Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 11. Halogen ring-substituted propyl 2-cyano-3-phenyl-2-propenoates. Issue 10 (3rd October 2018)

• Record Type: Journal Article
• Authors: Humanski, Kara E.; Patterson, Santanna D.; Pecorin, Paul J.; Perfitt, Madeline M.; Romero, Janet; Sassack, William R.; Sweeney, Samantha M.; Talwar, Camille O.; Tolentino, Dominique A.; Wilson, Megan E.; Schjerven, William S.; Kharas, Gregory B.
• Is Part Of: Journal of macromolecular science. Volume 55:Issue 10(2018)
• Page Start: 709
• Page End: 717
• Publication Date: 2018-10-03
• Subjects: Radical -- copolymerization -- styrene -- copolymers -- trisubstituted ethylenes; Polymers -- Periodicals; Polymerization -- Periodicals; 547.7
• DOI: 10.1080/10601325.2018.1526639
• Languages: English
• ISSNs: 1060-1325

Abstract

Abstract: Novel trisubstituted ethylenes, ring-substituted propyl 2-cyano-3-phenyl-2-propenoates, RPhCH=C(CN)CO2 C3 H7 (where R is 4-chloro-3-fluoro, 2-fluoro-5-iodo, 2-fluoro-6-iodo, 2-trifluoromethyl, 3-trifluoromethyl, 4-trifluoromethyl, 2-trifluoromethoxy, 3-trifluoromethoxy, and 4-trifluoromethoxy) were prepared and copolymerized with styrene. The ethylenes were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and propyl cyanoacetate and characterized by CHN analysis, FTIR, 1 H and 13 C 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 FTIR, 1 H and 13 C NMR. Decomposition of the copolymers in nitrogen (TGA) occurred in two steps, first in the 250–500 °C range with residue (0.5–3.1% wt.), which then decomposed in the 500–700 °C range.