Synthesis of New Hydroxylated Monomers Based on Methacrylate, Dimethacrylate, and Tetramethacrylate Michael Adducts and Photopolymerization Kinetics of Bulk Cross-Linkers

摘要

A series of new hydroxylated monomers was synthesized from the Michael addition reaction between ethanolamine, diethylene glycol amine, triethylene glycol amine, tetradecylamine, and adaman-tanamine with 3-(acryloyloxy)-2-hydroxypropyl methacrylate (AHM). Selective formation of secondary amine (mono adduct) or tertiary amine (bis adduct) products was obtained by controlling the stoichiometry of the reactants and reaction temperature. The Michael addition reactions were highly exothermic and carried out without the need of catalyst. The use of solvent, however, was required in some systems. The tetramethacrylate monomer was synthesized via the Michael addition reaction of 1,6-hexanediamine (HDA) to AHM. The photopolymerization kinetics of the synthesized monomers were investigated using differential scanning calorimeter. The rates of polymerization for the hydroxylated dimethacrylate systems were significantly higher than that of a typical dimethacrylate monomer (HDDMA) and approached that of the diacrylate HDDA, with overall conversions ranging from 80 to 87%.