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Optica Publishing Group
  • Applied Spectroscopy
  • Vol. 51,
  • Issue 3,
  • pp. 438-442
  • (1997)

1H NMR Study of the Reaction of Diacetylmelamine with Oxiranes

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Abstract

The reaction of 1 mole of melamine with 2 moles of acetic anhydride leads to diacetylmelamine (DAM), which is a mixture of two constitutional isomers: 90% <i>N,N'</i>-DAM and 10% <i>N,N'</i>-DAM. The reaction of 1 mole of DAM with 1-8 moles of oxiranes (ethylene and propylene oxides) was studied by <sup>1</sup>H NMR spectroscopy. At the molar ratio of substrates 1: ~ 2, no <i>N,N'</i>-diacetyl- <i>N,N'</i>-bis(2-hydroxyalkyl)melamine was formed, but the product of its intramolecular rearrangement, <i>N,N'</i>-bis(2-acetyloxyalkyl)melamine, was found. The latter reacted with the excess of oxiranes to appropriate tetrafunctional polyetherols containing s-triazine rings.

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