Synthesis and functionalization of bromomethylated poly(phenylene sulfide)

Kenji Miyatake; Hiroyuki Hara; Eishun Tsuchida

doi:10.1002/(SICI)1521-3935(19990801)200:8<1930::AID-MACP1930>3.0.CO;2-V

Synthesis and functionalization of bromomethylated poly(phenylene sulfide)

Kenji Miyatake, Hiroyuki Hara, Eishun Tsuchida^*

^*Corresponding author for this work

Graduate School of Advanced Science and Engineering

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

4 Citations (Scopus)

Abstract

A soluble poly(phenylene sulfide) (PPS) derivative was synthesized by oxidative polymerization of bis(3,5-dimethylphenyl) disulfide. The obtained poly(thio-2,6-dimethyl-1,4-phenylene) (I) (M̄_w = 22900, M̄_n = 8400) was brominated by the reaction with N-bromosuccinimide (NBS). The bromomethyl substituents on PPS are reactive and were converted quantitatively to hydroxymethyl groups by hydrolysis in NMP at 100°C. The reaction of the bromomethylated PPS with tertiary amines gave the quaternized polymer, which is stable up to 145°C in the solid state and in refluxing methanol.

Original language	English
Pages (from-to)	1930-1934
Number of pages	5
Journal	Macromolecular Chemistry and Physics
Volume	200
Issue number	8
DOIs	https://doi.org/10.1002/(SICI)1521-3935(19990801)200:8<1930::AID-MACP1930>3.0.CO;2-V
Publication status	Published - 1999 Aug

ASJC Scopus subject areas

Condensed Matter Physics
Physical and Theoretical Chemistry
Organic Chemistry
Polymers and Plastics
Materials Chemistry

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10.1002/(SICI)1521-3935(19990801)200:8<1930::AID-MACP1930>3.0.CO;2-V

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title = "Synthesis and functionalization of bromomethylated poly(phenylene sulfide)",

abstract = "A soluble poly(phenylene sulfide) (PPS) derivative was synthesized by oxidative polymerization of bis(3,5-dimethylphenyl) disulfide. The obtained poly(thio-2,6-dimethyl-1,4-phenylene) (I) ({\=M}w = 22900, {\=M}n = 8400) was brominated by the reaction with N-bromosuccinimide (NBS). The bromomethyl substituents on PPS are reactive and were converted quantitatively to hydroxymethyl groups by hydrolysis in NMP at 100°C. The reaction of the bromomethylated PPS with tertiary amines gave the quaternized polymer, which is stable up to 145°C in the solid state and in refluxing methanol.",

author = "Kenji Miyatake and Hiroyuki Hara and Eishun Tsuchida",

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T1 - Synthesis and functionalization of bromomethylated poly(phenylene sulfide)

AU - Miyatake, Kenji

AU - Hara, Hiroyuki

AU - Tsuchida, Eishun

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N2 - A soluble poly(phenylene sulfide) (PPS) derivative was synthesized by oxidative polymerization of bis(3,5-dimethylphenyl) disulfide. The obtained poly(thio-2,6-dimethyl-1,4-phenylene) (I) (M̄w = 22900, M̄n = 8400) was brominated by the reaction with N-bromosuccinimide (NBS). The bromomethyl substituents on PPS are reactive and were converted quantitatively to hydroxymethyl groups by hydrolysis in NMP at 100°C. The reaction of the bromomethylated PPS with tertiary amines gave the quaternized polymer, which is stable up to 145°C in the solid state and in refluxing methanol.

AB - A soluble poly(phenylene sulfide) (PPS) derivative was synthesized by oxidative polymerization of bis(3,5-dimethylphenyl) disulfide. The obtained poly(thio-2,6-dimethyl-1,4-phenylene) (I) (M̄w = 22900, M̄n = 8400) was brominated by the reaction with N-bromosuccinimide (NBS). The bromomethyl substituents on PPS are reactive and were converted quantitatively to hydroxymethyl groups by hydrolysis in NMP at 100°C. The reaction of the bromomethylated PPS with tertiary amines gave the quaternized polymer, which is stable up to 145°C in the solid state and in refluxing methanol.

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Synthesis and functionalization of bromomethylated poly(phenylene sulfide)

Abstract

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