IP Library Granted Patent US 8,399,386
Granted Patent B2
US 8,399,386 · App. 12/565,433 · Granted Mar 19, 2013

Foamers for downhole injection

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Quick Facts
Patent No.
US 8,399,386
App. No.
12/565,433
Granted
Mar 19, 2013
Kind
B2
Abstract

The present invention relates to a method for introducing a foaming composition including an imidazoline-based compound to a fluid. The foaming composition comprises at least one quaternized compound having an imidazoline moiety. An example of the quaternized compound is a quaternized imidazoline.

Claims (21)

1. A method of foaming a fluid and unloading the fluid from an oil or gas well, the method comprising:

(A) introducing into the fluid at the downhole end of the oil or gas well a foam-forming amount of a composition comprising at least one imidazoline-based compound of the general formula:

wherein, R 4 has the following structure:

(i) R 1 is a moiety selected from the group consisting of: substituted or unsubstituted branched, chain, or ring alkyl or alkenyl having from 5 to about 29 carbon atoms in its main chain; (ii) each R 2 is independently hydrogen or a linear alkyl or alkenyl moiety having from 1 to about 10 carbon atoms; (iii) each R 3 is independently a moiety selected from the group consisting of: —CO 2 H, —SO 3 H, —PO 3 H 2 , —CO 2 R 5 , —CONH 2 , —CONHR 5 , —CON(R 5 ) 2 , and combinations thereof; (iv) at least one R 6 is R 4 , and the other R 6 is H or R 4 ; (v) each R 5 is independently a moiety selected from the group consisting of: hydrogen, substituted and unsubstituted linear alkyl, branched alkyl, aryl, alkylaryl, cycloalkyl, and heteroaromatic groups having from 1 to about 10 carbon atoms in the main chain; (vi) n is from 0 to about 8; (vii) each o is independently from 0 to about 10; (viii) x is 0 or 1; and (ix) y is from 0 to about 4

wherein a method of monitoring foaming rates is used to decide an effective foam-forming amount of the composition to introduce into the fluid;

(B) forming a foam comprising the fluid and the composition; and

(C) recovering the foam from the well.

2. The method of claim 1 , wherein the imidazoline-based compound is formed from a reaction between at least one long chain fatty acid and at least one polyalkylene polyamine, the reaction producing an intermediate imidazoline, the intermediate imidazoline being further reacted with at least one unsaturated acid or acid derivative to form the imidazoline-based compound.

3. The method of claim 2 , wherein the long chain fatty acid is tall oil fatty acid.

4. The method of claim 2 , wherein the polyalkylene polyamine is selected from the group consisting of: diethylenetriamine, triethylenetetraamine, tetraethylenepentamine, pentaethylenehexamine, hexaethylenepentamine, and combinations thereof.

5. The method of claim 2 , wherein the polyalkylene polyamine has from about 2 to about 16 carbon atoms.

6. The method of claim 2 , wherein the unsaturated acid is selected from the group consisting of: acrylic acid, vinylsulfonic acid, 2-methyl vinyl sulfonic acid, maleic acid, and combinations thereof.

7. The method of claim 1 , further comprising introducing into the fluid the foam-forming amount of the composition into a downhole end of a well as batch addition or continuously.

8. The method of claim 1 , wherein R 1 has a substituent selected from the group consisting of: hydrogen, linear or branched alkyl, aryl, alkylaryl, cycloalkyl, and heteroaromatic groups having from 1 to about 10 carbon atoms, and combinations thereof.

9. The method of claim 8 , wherein the substituent is oxygenized, sulfurized, phosphorylized, or combinations thereof.

10. The method of claim 1 , wherein the composition further comprises a solvent selected from the group consisting of: organic solvent; water; xylene; alcohols including at least methanol, ethanol, isopropanol, isobutanol, and secondary butanol; glycols including at least ethylene glycol, propylene glycol, and ethylene glycol monobutyl ether; glycol ethers; glycerol; aliphatic hydrocarbons; aromatic hydrocarbons including at least naptha; and combinations thereof.

11. The method of claim 1 , wherein the foam-forming amount of the composition has from about 10 to about 90 weight percent of the imidazoline-based compound.

12. The method of claim 1 , further comprising introducing the composition to the fluid so that from about 10 to about 100,000 ppm of the imidazoline-based compound is present in the fluid.

13. The method of claim 1 , further comprising introducing the composition to the fluid so that from about 100 to about 20,000 ppm of the imidazoline-based compound is present in the fluid.

14. The method of claim 1 , further comprising introducing the composition to the fluid so that from about 200 to about 10,000 ppm of the imidazoline-based compound is present in the fluid.

15. The method of claim 1 , wherein the fluid is oil or gas and water.

Assignments (9)
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 Dec 7, 2023
From: CHAMPIONX USA INC.
To: CHAMPIONX LLC
Reel/Frame 065799/0403 →
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 Jan 27, 2021
From: ECOLAB USA INC.
To: CHAMPIONX USA INC.
Reel/Frame 055141/0093 →
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 Jul 28, 2017
From: NALCO COMPANY LLC
To: ECOLAB USA INC.
Reel/Frame 043134/0037 →
CHANGE OF NAME Recorded Jun 20, 2017
From: NALCO COMPANY LLC
To: NALCO COMPANY LLC
Reel/Frame 042914/0886 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 30, 2009
From: NGUYEN, DUY T.; MEYER, G. RICHARD
To: NALCO COMPANY
Reel/Frame 023446/0280 →