Distribution and Structure of Reagent Residues Resulting from Wet-Cure and Bake-Cure Crosslinking of Cotton with N-Ethylbis(2-Chloroethyl)Amine

Abstract

N-Ethyl-N-(2-chlorciethyl)aziridinium chloride, the water-soluble intermediate formed from N-ethylbis(2-chloroethyl)- amine, was found to be sufficiently stable to allow bake-cure as well as wet-cure crosslinking of cotton. An examination was made of the effects of wet-cure (25°C) vs bake-cure (120°C and 140°C) crosslinking upon the structures of the reagent residues (i.e., the fractions of simple substituents, simple crosslinks. and complex structures) and upon the sites of attach ment of reagent residues to the glucose units of the cellulose chain. The fraction of simple crosslinks was similar in products of both wet- and hake-cure reactions; however, the fraction of simple substituents was higher and the fraction of complex products was lower in the cotton modified by bake-cure reactions. The predominant crosslinks in all cases were those with 2,6'-O-linkages (i.e., from the hydroxyl at C-2 in one glucose unit to the hydroxyl at C-6 in another glucose unit).

Keywords

Cotton fabric N-ethylbis(2-chloroethyl)amine N-ethyl-N-(2-chlorotehyl)aziridinium chloride chemically modified cotton. Wet cure bake cure. Simple substituent simple crosslink crosslinking hydrolysis reduction. Electro phoresis chromatography.

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References

Roberts, E.J. , Brannan, M.A.F. , and Rowland , S.P. , Nature and Proportion of Cross Links in a Chemically Modified Cotton Cellulose, Textile Res. J. 40, 237-243 (1970).

Roberts, E.J. , Brannan, M.A.F. , and Rowland , S.P. , An Exploratory Characterization of Cotton Cellulose Modified with Tris(2-chloroethyl)phosphoramide , Textile Res. J. 40, 699-703 (1970).

Roberts, E.J. and Rowland, S.P. , Extent of Formation of Ether Linkages Between Tris(1-aziridinyl)phosphine Oxide and Cotton Cellulose, Textile Res. J. 40, 401-405 (1970).

Roberts, E.J. and Rowland, S.P. , Effect of Selected Reaction Conditions and Structural Variations on the Distribution of 2-(Diethytamino)ethyl Groups on D-Glucopyranosyl Residues of 2-(Diethylamino)ethylated Cellulose, Starch, and the Anomers of 4,6-0-Benzylidene-D-glucopyranoside, Carbohydrate Res. 5, 1-12 (1967).

Roberts, E.J. and Rowland, S.P. , Synthesis of the Substituted and Crosslinked Glucoses Corresponding to the Structural Units in a Cotton Cellulose Modified with N-Methyl-bis(2-chloroethyl)amine, Can. J. Chem. 48, 1383-1390 (1970).

Roberts, E.J. , Wade, C.P. , and Rowland, S.P. , A Pad-Cure Process for the Preparation of DEAE Cotton, Textile Res. J. 41, 710-712 (1971).

Roberts, E.J. , Wade, C.P. , and Rowland, S.P. , Structure of Reagent Residues in Cotton Cellulose Modified with Tris-(1-aziridinyl)phosphine Oxide, Textile Res. J. 40, 395-400 (1970).

Rowland, S.P. , Mechanisms of Durable Press, Textile Chem. Colorist, in press.

Rowland, S.P. , Cirino, V.O. , and Bullock, A.L. , Structural Components in Methyl Vinyl Sulfone Modified Cotton Cellulose, Can. J. Chem. 44, 1041-1058 (1966).

10.

Rowland, S.P. , Cirino, V.O. , and Bullock, A.L. , How the Structure of Cross-Linked Cotton Affects Fabric Performance, Textile Chem. Colorist 1, 450-457 (1969).

11.

Rowland, S.P. , Cirino, V.O. , and Bullock, A.L. , Structures of Reagent Residues Resulting from Reactions of Divinyl Sulfone with Cotton Cellulose, J. Polymer Sci. A-1, 9, 1677-1683 (1971 ).

12.

Rowland, S.P. , Roberts, E.J. , and Stark, S.M. , Network Formation in Cotton Celeulose Modified with Ttis(1-aziridinyl)phosphine Oxide, Textile Res. J. 40,405-410 (1970).

13.

Sowa, John R. and Price, Charles C. , Nitrogen Mustard Reactions by Nuclear Magnetic Resonance Spectroscopy, J. Org. Chem. 34, 474-476 (1969).

14.

Wilson, Evelyn and Tishler, Max, Nitrogen Mustards, J. Amer. Chem. Soc. 73, 3635-3641 (1951 ).