Synthesis of dicyano-substituted ε-caprolactone and its (co)polymers

Add time:09/27/2019    Source:sciencedirect.com

A synthetic approach to the dicyano-substituted ε-caprolactone was developed. It consists of a cyclohexanone ring assembly through the Diels-Alder reaction followed by the Baeyer-Villiger oxidation. Ring-opening polymerization of the synthesized monomer, catalyzed by the aluminum alkoxides, was performed in a well-controlled manner and provided the nitrile-polyester homopolymers of various molar masses. The synthesized nitrilePCL homopolymers are amorphous with a significantly higher glass transition temperature (66–69 °C) compared to the unsubstituted PCL. The dicyano-substituted ε-caprolactone monomer was copolymerized with the unsubstituted ε-caprolactone to prepare the statistical and block copolymers. Furthermore, the cyano groups of the nitrilePCL homopolymers were transformed into the amide groups by post-polymerization modification under anhydrous conditions using the Wilkinson’s catalyst. The resulting amide-functionalized polyesters are water-soluble when the degree of transformation is higher than 80%.

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