Polymerization reactions of functionalized vegetable oils with petroleum-based macromonomers

Abstract

The aim of this work is to synthesize new polymers from plant oils. Polymerization of plant oil triglycerides is possible by attaching a polymerizable group to the triglyceride. This strategy has been used by us and by others in many examples. Polymers derived from such monomers have low connectivity and low mechanical properties due to the bulky structure of the monomer. This manifests itself in low fracture toughness of the polymers obtained. In this work we changed our strategy by starting first with a suitably substituted polymer having a high molecular weight and attaching the triglyceride derivative to it. This strategy provides molecular weights that are higher and provides the entanglement lengths needed for higher fracture toughness. In this work styrene maleic anhydride copolymer (SMA), maleic modified polypropylene (MMPP), poly(4-vinylpyridine) (P4VP), maleic modified polybutadiene (MMPBD) is grafted and/or cross-linked with epoxidized methyl oleate (EMO), epoxidized soybean oil (ESO), methyl ricinoleate (MR), soybean oil maleic anhydride (SOMA), castor oil (CO) and soybean oil diglyceride (DG). Also a new radically polymerizable triglyceride based monomer, 1-(4-vinylbenzene sulfonyl)oxy-2-alkonols of epoxidized soybean oil (SESO), was synthesized by the reaction of epoxidized soybean oil (ESO) with 4-vinylbenzene sulfonic acid (4VBSA). The adduct was homopolymerized into a soft and insoluble polymer in the presence of a free-radical initiator and also copolymerized with a reactive diluents such as styrene. Physical, chemical and mechanical properties of these new polymers are characterized by FTIR, 1H NMR, DSC, DMA and TGA.