Polyarylene-based polymer, method for producing the polymer, and polymer electrolyte membrane for fuel cells using the polymer
A polyarylene and electrolyte membrane technology, which is applied in fuel cells, circuits, electrical components, etc., can solve problems such as the inability to achieve polymer growth, and achieve good dimensional stability, simplified production, and high proton conductivity.
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preparation example Construction
[0103] The above-mentioned preparation method is an example of the preparation method of the dihalide oligomer of formula 3, wherein Y is oxygen (O). Those skilled in the art can also prepare the dihalide oligomer of formula 3 in which Y is sulfur (S) or a chemical bond by referring to the above preparation method, and the preparation method is not intended to limit the present invention.
[0104] The coupling polymerization reaction can be carried out in the presence of an organic solvent, preferably at least one selected from dimethylacetamide, N-methylpyrrolidone, dimethylformamide, dimethyl sulfoxide, methylene chloride, chloroform, tetrahydrofuran, Solvent for benzene, toluene, and xylene.
[0105] According to the present invention, coupling polymerization may involve activating the mixture of monomers and oligomers at 50°C to 180°C for 2 to 4 hours, conducting polymerization at 25°C to 150°C for 2 to 24 hours, initiating precipitation, and washing and drying Precipitat...
manufacture example 1
[0132] [Production Example 1: Synthesis of Dihalide Monomer]
[0133]
[0134] Under nitrogen atmosphere, put about 200 mL of dimethoxyethane into a three-neck round bottom flask equipped with a condenser, magnetic stirring bar, bubbler, and solid addition tube. After adding titanium tetrachloride (about 10 g), slowly add about 4 g of LiAlH through the solid addition tube 4 . The reaction solution was heated at reflux for about 3 hours and then cooled to room temperature. Using a glass syringe, a solution of 4-benzophenonechloride (about 5.44 g) dissolved in dimethoxyethane (50 mL) was added.
[0135] Next, the reaction solution was heated under reflux for about 12 hours and cooled to room temperature. The reaction was terminated with pure water, and the organic phase was washed with 1M HCl solution. The by-products were extracted with diethyl ether, and the solvent was removed. Recrystallization was performed using ethylacetic acid and methanol to obtain the final p...
manufacture example 2
[0136] [Production Example 2: Synthesis of a Dihalide Monomer Having an Alkylsulfonyl Substituent]
[0137]
[0138] In a three-necked round-bottom flask equipped with a condenser, a magnetic stirring bar, a bubbler, and a dropping funnel, about 5 g of the product of Production Example 1 was dissolved in about 100 mL of dichloromethane under a nitrogen atmosphere. A solution containing about 7.3 g of chlorosulfonic acid dissolved in about 50 mL of dichloromethane was slowly added to the flask through the dropping funnel, and the flask was stirred for about 12 hours.
[0139] After neutralizing the reaction solution, about 8.8 g of thionyl chloride was added to the solution, after which the solution was stirred for about 1 hour, and after neopentyl alcohol (about 6.5 mL) was added, it was heated under reflux for about 12 hours. The reaction solution was cooled to room temperature, the reaction was terminated using pure water, and the organic phase was washed. Next, ethyl ...
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