CELL 138 |
New quaternary ammonium ion reagents from urea for fabric treatment
| Navzer D. Sachinvala1, Nicolette T. Prevost1, Jacqueline H. Campbell1, Leslie A. White1, Oliver D. Dailey Jr.2, Elena E. Graves1, John M. Bland3, and Karol Maskos4. (1) Cotton Textile Chemistry, USDA-ARS-SRRC, 1100 Robert E. Lee Blvd, New Orleans, LA 70124, (2) Commodity Utilization Research Unit, USDA-ARS-SRRC, 1100 Robert E. Lee Blvd., New Orleans, LA 70124, (3) Formosan Subterranean Termite Research Unit, USDA-ARS-SRRC, 1100 Robert E Lee Blvd, PO Box 19687, New Orleans, LA 70179, (4) Coordinated Instrumentation Facility, Tulane University, 604 Lindy Boggs Building, New Orleans, LA 70118 |
| Recently, we showed a one step conversion of urea to tertiary amines in water (J. Org. Chem., 2000, 65, 9234-9237). Of these, we used triallylamine to quaternize PEG, PPG, and aryl bromides (Figure 1). One and two-dimensional NMR and chemical ionization mass spectrometries were used to characterize the new quaternary ammonium salts, and formulations in water and alcohol were prepared for soaking fabrics. Two mechanisms of interaction with cotton fabric are being investigated. These are (a) entanglements, e.g., the Butler reaction, afforded by cycloaddition polymerization of allyl groups in the fiber matrix (Figure 2), and (b) crosslinking, wherein, e.g., allyl groups react with other functional groups that link cellulose. In this paper, we will report the preparation and characterization of new quaternary ammonium salts, explain our methods of entangling cellulose fibers in fabrics with these reagents, and examine their effects on material performance. In addition, we will discuss the effects of molecular weight, functional groups, and entanglement mechanisms on fabric performance.  |
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