Stearamidomethylpyridinium chloride reacts with cellulosic hydroxyl groups to produce a stearamidomethyl ether of cellulose. Substitutions of 1 stearamidomethyl group per 150 anhydroglucose units have been obtained. The permanent water-repellency obtained on treatment of cotton fabrics with amidomethylpyridinium salts is due to this reaction. AMIDOMETHYLPYRIDINIUM SALTS are widely used for the production of permanently waterrepellent cotton cloth [16]. According to most patent claims, these compounds impart permanent waterrepellency by chemical reaction with cellulose. Some workers, in studies from the theoretical point of view [6,24], have concluded that chemical reaction actually takes place, while others hold that the waterrepellency is due to the deposition of decomposition products from the amidomethylpyridinium salts and possibly their adsorption on the surface of the fiber [18].Little direct chemical evidence has been offered to support either of these views. Davis [6] did obtain chemical evidence of a reaction between stearamidomethylpyridinium chloride and cellulose, but he acknowledges that his work is not comprehensive. He treated cotton fabrics with Velan PF,'~' a British trade product similar to the Zelan t used in the United States. The active ingredient in these two products is stearamidomethylpyridinium chloride, CJ7H35CONHCHzN+C5H¡; Cl-.Davis concluded that 1% to 2 % of this compound reacts with cellulose to form the stearamidomethyl ether of cellulose. The mechanism proposed by Davis for the ether formation is hydrolysis of the pyridinium chloride to the methylolamide, which reacts with cellulose at curing temperatures. Any stearamidomethylpyridinium chloride in excess of 2% forms only decomposition products, which can be removed by chloroform extraction. The amount of cellulose ether can then be estimated from the amount of formaldehyde released by hydrolysis with 5% sulfuric acid. Davis reported that 1 mole of the ether yielded 1 mole of formaldehyde.