Preparation of aromatic polyesters by direct polymerization in the presence of boronic anhydride under non-stoichiometric condition

Masahiro Kihara, Yuma Sakakiyama, Shinichi Yamazaki, Kunio Kimura

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Direct polymerizations of p-hydroxybenzoic acid (HBA) and 2-hydroxy-6-naphthoic acid (HNA) in the presence of boronic anhydride were examined by using crystallization under non-stoichiometric condition. The polymerizations were carried out with the addition of monofunctional compounds such as an aromatic carboxylic acid and a phenol. High molecular weight poly(p-oxybenzoyl) (POB) and poly(2-oxy-6-naphthoyl) (PON) were obtained in the form of precipitates, and their molecular weights were much higher than those calculated according to the stoichiometric imbalance. Oligomers were formed by the direct polymerization with eliminating water in the solution, and then they were precipitated to form the crystals at the initial stage of the polymerization. Oligomers end-capped by monofunctional compounds were also formed in the solution, but the polymerization continued with the elimination of monofunctional compounds by the ester exchange reaction. The end-capped oligomers were precipitated in the middle of the polymerization, and the polymerization proceeded efficiently even in the precipitated crystals by not only the direct polymerization but also the ester exchange polymerization, resulting in the increase in molecular weight.

Original languageEnglish
Pages (from-to)222-229
Number of pages8
JournalPolymer
Volume66
DOIs
Publication statusPublished - Apr 20 2015

Fingerprint

Polyesters
Anhydrides
Polymerization
Oligomers
Molecular weight
Carboxylic acids
Esters
Crystals
Salicylic Acid
Acids
Carboxylic Acids
Crystallization
Phenol
Phenols
Precipitates
Ion exchange
Water

Keywords

  • Direct polymerization
  • Polyesters
  • Stoichiometry

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics

Cite this

Preparation of aromatic polyesters by direct polymerization in the presence of boronic anhydride under non-stoichiometric condition. / Kihara, Masahiro; Sakakiyama, Yuma; Yamazaki, Shinichi; Kimura, Kunio.

In: Polymer, Vol. 66, 20.04.2015, p. 222-229.

Research output: Contribution to journalArticle

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N2 - Direct polymerizations of p-hydroxybenzoic acid (HBA) and 2-hydroxy-6-naphthoic acid (HNA) in the presence of boronic anhydride were examined by using crystallization under non-stoichiometric condition. The polymerizations were carried out with the addition of monofunctional compounds such as an aromatic carboxylic acid and a phenol. High molecular weight poly(p-oxybenzoyl) (POB) and poly(2-oxy-6-naphthoyl) (PON) were obtained in the form of precipitates, and their molecular weights were much higher than those calculated according to the stoichiometric imbalance. Oligomers were formed by the direct polymerization with eliminating water in the solution, and then they were precipitated to form the crystals at the initial stage of the polymerization. Oligomers end-capped by monofunctional compounds were also formed in the solution, but the polymerization continued with the elimination of monofunctional compounds by the ester exchange reaction. The end-capped oligomers were precipitated in the middle of the polymerization, and the polymerization proceeded efficiently even in the precipitated crystals by not only the direct polymerization but also the ester exchange polymerization, resulting in the increase in molecular weight.

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