A review of the development of radical photopolymerization initiators used for designing light-curing dental adhesives and resin composites

Dental Materials Journal

Volumn 29, Issue 5, 2010, Pages 481-501

  Kunio, Ikemura ^a   Takeshi, Endo ^b  

^a Shofu Inc   (Japan)

^b KINKI UNIVERSITY   (Japan)

Author keywords

Light curing dental adhesive; Photoinitiator; Radical photopolymerization

Indexed keywords

ABSORPTION WAVELENGTHS; CAMPHORQUINONE; COLOR TONE; DENTAL ADHESIVES; HIGH MECHANICAL STRENGTH; IN-DEGREE; LIGHT CURING; OPERATION TIME; PHOSPHINE OXIDE; PHOTOINITIATOR; RADICAL PHOTOPOLYMERIZATION; RESIN COMPOSITES; SCIENTIFIC PAPERS; SPECTRAL BEHAVIORS; TERTIARY AMINE;

ADHESIVES; CURING; PHOSPHORUS COMPOUNDS; PHOTOPOLYMERIZATION; RESINS; SODIUM;

DENTAL COMPOSITES;

AMINE; BIOMEDICAL AND DENTAL MATERIALS; CAMPHOR; CAMPHORQUINONE; DRUG DERIVATIVE; PHOSPHINE DERIVATIVE; PHOTOINITIATOR; RESIN; TOOTH CEMENT;

CHEMISTRY; DENTAL EQUIPMENT; HUMAN; LIGHT; PHOTOCHEMISTRY; POLYMERIZATION; RADIATION EXPOSURE; REVIEW; SPECTROPHOTOMETRY; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

AMINES; CAMPHOR; COMPOSITE RESINS; CURING LIGHTS, DENTAL; DENTAL CEMENTS; DENTAL MATERIALS; HUMANS; LIGHT; PHOSPHINES; PHOTOCHEMICAL PROCESSES; PHOTOINITIATORS, DENTAL; POLYMERIZATION; SPECTROPHOTOMETRY; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 78149405718     PISSN: 02874547     EISSN: None     Source Type: Journal    
DOI: 10.4012/dmj.2009-137     Document Type: Review

References (55)

1. 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.
2. Wataha JC, Lockwood PE, Lewis JB, Rueggeberg FA, Messer RLW. Biological effects of blue light from dental curing units. Dent Mater 2004; 20: 150-157.
3. Dart EC, Nemcek J. Photopolymerisable composition. Great Britain Patent Specification No. 1408265 (1971); Japanese Patent No. Toku-Kou-Sho 54-10986 (1979).
4. Tay FR, King NM, Suh BI, Pashley DH. Effect of delayed activation of light-curing resin composites on bonding of allinone adhesives. J Adhes Dent 2001; 3: 207-225.
5. Jockusch S, Koptyug IV, McGarry PF, Sluggett GW, Turro NJ, Watkins DW. A steady-state and picosecond pumpprobe investigation of the photophysics of an acyl and a bis(acyl)phosphine oxide. J Am Chem Soc 1996; 119: 11495-11501.
6. Sumiyoshi T, Schnabel W, Henne A, Lechtken P. On the photolysis of acylphosphine oxides: 1. Laser flash photolysis studies with 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Polymer 1985; 26: 141-146.
7. Arikawa H, Takahashi H, Kanie T, Ban S. Effect of various visible light photoinitiators on the polymerization and color of light-activated resins. Dent Mater J 2009; 28: 454-460.
8. Ikemura K, Ichizawa K, Jogetsu Y, Endo T. Synthesis of a novel camphorquinone derivative having acylphosphine oxide group, characterization by UV-VIS spectroscopy and evaluation of photopolymerization performance. Dent Mater J 2009; 29: 122-131.
9. Masuhara E, Kojima K, Hirasawa T, Tarumi N, Kimura T. Studies on dental self-curing resins. 3. Effects of alkylboran on the adhesive force to ivory and tooth surface. Rep Inst Dent Mater Tokyo Med Dent Univ 1963; 2: 457-456.
10. Masuhara E. Über die Chemie eines neuen haftfähigen Kunststoff-Füllungsmaterials. DZZ 1969; 24: 620-628.
11. Hayakawa T, Horie K. Effect of water-soluble photoinitiator on the adhesion between composite and tooth substrate. Dent Mater J 1992; 8: 351-353.
12. Hayakawa T, Nemoto K, Horie K. Adhesion of composite to polished dentin retaining its smear layer. Dent Mater 1995; 11: 218-222.
13. Hayakawa T, Kikutake K, Nemoto K. Effectiveness of the addition of water-soluble photoinitiator into the self-etching primers on the adhesion of a resin composite to polished dentin and enamel. Dent Mater J 1999; 18: 324-333.
14. Hayakawa T, Kidokoro N. Water-based photo-curable adhesive composition. Japanese Patent No. Toku-Kou-3158422 (2001).
15. Hayakawa T, Kikutake-Sugiyama K, Fukushima T, Nemoto K. Development of self-etching primer adhesive in all-inone bonding system. Dent Mater J 2005; 24: 251-256.
16. Hayakawa T, Kikutake-Sugiyama K, Nemoto K. Efficacy of water-soluble photoinitiator on the adhesion of composite resin to bovine teeth in all-in-one bonding system. Dent Mater J 2005; 24: 213-218.
17. Kikutake K, Hayakawa T, Nemoto K. Study on the selfetching primer containing water-soluble photoinitiator. Adhes Dent 1998; 16: 152-160.
18. Kikutake K. Development of a one step adhesion system using photo curing self-etching primer. J J Dent Mater 1999; 18: 151-169.
19. Ikemura K, Ichizawa K, Fuchigami K, Ito S, Endo T. Design of a new dental adhesive - Effect of a water-soluble sodium acylphosphine oxide with crown ether on adhesion to dental hard tissues. Dent Mater J 2009; 28: 267-276.
20. Ikemura K, Ichizawa K, Endo T. Design of a new selfetching HEMA-free adhesive. Dent Mater J 2009; 28: 558-564.
21. Ikemura K, Endo T. A review of our development of dental adhesives - Effects of radical polymerization initiators and adhesive monomers on adhesion. Dent Mater J 2010; 29: 109-121.
22. Bowen RL, Cobb EN, Rapson JE. Adhesive bonding of various materials to hard tooth tissues: Improvement in bond strength to dentin. J Dent Res 1982; 61: 1070-1076.
23. Ikemura K, Endo T. Effect on adhesion of new polymerization initiator systems comprising 5- monosubstituted barbituric acids, aromatic sulfinate amides and tert-butylperoxymaleic acid in dental adhesive. J Appl Polym Sci 1999; 72: 1655-1668.
24. Lechtken PI, Jacobi M, Trimborn W. Acylphosphine oxide compounds: their preparation and use. United States Patent No. 4298738; 1981.
25. Kolczak U, Rist G, Dietliker K, Wirz J. Reaction mechanism of monoacyl- and bisacylphosphine oxide photoinitiators studied by 31P-, 13C-, and 1H-CIDNP and ESR. J Am Chem Soc 1996; 118: 6477-6489.
26. Rutsch W, Dietliker K, Leppard D, Kohler M, Misev L, Kolczak U. Recent developments in photoinitiators. Progress in Organic Coatings 1996; 27: 227-239.
27. Ikemura K, Ichizawa K, Yoshida M, Ito S, Endo T. UV-VIS spectra and photoinitiation behaviors of acylphosphine oxide and bisacylphosphine oxide derivatives in unfilled, lightcuring dental resins. Dent Mater J 2008; 27: 765-774.
28. Atai M, Watts DC. A new kinetic model for the photopolymerization shrinkage-strain of dental composites and resin-monomers. Dent Mater 2006; 22: 785-791.
29. Park YJ, Chae KH, Rawls HR. Development of a new photoinitiation system for dental light-cure composite resins. Dent Mater 1999; 15: 120-127.
30. Jandt KD, Mills RW, Blackwell GB, Ashworth SH. Depth of cure and compressive strength of dental composites cured with blue light emitting diodes (LEDs). Dent Mater 2000; 16: 41-47.
31. Teshima W, Nomura Y, Tanaka N, Urabe H, Okazaki M, Nahara Y. ESR study of camphorquinone/amine photoinitiator systems using blue light-emitting diodes. Biomaterials 2003; 24: 2097-2103.
32. Teshima W, Nomura Y, Tanaka N, Shibata S, Shintani T, Shirai K, Urabe H, Nahara Y, Shintani H. Kinetic analysis of photopolymerized dental resins supplemented with new photoinitiators cured by violet LEDs. J J Concerve Dent 2004; 47: 442-453.
33. Masuhara E, Komiya S, Sawamoto T, Satou Y. A Photoinitiator composition for visible light polymerizable adhesives. Japanese Patent No. 3442776 (2003).
34. Ikemura K, Ichizawa K. Visible-light polymerizable composition. Japanese Patent Toku-Kai 2005-171213; 2005.
35. Moriyama S, Murata S, Tanaka M, Makino Y. A Phosphine oxide compound. Japanese Patent Open, Toku-kai 2005-225793; 2005.
36. Imai Y, Kadoma Y, Kojima K. A photoinitiator. Japanese Patent Toku-Kai-Hei 3-243602 (1991).
37. Bhattacharya AK, Thyagarajan G. The Michaelis-Arbuzov rearrangement. Chem Rev 1981; 81: 415-430.
38. Murphy PJ. Practical approach in chemistry - Organophosphorus reagents, 1st ed. New York: Oxford University Press Inc; 2004. p.172-185.
39. Ikemura K, Ichizawa K, Jyougetsu Y. Camphorquinone derivative having acylphosphine oxide group, and containing the same, photopolymerization catalyst and photo/chemical polymerization catalyst, and containing these, hardenable composition. International Patent Application No. PCT/ JP2006/304911, WO/2007/105296; 2006.
40. De Groot JH, Dillingham K, Deuring H, Haitjema HJ, van Beijima FJ, Hodd K, Norrby S. Hydrophilic polymeric acylphosphine oxide photoinitiators/crosslinkers for in vivo blue-light photopolymerization. Biomacromol 2001; 2: 1271-1278.
41. Lai JH, Johnson AE. Measuring polymerization shrinkage of photo-activated restorative materials by a water-filled dilatometer. Dent Mater 1993; 16: 172-176.
42. Davis MJ, Gawne G, Green PN, Green WA. The synthesis and properties of a novel series of water soluble thioxanthone photoinitiators. Spec Chem 1986; 6: 363-369.
43. Pedersen CJ. Cyclic polyethers and their complexes with metal salts. J Am Chem Soc 1967; 89: 7017-7036.
44. Ikemura K, Ichizawa K, Fuchigami K. A Curable composition comprising clathrate compounds. Japanese Patent Open No. Toku-Kai-2005-248137 (2005).
45. Ulman A. An introduction to ultrathin organic films: From Langmuir-Blodgett to self-assembly. San Diego: Academic Press Inc; 1991.
46. Hendrixson RR, Mack MP, Palmer RA, Ottolenghi A, Ghirardelli RG. Oral toxicity of the cyclic polyethers - 12- crown-4, 15-crown-5, and 18-crown-6 in mice. Toxicol Appl Oharmacol 1978; 44: 263-268.
47. Tay FR, Pashley DH. Permeability of single-step, self-etch adhesives - the cost of saving time. "Self-etching Primer: Current Status and Its Evolution". Proceedings of the International Symposium'01 in Tokyo, First Edition, 2003. p. 23-39.
48. De Munck J, Arita A, Shirai K, Van Landuyt KL, Coutinho E, Poitevin A, Peumans M, Lambrechts P, Van Meerbeek B. Microrotary fatigue resistance of a HEMA-free all-in-one adhesive bonded to dentin. J Adhes Dent 2007; 9: 373-379.
49. Nishiyama N, Suzuki K, Yoshida H, Teshima H, Nemoto K. Hydrolytic stability of methacrylamide in acidic aqueous solution. Biomaterials 2004; 25: 965-969.
50. Katsuno K, Manabe A, Itoh K, Nakamura Y, Wakumoto S, Hisamitsu H, Yoshida T. Contact dermatitis caused by 2- HEMA and GM dentin primer solutions applied to guinea pigs and humans. Dent Mater J 1996; 15: 22-30.
51. Ichizawa K, Ikemura K. A pH-controlled adhesive composition. Japanese Patent Open No. Toku-Kai-2007-31339 (2007).
52. Freedman G. First impressions. Dentistry Today 2009; 28: 1.
53. Takeuchi F, Mizuta Y. Photocurable resin composition containing anthraquinone derivative. International Patent WO 2007/074782 A1 (2007).
54. Angiolini L, Caretti D, Carlini C. Polymeric photoinitiators bearing side-chain benzoyldiphenylphosphine oxide moieties for UV curable coatings. J Appl Polym Sci 1994; 51: 133-143.
55. Angiolini L, Caretti D, Carlini C. Polymeric systems bearing side-chain 2,6-dimethylbenzoyl-diphenylphosphine oxide moieties for UV curable coatings: Synthesis and photoinitiation activity. J Appl Polym Sci 1995; 57: 519-531.