Contents lists available at ScienceDirect Progress in Organic Coatings journal homepage: www.elsevier.com/locate/porgcoat Biobased poly(vinyl ether)s derived from soybean oil, linseed oil, and camelina oil: Synthesis, characterization, and properties of crosslinked networks and surface coatings Deep Joyti Kalita a , Ihor Tarnavchyk a , Mukund Sibi b , Bryan R. Moser c , Dean C. Webster a , Bret J. Chisholm a, ⁎ ,1 a Department of Coatings and Polymeric Materials, North Dakota State University, Fargo, ND, 58102, USA b Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND, 58102, USA c United StatesDepartment of Agriculture, Agricultural Research Service, National Center for Agricultural Utilization Research, Bio-Oils Research Unit, Peoria, IL, 61604, USA ARTICLE INFO Keywords: Poly(vinyl ether) Biobased Soybean oil Linseed oil Camelina oil Coating Paint Cationic polymerization Crosslinking Autoxidation Crosslinked network Living polymerization ABSTRACT A series of novel plant oil (PO)-based poly(vinyl ether)s were produced that varied with respect to PO com- position and molecular weight (MW). The POs investigated were soybean oil, linseed oil, and camelina oil. All of the polymers were liquids at room temperature and were used to produce crosslinked networks, both as free- standing films and as surface coatings on steel substrates. Crosslinking was achieved at ambient conditions through the process of autoxidation. Viscosity of the neat polymers as well as the viscoelastic and mechanical properties of crosslinked networks were highly dependent on parent PO composition. At a given polymer MW, viscosity decreased with increasing PO unsaturation, while glass transition temperature, Young’s modulus, and tensile strength of crosslinked networks increased with increasing PO unsaturation. For polymers derived from the most highly unsaturated PO, i.e. linseed oil, impact resistance of coatings was significantly compromised, due to the relatively high crosslink density of these coatings. Overall, these results demonstrated that viscosity and the properties of crosslinked films based on these novel PO-based poly(vinyl ether)s could be tailored through selection of the parent PO and control of polymer MW. This class of highly bio-based polymers appears to have particular utility for the production of one-component, ambient-cured coatings. One component, am- bient-cured thermoset coatings are highly desired because of their ease of use, lower waste production, and energy cost savings compared to other thermoset coating systems. 1. Introduction Prior to the abundant access to crude oil, chemicals and materials were derived from renewable resources, such as plant oils (POs), cel- lulosic biomass, tree resin, and insect secretions [1]. Due to the high demand for fossil fuels and the tremendous infrastructure put in place to meet the demand, research and development of chemicals and ma- terials from renewable materials was largely abandoned. At present, over ninety percent of all chemicals and materials are derived from oil and gas [2]. However, the finite supply of fossil resources, issues with climate change, and toxicity associated with many petrochemicals has caused a resurgence in the development of chemicals and materials from renewable resources [1]. Of the different renewable resources available for the development of chemicals and materials, POs are particularly attractive because they are relatively easy to isolate and their chemical components cannot be readily produced from oil and gas. The primary component of a PO is a mixture of triglycerides. [3] Depending on the species of the plant, fatty acid (FA) composition of the triglycerides can vary widely. For ex- ample, about 90 percent of the FAs from coconut oil triglycerides are saturated and are less than 18 carbons in length [4]. As a result, coconut oil has a melting temperature of about 24 °C and relatively good oxi- dative stability [5]. In contrast, linseed oil (LO) consists of FAs that are 18 carbons in length and about 90 percent contain unsaturation [4]. As a result, LO has a melting point of about -24 °C and is relatively easily oxidized [6]. With regard to industrial applications, POs have been used ex- tensively for paint and coating applications. [7] For example, prior to https://doi.org/10.1016/j.porgcoat.2018.09.033 Received 20 May 2018; Received in revised form 28 September 2018; Accepted 30 September 2018 ⁎ Corresponding author. 1 Current affiliation: PolyOne Corporation, Avon Lake, OH 44012, USA. E-mail address: bret.chisholm@polyone.com (B.J. Chisholm). Progress in Organic Coatings 125 (2018) 453–462 0300-9440/ © 2018 Published by Elsevier B.V. T