To improve the water resistance of the polysiloxane at the silica-resin interface, 3-methacryloyloxypropyltrimethoxysilane (3-MPS), 3-methacryloyloxypropyltriisocyanatosilane (3-MPI), 3-methacryloyloxypropyltrichlorosilane (3-MPC) and silane coupling agents containing a hydrophobic phenyl group such as 3-(4-methacryloyloxyphenyl) propyltrimethoxysilane (
p-MBS), 3-(4-methacryloyloxyphenyl) propyltriisocyanatosilane (
p-MBI) and 3-(4-methacryloyloxyphenyl) propyltrichlorosilane (
p-MBC) were used. The tensile bond strength of the resin cement and the contact angles of a monomer mixture (50%Bis-GMA, 50%TEGDMA) to the ceramic teeth modified with each silane were measured. The tensile bond strength of the resin cement to the ceramic teeth modified with 3-MPC and
p-MBC after thermal stress showed no significant decrease compared with a sample kept at room temperature for 1 day. The contact angles of the monomer to the ceramic teeth modified with 3-MPI, 3-MPC,
p-MBS,
p-MBI or
p-MBC were significantly lower compared with 3-MPS. It was suggested that silane coupling agents with chloro groups as hydrolyzable groups had high water resistance ability at the silica-resin interface.
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