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Evaluation of a photo-initiated copper(I)-catalyzed azide-alkyne cycloaddition polymer network with improved water stability and high mechanical performance as an ester-free dental restorative.

Authors
  • Wang, Xiance1
  • Gao, Guangzhe2
  • Song, Han Byul1
  • Zhang, Xinpeng1
  • Stansbury, Jeffrey W3
  • Bowman, Christopher N4
  • 1 Department of Chemical and Biological Engineering, University of Colorado Boulder, 596 UCB, Boulder, CO, United States. , (United States)
  • 2 Materials Science and Engineering Program, University of Colorado Boulder, 596 UCB, Boulder, CO, United States. , (United States)
  • 3 Department of Chemical and Biological Engineering, University of Colorado Boulder, 596 UCB, Boulder, CO, United States; Department of Craniofacial Biology, School of Dental Medicine, Anschutz Medical Campus, Aurora, CO, United States. , (United States)
  • 4 Department of Chemical and Biological Engineering, University of Colorado Boulder, 596 UCB, Boulder, CO, United States; Materials Science and Engineering Program, University of Colorado Boulder, 596 UCB, Boulder, CO, United States. Electronic address: [email protected] , (United States)
Type
Published Article
Journal
Dental materials : official publication of the Academy of Dental Materials
Publication Date
Oct 01, 2021
Volume
37
Issue
10
Pages
1592–1600
Identifiers
DOI: 10.1016/j.dental.2021.08.010
PMID: 34456051
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

The objective is to develop and characterize an ester-free ether-based photo-CuAAC resin with high mechanical performance, low polymerization-induced stress compared with common BisGMA/TEGDMA (70/30) resins, and improved water stability in comparison to previously developed urethane-based photo-CuAAC resins. Triphenyl-ethane-centered ether-linked tri-azide monomers were synthesized and co-photopolymerized with ether-linked tri-alkyne monomers under visible light irradiation using a copper(II) pre-catalyst and CQ/EDAB as the initiator. The ether-based CuAAC formulation was investigated for thermo-mechanical properties, polymerization kinetics and shrinkage stress, and flexural properties with respect to a conventional BisGMA/TEGDMA (70/30) dental resin. In addition, both the ether-based CuAAC resin and the urethane-based CuAAC resin were examined for their water stability using the BisGMA/TEGDMA (70/30) resin as a control. The ether-based CuAAC network (AK/AZ-1) exhibited a slightly lower glass-transition temperature compared with the BisGMA/TEGDMA network (108 °C vs 128 °C), but because of its much sharper glass transition, the AK/AZ-1 CuAAC-network maintained storage modulus higher than 1 GPa up to 100 °C. In addition, the ether-based AK/AZ-1 network exhibited reduced shrinkage stress (0.56 MPa vs 1.0 MPa) and much higher flexural toughness (7.6 MJ/m3vs 1.6 MJ/m3) while showing slightly lower flexural modulus and slightly higher flexural strength compared with the BisGMA/TEGDMA network. Moreover, the ether-based AK/AZ-1 CuAAC network displayed comparable water stability in comparison to the BisGMA/TEGDMA network with slightly higher water sorption (46 μg/mm3vs 38 μg/mm3) and much lower water solubility (2.3 μg/mm3vs 4.4 μg/mm3). Employing the ether-based hydrophobic CuAAC formulation significantly improved the water stability of the CuAAC network compared with previously developed urethane-based CuAAC networks. Furthermore, compared with the conventionally used BisGMA/TEGDMA formulation, the reduced shrinkage stress, comparable flexural strength/flexural modulus, and the superior flexural toughness of the ether-based CuAAC network make it a promising ester-free alternative to the currently widely-used methacrylate-based dental restoratives. Copyright © 2021 The Academy of Dental Materials. Published by Elsevier Inc. All rights reserved.

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