Synthesis, characterization, shrinkage and curing kinetics of a new low-shrinkage urethane dimethacrylate monomer for dental applications

Dental Materials

Volumn 23, Issue 8, 2007, Pages 1030-1041

  Atai, Mohammad ^a   Ahmadi, Mehdi ^b   Babanzadeh, Samal ^a   Watts, David C ^c  

^a IRAN POLYMER AND PETROCHEMICAL INSTITUTE   (Iran)

^b UNIVERSITY OF MAZANDARAN   (Iran)

^c UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Curing kinetics; Resin monomers; Shrinkage strain; UDMA

Indexed keywords

CHARACTERIZATION; CURING; DENTISTRY; KINETICS; POLYETHYLENE GLYCOLS; REFRACTIVE INDEX; SHRINKAGE; SYNTHESIS (CHEMICAL);

CURING KINETICS; RESIN MONOMERS; SHRINKAGE-STRAIN; UDMA;

MONOMERS;

ACRYLIC ACID RESIN; BIOMEDICAL AND DENTAL MATERIALS; ISOPHORONE POLYURETHANE; METHACRYLIC ACID DERIVATIVE; POLYURETHAN; POLYURETHANE DIMETHACRYLATE; UNCLASSIFIED DRUG;

ANALYSIS OF VARIANCE; ARTICLE; CHEMISTRY; DENTAL CARE; DIFFERENTIAL SCANNING CALORIMETRY; ENDODONTICS; FLOW KINETICS; HEAT; INFRARED SPECTROSCOPY; KINETICS; LIGHT; MATERIALS TESTING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE TRANSITION; RADIATION EXPOSURE; SYNTHESIS; VISCOSITY;

ACRYLIC RESINS; ANALYSIS OF VARIANCE; CALORIMETRY, DIFFERENTIAL SCANNING; DENTAL MATERIALS; DENTAL STRESS ANALYSIS; HEAT; KINETICS; LIGHT; MAGNETIC RESONANCE SPECTROSCOPY; MARGINAL ADAPTATION (DENTISTRY); MATERIALS TESTING; METHACRYLATES; PHASE TRANSITION; POLYURETHANES; RHEOLOGY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; VISCOSITY;

EID: 34250167517     PISSN: 01095641     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dental.2007.03.004     Document Type: Article

References (51)

1. Burel F., Lecamp L., Youssef B., Bunel C., and Saiter J.-M. Synthesis and photoinitiated polymerization of a new urethane acrylate monomer: influence of polymerization temperature. Thermochim Acta 326 (1999) 133-141
2. Moszner N., Völkel T., Fischer U.K., Klester A., and Rheinberger V. Synthesis and polymerisation of new multifunctional urethane methacrylates. Die Angewandte Makromolekulare Chemie 265 1 (1999) 31-35
3. Assumption Heidi J., and Mathias Lon J. Photopolymerization of urethane dimethacrylates synthesized via a non-isocyanate route. Polymer 44 (2003) 5131-5136
4. Milyavskii Y.S., Shcherbakov V.V., and Khamidulova Z.S. Ultraviolet hardenable urethane acrylate composites for coating fiber light-guides. J Opt Technol 70 (2003) 680-681
5. Wang W., and Cheng K. Synthesis and characterization of ultraviolet light-curable resin for optical fiber coating. Eur Polym J 39 (2003) 1891-1897
6. Xu J., Pang W., and Shi W. Synthesis of UV-curable organic-inorganic hybrid urethane acrylates and properties of cured films. Thin Solid Films 514 1-2 (2006) 69-75
7. Gasper Susan M., Schissel David N., Baker Linda S., Smith Diane L., Youngman Randall E., Wu L.-M., et al. Integrated approach to studying the development and final network properties of urethane acrylate coatings. Macromolecules 39 6 (2006) 2126-2136
8. Khudyakov I.V., Swiderski K.W., and Greer R.W. Structure-property relations in UV-curable urethane acrylate oligomers. J Appl Polym Sci 99 (2006) 489-494
9. Jiang L., Xu Q., and Hu C.P. Preparation and characterization of waterborne polyurethaneurea composed of dimer fatty acid polyester polyol. J Nanomater 2006 (2006) 1-10
10. Chang E.P., and Holguin D. Curable optically clear pressure-sensitive adhesives. J Adhesion 81 5 (2005) 495-508
11. Yaobin R., Huiming P., Longsi L., Jianming X., and Yongqiang Y. Synthesis of polyurethane acrylate and application to ultraviolet-curable pressure-sensitive adhesive. Polym-Plast Technol Eng 45 4 (2006) 495-502
12. Sarrionandia M., Mondragon I., Moschiar M., and Vazquez A. Analysis of kinetic parameters of a urethane-acrylate resin for pultrusion process. J Appl Polym Sci 77 (2000) 355-362
13. Finger W.J., and Fritz U.B. Resin bonding to enamel and dentin with one-component UDMA/HEMA adhesives. Eur J Oral Sci 105 2 (1997) 183-186
14. Asmussen E., and Peutzfeldt A. Influence of UEDMA, BisGMA and TEGDMA on selected mechanical properties of experimental resin composites. Dent Mater 14 (1998) 51-56
15. Krishnan V.K., Lizymol P.P., and Nair S.P. Urethane tetramethacrylates: novel substitutes as resin matrix in radiopaque dental composites. J Appl Polym Sci 74 (1999) 735-746
16. Tanaka J., Hashimoto T., Stansbury J.W., Antonucci J.M., and Suzuki K. Polymer properties on resins composed of UDMA and methacrylates with the carboxyl group. Dent Mater J 20 3 (2001) 206-215
17. Dickens S.H., Stansbury J.W., Choi K.M., and Floyd C.J.E. Photopolymerization kinetics of methacrylate dental resins. Macromolecules 36 16 (2003) 6043-6053
18. Floyd C.J., and Dickens S.H. Network structure of Bis-GMA- and UDMA-based resin systems. Dent Mater 22 12 (2006) 1143-1149
19. Sideridou I.D., and Achilias D.S. Elution study of unreacted Bis-GMA, TEGDMA, UDMA, and Bis-EMA from light-cured dental resins and resin composites using HPLC. J Biomed Mater Res B Appl Biomater 74 1 (2005) 617-626
20. Ahn K.-D., Chung C.-M., and Kim Y.-H. Synthesis and photopolymerization of multifunctional methacrylates derived from Bis-GMA for dental applications. J Appl Polym Sci 71 (1999) 2033-2037
21. Klee J.E., Neidhart F., Flammersheim H.-J., and Mulhaupt R. Monomers for low shrinking composites, 2a: synthesis of branched methacrylates and their application in dental composites. Macromol Chem Phys 200 (1999) 517-523
22. Chung C.-M., Kim J.-G., Kim M.-S., Kim K.-M., and Kim K.-N. Development of a new photocurable composite resin with reduced curing shrinkage. Dent Mater 18 (2002) 174-178
23. Chung C.-M., Kim M.-S., Kim J.-G., and Jang D.-O. Synthesis and photopolymerization of trifunctional methacrylates and their application as dental monomers. J Biomed Mater Res 62 (2002) 622-627
24. Khatri C.A., Stansbury J.W., Schultheisz C.R., and Antonucci J.M. Synthesis, characterization and evaluation of urethane derivatives of Bis-GMA. Dent Mater 19 (2003) 584-588
25. Kim Y., Kim C.K., Cho B.H., Son H.H., Um C.M., and Kim O.Y. A new resin matrix for dental composite having low volumetric shrinkage. J Biomed Mater Res Part B: Appl Biomater 70B (2004) 82-90
26. Chen M.-H., Chen C.-R., Hsu S.-H., Sun S.-P., and Su W.-F. Low shrinkage light curable nanocomposite for dental restorative material. Dent Mater 22 2 (2006) 138-145
27. Satsangi N., Rawls H.R., and Norling B.K. Synthesis of low-shrinkage polymerizable liquid-crystal monomers. J Biomed Mater Res Part B: Appl Biomater 71B (2004) 153-158
28. Ge J., Trujillo M., and Stansbury J. Synthesis and photopolymerization of low shrinkage methacrylate monomers containing bulky substituent groups. Dent Mater 21 12 (2005) 1163-1169
29. Weinmann W., Thalacker C., and Guggenberger R. Siloranes in dental composites. Dent Mater 21 1 (2005) 68-74
30. Kamal M.R., and Sourour S. Kinetic and thermal characterization of thermoset cure. Polym Eng Sci 13 1 (1973) 59-64
31. Kamal M.R. Thermoset characterization for moldability analysis. Polym Eng Sci 14 3 (1974) 231-239
32. Atai M., and Watts D.C. A new kinetic model for the photopolymerization shrinkage-strain of dental composites and resin-monomers. Dent Mater 22 8 (2006) 785-791
33. Atai M., Nekoomanesh M., Hashemi S.A., and Amani S. Physical and mechanical properties of an experimental dental composite based on a new monomer. Dent Mater 20 (2004) 663-668
34. Watts D.C., and Cash A.J. Kinetic measurements of photo-polymerization contraction in resins and composites. Meas Sci Technol 2 (1991) 788-794
35. Atai M., Watts D.C., and Atai Z. Shrinkage strain-rates of dental resin-monomer and composite systems. Biomaterials 26 (2005) 5015-5020
36. Kloosterboer J.G. Network formation by chain crosslinking photopolymerization and its applications in electronics. Adv Polym Sci 84 (1988) 1-61
37. Bowman C.N., and Peppas N.A. Coupling of kinetics and volume relaxation during polymerizations of multiacrylates and multimethacrylates. Macromolecules 24 (1991) 1914-1920
38. Andrzejewska E. Photopolymerization kinetics of multifunctional monomers. Prog Polym Sci 26 (2001) 605-665
39. Cook W.D. Photopolymerization kinetics of dimethacrylates using the camphorquinone/amine initiator system. Polymer 33 3 (1992) 600-609
40. Maffezzoli A., Della Pietra A., Rengo S., Nicolais L., and Valletta G. Photopolymerization of dental composite matrices. Biomaterials 15 15 (1994) 1221-1228
41. Nie J., Rabek J.F., and Linden L.-A. Photopolymerization of poly(melamine-co-formaldehyde) acrylate for dental restorative resins. Polym Int 48 (1999) 129-136
42. Khudyakov I.V., Legg J.C., Purvis M.B., and Overton B.J. Kinetics of photopolymerization of acrylates with functionality of 1-6. Ind Eng Chem Res 38 (1999) 3354-3359
43. Lee I.B., and Um C.M. Thermal analysis on the cure speed of dual cured resin cements under porcelain inlays. J Oral Rehabil 28 (2001) 186-197
44. Stansbury J.W., and Dickens S.H. Network formation and compositional drift during photo-initiated copolymerization of dimethacrylate monomers. Polymer 42 (2001) 6363-6369
45. Andrzejewska E., Linden L.-A., and Rabek J.F. Modelling the kinetics of photoinitiated polymerization of di(meth)acrylates. Polym Int 42 (1997) 179-187
46. Maffezzoli A., and Terzi R. Effect of irradiation intensity on the isothermal photopolymerization kinetics of acrylic resins for stereolithography. Thermochim Acta 321 (1998) 111-121
47. Kenny J.M. Determination of autocatalytic kinetic model parameters describing thermoset cure. J Appl Polym Sci 51 (1994) 761-784
48. Odian G. Principle of polymerization. 2nd ed. (1981), John Wiley & Sons, Inc.
49. Anseth K.S., Wang C.M., and Bowman C.N. Kinetic evidence of reaction diffusion during the polymerization of multi(meth)acrylate monomers. Macromolecules 27 (1994) 650-655
50. Watts D.C. Reaction kinetics and mechanics in photo-polymerised networks. Dent Mater 21 (2005) 27-35
51. Lovell L.G., Stansbury J.W., Syrpes D.C., and Bowman C.N. Effects of composition and reactivity on the reaction kinetics of dimethacrylate/dimethacrylate copolymerizations. Macromolecules 32 (1999) 3913-3921