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Principles of Reactivity of Nitrogenous Agents with Cotton

A new approach to circumvent the direct relationship between the reactivity of N-methylol agents and hydrolysis rates of the cellulose derivatives under acidic conditions has been studied. To achieve a more durable product from a reactive agent with cellulose, an irreversible system was sought through incorporation of a suitable leaving group, such as acetoxy, to activate the agent. Reactivities of acetoxymethyl, hydroxymethyl, and methoxymethyl derivatives of N-methyl-2- imidazolidinone (MI), methyl carbamate (MC), and benzamide (B) have been compared under selected, acidic conditions. Reactivity contributed by carbonium-immonium ion stability is in the expected order (parent amide given) MI>>MC>B. Reactivity is significantly altered by the leaving group and is in the order acetoxy >> hydroxy >> methoxy. Substrates for reactivity studies included isopropanol, water, and cotton. Acetic acid released by reaction with these substrates and an acetoxy derivative had only a minor catalytic effect upon the reaction rate except in the fabric treatments carried out in the presence of magnesium chloride. Acetoxy-derivatives of similar polyfunctional agents are similarly activated as long as the acetoxy groups are isolated from one another; however, vicinal diacetoxy glyoxal resins appear to be of the same general order of reactivity as the corresponding dihydroxy derivatives. Use of these active agents in nonaqueous solvent systems is suggested and limitations for use in aqueous systems are discussed.