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Synthesis of a Divinyl-functionalized Diamantane-Analogue from naturally occurring myo-Inositol and its application to polymer synthesis via the Thiol-ene reaction
Results in Chemistry ( IF 2.5 ) Pub Date : 2021-08-03 , DOI: 10.1016/j.rechem.2021.100167
Kimikatsu Ikeya 1 , Shusuke Okamoto 2 , Atsushi Sudo 1
Affiliation  

Myo-inositol, a naturally occurring cyclic compound obtained from rice bran, was transformed into a divinyl derivative bearing a rigid hexaoxadiamantane (HODAM) core composed of two orthoester moieties. The divinyl compound underwent radical polyaddition with dithiols to afford the corresponding semi-crystalline polythioethers, the melting temperatures (Tm) of which were above 240 °C. Furthermore, the divinyl compound was transformed into a HODAM-bearing diol via the radical addition of 2-mercaptoethanol to the vinyl groups. The diol product was used as a rigid monomer in polyurethane synthesis. The obtained polyurethanes exhibited glass transition temperatures (Tg) ranging from 55 to 110 °C.



中文翻译:

从天然存在的肌醇合成二乙烯基官能化二金刚烷类似物及其在通过硫醇 - 烯反应合成的聚合物中的应用

肌醇,从米糠中获得的天然存在的环化合物,转化成二乙烯基衍生物带有两个原酸酯基团所组成的刚性hexaoxadiamantane(HODAM)核心。所述二乙烯基化合物接受了根治性加聚用的二硫醇,得到相应的半结晶聚硫醚,熔融温度(Ť)是其中的高于240℃。此外,二乙烯基化合物通过 2-巯基乙醇与乙烯基的自由基加成转化为带有 HODAM 的二醇。二醇产品用作聚氨酯合成中的刚性单体。所得聚氨酯的玻璃化转变温度 ( T g ) 范围为 55 至 110 °C。

更新日期:2021-08-07
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