Hydrolysis resistance of an N-methylol finish in acidic solutions can generally be predicted based on chemical factors, i.e., electronic effects of substituent groups on the intermediate immonium-carbonium ion, but other factors can produce unexpected results. In this respect, 2:1 and 4:1 molar ratios of formaldehyde in the finishing of cotton with a model reactant system based on N-methylol-2-pyrrolidone produced greater resistance to hydrolysis than anticipated. This effect was small and occurred primarily in the early stages of hydrolysis, suggesting that accessibility of some of the nitrogen bonds in the finish may have been reduced by the formaldehyde crosslinks.
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