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

KAYA İ., Avci A.

MATERIALS CHEMISTRY AND PHYSICS, vol.133, no.1, pp.269-277, 2012 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 133 Issue: 1
  • Publication Date: 2012
  • Doi Number: 10.1016/j.matchemphys.2012.01.021
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.269-277
  • Çanakkale Onsekiz Mart University Affiliated: Yes


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.