Original Research Report
Synthesis and evaluation of novel dental monomer with branched carboxyl acid group
Linyong Song,
Qiang Ye,
Xueping Ge,
Anil Misra,
Jennifer S. Laurence,
Cynthia L. Berrie,
Paulette Spencer,
Linyong Song
Bioengineering Research Center, University of Kansas, Lawrence, Kansas, 66045
School of Chemistry and Chemical Engineering, Anhui University, Hefei, China
Search for more papers by this authorCorresponding Author
Qiang Ye
Bioengineering Research Center, University of Kansas, Lawrence, Kansas, 66045
Correspondence to: Q. Ye (e-mail: [email protected]) and P. Spencer (e-mail: [email protected])Search for more papers by this authorXueping Ge
Bioengineering Research Center, University of Kansas, Lawrence, Kansas, 66045
Search for more papers by this authorAnil Misra
Bioengineering Research Center, University of Kansas, Lawrence, Kansas, 66045
Department of Civil Engineering, University of Kansas, Lawrence, Kansas, 66045
Search for more papers by this authorJennifer S. Laurence
Department of Pharmaceutical Chemistry, University of Kansas, Lawrence, Kansas, 66047
Search for more papers by this authorCynthia L. Berrie
Department of Chemistry, University of Kansas, Lawrence, Kansas, 66045
Search for more papers by this authorPaulette Spencer
Bioengineering Research Center, University of Kansas, Lawrence, Kansas, 66045
Department of Mechanical Engineering, University of Kansas, Lawrence, Kansas, 66045
Search for more papers by this authorLinyong Song,
Qiang Ye,
Xueping Ge,
Anil Misra,
Jennifer S. Laurence,
Cynthia L. Berrie,
Paulette Spencer,
Linyong Song
Bioengineering Research Center, University of Kansas, Lawrence, Kansas, 66045
School of Chemistry and Chemical Engineering, Anhui University, Hefei, China
Search for more papers by this authorCorresponding Author
Qiang Ye
Bioengineering Research Center, University of Kansas, Lawrence, Kansas, 66045
Correspondence to: Q. Ye (e-mail: [email protected]) and P. Spencer (e-mail: [email protected])Search for more papers by this authorXueping Ge
Bioengineering Research Center, University of Kansas, Lawrence, Kansas, 66045
Search for more papers by this authorAnil Misra
Bioengineering Research Center, University of Kansas, Lawrence, Kansas, 66045
Department of Civil Engineering, University of Kansas, Lawrence, Kansas, 66045
Search for more papers by this authorJennifer S. Laurence
Department of Pharmaceutical Chemistry, University of Kansas, Lawrence, Kansas, 66047
Search for more papers by this authorCynthia L. Berrie
Department of Chemistry, University of Kansas, Lawrence, Kansas, 66045
Search for more papers by this authorPaulette Spencer
Bioengineering Research Center, University of Kansas, Lawrence, Kansas, 66045
Department of Mechanical Engineering, University of Kansas, Lawrence, Kansas, 66045
Search for more papers by this authorAbstract
To enhance the water miscibility and increase the mechanical properties of dentin adhesives, a new glycerol-based monomer with vinyl and carboxylic acid, 4-((1,3-bis(methacryloyloxy)propan-2-yl)oxy)-2-methylene-4-oxobutanoic acid (BMPMOB), was synthesized and characterized. Dentin adhesive formulations containing 2-hydroxyethyl methacrylate (HEMA), 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy) phenyl]propane (BisGMA), and BMPMOB were characterized with regard to real-time photopolymerization behavior, water sorption, dynamic mechanical analysis, and microscale three-dimensional internal morphologies and compared with HEMA/BisGMA controls. The experimental adhesive copolymers showed higher glass transition temperature and rubbery moduli, as well as improved water miscibility compared to the controls. The enhanced properties of the adhesive copolymers indicated that BMPMOB is a promising comonomer for dental restorative materials. © 2014 Wiley Periodicals, Inc. J Biomed Mater Res Part B: Appl Biomater, 102B: 1473–1484, 2014.
REFERENCES
- 1 Tjaderhane L, Nascimento FD, Breschi L, Mazzoni A, Tersariol ILS, Geraldeli S, Tezvergil-Mutluay A, Carrilho M, Carvalho RM, Tay FR, Pashley DH. Strategies to prevent hydrolytic degradation of the hybrid layer—A review. Dent Mater 2013; 29(10): 999–1011.
- 2 Burrow MF, Satoh M, Tagami J. Dentin bond durability after three years using a dentin bonding agent with and without priming. Dent Mater 1996; 12(5–6): 302–307.
- 3 Hashimoto M, Ohno H, Kaga M, Endo K, Sano H, Oguchi H. In vivo degradation of resin-dentin bonds in humans over 1 to 3 years. J Dent Res 2000; 79(6): 1385–1391.
- 4 Hashimoto M, Ohno H, Sano H, Tay FR, Kaga M, Kudou Y, Oguchi H, Araki Y, Kubota M. Micromorphological changes in resin–dentin bonds after 1 year of water storage. J Biomed Mater Res 2002; 63(3): 306–311.
- 5 Sano H, Yoshikawa T, Pereira PNR, Kanemura N, Morigami M, Tagami J, Pashley DH. Long-term durability of dentin bonds made with a self-etching primer, in vivo. J Dent Res 1999; 78(4): 906–911.
- 6 Spencer P, Swafford JR. Unprotected protein at the dentin–adhesive interface. Quintessence Int 1999; 30(7): 501–507.
- 7 Spencer P, Wang Y, Bohaty B. Interfacial chemistry of moisture-aged class II composite restorations. J Biomed Mater Res Part B: Appl Biomater 2006; 77B(2): 234–240.
- 8 Spencer P, Wang Y, Walker MP, Wieliczka DM, Swafford JR. Interfacial chemistry of the dentin/adhesive bond. J Dent Res 2000; 79(7): 1458–1463.
- 9 Wang Y, Spencer P. Hybridization efficiency of the adhesive/dentin interface with wet bonding. J Dent Res 2003; 82(2): 141–145.
- 10 Wang Y, Spencer P. Physicochemical interactions at the interfaces between self-etch adhesive systems and dentine. J Dent 2004; 32(7): 567–579.
- 11 Wang Y, Spencer P. Overestimating hybrid layer quality in polished adhesive/dentin interfaces. J Biomed Mater Res Part A 2004; 68A(4): 735–746.
- 12 Wang Y, Spencer P. Continuing etching of an all-in-one adhesive in wet dentin tubules. J Dent Res 2005; 84(4): 350–354.
- 13 Wang Y, Spencer P, Yao XM. Micro-Raman imaging analysis of monomer/mineral distribution in intertubular region of adhesive/dentin interfaces. J Biomed Opt 2006; 11(2).
- 14 Moszner N, Hirt T. New polymer-chemical developments in clinical dental polymer materials: Enamel–dentin adhesives and restorative composites. J Polym Sci Part A: Polym Chem 2012; 50(21): 4369–4402.
- 15 Moszner N, Salz U. New developments of polymeric dental composites. Prog Polym Sci 2001; 26(4): 535–576.
- 16 Moszner N, Salz U. Recent developments of new components for dental adhesives and composites. Macromol Mater Eng 2007; 292(3): 245–271.
- 17 Moszner N, Salz U, Zimmermann J. Chemical aspects of self-etching enamel–dentin adhesives: A systematic review. Dent Mater 2005; 21(10): 895–910.
- 18 Schwartz RS, Fransman R. Adhesive dentistry and endodontics: Materials, clinical strategies and procedures for restoration of access cavities: A review. J Endod 2005; 31(3): 151–165.
- 19 Vaidyanathan TK, Vaidyanathan J. Recent advances in the theory and mechanism of adhesive resin bonding to dentin: A critical review. J Biomed Mater Res Part B: Appl Biomater 2009; 88B(2): 558–578.
- 20 Park JG, Ye Q, Topp EM, Spencer P. Enzyme-catalyzed hydrolysis of dentin adhesives containing a new urethane-based trimethacrylate monomer. J Biomed Mater Res Part B: Appl Biomater 2009; 91B(2): 562–571.
- 21 Park JG, Ye Q, Topp EM, Kostoryz EL, Wang Y, Kieweg SL, Spencer P. Preparation and properties of novel dentin adhesives with esterase resistance. J Appl Polym Sci 2008; 107(6): 3588–3597.
- 22 Bowman CN, Lovell LG, Syrpes DS, Stansbury JW. Dimethacrylate dental resins: The effect of comonomer on the polymerization kinetics. In: Abstracts of Papers of the American Chemical Society, Vol. 246; 1998. pp U125–U125.
- 23 Moszner N. New monomers for dental application. Macromol Symp 2004; 217: 63–75.
- 24 Spencer P, Wang Y. Adhesive phase separation at the dentin interface under wet bonding conditions. J Biomed Mater Res 2002; 62(3): 447–456.
- 25 Tay FR, Pashley DH, Kapur RR, Carrilho MRO, Hur YB, Garrett LV, Tay KCY. Bonding BisGMA to dentin—A proof of concept for hydrophobic dentin bonding. J Dent Res 2007; 86(11): 1034–1039.
- 26 Liu Y, Tjaderhane L, Breschi L, Mazzoni A, Li N, Mao J, Pashley DH, Tay FR. Limitations in bonding to dentin and experimental strategies to prevent bond degradation. J Dent Res 2011; 90(8): 953–968.
- 27 Kostoryz EL, Dharmala K, Ye Q, Wang Y, Huber J, Park JG, Snider G, Katz JL, Spencer P. Enzymatic biodegradation of HEMA/BisGMA adhesives formulated with different water content. J Biomed Mater Res Part B: Appl Biomater 2009; 88B(2): 394–401.
- 28 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(11): 1016–1021.
- 29 Park JG, Ye Q, Topp EM, Misra A, Spencer P. Water sorption and dynamic mechanical properties of dentin adhesives with a urethane-based multifunctional methacrylate monomer. Dent Mater 2009; 25(12): 1569–1575.
- 30 Park J, Ye Q, Singh V, Kieweg SL, Misra A, Spencer P. Synthesis and evaluation of novel dental monomer with branched aromatic carboxylic acid group. J Biomed Mater Res Part B: Appl Biomater 2012; 100B(2): 569–576.
- 31 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(6): 824–831.
- 32 Ye Q, Park J, Topp E, Spencer P. Effect of photoinitiators on the in vitro performance of a dentin adhesive exposed to simulated oral environment. Dent Mater 2009; 25(4): 452–458.
- 33 Parthasarathy R, Misra A, Park J, Ye Q, Spencer P. Diffusion coefficients of water and leachables in methacrylate-based crosslinked polymers using absorption experiments. J Mater Sci: Mater Med 2012; 23(5): 1157–1172.
- 34 Park J, Ye Q, Topp EM, Misra A, Kieweg SL, Spencer P. Effect of photoinitiator system and water content on dynamic mechanical properties of a light-cured bisGMA/HEMA dental resin. J Biomed Mater Res Part A 2010; 93A(4): 1245–1251.
- 35 Park JG, Ye Q, Topp EM, Lee CH, Kostoryz EL, Misra A, Spencer P. Dynamic mechanical analysis and esterase degradation of dentin adhesives containing a branched methacrylate. J Biomed Mater Res Part B: Appl Biomater 2009; 91B(1): 61–70.
- 36
Anseth KS,
Goodner MD,
Reill MA,
Kannurpatti AR,
Newman SM,
Bowman CN. The influence of comonomer composition on dimethacrylate resin properties for dental composites. J Dent Res 1996; 75(8): 1607–1612.
10.1177/00220345960750081301 Google Scholar
- 37 Moszner N, Volkel T, Zeuner F, Rheinberger V. Radical ring-opening monomers for dental composites. In: Abstracts of Papers of the American Chemical Society, Vol. 214; 1997. pp 10-POLY.
- 38 Salz U, Burtscher P, Vogel K, Moszner N, Rheinberger V. New adhesive monomers for dental application. In: Abstracts of Papers of the American Chemical Society, Vol. 214; 1997. pp 175-POLY.
- 39 Pavlinec J, Zeuner F, Angermann J, Moszner N. Monomers for adhesive polymers, 5-synthesis and radical polymerization behavior of 2,4,6-trimethylphenyl 2,4-(dihydroxyphosphoryl)-2-oxa-butyl acrylate. Macromol Chem Phys 2005; 206(18): 1878–1886.
- 40 El-Deeb HA, Al Sherbiney HH, Mobarak EH. Bond durability of adhesives containing modified-monomer with/without-fluoride after aging in artificial saliva and under intrapulpal pressure simulation. Oper Dent 2013; 38(1): 48–56.
- 41 Atai M, Nekoomanesh M, Hashemi SA, Yeganeh H. Synthesis and characterization of BTDA-based dimethacrylate dental adhesive monomer and its interaction with Ca2+ ions. J Appl Polym Sci 2002; 86(13): 3246–3249.
- 42 Solhi L, Atai M, Nodehi A, Imani M, Ghaemi A, Khosravi K. Poly(acrylic acid) grafted montmorillonite as novel fillers for dental adhesives: Synthesis, characterization and properties of the adhesive. Dent Mater 2012; 28(4): 369–377.
- 43 Sideridou I, Tserki V, Papanastasiou G. Effect of chemical structure on degree of conversion in light-cured dimethacrylate-based dental resins. Biomaterials 2002; 23(8): 1819–1829.
- 44 Park J, Eslick J, Ye Q, Misra A, Spencer P. The influence of chemical structure on the properties in methacrylate-based dentin adhesives. Dent Mater 2011; 27(11): 1086–1093.
- 45 Santerre JP, Shajii L, Leung BW. Relation of dental composite formulations to their degradation and the release of hydrolyzed polymeric-resin-derived products. Crit Rev Oral Biol Med 2001; 12(2): 136–151.
- 46 Ye Q, Spencer P, Wang Y, Misra A. Relationship of solvent to the photopolymerization process, properties, and structure in model dentin adhesives. J Biomed Mater Res Part A 2007; 80A(2): 342–350.
- 47
Young JS,
Kannurpatti AR,
Bowman CN. Effect of comonomer concentration and functionality on photopolymerization rates, mechanical properties and heterogeneity of the polymer. Macromol Chem Phys 1998; 199(6): 1043–1049.
10.1002/(SICI)1521-3935(19980601)199:6<1043::AID-MACP1043>3.0.CO;2-Z CAS Web of Science® Google Scholar
- 48 Gao BT, Lin H, Zheng G, Xu YX, Yang JL. Comparison between a silorane-based composite and methacrylate-based composites: Shrinkage characteristics, thermal properties, gel point and vitrification point. Dent Mater J 2012; 31(1): 76–85.
- 49 Pavlinec J, Moszner N. Monomers for adhesive polymers, 8(a) crosslinking polymerization of selected N-substituted bis(acrylamide)s for dental filling materials. J Appl Polym Sci 2009; 113(5): 3137–3145.
- 50
Odian G. Principles of Polymerization, 4th ed. Hoboken, NJ: Wiley.; 2004.
10.1002/047147875X Google Scholar
- 51 Allen PEM, Simon GP, Williams DRG, Williams EH. Dynamic–mechanical properties and cross-polarized, proton-enhanced, magic angle spinning C-13 NMR time constants of polyoligo(ethylene glycol) dimethacrylates. Macromolecules 1989; 22(2): 809–816.
- 52 Simon GP, Allen PEM, Bennett DJ, Williams DRG, Williams EH. Nature of residual unsaturation during cure of dimethacrylates examined by cppemas C-13 NMR and simulation using a kinetic gelation model. Macromolecules 1989; 22(9): 3555–3561.
- 53 Simon GP, Allen PEM, Williams DRG. Properties of dimethacrylate copolymers of varying cross-link density. Polymer 1991; 32(14): 2577–2587.
- 54 Ye Q, Wang Y, Spencer P. Nanophase separation of polymers exposed to simulated bonding conditions. J Biomed Mater Res Part B: Appl Biomater 2009; 88B(2): 339–348.
- 55 Ye Q, Park JG, Topp E, Wang Y, Misra A, Spencer P. In vitro performance of nano-heterogeneous dentin adhesive. J Dent Res 2008; 87(9): 829–833.
- 56 Ito S, Hashimoto M, Wadgaonkar B, Svizero N, Carvalho RM, Yiu C, Rueggeberg FA, Foulger S, Saito T, Nishitani Y, et al. Effects of resin hydrophilicity on water sorption and changes in modulus of elasticity. Biomaterials 2005; 26(33): 6449–6459.
