Synthesis and characterization of low surface energy fluoropolymers as potential barrier coatings in oral care

Journal of Biomedical Materials Research - Part A

Volumn 84, Issue 4, 2008, Pages 994-1005

  Churchley, David P ^a   Barbu, Eugen ^a   Ewen, Richard J ^b   Shen, Zhihao ^c   Kim, Yongchul ^c   McHugh, Mark A ^c   Zhong, Yi Zhang ^a   Nevell, Thomas G ^a   Rees, Gareth D ^d   Tsibouklis, John ^a  

^a UNIVERSITY OF PORTSMOUTH   (United Kingdom)

^b UNIVERSITY OF THE WEST OF ENGLAND   (United Kingdom)

^c Virginia Commonwealth University   (United States)

^d GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Dental care; Fluoropolymers; Low surface energy

Indexed keywords

DENTAL CARE; ENERGY DETERMINATIONS; LOW SURFACE ENERGY; NANOSUSPENSIONS;

CHARACTERIZATION; DENTISTRY; INTERFACIAL ENERGY; PLASTIC COATINGS; POLYMER FILMS; SYNTHESIS (CHEMICAL);

FLUORINE CONTAINING POLYMERS;

CARBON DIOXIDE; COPOLYMER; FLUOROPOLYMER; HYDROXYAPATITE; POLY(METHYL METHACRYLATE); POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOGRAPHY; DENTAL PELLICLE; DENTURE; ENAMEL; ENERGY; FLUORINATION; MATERIAL COATING; MOUTH HYGIENE; SPECTROSCOPY;

BIOCOMPATIBLE MATERIALS; CARBON DIOXIDE; DURAPATITE; FLUORINE; MAGNETIC RESONANCE SPECTROSCOPY; MICROSCOPY, ELECTRON, SCANNING; MODELS, CHEMICAL; POLYMERS; POLYMETHYL METHACRYLATE; PROTECTIVE DEVICES; SOLUBILITY; SPECTROPHOTOMETRY; SURFACE PROPERTIES; TEMPERATURE;

EID: 39749202175     PISSN: 15493296     EISSN: 15524965     Source Type: Journal    
DOI: 10.1002/jbm.a.31462     Document Type: Article

References (68)

1. Ameduri B, Boutevin B, Kostov G. Fluoroelastomers: Synthesis, properties and applications. Prog Polym Sci 2001;26:105-187.
2. Brady RF Jr. Coming to an unsticky end. Nature 1994;368:16-17.
3. Scheirs J, editor. Modern Fluoropolymers. New York: Wiley; 1997.
4. Miyazawa H, Yokokura H, Ohkubo Y, Kondo Y, Yoshino N. Synthesis of phosphate-type fluorocarbon-hydrocarbon hybrid surfactants and their adsorption onto calcium hydroxyapatite. J Fluorine Chem 2005;126:301-306.
5. Jones FH. Teeth and bones: Applications of surface science to dental materials and related biomaterials. Surf Sci Rep 2001;42:79-205.
6. Stansbury JW, Antonucci JM. Dimethacrylate monomers with varied fluorine contents and distributions. Dent Mater 1999;15:166-173.
7. Yoshino N, Yamauchi T, Kondo Y, Kawase T, Teranaka T. Plaque-controlling surface modifier containing fluorocarbon chain. React Funct Polym 1998;37:271-282.
8. Brady RF Jr. In search of non-stick coatings. Chem Ind 1997;6:219-222.
9. Harris JM, editor. Polyethylene Glycol Chemistry. New York: Plenum Press; 1992.
10. Holmberg K, Bergström K, Brink C, Österberg E, Tiberg F, Harris JM. Effects on protein adsorption, bacterial adhesion and contact angle of grafting peg chains to polystyrene. J Adhes Sci Technol 1993;29:503-517.
11. Österberg E, Bergström K, Holmberg K, Schuman TP, Riggs JA, Burns NL, van Alstine JM, Harris JM. Protein-rejecting ability of surface-bound dextran in end-on and side-on configurations - comparison to peg. J Biomed Mater Res 1995;29:741-747.
12. Jeon SI, Lee JH, Andrade JD, de Gennes PG. Protein surface interactions in the presence of polyethylene oxide. I. Simplified theory. J Colloid Interface Sci 1991;142:149-158.
13. Andrade JD, editor. Polymer Surface Dynamics, New York: Plenum; 1988.
14. Merrill EW, Salzman EW. Polyethylene oxide as a biomaterial. J Am Soc Artif Intern Organs 1983;6:60-64.
15. Holland NB, Qiu YX, Ruegsegger M, Marchant RE. Biomimetic engineering of non-adhesive glycocalyx-like surfaces using oligosaccharide surfactant polymers. Nature 1998;392:799-801.
16. Vacheethasanee K, Marchant RE. Surfactant polymers designed to suppress bacterial (Staphylococcus epidermidis) adhesion on biomaterials. J Biomed Mater Res 2000;50:302-312.
17. Jeong JH, Lim DW, Han DK, Park TG. Synthesis, characterization and protein adsorption behaviors of PLGA/PEG di-block co-polymer blend films. Colloids Surf B 2000;18:371-379.
18. Green RJ, Frazier RA, Shakesheff KM, Davies MC, Roberts CJ, Tendler SJB. Surface plasmon resonance analysis of dynamic biological interactions with biomaterials. Biomaterials 2000;21:1823-1835.
19. Frazier RA, Matthijs G, Davies MC, Roberts CJ, Schacht E, Tendler SJB. Characterization of protein-resistant dextran monolayers. Biomaterials 2000;21:957-966.
20. Elbert DL, Hubbell JA. Surface treatments of polymers for biocompatibility. Annu Rev Mater Sci 1996;26:365-394.
21. Bos R, van der Mei HC, Busscher HJ. Physico-chemistry of initial microbial adhesive interactions - its mechanisms and methods for study. FEMS Microbiol Rev 1999;23:179-230.
22. An YH, Friedman RJ. Concise review of mechanisms of bacterial adhesion to biomaterial surfaces. J Biomed Mater Res 1998;43:338-348.
23. Ong YL, Razatos A, Georgiou G, Sharma MM. Adhesion forces between E. coli bacteria and biomaterial surfaces. Langmuir 1999;15:2719-2725.
24. Cunliffe D, Smart CA, Tsibouklis J, Young S, Alexander C, Vulfson EN. Bacterial adsorption to thermoresponsive polymer surfaces. Biotechnol Lett 2000;22:141-145.
25. Razatos A, Ong YL, Sharma MM, Georgiou G. Molecular determinants of bacterial adhesion monitored by atomic force microscopy. Proc Natl Acad Sci USA 1998;95:11059-11064.
26. Tsibouklis J, Stone M, Thorpe AA, Graham P, Peters V, Heerlien R, Smith JR, Green KL, Nevell TG. Preventing bacterial adhesion onto surfaces: The low-surface-energy approach. Biomaterials 1999;20:1229-1235.
27. Brady RF Jr. Properties which influence marine fouling resistance in polymers containing silicon and fluorine. Prog Org Coat 1999;35:31-35.
28. Harder P, Grunze M, Dahint R, Whitesides GM, Laibinis PE. Molecular conformation in oligo(ethylene glycol)-terminated self-assembled monolayers on gold and silver surfaces determines their ability to resist protein adsorption. J Phys Chem B 1998;102:426-436.
29. Ista LK, Fan H, Baca O, Lopez GP. Attachment of bacteria to model solid surfaces: Oligo(ethylene glycol) surfaces inhibit bacterial attachment. FEMS Microbiol Lett 1996;142:59-63.
30. Evans LV, Clarkson N. Antifouling strategies in the marine environment. J Appl Bacteriol Symp Suppl 1993;74:119S-124S.
31. Clare AS, Rittschof D, Gerhart DJ, Maki JS. Molecular approaches to nontoxic antifouling. Invertebr Reprod Dev 1992;22:67-76.
32. Vrolijk NH, Targett NM, Baier RE, Meyer AE. Surface characterisation of two gorgonian coral species: Implications for a natural antifouling defence. Biofouling 1990;2:39-54.
33. Tsibouklis J, Stone M, Thorpe AA, Graham PD, Nevell TG, Ewen RJ. Surface energy characteristics of polymer film structures: A further insight into the molecular design requirements. Langmuir 1999;15:7076-7079.
34. Tsibouklis J, Nevell TG. Ultra-low surface energy polymers: The molecular design requirements. Adv Mater 2003;15:647-650.
35. Lindner E. A low-surface-energy approach in the control of marine biofouling. Biofouling 1992;6:193-205.
36. Kaye GWC, Laby TH, editors. Table of Physical and Chemical Constants, 15th ed. Harlow: Longman Scientific and Technical; 1992.
37. Meilchen MA, Hasch BM, McHugh MA. Effect of copolymer composition on the phase behavior of mixtures of poly(ethylene-co-methyl acrylate) with propane and chlorodifluoromethane. Macromolecules 1991;24:4874-4882.
38. 2 and halogenated supercritical solvents. Macromolecules 1996;29:6548-6555.
39. Diguet R, Deul R, Franck EU. Static dielectric permittivity and density of liquid dichloromethane to 200 Mpa. Berichte Der Bunsen-Gesellschaft - Phys Chem Chem Phys 1985;89:800-804.
40. Sen YL, Kiran E. A new experimental system to study the temperature and pressure dependence of viscosity, density, and phase behavior of pure fluids and solutions. J Supercrit Fluids 1990;3:91-99.
41. Byun H-pressure densities of ethane, pentane, pentane-d(12), 25.5 wt % ethane in pentane-d(12), 2.4 wt % deuterated poly(-ethylene-co-butene) (PEB) in ethane, 5.3 wt % hydrogenated PEB in pentane, 5.1 wt % hydrogenated peb in pentane-d(12), and 4.9 wt % hydrogenated peb in pentane-d(12) + 23.1 wt % ethane. J Chem Eng Data 2000;45:810-814.
42. Storsberg J, Ritter H. Cyclodextrins in polymer synthesis: A green route to fluorinated polymers via cyclodextrin complexes in aqueous solution. Macromol Chem Phys 2002;203:812-818.
43. Cowie JMG. Polymers - Chemistry and Physics of Modern Materials. London: Blackie Academic and Professional; 1993.
44. Ciardelli F, Aglietto M, Passaglia E, Montagnini di Mirabello L, Ruggeri G. Molecular design of fluorinated acrylic polymers for coating. Pitture e Vernici -Europe 1996;72:21-30.
45. Wang JG, Mao GP, Ober CK, Krammer EJ. Liquid crystalline, semifluorinated side group block copolymers with stable low energy surfaces: Synthesis, liquid crystalline structure, and critical surface tension. Macromolecules 1997;30:1906-1914.
46. Andruzzi L, Chiellini E, Galli G, Li XF, Kang SH, Ober CK. Engineering low-surface-energy polymers through molecular design: Synthetic routes to fluorinated polystyrene-based block copolymers. J Mater Chem 2002;12:1684-1692.
47. Tsibouklis J, Graham P, Eaton PJ, Smith JR, Nevell TG, Smart JD, Ewen RJ. Poly(perfluoroalkyl methacrylate) film structures: Surface organization phenomena, surface energy determinations and force of adhesion measurements. Macromolecules 2000;33:8460-8465.
48. Morra M, Occhiello E, Garbassi F. Knowledge about polymer surfaces from contact-angle measurements. Adv Colloid Interface Sci 1990;32:79-116.
49. Nakajima A, Hashimoto K, Watanabe T. Recent studies on super-hydrophobic films. Monatshefte für Chemie 2001;132:31-41.
50. Good RJ. Contact angle, wetting and adhesion: A critical review. J Adhes Sci Technol 1992;6:1269-1302.
51. Park IJ, Lee S-B, Choi CK. Surface properties for poly(perfluoroalkylethyl methacrylate)/poly(n-alkyl methacrylate)s mixtures. J Appl Polym Sci 1994;54:1449-1454.
52. Thomas RR, Anton DR, Graham WF, Darmon MJ, Sauer BB, Stika KM, Swartzfager DG. Preparation and surface properties of acrylic polymers containing fluorinated monomers. Macromolecules 1997;30:2883-2890.
53. Krupers MJ, Sheiko SS, Moeller M. Micellar morphology of a semifluorinated diblock copolymers. Polym Bull 1998;40:211-217.
54. Krupers M, Moeller M. Semifluorinated diblock copolymers. Synthesis, modelling characterization and amphiphilic properties. Macromol Chem Phys 1997;198:2163-2180.
55. Shull KR, Winey KI, Thomas EL, Kramer EJ. Segregation of block copolymer micelles to surfaces and interfaces. Macromolecules 1991;24:2748-2751.
56. Ito H, Imae T, Nakamura T, Sugiura M, Oshibe Y. Self-association of water-soluble fluorinated diblock copolymers in solutions. J Colloid Interface Sci 2004;276:290-298.
57. Raynor MW, Bartle KD. Supercritical fluid chromatography and extraction in surface coatings analysis - Review of representative applications. J Supercrit Fluids 1993;6:39-49.
58. Hauthal WH. Advances with supercritical fluids. Chemosphere 2001;43:123-135.
59. Kameo A, Yoshimura T, Esumi K. Preparation of noble metal nanoparticles in supercritical carbon dioxide. Colloids Surf A 2003;215:181-189.
60. Dardin A, Cain JB, DeSimone JM, Johnson CS Jr, Samulski ET. High-pressure NMR of polymers dissolved in supercritical carbon dioxide. Macromolecules 1997;30:3593-3599.
61. Dardin A, DeSimone JM, Samulski ET. Fluorocarbon dissolved in supercritical carbon dioxide. NMR evidence for specific solute-solvent interactions. J Phys Chem B 1998;102:1775-1780.
62. Kazarian SG, Vincent MF, Bright FV, Liotta CL, Eckert CA. Specific intermolecular interaction of carbon dioxide with polymers. J Am Chem Soc 1996;118:1729-1736.
63. 2 interaction with polymers containing fluorinated groups: Computational chemistry of model compounds and molecular simulation of poly[bis(2,2,2-trifluoroethoxy) phosphazene]. Polymer 2003;44:4363-4377.
64. 2: Experimental and molecular modelling results. Macromolecules 2004;37:7799-7807.
65. McHugh MA, Garach-Domech A, Park LH, Li D, Barbu E, Graham P, Tsibouklis J. Impact of fluorination and side-chain length on poly(methylpropenoxyalkylsiloxane) and poly(alkylmethacrylate) solubility in supercritical carbon dioxide. Macromolecules 2002;35:6479-6482.
66. 2. Ind Eng Chem Res 2003;42:6499-6504.
67. Kirby CF, McHugh MA. Phase behavior of polymers in supercritical fluid solvents. Chem Rev 1999;99:565-602.
68. 2. J Phys Chem 1996;100:15581-15587.