Novel rubbers from cationic copolymerization of soybean oils and dicyclopentadiene. 1. Synthesis and characterization

Biomacromolecules
Dejan D Andjelkovic, Richard C Larock

Abstract

Novel thermosetting copolymers, ranging from tough and ductile to very soft rubbers, have been prepared by the cationic copolymerization of regular (SOY) and 100% conjugated soybean oils (C(100)SOY) with dicyclopentadiene (DCP) catalyzed by Norway fish oil (NFO)-modified and SOY- and C(100)SOY-diluted boron trifluoride diethyl etherate (BFE). The gelation time of the reactions varies from 4 to 991 min at 110 degrees C. The yields of the bulk copolymers are essentially quantitative, while the yields of the cross-linked copolymers remaining after Soxhlet extraction with methylene chloride range from 69% to 88%, depending on the monomer stoichiometry and the catalyst used. (1)H NMR spectroscopy and Soxhlet extraction data indicate that these copolymers consist of a cross-linked soybean oil-DCP network plasticized by certain amounts of methylene chloride-soluble linear or less cross-linked soybean oil-DCP copolymers, unreacted oil, and some low molecular weight hydrolyzed oil. The molecular weights of these soluble fractions are in the range from 400 to 10,000 g/mol based on polystyrene standards. The bulk copolymers have glass transition temperatures ranging from -22.6 to 56.6 degrees C, while their tan delta peak values range fro...Continue Reading

Citations

Feb 7, 2012·Journal of Agricultural and Food Chemistry·Byung-Jun Kollbe AhnXiuzhi Susan Sun
Apr 2, 2014·Organic & Biomolecular Chemistry·Nacú HernándezEric W Cochran
Aug 21, 2015·Chemical Reviews·Alessandro GandiniEliane Trovatti
May 28, 2011·ChemSusChem·Jennifer F WuDean C Webster
Sep 12, 2012·Journal of Biomedical Materials Research. Part a·R J González-PazV Cádiz
Jan 25, 2011·ChemSusChem·Ying Xia, Richard C Larock
Aug 1, 2009·Biomacromolecules·Marta SacristánVirginia Cádiz
May 3, 2007·Biomacromolecules·Gerard LligadasVirginia Cadiz
Sep 12, 2006·Biomacromolecules·Yongshang Lu, Richard C Larock

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