Monomers for adhesive polymers, 17.^a Synthesis, photopolymerization and adhesive properties of polymerizable phosphonic acids bearing urea groups

References

• Moszner N, Hirt T. New polymer-chemical developments in clinical dental polymer materials: enamel-dentin adhesives and restorative composites. J. Polym. Sci. A: Polym. Chem. 2012;50:4369–4402.10.1002/pola.v50.21
   Web of Science ®Google Scholar
• Van Meerbeek B, Yoshihara K, Yoshida Y, et al. State of the art of self-etch adhesives. Dent. Mater. 2011;27:17–28.10.1016/j.dental.2010.10.023
   PubMed Web of Science ®Google Scholar
• Van Landuyt KL, Snauwaert J, De Munck J, et al. Systematic review of the chemical composition of contemporary dental adhesives. Biomaterials. 2007;28:3757–3785.10.1016/j.biomaterials.2007.04.044
   PubMed Web of Science ®Google Scholar
• Moszner N, Catel Y. Phosphorus-based polymers: from synthesis to applications. In: Monge S, David G, editors, Cambridge: RSC polymer chemistry series. Vol. 11; 2014; Chapter 8. p.151–166.10.1039/2044-0804
   Google Scholar
• Moszner N, Salz U. Recent developments of new components for dental adhesives and composites. Macromol. Mater. Eng. 2007;292:245–271.10.1002/(ISSN)1439-2054
   Web of Science ®Google Scholar
• Van Landuyt KL, Yoshida Y, Hirata I, et al. Influence of the chemical structure of functional monomers on their adhesive performance. J. Dent. Res.. 2008;87:757–761.10.1177/154405910808700804
   PubMed Web of Science ®Google Scholar
• Yoshida Y, Van Meerbeek B, Nakayama Y, et al. Adhesion to and decalcification of hydroxyapatite by carboxylic acids. J. Dent. Res. 2001;80:1565–1569.10.1177/00220345010800061701
   PubMed Web of Science ®Google Scholar
• Yoshida Y, Nagakane K, Fukuda R, et al. Comparative study on adhesive performance of functional monomers. J. Dent. Res. 2004;83:454–458.10.1177/154405910408300604
   PubMed Web of Science ®Google Scholar
• Yoshihara K, Yoshida Y, Hayakawa S, et al. Self-etch monomer-calcium salt deposition on dentin. J. Dent. Res. 2011;90:602–606.10.1177/0022034510397197
   PubMed Web of Science ®Google Scholar
• Bilgici ZS, Turker SB, Avci D. Novel bisphosphonated methacrylates: synthesis, polymerizations, and interactions with hydroxyapatite. Macromol. Chem. Phys. 2013;214:2324–2335.10.1002/macp.v214.20
   Web of Science ®Google Scholar
• Catel Y, Degrange M, Le Pluart L, et al. Synthesis, photopolymerization, and adhesive properties of new bisphosphonic acid monomers for dental application. J. Polym. Sci. A: Polym. Chem. 2009;47:5258–5271.10.1002/pola.v47:20
   Web of Science ®Google Scholar
• Catel Y, Fischer UK, Moszner N. Monomers for adhesive polymers, 13. 1 Synthesis, radical photopolymerization and adhesive properties of polymerizable 2-substituted 1,3-propylidenediphosphonic acids. Des. Monomers Polym. 2014;17:286–299.10.1080/15685551.2013.840503
   Web of Science ®Google Scholar
• Catel Y, Bock T, Moszner N. Monomers for adhesive polymers, 15: synthesis, photopolymerization, and adhesive properties of polymerizable β-ketophosphonic acids. Polym. Chem J. Polym. Sci. A. 2014;52:3550–3563.
   Web of Science ®Google Scholar
• Altin A, Akgun B, Buyukgumus O, et al. Synthesis and photopolymerization of novel, highly reactive phosphonated-urea-methacrylates for dental materials. React. Funct. Polym. 2013;73:1319–1326.10.1016/j.reactfunctpolym.2013.07.006
   Web of Science ®Google Scholar
• Berchtold KA, Nie J, Stansbury JW, et al. Novel monovinyl methacrylic monomers containing secondary functionality for ultrarapid polymerization: steady-state evaluation. Macromolecules. 2004;37:3165–3179.10.1021/ma035862+
   Web of Science ®Google Scholar
• Jansen JFGA, Dias AA, Dorschu M, et al. Fast monomers: factors affecting the inherent reactivity of acrylate monomers in photoinitiated acrylate polymerization. Macromolecules. 2003;36:3861–3873.10.1021/ma021785r
   Web of Science ®Google Scholar
• Lee TY, Roper TM, Jönsson ES, et al. Influence of hydrogen bonding on photopolymerization rate of hydroxyalkyl acrylates. Macromolecules. 2004;37:3659–3665.10.1021/ma0305277
   Web of Science ®Google Scholar
• Zhou H, Li Q, Lee TY, et al. Photopolymerization of acid containing monomers: real-time monitoring of polymerization rates. Macromolecules. 2006;39:8269–8273.10.1021/ma061332c
   Web of Science ®Google Scholar
• Ibrahim OB, Refat MS, Salman M, et al. Chemical studies on the uses of urea complexes to synthesize compounds having electrical and biological applications. Int. J. Mater. Sci. 2012;2:67–82.
   Google Scholar
• Graillot A, Monge S, Faur C, et al. Synthesis by RAFT of innovative well-defined (co)polymers from a novel phosphorus-based acrylamide monomer. Polym. Chem. 2013;4:795–803.10.1039/C2PY20720F
   Web of Science ®Google Scholar
• Catel Y, Degrange M, Le Pluart L, et al. Synthesis, photopolymerization and adhesive properties of new hydrolytically stable phosphonic acids for dental applications.. J. Polym. Sci. A: Polym. Chem. 2008;46:7074–7090.10.1002/pola.v46:21
   Web of Science ®Google Scholar
• Derbanne MA, Besse V, Le Goff S, et al. Hydrolytically stable acidic monomers used in two steps self-etch adhesives. Polym. Degrad. Stab. 2013;98:1688–1698.10.1016/j.polymdegradstab.2013.06.006
   Web of Science ®Google Scholar
• Tarasow TM, Tarasow SL, Tu C, et al. Characteristics of an RNA diels−alderase active site. J. Am. Chem. Soc. 1999;121:3614–3617.10.1021/ja983989m
   Web of Science ®Google Scholar
• Anseth KS, Wang CM, Bowman CN. Kinetic evidence of reaction-diffusion during the polymerization of multi(meth)acrylate monomers. Macromolecules. 1994;27:650–655.10.1021/ma00081a004
   Web of Science ®Google Scholar
• ISO29022: 2013.
   Google Scholar
• Salz U, Zimmermann J, Zeuner F, et al. Hydrolytic stability of self-etching adhesive systems. J. Adhes. Dent. 2005;7:107–116.
   PubMed Web of Science ®Google Scholar
• Teshima I. J. Dent. Res. 2010;89:1281–1286.10.1177/0022034510379018
   PubMed Web of Science ®Google Scholar
• Moszner N, Angermann J, Fischer U, et al. Monomers for adhesive polymers, 9-synthesis, radical photopolymerization, and properties of (meth)acrylamido dihydrogen phosphates. Macromol. Mater. Eng. 2013; 298: 454–461.10.1002/mame.v298.4
   Web of Science ®Google Scholar
• Klee JE, Lehmann U. N-alkyl-N-(phosphonoethyl) substituted (meth)acrylamides – new adhesive monomers for self-etching self-priming one part dental adhesive. Beil. J. Org. Chem. 2009;5.
   PubMed Web of Science ®Google Scholar
• Catel Y, Fischer UK, Moszner N. Monomers for adhesive polymers: 11. Structure–adhesive properties relationships of new hydrolytically stable acidic monomers.  Polym. Int. 2013;62:1717–1728.10.1002/pi.2013.62.issue-12
   Web of Science ®Google Scholar
• Altin A, Akgun B, Bilgici ZS, et al. Synthesis, photopolymerization, and adhesive properties of hydrolytically stable phosphonic acid-containing (meth)acrylamides.  J. Polym. Sci. A: Polym. Chem. 2014;52:511–522.10.1002/pola.27025
   Web of Science ®Google Scholar
• Moszner N, Zeuner F, Lamparth I, et al. Benzoylgermanium derivatives as novel visible-light photoinitiators for dental composites. Macromol. Mater. Eng. 2009;294:877–886.10.1002/mame.v294:12
   Web of Science ®Google Scholar
• Feitosa VP, Ogliari FA, Van Meerbeek B, et al. Can the hydrophilicity of functional monomers affect chemical interaction? J. Dent. Res. 2014;93:201–206.10.1177/0022034513514587
   PubMed Web of Science ®Google Scholar
• Catel Y, Schörpf S, Moszner N. Monomers for adhesive polymers, 16 synthesis of acidic dimethacrylates starting from thioglycerol. Macromol. Mater. Eng. 2015. doi:10.1002/mame.201500118.
   Web of Science ®Google Scholar