Effect of residual solvent on performance of acrylamide-containing dental materials

A. P. Fugolin, Adam Dobson, Jack Ferracane, Carmem Pfeifer

Research output: Contribution to journalArticle

Abstract

Objective: Methacrylamide-based monomers are being pursued as novel, hydrolytically stable materials for use in dental adhesives. The impact of residual solvents, due to the chemical synthesis procedures or the need for solvated adhesives systems, on the kinetics of polymerization and mechanical properties was the aim of the present investigation. Methods: Two base monomers (70 wt% BisGMA or HEMAM-BDI — newly synthesized secondary methacrylamide) were combined with 30 wt% N,N-dimethylacrylamide. Eethyl acetate (EtOAc), or 75 vol% ethanol/25 vol% water (EtOH/H2O) were added as solvents in concentrations of 2, 5, 15 and 20 wt%. The resins were made polymerizable by the addition of 0.2 wt% 2,2-dimethoxy-2-phenyl acetophenone (DMPA) and 0.4 wt% diphenyliodonium hexafluorophosphate (DPI-PF6). Specimens (n = 3) were photoactivated with a mercury arc lamp (Acticure 4000, 320–500 nm, 250 mW/cm2) for 5 min. Degree of conversion (DC, %) was tracked in near-IR spectroscopy in real time and yield strength and modulus of elasticity were measured in three-point bending after dry and wet storage (n = 6). The data was subject to one-way ANOVA/Tukey's Test (p ≤ 0.05), or Student's t-test (p ≤ 0.001). Results: In all groups for both BisGMA and HEMAM-BDI-based materials, DC and DC at Rpmax increased and maximum rate of polymerization decreased as solvent concentration increased. Despite the increased DC, BisGMA mixtures showed a decrease in FS starting at 5 wt% EtOAc or 15 wt% EtOH/H2O. Yield strength for the HEMAM-BDI groups was overall lower than that of the BisGMA groups, but the modulus of elasticity was significantly higher. Significance: The presence of residual solvent, from manufacturing or from practitioner's handling, affects polymerization kinetics and mechanical properties of resins. Methacrylates appear to be more strongly influenced than methacrylamides.

Original languageEnglish (US)
JournalDental Materials
DOIs
StatePublished - Jan 1 2019

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Dental materials
Dental Materials
Acrylamide
Polymerization
Elastic Modulus
Yield stress
Adhesives
Resins
Monomers
Elastic moduli
Arc lamps
Dental Cements
Mercury vapor lamps
Mechanical properties
Kinetics
Methacrylates
Analysis of variance (ANOVA)
Mercury
Infrared spectroscopy
Spectrum Analysis

Keywords

  • Dental materials
  • Polymerization
  • Scrylamide
  • Solvent

ASJC Scopus subject areas

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

Cite this

Effect of residual solvent on performance of acrylamide-containing dental materials. / Fugolin, A. P.; Dobson, Adam; Ferracane, Jack; Pfeifer, Carmem.

In: Dental Materials, 01.01.2019.

Research output: Contribution to journalArticle

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title = "Effect of residual solvent on performance of acrylamide-containing dental materials",
abstract = "Objective: Methacrylamide-based monomers are being pursued as novel, hydrolytically stable materials for use in dental adhesives. The impact of residual solvents, due to the chemical synthesis procedures or the need for solvated adhesives systems, on the kinetics of polymerization and mechanical properties was the aim of the present investigation. Methods: Two base monomers (70 wt{\%} BisGMA or HEMAM-BDI — newly synthesized secondary methacrylamide) were combined with 30 wt{\%} N,N-dimethylacrylamide. Eethyl acetate (EtOAc), or 75 vol{\%} ethanol/25 vol{\%} water (EtOH/H2O) were added as solvents in concentrations of 2, 5, 15 and 20 wt{\%}. The resins were made polymerizable by the addition of 0.2 wt{\%} 2,2-dimethoxy-2-phenyl acetophenone (DMPA) and 0.4 wt{\%} diphenyliodonium hexafluorophosphate (DPI-PF6). Specimens (n = 3) were photoactivated with a mercury arc lamp (Acticure 4000, 320–500 nm, 250 mW/cm2) for 5 min. Degree of conversion (DC, {\%}) was tracked in near-IR spectroscopy in real time and yield strength and modulus of elasticity were measured in three-point bending after dry and wet storage (n = 6). The data was subject to one-way ANOVA/Tukey's Test (p ≤ 0.05), or Student's t-test (p ≤ 0.001). Results: In all groups for both BisGMA and HEMAM-BDI-based materials, DC and DC at Rpmax increased and maximum rate of polymerization decreased as solvent concentration increased. Despite the increased DC, BisGMA mixtures showed a decrease in FS starting at 5 wt{\%} EtOAc or 15 wt{\%} EtOH/H2O. Yield strength for the HEMAM-BDI groups was overall lower than that of the BisGMA groups, but the modulus of elasticity was significantly higher. Significance: The presence of residual solvent, from manufacturing or from practitioner's handling, affects polymerization kinetics and mechanical properties of resins. Methacrylates appear to be more strongly influenced than methacrylamides.",
keywords = "Dental materials, Polymerization, Scrylamide, Solvent",
author = "Fugolin, {A. P.} and Adam Dobson and Jack Ferracane and Carmem Pfeifer",
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T1 - Effect of residual solvent on performance of acrylamide-containing dental materials

AU - Fugolin, A. P.

AU - Dobson, Adam

AU - Ferracane, Jack

AU - Pfeifer, Carmem

PY - 2019/1/1

Y1 - 2019/1/1

N2 - Objective: Methacrylamide-based monomers are being pursued as novel, hydrolytically stable materials for use in dental adhesives. The impact of residual solvents, due to the chemical synthesis procedures or the need for solvated adhesives systems, on the kinetics of polymerization and mechanical properties was the aim of the present investigation. Methods: Two base monomers (70 wt% BisGMA or HEMAM-BDI — newly synthesized secondary methacrylamide) were combined with 30 wt% N,N-dimethylacrylamide. Eethyl acetate (EtOAc), or 75 vol% ethanol/25 vol% water (EtOH/H2O) were added as solvents in concentrations of 2, 5, 15 and 20 wt%. The resins were made polymerizable by the addition of 0.2 wt% 2,2-dimethoxy-2-phenyl acetophenone (DMPA) and 0.4 wt% diphenyliodonium hexafluorophosphate (DPI-PF6). Specimens (n = 3) were photoactivated with a mercury arc lamp (Acticure 4000, 320–500 nm, 250 mW/cm2) for 5 min. Degree of conversion (DC, %) was tracked in near-IR spectroscopy in real time and yield strength and modulus of elasticity were measured in three-point bending after dry and wet storage (n = 6). The data was subject to one-way ANOVA/Tukey's Test (p ≤ 0.05), or Student's t-test (p ≤ 0.001). Results: In all groups for both BisGMA and HEMAM-BDI-based materials, DC and DC at Rpmax increased and maximum rate of polymerization decreased as solvent concentration increased. Despite the increased DC, BisGMA mixtures showed a decrease in FS starting at 5 wt% EtOAc or 15 wt% EtOH/H2O. Yield strength for the HEMAM-BDI groups was overall lower than that of the BisGMA groups, but the modulus of elasticity was significantly higher. Significance: The presence of residual solvent, from manufacturing or from practitioner's handling, affects polymerization kinetics and mechanical properties of resins. Methacrylates appear to be more strongly influenced than methacrylamides.

AB - Objective: Methacrylamide-based monomers are being pursued as novel, hydrolytically stable materials for use in dental adhesives. The impact of residual solvents, due to the chemical synthesis procedures or the need for solvated adhesives systems, on the kinetics of polymerization and mechanical properties was the aim of the present investigation. Methods: Two base monomers (70 wt% BisGMA or HEMAM-BDI — newly synthesized secondary methacrylamide) were combined with 30 wt% N,N-dimethylacrylamide. Eethyl acetate (EtOAc), or 75 vol% ethanol/25 vol% water (EtOH/H2O) were added as solvents in concentrations of 2, 5, 15 and 20 wt%. The resins were made polymerizable by the addition of 0.2 wt% 2,2-dimethoxy-2-phenyl acetophenone (DMPA) and 0.4 wt% diphenyliodonium hexafluorophosphate (DPI-PF6). Specimens (n = 3) were photoactivated with a mercury arc lamp (Acticure 4000, 320–500 nm, 250 mW/cm2) for 5 min. Degree of conversion (DC, %) was tracked in near-IR spectroscopy in real time and yield strength and modulus of elasticity were measured in three-point bending after dry and wet storage (n = 6). The data was subject to one-way ANOVA/Tukey's Test (p ≤ 0.05), or Student's t-test (p ≤ 0.001). Results: In all groups for both BisGMA and HEMAM-BDI-based materials, DC and DC at Rpmax increased and maximum rate of polymerization decreased as solvent concentration increased. Despite the increased DC, BisGMA mixtures showed a decrease in FS starting at 5 wt% EtOAc or 15 wt% EtOH/H2O. Yield strength for the HEMAM-BDI groups was overall lower than that of the BisGMA groups, but the modulus of elasticity was significantly higher. Significance: The presence of residual solvent, from manufacturing or from practitioner's handling, affects polymerization kinetics and mechanical properties of resins. Methacrylates appear to be more strongly influenced than methacrylamides.

KW - Dental materials

KW - Polymerization

KW - Scrylamide

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