Synthesis of poly(arylene sulfide)s by cationic oxidative polymerization of diaryl disulfides

Kimihisa Yamamoto, Mitsutoshi Jikei, Junya Katoh, Hiroyuki Nishide, Eishun Tsuchida

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Abstract

Alkyl-substituted poly(arylene sulfide)s (PASs) are prepared by the oxidative polymerization of diaryl disulfides with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The structures of the formed poly(arylene sulfide)s are confirmed by spectroscopic measurements. The linear structure of poly(2-methyl-1,4-phenylene sulfide) is confirmed by comparing its spectroscopic data with those of the polymer prepared from bis(2-methylphenyl) disulfide, bis(3-methylphenyl) disulfide and (4-bromo-2-methylthiophenoxy) copper salt. Bis(2,5-dimethylphenyl) disulfide is easily polymerized to poly(2,5-dimethyl-1,4-phenylene sulfide) with high yield and high melting point in comparison with the other methyl-substituted poly(arylene sulfide)s, due to the symmetry of the polymer structure. The polymerization reaction, with the exception of bis(3,5-dimethylphenyl) disulfide, produces low molecular weight polymers because of the solvent insolubility of PASs and the low reactivity of diaryl disulfides. Soluble poly(2,6-dimethylphenylene sulfide) is isolated by the polymerization of bis(3,5-dimethylphenyl) disulfide as a white powder with ca. 3 × 104 weight-average molecular weight.

Original languageEnglish
Pages (from-to)2698-2704
Number of pages7
JournalMacromolecules
Volume25
Issue number10
Publication statusPublished - 1992 Jan 1

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Sulfides
Disulfides
Polymerization
Polymers
Molecular weight
Powders
Melting point
Copper
Solubility
Salts

ASJC Scopus subject areas

  • Materials Chemistry

Cite this

Yamamoto, K., Jikei, M., Katoh, J., Nishide, H., & Tsuchida, E. (1992). Synthesis of poly(arylene sulfide)s by cationic oxidative polymerization of diaryl disulfides. Macromolecules, 25(10), 2698-2704.

Synthesis of poly(arylene sulfide)s by cationic oxidative polymerization of diaryl disulfides. / Yamamoto, Kimihisa; Jikei, Mitsutoshi; Katoh, Junya; Nishide, Hiroyuki; Tsuchida, Eishun.

In: Macromolecules, Vol. 25, No. 10, 01.01.1992, p. 2698-2704.

Research output: Contribution to journalArticle

Yamamoto, K, Jikei, M, Katoh, J, Nishide, H & Tsuchida, E 1992, 'Synthesis of poly(arylene sulfide)s by cationic oxidative polymerization of diaryl disulfides', Macromolecules, vol. 25, no. 10, pp. 2698-2704.
Yamamoto, Kimihisa ; Jikei, Mitsutoshi ; Katoh, Junya ; Nishide, Hiroyuki ; Tsuchida, Eishun. / Synthesis of poly(arylene sulfide)s by cationic oxidative polymerization of diaryl disulfides. In: Macromolecules. 1992 ; Vol. 25, No. 10. pp. 2698-2704.
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