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Bio-based polyfunctional reactive diluent derived from tung oil by thiol-ene click reaction for high bio-content UV-LED curable coatings
Industrial Crops and Products ( IF 5.9 ) Pub Date : 2020-11-26 , DOI: 10.1016/j.indcrop.2020.113117
Zhuangzhuang Chu , Yechang Feng , Bingqing Xie , Yu Yang , Yang Hu , Xiaohua Zhou , Teng Yuan , Zhuohong Yang

Materials with high bio-content have gradually replaced petroleum-based materials due to their sustainability, low cost, low toxicity and excellent performance in the field of UV-LED curable coatings. A novel tung oil-based methacrylate (TDMM) with low viscosity and multiple photopolymerizable methacrylates was designed and synthesized through three steps containing amidation, thiol-ene click reaction and esterification. The reaction conditions for thiol-ene click reaction were optimized by calculating double bond conversion and degree of functionalization of polyols. The chemical structures of the as-prepared TDMM were characterized by 1H NMR and FTIR. The rheological behavior analysis indicated that TDMM exhibited lower viscosity than petrochemical-based reactive diluent pentaerythritol triacrylate (PETA). Subsequently, TDMM showed good copolymerization ability with soybean oil-based reactive monomer (AESO) under the “green + green” UV-LED curable systems with high bio-content (61–81% in theory). The TDMM/AESO systems showed higher Tg but lower thermal stability, better modulus and tensile strength than the neat AESO. Besides, the UV-LED cured coatings exhibited excellent physical and chemical properties. This bio-renewable tung oil-based monomer is shown to be an effective reactive diluent and considered to have good potential in the development of the UV-LED curable coatings.



中文翻译:

通过硫醇-烯点击反应从桐油中提取的生物基多官能活性稀释剂,用于高生物含量的UV-LED固化涂料

具有高生物含量的材料由于其可持续性,低成本,低毒性以及在UV-LED固化涂料领域中的出色性能,已逐渐取代了石油基材料。通过酰胺化,硫醇-烯点击反应和酯化三个步骤,设计并合成了一种新型的低粘度桐油基甲基丙烯酸酯(TDMM)和多种可光聚合的甲基丙烯酸酯。通过计算双键转化率和多元醇的官能度,优化了硫醇-烯点击反应的反应条件。所制备的TDMM的化学结构的特征为11 H NMR和FTIR。流变行为分析表明,TDMM的粘度低于石化基反应性稀释剂季戊四醇三丙烯酸酯(PETA)。随后,在具有高生物含量(理论上为61–81%)的“绿色+绿色” UV-LED固化体系下,TDMM与大豆油基反应性单体(AESO)表现出良好的共聚能力。TDMM / AESO系统比纯AESO显示出更高的T g,但热稳定性更低,模量和拉伸强度更高。此外,UV-LED固化涂料具有优异的物理和化学性能。这种生物可再生的基于桐油的单体被证明是有效的反应性稀释剂,并被认为在开发UV-LED固化涂料方面具有良好的潜力。

更新日期:2020-11-27
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