Polymerization of diphenyl disulfide by the S-S bond cleavage with a Lewis acid: a novel preparation route to poly(p-phenylene sulfide)

Tsuchida, Eishun; Yamamoto, Kimihisa; Nishide, Hiroyuki; Yoshida, Shu; Jikei, Mitsutoshi

doi:10.1021/ma00210a001

Cited by 54 publications

(27 citation statements)

References 4 publications

(4 reference statements)

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“…7 Diphenyl disulfide is oxidized to yield phenylbis (phenylthio) sulfonium cation. This cation is an active species and electrophilically reacts with the p -position of the benzene ring of the monomer or the oligomer.…”

Section: Resultsmentioning

confidence: 99%

Acid effect on oxidative polymerization of diphenyl disulfide with DDQ

Yamamoto

Jikei

et al. 1991

J. Polym. Sci. A Polym. Chem.

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Section: Resultsmentioning

confidence: 99%

Acid effect on oxidative polymerization of diphenyl disulfide with DDQ

Yamamoto

Jikei

et al. 1991

J. Polym. Sci. A Polym. Chem.

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“…It can be observed that the intensity of the band at 1100 cm À 1 is less intense in the bare CNTs indicating that grafting of the molecules causes their appearance. The band at 1450 cm À 1 could be assigned to the aromatic C-C stretching of diarylsulphur groups, observed in PPS (Tsuchida et al, 1990).…”

Section: Extent Of Reaction Validation and Product Characterizationmentioning

confidence: 95%

The functionalization of carbon nanotubes using a batch oscillatory flow reactor

Melendi

Bonyadi

Castell³

et al. 2012

Chemical Engineering Science

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This paper describes an efficient method for the functionalizing of multi-walled carbon nanotubes (MWCNT) using oscillatory flow mixing (OFM). A 3. l batch oscillatory flow reactor (OFR) was designed and constructed for pilot scale functionalization of MWCNT in order to potentially improve their compatibility within a thermoplastic polyphenylene sulphide (PPS) matrix. The OFM batch reactor consisted of a jacketed cylindrical vessel with a vertical axial oscillator that contained a series of baffled mixing plates. MWCNTs dispersed in dimethylformamide (DMF) were introduced into the reactor and a two stage reaction for functionalizing MWCNTs with PPS compatible groups was carried out under oscillation of baffles at elevated temperatures. Fluid mixing observations in the reactor showed that MWCNTs formed a uniform dispersion of aggregated flocs before and during the functionalization reaction. On completion of the reaction and cessation of the oscillation, the aggregated flocs of MWCNT rapidly sedimented at the bottom of the reactor; hence could be collected as a concentrated mass thereby facilitating the separation of functionalized MWCNTs from the solvent. The functionalized MWCNTs were dried and then characterized by transmission electron microscopy, infrared spectroscopy as well as thermal gravimetric analysis in order to investigate the extent of MWCNT functionalization. The characterization results confirmed the effective and relatively uniform functionalization of the MWCNTs despite formation of aggregates, indicating that OFM provides a viable approach for functionalizing MWCNTs. © 2012

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“…We have already concluded that the polymerization proceeds via oxidation of diary1 disulfides followed by electrophilic reaction of the resulting sulfonium cation 14). The polymerization rate of 5 is larger than that of bis (3,5-dimethylphenyl) disulfide due to its higher electron density of the phenylene ring binding ether bond.…”

Section: ') 516mentioning

confidence: 99%

Synthesis of amorphous poly(thioarylene)s via oxidative polymerization of diaryl disulfides

Miyatake

Jikei

Yamamoto

et al. 1996

Macro Chemistry & Physics

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Amorphous poly(thioary1ene)s containing a methyl substituent and/or an ether bond in the main chain were prepared via oxidative polymerization of diaryl disulfides using 2,3-dichloro-5,6-dicyanobenzoquinone. The resulting poly(thio-2,6-dimethyl-l,4-phenyleneoxy-l,4-phenylene) having alternating ether and thioether bonds shows a better solvent solubility and has a higher glass transition temperature (Tg) (1 82 "C) than non-substituted poly(thio-l,4-phenylene). Polymerization of methyl substituted diphenyl ether derivatives with disulfur dichloride has been also developed for a one-pot synthesis of amorphous poly(thioary1ene)s.

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Polymerization of diphenyl disulfide by the S-S bond cleavage with a Lewis acid: a novel preparation route to poly(p-phenylene sulfide)

Cited by 54 publications

References 4 publications

Acid effect on oxidative polymerization of diphenyl disulfide with DDQ

Acid effect on oxidative polymerization of diphenyl disulfide with DDQ

The functionalization of carbon nanotubes using a batch oscillatory flow reactor

Synthesis of amorphous poly(thioarylene)s via oxidative polymerization of diaryl disulfides

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