Novel copolymers of 4-fluorostyrene. 7. halogen ring-disubstituted 2-phenyl-1,1-dicyanoethylenes

Gregory B. Kharas, Katherine T. Flynn, Benjamin L. Hill, Mustafa R. Ishaq, Darin A. Kopp, Brittany G. Koroll, Kristin M. Kupczyk, Danielle M. Schulte, Ubaldo Vera, Mark D. Aparece, Salima Atlas, Mustapha Raihane

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Novel copolymers of trisubstituted ethylene monomers, halogen ring-disubstituted 2-phenyl-1,1-dicyanoethylenes, RC6H3CH= C(CN)2 (where R is 2,3-Cl2, 2,4-Cl2, 2,6-Cl2, 3,4-Cl2, 3,5-Cl2, 2-Cl-4-F, 2-Cl-6-F, 3-Cl-4-F) and 4-fluorostyrene were prepared at equimolar monomer feed composition by solution copolymerization in the presence of a radical initiator (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/r1) for the monomers is 2-Cl-4-F (2.42) > 3,4-Cl2(2.40) > 2,4-Cl 2(1.97) > 2-Cl-6-F (1.86)> 3-Cl-4-F (1.68)> 2,3-Cl 2 (0.89) > 3,5-Cl2 (0.70) > 2,6-Cl2 (0.47). High Tg of the copolymers, in comparison with that of poly(4-fluorostyrene) indicates a substantial decrease in chain mobility of the copolymer due to the high dipolar character of the trisubstituted ethylene monomer unit. Softening of the copolymers started in 194-216°C range. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 290-400°C range with residue, which then decomposed in 400-800°C range.

Original languageEnglish (US)
Pages (from-to)95-99
Number of pages5
JournalJournal of Macromolecular Science, Part A: Pure and Applied Chemistry
Volume48
Issue number2
DOIs
StatePublished - Feb 2011

Keywords

  • 4-fluorostyrene copolymers
  • radical copolymerization
  • Trisubstituted ethylenes

ASJC Scopus subject areas

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

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