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Cold-Resistance Plasticizers Derived from Bio-Based Trans-Aconitic Acid with High Performance on Solvent Extraction
Yirui Shen1,2,3, Xiaomei Wang2, Yangyang Xiong2
1The National and Local Joint Engineering Research Center for Biomanufacturing of Chiral Chemicals, Zhejiang University of Technology, Hangzhou 310014, China.
Abstract:
Dioctyl adipate (DOA) and dioctyl sebacate (DOS) are widely used cold-resistance plasticizers; however, their low molecular weight and weak polarity result in poor thermal stability and migration resistance. Here, we report the synthesis and performance of bio-based cold-resistance plasticizers derived from trans-aconitic acid with enhanced migration resistance. Tri-n-butyl trans-aconitate (TBTA), tri-n-hexyl trans-aconitate (THTA), and tri-n-octyl trans-aconitate (TOTA) were synthesized via one-step esterification with aliphatic alcohols and applied in poly(vinyl chloride) (PVC). Compared with commercial plasticizers di-(2-ethylhexyl) phthalate (DEHP), tributyl citrate (TBC) and DOA, the synthesized plasticizers demonstrated excellent thermal stability and cold-resistance. After freezing treatment, the Tg values of TBTA/PVC (18.99 °C) and THTA/PVC (20.88 °C) were lower than those of DEHP/PVC (22.74 °C). The branched architecture was supposed to strengthen interactions between plasticizers and PVC, improving volatility resistance and solvent extraction resistance. Compared with DOA/PVC at 48 h, TBTA/PVC, THTA/PVC and TOTA/PVC displayed volatility mass loss reduction of ~1.5%, 4% and 7%, respectively. Their extraction mass loss in ethanol decreased by 5-6%, while in petroleum ether, TBTA/PVC and TOTA/PVC dropped by 11.95% and 2.63%, respectively. These bio-based plasticizers are promising alternatives to the poor migration resistance of conventional low-temperature plasticizers.
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