Sulfonic acid group-containing polymer, sulfonic acid group-containing aromatic compound and method of making same, as well as polymer electrolyte material, polymer electrolyte molded product and solid polymer fuel cell using same

A technology of aromatic compounds and electrolyte materials, applied in the direction of solid electrolyte fuel cells, sulfonic acid preparation, fuel cell parts, etc., can solve the problems of increased number of reaction steps, increased costs, insufficient chemical stability, etc., and achieve high output , excellent physical durability, the effect of excellent proton conductivity

Active Publication Date: 2014-05-21
TORAY IND INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the present invention considers that there is also a problem of insufficient chemical stability, and post-sulfonation reaction and reprecipitation are required, so the number of reaction steps will increase, resulting in an increase in cost
[0009] Likewise, the polymer electrolyte materials obtained with the prior art are insufficient as a means of improving economics, processability, proton conductivity, mechanical strength, chemical stability, and physical durability to become industrially useful polymers. electrolyte material

Method used

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  • Sulfonic acid group-containing polymer, sulfonic acid group-containing aromatic compound and method of making same, as well as polymer electrolyte material, polymer electrolyte molded product and solid polymer fuel cell using same
  • Sulfonic acid group-containing polymer, sulfonic acid group-containing aromatic compound and method of making same, as well as polymer electrolyte material, polymer electrolyte molded product and solid polymer fuel cell using same
  • Sulfonic acid group-containing polymer, sulfonic acid group-containing aromatic compound and method of making same, as well as polymer electrolyte material, polymer electrolyte molded product and solid polymer fuel cell using same

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0324] Synthesis of 2,2-bis(4-hydroxyphenyl)-1,3-dioxolane (K-DHBP) having the following formula (G1):

[0325] [chemical formula 29]

[0326]

[0327] Add 495 grams of 4,4'-dihydroxybenzophenone, 134 grams of ethylene glycol, 969 grams of trimethyl orthoformate, and 050 grams of p-Toluenesulfonic acid monohydrate, the material was dissolved. The temperature was then maintained at 78 to 82°C and the mixture was stirred for 2 hours. Then, the internal temperature was gradually increased to 120° C., and heating was carried out until the distillation of methyl formate, methanol and trimethyl orthoformate was completely stopped. After cooling to room temperature, the reaction solution was diluted with ethyl acetate, the organic layer was washed with 100 mL of 5% potassium carbonate aqueous solution, the layers were separated, and the solvent was evaporated. 80 ml of dichloromethane was added to the residue to precipitate crystals, which were filtered and dried to obtain 52.0...

Embodiment 1

[0334] (Synthesis of tetrasodium 3,5,3',5'-tetrasulfonic acid-4,4'-difluorodiphenylketone having the following formula (G2))

[0335] Add 1091 grams of 4,4'-difluorodiphenyl ketone to a 1000 ml 3-necked flask equipped with a stirrer and a concentrator

[0336] (Aldrich reagent), 210 milliliters of oleum (60% SO 3 ) (Aldrich reagent), then forcefully pass nitrogen gas into the nitrogen conduit connected to the upper part of the concentrator and the bubbler leading to the outside of the system, and react at 180 ° C for 24 hours. Suppress the evaporation of sulfur trioxide by forcefully blowing nitrogen. The reactant was then slowly placed in a large amount of water, neutralized with NaOH, precipitated with ethanol three times, and sodium sulfate was removed to obtain an aromatic compound containing a sulfonic acid group having the following formula (G2). by 1 H-NMR confirmed the structure. The starting material, disulfonated product, and trisulfonated product were not detect...

Embodiment 2

[0342] (Synthesis of 3,5,3',5'-tetrasulfonic acid-4,4'-dichlorodiphenylsulfone tetrasodium having the following formula (G3))

[0343] Add 143.6 grams of 4,4'-dichlorodiphenyl sulfone in a 1000 ml 3-necked flask equipped with a stirrer and a concentrator

[0344] (Aldrich reagent), 210 milliliters of oleum (60% SO 3 ) (Aldrich reagent), then forcefully pass nitrogen gas into the nitrogen conduit connected to the upper part of the concentrator and the bubbler leading to the outside of the system, and react at 200 ° C for 24 hours. At this time, the vigorously flowing nitrogen suppresses the volatilization of sulfur trioxide. After the reaction solution was gradually placed in a large amount of water and neutralized with NaOH, sodium sulfate was removed by ethanol precipitation three times to obtain a sulfonic acid group-containing aromatic compound having the following formula (G3). by 1 H-NMR confirmed the structure. It did not identify the starting material, disulfonated ...

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Abstract

It is an object of the present invention to provide a sulfonic acid group- containing polymer and a sulfonic acid group-containing aromatic compound, which have excellent proton conductivity even under the low humidification condition, are excellent in mechanical strength and chemical stability and, moreover, can attain high output and excellent physical durability when processed into a solid polymer fuel cell, as well as a polymer electrolyte material, a polymer electrolyte molded product and a solid polymer fuel cell respectively using the same. The sulfonic acid group-containing polymer of the present invention is a sulfonic acid group-containing polymer comprising a constituent unit containing a sulfonic acid group (A1), and a constituent unit not containing a sulfonic acid group (A2), wherein the polymer contains a constituent unit having a specified structure as at least one constituent unit containing a sulfonic acid group (A1) at 25 mol% or more based on a sum of the constituent unit containing a sulfonic acid group (A1). Further, the polymer electrolyte material, polymer electrolyte molded product and solid polymer fuel cell of the present invention are constituted using such a sulfonic acid group-containing polymer.

Description

technical field [0001] The invention relates to a sulfonic acid group-containing polymer, a sulfonic acid group-containing aromatic compound and a preparation method thereof, in particular to a highly practical polymer electrolyte material, which still has excellent proton conductivity even under low humidity conditions , and can obtain excellent mechanical properties, chemical stability and physical durability; and polymer electrolyte molded body and solid polymer fuel cell. Background technique [0002] A fuel cell is a power generator that generates electricity by electrochemically oxidizing fuel, such as hydrogen or methanol, and has attracted much attention in recent years because it is a clean energy source. Especially since solid polymer type fuel cells have a relatively low standard operating temperature of about 100°C and high energy density, they are expected to be widely used in small-scale or decentralized power generation facilities, or movable bodies such as au...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/40C07C303/06H01M8/02H01M8/10H01B1/06
CPCY02E60/50Y02P70/50
Inventor 陈桥邵芳可吴刚出原大辅梅田浩明
Owner TORAY IND INC
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