Additional studies have been made on partial carboxymethylation—the reaction between mono chloroacetic acid and cotton in the presence of sodium hydroxide—and on the products ob tained. A thorough investigation of the time and temperature of reaction and concentration of reagents showed that relatively small amounts of monochloroacetic acid, properly applied, alter the properties of cotton considerably. Pilot-scale carboxymethylation of cloth was conducted which showed that it is possible to use standard textile machinery in the process. The cloth resulting from this treatment had a crisp liand with a slightly starched feel. More detailed investigations than reported previously were made, and it was found that the tensile strength and elongation of treated cotton are increased, dyeing properties are changed, and soiling-resistance and soil removal are increased. It was also learned that the treated materials are unaffected after one year's storage.

Water- and alkali-soluble cotton fibers, yarns, and threads have been prepared by two methods. The cotton is preferably pretreated by pressure-kiering in 2% sodium hydroxide to remove the noncellulosic materials, and then treated with monochloroacetic acid and sodium hydroxide by either a one-step or a two-step process. Where only disintegration or partial solubility is required, the one-step method is sufficient. Where complete solubility of the cot ton is required, the process must be carried out in two steps: a mild, followed by a stronger treatment. The treated cotton is neutralized in alcohol with acetic acid to produce water soluble products or with strong acids in alcohol to produce water-insoluble but alkali-soluble products. Cotton in the form of sliver, yarn, and thread has been successfully treated.

The preparation of partially cyanoethylated cotton with acrylonitrile in the presence of sodium hydroxide is described, including effects of changes in time, temperature, and concentration of reagents. Products with retention of the fibrous form have been ob tained with degrees of substitution up to 2.7 cyanoethyl groups per anhydroglucose unit. Hydrolysis of the cyanoethyl group occurs readily under alkaline conditions and re sults in both cleavage and conversion to the carboxyethyl group. Maximum conversion in the latter case was 29%.

For the purpose of obtaining quickly swellable fibers to aid in making cloth less pervious to water, cotton fibers have been partially carboxymethylated. Different degrees of swelling have been obtained and the properties of the resulting products are described.

β-Propiolactone was reacted with purified cotton in the presence of organic solvents. The reaction was found to be affected by time, temperature, and concentration of reagents. Weight gains of upwards of 60% were obtained.In all reactions of purified cotton with β-propiolactone in organic solvents, etherification occurs, apparently followed by polyesterification of the attached groups by additional lactone. Attempts to direct the reaction towards either etherification or esterification by means of acid and base catalysis were not successful.Increases in the extent of reaction were obtained by "activation" of purified cotton with acetic acid prior to the treatments with β-propiolactone.