Monomers for Adhesive Polymers, 4

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  • Part 3: cf. ref.1

Abstract

Hydrolytically stable, crosslinking bis(acrylamide)s 1a1l or bis(methacrylamide)s 2a2c were synthesized by reaction of acryloyl or methacryloyl chloride using primary or secondary amines. In addition, monomers 3a and 3b were obtained by amidation of 2,6-dimethylene-4-oxaheptane-1,7-dicarboxylic acid (DMOHDA) with propylamine and diethylamine, respectively. The structures of the monomers were characterized by IR, 1H, and 13C NMR spectroscopy. All monomers containing N,N′-monosubstituted carbamide groups were solids. Those containing N,N′-disubstituted carbamide groups were water-soluble liquids. Water-soluble bis(acrylamide) 1d (N,N′-diethyl-1,3-bis(acrylamido)propane) shows a radical polymerization reactivity in the presence of 2,2′-azobis(2-methylpropionamidine) dihydrochloride (AMPAHC) similar to that of glycerol dimethacrylate, as revealed by gelation experiments in water. 1d is hydrolytically stable in 20 wt.-% phosphoric acid and can be used to substitute dimethacrylates in self-etching dentin adhesives. Furthermore, this monomer was also suitable as a reactive diluent in composites.

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Ancillary