Title

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

Document Type

Article

Publication Date

1-26-2010

Department

Chemistry and Biochemistry

Abstract

A functional derivative of epsilon-caprolactam, 5-azepane-2-one ethylene ketal or gamma-ethylene ketal epsilon-caprolactam, has been synthesized by a very straightforward and highly efficient Beckmann rearrangement reaction. Homopolymers of this new monomer and its copolymers with epsilon-caprolactam have been synthesized by anionic ring-opening polymerization using N-acetyl-epsilon-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 (co)polymers 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 it large number of application areas.

Publication Title

Macromolecules

Volume

43

Issue

2

First Page

968

Last Page

974