Poly(vinylphosphonic acid) and its derivatives

Progress in Polymer Science (Oxford)

Volumn 35, Issue 8, 2010, Pages 1078-1092

  MacArie, Lavinia ^a   Ilia, Gheorghe ^a,b  

^a ACADEMY OF ROMANIAN SCIENTISTS   (Romania)

^b WEST UNIVERSITY OF TIMISOARA   (Romania)

Author keywords

Applications; Poly(vinylphosphonic acid); Poly(vinylphosphonic acid) derivatives; Synthesis

Indexed keywords

APPLICATIONS; CERAMIC MATERIALS; MATERIALS SCIENCE; SYNTHESIS (CHEMICAL);

DAILY LIVES; INNOVATIVE PRODUCT; POLYMER APPLICATIONS; SPECIAL PROPERTIES; SYNTHETIC POLYMERS; VINYL POLYMER; VINYLPHOSPHONATES; VINYLPHOSPHONIC ACIDS;

POLYMERS;

EID: 77955421340     PISSN: 00796700     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.progpolymsci.2010.04.001     Document Type: Review

References (105)

1. H.-G. Elias An introduction to plastics 2003 Wiley-VCH Weinheim
2. A. Akelah, and A. Moet Functionalized polymers and their application 1990 Chapman and Hall New York p. 15-48
3. J.M.J. Frechet Functional polymers: from plastic electronics to polymer-assisted therapeutics Prog Polym Sci 30 2005 844 857
4. A.H. Ford-Moore, and J.H. Williams The reaction between trialkyl phosphites and alkyl halides J Chem Soc 1947 1465 1467
5. G.M. Kosolapoff Isomerization of alkyl phosphites. VII. Some derivatives of 2-bromoethane phosphonic acid J Am Chem Soc 70 1948 1971 1972
6. K.D. Berlin, and G.B. Butler Poly(diphenylvinylphosphine oxide) J Org Chem 26 1961 2537 2538
7. Becker LW. Poly(alkenyl)phosphonic acid and methods of use thereof. US Patent 4,446,046 assigned to Betz Laboratories, Inc.; 1984.
8. J. Korlach, P.J. Marks, R.L. Cicero, J.J. Gray, D.L. Murphy, and D.B. Roitman Selective aluminum passivation for targeted immobilization of single DNA polymerase molecules in zero-mode waveguide nanostructures Proc Natl Acad Sci USA 105 2008 1176 1181
9. J. van den Brand, S. Van Gils, P.C.J. Beentjes, H. Terryn, V. Sivel, and J.H.W. de Wit Improving the adhesion between epoxy coatings and aluminium substrates Prog Org Coat 51 2004 339 350
10. M. Yamada, and I. Honma Anhydrous proton conducting polymer electrolytes based on poly (vinylphosphonic acid)-heterocycle composite material Polymer 46 2005 2986 2992
11. M. Schuster, T. Rager, A. Noda, K.D. Kreuer, and J. Maier About the choice of the protogenic group in PEM separator materials for intermediate temperature, low humidity operation: a critical comparison of sulfonic acid, phosphonic acid and imidazole functionalized model compounds Fuel Cells 3 2005 355 365
12. G. Ellis, and A.D. Wilson Polyphosphonate cements: a new class of dental materials J Mater Sci Lett 9 1990 1058 1060
13. A.O. Akinmade, J.H. Braybrook, and J.W. Nicholson Glass polyalkenoate dental cements based on physical blends of poly(acrylic acid) and poly(vinyl phosphonic acid) Polym Int 34 1994 81 88
14. K. Ikemura, F.R. Tay, N. Nishiyama, D.H. Pashley, and T. Endo Design of new phosphonic acid monomers for dental adhesives Dent Mater J 25 3 2006 566 575
15. B. Fennel, R.G. Hill, and A. Akinmade Failure and fracture characteristics of glass poly(vinylphosphonate) cements Dent Mater 14 1998 358 364
16. J. Ellis, H.M. Anstice, and A.D. Wilson The glass polyphosphonate cement: a novel glass-ionomer cement based on poly(vinylphosphonic acid) Clin Mater 7 1991 341 346
17. U. Salz, R. Moszner, and J. Zimmermann Enamel and dentin adhesion W.S. Shalaby, U. Salz, Polymer for dental and orthopedic applications 2007 CRC Press Taylor & Francis Group Boca Raton, London, New York 109 112
18. G.T. Eom, S.Y. Oh, and T.G. Park In situ thermal gelation of water-soluble poly(N isopropylacrylamide-co-vinylphosphonic acid) J Appl Polym Sci 70 1998 1947 1953
19. S. Jin, and K.E. Gonsalves Synthesis and characterization of functionalized poly(ε-caprolactone) copolymers by free-radical polymerization Macromolecules 31 1998 1010 1015
20. M.I. Kabachnik, and T. Medved Vinylphosphonic acid and some of its derivatives Russ Chem Bull 8 1959 2043 2045
21. R. Rabinowitz The reactions of phosphonic acid esters with acid chlorides. A very mild hydrolytic route J Org Chem 28 1963 2975 2978
22. F. Rochlitz, and H. Vilcsek β-Chloroethylphosphonic dichloride: its synthesis and use Angew Chem Int Ed 1 1962 652 656
23. Kleiner H-J, Roscher G. Process for preparing vinylphosphonic acids. US Patent 5,811,575 assigned to Clariant GmbH; 1998.
24. Krause W, Pieper W. Process for making vinylphosphonic acid or vinylpyrophosphonic acid. US Patent 4,486,357 assigned to Hoechst Aktiengesellschaft; 1984.
25. Kleiner H-J, Dursch W. Process for the preparation of vinylphosphonic acid diesters and vinylphosphonic acid. US Patent 4,493,803 assigned to Hoechst Aktiengesellschaft; 1985.
26. Dursch W, Kleiner HJ, Thamm HD. Preparation of phosphonic and/or phosphinic acids. US Patent 4,069,245 assigned to Hoechst Aktiengesellschaft; 1978.
27. Kleiner HJ. Preparation of phosphonic and/or phosphinic acids. US Patent 4,069,247 assigned to Hoechst Aktiengesellschaft; 1978.
28. M.I. Kabachnik, T.A. Mastryukova, and T.A. Melenteva Synthesis of vinylphosphonic acid derivatives Zh Obshch Khim 33 1963 382 384
29. R. Rabinowitz, and J. Pellon Phosphorus-containing monomers. I. The synthesis of vinyl phosphines, oxides, sulfides, and phosphonium compounds J Org Chem 26 1961 4623 4626
30. B. Bingol, W. Meyer, M. Wagner, and G. Wegner Synthesis, microstructure, and acidity of poly(vinylphosphonic acid) Macromol Rapid Commun 27 2006 1719 1724
31. J.H. Braybook, and J.W. Nicholson Incorporation of crosslinking agents into poly(vinyl phosphonic acid) as a route to glass-polyalkenoate cements of improved compressive strength J Mater Chem 3 1993 361 367
32. Y.J. Lee, B. Bingöl, T. Murakhtina, D. Sebastiani, W.H. Meyer, and G. Wegner High-resolution solid-state NMR studies of poly(vinyl phosphonic acid) proton-conducting polymer: molecular structure and proton dynamics J Phys Chem B 111 2007 9711 9721
33. A. Kaltbeitzel, S. Schauff, H. Steininger, B. Bingol, G. Brunklaus, and W.H. Meyer Water sorption of poly(vinylphosphonic acid) and its influence on proton conductivity Solid State Ionics 178 2007 469 474
34. G. David, B. Boutevin, S. Seabrook, M. Destarac, G. Woodward, and G. Otter Radical telomerisation of vinyl phosphonic acid with a series of chain transfer agents Macromol Chem Phys 208 2007 635 642
35. B. Boutevin From telomerization to living radical polymerization J Polym Sci Polym Chem 38 2000 3235 3243
36. G. David, C. Boyer, R. Tayouo, S. Seabrook, B. Ameduri, and B. Boutevin Process for polymerizing vinylphosphonic acid with C6F13I perfluoroalkyliodide chain transfer agent Macromol Chem Phys 209 2007 75 83
37. Rowe W, Saraiya S, Shah A. Method for preparation of poly(vinylphosphonic acid). US Patent 4,822,861 assigned to Polychrome Corporation; 1989.
38. Braybrook JH, Ellis J. Synthesis of poly(vinyl phosphonic acid). US Patent 5,278,266 assigned to British Technology Group Limited; 1994.
39. Dursch W, Herwig FE, Engelhardt F. Process for the preparation of polymers of vinylphosphonic acid in protic solvents. US Patent 4,696,987 assigned to Cassela Aktiengesellschaft; 1987.
40. R.M. Pike, and R.A. Cohen Organophosphorus polymers. I. Peroxide-initiated polymerization of diethyl and diisopropyl vinylphosphonate J Polym Sci 44 1960 531 538
41. Leute M. Macromolecules with phosphorus functionality. PhD Dissertation, University of Ulm 2007. p. 18-30.
42. Bingol B. Synthesis and characterization of poly(vinylphosphonic acid) for proton exchange membranes in fuel cells. PhD Dissertation, University of Mainz; 2007. p. 36-8.
43. H. Emsley, and D. Hall Chemistry of phosphorus 1976 John Wiley & Sons, Inc. New York
44. B. Bingöl, G. Hart-Smith, C. Barner-Kowollik, and G. Wegner Characterization of oligo(vinyl phosphonate)s by high-resolution electrospray ionization mass spectrometry: implications for the mechanism of polymerization Macromolecules 41 2008 1634 1639
45. T. Sato, M. Hasegawa, M. Seno, and T. Hirano Radical polymerization of dimethylvinylphosphonate: homopolymerization and copolymerization with trimethoxyvinylsilane J Appl Polym Sci 109 2008 3746 3752
46. F. Damay, and L.C. Klein Transport properties of Nafion composite membrane for proton-exchange membranes fuel cell Solid State Ionics 162-163 2003 261 267
47. S. Gottesfeld, and T.A. Zawodzinski Polymer electrolyte fuel cells R.C. Alkire, H. Gerischer, D.M. Kolb, C.W. Tobias, Advances in electrochemical science and engineering vol. 5 1997 Wiley-VCH New York 195 196
48. B.K. Datta, G. Velayutham, and A.P. Goud Fuel cell power source for a cold region J Power Sources 106 2002 270 276
49. S.J. Paddison, and R. Paul The nature of proton transport in fully hydrated Nafion(R) Phys Chem Chem Phys 4 2002 1158 1163
50. J.A. Kerres Development of ionomer membranes for fuel cell J Membr Sci 185 2001 3 27
51. K.D. Kreuer On the development of proton conducting polymer membranes for hydrogen and methanol fuel cells J Membr Sci 185 2001 29 39
52. S.M.J. Zaidi, S.D. Mikhailenko, G.P. Robertson, M.D. Guiver, and S. Kaliaguine Proton conducting composite membranes from polyether ether ketone and heteropolyacids for fuel cell applications J Membr Sci 173 2000 17 34
53. L.C. Klein, Y. Daiko, M. Aparicio, and F. Damay Methods for modifying proton exchange membranes using the sol-gel process Polymer 46 2005 4504 4509
54. F. Wang, M. Hickner, Y.S. Kim, T.A. Zawodzinski, and J.E. McGrath Direct polymerization of sulfonated poly(aryleneethersulfone) random (statistical) copolymers: candidates for new proton exchange membranes J Membr Sci 197 2002 231 242
55. M. Kawahara, M. Rikukawa, K. Sanui, and N. Ogata Synthesis and proton conductivity of sulfopropylated poly(benzimidazole) film Solid State Ionics 136-137 2000 1193 1996
56. L. Depre, J. Kappel, and M. Popall Inorganic-organic proton conductors based on alkylosulfone functionalities and their patterning by photoinduced methods Electrochim Acta 43 1998 1301 1306
57. K. Tadanaga, H. Yoshida, A. Matsuda, T. Minami, and M. Tatsumisago Inorganic-organic hybrid films using epoxycyclohexylethyl trimethoxysilane and orthophosphoric acid for PEFC operated at medium temperatures Solid State Ionics 176 2005 2997 2999
58. J. Wainright, J. Wang, D. Weng, R. Savinell, and M. Litt Acid-topped polybenzimidazoles: a new polymer electrolyte J Electrochem Soc 42 1995 L121 L123
59. C. Yang, P. Costamanga, S. Srinivasan, J. Benziger, and A.B. Bocarsly Approaches and technical challenges to high temperature operation of proton exchange membrane fuel cell J Power Sources 103 2001 1 9
60. D.R. Vernon, F. Meng, S.F. Dec, D.L. Williamson, J.A. Turner, and A.M. Herring Synthesis, characterization and conductivity measurements of hybrid membranes containing mono-lacunary heteropolyacid for PEM fuel cell applications J Power Sources 139 2005 141 151
61. A. Schechter, and R.F. Savinell Imidazole and 1-methyl imidazole in phosphoric acid doped polybenzimidazole, electrolyte for fuel cells Solid State Ionics 147 2002 181 187
62. 4 J Polym Sci Polym Phys 40 2002 663 669
63. M.F.H. Schuster, and W.H. Meyer Anhydrous proton-conducting polymers Annu Rev Mater Res 33 2003 233 261
64. K.D. Kreuer, A. Fuchs, M. Ise, M. Spaeth, and J. Laier Imidazole and pyrazole based proton conducting polymers and liquids Electrochim Acta 43 1998 1281 1288
65. Ya. Levin, V.G. Romanov, and B.Y. Ivanov Polyelectrolyte properties of poly(vinylphosphonic acid) and copolymers of vinylphosphonic acid Vysokomol Soed A17 1975 766 771
66. K.D. Kreuer, S.J. Paddison, E. Spohr, and M. Schuster Transport in proton conductors for fuel-cell applications: simulations, elementary reactions, and phenomenology Chem Rev 104 2004 4637 4768
67. K.D. Kreuer Proton conductivity: materials and applications Chem Mater 8 1996 610 641
68. A. Bozkurt, W.H. Meyer, and G. Wegner PAA/imidazol-based proton conducting polymer electrolytes J Power Sources 123 2003 126 131
69. K. Matyjaszewski, V. Coessens, Y. Nakagawa, J. Xia, J. Qiu, and S. Gaynor Synthesis of functional polymers by atom transfer radical polymerization ACS Symp Ser 704 1998 16 27 (Pubitemid 128438872)
70. F. Sevil, and A. Bozkurt Proton conduction in PVPA-benzimidazole hybrid electrolytes Turk J Chem 29 2005 377 383 (Pubitemid 41323636)
71. K. Matyjaszewski, Y. Nakagawa, and S.G. Gaynor Synthesis of well-defined azido and amino end-functionalized polystyrene by atom transfer radical polymerization Macromol Rapid Commun 18 1997 1057 1066
72. Sukumar PR. New proton conducting membranes for fuel cell applications. PhD Dissertation, University of Mainz; 2006. p. 51-3.
73. A. Bozkurt, W.H. Meyer, J. Gutmann, and G. Wegner Proton conducting copolymers on the basis of vinylphosphonic acid and 4-vinylimidazole Solid State Ionics 164 2003 169 176
74. S.U. Celik, U. Akbey, R. Graf, A. Bozkurt, and W. Spiess Anhydrous proton-conducting properties of triazole-phosphonic acid copolymers: a combined study with MAS and NMR Phys Chem Chem Phys 10 2008 6058 6066
75. M. Kato, W. Sakamoto, and T. Yogo Synthesis of proton-conductive sol-gel membranes from trimethoxysilylmethylstyrene and phenylvinyl-phosphonic acid J Membr Sci 303 2007 43 53
76. A. Zouahri, A. Elmidaoui, B. Ameduri, Y. Hervaud, and B. Boutevin Synthesis of ion-exchange membranes from ozonized high density polyethylene Eur Polym J 38 2002 2247 2254
77. A. Elmidaoui, T. Sarraf, C. Gavach, and B. Boutevin Synthesis and characterization of new ion-exchange membranes J Appl Polym Sci 42 1991 2551 2561
78. Kefelli AA. Reaction of ozone with saturated polymers and model compounds. PhD Dissertation, University of Moscow; 1973.
79. F. Gotkepe, S.U. Celik, and A. Bozkurt Preparation and the proton conductivity of chitosan/poly(vinylphosphonic acid) complex polymer electrolytes J Non-Cryst Solids 354 2008 3637 3642
80. J. Parvole, and P. Jannasch Polysulfones grafted with poly(vinylphosphonic acid) for highly proton conducting fuel cell membranes in the hydrated and nominally dry state Macromolecules 41 2008 3893 3903
81. R. Perrin, M. Elomaa, and P. Jannasch Nanostructured proton conducting polystyrene-poly(vinylphosphonic acid) block copolymers prepared via sequential anionic polymerizations Macromolecules 42 2009 5146 5154
82. G. Wei, and P.X. Ma Structure and properties of nano-hydroxyapatite/ polymer composite scaffolds for bone tissue engineering Biomaterials 25 2004 4749 4757
83. M. Zahouily, Y. Abrouki, B. Bahlaouan, A. Rayadh, and S. Sebti Structure and properties of nano-hydroxyapatite/polymer composite scaffolds for bone tissue engineering Catal Comm 4 2003 521 524
84. A. Liebendorfer, B. Schmitz, R. Wenz, R. Specht, and K. Bonath Experimental studies on a new bone cement: hydroxyapatite composite resin The 21st annual meeting of the society for biomaterials San Francisco, USA 1995 335
85. R.R. Lee, M. Ogiso, A. Watanabe, and K. Ishihara Examination of hydroxyapatite filled 4-META/MMA-TBB adhesive bone cement in in vitro and in vivo environment J Biomed Mater Res B 38 1997 11 16
86. L. Borum-Nicholas, and O.C. Wilson Jr. Surface modification of hydroxyapatite. Part I. Dodecyl alcohol Biomaterials 24 2003 3671 3679
87. E.D. Vega, G.E. Narda, and F.H. Ferretti Adsorption of citric acid from dilute aqueous solutions by hydroxyapatite J Colloid Interface Sci 268 2003 37 42
88. M. Anbar, G.A. St John, and A.C. Scott Organic polymeric polyphosphonates as potential preventive agents of dental caries J Dent Res 53 1974 867 878
89. M. Anbar, and E.P. Farley Potential use of organic polyphosphonates adhesives in the restoration of teeth J Dent Res 53 1974 879 888
90. W.J. Peers, D.D. Wright-Charlesworth, and I. Miskioglu Pin-on-disc evaluation of self-reinforced composite poly(methyl methacrylate) for total joint replacements J Biomed Mater Res B 79B 2006 16 24
91. C.W. Shyang, L.Y. Khim, A. Ariffin, Z. Ariffin, and M. Ishak Flexural properties of hydroxyapatite reinforced poly(methyl methacrylate) composites J Reinf Plast Comp 27 2008 945 952
92. J.M. Yang, H.L. You, and C.H. Shih Calorimetric characterization of the formation of acrylic type bone cements J Biomed Mater Res 33 1996 83 88
93. M.H. Chae, Y.T. Lee, K.N. Kim, J.H. Lee, B.J. Choi, and H.J. Choi The effect of hydroxyapatite on bonding strength in light curing glass ionomer dental cement Key Eng Mater 309-311 2006 881 884
94. Y.E. Greish, and P.W. Brown Chemically formed Hal-Ca poly(vinylphosphonate) composites Biomaterials 22 2001 807 816
95. Y.E. Greish, and P.W. Brown Preparation and characterization of calcium phosphate-poly(vinylphosphonic acid) composites J Mater Sci-Mater Med 12 2001 407 411
96. Y.E. Greish, and P.W. Brown Formation and properties of hydroxyapatite-calcium poly(vinylphosphonate) composites J Am Ceram Soc 85 2002 1738 1744
97. A. Gaffar, E.C. Moreno, J. Afflitto, and Y-R.K. Mirajkar Crystal growth of hydroxyapatite in vitro and dental calculus and plaque formation on human teeth in vivo Z. Amjad, Water soluble polymers. Solutions properties and applications 1998 Plenum Press New York 91 104
98. A. Gaffar, J. Afflitto, and N. Nabi Chemical agents for the control of plaque and plaque microflora: an overview Eur J Oral Sci 105 2007 502 507
99. S. Munisamy, T.K. Vaidyanathan, and J. Vaidyanathan A bone-like precoating strategy for implants: collagen immobilization and mineralization on pure titanium implant surface J Oral Implant 34 2008 67 75
100. C.A. Kang, and E.J. Gemeinhart Cellular alignment by grafted adhesion peptide surface density gradients J Biomed Mater Res A 71A 2004 403 411
101. R.A. Gemeinhart, C.M. Bare, R.T. Haash, and E.J. Gemeinhart Osteoblast-like cell attachment to and calcification of novel phosphonate-containing polymeric substrates J Biomed Mater Res A 78A 2006 433 440
102. J. Tan, R.A. Gemeinhart, M. Ma, and W.N. Saltzman Improved cell adhesion and proliferation on synthetic phosphonic acid-containing hydrogels Biomaterials 26 2005 3663 3671
103. H.W. Choi, H.J. Lee, K.J. Kim, H.-M. Kim, and S.C. Lee Surface modification of hydroxyapatite nanocrystals by grafting polymers containing phosphonic acid groups J Colloid Interface Sci 304 2006 277 281
104. G.O. Adusei, S. Deb, and J.W. Nicholson A preliminary study of experimental polyacid-modified composite resins ("compomers") containing vinylphosphonic acid Dent Mater 21 2005 491 497
105. B. Bingol, C. Strandberg, A. Szabo, and G. Wegner Copolymers and hydrogels based on vinylphosphonic acid Macromolecules 41 2008 2785 2790