Synthesis and characterization of curable methacrylate-based monomers



The synthesis of new methacrylate-based, curable macromonomers, 4,4′-bis[2-hydroxy-3-aminopropylmethacrylate] diphenyl ether (BHAPE) and 4,4′-bis[2-hydroxy-3-aminopropylmethacrylate] diphenyl methane (BHAPM), is reported. BHAPE and BHAPM were prepared by the reaction of glycidyl methacrylate (GMA) with 4,4′-diaminodiphenyl ether and 4,4′-diaminodiphenyl methane, respectively. The progress of the reaction was monitored by thin-layer chromatography (TLC), and the structure of the monomers was characterized by Fourier transform infrared (FTIR) and 1H-NMR spectroscopy. Thermal curing of the monomers was conducted in a differential scanning calorimeter (DSC) with peroxide as the initiator. Thermal curing of the monomers showed the highest rate at 100°C with the activation energy value in the range 80–90 kJ distilled/mol. The water absorption properties of the cured samples in water, acidic, and basic solutions were studied. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010