Systematic review of the chemical composition of contemporary dental adhesives
TL;DR: The aim of this article is to systematically review the ingredients commonly used in current dental adhesives as well as the properties of these ingredients.
About: This article is published in Biomaterials.The article was published on 2007-09-01. It has received 1218 citations till now. The article focuses on the topics: Dental bonding.
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TL;DR: Five experimental strategies developed by different research groups for extending the longevity of resin-dentin bonds are examined, finding a combination of several of these strategies should result in overcoming the critical barriers to progress currently encountered in dentin bonding.
Abstract: The limited durability of resin-dentin bonds severely compromises the lifetime of tooth-colored restorations Bond degradation occurs via hydrolysis of suboptimally polymerized hydrophilic resin components and degradation of water-rich, resin-sparse collagen matrices by matrix metalloproteinases (MMPs) and cysteine cathepsins This review examined data generated over the past three years on five experimental strategies developed by different research groups for extending the longevity of resin-dentin bonds They include: (1) increasing the degree of conversion and esterase resistance of hydrophilic adhesives; (2) the use of broad-spectrum inhibitors of collagenolytic enzymes, including novel inhibitor functional groups grafted to methacrylate resins monomers to produce anti-MMP adhesives; (3) the use of cross-linking agents for silencing the activities of MMP and cathepsins that irreversibly alter the 3-D structures of their catalytic/allosteric domains; (4) ethanol wet-bonding with hydrophobic resins to completely replace water from the extrafibrillar and intrafibrillar collagen compartments and immobilize the collagenolytic enzymes; and (5) biomimetic remineralization of the water-filled collagen matrix using analogs of matrix proteins to progressively replace water with intrafibrillar and extrafibrillar apatites to exclude exogenous collagenolytic enzymes and fossilize endogenous collagenolytic enzymes A combination of several of these strategies should result in overcoming the critical barriers to progress currently encountered in dentin bonding
560 citations
TL;DR: The enamel bond strength of universal adhesives is improved with prior phosphoric acid etching, however, this effect was not evident for dentin with the use of mild universalAdhesives with the etch-and-rinse strategy.
400 citations
Cites background from "Systematic review of the chemical c..."
...They are a blend of hydrophilic and hydrophobic monomers, polymerization initiators, solvents, stabilizers, and filler particles.(8) Additionally, self-etch adhesives contain specific monomer molecules with carboxylate or phosphate acidic groups that simultaneously act as conditioner (that allow dental superficial demineralization) and primer agents (resin monomers that infiltrates into the dentin) upon the dental substrates....
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TL;DR: The article will examine the various avenues that have been pursued to address problems and it will explore how alterations in material chemistry could address the detrimental impact of physico-chemical stresses on the bond formed at the adhesive/dentin interface.
Abstract: Results from clinical studies suggest that more than half of the 166 million dental restorations that were placed in the United States in 2005 were replacements for failed restorations. This emphasis on replacement therapy is expected to grow as dentists use composite as opposed to dental amalgam to restore moderate to large posterior lesions. Composite restorations have higher failure rates, more recurrent caries, and increased frequency of replacement as compared to amalgam. Penetration of bacterial enzymes, oral fluids, and bacteria into the crevices between the tooth and composite undermines the restoration and leads to recurrent decay and premature failure. Under in vivo conditions the bond formed at the adhesive/dentin interface can be the first defense against these noxious, damaging substances. The intent of this article is to review structural aspects of the clinical substrate that impact bond formation at the adhesive/dentin interface; to examine physico-chemical factors that affect the integrity and durability of the adhesive/dentin interfacial bond; and to explore how these factors act synergistically with mechanical forces to undermine the composite restoration. The article will examine the various avenues that have been pursued to address these problems and it will explore how alterations in material chemistry could address the detrimental impact of physico-chemical stresses on the bond formed at the adhesive/dentin interface.
384 citations
TL;DR: This review will examine both the principles and outcomes of techniques to prevent collagen hydrolysis in dentin-resin interfaces, and shows that enzyme inhibition is a promising approach to improve hybrid layer preservation and bond strength durability.
332 citations
TL;DR: A meta-analytical study on the short and long-term release of components from resin-based dental materials, and how much (order of magnitude) of those components may leach out in the oral cavity is presented in this paper.
323 citations
References
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Book•
01 Jan 1981TL;DR: In this paper, the authors present an overview of the properties of polymers and their applications in the literature, including the following: 1.1 Types of Polymers and Polymerization. 2.3 Linear, Branched, and Crosslinked Polymers.
Abstract: Preface. 1. Introduction. 1.1 Types of Polymers and Polymerizations. 1.2 Nomenclature of Polymers. 1.3 Linear, Branched, and Crosslinked Polymers. 1.4 Molecular Weight. 1.5 Physical State. 1.6 Applications of Polymers. 2. Step Polymerization. 2.1 Reactivity of Functional Groups. 2.2 Kinetics of Step Polymerization. 2.3 Accessibility of Functional Groups. 2.4 Equilibrium Considerations. 2.5 Cyclization versus Linear Polymerization. 2.6 Molecular Weight Control in Linear Polymerization. 2.7 Molecular Weight Distribution in Linear Polymerization. 2.8 Process Condition. 2.9 Multichain Polymerization. 2.10 Crosslinking. 2.11 Molecular Weight Distributions in Nonlinear Polymerizations. 2.12 Crosslinking Technology. 2.13 Step Copolymerization. 2.14 High-Performance Polymers. 2.15 Inorganic and Organometallic Polymers. 2.16 Dendric (Highly Branched) Polymers. 3. Radical Chain Polymerization. 3.1 Nature and Radical Chain Polymerization. 3.2 Structural Arrangement of Monomer Units. 3.3 Rate of Radical Chain Polymerization. 3.4 Initiation. 3.5 Molecular Weight. 3.6 Chain Transfer. 3.7 Inhibition and Retardation. 3.8 Determination of Absolute Rate Constants. 3.9 Energetic Characteristics. 3.10 Autoacceleration. 3.11 Molecular Weight Distribution. 3.12 Effect of Pressure. 3.13 Process Conditions. 3.14 Specific Commercial Polymers. 3.15 Living Radical Polymerization. 3.16 Other Polymerizations. 4. Emulsion Polymerization. 4.1 Description of Process. 4.2 Quantitative Aspects. 4.3 Other Characteristics of Emulsion Polymerization. 5. Ionic Chain Polymerization. 5.1 Comparison of Radical and Ionic Polymerization. 5.2 Cationic Polymerization of the Carbon-Carbon Double Bond. 5.3 Anionic Polymerization of the Carbon-Carbon Double. 5.4 Block and Other Polymer Architecture. 5.5 Distinguishing Between Radical, Cationic, and Anionic Polymerizations. 5.6 Carbonyl Polymerization. 5.7 Miscellaneous Polymerizations. 6. Chain Copolymerization. 6.1 General Considerations. 6.2 Copolymer Composition. 6.3 Radical Copolymerization. 6.4 Ionic Copolymerization. 6.5 Deviations from Terminal Copolymerization Model. 6.6 Copolymerizations Involving Dienes. 6.7 Other Copolymerizations. 6.8 Applications of Copolymerizations. 7. Ring-Opening Polymerization. 7.1 General Characteristics. 7.2 Cyclic Ethers. 7.3 Lactams. 7.4 N-Carboxy-alphaAmino Acid Anhydrides. 7.5 Lactones. 7.6 Nitrogen Heterocyclics. 7.7 Sulfur Heterocyclics. 7.8 Cycloalkenes. 7.9 Miscellaneous Oxygen Heterocyclics. 7.10 Other Ring-Opening Polymerizations. 7.11 Inorganic and Partially Inorganic Polymers. 7.12 Copolymerization. 8. Stereochemistry of Polymerizaton. 8.1 Types of Stereoisomerism in Polymers. 8.2 Properties of Stereoregular Polymers. 8.3 Forces of Stereoregulation in Alkene Polymerization. 8.4 Traditional Ziegler-Natta Polymerization of Nonpolar Alkene Monomers. 8.5 Metallocene Polymerization of Nonpolar Alkene Monomers. 8.6 Other Hydrocarbon Monomers. 8.7 Copolymerization. 8.8 Postmetallocene: Chelate Initiators. 8.9 Living Polymerization. 8.10 Polymerization of 1,3-Dienes. 8.11 Commercial Applications. 8.12 Polymerization of Polar Vinyl Monomers. 8.13 Alehydes. 8.14 Optical Activity in Polymers. 8.15 Ring-Opening Polymerization. 8.16 Statistical Models of Propagation. 9. Reactions of Polymers. 9.1 Principles of Polymers Reactivity. 9.2 Crosslinking. 9.3 Reactions of Cellulose. 9.4 Reactions of Poly(vinyl) acetate). 9.5 Halogenation. 9.6 Aromatic Substitution. 9.7 Cyclization. 9.8 Other Reactions. 9.9 Graft Copolymers. 9.10 Block Copolymers. 9.11 Polymers as Carriers or Supports. 9.12 Polymer Reagents. 9.13 Polymer Catalysts. 9.14 Polymer Substrates. Index.
4,933 citations
"Systematic review of the chemical c..." refers background in this paper
...Initiators are generally molecules that possess atomic bonds with low dissociation energy that will form radicals under certain conditions [14]....
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...Sun and Chae showed that PPD yields higher mechanical strengths, and PPD has comparable or better polymerization efficiency than CQ [116,123,135]....
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...When used in combination with CQ, PPD acts synergistically [123]....
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...This physical state allows PPD good compatibility with resin, where it serves as a diluent as opposed to CQ....
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...Unlike CQ, PPD is a slightly yellow viscous fluid at room temperature....
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TL;DR: This paper critically appraises methodologies that focus on chemical degradation patterns of hydrolysis and elution of interface components, as well as mechanically oriented test set-ups, such as fatigue and fracture toughness measurements, to assess adhesion durability.
Abstract: The immediate bonding effectiveness of contemporary adhesives is quite favorable, regardless of the approach used. In the long term, the bonding effectiveness of some adhesives drops dramatically, whereas the bond strengths of other adhesives are more stable. This review examines the fundamental processes that cause the adhesion of biomaterials to enamel and dentin to degrade with time. Non-carious class V clinical trials remain the ultimate test method for the assessment of bonding effectiveness, but in addition to being high-cost, they are time- and labor-consuming, and they provide little information on the true cause of clinical failure. Therefore, several laboratory protocols were developed to predict bond durability. This paper critically appraises methodologies that focus on chemical degradation patterns of hydrolysis and elution of interface components, as well as mechanically oriented test set-ups, such as fatigue and fracture toughness measurements. A correlation of in vitro and in vivo data revealed that, currently, the most validated method to assess adhesion durability involves aging of micro-specimens of biomaterials bonded to either enamel or dentin. After about 3 months, all classes of adhesives exhibited mechanical and morphological evidence of degradation that resembles in vivo aging effects. A comparison of contemporary adhesives revealed that the three-step etch-and-rinse adhesives remain the 'gold standard' in terms of durability. Any kind of simplification in the clinical application procedure results in loss of bonding effectiveness. Only the two-step self-etch adhesives approach the gold standard and do have some additional clinical benefits.
1,778 citations
"Systematic review of the chemical c..." refers background in this paper
...sorption [37], more nanoleakage [38], degradation of the tooth-composite bond [39] and more leaching of residual uncured monomers and thus lower biocompatibility of dental adhesives....
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Journal Article•
TL;DR: The basic bonding mechanism to enamel and dentin of these three approaches is demonstrated by means of ultramorphological and chemical characterization of tooth-biomaterial interfacial interactions and confirms that conventional three-step etch&rinse adhesives still perform most favorably and are most reliable in the long-term.
Abstract: Bonding to tooth tissue can be achieved through an "etch&rinse," "self-etch" or "glass-ionomer" approach. In this paper, the basic bonding mechanism to enamel and dentin of these three approaches is demonstrated by means of ultramorphological and chemical characterization of tooth-biomaterial interfacial interactions. Furthermore, bond-strength testing and measurement of marginal-sealing effectiveness (the two most commonly employed methodologies to determine "bonding effectiveness" in the laboratory) are evaluated upon their value and relevance in predicting clinical performance. A new dynamic methodology to test biomaterial-tooth bonds in a fatigue mode is introduced with a recently developed micro-rotary fatigue-testing device. Eventually, today's adhesives will be critically weighted upon their performance in diverse laboratory studies and clinical trials. Special attention has been given to the benefits/drawbacks of an etch&rinse versus a self-etch approach and the long-term performance of these adhesives. Correlating data gathered in the laboratory with clinical results clearly showed that laboratory research CAN predict clinical effectiveness. Although there is a tendency to simplify bonding procedures, the data presented confirm that conventional three-step etch&rinse adhesives still perform most favorably and are most reliable in the long-term. Nevertheless, a self-etch approach may have the best future perspective. Clinically, when adhesives no longer require an "etch&rinse" step, the application time, and probably more importantly, the technique-sensitivity are substantially reduced. Especially "mild," two-step self-etch adhesives that bond through a combined micromechanical and chemical interaction with tooth tissue closely approach conventional three-step systems in bonding performance.
1,721 citations
"Systematic review of the chemical c..." refers background or methods in this paper
...The adhesives are categorized according to the classification of Van Meerbeek [5]....
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...This is achieved by an exchange process by which inorganic tooth material is replaced by resin monomers that become interlocked in the retentions upon curing [4,5]....
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...: +3216 33 75 87; fax: +3216 33 27 52. ess: bart.vanmeerbeek@med.kuleuven.ac.be (B. Van Meerbeek)....
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26 Jul 2002
TL;DR: Krzysztof Matyjaszewski and Thomas P. Davis as discussed by the authors discussed the fundamental concepts and history of living radical polymers and their application in industrial applications and processes.
Abstract: Introduction (Krzysztof Matyjaszewski and Thomas P. Davis). Contributors. 1. Theory of Radical Reactions (Johan P. A. Heuts). 2. Small Radical Chemistry (Martin Newcomb). 3. General Chemistry of Radical Polymerization (Bunichiro Yamada and Per B. Zetterlund). 4. The Kinetics of Free Radical Polymerization (Christopher Barner-Kowollik, Philipp Vana, and Thomas P. Davis). 5. Copolymerization Kinetics (Michelle L. Coote and Thomas P. Davis). 6. Heterogeneous Systems (Alex M. van Herk and Michael Monteiro). 7. Industrial Applications and Processes (Michael Cunningham and Robin Hutchinson). 8. General Concepts and History of Living Radical Polymerization (Krzysztof Matyjaszewski). 9. Kinetics of Living Radical Polymerization (Takeshi Fukuda, Atsushi Goto, and Yoshinobu Tsujii). 10. Nitroxide Mediated Living Radical Polymerization (Craig J. Hawker). 11. Fundamentals of Atom Transfer Radical Polymerization (Krzysztof Matyjaszewski and Jianhui Xia). 12. Control of Free Radical Polymerization by Chain Transfer Methods (John Chiefari and Ezio Rizzardo). 13. Control of Stereochemistry of Polymers in Radical Polymerization (Akikazu Matsumoto). 14. Macromolecular Engineering by Controlled Radical Polymerization (Yves Gnanou and Daniel Taton). 15. Experimental Procedures and Techniques for Radical Polymerization (Stefan A. F. Bon and David M. Haddleton). 16. Future Outlook and Perspectives (Krzysztof Matyjaszewski and Thomas P. Davis). Index.
1,407 citations
"Systematic review of the chemical c..." refers background in this paper
...Combination refers to the reaction of two radical chain ends and disproportioning involves hydrogentransfer and formation of two dead polymer chains (one saturated and one unsaturated) [113,114]....
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TL;DR: Scanning electron microscopic studies suggested that the monomers possess affinity with the hard tissue as indicated by the good adhesion provided by the interlocking at the tubules.
Abstract: The effectiveness of 4-methacryloxyethyl trimellitate anhydride (4-META) on the adhesion of an acrylic rod with etched dentine and enamel was studied. Etching of tooth substrates with a 10% citric acid-3% ferric chloride solution prior to the adhesion proved effective. Monomers with both hydrophobic and hydrophilic groups like 4-META promoted the infiltration of monomers into the hard tissue. The infiltrated monomers polymerized in situ and good adhesion with the tooth substrates took place. The tensile adhesive strength was 18 MPa on the etched dentine. Scanning electron microscopic studies suggested that the monomers possess affinity with the hard tissue. The good adhesion was not provided by the interlocking at the tubules as had been considered previously.
1,404 citations
Additional excerpts
...Microscopically, this process is called ‘hybridization’ [6]....
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