The reaction of (+)-catechin with N-Hydroxymethylacetamide : a model for cross-linking PVA resins with tannins Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/z029p685d

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  • Equal molar amounts of (+)-catechin and N-Hydroxymethylacetamide were reacted under acidic conditions. Thin-layer chromatography (TLC) was used to monitor the reaction. The reaction products were isolated by column chromatography using Sephadex LH-20 and elution with 95 percent ethanol. Three reaction products isolated included one disubstituted and two monosubstituted compounds. The structures of these compounds were determined by using ¹H and ¹³C nuclear magnetic spectroscopy (NMR), and verified by utilizing both positive and negative ion fast atom bombardment mass spectrometry (FAB-MS). The pattern of substitution on the two monosubstituted products was determined using a two-dimensional NMR technique called a HET-COSY, which showed long distance C-H coupling interactions. This reaction can be used as a model to cross-link polyvinyl acetate resins (PVA) with condensed tannin derivatives. Such cross-linked resins could possibly make PVA adhesives more suitable for structural applications.
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