IP Library Granted Patent US 12,240,999
Granted Patent B2
US 12,240,999 · App. 17/985,445 · Granted Mar 4, 2025

BHM in adhesive compositions

Inventors: Zheng Chai (Houston, TX); Jefferson Thomas Ebert (Houston, TX)
Assignee: Ascend Performance Materials Operations LLC
C09J163/00C08G59/5013C09J11/04C09J11/06C09J2301/312C09J2301/408C09J2301/50
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Quick Facts
Patent No.
US 12,240,999
App. No.
17/985,445
Granted
Mar 4, 2025
Kind
B2
Abstract

An adhesive composition comprising a first part comprising an epoxy resin and a second part comprising a multifunctional amine package. The multifunctional amine package comprises bis(hexamethylene)triamine and a synergist. The amine concentration is at least 10% less than the epoxy resin concentration and the adhesive composition demonstrates a sag resistance of greater than 40 mm.

Claims (31)

1. An adhesive composition comprising:

a first part comprising an epoxy resin; and

a second part comprising a multifunctional amine package comprising:

bis(hexamethylene)triamine; and

a synergist;

wherein, in the adhesive composition, the amine concentration is at least 10% less than the epoxy resin concentration, and

wherein the adhesive composition demonstrates a sag resistance ranging from 10 mm to 300 mm; and

wherein, when cured, the cured composition demonstrates a Koenig hardness from 2 to 70, with a Koenig Hardness (1 day) from 2 to 20.

2. The composition of claim 1 , wherein the synergist comprises acetonitrile, caprolactam, aminohexanol, aminocephalosporanic acid, aminocapronitrile, or adiponitrile, or combinations thereof.

3. The composition of claim 1 , wherein the adhesive composition comprises less than 35 wt % cyclic amines, based on the total amine content.

4. The composition of claim 1 , wherein the adhesive composition comprises a solvent, and wherein the solvent to bis(hexamethylene) triamine weight ratio ranges from 0.1 to 4.0.

5. The composition of claim 1 , wherein the first part and the second part each has a volume, and wherein the volume ratio of the first part to the second part ranges from 0.2 to 5.

6. The composition of claim 1 , wherein the adhesive composition, when mixed, has a Brookfield viscosity from 100 to 2000 cps.

7. The composition of claim 1 , wherein the adhesive composition further comprises a solvent, a rheology modifier, or combinations thereof.

8. The composition of claim 1 , wherein the adhesive composition comprises from 40 wt % to 90 wt % epoxy resin, based on the total weight of the adhesive composition.

9. The composition of claim 1 , wherein the adhesive composition comprises from 1 wt % to 35 wt % bis(hexamethylene) triamine, based on the total weight of the adhesive composition.

10. The composition of claim 1 , wherein the adhesive composition comprises from 1 wt % to 50 wt % of a phenol solvent based on the total weight of the adhesive composition.

11. The composition of claim 10 , wherein the phenol comprises a nonyl phenol.

12. The composition of claim 1 , wherein the adhesive composition comprises from 0.1 wt % to 20 wt % of a silica rheology modifier based on the total weight of the adhesive composition.

13. The composition of claim 1 , wherein the second part is not a solid.

14. The composition of claim 1 , wherein the adhesive composition has a hydrogen active equivalent weight less than 65.

15. The composition of claim 1 , wherein the adhesive composition demonstrates a cross hatch adhesion score of at least 2B, as measured via ASTM D3359 method B.

16. The composition of claim 1 , wherein the adhesive composition demonstrates a gel time greater than 10 minutes.

17. The composition of claim 1 , wherein the adhesive composition, when cured, demonstrates yellowing index greater than 1.

18. A process for making an adhesive composition, comprising:

dissolving in a solvent a multifunctional amine package comprising bis(hexamethylene) triamine and a synergist to form a second part;

contacting the second part with a first part comprising an epoxy resin to form the adhesive composition; and

wherein, when cured, the cured composition demonstrates a Koenig hardness from 2 to 70, with a Koenig Hardness (1 day) from 2 to 20.

19. The process of claim 18 , further comprising adding a rheology modifier to the second part, such that the second part has a viscosity less than 1500 cps.

20. The process of claim 18 , wherein the adhesive composition has a viscosity from 100 to 2000 cps.

21. The process of claim 18 , wherein the synergist comprises acetonitrile, caprolactam, aminohexanol, aminocephalosporanic acid, aminocapronitrile, or adiponitrile, or combinations thereof.

Assignments (7)
RELEASE OF SECURITY INTEREST Recorded Dec 23, 2025
From: WILMINGTON SAVINGS FUND SOCIETY, FSB
To: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
Reel/Frame 074050/0090 →
SECURITY INTEREST Recorded Dec 23, 2025
From: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
To: WILMINGTON SAVINGS FUND SOCIETY, FSB
Reel/Frame 074056/0183 →
SECURITY INTEREST Recorded Dec 19, 2025
From: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
To: WELLS FARGO BANK, NATIONAL ASSOCIATION
Reel/Frame 074007/0183 →
SECURITY INTEREST Recorded Apr 10, 2025
From: BANK OF AMERICA, N.A.
To: WILMINGTON SAVINGS FUND SOCIETY, FSB
Reel/Frame 070811/0705 →
SECURITY INTEREST Recorded Mar 27, 2025
From: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
To: WELLS FARGO CAPITAL FINANCE, LLC
Reel/Frame 070648/0190 →
SECURITY INTEREST Recorded Mar 7, 2025
From: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 070440/0731 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 11, 2022
From: CHAI, ZHENG; EBERT, JEFFERSON THOMAS
To: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
Reel/Frame 061739/0294 →
Continuity (2)
Provisional Application 63278668 · Nov 12, 2021
Related Publication 20230151253A1 · May 18, 2023
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