Cotton fabric was esterified with C4-18 aliphatic monobasic acid chlorides in dimethyl formamide, with pyridine as acid scavenger, at temperatures of 30-85°C. Reaction for 15-60 min at 85°C produced 0.02-0.36 ester groups per monomer unit, which provided water-repellency ratings of 50-80 in the AATCC spray test; water-repellency generally improved with increasing chain length and reaction temperature. Dry-cleaning resistance was good in perchloroethylene alone, but addition of alkaline soap required longer chain lengths and preferably an aqueous post-rinse to retain water repellency. Air permeability decreased during the reaction, but this was due primarily to shrinkage rather than inherent in the pro duction of water repellency. Tensile strength decreased gradually with increasing chain length, temperature, and time, but it was possible to produce a maximum spray rating of 80 with a tensile loss of only 33% and spray ratings of 70 with tensile losses as low as 12%.
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American Association of Textile Chemists and Colorists, Drycleaning: Durability of Applied Designs and Fabrics, AATCC Technical Manual44, 132-133 (1968).
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American Association of Textile Chemists and Colorists, Water Repellency: Spray Test, AATCC Technical Manual44, 154-155 (1968).
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American Society for Testing and Materials , Air Permeability of Textile Fabric, ASTM Standards, 24, 148-151 (1968).
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American Society for Testing and Materials , Breaking Load and Elongation of Textile Fabrics, ASTM Standards, 24, 361-370 (1968).
8.
Baldwin, A.W. , Evans, J.G., and Salkeld, C.E., Waterproofing Cellulosic Textile Materials, Films, Paper, etc., (to Imperial Chemical Industries) , Brit . 477,991 (January 10, 1938).
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Baldwin, A.W. and Walker, E.E., Quaternary Ammonium Salts (Wetting, Penetrating, Softening, and Waterproofing Agents for Cellulosic Textile Materials, etc.), (to Imperial Chemical Industries)U. S.2,146,392 (February 7, 1939).
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Berni, R.J. , Benerito, R.R., and Fagley, T.F., Preparation and Rates of Hydrolysis of Perfluoro-Esters of Cellulose, Textile Res. J . 30, 393-399 (1960).
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Billmeyer, F.W. , Jr., Textbook of Polymer Science, New York, Interscience, 1964, pp. 18-19, 231.
Caufield, J. , Rendering Fabrics Water-Repellent, (to William Smith (Poplar)), Brit. 1,066,285 (April 26, 1967).
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Deutsche Hydrierwerke A.G., Rendering Textiles, Paper, Leather and Furs Water-Repellent, Brit. 522,204 (June 12, 1940).
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Dolid, J., Aluminum Soap Solution Suitable for Waterproofing Fabrics, Stone, etc., U. S. 2,032,528 (March 3, 1936).
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E.I. du Pont de Nemours, Oil- and Water-Repellent Compositions and Their Application, Brit. 1,058,955 (February 15, 1967).
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Establishment Kuhlmann, Flame- and Waterproofing Treatment for Textiles, Brit. 1,081,959 (September 6, 1967).
19.
Gagliardi, D.D., Jutras, W.J., Jr., Cicione , R.J., and Kenney, V.S., Oxazoline Waxes—A New Class of Reactive Water Repellents for Textiles . Amer. Dyestuff Reptr. 56 (9), 325-329 (1967).
Genung, L.B. and Mallatt, R.C., Analysis of Cellulose Derivatives—Determination of Total Combined Acyl in Cellulose Organic Esters, Ind. Eng. Chem., Anal. Ed. 13 (6), 369-374 (1941).
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Horry, W.T. (to John Waddington Ltd.), Improvements in and Relating to Cartons and like Containers, Brit. 818,942 (August 29, 1959).
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Iler, R.K., Increasing the Hydrophobic Properties of Surfaces Such As Cloth, Paper, Sand or Asbestos, (to E. I. du Pont de Nemours), U. S. 2,273,040 (February 14, 1942).
24.
Johnson, G.W. , Waterproofing Textile Materials, (to I. G. Farbenindustrie A.G.), Brit. 460,602 (February 1, 1937).
25.
Johnson, G.W. , Wetting Agents , etc., (to I. G. Farbenindustrie A.G.), Brit . 466,853 (June 4, 1937).
26.
Karrer, P. , Modifying the Properties of Cotton Fabrics, etc., (Haberlein & Co.), U. S. 1,897,026 (February 7, 1933).
27.
Marsh, J.T. , "An Introduction to Textile Finishing," London , Chapman & Hall, 1966, pp. 458-494.
28.
McKelvey, J.B. , Benerito, R.R., and Berni, R.J., Esterification of Cotton with Certain Monofunctional Acid Chlorides and the Effect on Crease Recovery, Textile Res. J. 35 (4), 365 (1965).
29.
McKelvey, J.B. , Benerito, R.R., and Berni, R.J., Esterification of Cotton with Certain Monofunctional Add Chlorides and the Effect on Crease Recovery, Textile Res. J. 35, 370-373 (1965).
30.
McKelvey, J.B. , Berni, R.J., Benerito , R.R., and O'Connor , J.A., Partial Monobasic Esters of Cotton Cellulose. Part II: Effects of Substitution and Unsaturation in Acyl and Aroyl Esters on Crease Recovery, Textile Res. J. 36, 828-836 (1966).
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Nathanson, A., Rendering Textile Materials Water-Repellent , U. S. 2,092,702 (September 7, 1937).
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Nathanson, A., Rendering Cotton Textiles Water-Repellent , U. S. 2,130,150 (September 13, 1938).
33.
' O'Connor, R.T. , DuPré, E.F., and McCall, E.R., Infrared Spectrophotometric Procedure for Analysis of Cellulose and Modified Cellulose, Anal. Chem . 29 (7), 998-1005 (1957).
34.
Rowen, J.W. and Gagliardi, D.D., Properties of Water Repellent Fabrics , Amer. Dyestuff Reptr. 36 (18), 533 (1947).
35.
Rust, J.B. , Textile-Treating Compounds, (to Ellis Foster Co.), U. S. 2,285,948 (June 9, 1942).
36.
Stewart, R. , The Investigation of Organic Reactions, Princeton-Hall , 1966, Page 12.
