Synthesis of a novel camphorquinone derivative having acylphosphine oxide group, characterization by UV-VIS spectroscopy and evaluation of photopolymerization performance.
Camphorquinone (CQ) derivatives having acylphosphine oxide (APO) group are unknown. This study synthesized such a novel 7,7dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carbonyldiphenyl phosphine oxide (DOHC-DPPO = CQ-APO). Ultraviolet and visible (UVVIS) 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 (lambda(max)) [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 (114.3-133.8 MPa). It was concluded that CQ-APO possessed two lambda(max )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.
Ikemura
Kunio
K
Department of Research and Development, Shofu Inc. k-ikemura@shofu.co.jp
Ichizawa
Kensuke
K
Jogetsu
Yoshiyuki
Y
Endo
Takeshi
T
D017438:Bisphenol A-Glycidyl Methacrylate / Q000737:chemistry / Q000528:radiation effects; D002152:Calorimetry, Differential Scanning; D002264:Carboxylic Acids / Q000138:chemical synthesis; D003116:Color; D003188:Composite Resins / Q000737:chemistry / Q000528:radiation effects; D055119:Elastic Modulus; D006536:Heptanes / Q000138:chemical synthesis; D006801:Humans; D008027:Light; D008422:Materials Testing; D008689:Methacrylates / Q000737:chemistry / Q000528:radiation effects; D009947:Organotin Compounds / Q000737:chemistry / Q000528:radiation effects; D010720:Phosphines / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D018583:Pliability; D011108:Polymers / Q000737:chemistry / Q000528:radiation effects; D011140:Polyurethanes / Q000737:chemistry / Q000528:radiation effects; D012117:Resins, Synthetic / Q000737:chemistry / Q000528:radiation effects; D012822:Silicon Dioxide / Q000737:chemistry; D013053:Spectrophotometry; D013056:Spectrophotometry, Ultraviolet; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D013997:Time Factors; D014233:Tricarboxylic Acids / Q000737:chemistry / Q000528:radiation effects
C111562:4-acryloxyethyltrimellitic acid; D002264:Carboxylic Acids; D003188:Composite Resins; D006536:Heptanes; D008689:Methacrylates; D009947:Organotin Compounds; D010720:Phosphines; D011108:Polymers; D011140:Polyurethanes; D012117:Resins, Synthetic; D013729:Terpenes; D014233:Tricarboxylic Acids; C029824:urethane dimethacrylate luting resin; D017438:Bisphenol A-Glycidyl Methacrylate; C048339:camphoroquinone; D012822:Silicon Dioxide; C044646:phosphine; C010409:dibutyltin dilaurate; C028643:trimethylolpropane trimethacrylate