Degradation of 10-Methacryloyloxydecyl Dihydrogen Phosphate

Abstract

To understand the mechanism of 10-methacryloyloxydecyl dihydrogen phosphate (MDP) hydrolysis, we investigated the degradation of 2-methacryloyloxyethyl dihydrogen phosphate (MEP), because the MEP molecule has the methacryloxy and phosphate ester portions of MDP but, unlike the latter, is water-soluble. The MEP-N-methcryloyl glycine (NMGly), MDP-NMGly, and MDP-2-hydroxyethyl methacrylate (HEMA) primers were designed, stored for different periods, and then analyzed. Our null hypotheses were that (1) the mechanism of MDP hydrolysis differs from that of MEP and (2) the type of hydrophilic monomer--NMGly or HEMA--has no effect on the MDP hydrolysis rate. Similar to the production of methacrylic acid (MA) and 2-hydroxyethyl dihydrogen phosphate (HEP) during MEP hydrolysis, MDP produced MA and 10-hydroxydecyl dihydrogen phosphate (HDP) during hydrolysis. However, the rate of MDP hydrolysis depended on the type of hydrophilic monomer: Compared with HEMA, NMGly significantly increased the rate of MDP hydrolysis.

Monomers for adhesive polymers. XV. Synthesis, photopolymerization, and adhesive properties of polymerizable β-ketophosphonic acids

“…After 1 min of acquisition, the samples were irradiated for 2 min at 37 C with a LED curing light (Bluephase, monowave LED with a maximum intensity at 470 nm; Ivoclar Vivadent AG). The incident light intensity was 15 mW cm 22 . Each experiment was repeated three times.…”

Effect of thermocycling on the durability of etch-and-rinse and self-etch adhesives on dentin

“…Three possible mechanisms might explain this: (1) physical degradation due to higher thermal contraction/ expansion coefficients of the restorative material generate stress at the resin/tooth structure interface, resulting in crack propagation along the bonded interface and gap formation 3) ; (2) chemical degradation due to hot water accelerating the hydrolysis of the adhesive monomer 32,33) ; and (3) biological degradation of denuded collagen within the hybrid layers by activation of the MMP enzyme at the activation site 34) . The effect of thermocycling on the durability of adhesion to dentin was clearly observed, especially with the etch-and-rinse adhesives in this study.…”

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

“…It is well known that (meth)acrylates are not hydrolytically stable during the storage of some SEAs. [1,26,27] Indeed, SEAs are acidic aqueous solutions. In these conditions of storage, (meth)acrylates might undergo hydrolysis, leading to a modification of the chemical composition of the adhesive.…”