Journal of Dentistry
Volume 34, Issue 7 , Pages 472-477 , August 2006

2,3-Epithiopropyl methacrylate as functionalized monomer in a dental adhesive

  • Fabrício Aulo Ogliari

      Affiliations

    • Department of Operative Dentistry, School of Dentistry, Federal University of Pelotas, RS, Brazil
    • Corresponding Author InformationCorresponding author. Tel.: +55 53 3222 6690; fax: +55 53 3222 6690.
    • ,
  • Marli Luiza Tebaldi de Sordi

      Affiliations

    • Department of Organic Chemistry, Chemistry Institute, Federal University of Rio Grande do Sul, RS, Brazil
    • ,
  • Marco Antônio Ceschi

      Affiliations

    • Department of Organic Chemistry, Chemistry Institute, Federal University of Rio Grande do Sul, RS, Brazil
    • ,
  • Cesar Liberato Petzhold

      Affiliations

    • Department of Organic Chemistry, Chemistry Institute, Federal University of Rio Grande do Sul, RS, Brazil
    • ,
  • Flávio Fernando Demarco

      Affiliations

    • Department of Operative Dentistry, School of Dentistry, Federal University of Pelotas, RS, Brazil
    • ,
  • Evandro Piva

      Affiliations

    • Department of Operative Dentistry, School of Dentistry, Federal University of Pelotas, RS, Brazil

Received 2 September 2005 ,Revised 3 November 2005 ,Accepted 7 November 2005.

References 

  1. Nakabayashi N, Kojima K, Masuhara E. The promotion of adhesion by the infiltration of monomers into tooth substrates. Journal of Biomedical Materials Research. 1982;16:267–273
  2. Bergenholtz G. Evidence for bacterial causation of adverse pulpal responses in resin-based dental restorations. Critical Reviews in Oral Biology & Medicine. 2000;11:467–480
  3. Gordan VV, Mjor IA, Vazquez O, Watson RE, Wilson N. Self-etching primer and resin-based restorative material: two-year clinical evaluation. Journal of Esthetic and Restorative Dentistry. 2002;14:296–302
  4. Deliperi S, Bardwell DN, Papathanasiou A. Effect of different polymerization methods on composite microleakage. American Journal of Dentistry. 2003;16:73a–76a
  5. Koshiro K, Inoue S, Tanaka T, Koase K, Fujita M, Hashimoto M, et al. In vivo degradation of resin–dentin bonds produced by a self-etch vs. a total-etch adhesive system. European Journal of Oral Sciences. 2004;112:368–375
  6. Donmez N, Belli S, Pashley DH, Tay FR. Ultrastructural correlates of in vivo/in vitro bond degradation in self-etch adhesives. Journal of Dental Research. 2005;84:355–359
  7. Peumans M, Kanumilli P, De Munck J, Van Landuyt K, Lambrechts P, Van Meerbeek B. Clinical effectiveness of contemporary adhesives: a systematic review of current clinical trials. Dental Materials. 2005;21:864–881
  8. Demarco FF, Tarquinio SBC , Jaeger MMM, de Araujo VC, Matson E. Pulp response and cytotoxicity evaluation of 2 dentin bonding agents. Quintessence International. 2001;32:211–220
  9. Egawa H, Ishikawa M, Tsunooka M, Ueda T, Tanaka M. Photocrosslinking of poly(2,3-epithiopropyl methacrylate) film with 254nm irradiation. Journal of Polymer Science. 1983;21:479–486
  10. Nonaka T, Matsumura S, Ogata T, Kurihara S. Synthesis of amphoteric polymer membranes from epithiopropyl methacrylate-butylmethacrylate-N,N-dimethylaminopropyl acrylamide-methacrylic acid copolymers and the permeation behavior of various solutes through the membranes. Journal of Membrane Science. 2003;212:39–53
  11. Kadoma Y. Surface treatment agent for dental metals using a thiirane monomer and a phosphoric acid monomer. Dental Materials Journal. 2002;21:156–169
  12. Rogers FE. Polymerization of monomers containing thiiran rings. Journal of Polymer Science. 1965;A3:2701–2703
  13. Iranpoor N, Kazemi F. Stereospecific formation of S(-) styrene sulfide: efficient conversion of epoxides to thiiranes catalysed with Ru(III). Tetrahedron. 1997;53:11377–11382
  14. Inoue S, Vargas MA, Van Meerbeek B, Abe Y, Yoshida Y, Lambrechts P, et al. Micro-tensile bond strength of eleven modern adhesives to dentin. Journal of Adhesive Dentistry. 2001;3:237–246
  15. Reis A, Loguercio AD, Carvalho RM, Grande RHM. Durability of resin dentin interfaces: effects of surface moisture and adhesive solvent component. Dental Materials. 2004;20:669–676
  16. Okuda M, Pereira PN, Nakajima M, Tagami J. Relationship between nanoleakage and long-term durability of dentin bonds. Operative Dentistry. 2001;26:482–490
  17. Tjäderhane L, Larjava H, Sorsa T, Uitto V-J, Larmas M, Salo T. The activation and function of host matrix metalloproteinases in dentin matrix breakdown in caries lesions. Journal of Dental Research. 1998;77:1622–1629
  18. Pashley DH, Tay FR, Yiu C, Hashimoto M, Breschi L, Carvalho RM, et al. Collagen degradation by host-derived enzymes during aging. Journal of Dental Research. 2004;83:216–221
  19. Takahashi A, Sato Y, Uno S, Pereira PNR, Sano H. Effects of mechanical properties of adhesive resins on bond strength to dentin. Dental Materials. 2002;18:263–268
  20. Sano H, Takatsu T, Ciucchi B, Russel CM, Pashley DH. Tensile properties of resin-infiltrated demineralized human dentin. Journal of Dental Research. 1995;74:1093–1102
  21. Carrilho MRD, Tay FR, Pashley DH, Tjaderhane L, Carvalho RM. Mechanical stability of resin–dentin bond components. Dental Materials. 2005;21:232–241
  22. Drummond R, Boydston GL, Peppas NA. Properties of positives resists. III. The dissolution behavior of poly(methyl methacrylate-co-maleic-anhydride). Journal of Applied Polymer Science. 1990;39:2267–2277
  23. He Y, Zhu B, Inoue Y. Hydrogens bonds in polymer blends. Progress in Polymer Science. 2004;29:1021–1051
  24. Gillham JK. Formation and properties of network polymeric materials. Polymer Engineering and Science. 1979;19:676–682
  25. Hanks CT, Wataha JC, Parsell RR, Strawn SE. Delineation of cytotoxic concentrations of two dentin bonding agents in vitro. Journal of Endodontics. 1992;18:589–596
  26. Wennberg A, Mjor IA, Hensten-Pettersen A. Biological evaluation of dental restorative materials—a comparison of different test methods. Journal Biomedical Materials Research. 1983;17:23–36
  27. Costa CA, Vaerten MA, Edwards CA, Hanks CT. Cytotoxic effects of current dental adhesive systems on immortalized odontoblast cell line MDPC-23. Dental Materials. 1999;15:434–441
  28. Tsunooka M, Tanaka S, Tanaka M. Photocrosslinking of poly(2,3-epithiopropyl methacrylate) by the oxidation of pendant episulfide groups. Journal of Polymer Science. 1985;23:2495–2505
  29. Nonaka T, Maeda H, Nakayama M, Egawa H. Transport of alkali metal ions against its concentration gradient through 2,3-epithiopropyl methacrylate-methacrylic acid copolymer membrane. Journal of Applied Polymer Science. 1987;34:1025

PII: S0300-5712(05)00199-5

doi: 10.1016/j.jdent.2005.11.001

Journal of Dentistry
Volume 34, Issue 7 , Pages 472-477 , August 2006

Article Tools

* Image Usage & Resolution