Novel Copolymers of Styrene. 3. Halogen Ring-Substituted Ethyl 2-Cyano-3-Phenyl-2-Propenoates

Autor: Gregory B. Kharas, Eric S. Molina, Kathleen E. Abma, Roshan A. Ali, Kiki D. Bairaktaris, Fred P. Biasiello, Eva A. Cygan, Jami Gibson, Syed Haq, Dawn E. Hoag, Kasandra Johnson, Shenik I. Jordan, Michael B. Mathews, Caitlyn A. Shadduck, Nora Tuzik
Rok vydání: 2013
Předmět:
Zdroj: Journal of Macromolecular Science, Part A. 50:139-143
ISSN: 1520-5738
1060-1325
Popis: Electrophilic trisubstituted ethylenes, ring-substituted ethyl 2-cyano-3-phenyl-2-propenoates, RPhCH˭C(CN)CO2C2H5 (where R is 2-Cl, 3-Cl, 4-Cl, 2-Br, 3-Br, 4-Br, 2-F, 3-F, 4-F, 2-Cl-4-F, 2-Cl-6-F, 3-Cl-4-F) were prepared and copolymerized with styrene. The monomers were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and ethyl cyanoacetate, and characterized by CHN analysis, IR, 1H and 13C-NMR. All the ethylenes were copolymerized with styrene (M1) 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. The order of relative reactivity (1/r 1) for the monomers is 4-Br (7.74) > 2-Br (1.62) > 3-Cl (1.56) > 3-Br (1.39) > 4-F (0.97) > 3-F (0.86) = 4-Cl (0.86) > 2-Cl-6-F (0.57) > 3-Cl-4-F (0.51) > 2-Cl (0.49) > 2-F (0.42) > 2-Cl-4-F (0.37). Relatively high Tg of the copolymers in comparison with that of polystyrene indicates a decrease i...
Databáze: OpenAIRE
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