IP Library Granted Patent US 12,209,184
Granted Patent B2
US 12,209,184 · App. 17/479,367 · Granted Jan 28, 2025

Asphalt additives

Inventors: Chinenyeze Nwankwoala (Houston, TX); Zheng Chai (Houston, TX); Jefferson Thomas Ebert (Decatur, AL); David W. McNeece (Houston, TX)
Assignee: Ascend Performance Materials Operations LLC
C08L95/00C08K5/17C08L2555/60
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Quick Facts
Patent No.
US 12,209,184
App. No.
17/479,367
Granted
Jan 28, 2025
Kind
B2
Abstract

Provided herein are antistripping compositions which may be used, for example, as additives to bitumen compositions such as asphalt concrete to prevent or reduce susceptibility to water damage. In particular, the antistripping compositions of the present disclosure have a triamine component and a nitrile component. Also provided herein are bitumen compositions, such as asphalt, having a portion of the described antistripping compositions as an additive.

Claims (59)

1. An antistripping composition, comprising:

a triamine component; and

a nitrile component;

wherein the nitrile component has a chemical formula C x H 2x-1 (CN) 3 , Wherein x is from 4 to 10.

2. The antistripping composition of claim 1 , wherein the nitrile component comprises tricyanohexane.

3. The antistripping composition of claim 1 , wherein the nitrile component comprises a trinitrile compound having a chemical structure:

wherein a, b, and c are independently from 0 to 4.

4. The antistrippping composition of claim 1 , wherein the nitrile is present in an amount ranging from 1 wt % to 40 wt %.

5. The antistripping composition of claim 1 , wherein the triamine is present in an amount ranging from 60 wt % to 99 wt %.

6. The antistripping composition of claim 1 , wherein the triamine component comprises a triamine compound having a chemical structure:

wherein x and y are independently from 1 to 10, and wherein R is hydrogen, a C 1 -C 5 alkyl group, a C 2 -C 5 alkenyl group, or a C 1 -C 5 alcohol group.

7. The antistripping composition of claim 1 , wherein the triamine component comprise a triamine compound comprising bis (hexamethylene)triamine (BHMT), an ethyleneamine, or an amidoamine, or combinations thereof.

8. The antistripping composition of claim 1 , further comprising an organic additive.

9. The antistripping composition of claim 8 , wherein the organic additive comprises an ester having a chemical structure:

wherein a and b are independently from 0 to 4.

10. The antistripping composition of claim 8 , wherein the organic additive comprises ethanol, propanol, or an alkylene glycol, or corresponding esters of thereof, or combinations thereof.

11. An antistripping composition, comprising:

from 60 wt % to 99 wt % of a triamine component comprising bis (hexamethylene) triamine (BHMT), an ethyleneamine, or an amidoamine, or combinations thereof;

from 1 wt. % to 20 wt. % of a nitrile component comprising tricyanohexane (TCH), or adiponitrile (ADN), or a combination thereof;

from 2 wt. % to 20 wt. % of an organic additive comprising ethanol, propanol, or an alkylene glycol, or corresponding esters of thereof, or combinations thereof.

12. A bitumen composition, comprising:

a bituminous material; and

the antistripping composition of claim 1 ;

wherein the bitumen composition comprises from 0.1 wt. % to 5 wt. % of the antistripping composition.

13. The bitumen composition of claim 12 , wherein the bitumen composition exhibits at least 60% coating retention, measured according to ASTM D 3625 (2020) and/or a tensile strength ratio greater than 80, measured according to AASHTO T 283 (2020).

14. The bitumen composition of claim 12 , wherein the bitumen composition exhibits a Hamburg wheel track testing rut depth of less than 10 mm, measured according to AASHTO T 324 (2020).

15. A process for improving durability in a bitumen composition comprising a bituminous material, the process comprising:

adding the antistripping composition of claim 1 to the bitumen composition to form a treated bitumen composition,

wherein, upon aging for 40 days, the treated bitumen composition demonstrates a BBR stiffness less than 247 MPa, as measured in accordance with AASHTO T313 (2020).

16. An antistripping composition, comprising:

a triamine component; and

a nitrile component;

wherein the nitrile component comprises a trinitrile compound having a chemical

wherein a, b, and c are independently from 0 to 4.

17. The antistripping composition of claim 16 , wherein the nitrile component comprises tricyanohexane.

18. The antistripping composition of claim 16 , wherein the triamine is present in an amount ranging from 60 wt % to 99 wt %.

19. The antistripping composition of claim 16 , further comprising an organic additive comprising ethanol, propanol, or an alkylene glycol, or corresponding esters of thereof, an ester having a chemical structure:

wherein a and b are independently from 0 to 4, or combinations thereof.

20. An antistripping composition, comprising:

a triamine component; and

a nitrile component;

wherein the triamine is present in an amount ranging from 60 wt % to 99 wt %.

21. The antistripping composition of claim 20 , wherein the nitrile component has a chemical formula C x H 2x-1 (CN) 3 , Wherein x is from 4 to 10.

22. The antistripping composition of claim 20 , wherein the nitrile component comprises tricyanohexane.

23. An antistripping composition, comprising:

a triamine component;

a nitrile component; and

an organic additive comprising an ester having a chemical structure:

wherein a and b are independently from 0 to 4.

24. The antistripping composition of claim 23 , wherein the triamine is present in an amount ranging from 60 wt % to 99 wt %.

25. The antistripping composition of claim 23 , wherein the nitrile component has a chemical formula C x H 2x-1 (CN) 3 , wherein x is from 4 to 10.

26. The antistripping composition of claim 23 , wherein the nitrile component comprises tricyanohexane.

27. An antistripping composition, comprising:

a triamine component;

a nitrile component; and

an organic additive comprising ethanol, propanol, or an alkylene glycol, or corresponding esters of thereof, or combinations thereof.

28. The antistripping composition of claim 27 , wherein the triamine is present in an amount ranging from 60 wt % to 99 wt %.

29. The antistripping composition of claim 27 , wherein the nitrile component has a chemical formula C xH 2x-1 (CN) 3 , wherein x is from 4 to 10.

30. The antistripping composition of claim 27 , wherein the nitrile component comprises tricyanohexane.

Assignments (6)
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 Dec 8, 2022
From: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
To: WELLS FARGO CAPITAL FINANCE, LLC
Reel/Frame 062094/0172 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 14, 2022
From: NWANKWOALA, CHINENYEZE; CHAI, ZHENG; EBERT, JEFFERSON THOMAS; MCNEECE, DAVID W.
To: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
Reel/Frame 060191/0921 →