Hydroxyethyl methacrylate (HEMA)와 Triethylene glycol ...

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Ⅰ. 치과용 복합레진의 주성분으로 사용되는 Bis- GMA는 점도가 높아서 제조와 조작상의 어려움이 있기 때문에 희석제를 배합하여 복합레진 점도를 감 소시킨다. 이 목적으로 널리 사용되어 온 것이 Triet- hylene glycol dimethacrylate (TEGDMA)이다. 1) TEGDMA는 분자 구조중에 수산기(-OH)나 카르 복실기(-COOH)를 가지지 않으므로 친수성이 나쁘 고 이에 따라 결합강도가 낮다. 따라서 상아질접착 제와 같이 치질결합을 목적으로 하는 제품에는 희석 제와 함께 친수성기를 가지고 있는 Hydroxyethyl methacrylate (HEMA)가 주로 사용되며, TEGDMA 와 Bis-GMA를 주성분으로 사용하지는 않는다. HEMA의 가장 큰 특징은 상아질에 대한 친화성과 침투성이며, 그 때문에 상아질접착제의 결합강도를 증가시키는 성분으로 사용되고 있다. 2) 일반적으로 상아질접착시에는 상아질접착제를 도포하고 그위에 복합레진을 결합시킨다. 복합레진 성분에 HEMA를 배합하면 복합레진의 상아질에 대한 결합강도가 증 가할 가능성이 있으며, 그러한 경우에는 별도의 상 아질접착제 도포과정이 생략될 있다. 아울러 HEMA의 친수성으로 인한 부피팽창을 가정할 수 있으며, 이와 같은 부피팽창은 레진의 중합수축을 보상하는 효과를 나타낼 수도 있다. HEMA의 상아질에 대한 친화성과 침투성에 관하 여는 많은 보고가 되어 왔는데, Gerzina와 Hume 3) TEGDMA와 HEMA의 상아질 침투성에 관한 연구 에서 치수강내에 압력을 가하여 단량체가 상아질 표 면으로부터 침투하기 어려운 조건을 부여하여도 HEMA는 여전히 높은 침투성을 보인다고 하였다. HEMA는 그것의 우수한 침투성 때문에 상아질 접착 제의 주성분으로 사용되고 있다. Gerzina와 Hume 4) 은 HEMA는 상아질에 대한 침 투성이 우수하기 때문에 HEMA와 TEGDMA를 함 께 사용할 경우 TEGDMA의 침투성까지 증진시킬 있다고 하였으며, Hamid와 Hume 5) 은 Bis-GMA TEGDMA 그리고 HEMA의 상아질 침투 및 투과 성을 분석하였는데, 그 결과에 따르면, HEMA는 1190.21nmol이 침투되는 것으로 나타났으며, TEGDMA는 86.21nmol을, Bis-GMA는 전혀 침투되지 않는 것으로 나타났다. 즉, HEMA는 TEGDMA에 비해 10배 이상 상아질에 대한 침투성 향을 가지며, 만약 Bis-GMA로만 복합레진을 제조한 다면 상아질에 대한 결합강도가 전무함을 의미한다. 이와 같은 HEMA의 침투성은 비닐라텍스도 침투 하여 통과할 있으며, 치과용 레진의 성분들이 비 닐라텍스를 통과하는데 소요되는 시간에 관하여 보 고한 Munksgaard 6) 에 의하면 HEMA의 경우 최대 7.54분이 소요되고, TEGDMA는 다소 길어진 8.61 분이었으며, 반면 Bis-GMA는 최대 100분 이상이라 고 하였다. 또한 HEMA는 TEGDMA에 비하여 생체친화성이 우수하다. Geurtsen등 7) 에 의하면 광중합형 글래스아 대한치과보철학회지:Vol. 41, No. 4, 2003 476 Hydroxyethyl methacrylate (HEMA)와 Triethylene glycol dimethacrylate (TEGDMA)가 실험적 복합레진의 특성에 미치는 영향 경희대학교 치과대학 치과보철학교실 한만형∙최부병∙우이형

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GMA

. Triet-
hylene glycol dimethacrylate (TEGDMA).1)
.

Hydroxyethyl
methacrylate (HEMA) , TEGDMA
Bis-GMA .
HEMA
,
.2)


,
.
HEMA
,
.
HEMA
, Gerzina Hume3)
TEGDMA HEMA


HEMA .
HEMA
.
, Hamid Hume5) Bis-GMA
TEGDMA HEMA
, , HEMA
1190.21nmol ,
TEGDMA 86.21nmol, Bis-GMA
TEGDMA 10
, Bis-GMA
.
HEMA
,

Munksgaard6) HEMA
7.54 , TEGDMA 8.61
, Bis-GMA 100
.
476

HEMA TEGDMA
diphenyliodoniumchloride
(DPICI) .
TEGDMA
.
HEMA
.
Asmussen Peutzfeldt8) Bis-GMA 25%
75% 75% TEGDMA
50% HEMA
134MPa
, Peutzfeldt Asmussen9) Bis-GMA
20% 20% HEMA
TEGDMA 69MPa
68MPa , 198MPa

.
Peutzfeldt Asmussen10,31) Urethane dimet-
Bis-GMA TEGDMA

, Eliades Palaghias11) HEMA

.
HEMA ,
.
Yap Lee12) HEMA
, Catani-
Lorente13) HEMA
.
HEMA TEGDMA
,
.

HEMA
.
. Bis-GMA TEGDMA HEMA
,
15%, 20%, 25% 30% .
1% 25
75%
. Camphoro-
quinone 0.4% . Aldrich
(Sigma-Aldrich Co., USA) .
TEGDMA HEMA
Fig. 1 Fig. 2 .
8, Bis-GMA
TEGDMA HEMA 15%, 20%, 25%, 30%
,
TEGDMA HEMA
477
dimethacrylate (TEGDMA).
late (HEMA).
Table I .

.
2.

10mm
40
1kg
.
. 10 .

. (4467, Instron
Co., USA)
1mm
,
. 10.
FS=3WL/2bd2
W: Load
L: Distance
b: Width
d: Thickness
2.5cm 2.0cm
.
600
3mm .
37% 60

3mm 1mm
40 .
37 24

, 1mm
. 10
.
2.5cm 2.0cm
.
600
3mm .
10% 30

3mm 1mm
40 .
37 24

478
T-1 21.25 3.75 - 75 100 15%
T-2 20.00 5.00 - 75 100 20%
T-3 18.75 6.25 - 75 100 25%
T-4 17.50 7.50 - 75 100 30%
H-1 21.25 - 3.75 75 100 15%
H-2 20.00 - 5.00 75 100 20%
H-3 18.75 - 6.25 75 100 25%
H-4 17.50 - 7.50 75 100 30%
Unit : Weight %.
Concentration(%)
.
.

1mm 5mm
40 .
37 24 10-4g
.
,
/mm3 .
11
,
,
.

,
.
range test 0.05
,
Two-way ANOVA .
.
1.
3.67mm, 4.57mm, 4.49mm, 4.71mm
, HEMA 4.00mm,
4.21mm, 4.62mm, 4.56mm .

, 25%
.
Fig. 4 .
.
.

(p=0.695)
(p<0.001).
T-1 3.67 0.16 4.40 3.93 3.50 C
T-2 4.57 0.24 5.18 5.02 4.25 A
T-3 4.49 0.36 7.96 5.15 3.93 A
T-4 4.71 0.37 7.96 5.35 4.24 A
H-1 4.00 0.19 4.81 4.26 3.67 B
H-2 4.21 0.27 6.36 4.63 3.87 B
H-3 4.62 0.30 6.51 5.08 4.28 A
H-4 4.56 0.32 7.07 4.88 3.95 A
Unit: mm, S.D.: Standard Deviation, C.V.: Coefficient of Variance.
Same characters written in column of Duncan's group mean no statistical differences between groups at 0.05
level.
Group
120.47MPa, 119.34MPa, 124.85MPa
108.76MPa, 116.33MPa, 118.30MPa, 127.75
MPa .
.
.
Table V ANOVA

(p=0.766)
(p=0.011).
Fig. 3. Comparison of depth of cure. Increase of the
contents of diluents made the depth of cure deeper.
At high contents groups such as 3 or 4, any significant
differences were not detected (Abbreviation,
T:TEGDMA, H:HEMA).
Fig. 4. Result of regression analysis for depth of cure
obtained by two diluents. Increase of the depth of cure
was obvious.
Table III. Result of ANOVA test for Depth of Cure
A N A L Y S I S O F V A R I A N C E
SCORE
X1 .010 1 .010 .155 .695
X2 7.730 3 2.577 38.666 .000
2-way Interactions .887 3 .296 4.438 .007
X1 X2 .887 3 .296 4.438 .007
Explained 8.619 7 1.231 18.477 .000
Residual 3.998 60 .067
Total 12.617 67 .188
of F
T-1 112.01 12.82 11.44 129.72 93.48 B
T-2 120.47 11.59 9.62 132.39 99.72 A
T-3 119.34 8.50 7.12 132.17 105.53 A
T-4 124.85 15.16 12.14 143.77 102.63 A
H-1 108.76 18.60 17.10 136.11 74.63 C
H-2 116.33 17.42 14.97 142.88 93.71 A
H-3 118.30 8.67 7.33 129.06 107.39 A
H-4 127.75 14.21 11.12 149.58 107.15 A
Unit: MPa, S.D.: Standard Deviation, C.V.: Coefficient of Variance.
Same characters written in column of Duncan's group mean no statistical differences between groups at 0.05 level.
Groups Mean S.D. C.V. Max. Min. Duncan's
Group
Fig. 5. Comparison of the flexural strength. Slight increase of flexural strength by the increase of the diluents was exhibited. But the significant differences between diluents were not clear (Abbreviation, T:TEGDMA, H:HEMA).
Fig. 6. Regression analysis result.
Table V. Result of ANOVA test for Flexural Strength
A N A L Y S I S O F V A R I A N C E
SCORE
X1 17.167 1 17.167 .090 .766
X2 2293.900 3 764.633 3.996 .011
2-way Interactions 102.410 3 34.137 .178 .911
X1 X2 102.410 3 34.137 .178 .911
Explained 2414.166 7 344.881 1.802 .102
Residual 12056.368 63 191.371
Total 14470.534 70 206.722
of F
. TEGDMA
29.13MPa, 30.28MPa, 35.93MPa
26.51MPa , HEMA
14.35MPa, 30.80MPa, 36.31MPa
27.01MPa .
Fig. 7 , T-2 H-2, T-3
H-3, T-4 H-4
.
.
, 25%
.
(p=0.186)
(p<0.001).
bovine enamel. Both of diluents showed the peak at
code-3 groups (Abbreviation, T:TEGDMA, H:HEMA).
Fig. 8. Result of regression test for enamel bond
strength. At 20%, 25%, 30%, two curves were over-
lapped.
Unit : MPa, S.D.: Standard Deviation, C.V.: Coefficient of Variance.
Same characters written in column of Duncan's group mean no statistical differences between groups at 0.05 level.
Groups Mean S.D. C.V. Max. Min. Duncan's
Group
483
Table VII. Result of ANOVA test for Enamel Bond Strength
A N A L Y S I S O F V A R I A N C E
SCORE
X1 116.500 1 116.500 1.792 .186
X2 1966.539 3 655.513 10.081 .000
2-way Interactions 635.932 3 211.977 3.260 .028
X1 X2 635.932 3 211.977 3.260 .028
Explained 2766.055 7 395.151 6.077 0.00
Residual 3901.481 60 65.025
Total 6667.536 67 99.515
of F
T-1 8.55 1.19 13.88 9.84 6.71 C
T-2 8.59 1.98 23.01 10.62 6.15 C
T-3 8.31 2.32 27.97 10.95 5.92 C
T-4 11.91 8.98 75.46 29.84 5.37 B
H-1 12.38 5.20 41.98 19.45 7.82 B
H-2 15.07 4.72 31.33 23.03 9.84 A
H-3 13.77 3.83 27.82 22.25 9.28 B
H-4 20.33 4.42 21.74 26.94 12.07 A
Unit: MPa, S.D.: Standard Deviation, C.V.: Coefficient of Variance.
Same characters written in column of Duncan's group mean no statistical differences between groups at 0.05 level.
Groups Mean S.D. C.V. Max. Min. Duncan's
Group
. Table
VIII Fig. 9 .
TEGDMA , 8.55MPa,
8.59MPa, 8.31MPa, 11.91MPa ,
HEMA 12.38MPa, 15.07MPa, 13.77
MPa, 20.33MPa .
TEGDMA
HEMA .
Table IX ANOVA
(p<0.001)
,
(p=0.010).
5.
. TEGDMA 16.60
/mm3, 16.28/mm3, 19.31/mm3, 18.86/mm3
, HEMA
22.93/mm3, 21.08/mm3, 24.02/mm3, 45.32
/mm3 .
HEMA TEGDMA
HEMA 30%
.
HEMA 30%
.
(p=0.002)
, (p=
0.022).
484
Table IX. Result of ANOVA test for Dentin Bond Strength
A N A L Y S I S O F V A R I A N C E
SCORE
X1 528.128 1 528.128 21.669 .000
X2 304.844 3 101.615 4.169 .000
2-way Interactions 40.213 3 13.404 .550 .651
X1 X2 40.213 3 13.404 .550 .651
Explained 832.865 7 118.981 4.882 0.00
Residual 1194.241 49 24.372
Total 2027.106 56 36.198
of F
HEMA and TEGDMA. HEMA always showed the
higher bond strength to dentin than TEGDMA
(Abbreviation, T:TEGDMA, H:HEMA).
the higher bond strength of HEMA to dentin
485
T-1 16.60 3.506 21.1 25.87 13.43 B
T-2 16.28 1.318 8.10 19.40 14.93 B
T-3 19.31 2.466 12.8 22.89 15.92 B
T-4 18.86 1.248 6.60 20.90 16.42 B
H-1 22.93 5.220 22.8 37.31 18.41 B
H-2 21.08 1.376 6.50 28.88 19.40 B
H-3 24.02 4.528 18.9 32.84 18.91 B
H-4 45.32 45.60 96.2 173.6 20.90 A
Unit: /mm2, S.D.: Standard Deviation, C.V.: Coefficient of Variance.
Same characters written in column of Duncan's group mean no statistical differences between groups at 0.05 level.
Groups Mean S.D. C.V. Max. Min. Duncan's
Group
increase of water absorption was occured at 30%
HEMA containing monomer group (Abbreviation,
T:TEGDMA, H:HEMA).
monomer. TEGDMA showed almost unchanged
trends compared to HEMA.
Table XI. Result of ANOVA test for Water Absorption
A N A L Y S I S O F V A R I A N C E
SCORE
X1 .002 1 .002 10.014 .002
X2 .003 3 .001 3.382 .022
2-way Interactions .002 3 .001 2.515 .064
X1 X2 .002 3 .001 2.515 .064
Explained .007 7 .001 3.958 0.01
Residual .020 80 .000
Total .027 87 .000
of F
HEMA ,
.
Fig. 13 . HEMA
,

.
50% 15% 25%
. 2-Hydroxyethyl methacrylate
(HEMA)
30% 55% .14)
HEMA
Qvist15) ,

Asmussen16) .
HEMA ,
Gerzina Hume3) .
TEGDMA HEMA


, TEGDMA
50nmol HEMA
150nmol
HEMA
.
HEMA
HPLC (High Performance Liquid Chromatograph)
. Bis-GMA
, TEGDMA
HEMA 13
.
,18)
486
Unit: /mm2, S.D.: Standard Deviation, C.V.: Coefficient of Variance.
Same characters written in column of Duncan's group mean no statistical differences between groups at 0.05 level.
Groups Mean S.D. C.V. Max. Min. Duncan's
Group
TEGDMA, H:HEMA).
,

.
HEMA TEGDMA
Bis-GMA 30%
20.33MPa 11.91
MPa HEMA
.
Bis-GMA 25%
30% .
7.5% HEMA
7.5%
.
HEMA

,
.
24
HEMA
,

.
HEMA TEGDMA
Bis-GMA 15% 30%
.

.
Bis-GMA
25%

.19)
HEMA
. Donly
Ingram20)
,
.
HEMA

.
Dragoo21)
HEMA
Qvist23) ,
HEMA
,
.
Camphoroquinone (CQ) Diphenyliod-
,
TEGDMA DPICI .
.
Bis-GMA HEMA
TEGDMA .
Bis-GMA

.

Peutzfeldt Asmussen10)
, TEGDMA
126MPa 155MPa
.
.

50%
.
.
,

.
487
75.2% ,
.
Peutzfeldt28)
.

.

.
.
Asmussen Peutzfeldt8) Bis-GMA
25% , 75% ,
75% TEGDMA , TEGDMA 25%
UDMA 25% , TEGDMA 25%
UDMA 25% HEMA 25% ,
TEGDMA 25% HEMA 50% 4
. 53MPa,
58MPa, 60MPa, 55MPa ,
134MPa, 181MPa, 186MPa 134MPa
. TEG-
DMA 75% TEGDMA 25% HEMA
50% ,
53MPa 55MPa HEMA
, 134MPa

. TEGDMA 124.85
MPa HEMA 127.75MPa
HEMA .
Asmussen Peutzfeldt8)

.
Asmussen Peutzfeldt29) TEGDMA
30%, 40%, 50%, 60%, 70%
52MPa, 52MPa, 52MPa, 54MPa,
53MPa , 140MPa, 149MPa,
152MPa, 140MPa, 141MPa 50%
.
, Asmussen
Peutzfeldt8) UDMA
.

.

.
Wendt30)
HEMA
TEGDMA

.
Peutzfeldt Asmussen31) Bis-GMA TEGDMA
.
Bis-GMA
,

,
.
Bis-GMA

,

.
, HEMA

, Eliades Palaghias11) HEMA

.
,
.
TEGDMA Matsukawa33)
. UDMA, Bis-GMA, TEGDMA,
MMA , ,
. 2.71%, 3.17%, 5.85%,
2.27% TEGDMA Bis-GMA
. HEMA
.
Yap Lee12) HEMA
488
.

.
Catani-Lorente13) HEMA
,

.
,

. Lee35)
.

.
Arima36)
, Tanaka36) O-methacryloyl-N- acryl tyrosines
(MAATY) , Fukushima38)
N-methylolacrylamide (MEAA) N-methylol-
, MEAA 5
.
HEMA TEGDMA
, ,
,
.
.

,

.
TEGDMA HEMA .
.
,
15%, 20%, 25%, 30% ,
8
. 25% TEGDMA
.
,
. 10
,
,

, 0.05 Duncan's
test ,
Two-way ANOVA test .
.
1. HEMA TEGDMA

(p>0.05).
(p<0.05) .
TEGDMA
(p<0.001).
(p<0.01).

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N-methylolacrylamide or N-methylol-
ty of a resin composite after 5 years.
491
Department of Prosthodontics, Division of Dentistry, Graduate School, Kyung Hee University
#1, Hoigi-Dong, Dongdaimun-Gu, Seoul, 130-701, Korea
[email protected]
Purpose : The purpose of this study was to compare HEMA and TEGDMA as diluents for the
composite resin.
Material and methods : Eight kinds of experimental light curable composite resins were pre-
pared and used. Concentrations of monomer and filler were same for all experimental compos-
ites, except, the diluent's ratios to the monomer. The ratio of diluents to Bis-GMA were 15%, 20%,
25%, and 30%, and two kinds of diluents were used, so total experimental groups were eight includ-
ing one control group of 25% TEGDMA.
Results : Depth of cure, flexural strength, shear bond strength to bovine enamel, shear bond
strength to bovine dentin, water absorption and solubility of composites in water were measured.
Sample size for each groups were 10. Arithmetic means were used as each groups representative
values, and regression test for two diluents and four concentrations, Duncan's multiple range test,
and Two-way ANOVA test were done for kinds of diluents and its concentrations at level of 0.05.
Conclusion :
Following results were obtained;
1. There were not significant differences in effects of HEMA and TEGDMA to depth of cure, flex-
ural strength of composites and shear bond strength to bovine enamel (p>0.05).
2. Increase of the concentrations of the diluents made the depth of cure (p<0.001) and flexural
strength (p<0.05) a little higher.
3. Shear bond strength to dentin was higher on HEMA containing composites than TEGDMA
containing composites (p<0.001).
4. Water absorption was higher on HEMA containing composites than TEGDMA containing com-
posites (p<0.01).
EFFECT OF HEMA AND TEGDMA ON THE PROPERTIES OF EXPERIMENTAL COMPOSITE RESINS
Man-Hyun Han, D.M.D., M.S.D., Boo-Byung Choi, D.M.D., D.D.Sc.,
Yi-Hyung Woo, D.M.D., M.S.D., Ph.D.
Department of Prosthodontics, Division of Dentistry, Graduate School, Kyung-Hee University, Seoul, Kores
492
ABSTRACT