Extent of Formation of Ether Linkages Between Tris(1-aziridinyl)phosphine Oxide and Cotton Cellulose

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Abstract
Cotton cellulose modified with tris(1-aziridinyl)phosphine oxide (APO) was prepared with and without zinc fluoborate catalyst. The modified cotton samples were hydrolyzed. Attempts to detect the expected 0-(2-aminoethyl)-D-glucopy- ranoses were complicated by reactions between the functional group at C-1 of the glucose unit and the amine function of the substituent. The ratio of substituents in the 2-0-, 3-0-, and 6-0-positions of the glucopyranosyl units in samples of APO-modified cotton cellulose could be measured when the amino groups were converted to hydroxyl groups by diazo tization prior to hydrolysis. The APO-modified cotton cellulose prepared with zinc fluoborate catalysis and containing 3.08, 5.77, and 14.62% APO exhibited substituent ratios of 0.23:0.21:1.00, 0.29:0.26:1.00, and 0.38:0.37:1.00, respec tively, at the 2-0-, 3-0-, and 6-0-positions. A sample of APO-modified cotton cellulose (6.38% APO) prepared without catalyst exhibited a substituent distribution of 0.65:0.35:1.00. The actual DS values of these samples were estimated to be 0.0040, 0.0071, 0.0084, and 0.0098 for the fabrics containing 3.08, 5.77, 6.38, and 14.62% of incorporated APO, respectively.