FT-IR spectroscopy further validated the kinetic model by showing that the spontaneous reaction between chitosan and PCA did not occur at a pH of 1. Since the pKa of chitosan is below 7, spontaneous reactions with catechols were expected, as was confirmed using FT-IR and UV–Vis spectroscopy where spontaneous reactions occurred at pH 5 and 6.5. Kinetic models for the C–N bond formation between primary amines and catechols via Michael-type addition suggest that the reaction is promoted by a low pKa value of the primary amine used and a neutral or mildly acidic reaction pH. In order to develop such an adhesive, chitosan was functionalized with protocatechuic acid (PCA) via a Michael-type addition. Mussel-inspired catechol-containing polymers provide a promising basis for developing strong biogenic adhesives.
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