Synthesis and characterization of novel fluoride-releasing monomers. II. Dimethacrylates containing bis(aminodiacetic acid) and their ternary zirconium fluoride complexes

摘要

Novel dimethacrylate monomers containing bis(aminodiacetic acid) chelating ligands with or without additional hydroxyl groups were synthesized, starting from 2,2-bis(4-hydroxy-3-methylphenyl)propane. The structures of the monomers were characterized by electrospray mass spectrometry (ESMS), H-1 NMR, and C-13 NMR. The structures and relative stability of fluoride-releasing monomers containing one or more ternary zirconium fluoride complex moieties were studied by ESMS. The most stable ternary zirconium fluoride complex was in the form of [LZrF](-), where H4L is the monomer containing bis(aminodiacetic acid) without additional hydroxyl groups. The synthesized monomer was photopolymerized with camphorquinone and 1-phenyl-1,2-propane-dione as initiators and N,N-dimethylaminoethyl methacrylate as the accelerator. The fluoride release, fluoride recharge, compressive strength, and flexure strength were tested on the experimental dental composite containing 13.7 wt % synthesized monomer and three commercial flowable dental composites. The results showed that the experimental composite has significantly higher fluoride release and recharge capabilities than the commercial flowable composites. The compressive strength was comparable to that of the commercial materials. The water sorption and solubility met the requirement of the ISO Specification 4049. (c) 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 3153-3166, 2005.