New aromatic poly(azomethine urethane)s containing o-tolidine moiety in the polymer backbone

Abstract

A new bisphenol containing azomethine groups, N,N′-bis (4-hydroxy-3-methoxy benzyl-idene)-o-tolidine (I) was synthesized and characterized by 1H-NMR, FTIR, UV, CHN analysis and mass spectroscopy. The polymerization was carried out with various diisocyanates such as hexamethylene diisocyanate (HDI) (a), methylene-4,4′-diphenyl diisocyanate (MDI) (b) and toluene-2,4-diisocyanate (TDI) (c). The resulting polymers Ia-c were confirmed by 1H-NMR, FT-IR, UV and CHN analysis. Thermogravimetric analysis (TGA) revealed polymers have high thermal stability. A semicrystalline behavior was noticed for polymers by wide-angle X-ray diffraction (WAXD) and differential scanning calorimetry (DSC).