Structure of Reagent Residues in Cotton Cellulose Modified with Tris(1-aziridinyl)phosphine Oxide

Several samples of tris(1-aziridinyl)phosphine oxide (APO)-modified cotton were prepared with 5.8-14.6% APO in corporation. The samples were degraded by acid hydrolysis and attempts were made to isolate the expected 0-(2-amino ethyl)-D-glucopyranoses and 0-[N-(2-aminoethyl)-2-aminoethyl]-D-glucopyranoses by a variety of techniques. Neither of these glucose derivatives could be detected in the hydrolyzates; however, the hydrolyzates were found to contain a considerable quantity of ethanolamine along with N-(2-aminoethyl)ethanolamine and complex products resulting from reaction of the functional group at C-1 of glucose and the amino compounds derived from the APO during acid hydrolysis. The ethanolamine in the hydrolyzates of two samples of APO-modified cotton was estimated to account for about 85% of the total nitrogen in the samples. The N-(2-aminoethyl)ethanolamine was estimated to account for about 5% of the original nitrogen. The remaining 10% was in the form of polyethylenimines, N-glucosylamine compl...