Synthesis and evaluation of new phosphonic, bisphosphonic and difluoromethylphosphonic acid monomers for dental application

European Polymer Journal

Volumn 48, Issue 2, 2012, Pages 318-330

  Catel, Yohann ^a   Besse, Vincent ^a   Zulauf, Anaïs ^a   Marchat, David ^c   Pfund, Emmanuel ^a   Pham, Thi Nhàn ^a   Bernache Assolant, Didier ^c   Degrange, Michel ^b   Lequeux, Thierry ^a   Madec, Pierre Jean ^a   Le Pluart, Loïc ^a  

^a UNIVERSITÉ DE CAEN   (France)

^b UNIVERSITÉ PARIS DESCARTES   (France)

^c UMR CNRS 5148   (France)

Author keywords

Adhesion; Dental adhesives; Hydroxyapatite; Photopolymerization; Synthesis

Indexed keywords

ADHESIVE PROPERTIES; BISPHOSPHONIC ACID; DENTAL ADHESIVES; DENTAL APPLICATIONS; PHOSPHONIC; PHOSPHONIC ACIDS; PHOTO-DIFFERENTIAL SCANNING CALORIMETRY; SHEAR BOND STRENGTHS;

ADHESION; ADHESIVES; APATITE; DENTAL MATERIALS; DIFFERENTIAL SCANNING CALORIMETRY; HYDROXYAPATITE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS; PHOTOPOLYMERIZATION; PROPANE; SYNTHESIS (CHEMICAL);

MONOMERS;

EID: 84855818262     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2011.09.020     Document Type: Article

References (50)

1. N. Moszner, and U. Salz Recent developments of new components for dental adhesives and composites Macromol Mater Eng 292 2007 245 271 (Pubitemid 46980930)
2. M.J. Tyas, and M.F. Burrow Adhesive restorative materials: a review Aust Dent J 49 2004 112 121 (Pubitemid 39334833)
3. B. Van Meerbeek, M. Vargas, S. Inoue, Y. Yoshida, M. Peumans, and P. Lambrechts Adhesives and cements to promote preservation dentistry Oper Dent 6 Suppl 2001 119 144
4. K.L. Van Landuyt, J. Snauwaert, J. De Munck, M. Peumans, Y. Yoshida, and A. Poitevin Systematic review of the chemical composition of contemporary dental adhesives Biomaterials 28 2007 3757 3785 (Pubitemid 47053932)
5. N. Moszner, U. Salz, and Zimmermann Chemical aspects of self-etching enamel-dentin adhesives: a systematic review J Dent Mater 21 2005 895 910 (Pubitemid 41336632)
6. N. Nakabayashi, and D.H. Pashley Hybridisation of dental hard tissues 1998 Quintessence Publishing Tokyo
7. M. Peumans, P. Kanumilli, J. De Munck, K. Van Landuyt, P. Lambrechts, and B. Van Meerbeek Clinical effectiveness of contemporary adhesives: a systematic review of current clinical trials Dent Mater 21 2005 864 881 (Pubitemid 41108347)
8. L. Bresci, A. Mazzoni, A. Ruggeri, M. Cadenaro, R. Di Lenarda, and E. De Stefano Dorigo Dental adhesion review: aging and stability of the bonded interface Dent Mater 24 2008 90 101 (Pubitemid 350250812)
9. J. De Munck, K. Van Landuyt, M. Peumans, A. Poitevin, P. Lambrechts, and M. Braem A critical review of the durability of adhesion to tooth tissue: methods and results J Dent Res 84 2005 118 132 (Pubitemid 43822043)
10. M. Hashimoto A review - Micromorphological evidence of degradation in resin-dentin bonds and potential preventional solutions J Biomed Mat Res B 92B 2010 268 280
11. M. Hashimoto, H. Ohno, H. Sano, M. Kaga, and H. Oguchi In vitro degradation of resin-dentin bonds analyzed by microtensile bond test, scanning and transmission electron microscopy Biomaterials 24 2003 3795 3803 (Pubitemid 36773613)
12. D.H. Pashley, F.R. Tay, C.K.Y. Yiu, M. Hashimoto, L. Breschi, and R.M. Carvalho Collagen degradation by host-derived enzymes during aging J Dent Res 83 2004 216 221 (Pubitemid 41713778)
13. F.R. Tay, D.H. Pashley, R.J. Loushine, R.N. Weller, F. Monticelli, and R. Osorio Self-etching adhesives increase collagenolytic activity in radicular dentin J Endod 32 2006 862 868 (Pubitemid 44247139)
14. Y. Nishitani, M. Yoshiyama, B. Wadgaonkar, L. Breschi, F. Mannello, and R.M. Mazzoni Carvalho Activation of gelatinolytic/ collagenolytic activity in dentin by self-etching adhesives Eur J Oral Sci 114 2006 160 166 (Pubitemid 43480639)
15. A. Tezvergil-Mutluay, K.A. Agee, T. Hoshika, F.R. Tay, and D.H. Pashley The inhibitory effect of polyvinylphosphonic acid on functional matrix metalloproteinase activities in human demineralized dentin Acta Biomater 6 10 2010 4136 4142
16. Y. Yoshida, K. Nagakane, R. Fukuda, Y. Nakayama, M. Okazaki, and H. Shintani Comparative study on adhesive performance of functional monomers J Dent Res 83 2004 454 458 (Pubitemid 41756839)
17. Y. Yoshida, B. Van Meerbeek, Y. Nakayama, M. Yoshioka, J. Snauwaert, and Y. Abe Adhesion to and decalcification of hydroxyapatite by carboxylic acids J Dent Res 80 2001 1565 1569
18. B. Fu, X. Sun, W. Qian, Y. Shen, R. Chen, and M. Hannig Evidence of chemical bonding to hydroxyapatite by phosphoric acid esters Biomaterials 26 2005 5104 5110 (Pubitemid 40387834)
19. S. Inoue, K. Koshiro, Y. Yoshida, J. De Munck, K. Nagakane, and K. Suzuki Hydrolytic stability of self-etch adhesives bonded to dentin J Dent Res 84 2005 1160 1164 (Pubitemid 43827785)
20. K. Ikemura, F.R. Tay, N. Nishiyama, D.H. Pashley, and T. Endo Multi-purpose bonding performance of newly synthesized phosphonic acid monomers Dent Mater J 25 2006 566 575
21. G. Sahin, A.Z. Albayrak, Z.S. Bilgici, and D. Avci Synthesis and evaluation of new dental monomers with both phosphonic and carboxylic acid functional groups J Polym Sci A: Polym Chem 47 2009 1953 1965
22. M. Anbar, and G.A. St. John Adsorption of polyphosphonated polyethylene on enamel of teeth J Dent Res 50 1971 778 783
23. F. Zeuner, N. Moszner, T. Völkel, K. Vogel, and V. Rheinberger Synthesis and dental aspects of acrylic phosphoric and phosphonic acids Phosphorus, Sulfur, Silicon 144 1999 133 136
24. Abuelyaman AS. US patent 0 206 932 A1, 3M Innovative Properties Company; 2004.
25. Y. Catel, M. Degrange, L. Le Pluart, P.-J. Madec, T.-N. Pham, and F. Chen Synthesis, photopolymerisation and adhesive properties of new bisphosphonic acid monomers for dental application J Polym Sci A: Polym Chem 47 2009 5258 5271
26. D. O'Hagan, and H.S. Rzepa Some influences of fluorine in bioorganic chemistry Chem Commun 1997 645 652 (Pubitemid 127498767)
27. R.G.G. Russell, and M.J. Rogers Bisphosphonates: from the laboratory to the clinic and back again Bone 25 1999 97 106 (Pubitemid 29322070)
28. H. Fleisch The role of bisphosphonates in breast cancer: development of bisphosphonates Breast Cancer Res 4 2002 30 34
29. V. Hengst, C. Oussoren, T. Kissel, and G. Storm Bone targeting potential of bisphosphonate-targeted liposomes preparation, characterization and hydroxyapatite binding in vitro Int J Pharm 331 2007 224 227 (Pubitemid 46216674)
30. G.H. Nancollas, R. Tang, R.J. Phipps, Z. Henneman, S. Gulde, and W. Wu Novel insights into actions of bisphosphonates on bone: differences in interactions with hydroxyapatite Bone 38 2006 617 627
31. H. Fleisch Bisphosphonates: mechanisms of action Endocr Rev 19 1998 80 100 (Pubitemid 29122075)
32. S.G. Senaratne, and K.W. Colston The role of bisphosphonates in breast cancer: direct effects of bisphosphonates on breast cancer cells Breast Cancer Res 4 2002 18 23 (Pubitemid 34097552)
33. O. Teronen, M. Laitinen, T. Salo, R. Hanemaaijer, P. Heikkilä, and Y.T. Konttinen Inhibition of matrix metalloproteinases by bisphosphonates may in part explain their effects in the treatment of multiple myeloma Blood 96 2000 4006 4007
34. S. Boissier, M. Ferreras, O. Peyruchaud, S. Magnetto, F.H. Ebetino, and M. Colombel Bisphosphonates inhibit breast and prostate carcinoma cell invasion, an early event in the formation of bone metastases Cancer Res 60 2000 2949 2954 (Pubitemid 30395820)
35. S.W. Baldwin, J.D. Wilson, and J. Aube Regiochemistry in the Intramolecular cycloadditions of substituted 5-alkenyl and 6-alkenyl nitrones J Org Chem 50 1985 4432 4439
36. N. Moszner, F. Zeuner, J. Angermann, U. Karl Fischer, and V. Rheinberger Monomers for adhesive polymers Macromol Mater Eng 288 2003 621 628
37. P. Ozouf, G. Binot, J.-C. Pommelet, and T. Lequeux Syntheses of ω(hydroxy-a,a-difluoromethylphosphonates by oxacycle ring-opening reactions Org Lett 6 2004 3747 3750 (Pubitemid 39421934)
38. International Standard ISO 13779-3, Implants for surgery - Hydroxyapatite - Part 3: Chemical analysis and characterization of crystallinity and phase purity; 2008.
39. S. Raynaud, E. Champion, D. Bernache-Assollant, and J.-P. Laval Determination of calcium/phosphorus atomic ratio of calcium phosphate apatites using X-ray diffractometry J Am Ceramic Soc 84 2001 359 366 (Pubitemid 32253101)
40. D. Francova, and G. Kickelbick Synthesis of methacrylate-functionalized phosphonates and phosphates with long alkyl-chain spacers and their self-aggregation in aqueous solutions Monatshefte Chem 140 2009 413 422
41. D. Fukegawa, S. Hayakawa, Y. Yoshida, K. Suzuki, A. Osaka, and B. Van Meerbeek Chemical interaction of phosphoric acid ester with hydroxyapatite J Dent Res 85 10 2006 941 944 (Pubitemid 44578608)
42. Y. Catel, M. Degrange, L. Le Pluart, P.-J. Madec, -N Pham T, and L. Picton Synthesis, photopolymerization and adhesive properties of new hydrolytically stable phosphonic acids for dental applications J Polym Sci A: Polym Chem 46 2008 7074 7090
43. Y. Yagci, S. Jockusch, and N.J. Turro Photoinitiated polymerization: advances, challenges, and opportunities Macromolecules 43 15 2010 6245 6260
44. J.-P. Gourves, H. Couthon, and G. Sturtz A new efficient synthesis of omega-aminoalkylidene-1,1-bisphosphonate tetraethylesters Phosphorus, Sulfur, Silicon 132 1998 219 229 (Pubitemid 128386605)
45. C.E. Mc Kenna, M.T. Higa, N.H. Cheung, and M.-C. Mc Kenna The facile dealkylation of phosphonic acid dialkyl esters by bromotrimethylsilane Tetrahedron Lett. 2 1977 155 158
46. C. Dufau, and G. Sturtz Preparation of tetraethyl but-3-enylidene-1,1- bisphosphonate and study of its reactivity as a synthon of tetraethyl 3,4-diaminobutylidene-1,1-bisphosphonate Phosphorus, Sulfur, Silicon 69 1992 93 102
47. A. Henry-dit-Quesnel, L. Toupet, J.-C. Pommelet, and T. Lequeux A difluorosulfide as a Freon-free source of phosphonodifluoromethyl carbanion Org Biomol Chem 1 2003 2486 2491
48. T.Y. Lee, T.M. Roper, E.S. Johnson, C.A. Guymon, and C.E. Hoyle Influence of hydrogen bonding on photopolymerization rate of hydroxyalkyl acrylates Macromolecules 37 2004 3659 3665
49. J.F.G.A. Jansen, A.A. Dias, M. Dorschu, and B. Coussens Fast monomers: factors affecting the inherent reactivity of acrylate monomers in photoinitiated acrylate polymerization Macromolecules 36 2003 3861 3873
50. H. Kilambi, E.R. Beckel, K.A. Berchtold, J.W. Stansbury, and C.N. Bowman Influence of molecular dipole on acrylate reactivity Polymer 46 2005 4735 4742 (Pubitemid 40688476)