IP Library Granted Patent US 11,279,864
Granted Patent B2
US 11,279,864 · App. 16/593,820 · Granted Mar 22, 2022

Method of application of sliding-ring polymers to enhance elastic properties in oil-well cement

Inventors: Hasmukh A. Patel (Houston, TX); Peter Boul (Houston, TX); Carl Thaemlitz (Cypress, TX)
Assignee: Saudi Arabian Oil Company
C09K8/467C04B24/24C04B24/285C04B24/32C04B24/383C04B28/02E21B33/14C04B2103/0062C04B2103/40
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Quick Facts
Patent No.
US 11,279,864
App. No.
16/593,820
Granted
Mar 22, 2022
Kind
B2
Abstract

This document relates to methods for improving the tensile and elastic properties of cement of an oil well using cement compositions that contain sliding-ring polymer additives. The cement compositions containing the sliding-ring polymer additives exhibit increased stiffness while having a minimum impact on compressive strength, as compared to the same cement without the sliding-ring polymer additive.

Claims (47)

1. A cement composition comprising:

cement; and

a sliding-ring polymer additive comprising at least two molecules of a polyrotaxane, wherein the polyrotaxane comprises:

a linear polymer;

at least one ring compound, wherein the linear polymer is threaded through the opening of the ring compound; and

stopper groups disposed at both end terminals of the linear polymer;

wherein at least one of the linear polymer and the ring compound is substituted with a hydrophobic group or a non-ionic group or combination thereof; and

the at least two molecules of polyrotaxane are cross-linked to each other through a chemical bond.

2. The composition of claim 1 , wherein the linear polymer is selected from the group consisting of polyvinyl alcohol, polyvinylpyrrolidone, poly(meth)acrylic acid, a cellulose-based resin, polyacrylamide, polyethylene oxide, polyethylene glycol, polypropylene glycol, a polyvinyl acetal-based resin, polyvinyl methyl ether, polyamine, polyethyleneimine, casein, gelatin, starch, a polyolefin-based resin, a polyester resin, a polyvinyl chloride resin, a polystyrene-based resin, an acrylic resin, a polycarbonate resin, a polyurethane resin, a vinyl chloride-vinyl acetate copolymer resin, a polyvinylbutyral resin, polyisobutylene, polytetrahydrofuran, polyaniline, acrylonitrile-butadiene-styrene copolymer (ABS resin), a polyamide, a polyimide, a polydiene, a polysiloxane, a polysulfone, a polyimine, a polyacetic anhydride, a polyurea, a polysulfide, a polyphosphazene, a polyketone, a polyphenylene, a polyhaloolefin; and derivatives and copolymers thereof.

3. The composition of claim 2 , wherein the linear polymer is selected from the group consisting of polypropylene glycol, polytetrahydrofuran, polydimethylsiloxane, polyethylene and polypropylene copolymer, and polyethylene glycol.

4. The composition of claim 3 , wherein the linear polymer is polyethylene glycol.

5. The composition of claim 1 , wherein the linear polymer has a molecular weight of about 2000 g/mol to about 50,000 g/mol, about 8000 g/mol to about 30,000 g/mol, about 15,000 g/mol to about 25,000 g/mol, or about 10,000 g/mol to about 50,000 g/mol.

6. The composition of claim 1 , wherein the linear polymer has a molecular weight greater than about 10,000 g/mol, greater than about 20,000 g/mol, or greater than about 35,000 g/mol.

7. The composition of claim 1 , wherein the ring compound comprises one or more of an —OH group, an —NH 2 group, a —COOH group, an epoxy group, a vinyl group, a thiol group, a photo-crosslinkable group, and combinations thereof.

8. The composition of claim 7 , wherein the photo-crosslinkable group is selected from the group consisting of cinnamic acid, coumarin, chalcone, anthracene, styrylpyridine, styrylpyridinium salt, and styrylquinolium salt.

9. The composition of claim 7 , wherein the ring compound is a cyclodextrin or cyclodextrin derivative.

10. The composition of claim 9 , wherein the cyclodextrin is selected from the group consisting of α-cyclodextrin (α-CD), β-cyclodextrin (β-CD), and γ-cyclodextrin (γ-CD) and combinations thereof.

11. The composition of claim 9 , wherein the ring compound is a cyclodextrin and a part or all of the hydroxyl groups (—OH) of the cyclodextrin is substituted with a hydrophobic group or non-ionic group or combination thereof.

12. The composition of claim 11 , wherein substitution of the hydroxyl group with the hydrophobic group or non-ionic group or combination thereof is about 10% to about 100% of the total hydroxyl groups of the total cyclodextrin molecules.

13. The composition of claim 9 , wherein at least one hydroxyl group of at least one cyclodextrin molecule in each of the at least two molecules of polyrotaxane is involved in cross-linking.

14. The composition of claim 1 , wherein ring compound has an inclusion amount ranging from 0.001 to 0.61 relative to 1 which is the maximum inclusion amount of the ring compound capable of being included by the linear polymer.

15. The composition of claim 1 , wherein the stopper group is selected from the group consisting of a dinitrophenyl, a cyclodextrin, adamantane, trityl, a fluorescein, a pyrene, a substituted benzene, a polycyclic aromatic, and steroids.

16. The composition of claim 15 , wherein the stopper group is adamantane or trityl.

17. The composition of claim 1 , wherein the hydrophobic group is selected from the group consisting of alkyl group, benzyl group, benzene derivative-containing group, acyl group, silyl group, trityl group, tosyl group, a polymer, and groups bonded through a urethane bond, ester bond or ether bond.

18. The composition of claim 17 , wherein the polymer is a polycaprolactone.

19. The composition of claim 1 , wherein the non-ionic group is selected from the group consisting of:

an —OR group, wherein R is a linear or branched alkyl group having 1-12 carbons, a linear or branched alkyl group having 2-12 carbons and at least one ether group, a cycloalkyl group having 3-12 carbons, a cycloalkyl ether group having 2-12 carbons or a cycloalkyl thioether group having 2-12 carbons;

an —O—R′—X group, wherein R′ is a group resulting from removal of one hydrogen in a linear or branched alkyl group having 1-12 carbons, a group resulting from removal of one hydrogen in a linear or branched alkyl group having 2-12 carbons and at least one ether group, a group resulting from removal of one hydrogen in a cycloalkyl group having 3-12 carbons, a group resulting from removal of one hydrogen in a cycloalkyl ether group having 2-12 carbons or a group resulting from removal of one hydrogen in a cycloalkyl thioether group having 2-12 carbons, and X is —OH, —NH 2 or —SH;

an —O—CO—NH—R 1 group, wherein R 1 is a linear or branched alkyl group having 1-12 carbons, a linear or branched alkyl group having 2-12 carbons and at least one ether group, a cycloalkyl group having 3-12 carbons, a cycloalkyl ether group having 2-12 carbons or a cycloalkyl thioether group having 2-12 carbons;

an —O—CO—R 2 group, wherein R 2 is a linear or branched alky 1 group having 1-12 carbons, a linear or branched alkyl group having 2-12 carbons and at least one ether group, a cycloalkyl group having 3-12 carbons, a cycloalkyl ether group having 2-12 carbons or a cycloalkyl thioether group having 2-12 carbons;

an —O—Si—R 3 group, wherein R 3 is a linear or branched alkyl group having 1-12 carbons, a linear or branched alkyl group having 2-12 carbons and at least one ether group, a cycloalkyl group having 3-12 carbons, a cycloalkyl ether group having 2-12 carbons or a cycloalkyl thioether group having 2-12 carbons; and

an —O—CO—O—R 4 group, wherein R 4 is a linear or branched alkyl group having 1-12 carbons, a linear or branched alkyl group having 2-12 carbons and at least one ether group, a cycloalkyl group having 3-12 carbons, a cycloalkyl ether group having 2-12 carbons or a cycloalkyl thioether group having 2-12 carbons.

20. The composition of claim 1 , wherein the at least two molecules of polyrotaxane are chemically bonded by a cross-linking agent.

21. The composition of claim 20 , wherein the cross-linking agent is selected from the group consisting of cyanuric chloride, trimesoyl chloride, terephthaloyl chloride, epichlorohydrin, dibromobenzene, glutaraldehyde, phenylene diisocyanates, tolylene diisocyanates, divinylsulfone, 1,1′-carbonyldiimidazole, and alkoxysilanes.

22. The composition of claim 1 , wherein the sliding-ring polymer additive comprises a polyrotaxane wherein the linear polymer is polyethylene glycol having a molecular weight of about 20,000 g/mol; the ring compound is a cyclodextrin wherein a part or all of the hydroxyl groups (—OH) of the cyclodextrin are substituted with a hydrophobic group or non-ionic group or combination thereof; and the stopper groups are adamantane.

23. The composition of claim 22 , wherein a part or all of the hydroxyl groups (—OH) of the cyclodextrin are substituted with a polycaprolactone, a hydroxypropyl group, or both.

24. The composition of claim 1 , wherein the amount of sliding-ring polymer additive in the cement composition is between about 0.1% to about 6%, about 1% to about 4%, or about 2% to about 3% by weight of the cement composition.

25. The composition of claim 24 , wherein the amount of sliding-ring polymer additive in the cement composition is about 1%, about 2%, or about 3% by weight of the cement composition.

26. The composition of claim 1 , wherein the cement composition comprises a suspending agent.

27. The composition of claim 26 , wherein the suspending agent is selected from the group consisting of a polymer, hydroxyethylcellulose, a polyacrylate, a hydrophilic polymers, a cellulose derivative, a block co-polymer of ethylene glycol and propylene glycol, and mixtures of these polymers.

28. The composition of claim 1 , wherein the cement composition further comprises water.

29. The composition of claim 28 , wherein the ratio of cement to water in the cement composition is about 50:50, about 60:40, or about 70:30 wt/v.

30. The composition of claim 1 , wherein the cement composition has a Young's modulus of about 0.1 GPa to about 40 GPa, about 3 GPa to about 25 GPa, or about 5 GPa to about 20 GPa at a pressure of about 0.1 MPa to about 150 MPa, about 10 MPa to about 100 MPa, or about 20 MPa to about 40 MPa, at a temperature of about 77° F. to about 450° F., about 125° F. to about 350° F., or about 150° F. to about 200° F.

31. The composition of claim 30 , wherein the cement composition has a Young's modulus of about 5 GPa to about 10 GPa at a pressure of about 20 MPa and a temperature of about 180° F.

32. The composition of claim 1 , wherein the cement composition has a compressive strength of about 1000 psi to about 15,000 psi, about 2000 psi to about 10,000 psi, or about 6500 psi to about 8500 psi, at a pressure of about 0.1 MPa to about 150 MPa, about 10 MPa to about 100 MPa, or about 20 MPa to about 40 MPa, at a temperature of about 77° F. to about 450° F., about 125° F. to about 350° F., or about 150° F. to about 200° F.

33. The composition of claim 32 , wherein the cement composition has a compressive strength of about 7800 psi to about 9500 psi at a pressure of about 20 MPa and a temperature of about 180° F.

34. The composition of claim 1 , wherein the cement composition exhibits improved tensile strength as compared to the same composition without the sliding-ring polymer additive.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2020
From: ARAMCO SERVICES COMPANY
To: SAUDI ARAMCO UPSTREAM TECHNOLOGY COMPANY
Reel/Frame 052437/0525 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2020
From: SAUDI ARAMCO UPSTREAM TECHNOLOGY COMPANY
To: SAUDI ARABIAN OIL COMPANY
Reel/Frame 052437/0776 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ATTORNEY DOCKET NUMBER PREVIOUSLY RECORDED AT REEL: 50698 FRAME: 793. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Oct 16, 2019
From: PATEL, HASMUKH A.; BOUL, PETER; THAEMLITZ, CARL
To: ARAMCO SERVICES COMPANY
Reel/Frame 050731/0236 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2019
From: PATEL, HASMUKH A.; BOUL, PETER; THAEMLITZ, CARL
To: ARAMCO SERVICES COMPANY
Reel/Frame 050698/0793 →
Continuity (1)
Related Publication 20210102112A1 · Apr 8, 2021
Cited By (1)
US 12,269,944