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Synthesis of L-Malic Acid Based Poly(ester-thioether)s via Thiol-Ene Click Polymerization and Their Biodegradability
ChemistrySelect ( IF 1.9 ) Pub Date : 2021-09-17 , DOI: 10.1002/slct.202101160
Yuka Sato 1 , Akinori Takasu 1
Affiliation  

Many bio-based polymers made from natural resources do not show satisfactory biodegradability, leading to micro-plastic pollution. Here, thiol-ene click polymerization of di-3-butenyl l-malate (BMA) and diallyl l-malate (AMA) with several dithiols including 1,8-octanedithiol (OD) proceeded at 80 °C to give poly(ester-thioether)s in excellent yields (70 %–90 %). Using an azo-type radical trigger, polymerization proceeded more rapidly to give the expected poly(ester-thioether)s with Mn ranging from 1.9×103 to 9.4×103 and a molecular dispersity index (Mw/Mn) of 2.19–3.66. Click polymerization using 1,2-ethanedithiol (ED), ethylene bis(thioglycolate), and 2,3-butanedithiol proceeded to give similar poly(ester-thioether)s. In differential scanning calorimetry, all samples except for poly(BMA-alt-OD) had single Tg values between −37 and −47 °C. In biodegradation tests using activated sludge, poly(BMA-alt-OD) and poly(AMA-alt-ED) hardly showed biodegradability, but the other poly(ester-thioether)s showed 13 %–22 % biodegradation after 28 days. Our results open up new avenues in the design of bio-based polymers to reduce micro-plastic pollution.

中文翻译:

L-苹果酸基聚(酯-硫醚)的硫醇-烯点击聚合合成及其生物降解性

许多由自然资源制成的生物基聚合物没有表现出令人满意的生物降解性,导致微塑料污染。在这里,二-3-丁烯基l-苹果酸酯(BMA)和二烯丙基l-苹果酸酯(AMA)与包括1,8-辛二硫醇(OD)在内的几种二硫醇的硫醇-烯点击聚合在80°C下进行,得到聚(酯-硫醚)以优异的产率(70 %–90 %)。使用偶氮型自由基引发剂,聚合反应进行得更快,得到预期的聚(酯-硫醚),其M n范围为 1.9×10 3至 9.4×10 3,分子分散指数(M w / M n)为2.1 9 –3.6 6. 使用 1,2-乙二硫醇 (ED)、亚乙基双(巯基乙酸盐)和 2,3-丁二硫醇进行点击聚合,得到类似的聚(酯-硫醚)。在差示扫描量热法中,除聚 (BMA- alt -OD)外的所有样品都具有在 -37 和 -47 °C 之间的单一T g值。在使用活性污泥的生物降解试验中,聚(BMA- alt -OD)和聚(AMA- alt -ED)几乎没有显示出生物降解性,但其他聚(酯 - 硫醚)在 28 天后显示出 13%–22% 的生物降解。我们的研究结果为设计生物基聚合物以减少微塑料污染开辟了新途径。
更新日期:2021-09-17
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