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Synthesis and fundamental properties of methacrylate polymer containing five‐membered cyclic trithiocarbonate group
Author(s) -
Nishi Masayuki,
Komeda Masahiro,
Aoyagi Naoto,
Yoshida Yoshiaki,
Endo Takeshi
Publication year - 2020
Publication title -
journal of polymer science
Language(s) - English
Resource type - Journals
eISSN - 2642-4169
pISSN - 2642-4150
DOI - 10.1002/pol.20200201
Subject(s) - glycidyl methacrylate , acrylonitrile , polymer chemistry , methacrylate , monomer , carbon disulfide , moiety , acrylate , copolymer , chemistry , polymerization , ethyl acrylate , thiourea , polymer , organic chemistry
4‐(1,3‐Dithia‐2‐thioxocyclopenthyl)methacrylate (TCMA), containing the five‐membered trithiocarbonate moiety, was prepared from glycidyl methacrylate (GMA) through 2,3‐epithiopropyl methacrylate (ETMA). At first step, GMA was converted to ETMA by the reaction using thiourea. At second step, ETMA was reacted efficiently with carbon disulfide in the presence of a catalytic amount of 1,2‐dimethyltetrahydropyrimidine to give TCMA. The polymerization of TCMA proceeded under standard radical conditions to give the polymeric TCMA in 94% yield. The copolymerizations of TCMA with ethyl acrylate (EA) or acrylonitrile (AN) were conducted by changing the feed molar ratios of the monomers, in which the corresponding copolymers were obtained in over 83% yields. In addition, the obtained polymers showed the high values of refractive index over ca. 1.6 due to the presence of the cyclic trithiocarbonate structure.