Novel co-polymers of vinyl acetate and alkoxy ring-substituted 2-phenyl-1,1-dicyanoethylenes

Authors: Kharas, Gregory B.; Russell, Selena M.; Johnson, Elissa A.; McCreary, Karen E.; Chlupsa, Erica; Nguyen, Van A.T.; O'Brien, Maura R.; Rodriguez, Juan C.; Ogden-Schuette, Michael E.; Oliver, Julie A.; Walia, Naiha

Source: Designed Monomers & Polymers, Volume 10, Number 6, 2007 , pp. 585-592(8)

Publisher: VSP, an imprint of Brill

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Abstract:

Electrophilic tri-substituted ethylene monomers, alkyl ring-substituted 2-phenyl-1,1-dicyanoethylenes, RC₆H₄CH=C(CN)₂ (where R is 2-OCH₃, 3-OCH₃, 4-OCH₃, 2-OC₂H₅, 3-OC₂H₅, 4-OC₂H₅, 4-OC₃H₇, 4-OC₄H₉, 4-OC₆H₁₁), were synthesized by piperidine-catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and malononitrile, and characterized by CHN elemental analysis, IR, ¹H- and ¹³C-NMR. Novel co-polymers of the ethylenes and vinyl acetate were prepared at equimolar monomer feed composition by solution co-polymerization in the presence of a radical initiator (ABCN) at 70°C. The composition of the co-polymers was calculated from nitrogen analysis, and the structures were analyzed by IR, ¹H- and ¹³C-NMR, GPC, DSC and TGA. High T_g of the co-polymers, in comparison with that of polyvinyl acetate, indicates a substantial decrease in chain mobility of the co-polymer due to the high dipolar character of the tri-substituted ethylene monomer unit. The gravimetric analysis indicated that the co-polymers decompose in the 190-800°C range.

Keywords: TRI-SUBSTITUTED ETHYLENES; RADICAL CO-POLYMERIZATION; VINYL ACETATE CO-POLYMERS

Document Type: Research article

DOI: http://dx.doi.org/10.1163/156855507782401150

Affiliations: 1: DePaul University, Chemistry Department, 1036 West Belden Avenue, Chicago, IL 60614-3214, USA

Publication date: 2007-11-01