IP Library Granted Patent US 10,738,138
Granted Patent B2
US 10,738,138 · App. 15/718,566 · Granted Aug 11, 2020

Paraffin inhibitors, and paraffin suppressant compositions and methods

Inventors: Kousik Kundu (Houston, TX); Susan Amy Garner (Sugar Land, TX); Thomas O. Painter (Rosenberg, TX)
Assignee: Ecolab USA Inc.
C08F8/32C08F8/14C08F210/14C08F220/08C08F222/06C08F222/12C08F222/38C08F222/40C08L33/00C09K8/524C10L1/143C10L1/146C10L1/1966C10L1/2225C10L1/2364C10L10/16F17D3/12C10L1/1852C10L1/1985C10L1/236C10L1/2387C10L1/2437C10L10/14C10L2250/04
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Quick Facts
Patent No.
US 10,738,138
App. No.
15/718,566
Granted
Aug 11, 2020
Kind
B2
Abstract

Disclosed are paraffin inhibitors, paraffin suppressant compositions, and methods of making and using them. The paraffin inhibitors comprise polymers of a maleic moiety polymerized with at least two olefins having hydrocarbon chains of a different length from each other. When added to hydrocarbon media such as crude oils to form crude oil compositions, the paraffin inhibitors inhibit the precipitation of paraffin waxes in the crude oil compositions and exhibit reduced precipitation, gelling, and/or crystallization from the hydrocarbon media when the media are subjected to sustained low temperatures.

Claims (33)

1. A composition comprising: an organic-ammonium salt of an alkylbenzene sulfonic acid; and

a polymer, the polymer comprising the residues of

an α-olefin having the formula (I)

wherein R 1 is C10-C14 alkyl,

an α-olefin selected from formula (II) and formula (III)

wherein R 2 is C15-C19 alkyl and R 3 is C20-C30 alkyl, and

an imide having the formula (V) or a compound having formula (Va) or an ester having formula (VI)

wherein R 5 is a C15 to C19 alkyl, R 15 and R 16 are selected from hydrogen and C1 to C50 alkyl wherein at least one of R 15 and R 16 are hydrogen, and R 6 and R 7 are independently selected from hydrogen or C15 to C50 alkyl.

2. The composition of claim 1 , wherein the α-olefin has formula (III) and R 3 is C20-C24 alkyl.

3. The composition of claim 1 , the polymer further comprising the residue of an α-olefin having formula (IV)

wherein R 4 is a C30-C50 alkyl.

4. The composition of claim 1 , wherein R 5 is C18 alkyl.

5. The composition of claim 1 , wherein R 1 is C12-C14 alkyl.

6. The composition of claim 1 , wherein the alkyl of the alkylbenzene sulfonic acid is a C10 to C20 alkyl.

7. The composition of claim 1 , the alkylbenzene sulfonic acid having the formula (VII)

8. The composition of claim 7 , wherein the organic-ammonium is selected from primary ammonium, secondary ammonium, tertiary ammonium, or quaternary ammonium.

9. The composition of claim 7 wherein the organic-ammonium is ethanolammonium.

10. The composition of claim 1 , further comprising a paraffin dispersant selected from a dispersant having the formula (VIII)

a dispersant having the formula (IX)

a dispersant having the formula (X)

a dispersant having the formula (XI)

or mixtures thereof, wherein x is from 1 to 27, n is from 1 to 100, m is from 1 to 100, and R 8 is hydrogen or alkyl.

11. The composition of claim 1 , further comprising one or more C1-C12 alcohols, C5 to C18 linear alkanes, C5 to C18 branched alkanes, C5 to C8 cycloalkanes, benzene, toluene, o-xylene, m-xylene, p-xylene, refined petroleum solvent, or a mixture thereof.

12. The composition of claim 1 further comprising a C4-C50 alkyl phenol-formaldehyde resin.

13. A crude oil composition comprising one or more crude oils and about 0.5 ppm to 10,000 ppm of a composition of claim 1 .

14. A method comprising applying about 0.5 ppm to 10,000 ppm of a composition claim 1 to a crude oil to make a paraffin suppressed crude oil composition, and subjecting the paraffin suppressed crude oil composition to a temperature of between 4° C. and −60° C.

15. The method of claim 14 further comprising pumping the paraffin suppressed crude oil composition through a pipe.

16. The method of claim 14 wherein the applying is conveying through an umbilical cable.

17. A paraffin suppressant concentrate consisting essentially of:

about 1 wt % to 50 wt % of a composition of claim 1 ; and

a solvent selected from C1-C12 alcohols, C5 to C18 linear alkanes, C5 to C18 branched alkanes, C5 to C8 cycloalkanes, benzene, toluene, o-xylene, m-xylene, p-xylene, refined petroleum solvent, or mixtures thereof.

18. The composition of claim 1 , wherein the polymer comprises the residue of the imide having the formula (V).

19. The composition of claim 1 , wherein the polymer consists essentially of the residues of the alpha α-olefin having the formula (I), the α-olefin selected from formula (II) and formula (III), and the imide having the formula (V).

Assignments (8)
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Jul 17, 2025
From: JPMORGAN CHASE BANK, N.A.
To: CHAMPIONX LLC; APERGY ESP SYSTEMS, LLC; APERGY BMCS ACQUISITION CORP; HARBISON-FISCHER, INC.; NORRIS RODS, INC.,; NORRIS RODS, INC.,; NORRISEAL-WELLMARK, INC.; PCS FERGUSON, INC.; QUARTZDYNE, INC.; US SYNTHETIC CORPORATION
Reel/Frame 072004/0019 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 19, 2024
From: CHAMPIONX USA INC.
To: CHAMPIONX LLC
Reel/Frame 067768/0888 →
RELEASE OF SECURITY INTEREST Recorded Jun 7, 2022
From: BANK OF AMERICA, N.A.
To: CHAMPIONX USA INC.
Reel/Frame 060304/0267 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2020
From: ECOLAB USA INC.
To: CHAMPIONX USA INC.
Reel/Frame 053749/0001 →
SECURITY INTEREST Recorded Jun 5, 2020
From: CHAMPIONX USA INC.
To: BANK OF AMERICA, N.A.
Reel/Frame 052848/0368 →
SECURITY INTEREST Recorded Jun 5, 2020
From: CHAMPIONX USA INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 053250/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 26, 2019
From: PAINTER, THOMAS O.
To: ECOLAB USA INC.
Reel/Frame 048697/0667 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 20, 2017
From: KUNDU, KOUSIK; GARNER, SUSAN AMY
To: ECOLAB USA INC.
Reel/Frame 044179/0767 →