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J Dent Res 82(8): 597-601, 2003
© 2003 International and American Associations for Dental Research

RESEARCH REPORT
Biomaterials & Bioengineering

Effects of HEMA/Solvent Combinations on Bond Strength to Dentin

R.M. Carvalho1,*, J.S. Mendonça1, S.L. Santiago1, R.R. Silveira1, F.C.P. Garcia1, F.R. Tay2, and D.H. Pashley3

1 Department of Operative Dentistry, Endodontics and Dental Materials, University of São Paulo, Bauru School of Dentistry, FOB USP, Depto. Dentística, Al. Otávio P. Brisola 9-75, Bauru, SP, 17012-101, Brazil;
2 Conservative Dentistry, Faculty of Dentistry, University of Hong Kong, Hong Kong, SAR, China; and
3 Department of Oral Biology and Maxillofacial Pathology, School of Dentistry, Medical College of Georgia, Augusta, GA, USA;

* corresponding author, ricfob{at}fob.usp.br


   ABSTRACT
TOP
 ABSTRACT
INTRODUCTION
 MATERIALS & METHODS
 RESULTS
 DISCUSSION
 REFERENCES
 
Re-expansion of dried demineralized dentin is required to optimize resin adhesion. This study tested the hypothesis that bond strengths to dentin depend upon the ability of experimental HEMA(2-hydroxy-ethyl-methacrylate)/solvent primers to re-expand the matrix. Dentin surfaces were acid-etched with 37% phosphoric acid for 20 sec, air-dried for 30 sec, primed with either 35/65% (v/v) HEMA/water, HEMA/methanol, HEMA/ethanol, or HEMA/propanol for 60 sec, and bonded with 4-META-TBBO(4-methacryloyloxyethyl trimellitate anhydride-tri-n-butyl borane) adhesive. After storage in water for 1 day at 37°C, the samples were prepared for microtensile bond strength testing. We used transmission electron microscopy to measure the width of interfibrillar spaces in the hybrid layers. The HEMA/ethanol primer and the HEMA/propanol primer produced the highest and the lowest bond strengths, respectively (p < 0.05). Bond strengths were directly correlated with the width of the interfibrillar spaces (p < 0.05). Bond strengths are related to the ability of the primer to maintain the re-expansion of collapsed demineralized dentin matrix.

KEY WORDS: microtensile bond strength • dentin • solvents


   INTRODUCTION
TOP
 ABSTRACT
 INTRODUCTION
MATERIALS & METHODS
 RESULTS
 DISCUSSION
 REFERENCES
 
When demineralized dentin matrix is air-dried, it may collapse up to 65% in volume (Carvalho et al. 1996). During dehydration, collagen fibrils are brought into closer contact, facilitating a variety of weak molecular associations between polypeptide chains that were not possible in the presence of water. Such interpeptide forces stabilize the structure of dry dentin and make it stiffer (Maciel et al., 1996). This shrinkage phenomenon reduces the interfibrillar spaces that serve as diffusion channels for resin infiltration, and ultimately compromises the bonding of adhesive systems to dentin (Gwinnett, 1994).

One way to overcome the shrinkage problem is to re-wet the dentin surface with water before bonding (Gwinnett, 1994). Water is the strongest known hydrogen bonding (H-bonding) solvent (Barton, 1991). It forms clusters around the collagen residues that prevent interpeptide H-bonding. Water breaks the interpeptide bonds in dried collagen due to its higher H-bonding capacity, plasticizing the collagen fibrils and filling the interfibrillar spaces. This causes the matrix to re-expand to its full extent (Carvalho et al., 1996; Pashley et al., 2001) and re-creates the interfibrillar spaces that are necessary for resin infiltration (Pashley et al., 2000). Another approach is to use a bonding agent that contains water or other strong H-bonding solvents that are capable of breaking any interpeptide collagen H-bonds in dried dentin. The ability of water-based primers to re-expand dried, demineralized dentin, originally described by Sugizaki (1991), has been recently confirmed and described as a self-expansion phenomenon (Van Meerbeek et al., 1998).

While some adhesives are water-based, others use ethanol or acetone as solvents. If such water-free adhesives are applied to demineralized, dried, collapsed dentin, the re-expansion will be dependent on the ability of solvents or monomers to associate with collagen and break interpeptide H-bonds (Pashley et al., 2001). Ideally, a primer solution that is applied to demineralized, dried dentin should contain solvents that have a higher ability to H-bond with collagen than the peptides have for themselves, to permit adequate opening of the interfibrillar spaces for resin penetration. Incomplete expansion may impair resin infiltration and compromise bonding. This study tested the effects of several HEMA(2-hydroxy-ethyl-methacrylate)/solvent mixtures as primer on the bond strength of resin applied to demineralized, dried dentin surfaces. The rationale was that different solvents will produce different degrees of re-expansion, depending upon their H-bonding capacity, thus allowing for different degrees of resin infiltration that ultimately result in different bond strengths. The null hypothesis tested is that there is no effect of HEMA/solvent mixtures on the resin/dentin bond strength.


   MATERIALS & METHODS
TOP
 ABSTRACT
 INTRODUCTION
 MATERIALS & METHODS
RESULTS
 DISCUSSION
 REFERENCES
 
Flat dentin surfaces were created on mid-coronal dentin of extracted human third molars by means of a slow-speed diamond saw (Isomet, Buehler Ltd., Lake Bluff, IL, USA). The teeth were collected after the patient’s informed consent was obtained under a protocol approved by the Medical College of Georgia Institutional Review Board. The flat dentin surfaces were polished with wet 600-grit silicon carbide paper and then etched with 35% phosphoric acid (3M ESPE, St. Paul, MN, USA) for 20 sec, rinsed with water, and air-dried for 30 sec with oil-free compressed air. The dried surface was then immediately primed with 20 µL of one of the 35 vol% HEMA/65 vol% solvent solutions. The solvents used were: water (control), methanol, ethanol, and n-propanol. The primed surfaces were left undisturbed for 60 sec, gently air-dried with air (5 sec), and subsequently bonded with 4-META/TBBO(4-methacryloyloxyethyl trimellitate anhydride-tri-n-butyl borane) adhesive agent (Amalgambond, Parkell, Farmingdale, NY, USA) without using the primer in the adhesive kit. Composite buildups were constructed with Z-100 resin composite (3M ESPE) in five 1-mm increments. The bonded teeth (3 per group x 4 groups = 12 teeth) were stored in 37°C distilled water for 24 hrs before being tested.

Tensile Bond Strength Testing and Failure Mode Analysis
The bonded teeth were vertically, serially sectioned in both "x" and "y" directions at approximately 0.8-mm intervals by means of an Isomet saw. After examination under a microscope at 10X, some beams were discarded due to the presence of peripheral enamel or imperfections in the bonded interface. This procedure yielded 20–25 bonded beams per group. Each beam was tested in tension in a testing machine (Model 4440, Instron Inc., Canton, MA, USA) operating at a cross-head speed of 1.0 mm/min, by the microtensile testing method (Pashley et al., 1999). After being tested, the fractured specimens were removed, and the cross-sectional area at the site of fracture was measured with a digital caliper (Starret, CA505, Starret Inc., SP, Brazil) so that bond strengths could be calculated in megapascals (MPa).

The fractured specimens were examined under 40X and the failure mode classified as being cohesive within the material or substrate, adhesive at the interface, or mixed failures.

Ultrastructural Analysis of Untested Resin-Dentin Interfaces and Silver Uptake
Separate bonded dentin discs were produced according to the 4 experimental groups. Discs were cut in halves that were either completely demineralized in buffered ethylene-diamine-tetraacetic-acid (EDTA, pH = 7.0) or immersed in 50% ammoniacal silver nitrate for 24 hrs, followed by exposure to light and photodeveloper (Tay et al., 2002). They were then processed for electron microscopy according to the protocol described by Tay et al.(1999). Demineralized, epoxy-resin-embedded, 70- to 90-nanometer-thick ultrathin sections were double-stained with 1% phosphotungstic acid and 2% uranyl acetate for 10 min each and examined under a transmission electron microscope (Philips EM208S, Philips, Eindhoven, The Netherlands) operating at 80 kV. Undemineralized, silver-exposed sections were not stained. Digitized images were recorded by means of the charge couple device (CCD) camera (Bioscan, Model 792, Gatan Inc., Pleasanton, CA, USA). All micrographs were taken at the same magnification from regions that were within 1.5 µm of the bonded surface. The average width of the interfibrillar spaces and the average diameter of the collagen fibrils were directly measured on the images with the aid of Image Tool software (UTHSCSA, San Antonio, TX, USA).

Statistical Analyses
Load at failure and cross-sectional area data were analyzed by Sigma Stat 2.03 (Jandel Sci. Ltd., Chicago IL, USA). Since there were slight differences among the mean cross-sectional areas of the 4 groups, bond strengths of all groups were adjusted by the least-squares means to a standard cross-sectional area of 0.8 mm2 (Nakajima et al., 1995). For each group, we applied a regression analysis (MPa vs. cross-sectional area) to find the best least-squares method line that fit the data. Each individual bond strength value (MPa) was then re-calculated to a new value for a standard cross-sectional area by use of the equation of the least-squares line. The averaged, adjusted bond strength values were then expressed as least-squares means values. Adjusted bond strength values were analyzed by one-way analysis of variance and Student-Newman-Keuls tests. Statistical significance was set in advance at {alpha} = 0.05. Regression analysis was used to obtain the best least-squares fit of bond strengths vs. Hansen’s solubility parameters (Barton, 1991) of the HEMA/solvent mixtures, and of bond strength values vs. the average width of the interfibrillar spaces.


   RESULTS
TOP
 ABSTRACT
 INTRODUCTION
 MATERIALS & METHODS
 RESULTS
DISCUSSION
 REFERENCES
 
The highest bond strength was obtained after dry dentin was treated with HEMA/ethanol primer (p < 0.05) followed by HEMA/methanol and HEMA/water, which were not different between each other (p > 0.05). Lower bond strengths were observed after dentin was treated with HEMA/propanol primer (p < 0.05) (TableGo). Most of the bond failures were either adhesive or mixed. The HEMA/propanol group showed only adhesive failures. No cohesive failures in dentin or resin were observed.


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  		Table. Bond Strengths, Interfibrillar Widths, and Fibril Diameters of HEMA/Solvent-primed Dentin
 
Regression analysis demonstrated that the correlation between average bond strength and Hansen’s triple solubility parameters of the solvents ({delta}d, {delta}p, {delta}h for dispersive, polar, and hydrogen bonding forces, respectively) and the primer mixtures was not significant (R2 values ranging from 0.19 to 0.49, p > 0.05; data not shown). However, when bond strengths were plotted against the average width of the interfibrillar spaces, a moderate to strong correlation was observed (R2 = 0.84, r = 0.92, p < 0.1; Fig. 1Go).



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  		Figure 1. Regression analysis of bond strength vs. width of interfibrillar spaces.

 
Transmission Electron Microscopic (TEM) Analysis of the Interfaces
Transmission electron micrographs of the hybrid layers formed with the 4 experimental primers (Fig. 2Go) show that interfibrillar space widths and fibril diameters in both the ethanol and methanol groups were significantly wider (TableGo, p < 0.05) than those in the water and propanol groups. The diameters of the collagen fibrils were not significantly different in the water, methanol, and ethanol groups (p > 0.05), but they were significantly smaller in the propanol group (p < 0.05). Silver uptake was minimal in the methanol group, slight in the ethanol group, moderate in the water group, and heavy in the propanol group. For the ethanol, water, and propanol groups, there was a predilection for silver uptake along the base of the hybrid layer.



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  		Figure 2. Representative transmission electron micrographs of silver-impregnated and non-impregnated bonded interfaces. (A,B) Specimens primed with 35 vol% HEMA in water. (A) Stained demineralized specimen. (B) Unstained, non-demineralized specimen immersed in silver nitrate. (C,D) Specimens primed with 35 vol% HEMA in methanol. (C) Stained demineralized specimen. (D) Unstained, non-demineralized specimen immersed in silver nitrate. (E,F) Specimens primed with 35 vol% HEMA in ethanol. (E) Stained, demineralized specimen. (F) Unstained, non-demineralized specimen immersed in silver nitrate. (G,H) Specimens primed with 35 vol% HEMA in propanol. (G) Stained, demineralized specimen. (H) Unstained, non-demineralized specimen immersed in silver nitrate. For all figures: CA = adhesive layer; D = demineralized dentin; U = undemineralized dentin; H = hybrid layer; ER = embedding resin infiltrated at a fractured site above the hybrid layer, which occurred during specimen preparation; and Pointer = interfibrillar spaces.

 

   DISCUSSION
TOP
 ABSTRACT
 INTRODUCTION
 MATERIALS & METHODS
 RESULTS
 DISCUSSION
REFERENCES
 
The results showed that the type of solvent in the primer solutions significantly affected resin/dentin bond strengths. This requires the rejection of the tested null hypothesis. The differences in bond strengths can be explained by the differences in the ability of the respective primers to re-expand the previously dried demineralized matrix. Collagen is a fibrous biopolymer that normally exists in an aqueous environment (Lazarev et al., 1992). Interpeptide H-bonding is important for maintaining the helical structure of collagen (Lee, 1986). In an aqueous environment, collagen peptides form H-bonds with water clusters, due to the very high {delta}h value of water, 37.3 (J/cm3)1/2, relative to the collagen peptides (Pashley et al., 2001). In demineralized dentin matrix, the presence of rinsing water maintains the matrix in a fully expanded state (Carvalho et al., 1996; Pashley et al., 2000, 2001). When dentin surfaces were dried with an air-stream for 30 sec, much of the water located in the matrix was removed (Nakaoki et al., 2000). This caused the matrix to collapse, approximating collagen fibrils. As collagen peptides touch, they form new interpeptide H-bonds that stabilize and stiffen the matrix in a shrunken state (Maciel et al., 1996). Air-dried, shrunken dentin has few interfibrillar spaces for resin penetration, thereby compromising the bonding of resins to dentin (Pashley et al., 1993; Gwinnett, 1994).

For such an undesirable situation to be reversed, primers must be able to re-expand the collapsed matrix. Since HEMA alone is not capable of re-expanding dry dentin matrix (Carvalho et al., 1996; Nakaoki et al., 2000), the solvents used in this study were chosen based on their graduated ability to re-expand demineralized, dry dentin matrix (Pashley et al., 2001). It was expected that the HEMA/water primer would induce the highest degree of expansion and would therefore result in the highest bond strength, assuming that the wide interfibrillar spaces are preserved during bonding procedures. Although it has been demonstrated that solvents with higher {delta}h values induced higher degrees of expansion when applied to dry, demineralized dentin matrix (Pashley et al., 2001), the current results indicate that the maintenance of matrix expansion during bonding procedures is more important than the pre-bonding expansion of the matrix. It is clear that higher bond strengths were obtained when the interfibrillar spaces are maximally preserved (TableGo, Fig. 1Go). However, our attempts to correlate the {delta}h values of the HEMA/solvent mixtures with the resultant bond strengths were statistically insignificant. Although the HEMA/water primer may have induced the highest expansion of the dried matrix (Pashley et al., 2001), the TEM images showed that the interfibrillar spaces of HEMA/water primer-infiltrated matrices were significantly smaller than those resulting from the application of the HEMA/methanol or HEMA/ethanol primers. Residual water located within the fibrils not only maintains their normal diameter (Fig. 2Go), but also preserves their compliance. We speculate that, during evaporation of the solvent in the HEMA/water specimens, the more compliant matrix shrank, reducing the width of resin-filled interfibrillar spaces in the hybrid layer, decreasing the resin uptake, and lowering the bond strength obtained in the HEMA/water group. Conversely, when methanol and ethanol were used as solvents, although the matrix may have expanded somewhat less, that expansion was sustained after solvent evaporation, because these water-free solvents stiffened the matrix, allowing for better resin infiltration (Maciel et al., 1996; Pashley et al., 2003). The fast evaporation rates of methanol and ethanol (ca. 120 and 54 torr, respectively) may also have helped to remove residual solvent and water from the matrix, allowing the relatively hydrophobic 4-META/TBBO resin to better wet the collagen fibrils, thus reducing porosities available for silver uptake (Fig. 2Go). The 60-second dwell time was chosen to maximize re-expansion and solvent evaporation (Perdigão and Frankenberger, 2001). Reduced (30 sec) dwell time had no effect on the trend of the results (Carvalho et al., unpublished observations); however, it is possible that further reduction of the dwell time could affect the results, particularly with the HEMA/water mixture (Kanca, 1998; Perdigão and Frankenberger, 2001).

The significantly higher bond strengths obtained when ethanol was used may be due to its {delta}h value, 19.4 (J/cm2)1/2 being higher than the {delta}h of dried collagen (18.2, Pashley et al., 2001), allowing it to dehydrate and stiffen the matrix without allowing interpeptide H-bonding to collapse the matrix. Propanol’s {delta}h value, 16.4 (J/cm3)1/2, is too low to break interpeptide H-bonds that collapsed the matrix and shrank the fibrils. We speculate that this prevented resin infiltration, resulting in porosities for silver uptake. Silver uptake appears to be inversely related to resin uptake (Sano et al., 1995). Our silver uptake findings support the concepts that high bond strengths require wider interfibrillar spaces and that such spaces should be properly infiltrated with resin.

It has been generally accepted that only air-drying was responsible for the shrinkage of the demineralized dentin during bonding procedures (Gwinnett, 1994). However, a recent study showed that solvents and monomers are also responsible for dimensional changes in the demineralized dentin matrix, and that those changes are related to the solubility parameters of the solvents commonly used in the bonding agents (Pashley et al., 2001). The current study confirms that the solubility parameters of HEMA/solvent mixtures can significantly affect bond strengths to dentin, by modifying the final degree of expansion of dried matrix. These findings reflect the use of experimental, single HEMA/solvent mixtures. Although results with the use of more complex mixtures such as HEMA/solvent/water cannot be predicted from this study, we may speculate that the degree of expansion will be proportional to the amount of water present in the mixture (Pashley et al., 2001). This advances our understanding of the mechanism(s) of dentin bonding that should challenge manufacturers to devise new products that include solvents capable of maintaining the structure of the demineralized dentin matrix in an expanded configuration during and after resin infiltration.


   ACKNOWLEDGMENTS
 
This study was partially supported by grants #300481/95-0 from Conselho Nacional de Desenvolvimento Cient’fico e Tecnol—gico (CNPq, Brazil), #01/06140-1 and 02/06682-1 from Fundação de Amparo a Pesquisa do Estado de São Paulo (FAPESP, Brazil), and #DE 014911 from the National Institute of Dental and Craniofacial Research (NIDCR, Bethesda, MD, USA). The authors are grateful to Mrs. Michelle Barnes for her secretarial support.

Received September 19, 2002; Last revision April 21, 2003; Accepted May 27, 2003


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 ABSTRACT
 INTRODUCTION
 MATERIALS & METHODS
 RESULTS
 DISCUSSION
 REFERENCES
 
Barton AFM (1991). Expanded cohesion parameters. Chapter 5. In: Handbook of solubility parameters and other cohesion parameters. 2nd ed. Boca Raton, FL: CRC Press, pp. 98–103.

Carvalho RM, Yoshiyama M, Pashley EL, Pashley DH (1996). In vitro study on the dimensional changes of human dentine after demineralization. Arch Oral Biol 41:369–377.[ISI][Medline]

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Lasarev YA, Grishkovsky BA, Khromova TB, Lazareva AV, Grechishko VS (1992). Bound water in the collagen-like triple-helical structure. Biopolymers 32:189–195.[ISI][Medline]

Lee S (1986). Water content in type I collagen tissues calculated from the generalized packing model. Int J Macromol 8:66–69.

Maciel KT, Carvalho RM, Ringle RD, Preston CD, Russell CM, Pashley DH (1996). The effects of acetone, ethanol, HEMA, and air on the stiffness of human decalcified dentin matrix. J Dent Res 75:1851–1858.[Abstract/Free Full Text]

Nakajima M, Sano H, Burrow MF, Tagami J, Yoshiyama M, Ebisu S, et al. (1995). Tensile bond strength and SEM evaluation of caries-affected dentin using dentin adhesives. J Dent Res 74:1679–1688.[Abstract/Free Full Text]

Nakaoki Y, Nikaido T, Pereira PN, Inokoshi S, Tagami J (2000). Dimensional changes of demineralized dentin treated with HEMA primers. Dent Mater 16:441–446.[ISI][Medline]

Pashley DH, Ciucchi B, Sano H, Horner JA (1993). Permeability of dentin to adhesive agents. Quintessence Int 24:618–631.[Medline]

Pashley DH, Carvalho RM, Sano H, Nakajima M, Yoshiyama M, Stone Y, et al. (1999). The microtensile bond test: a review. J Adhes Dent 1:299–309.

Pashley DH, Zhang Y, Agee KA, Rouse CJ, Carvalho RM, Russell CM (2000). Permeability of demineralized dentin to HEMA. Dent Mater 16:7–14.[ISI][Medline]

Pashley DH, Agee KA, Nakajima M, Tay FR, Carvalho RM, Terada RS, et al. (2001). Solvent-induced dimensional changes in EDTA-demineralized dentin matrix. J Biomed Mater Res 56:273–281.[ISI][Medline]

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