Synthesis and Styrene Copolymerization of Novel Chloro and Fluoro Ring-Trisubstituted Propyl Cyanophenylpropenoates


  •  Jessica Bates    
  •  Ashleigh L. Krider    
  •  Sana A. Malik    
  •  Denny P. May    
  •  Maryana Stryelkina    
  •  Chloe G. Williams    
  •  Daniel T. Wood    
  •  Sara M. Rocus    
  •  Gregory B. Kharas    

Abstract

Novel trisubstituted ethylenes, ring-substituted propyl 2-cyano-3-phenyl-2-propenoates, RPhCH=C(CN)CO2C3H7 (where R is 2,3,6-trichloro, 2,3,4-trifluoro, 2,3,5-trifluoro, 2,4,5-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro) were prepared by the piperidine catalyzed Knoevenagel condensation of ring-trisubstituted benzaldehydes and propyl cyanoacetate.

The ethylenes when copolymerized with styrene in solution with radical initiation (ABCN) at 70°C resulted in formation of copolymers. The composition of the copolymers was calculated from nitrogen analysis. The structures and properties were characterized by IR, 1H and 13C-NMR, GPC, DSC, and TGA.



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