Processing polyvinyl chloride (PVC) artificial material requires plasticizer that softens the PVC coating. Currently, utilizing unsaturated fatty acid methyl esters to obtain epoxidized fatty acid methyl ester (EFAME) bio-plasticizers constitutes an environmentally responsible solution to substitute conventional ortho-phthalates that are endocrine disruptors or probable carcinogens. However, commercial EFAMEs, even with the highest epoxy value (ca. 5.5–5.8%) so far, still suffer from fast leaching from the PVC matrix, burdening the environment and shortening lifespan of the artificial material. Here, we report a proof-of-principle demonstration of a new strategy to obtain migration-resistant EFAME that harnesses the midchain hydroxyl of methyl ricinoleate and covalently attachment of a pendant acetate ester. Despite a low epoxy value (3.0%), the engineered bio-plasticizer displays significantly suppressed migration in multiple scenarios compared with one conventional EFAME with much higher epoxy value (5.8%). Circumventing the limit confronting previous strategy that highlights the sole contribution of epoxy value to achievable migration resistance, the rationale herein may provide guidance for designing new EFAMEs with comparable performance to ortho-phthalates, thus bringing the old and oft-maligned PVC artificial material industry one step closer to sustainability.

中文翻译：

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用于PVC人造材料的带有侧酯乙酸酯的环氧化蓖麻油酸甲酯生物增塑剂：克服了对可达到的耐迁移性的现有限制

加工聚氯乙烯（PVC）人造材料需要增塑剂，以软化PVC涂层。当前，利用不饱和脂肪酸甲酯获得环氧化脂肪酸甲酯（EFAME）生物增塑剂构成了一种对环境负责的解决方案，以替代作为内分泌干扰物或可能致癌物的常规邻苯二甲酸酯。但是，到目前为止，即使商用环氧树脂的环氧值最高（约5.5-5.8％），仍然会从PVC基质中快速浸出，给环境造成负担，并缩短了人造材料的使用寿命。在这里，我们报告了一项新策略的原理证明，该策略获得了抗迁移的EFAME，该方案利用了蓖麻油酸甲酯的中链羟基和乙酸酯侧链的共价连接。尽管环氧值较低（3.0％），与一种具有更高环氧值（5.8％）的常规EFAME相比，该工程化生物增塑剂在多种情况下均显示出显着抑制的迁移。规避先前策略的局限性，即突出环氧值对可实现的耐迁移性的唯一贡献，此处的原理可以为设计性能与邻苯二甲酸酯相媲美的新型EFAME提供指导，从而使老旧的PVC人造材料行业成为一个现实。迈向可持续发展。