Eur J Oral Sci 2009; 117: 442–446  2009 The Authors.

Printed in Singapore. All rights reserved Journal compilation  2009 Eur J Oral Sci
European Journal of
Oral Sciences

Flvia GonÅalves1, Yoshio Kawano2,

Influence of BisGMA, TEGDMA, and Carmem Pfeifer3, Jeffrey W.
Stansbury3, Roberto R. Braga1
BisEMA contents on viscosity, 1
Department of Dental Materials, University of
S¼o Paulo, S¼o Paulo ; 2Department of

conversion, and flexural strength of Fundamental Chemistry, University of S¼o

Paulo, S¼o Paulo, Brazil; 3Department of
Craniofacial Biology, University of Colorado

experimental resins and composites Health Science Center, Aurora, CO, USA

Gonçalves F, Kawano Y, Pfeifer C, Stansbury JW, Braga RR. Influence of BisGMA,

TEGDMA, and BisEMA contents on viscosity, conversion, and flexural strength of
experimental resins and composites. Eur J Oral Sci 2009; 117: 442–446.  2009
The Authors. Journal compilation  2009 Eur J Oral Sci

Different monomer structures lead to different physical and mechanical properties for
both the monomers and the polymers. The objective of this study was to determine the
influence of the bisphenylglycidyl dimethacrylate (BisGMA) concentration (33, 50 or
66 mol%) and the co-monomer content [triethylene glycol dimethacrylate (TEG-
DMA), ethoxylated bisphenol-A dimethacrylate (BisEMA), or both in equal parts] on
viscosity (g), degree of conversion (DC), and flexural strength (FS). g was measured
using a viscometer, DC was obtained by Fourier transfer Raman (FT-Raman) spec-
troscopy, and FS was determined by three-point bending. At 50 and 66% BisGMA,
increases in g were observed following the partial and total substitution of TEGDMA
by BisEMA. For 33% BisGMA, g increased significantly only when no TEGDMA
was present. The DC was influenced by BisGMA content and co-monomer type.
Roberto R. Braga, Department of Materiais
Mixtures containing 66% BisGMA showed a lower DC compared with mixtures
Dentrios, FOUSP, Av. Prof. Lineu Prestes,
containing other concentrations of BisGMA. The BisEMA mixtures had a lower DC 2227, 05508-000 S¼o Paulo, SP, Brazil
compared with the TEGDMA mixtures. The FS was influenced by co-monomer
content only. BisEMA mixtures presented a statistically lower FS, followed by Telefax: +55–11–30917840, ext. 201
E-mail: rrbraga@usp.br
TEGDMA + BisEMA mixtures, and then by TEGDMA mixtures. Partial or total
replacement of TEGDMA by BisEMA increased g, which was associated with the Key words: degree of conversion; physical
properties; resin composite
observed decreases in DC and FS. Although the BisGMA content influenced the DC,
it did not affect the FS results. Accepted for publication March 2009

The majority of commercial dental composites use
bisphenylglycidyl dimethacrylate [BisGMA, molecular
weight (MW) = 512 g] as the base monomer of the resin
matrix (1). As a result of its high viscosity
(600–1,000 PaÆs), the use of diluent co-monomers becomes
necessary to allow incorporation of the inorganic filler
(2, 3). The co-monomer most commonly used is triethylene
glycol dimethacrylate (TEGDMA). Its low MW
(286 g mol)1) and low viscosity (g = 0.05 PaÆs) reduce
the viscosity of the mixture, significantly increasing the
polymer degree of conversion (DC) (4, 5). However, the
increased conversion granted by TEGDMA causes a
clinically undesirable increase in polymerization shrink-
age (5, 6). For this reason, monomers with low viscosity
and high MW, such as ethoxylated bisphenol-A dimeth-
acrylate (BisEMA:MW = 540 g mol)1; g = 3 PaÆs), are
present in several commercial formulations, partially or
totally replacing TEGDMA.
The mechanical performance of resin composites is
closely related to their formulation (7, 8). Generally
speaking, the molecular backbone characteristics of the
co-monomers involved will determine the hydrophilicity,
mobility, and kinetic parameters, which, in turn will
influence the DC (5, 9, 10). However, the effect of
co-monomer composition on the resistance of a material
to fracture and deformation is controversial. For exam-
ple, a study analyzing composites with different Bis-
GMA : TEGDMA ratios observed that high
concentrations of the former resulted in higher flexural
strength (FS) (7). Another study, however, verified that
increasing the base-monomer concentration in
BisGMA : TEGDMA composites did not affect their
FS, although the DC was significantly reduced (5).
Similarly, the increase in BisGMA concentration in
composites containing diurethane dimethacrylate
(UDMA) and TEGDMA led to significant reductions
only in the DC, whereas their mechanical properties were
not substantially affected (11).
The influence of the BisEMA content on the
mechanical behavior of resin composites has not been
extensively investigated. Unfilled resins containing Bis-
GMA and BisEMA at concentrations of 50:50 or

30:70 wt% showed a significantly lower DC (approxi-
mately 25% lower) and elastic modulus (up to 34%
lower) compared with BisGMA : TEGDMA resins at
similar ratios (12, 13). Another study verified that the
total replacement of BisGMA by BisEMA in composites
with TEGDMA resulted in higher conversion, but no
improvement was observed in flexural and diametral
tensile strengths (14).
Composite initial (i.e. uncured) viscosity is a determi-
nant of its potential DC (15, 16). High-viscosity mono-
mers have a relatively high glass transition temperature
(Tg) and therefore there is limited range for conversion
before the Tg of the developing polymer reaches the cure
temperature, resulting in vitrification. As a consequence,
polymerization is prevented from progressing further at
relatively low conversion values (12). Initial viscosity is
also directly related to polymerization shrinkage (17, 18)
and to shrinkage stress (19). However, other studies
observed, in vitro, a lower incidence of marginal gaps in
restorations created using low-viscosity (flowable)
commercial composites, supposedly because of a higher
stress relief caused by viscoelastic deformation (18).
Clinically, low-viscosity composites showed improved
adaptation to cavity preparations compared with mate-
rials of regular viscosity, with a lower incidence of
defects and porosities at the interface (20, 21).
The objective of this study was to evaluate the influence
of BisGMA concentration and co-monomer content
(TEGDMA, BisEMA, or both, in equal parts) on the
viscosity and DC of unfilled resins and on the FS of
composites. For each of the variables evaluated, the null
hypothesis was that the studied response is not affected by
the BisGMA concentration or the co-monomer content.
Material and methods
Formulation of the experimental composites
All chemicals were used as received. Nine formulations were
prepared (Table 1) containing BisGMA (bisphenylglycidyl
dimethacrylate or 2,2-bis[4-(2-hydroxy-3-methylacryloxy
propoxy)phenyl]propane; Esstech, Essington, PA, USA)
associated with TEGDMA (triethylene glycol dimeth-
acrylate or 2-methyl-2-propenoic acid; Esstech), BisEMA
(ethoxylated bisphenol-A dimethacrylate or 2,2-bis[4-
(2-hydroxy-3-methylacryloxyethoxy)-phenyl]propane; Sigma-
Aldrich, St Louis, MO, USA) or both monomers in equal
parts. Co-initiator [2-(dimethylamino)ethyl methacrylate;
Sigma-Aldrich], inhibitor (2,6-di-tetra-butyl-4-methylphe-
Table 1
Formulations of the experimental resins
A B C D
BisGMA 33.3 33.3 33.3 50
TEGDMA 66.6 33.3 – 50
BisEMA – 33.3 33.3 – 25
For testing the flexural strength, 40 wt% of fumed silica was added.
BisEMA, ethoxylated bisphenol-A dimethacrylate; BisGMA, bisphenylglycidyl dimethacrylate; TEGDMA, triethylene glycol
dimethacrylate.
Properties of dimethacrylate resins 443
nol; Sigma-Aldrich), and camphorquinone (camphorqui-
none; Sigma-Aldrich) were added, each at 0.5 wt%. For
flexural tests, silanated fumed silica (OX-50, 0.04 lm;
Degussa, Americana, Brazil) was added to mixtures at
40 wt%. Composites were mixed by hand, in an environ-
ment without any artificial light, and stored for 2 d in
the dark at room temperature before use. This procedure
allowed time for air bubbles, admixed in the material during
preparation, to surface because the resulting composites had
relatively low viscosity.
Viscosity
The viscosities of the unfilled resins (n = 3) were determined
in a viscometer (CAP 200+ Viscometer; Brookfield Engi-
neering Laboratories, MA, USA), at 2,684 g and 25C.
Samples were held in place for 5 s before being submitted to
shear for 30 s. Shear rates of 667 s)1 (small-diameter spindle)
or 2,667 s)1 (high-diameter spindle) were used for higher-
viscosity and lower-viscosity samples, respectively.
Degree of conversion
Degree of conversion, assessed by Fourier-transformed
Raman spectrometry (FT-Raman; RFS 100/S; Bruker Op-
tics, Billerica, MA, USA), was performed in cylindrical
specimens, prepared by sandwiching the uncured material
confined by a plastic mould, 5 mm in diameter and 1 mm
thick, between mylar strips and glass slides. A radiant
exposure of 16 J cm)2 (420 mW cm)2 for 38 s) was deliv-
ered to the resin using a quartz–tungsten–halogen light-
curing unit (VIP Junior; BISCO, Schaumburg, IL, USA).
Specimens were dry stored for 48 h at 37C before testing.
Spectra of the polymerized specimens were collected from
the non-irradiated bottom surface. The same procedure was
carried out for the uncured materials. Spectra were obtained
by the co-addition of 64 scans at a resolution of 4 cm)1. The
Raman spectrometer is equipped with a neodymium-doped
yttrium aluminium garnet (Nd-YAG) laser, emitting radi-
ation at 1,064 nm at an intensity of 100 mW. The ratio
between the peak heights of the aliphatic (1,640 cm)1) and
aromatic (1,610 cm)1) carbon double bond absorptions for
the cured and uncured composite was used to calculate the
DC according to the formula:
 
polymerized
DC ¼ 1  100
unpolymerized
Flexural strength
For each experimental group, bar-shaped specimens
(10 · 2 · 1 mm3, n = 10) were built using a stainless-steel
Resins
E F G H I
50 50 66.6 66.6 66.6
25 – 33.3 16.5
50 16.5 33.3
444 Gonçalves et al.
split mould. The composite confined by the mould was
sandwiched between mylar strips and glass slides, with
pressure applied to ensure consistent thickness in all speci-
mens. Photoactivation was performed as described for DC.
After dry storage at 37C for 48 h, the specimens were
submitted to three-point bend testing in a universal testing
machine (Instron 5565; Instron, Canton, MA, USA), with a
6-mm span between the supports at a crosshead speed of
0.5 mm min)1. The load at fracture and the specimen
dimensions (determined individually using a digital caliper)
were used to calculated the FS, according the formula:
3LD
FS ¼
2  w  h2
where L is the load at fracture (N), D is the distance
between the supports, w is the width, and h is the height
of the specimen, all in mm.
The small-sized bars were used with the intent of irradi-
ating the entire sample with one shot of light, so radiant
exposure would be standardized. As the intent was to rank
the materials according to their FS, and not to compare our
results with others reported in the literature, we opted for
standardizing the radiant exposure, which would not have
been possible with the use of longer specimens that would
have required multiple exposures to light.
Statistical analysis
Data were analyzed using the two-way analysis of variance
(anova)/Tukey test, with BisGMA concentration and
co-monomer content as main factors. A pre-set global
level significance of 5% was used for all tests. Previously,
data were tested for homogeneity of variance and normality,
using Levene and Anderson–Darling tests, respectively.
Results
Means and standard deviations for viscosity are shown
in Table 2. The interaction between the factors BisGMA
concentrations and co-monomer content was statisti-
cally significant (P < 0.001). At BisGMA concentra-
tions of 50 and 66%, statistically significant increases
in viscosity were observed both with the partial and
total substitution of TEGDMA by BisEMA. For
resins containing 33% BisGMA, however, viscosity
increased significantly only when no TEGDMA was
present.
Table 2
Mean and standard deviations of viscosity
TEGDMA
E E
33% BisGMA 0.15 ± 0.001
50% BisGMA 0.76 ± 0.02E
66% BisGMA 5.7 ± 0.02C
Viscosity (PaÆs) of experimental resins containing different BisGMA concentrations and types of co-monomer. Similar letters indicate
the absence of statistically significant differences [two-way analysis of variance (anova)/Tukey test, a = 0.05]. Comparisons among
all groups (P < 0.001).
BisEMA, ethoxylated bisphenol-A dimethacrylate; BisGMA, bisphenylglycidyl dimethacrylate; TEGDMA, triethylene glycol
dimethacrylate.
Results of DC are shown in Table 3. The interaction
was not significant (P = 0.649). However, the DC was
influenced both by BisGMA concentration and by
co-monomer content (P < 0.001 and P < 0.05, respec-
tively). The DC did not change between 33 and 50%
BisGMA (66.9 ± 1.6 and 65.0 ± 2.7%, respectively),
but it was significantly lower for the resins containing
66% BisGMA (56.4 ± 1.5%). Mixtures with TEGDMA
showed statistically higher conversion (64.0 ± 4.9%)
than those with BisEMA (61.3 ± 4.5%), while resins
containing both co-monomers reached intermediate
conversion (63.0 ± 5.8%), statistically similar to
composites with only TEGDMA or only BisEMA as
co-monomer.
The means and standard deviations of FS are dis-
played in Table 4. anova did not reveal a statistically
significant effect for the interaction (P = 0.157) or Bis-
GMA concentration (P = 0.160). Only for co-monomer
content were statistically significant results obtained
(P < 0.001). The composites containing TEGDMA
(108.8 ± 17.1 MPa) showed higher FS than those with
both TEGDMA and BisEMA (95.1 ± 11.8 MPa),
which, in turn had higher FS than the composites for-
mulated with BisEMA (80.5 ± 9.9 MPa).
Discussion
The null hypothesis can be rejected with respect to vis-
cosity because a significant interaction between BisGMA
concentration and co-monomer content was verified.
One possible explanation for this finding relies on the
fact that BisGMA is capable of promoting strong
hydrogen bonding through the hydroxyl group. Its rigid
backbone favors intermolecular bonding rather than
intramolecular interactions (10) and also restricts
mobility, which is a function of its high molecular weight
(2, 12). Other factors, like the less favorable molecular
packing and consequently higher free volume, help to
explain the higher viscosity for BisGMA-rich mixtures.
The fact that mixtures with BisEMA, a monomer with a
structure which is almost identical to that of BisGMA,
except for the fact that the hydroxyl groups are not
present, showed decreased viscosity values, adds evi-
dence to the importance of hydrogen bonding in deter-
mining viscosity. Conversely, mixtures where TEGDMA
Viscosity (PaÆs)
TEGDMA + BisEMA BisEMA
0.65 ± 0.02 3.7 ± 0.06D
3.2 ± 0.02D 14.9 ± 0.65B
14.6 ± 0.35B 29.2 ± 0.45A
 Properties of dimethacrylate resins 445

Table 3
Mean and standard deviations of degree of conversion (%)

Degree of conversion (%)

TEGDMA TEGDMA + BisEMA BisEMA BisGMA factor mean
A A B
33% BisGMA 67.6 ± 0.6 67.7 ± 1.0 65.3 ± 1.6 66.9 ± 1.6a
50% BisGMA 66.7 ± 2.1A 65.3 ± 3.4A 62.9 ± 1.6B 65.0 ± 2.7a
66% BisGMA 57.6 ± 0.6A 55.8 ± 1.5A 55.7 ± 1.9B 56.4 ± 1.5b
Co-monomer factor mean 64.0 ± 4.9a 63.0 ± 5.8ab 61.3 ± 4.5b

Degree of conversion (%) of experimental resins containing different BisGMA concentrations and co-monomer type. Similar letters
indicate the absence of statistically significant differences [two-way analysis of variance (anova)/Tukey test, a = 0.05]. Upper case
letters refer to comparisons among all groups values (P = 0.649), whereas lower case letters refer to comparisons among pooled
averages for each factor (BisGMA concentration: P < 0.001; co-monomer: P = 0.015).
BisEMA, ethoxylated bisphenol-A dimethacrylate; BisGMA, bisphenylglycidyl dimethacrylate; TEGDMA, triethylene glycol
dimethacrylate.

Table 4
Mean and standard deviations of flexural strength (%)

Flexural strength (MPa)

TEGDMA TEGDMA + BisEMA BisEMA BisGMA factor mean
ABC ABC D
33% BisGMA 100.8 ± 13.4 99.3 ± 13.7 79.6 ± 10.5 93.2 ± 15.6a
50% BisGMA 116.0 ± 19.6A 95.5 ± 11.9BCD 84.1 ± 8.0CD 98.5 ± 19.1a
66% BisGMA 109.6 ± 15.6AB 90.4 ± 8.9CD 77.8 ± 11.0D 92.6 ± 17.7a
Co-monomer factor mean 108.8 ± 17.1a 95.1 ± 11.8b 80.5 ± 9.9c

Flexural strength (%) of experimental composites containing different BisGMA concentrations and co-monomer types. Similar
letters indicate the absence of statistically significant differences [two-way analysis of variance (anova)/Tukey test, a = 0.05]. Upper
case letters refer to comparisons among all groups (P = 0.157), and lower case letters refer to comparisons among pooled averages
for each factor (BisGMA concentration, P = 0.160; co-monomer, P < 0.001).

or both co-monomers were present, showed lower vis-
cosity, as expected (2, 10, 12), based on the previous
discussion. It was observed that mixtures with a high
concentration of TEGDMA (50 and 66%) and also the
formulation of 66% TEGDMA + BisEMA, which had
a relatively lower concentration of hydrogen bonds to be
disrupted, had lower viscosity.
The null hypotheses also can be rejected with respect
to DC. Although the interaction was not statistically
significant, the DC was influenced by both co-monomer
content and BisGMA concentration. Mixtures with
TEGDMA showed a higher DC than those with
BisEMA. Some molecular features that influence the
kinetic parameters can be considered to explain this fact.
First, the lower molecular weight of TEGDMA facili-
tates packing, once the free volume among the specimens
can be better accommodated with the presence of a
smaller molecule. This alone increases the chance of
termination by disproportionation [when two free radi-
cals terminate each other (22)]. Second, this molecule is
highly flexible as a result of the presence of ether linkages
in the backbone, which leads to primary cyclization
(which contributes to conversion but not to overall
mechanical properties) and increases the rate of termi-
nation at higher conversion levels (5, 12, 23, 24). Also,
the low Tg of TEGDMA ()83.4C), in comparison with
the other dimethacrylate monomers (BisGMA: )7.7C,
BisEMA: )46.1C) lowers the Tg of the monomeric
mixture, leading to higher DC before polymer vitrifica-
tion (12, 14). Regarding the BisGMA concentration, the
statistically lower conversion reached by the resin con-
taining 66% BisGMA can be explained by the mobility
restrictions imposed by vitrification reached at relatively
low conversion (12). Also based on the mobility of the
reactive species, it could be expected that the resin con-
taining 33% BisGMA would show higher conversion
than that containing 50% BisGMA. However, it has
been observed that higher polymerization rates cause the
onset of autodeceleration and vitrification to occur at a
later stage in conversion (16, 25). Therefore, it is possible
that the higher reaction rate of the more viscous 50%
BisGMA material would have offset the effect of the
lower mobility of the reaction medium (16).
In the present study, no relationship between viscosity
and DC was verified, probably because of the little vari-
ation in conversion observed among materials. Because of
their different structures and reactivities, and also the fact
that intermolecular and intramolecular interactions in the
uncured state and during the polymerization are not the
same, it is possible to obtain similar degrees of conversion
from mixtures with very dissimilar viscosities (26, 27).
Furthermore, for resins containing the same monomers in
different concentrations, no relationship between con-
version and viscosity was found. This could be explained
by the fact that viscosity is inversely related to the degree
of conversion only up to a level where the decrease in
viscosity starts to negatively affect conversion as a result
of increased diffusion-controlled termination (16).
446 Gonçalves et al.
Regarding flexural strength, the null hypotheses can be
partially rejected because, although flexural strength was
not influenced by the BisGMA concentration, it did vary
with the co-monomer content. Composites formulated
with TEGDMA had a higher FS than those formulated
using BisEMA or both co-monomers. These results agree
with previous findings indicating that a higher discrep-
ancy in chain length between monomers increases poly-
mer strength (8) and it can be explained by a number of
factors. TEGDMA mixtures reached a higher DC than
BisEMA mixtures. Moreover, the fact that TEGDMA
has three ether linkages from the glycol group (not ste-
rically hindered from a stiff backbone) besides the two
carbonyls from the methacrylate (10), makes it a more
efficient hydrogen bond acceptor than BisEMA, which
presents the ether linkages and the methacrylate carbo-
nyls shielded by a large, relatively stiff molecule. So, an
increased crosslink density is attributed to a synergic
effect between TEGDMA and BisGMA, whereas an
internal plasticizing effect is attributed to BisEMA, as a
result of its high molecular weight, which reduces the
crosslink density of the polymer (8, 13).
The lack of a statistically significant influence of
BisGMA concentration on FS confirms the findings of
previous investigations (5, 11). The FS of the composites
is the result of the interplay between antagonistic factors.
On the one hand, the increase in BisGMA concentration
reduces FS as a result of lower polymer conversion and
crosslink density (5, 12). On the other hand, the stiff
backbone of BisGMA, as well as the strong hydrogen
bonding responsible for maintaining the conformation of
the network structure, contributes to the increase in
polymer strength (5, 10, 15).
It can be concluded, within the conditions of this study,
that the best compromise between increased conversion
and high FS was obtained with resin matrix containing up
to 50 mol% BisGMA and either TEGDMA or both
TEGDMA and BisEMA in equimolar concentrations.
The total replacement of TEGDMA by BisEMA
negatively affected the DC and the composite FS.
Acknowledgements – The authors would like to express their
gratitude to FAPESP (04/059750) and CNPq for funding this
project, and to Esstech and Degussa for kindly donating,
respectively, the monomers and the filler used in the composite
preparation.
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