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Novel synthesis routes for the preparation of low toxic vinyl ester and vinyl carbonate monomers
Synthetic Communications ( IF 1.8 ) Pub Date : 2020-09-22 , DOI: 10.1080/00397911.2020.1808995
Andreas Hofecker 1 , Patrick Knaack 1 , Patrick Steinbauer 1 , Marica Markovic 2 , Aleksandr Ovsianikov 2 , Robert Liska 1
Affiliation  

Abstract 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. Graphical Abstract

中文翻译:

制备低毒乙烯基酯和碳酸乙烯基酯单体的新合成路线

摘要 光聚合单体(如(甲基)丙烯酸酯)的 UV 固化已被用于涂料半个多世纪,最近又用于进一步发展的领域,如组织工程。然而,这些单体具有主要缺点,例如高刺激性和细胞毒性,这导致在有关健康问题的组织工程中的应用受到限制。乙烯基酯(VE)和碳酸乙烯酯(VC)在材料性能方面可以与(甲基)丙烯酸酯竞争,并且毒性明显较低,但缺乏成本效益好的合成方法。这种交流的目的是建立新的途径来克服这个缺点。结果表明,VE 可以通过乙烯氧基三甲基硅烷或乙醛以优异的产率合成。而且,通过乙烯氧基三甲基硅烷与光气溶液的催化反应,开发了一种在实验室规模合成氯甲酸乙烯酯作为 VC 前体的新方法。最后,细胞毒性试验显示了良好的结果。图形概要
更新日期:2020-09-22
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