Quantitative and qualitative 1H, 13C,and 15N NMR spectroscopic investigation of the urea–formaldehyde resin synthesis |
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Authors: | Oliver Steinhof Éléonore J Kibrik Günter Scherr Hans Hasse |
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Institution: | 1. Institute of Thermodynamics and Thermal Process Engineering, Universit?t Stuttgart, , 70569 Stuttgart, Germany;2. Laboratory of Engineering Thermodynamics, University of Kaiserslautern, , 67663 Kaiserslautern, Germany;3. BASF SE, , 67056 Ludwigshafen, Germany |
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Abstract: | Urea–formaldehyde resins are bulk products of the chemical industry. Their synthesis involves a complex reaction network. The present work contributes to its elucidation by presenting results from detailed NMR spectroscopic studies with different methods. Besides1H NMR and13C NMR,15N NMR spectroscopy is also applied.15N‐enriched urea was used for the investigations. A detailed NMR signal assignment and a model of the reaction network of the hydroxymethylation step of the synthesis are presented. Because of its higher spectral dispersion and the fact that all key reactions directly involve the nitrogen centers,15N NMR provides a much larger amount of detail than do1H and13C NMR spectroscopy. Symmetric and asymmetric dimethylol urea can be clearly distinguished and separated from monomethylol urea, trimethylol urea, and methylene‐bridged urea. The existence of hemiformals of methylol urea is confirmed. 1,3,5‐Oxadiazinan‐4‐on (uron) and its derivatives were not found in the reaction mixtures investigated here but were prepared via alternative routes. The molar ratios of formaldehyde to urea were 1, 2, and 4, the pH values 7.5 and 8.5, and the reaction temperature 60 °C. Copyright © 2014 John Wiley & Sons, Ltd. |
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Keywords: | NMR 1H 15N 13C urea– formaldehyde quantitative NMR virtual reference 2D NMR hydroxymethylation adhesives |
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