Novel synthesis of linear perfluorinated poly(phenylene sulfide) from aryl sulfoxide

Kenji Miyatake; Kimihisa Yamamoto; Yoshihiro Yokoi; Eishun Tsuchida

doi:10.1021/ma9713567

Novel synthesis of linear perfluorinated poly(phenylene sulfide) from aryl sulfoxide

Kenji Miyatake, Kimihisa Yamamoto, Yoshihiro Yokoi, Eishun Tsuchida^*

^*Corresponding author for this work

Graduate School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

The linear perfluorinated poly(phenylene sulfide) [poly(thio-2,3,5,6-tetrafluoro-1,4-phenylene)] has been successfully prepared by polycondensation of 4-(methylsulfinyl)-2,3,5,6-tetrafluorophenyl 2,3,5,6-tetrafluorophenyl sulfide in an electrophilic reaction via the polysulfonium salt as a precursor. The polymerization proceeds efficiently in trifluoromethanesulfonic acid with the addition of phosphorus pentoxide as a dehydrating agent to produce the polymer in 100% yield. The polymer obtained is only partly soluble in 1-chloronaphthalene at 210 °C. The molecular weight (M_w) of the soluble part of the polymer is ∼4000 as determined by high-temperature gel permeation chromatography. The polymer has a melting temperature of 373 °C, which is 88 °C higher than that of the unfluorinated analog (285 °C). The contact angle measurements show that the surface energy of the polymer (σ_s = 41 mN/m) is comparable to those of poly(ethylene terephthalate) and polystyrene.

Original language	English
Pages (from-to)	403-407
Number of pages	5
Journal	Macromolecules
Volume	31
Issue number	2
DOIs	https://doi.org/10.1021/ma9713567
Publication status	Published - 1998 Jan 27

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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title = "Novel synthesis of linear perfluorinated poly(phenylene sulfide) from aryl sulfoxide",

abstract = "The linear perfluorinated poly(phenylene sulfide) [poly(thio-2,3,5,6-tetrafluoro-1,4-phenylene)] has been successfully prepared by polycondensation of 4-(methylsulfinyl)-2,3,5,6-tetrafluorophenyl 2,3,5,6-tetrafluorophenyl sulfide in an electrophilic reaction via the polysulfonium salt as a precursor. The polymerization proceeds efficiently in trifluoromethanesulfonic acid with the addition of phosphorus pentoxide as a dehydrating agent to produce the polymer in 100% yield. The polymer obtained is only partly soluble in 1-chloronaphthalene at 210 °C. The molecular weight (Mw) of the soluble part of the polymer is ∼4000 as determined by high-temperature gel permeation chromatography. The polymer has a melting temperature of 373 °C, which is 88 °C higher than that of the unfluorinated analog (285 °C). The contact angle measurements show that the surface energy of the polymer (σs = 41 mN/m) is comparable to those of poly(ethylene terephthalate) and polystyrene.",

author = "Kenji Miyatake and Kimihisa Yamamoto and Yoshihiro Yokoi and Eishun Tsuchida",

year = "1998",

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doi = "10.1021/ma9713567",

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T1 - Novel synthesis of linear perfluorinated poly(phenylene sulfide) from aryl sulfoxide

AU - Miyatake, Kenji

AU - Yamamoto, Kimihisa

AU - Yokoi, Yoshihiro

AU - Tsuchida, Eishun

PY - 1998/1/27

Y1 - 1998/1/27

N2 - The linear perfluorinated poly(phenylene sulfide) [poly(thio-2,3,5,6-tetrafluoro-1,4-phenylene)] has been successfully prepared by polycondensation of 4-(methylsulfinyl)-2,3,5,6-tetrafluorophenyl 2,3,5,6-tetrafluorophenyl sulfide in an electrophilic reaction via the polysulfonium salt as a precursor. The polymerization proceeds efficiently in trifluoromethanesulfonic acid with the addition of phosphorus pentoxide as a dehydrating agent to produce the polymer in 100% yield. The polymer obtained is only partly soluble in 1-chloronaphthalene at 210 °C. The molecular weight (Mw) of the soluble part of the polymer is ∼4000 as determined by high-temperature gel permeation chromatography. The polymer has a melting temperature of 373 °C, which is 88 °C higher than that of the unfluorinated analog (285 °C). The contact angle measurements show that the surface energy of the polymer (σs = 41 mN/m) is comparable to those of poly(ethylene terephthalate) and polystyrene.

AB - The linear perfluorinated poly(phenylene sulfide) [poly(thio-2,3,5,6-tetrafluoro-1,4-phenylene)] has been successfully prepared by polycondensation of 4-(methylsulfinyl)-2,3,5,6-tetrafluorophenyl 2,3,5,6-tetrafluorophenyl sulfide in an electrophilic reaction via the polysulfonium salt as a precursor. The polymerization proceeds efficiently in trifluoromethanesulfonic acid with the addition of phosphorus pentoxide as a dehydrating agent to produce the polymer in 100% yield. The polymer obtained is only partly soluble in 1-chloronaphthalene at 210 °C. The molecular weight (Mw) of the soluble part of the polymer is ∼4000 as determined by high-temperature gel permeation chromatography. The polymer has a melting temperature of 373 °C, which is 88 °C higher than that of the unfluorinated analog (285 °C). The contact angle measurements show that the surface energy of the polymer (σs = 41 mN/m) is comparable to those of poly(ethylene terephthalate) and polystyrene.

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Novel synthesis of linear perfluorinated poly(phenylene sulfide) from aryl sulfoxide

Abstract

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