Synthesis and Ring-opening Polymerization of 5-Azepane-2-one Ethylene Ketal: A New Route to Functional Aliphatic Polyamides

Lon J. Mathias, University of Southern Mississippi

Originally published in Macromolecules, Volume 43, Issue 2, 26 January 2010, Pages 968-974

Full-text available for USM authenticated users


A functional derivative of e-caprolactam, 5-azepane-2-one ethylene ketal or y-ethylene ketal e-caprolactam, has been synthesized by a very straightforward and highly efficient Beckmann rearrangement reaction. Homopolymers of this new monomer and its copolymers with ε-caprolactam have been synthesized by anionic ring-opening polymerization using N-acetyl-ε -caprolactam and NaH. The ketone groups can be easily released by deacetalyzation, and subsequent reaction leads to complete reduction to hydroxyl pendant groups. The ketone-containing ( copolymers respond sensitively to both thermal and photo-cross-linking in this novel class of materials. These new aliphatic polyamides bearing either ketone or hydroxyl pendant groups provide entries into a large number of application areas. © 2009 American Chemical Society.