Monomers for Adhesive Polymers, 3. Synthesis, Radical Polymerization and Adhesive Properties of Hydrolytically Stable Phosphonic Acid Monomers

Phosphonic acid‐based amphiphilic diblock copolymers derived from ROMP

“…[15][16][17] Phosphorus-containing polymers have broad application areas; besides their flameretardant properties, 18 they are also used in biomaterials for their adhesive properties to metals, bone, and dentin. [19][20][21][22] The incorporation of phosphonic acid into acrylic monomers used in the dental industry can promote both biocompatibility and adhesion to the teeth, because of the formation of calcium phosphonates and phosphonate complexes. 21,[23][24][25] Phosphonates, corresponding anions of phosphonic acid, have strong interactions with and adsorb very powerfully onto mineral surfaces.…”

Multi-purpose Bonding Performance of Newly Synthesized Phosphonic Acid Monomers

“…Further, it was found that a self-etching primer comprising 10-MDP provided efficient bonding of composite-type resin cement to titanium (Ti) 42) , while an adhesive primer containing 6-MHPA was found to exhibit strong adhesion to zirconia-and alumina-based all-ceramic prostheses 43) . On this note, hydrolytically stable adhesive monomers should be incorporated in single-bottle water-based self-etch primers or all-in-one adhesives [7][8][9][10][11][12][13] . In addition to phosphonic acid and flexible methylene chain moieties, it was suggested that a super-adhesive monomer should possess hydrolytically stable moieties in the molecular structure.…”

“…However, they formulated with ethyl alcohol, and did not show significant efficacy on bonding to the teeth 6) . Despite the lack of early success, recently synthesized phosphonic acid monomers appeared to be hydrolytically stable in self-etching primers or adhesives [7][8][9][10][11][12][13] and hence seemed promising. However, since these investigations [7][8][9][10][11][12][13] have not been extended beyond water-based adhesives, little is known about the multi-purpose bonding performance of phosphonic acid monomers with polymerization initiators in hydrophobic adhesive resins.…”

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

“…[23,24] It was also demonstrated that N-alkylacrylamides exhibit a great stability in such acidic conditions. [2,9,10,25] Monomers 4, 8, 10a and 10b bearing a methacrylate group, their storage in aqueous solutions would require low temperatures (storage in the refrigerator).…”