IP Library Granted Patent US 12,163,103
Granted Patent B2
US 12,163,103 · App. 18/157,198 · Granted Dec 10, 2024

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 12,163,103
App. No.
18/157,198
Granted
Dec 10, 2024
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 (31)

1. An alkylphenol copolymer having the following repeating units (A) and (B):

wherein,

x is an integer from 1 to 200;

y is an integer from 2 to 200;

R 1 is a branched C 8 -C 14 alkyl; and

R2 is a straight C22-C40 alkyl,

wherein the alkyl of R 2 contains 3 or more carbon atoms than the alkyl of R 1 , and

wherein the alkylphenol copolymer is a block copolymer.

2. The alkylphenol copolymer of claim 1 , wherein R 1 is a C 12 alkyl.

3. The alkylphenol copolymer of claim 1 , wherein R 2 is a C 20 -C 34 alkyl.

4. The alkylphenol copolymer of claim 1 , wherein x and y are independently from 5 to 25.

5. The alkylphenol copolymer of claim 1 , wherein the ratio of the moles of repeating unit (A) to the moles of repeating unit (B) is from about 0.2 to about 3.

6. The alkylphenol copolymer of claim 1 , wherein the number average molecular weight of the alkylphenol copolymer is from about 4,000 to about 60,000 Daltons using gel permeation chromatography.

7. The alkylphenol copolymer of claim 1 , wherein the block copolymer is formed by a process that comprises:

reacting a phenol monomer used to form the repeating unit (A) with a formaldehyde source in a first reaction vessel to form a first oligomer;

reacting a phenol monomer used to form the repeating unit (B) with a formaldehyde source in a second reaction vessel to form a second oligomer; and

thereafter, reacting the first oligomer and the second oligomer with a formaldehyde source to form the block copolymer.

8. The alkylphenol copolymer of claim 7 , wherein the ratio of the total number of moles of the formaldehyde source added to the first reaction vessel to the total number of moles of the phenol monomer used to form the repeating unit (A) is from about 0.5 to about 1 and/or the ratio of the total number of moles of the formaldehyde source added to the second reaction vessel to the total number of moles of the phenol monomer used to form the repeating unit (B) is from about 0.5 to about 1.

9. The alkylphenol copolymer of claim 7 , wherein the phenol monomer used to form the repeating unit (A) includes dodecylphenol and/or the phenol monomer used to form the repeating unit (B) includes tetracosanylphenol, pentacosanylphenol, hexacosanylphenol, heptacosanylphenol, octacosanylphenol, or a combination thereof.

10. 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%.

11. The alkylphenol copolymer of claim 1 , wherein the alkylphenol copolymer exhibits a percent asphaltene inhibition of about 80% or more as determined at a non-volatile residue percentage of 15%.

12. The alkylphenol copolymer of claim 1 , wherein the alkylphenol copolymer exhibits a Cold Finger paraffinic wax inhibition of about 50% or more.

13. The alkylphenol copolymer of claim 1 , wherein the alkylphenol copolymer exhibits a no-flow point of about −20° C. or less as determined at a non-volatile residue concentration of 15%.

14. The alkylphenol copolymer of claim 1 , wherein the alkylphenol copolymer exhibits a static time to gel of about 500 seconds or more as determined at a temperature of −15° C. and at a non-volatile residue concentration of 15%.

15. A method for modifying a petroleum source, the method comprising adding the alkylphenol copolymer of claim 1 to the petroleum source.

16. The method of claim 15 , wherein the alkylphenol copolymer is present in a concentration of from about 1 to about 2,000 ppm.

17. The method of claim 15 , wherein a copolymer composition is added to the petroleum source, wherein the copolymer composition comprises the alkylphenol copolymer and a petroleum-based solvent.

18. The method of claim 17 , wherein the copolymer composition further comprises a corrosion inhibitor, a surfactant, a neutralizer, a stabilizer, a plasticizer, a biocide, a preservative, or a combination thereof.

19. A petroleum composition comprising the alkylphenol copolymer of claim 1 and a petroleum source.

20. The petroleum composition of claim 19 , wherein the alkylphenol copolymer is present in a concentration of from about 1 to about 1,000 ppm.

21. The alkylphenol copolymer of claim 1 , wherein R2 is a straight C24-C32 alkyl.

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 Jan 20, 2023
From: CHICHAK, KELLY S.; DOANE, JOSEPH T.; CRISTOFEL, BRIAN; SHANKLIN, ELLIOT W.
To: SI GROUP, INC.
Reel/Frame 062433/0422 →
Continuity (8)
Continuation 16293878 · Mar 6, 2019
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 20230212472A1 · Jul 6, 2023