2003
DOI: 10.1002/mame.200350003
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Monomers for Adhesive Polymers, 4

Abstract: 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, 1H, and 13C NMR spectroscopy. All monomers containing N,N′‐monosubstituted carbamide groups were … Show more

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Cited by 53 publications
(56 citation statements)
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“…On the other hand, the increasing residual unsaturation in copolymers formed in Table 5. Copolymerization of 1 with 3 (combination (iii)), [1] [19] It was evident that in the present system (iii), the polar phosphonic acid groups shield the second double bonds of the copolymerized difunctional monomer. The pendant double bonds, as well as the growing polymer radicals become less accessible to other propagating chain radicals.…”
Section: Copolymerizationsmentioning
confidence: 79%
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“…On the other hand, the increasing residual unsaturation in copolymers formed in Table 5. Copolymerization of 1 with 3 (combination (iii)), [1] [19] It was evident that in the present system (iii), the polar phosphonic acid groups shield the second double bonds of the copolymerized difunctional monomer. The pendant double bonds, as well as the growing polymer radicals become less accessible to other propagating chain radicals.…”
Section: Copolymerizationsmentioning
confidence: 79%
“…[5] Monomers 2 and 3 (Scheme 2) were prepared as previously described. [1,3] Methyl methacrylate (MMA) was washed with a 5.0 wt.-% NaOH solution, dried over anhydrous sodium sulfate, and distilled from calcium hydride under argon. AIBN was purified by recrystallization from methanol.…”
Section: Experimental Partmentioning
confidence: 99%
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“…[6] In this context, new bis(acrylamide)s, for example, monomer 2, showed excellent solubility in water and organic solvents and both improved hydrolytic stability and biocompatibility compared to the currently used dimethacrylates. [7] In addition, it was found, [8] e.g., that both N-(2-hydroxyethyl)methacrylamide and monomer 1 demonstrate improved hydrolytic stability and very low cytotoxicity and therefore can be used to substitute the frequently used 2-hydroxyethyl methacrylate of current enamel-dentin adhesives.…”
Section: Full Papermentioning
confidence: 99%