journal of dentistry 40 (2012) 711–717

Available online at www.sciencedirect.com

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Degree of conversion of two-step etch-and-rinse adhesives:

In situ micro-Raman analysis

Chiara Ottavia Navarra a, Lorenzo Breschi a,b,*, Gianluca Turco a, Marina Diolosà a,
Luca Fontanive a, Lucia Manzoli c, Roberto Di Lenarda a, Milena Cadenaro a
a
Department of Medical Sciences, University of Trieste, Piazza dell’Ospitale, 1, I-34125 Trieste, Italy
b
IGM, Unit of Bologna, C.N.R. – IOR, Bologna, Italy
c
Department of SAU&FAL, University of Bologna, Bologna, Italy

article info abstract

Article history: Objectives: DC of three commercial two-step etch-and-rinse adhesives across the dentine–
Received 8 February 2012 adhesive interface was investigated using micro-Raman spectroscopy. The hypothesis
Received in revised form tested was that no difference in DC would exist among the adhesives tested.
2 May 2012 Methods: Adper Scotchbond 1XT (3M ESPE), Prime&Bond NT (Dentsply DeTrey), and Ambar
Accepted 3 May 2012 (FGM) were applied on human dentine disks (n = 9). Composite increments of 2 mm were
then applied on the adhesive surface. Raman spectra were collected along the dentine–
adhesive interface. The relative intensities of the peaks associated with the mineral (PO43
Keywords: at 960 cm1) and the adhesive (C C at 1640 cm1; phenyl C C at 1610 cm1) were used to
Two-step etch-and-rinse adhesives identify the adhesive within the hybrid layer and calculate its DC.
Degree of conversion Results: Adper Scotchbond 1XT and Ambar showed similar DC (79  7% and 77  7%,
Micro-Raman spectroscopy respectively), while a lower DC was found for Prime&Bond NT (70  7%; p < 0.05).
Hybrid layer Conclusions: The hypothesis tested was rejected because differences were found among the
adhesives tested. The difference in DC among the three adhesive systems can be attributed
to different monomer compositions and solvents. Further studies are needed to correlate DC
with other mechanical properties of these adhesives.
Clinical significance: Insufficient polymerization of an adhesive can result in a weak
hybrid layer, and the presence of unreacted monomers may result in degradation of the
polymeric network, decreasing the strength and longevity of the bond. In the present study,
Adper Scotchbond 1XT and Ambar performed significantly better than Prime&Bond NT.
# 2012 Elsevier Ltd. All rights reserved.

clinical time, and reducing the technique sensitivity of

1. Introduction
The clinical performance of present day adhesives has
significantly improved, allowing adhesive restorations to be
placed with a high predictable level of clinical success.
The versatility of adhesive dentistry has prompted the
steady development of new bonding agents, with the aims of
simplifying their clinical application, shortening side-chair
procedures. In accordance with their application mode,
dentine bonding systems can be divided into etch-and-rinse
and self-etch (or etch-and-dry) adhesives.1,2 Because the
adhesive mixture should be able to prime and bond simulta-
neously to the hydrophilic collagen network, high concentra-
tions of hydrophilic monomer and solvents characterize the
formulations of two-step etch-and-rinse adhesives.3 In-
creased hydrophilicity of monomers favours phase separation

* Corresponding author at: Department of Medical Sciences, University of Trieste, Piazza dell’Ospitale, 1, I-34125 Trieste, Italy.
Tel.: +39 0403992192; fax: +39 0403996128.
E-mail address: lbreschi@units.it (L. Breschi).
0300-5712/$ – see front matter # 2012 Elsevier Ltd. All rights reserved.
http://dx.doi.org/10.1016/j.jdent.2012.05.001
712 journal of dentistry 40 (2012) 711–717

within the hybrid layer4,5 resulting in a marked reduction in

mechanical strength which may compromise the durability of
resin-dentine bonds.6,7
In fact, bond stability to dentine can differ among the
various adhesives used,8–10 and the supposed benefit of
time-saving in two-step versus three-step etch-and-rinse
adhesives can be nullified if the quality of the bond is
compromised.7
A low percentage of monomer to polymer conversion of
adhesives11 is related to low physicochemical properties,12
and suboptimally polymerized resins may exhibit higher
elution of monomers than specimens with higher degrees of
conversion (DCs),12–14 and this in turn, may influence the
stability of the bond.11,12 Only a few studies have investigated
the DC of etch-and-bond adhesives,15 moreover only a few
studies estimated adhesives’ DC and the kinetic of the
polymerization reaction without considering the interactions
of the material with the dentinal tissue.16 Thus, an in situ
analysis of their DC may be an important factor in predicting
adhesive performance in vivo.
Thus, the aim of this study was the evaluation of the
ability of three commercially available two-step etch-and-
rinse systems to polymerize into the hybrid layer. The
hypothesis tested was that no difference would exist in the
DCs of adhesives tested, as assessed using micro-Raman
spectroscopy.
2. Materials and methods
2.1. Teeth preparation and bonding procedures
Non-carious human third molars (n = 9) stored in 0.5%
chloramine in water at 4 8C were collected after informed
consent was obtained from patients under a protocol
approved by the University of Trieste, Italy. A low-speed
diamond saw with water cooling (Micromet; Remet, Bologna,
Italy) was used to expose middle/deep dentine, and a uniform
smear layer was obtained with 180-grit silicon carbide paper to
simulate the bur’s action.
The dentine disks were then randomly and equally
assigned to the three tested adhesives (n = 3): Group 1, Adper
Scotchbond 1XT (SB; 3M ESPE, St. Paul, MN, USA. Lot 8RH),
Group 2, Prime&Bond NT (PB; Dentsply DeTrey, Konstanz,
Germany. Lot 0810002903), and Group 3, Ambar (AM; FGM,
Joinville, SC, Brazil. Lot 160410). Adhesive compositions and
application modes are listed in Table 1. Dentine bonding
systems were applied in accordance with the manufacturers’
instructions and polymerized for 10 s using a quartz-halogen
lamp (Elipar 2500; 3 M ESPE) with an irradiance of
600 mW mm2, as previously assayed using a 400–500 nm
radiometer (100 Optilux radiometer; SDS Kerr, Danbury, CT,
USA) and a tip to adhesive surface distance of 1 mm. A 2-mm

Table 1 – Composition, mode of application, and DC for each of the adhesives tested, as recommended by the respective
manufacturer.
Adhesive system Composition Application mode (after 15 s dentine etch) DC (%)
Group 1: SB Ethyl alcohol Apply to tooth surface and brush for 15 s 79  7 b
Silane-treated silica Expose to airstream
BisGMA Light cure for 10 s
HEMA
Glycerol 1,3-dimethacrylate
Copolymer of acrylic and itaconic acids
Water
UDMA
Photoinitiators
Group 2: PB Acetone Apply to dentine and let it wet for 20 s with continuous 70  7 a
UDMA brushing
Polymerizable dimethacrylate resins Expose to a gentle airstream at least for 5 s
Polymerizable trimethacrylate resins Light cure for 10 s
PENTA
Nanofillers-amorphous silicon dioxide
Photoinitiators
Stabilizers
Cetylamine hydrofluoride
Group 3: AM UDMA Apply to dentine in two layers with continuous brushing 77  7 b
HEMA Gently air dry for 10 s
Acid methacrylated monomers Light cure for 10 s
Hydrophilic methacrylated monomers
Ethanol
Silica nanofiller
Photoinitiators
Coinitiators
Stabilizers
Different superscript letters indicate statistical differences ( p < 0.05).
Abbreviations: bisphenol A diglycidyl ether dimethacrylate (BisGMA), dipentaerythritol penta acrylate monophosphate (PENTA), 2-hydroxyethyl
methacrylate (HEMA), urethane dimethacrylate (UDMA).
 journal of dentistry 40 (2012) 711–717
increment of resin composite (Filtek Z250; 3 M ESPE. Lot
N248789) was layered on the adhesive surface and light-cured
for 20 s. Each specimen was then cut transversally to obtain
two 2-mm slabs which were polished to expose the adhesive
interface for micro-Raman analysis, in accordance with
Navarra et al.17. Polishing was performed as follows: a first
polish for 30 s with wet SiC papers up to 800 grit, followed by 6,
1, and 0.05 mm diamond pastes, with distilled water rinsing
between each step. Slabs were then cleaned with soap,
sonicated for 30 min and rubbed with a cotton swab saturated
with 5% sodium hypochlorite to rid the surface of smeared
proteins produced by polishing. The specimens were stored in
air and analyzed in 24 h. The specimens were stored dry in a
dedicated cupboard at controlled room temperature (22 8C)
with silica gel to obtain a dry environment.
2.2. Micro-Raman spectroscopy
The equipment used consisted of a computer-controlled laser
Raman microprobe connected to a DM/LM optical microscope
with a 100 objective (NA 0.9; N Plan EPI objective; Leica,
Wetzlar, Germany) and a CCD detector attached to a modular
research spectrograph (Renishaw InVia; Renishaw PLC, New
Mills, Wotton-under-Edge, Gloucestershire, UK). The 100
objective increased the precision of the beam, resulting in a
laser spot size of 1 mm. A monochromatic, near-infrared
diode 785-nm laser was used to induce the Raman scattering
effect. The spectral range of this model was from 100 to
3450 cm1, with an average spectral resolution of 5 cm1. A
wavelength and intensity calibration was performed with a
silicon standard using the calibration system integrated with
the software (WiRE 2.0; Renishaw PLC) before each experiment
following the manufacturer’s specifications.
The 18 dentine slabs were analyzed by acquiring spectra
in three line-scans for each slab, starting in the sound
mineralized dentine and ending in the adhesive resin layer.
One Raman spectrum was collected every 1 mm along the
Fig. 1 – Representative micro-Raman spectrum of mineralized dentine. At 960 cmS1, the band associated with the mineral
PO43S group is clearly visible (arrow), while the bands at 1245 cmS1 (C–N), 1450 cmS1 (CH2), and 1667 cmS1 (C O) are
associated with the dentine organic components (pointers).
713
dentine–adhesive interface in the intertubular region (laser
wavelength 785 nm; Renishaw InVia; Renishaw PLC) using a
computer-controlled motorized x–y–z stage, with an expo-
sure time of 40 s and a laser power on the specimen of
8 mW. Data were acquired over the spectral region from
400 to 1900 cm1. They were analyzed with software
developed for spectrographic analysis (Grams/AI 7.02;
Thermo Galactic Industries, Salem, NH, USA).
2.3. Conversion calculation
To detect the hybrid layer within the adhesive interface, the
relative intensities of bands associated with mineral dentine
components (the PO43 functional group at 960 cm1) and
adhesive (vinyl C C at 1640 cm1 and phenyl C C at
1610 cm1) were identified. Fig. 1 shows a Raman spectrum
of human dentine. The major peak at 960 cm1 is associated
with the mineral PO43 group, while the bands at 1245 (C–N),
1450 (CH2), and 1667 cm1 (C O) are associated with the
dentine organic components.18 Raman spectra of each
uncured adhesive were also collected to identify the reference
and reaction peaks needed for conversion calculations (Fig. 2).
The phenyl C C peak at 1610 cm1, stable and unchanging
during polymerization, was selected as a reference peak, while
the vinyl C C 1640 cm1 peak was selected as a reaction peak.
The DC was calculated using the ratio between the reaction
(Arxn) and internal reference (Aref) peak areas, as follows:
( )
½Arnx ð pÞ=Are f ð pÞ
%conversion ¼ 1   100
½Arnx ðuÞ=Are f ðuÞ
where ‘‘u’’ refers to unpolymerized and ‘‘p’’ to the polymerized
adhesive system.
2.4. Statistical analysis
The data were checked for normality and equal variances
using Kolmogorov–Smirnov and Bartlett’s tests and analyzed
714 journal of dentistry 40 (2012) 711–717
Fig. 2 – Spectra of representative uncured adhesives. The peaks at 1610 cmS1 (phenyl, C C) and 1640 cmS1 (vinyl C C group)
were considered as reference and reaction peaks, respectively, for the DC calculation in the systems examined.
using one-way ANOVA. Statistical significance was set at
p < 0.05.
3. Results
Representative Raman spectra acquired in line scans across
the adhesive interface are shown in Fig. 3. Overlapping spectra
acquired in the same region demonstrated the technique’s
reproducibility.
Means and standard deviations (SDs) of DC percentages
and statistical differences among adhesives are reported in
Table 1. SB and AM showed similar values of DC (79  7% and
77  7%, respectively), while a significantly lower DC was
found for PB (70  7%; p < 0.05).
4. Discussion
The present study investigated the curing capabilities of three
commercially available two-step etch-and-rinse adhesives
(SB, PB, AM) within the hybrid layer using micro-Raman
spectroscopy when applied on human dentine.
The spectroscopic techniques are suitable methods to
acquire chemical information from a substrate, and although
the micro-FTIR spectroscopy can also provide a high spatial
resolution map of molecular vibrational changes, micro-
Raman spectroscopy was chosen because it is less sensitive
to water, requires minimal specimen preparation and it can
directly measure the double-bond converted percentage in situ
within the hybrid layer, with the advantage that it is a
nondestructive technique.17–21 In this study, spectra of
uncured materials were acquired (assumed to have DC = 0%)
to calculate the C C bond peak ratio by comparing them to the
spectra obtained with the cured adhesives. The spectroscopic
analysis clearly showed in all specimens a gradual decrease in
the intensity of the hydroxyapatite peak at 960 cm1 towards
the dentine on the adhesive side of the hybrid layer with a
simultaneous increase in the peaks attributable to the
adhesives (1640 cm1 and 1610 cm1). The 1610 cm1 was
attributable to the phenyl C C bond, and although an
aromatic compound was disclosed by the manufacturer only
for the SB composition, the 1610 cm1 peak was also clearly
visible in AM and PB; thus, it was chosen as a reference peak
(Fig. 2).
The hypothesis tested was rejected because the selected
adhesives showed significantly different DCs.
The tested materials have a different composition, as
showed in Table 1, and this can have influenced the obtained
results. A first difference consists in the type of organic solvent
used (acetone in PB, and ethanol in AM and SB).
Previous studies showed that acetone-based adhesives are
more technique-sensitive because of the extreme volatility of
this solvent (four times higher than that of ethanol),22 and Bail
et al. demonstrated that incomplete solvent evaporation can
negatively affect the DC, the solubility, and the water sorption
of acetone-based experimental resins.23 Yiu et al. reported
that when experimental mixtures with known compositions
were analyzed, more solvent was retained in ethanol-based
than in acetone-based mixtures,24 but the authors did not
correlate these results with polymerization of the mixtures
tested; thus, the results could have been different if
commercial adhesives had been considered. Regardless of
the type of solvent used, its concentration can negatively
affect DC; residual solvents may dilute the monomers,
curbing the process of reticulation.25,26 If residual solvent
remains entrapped in the polymer network, localized areas of
incomplete polymerization are present,27 leaving residual
unreacted monomers more susceptible to leaching.28,29
Cadenaro et al.25 demonstrated that high ethanol percen-
tages (>50 mass%) may compromise the extent of polymeri-
zation of dental adhesives, measured by differential scanning
 journal of dentistry 40 (2012) 711–717 715

Fig. 3 – Micro-Raman spectra acquired with 1-mm step across the adhesive–dentine interface produced by SB (3a), PB (3b),
and AM (3c). In all figures, the first spectrum was collected in mineralized dentine: the arrows indicate the PO43S group. The
simultaneous decrease in the phosphate peak and increases in the adhesive peaks at 1610 cmS1 and at 1640 cmS1
(pointers) suggest the beginning of the hybrid layer.
716 journal of dentistry 40 (2012) 711–717
calorimetry, due to residual solvent entrapped within the
polymer network.
Adhesives that in the present study showed similar DC
in situ (AM and SB) were previously shown to have comparable
bond strengths.30 Moreover, two-step etch-and-rinse adhe-
sives containing acetone were previously demonstrated to
have low polymerization,15 failure of the bond over time,28,31
and poor in vivo performance.32,33 Sarr et al.34 compared the
bonding effectiveness of 11 commercial dental adhesives,
finding that when PB was compared to SB in terms of
immediate micro-tensile bond strength, PB showed the lowest
values among all etch-and-rinse adhesives tested and partic-
ularly lower results than SB. The same findings were also
reported in long-term micro-tensile studies.35,36
A second difference in composition among the tested
adhesive is the monomer mixture. The role of monomer
viscosity in the DC of the methacrylate-based adhesive was
previously assayed using mixtures of known compositions:
decreasing the viscosity increased the DC.37,38 The UDMA
present in SB and AB is a linear, long-chain cross-linker that
has a molecular weight comparable with Bis-GMA, but higher
flexibility,3 and consequently would be expected to react more
readily due to its vinyl functional monomer. The –NH– groups
of UDMA increase the mobility of radical sites of the polymer
network.39 On the other hand, the PENTA (contained in PB) has
a high molecular weight due to a long principal linear organic
chain with four long lateral chains; this structure negatively
affects its mobility and flexibility and thus restricts the
probability for the lateral functional monomers to react.
SB and AB also contain HEMA, a small and fluid molecule
with a ‘‘solvent-like’’ behaviour. After the majority of the
polymerization occurs, the long chain monomers are restricted
in the polymer network, while low-molecular-weight HEMA can
flow in the resins, continuing to react with the unreacted C C.
Previous studies clarified that simplified adhesives (i.e.,
two-step etch-and-rinse and one-step self-etch) adhesives
exhibit a lower DC and higher adhesive permeability than
their un-simplified counterparts (i.e., three-step etch-and-
rinse and two-step self-etch) due to the presence of hydro-
philic monomers and solvents.40–42,2,43 This in situ study
suggests that two-step etch-and-rinse have the different
behaviour when applied on human dentine, related probably
to the different solvent content.
5. Conclusions
The overall result of this study demonstrated that the DC of
the three two-step etch-and-rinse commercial adhesives,
evaluated within the hybrid layer at the dentine–adhesive
interface, is material-dependent. Additional studies are
required to clarify how the different DC can influence the
stability of the hybrid layer over time, and thus the clinical
performance of the different bonding agents.
Acknowledgments
The authors report no conflict of interest and wish to thank
Mr. Aurelio Valmori for technical assistance. The study was
partially founded with grants from MIUR (Italy): FIRB
RBAP1095CR to Breschi L (P.I.) and to Cadenaro M (P.I.), PRIN
2009SAN9K5 to Breschi L (P.I.) and to Manzoli L (P.I.) PRIN
2009FXT3WL to Di Lenarda R (P.I.).
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