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In this study, we modified silica nanoparticles with bis[3-(trimethoxysilyl)propyl]amine (BTMA) silane coupling agent to introduce secondary amino groups on the silica surface. After modification of silica, we investigated effects of different types of (meth)acrylate group containing monomers on the Michael addition reaction to introduce reactive (meth)acrylate groups on the BTMA modified silica surface. We used two kinds of (meth)acrylate monomers, trimethylolpropane ethoxylate triacrylate (TMPET) which has three identical acrylate groups, and 3-(acryloyloxy)-2-hydroxypropyl methacrylate (AHM) which has one acrylate and one methacrylate group. We used fourier transform infrared spectroscopy (FTIR), elemental analysis (EA) and solid state cross-polarization magic angle spinning (CP/MAS) nuclear magnetic resonance spectroscopy (NMR) to understand reactions between NH groups on the silica surface with (meth)acrylate groups of TMPET and AHM monomers. We found almost complete Michael addition reaction between all three acrylate groups of TMPET with NH groups on the BTMA modified silica. But, for the AHM treatment of BTMA modified silica, we found Michael addition reaction occurred only between acrylate groups of AHM and NH groups of silica surface, not between methacrylate groups of AHM and NH groups of BTMA modified silica surface.

Spectroscopic Analysis on the Michael Addition Reaction between Secondary Amino Group Containing Silica Nanoparticles with (Meth)acrylate Monomers