Katherine Kim, M. Morales, M. J. Scully
1999
Citations
0
Influential Citations
11
Citations
Journal
Designed Monomers and Polymers
Abstract
Electrophilic trisubstituted ethylenes, ring-disubstituted methyl 2-cyano-3-phenyl-2-propenoates, RCH=C(CN)CO2CH3 (where R = 2,3-dichlorophenyl, 2,4-dichlorophenyl, 2,6-dichlorophenyl, 3,4-dichlorophenyl, 4-chloro-3-nitrophenyl, 5-chloro-2-nitrophenyl, 2-chloro-6-fluoro), were prepared and characterized. All the propenoates, except methyl 2-cyano-3-(4-chloro-3-nitrophenyl)-2-propenoate, were copolymerized with styrene (M1) in solution with radical initiation (AIBN) at 70°C. The compositions of the copolymers were calculated from nitrogen analysis and the structures were analyzed by IR, 1H-, and 13C-NMR. The order of relative reactivity (1/r1) for the monomers is 2,4-dichloro (2.1) = 3,4-dichloro (2.1) > 2,6-dichloro (0.8) = 2,3-dichloro (0.8) > 2-chloro-6-fluoro (0.6) > 5-chloro-2-nitro (0.2). The high glass transition temperatures of the copolymers (> 190°C) in comparison with that of polystyrene indicate a substantial decrease in the chain mobility of the copolymers due to the high dipolar character of ...