The 6,6'-bis(3-benzonitrile-3,4-dihydro-2H-benzo[e][1,3]oxazinyl) isopropane (BA-PABN) was synthesized from bisphenol-A, p-aminobenzonitrile and paraformaldehyde via solventless method. The chemical structure of BA-PABN was confirmed by H-1 and C-13 nuclear magnetic resonance (NMR) spectroscopy, Fourier transform infrared (FTIR) spectroscopy, and elemental analysis, and the polymerization of BA-PABN was investigated by FTIR, solid-state C-13 NMR, and differential scanning calorimetry. BA-PABN undergoes the oxazine ring-opening polymerization and the cyclotrimerization of cyano groups with the formation of the corresponding polybenzoxazine (PBA-PABN). Dynamic mechanical analysis results show the storage modulus of PBA-PABN at 25 degrees C is about 2.7 GPa, and the glass transition temperature is 190 degrees C. The 5% and 10% weight loss temperatures of PBA-PABN are 300 and 325 degrees C in both air and nitrogen, respectively. The char yield is about 43% at 800 degrees C in nitrogen, whereas almost no degradation residue is remained at 750 degrees C in air. (C) 2012 Elsevier B.V. All rights reserved.