IP Library Granted Patent US 11,292,871
Granted Patent B2
US 11,292,871 · App. 16/000,277 · Granted Apr 5, 2022

Epoxy resin systems for composites

Inventors: Larry Steven Corley (Houston, TX); Wilbur Paul Ubrich (Katy, TX); Jennifer W. Chung (Katy, TX); Amitabh Bansal (Sugar Land, TX); Terry Loy (San Clemente, CA)
Assignee: HEXION INC.
C08G59/1466B29C70/42B29C70/52B29C70/54C08G59/02C08G59/686C08J5/04C08L63/00B29K2063/00B29K2105/0809B29L2031/085C08J2363/00C08J2433/06C08J2471/02F03D1/0675F05B2230/20F05B2240/2211F05B2280/4003
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Quick Facts
Patent No.
US 11,292,871
App. No.
16/000,277
Granted
Apr 5, 2022
Kind
B2
Abstract

Compositions and methods for forming epoxy resin systems are provided. In one embodiment, a composition is provided for an epoxy resin system including a liquid epoxy resin component including a liquid epoxy resin and an acrylate monomer, a curing agent component including a compound having an imidazole group and, optionally, a co-curing agent for the compound having an imidazole group comprising a phenolic monomer compound, a branched chain carboxylic acid, and combinations thereof, and a non-aromatic polyol compound. The composition may be used to form composites, such as used in commercial wind turbine blade manufacturing.

Claims (30)

1. An epoxy resin system, the epoxy resin system consisting essentially of:

a liquid epoxy resin component comprising:

a liquid epoxy resin; and

an acrylate monomer;

a curing agent component consisting essentially of:

a compound having an imidazole group; and

optionally, a co-curing agent for the compound having the imidazole group comprising a phenolic monomer compound, a branched chain carboxylic acid, or a combination thereof; and

a non-aromatic polyol compound, wherein the epoxy resin system is free of a radical initiator, wherein the non-aromatic polyol compound optionally comprises part of the epoxy resin component, optionally comprises part of the curing agent component, optionally comprises part of the epoxy resin system with the liquid epoxy resin component and the curing agent component, or a combination thereof.

2. The epoxy resin system of claim 1 , wherein the liquid epoxy resin component comprises an aromatic or a non-aromatic epoxy resin based on bisphenol A, bisphenol F, phenolic novolacs, hydrogenated bisphenol A, non-aromatic diols, or a combination thereof.

3. The epoxy resin system of claim 1 , wherein the liquid epoxy resin component comprises:

from 50 to 99 parts of liquid epoxy resin; and

from 1 to 50 parts of the acrylate ester of a mono-ol or polyol, the methacrylate ester of a mono-ol or polyol, or a combination thereof.

4. The epoxy resin system of claim 1 , wherein the acrylate monomer comprises an acrylate ester of a mono-ol or polyol, the methacrylate ester of a mono-ol or polyol, or a combination thereof.

5. The epoxy resin system of claim 1 , wherein the compound having an imidazole group is a compound selected from the group consisting of imidazole, 1-methylimidazole, 2-methylimidazole, 2-propylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, benzimidazole, toluimidazole, and combinations thereof.

6. The epoxy resin system of claim 1 , wherein the compound having an imidazole group is present in the amount of 1 to 15 parts based on a total of 100 parts of the liquid epoxy resin component.

7. The epoxy resin system of claim 1 , wherein the non-aromatic polyol compound comprises a number average molecular weight between about 1000 and 10000.

8. The epoxy resin system of claim 1 , wherein the non-aromatic polyol compound comprises a glycol selected from the group consisting of poly(ethylene oxide) glycol, poly(propylene oxide) glycol, poly(butylene oxide) glycol, polytetrahydrofuran glycols, poly(ethylene adipate) glycol, poly(propylene sebacate) glycol, poly(hexamethylene carbonate) glycol, silicone-alkylene oxide copolymer, poly(butadiene-co-acrylonitrile) glycol, and combinations thereof.

9. The epoxy resin system of claim 1 , wherein, if present, the phenolic monomer compound is selected from the group consisting of benzenediols, bisphenols, and combinations thereof.

10. The epoxy resin system of claim 1 , wherein, if present, the branched chain carboxylic acid has 5-40 carbon atoms.

11. The epoxy resin system of claim 1 , wherein the epoxy resin system is free of anhydride compounds, wherein the epoxy resin system is free of a core-shell rubber, or a combination thereof.

12. A composite prepared using the epoxy resin system of claim 1 .

13. The composite of claim 12 , wherein the composite is in the form of a windmill blade component.

14. A method for manufacturing a composite, comprising:

providing a reinforcing fiber substrate;

mixing the epoxy resin system of claim 1 ;

contacting the reinforcing fiber substrate with the epoxy resin system; and

curing the epoxy resin system to form the composite.

15. The method of claim 14 , wherein contacting the reinforcing fiber substrate with the epoxy resin system comprises a pultrusion process.

16. The method of claim 14 , wherein the non-aromatic polyol compound is provided with the liquid epoxy resin component, the curing agent component, or both.

17. The method of claim 14 , wherein the epoxy resin system is free of anhydride compounds, wherein the epoxy resin system is free of a core-shell rubber, or a combination thereof.

Assignments (10)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 17, 2022
From: HEXION INC.
To: WESTLAKE EPOXY INC.
Reel/Frame 061611/0876 →
PARTIAL TERMINATION AND RELEASE OF SECURITY INTEREST IN SPECIFIED PATENTS (ABL) Recorded Feb 1, 2022
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 058932/0915 →
PARTIAL TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS (TERM LOAN) Recorded Feb 1, 2022
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 058932/0923 →
PATENT SECURITY INTEREST (ABL) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049740/0770 →
PATENT SECURITY INTEREST (TERM LOAN) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049741/0425 →
SECURITY INTEREST Recorded Feb 1, 2019
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 048216/0683 →
SECURITY INTEREST Recorded Feb 1, 2019
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 048216/0628 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 24, 2018
From: CORLEY, LARRY STEVEN; UBRICH, WILBUR PAUL; CHUNG, JENNIFER W.; BANSAL, AMITABH
To: HEXION INC.
Reel/Frame 046700/0089 →
EMPLOYMENT AGREEMENT WITH OBLIGATION TO ASSIGN INVENTIONS Recorded Aug 24, 2018
From: LOY, TERRY
To: HEXION INC.
Reel/Frame 046937/0383 →
SECURITY INTEREST Recorded Jul 18, 2018
From: HEXION INC.
To: WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT
Reel/Frame 046380/0855 →
Continuity (2)
Provisional Application 62517499 · Jun 9, 2017
Related Publication 20180355096A1 · Dec 13, 2018