Novel Copolymers of Trisubstituted Ethylenes and Styrene. II. Halogen Ring‐Substituted Ethyl 2‐Cyano‐1‐oxo‐3‐phenyl‐2‐propenylcarbamates

Autor:	Mary E. Pepper, Erica L. Feitl, Kenneth Watson, Lauren Umek, Adeeb Z. Tadros, Gina M. Rogers, Fred C. Prillaman, Antonia M. Fuerst, Gregory B. Kharas, Jiyoun R. Pyo
Rok vydání:	2004
Předmět:	Polymers and Plastics Nitrile General Chemistry Styrene chemistry.chemical_compound Monomer chemistry Polymer chemistry Materials Chemistry Ceramics and Composites Copolymer Knoevenagel condensation Reactivity (chemistry) Polystyrene Piperidine
Zdroj:	Journal of Macromolecular Science, Part A. 41:629-635
ISSN:	1520-5738 1060-1325
Popis:	Electrophilic trisubstituted ethylenes (TSE), halogen ring‐substituted ethyl 2‐cyano‐1‐oxo‐3‐phenyl‐2‐propenylcarbamates, RC6H4CH˭C(CN)CONHCO2C2H5 (where R is 3‐Br, 4‐Br, 3‐Cl, 4‐Cl, 2‐F, 3‐F, and 4‐F) were prepared and copolymerized with styrene (ST). The monomers were synthesized by the piperidine catalyzed Knoevenagel condensation of ring‐substituted benzaldehydes and N‐cyanoacetylurethane, and characterized by CHN analysis, IR, 1H, and 13C NMR. All the ethylenes were copolymerized with ST (M1) in solution with radical initiation (AIBN) at 70°C. The compositions of the copolymers were 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 2‐F (3.81) > 3‐Cl (1.36) > 4‐Br (1.31) > 3‐Br (1.13) > 4‐F (0.90) > 3‐F (0.63) > 4‐Cl (0.37). Higher T g of the copolymers in comparison with that of polystyrene indicates decrease in chain mobility of the copolymer due to the high dipolar character of the TSE str...
Databáze:	OpenAIRE
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