Tung oil based plasticizer and auxiliary stabilizer for poly(vinyl chloride) Mei Li a,b,c,d,e , Shouhai Li a,b,c,d,e , Jianling Xia a,b,c,d,e , Chengxiang Ding a , Mei Wang a , Lina Xu a,b,d,e , Xiaohua Yang a,b,d,e , Kun Huang a,b,d,e, ⁎ a Institute of Chemical Industry of Forestry Products, CAF, Nanjing 210042, PR China b Jiangsu Province Biomass Energy and Materials Laboratory, Nanjing 210042, PR China c Institute of Forest New Technology, CAF, Beijing 100091, PR China d National Engineering Lab. for Biomass Chemical Utilization, Nanjing 210042, PR China e Key and Lab. on Forest Chemical Engineering, SFA, Nanjing 210042, PR China HIGHLIGHTS • Tung oil was successfully converted in- to epoxidized dicarboxylic acid dimeth- yl ester (epoxidized-C21-DAE). • Epoxidized-C21-DAE are introduced as primary plasticizer and auxiliary thermal stabilizer for poly(vinyl chloride)(PVC). • The epoxidized-C21-DAE as a primary plasticizer for PVC significantly im- proved PVC thermal stability and flexi- bility. • The epoxidized-C21-DAE plasticizer was compatible with PVC and could not be easily extracted GRAPHICAL ABSTRACT A tung oil derivative, epoxidized dicarboxylic acid dimethyl ester, was successfully prepared and used as both a green primary plasticizer and a high efficiency auxiliary thermal stabilizer for poly(vinyl chloride). abstract article info Article history: Received 3 November 2016 Received in revised form 6 March 2017 Accepted 7 March 2017 Available online 08 March 2017 A tung oil derived epoxidized dicarboxylic acid dimethyl ester (epoxidized-C21-DAE), was synthesized through transesterification, a Diels-Alder reaction, and epoxidation. The chemical structure of the epoxidized-C21-DAE was confirmed using Fourier transform infrared spectroscopy (FTIR), proton nuclear magnetic resonance ( 1 H NMR) and carbon-13 nuclear magnetic resonance ( 13 C NMR). The thermal and migration stabilities and the mechanical properties of PVC samples were investigated using discoloration, tensile, exudation, volatility, and extraction tests as well as thermal gravity analysis (TGA), TGA–FTIR analysis, and dynamic mechanical analysis (DMA). The petroleum-based plasticizer, dioctyl terephthalate (DOTP), and the biobased plasticizer, ep- oxidized fatty acid methyl ester (EFAME), were chosen as controls and their properties compared with epoxidized-C21-DAE. The application of epoxidized C21-DAE as a biobased, primary plasticizer for poly(vinyl chloride) significantly improved PVC thermal stability over that of DOTP and EFAME. The mechanical properties of this type of PVC were superior to those of DOTP. In addition, the migration and volatility stabilities of epoxidized- C21-DAE were much better than EFAME. Epoxidized-C21-DAE could, therefore, be fully substituted for commercial DOTP or EFAME. Tung oil derived epoxidized-C21-DAE has good potential as a primary PVC plasticizer. © 2017 Elsevier Ltd. All rights reserved. Keywords: Poly(vinyl chloride) Tung oil Epoxidized dicarboxylic acid dimethyl ester Plasticizer Thermal stability Materials and Design 122 (2017) 366–375 ⁎ Corresponding author at: Institute of Chemical Industry of Forestry Products, Chinese Academy of Forestry, No. 16 Suojin 5th village, Nanjing 210042, PR China. E-mail address: kunhuang@caf.ac.cn (K. Huang). http://dx.doi.org/10.1016/j.matdes.2017.03.025 0264-1275/© 2017 Elsevier Ltd. All rights reserved. Contents lists available at ScienceDirect Materials and Design journal homepage: www.elsevier.com/locate/matdes