Sulfonated aromatic diamine and sulfonated polyimide resin and preparation methods thereof

A technology of sulfonated polyimide resin and sulfonated aromatic diamine, which is applied in the preparation of sulfonic acid, thioether, organic chemistry, etc., can solve the problem of reducing the thermal stability of thin films, restricting the application of polymers, and making public reports of research results and other problems, to achieve the effects of excellent thermal stability, good proton conductivity, and low methanol permeability

Active Publication Date: 2010-06-16
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the presence of a large number of fatty side chains in the polymer, the thermal stability of the film is greatly redu

Method used

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  • Sulfonated aromatic diamine and sulfonated polyimide resin and preparation methods thereof
  • Sulfonated aromatic diamine and sulfonated polyimide resin and preparation methods thereof
  • Sulfonated aromatic diamine and sulfonated polyimide resin and preparation methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Embodiment 1, the preparation of sulfonated aromatic diamine

[0055] In a three-neck flask equipped with magnetic stirring, condenser and nitrogen inlet and outlet, add 18.00 grams (0.15 moles) of lithium trifluoroacetate, 2.88 grams (0.12 moles) of magnesium powder and 200 milliliters (2.47 moles) of tetrahydrofuran, under nitrogen protection , stirred and added dropwise 29.13 g (0.12 mol) of 4-bromodiphenyl ether. After the reaction mixture was stirred at room temperature for 4 hours, it was refluxed at 60-70° C. for 4 hours to obtain an off-white turbid solution. After the reaction system was cooled to room temperature, excess magnesium powder and Grignard reagent were reacted with 10% hydrochloric acid aqueous solution. The organic phase was collected and distilled under reduced pressure to obtain 4-phenoxy-α,α,α-trifluoromethylacetophenone liquid.

[0056] 1 H-NMR (400MHz, DMSO-d 6 , ppm): 7.14-7.16 (d, 2H), 7.19-7.21 (d, 2H), 7.29-7.33 (t, 1H), 7.48-7.52 (t, ...

Embodiment 2

[0061] Embodiment 2, the preparation of sulfonated aromatic diamine

[0062] In a three-neck flask equipped with magnetic stirring, condenser and nitrogen inlet and outlet, add 18.00 grams (0.15 moles) of lithium trifluoroacetate, 3.60 grams (0.15 moles) of magnesium powder and 300 milliliters (3.70 moles) of tetrahydrofuran, under nitrogen protection , stirred and added dropwise 31.82 g (0.12 mol) of 4-bromodiphenyl sulfide. After the reaction mixture was stirred at room temperature for 4 hours, it was refluxed at 60-70° C. for 4 hours to obtain an off-white turbid solution. After the reaction system was cooled to room temperature, excess magnesium powder and Grignard reagent were reacted with 15% hydrochloric acid aqueous solution. The organic phase was collected and distilled under reduced pressure to obtain 4-phenylthio-α,α,α-trifluoromethylacetophenone liquid.

[0063] 1 H-NMR (400MHz, DMSO-d 6 , ppm): 7.17-7.19 (t, 1H), 7.23-7.25 (t, 2H), 7.39-7.41 (d, 2H), 7.50-7.52 (...

Embodiment 3

[0068] Embodiment 3, the preparation of sulfonated aromatic diamine

[0069] In the there-necked flask equipped with magnetic stirring, condenser and nitrogen inlet and outlet, add 23.99 grams (0.20 moles) of lithium trifluoroacetate, 4.32 grams (0.18 moles) of magnesium powder and 325 milliliters (4.00 moles) of tetrahydrofuran, under nitrogen protection , stirred and added dropwise 32.50 g (0.15 mol) of 4-chlorobenzophenone. After the reaction mixture was stirred at room temperature for 1 hour, it was refluxed at 60-70° C. for 4 hours to obtain an off-white turbid solution. After the reaction system was cooled to room temperature, excess magnesium powder and Grignard reagent were reacted with 15% hydrochloric acid aqueous solution. The organic phase was collected and distilled under reduced pressure to obtain 4-benzoyl-α,α,α-trifluoromethylacetophenone liquid.

[0070] 1 H-NMR (400MHz, DMSO-d 6 , ppm): 7.50-7.55 (t, 2H), 7.60-7.64 (t, 1H), 7.76-7.78 (d, 2H), 7.87-7.89 (d...

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Abstract

The invention discloses sulfonated aromatic diamine and sulfonated polyimide resin and preparation methods thereof. The fluorine-containing aromatic diamine with a sulfonated aromatic side chain in the invention has the advantages of compact synthetic route, readily available raw materials, easy purification and higher product yield. The aromatic diamine is structurally characterized in that a sulfonic acid group is connected to the aromatic side chain, and the structure contains hydrophobic trifluoromethyl; and compared with the traditional sulfonated polyimide, the sulfonated polyimide prepared by copolymerizing the fluorine-containing aromatic diamine with the sulfonated aromatic side chain, non-sulfonated aromatic diamine and naphthalene-containing dianhydride is easier in forming micro-phase separation structures of hydrophilic and hydrophobic areas so as to endow a film with good proton conduction property. Moreover, the sulfonated polyimide provided by the invention not only has good dissolubility and film-forming property, but also shows good thermal stability and lower methanol permeability, and has important application value in a proton exchange membrane fuel cell, particularly a direct methanol fuel cell.

Description

technical field [0001] The invention relates to a sulfonated aromatic diamine and a sulfonated polyimide resin and their preparation methods. Background technique [0002] Proton exchange membrane fuel cells (hereinafter referred to as PEMFC) are considered to be the most promising alternatives to traditional power sources for electric vehicles due to their rapid startup at room temperature, high energy conversion efficiency, high power density, and no pollution. Small power supply systems, uninterruptible power supplies for electronic devices, and clean, efficient new power supplies for portable electronics power supplies (P. Costamagna and S. Srinivasan, Quantumjumps in the PEMFC science and technology from the 1960s to the year 2000: Part I . Fundamental scientific aspects, Journal of Power Sources, 2001, 102(1-2), 242-252). The core component of PEMFC is a three-in-one membrane electrode (MEA) formed by hot pressing of cathode, anode and proton exchange membrane. The pr...

Claims

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Application Information

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IPC IPC(8): C07C309/49C07C303/06C07C323/66C07C319/20C07C309/52C07C309/48C08G73/10C08L79/08H01M8/02H01M2/16H01M8/0202H01M8/1011H01M8/1018
CPCY02E60/12Y02E60/50
Inventor 范琳孙飞杨士勇
Owner INST OF CHEM CHINESE ACAD OF SCI
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