Residual soy flour sugars as crosslinkers for enhancing mechanical performance of protein fibers

Patent metadata

Field	Value
Publication number	US-11530300-B2
Application number	US-202016813694-A
Country	US
Kind code	B2
Filing date	Mar 9, 2020
Priority date	May 1, 2014
Publication date	Dec 20, 2022
Grant date	Dec 20, 2022

Abstract

Disclosed is a method of crosslinking protein fibers, including wool fibers, by (i) providing a crosslinking agent including an oxidized sugar mixture having a plurality of different oxidized sugars of different molecular lengths and having at least two aldehyde groups (e.g., oxidized soy flour sugars); and (ii) infiltrating a plurality of non-crosslinked protein fibers with the crosslinking agent under conditions effective to cause protein molecules contained in the non-crosslinked protein fibers to become crosslinked. This method yields a population of crosslinked protein fibers, where the protein molecules of the non-crosslinked protein fibers include amine groups that react with the aldehyde groups of the oxidized sugars to achieve the crosslinking of the protein molecules to yield the crosslinked protein fibers.

First claim

What is claimed is:

1. A method of crosslinking keratin-containing fibers, said method comprising:
providing a crosslinking agent comprising an oxidized sugar mixture comprising a plurality of different oxidized sugars having at least two aldehyde groups, wherein the sugars are selected from the group consisting of monosaccharides, disaccharides, trisaccharides, and tetrasaccharides; and
infiltrating a plurality of keratin-containing fibers with the crosslinking agent under conditions effective to cause protein molecules contained in the keratin-containing fibers to become crosslinked, thereby yielding a population of crosslinked keratin-containing fibers,
wherein the protein molecules of the keratin-containing fibers comprise amine groups that react with the at least two aldehyde groups of the oxidized sugars to achieve the crosslinking of the protein molecules to yield the crosslinked keratin-containing fibers.

2. The method according to claim 1 , wherein said infiltrating step is carried out at a temperature and for a length of time sufficient to yield crosslinked keratin-containing fibers having improved tensile properties selected from the group consisting of increased tensile strength and increased Young's modulus compared to the non-crosslinked keratin-containing fibers.

3. The method according to claim 2 , wherein the increased tensile strength comprises an increase in tensile strength selected from the group consisting of at least 20 percent, at least 25 percent, at least 30 percent, and at least 35 percent.

4. The method according to claim 2 , wherein the increased Young's modulus comprises an increase in Young's modulus selected from the group consisting of at least 20 percent, at least 25 percent, at least 30 percent, at least 35 percent, at least 40 percent, at least 45 percent, at least 50 percent, at least 55 percent, and at least 60 percent.

5. The method according to claim 2 , wherein said temperature used in the infiltrating step is between about 130° C. and about 160° C. for a period of time of between about 15 minutes and 25 minutes.

6. The method according to claim 2 , wherein the temperature is increased above room temperature by heating that is carried out by applying a source of heat during the infiltrating step, wherein the source of heat is selected from the group consisting of a flat iron, hot rollers, a hot plate, a curling iron, a hair dryer, an iron, a clothes dryer, and an oven.

7. The method according to claim 1 further comprising:
washing the population of keratin-containing fibers to remove residual crosslinking agent or to remove crosslinking agent adhering to the keratin-containing fibers, thereby substantially removing the crosslinking agent.

8. The method according to claim 1 , wherein the keratin-containing fibers are human hair fibers.

9. The method according to claim 1 , wherein the keratin-containing fibers are animal fibers selected from the group consisting of wool, alpaca, angora, fur, cashmere, mohair, and qiviut.

10. The method according to claim 1 , wherein the keratin-containing fibers are animal fibers from animals selected from the group consisting of sheep, vicuna, alpaca, llama, muskox, goats, bison, camel, yak, horse, chinchilla, and rabbit.

11. The method according to claim 1 , wherein the keratin-containing fibers are animal fibers having a form selected from the group consisting of raw fibers, yarns, felts, and woven or knitted fabrics.

12. The method according to claim 1 , wherein the sugars are water soluble.

13. The method according to claim 1 , wherein the oxidized sugar mixture comprises oxidized soy flour sugars (OSFS) having sugars selected from the group consisting of galactose, xylose, mannose, fructose, glucose, sucrose, raffinose, and stachyose.

14. The method according to claim 1 , wherein the sugars have a ratio of aldehyde per saccharide unit selected from the group consisting of ≥1, >1, >1.5, and ≥2.

15. The method according to claim 1 , wherein the crosslinking agent is prepared according to a method comprising the steps of:
providing a mixture of non-oxidized sugar molecules comprising a plurality of different sugars; and
reacting the non-oxidized sugar molecules with an oxidizing agent comprising sodium periodate (NaIO 4 ) to cause oxidation of the non-oxidized sugar molecules to yield a reaction mixture comprising an oxidized sugar mixture comprising a plurality of different oxidized sugars having at least two aldehyde groups, said oxidized sugar molecules corresponding to the crosslinking agent.

16. The method according to claim 15 further comprising:
introducing barium chloride (BaCl 2 ) to the reaction mixture to inhibit further oxidation of the sugar molecules.

17. The method according to claim 15 , wherein the crosslinking agent comprises an oxidized soy flour sugars (OSFS) mixture having a pH of about 3.

18. A method of making a crosslinking formulation for crosslinking keratin-containing fibers, said method comprising the steps of:
providing a mixture of non-oxidized sugar molecules comprising a plurality of different sugars; and
reacting the non-oxidized sugar molecules with an oxidizing agent comprising sodium periodate (NaIO 4 ) to cause oxidation of the non-oxidized sugar molecules to yield a crosslinking formulation comprising an oxidized sugar mixture comprising a plurality of different oxidized sugars having at least two aldehyde groups,
wherein the sugars are selected from the group consisting of monosaccharides, disaccharides, trisaccharides, and tetrasaccharides, and
wherein said mixture of oxidized sugars are crosslinking agents effective to react with amine groups of protein molecules contained in non-crosslinked keratin-containing fibers to yield a population of crosslinked keratin-containing fibers.

19. A crosslinking formulation produced according to the method of claim 18 .

20. A method of treating keratin-containing fibers to improve their tensile properties, said method comprising the steps of:
providing a crosslinking formulation according to claim 19 ; and
treating a population of non-crosslinked keratin-containing fibers with the crosslinking formulation so as to yield a population of crosslinked keratin-containing fibers having improved tensile properties as compared to the population of non-crosslinked keratin-containing fibers, wherein the population of non-crosslinked keratin-containing fibers comprises non-crosslinked keratin-containing fibers having protein molecules having amine groups that react with the aldehyde groups of the different oxidized sugars of the crosslinking formulation,
wherein the sugars are selected from the group consisting of monosaccharides, disaccharides, trisaccharides, and tetrasaccharides, and
wherein the improved tensile properties are selected from the group consisting of increased tensile strength and increased Young's modulus compared to the non-crosslinked keratin-containing fibers.

21. The method according to claim 1 , wherein the monosaccharides comprise 5 carbon sugars, 6 carbon sugars, or both 5 and 6 carbon sugars.

22. The method according to claim 18 , wherein the monosaccharides comprise 5 carbon sugars, 6 carbon sugars, or both 5 and 6 carbon sugars.

23. The method according to claim 20 , wherein the monosaccharides comprise 5 carbon sugars, 6 carbon sugars, or both 5 and 6 carbon sugars.

Assignees

• Univ Cornell

Inventors

• Netravali Anil N
• Patil Namrata V

Classifications

• A61Q5/04

  Preparations for permanent waving or straightening the hair · CPC title

• C08H1/06 Primary

  derived from horn, hoofs, hair, skin or leather · CPC title

• D06M2101/12

  Keratin fibres or silk · CPC title

• A61K8/60

  Sugars; Derivatives thereof · CPC title

• A61K2800/95

  Involves in-situ formation or cross-linking of polymers · CPC title