Industrial & Engineering Chemistry Research, Vol.36, No.10, 4231-4235, 1997
Preparation of N-Alkyl-Substituted Poly(Oxyalkylene)Amines and Their Reactivities Toward Blocked Isocyanates
Poly(oxyalkylene)polyamines can be readily converted to the corresponding secondary amines by one-step reductive amination. The reaction involved in-situ hydrogenation of the mixture of a polyether primary amine and ketone under the conditions of 80-180 degrees C and 1500-3000 psi of hydrogen, using a Ni/Cu/Cr or Pd catalyst. The synthetic methodology was generalized with molecular weights of starting primary amines ranging from approximately 150 to 2000. The reaction mechanism involving an imine (C=N) intermediate is postulated. The relative reactivity and industrial application of these secondary amines have also been demonstrated by the reactions with blocked isocyanates. In comparison with their primary amine precursors, N,N’-dialkyl-substituted poly(oxyalkylene)polyamines lowered the reactivities toward blocked isocyanates in one-component coating applications and consequently improved the storage stability. When the one-component amine-isocyanate system is heated, the secondary amines cured well with the blocked isocyanate to form a desirable polyurea coating.