IP Library Granted Patent US 11,359,047
Granted Patent B2
US 11,359,047 · App. 16/126,612 · Granted Jun 14, 2022

Epoxy resin systems

Inventors: Amitabh Bansal (Sugar Land, TX); Larry Steven Corley (Houston, TX); Diana Sepulveda-Camarena (Sugar Land, TX); Jennifer W. Chung (Katy, TX); Leeanne Taylor (Columbus, OH); Alla Hale (South San Francisco, CA)
Assignee: HEXION INC.
C08G59/36C08G59/3245C08G59/4071C08G59/5073C08G59/56C08G59/686
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,359,047
App. No.
16/126,612
Granted
Jun 14, 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 an epoxy resin blend comprising an epoxy resin, a first curing agent selected from the group of a polyarylene alkylphosphonate, a polyarylene arylphosphonate, and combinations thereof, and a second curing agent.

Claims (25)

1. An epoxy resin system, consisting essentially of:

an epoxy resin blend consisting essentially of:

a liquid epoxy resin based on aromatic compounds selected from the group consisting of bisphenol F, bisphenol A, 1,1-bis(4-hydroxyphenyl)ethane, 1,1-dichloro-2,2-bis(4-hydroxyphenyl)ethene, phenolic novolacs, phenolic resoles, and combinations thereof;

a first curing agent consisting essentially of:

a polyarylene alkylphosphonate; and

a polyarylene arylphosphonate;

an optional monofunctional epoxy additive; and

an optional additive selected from the group consisting of an additive phosphorus compound, a diluent, and combinations thereof; and

a second curing agent selected from the group consisting of a compound having an imidazole group, a compound having a fused imidazole ring, and combinations thereof.

2. The epoxy resin system of claim 1 , wherein the polyarylene alkylphosphonate or polyarylene arylphosphonate is selected from the group of poly-(m-phenylene methylphosphonate), poly-(m-phenylene phenylphosphonate), and combinations thereof.

3. The epoxy resin system of claim 1 , wherein, if present, the additive phosphorus compound is selected from the group consisting of a non-polyarylene phosphonate, a phosphazene, an alkyl phosphate, an aryl phosphate, an alkyl phosphite, an aryl phosphite, and combinations thereof.

4. The epoxy resin system of claim 3 , wherein the additive phosphorus compound is selected from the group of dimethyl methylphosphonate, diethyl ethylphosphonate, P,P′,P″,P,P′,P″-hexamethoxyphosphazene, P,P′,P″,P,P′,P″-hexaphenoxyphosphazene, dimethyl phosphite, diethyl N,N-bis (2-hydroxyethyl) aminomethylphosphonate, tributyl phosphate, triphenyl phosphate, diphenyl methylphosphonate, diphenyl phenylphosphonate, resorcinol bis(diphenyl phosphate), t-butylated triphenyl phosphate, bisphenol A bis(diphenyl phosphate), bisphenol F bis(diphenyl phosphate), and combinations thereof.

5. The epoxy resin system of claim 1 , wherein the total phosphorus content is greater than 4 wt. % of the epoxy resin system/epoxy resin blend.

6. The epoxy resin system of claim 1 , wherein, if present, the diluent is selected from the group consisting of monoglycidyl ethers of alcohols, polyglycidyl ethers of non-aromatic glycols or triols or polyols, polyglycols, glycidyl esters, and combinations thereof.

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

8. The epoxy resin system of claim 1 , wherein the compound having a fused imidazole ring is selected from the group consisting of benzimidazole, toluimidazole, and combinations thereof.

9. The epoxy resin system of claim 1 , wherein the epoxy resin blend consists essentially of:

from about 40 wt. % to about 85 wt. % of the epoxy resin;

from about 15 wt. % to about 60 wt. % of the first curing agent comprising polyarylene alkylphosphonate and a polyarylene arylphosphonate;

from about 0 wt. % to about 30 wt. % of an additive phosphorus compound; and

from about 0 wt. % to about 20 wt. % of a diluent, wherein the total of all components are 100 wt. % of the epoxy resin blend.

10. The epoxy resin system of claim 1 , wherein the epoxy resin system consists essentially of:

from about 60 wt. % to about 99.8 wt. % of the epoxy resin blend; and

from about 0.2 wt. % to about 40 wt. % of the second curing agent.

11. The epoxy resin system of claim 1 , wherein the epoxy resin system is free of fillers.

Assignments (9)
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 (TERM LOAN) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049741/0425 →
PATENT SECURITY INTEREST (ABL) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049740/0770 →
SECURITY INTEREST Recorded Feb 1, 2019
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 048216/0628 →
SECURITY INTEREST Recorded Feb 1, 2019
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 048216/0683 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 26, 2018
From: BANSAL, AMITABH; CORLEY, LARRY STEVEN; SEPULVEDA-CAMARENA, DIANA; CHUNG, JENNIFER W.; TAYLOR, LEEANNE; HALE, ALLA
To: HEXION INC.
Reel/Frame 047584/0127 →
SECURITY INTEREST Recorded Oct 15, 2018
From: HEXION INC.
To: WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT
Reel/Frame 047163/0364 →
Continuity (2)
Provisional Application 62558182 · Sep 13, 2017
Related Publication 20190077905A1 · Mar 14, 2019