Poly(2-oxazoline)s Based on Phenolic Acids

Abstract

A series of phenolic-acid-based 2-oxazoline monomers with methoxy-substituted phenyl and cinnamyl side chains is synthesized and polymerized in a microwave reactor at 140 °C using methyl tosylate as the initiator. The obtained poly(2-oxazoline)s are characterized by NMR spectroscopy, MALDI-TOF mass spectrometry, and size-exclusion chromatography (SEC). Kinetic studies reveal that the microwave-assisted polymerization is fast and completed within less than ≈10 min for low monomer-to-initiator ratios of ≤25. Polymers with number-average molar masses of up to 6500 g mol^-1 and low dispersity (1.2-1.3) are produced. The aryl methyl ethers are successfully cleaved with aluminum triiodide/N,N'-diisopropylcarbodiimide to give a poly(2-oxazoline) with pendent catechol groups.

Keywords: 2-oxazoline; catechol; cationic ring-opening polymerization; microwave; phenolic acid.