Chemical affinity of 10-methacryloyloxydecyl dihydrogen phosphate to dental zirconia: Effects of molecular structure and solvents

Ying Chen, Zhicen Lu, Mengke Qian, Huaiqin Zhang, Chen Chen, Haifeng Xie, Franklin Chi Meng Tay

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Objectives To examine whether solvents and changing the molecular structure of 10-Methacryloyloxydecyl dihydrogen phosphate (10-MDP) affect its chemical affinity to Yttria-stabilized tetragonal zirconia polycrystals (Y-TZP). Methods The present work investigated the chemical affinity between Y-TZP and 10-MDP dissolved in different solvents (acetone/ethanol/water or mixture) using X-ray photoelectron spectroscopy, Fourier-transform infrared spectroscopy, and thermodynamic calculations. Shear bond strength (SBS) tests were used to evaluate the influence of different solvents on 10-MDP bonding. In addition, several phosphate ester monomer variants were created by changing the 10-MDP molecular structure. Changes included extending/shortening the spacer chain-length, and installing hydroxyl or carboxyl groups as side chains at different positions along the spacer chain. The thermodynamic parameters of the complexes formed between the 10-MDP variants and tetragonal zirconia were evaluated. Results The acquired data indicated that solvent is necessary for the formation of Zr–O–P bonds between 10-MDP and Y-TZP. Solvents affected the chemical affinity of 10-MDP to Y-TZP; acetone facilitated the best bonding, followed by ethanol. Changing the molecular structure of 10-MDP affected its chemical affinity to Y-TZP. The variants 15-MPDP, 12-MDDP, 6-hydroxyl-10-MDP and 6-carboxy-10-MDP all exhibited higher thermodynamic stability than 10-MDP when coordinated with tetragonal zirconia. In contrast, 2-MEP, 5-MPP, 10-hydroxyl-MDP, 10-carboxy-MDP, 5,6-dihydroxyl-10-MDP and 5,6-dicarboxy-10-MDP exhibited lower thermodynamic stability. Significance 10-MDP coordinates with zirconia through dissociating in solvents. Changing the molecular structure of 10-MDP theoretically affects its chemical affinity to Y-TZP.

Original languageEnglish (US)
Pages (from-to)e415-e427
JournalDental Materials
Volume33
Issue number12
DOIs
StatePublished - Dec 2017

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Molecular Structure
Zirconia
Molecular structure
Tooth
Phosphates
Polycrystals
Yttria stabilized zirconia
Thermodynamics
Hydroxyl Radical
zirconium oxide
methacryloyloxydecyl dihydrogen phosphate
Acetone
Thermodynamic stability
Ethanol
Shear Strength
Photoelectron Spectroscopy
Fourier Transform Infrared Spectroscopy
Chemical bonds
Chain length
yttria stabilized tetragonal zirconia

Keywords

  • MDP
  • Phosphate ester monomer
  • Primer
  • Surface conditioning
  • Yttria-stabilized tetragonal zirconia polycrystals

ASJC Scopus subject areas

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

Cite this

Chemical affinity of 10-methacryloyloxydecyl dihydrogen phosphate to dental zirconia : Effects of molecular structure and solvents. / Chen, Ying; Lu, Zhicen; Qian, Mengke; Zhang, Huaiqin; Chen, Chen; Xie, Haifeng; Tay, Franklin Chi Meng.

In: Dental Materials, Vol. 33, No. 12, 12.2017, p. e415-e427.

Research output: Contribution to journalArticle

Chen, Ying ; Lu, Zhicen ; Qian, Mengke ; Zhang, Huaiqin ; Chen, Chen ; Xie, Haifeng ; Tay, Franklin Chi Meng. / Chemical affinity of 10-methacryloyloxydecyl dihydrogen phosphate to dental zirconia : Effects of molecular structure and solvents. In: Dental Materials. 2017 ; Vol. 33, No. 12. pp. e415-e427.
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abstract = "Objectives To examine whether solvents and changing the molecular structure of 10-Methacryloyloxydecyl dihydrogen phosphate (10-MDP) affect its chemical affinity to Yttria-stabilized tetragonal zirconia polycrystals (Y-TZP). Methods The present work investigated the chemical affinity between Y-TZP and 10-MDP dissolved in different solvents (acetone/ethanol/water or mixture) using X-ray photoelectron spectroscopy, Fourier-transform infrared spectroscopy, and thermodynamic calculations. Shear bond strength (SBS) tests were used to evaluate the influence of different solvents on 10-MDP bonding. In addition, several phosphate ester monomer variants were created by changing the 10-MDP molecular structure. Changes included extending/shortening the spacer chain-length, and installing hydroxyl or carboxyl groups as side chains at different positions along the spacer chain. The thermodynamic parameters of the complexes formed between the 10-MDP variants and tetragonal zirconia were evaluated. Results The acquired data indicated that solvent is necessary for the formation of Zr–O–P bonds between 10-MDP and Y-TZP. Solvents affected the chemical affinity of 10-MDP to Y-TZP; acetone facilitated the best bonding, followed by ethanol. Changing the molecular structure of 10-MDP affected its chemical affinity to Y-TZP. The variants 15-MPDP, 12-MDDP, 6-hydroxyl-10-MDP and 6-carboxy-10-MDP all exhibited higher thermodynamic stability than 10-MDP when coordinated with tetragonal zirconia. In contrast, 2-MEP, 5-MPP, 10-hydroxyl-MDP, 10-carboxy-MDP, 5,6-dihydroxyl-10-MDP and 5,6-dicarboxy-10-MDP exhibited lower thermodynamic stability. Significance 10-MDP coordinates with zirconia through dissociating in solvents. Changing the molecular structure of 10-MDP theoretically affects its chemical affinity to Y-TZP.",
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AU - Chen, Ying

AU - Lu, Zhicen

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AU - Zhang, Huaiqin

AU - Chen, Chen

AU - Xie, Haifeng

AU - Tay, Franklin Chi Meng

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N2 - Objectives To examine whether solvents and changing the molecular structure of 10-Methacryloyloxydecyl dihydrogen phosphate (10-MDP) affect its chemical affinity to Yttria-stabilized tetragonal zirconia polycrystals (Y-TZP). Methods The present work investigated the chemical affinity between Y-TZP and 10-MDP dissolved in different solvents (acetone/ethanol/water or mixture) using X-ray photoelectron spectroscopy, Fourier-transform infrared spectroscopy, and thermodynamic calculations. Shear bond strength (SBS) tests were used to evaluate the influence of different solvents on 10-MDP bonding. In addition, several phosphate ester monomer variants were created by changing the 10-MDP molecular structure. Changes included extending/shortening the spacer chain-length, and installing hydroxyl or carboxyl groups as side chains at different positions along the spacer chain. The thermodynamic parameters of the complexes formed between the 10-MDP variants and tetragonal zirconia were evaluated. Results The acquired data indicated that solvent is necessary for the formation of Zr–O–P bonds between 10-MDP and Y-TZP. Solvents affected the chemical affinity of 10-MDP to Y-TZP; acetone facilitated the best bonding, followed by ethanol. Changing the molecular structure of 10-MDP affected its chemical affinity to Y-TZP. The variants 15-MPDP, 12-MDDP, 6-hydroxyl-10-MDP and 6-carboxy-10-MDP all exhibited higher thermodynamic stability than 10-MDP when coordinated with tetragonal zirconia. In contrast, 2-MEP, 5-MPP, 10-hydroxyl-MDP, 10-carboxy-MDP, 5,6-dihydroxyl-10-MDP and 5,6-dicarboxy-10-MDP exhibited lower thermodynamic stability. Significance 10-MDP coordinates with zirconia through dissociating in solvents. Changing the molecular structure of 10-MDP theoretically affects its chemical affinity to Y-TZP.

AB - Objectives To examine whether solvents and changing the molecular structure of 10-Methacryloyloxydecyl dihydrogen phosphate (10-MDP) affect its chemical affinity to Yttria-stabilized tetragonal zirconia polycrystals (Y-TZP). Methods The present work investigated the chemical affinity between Y-TZP and 10-MDP dissolved in different solvents (acetone/ethanol/water or mixture) using X-ray photoelectron spectroscopy, Fourier-transform infrared spectroscopy, and thermodynamic calculations. Shear bond strength (SBS) tests were used to evaluate the influence of different solvents on 10-MDP bonding. In addition, several phosphate ester monomer variants were created by changing the 10-MDP molecular structure. Changes included extending/shortening the spacer chain-length, and installing hydroxyl or carboxyl groups as side chains at different positions along the spacer chain. The thermodynamic parameters of the complexes formed between the 10-MDP variants and tetragonal zirconia were evaluated. Results The acquired data indicated that solvent is necessary for the formation of Zr–O–P bonds between 10-MDP and Y-TZP. Solvents affected the chemical affinity of 10-MDP to Y-TZP; acetone facilitated the best bonding, followed by ethanol. Changing the molecular structure of 10-MDP affected its chemical affinity to Y-TZP. The variants 15-MPDP, 12-MDDP, 6-hydroxyl-10-MDP and 6-carboxy-10-MDP all exhibited higher thermodynamic stability than 10-MDP when coordinated with tetragonal zirconia. In contrast, 2-MEP, 5-MPP, 10-hydroxyl-MDP, 10-carboxy-MDP, 5,6-dihydroxyl-10-MDP and 5,6-dicarboxy-10-MDP exhibited lower thermodynamic stability. Significance 10-MDP coordinates with zirconia through dissociating in solvents. Changing the molecular structure of 10-MDP theoretically affects its chemical affinity to Y-TZP.

KW - MDP

KW - Phosphate ester monomer

KW - Primer

KW - Surface conditioning

KW - Yttria-stabilized tetragonal zirconia polycrystals

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