Development of a DOPO-containing benzoxazine and its high-performance flame retardant copolybenzoxazines

A DOPO-containing benzoxazine, which could not be prepared by the traditional approaches, was successfully prepared from phenol, aniline and DOPO by a three-step procedure. The first step is the condensation of 2-hydroxybenzaldehyde with aniline, forming an intermediate imine. The second step is the addition of DOPO to the imine resulting a secondary amine. The third step is the ring closure condensation leading to DOPO-containing benzoxazine. All these structures were confirmed by 1D and 2D NMR spectra. The curing of mixtures of DOPO-containing benzoxazine and benzoxazine of bisphenol A has been studied. In the samples the molar ratio of benzoxazine monomers was varied to achieve different phosphorus content. The phosphorus-containing polybenzoxazines have been characterized by dynamic mechanical thermal analysis and thermogravimetric analysis. Limiting oxygen index values indicates good flame retardant properties. (C) 2009 Elsevier Ltd. All rights reserved.