Synthesis and stability study of dental monomers containing methacrylamidoethyl phosphonic acids

Abstract

Three new dental monomers containing methacrylamidoethyl phosphonic acids were synthesized. The structures of the synthesized monomers were determined with electrospray mass spectrometry (ESMS), Fourier transform infrared, and NMR. The hydrolytic stabilities of the synthesized monomers and a commercial monomer, 2-methacryloyloxyethyl phosphoric acid (MEP; used as a control), were studied with flow injection (FI)/ESMS, 1 H NMR, and 31 P NMR analysis of a CD 3 OD/D 2 O (4:1 v/v) solution of each monomer before and after storage at 60 8C for 2 months. The 1 H NMR and 31 P NMR chemical shifts of the monomers 2-methacrylamidoethylphosphonic acid (I) and N,N 0 -[4,4 0 -(propane-2,2-diyl)-bis(phenoxy-2-hydroxypropyl)]-bis(2methacrylamidoethylphosphonic acid) (II) showed little change after storage at 60 8C for 2 months, but those of MEP changed significantly. FI/ESMS also showed that MEP was nearly completely decomposed, whereas monomers I and II remained largely intact. MEP could react with H 2 ZrF 6 to form ternary zirconium fluoride complexes that were partially soluble in methanol, but all the monomers containing phosphonic acids formed precipitates. This study demonstrates that ESMS is a more sensitive and effective method than NMR for studying the hydrolytic stability or degradation of dental monomers. The new monomers containing methacrylamidoethyl phosphonic acids have higher hydrolytic stability than methacrylate phosphate monomers and may be used in dental bonding agents and other dental materials.

Thermal oxidative degradation kinetics of PP and PP/mg (OH)2 flame‐retardant composites

“…They have also been used in biomedical field as adhesion promoters to dental tissue, bone and metals. For example, monomers with phosphonic and phosphoric acid functional groups have been used in dental composites and self‐etching dental adhesives 3–6. Bisphosphonate‐containing polymers are used in bone‐targeted drug delivery applications 7.…”

Dental Applications

“…While this procedure possibly holds great interest to dentists, there exist concerns about promoting and achieving lasting marginal integrity with such one-step bonding agents. Not surprising, there has always been high interest in coming up with new monomers and methods to improve the etching and adhesion processes (192,193). A systematic review of the chemical aspects of self-etching enamel-dentin bonding was fairly recently published (194).…”

Grafting of phosphonate groups onto PVA by acetalyzation. Evaluation of the anti-corrosive properties for the acetalyzed PVA coatings

“…As methacrylates undergo hydrolysis, some authors proposed the use of (meth)acrylamide bearing phosphonic acid groups. The resulting cross-linked polymers improved adhesion and were efficiently used in dental application [19][20][21][22]. The post-phosphonation of pre-made polymers, which are highly stable towards hydrolysis, is another strategy to introduce phosphonic acid groups.…”