OBJECTIVES:The effect of experimental dentin primers containing N-methylolacrylamide (MEAA) or N-methylolmethacrylamide (MEMA) on bond durability of a resin composite (Photo Clearfil A) with a bonding agent (Clearfil Photo Bond) to bovine dentin was investigated. METHODS:The etching agents were 10% maleic acid (10% MA), 10% phosphoric acid (10% PA) and 10% citric acid-3% ferric chloride (10-3 solution). Water solutions of 35% hydroxyethyl methacrylate (HEMA), 50% MEAA or 30% MEMA were used as dentin primers. The etched dentin was pre-treated with the dentin primers for 30s. The resin composite systems were applied in a Teflon tube positioned onto pre-treated dentin surfaces. After water immersion for 1 day and 5 years, the shear bond strengths were measured. The amounts of calcium dissolved with etching agents were measured using atomic absorption spectrometry. The thicknesses of hybrid layers at the dentin-resin interfaces treated with 6 mol/l HCl and 1% NaOCl were measured using scanning electron microscopy. RESULTS:The bond strengths of the specimens (Controls) without primers to dentin etched with 10% MA and 10-3 solution significantly decreased after immersion in water for 5 years (p<0.05) while other bond strengths did not decrease. The bond strengths of the composites to MEMA- and MEAA-primed dentin were significantly higher than that of the control after 1 day, regardless of the types of etching agents (p<0.05). The 5 year bond strengths of the composites to HEMA-, MEMA- and MEAA-primed dentin were significantly higher than that of the control, regardless of the types of etching agents (p<0.05). The 1 day and 5 year bond strengths of the composite to MEAA-primed dentin were significantly higher than those of the composites to HEMA-primed dentin, regardless of the types of etching agents (p<0.05). The highest amount (182.3+/-8.0 microg/cm(2)) of dissolved calcium was determined for the pre-treatment with 10% PA, followed by that (152.0+/-6.9 microg/cm(2)) with 10% MA and that (140.1+/-2.8 microg/cm(2)) with 10-3 solution (p<0.05). The hybrid layer thicknesses (approximately 1 microm) for 10-3 solution were thinner than those (approximately 2 microm) for others after HCl immersion. For the controls, the hybrid layers after NaOCl immersion become narrower or disappeared. The main fracture pattern of specimens was a mixture of resin-dentin interface failure and dentin cohesive fracture after the bond test. CONCLUSIONS:MEAA solution was more effective in improving the bond strength of the controls to etched dentin than was HEMA after 1 day and 5 years. Clearfil Photo Bond created good hybrid dentin layers which could resist NaOCl-attack and showed good dentin bond durability when dentin primers were used, regardless of the type of etching agent.