Journal of Dentistry
Volume 36, Issue 3 , Pages 171-177 , March 2008

Synthesis of phosphate monomers and bonding to dentin: Esterification methods and use of phosphorus pentoxide

  • Fabrício Aulo Ogliari

      Affiliations

    • Operative Dentistry Department, School of Dentistry, Federal University of Pelotas, RS, Brazil
    • ,
  • Eduardo de Oliveira da Silva

      Affiliations

    • Organic Chemistry Department, Chemistry Institute, Federal University of Rio Grande do Sul, RS, Brazil
    • ,
  • Giana da Silveira Lima

      Affiliations

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

      Affiliations

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

      Affiliations

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

      Affiliations

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

      Affiliations

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

      Affiliations

    • Organic Chemistry Department, Chemistry Institute, Federal University of Rio Grande do Sul, RS, Brazil
    • ,
  • Evandro Piva

      Affiliations

    • Operative Dentistry Department, School of Dentistry, Federal University of Pelotas, RS, Brazil
    • Corresponding Author InformationCorresponding author at: CDC-Bio, School of Dentistry, Federal University of Pelotas, Rua Gonçalves Chaves 457, CEP 96015-560, Pelotas, RS, Brazil. Tel.: +55 53 3222 6690; fax: +55 53 3222 6690.

Received 31 July 2007 ,Revised 24 October 2007 ,Accepted 3 November 2007.

References 

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  3. Tay FR, Pashley DH. Aggressiveness of contemporary self-etching systems. I. Depth of penetration beyond dentin smear layers. Dental Materials. 2001;17:296–308
  4. Salz U, Mucke A, Zimmermann J, Tay FR, Pashley DH. pKa value and buffering capacity of acidic monomers commonly used in self-etching primers. Journal of Adhesive Dentistry. 2006;8:143–150
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  8. Okada K, Ohtsuki J, Takahashi K, Minami Y, Terakawa E, Harada M. Kuraray Co, Ltd., assignee. Organophosphorus compounds for dental polymerizable compositions. US patent 6,458,868; 2002.
  9. Elias A, Didi MA, Villemin D, Semaoune T, Ouattas S. Synthesis of mono-and dialkylphosphates by the reactions of hydroxycompounds with the phosphorus pentoxide under microwave irradiation. Phosphorus Sulfur and Silicon and the Related Elements. 2004;179:2599–2607
  10. Aafaqi R, Mohamed AR, Bhatia S. Kinetics of esterification of palmitic acid with isopropanol using p-toluene sulfonic acid and zinc ethanoate supported over silica gel as catalysts. Journal of Chemical Technology and Biotechnology. 2004;79:1127–1134
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  13. Smith H. Kinetics of the catalyzed esterification of normal aliphatic acids in methyl alcohol. Journal of the American Chemical Society. 1939;61:254–260
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  16. De Munck J, Van Landuyt K, Peumans M, Poitevin A, Lambrechts P, Braem M, et al. A critical review of the durability of adhesion to tooth tissue: methods and results. Journal of Dental Research. 2005;84:118–132
  17. 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
  18. Reis A, Grandi V, Carlotto L, Bortoli G, Patzlaff R, Rodrigues Accorinte Mde L, et al. Effect of smear layer thickness and acidity of self-etching solutions on early and longterm bond strength to dentin. Journal of Dentistry. 2005;33:549–559
  19. Ogliari FA, de Sordi ML, Ceschi MA, Petzhold CL, Demarco FF, Piva E. 2,3-Epithiopropyl methacrylate as functionalized monomer in a dental adhesive. Journal of Dentistry. 2006;34:472–477
  20. Ikemura K, Tay FR, Nishyama N, Pashley DH, Endo T. Design of new phosphonic acid monomers for dental adhesives—synthesis of (meth)acryloxyalkyl 3-phosphonopropionates and evaluation of their adhesion-promoting functions. Dental Materials Journal. 2006;25:566–575
  21. Hiraishi N, Nishiyama N, Ikemura K, Yau JY, King NM, Tagami J, et al. Water concentration in self-etching primers affects their aggressiveness and bonding efficacy to dentin. Journal of Dental Research. 2005;84:653–658
  22. Tay FR, Pashley DH. Have dentin adhesives become too hydrophilic?. Journal of the Canadian Dentistry Association. 2003;69:726–731
  23. Pashley EL, Zhang Y, Lockwood PE, Rueggeberg FA, Pashley DH. Effects of HEMA on water evaporation from water–HEMA mixtures. Dental Materials. 1998;14:6–10

PII: S0300-5712(07)00235-7

doi: 10.1016/j.jdent.2007.11.003

Journal of Dentistry
Volume 36, Issue 3 , Pages 171-177 , March 2008

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