Journal of Thermal Analysis and Calorimetry

, Volume 114, Issue 3, pp 1207–1215 | Cite as

The structure and thermal properties of novel DOPO-containing 1,3-benzoxazines

  • Haixiao Su
  • Zhiguo Liu


Three DOPO (9,10-dihydro-9-oxa-10-phospha-phenanthrene-10-oxide)-containing benzoxazin (3a3c) were successfully prepared from 2-hydroxybenzaldehyde, p-substituted aniline, and DOPO by a three-step procedure. Since the phosphorus and the adjacent aliphatic carbon are both chiral centers, two pairs of enantiomers exist in 3a, 3b, or 3c. Compound 3a′, which is a pair of enantiomers existing in 3a, was isolated using recrystallization in ethyl acetate solvent. All the structures were confirmed by FT-IR, NMR, and MS spectra. The X-ray analysis indicated that the 3a′ is the RR/SS enantiomers and belongs to the monoclinic crystal system, its space group being P21/c. The thermal properties were investigated by DSC and TG. It has been found that the peak temperature of thermally induced ring-opening reaction was around 260–270 °C. Compounds (3a3c, 3a′, and 3c′) had two similar thermal processes from 50 to 600 °C in TG, whereas the compound 3b′ had three thermal processes. The char yields of 3a3c were 18.10, 16.84, and 16.34 %, respectively, while those of 3a′–3c′ were 26.00, 31.80, and 19.21 %, respectively. The results indicated that compounds 3a′–3c′ had better char properties than 3a3c.


DOPO-containing benzoxazine Synthesis Enantiomers XRD Char property 



The authors acknowledge the financial support for this study from the Education Department of Sichuan Province, Xihua University, open laboratory of State Key Laboratory of Polymer Materials and Engineering(Sichuan University).


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Copyright information

© Akadémiai Kiadó, Budapest, Hungary 2013

Authors and Affiliations

  • Haixiao Su
    • 1
  • Zhiguo Liu
    • 2
  1. 1.School of Materials Science and EngineeringXihua UniversityChengduPeople’s Republic of China
  2. 2.School of Physics and ChemistryXihua UniversityChengduPeople’s Republic of China

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