2-(Vinyloxy)ethyl soyate as a versatile platform chemical for coatings: An overview

A plant oil-based polymer technology was recently developed that enables high molecular weight polyvinylether polymers to be produced using cationic polymerization. The plant oil monomer synthesis involves simple base-catalyzed transesterification of a plant oil triglyceride with a hydroxy-functional vinyl, ether such as 4-(vinyloxy)butanol or 2-(vinyloxy)ethanol, to produce a mixture of vinyl ether monomers that possess fatty acid ester groups in their structure. A key aspect of the technology involves the polymerization process that allows for high molecular weight polymers to be produced by polymerization exclusively through the vinyl ether double bonds. This feature enables polymers to be produced that possess unsaturation in the fatty acid ester pendent groups derived from the plant oil starting material. As has been done for conventional plant oil triglycerides, the double bonds can be used to produce thermoset materials either directly through an oxidative process or by derivatization to produce other functional groups, such as epoxides, acrylates, and hydroxyls that can be subsequently used to produce crosslinked networks. The polymerization process also results in a living polymerization that allows for control of polymer molecular weight, narrow molecular weight distributions, and the production of unique polymer architectures such as block copolymers. Another very important feature of the technology involves the ability to copolymerize the plant oil-based vinyl ether monomers with other monomers to tailor polymer properties such as glass transition temperature, mechanical properties, and solubility/compatibility with other materials. This document provides an overview of the present state of the technology using soybean oil as a representative plant oil source.