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HOME > Restor Dent Endod > Volume 29(3); 2004 > Article
Original Article Effect of pH and storage time on the elution of residual monomers from polymerized composite resins
Cheol-Min Jeon1, Hyun-Mi Yoo2, Hyuk-Choon Kwon1
2004;29(3):-266.
DOI: https://doi.org/10.5395/JKACD.2004.29.3.249
Published online: May 31, 2004

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Corresponding author: Hyuk-Choon Kwon. Department of Conservative Dentistry, College of Dentistry, Seoul National University, 28-2 Yeongun-dong, Chongro-gu, Seoul, Korea, 110-749. Tel: 82-2-2647-2882, Fax: 82-2-2647-7528, juhohyun@hanmail.net

Copyright © 2004 Korean Academy of Conservative Dentistry

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  • Objectives
    The purpose of this study was to determine whether pH and time has any influence on the degradation behavior of composite restoration by analyzing the leached monomers of dental composites qualitatively and quantitatively after storage in acetate buffer solution as a function of time using high performance liquid chromatography (HPLC) / mass spectrometer.
  • Materials and Methods
    Three commercial composite restorative resin materials (Z-250, Heliomolar and Aeliteflo) with different matrix structure and filler composition were studied. Thirty specimens (7mm diameter×2mm thick) of each material were prepared. The cured materials were stored in acetate buffer solution at different pH (4, 7) for 1, 7 and 45days. As a reference, samples of unpolymerized composite materials of each product were treated with methanol (10 mg/ml). Identification of the various compounds was achieved by comparison of their mass spectra with those of reference compound, with literature data, and by their fragmentation patterns. Data were analysed statistically using ANOVA and Duncan's test.
  • Results
    1. Amounts of leached TEGDMA in Aeliteflo were significantly larger than those of UDMA in Z-250 and Heliomolar at experimental conditions of different storage time and pH variation (p < 0.001).
    2. As to comparison of the amounts of leached monomers per sorage time, amounts of leached TEGDMA in Aeliteflo and UDMA in Z-250 and Heliomolar were increased in the pH 4 solution more significantly than in the pH 7 solution after 1day, 7days and 45days, respectively (p < 0.001).
    3. In total amounts of all the leached monomers with storage times, the overall amounts of pH 4 extracts were larger than those of pH 7 extracts for all resin groups, but there was no significant difference (p > 0.05).
  • Keywords: Light cured composite resin; Leaching of residual monomers; pH variation; High performance liquid chromatography (HPLC)
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Figure 1
LC / MS-chromatogram of STD from Aeliteflo (Unpolymerized material)
jkacd-29-249-g001.jpg
Figure 2
LC / MS-chromatogram of pH 4 extract from Aeliteflo (Polymerized material)
jkacd-29-249-g002.jpg
Figure 3
LC / MS-chromatogram of pH 7 extract from Aeliteflo (Polymerized material)
jkacd-29-249-g003.jpg
Figure 4
LC / MS-chromatogram of STD from Z-250 (Unpolymerized material)
jkacd-29-249-g004.jpg
Figure 5
LC / MS-chromatogram of pH 4 extract from Z-250 (Polymerized material)
jkacd-29-249-g005.jpg
Figure 6
LC / MS-chromatogram of pH 7 extract from Z-250 (Polymerized material)
jkacd-29-249-g006.jpg
Figure 7
LC / MS-chromatogram of STD from Heliomolar (Unpolymerized material)
jkacd-29-249-g007.jpg
Figure 8
LC / MS-chromatogram of pH 4 extract from Heliomolar (Polymerized material)
jkacd-29-249-g008.jpg
Figure 9
LC / MS - chromatogram of pH 7 extract from Heliomolar (Polymerized material)
Peak A ; Internal caffeine standard, fragmented methyl methacrylate, methacrylic acid, etc.
Peak B ; TEGDMA (triethyleneglycol dimethacrylate)
Peak C ; UDMA (urethane dimethacrylate)
Peak D ; Bis-GMA (Bisphenol A diglycidyl ether dimethacrylate)
Peak E ; Unidentified, probably related to Bis-EMA (Ethoxylated bisphenol A dimethacrylate)
Peak F,G ; A certain dimer or oligomer
jkacd-29-249-g009.jpg
Figure 10
MS spectra of Caffeine (9min)
jkacd-29-249-g010.jpg
Figure 11
MS spectra of TEGDMA (14min)
jkacd-29-249-g011.jpg
Figure 12
MS spectra of UDMA (21min)
jkacd-29-249-g012.jpg
Figure 13
MS spectra of Bis-GMA (23min)
jkacd-29-249-g013.jpg
Figure 14
Leached TEGDMA of Aeliteflo
jkacd-29-249-g014.jpg
Figure 15
Leached UDMA of Z-250
jkacd-29-249-g015.jpg
Figure 16
Leached UDMA of Heliomolar
jkacd-29-249-g016.jpg
Figure 17
Total amount of leached monomers according to storage time
jkacd-29-249-g017.jpg
Table 1
Commercial light-cured dental composite resins used in this study.

Bis-GMA = Bisphenol A diglycidyl ether dimethacrylate

TEGDMA = Triethyleneglycol dimethacrylate

Bis-EMA = Etoxylated Bisphenol A dimethacrylate

Bis-EMA (6) = Bisphenol A polyetheylene glycol diether dimethacrylate

UEDMA = Urethane dimethacrylate

D3MA = Decamethacrylate

jkacd-29-249-i001.jpg
Table 2
Experimental conditions according to different pH and storage time.
jkacd-29-249-i002.jpg
Table 3
Dilution of standard solution (STD) and storage solution

*ppm = mg/L

jkacd-29-249-i003.jpg
Table 4
Conditions of HPLC
jkacd-29-249-i004.jpg
Table 5
Isolated monomers released at its specific retention time.

*Bis-EMA (6) ; Bisphenol A polyetheylene glycol diether dimethacrylate.

jkacd-29-249-i005.jpg
Table 6
Chemical structure of fragmented ions related to TEGDMA
jkacd-29-249-i006.jpg
Table 7
Chemical structure of fragmented ions related to UDMA
jkacd-29-249-i007.jpg
Table 8
Leached monomer content of Aelitflo groups

*%CF = percentage related to the internal caffeine standard

*STD = standard solution (unpolymerized material)

jkacd-29-249-i008.jpg
Table 9
Leached monomer content of Z-250 groups
jkacd-29-249-i009.jpg
Table 10
Leached monomer content of Heliomolar groups
jkacd-29-249-i010.jpg
Table 11
Amount of leached TEGDMA and UDMA according to storage time (%CF), n = 15

*: significantly different on the horizontal line (p < 0.001)

▸values with the same subscript letter in the same row are not significantly different (p > 0.05)

jkacd-29-249-i011.jpg
Table 12
Relative percentage of cumulative monomers following 45days storage as to original concentration

▾%CF = percentage related to the internal caffeine standard

*%Sol = percentage related to original concentration of STD

jkacd-29-249-i012.jpg

Tables & Figures

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      Effect of pH and storage time on the elution of residual monomers from polymerized composite resins
      J Korean Acad Conserv Dent. 2004;29(3):249-266.   Published online May 31, 2004
      DOI: https://doi.org/10.5395/JKACD.2004.29.3.249
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    Related articles
    Effect of pH and storage time on the elution of residual monomers from polymerized composite resins
    Image Image Image Image Image Image Image Image Image Image Image Image Image Image Image Image Image
    Figure 1 LC / MS-chromatogram of STD from Aeliteflo (Unpolymerized material)
    Figure 2 LC / MS-chromatogram of pH 4 extract from Aeliteflo (Polymerized material)
    Figure 3 LC / MS-chromatogram of pH 7 extract from Aeliteflo (Polymerized material)
    Figure 4 LC / MS-chromatogram of STD from Z-250 (Unpolymerized material)
    Figure 5 LC / MS-chromatogram of pH 4 extract from Z-250 (Polymerized material)
    Figure 6 LC / MS-chromatogram of pH 7 extract from Z-250 (Polymerized material)
    Figure 7 LC / MS-chromatogram of STD from Heliomolar (Unpolymerized material)
    Figure 8 LC / MS-chromatogram of pH 4 extract from Heliomolar (Polymerized material)
    Figure 9 LC / MS - chromatogram of pH 7 extract from Heliomolar (Polymerized material) Peak A ; Internal caffeine standard, fragmented methyl methacrylate, methacrylic acid, etc. Peak B ; TEGDMA (triethyleneglycol dimethacrylate) Peak C ; UDMA (urethane dimethacrylate) Peak D ; Bis-GMA (Bisphenol A diglycidyl ether dimethacrylate) Peak E ; Unidentified, probably related to Bis-EMA (Ethoxylated bisphenol A dimethacrylate) Peak F,G ; A certain dimer or oligomer
    Figure 10 MS spectra of Caffeine (9min)
    Figure 11 MS spectra of TEGDMA (14min)
    Figure 12 MS spectra of UDMA (21min)
    Figure 13 MS spectra of Bis-GMA (23min)
    Figure 14 Leached TEGDMA of Aeliteflo
    Figure 15 Leached UDMA of Z-250
    Figure 16 Leached UDMA of Heliomolar
    Figure 17 Total amount of leached monomers according to storage time

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    Effect of pH and storage time on the elution of residual monomers from polymerized composite resins

    Commercial light-cured dental composite resins used in this study.

    Bis-GMA = Bisphenol A diglycidyl ether dimethacrylate

    TEGDMA = Triethyleneglycol dimethacrylate

    Bis-EMA = Etoxylated Bisphenol A dimethacrylate

    Bis-EMA (6) = Bisphenol A polyetheylene glycol diether dimethacrylate

    UEDMA = Urethane dimethacrylate

    D3MA = Decamethacrylate

    Experimental conditions according to different pH and storage time.

    Dilution of standard solution (STD) and storage solution

    *ppm = mg/L

    Conditions of HPLC

    Isolated monomers released at its specific retention time.

    *Bis-EMA (6) ; Bisphenol A polyetheylene glycol diether dimethacrylate.

    Chemical structure of fragmented ions related to TEGDMA

    Chemical structure of fragmented ions related to UDMA

    Leached monomer content of Aelitflo groups

    *%CF = percentage related to the internal caffeine standard

    *STD = standard solution (unpolymerized material)

    Leached monomer content of Z-250 groups

    Leached monomer content of Heliomolar groups

    Amount of leached TEGDMA and UDMA according to storage time (%CF), n = 15

    *: significantly different on the horizontal line (p < 0.001)

    ▸values with the same subscript letter in the same row are not significantly different (p > 0.05)

    Relative percentage of cumulative monomers following 45days storage as to original concentration

    ▾%CF = percentage related to the internal caffeine standard

    *%Sol = percentage related to original concentration of STD
    Table 1 Commercial light-cured dental composite resins used in this study.

    Bis-GMA = Bisphenol A diglycidyl ether dimethacrylate

    TEGDMA = Triethyleneglycol dimethacrylate

    Bis-EMA = Etoxylated Bisphenol A dimethacrylate

    Bis-EMA (6) = Bisphenol A polyetheylene glycol diether dimethacrylate

    UEDMA = Urethane dimethacrylate

    D3MA = Decamethacrylate

    Table 2 Experimental conditions according to different pH and storage time.

    Table 3 Dilution of standard solution (STD) and storage solution

    *ppm = mg/L

    Table 4 Conditions of HPLC

    Table 5 Isolated monomers released at its specific retention time.

    *Bis-EMA (6) ; Bisphenol A polyetheylene glycol diether dimethacrylate.

    Table 6 Chemical structure of fragmented ions related to TEGDMA

    Table 7 Chemical structure of fragmented ions related to UDMA

    Table 8 Leached monomer content of Aelitflo groups

    *%CF = percentage related to the internal caffeine standard

    *STD = standard solution (unpolymerized material)

    Table 9 Leached monomer content of Z-250 groups

    Table 10 Leached monomer content of Heliomolar groups

    Table 11 Amount of leached TEGDMA and UDMA according to storage time (%CF), n = 15

    *: significantly different on the horizontal line (p < 0.001)

    ▸values with the same subscript letter in the same row are not significantly different (p > 0.05)

    Table 12 Relative percentage of cumulative monomers following 45days storage as to original concentration

    ▾%CF = percentage related to the internal caffeine standard

    *%Sol = percentage related to original concentration of STD

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    Restor Dent Endod : Restorative Dentistry & Endodontics
    © The Korean Academy of Conservative Dentistry.
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