IP Library Granted Patent US 11,377,519
Granted Patent B1
US 11,377,519 · App. 16/404,979 · Granted Jul 5, 2022

High glass transition temperature epoxy formulations for cryogenic applications

Inventors: Wenhong Fan (Cupertino, CA); Ryan Christopher Kennett (Manhattan Beach, CA); Joshua James Conlon (Redondo Beach, CA)
Assignee: Space Exploration Technologies Corp.
C08G59/245C08G59/504C08G59/5006C08G59/5026C08J5/24C08K5/1515C08L63/00F17C1/16C08J2363/02C08L2205/16F17C2201/0109F17C2203/0604F17C2203/0619F17C2203/0636F17C2203/0673F17C2221/014F17C2223/0161F17C2270/0168
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Quick Facts
Patent No.
US 11,377,519
App. No.
16/404,979
Granted
Jul 5, 2022
Kind
B1
Abstract

A method of increasing the glass transition point of a cured epoxy comprising a bisphenol A diglycidyl ether and a polyetheramine includes the step of including 1,8-diamino-p-menthane as an additional hardener for curing the epoxy. An epoxy formulation includes bisphenol A diglycidyl ether and a hardener including a polyetheramine and 1,8-diamino-p-menthane.

Claims (28)

1. A method of increasing the glass transition point of a cured epoxy comprising a glycidyl ether resin and a polyetheramine, the method comprising:

including 1,8-diamino-p-menthane as an additional hardener for curing the epoxy,

wherein a ratio of polyetheramine to 1,8-diamino-p-menthane is 1:2.5±15% by weight.

2. The method of claim 1 , wherein the ratio of polyetheramine to 1,8-diamino-p-menthane is 1:2.5±10% by weight.

3. The method of claim 1 , wherein the glass transition point is at least 280° F.

4. An uncured epoxy formulation, comprising:

a glycidyl ether resin; and

a hardener including a polyetheramine and 1,8-diamino-p-menthane,

wherein a ratio of the polyetheramine to 1,8-diamino-p-menthane is 1:2.5±15% by weight.

5. The uncured epoxy formulation of claim 4 , wherein the glycidyl ether resin is 2,2-bis[p-(2,3-epoxypropoxy)phenyl]propane.

6. The uncured epoxy formulation of claim 4 , wherein the ratio of the polyetheramine to 1,8-diamino-p-menthane is 1:2.5±10% by weight.

7. The uncured epoxy formulation of claim 4 , wherein a ratio of the glycidyl ether resin to hardener is 100:28±10% by weight.

8. The uncured epoxy formulation of claim 4 , having a viscosity greater than 3,000 cps.

9. The uncured epoxy formulation of claim 4 , having a gel life of at least 24 hours at ambient temperature (about 73° F.) and a gel life of at least 10 hours at 120° F.

10. The uncured epoxy formulation of claim 4 , further comprising an additive.

11. The uncured epoxy formulation of claim 10 , wherein the additive is propoxylated glycerin triglycidyl ether or brominated bisphenol A diglycidyl ether.

12. The uncured epoxy formulation of claim 4 , wherein the glycidyl ether resin and the hardener of the polyetheramine and 1,8-diamino-p-menthane account for about 100% by weight of the uncured epoxy formulation.

13. A cured epoxy formulation, comprising:

the cured product of a glycidyl ether resin, and a hardener of a polyetheramine and 1,8-diamino-p-menthane, wherein a ratio of the polyetheramine to 1,8-diamino-p-menthane is 1:2.5±15% by weight.

14. The cured epoxy formulation of claim 13 , having a glass transition point at about 280° F. or greater.

15. The cured epoxy formulation of claim 13 , comprising a density of 1.14 g/cm3.

16. The cured epoxy formulation of claim 13 , comprising a hardness of 82 shore D.

17. The cured epoxy formulation of claim 13 , comprising a tensile strength of about 22.6+/−2.6 ksi at −320° F.

18. The cured epoxy formulation of claim 13 , comprising a tensile elongation of about 2.6+/−0.5% at −320° F.

19. The cured epoxy formulation of claim 13 , further comprising fibers selected from the group consisting of carbon, glass, aromatic polyamide, and a combination thereof.

20. A composite overwrapped pressure vessel, comprising:

a metal liner overwrapped with fibers impregnated with the cured product of a glycidyl ether resin; and a hardener of a polyetheramine and 1,8-diamino-p-menthane, wherein a ratio of the polyetheramine to 1,8-diamino-p-menthane is 1:2.5±15% by weight.

21. The composite overwrapped pressure vessel of claim 20 , having a burst pressure of at least 8,000 psi.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Feb 14, 2025
From: BANK OF AMERICA, N.A.
To: SPACE EXPLORATION TECHNOLOGIES CORP.
Reel/Frame 070237/0157 →
CERTIFICATE OF CONVERSION (STATE OF DELAWARE TO STATE OF TEXAS; NEW FILE NO.: 805421124 ; FILED: 02-14-2024) Recorded Feb 12, 2025
From: SPACE EXPLORATION TECHNOLOGIES CORP.
To: SPACE EXPLORATION TECHNOLOGIES CORP.
Reel/Frame 070203/0322 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2020
From: FAN, WENHONG; KENNETT, RYAN CHRISTOPHER; CONLON, JOSHUA JAMES
To: SPACE EXPLORATION TECHNOLOGIES CORP.
Reel/Frame 051900/0926 →
SECURITY AGREEMENT Recorded Feb 18, 2020
From: SPACE EXPLORATION TECHNOLOGIES CORP.
To: BANK OF AMERICA, N.A.
Reel/Frame 051952/0699 →
Continuity (1)
Provisional Application 62674220 · May 21, 2018