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

Abstract

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.

Sustainable Elastomers from Renewable Biomass

“…Chisholm and coworkers prepared a vinyl ether monomer, 2-VOES, by transesterification between ethylene glycol vinyl ether and soybean oil. 21 By the use of 1-isobutoxyethyl acetate as an initiator and ethylaluminum sequichloride as a co-initiator, a viscous polymer with a T g of −92 °C was prepared. 22 Since both oxazoline and vinyl ether monomers were polymerized by living cationic polymerization, which requires quite strict reaction conditions and high purity of monomers, strategies toward polymerizable monomers under less stringent conditions were sought.…”

Supramolecular Polymer Nanocomposites Derived from Plant Oils and Cellulose Nanocrystals

“…A vinyl ether monomer was prepared from the transesterification of 2-(vinyloxy)ethanol with soybean oil and polymerized by living cationic polymerization. 29,30 We reported the preparation of a series of different (meth)acrylate monomers from soybean oil via facile amidation. 31−35 Thermoplastic polymers with glass transition temperature in the range −54 to 60 °C were prepared after simple free radical polymerizations of these monomers.…”

“…Plant oils are one of the most abundant and low-cost biomass and have been widely used in chemical industry (i.e., surfactants, paper sizing agents). − Thermoset materials have been widely achieved from plant oils for numerous applications (i.e., surface coatings, polyurethane foam, rubbers). , For example, polyols were prepared from epoxidized vegetable oils and used for making thermosets. − Recently, processable polymers prepared from plant oils were reported. , A new trend is on the conversion of plant oils into monofunctional monomers for making reprocessable polymers. A vinyl ether monomer was prepared from the transesterification of 2-(vinyloxy)­ethanol with soybean oil and polymerized by living cationic polymerization. , We reported the preparation of a series of different (meth)­acrylate monomers from soybean oil via facile amidation. − Thermoplastic polymers with glass transition temperature in the range −54 to 60 °C were prepared after simple free radical polymerizations of these monomers. However, the highest tensile strength from these polymers is only 3.0 MPa.…”

Plant Oil‐Derived Epoxy Polymers toward Sustainable Biobased Thermosets

“…Since unsaturated double bonds could be easily converted to epoxy, soy derivatives with a higher number of epoxides could be achieved for fabricating sustainable epoxy resins. Chisholm and co‐workers prepared epoxidized poly(2‐vinyloxyethyl soylate) and demonstrated its application for epoxy resins …”