Dental Materials
Volume 25, Issue 3 , Pages 302-313 , March 2009

Synthesis and evaluation of modified urethane dimethacrylate resins with reduced water sorption and solubility

  • Ronald E. Kerby

      Affiliations

    • Division of Restorative and Prosthetic Dentistry, The Ohio State University, College of Dentistry, Columbus, OH 43210, United States
    • Corresponding Author InformationCorresponding author at: Division of Restorative and Prosthetic Dentistry, The Ohio State University, College of Dentistry, Room 3005B, 305 West 12th Avenue, Columbus, OH 43210, United States. Tel.: +1 614 292 0880; fax: +1 614 292 9422.
  • ,
  • Lisa A. Knobloch

      Affiliations

    • Division of Restorative and Prosthetic Dentistry, The Ohio State University, College of Dentistry, Columbus, OH 43210, United States
  • ,
  • Scott Schricker

      Affiliations

    • Division of Restorative and Prosthetic Dentistry, The Ohio State University, College of Dentistry, Columbus, OH 43210, United States
  • ,
  • Benjamin Gregg

      Affiliations

    • Private Orthodontic Practice, Ashland, OH, United States

Received 12 May 2008 ,Revised 8 July 2008 ,Accepted 17 July 2008.

References 

  1. Siderdou I, Tserki V, Papanastasiou G. Effect of chemical structure on degree of conversion in light-cured dimethacrylate-based dental resins. Biomaterials. 2002;23:1819–1829
  2. Shobha HK, Sankarapandian M, Kalachandra S, Taylor DF, McGrath JE. Structure property relationship among novel dental composite matrix resins. J Mater Sci: Mater Med. 1997;8:385–389
  3. Khatri CA, Stansbury JW, Shultheisz CR, Antonucci JM. Synthesis, characaterization and evaluation of urethane derivatives of Bis-GMA. Dent Mater. 2003;19:584–588
  4. Stansburgy JW, Antonucci JM. Dimethacrylate monomers with varied fluorine contents and distributions. Dent Mater. 1999;15:166–173
  5. Kerby RE, Tiba A, Knobloch LA, Schricker SR, Tiba O. Fracture toughness of modified dental resin systems. J Oral Rehab. 2003;30:780–784
  6. Wang G, Culbertson BM, Xie D, Seghi RR. Effect of fluorinated triethylene glycol dimethacrylate on the properties of unfilled, light cured dental resins. J Macromol Sci Pure Appl Chem. 1999;36:237–252
  7. Siderdou I, Tserki V, Papanastasiou G. Study of water sorption, solubility and modulus of elasticity of light cured dimethacrylate resins. Biomaterials. 2003;24:655–665
  8. Foster J, Walker RJ. Dental Filling Materials. US Patent 3,825,518; 1974.
  9. Peutzfeldt A. Resin composites in dentistry: the monomer systems. Eur J Oral Sci. 1997;105:97–116
  10. Beatty MW, Swartz ML, Moore BK, Phillips RW, Roberts TA. Effect of crosslinking agent content, monomer functionality, and repeat unit chemistry on properties of unfilled resins. J Biomed Mater Res. 1993;27:403–413
  11. Asmussen E, Peutzfeldt A. Mechanical properties of heat treated restorative resins for use in the inlay/onlay techniques. Scand J Dent Res. 1990;98:564–567
  12. Renz S, Dickens B. NIR-spectroscopic investigation of water sorption characteristics of dental resins and composites. J Biomed Mater Res. 1991;25:1231–1248
  13. Braden M, Davy KW. Water absorption characteristics of some unfilled resins. Biomaterials. 1986;7:474–475
  14. Ferracane JL. Hygroscopic and hydrolytic effects in dental polymer networks. Dent Mater. 2006;22:211–222
  15. Örtengren U, Wellendorf H, Karlsson , Ruyter IE. Water sorption and solubility of dental composites and identification of monomers released in an aqueous environment. J Oral Rehab. 2001;28:1106–1115
  16. Tanaka J, Hashimoto T, Stansbury JW, Antonucci JM, Suzuki K. Polymer properties on resins composed of UDMA and methacrylates with the carboxyl group. Dent Mater J. 2001;20:206–215
  17. Matsukawa S, Hayakawa T, Nemoto K. Development of high-toughness resin for dental applications. Dent Mater. 1994;10:343–346
  18. Atai M, Ahmadi M, Babanzadeh S, Watts DC. Synthesis, characterization, shrinkage and curing kinetics of a new low-shrinkage urethane dimethacrylate monomer for dental applications. Dent Mater. 2007;23:1030–1041
  19. Takitani S, Asabe Y, Kato T, Suzuki M, Uena Y. Spectrodensitometric determination of trichothecene mycotoxins with 4-(p-nitrobenzyl) pyridine on silica gel thin-layer chromatograms. J Chromatogr. 1979;172:335–342
  20. Moszner N, Völkel T, Fischer UK, Klester A, Rheinberger V. Synthesis and polymerization of new multi-functional urethane methacrylates. Angew Makromol Chem. 1999;265:31–35
  21. Kerby RE, Knobloch L, Lilley H, Schricker S and Culbertson B. Flexural strength and modulus of aromatic and aliphatic urethane dimethacrylates. J. Dent Res 2002 [Special Issue, Abstr. No. 0061].
  22. ADA. New American Dental Association Specification No. 27 for direct filling resins. J Am Dent Assoc 1977;94:1191–4.
  23. Van Krevelen DW. Properties of polymers. Their correlation with chemical structure; their estimation and prediction from additive group contribution. 3rd ed.. Amsterdam: Elsevier Science Publishers, BV; 1990;p. 196–7
  24. Barton AFM. Calculated cohesion parameters. CRC handbook of solubility parameters and other cohesion parameters. 2nd ed.. Boca Raton, FL: CRC Press; 1991;p. 157–93 [Chapter 6]
  25. Pashley DH, Tay FR, Carvalho RM, Rueggeberg FA, Agee KA, Carrilho M, et al. From dry bonding to water wet bonding to ethanol-wet bonding—a review of the interactions between dentin matrix an solvated resins using a macro-model of the hybrid layer. Am J Dent. 2007;20:7–21
  26. Fan PL, Edahl A, Leung RL, Stanford JW. Alternative interpretation of water sorption values of composite resin. J Dent Res. 1985;64:78–80
  27. Kanerva L, Estlander T, Jolanki R. Dental problems. In:  Guin JD editors. Handbook of contact dermatitis. New York: McGraw-Hill; 1995;p. 297–432
  28. Bellenger V, Verdu J, Morel E. Structure-property relationships of cross-linked epoxide-amine systems based on epoxide aramine mixtures II. Water sorption and diffusion. J Mater Sci. 1989;24:63–68
  29. Pace RJ, Datyner A. Model of sorption of simple molecules in polymers. J Polym Sci, Polym Phys Ed. 1980;18:1103–1124
  30. Ferracane JL. Water sorption and solubility of experimental dental composites. Polym Preprints. 1997;38:116–117
  31. Venz S, Dickens B. NIR-spectroscopic investigation of water sorption characteristics of dental resins and composites. J Biomed Mater Res. 1991;25:1231–1248
  32. Moshen NM, Craig RG, Filisko FE. The effects of moisture on the dielectric relaxation of urethane dimethacrylate polymer and composites. J Oral Rehab. 2001;28:376–392
  33. Puffer R, Sebenda J. On the structure and properties of polyamides XXVII. The mechanism of water sorption in polyamides. J Polym Sci: Part C. 1967;16:79
  34. Yifu D, Liu M, Li S, Zhang S, Zhou WF, Wang B. Contributions of the side groups to the characteristics of water sorption in cured epoxy resins. Macromol Chem Phys. 2001;202:2681–2685
  35. Merdas I, Tcharkhtchi A, Thominette F, Verdu J, Dean K, Cook W. Water sorption by uncrosslinked polymers, networks, and IPNs having medium to high polarity. Polymer. 2002;43:4619–4625
  36. Fluid properties. Handbook of chemistry and physics. 88th ed.. Boca Raton, FL: CRC Press; 2007;p. 135–57 [Section 6]
  37. Oysaed H, Ruyter IE, Sjovik-Kleven IJ. Release of formaldehyde from dental composites. J Dent Res. 1988;67:1289–1294
  38. Ferracane JL, Condon JR. Rate of elution of leachable components from composite. Dent Mater. 1990;6:282–287
  39. Watts DC. Reaction kinetics and mechanics in photo-polymerized networks. Dent Mater. 2005;21:27–35
  40. March J. Advanced organic chemistry: reactions, mechanisms and structure. 5th ed.. John Wiley and Sons; 2001;p. 131–89
  41. Asmussen E. Restorative resin-hardness and strength vs. quantity of remaining double-bonds. Scand J Dent Res. 1982;90:484–489
  42. Ferracane JL, Greener EH. The effect of resin formulation of the degree of conversion and mechanical properties of dental restorative resins. J Biomed Mater Res. 1986;20:121–131
  43. Dlubek G, Bamford D, Rodriguez-Gonzalez A, Bornemann S, Stejny J, Schade B, et al. Free volume, glass transition, and degree of branching in metallocene-based propylene/α-olefin copolymers: positron lifetime density and differential scanning calorimeter studies. J Polym Sci: Part B: Polym Phys. 2002;40:434–453
  44. Ayala D, Lozano A, De Abajo J, De La Campa J. Synthesis and characterization of novel polyimides with bulky pendant groups. J Polym Sci A: Polym Chem. 1999;37:805–814
  45. Atsuta M, Nakabayashi N, Masuhara E. Hard methacrylic polymers. II. Copolymers of methyl methacrylate and 2,2 di(4-methacryloxyphenyl) propane. J Biomed Mater Res. 1971;5:183–195
  46. Kawaguchi M, Fukushima T, Miyazaki K, Horibe I, Habu T, Sawamura N. Synthesis and physical preparation of aromatic dimethacylate copolymers. Dent Mater J. 1984;3:272–279
  47. Arendt VD, Logan RE, Saxon R. m- and p-TMXDI: two new isocyanates for the polyurethane industry. J Cell Plast. 1982;8:376–383
  48. Nishitani Y, Yoshiyama M, Hosaka K, Tagami J, Donnelly A, Carrilho M, et al. Use of Hoy's solubility parameters to predict water sorption/solubility of experimental primers and adhesives. Eur J Oral Sci. 2007;115:81–86
  49. Yoshiyama M, Tay FR, Pashley DH. Effect of resin hydrophilicity on water sorption and changes in modulus of elasticity. Biomaterials. 2005;26:6449–6459
  50. Hosaka K, Tagami J, Nishitani Y, Yoshiyama M, Carrilho M, Tay FR, et al. Effect of wet vs. dry testing on the mechanical properties of hydrophilic self-etching primer polymers. Eur J Oral Sci. 2007;115:239–245
  51. Yiu CKY, King NM, Carrilho MR, Sauro S, Rueggeberg FA, Prati C, et al. Effect of resin hydrophilicity and temperature on water sorption of dental adhesive resins. Biomaterials. 2006;27:1695–1703
  52. Ito S, Hashimoto M, Wadgaonkar B, Svizero N, Carvalho RM, Yiu C, et al. Effects of resin hydrophilicity on water sorption and changes on modules of elasticity. Biomaterials. 2005;26:6449–6459

PII: S0109-5641(08)00200-5

doi: 10.1016/j.dental.2008.07.009

Dental Materials
Volume 25, Issue 3 , Pages 302-313 , March 2009