IP Library Granted Patent US 11,560,526
Granted Patent B2
US 11,560,526 · App. 16/293,878 · Granted Jan 24, 2023

Thermally stable macromolecular compound and petroleum composition including the same

Inventors: Kelly S. Chichak (Halfmoon, NY); Joseph T. Doane (Rotterdam Junction, NY); Brian Christofel (Glenville, NY); Elliott W. Shanklin (Altamont, NY)
Assignee: SI Group, Inc.
C10L1/1981C07C39/06C07C39/15C08G8/08C08G8/10C08L61/06C10G71/00C10G75/02C10G75/04C10L1/195C10L10/16C10G2300/206C10G2300/80
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Quick Facts
Patent No.
US 11,560,526
App. No.
16/293,878
Granted
Jan 24, 2023
Kind
B2
Abstract

In one embodiment, an alkylphenol copolymer is disclosed wherein the copolymer comprises at least one alkylphenol monomer and the alkylphenol copolymer exhibits the following: an oscillation displacement Θ of greater than 0 at a temperature of −5° C. in a first oscillation temperature sweep and an oscillation displacement Θ in a second oscillation temperature sweep within 25% of the oscillation displacement Θ in the first oscillation temperature sweep at a temperature of −5° C. In a further embodiment, a petroleum composition is disclosed wherein the composition comprises a petroleum source and a macromolecular compound wherein the macromolecular compound exhibits the following: an oscillation displacement Θ of greater than 0 at a temperature of −10° C. in a first oscillation temperature sweep, and an oscillation displacement Θ in a second oscillation temperature sweep within 25% of the oscillation displacement Θ in the first oscillation temperature sweep at a temperature of −10° C.

Claims (30)

1. An alkylphenol copolymer comprising at least two different alkylphenol monomers, wherein the alkylphenol copolymer exhibits the following:

an oscillation displacement Θ of greater than 0 at a temperature of −5° C. in a first oscillation temperature sweep, and

an oscillation displacement Θ in a second oscillation temperature sweep within 25% of the oscillation displacement Θ in the first oscillation temperature sweep at a temperature of −5° C.,

wherein the first oscillation temperature sweep starts at 30° C. and ends at either −20° C. or an oscillation displacement Θ of 0 and is conducted with a stress of 0.4 Pa at an angular frequency of 0.25 rad/s and each subsequent oscillation temperature sweep starts at 25° C. and ends at either −20° C. or an oscillation displacement Θ of 0 and is conducted with a stress of 0.4 Pa at an angular frequency of 0.25 rad/s,

wherein at least one of the at least two different alkylphenol monomers as the following repeating unit (B):

wherein,

y is an integer from 1 to 200; and

R 2 includes a straight or branched C 22 -C 40 alkyl.

2. The alkylphenol copolymer of claim 1 , wherein the oscillation displacement Θ in the second oscillation temperature sweep is within 20% of the oscillation displacement Θ in the first oscillation temperature sweep.

3. The alkylphenol copolymer of claim 1 , wherein the oscillation displacement Θ in the second oscillation temperature sweep is within 5% of the oscillation displacement Θ in the first oscillation temperature sweep.

4. The alkylphenol copolymer of claim 1 , wherein the oscillation displacement Θ in a third oscillation temperature sweep is within 25% of the oscillation displacement Θ in the first oscillation temperature sweep at a temperature of −5° C.

5. The alkylphenol copolymer of claim 1 , wherein the oscillation displacement Θ in a fourth oscillation temperature sweep is within 25% of the oscillation displacement Θ in the first oscillation temperature sweep at a temperature of −5° C.

6. The alkylphenol copolymer of claim 1 , wherein the oscillation displacement Θ in the second oscillation temperature sweep is within 25% of the oscillation displacement Θ in the first oscillation temperature sweep at a temperature of −10° C.

7. The alkylphenol copolymer of claim 1 , wherein the oscillation displacement Θ in the first oscillation temperature sweep is greater than 0 at a temperature of −20° C.

8. The alkylphenol copolymer of claim 1 , wherein the oscillation displacement Θ in the first oscillation temperature sweep is greater than 0 at a temperature of −40° C.

9. The alkylphenol copolymer of claim 1 , wherein the other of the at least two different alkylphenol monomers of the alkylphenol copolymer comprises the following repeating unit (A):

wherein,

x is an integer from 1 to 200; and

R 1 includes a straight or branched C 1 -C 40 alkyl.

10. The alkylphenol copolymer of claim 1 , wherein the other of the at least two different alkylphenol monomers of the alkylphenol copolymer comprises the following repeating unit (A):

wherein,

x is an integer from 1 to 200; and

R 1 includes a straight or branched C 1 -C 15 alkyl.

11. The alkylphenol copolymer of claim 1 , wherein the oscillation displacement Θ in the second oscillation temperature sweep is within 10% of the oscillation displacement Θ in the first oscillation temperature sweep.

12. The alkylphenol copolymer of claim 1 , wherein the oscillation displacement Θ in the second oscillation temperature sweep is within 25% of the oscillation displacement Θ in the first oscillation temperature sweep at a temperature of −15° C.

13. The alkylphenol copolymer of claim 1 , wherein the oscillation displacement Θ in a third oscillation temperature sweep is within 25% of the oscillation displacement Θ in the first oscillation temperature sweep at a temperature of −10° C. and wherein the oscillation displacement Θ in a fourth oscillation temperature sweep is within 25% of the oscillation displacement Θ in the first oscillation temperature sweep at a temperature of −10° C.

14. The alkylphenol copolymer of claim 1 , wherein the alkylphenol copolymer is a block copolymer.

15. The alkylphenol copolymer of claim 1 , wherein the alkylphenol copolymer exhibits an asphaltene dispersancy parameter of about 500 or less as determined at a non-volatile residue percentage of 15% and/or wherein the alkylphenol copolymer exhibits a percent asphaltene dispersancy of about 80% or more as determined at a non-volatile residue percentage of 15%.

16. The alkylphenol copolymer of claim 1 , wherein the alkylphenol copolymer exhibits a Cold Finger paraffinic wax inhibition of about 60% or more.

17. The alkylphenol copolymer of claim 1 , wherein the oscillation temperature sweeps are conducted in a composition consisting essentially of the alkylphenol copolymer and a hydrocarbon solvent at a non-volatile residue concentration of 15%.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Dec 30, 2025
From: ALTER DOMUS (US) LLC, AS COLLATERAL AGENT
To: SI GROUP, INC.
Reel/Frame 074136/0039 →
ASSIGNMENT OF SECURITY INTEREST IN PATENTS [REEL 068968/FRAME 0001] Recorded Dec 24, 2024
From: JPMORGAN CHASE BANK, N.A.
To: ALTER DOMUS (US) LLC
Reel/Frame 069770/0736 →
SECURITY INTEREST Recorded Sep 19, 2024
From: SI GROUP, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 068968/0001 →
SECURITY INTEREST Recorded Sep 19, 2024
From: SI GROUP, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 068968/0024 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 6, 2019
From: CHICHAK, KELLY S.; DOANE, JOSEPH T.; CHRISTOFEL, BRIAN; SHANKLIN, ELLIOT
To: SI GROUP, INC.
Reel/Frame 048514/0865 →
Continuity (7)
Provisional Application 62799858 · Feb 1, 2019
Provisional Application 62795262 · Jan 22, 2019
Provisional Application 62671728 · May 15, 2018
Provisional Application 62671800 · May 15, 2018
Provisional Application 62671850 · May 15, 2018
Provisional Application 62639037 · Mar 6, 2018
Related Publication 20190276759A1 · Sep 12, 2019