Novel copolymers of styrene. 6. halogen ring-substituted 2-Cyano-3-phenyl-2-propenamides

Gregory B. Kharas, Lawrence J. Kray, Sansi L. Mitchell, Jabar Muhammad, Farah Numir, Elizabeth A. Plass, Jon R. Reens, Joe M. Skariah, Emily R. Sosnoski, Caryn J. Svienty

Research output: Contribution to journalArticlepeer-review


Novel trisubstituted ethylenes, ring-substituted 2-cyano-3-phenyl-2-propenamides, RPhCH D C(CN)CONH2 (where R is 3-bromo- 4-methoxy, 5-bromo-2-methoxy, 3-fluoro-2-methyl, 3-fluoro-4-methoxy, 5-bromo-2,4-dimethoxy, and 6-bromo-3,4-dimethoxy) were synthesized by potassium hydroxide catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and cyanoacetamide prepared and characterized by CHN elemental analysis, IR, 1H- and 13C-NMR. Novel copolymers of the ethylenes and styrene were prepared at equimolar monomer feed composition by solution in the presence of a radical initiation (AIBN) 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. Thus, the order of relative reactivity (1/r1) and the tendency toward alternation of monomer units in the copolymer for the CPA monomers is 5-Br-2,4-(CH3O)2 (0.83) > 3-F-2-CH3 (0.70) > 6-Br-3,4-(CH3O)2 (0.57) > 3-Br-4-CH3O (0.35) > 5-Br-2-CH3O (0.33) > 3-F-4-CH3O (0.25). High Tg of the copolymers in comparison with that of polystyrene indicates a substantial decrease in chain mobility of the copolymer due to the high dipolar character of the trisubstituted ethylene monomer unit. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200-500°C range with residue (3.2-5.7 wt%), which then decomposed in the 500-800°C range.

Original languageEnglish (US)
Pages (from-to)85-89
Number of pages5
JournalJournal of Macromolecular Science - Pure and Applied Chemistry
Issue number2
StatePublished - Feb 1 2015
Externally publishedYes


  • Radical copolymerization
  • Styrene copolymers
  • Trisubstituted ethylenes

ASJC Scopus subject areas

  • Ceramics and Composites
  • General Chemistry
  • Polymers and Plastics
  • Materials Chemistry


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