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Monomers for Adhesive Polymers, 4
Author(s) -
Moszner Norbert,
Zeuner Frank,
Angermann Jörg,
Fischer Urs Karl,
Rheinberger Volker
Publication year - 2003
Publication title -
macromolecular materials and engineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.913
H-Index - 96
eISSN - 1439-2054
pISSN - 1438-7492
DOI - 10.1002/mame.200350003
Subject(s) - monomer , acryloyl chloride , polymer chemistry , methacrylamide , acrylamide , materials science , propylamine , polymerization , diethylamine , polymer , dimethylamine , glycidol , phosphoric acid , organic chemistry , amine gas treating , chemistry , acrylate , catalysis
Hydrolytically stable, crosslinking bis(acrylamide)s 1a – 1l or bis(methacrylamide)s 2a – 2c 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, 1 H, and 13 C 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.