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

Cheol-Min Jeon; Hyun-Mi Yoo; Hyuk-Choon Kwon

doi:10.5395/JKACD.2004.29.3.249

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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; Journal of Korean Academy of Conservative Dentistry 2004;29(3):249-266.
DOI: https://doi.org/10.5395/JKACD.2004.29.3.249
Published online: May 31, 2004

¹Department of Conservative Dentistry, College of Dentistry, Seoul National University, Korea.

²Department of Conservative Dentistry, The Institute of Oral Health Science, Samsung Medical Center, Sungkyunkwan University, School of Medicine, Korea.

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

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Abstract
REFERENCES

Abstract

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)

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

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

Tables & Figures

REFERENCES

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

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

Figure 1

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Figure 8

Figure 9

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Figure 11

Figure 12

Figure 13

Figure 14

Figure 15

Figure 16

Figure 17

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

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

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