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Degradable and renewably-sourced poly(ester-thioethers) by photo-initiated thiol–ene polymerization†
Polymer Chemistry ( IF 4.1 ) Pub Date : 2018-05-28 00:00:00 , DOI: 10.1039/c8py00502h
Leon M. Lillie 1, 2, 3, 4 , William B. Tolman 5, 6, 7, 8, 9 , Theresa M. Reineke 1, 2, 3, 4
Affiliation  

With the aim of preparing sustainable and degradable polymers from sugar-derived precursors, a family of five poly(ester-thioethers) were synthesized by photoinitiated thiol–ene polymerization of monomers incorporating D-glucaro-1,4:6,3-dilactone (GDL). Various dithiols were used to produce linear poly(ester-thioethers) of glucarodilactone 10-undecenoate (GDLU) to probe the effect of the dithiols on the observed mechanical performance and degradability. The samples exhibited glass transition (Tg) values from −8.7 to 19 °C. The polymers with the simplest dithiols, 1,2-ethanedithiol (EtDT) and 3,6-dioxa-1,8-octane-dithiol (DODT), were found to exhibit crystallinity, while the more structurally complex and rigid dithiol structures were found to produce amorphous materials. Due to the GDL units in the polymers, rapid degradation under basic aqueous conditions and stability in acidic and neutral conditions were observed. Tensile testing of these materials showed robust mechanical properties, including tunable moduli (0.011 to 0.29 GPa), strength (21 to 42 MPa), and ductility (410 to 590%).

中文翻译:

通过光引发的硫醇-烯聚合可降解和可再生来源的聚(酯-硫醚)

为了从糖衍生的前体制备可持续的和可降解的聚合物,通过光引发的硫醇-烯聚合掺入D -glucaro-1,4:6,3-二内酯的单体合成了五种聚(酯-硫醚)( GDL)。各种二硫醇被用于生产线性葡糖二内酯10-十一碳酸酯(GDLU)的聚(酯-硫醚),以探测二硫醇对观察到的机械性能和降解性的影响。样品表现出玻璃化转变温度(T g)值在-8.7至19°C之间。发现具有最简单的二硫醇,1,2-乙二硫醇(EtDT)和3,6-二氧杂-1,8-辛烷-二硫醇(DODT)的聚合物表现出结晶度,而发现结构更复杂且刚性更高的二硫醇结构生产无定形材料。由于聚合物中的GDL单元,在碱性水溶液条件下可快速降解,在酸性和中性条件下可观察到稳定性。这些材料的拉伸测试显示出强大的机械性能,包括可调模量(0.011至0.29 GPa),强度(21至42 MPa)和延展性(410至590%)。
更新日期:2018-05-28
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