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Synthesis and Styrene Copolymerization of Novel Halogen, Alkoxy, and Alkyl Ring-Disubstituted Isopropyl 2-Cyano-3-Phenyl-2-Propenoates

submitted on 03.10.2019, 01:43 and posted on 04.10.2019, 22:20 by Kumail M. Hussain, Rachel M. Breault, Noreen J. Caporusso, Cathleen J. Cu, Kyle J. Decker, Tara K. Gill, Emily K. Gray, Christopher J. Homsi, Melina F. Kanji, Rachel M. Stone, Jose L. Zepeda, Sara M. Rocus, William S. Schjerven, Gregory Kharas

Novel trisubstituted ethylenes, ring-disubstituted isopropyl 2-cyano-3-phenyl-2-propenoates, RPhCH=C(CN)CO2CH(CH3)2 (where R is 2-bromo-5-methoxy, 3-bromo-4-methoxy, 5-bromo-2-methoxy, 2-chloro-3-methoxy, 3-chloro-4-methoxy, 2-chloro-6-methyl, 2-fluoro-6-methyl, 3-fluoro-2-methyl, 3-fluoro-4-methyl, 4-fluoro-2-methyl, 4-fluoro-3-methyl) were prepared and copolymerized with styrene. The monomers were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and isopropyl cyanoacetate and characterized by CHN elemental analysis, IR, 1H- and 13C-NMR. All the ethylenes were copolymerized with styrene in solution with radical initiation (ABCN) 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. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200-500ºC range with residue (1-8% wt.), which then decomposed in the 500-800ºC range.


Coatings Industry Education Fund (CIEF) and Chicago Society of Coating Technology (CSCT). Kumail M. Hussain was partially supported by CSCT funds, and the CIEF Joseph A. Vasta Scholarship.


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DePaul University



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Declaration of Conflict of Interest

No conflict of interest