825
Views
12
CrossRef citations to date
0
Altmetric
Articles

Monomers for adhesive polymers, 13.1 Synthesis, radical photopolymerization and adhesive properties of polymerizable 2-substituted 1,3-propylidenediphosphonic acids

, &
Pages 286-299 | Received 07 Feb 2013, Accepted 23 Mar 2013, Published online: 14 Oct 2013

References

  • Pavlinec J, Kleinova A, Angermann J, Lamparth I, Moszner, N. Monomers for adhesive polymers, 12. Synthesis and free-radical homo- and copolymerization of 2-ethoxycarbonyl-allyl 5-(1,2-dithiolane-3-yl)-pentanoate. Macromol. Mater. Eng. doi:10.1002/mame.201200382.
  • Moszner N, Hirt T. New polymer-chemical developments in clinical dental polymer materials: enamel–dentin adhesives and restorative composites. J. Polym. Sci., Part A: Polym. Chem. 2012;50:4369–4402.
  • Van Meerbeek B, Yoshihara K, Yoshida Y, Mine A, De Munck J, Van Landuyt KL. State of the art of self-etch adhesives. Dental Mater. 2011;27:17–28.
  • Van Landuyt KL, Snauwaert J, De Munck J, Peumans M, Yoshida Y, Poitevin A, Coutinho E, Suzuki K, Lambrechts P, Van Meerbeek B. Systematic review of the chemical composition of contemporary dental adhesives. Biomaterials. 2007;28:3757–3785.
  • Van Landuyt KL, Yoshida Y, Hirata I, Snauwaert J, De Munck J, Okazaki M, Suzuki K, Lambrechts P, Van Meerbeek B. Influence of the chemical structure of functional monomers on their adhesive performance. J. Dental Res. 2008;87:757–761.
  • Yoshida Y, Van Meerbeek B, Nakayama Y, Yoshioka M, Snauwaert J, Abe Y, Lambrechts P, Vanherle G, Okazaki M. Adhesion to and decalcification of hydroxyapatite by carboxylic acids. J. Dental Res. 2001;80:1565–1569.
  • Yoshioka M, Yoshida Y, Inoue S, Lambrechts P, Vanherle G, Nomura Y, Okazaki M, Shintani H, Van Meerbeek B. Adhesion/decalcification mechanisms of acid interactions with human hard tissues. J. Biomed. Mater. Res. 2002;59:56–62.
  • Catel Y, Fischer U, Moszner N. Monomers for adhesive polymers, 10. Synthesis, radical photopolymerization and adhesive properties of methacrylates bearing phosphonic acid groups. Macromol. Mater. Eng. 2013;298:740–756.
  • Moszner N, Angermann J, Fischer U, Bock T. Monomers for adhesive polymers, 9. Synthesis, radical photopolymerization, and properties of (meth)acrylamido dihydrogen phosphates. Macromol. Mater. Eng. 2013;298:454-461.
  • Catel Y, Degrange M, Le Pluart L, Madec PJ, Pham TN, Chen F, Cook WD. Synthesis, photopolymerization, and adhesive properties of new bisphosphonic acid monomers for dental application. J. Polym. Sci., Part A: Polym. Chem. 2009;47:5258–5271.
  • Catel Y, Besse V, Zulauf A, Marchat D, Pfund E, Pham TN, Bernache-Assolant D, Degrange M, Lequeux T, Madec PJ, Le Pluart L. Synthesis and evaluation of new phosphonic, bisphosphonic and difluoromethylphosphonic acid monomers for dental application. Eur. Polym. J. 2012;48:318–330.
  • Akgun B, Savci E, Avci D. Synthesis and polymerizations of phosphonated-bis(methacrylamide)s for dental applications. J. Polym. Sci., Part A: Polym. Chem. 2012;50:801–810.
  • Ikemura K, Kadoma Y, Endo T. A review of the developments of self-etching primers and adhesives – Effects of acidic adhesive monomers and polymerization initiators on bonding to ground, smear layer-covered teeth. Dent. Mat. J. 2001;30:769–789.
  • Phillips AMMM, Mphahlele ML, Modro AM, Modro TA, Zwiezak A. Phosphonic systems, 7. Reactions of 2,3-epoxyphosphonates with nucleophiles: preparation of 2,3-disubstituted alkylphosphonic esters and related systems. Phosphorus, Sulfur Silicon Relat. Elem. 1992;71:165–174.
  • Bodesheim F, Velker E, Bentz F, Nischk G. Reaktionen von 2-methylen-propan-1,3-diol-derivaten mit organischen phosphorverbindungen. Chemiker-Zeitung. 1972;96:581–582.
  • Cattaneo M, Lecchi A, Ohno M, Joshi BV, Besada P, Tchilibon S, Lombardi R, Bischofberger N, Harden TK, Jacobson KA. Antiaggregatory activity in human platelets of potent antagonists of the P2Y1 receptor. Biochem. Pharmacol. 2004;68:1995–2002.
  • Anseth KS, Wang CM, Bowman CN. Kinetic evidence of reaction-diffusion during the polymerization of multi(meth)acrylate monomers. Macromolecules. 1994;27:650–655.
  • Ulrich G, Burtscher P, Salz U, Moszner N, Liska R. Phenylglycine derivatives as coinitiators for the radical photopolymerization of acidic aqueous formulations. J. Polym. Sci., Part A: Polym. Chem. 2006;44:115–125.
  • Sardarian AR, Shahsavari-Fard Z. Convenient and regioselective one-pot solvent-free synthesis of ß-hydroxyphosphonates. Synth. Commun. 2007;37:289–295.
  • Dubosclard-Gottardi C, Caubère P, Fort Y. New selective syntheses of (meth)acrylic monomers: isocyanates, isocyanurates, carbamates and ureas derivatives. Tetrahedron. 1995;51:2561–2572.
  • Salz U, Zimmermann J, Zeuner F, Moszner N. Hydrolytic stability of self-etching adhesive systems. J. Adhes. Dent. 2005;7:107–116.
  • Teshima I. Degradation of 10-methacryloyloxydecyl dihydrogen phosphate. J. Dental Res. 2010;89:1281–1286.
  • Moszner N, Zeuner F, Pfeiffer S, Schurte I, Rheinberger V, Drache M. Monomers for adhesive polymers, 3. Synthesis, radical polymerization and adhesive properties of hydrolytically stable phosphonic acid monomers. Macromol. Mater. Eng. 2001;286:225–231.
  • Klee JE, Lehmann U. Novel 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers for self-etching self-priming one part adhesive. Beilstein J. Org. Chem. 2010;6:766–772.
  • Catel Y, Degrange M, Le Pluart L, Madec PJ, Pham TN, Picton L. Synthesis, photopolymerization and adhesive properties of new hydrolytically stable phosphonic acids for dental applications. J. Polym. Sci., Part A: Polym. Chem. 2008;46:7074–7090.
  • Moszner N, Zeuner F, Lamparth I, Fischer U. Benzoylgermanium derivatives as novel visible-Light photoinitiators for dental composites. Macromol. Mater. Eng. 2009;12:877–886.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.