Synthesis of α‐1,3‐ and β‐1,3‐glucan esters with carbon–carbon double bonds and their surface modification,Polymer International

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Synthesis of α‐1,3‐ and β‐1,3‐glucan esters with carbon–carbon double bonds and their surface modification
Polymer International ( IF 2.9 ) Pub Date : 2020-11-27 , DOI: 10.1002/pi.6157
Yuki Hori ₁ , Yukiko Enomoto ₁ , Satoshi Kimura ₁ , Tadahisa Iwata ₁

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α‐1,3‐glucan and β‐1,3‐glucan esters with carbon–carbon double bonds (C=C), namely, α‐1,3‐glucan butenoate (α₁₃GB) and β‐1,3‐glucan butenoate (β₁₃GB), were synthesized from 3‐butenoic acid and trifluoroacetic anhydride. NMR analysis of the two esters revealed that the 3‐butenoyl groups were partially transformed to 2‐butenoyl groups. The total degree of substitution (DS_total) of the esters was calculated to be 3.0. According to gel permeation chromatography analysis, α₁₃GB had a molecular weight (M_w) of 2.2 × 10⁵ and β₁₃GB had an M_w of 11.0 × 10⁵, which was unexpectedly higher than that of the original glucan. This suggests that the β₁₃GB chains were partially and intramolecularly crosslinked via the C=C bond. The α₁₃GB and β₁₃GB obtained had thermal degradation temperatures of 398 and 375 °C, respectively, and glass transition temperatures of 117 and 119 °C, respectively, which were higher than those of the corresponding saturated glucan butyrates. The surfaces of cast films of the esters were modified with 1H,1H,2H,2H‐perfluorodecanethiol, n‐dodecyl mercaptan or 3‐mercapto‐1,2‐propanediol via thiol‐ene reactions. Attenuated total reflection Fourier transform infrared spectroscopy and scanning electron microscopy energy‐dispersive X‐ray spectroscopy analyses revealed that the surface of α₁₃GB was more successfully modified with these thiol compounds than that of β₁₃GB. The water contact angle of the surface of each cast film was measured to evaluate its hydrophobicity and hydrophilicity, and indicated the successful surface modification of the film by the thiol compounds © 2020 Society of Chemical Industry

中文翻译：

具有碳-碳双键的α-1,3-和β-1,3-葡聚糖酯的合成及其表面改性

具有碳-碳双键的α-1,3-葡聚糖和β-1,3-葡聚糖酯（C = C），即，α-1,3-葡聚糖丁烯酸甲酯（α ₁₃ GB）和β-1,3-葡聚糖丁烯酸甲酯（β ₁₃ GB）中，从3-丁烯酸和三氟乙酸酐合成。两种酯的NMR分析表明，3-丁烯酰基被部分转化为2-丁烯酰基。酯的_总取代度（DS _total）经计算为3.0。根据凝胶渗透色谱法分析，α ₁₃ GB具有分子量（中号_瓦特的2.2×10）⁵，β ₁₃ GB有一个中号_瓦特的11.0×10 ⁵，其出乎意料地高于原始葡聚糖。这表明，β _13支GB链被部分和分子内通过C = C键交联。所述α ₁₃ GB和β ₁₃ GB得到的具有398和375℃，分别，和玻璃化转变的117和119的温度℃，分别均较相应的饱和葡聚糖丁酸酯的更高的热降解温度。酯的流延膜的表面用1进行了修改ħ，1 ħ，2 ħ，2 ħ -perfluorodecanethiol，Ñ十二烷基硫醇或3-巯基1,2-丙二醇通过硫醇反应。衰减全反射傅里叶变换红外光谱和扫描电子显微镜能量分散X射线光谱仪分析显示，α的表面₁₃ GB被更成功地修改了这些硫醇化合物比β的₁₃ GB。测量每个流延膜表面的水接触角以评估其疏水性和亲水性，并表明硫醇化合物对膜的成功表面改性©2020年化学工业协会

更新日期：2020-11-27

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