Synthesis and characterization of dimethacrylates containing quaternary ammonium functionalities for dental applications

Dental Materials

Volumn 28, Issue 2, 2012, Pages 219-228

  Antonucci, Joseph M ^a   Zeiger, Diana N ^a   Tang, Kathy ^a   Lin Gibson, Sheng ^a   Fowler, Bruce O ^a   Lin, Nancy J ^a  

^a NATIONAL INSTITUTE OF STANDARDS AND TECHNOLOGY   (United States)

Author keywords

Bacterial adhesion; Cytotoxicity; Degree of conversion; Dental restorative material; Dimethacrylate monomer; Menschutkin reaction; MTT assay; Quaternary ammonium salts; Streptococcus mutans; Surface charge density

Indexed keywords

BACTERIAL ADHESION; DEGREE OF CONVERSION; DENTAL RESTORATIVE MATERIALS; DIMETHACRYLATES; MENSCHUTKIN REACTION; MTT ASSAYS; QUATERNARY AMMONIUM SALT; STREPTOCOCCUS MUTANS;

ACRYLIC MONOMERS; ADHESION; CHARGE DENSITY; CYTOTOXICITY; DENTAL COMPOSITES; DENTAL MATERIALS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GLYCOLS; MACROPHAGES; MAMMALS; MEDICAL APPLICATIONS; METABOLISM; MONOMERS; PHENOLS; POLYMERS; RESINS; SALTS; SURFACE CHARGE; SURFACES; SYNTHESIS (CHEMICAL); VISCOSITY;

AMMONIUM COMPOUNDS;

2-(DIMETHYLAMINO)ETHYL METHACRYLATE; ANTIINFECTIVE AGENT; BIOMEDICAL AND DENTAL MATERIALS; BISPHENOL A BIS(2 HYDROXYPROPYL) ETHER DIMETHACRYLATE; DIAGNOSTIC AGENT; FLUORESCEIN DERIVATIVE; FLUORESCENT DYE; MACROGOL DERIVATIVE; METHACRYLIC ACID DERIVATIVE; METHACRYLIC ACID DIMETHYLAMINOETHYL ESTER; POLYMETHACRYLIC ACID DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE; TRIETHYLENE GLYCOL DIMETHACRYLATE;

ANIMAL; ARTICLE; BACTERIUM ADHERENCE; CELL COUNT; CELL LINE; CELL SURVIVAL; CHEMISTRY; DRUG EFFECT; FLOW KINETICS; INFRARED SPECTROSCOPY; MACROPHAGE; MATERIALS TESTING; MICROBIAL VIABILITY; POLYMERIZATION; STREPTOCOCCUS MUTANS; SURFACE PROPERTY; SYNTHESIS; VISCOSITY;

ANIMALS; ANTI-INFECTIVE AGENTS; BACTERIAL ADHESION; BISPHENOL A-GLYCIDYL METHACRYLATE; CELL COUNT; CELL LINE; CELL SURVIVAL; DENTAL MATERIALS; FLUORESCEINS; FLUORESCENT DYES; MACROPHAGES; MATERIALS TESTING; METHACRYLATES; MICROBIAL VIABILITY; POLYETHYLENE GLYCOLS; POLYMERIZATION; POLYMETHACRYLIC ACIDS; QUATERNARY AMMONIUM COMPOUNDS; RHEOLOGY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STREPTOCOCCUS MUTANS; SURFACE PROPERTIES; VISCOSITY;

EID: 84855765450     PISSN: 01095641     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dental.2011.10.004     Document Type: Article

References (29)

1. R.L. Bowen Properties of a silica-reinforced polymer for dental restorations J Am Dent Assoc 66 1963 57 64
2. J.M. Antonucci, and J.W. Stansbury Molecularly designed dental polymers R. Arshady, Desk reference of functional polymers: syntheses and applications 1997 American Chemical Society Washington, DC 719 738
3. S.M. Mota, C. Enoki, I.Y. Ito, A.M. Elias, and M.A. Matsumoto Streptococcus mutans counts in plaque adjacent to orthodontic brackets bonded with resin-modified glass ionomer cement or resin-based composite Braz Oral Res 22 1 2008 55 60
4. E.R. Kenawy, S.D. Worley, and R. Broughton The chemistry and applications of antimicrobial polymers: a state-of-the-art review Biomacromolecules 8 5 2007 1359 1384 (Pubitemid 46865105)
5. S. Imazato, M. Torii, Y. Tsuchitani, J.F. Mccabe, and R.R.B. Russell Incorporation of bacterial inhibitor into resin composite J Dent Res 73 8 1994 1437 1443
6. Y.H. Xiao, J.H. Chen, M. Fang, X.D. Xing, H. Wang, and Y.J. Wang Antibacterial effects of three experimental quaternary ammonium salt (QAS) monomers on bacteria associated with oral infections J Oral Sci 50 3 2008 323 327
7. S. Imazato, Y. Kinomoto, H. Tarumi, S. Ebisu, and F.R. Tay Antibacterial activity and bonding characteristics of an adhesive resin containing antibacterial monomer MDPB Dent Mater 19 4 2003 313 319
8. F. Li, J. Chen, Z. Chai, L. Zhang, Y. Xiao, and M. Fang Effects of a dental adhesive incorporating antibacterial monomer on the growth, adherence and membrane integrity of Streptococcus mutans J Dent 37 4 2009 289 296
9. S. Imazato, T. Imai, R.R. Russell, M. Torii, and S. Ebisu Antibacterial activity of cured dental resin incorporating the antibacterial monomer MDPB and an adhesion-promoting monomer J Biomed Mater Res 39 4 1998 511 515 (Pubitemid 28079710)
10. S. Imazato, N. Ebi, Y. Takahashi, T. Kaneko, S. Ebisu, and R.R.B. Russell Antibacterial activity of bactericide-immobilized filler for resin-based restoratives Biomaterials 24 20 2003 3605 3609 (Pubitemid 36703135)
11. N. Beyth, I. Yudovin-Farber, R. Bahir, A.J. Domb, and E.I. Weiss Antibacterial activity of dental composites containing quaternary ammonium polyethylenimine nanoparticles against Streptococcus mutans Biomaterials 27 21 2006 3995 4002
12. N. Menschutkin Über die affinitätskoeffizienten der alkylhaloide und der amine Z Phys Chem 6 1890 41 57
13. H. Noguchi, and A. Rembaum Reactions of N,N,N′,N′- tetramethyl-alpha,w-diaminoalkanes with alpha,w-dihaloalkanes. I. 1 - y reactions Macromolecules 5 3 1972 253 260
14. Rembaum A. Ionene polymers for selectively inhibiting the vitro growth of malignant cells. US Patent no. 4,013,507; 1977.
15. D.N. Zeiger, C.M. Stafford, Y.J. Cheng, S.D. Leigh, S. Lin-Gibson, and N.J. Lin Effects of sample preparation on bacterial colonization of polymers Langmuir 26 4 2010 2659 2664
16. N.J. Lin, P.L. Drzal, and S. Lin-Gibson Two-dimensional gradient platforms for rapid assessment of dental polymers: a chemical, mechanical and biological evaluation Dent Mater 23 10 2007 1211 1220 (Pubitemid 47223409)
17. J.C. Tiller, C.J. Liao, K. Lewis, and A.M. Klibanov Designing surfaces that kill bacteria on contact Proc Natl Acad Sci U S A 98 11 2001 5981 5985 (Pubitemid 32488179)
18. A.P. Wilson Cytotoxicity and viability assays J.R.W. Masters, Animal cell culture: a practical approach 3rd ed. 2003 Oxford University Press Inc. New York 175 213
19. D. Lin-Vien, N. Colthup, W. Fately, and J. Grasselli The handbook of infrared and Raman characteristic frequencies of organic molecules 1991 Academic Press Boston
20. D.C. Mckean, J.L. Duncan, and L. Batt CH stretching frequencies, bond lengths and dissociation energies Spectrochim Acta A A29 6 1973 1037 1049
21. C.J. Pouchert The Aldrich library of FT-IR spectra 2nd ed. 1997 Aldrich Milwaukee
22. F. Goncalves, Y. Kawano, C. Pfeifer, J.W. Stansbury, and R.R. Braga Influence of BisGMA TEGDMA, and BisEMA contents on viscosity, conversion, and flexural strength of experimental resins and composites Eur J Oral Sci 117 4 2009 442 446
23. S. Imazato, R.R. Russell, and J.F. Mccabe Antibacterial activity of MDPB polymer incorporated in dental resin J Dent 23 3 1995 177 181
24. J.L. Ferracane, and J.R. Condon Rate of elution of leachable components from composite Dent Mater 6 4 1990 282 287
25. Z. Chai, F. Li, M. Fang, Y. Wang, S. Ma, and Y. Xiao The bonding property and cytotoxicity of a dental adhesive incorporating a new antibacterial monomer J Oral Rehabil 2011
26. S. Imazato, N. Ebi, H. Tarumi, R.R. Russell, T. Kaneko, and S. Ebisu Bactericidal activity and cytotoxicity of antibacterial monomer MDPB Biomaterials 20 9 1999 899 903 (Pubitemid 29184771)
27. N.M. Milovic, J. Wang, K. Lewis, and A.M. Klibanov Immobilized N-alkylated polyethylenimine avidly kills bacteria by rupturing cell membranes with no resistance developed Biotechnol Bioeng 90 6 2005 715 722 (Pubitemid 40741095)
28. R. Kugler, O. Bouloussa, and F. Rondelez Evidence of a charge-density threshold for optimum efficiency of biocidal cationic surfaces Microbiology 151 Pt 5 2005 1341 1348 (Pubitemid 40711781)
29. H. Murata, R.R. Koepsel, K. Matyjaszewski, and A.J. Russell Permanent, non-leaching antibacterial surface - 2: How high density cationic surfaces kill bacterial cells Biomaterials 28 32 2007 4870 4879 (Pubitemid 47285332)