Functionalized fibrous material

Patent metadata

Field	Value
Publication number	US-10640918-B2
Application number	US-201815998782-A
Country	US
Kind code	B2
Filing date	Aug 15, 2018
Priority date	Aug 15, 2017
Publication date	May 5, 2020
Grant date	May 5, 2020

Abstract

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.

First claim

What is claimed is:

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.

Assignees

• Hbi Branded Apparel Entpr Llc
• Cotton Inc
• Univ North Carolina State

Inventors

• Freeman Harold S
• Szymczyk Malgorzata
• Zimmerman Keith
• Farrell Matthew J

Classifications

• D06P1/66

  containing quaternary ammonium groups · CPC title

• D06M2400/01

  Creating covalent bondings between the treating agent and the fibre · CPC title

• D06M13/463

  derived from monoamines · CPC title

• D06P1/38

  using reactive dyes · CPC title

• D06M2101/06

  cellulosic · CPC title