Wholly aromatic side chain type sulfonated diamine and preparation method thereof

A sulfonated diamine and side chain technology, which is applied in the field of fully aromatic side chain sulfonated diamine and its preparation, can solve the problem that it is difficult to meet the actual use requirements, the resistance to free radical oxidation and thermal stability is deteriorated, and the research results Issues such as public reports, to achieve the effects of excellent mechanical properties, excellent film-forming properties, and wide application prospects

Inactive Publication Date: 2009-06-03
SHANGHAI JIAO TONG UNIV
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  • Application Information

AI Technical Summary

Problems solved by technology

This sulfonated polyimide membrane is easy to form a microscopic phase separation structure, has excellent water resistance and high proton conductivity, but the presence of fatty side groups leads to the free radical oxidation resistance of this sulfonated polyimide and thermal stability become poor, it is difficult to meet the actual use requirements
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Method used

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  • Wholly aromatic side chain type sulfonated diamine and preparation method thereof
  • Wholly aromatic side chain type sulfonated diamine and preparation method thereof
  • Wholly aromatic side chain type sulfonated diamine and preparation method thereof

Examples

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Effect test

Embodiment 1

[0030] Preparation of 2,2'-bis(4-sulfophenoxy)biphenyldiamine

[0031] Under the conditions of nitrogen protection and magnetic stirring, add 6.95g (0.05mol) 3-nitrophenol, 13g (0.2mol) zinc powder, 50ml ethanol, 25ml (12mol / L) sodium hydroxide solution in the dry reaction flask, React for 10 hours, cool, add 45ml of concentrated hydrochloric acid, stir for 10 hours, add 25ml (12mol / L) sodium hydroxide solution, filter with suction, add 30ml of glacial acetic acid to the filtrate, collect the precipitate, and wash with deionized water until neutral , dried to obtain 3.8g of product, the yield was 70%. The resulting products were characterized structurally, including 1 H NMR spectrum, see figure 1 , proving that the synthesized product is 2,2'-dihydroxybenzidinediamine.

[0032] The specific characterization results are as follows:

[0033] figure 1 is 2,2'-dihydroxybenzidinediamine 1 HNMR with DMSO-d 6 It is the solvent, and the attribution of each peak is indicated in ...

Embodiment 2

[0039] Preparation of 2,2'-bis[4-(4-sulfonylsulfone)phenoxy]biphenyldiamine

[0040]Under the conditions of nitrogen protection and magnetic stirring, 1.98g (0.01mol) sodium p-fluorobenzenesulfonate, 1.445g (0.01mol) p-chlorothiophenol, 4g anhydrous potassium carbonate, 10mL dimethyl methoxide were added to the dry reaction flask. sulfone and 10mL toluene, heat the reaction system to 150°C, distill the toluene and water, and react at this temperature for 20 hours. After the reaction, cool the reaction system to room temperature, then pour it into 300mL acetone, filter with suction, and The obtained solid was dissolved in 100 mL of hot water, suction filtered, the filtrate crystallized, the precipitate was collected, washed with deionized water until neutral, and dried to obtain 2.3 g of the target product with a yield of 70%. The resulting products were characterized structurally, including 1 H NMR see, image 3 , proving that the synthesized product is 4-chlorodiphenylsulfi...

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Abstract

The invention relates to a wholly aromatic side chain type sulfonated diamine and a preparation method thereof. Metanitrophenol is used as raw material to prepare a 2, 2'-dihydroxyl benzidine intermediate product by reduction and rearrangement to react with sulfonated halogenated aryl hydrocarbon to prepare a series of wholly aromatic side chain type sulfonated diamine. Sulfonic group in a molecular structure of sulfonated aryl diamine is connected with a side group; sulfonated polyimide is prepared by the sulfonated aryl diamine, and the sulfonic group is far from the main chain, so that a microscopic phase separation structure is expected to form easily, thereby being good for the efficient conduction of proton. In addition, the compound can also be used as an important intermediate product for producing water-soluble dye, etc. The sulfonated aryl diamine prepared by the invention can react with dicarboxylic anhydride to prepare the sulfonated polyimide. Due to the good film-forming property, the excellent mechanical property, heat resistance and solvent resistance, the wholly aromatic side chain type sulfonated diamine has wide application prospect at the aspects of proton conducting membrane and separation membrane used for a fuel cell, ion exchange membrane used for chlor-alkali industry, etc.

Description

technical field [0001] The invention relates to a fully aromatic side chain type sulfonated diamine and a preparation method thereof. The prepared fully aromatic side chain type sulfonated diamine can be used to prepare high-performance fuel cell membranes. It belongs to the technical field of chemical polymers. Background technique [0002] In recent years, sulfonated polymers have attracted much attention due to their application prospects in polymer electrolyte fuel cells. Among them, sulfonated polyimide has become the most promising class of materials for practical applications because of its excellent film-forming properties, good mechanical properties, heat resistance and solvent resistance. Sulfonated diamine is an important monomer for preparing sulfonated polyimide. The structure of sulfonated diamine significantly affects the performance of the prepared sulfonated polyimide. The literature Journal of Materials Chemistry 2004, 14, 1062-1070 reports a sulfonated ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/42C07C303/22C07C317/22C07C315/04
Inventor 房建华郭晓霞曾圆
Owner SHANGHAI JIAO TONG UNIV
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