Novel poly(azomethine-urethane)s and their polyphenol derivatives derived from aliphatic diisocyanate compound: Synthesis and thermal characterization

Abstract

Until now, only a few kinds of poly(azomethine-urethane)s (PAMUs) including aromatic hydroxy benzaldehyde and aminophenol compounds were obtained and studied with thermal degradation steps. However, oligo/polyphenol-based PAMUs have not been synthesized yet. In this study, some kinds of this class of PAMUs were synthesized in three steps. At the first step polyurethane (PU) was synthesized by the copolymerization reaction of 2,4-dihydroxybenzaldehyde with hexamethylene diisocyanate (HDI) under argon atmosphere. At the second step, the poly(azomethine-urethane)s (PAMUs) were obtained by graft copolymerization of the preformed PU with aminophenols (2-aminophenol, 3-aminophenol, and 4-aminophenol). At the last step the obtained PAMUs were converted to the polyphenol derivatives via oxidative polycondensation reaction (OP). The structures of the obtained compounds were confirmed by FTIR, UV-vis, 1H-NMR, and 13C-NMR techniques. The number-average molecular weight (Mn), weight average molecular weight (Mw) and polydispersity index (PDI) values 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. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012