IP Library Granted Patent US 10,899,873
Granted Patent B2
US 10,899,873 · App. 15/702,401 · Granted Jan 26, 2021

Process for preparing epoxy resins

Inventors: David Flosser (Missouri City, TX); Jerry R. Hite (Sugar Land, TX); Larry Steven Corley (Houston, TX); Bedri Erdem (Stafford, TX)
Assignee: HEXION INC.
C08G59/686C08G59/022C08G59/066C08G59/245C08G59/621
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Quick Facts
Patent No.
US 10,899,873
App. No.
15/702,401
Granted
Jan 26, 2021
Kind
B2
Abstract

An epoxy oligomerization catalyst can be employed to prepare an epoxy resin employing a method including admixing a first epoxy resin having a first epoxy equivalent weight of from about 100 to about 600 with a diphenolic compound, and a catalyst, thereby forming a second epoxy resin having a second epoxy equivalent weight of from about 200 to about 10,000; wherein the catalyst is a guanidinium catalyst. The second equivalent weight is greater than the first equivalent weight.

Claims (21)

1. A process for making an epoxy resin comprising:

admixing:

a first epoxy resin having a first epoxy equivalent weight of from about 100 to about 600,

a diphenolic compound, and

a guanidinium catalyst, wherein the guanidinium catalyst is present at a concentration of from about 0.004 to about 0.070 weight percent based upon the weight of the first epoxy resin and diphenolic compound; and

forming a second epoxy resin by reacting the admixture, to build the first epoxy equivalent weight to a higher second epoxy equivalent weight of from about 200 to about 10,000; and

wherein the guanidinium catalyst has a general formula:

wherein each R 1 -R 6 is independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, isopropyl, isobutyl, t-butyl, phenyl, and benzyl; and X is an anion selected from the group consisting of halides, alkoxides, organic acid anions, hydroxides, and combinations thereof.

2. The process of claim 1 wherein X is selected from the group consisting of chloride, bromide, iodide, fluoride, t-butoxide, n-butoxide, isobutoxide, tosylate, acetate, methoxide, ethoxide, and combinations thereof.

3. The process of claim 1 wherein the second epoxy resin has a second epoxy equivalent weight of from about 600 to about 3500.

4. The process of claim 1 wherein R 1 -R 6 are the same and are ethyl groups.

5. The process of claim 1 wherein R 1 -R 6 are the same and are n-butyl groups.

6. The process of claim 1 , wherein the guanidinium catalyst is present at a concentration of from about 0.025 to about 0.050 weight percent based upon the weight of the first epoxy resin and diphenolic compound.

7. The process of claim 1 additionally comprising employing an optional solvent with the first epoxy resin, diphenolic compound, or both.

8. The process of claim 7 wherein the solvent is selected from the group consisting of methyl ethyl ketone, methyl isobutyl ketone, and combinations thereof.

9. The process of claim 1 wherein the diphenolic compound comprises Bisphenol A.

10. The process of claim 1 wherein the diphenolic compound comprises Bisphenol A, and the second epoxy resin has less than 40 parts per million (PPM) of residual free Bisphenol A.

11. An epoxy resin prepared by the method of claim 1 having an epoxy equivalent weight of from about 200 to about 10,000.

12. An article of manufacture prepared from a composition comprising the epoxy resin of claim 11 .

13. The article of manufacture of claim 12 wherein the article of manufacture is a composite.

14. The article of manufacture of claim 12 wherein the article of manufacture is a paint, coating, or adhesive.

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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 6, 2018
From: FLOSSER, DAVID; HITE, JERRY; CORLEY, LARRY STEVEN; ERDEM, BEDRI
To: HEXION INC.
Reel/Frame 044846/0243 →
SECURITY INTEREST Recorded Feb 2, 2018
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 044814/0825 →
SECURITY INTEREST Recorded Feb 2, 2018
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 044814/0920 →
SECURITY INTEREST Recorded Feb 2, 2018
From: HEXION INC.
To: WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT
Reel/Frame 044814/0971 →
SECURITY INTEREST Recorded Oct 19, 2017
From: HEXION INC.
To: WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT
Reel/Frame 043905/0399 →
Continuity (1)
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