Methods and formulations for crosslinking hair or other keratin fibers using oxidized sugars as crosslinking agents

Patent metadata

Field	Value
Publication number	US-12364658-B2
Application number	US-202017763174-A
Country	US
Kind code	B2
Filing date	Sep 28, 2020
Priority date	Sep 26, 2019
Publication date	Jul 22, 2025
Grant date	Jul 22, 2025

Abstract

Disclosed is a method of crosslinking hair or other keratin fibers by (i) providing a crosslinking agent comprising an oxidized sugar having at least two aldehyde groups; and (ii) infiltrating a plurality of non-crosslinked hair or other keratin fibers with the crosslinking agent under conditions effective to cause protein molecules contained in the non-crosslinked hair or other keratin fibers to become crosslinked, thereby yielding a population of crosslinked hair or other keratin fibers. The protein molecules include amine groups that react with the aldehyde groups of the oxidized sugar to yield the crosslinked hair or other keratin fibers. Also disclosed are formulations for crosslinking hair or other keratin fibers and methods of using the formulations to treat human hair to maintain a desired three dimensional structure. This formulation includes a crosslinking agent having a plurality of oxidized sugars having at least two aldehyde groups or mixture thereof.

First claim

What is claimed is:

1. A method of crosslinking hair or other keratin fibers, said method comprising:
providing a crosslinking agent comprising an oxidized sugar having at least two aldehyde groups; and
infiltrating a plurality of non-crosslinked hair or other keratin fibers with the crosslinking agent under conditions effective to cause protein molecules contained in the non-crosslinked hair or other keratin fibers to become crosslinked, thereby yielding a population of crosslinked hair or other keratin fibers,
wherein the protein molecules of the non-crosslinked hair or other keratin fibers comprise amine groups that react with the aldehyde groups of the oxidized sugar to achieve the crosslinking of the protein molecules to yield the crosslinked hair or other keratin fibers, and
wherein at least 50% of the sugar rings are opened in the oxidized sugar.

2. The method according to claim 1 , wherein the hair or other keratin fibers comprise human hair, animal fibers, or a mixture thereof.

3. The method according to claim 2 , wherein the human hair is selected from the group consisting of straight hair, wavy hair, and curly hair, or variations thereof, or wherein the animal fibers are selected from the group consisting of wool, alpaca, angora, fur, cashmere, mohair, dog fur, and qiviut.

4. The method according to claim 2 , wherein the animal fibers are from animals selected from the group consisting of sheep, vicuna, alpaca, llama, muskox, goats, bison, camel, yak, horse, chinchilla, dog, and rabbit.

5. The method according to claim 2 , wherein the animal fibers have a form selected from the group consisting of raw fibers, yarns, felts, and woven or knitted fabrics.

6. The method according to claim 1 , wherein the sugar is selected from the group consisting of monosaccharides, disaccharides, trisaccharides, tetrasaccharides, and oligosaccharides, or mixtures thereof.

7. The method according to claim 1 , wherein the sugar is selected from the group consisting of galactose, sucrose, maltose, lactose, raffinose, and stachyose.

8. The method according to claim 1 , wherein the crosslinking agent is prepared according to a method comprising:
providing a mixture of non-oxidized sugar molecules; and
reacting the non-oxidized sugar molecules with a benign oxidizing agent to cause oxidation of the non-oxidized sugar molecules to yield a reaction mixture comprising oxidized sugar molecules having at least two aldehyde groups, said oxidized sugar molecules corresponding to the crosslinking agent.

9. The method according to claim 8 , wherein the benign oxidizing agent is sodium periodate (NaIO 4 ).

10. The method according to claim 1 , wherein the crosslinking agent primarily alters the amine groups of the keratin protein molecules, thereby leaving other groups of the keratin protein molecules unaltered.

11. The method according to claim 1 , wherein pairs of adjacent aldehyde groups in the oxidized sugar are directly linked by —CR 1 R 2 —O—CR 3 R 4 — or —CR 1 R 2 —O—CR 3 R 4 —CR 5 R 6 —, wherein R 1 , R 2 , R 3 , R 4 , R 5 or R 6 is selected from H, —CH 2 OH, C 1 -C 3 alkyl group, or a moiety of an oxidize sugar comprising aldehyde groups.

12. The method according to claim 1 , wherein pairs of adjacent aldehyde groups in the oxidized sugar have an average distance between two adjacent aldehyde groups of no more than the distance of —CR 1 R 2 —O—CR 3 R 4 — or —CR 1 R 2 —O—CR 3 R 4 —CR 5 R 6 —, wherein R 1 , R 2 , R 3 , R 4 , R 5 or R 6 is selected from H or —CH 2 OH.

13. The method according to claim 1 , wherein the oxidized sugar comprises over 1.5 aldehyde groups per sugar unit on average.

14. The method according to claim 1 , wherein the oxidized sugar comprises less than 0.2 carboxyl group per sugar unit on average.

15. The method according to claim 1 , wherein the oxidized sugar has 2-10 sugar units.

16. The method according to claim 1 , wherein the crosslinking is carried out at neutral pH.

17. The method according to claim 1 , wherein the oxidized sugar crosslinks the hair or keratin fibers through the reaction between the aldehyde groups of the oxidized sugar and the amine groups of the keratin in hair fibers to form crosslinks, and wherein each oxidized sugar forms at least four covalent bonds linked to one or more molecules within hair or keratin fibers.

18. The method according to claim 1 , wherein the hair or keratin fibers are reshaped without breaking the disulfide covalent bonds in hair or keratin fibers.

19. The method according to claim 1 , wherein the oxidized sugar has a structure of

wherein:
L is selected from —O—, —CR 1 R 2 —, —CR 1 R 2 —O—, —O—CR 1 R 2 —, —CR 1 R 2 —O—CR 3 R 4 —, or any combination thereof,
n is selected from any number in a range of 1 to 20, and
R 0 , R 1 , R 2 , R 3 or R 4 is selected from H, —OH, —CH 2 OH, or a C1-C3 alkyl group, and

wherein:
R 0 is different or identical in the n

units,
L is different or identical in the n

units, and
R 1 , R 2 , R 3 or R 4 is different or identical in the n

units, respectively.

20. A method of treating human hair to maintain a desired three dimensional structure, said method comprising:
providing a formulation for crosslinking hair or other keratin fibers, said formulation comprising:
a crosslinking agent comprising a plurality of oxidized sugars having at least two aldehyde groups or mixture thereof,
wherein said crosslinking agent is formulated so that the aldehyde groups of the oxidized sugars are effective to react with amine groups of protein molecules contained in a plurality of non-crosslinked hair or other keratin fibers to yield a population of crosslinked hair or other keratin fibers; and

treating a population of human hair with the formulation so as to maintain the desired three dimensional (3D) structure of the population of human hair, wherein the human hair comprises non-crosslinked protein fibers having protein molecules having amine groups that react with the aldehyde groups of the oxidized sugar of the formulation, and wherein at least 50% of the sugar rings are opened in the oxidized sugar.

21. The method according to claim 20 , wherein the formulation is in a form of a paste or an aqueous solution.

22. A method of crosslinking hair or other keratin fibers, said method comprising:
providing a crosslinking agent comprising an oxidized sugar having at least two aldehyde groups; and
infiltrating a plurality of non-crosslinked hair or other keratin fibers with the crosslinking agent under conditions effective to cause protein molecules contained in the non-crosslinked hair or other keratin fibers to become crosslinked, thereby yielding a population of crosslinked hair or other keratin fibers,
wherein the protein molecules of the non-crosslinked hair or other keratin fibers comprise amine groups that react with the aldehyde groups of the oxidized sugar to achieve the crosslinking of the protein molecules to yield the crosslinked hair or ot

Assignees

• Univ Cornell

Inventors

• Netravali Anil N
• Patil Namrata V

Classifications

• A61Q5/06

  Preparations for styling the hair, e.g. by temporary shaping or colouring · CPC title

• A61Q5/04

  Preparations for permanent waving or straightening the hair · CPC title

• A61K8/04

  Dispersions; Emulsions · CPC title

• A45D7/06

  combined chemical and thermal · CPC title

• D06M2101/12

  Keratin fibres or silk · CPC title