Materials Chemistry and Physics, Vol.133, No.1, 269-277, 2012
Synthesis, characterization, and thermal stability of novel poly(azomethine-urethane)s and polyphenol derivatives derived from 2,4-dihydroxy benzaldehyde and toluene-2,4-diisocyanate
Up to date, only a few kinds of poly(azomethine-urethane)s (PAMUs) were synthesized and studied with thermal degradation steps. However, polyphenol based PAMUs including azomethine linkages have not been investigated yet. The polyurethanes were prepared by condensation reaction of 2,4-dihydroxybenzaldehyde (2,4-DHBA) with toluene-2,4-diisocyanate (TDI) under argon atmosphere. Synthesized polyurethane was converted to its poly(azomethine urethane) species (TP-2AP, TP-3AP, and TP-4AP) by graft copolymerization reactions with amino phenols (2-amino phenol, 3-amino phenol, and 4-amino phenol). Obtained poly(azomethine urethane)s were converted to their polyphenol species (P-TP-2AP, P-TP-3AP, and P-TP-4AP) by oxidative polymerization reaction (OP) using NaOCl as the oxidant. The structures of the obtained compounds were confirmed by FT-IR. UV-vis, H-1 NMR, and C-13 NMR techniques. The molecular weight distribution parameters of the synthesized compounds were determined by the size exclusion chromatography (SEC). The synthesized compounds were also characterized by solubility tests, TG-DTA, and DSC. Fluorescence measurements were carried out in various concentrated DMF solutions to determine the optimum concentrations to obtain the maximal PL intensities. (C) 2012 Elsevier B.V. All rights reserved.
Keywords:Thermogravimetric analysis;Differential scanning calorimetry;Luminescence;Poly(azomethine-urethane)s