Mechanistic studies on ring-opening polymerization of benzoxazines: A mechanistically based catalyst design

Chao Liu, Dongmei Shen, Rosa María Sebastián, Jordi Marquet, Rainer Schönfeld

Research output: Contribution to journalArticleResearchpeer-review

155 Citations (Scopus)

Abstract

Ring-opening polymerization behavior of a model p-cresol-aniline-based benzoxazine under various conditions was investigated in detail by 1H NMR analysis in deuterated DMSO. An improved mechanistic scheme was proposed to explain the observed experimental results. In light of this mechanistic scheme, several bifunctional catalysts were studied, and lithium iodide was found to be a very active and effective catalyst. Lithium cation is the Lewis acid part and effectively coordinates with oxygen or nitrogen atoms and promotes ring-opening of benzoxazines. Iodide ion is the nucleophilic part with good leaving ability and can react with the ring-opened imminium intermediates to prevent its rapid recombination with the phenolate. © 2011 American Chemical Society.
Original languageEnglish
Pages (from-to)4616-4622
JournalMacromolecules
Volume44
Issue number12
DOIs
Publication statusPublished - 28 Jun 2011

Fingerprint

Dive into the research topics of 'Mechanistic studies on ring-opening polymerization of benzoxazines: A mechanistically based catalyst design'. Together they form a unique fingerprint.

Cite this