Design of a new dental adhesive - Effect of a water-soluble sodium acylphosphine oxide with crown ether on adhesion to dental hard tissues

Dental Materials Journal

Volumn 28, Issue 3, 2009, Pages 267-276

  Ikemura, Kunio ^a   Ichizawa, Kensuke ^a   Fuchigami, Kiyomi ^a   Ito, So ^a   Endo, Takeshi ^b  

^a Shofu Inc   (Japan)

^b KINKI UNIVERSITY   (Japan)

Author keywords

Crown ether; Sodium acylphosphine oxide; Water soluble photoinitiator

Indexed keywords

4 METHACRYLOXYETHYLTRIMELLITIC ACID; 4-METHACRYLOXYETHYLTRIMELLITIC ACID; BEAUTIFIL COMPOSITE RESIN; BISPHENOL A BIS(2 HYDROXYPROPYL) ETHER DIMETHACRYLATE; CROWN ETHER; IONOPHORE; MACROGOL DERIVATIVE; METHACRYLIC ACID DERIVATIVE; PHENYLPHOSPHINIC ACID; PHOSPHINE DERIVATIVE; PHOSPHINIC ACID DERIVATIVE; PHOSPHONOACETIC ACID; POLYMETHACRYLIC ACID DERIVATIVE; RESIN; RESIN CEMENT; TOOTH CEMENT; TRICARBOXYLIC ACID; TRIETHYLENE GLYCOL DIMETHACRYLATE; WATER;

ACYLATION; ANIMAL; ARTICLE; CATTLE; CHEMISTRY; DENTAL BONDING; DENTAL CARE; DENTAL CURING LIGHT; DENTIN; ENAMEL; HYDROPHOBICITY; INSTRUMENTATION; SHEAR STRENGTH; SOLUBILITY; SYNTHESIS; ULTRASTRUCTURE;

ACYLATION; ANIMALS; BISPHENOL A-GLYCIDYL METHACRYLATE; CATTLE; COMPOSITE RESINS; CROWN ETHERS; CURING LIGHTS, DENTAL; DENTAL BONDING; DENTAL CEMENTS; DENTAL ENAMEL; DENTAL STRESS ANALYSIS; DENTIN; HYDROPHOBICITY; IONOPHORES; METHACRYLATES; PHOSPHINES; PHOSPHINIC ACIDS; PHOSPHONOACETIC ACID; POLYETHYLENE GLYCOLS; POLYMETHACRYLIC ACIDS; RESIN CEMENTS; SHEAR STRENGTH; SOLUBILITY; TRICARBOXYLIC ACIDS; WATER;

EID: 67649531375     PISSN: 02874547     EISSN: None     Source Type: Journal    
DOI: 10.4012/dmj.28.267     Document Type: Article

References (34)

1. 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.
2. Hayakawa T, Kikutake K, Nemoto K. Influence of self-etching primer treatment on the adhesion of resin composite to polished dentin and enamel. Dent Mater 1998; 14: 99-105.
3. Hayakawa T, Kidokoro N. Water-based photocurable adhesive composition. Japanese Patent No. Toku-Kou-3158422 (2001).
4. Hayakawa T, Kikutake-Sugiyama K, Nemoto K. Efficacy of water-soluble photoinitiator on the adhesion of composite resin to bovine teeth in all-inone bonding system. Dent Mater J 2005; 24: 213-218.
5. Kikutake K. Development of one step adhesive system using photo curing self-etching primer. J Jpn Dent Mater 1999; 18: 151-169.
6. Tay FR, King NM, Suh BI, Pashley DH. Effect of delayed activation of light-cured resin composites on bonding of all-in-one adhesives. J Adhes Dent 2001; 3: 207-225.
7. 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.
8. 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.
9. Jockusch S, Koptyug IV, McGarry PF, Sluggett GW, Turro NJ, Watkins DW. A steady-state and picoseconds pump-probe investigation of the photophysics of an acyl and a bis(acyl)phosphine oxide. J Am Chem Soc 1996; 119: 11495-11501.
10. 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, light-cured dental resins. Dent Mater J 2008; 27: 765-774.
11. Pedersen CJ. Cyclic polyethers and their complexes with metal salts. J Am Chem Soc 1967; 89: 7017-7036.
12. Henne A, Hesse A, Jacobi M, Wallbilich G, Bronstert B. Acylphosphine compounds and their use as photoinitiators. United States Patents No. 4719297 (1988); (BASF Aktiengesellschaft).
13. Murphy PJ. Practical approach in chemistry - Organophosphorus reagents, 1st ed, Oxford University Press, New York, 2004, pp.172-185.
14. Bhattacharya AK, Thyagarajan G. The Michaelis-Arbuzov rearrangement. Chem Rev 1981; 81: 415-430.
15. Ikemura K, Tay FR, Nishiyama N, Pashley DH, Endo T. Multi-purpose bonding performance of newly synthesized phosphonic acid monomers. Dent Mater J 2007; 26: 105-115.
16. Nakabayashi N, Takeyama M, Kojima K, Masuhara E. Studies on dental self-curing resins (19) - Adhesion of 4-META/MMA-TBB resin to pretreated dentin. J J Dent Mater 1982; 23: 29-33.
17. Bowen RL. Dental filling material comprising vinyl silane treated fused silica and a binder consisting of the reaction product of Bisphenol and glycydyl acrylate. United States Patent No. 3066112 (1962).
18. Schilke R, Bauss O, Lisson JA, Geurtsen W. Bovine dentin as a substitute for human dentin in shear bond strength measurements. Am J Dent 1999; 12: 92-96.
19. Ikemura K, Ichizawa K, Fuchigami K. A curable composition comprising a clathrate compound. Japanese Patent Open No. Toku-Kai-2005-248137 (2005). (Shofu Inc.).
20. 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. Biomacromolecules 2001; 2: 1271-1278.
21. Tay FR, Pashley DH. Permeability of single-step, self-etch adhesives - the cost of saving time. "Selfetching Primer: Current Status and Its Evolution" Proceedings of the International Symposium '01 in Tokyo, First Edition, 2003, pp.23-39.
22. De Munck J, Arita A, Shirai K, Van Landuyt KL, Coutinho E, Poitevin A, Peumans M, Lambrechts, Van Meerbeek B. Microrotary fatigue resistance of a HEMA-free all-in-one adhesive bonded to dentin. J Adhes Dent 2007; 9: 373-379.
23. Nishiyama N, Suzuki K, Yoshida H, Teshima H, Nemoto K. Hydrolytic stability of methacrylamide in acidic aqueous solution. Biomater 2004; 25: 965-969.
24. 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.
25. Ikemura K, Tay FR, Hironaka T, Endo T, Pashley DH. Bonding mechanism and ultrastructural interfacial analysis of a single-step adhesive to dentin. Dent Mater 2003; 19: 703-715.
26. Moszner N, Salz U, Zimmermann J. Chemical aspects of self-etching enamel-dentin adhesives: a systematic review. Dent Mater 2005; 21: 895-910.
27. Sano H, Shono T, Takatsu T, Hosoda H. Microporous dentin zone beneath resin-impregnated layer. Oper Dent 1994; 19: 59-64.
28. Tay FR, Pashley DH, Suh BI, Hiraishi N, Yiu CK. Water treeing in simplified dentin adhesives - déjà vu? Oper Dent 2005; 30: 561-579.
29. Tay FR, Pashley DH. Water-treeing - a potential mechanism for degradation of dentin adhesives. Am J Dent 2003; 16: 6-12.
30. Hashimoto M, Fujita S, Kaga M, Yawaka Y. In vitro durability of one-bottle resin adhesives bonded to dentin. Dent Mater J 2007; 25: 677-686.
31. Ulman A. An introduction to ultrathin organic films from Langmuir-Blodgett to self-assembly, Academic Press, Inc. San Diego, 1991.
32. 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.
33. Takayama K, Hasegawa S, Sasagawa N, Nambu N, Nagai T. Apparent oral toxicity of 18-crown-6 in dogs. Chem Pharm Bull 1977; 25: 3125-3130.
34. Gad SC, Conroy WJ, McKelvey JA, Turney RA. Behavioral and neuropharmacological toxicology of the macrocyclic ether 18-crown-6. Drug Chem Toxicol 1978; 1: 339-353.