Camphorquinone (CQ) derivatives having acylphosphine oxide (APO) group are unknown. This study synthesized such a novel 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carbonyldiphenyl phosphine oxide (DOHC-DPPO = CQ-APO). Ultraviolet and visible (UV-VIS) spectra of CQ-APO, CQ, and APO were measured. Photopolymerization performances of experimental light-cured resins comprising these photoinitiators were investigated. Newly synthesized CQ-APO showed as a pale yellow crystal (mp 365K). UV-VIS spectrum of CQ-APO showed two maximum absorption wavelengths (λmax) [372 nm (from APO group) and 475 nm (from CQ moiety)] within 350-500 nm. Unfilled resin containing CQ-APO exhibited good photopolymerization time (9.6 sec) and relaxed operation time (50 sec), as well as a pronouncedly lower b value (4.0) in the CIELab color specification system than that containing CQ (84.0). Resin composites containing CQ-APO, exhibited high flexural strength . It was concluded that CQ-APO possessed two λmax peaks within 350-500 nm, and that CQ-APO-containing resins exhibited excellent color tone, good photopolymerization reactivity, relaxed operation time, and high mechanical strength.

This study investigated the bonding effectiveness of newly designed self-etching adhesives to four types of adherends -enamel, dentin, zirconia, and gold (Au) alloy. Five experimental adhesives were prepared, which contained 3.0-5.0 wt% 6-methacryloyloxyhexyl phosphonoacetate (6-MHPA) or 6-methacryloyloxyhexyl 3-phosphonopropionate (6-MHPP), 3.0 wt% 4-acryloyloxyethoxycarbonylphthalic acid (4-AET) or 17.0 wt% 4-methacryloyloxyethoxycarbonylphthalic acid (4-MET), 0-0.5 wt% 6-methacryloyloxyhexyl 6,8-dithiooctanoate (6-MHDT) or 10-methacryloyloxydecyl 6,8-dithiooctanoate (10-MDDT), and varying contents of Bis-GMA, dimethacrylate monomers, water, acetone, and a photoinitiator system. After 2,000 times of thermal cycling, shear bond strengths (SBSs) between a resin composite (Beautifil II, Shofu Inc., Japan) and the four adherends, bonded using the experimental adhesives, were measured at 1.0 mm/min. No statistically significant differences in SBS for bonding to ground enamel, dentin, sandblasted zirconia and Au alloy (p>0.05) were found between experimental adhesives which contained 6-MHPA and/or 6-MHPP, 4-MET or 4-AET, 6-MHDT and/or 10-MDDT, Bis-GMA, and dimethacrylates. An adhesive layer of less than 5.0 µm thickness, by scanning electron microscopy observation, revealed strong adhesion to the four adherends. Therefore, the newly designed multi-purpose, self-etching adhesive strongly adhered to all the four adherend materials tested.