Dental Materials
Volume 24, Issue 7 , Pages 901-907 , July 2008

Benzoyl germanium derivatives as novel visible light photoinitiators for dental materials

  • Norbert Moszner

      Affiliations

    • Research & Development, Ivoclar Vivadent AG, FL-9494 Schaan, Liechtenstein
    • Corresponding Author InformationCorresponding author. Tel.: +423 2353429; fax: +423 2331279.
  • ,
  • Urs Karl Fischer

      Affiliations

    • Research & Development, Ivoclar Vivadent AG, FL-9494 Schaan, Liechtenstein
  • ,
  • Beate Ganster

      Affiliations

    • Vienna University of Technology, Institute of Applied Synthetic Chemistry, Getreidemarkt 9/163/MC, A-1060 Vienna, Austria
  • ,
  • Robert Liska

      Affiliations

    • Vienna University of Technology, Institute of Applied Synthetic Chemistry, Getreidemarkt 9/163/MC, A-1060 Vienna, Austria
  • ,
  • Volker Rheinberger

      Affiliations

    • Research & Development, Ivoclar Vivadent AG, FL-9494 Schaan, Liechtenstein

Received 18 September 2007 ,Revised 7 November 2007 ,Accepted 8 November 2007.

References 

  1. Monroe BM, Weiner SA, Hamond GS. Mechanism of photochemical reactions in solutions LVII. Photoreduction of camphorquinone. J Am Chem Soc. 1968;90:1913–1914
  2. Monroe BM, Weiner SA. Mechanism of photochemical reactions in solutions LVIII. Photoreduction of camphorquinone. J Am Chem Soc. 1969;91:450–456
  3. Singh A, Scott AR, Sopchyshyn F. Flash photolysis of camphorquinone and biacetyl. J Phys Chem. 1969;73:2633–2643
  4. Dart EC, Cantwell JB, Traynor JR, Jaworzyn JF, Nemcek J. (Invs.). Cureable dental filling compositions. US-PS 4,110,184, Imperial Chemical Industries; 1978.
  5. Crivello JV, Dietliker K. In: 2nd ed..  Bradley G editors. Photoinitiators for free radical cationic & anionic photopolymerization surface coatings technology. vol. III:Chichester etc.: John Wiley and Sons; 1998;p. 266–268
  6. Antonucci JM, Toth EE. Extent of polymerization of dental resins by differential scanning calorimetry. J Dent Res. 1983;62:121–125
  7. Ban S, Takahashi Y, Tanase H, Hasegawa J. Heat curing of light-cured composite resins investigated by dynamic differential scanning calorimetry. Dent Mater J. 1990;9:153–162
  8. Ferracane JL, Greener EH. Fourier transformation infrared analysis of degree of polymerization in unfilled resins—methods comparison. J Dent Res. 1984;63:1093–1095
  9. Rueggeberg FA, Hashinger DT, Fairhust CW. Calibration of FTIR conversion analysis of contemporary dental resin composites. Dent Mater. 1990;6:241–249
  10. Ferracane JL, Greener EH. The effect of resin formulation on the degree of conversion and mechanical properties of dental restorative resins. J Biomed Mater Res. 1986;20:121–131
  11. Ferracane JL, Mitchem JC, Condon JR, Todd R. Wear and marginal breakdown of composites with various degrees of cure. J Dent Res. 1997;76:1508–1516
  12. Peitzfeldt A, Asmussen E. Hardness of restorative resins: effect of camphorquinone, amine, and inhibitor. Acta Odont Scand. 1989;47:229–231
  13. Mateo JL, Bosch P, Lozana AE. Reactivity of radicals derived from dimethyl-anilines in acrylic photopolymerization. Macromolecules. 1994;27:7794–7799
  14. Cook WD. Photopolymerization kinetics of dimethacrylate using the camphorquinone/amine initiator system. Polymer. 1992;33:600–609
  15. Kucybala Z, Pietrzak M, Paczkowski J, Linden LA, Rabek JF. Kinetic studies of a new photoinitiator hybrid system based on camphorquinone-N-phenylglycine derivatives for laser polymerization of dental restorative and stereolithographic (3D) formulations. Polymer. 1996;20:4585–4591
  16. Jakubiak J, Allonas X, Fouassier JP, Sionkowska A, Andrzejewska E, Linden LA, et al. Camphorquinone-amines photoinitiating systems for the initiation of free radical polymerization. Polymer. 2003;44:5219–5226
  17. Park YJ, Chae KH, Rawls HR. Development of a new photoinitiation systems for dental light-cure composite resins. Dent Mater. 1999;15:120–127
  18. Angiolini L, Caretti D, Salatelli E. Synthesis and photoinitiation activity of radical polymeric photoinitiators bearing side-chain camphorquinone moieties. Macromol Chem Phys. 2000;201:2646–2653
  19. Allonas X, Fouassier JP, Angiolini L, Caretti D. Excited state properties of camphorquinone based monomeric and polymeric photoinitiators. Helv Chim Acta. 2001;84:2577–2588
  20. Ullrich G, Herzog D, Liska R, Burtscher P, Moszner N. Photoinitiators with functional groups VII. Covalently bonded camphorquinone-amines. J Polym Sci: Part A: Polym Chem. 2004;42:4949–4963
  21. Ullrich G, Ganster B, Salz U, Moszner N, Liska R. Photoinitiators with functional groups IX. Hydrophilic bisacylphosphine oxides for acidic formulations. J Polym Sci: Part A: Polym Chem. 2006;442:1686–1700
  22. Fouassier JP, Allonas X, Burget D. Photopolymerization reactions under visible light: principle, mechanism and examples of applications. Prog Org Coat. 2003;47:16–36
  23. Guggenberger R, Lechner G, Weinmann W, Bisacylphosphane . Oxides as photoinitiators in dental materials. Am Chem Soc, Div Polym Chem, Polym Prepr. 1997;38:105
  24. Richards ND, Dickens SH, Antonucci JM. Dental polymeric composites activated with camphorquinone or diacyl phosphine oxide photoinitiators. Am Chem Soc, Div Polym Chem, Polym Prepr. 2004;45:362–363
  25. Whitten D, Venz S. (Invs.). Titanate initiators for light cured compositions. EP-PS 334,338 A2, Dentsply International Inc.; 1989.
  26. Cunningham AF, Kunz M, Kura H. (Invs.). Borate photoinitiators from monoboranes. US-PS 6,045,974, Ciba Specialty Chemicals; 2000.
  27. Mochida K, Ichikawa K, Okui S, Sakaguchi Y, Hayashi H. Direct observation of germyl radicals by a laser-photolysis of germyl ketones. Chem Lett. 1985;1433–1436
  28. Wakassa M, Mochida K, Sakaguchi Y, Nakamura J, Hayashi H. Fluorescence of silyl and germanyl ketones and their primary photochemical processes. J Phys Chem. 1991;95:2241–2246
  29. Ganster B, Liska R, Gruber H, Salz U, Moszner N, New visible light photo-initiators for dental materials. RadTech Europe 2007, Vienna, Conf. Proced.
  30. Ganster B, Fischer UK, Moszner N, Liska R. New photocleavable structures. IV. Acylgerman based photoinitiator for visible light curing. Macromol Rapid Commun. 2008;29:57–62
  31. Moszner N, Zeuner F, Fischer UK, Rheinberger V. Monomers for adhesive polymers 2: Synthesis and radical polymerisation of hydrolytically stable acrylic phosphonic acids. Macromol Chem Phys. 1999;200:1062–1067
  32. Roehm NW, Rodgers GH, Hatfield SM, Glasebrook AL. An improved colorimetric assay for cell proliferation and viability utilizing the tetrazolium salt XTT. J Immunol Methods. 1991;142:257–265
  33. International standard ISO 4049, Dentistry–polymer-based filling restorative and luting materials; 2000.
  34. International standard ISO 7491, Dental materials–determination of color stability of dental resin materials; 1984.
  35. RCC-Report. In vitro single cell gel electrophoresis (comet assay) in Chinese Hamster V79 cells with K-37. 2006;1–14.
  36. RCC-Report. Salmonella Typhimurium and Escherichia Coli reverse mutation assay with K-37. 2007;1–31.
  37. RCC-Report. Salmonella Typhimurium and Escherichia Coli reverse mutation assay with K-42. 2007;1–31.
  38. Ganster B, Fischer UK, Moszner N, Liska R. New photocleavable structures. V. Bisacylgermane based photoinitiators for visible light curing. Macromolecules 2007, submitted for publication.
  39. Chen Y-C, Ferracane JL, Prahl SA. Quantum yield of conversion of the photoinitiator camphorquinone. Dent Mater. 2007;23:655–664
  40. Moszner N. 2004, unpublished results.
  41. Moszner N, Salz U, Zimmermann J. Chemical aspects of self-etching enamel-dentin adhesives—a systematic review. Dent Mater. 2005;21:895–910

PII: S0109-5641(07)00258-8

doi: 10.1016/j.dental.2007.11.004

Dental Materials
Volume 24, Issue 7 , Pages 901-907 , July 2008