d e n t a l m a t e r i a l s 2 8 ( 2 0 1 2 ) 467–477
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Review
Aspects of silane coupling agents and surface conditioning in dentistry: An overview Christie Ying Kei Lung, Jukka Pekka Matinlinna ∗ Dental Materials Science, Faculty of Dentistry, The University of Hong Kong, Hong Kong, China
a r t i c l e
i n f o
a b s t r a c t
Article history:
Objectives. To give an overview of aspects of silane coupling agents and surface conditioning
Received 31 May 2011
in dentistry.
Received in revised form
Methods. Currently, silane coupling agents are used as adhesion promoters. Silanes are effec-
11 November 2011
tive in enhancing adhesion between resin composite and silica-based ceramics. They do not
Accepted 17 February 2012
bond effectively to non-silica based dental restorative materials. Surface conditioning of non-silica based ceramics with silica coating improves the bonding. This current overview will focus on the silane coupling agents: their properties, limitations in adhesion promotion
Keywords:
and the clinical problems with the use of silanes. It will also focus on the current surface con-
Silane
ditioning methods as well as new surface conditioning techniques to enhance the bonding
Adhesion
through conventional silanization approaches.
Dental materials
Results. Several surface conditioning methods are being used clinically to enhance the adhe-
Zirconia
sion of resin composites to non-silica based restorative materials. Other approaches are
Titanium
under investigation. The clinical problem of using silanes in adhesion promotion is the
Resin composites and cements
bond degradation over time in oral environment. Significance. The current silane coupling agents are not ideal. The current silane coupling agents can fulfill the minimum requirements in clinical practice to enhance the bonding of resin composite to dental restorative materials. Developments of novel surface conditioning methods and silane coupling agents are required to address the bond durability problem. © 2012 Academy of Dental Materials. Published by Elsevier Ltd. All rights reserved.
Contents 1. 2. 3.
Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Pre-activated silanes in dentistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Surface conditioning . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3.1. Grit blasting . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3.2. Pyrochemical silica-coating . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3.3. Tribochemical silica-coating . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3.4. Chemical treatment of ceramic materials . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
468 468 468 468 470 470 470
∗ Corresponding author at: Dental Materials Science, Faculty of Dentistry, The University of Hong Kong, 4/F, Prince Philip Dental Hospital, 34 Hospital Road, Sai Ying Pun, Hong Kong, China. Tel.: +852 2859 0380; fax: +852 2548 9464. E-mail addresses:
[email protected] (C.Y.K. Lung),
[email protected] (J.P. Matinlinna). 0109-5641/$ – see front matter © 2012 Academy of Dental Materials. Published by Elsevier Ltd. All rights reserved. doi:10.1016/j.dental.2012.02.009
468
4.
5.
6. 7. 8.
1.
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3.5. Selective infiltration etching (SIE) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3.6. Other surface conditioning methods. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Functional and non-functional silanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4.1. Functional silanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4.2. Non-functional silanes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4.3. Some uncommon silanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4.4. Silane activation mechanism . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Silane application in dentistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5.1. Ceramic restorations and repairs. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5.2. Glass fiber-reinforced composites . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5.3. Resin composite filling materials. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5.4. Titanium, base metal and noble metal alloys. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5.5. Dentin bonding . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Limitations of silane adhesion promotion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Current trends and future development of coupling agents in dentistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Introduction
Numerous applications in industry, medicine and dentistry rely heavily on connecting dissimilar inorganic and organic materials to achieve specific technical purposes. However, owing to difference in nature of chemical bonding in these materials, the interaction is very weak at the interfacial layer that there are no significant practical values in real situation. This problem can be resolved with the introduction of coupling agents. In dentistry, bonding of resin composite to some dental restorative materials can be enhanced through the application of silane coupling agents. Silanes are very effective in promoting adhesion for silica-based materials such as porcelain. However, for non-silica based restorative materials such as zirconia, metals or metal alloys, the adhesion performance using silanes only is not satisfactory. Approaches to solve this problem focus on the surface conditioning. A widely used current method is tribochemical silica-coating. A silica-coated layer is anchored to the substrate surface such that silane coupling agents can form durable bond with non-silica based materials through this layer. It also enhances micro-mechanical retention due to the increased surface roughness. Silanes are mainly used as adhesion promotions in ceramic restorations and their repairs with resin composites [1–3], glass fiber reinforced polymer composites [4], glassy fillers in resin composite [5] and to form durable bond between resin composite to silica-coated metal and metal alloys [6]. Perhaps, surprisingly, silanes do not have intrinsic toxicity [7] This overview will focus on silane bonding mechanism, adhesion promotion of resin composites to dental restorative materials, the weaknesses and limitations in promoting bonding. Contemporary surface conditioning methods as well as new surface conditioning techniques that are under development to enhance the chemical bonding (and micromechanical retention) will also be discussed.
2.
Pre-activated silanes in dentistry
3-Methacryloxyproyltrimethoxysilane (MPS) is the commonly used in clinical commercial silane primers (Table 1). They
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are applied as pre-hydrolysed in a solvent mixture consisting of ethanol and water. The silane content is usually about 1–5 vol%. However, one bottle pre-hydrolyzed silane solutions have relatively short shelf life. Over time, the solution may appear cloudy or turn milky after opening and then it cannot be used. Subsequently, the two-bottle silane systems were introduced into dentistry. These systems consist of an unhydrolyzed silane in ethanol in one bottle and an aqueous acetic acid solution in the other [8]. The two solutions are mixed to allow hydrolysis of the silane at a low pH before use. These systems increase the shelf life of silanes in comparison to the one-bottle systems. An example is the Silicoup A and B from Heraeus Kulzer (Table 1).
3.
Surface conditioning
Surface conditioning of dental materials is a treatment of a surface that increases the surface roughness, i.e., the surface energy. Surface treatments also create micropores for infiltration of silanes and resin cements [9]. Increase in the surface energy results in better wetting for bonding. We will discuss in the following sections some of the most important surface conditioning methods for zirconia, metals, base and noble metal alloys and porcelain (including repair of fractured porcelain), used in dentistry.
3.1.
Grit blasting
In dental laboratories, the typical procedure is blasting the surfaces with alumina particles of an average size of, e.g. 50 m under an air pressure of 380 kPa for around 10–15 s at a perpendicular short distance (ca. 10 mm) from the nozzle to the surface [10]. However, some alumina particles may be embedded into the surfaces during grit blasting. Given this, a layer of alumina-coating formed onto the substrate surfaces after such a grit-blasting. The amount of alumina increased with increasing blasting pressure [11]. After silanization, Al O Si bonds may be formed. However, they are hydrolytically unstable [12].
Table 1 – Examples of commercial silanes used in dentistry. Name Bisco Porcelain Primer Bisco Bis Silane
Clearfil Porcelain Bond Activator ESPE Sil ESPE RelyX Ceramic Primer Monobond-S Pulpdent Silane Bond Enhancer Silicoup A and B (a two bottle system) Ultradent Silane Vectris Wetting Agent VITA Zahnfabrik
Bisco, Schaumburg, IL, USA Bisco, Schaumburg, IL, USA VOCO, Cuxhaven, Germany Kuraray, Osaka, Japan
Effective silane (%) ‘A silane’, >1 ‘A silane’, 1–10 ‘Silane’, N/A MPS, 45, Acetone > 45’ ‘Alcohol 30–95’
Porcelain, composite
April 2010
Porcelain, composite
November 2007
2-Propanol 50–100
Repair of ceramics, metals Porcelain, ceramics, resin-based materials Porcelain
January 2011
4 5.5 3
Kuraray, Osaka, Japan
MPS 40–60
2.3
ESPE Dental, Seefeld, Germany 3M ESPE, St. Paul, MN, USA Ivoclar Vivadent, Schaan, Liechtenstein Pulpdent, Watertown, MN, USA Heraeus Kulzer, Hanau, Germany
‘MPS’, C C< bond in the resin monomer or in the silane molecule to generate a new reactive free radical species. Addition of these free radicals between resin composite monomers and silane molecules forms new C C sigma bonds. Thus, a linkage is formed between resin composite and substrate surface [58].
5.
Silane application in dentistry
5.1.
Ceramic restorations and repairs
Various ceramic materials such as yttria partially stabilized tetragonal zirconia polycrystalline (TZP), feldspathic, glassinfiltrated alumina and leucite-reinforced ceramics are used in ceramic restoration owing to superior esthetic appearance and metal-free substructure. Silane coupling agents are applied onto silica-coated ceramics to give durable bonding between resin and ceramics [59]. The fracture of dental ceramics is the challenging problems in restorative dentistry. There are many reasons for the dental ceramics to fracture, e.g. micro-defects in the material, impact and fatigue load, imperfect design and manufacturing, mastication, parafunction and intraoral occlusal forces create repetitive dynamic loading [60]. It is more economical and time-saving to repair than to remake the whole ceramic crown or bridge. The repairs of ceramic restoration involve, in general, three alternative steps to treat the ceramic surface:
(a) roughening with diamond burs, (b) sandblasting, (c) acid etching with hydrofluoric acid, followed by silanization, and bonding to resin composite [61].
5.2.
Glass fiber-reinforced composites
Several applications of glass fiber in dentistry include, removable prosthodontics, periodontal splints, fixed partial dentures and retention splints [62]. The silanized glass fibers are embedded in acrylic resin to reinforce denture base resin. The impact and tensile strengths of fiber reinforced composite acrylic resin dentures are higher than those un-reinforced acrylic resin dentures [63–65]. Furthermore, the adhesion of glass fibers to resin composite was enhanced when glass fibers were silanized with silane coupling agents before being embedded into the resin matrix [66–68]. Statistical analysis revealed there was significant difference in the adhesion for different silane coupling agents used [67]. The addition of 3-(trimethoxysilyl) propyl methacrylate in hydroxyapatite (HA) reinforced poly(methyl methacrylate) (PMMA) could improve the mechanical properties by strengthening the chemical bonding and increasing the mechanical interlocking between HA and PMMA [69]. The molecular structures of the silane coupling agents may have different effects on the mechanical properties of dental composites. The hydrolytic stability of silanized glass fibers embedded in dental composites with a long hydrocarbon chain silane, 10-methacryloxydecltrimethoxysilane is higher than that of 3-methacryloxypropyltrimethoxysilane [66]. This may be due to the increase in hydrophobicity of 10-methacryloxydecyltrimethoxysilane. Moreover, the selection of the silane coupling agents with different functional groups may also affect the mechanical properties of reinforced composites. It was reported that there was no significant difference in interfacial shear bond strength between the control of unsilanized fiber reinforced glass resin composite specimens and that of specimens silanized with 5% glycidoxypropyltrimethoxysilane (GPS). Statistically difference between the control and 5% 3-methacryloxypropyltrimethoxysilane (MPS) silanized specimens was significant [67]. The resin studied was a mixture of bis-phenol-A bis-(2-hydroxypropyl)methacrylate (bisGMA) and tri(ethylene glycol)dimethacrylate (TEGDMA) which both contained the >C C< functional group. The organofunctional groups of these two silanes are >C C< for MPS and for GPS. Therefore, the reactivity of MPS is higher than GPS toward the resin, which may explain the increasing in the bond strength of glass reinforced composite silanized with MPS.
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5.3.
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Resin composite filling materials
Modern dental composites are composed of an organic matrix which contains monomers, a free-radical initiator, an inhibitor, filler materials such as silica, lithium aluminum silicates, hydroxyapatite and boron silicates, and a silane coupling agent that can increase the bonding between the fillers and the organic matrix [70]. The filler materials are added to improve the physical and mechanical properties of the resin. Fillers reduce curing shrinkage during and after polymerization, and they improve the esthetic appearance and radio-opacity [71]. An experimental resin with increasing volume fraction of silanized fillers is reported to have higher diametral tensile strength and compressive strength than that without silanization, when tested under dry conditions and stored in an alcoholic solution [72].
5.4.
Titanium, base metal and noble metal alloys
Extensive studies suggest that silane coupling agents can promote adhesion between resin composites and titanium, base and noble metal alloys and steel [73–76]. Yanagida et al. [74] stated that silane coupling agent is not effective for bonding between resin composite and metal substrates unless the surfaces of metal/metal alloys are pre-treated by sandblasting of silica-coated alumina, i.e., a silica layer is formed onto the surface. During sandblasting, the metal/metal alloy surfaces are bombarded with high energy silica-coated alumina particles. A bonding is formed between these particles and metal (M) surfaces, i.e., O Si O M linkage is formed. When silane is applied onto the silica-coated metal surfaces, a (Si O Si) O M siloxane linkage is formed. Alternatively, the so-called metal and alloy primers are used for bonding resin composite to noble metals/noble metal alloys. These primers are reported to be as effective as silane coupling agents and even in some cases; it is more superior in performance [77]. The metal or alloy primers are generally phosphate for base metal alloys and thione or thiol for noble metal alloys [78].
5.5.
Dentin bonding
There are very few studies reporting the effect of silane coupling agents on the bond strength between dentin and dental restorative materials. In a study [79], the ceramic surfaces were airborne-particle abraded and etched with hydrofluoric acid. Then, the surface treated specimens were cemented with dual-polymerized luting cement and finally treated with silane coupling agent. The ceramic specimens were cemented onto the dentin surface which was first treated with the same luting cement. Shear bond strengths were increased with the application of the silane coupling agent.
6. Limitations of silane adhesion promotion In this current overview, some aspects of silane coupling agents have been discussed. Silanes are good coupling agent to promote adhesion between resin composites and dental
restorative materials. However, there are also some limitations for silane coupling agents. The adhesion promotion using silane coupling agents for non-silica based restorative materials such as zirconia, alumina, metal and metal alloys, e.g. CrCo alloys is weaker than silica-coated of these restorative materials [80–83,76]. The mean bond strength values measured were significantly lower. Therefore, the surface of non-silica based restorative materials (except for porcelain which only requires acid etching to form a microscopically porous, high energy and microretentive surface for bonding) must be silica-coated to ensure durable bonding, siloxane linkage, is formed. For noble metals or noble metal alloys without silica coating, the thione or thiol-based coupling agents can be used to promote adhesion.
7. Current trends and future development of coupling agents in dentistry Nowadays, not only silane coupling agents are used for adhesion promotion of resin composite to dental restorative materials, but there are some other coupling agents such as phosphate ester, e.g. MDP, added in self adhesive resin cements and adhesive primers, metal and alloy primers, e.g. thione and thiol and carboxylic acid primers, e.g. 4-META and MAC-10 [84–87]. Phosphate esters can bond directly with the surface hydroxyl groups of non-silica containing ceramics such as zirconia [88]. Moreover, application of this coupling agent on bonding resin composites to ceramics is reported to enhance the hydrolytic stability of bonding more than using silane coupling agents [89]. For non-silica containing materials such as noble metals and noble metal alloys, thione and thiol primers are used for adhesion promotion. These coupling agents have different bonding mechanisms with various dental restorative materials. For thione and thiol coupling agents, the sulphur atoms form dative coordinative bonding to noble metals/metal alloys [90]. The application of silane coupling agents in adhesion promotion of resin composite to dental restorative materials has been used more than 50 years since their first introduction in dentistry. The main problem of resin composites bonded to silica-coated restorative materials with the application of commercial silane coupling agents is the bond degradation over time in vivo and in vitro [91–94]. To solve this problem, there are two approaches: (a) the development of novel surface treatments of restorative materials that can enhance the chemical bonding through conventional silanation approaches – and these are under investigation (Section 3). (b) The design of novel silane monomers with durable bonding and enhanced hydrolytic stability. Silane coupling agents ( , n > 10) with long hydrocarbon chain are much more hydrophobic than those with the short hydrocarbon chain, such as pre-hydrolysed commercial silane coupling agents products. The bond hydrolytic stability, in principle, should be enhanced. In vitro studies of bond durability of resin composites bonded to silica-coated dental restorative materials that are primed with these new type of silane coupling agents merit future investigation. The combination of these two approaches might be the ultimate solution.
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8.
Conclusions
Virtually all applications in dentistry involve the joining of two dissimilar materials. Silane coupling agents play a critical role as mediators to fulfill the clinical requirements for durable bonding. Nowadays, surface conditioning of dental materials combines with silanation is a standard laboratory protocol in dental restorations and chair-side repairs. However, concerns about the hydrolytic stability of siloxane linkage formed from silane coupling agents with resin composites and dental restorative materials are currently addressed. Silane coupling agents have shown recent applications in bio-medicine and justified their special role in dentistry and some may support our idea that silanes will play a leading role in biomaterials science.
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