Abstract
For the purpose of obtaining a polymer with a high dielectric constant, a new monomer, 2-(2, 2-dicyanoethylene)-2, 3-dihydropyran, was synthesized and polymerized with cationic initiators such as BF3OEt2, I2 and SnCl4 in dichloromethane, carbon tetrachloride or in diethyl ether at 25°C or at −78°C. Also, related monomers, 2-(2-cyano-2-carboethoxyethylene)-2, 3-dihydropyran and 2-(2, 2-dicarboalkoxyethylene)-2, 3-dihydropyran were synthesized and polymerized with cationic initiators described above. Polymerization features were compared among these monomers and complex formation of the monomer with the catalyst was indicated in the case of 2-(2, 2-dicyanoethylene)-2, 3-dihydropyran. The infrared spectra of the polymers indicated that the polymer had the tetrahydropyran ring and that the polymerization proceeded at the vinylic double bond. The dielectric constants (ε) measured at 1 kHz were 5.25 for ply[2-(2, 2-dicyanoethylene)-2, 3-dihydropyran], 4.38 for poly[2-(2, 2-dicarboethoxyethylene)-2, 3-dihydropyran] and 8.70 for poly[2-(2-cyano-2-carboethoxyethylene)-2, 3-dihydropyran], respectively.
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Oshiro, Y., Shirota, Y. & Mikawa, H. Synthesis of the Polymer with Polar Side Groups. I. The Syntheses and Polymerizations of 2-(2, 2-Dicyanoethylene)-2, 3-dihydropyran, 2-2(-Cyano-2-carboethoxyethylene)-2, 3-dihydropyran and 2-(2, 2-Dicarboalkoxyethylene)-2, 3-dihydropyran. Polym J 3, 217–225 (1972). https://doi.org/10.1295/polymj.3.217
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DOI: https://doi.org/10.1295/polymj.3.217