SYNTHESIS OF AROMATIC DIAMINE-BASED BENZOXAZINES AND EFFECT OF THEIR BACKBONE STRUCTURE ON THERMAL AND FLAMMABILITY PROPERTIES OF POLYMERS

Tao Zhang ^1,2,3 ,
Hong-qiang Yan ^4,, ,
Zheng-ping Fang ^1,5,3 ,
Mao Penga ⁶

1.
1. MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China
2.
2. Department of Packaging Engineering, College of Materials and Textiles, Zhejiang Sci-tech University, Hangzhou 310018, China
3.
4.
Lab of Polymer Materials and Engineering, Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, China
5.
2. Lab of Polymer Materials and Engineering, Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, China
6.
MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China

Corresponding author: Hong-qiang Yan,
Received Date: 15 October 2012
Revised Date: 28 December 2012

Fund Project: National Natural Science Foundation of China (No. 51103129), the National Basic Research Program of China (973 Program, No. 2010CB631105), the Ningbo Natural Science Foundation (No. 2012A610084), the Open Fund of Zhejiang Provincial Top Key Discipline of New Materials and Process Engineering (No. 20110939).

Three kinds of novel aromatic diamine-based benzoxazines containing naphthalene, propane-2, 2-diyldibenzene and neopentyl groups in the backbone, respectively (designated as BAPNCP, BAPBACP and BAPNPGCP, respectively), were synthesized and characterized. In addition, the effects of backbone structures on curing behaviors of the monomers and thermal and flammability properties of the resulting polymers were systematically studied. The results indicated that BAPNPGCP displayed the highest enthalpy of the curing reaction associated with the ring-opening of benzoxazine, which was due to the effect of benzoxazine ring content per unit mass. Interestingly, the 5 wt% weight loss temperature and char residue after thermogravimetric test for poly(BAPNPGCP) were 8 ℃ and 7% higher than those of poly(BAPBACP). Meanwhile, the total heat release of poly(BAPNPGCP) was less than half of that for poly(BAPBACP), indicating the substantial effect of benzoxazine ring content on flammability and char formation. Furthermore, it was found that poly(BAPNCP) gave the best thermal stability and flame retardancy, which was due to the synergistic effect between naphthalene group and benzoxazine ring content. This study provides new insight into the curing behavior of benzoxazine and further understanding on the high performance of polybenzoxazine.

SYNTHESIS OF AROMATIC DIAMINE-BASED BENZOXAZINES AND EFFECT OF THEIR BACKBONE STRUCTURE ON THERMAL AND FLAMMABILITY PROPERTIES OF POLYMERS

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