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Synthesis and Styrene Copolymerization of Novel Fluoro and Oxy Ring-Disubstituted Isopropyl Phenylcyanoacrylates

preprint
submitted on 10.11.2019 and posted on 20.11.2019 by Abby R. Krause, Haley E. Aynessazian, Monica C. Gonzalez, Adnan M. Khan, Lara R. Lieberman, Meghan H. McNicholas, Nina M. Pelsi, Zachary S. Pierard, Sara M. Rocus, William S. Schjerven, Gregory Kharas

Novel fluoro and oxy ring-disubstituted isopropyl phenylcyanoacrylates, RPhCH=C(CN)CO2CH(CH3)2 (where R is 2-fluoro-3-methoxy, 2-fluoro-4-methoxy, 2-fluoro-5-methoxy, 2-fluoro-6-methoxy, 3-fluoro-4-methoxy, 4-fluoro-3-methoxy, 5-fluoro-2-methoxy, 4-fluoro-3-phenoxy) 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.

Funding

Chicago Society of Coating Technology

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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