qaternized aromatic compound, polyketone with quaternary aromatic groups and methods for preparing quaternized aromatic compound and polyketone with quaternary aromatic groups
  • Qaternized aromatic compound, polyketone with quaternary aromatic groups and methods for preparing quaternized aromatic compound and polyketone with quaternary aromatic groups
  • Qaternized aromatic compound, polyketone with quaternary aromatic groups and methods for preparing quaternized aromatic compound and polyketone with quaternary aromatic groups

Examples

Experimental program
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Effect test

Embodiment 1

[0110] Embodiment 1: the synthesis of quaternized diaryl monomer

[0111] Add 1.0 moles of 2,2'-dihydroxybiphenyl, 2.0 moles of potassium carbonate, 2.0 moles of 4-bromobutyltrimethylammonium bromide and 15 liters of acetonitrile into the 25 liter reaction flask, mechanically stirred at 75°C for 24 hours, filtered, and the solvent was removed by distillation under reduced pressure. Oxydiphenyl dibromide, abbreviated as DNODP, 1 H NMR (400MHz, D 2 O) δ (ppm): 7.41 (Ar-H4, t, 2H), 7.27 (Ar-H6, d, 2H), 7.09-7.16 (Ar-H3 & Ar-H5, m, 4H), 4.03 (OCH 2 , t, 4H), 3.06 (CH 2 N, t, 4H), 2.88 (NCH 3 , t, 18H), 1.52-1.70 (CH 2 CH 2 CH 2 CH 2 , m, 8H), confirmed the structure of compound, reaction formula is as follows:

[0112]

[0113] Other quaternized diaryl monomers containing different alkyl lengths and quaternary ammonium groups were synthesized in a similar manner, except that different quaternizing agents were used instead of 4-bromobutyltrimethylammonium bromide.

Embodiment 2

[0115]0.01 mole of DNODP in Example 1, 1.00 mole of 4,4'-diphenyl ether dicarboxylic acid, 0.99 mole of 2,2'-dimethoxybiphenyl and 2 liters of trifluoromethanesulfonic acid were added to the In a nitrogen reaction flask, stir and react at 40°C for 24 hours, cool the reaction solution and pour it into an ice / water mixture to precipitate a polymer, filter and wash repeatedly with deionized water until the filtrate is neutral, and use After soaking in 1mol / L sodium hydroxide aqueous solution at room temperature for 24 hours, then vacuum-dry at room temperature to obtain OH - Polymers with side chains containing quaternary ammonium groups in the form of polymers. A strong carbonyl absorption peak appears in the infrared spectrogram and almost no carboxyl absorption peak is observed, indicating the occurrence of polyacylation; the proton nuclear magnetic resonance spectrum confirms the structure of the obtained polymer and the ratio of each structural unit calculated by the integra...

Embodiment 3

[0117] 0.50 moles of DNODP in Example 1, 1.00 moles of 4,4`-diphenyl ether dicarboxylic acid, 0.50 moles of 2,2`-dimethoxybiphenyl and 2 liters of trifluoromethanesulfonic acid were added to the In a nitrogen reaction flask, stir and react at 60°C for 24 hours. After cooling the reaction solution, pour it into an ice / water mixture to precipitate a polymer. Filter and wash repeatedly with deionized water until the filtrate is neutral. After soaking in 1mol / L sodium hydroxide aqueous solution at room temperature for 24 hours, then vacuum-dry at room temperature to obtain OH - Polymers with side chains containing quaternary ammonium groups in the form of polymers. A strong carbonyl absorption peak appears in the infrared spectrogram and almost no carboxyl absorption peak is observed, indicating the occurrence of polyacylation; the proton nuclear magnetic resonance spectrum confirms the structure of the obtained polymer and the ratio of each structural unit calculated by the integ...

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Abstract

The invention provides a quaternized aromatic compound, a polyketone with quaternary aromatic groups and methods for preparing the quaternized aromatic compound and the polyketone with quaternary aromatic groups. The content of the quaternary aromatic groups on the polyketone is controllable, and the polyketone with quaternary aromatic groups can be used for preparing an anion exchange membrane with high electric conductivity, good mechanical properties and low cost.

Description

technical field [0001] The invention relates to the field of polymers and preparation methods thereof, in particular to a quaternized aromatic compound, a polyketone containing quaternized aromatic groups and a preparation method thereof. Background technique [0002] Anion exchange membrane is a membrane material with positively charged ionic groups fixed on the membrane body, which can selectively pass through anions. It has excellent ion selectivity and mechanical properties. In recent years, it has been used in many fields such as electrolysis and fuel cells. been widely studied and applied. [0003] Anion exchange membranes are usually prepared from polymers containing quaternary ammonium groups. Traditional polymers containing quaternary ammonium groups usually require chloromethylation of the synthetic polymer backbone, aryl groups on the polymer backbone, and reaction with tertiary ammonium to convert benzyl chloride into quaternary ammonium groups. Groups, not onl...

Claims

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Application Information

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IPC IPC(8): C07C217/20C07C213/06C08G67/00C08L73/00
Inventor 徐铜文张正辉
Owner UNIV OF SCI & TECH OF CHINA
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