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New Dental Composites Containing Multimethacrylate Derivatives of Bile Acids: A Comparative Study with Commercial Monomers

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    Research Article

    New Dental Composites Containing Multimethacrylate Derivatives of Bile Acids: A Comparative Study with Commercial Monomers
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    Département de Chimie, Université de Montréal, C.P. 6128, Succ. Centre-ville, Montreal, Quebec H3C 3J7, Canada, and Department of Chemistry, Shanxi University, Taiyuan, Shanxi 030006, China
    * To whom correspondence should be addressed. E-mail: [email protected]
    †Université de Montréal.
    ‡Shanxi University.
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    ACS Applied Materials & Interfaces

    Cite this: ACS Appl. Mater. Interfaces 2009, 1, 4, 824–832
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    https://doi.org/10.1021/am8002395
    Published March 12, 2009
    Copyright © 2009 American Chemical Society
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    Abstract

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    We have prepared multifunctional methacrylate derivatives of bile acids as cross-linkable monomers for use in dental composites. By modifying the chemical structure of the monomers, we were able to vary the viscosity, hydrophobicity, and reactivity and have studied the effect of these parameters on the conversion of the monomers, the shrinkage during polymerization, and the mechanical properties of the resulting polymers and composites. Materials containing these new monomers generally had physical, thermal, and mechanical properties comparable to those containing the commonly used dental monomers BisGMA or UDMA and had lower polymerization shrinkage. The multimethacrylate derivatives of cholic acid, which are known to be less cytotoxic than BisGMA and UDMA, are shown to be promising materials for dental applications.

    Copyright © 2009 American Chemical Society

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    Supporting Information

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    FTIR spectra of filler particles confirming the presence of methacrylate groups, thermogravimetric analyses of silanized fillers to determine the extent of silanization, and thermogravimetric analysis of a TEGDMA homopolymer to determine the onset of thermal decomposition. This material is available free of charge via the Internet at http://pubs.acs.org.

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    This article is cited by 25 publications.

    1. Eric Habib, Ruili Wang, Yazi Wang, Meifang Zhu, and X. X. Zhu . Inorganic Fillers for Dental Resin Composites: Present and Future. ACS Biomaterials Science & Engineering 2016, 2 (1) , 1-11. https://doi.org/10.1021/acsbiomaterials.5b00401
    2. Jiawei Zhang, Matthias J. N. Junk, Juntao Luo, Dariush Hinderberger and X. X. Zhu . 1,2,3-Triazole-Containing Molecular Pockets Derived from Cholic Acid: The Influence of Structure on Host−Guest Coordination Properties. Langmuir 2010, 26 (16) , 13415-13421. https://doi.org/10.1021/la102158a
    3. Madiana Magalhães Moreira, Ana Larissa da Silva, Rita de Cássia Sousa Pereira, Lucas Renan Rocha da Silva, Victor Pinheiro Feitosa, Diego Lomonaco. Effect of replacing Bis-GMA with a biobased trimethacrylate on the physicochemical and mechanical properties of experimental resin composites. Clinical Oral Investigations 2024, 28 (11) https://doi.org/10.1007/s00784-024-05959-x
    4. Madiana Magalhães Moreira, Ana Larissa da Silva, Rita de Cássia Sousa Pereira, Lucas Renan Rocha da Silva, Victor Pinheiro Feitosa, Diego Lomonaco. Effect of replacing Bis-GMA by a biobased trimethacrylate on the physicochemical and mechanical properties of experimental resin composites. 2024https://doi.org/10.21203/rs.3.rs-4648523/v1
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    8. Yazi Wang, Meifang Zhu, X.X. Zhu. Functional fillers for dental resin composites. Acta Biomaterialia 2021, 122 , 50-65. https://doi.org/10.1016/j.actbio.2020.12.001
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    10. Eric Habib, Ruili Wang, X.X. Zhu. Correlation of resin viscosity and monomer conversion to filler particle size in dental composites. Dental Materials 2018, 34 (10) , 1501-1508. https://doi.org/10.1016/j.dental.2018.06.008
    11. Ana M. Herrera‐González, José Abraham González‐López, Carlos E. Cuevas‐Suárez, Miguel A. García‐Castro, M. Vargas‐Ramírez. Formulation and evaluation of dental composite resins with allylcarbonate monomer as eluent for Bis‐GMA. Polymer Composites 2018, 39 (S1) https://doi.org/10.1002/pc.24453
    12. Seunghan Shin, Young-Jae Kim, Mai Toan, Jong-Gyu Kim, TanPhat Nguyen, Jin Ku Cho. Property enhancement of dental composite prepared with an isosorbide-based photocurable compound by mixing with TEGDMA. European Polymer Journal 2017, 92 , 338-345. https://doi.org/10.1016/j.eurpolymj.2017.05.009
    13. Gedalias C. Martim, Carmem S. Pfeifer, Emerson M. Girotto. Novel urethane-based polymer for dental applications with decreased monomer leaching. Materials Science and Engineering: C 2017, 72 , 192-201. https://doi.org/10.1016/j.msec.2016.11.050
    14. Alexander J. Cunningham, X.X. Zhu. Polymers made of bile acids: from soft to hard biomaterials. Canadian Journal of Chemistry 2016, 94 (8) , 659-666. https://doi.org/10.1139/cjc-2016-0068
    15. Meng Zhang, Satu Strandman, Karen C. Waldron, X. X. Zhu. Supramolecular hydrogelation with bile acid derivatives: structures, properties and applications. Journal of Materials Chemistry B 2016, 4 (47) , 7506-7520. https://doi.org/10.1039/C6TB02270G
    16. Mei Yin, Sen Guo, Fang Liu, Jingwei He. Synthesis of fluorinated dimethacrylate monomer and its application in preparing Bis-GMA free dental resin. Journal of the Mechanical Behavior of Biomedical Materials 2015, 51 , 337-344. https://doi.org/10.1016/j.jmbbm.2015.07.025
    17. Sebastian Reinelt, Monir Tabatabai, Norbert Moszner, Urs Karl Fischer, Andreas Utterodt, Helmut Ritter. Synthesis and Photopolymerization of Thiol‐Modified Triazine‐Based Monomers and Oligomers for the Use in Thiol‐Ene‐Based Dental Composites. Macromolecular Chemistry and Physics 2014, 215 (14) , 1415-1425. https://doi.org/10.1002/macp.201400174
    18. Weijian Ye, Yun Li, Zhengquan Zhou, Xingbin Wang, Juan Yao, Juanjuan Liu, Cunde Wang. Synthesis and antibacterial activity of new long-chain-alkyl bile acid-based amphiphiles. Bioorganic Chemistry 2013, 51 , 1-7. https://doi.org/10.1016/j.bioorg.2013.08.003
    19. Shiv P. Mantri, Sneha S. Mantri. Management of Shrinkage Stresses in Direct Restorative Light‐Cured Composites: A Review. Journal of Esthetic and Restorative Dentistry 2013, 25 (5) , 305-313. https://doi.org/10.1111/jerd.12047
    20. Jinrong Lu, Chulong Liu, Jun Hu, Yong Ju. Synthesis and micellar mimic properties of bile acid trimers. Bioorganic & Medicinal Chemistry Letters 2013, 23 (5) , 1302-1305. https://doi.org/10.1016/j.bmcl.2012.12.102
    21. K. Lizenboim, H. Dodiuk, N. Iuster, T. Kidan, I. Suvorov, S. Kenig, B. Zalsman. Bisphenol-A free dental polymeric materials. Journal of Adhesion Science and Technology 2013, 27 (4) , 354-370. https://doi.org/10.1080/01694243.2012.705540
    22. Norbert Moszner, Thomas Hirt. New polymer‐chemical developments in clinical dental polymer materials: Enamel–dentin adhesives and restorative composites. Journal of Polymer Science Part A: Polymer Chemistry 2012, 50 (21) , 4369-4402. https://doi.org/10.1002/pola.26260
    23. Christine Lavigueur, X. X. Zhu. Recent advances in the development of dental composite resins. RSC Adv. 2012, 2 (1) , 59-63. https://doi.org/10.1039/C1RA00922B
    24. N.B. Cramer, J.W. Stansbury, C.N. Bowman. Recent Advances and Developments in Composite Dental Restorative Materials. Journal of Dental Research 2011, 90 (4) , 402-416. https://doi.org/10.1177/0022034510381263
    25. Jack L. Ferracane. Resin composite—State of the art. Dental Materials 2011, 27 (1) , 29-38. https://doi.org/10.1016/j.dental.2010.10.020
    26. JiaWei Zhang, XiaoXia Zhu. Biomaterials made of bile acids. Science in China Series B: Chemistry 2009, 52 (7) , 849-861. https://doi.org/10.1007/s11426-009-0124-x
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    ACS Applied Materials & Interfaces

    Cite this: ACS Appl. Mater. Interfaces 2009, 1, 4, 824–832
    Click to copy citationCitation copied!
    https://doi.org/10.1021/am8002395
    Published March 12, 2009
    Copyright © 2009 American Chemical Society
    Request reuse permissions

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