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Sulfonated aromatic compound, polyketone with sulfonated aromatic groups and methods for preparing sulfonated aromatic compound and polyketone with sulfonated aromatic groups

An aromatic compound and aromatic-based technology, which is applied in the preparation of sulfonates and organic chemistry, can solve the problems of harsh polymerization conditions and complex purification of polymerization products, and achieve low cost, good mechanical properties and temperature resistance, and raw materials Easy to get effect

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

In addition, the coupling polymerization of aryl dihalogen monomers described in this patent must be carried out in the presence of a large amount of metal reducing agents, metal catalysts and ligands. The polymerization conditions are harsh and the purification of polymerization products is complicated.

Method used

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  • Sulfonated aromatic compound, polyketone with sulfonated aromatic groups and methods for preparing sulfonated aromatic compound and polyketone with sulfonated aromatic groups
  • Sulfonated aromatic compound, polyketone with sulfonated aromatic groups and methods for preparing sulfonated aromatic compound and polyketone with sulfonated aromatic groups
  • Sulfonated aromatic compound, polyketone with sulfonated aromatic groups and methods for preparing sulfonated aromatic compound and polyketone with sulfonated aromatic groups

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] Embodiment 1: the synthesis of sulfonated polyaryl monomer

[0105] Add 1.0 moles of 2,2'-dihydroxybiphenyl, 2.0 moles of sodium tert-butoxide and 2.5 liters of dimethyl sulfoxide into a 4.0-liter reaction flask blown with nitrogen in turn, and react with mechanical stirring at 65°C for 1 hour. Then add 2.0 moles of 3-bromopropyl sodium sulfonate, continue to stir and react at 65°C for 24 hours, distill off the solvent under reduced pressure, recrystallize the obtained solid through ethanol / water with a weight ratio of 95 / 5, filter, and dry in vacuo That is, 2,2`-bis(3-sulfonated propoxy)biphenyl disodium in the form of sodium salt, 1 H NMR (400MHz, D 2 O) δ (ppm): 7.40 (Ar-H4, t, 2H), 7.25 (Ar-H6, d, 2H), 7.09-7.15 (Ar-H3 & Ar-H5, m, 4H), 4.07 (OCH 2 , t, 4H), 2.72 (CH 2 S, t, 4H), 1.97 (CH 2 CH 2 CH 2 , m, 4H), confirmed the structure of the compound. The reaction formula is as follows:

[0106]

[0107] Other sulfonated polyaryl monomers with different al...

Embodiment 2

[0109] 0.01 moles of 2,2'-bis(3-sulfonated propoxy)biphenyl disodium in Example 1, 1.00 moles of 4,4'-diphenyl ether dicarboxylic acid, 0.99 moles of 2,2 `-Dimethoxybiphenyl and 4 liters of Eaton's reagent were added to a nitrogen-gassed reaction flask, stirred and reacted at 40°C for 48 hours, and the reaction liquid was poured into a large amount of deionized water while it was hot to obtain a polymer precipitate, filtered and deionized water Wash repeatedly until the filtrate is neutral, soak the obtained polymer with 0.1mol / L dilute hydrochloric acid at room temperature for 24 hours, then wash repeatedly with deionized water until the washing liquid is neutral, and dry in vacuum to obtain H + A polymer with sulfonic acid groups in the side chain that exists in the form. 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 sp...

Embodiment 3

[0111] 0.01 moles of 2,2'-bis(3-sulfonated propoxy)biphenyl disodium in Example 1, 1.00 moles of 4,4'-diphenyl ether dicarboxylic acid, 0.99 moles of 2,2 `-Dimethoxybiphenyl and 4 liters of Eaton's reagent were added to a nitrogen-gassed reaction flask, stirred and reacted at 60°C for 24 hours, and the reaction solution was poured into a large amount of deionized water while it was hot to obtain a polymer precipitate, filtered and deionized water Wash repeatedly until the filtrate is neutral, soak the obtained polymer with 0.1mol / L dilute hydrochloric acid at room temperature for 24 hours, then wash repeatedly with deionized water until the washing liquid is neutral, and dry in vacuum to obtain H + Polymers with side chains containing sulfonic acid 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 resona...

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Abstract

The invention provides a sulfonated aromatic compound and a polyketone with sulfonated aromatic groups, wherein the polyketone is obtained by polymerization by taking the sulfonated aromatic compound as a monomer. The content of the sulfonated aromatic groups on the polyketone is controllable, and the polymer with sulfonated aromatic groups can be used for preparing a proton exchange membrane with high electric conductivity, good mechanical properties and low cost. The invention also provides methods for preparing the sulfonated aromatic compound and the polyketone with sulfonated aromatic groups. In addition, the invention further provides the proton exchange membrane.

Description

technical field [0001] The invention relates to the field of polymers and their preparation, in particular to a sulfonated aromatic compound, a polyketone containing sulfonated aromatic groups and a preparation method thereof. Background technique [0002] Proton exchange membrane fuel cell (PEMFC) is regarded as a clean and efficient energy source in the 21st century due to its remarkable advantages such as high energy conversion rate, low temperature start-up, and no pollution. The proton exchange membrane is a key component of PEMFC, which mainly plays the role of conducting protons and isolating fuel and oxidant. Currently, the commonly used proton exchange membranes are Nafion series perfluorosulfonic acid membranes produced by DuPont of the United States, but perfluorosulfonic acid membranes are expensive, so the development of new low-cost proton exchange membranes has become a research hotspot. Among them, side-chain sulfonated polymers have high proton conductivity...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/11C07C303/32C08G67/00C08L73/00
Inventor 徐铜文张正辉
Owner UNIV OF SCI & TECH OF CHINA
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