Synthesis and Properties of Phthalocyanine and Cyano-Containing Epoxy Resin

doi:10.11901/1005.3093.2017.248

Chinese Journal of Materials Research

2017, Vol. 31

Issue (12): 925-930 DOI: 10.11901/1005.3093.2017.248

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Synthesis and Properties of Phthalocyanine and Cyano-Containing Epoxy Resin

Yangran JI¹, Xuhai XIONG², Ping CHEN¹(

), Xiaoyu ZHU¹

1 State Key Laboratory of Fine Chemicals＆ School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China
2 Liaoning Key Laboratory of Advanced Polymer Matrix Composites, Shenyang Aerospace University, Shenyang 110136, China

Cite this article:

Yangran JI, Xuhai XIONG, Ping CHEN, Xiaoyu ZHU. Synthesis and Properties of Phthalocyanine and Cyano-Containing Epoxy Resin. Chinese Journal of Materials Research, 2017, 31(12): 925-930.

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Abstract

A new phthalocyanine cyano bisphenol compound PPCN was synthesized by nucleophilic substitution reaction with phenolphthalein (PP) and 2,6-dichlorobenzonitrile as raw material and then reacts with epichlorohydrin to synthesize phthalocyanine cyano group epoxy resin. The structure of the target product is verified by ¹H-NMR spectroscopy and Fourier transform infrared spectroscopy (FTIR). The curing performance and kinetics of PPCE/methyl nadic anhydride (MNA) were investigated by DSC. The apparent activation energy evaluated according to Kissinger model is 57.78 kJ/mol, and the calculated reaction order is 0.76 based on Crane method. The results of the DMA and TGA show that the cured resin possesses excellent thermos-stability with a glass transition temperature 179℃ for the completely cured resin, and the activation energy of the thermos-degradation process is 52.88 kJ/mol and 13.21 kJ/mol for temperature ranges 327℃~357℃ and 357℃~574℃ respectively.

Key words: organic polymer materials epoxy resin addition polymerization phthalocyanine-containing compound cyano-containing compound

Received: 11 April 2017

ZTFLH:

TQ332.4

Fund: Supported by National Defense Key Program Fundamental Research Program (No. A35201xxxxx), National Natural Science Foundation of China (No. 51303107), Liaoning Key Laboratory Fundamental Research Project (Nos. LZ2015057&LZ2015058) and Natural Science Foundation of Liaoning Province (No. 201602569)

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https://www.cjmr.org/EN/10.11901/1005.3093.2017.248 OR https://www.cjmr.org/EN/Y2017/V31/I12/925

Fig.1 Synthesis route of PPCE

Fig.2 FTIR spectra of PPCN and PPCE (a) PPCN, (b) PPCE

Fig.3 ¹H-NMR spectra of PPCN

Table 1 Solubility of PPCE

Fig.4 DSC curves of PPCE/MNA system at different heating rates

Fig.5 Plots of ln(β/T_P²) and lnβ versus 1000/T_p

Table 2 DSC curing characteristics of the PPCE/MNA at different heating rates

Fig.6 Relationship of T and β

Fig.7 DMA thermograph of cured PPCE/MNA and E-51/MNA system

Fig.8 TG and DTG curves of cured PPCE/MNA system

Fig.9 Plots of

ln ln 1 1 - α

versus 1/T

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