Crosslinked thermoset resins and methods thereof

Patent metadata

Field	Value
Publication number	US-10179807-B2
Application number	US-201314650206-A
Country	US
Kind code	B2
Filing date	Dec 9, 2013
Priority date	Dec 7, 2012
Publication date	Jan 15, 2019
Grant date	Jan 15, 2019

Abstract

The present invention relates to a method of making a crosslinked thermoset resin. One embodiment of this method comprises: (i) separating a plant-derived flour mixture into a protein fraction comprising proteins and a carbohydrate fraction comprising carbohydrates; (ii) subjecting the carbohydrate fraction to an oxidizing agent to yield oxidized carbohydrates comprising aldehyde functional groups or both aldehyde functional groups and carboxyl functional groups; and (iii) reacting the oxidized carbohydrates with the protein fraction under conditions effective to crosslink the proteins, thereby yielding a crosslinked thermoset resin. The present invention also relates to a crosslinked thermoset resin and composites, nanofiber membranes, and adhesives comprising the crosslinked thermoset resin.

First claim

What is claimed is:

1. A method of making a crosslinked thermoset resin from soy flour, said method comprising:
separating a plant-derived flour mixture into a protein fraction comprising proteins and a carbohydrate fraction comprising carbohydrates, thereby causing said protein fraction and said carbohydrate fraction to become isolated from one another, wherein said plant-derived flour mixture is soy flour;
subjecting said carbohydrate fraction to an oxidizing agent to yield oxidized carbohydrates comprising aldehyde functional groups or both aldehyde functional groups and carboxyl functional groups, thereby causing said oxidized carbohydrates to be effective as a crosslinking agent for said protein fraction; and
reacting said oxidized carbohydrates produced from the subjecting step directly with said protein fraction produced from the separating step under conditions effective to cause said oxidized carbohydrates to act as a crosslinking agent for said protein fraction so as to crosslink the proteins, thereby yielding a crosslinked thermoset resin.

2. The method according to claim 1 , wherein the step of reacting the oxidized carbohydrates directly with the protein fraction comprises:
denaturing the proteins of the protein fraction to expose reactive functional groups on the denatured proteins; and
directly contacting the oxidized carbohydrates with the functional groups of the denatured proteins to crosslink the proteins.

3. The method according to claim 1 , wherein said carbohydrates comprise soluble carbohydrates comprising a sugar selected from the group consisting of glucose, fructose, sucrose, raffinose, maltose, galactose, stachyose, and mixtures thereof.

4. The method according to claim 1 further comprising:
electrospinning a composition comprising the crosslinked thermoset resin into a nanofiber, a nanofiber membrane, or a composite.

5. The method according to claim 1 , wherein the oxidizing agent is selected from the group consisting of CrO 3 , KMnO 4 , HNO 3 , and HIO 6 .

6. The method according to claim 1 , wherein the oxidizing agent is a benign or non-toxic oxidizing agent.

7. The method according to claim 6 , wherein the benign or non-toxic oxidizing agent is hydrogen peroxide.

8. The method according to claim 7 , wherein the hydrogen peroxide is acidified.

9. The method according to claim 1 , wherein the step of separating the plant-derived flour mixture into the protein fraction and the carbohydrate fraction comprises performing either a water-based separation procedure or a solvent-based separation procedure.

10. The method according to claim 9 , wherein the water-based separation procedure comprises an isoelectric filtration process whereby the proteins are rendered insoluble at their isoelectric point in water while the carbohydrates remain soluble in water.

11. A method of making a crosslinked thermoset resin from a grain having carbohydrates in the form of sugars rather than starch, said method comprising:
separating a plant-derived flour mixture into a protein fraction comprising proteins and a carbohydrate fraction comprising carbohydrates, thereby causing said protein fraction and said carbohydrate fraction to become isolated from one another, wherein said plant-derived flour mixture is a flour from a grain having carbohydrates in the form of sugars rather than starch, and wherein said grain is not corn;
subjecting said carbohydrate fraction to an oxidizing agent to yield oxidized carbohydrates comprising aldehyde functional groups or both aldehyde functional groups and carboxyl functional groups, thereby causing said oxidized carbohydrates to be effective as a crosslinking agent for said protein fraction; and
reacting said oxidized carbohydrates produced from the subjecting step directly with said protein fraction produced from the separating step under conditions effective to cause said oxidized carbohydrates to act as a crosslinking agent for said protein fraction so as to crosslink the proteins, thereby yielding a crosslinked thermoset resin.

12. The method according to claim 11 , wherein the step of reacting the oxidized carbohydrates directly with the protein fraction comprises:
denaturing the proteins of the protein fraction to expose reactive functional groups on the denatured proteins; and
directly contacting the oxidized carbohydrates with the functional groups of the denatured proteins to crosslink the proteins.

13. The method according to claim 11 , wherein said carbohydrates comprise soluble carbohydrates comprising a sugar selected from the group consisting of glucose, fructose, sucrose, raffinose, maltose, galactose, stachyose, and mixtures thereof.

14. The method according to claim 11 further comprising:
electrospinning a composition comprising the crosslinked thermoset resin into a nanofiber, a nanofiber membrane, or a composite.

15. The method according to claim 11 , wherein the oxidizing agent is selected from the group consisting of CrO 3 , KMnO 4 , HNO 3 , and HIO 6 .

16. The method according to claim 11 , wherein the oxidizing agent is a benign or non-toxic oxidizing agent.

17. The method according to claim 16 , wherein the benign or non-toxic oxidizing agent is hydrogen peroxide.

18. The method according to claim 17 , wherein the hydrogen peroxide is acidified.

19. The method according to claim 11 , wherein the step of separating the plant-derived flour mixture into the protein fraction and the carbohydrate fraction comprises performing either a water-based separation procedure or a solvent-based separation procedure.

20. The method according to claim 19 , wherein the water-based separation procedure comprises an isoelectric filtration process whereby the proteins are rendered insoluble at their isoelectric point in water while the carbohydrates remain soluble in water.

Assignees

• Univ Cornell

Inventors

• Netravali Anil N
• Ghosh Dastidar Trina

Classifications

• C08J5/00

  Manufacture of articles or shaped materials containing macromolecular substances (manufacture of semi-permeable membranes B01D67/00 - B01D71/00) · CPC title

• C08H1/02

  Protein-aldehyde condensates · CPC title

• C08J5/24

  Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs · CPC title

• C08J5/04

  Reinforcing macromolecular compounds with loose or coherent fibrous material · CPC title

• C08L89/00

  Compositions of proteins; Compositions of derivatives thereof (foodstuff preparations A23J3/00) · CPC title