Coupling of 10-methacryloyloxydecyldihydrogenphosphate to tetragonal zirconia: Effect of pH reaction conditions on coordinate bonding

Haifeng Xie, Franklin Chi Meng Tay, Feimin Zhang, Yi Lu, Shuping Shen, Chen Chen

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Objectives Identification of the mechanism of chemical coupling of a phosphate ester monomer to zirconia via a computational modeling approach enables materials scientists to design new coupling agents that can resist hydrolytic degradation of bonds made by methacrylate resins to zirconia. We investigated the possibility of chemical bonding between 10-methacryloyloxydecyldihydrogenphosphate (MDP) and tetragonal zirconia, and the effect of pH reaction conditions on such prospective chemical bonds. Methods A tetragonal zirconia crystal model was created. An "Our-own N-layered integrated molecular orbital and molecular mechanics" (ONIOM) method was used to simulate two potential configurations of the MDP-ZrO2 system: double-coordinate and single-coordinate. Thermodynamic calculations were used to ascertain if the reaction could proceed spontaneously and to compare the stability of the two possible configurations. Short-term testing of shear bond strength (SBS) was done to evaluate bonding improvement of MDP to alumina-sandblasted zirconia surfaces in neutral, acidic or alkaline environments. Results Digital models of coordinate bonds between MDP and tetragonal zirconia were constructed. Thermodynamic calculations indicated that the Gibbs free energy for forming double-coordinate and single-coordinate configurations were -461.2 kJ/mol and -450.9 kJ/mol, respectively. Equilibrium constants for the double-coordinate and single-coordinate configurations were 6.4 × 1080 and 9.8 × 1078, respectively. Application of MDP in alkaline conditions showed the highest SBS, whereas acid conditions resulted in lower SBS. Significance MDP can establish a "true" chemical bond with zirconia spontaneously. The double-coordinate configuration was identified to be more energetically favorable than the single-coordinate configuration for the coupling of MDP to zirconia. Alkaline conditions may positively affect formation of MDP-ZrO2 coordination bonds.

Original languageEnglish (US)
Pages (from-to)e218-e225
JournalDental Materials
Volume31
Issue number10
DOIs
StatePublished - Oct 1 2015

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Zirconia
Shear Strength
Chemical bonds
Thermodynamics
Molecular mechanics
Methacrylates
zirconium oxide
Aluminum Oxide
Coupling agents
Equilibrium constants
Molecular orbitals
Gibbs free energy
Mechanics
Esters
Phosphates
Alumina
Resins
Monomers
Degradation
Crystals

Keywords

  • Adhesion
  • Adhesive monomer
  • Bond
  • Bonding
  • MDP
  • Primer
  • Surface conditioning
  • Zirconia

ASJC Scopus subject areas

  • Materials Science(all)
  • Dentistry(all)
  • Mechanics of Materials

Cite this

Coupling of 10-methacryloyloxydecyldihydrogenphosphate to tetragonal zirconia : Effect of pH reaction conditions on coordinate bonding. / Xie, Haifeng; Tay, Franklin Chi Meng; Zhang, Feimin; Lu, Yi; Shen, Shuping; Chen, Chen.

In: Dental Materials, Vol. 31, No. 10, 01.10.2015, p. e218-e225.

Research output: Contribution to journalArticle

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title = "Coupling of 10-methacryloyloxydecyldihydrogenphosphate to tetragonal zirconia: Effect of pH reaction conditions on coordinate bonding",
abstract = "Objectives Identification of the mechanism of chemical coupling of a phosphate ester monomer to zirconia via a computational modeling approach enables materials scientists to design new coupling agents that can resist hydrolytic degradation of bonds made by methacrylate resins to zirconia. We investigated the possibility of chemical bonding between 10-methacryloyloxydecyldihydrogenphosphate (MDP) and tetragonal zirconia, and the effect of pH reaction conditions on such prospective chemical bonds. Methods A tetragonal zirconia crystal model was created. An {"}Our-own N-layered integrated molecular orbital and molecular mechanics{"} (ONIOM) method was used to simulate two potential configurations of the MDP-ZrO2 system: double-coordinate and single-coordinate. Thermodynamic calculations were used to ascertain if the reaction could proceed spontaneously and to compare the stability of the two possible configurations. Short-term testing of shear bond strength (SBS) was done to evaluate bonding improvement of MDP to alumina-sandblasted zirconia surfaces in neutral, acidic or alkaline environments. Results Digital models of coordinate bonds between MDP and tetragonal zirconia were constructed. Thermodynamic calculations indicated that the Gibbs free energy for forming double-coordinate and single-coordinate configurations were -461.2 kJ/mol and -450.9 kJ/mol, respectively. Equilibrium constants for the double-coordinate and single-coordinate configurations were 6.4 × 1080 and 9.8 × 1078, respectively. Application of MDP in alkaline conditions showed the highest SBS, whereas acid conditions resulted in lower SBS. Significance MDP can establish a {"}true{"} chemical bond with zirconia spontaneously. The double-coordinate configuration was identified to be more energetically favorable than the single-coordinate configuration for the coupling of MDP to zirconia. Alkaline conditions may positively affect formation of MDP-ZrO2 coordination bonds.",
keywords = "Adhesion, Adhesive monomer, Bond, Bonding, MDP, Primer, Surface conditioning, Zirconia",
author = "Haifeng Xie and Tay, {Franklin Chi Meng} and Feimin Zhang and Yi Lu and Shuping Shen and Chen Chen",
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T1 - Coupling of 10-methacryloyloxydecyldihydrogenphosphate to tetragonal zirconia

T2 - Effect of pH reaction conditions on coordinate bonding

AU - Xie, Haifeng

AU - Tay, Franklin Chi Meng

AU - Zhang, Feimin

AU - Lu, Yi

AU - Shen, Shuping

AU - Chen, Chen

PY - 2015/10/1

Y1 - 2015/10/1

N2 - Objectives Identification of the mechanism of chemical coupling of a phosphate ester monomer to zirconia via a computational modeling approach enables materials scientists to design new coupling agents that can resist hydrolytic degradation of bonds made by methacrylate resins to zirconia. We investigated the possibility of chemical bonding between 10-methacryloyloxydecyldihydrogenphosphate (MDP) and tetragonal zirconia, and the effect of pH reaction conditions on such prospective chemical bonds. Methods A tetragonal zirconia crystal model was created. An "Our-own N-layered integrated molecular orbital and molecular mechanics" (ONIOM) method was used to simulate two potential configurations of the MDP-ZrO2 system: double-coordinate and single-coordinate. Thermodynamic calculations were used to ascertain if the reaction could proceed spontaneously and to compare the stability of the two possible configurations. Short-term testing of shear bond strength (SBS) was done to evaluate bonding improvement of MDP to alumina-sandblasted zirconia surfaces in neutral, acidic or alkaline environments. Results Digital models of coordinate bonds between MDP and tetragonal zirconia were constructed. Thermodynamic calculations indicated that the Gibbs free energy for forming double-coordinate and single-coordinate configurations were -461.2 kJ/mol and -450.9 kJ/mol, respectively. Equilibrium constants for the double-coordinate and single-coordinate configurations were 6.4 × 1080 and 9.8 × 1078, respectively. Application of MDP in alkaline conditions showed the highest SBS, whereas acid conditions resulted in lower SBS. Significance MDP can establish a "true" chemical bond with zirconia spontaneously. The double-coordinate configuration was identified to be more energetically favorable than the single-coordinate configuration for the coupling of MDP to zirconia. Alkaline conditions may positively affect formation of MDP-ZrO2 coordination bonds.

AB - Objectives Identification of the mechanism of chemical coupling of a phosphate ester monomer to zirconia via a computational modeling approach enables materials scientists to design new coupling agents that can resist hydrolytic degradation of bonds made by methacrylate resins to zirconia. We investigated the possibility of chemical bonding between 10-methacryloyloxydecyldihydrogenphosphate (MDP) and tetragonal zirconia, and the effect of pH reaction conditions on such prospective chemical bonds. Methods A tetragonal zirconia crystal model was created. An "Our-own N-layered integrated molecular orbital and molecular mechanics" (ONIOM) method was used to simulate two potential configurations of the MDP-ZrO2 system: double-coordinate and single-coordinate. Thermodynamic calculations were used to ascertain if the reaction could proceed spontaneously and to compare the stability of the two possible configurations. Short-term testing of shear bond strength (SBS) was done to evaluate bonding improvement of MDP to alumina-sandblasted zirconia surfaces in neutral, acidic or alkaline environments. Results Digital models of coordinate bonds between MDP and tetragonal zirconia were constructed. Thermodynamic calculations indicated that the Gibbs free energy for forming double-coordinate and single-coordinate configurations were -461.2 kJ/mol and -450.9 kJ/mol, respectively. Equilibrium constants for the double-coordinate and single-coordinate configurations were 6.4 × 1080 and 9.8 × 1078, respectively. Application of MDP in alkaline conditions showed the highest SBS, whereas acid conditions resulted in lower SBS. Significance MDP can establish a "true" chemical bond with zirconia spontaneously. The double-coordinate configuration was identified to be more energetically favorable than the single-coordinate configuration for the coupling of MDP to zirconia. Alkaline conditions may positively affect formation of MDP-ZrO2 coordination bonds.

KW - Adhesion

KW - Adhesive monomer

KW - Bond

KW - Bonding

KW - MDP

KW - Primer

KW - Surface conditioning

KW - Zirconia

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