Monomers for adhesive polymers, 18. Synthesis, photopolymerization and adhesive properties of polymerizable α-phosphonooxy phosphonic acids

Designed Monomers and Polymers
Yohann CatelNorbert Moszner

Abstract

Four polymerizable α-phosphonooxy phosphonic acids7a,7b,9and16were synthesized in seven steps. They were characterized by1H,13C and31P NMR spectroscopy and by high-resolution mass spectroscopy. The copolymerization of acidic monomers7a,7b,9and16with 2-hydroxyethyl methacrylate was studied using a differential scanning calorimeter. Due to the presence of two acidic groups, those monomers are significantly more reactive than 10-methacryloyloxydecylphosphonic acid (MDPA) and 10-methacryloyloxydecyl dihydrogen phosphate (MDP). Self-etch adhesives based on monomers7a,7b,9and16were formulated and used to mediate a bond between a dental composite and the dental hard tissues (dentin and enamel). These adhesives exhibit excellent performances and provide significantly higher dentin and enamel shear bond strength than adhesives based on MDP or MDPA.

References

Aug 14, 2001·Journal of Dental Research·Y YoshidaM Okazaki
May 22, 2004·Journal of Dental Research·Y YoshidaB Van Meerbeek
Jun 5, 2007·Biomaterials·Kirsten L Van LanduytBart Van Meerbeek
Jul 25, 2008·Journal of Dental Research·K L Van LanduytB Van Meerbeek
Nov 27, 2010·Dental Materials : Official Publication of the Academy of Dental Materials·B Van MeerbeekK L Van Landuyt
Feb 22, 2011·Journal of Dental Research·K YoshiharaK L Van Landuyt

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Methods Mentioned

BETA
column chromatography
acylation

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