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Abstract

A new series including eight structurally different self-curing epoxy compounds bearing azomethine linkages were synthesized, characterized and polymerized. 4-(2,3-Epoxypropoxy)-benzaldehyde (EPB) or 2,3-epoxypropyl glyoxylate monohydrate (EPG), prepared by reacting 4-hydroxybenzaldehyde or glyoxylic acid monohydrate, respectively, with excess of epichlorohydrin in the presence of benzyltrimethylammonium bromide as catalyst, were used as starting materials. EPB or EPG reacted with an equimolar amount of a substituted aromatic amine (4-aminobenzoic acid, 5-aminoisophthalic acid, 4-aminophenol, or 1,4-phenylene-diamine) to afford the epoxy compounds. They were characterized by IR and 1H-NMR spectroscopy. Their thermal polymerization was investigated by DTA. The thermal stabilities of cured resins were evaluated by dynamic TGA and isothermal gravimetric analysis (IGA). The polymers of the epoxy compounds derived from EPB were stable up to 225–298°C in N2 and afforded anaerobic char yield of 57–62% at 800°C.