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Enzymatic oxidative polymerization of bisphenol‐a to a new class of soluble polyphenol
Author(s) -
Kobayashi Shiro,
Uyama Hiroshi,
Ushiwata Takami,
Uchiyama Takao,
Sugihara Junji,
Kurioka Hideharu
Publication year - 1998
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/(sici)1521-3935(19980501)199:5<777::aid-macp777>3.0.co;2-8
Subject(s) - chemistry , polymerization , polymer chemistry , polymer , solvent , thermal stability , organic chemistry , dimethylformamide , aqueous solution , cationic polymerization
Enzymatic oxidative polymerization of bisphenol‐A was carried out in an aqueous organic solvent using horseradish and soybean peroxidases (HRP and SBP, respectively) as catalysts. The SBP‐catalyzed polymerization in an equivolume mixture of methanol and phosphate buffer (pH 7.0) affords a new class of polyphenol quantitatively, which is readily soluble in polar organic solvents such as acetone, methanol, N , N ‐dimethylformamide, and dimethyl sulfoxide, but insoluble in chloroform, diethyl ether, and water. NMR and IR analyses show that the polymer is mainly composed of a mixture of phenylene and oxyphenylene units. The effects of the type of enzyme and the solvent composition were systematically investigated in respect to the yield and molecular weight of the polymer. The thermal treatment of the polymer produces an insoluble product and the curing temperature and the molecular weight of the starting polymer affect the thermal properties of the product. Crosslinking reaction of the present polyphenol with an epoxide resin affords insoluble polymeric material showing high thermal stability.