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Synthesis and Styrene Copolymerization of Novel Ring-Disubstituted Isopropyl Cyanoarylacrylates

preprint
submitted on 23.09.2019 and posted on 24.09.2019 by Paige M. Whelpley, Sejla Bajramovic, Destiny M. Bracamontes, Garrett A. Buechner, Alexander D. Eremin, Erik J. Kowalczyk, David D. Lender, Rachel McCann, William S. Schjerven, Gregory Kharas

Novel oxy ring-substituted isopropyl 2-cyano-3-arylacrylates, RPhCH=C(CN)CO2CH(CH3)2 (where R is 3,4-dibenzyloxy, 3-benzyloxy-4-methoxy, 4-benzyloxy-3-methoxy, 2,3-methylenedioxy, 3-iodo-4-methoxy, 5-iodo-2-methoxy, 3,4-difluoro, 3,5-difluoro) were prepared and copolymerized with styrene. The acrylates were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-disubstituted benzaldehydes and isopropyl cyanoacetate and characterized by CHN elemental analysis, FTIR, 1H and 13C-NMR. All the acrylates 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 FTIR, 1H and 13C-NMR. Thermal properties of the copolymers are characterized by DSC and TGA. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200-500ºC range with a residue, which then decomposed in the 500-800ºC range.

History

Email Address of Submitting Author

gkharas@depaul.edu

Institution

DePaul University

Country

USA

ORCID For Submitting Author

0000-0003-3778-7970

Declaration of Conflict of Interest

No conflict of interest

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