Direct synthesis of poly(4′-oxy-4-biphenylcarbonyl) and poly(2-oxy-6-naphthoyl) under nonstoichiometric conditions

Shin ichiro Kohama, Kunio Kimura, Tetsuya Uchida, Shin ichi Umehara, Yume Ikemoto, Yuhiko Yamashita

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Direct synthesis of poly(4′-oxy-4-biphenylcarbonyl) (POBP) and poly(2-oxy-6-naphthoyl) (PON) was examined by polycondensation of 4′-hydroxy-4-biphenylcarboxylic acid (HBPA) and 2-hydroxy-6-naphthoic acid (HNA) in the presence of 4-ethoxybenzoic anhydride or 2-naphthoic anhydride as condensation reagents. Polymerizations were carried out at 320°C in aromatic solvents and liquid paraffin. POBP, having a number-average degree of polymerization (DPn) of 38, was obtained as plate-like crystals at the molar ratio of HBPA and anhydride of 50 mol%. PON was also obtained as plate-like crystals but the DPn was only 13. HBPA and HNA were first converted to reactive acyloxyaromatic acid intermediates. Then the DPn was increased by means of reaction-induced crystallization of oligomers and subsequent solid-state polymerization via an acid-ester exchange under nonstoichiometric conditions caused by the monocarboxylic acid by-product. Even though the DPn of PON was not as high, direct polycondensation of HBPA and HNA proceeded successfully with aromatic anhydrides.

Original languageEnglish
Pages (from-to)471-480
Number of pages10
JournalPolymer International
Volume54
Issue number2
DOIs
Publication statusPublished - Feb 2005

    Fingerprint

Keywords

  • Crystallization
  • Nonstoichiometric conditions
  • Oligomer
  • Polycondensation
  • Polyesters
  • Solid-state polymerization

ASJC Scopus subject areas

  • Polymers and Plastics

Cite this