Dental restorative composites containing 2,2-bis-[4-(2-hydroxy-3- methacryloyloxy propoxy) phenyl] propane derivatives and spiro orthocarbonates

Journal of Biomedical Materials Research - Part B Applied Biomaterials

Volumn 73, Issue 2, 2005, Pages 338-346

  Moon, E J ^a   Lee, J Y ^a   Kim, C K ^a   Cho, B H ^b  

^a Chung Ang University   (South Korea)

^b School of Dentistry   (South Korea)

Author keywords

Bis GMA derivatives; Dental restorative composite; Resin mixture; Spiro orthocarbonate; Volumetric shrinkage

Indexed keywords

CARBONATES; COMPOSITE MATERIALS; DENTAL MATERIALS; PROPANE; SHRINKAGE;

DENTAL RESTORATIVE COMPOSITE RESINS; RING-OPENING REACTIONS; SPIRO ORTHOCARBONATES (SOC); VOLUMETRIC SHRINKAGE;

RESINS;

2,2 BIS[3,5 DIMETHYL 4 (2 HYDROXY 3 METHACRYLOXYPROPOXY)PHENYL]PROPANE; 2,2 BIS[4 (2 HYDROXY 3 METHACRYLOYLOXYPROPOXY)PHENYL]PROPANE DERIVATIVE; CARBONIC ACID DERIVATIVE; METHACRYLIC ACID DERIVATIVE; RESIN; SPIRO COMPOUND; SPIRO ORTHOCARBONATE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DENTAL SURGERY; MECHANICS; POLYMERIZATION; RING OPENING; VOLUMETRY;

BIOCOMPATIBLE MATERIALS; BISPHENOL A-GLYCIDYL METHACRYLATE; COMPOSITE RESINS; MAGNETIC RESONANCE SPECTROSCOPY; MATERIALS TESTING; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 18244388953     PISSN: 00219304     EISSN: None     Source Type: Journal    
DOI: 10.1002/jbm.b.30222     Document Type: Article

References (24)

1. Moszner N, Salz U. New developments of polymeric dental composites. Prog Polym Sci 2001;26:535-576.
2. Sanda F, Endo T. Radical ring-opening polymerization. J Polym Sci A: Polym Chem 2001;39:265-276.
3. Kostoryz EL, Tong PY, Chappelow CC, Eick JD, Glaros AG, Yourtee DM. In vitro cytotoxicity of solid epoxy-based dental resins and their components. Dent Mater 1999;15;363-373.
4. Eick JD, Robinson SJ, Byerley TJ, Chappelow CC. Adhesive and nonshrinking dental resins of the future. Quintessence Int 1993;24;632-640.
5. Retief DH. Do adhesives prevent microleakage? Int Dent J 1994;44:19-26.
6. Van Dijken JWV. A 6-year clinical evaluation of class I poly-acid modified resin composite/resin composite laminate restorations cured with a two-step curing technique. Dent Mater 2003;19:423-428.
7. Cho BH, Dickens SH, Bae JH, Chang CG, Son HH, Um CM. Effect of the interfacial bond quality on the direction of the polymerization shrinkage flow in composite resin restorations. Oper Dent 2002;27;297-304.
8. Van Krevelen DW. Properties of polymers (3rd ed.). New York: Elsevier Science; 1990. p 20-87.
9. Bailey WJ, Sun RL. Synthesis and radical ring opening polymerization of spiro o-carbonates. Polym Prepr (Am Chem Soc, Div Polym Chem) 1972;13:281.
10. Endo T, Bailey WJ. Synthesis and radical ring-opening polymerization of 2-methyl-1,4,6-trioxaspiro[4,4]nonane. J Polym Sci Polym Lett Ed 1980;18:25-27.
11. Endo T, Okawara M, Yamazaki N, Bailey WJ. Preparation and ring-opening polymerization of unsaturated spiro orthoester. J Polym Sci Polym Chem Ed 1981;19:1283-1286.
12. Tanigaki K, Saigo K, Ohnishi Y, Kato H, Mizutani K, Ogasawara T, Endo T. Behavior of polymers containing spiroorthoester or bicycloorthoester structure under EB and X-ray irradiation conditions. J Appl Polym Sci 1985;30:1419-1428.
13. Holder AJ, White DA, Harris CD, Eick JD, Chappelow CC. A semiemprical quantum mechanical study of the cationic homopolymerization of expanding and potentially expanding monomer systems. Mole Struct (Theochem) 2001;541;159-169.
14. Schaefer R, Heindl D, Schöde D, Nuyken O, Böhner R. Erdmann C. Polymerizable materials. U. S. Patent No. 5,750,590; 1998.
15. Fukuchi I. Sanda F. Endo T. Synthesis and cationic polymerization of 2-phenyl-1,6-dioxaspiro[4,6]undecane. A novel expandable monomer undergoing cationic double ring-opening polymerization. Macromolecules 2001;34:4296-4298.
16. Chappelow CC, Pinzino CS, Jeang L, Harris CD, Holder AJ, Eick JD. Photoreactivity of expanding monomers and epoxy-based matrix resin system, J Appl Polym Sci 2000;76:1715-1724.
17. Wang CS. Study on epoxy resin modified with prepolymers containing spiro orthocarbonate J Mater Sci Lett 1999;18: 1259-1262.
18. Sanda F, Takata T, Endo T. Synthesis and radical polymerization of spiro orthocarbonates bearing exomethylene groups. J Polym Sci A Polym Chem 1994;32:323-332.
19. Zhou Z, Jin B, He P. Copolymerization behavior and kinetics of an epoxy copolymer with zero shrinkage. J Appl Polym Sci 2002;84:1457-1464.
20. Komatsu S, Takata T, Endo T. New polymerization of spiroorthocarbonate: cationic single ring-opening polymerization of 2,3-benzo-1,4,6,12- tetraoxaspiro[4,7]dodecane. Macromolecules 1993;26:875-878.
21. Endo T, Maruoka S, Yokozawa T. Spiro orthocarbonate undertaking radical and cationic polymerization. Macromolecules 1987;20:2690-2693.
22. Stansbury JW. Synthesis and evaluation of new oxaspiro monomers for double ring-opening polymerization. J Dent Res 1992; 71:1408-1412.
23. Stansbury JW. Free radical ring-opening polymerization of unsaturated, asymmetric spiro orthocarbonates [dissertation]. College Park: University of Maryland; 1988.
24. Kim Y, Kim CK, Cho BH, Um JM, Son H, Kim OY. A new resin matrix for dental composite having low volumetric shrinkage. J Biomed Mater Res B Appl Biomater 2004;70B:82-90.