Resin composites in dentistry: the monomer systems

European Journal of Oral Sciences - Tập 105 Số 2 - Trang 97-116 - 1997
Anne Peutzfeldt1
1Department of Dental Materials, School of Dentistry, Faculty of Health Sciences, University of Copenhagen, Denmark. [email protected]

Tóm tắt

The present review outlines the history of monomers, used in resin composites, motivates further development, and highlights recent and ongoing research reported in the field of dental monomer systems. The monomer systems of most present‐day resin composites are based on BisGMA, developed some 40 years ago, or derivatives of BisGMA. In the remaining resin composites, urethane monomers or oligorners are used as the basis of the monomer system. The main deficiencies of current resin composites are polymerization shrinkage and insufficient wear resistance under high masticatory forces. Both factors are highly influenced by the mooonier system, and considerable efforts are being made around the world to reduce or eliminate these undesirable properties. The use of fluoride‐releasing monomer systems, some of which are under investigation, has been suggested to mitigate the negative effects of marginal gaps formed in consequence of polymerization shrinkage. The very crux of the problem has also been approached with the synthesis of potentially low‐shrinking/non‐shrinking resin composites involving ring opening or cyclopolymerizable monomers. By the use of additives with a supposed chain transfer agent function, monomer systems have been formulated that improve the degree of conversion of methacrylate double bonds and mechanical properties. Many promising monomer systems have been devised, the implementation of which may be expected to improve the longevity of resin composite fillings and expand the indications for resin composites.

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Tài liệu tham khảo

BowenRL.Dental filling material comprising vinyl‐silane treated fused silica and a binder consisting of the reaction product of bisphenol and glycidyl methacrylate.US Potent1962;3 066 112.

BowenRL.Silica‐resin direct filling material and method of preparation. US Patents 1965; 3 194 783 and 3 194 784.

Full CA, 1993, The composite resin restoration. A literature review part III. What the future holds, J Dent Child, 60, 57

Ferracane JL., 1992, Using posterior composites appropriately, J Am Dent Assoc, 123, 53

Phillips RW., 1973, Skinner's science of dental materials

10.1016/0109-5641(89)90128-0

10.1177/00220345840630111401

10.3109/00016358309162298

Asmussen E., 1984, Softening of BISGMA‐based polymers by ethanol and by organic acids of plaque, Scand J Dent Res, 92, 257

10.3109/00016357509004638

Munksgaard EC, 1987, Wall‐to‐wall polymerization contraction of composite resins versus filler content, Scand J Dent Res, 95, 526

10.1016/0022-3913(84)90334-2

Asmussen E, 1990, Mechanical properties of heat treated restorative resins for use in the inlay/onlay technique, Scand J Dent Res, 98, 564

10.1177/00220345920710081101

10.1016/S0109-5641(96)80076-5

Ruyter IE., 1985, Posterior composite resin dental restorative materials, 109

Luskin LS., 1967, Milestones in the history of acrylic products, Or-chem Topics, 23

Paffenbarger GC, 1974, Composite restorative materials in dental practice: a review, Int Dent J, 24, 1

Tylman SC, 1946, Acrylics and other synthetic resins used in dentistry

CzappAE SchnebelE GoelzA.Verfahren zur Schnellpolymerisation von Gemischen aus monomeren umd polymeren Vinylverbindungen.Dtsch Patentamt1941; 975072.

Schnebel E., 1940, Verfahren zur Herstellung von Zaltner‐satzteilen, insbesondere Füllungen, aus Polymerisations‐kunstharzen, Dtsch Reichspatentamt, 7603

Henschel CJ., 1949, Observations concerning in vivo disintegration of silicate cement restorations, J Dent Res, 28, 528

Bowen RL, 1968, A laboratory and clinical comparison of silicate cements and a direct‐filling resin: A progress report, J Prosthet Dent, 20, 426, 10.1016/S0022-3913(68)80020-4

10.14219/jada.archive.1953.0215

Coy HD., 1953, Direct resin fillings, J Am Dent Assoc, 47, 532, 10.14219/jada.archive.1953.0212

10.1177/00220345560350030501

KnockFE GlennJF.Dental material and method. US Patent 1951; 2 558 139.

Bowen RL, 1985, Posterior composite resin dental restorative materials, 95

BowenRL.Method of preparing a monomer having phenoxy and methacrylate groups linked by hydroxy glyceryl groups. US Patent 1965; 3 179 623.

10.14219/jada.archive.1963.0010

10.3109/00016357509026353

10.3109/00016358109162272

10.1177/00220345810600120601

10.1002/jbm.820210107

Kaye GWC, 1959, Tables of physical and chemical constants find some mathematical functions

10.3109/00016357709004652

Mcmurrt J., 1986, Fundamentals of organic chemistry

10.1007/978-1-4757-9510-3_27

Moore JE., 1976, Photopolymerization of multifunctional acrylates and methacrylates, Am Chern Sac, Coatings and Plastics Preprints, 36, 747

10.3109/00016357809027569

Asmussen E., 1982, Factors affecting the quantity of remaining double bonds in restorative resin polymers, Scand J Dent Res, 90, 490

10.1002/jbm.820200111

Asmussen E., 1982, Restorative resins: hardness and strength vs. quantity of remaining double bonds, Scand J Dent Res, 90, 484

Solomons TWG., 1988, Organic chemistry

March J., 1977, Advanced organic chemistry: reactions, mechanisms, and structure, 126

10.1177/00220345940730080901

10.1177/00220345870660050801

10.1111/j.1365-2842.1994.tb01158.x

10.1002/jbm.820210804

10.1016/S0109-5641(85)80058-0

10.1177/00220345880670060801

Grassie N., 1966, Encyclopedia of polymer science and technology, 647

10.1177/00220345830620020701

10.1177/00220345880670100901

Munksgaard EC, 1990, Enzymatic hydrolysis of (di)methacrylates and their polymers, Scand J Dem Res, 98, 261

10.1289/ehp.96104298

Munksgaard EC., 1995, Plastmaterialer og østrogener, Tandlaegebladet, 99, 560

Dahl JE, 1995, Uberettiget frykt for helseskader, Niom-Inf, 1, 8

10.1016/0142-9612(91)90022-3

10.1016/0022-3913(94)90028-0

10.1016/0022-3913(87)90104-1

10.1016/S0109-5641(05)80012-0

10.1177/00220345700490041801

10.1177/00220345730520041501

10.1177/00220345730520052201

10.1177/00220345750540033101

10.1007/978-1-4757-9510-3_25

10.1177/00220345750540033201

10.1177/00220345760550012901

Viohl J, 1979, Wasseraufnahme und Löslichkeit von Füllungskunststoffen in Abhängigkeit vom Mischungsverhältnis bzw. von der Bestrahlungszeit, Dtsch Zahnärztl Z, 34, 687

10.1177/00220345820610050701

10.3109/00016357209004588

10.1177/00220345840630101701

10.1002/jbm.820200214

10.1177/00220345900690120501

10.1177/00220345810600110701

StoffeyDG LeeHL.Triglycidyl ether of trihydroxy bisphenyl ester of acrylic acid. US Patent 1973; 3 755 420.

WallerDE.Dental compositions containing adduct of 2.2‐propane bis 3‐(4‐phenoxy)‐1 2‐hydroxy propane‐1‐methacrylate and isocyanate. US Patent 1971; 3 629 187.

Kollmannsperger P., 1978, Biegefestigkeit von Composites nach Wasserlagerung von einem Tag bis 3 Monate, Dtsch Zahnärztl Z, 33, 477

10.1016/0022-3913(78)90019-7

10.1002/jbm.820050306

SchmittW PurrmannR JochumP ZahlerWD.Novel diacrylic and dimethacrylic acid esters. US Patent 1974; 3 810 938.

Viohl J., 1974, Werkstoffkundliche Untersuchungen der Wasseraufnahme und Biegefestigkeit von Kunststoff‐Fullungsmalenalien, Dtsch Zahnärzlt Z, 29, 442

10.1016/0022-3913(83)90160-9

Leinfelder KF., 1985, Posterior composite resin dental restorative materials, 501

10.1007/978-1-4899-1283-1

10.1177/00220345790580100401

10.1177/00220345800590090901

10.1177/00220345820610010901

AntonucciJM.Hydrophobic dental composites based on a polyfluorinated dental resin. US Patent 1986; 4 616 073.

FosterJ WalkerRJ.Zahnfüllungsmaterial.Dtsch Patentamt1973; 2312559.

DartEC PerryAR NemcekJ.Photocurable resin impregnated fabric for forming rigid orthopaedic devices and method. US Patent 1975; 3 874 376.

DartEC PerryAR NemcekJ.Photocurable dental filling compositions. US Patent 1978; 4 110 184.

Glenn JF., Biocompatibility of dental materials, 98

10.14219/jada.archive.1979.0365

Reinhardt KJ., 1978, Untersuchungen physikalischer Eigenschaften hoehglanzpoherbarer Füllungsmaterialien im Vergleich zu Compositen, Dtsch Zahnärztl Z, 33, 547

Hansen EK., 1982, Visible light‐cured composite resins: polymerization contraction, contraction pattern and hygroscopic expansion, Scand J Dent Res, 90, 329

Knudsen MB, 1983, Abrasion of microfill restorative resins in Class 1 cavities, Scand J Dent Res, 91, 159

Städtler P, 1989, Abrasion von Komposites nach Bearbeitung mit Mohnsamen, Z Stomatol, 86, 217

10.14219/jada.archive.1985.0235

10.1016/0109-5641(92)90089-U

10.1016/0022-3913(80)90327-3

10.1016/0300-5712(95)98976-A

10.1016/0109-5641(95)80019-0

10.4012/dmj.3.272

10.1016/0109-5641(94)90057-4

10.1016/0142-9612(87)90030-5

10.1111/j.1834-7819.1983.tb05272.x

10.1016/0022-3913(88)90176-X

10.14219/jada.archive.1967.0078

10.1038/sj.bdj.4805746

10.1038/sj.bdj.4806750

10.1111/j.1365-2842.1993.tb01636.x

10.1080/00222337508065898

10.1016/0921-5093(90)90133-N

10.1177/00220345790580051701

10.1007/978-1-4899-0768-4_14

10.1177/00220345920710070901

10.1016/0109-5641(92)90016-6

10.1016/0109-5641(93)90088-8

Yourtee DM, 1994, The effect of spiroorthocarbonate volume modifier co‐monomers on the in vitro toxicology of trial non‐shrinking dental epoxy co‐polymers, Res Commun Mol Pathol Pharmcol, 86, 347

Murphy J, 1995, Effect of spiro orthocarbonate addition on polymerization shrinkage of acrylate systems, J Dent Res, 74, 183

10.1021/ma00174a065

Butler GB., 1966, Encyclopedia of polymer science and technology, 568

10.1177/00220345900690030201

10.1177/00220345920710030201

Butler GB., 1975, Proceedings of the international symposium on macromolecules, 57

10.1177/00220345950740041201

10.1016/0300-5712(76)90048-8

10.1111/j.1600-9657.1993.tb00265.x

10.1177/00220345550340060801

Van Meerbeek B, 1992, Dentin‐and enamel‐bonding agents, Curr Opin Dent, 2, 117

Swift EJ, 1995, Bonding to enamel and dentin: A brief history and state of the art, 1995, Quintessence hit, 26, 95

Asmussen E, 1993, State of the art on direct posterior filling materials and dentine bonding, 33

10.1002/jbm.820160307

10.1111/j.1365-2842.1983.tb00133.x

Takemura K, 1983, Antibacterial activity of a Bis‐GMA based composite resin and antibacterial effect of chlorhexidine incorporation, Jpn J Conserv Dent, 26, 540

Ribeiro J, 1991, In vitro antibacterial effect of chlorhexidine added to glass‐ionomer cements, Scand J Dent Res, 99, 533

Imazato S, 1993, Immobilization of an antibacterial component in composite resin, Dent Jpn, 30, 63

10.1177/00220345940730080701

10.1177/00220345940730100901

10.1016/0300-5712(95)93576-N

10.1159/000260711

10.1177/00220345860650010201

10.1177/00220345860650010301

10.14219/jada.archive.1957.0106

10.1177/00220345600390010301

Forsten L, 1972, Fluoride release by silicate cements and composite resins, Scand J Dent Res, 80, 515

10.1038/sj.bdj.4803032

Forsten L., 1976, Fluoride release from a fluoride‐containing amalgam and two luting cements, Scand J Dent Res, 84, 348

10.14219/jada.archive.1978.0195

10.1159/000260773

Arends J, 1988, Fluoride release from a composite resin, Quintessence Int, 19, 513

10.1159/000261467

Cooley RL, 1988, Fluoride release and color stability of a fluoride‐containing composite resin, Quintessence Int, 19, 899

10.1016/S0109-5641(88)80061-7

10.1016/0109-5641(89)90096-1

Swift EJ., 1989, Fluoride release from two composite resins, Quintessence Int, 20, 895

O'ConxellJJ KwanSCM.Fluorine‐containing dental materials. US Patent 1988; 4 772 325.

10.1021/ma00232a032

10.1177/00220345870660101601

Masuhara E, 1985, Current status of release of fluoride ions and other bioactive agents from dental materials: prospects for controlled release, Crit Rev Therap Drug Carrier Systems, 1, 91

10.1177/088532828600100406

10.1177/00220345840630051701

10.1016/0889-5406(89)90250-3

10.1016/0109-5641(92)90098-W

Mörmann W, 1982, Komposit‐Inlays: Marginale Adaptation. Randdichtigkeit, Porosität und okklusaler Verschleiss, Dtsch Zahnärztl Z, 37, 458

Lutz F, 1987, Die Zahnfarbene Seitenzahn‐Restauration, Phillip J, 3, 127

Robinson PB, 1987, Comparison of microleakage in direct and indirect composite resin restorations. in vitro, Oper Dent, 12, 113

Shortall AC, 1989, Marginal seal comparisons between resin‐bonded Class II porcelain inlays, posterior composite restorations, and direct composte resin inlays, Int J Prosthodont, 2, 217

10.1038/sj.bdj.4807685

10.1016/0109-5641(95)80034-4

10.1177/00220345910700121201

Peutzfeldt A, 1992, Effect of temperature and duration of post‐cure on selected mechanical properties of resin composites containing carboxylic anhydrides, Scand J Dent Res, 100, 296

10.1111/j.1600-0722.1995.tb00170.x

10.1177/00220345920710111601

10.3109/00016359209012770

10.1177/00220345940730020501

10.1177/00220345940730101101

10.1111/j.1600-0722.1996.tb00082.x

10.3109/00016359709115399