Coatings derived from novel, soybean oil-based polymers produced using carbocationic polymerization

Abstract

In this study, a process was developed to obtain vinylether-functional monomers containing fatty acid pendent groups directly from soybean oil (SBO) using base-catalyzed transesterification. In addition, a carbocationic polymerization process was developed for the vinylether monomers, which allowed for high molecular weight polymers to be produced without consuming any of the vinyl groups present in the fatty acid portion of the monomers. Compared to SBO, which possesses on average 4.5 vinyl groups per molecule, the polyvinylethers based on the soybean oilderived vinylether monomers (polyVESFA) possess tens to thousands of vinyl groups per molecule depending on the polymer molecular weight produced. As a result of this difference, coatings based on polyVESFA were shown to possess much higher crosslink density at a given degree of functional group conversion compared with analogs based on conventional SBO. In addition, the dramatically higher number of functional groups per molecule associated with polyVESFA results in gel-points being reached at much lower functional group conversion, which was shown to dramatically reduce cure-time compared with SBO-based analogs. Based on the results obtained, it appears that these new renewable materials may have tremendous commercial utility in the coatings industry.

Acrylated betulin as a comonomer for bio-based coatings. Part I: Characterization, photo-polymerization behavior and thermal stability

“…For instance, polymeric materials have been developed for textiles (Zhang et al, 2013), adhesives (O'Dell et al, 2013;Xing et al, 2013) and coatings (Alam and Chisholm, 2011;Chen et al, 2011). Vegetable oils are an excellent source of polymer synthesis raw materials (Meier et al, 2007).…”

Evaluation of soy‐based surface active copolymers as surfactant ingredients in model shampoo formulations

“…The soybean oil-based vinyl ether monomer, 2-(vinyloxy)ethyl soyate (2-VOES), was synthesized as described elsewhere [32]. The soybean oil-based vinyl ether monomer, 2-(vinyloxy)ethyl soyate (2-VOES), was synthesized as described elsewhere [32].…”

“…Synthesis. The soybean oil-based vinyl ether monomer, 2-(vinyloxy)ethyl soyate (2-VOES), was synthesized as described elsewhere [32]. The hydrophilic vinyl ether monomer, penta(ethylene glycol) ethyl vinyl ether (PEGEVE), was synthesized by first producing the tosylate of tri(ethylene glycol) ethyl ether (TsTEGEE) and reacting it with diethylene glycol vinyl ether (DEGVE).…”

Plant Oil‐Derived Epoxy Polymers toward Sustainable Biobased Thermosets

“…Chisholm and co-workers prepared epoxidized poly(2-vinyloxyethyl soylate) and demonstrated its application for epoxy resins. [14] Herein, four soybean oil derived polymers, EP1, EP2, EP3, and EP4 were used for formulating epoxy resins in a systematic manner ( Figure 1). It should be mentioned that the glass transition temperatures (T g s) of these epoxidized polymers were in the range of −33 to 22 °C, making it possible to uncover the influence of polymer structures.…”