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

Abstract

This paper reviews the developments of self-etching primers and adhesives, with a special focus on the effect of acidic adhesive monomers and polymerization initiators on bonding to ground, smear layer-covered teeth. Ionized acidic adhesive monomers chemically interact with tooth substrates and facilitate good bonding to ground dentin. Polymerization initiators in self-etching primers further promote effective bonding to ground dentin. To promote bonding to both dentin and enamel, phosphonic acid monomers such as 6-methacryloyloxyhexyl phosphonoacetate (6-MHPA) were developed. These novel adhesive monomers also have a water-soluble nature and are hence endowed with sufficient demineralization capability. A new single-bottle, self-etching, 2-hydroxyethyl methacrylate (HEMA)-free adhesive comprising 6-MHPA and 4-acryloyloxyethoxycarbonylphthalic acid (4-AET) was developed. This novel adhesive enabled strong adhesion to both ground enamel and dentin, but its formulation stability was influenced by pH value of the adhesive. To develop hydrolytically stable, single-bottle, self-etching adhesives, hydrolytically stable, radical-polymerizable acidic monomers with amide or ether linkages have been developed.

Bonding performance of a temporary tooth coating material to enamel

“…However, it has been reported that the phosphonate ion possesses the capacity to exchange with the PO −3 4 in hydroxyapatite crystals and to bind with the calcium in hydroxyapatite through a chemical reaction [22] that promotes an increase in bond strength to the enamel. [23][24][25] Therefore, it seemed likely that the presence of the 6-MHPA monomer in the primer played an important role in the bonding to the enamel despite the mildness of the demineralization observed in this study. An activator containing carboxylic acid is designed to enhance the bonding ability to primer-pretreated enamel.…”

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

“…The structures of the new acidic monomers were confirmed by 1 H NMR, 31 P NMR, 13 C NMR spectroscopy as well as by HRMS. As an example, the 13 C NMR spectrum of monomer 12 is represented on Figure 3.…”

“…1 H NMR, 13 C NMR and 31 P NMR spectra were recorded on a DPX-400 spectrometer using TMS as internal reference for 1 H NMR and 13 C NMR chemical shifts and using H 3 PO 4 (85%) as external reference for 31 P NMR chemical shifts. Data are given in the following order: chemical shift in ppm, multiplicity (s, singlet; d, doublet; t, triplet; q, quadruplet; qt, quintuplet; m, multiplet), coupling constant in Hertz, assignment.…”

“…As an example, the 13 C NMR spectrum of monomer 12 is represented on Figure 3. The monomer 12 is identified by four methylene groups at 28.8 (2C, dd), 62.0, 69.3 and 72.6 ppm (t) as well as by a methyl group at 13.3 ppm and a carbonyl carbon at 168.0 ppm.…”

“…[5][6][7] This last parameter being obviously related to the structure of the acidic monomer, a wide range of polymerizable dihydrogen phosphates, phosphonic and bisphosphonic acids were synthesized in order to improve the SEAs performance. [1,2,[8][9][10][11][12][13] Recently, the synthesis of the 3-(methacryloyloxy)-2,2-[di((dihydroxyphosphoryl)methyl)]propyl methacrylate (MDMP) was reported ( Figure 1). [8] This monomer exhibits great adhesive properties and is a potential candidate to enter new adhesive formulations.…”