The effect of the strength and wetting characteristics of Bis-GMA/TEGDMA-based adhesives on the bond strength to dentin

2,2-Bis[4-(2-methoxy-3-methacryloyloxy propoxy) phenyl] propane을 함유한 상아질 접착레진의 물성이 접착강도에 미치는 영향

  • Park, Eun-Sook (Department of Conservative Dentistry, Seoul National University School of Dentistry and Dental Research Institute) ;
  • Kim, Chang-Keun (School of Chemical Engineering and Materials Science, Chung-Ang University) ;
  • Bae, Ji-Hyun (Department of Conservative Dentistry, Section of Dentistry, Seoul National University Bundang Hospital) ;
  • Cho, Byeong-Hoon (Department of Conservative Dentistry, Seoul National University School of Dentistry and Dental Research Institute)
  • 박은숙 (서울대학교 치의학대학원 치과보존학교실) ;
  • 김창근 (중앙대학교 공과대학) ;
  • 배지현 (분당서울대학교병원 치과보존과) ;
  • 조병훈 (서울대학교 치의학대학원 치과보존학교실)
  • Received : 2011.03.02
  • Accepted : 2011.03.06
  • Published : 2011.03.31


Objectives: This study investigated the effect of the strength and wetting characteristics of adhesives on the bond strength to dentin. The experimental adhesives containing various ratios of hydrophobic, low-viscosity Bis-M-GMA, with Bis-GMA and TEGDMA, were made and evaluated on the mechanical properties and bond strength to dentin. Materials and Methods: Five experimental adhesives formulated with various Bis-GMA/Bis-MGMA/TEGDMA ratios were evaluated on their viscosity, degree of conversion (DC), flexural strength (FS), and microtensile bond strength (MTBS). The bonded interfaces were evaluated with SEM and the solubility parameter was calculated to understand the wetting characteristics of the adhesives. Results: Although there were no significant differences in the DC between the experimental adhesives at 48 hr after curing (p > 0.05), the experimental adhesives that did not contain Bis-GMA exhibited a lower FS than did those containing Bis-GMA (p < 0.05). The experimental adhesives that had very little to no TEGDMA showed significantly lower MTBS than did those containing a higher content of TEGDMA (p < 0.05). The formers exhibited gaps at the interface between the adhesive layer and the hybrid layer. The solubility parameter of TEGDMA approximated those of the components of the primed dentin, rather than Bis-GMA and Bis-M-GMA. Conclusions: To achieve a good dentin bond, a strong base monomer, such as Bis-GMA, cannot be completely replaced by Bis-M-GMA for maintaining mechanical strength. For compatible copolymerization between the adhesive and the primed dentin as well as dense cross-linking of the adhesive layer, at least 30% fraction of TEGDMA is also needed.


  1. Schwartz RS, Summitt JB, Robbins JW. Fundamentals of operative dentistry.1st ed. Chicago: Quintessence Publishing Co; 1996. p162-167.
  2. Van Meerbeek B, Willems G, Celis JP, Roos JR, Braem M, Lambrechts P, Vanherle G. Assessment by nano-indentation of the hardness and elasticity of the resin-dentin bonding area. J Dent Res 1993;72:1434-1442.
  3. Dickens SH, Cho BH. Interpretation of bond failure through conversion and residual solvent measurements and Weibull analyses of flexural and microtensile bond strengths of bonding agents. Dent Mater 2005;21:354-364.
  4. Bae JH, Cho BH, Kim JS, Kim MS, Lee IB, Son HH, Um CM, Kim CK, Kim OY. Adhesive layer properties as a determinant of dentin bond strength. J Biomed Mater Res B Appl Biomater 2005;74:822-828.
  5. Miyazaki M, Ando S, Hinoura K, Onose H, Moore BK. Influence of filler addition to bonding agents on shear bond strength to bovine dentin. Dent Mater 1995;11:234-238.
  6. Montes MA, de Goes MF, da Cunha MR, Soares AB. A morphological and tensile bond strength evaluation of an unfilled adhesive with low-viscosity composites and a filled adhesive in one and two coats. J Dent 2001;29:435-441.
  7. Conde MC, Zanchi CH, Rodrigues-Junior SA, Carreno NL, Ogliari FA, Piva E. Nanofiller loading level: influence on selected properties of an adhesive resin. J Dent 2009;37:331-335.
  8. 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.
  9. Cadenaro M, Breschi L, Antoniolli F, Navarra CO, Mazzoni A, Tay FR, Di Lenarda R, Pashley DH. Degree of conversion of resin blends in relation to ethanol content and hydrophilicity. Dent Mater 2008;24:1194-1200.
  10. Ogliari FA, Ely C, Lima GS, Conde MC, Petzhold CL, Demarco FF, Piva E. Onium salt reduces the inhibitory polymerization effect from an organic solvent in a model dental adhesive resin. J Biomed Mater Res B Appl Biomater 2008;86:113-118.
  11. Guo X, Wang Y, Spencer P, Ye Q, Yao X. Effects of water content and initiator composition on photopolymerization of a model BisGMA/HEMA resin. Dent Mater 2008;24:824-831.
  12. Malacarne J, Carvalho RM, de Goes MF, Svizero N, Pashley DH, Tay FR, Yiu CK, Carrilho MR. Water sorption/solubility of dental adhesive resins. Dent Mater 2006;22:973-980.
  13. Peutzfeldt A. Resin composites in dentistry: the monomer systems. Eur J Oral Sci 1997;105:97-116.
  14. Kim JW, Kim LU, Kim CK, Cho BH, Kim OY. Characteristics of novel dental composites containing 2,2-Bis[4-(2-methoxy-3-methacryloyloxy propoxy)phenyl] propane as a base resin. Biomacromolecules 2006;7:154-160.
  15. Navarra CO, Cadenaro M, Armstrong SR, Jessop J, Antoniolli F, Sergo V, Di Lenarda R, Breschi L. Degree of conversion of Filtek Silorane Adhesive System and Clearfil SE Bond within the hybrid and adhesive layer: an in situ Raman analysis. Dent Mater 2009;25:1178-1185.
  16. Ge J, Trujillo M, Stansbury J. Synthesis and photopolymerization of low shrinkage methacrylate monomers containing bulky substituent groups. Dent Mater 2005;21:1163-1169.
  17. Rueggeberg FA, Hashinger DT and Fairhurst CW. Calibration of FTIR conversion analysis of contemporary dental resin composites. Dent Mater 1990;6:241-249.
  18. Hoy KL. Tables of solubility parameters. Solvent and coatings materials research and development department: Union carbide corporation; 1985.
  19. Van Krevelen DW. Properties of polymers, 3rd ed. N.Y.: Elsevier science publishing co., Inc.; 1990.
  20. Kalachandra S. Sankarapandian M, Shobha HK, Taylor DF, Mcgrath JE. Influence of hydrogen bonding on properties of Bis-GMA analogues. J Mater Sci Mater Med 1997;8: 283-286.
  21. Pereira SG, Nunes TG, Kalachandra S. Low viscosity dimethacrylate comonomer compositions [Bis-GMA and CH3Bis-GMA] for novel dental composites; analysis of the network by stray-field MRI, solid-state NMR and DSC & FTIR. Biomaterials 2002;23:3799-3806.
  22. Pereira SG, Osorio R, Toledano M, Nunes TG. Evaluation of two Bis-GMA analogues as potential monomer diluents to improve the mechanical properties of light-cured composite resins. Dent Mater 2005;21:823-830.
  23. Tay FR, Pashley DH. Have dentin adhesives become too hydrophilic? J Can Dent Assoc 2003;69: 726-731.
  24. Ito S, Hashimoto M, Wadgaonkar B, Svizero N, Carvalho RM, Yiu C, Rueggeberg FA, Foulger S, Saito T, Nishitani Y, Yoshiyama M, Tay FR, Pashley DH. Effects of resin hydrophilicity on water sorption and changes in modulus of elasticity. Biomaterials 2005;26:6449-6459.
  25. Nishitani Y, Yoshiyama M, Donnelly AM, Agee KA, Sword J, Tay FR, Pashley DH. Effects of resin hydrophilicity on dentin bond strength. J Dent Res 2006;85:1016-1021.
  26. Asmussen E. Restorative resins: hardness and strength vs. quantity of remaining double bonds. Scand J Dent Res 1982;90:484-489.
  27. Seong SR, Seo DK, Lee IB, Son HH, Cho BH. Effect of exponential curing of composite resin on the microtensile dentin bond strength of adhesives. J Kor Acad Cons Dent 2010;35:125-133.
  28. Shin HJ, Song CK, Park SH, Kim JW, Cho KM. Physical properties of different self-adhesive resin cements and their shear bond strength on lithium disilicate ceramic and dentin. J Kor Acad Cons Dent 2009;34:184-191.
  29. Ko EJ, Shin DH. Difference in bond strength according to filling techniques and cavity walls in box-type occlusal composite resin restoration. J Kor Acad Cons Dent 2009;34:350-356.
  30. Erickson RL. Surface interactions of dentin adhesive materials. Oper Dent 1992;(Supplement 5):81-94.
  31. Asmussen E, Uno S. Solubility parameters, fractional polarities, and bond strengths of some intermediary resins used in dentin bonding. J Dent Res 1993;72:558-565.
  32. Miller RG, Bowles CQ, Chappelow CC, Eick JD. Application of solubility parameter theory to dentin-bonding systems and adhesive strength correlations. J Biomed Mater Res 1998;41:237-243.<237::AID-JBM8>3.0.CO;2-J
  33. Hildebrand JH. The solubility of non-electrolytes. New York: Reinhold; 1936.
  34. Vaidyanathan TK, Vaidyanathan J. Recent advances in the theory and mechanism of adhesive resin bonding to dentin: a critical review. J Biomed Mater Res B App Biomater 2009:88:558-578.
  35. Asmussen E, Hansen EK, Peutzfeldt A. Influence of the solubility parameter of intermediary resin on the effectiveness of the Gluma bonding system. J Dent Res 1991;70:1290-1293.
  36. Finger WJ, Inoue M, Asmussen E. Effect of wettability of adhesive resins on bonding to dentin. Am J Dent 1994;7:35-38.