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Synthesis of a novel polymethacrylamide bearing cyclic perfluoroalkyl groups
Author(s) -
Hayakawa Yoshio,
Hayashi Eiji
Publication year - 2001
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.2305
Subject(s) - methacrylamide , diastereomer , enantiomer , column chromatography , hexane , polymer , high performance liquid chromatography , polymerization , chemistry , materials science , polymer chemistry , copolymer , organic chemistry , chemical engineering , acrylamide , engineering
Abstract A novel chiral methacrylamide bearing perfluoropyrrolidino groups was synthesized. Perfluoro(2‐pyrrolidinopropionyl fluoride), the starting material, was prepared by electrochemical fluorination and resolved into enantiomeric derivatives by preparative high performance liquid chromatography (HPLC) performed with optically active 1‐phenethylamine as the diastereomeric counterpart. The polymethacrylamide was obtained by radical polymerization. A clear, colorless, tough film of the polymer was formed by the solution‐casting technique, which showed excellent water repulsion with a contact angle of water greater than 100°. Column packings prepared by the coating of silica gels with the optically active polymer showed potential as the chiral stationary phase for HPLC resolving racemic 1,1′‐bi‐2‐naphthol (separation factor = 1.56) with a hexane–isopropanol mixture as the eluent. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 83: 1443–1448, 2002