Cellulose acetate esters containing amino nitrogen

Nitrogen was introduced into cellulose acetate by the incorporation of amino acid groups. Some of the mixed esters were soluble in organic solvents. Cast films were examined for dyeing properties with wool‐type dyes. Many of the mixed esters containing above 1% nitrogen dyed well with xylene brilliant blue, a typical wool‐type dye, Mixed cellulose acetate esters were synthesized containing glycine, dl ‐α‐alanine, β‐alanine, and α‐isoaminobutyric, d ‐glutamic, and p ‐aminobenzoic acids. The amino groups were protected by acetylation prior to use. The N ‐acetyl amino acids were treated with cellulose diacetate in dioxane solution containing chloroacetic anhydride and magnesium perchlorate as impellor and catalyst, respectively. Cellulose acetate metanilate was prepared by use of the aminosulfo acid chloride. An attempt was made to prepare 6‐aminocellulose by the reaction of aqueous ammonia, and also sodamide in liquid ammonia on 6‐iodotosylcellulose acetate. Only traces of nitrogen were introduced by this procedure and the recovered products showed signs of extreme degradation.