Synthesis, characterization and polymerization of new epoxy compounds containing azomethine linkages

New epoxy compounds bearing azomethine linkages were synthesized and characterized. A series of epoxy derivatives of bis(azomethine)s (2a – d) was synthesized by reacting an aromatic diamine with 4‐hydroxybenzaldehyde in a 1:2 mole ratio to afford the corresponding bis(azomethine)s (1a – d), and subsequent reaction with excess 1‐chloro‐2,3‐epoxypropane in presence of a quarternary ammonium bromide as catalyst. In addition, epoxy compounds 4a, b and 5b were synthesized by reacting 1,4‐benzenedicarbaldehyde with 4‐aminophenol, 4‐aminobenzoic acid or 5‐aminoisophthalic acid in a 1:2 mole ratio and then with 1‐chloro‐2,3‐epoxypropane. The epoxy compounds were characterized by elemental analyses as well as by IR and 1H NMR spectroscopy. All epoxy compounds were thermally polymerized in the presence of 4,4′‐sulfonyl dianiline (6). The polymerization was investigated by DTA. The thermal stabilities of the resulting polymers were evaluated by dynamic TG and isothermal gravimetric analysis (IGA). The polymers derived from diepoxy compounds are stable in nitrogen up to 293–340°C and afford an anaerobic char yield of 43–62% at 800°C.