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

Anhydrides
Polymerization
Acids
Hydroxy Acids
Polycondensation
Mineral Oil
Crystals
Crystallization
Oligomers
Byproducts
Condensation
Ion exchange
Esters
Paraffins
1-naphthoic acid
Liquids

Keywords

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

ASJC Scopus subject areas

  • Polymers and Plastics

Cite this

Direct synthesis of poly(4′-oxy-4-biphenylcarbonyl) and poly(2-oxy-6-naphthoyl) under nonstoichiometric conditions. / Kohama, Shin ichiro; Kimura, Kunio; Uchida, Tetsuya; Umehara, Shin ichi; Ikemoto, Yume; Yamashita, Yuhiko.

In: Polymer International, Vol. 54, No. 2, 02.2005, p. 471-480.

Research output: Contribution to journalArticle

Kohama, Shin ichiro ; Kimura, Kunio ; Uchida, Tetsuya ; Umehara, Shin ichi ; Ikemoto, Yume ; Yamashita, Yuhiko. / Direct synthesis of poly(4′-oxy-4-biphenylcarbonyl) and poly(2-oxy-6-naphthoyl) under nonstoichiometric conditions. In: Polymer International. 2005 ; Vol. 54, No. 2. pp. 471-480.
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