Citation: Qian Liu, Yu-xue Yang, Shou-hai Zhang, Ren-dong Xue, Xi-gao Jian. Synthesis and Characterization of Perfluorocyclobutyl Copoly(aryl ether)s Containing Biphenyl and Sulfonyl Moieties[J]. Acta Polymerica Sinica, ;2018, 0(5): 581-587. doi: 10.11777/j.issn1000-3004.2017.17211 shu

Synthesis and Characterization of Perfluorocyclobutyl Copoly(aryl ether)s Containing Biphenyl and Sulfonyl Moieties

School of Chemical Engineering, Dalian University of Technology, Liaoning High Performance Polymer Engineering Research Center, Liaoning Key Laboratory of Polymer Science and Engineering, Dalian 116024

Corresponding author: Shou-hai Zhang, zhangshh@dlut.edu.cn
Received Date: 2 August 2017
Revised Date: 9 October 2017
Available Online: 1 March 2018

High temperature solution copolymerization of 4,4′-sulfonyl-bis(trifluorovinyloxy)biphenyl (DTS) and 4,4 ′-bis(trifluorovinyloxy)biphenyl (DTB) were carried out in diphenyl ether as the solvent. A series of perfluorocyclobutyl copoly(aryl ether)s containing biphenyl and sulfonyl moieties (PFCB-S-BP) were prepared via thermal [2π + 2π] cycloaddition polymerization by controlling the ratio of DTS to DTB. PFCB-S-BP was synthesized when the ratio of DTS to DTB ranged from 3/7 to 7/3. Molecular weight and its distribution of PFCB-S-BP were measured by gel permeation chromatography (GPC). The GPC curves showed a narrow and unimodal elution peak. The number-average molecular weight of PFCB-S-BP was larger than 1.4 × 10⁴, with a narrow molecular weight distribution ranging from 1.4 to 1.6. The chemical structures was characterized by Fourier transform infrared spectroscopy Fourier transform infrared spectroscopy (FTIR), hydrogen nuclear magnetic resonance (¹H-NMR) and fluorine nuclear magnetic resonance (¹⁹F-NMR). The characteristic signal of trifluorovinyl ether group of monomers at 1824 cm⁻¹ disappeared in Fourier transform infrared spectroscopy (FTIR) spectra of PFCB-S-BP and the strong perfluorocyclobutyl group characteristic peak at 957 cm⁻¹ appeared. The intensities of sulfonyl group characteristic absorption peaks at 1100 and 1315 cm⁻¹ increased with the increase in the ratio of DTS to DTB. From ¹H-NMR of PFCB-S-BP, the signal at 7.9 was assigned to the protons of benzene ring adjacent to sulfonyl group. The intensity of the signal increased with an increase in the ratio of DTS to DTB. For ¹⁹F-NMR of PFCB-S-BP, the multiple peaks ranging from −127 to −134 were ascribed to the cis- and trans-substituted PFCB rings. These results indicated that DTS copolymerized with DTB, and PFCB-S-BP copolymers were successfully synthesized. The thermal property and solubility of PFCB-S-BP were also tested. T_g of PFCB-S-BP increased slightly from 146 °C to 153 °C with an increase in the ratio of DTS to DTB from 3/7 to 7/3. The decomposition temperature for 5% weight loss of PFCB-S-BP was above 470 °C. These results showed that PFCB-S-BP exhibited high thermal stability and was soluble in common organic solvents such as N-methyl-2-pyrrolidinone, N,N-dimethylacetamide and chloroform.
- Trifluorovinyloxy,
- Perfluorocyclobutyl,
- Poly(aryl ether),
- Copolymerization
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