Electronic Effects of Substituent Groups upon Acid Hydrolysis of Amido-Methylol Finishes on Cotton

Abstract

The results of a study on the susceptibility to acid hydrolysis of the products from the reaction of amido-methylol compounds with cotton are reported. A correlation was found between electron displacement and ease of hydrolysis. Substituent groups in the amido-methylol compounds play an important role in the electron displacement. Electron- releasing groups attached to either the amido nitrogen or the carbonyl carbon facilitate acid hydrolysis; electron-attracting groups hinder hydrolysis, Various hydrolysis mech anisms are considered for explaining the observed inductive and resonance effects. A mechanism wherein initial electrophilic attack is at the ethe al oxygen a fission of the link with cellulose is through carbonium ion formation appears co pletely satis factory in explaining the observed facts.