Synthesis and properties of high temperature phthalonitrile polymers based on o, m, p-dihydroxybenzene isomers

Xinggang Chen; Shuyan Shan; Jiayu Liu; Xiongwei Qu; Qingxin Zhang

doi:10.1039/C5RA15321B

Synthesis and properties of high temperature phthalonitrile polymers based on o, m, p-dihydroxybenzene isomers

Xinggang Chen,^a^b^c Shuyan Shan,^b Jiayu Liu,^b Xiongwei Qu^a^b and Qingxin Zhang*^a^b

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* Corresponding authors

^a Key Lab for Micro- and Nano-Scale Boron Nitride Materials in Hebei Province, School of Materials Science and Engineering, Hebei University of Technology, Tianjin 300130, China
E-mail: zhqxcn@163.com

^b Institute of Polymer Science and Engineering, School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130, China

^c Hebei Province Key Laboratory of Inorganic Nonmetallic Materials, School of Materials Science and Engineering, North China University of Science and Technology, Tangshan, China

Abstract

A series of high-temperature phthalonitrile monomers with o, m, p-dihydroxybenzene isomers, namely, 1,2-bis(3,4-dicyanophenoxy) benzene (o-BDB), 1,3-bis(3,4-dicyanophenoxy) benzene (m-BDB) and 1,4-bis(3,4-dicyanophenoxy) benzene (p-BDB), were synthesized via a facile nucleophilic displacement of a nitro-substituent from 4-nitrophthalonitrile. The structures of the monomers were characterized by FTIR, ¹H NMR and WXRD. Curing behaviors of the monomers with 4,4′-diaminodiphenyl ether were recorded by DSC. The result shows that the processabilities of o-BDB and m-BDB are superior to p-BDB due to lower melting points and broader processing windows. The structures of the cured phthalonitrile polymers were characterized by FTIR and WXRD, and thermal stabilities were evaluated by TGA and all the polymers exhibit excellent thermal and thermal-oxidative stabilities. Dynamic mechanical analysis reveals that the polymers have high storage modulus and high glass-transition temperatures. Consequently, o-BDB and m-BDB polymers show more outstanding processability, thermal stability and mechanical properties than p-BDB polymers, which may be good candidates for high-temperature phthalonitrile polymers.

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The article was received on 01 Aug 2015, accepted on 16 Sep 2015 and first published on 16 Sep 2015

Article type: Paper

DOI: 10.1039/C5RA15321B

Author version available: Download Author version (PDF)

Citation: RSC Adv., 2015,5, 80749-80755

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Synthesis and properties of high temperature phthalonitrile polymers based on o, m, p-dihydroxybenzene isomers

X. Chen, S. Shan, J. Liu, X. Qu and Q. Zhang, RSC Adv., 2015, 5, 80749
DOI: 10.1039/C5RA15321B
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Synthesis and properties of high temperature phthalonitrile polymers based on o, m, p-dihydroxybenzene isomers

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Synthesis and properties of high temperature phthalonitrile polymers based on o, m, p-dihydroxybenzene isomers

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