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Novel synthesis routes for the preparation of low toxic vinyl ester and vinyl carbonate monomers
Synthetic Communications ( IF 2.1 ) Pub Date : 2020-09-22
Andreas Hofecker, Patrick Knaack, Patrick Steinbauer, Marica Markovic, Aleksandr Ovsianikov, Robert Liska

UV curing of photopolymerizable monomers, like (meth)acrylates, has been utilized for coatings for more than half a century and more recently in further developed areas such as tissue engineering. However, these monomers have major disadvantages, e.g., high irritancy and cytotoxicity, which leads to limited use in tissue engineering regarding health issues. Vinyl esters (VE) and vinyl carbonates (VC) can compete with (meth)acrylates in terms of material properties and have significantly lower toxicity, but lack in cost efficient synthesis methods. The purpose of this communication is to establish new pathways to overcome this drawback. It was shown that VEs can be synthesized either by vinyloxy trimethylsilane or by acetaldehyde in excellent yields. Moreover, a new method to synthesize vinyl chloroformate as precursor for VCs in lab scale was evolved by a catalyzed reaction of vinyloxy trimethylsilane with a phosgene solution. Finally, the cytotoxicity tests showed auspicious results.



中文翻译:

制备低毒乙烯基酯和碳酸乙烯基酯单体的新型合成途径

可光聚合单体(如(甲基)丙烯酸酯)的UV固化已被用于涂料超过半个世纪,最近更是在诸如组织工程学等进一步发展的领域中使用。然而,这些单体具有主要缺点,例如高刺激性和细胞毒性,这导致有关健康问题的组织工程用途有限。乙烯基酯(VE)和碳酸乙烯基酯(VC)在材料性能方面可以与(甲基)丙烯酸酯竞争,并且毒性显着降低,但缺乏经济高效的合成方法。这种交流的目的是建立克服这一缺陷的新途径。结果表明,可以通过乙烯基氧基三甲基硅烷或通过乙醛以优异的产率合成VE。此外,通过乙烯氧基三甲基硅烷与光气溶液的催化反应,开发了一种新的合成氯甲酸乙烯酯作为实验室规模的VCs前体的新方法。最后,细胞毒性试验显示出吉祥的结果。

更新日期:2020-09-22
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