Synthesis and characterization of imine-functionalized polyphenol via enzymatic oxidative polycondensation of a bisphenol derivative
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Date
2016
Journal Title
Journal ISSN
Volume Title
Publisher
SPRINGER
Access Rights
info:eu-repo/semantics/closedAccess
Abstract
Enzymatic oxidative polycondensation of a new bisphenol derivative 3,3'-((1E,1'E)-(1,3-phenylenebis(azanylylidene))bis(methanylylidene))diphenol, (3,3'-PBAMD), using horseradish peroxidase (HRP) enzyme and hydrogen peroxide (H2O2) oxidizer for initiation of the reaction, has been investigated in an equivolume mixture of an organic solvent (acetone, methanol, ethanol, dichloromethane, 1,4-dioxane and tetrahydrofuran) and phosphate buffer (pH = 5.0, 6.0, 7.0, 8.0 and 9.0) at different temperatures under air for 24 h. The resulting polymer, poly(3,3'-PBAMD), was characterized using ultraviolet-visible (UV-Vis), Fourier transform infrared (FT-IR), H-1 nuclear magnetic resonance (NMR), gel permeation chromatography (GPC) and thermogravimetric (TGA) analyses. Effects of solvent system, reaction temperature and pH on the polymerization have been investigated with respect to the yield and molecular weight (M-n) of the product. The optimum reaction condition in terms of the highest yield (81 %) and molecular weight (M-n = 10,500 g/mol, DP similar to 33) was achieved in an equivolume mixture of tetrahydrofuran/pH 7.0 phosphate buffer medium at 25 degrees C. Polymerization involved hydrogen elimination from the monomer, and terminal units of the polymer structure consisted of phenolic hydroxyl (-OH) groups at the ends. The polymer is mainly composed of a mixture of phenylene and oxyphenylene units according to H-1 NMR and FT-IR analyses. The resulted product has shown relatively high thermal stability against thermal decomposition, and 35 % of the initial weight of the sample (carbonaceous residue) remained after heating to 1000 degrees C.
Description
Keywords
Enzymatic oxidative polymerization, Horseradish peroxidase (HRP), Schiff base, Hydrogen peroxide, pH, Bisphenol
Journal or Series
POLYMER BULLETIN
WoS Q Value
Q3
Scopus Q Value
Q2
Volume
73
Issue
1
