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The aza-Michael reaction as an alternative strategy to generate advanced silicon-based (macro)molecules and materials
Progress in Polymer Science ( IF 26.0 ) Pub Date : 2017-02-20 , DOI: 10.1016/j.progpolymsci.2017.02.002
Aymeric Genest , Daniel Portinha , Etienne Fleury , François Ganachaud

Aza-Michael reaction is a simple and accessible addition reaction performed at moderate temperature, possibly without a catalyst and without releasing by-products. Its versatility allows designing specific structures thanks to the availability of a multitude of Michael acceptors and Michael donors. The reaction rate of the aza-Michael reaction can be improved by adding different co-reactants (polar protic solvents, catalysts) and/or adjusting the external energy sources (e.g. moderate to high temperatures or high pressures). Here, we show that this addition reaction is efficient for modifying or curing silicon-containing molecules, oligomers and polymers. The pros and cons of applying the aza-Michael reaction to silicon-containing molecules (including alkoxysilanes and PDMS) are highlighted. A large variety of intermediates such as coupling agents, reactive diluents, and sol-gel precursors prepared by the aza-Michael reaction are presented. Finally, applications of these, including products ranging from functional silicone intermediates to soft (unfilled) elastomers, are reported.



中文翻译:

氮杂-迈克尔反应是生成先进的硅基(大分子)分子和材料的替代策略

氮杂-迈克尔反应是在中等温度下进行的简单且易于接近的加成反应,可能没有催化剂也没有释放副产物。由于具有多种迈克尔受体和迈克尔供体,其多功能性允许设计特定的结构。氮杂-迈克尔反应的反应速率可以通过添加不同的共反应物(极性质子溶剂,催化剂)和/或调节外部能源(例如中度到高温或高压)来提高。在这里,我们表明该加成反应对于改性或固化含硅分子,低聚物和聚合物是有效的。突出了将氮杂-迈克尔反应应用于含硅分子(包括烷氧基硅烷和PDMS)的利弊。各种各样的中间体,例如偶联剂,给出了反应性稀释剂和通过aza-Michael反应制备的溶胶-凝胶前体。最后,报道了这些产品的应用,包括从功能性有机硅中间体到软(未填充)弹性体的产品。

更新日期:2017-02-20
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