Novel Copolymers of Styrene and Some Halogen Ring-substituted 2-Phenyl-1,1-dicyanoethylenes

Abstract

Novel copolymers of trisubstituted ethylene monomers, ring-substituted 2-phenyl-1,1-dicyanoethylenes, RC₆H₃CH═C(CN)₂ (where R is 2-bromo,3-bromo, 3-chloro, 2,3-dichloro, 2-chloro-6-fluoro, 2,6-difluoro, 3,4-difluoro, and 3,5-difluoro) and styrene were prepared at equimolar monomer feed composition by solution copolymerization in the presence of a radical initiator (AIBN) at 70°C. The composition of the copolymers was calculated from nitrogen analysis, and the structures were analyzed by IR, ¹H and ¹³C-NMR, GPC, DSC, and TGA. High T _g of the copolymers in comparison with that of polystyrene indicates a substantial decrease in chain mobility of the copolymer due to the high dipolar character of the trisubstituted ethylene monomer unit. The gravimetric analysis indicated that the copolymers decompose in the 200–800°C range.

Keywords:

• Trisubstituted ethylenes
• radical copolymerization
• styrene copolymers

Acknowledgment

We are grateful that the project was supported by the research and equipment grants from the National Science Foundation (DMR 0710520), Coating Industry Education Fund (CIEF), Chicago Society of Coatings Technology, the DePaul University Research Council, and Office of Sponsored Programs and Research. Emi Hanawa was supported by the CIEF graduate fellowship.

Notes

^a Polymerization time was 8 h.