Functionalized fibrous material
Functionalizing a fibrous material having a plurality of hydroxyl groups includes reacting the fibrous material with a compound of Formula I: where X is a monovalent counteranion for the quaternary ammonium cation of Formula I and Hal is a halogen atom, to obtain the functionalized fibrous material. Also provided is a functionalized fibrous material prepared by any one of the methods described herein (e.g., a functionalized fiber including a moiety of Formula II: having an odor of free amine below the threshold of detection, or having an odor of free amine with degree of offensiveness of about 3 or less. The functionalized fibrous material may be dyed, and articles of clothing may be made from the dyed functionalized fibrous material.
1. A method of functionalizing a fibrous material comprising a plurality of hydroxyl groups, the method comprising:
reacting the fibrous material with a compound of Formula I:
wherein X is a monovalent counteranion for the quaternary ammonium cation of Formula I and Hal is a halogen atom, to obtain the functionalized fibrous material.
2. The method of claim 1 , wherein Hal is selected from Cl and Br.
3. The method of claim 1 , wherein Xis selected from Cl and Br.
4. The method of claim 1 , wherein the fibrous material comprises cellulosic fibrous material.
5. The method of claim 4 , wherein the cellulosic fibrous material is a natural fibrous material.
6. The method of claim 5 , wherein the natural fibrous material comprises cotton.
7. The method of claim 4 , wherein the cellulosic fibrous material is a synthetic fibrous material.
8. The method of claim 7 , wherein the synthetic fibrous material comprises rayon.
9. The method of claim 1 , wherein the reacting is carried out in an aqueous solvent.
10. The method of claim 1 , wherein the reacting comprises forming a covalent bond between the carbon atom to which Hal is attached and the oxygen atom of a hydroxyl group of the fibrous material.
11. The method of claim 1 , wherein the functionalized fibrous material comprises at least one moiety of formula:
wherein a denotes a point of attachment of the moiety of Formula II to an oxygen atom of a hydroxyl group of the fibrous material.
12. The method of claim 1 , wherein the reacting is carried out in the presence of a base.
13. The method of claim 12 wherein a molar ratio of the base to the compound of Formula I is from about 1:1 to about 2:1.
14. The method of claim 13 , wherein the base is an alkali hydroxide.
15. The method of claim 1 , wherein the reacting is carried out at about room temperature.
16. A functionalized fibrous material prepared by the method of claim 1 .
17. A fibrous material comprising a plurality of hydroxyl groups, wherein at least one hydroxyl group of the fibrous material is functionalized with a moiety of Formula II:
wherein X is a monovalent counteranion for the quaternary ammonium cation of Formula II, and a denotes a point of attachment of the moiety of Formula II to the oxygen atom of the hydroxyl group of the fibrous material.
18. The fibrous material of claim 17 , having an odor below the threshold of detection.
19. The fibrous material of claim 17 , having an odor with a degree of offensiveness of about 3 or less.
20. A method of dyeing the fibrous material of claim 17 , the method comprising contacting the fibrous material with a dye.