A series of new hydroxylated monomers was synthesized from the Michael addition reaction between ethanolamine, diethylene glycol amine, triethylene glycol amine, tetradecylamine, and adamantanamine 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%.

ABSTRACT:The effect of synthetic clay on the photopolymerization kinetics and coating properties of methyl ␣-hydroxymethylacrylate (MHMA) systems in the presence of novel hydroxylated dimethacrylate crosslinkers is reported. In the presence of clay earlier onset of autoacceleration was observed, high rates of polymerization were achieved, and high final overall conversions were reached. Higher rates and increase in conversions were also observed as the clay content increased in the medium. To increase compatibility between clay and polymer matrix the use of Jeffamines as polymer/clay compatibilizers, based on ion-dipole interactions between ethylene oxide units and clay ions, was also investigated. Nanocomposite-based films by photopolymerization of the mixtures coated on glass microscope slides were prepared and evaluated using X-ray and TEM. The absence of Bragg diffraction peaks in all nanocomposite films indicated loss of organization of the clay layers and formation of well-dispersed, exfoliated systems was confirmed by TEM.