IP Library Granted Patent US 10,882,972
Granted Patent B2
US 10,882,972 · App. 15/850,871 · Granted Jan 5, 2021

Functionalized graphene oxide curable formulations

Inventors: Junhua Wei (Mountain View, CA); Gabriel Iftime (Dublin, CA); David Mathew Johnson (San Francisco, CA); Jessica Louis Baker Rivest (Palo Alto, CA)
Assignee: PALO ALTO RESEARCH CENTER INCORPORATED
C08K3/042B29C64/00B33Y70/00C01B32/198C07C69/54C07D303/24C07D493/22C08G59/50C08J5/005C08J5/18C08L33/08C08L33/10C08L63/00
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Quick Facts
Patent No.
US 10,882,972
App. No.
15/850,871
Granted
Jan 5, 2021
Kind
B2
Abstract

A method of manufacturing a cured polymer resin using functionalized graphene oxide, includes mixing functionalized graphene oxide with a resin precursor and an optional solvent to produce a functionalized graphene solution wherein the particles contain functional groups nearly identical to, or identical to, a polymer precursor material, adding a curing initiator to the resin solution and mixing to produce a resin solution, depositing the formulation into a desired shape, and curing the formulation to form a polymer having functionalized graphene oxide groups in a base polymer material. A method of producing functionalized graphene oxide includes dispersing graphene oxide into a solvent to produce dispersed graphene oxide, mixing the dispersed graphene oxide with a reactive molecule containing at least one epoxy functional group and a secondary functional group that is selected from vinyl, acrylate, methacrylate and epoxy to form a solution, adding an activation agent, heating and stirring the solution, cooling the solution, separating the particles from solution, and drying the particles to produce functionalized graphene oxide. A composition of matter includes exfoliated, functionalized graphene oxide particles, a curing initiator, a polymer precursor material, wherein the particles contain functional groups nearly identical to, or identical to, a polymer precursor material.

Claims (32)

1. A composition of matter of matter, comprising:

exfoliated, functionalized graphene oxide particles;

a curing initiator; and

a polymer precursor material;

wherein the graphene oxide particles have functional groups attached onto the graphene oxide particles, the functional groups being identical to the polymer precursor material and comprise one of either vinyl groups, acrylate, or methacrylate groups, and the polymer precursor material comprises a vinyl, acrylate, or methacrylate reactive monomer.

2. The composition of matter of claim 1 wherein the curing initiator is a thermal radical initiator.

3. The composition of matter of matter of claim 1 , wherein a concentration of functional graphene oxide in the composition of matter of matter is comprised in a range from 0.1 to 80 percent weight percent.

4. The composition of matter of matter of claim 1 , wherein a concentration of functional graphene oxide in the composition of matter of matter is higher than 20 percent weight percent.

5. The composition of matter of claim 1 , wherein the heat of curing is higher and the activation energy is lower for the composition of matter than the polymer precursor material without exfoliated, functionalized graphene oxide particles.

6. The composition of matter of claim 1 , wherein the heat of curing is higher and the activation energy is lower for the composition of matter than the polymer precursor material with unfunctionalized exfoliated graphene or with unfunctionalized exfoliated graphene oxide.

7. The composition of matter of claim 1 , wherein the composition of matter of matter with exfoliated, functionalized graphene oxide particles presents stronger shear thinning behavior when compared to a plain polymer precursor material.

8. The composition of matter of claim 1 , wherein the composition of matter of matter with exfoliated, functionalized graphene oxide particles presents stronger shear thinning behavior when compared to a polymer precursor material with unfunctionalized exfoliated graphene or with unfunctionalized exfoliated graphene oxide.

9. The composition of matter of claim 1 , wherein the composition of matter of matter, when cured, shows increasing of the modulus and of the strength when increasing the loading of the functionalized graphene oxide particles from 0.1 wt % to 25 wt %.

10. The composition of matter of claim 1 , wherein the composition of matter of matter, when cured, shows increasing of the modulus and of the strength when increasing the loading of the functionalized graphene oxide particles from 0.1 wt % to 80 wt %.

11. The composition of matter of claim 1 , wherein the exfoliated, functionalized graphene oxide particles contain 0.1 to 30 wt % functionalization groups.

12. The composition of matter of claim 1 , where thein exfoliated, functionalized graphene oxide particles contain 0.1 to 60 wt % functionalization groups.

13. A composition of matter of matter, comprising:

exfoliated, functionalized graphene oxide particles;

a curing initiator; and

a polymer precursor material comprising an epoxy material;

wherein the graphene oxide particles have functional groups comprising epoxy groups identical to the polymer precursor material directly chemically linked to the graphene oxide particles and the graphene oxide particles have a concentration of at least 10 wt %.

14. The composition of matter of matter of claim 13 , wherein the polymer precursor material comprises the epoxy material and an ionic liquid curing agent.

15. The composition of matter of matter of claim 13 , wherein the polymer precursor material comprises the epoxy material and an organic amino hardener material curing initiator.

16. The composition of matter of matter of claim 13 , wherein a concentration of functional graphene oxide in the composition has a range from 10 to 80 percent weight percent.

17. The composition of matter of claim 13 , wherein the heat of curing is higher and the activation energy is lower for the composition of matter than the polymer precursor material without exfoliated, functionalized graphene oxide particles.

18. The composition of matter of claim 13 , wherein the heat of curing is higher and the activation energy is lower for the composition of matter than the polymer precursor material with unfunctionalized exfoliated graphene or with unfunctionalized exfoliated graphene oxide.

19. The composition of matter of claim 13 , wherein the composition of matter with exfoliated, functionalized graphene oxide particles presents stronger shear thinning behavior when compared to a plain polymer precursor material.

20. The composition of matter of claim 13 , wherein the composition of matter with exfoliated, functionalized graphene oxide particles presents stronger shear thinning behavior when compared to a polymer precursor material with unfunctionalized exfoliated graphene or with unfunctionalized exfoliated graphene oxide.

21. The composition of matter of claim 13 , wherein the composition of matter, when cured, shows increasing of the modulus and of the strength when increasing the loading of the functionalized graphene oxide particles from 10 wt % to 25 wt %.

22. The composition of matter of claim 13 , wherein the composition of matter, when cured, shows increasing of the modulus and of the strength when increasing the loading of the functionalized graphene oxide particles from 10 wt % to 80 wt %.

23. The composition of matter of claim 13 , wherein the exfoliated, functionalized graphene oxide particles contain 0.1 to 30 wt % functional groups.

24. The composition of matter of claim 13 , wherein the exfoliated, functionalized graphene oxide particles contain 0.1 to 60 wt % functional groups.

Assignments (10)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 14, 2025
From: XEROX CORPORATION
To: GENESEE VALLEY INNOVATIONS, LLC
Reel/Frame 073562/0677 →
SECOND LIEN NOTES PATENT SECURITY AGREEMENT Recorded Jul 2, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 071785/0550 →
FIRST LIEN NOTES PATENT SECURITY AGREEMENT Recorded Apr 11, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 070824/0001 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT RF 064760/0389 Recorded Feb 13, 2024
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: XEROX CORPORATION
Reel/Frame 068261/0001 →
SECURITY INTEREST Recorded Feb 13, 2024
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 066741/0001 →
SECURITY INTEREST Recorded Nov 20, 2023
From: XEROX CORPORATION
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 065628/0019 →
CORRECTIVE ASSIGNMENT TO CORRECT THE REMOVAL OF US PATENTS 9356603, 10026651, 10626048 AND INCLUSION OF US PATENT 7167871 PREVIOUSLY RECORDED ON REEL 064038 FRAME 0001. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 28, 2023
From: PALO ALTO RESEARCH CENTER INCORPORATED
To: XEROX CORPORATION
Reel/Frame 064161/0001 →
SECURITY INTEREST Recorded Jun 22, 2023
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 064760/0389 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 20, 2023
From: PALO ALTO RESEARCH CENTER INCORPORATED
To: XEROX CORPORATION
Reel/Frame 064038/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 21, 2017
From: WEI, JUNHUA; IFTIME, GABRIEL; JOHNSON, DAVID MATHEW; BAKER RIVEST, JESSICA LOUIS
To: PALO ALTO RESEARCH CENTER INCORPORATED
Reel/Frame 044464/0642 →
Continuity (1)
Related Publication 20190194417A1 · Jun 27, 2019