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

School

Mathematics and Natural Sciences

Abstract

A functional derivative of ε-caprolactam, 5-azepane-2-one ethylene ketal or γ-ethylene ketal ε-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 (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 a large number of application areas.

Publication Title

Macromolecules

Volume

43

Issue

2

First Page

968

Last Page

974

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