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Chain-End Functional di-Sorbitan Oleate Monomer Obtained from Renewable Resources as Precursors for Bio-Based Polyurethanes
Journal of Polymers and the Environment ( IF 4.7 ) Pub Date : 2020-03-03 , DOI: 10.1007/s10924-020-01692-0
Susana Valencia-Bermudez , Susana Hernández-López , Manuel Gutiérrez-Nava , José-Manuel Rojas-García , Luis-Edmundo Lugo-Uribe

A three-step synthetic route was proposed and tested to obtain a chain-end functional di-sorbitan oleate monomer: First, 1,18-octadec-9-enedioic acid compound was produced by self-metathesis reaction of an oleic acid; then, the 1,18-octadec-9-enoyl dichloride compound was yielded by chlorination of the di-acid with thionyl chloride, and finally, the 1,18-di-sorbitan oleate monomer was yielded by esterification of the dichloride with 1,4-sorbitan. The di-sorbitan oleate monomer was purified and then characterized by FTIR, 1H-NMR, DSC and TGA to establish its structure and properties. A bio-based polyurethane (PU) was synthesized by reacting the obtained 1,18-di-sorbitan oleate monomer and MDI. Rheological analysis showed that a curing reaction occurs as a significant increase of the storage modulus (G’) and the complex viscosity (η*) at 100 °C. The obtained bio-based PU was characterized by FTIR, TGA and DMA, confirming that 1,18-di-sorbitan oleate is a feasible monomer for synthesizing polyurethanes.



中文翻译:

从可再生资源中获得的链端功能性双山梨糖醇油酸酯单体,作为生物基聚氨酯的前体

提出了三步合成路线并进行了测试,以获得链端官能的双脱水山梨糖醇油酸酯单体:首先,通过油酸的自我复分解反应制备1,18-十八烷基-9-烯二酸化合物。然后,将二酸用亚硫酰氯氯化,得到1,18-十八烷基-9-烯酰二氯化合物,最后,通过将二氯化物与1酯化,得到1,18-二脱水山梨糖醇油酸酯单体。 4-脱水山梨糖醇。纯化二脱水山梨糖醇油酸酯单体,然后通过FTIR,1表征H-NMR,DSC和TGA建立其结构和性质。通过使获得的1,18-二脱水山梨糖醇油酸酯单体与MDI反应,合成生物基聚氨酯(PU)。流变学分析表明,在100°C下,固化反应会随着储能模量(G')和复数粘度(η*)的显着增加而发生。通过FTIR,TGA和DMA对获得的生物基PU进行了表征,证实了1,18-二脱水山梨糖醇油酸酯是用于合成聚氨酯的可行单体。

更新日期:2020-04-21
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