Synthesis and properties of a novel cycloaliphatic epoxide

The novel cycloaliphatic epoxide 3,4-epoxycyclohexylmethyl-2′,3′-epoxycyclohexyl ether (II) containing an unsymmetrical epoxycyclohexyl moiety linked via an ether bond, and its precursor 3-cyclohexene 1-methyl-2′-cyclohexene ether (I) were synthesized. Their structure was confirmed by means of elemental analysis, FT-IR and ¹H NMR spectroscopy. Compared with commercial epoxide ERL-4221, the newly synthesized epoxide II shows a higher epoxy value (0.85 eq/g.) and lower viscosity (86 mpa · s/25°C). The cured product, based on epoxide II and curing agent hexahydro-4-methylphthalic anhydride (HMPA), showed higher glass transition temperature (162 °C), higher storage modulus at the glass transition region (2.95 GPa), higher crosslinking density (1.60 × 10^-3 mol/cm³) and a lower coefficient of thermal expansion (6.22 × 10^-5/°C).