Abstract
Four polymerizable phosphonic acids bearing urea groups 4a, 4b, 9a, and 9b as well as the 10-(methacryloyloxy)decylphosphonic acid 10 were synthesized in four to six steps. They were characterized by 1H, 13C, and 31P NMR spectroscopy and by high-resolution mass spectroscopy. Contrary to methacrylates 4a and 4b, methacrylamides 9a and 9b were hydrolytically stable in deuterated water/deuterated ethanol solutions. The photopolymerization behavior of acidic monomers 4a, 4b, 9a, 9b, and 10 and their corresponding phosphonates were studied using a differential scanning calorimeter. Homopolymerizations and copolymerizations with N-butyl-N-ethylacrylamide were carried out. The presence of a urea group was found to significantly increase the rate of polymerization. Monomers bearing a phosphonic acid group were more reactive than their corresponding phosphonates. Self-etch adhesives based on monomers 4a, 4b, 9a, and 9b were able to provide a strong bond between a composite and the dental hard tissues (dentin and enamel). The presence of a urea group led to a significant increase in the shear bond strength to both dentin and enamel.
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