Abstract
Four polymerizable α-phosphonooxy phosphonic acids 7a, 7b, 9 and 16 were synthesized in seven steps. They were characterized by 1H, 13C and 31P NMR spectroscopy and by high-resolution mass spectroscopy. The copolymerization of acidic monomers 7a, 7b, 9 and 16 with 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 monomers 7a, 7b, 9 and 16 were 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.
Highlights
Self-etch adhesives (SEAs) are nowadays often used to achieve a bond between the dental hard tissues and a restorative material.[1,2,3] A selfetch adhesive (SEA) is an aqueous formulation containing different monomers, cosolvents and additives (photoinitiator(s), co-initiator(s), stabilizers, fillers, etc.)
It has been demonstrated that the adhesion of SEAs can be improved when polymerizable diphosphonic acids,[10,11,12] β-ketophosphonic acids [13] or phosphonic acids bearing urea groups [14] are used as acidic monomer
Acidic monomer 9 was synthesized in two steps, starting from alcohol 5a (Scheme 2)
Summary
Self-etch adhesives (SEAs) are nowadays often used to achieve a bond between the dental hard tissues (dentin and enamel) and a restorative material (composite).[1,2,3] A SEA is an aqueous formulation containing different monomers (acidic, monofunctional and crosslinking monomers), cosolvents (ethanol, acetone, etc.) and additives (photoinitiator(s), co-initiator(s), stabilizers, fillers, etc.). The acidic monomer is responsible for the etching of the tooth surface Monomers such as polymerizable dihydrogen phosphates, carboxylic or phosphonic acids can be found in SEA formulations.[4] In SEAs, the acidic monomer should exhibit good etching properties, sufficient storage stability and a low oral toxicity.[5] It has to show a high rate of homo- or copolymerization with the comonomers of the formulation. Acidic monomers exhibiting strong chelating properties were synthesized and tested in SEAs. It has been demonstrated that the adhesion of SEAs can be improved when polymerizable diphosphonic acids,[10,11,12] β-ketophosphonic acids [13] or phosphonic acids bearing urea groups [14] are used as acidic monomer
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