Synthesis of Polymers Bearing 1,3-Benzoxazine Moiety in the Side Chains from Poly(allylamine) and Their Crosslinking Behaviors

A polymer bearing 1,3-benzoxazine moiety in the side chain was synthesized successfully from poly(allylamine) based on a stepwise strategy consisted of three steps: (1) treatment of poly(allylamine) with salicylaldehyde to convert the amino group in the side chain into the corresponding o-(iminomethyl) phenol moiety, (2) reduction of the o-(iminomethyl) phenol to obtain the corresponding o-(aminomethyl) phenol moiety, and (3) formation of 1,3-benzoxazine moiety by the reaction of the o-(aminomethyl) phenol with formaldehyde. The content ratio of benzoxazine moieties and o-(aminomethyl) phenol moieties in the polymer were tunable by varying amount of formaldehyde. The presence of o-(aminomethyl) phenol moieties exhibited a significant promoting effect on the cross-linking reaction. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 3174-3183, 2011