Abstract
To investigate the role of position of oxazine ring in the benzoxazine backbone on their ring-opening polymerization (ROP) and thermal stability of resulting polybenzoxazine, we have synthesized difunctional monomers solely containing benzoxazine moieties (BZ2) with attached oxazine ring at the para-, meta-, and ortho-position. The ROP was examined by DSC analysis, which revealed a reduction in curing temperature in the order of meta (225 °C) < ortho (239 °C) < para (251 °C). The differences in structural and geometrical parameters were investigated by NMR (1H, 13C, 1H–1H NOESY) and X-ray crystallography analysis. The electronic effects and the intramolecular interaction between oxazine ring and aromatic hydrogen were higher when the attached oxazine ring was at the meta-position. The differences in their positioning also changed their ROP mechanism, an unusual intramolecular polymerization was observed in meta, while in ortho and para the polymerization proceeded in a regular manner. A curing mechanism r...
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