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Application of selective 1 : 2 addition of ketene N,N-acetal and isocyanates to novel polyamide syntheses

✍ Scribed by Nobuhiro Kihara; Yoriatsu Sugimoto; Takeshi Endo

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 171 KB
Volume: 37
Category: Article
ISSN: 0887-624X
DOI: 10.1002/(sici)1099-0518(19990815)37:16<3079::aid-pola5>3.0.co;2-2

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✦ Synopsis

1,1-Bis(dimethylamino)ethylene (ketene N,N-acetal) (1) reacted with isocyanates to give either 1 : 1 adduct 3,3-bis(dimethylamino)acrylamides (3) or 1 : 2 adduct bis(dimethylamino)methylenemalonamides ( 4), depending on the amount of the charged isocyanate. 3 was obtained selectively in the case of isocyanate/1 ϭ 1, while 4 was exclusively yielded in the case of isocyanate/1 ϭ 2. Isothiocyanate showed similar reaction behavior as isocyanate. Polyaddition of 1 with diisocyanates afforded polyamides bearing a bis(dimethylamino)methylenemalonamide group with higher molecular weight. The obtained novel polyamides are soluble in various organic solvents, and reacted with diacid chloride to give crosslinked polymer quantitatively.

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