modalidad estabilidad de color de resinas compuestas

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Color stability, conversion, water sorption and solubility of

dental composites formulated with different photoinitiator

systems

Pedro Paulo A.C. Albuquerque a, Allana D.L. Moreira a, Rafael R. Moraes b,Larissa M. Cavalcante a, Luis Felipe J. Schneidera,c,*a School of Dentistry, Federal Fluminense University, LABiom-R, R. Mario Santos Braga 30, 24020-140 Niteroi, RJ, BrazilbSchool of Dentistry, Federal University of Pelotas, R. Goncalves Chaves 457, 96015-560 Pelotas, RS, BrazilcSchool of Dentistry, Veiga de Almeida University, R. Ibituruna 108, Casa 3, 20271-020 Rio de Janeiro, RJ, Brazil

1. Introduction

Dental resin-based composites have been widely used as

direct and indirect restorative materials for anterior and

posterior teeth. Basically, these materials are composed of an

organic matrix, considered the active component, and

inorganic fillers as dispersive phase to ensure materials

properties.

The resin phase consists of dimethacrylate monomers

such as BisGMA (bisphenol-glycidyl dimethacrylate), UDMA

j o u r n a l o f d e n t i s t r y 4 1 s ( 2 0 1 3 ) e 6 7 e 7 2

a r t i c l e i n f o

Article history:

Received 26 September 2012

Received in revised form

6 November 2012

Accepted 27 November 2012

Keywords:

CamphorquinoneDental composites

FTIR spectroscopy

Phosphine oxides

Photosensitizers

Polymerization

a b s t r a c t

Objectives: The aim of this study was to formulate materials with high color stability and

reduced degradation by using photoinitiator systems derived from phosphine oxides

alternative to the traditional camphorquinone (CQ)/amine system.

Methods: Materials were formulated with the monomers BisGMA and TEGDMA as organic

matrix. The photoinitiators tested were CQ + amine (EDMAB), phenylbis(2,4,6-trimethylben-

zoyl)phosphine oxide (BAPO), BAPO + EDMAB, diphenyl(2,4,6-trimethylbenzoyl)-phosphine

oxide(TPO) andTPO + EDMAB.A 60%massof silanatedglass fillerparticles wasadded. Degree

of C C conversion was evaluated by Fourier-transformedinfrared spectroscopy 10 min after

photopolymerization. The color properties were evaluated by a digital spectrophotometer,applying the CIELab parameters, either before p hotoactivation, immediately after photoacti-

vation, 24 h after dry storage, and one month after water immersion. Water sorption and

solubility were assessed by mass gain or loss after storage in water for 30 days. Data were

analyzed using ANOVA and Tukeys test (5%).

Results: Degree of conversion did not differ statistically among all the tested formulations.

Regardingcolor, onlygroupswith TPO presented satisfactory color stability afterone month of

water storage (DE


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(urethane dimethacrylate), BisEMA (bisphenol-A-ethoxy

dimethacrylate) or TEGDMA (triethyleneglycol dimethacry-

late). In addition, radical scavenger is added to avoid

premature curing, as well as a photoinitiator system to trigger

the process of free radical development and complete the

polymerization reaction.1 Initially, these materials were

photoactivated by light sources emitting radiation in the

ultraviolet region(UV) of the spectrum, which has beenshownto cause oral and visual disorders for patients and clinicians

respectively.2,3 In addition, low depth of cure has been

associated with UV-cured materials. To address this situation,

visible-light curable composites were developed4 and the

photosensitizer camphorquinone (CQ) has been widely used

since then.5

Despite its popularity and relative success as photoinitia-

tor, CQ has some shortcomings. Besides presenting an intense

yellow coloration, CQ requires a co-initiator component,

which undergoes oxidation with time. Because these factors

negatively impact the optical properties of restorations with

time, other photoinitiator systems have been investigated to

replace or act jointly with CQ, such as phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (BAPO) and diphe-

nyl(2,4,6-trimethylbenzoyl)-phosphine oxide TPO. Basically,

these photoinitiators are classified as Norrish Type-I mole-

cules, which means that they do not need an amine co-

initiator and might react by direct cleavage.57 As aesthetic

qualities are one of the main reason for utilizing these

components, few studies exist that looked the degradation of

such materials and resultant changes in optical properties.810

To date there is no published data that investigated color

stability after storage conditions that simulate the oral

conditions.

The objectives of the present study were to evaluate the

degree of C C conversion (DC), water sorption and solubility,and to determine the color stability of dental composites

formulated with CQ + amine (EDMAB), TPO, TPO + EDMAB,

BAPO and BAPO + EDMAB. The following research hypotheses

were tested:

i. the alternative photoinitiator systems would be able to

promote similar DC as CQ + amine;

ii. groups formulated with BAPO and TPO would be able

to produce materials with lower water sorption and

water solubility than that material formulated with

CQ + amine;

iii. materials formulated with BAPO and TPO would show

improved color stability and lower yellowing effect thanthose materials formulated with CQ + amine.

2. Materials and methods

2.1. Preparation of the experimental composites

A BisGMA/TEGDMA (Esstech Inc., Essington, PA, USA) como-

nomer was obtained at a molar ratio of 60:40. The following

photoinitiator and co-initiator components (SigmaAldrich,

USA) were added, defining the groups to be studied:

CQ (1 mol%) + amine EDMAB (1 mol%)

TPO (1 mol%)

TPO (1 mol%) + amine EDMAB (1 mol%)

BAPO (1 mol%)

BAPO (1 mol%) + amine EDMAB (1 mol%)

Silanated filler particles were added at a 60% final weight:

20% of 2-mm bariumaluminiumsilicate (Esstech); 20% of 0.7-

mm bariumaluminiumsilicate (Esstech), 60% of 14-nm

silicon dioxide (Evonik Industries AG, Hanau-Wolfgang,Germany). All photoactivation procedures were carried out

with a quartztungstenhalogen curing unit (Optilux 501;Kerr,

Orange, CA, USA) with 600-mW cm2 irradiance.

2.2. Degree of C C conversion

The DC was evaluated using Fourier transform mid-infrared

spectroscopy (Prestige21; Shimadzu, Tokyo, Japan) with an

attenuated total reflectance device composed of a horizontal

multiple-reflection ZnSe crystal with 458 mirror angle (Pike

Technologies; Madison, WI, USA). A preliminary reading for

the unpolymerized material was taken under the following

conditions: 24 scans co-addition, 4 cm1 resolution, Happ-Genzel apodization, and 2.8 mm s1 mirror speed. After the

monomer reading, the composite was immediately photo-

activated for 40 s. A support was coupled to the spectrometer

to hold the curing unit and standardize a 0.5 mm distance

between the fibre tip and material.

TheDC was evaluated in theabsorbance mode 10 minafter

photoactivation. Calculation was carried out using a baseline

technique, considering the intensity of C C stretching

vibration (peak height) at 1635 cm1 and as an internal

standard, using the symmetric ring stretching at 1608 cm1.

Five specimens per material were tested under controlled

temperature (252 8C) and humidity (45 5%) conditions. DC

was calculated with the following formula:

%DC 100 1 CCcured=aromaticcuredCCuncured=aromaticuncured

2.3. Water sorption and solubility

Disc specimens were prepared by placing the resin composite

in a stainless steel mould (8.66 mm inner diameter, 0.6 mm

thickness) sandwiched between clear matrix strips (n= 6).

These measurements were used to produce a specimen with

the same dimensions ratio as specified in the ISO 4049

specification,11 and similar diameter of the light guide tip of

the curing unit. The specimen was photoactivated for 20 s ateach side with the light tip in direct contact with the strip.

Immediatelyafter curing, the specimens were transferred to a

desiccator maintained at 371 8C. After 22 h, specimens were

removed and stored in a second desiccator maintained at

251 8C for 2 h and weighed in a digital balance (AX200;

Shimadzu). This cycle was repeated until a constant mass (m1)

was obtained. The specimens were immersed in distilled

water at 371 8C for 30 days. After this period, the discs were

removed and washed with water. The excess water was

removed by blotting with a tissue and the specimens were re-

weighed (m2). After this weighing, the specimens were

reconditioned to constant dry mass (m3) in the desiccators

using the cycle described above for m1. The percentage

j o u r n a l o f d e n t i s t r y 4 1 s ( 2 0 1 3 ) e 6 7 e 7 2e68


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of water sorption (Wsp) and water solubility (Wsl) were

calculated as: Wsp = 100((m2m1)/m1), and Wsl = 100

((m1m3)/m1).

2.4. Color stability

A spectrophotometer (CM2600d; Konica Minolta, Ramsey, NJ,

USA) was used to evaluate the CIELab parameters of thespecimens. CIELab system is composed of 3 axes: L* (lightness,

from 0 = black up to 100 = white), a* (from a= green up to

+a= red) andb* (fromb= blue up to +b= yellow). The values

were based on D65 illuminant and a 108 observer. The color

changes (DE) were calculated by the following formula:

DE DL2 Da2 Db21=2

:

The resin composite was photoactivated for 40 s inside a

stainless steel mould (8.7 mm diameter, 1 mm thickness)

sandwiched between clear matrix strips (n= 5). Color read-

ings were performed before photoactivation, immediately

after the photoactivation procedure, and repeated after

90 min and 24 h storage at room temperature (251 8C)under dry conditions. Subsequently, the samples were

immersed in distilled water at room temperature and read-

ings were repeated after one month of storage (considering

the reading performed immediately after the photoactivation

procedure as baseline).

2.5. Statistical analysis

For each response variable tested (DC, Wsp, Wsl, and DEafter

one month), data were submitted to ANOVA and Tukeys post

hoctest (95% significance level).

3. Results

Table1 presents theresults forDC, Wsp, Wsl, andDE after one

month of water storage. The monomer conversion analysis

showed similar results for all groups (p= 0.052). There were

no statistical differences among the tested groups for the

water sorption (p= 0.340) and solubility (p= 0.390) tests.

Regarding the color stability, there were statistical differ-

ences(p

TPO. After40 s of lightexposure,there was a sharp decrease of

yellowing for CQ + EDMAB, whereas for BAPO and BAPO +

EDMAB the same decrease behaviour was not pronounced.

In contrast, those groups formulated with TPO and TPO +

EDMAB had a slight increase in yellow after the photoactiva-

tion procedure, but the b* were still lower than the other

groups.

Table 1 Means (standard deviations) for degree of C55Cconversion (DC), water sorption (Wsp), solubility (Wsl),and color change (DE) after one month of water storage.

DC, % Wsp, % Wsl, % DE

CQ + EDMAB 58.5 (1.0) 1 .5 (0.1) 0.3 (0.1) 3.8 (0.5) a

TPO 55.1 (1.5) 1.5 (0.1) 0.3 (0.1) 1.6 (0.9) b

TPO + EDMAB 53.5 (3.5) 1 .6 (0.1) 0.3 (0.1) 2.0 (0.3) b

BAPO 57.7 (5.0) 1.8 (0.1) 0.1 (0.1) 4.5 (0.9) aBAPO + EDMAB 57.1 (1.0) 1.7 (0.1) 0.2 (0.1) 4.8 (0.8) a

Distinct lowercase letters in a same column indicate significant

differences (p


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4. Discussion

In order to improve the optical and mechanical propertiesand overcome the shortcomings of dental composites

formulated with the CQ + amine system, alternative photo-

initiators have been studied. The use of such systems in the

formulation of dental composites could result, in theory,

in materials with high color stability and enhanced

resistance to degradation by hydrolysis, thus reducing the

necessity of replacing restorations. Due to the lack of

studies investigating these hypotheses, the current research

evaluated the DC, water sorption, water solubility and

color stability of dental composites formulated with

CQ + amine (EDMAB), TPO, TPO + EDMAB, BAPO and

BAPO + EDMAB.

The first hypothesis tested in the study was accepted, asthe DC was similar for all materials tested. Although the

alternative photoinitiators could present lower conversion

than CQ due to the fact that their maximum peak of light

absorption is in the UV region, such molecules also present a

light absorption curve extending towards the blue spectrum.13

Another factor that might account for the similarity in the

monomer conversion is the good light absorption of both TPO

and BAPO exposed to a visible light source. This significant

absorption observed at wavelengths between 440 and 420 nm

[

Fig. 2 a-Values (average and standard deviations) according to photoinitiator system used and the storage time/condition.

[

Fig. 4 b-Values (average and standard deviations) for each material before and after the photoactivation procedure.

[

Fig. 3 b-Values (average and standard deviations) according to photinitiator system used and the storage time/condition.



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is related to their effect on the polymerization of resin, which

provides a high efficiency of polymerization of the composite.8

For the current study, BAPO and TPO were tested with and

without the addition of an amine as co-initiator, and it is clear

that the addition of EDMAB did not lead to significant change

in DC. This outcome confirms previous studies suggesting that

BAPO and TPO do not require a co-initiator for effective

photopolymerization.1315 Following light absorption, BAPOand TPO are cleaved, generating reactive molecules capable of

initiating the polymerization process.13 CQ, in contrast, is

extremelydependent on the amine content, with directeffects

on the mechanical and optical properties of the material.15,16

The second hypothesis, that materials formulated with

BAPO and TPO would result in composites with lower

hydrolytic degradation, was rejected. The rationale of the

hypothesis was based on the results of a previous study

showing that TPO promotes a reaction rate much higher than

that produced by CQ15; the higher rate could generate

increased crosslink density of the polymer network. However,

allgroups showed similarwatersorptionand solubility. Thisis

in line with the results for DC, and could be explained by theuse of the same comonomer for all materials, with conse-

quently similar hydrophilicity.17

According to the color analysis, the third research

hypothesis that the experimental composites formulated

with BAPO or TPO would produce materials with higher color

stability than CQ/amine was partially accepted, as only the

groups formulatedwith the TPOhad better color stability. This

result is most likely related to the fact that TPO exhibits a

much higher molar extinction coefficient than BAPO,18

meaning that the first component presents a much higher

probability of molecule consumption than the latter. A

detailed analysis of the different axes is also important, as

follows.Analysis of the color coordinates indicates that all groups

showed L* values quite constant during the experiment.

Regarding the a*-axis, the outcomes ranged from negative

(green) to positive values (red), indicating that all groups

showed a reddish color after 1 month of water storage. This

finding might be related to the proximity of the colors yellow

and red in the electromagnetic spectrum, with leaching of the

photoinitiators also potentially influencing these values.19

Regarding the b*-axis values over time (Fig. 3) it can be

observed that 24 h after the initial measurements, all speci-

mens became more yellow than immediately after photo-

activation. This behaviour can be explained by the fact that

photoinitiators that were not consumed during the polymeri-zation process might return to their original state a slow

process due to vitrification of the polymer. In Fig. 3it can also

be seen an abrupt decrease ofb*-values after one month of

water storage for all groups this is explained by the leaching

of such photoinitiator components that were not consumed

during light exposure.

On onehand, thegroupsformulated with TPOexhibitedthe

lowest overall yellowing tint, regardlessof the addition of a co-

initiator, reading period or storage condition.Fig. 4details the

b*-axis values obtained before and immediately after the

photoactivation procedure, where and it is clear the photo-

bleaching ability of CQ. In contrast, BAPO did not show high

photobleaching, while TPO exhibited higher yellowing after

photoactivation. According to Hadis et al.,9 this effect might be

related to monomer discoloration and that such effect would

be more pronounced at the initial stages of polymerization,

when monomer molecules surround oxygen present in the

mixture. Additionally, the authors claim that TPO is a very

reactive molecule and presents a very high rate of polymeri-

zation. As a consequence, there is a high temperature

development that might cause the formation of coloredperoxides, which would develop this yellowing effect follow-

ing photoactivation. This is an interesting approach to explain

the results, but it should also bore in mind that new radicals

are formed after the cleavage of TPO. Consequently, the

formation of colored radicals that are not consumed after the

polymerization process should also be considered, and

additional studies regarding this subject are encouraged.

5. Conclusion

Within the limitations of the present study, the following

conclusions can be drawn:

I. Groups formulated with BAPO and TPO generate materials

with a degree of C C conversion similar to composites

made with CQ, regardless of the presence of a co-initiator;

II. The photoinitiator type did not affect water sorption and

solubility of the composites;

III. Materials formulated with TPO presented higher color

stability than composites containing BAPO and CQ after

ageing in water.

Conflict of interest statement

There is no conflict of interest to declare.

Acknowledgements

This work was supported by FAPERJ/Brazil grant E-26/111.658/

2010. The authors thank Esstech Inc. and Degussa Evonik for

donation of the materials. P.P.A.C.A. and A.D.L.M. gratefully

acknowledge the scientific initiation scholarships granted by

CNPq/PIBITI/UFF, Brazil.

r e f e r e n c e s

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2. Rueggeberg FA. From vulcanite to vinyl, a history of resins inrestorative dentistry.The Journal of Prosthetic Dentistry2002;87:36479.

3. Ruyter IE, Oysaed H. Conversion in different depths ofultraviolet and visible light activated composite materials.

Acta Odontologica Scandinavica 1982;40:17992.4. Cook WD. Factors affecting the depth of cure of UV-

polymerized composites.Journal of Dental Research

1980;59:8008.

j o u r n a l o f d e n t i s t r y 4 1 s ( 2 0 1 3 ) e 6 7 e 7 2 e71
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