Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 1. Alkyl ring-substituted isopropyl 2-cyano-3-phenyl-2-propenoates

ABSTRACT

Novel trisubstituted ethylenes, alkyl ring-substituted isopropyl 2-cyano-3-phenyl-2-propenoates, RPhCH = C(CN)CO₂CH(CH₃)₂ (where R is H, 2-methyl, 3-methyl, 4-methyl, 4-ethyl, 4-propyl, 4-i-propyl, 4-butyl, 4-i-butyl, 4-t-butyl) were prepared and copolymerized with styrene. The ethylenes were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and isopropyl cyanoacetate, and characterized by CHN analysis, IR, ¹H and ¹³C NMR. All the ethylenes were copolymerized with styrene in solution with radical initiation (ABCN) at 70°C. The compositions of the copolymers were calculated from nitrogen analysis and the structures were analyzed by FTIR, ¹H and ¹³C NMR. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 250–500°C range with residue (2-5% wt.), which then decomposed in the 500–800°C range.

KEYWORDS:

• Radical copolymerization
• styrene copolymers
• trisubstituted ethylenes

Acknowledgments

The authors are grateful to acknowledge that the project was partly supported by the Coatings Industry Education Fund (CIEF) and Chicago Society of Coating Technology (CSCT). Rachel L. Pride was partially supported by CSCT funds and the CIEF Joseph A. Vasta Scholarship.