Isocyanate-terminated urethane-based dental adhesive bridges dentinal matrix collagen with adhesive resin

Rongchen Xu, Fan Yu, Li Huang, Wei Zhou, Yan Wang, Fu Wang, Xiang Sun, Gang Chang, Ming Fang, Ling Zhang, Fang Li, Franklin Chi Meng Tay, Lina Niu, Jihua Chen

Research output: Contribution to journalArticle

Abstract

Commercially available dental adhesives fail to chemically unite the demineralized collagen matrix with resinous materials within the resin-dentin interface. Sub-micron separations between the collagen fibrils and polymerized resin provide the backdrop for bond deterioration. Here, novel isocyanate-terminated urethane methacrylate precursors (UMP) were synthesized with the capacity to bond chemically to dentin collagen via covalent and hydrogen bonds. Collagen grafted with UMP also copolymerized with other methacrylate resin monomers, thereby producing a monoblock of chemically-linked biocomposite. The viscosity, degree of conversion and biocompatibility of UMP are comparable with commercially available resin monomers. An experimental adhesive containing 40% UMP demonstrated co-polymerization capability, good infiltration capacity and achieved higher immediate bond strength to dentin than the control commercially available adhesive. Improvement of dentin bonding by incorporation of UMP into dentin adhesives justifies future evaluation of the potential of these UMP-based adhesives in extending the longevity of resin-dentin bonds. Statement of Significance: Composite-adhesive restorations have become an indispensable treatment modality in contemporary restorative dentistry. While the inability of these adhesives to bond chemically with collagen undermines the bond quality. This study describes a novel isocyanate-terminated urethane multi methacrylate precursors (UMP) which can bridge dentinal matrix collagen with adhesive resin by covalent and hydrogen bonds. Furthermore, an experimental UMP-based adhesive shows better co-polymerization capability, good infiltration capacity and higher immediate bond strength than the putatively effective adhesive Single Bond 2. The new chemical bonding mechanism based on UMP would theoretically produce more stable bonding interface that are more resistant to degradation.

Original languageEnglish (US)
Pages (from-to)140-152
Number of pages13
JournalActa biomaterialia
Volume83
DOIs
StatePublished - Jan 1 2019

Fingerprint

Dental Cements
Isocyanates
Methacrylates
Urethane
Collagen
Adhesives
Resins
Dentin
Covalent bonds
Infiltration
Polymerization
Copolymerization
Hydrogen
Hydrogen bonds
Monomers
Dentistry
Chemical bonds
Biocompatibility
Viscosity
Restoration

Keywords

  • Adhesive
  • Collagen
  • Dentin bonding
  • Isocyanate
  • Urethane-based

ASJC Scopus subject areas

  • Biotechnology
  • Biomaterials
  • Biochemistry
  • Biomedical Engineering
  • Molecular Biology

Cite this

Isocyanate-terminated urethane-based dental adhesive bridges dentinal matrix collagen with adhesive resin. / Xu, Rongchen; Yu, Fan; Huang, Li; Zhou, Wei; Wang, Yan; Wang, Fu; Sun, Xiang; Chang, Gang; Fang, Ming; Zhang, Ling; Li, Fang; Tay, Franklin Chi Meng; Niu, Lina; Chen, Jihua.

In: Acta biomaterialia, Vol. 83, 01.01.2019, p. 140-152.

Research output: Contribution to journalArticle

Xu, R, Yu, F, Huang, L, Zhou, W, Wang, Y, Wang, F, Sun, X, Chang, G, Fang, M, Zhang, L, Li, F, Tay, FCM, Niu, L & Chen, J 2019, 'Isocyanate-terminated urethane-based dental adhesive bridges dentinal matrix collagen with adhesive resin', Acta biomaterialia, vol. 83, pp. 140-152. https://doi.org/10.1016/j.actbio.2018.11.007
Xu, Rongchen ; Yu, Fan ; Huang, Li ; Zhou, Wei ; Wang, Yan ; Wang, Fu ; Sun, Xiang ; Chang, Gang ; Fang, Ming ; Zhang, Ling ; Li, Fang ; Tay, Franklin Chi Meng ; Niu, Lina ; Chen, Jihua. / Isocyanate-terminated urethane-based dental adhesive bridges dentinal matrix collagen with adhesive resin. In: Acta biomaterialia. 2019 ; Vol. 83. pp. 140-152.
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abstract = "Commercially available dental adhesives fail to chemically unite the demineralized collagen matrix with resinous materials within the resin-dentin interface. Sub-micron separations between the collagen fibrils and polymerized resin provide the backdrop for bond deterioration. Here, novel isocyanate-terminated urethane methacrylate precursors (UMP) were synthesized with the capacity to bond chemically to dentin collagen via covalent and hydrogen bonds. Collagen grafted with UMP also copolymerized with other methacrylate resin monomers, thereby producing a monoblock of chemically-linked biocomposite. The viscosity, degree of conversion and biocompatibility of UMP are comparable with commercially available resin monomers. An experimental adhesive containing 40{\%} UMP demonstrated co-polymerization capability, good infiltration capacity and achieved higher immediate bond strength to dentin than the control commercially available adhesive. Improvement of dentin bonding by incorporation of UMP into dentin adhesives justifies future evaluation of the potential of these UMP-based adhesives in extending the longevity of resin-dentin bonds. Statement of Significance: Composite-adhesive restorations have become an indispensable treatment modality in contemporary restorative dentistry. While the inability of these adhesives to bond chemically with collagen undermines the bond quality. This study describes a novel isocyanate-terminated urethane multi methacrylate precursors (UMP) which can bridge dentinal matrix collagen with adhesive resin by covalent and hydrogen bonds. Furthermore, an experimental UMP-based adhesive shows better co-polymerization capability, good infiltration capacity and higher immediate bond strength than the putatively effective adhesive Single Bond 2. The new chemical bonding mechanism based on UMP would theoretically produce more stable bonding interface that are more resistant to degradation.",
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AU - Zhou, Wei

AU - Wang, Yan

AU - Wang, Fu

AU - Sun, Xiang

AU - Chang, Gang

AU - Fang, Ming

AU - Zhang, Ling

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AU - Tay, Franklin Chi Meng

AU - Niu, Lina

AU - Chen, Jihua

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N2 - Commercially available dental adhesives fail to chemically unite the demineralized collagen matrix with resinous materials within the resin-dentin interface. Sub-micron separations between the collagen fibrils and polymerized resin provide the backdrop for bond deterioration. Here, novel isocyanate-terminated urethane methacrylate precursors (UMP) were synthesized with the capacity to bond chemically to dentin collagen via covalent and hydrogen bonds. Collagen grafted with UMP also copolymerized with other methacrylate resin monomers, thereby producing a monoblock of chemically-linked biocomposite. The viscosity, degree of conversion and biocompatibility of UMP are comparable with commercially available resin monomers. An experimental adhesive containing 40% UMP demonstrated co-polymerization capability, good infiltration capacity and achieved higher immediate bond strength to dentin than the control commercially available adhesive. Improvement of dentin bonding by incorporation of UMP into dentin adhesives justifies future evaluation of the potential of these UMP-based adhesives in extending the longevity of resin-dentin bonds. Statement of Significance: Composite-adhesive restorations have become an indispensable treatment modality in contemporary restorative dentistry. While the inability of these adhesives to bond chemically with collagen undermines the bond quality. This study describes a novel isocyanate-terminated urethane multi methacrylate precursors (UMP) which can bridge dentinal matrix collagen with adhesive resin by covalent and hydrogen bonds. Furthermore, an experimental UMP-based adhesive shows better co-polymerization capability, good infiltration capacity and higher immediate bond strength than the putatively effective adhesive Single Bond 2. The new chemical bonding mechanism based on UMP would theoretically produce more stable bonding interface that are more resistant to degradation.

AB - Commercially available dental adhesives fail to chemically unite the demineralized collagen matrix with resinous materials within the resin-dentin interface. Sub-micron separations between the collagen fibrils and polymerized resin provide the backdrop for bond deterioration. Here, novel isocyanate-terminated urethane methacrylate precursors (UMP) were synthesized with the capacity to bond chemically to dentin collagen via covalent and hydrogen bonds. Collagen grafted with UMP also copolymerized with other methacrylate resin monomers, thereby producing a monoblock of chemically-linked biocomposite. The viscosity, degree of conversion and biocompatibility of UMP are comparable with commercially available resin monomers. An experimental adhesive containing 40% UMP demonstrated co-polymerization capability, good infiltration capacity and achieved higher immediate bond strength to dentin than the control commercially available adhesive. Improvement of dentin bonding by incorporation of UMP into dentin adhesives justifies future evaluation of the potential of these UMP-based adhesives in extending the longevity of resin-dentin bonds. Statement of Significance: Composite-adhesive restorations have become an indispensable treatment modality in contemporary restorative dentistry. While the inability of these adhesives to bond chemically with collagen undermines the bond quality. This study describes a novel isocyanate-terminated urethane multi methacrylate precursors (UMP) which can bridge dentinal matrix collagen with adhesive resin by covalent and hydrogen bonds. Furthermore, an experimental UMP-based adhesive shows better co-polymerization capability, good infiltration capacity and higher immediate bond strength than the putatively effective adhesive Single Bond 2. The new chemical bonding mechanism based on UMP would theoretically produce more stable bonding interface that are more resistant to degradation.

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