IP Library Granted Patent US 8,669,304
Granted Patent B2
US 8,669,304 · App. 12/996,055 · Granted Mar 11, 2014

Drag reducing compositions and methods of manufacture and use

Inventors: Brad A. Bucher (Houston, TX); Michael Cox (Georgetown, TX); Tom M. Weatherford (Magnolia, TX)
Assignee: Flowchem, Ltd.
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Quick Facts
Patent No.
US 8,669,304
App. No.
12/996,055
Granted
Mar 11, 2014
Kind
B2
Abstract

A drag reducing composition comprising a primary polyolefin obtained by polymerizing mono-olefins containing from about 2 to about 30 carbon atoms, and a surfactant having an HLB in the range of 6.5 to 8.5 in an aqueous suspending media.

Claims (62)

1. An aqueous drag reducing composition comprising:

from about 10 to about 45% by weight of a finely divided solid polyolefin, friction-reducing agent formed from mono-olefins containing from 2 to 30 carbon atoms and produced by solution polymerization or bulk polymerization;

from about 0.1 to about 8% by weight of a surfactant having an HLB of from about 6.5 to about 8.5; and

an aqueous suspending medium.

2. The composition of claim 1 , wherein said aqueous suspending medium comprises water.

3. The composition of claim 1 , wherein said drag reducing agent is present in an amount of from about 30 to about 41% by weight.

4. The composition of claim 1 further including from 0.1 to 25% by weight of a coating agent.

5. The composition of claim 4 , wherein said coating agent comprises a wax.

6. The composition of claim 5 , wherein said wax is a hydrocarbon wax.

7. The composition of claim 4 , wherein said coating agent comprises a metallic salt of a fatty acid.

8. The composition of claim 1 , further comprising:

a freeze point depressant in an amount of up to about 20% by weight of the composition.

9. The composition of claim 8 , wherein said freeze point depressant is selected from the group consisting of alcohols and glycols containing from 1 to 14 carbon atoms.

10. The composition of claim 1 further including an effective amount of a biocide.

11. The composition of claim 1 , wherein surfactant comprises a highly branched surfactant having the general formula:

wherein

is the hydrophobic portion and represents a hydrocarbon parent chain having from 6 to 40 carbon atoms;

wherein m represents the number of R groups and is from 2 to 20;

wherein each of the R groups is attached to a carbon atom in the hydrocarbon parent chain;

wherein each of the R groups is independently a C 1 -C 18 alkyl group with the proviso that at least two of the R groups attached to the hydrocarbon parent chain are branched alkyl groups containing from 3 to 18 carbon atoms;

wherein HL represents the hydrophilic portion with the proviso that HL can be attached to any carbon atom in the hydrophobic portion; and

wherein the hydrocarbon parent chain and any one or more of the R groups can be connected in such a way as to form one or more cyclic groups.

12. The composition of claim 11 , wherein said hydrophilic portion (HL) is an alkoxylate grouping.

13. The composition of claim 12 , wherein said alkoxylate grouping is an alkoxylate grouping having at least two ethoxy groups.

14. The composition of claim 11 , wherein the highly branched surfactant is selected from the group consisting of:

a 2-pentyl-4-butyl hexanol alkoxylate having the formula:

wherein R 1 is a branched C 4 alkyl group, R 2 is a branched C 5 alkyl group, and a is the average number of ethylene oxide groups necessary to achieve an HLB range of from 6.5 to 8.5;

a dinonylphenol alkoxylate having the formula:

wherein each R 3 is independently a branched C 6 -C 18 alkyl group and b is the average number ethoxy groups required to achieve an HLB in the range of 6.5 to 8.5;

a triglyceride alkoxylate having the formula:

wherein R 4 , R 5 and R 6 are independently C 6 -C 18 alkyl groups and c, d and e are equal to the average number of ethoxy groups required to reach an overall HLB of from 6.5 to 8.5, and mixtures thereof.

15. The composition of claim 1 , wherein said surfactant is selected from the group consisting of:

a linear alcohol ethoxylate having the formula:

CH 3 (CH 2 ) n —O(C 2 H 4 O) f H  V

wherein n is 5 to 27, and f is the average number of ethoxy groups required to achieve an overall HLB of from 6.5 to 8.5,

a secondary alcohol ethoxylate having the formula:

wherein each R 7 and R 8 are independently alkyl groups having from 0 to 23 carbon atoms, e and t are each from 0 to 23 and f is the average number of ethoxy groups required to achieve an overall HLB of from 6.5 to 8.5,

and a nonylphenol alkoxylate having the formula:

wherein R g is a branched C 6 -C 18 alkyl group and h is the average number of ethoxy groups required to achieve an overall HLB in the range of 6.5 to 8.5, and mixtures thereof.

16. The composition of claim 15 , comprising a polymeric coupling agent having negligible surface activity.

17. The composition of claim 16 , wherein said coupling agent is selected from the group consisting of partially sulfonated naphthalene formaldehyde condensates, polymeric condensates of linear alkyl benzene sulfonic acids, and naphthalene sulfonic acids with formaldehyde and mixtures thereof.

18. The composition of claim 17 , wherein said coupling agent is present in an amount of from about 0.1 to about 4% by weight.

19. The composition of claim 1 , wherein said surfactant consists essentially of:

(i) a highly branched surfactant having the formula:

wherein each R 3 is independently a branched C 6 -C 18 alkyl group and b is the average number of ethoxy groups required to achieve an overall HLB in the range of 6.5 to 8.5;

a (ii) a branched surfactant having the formula:

wherein R 9 is a branched C 6 -C 18 alkyl group and h is the average number of ethoxy groups required to achieve an overall HLB in the range of 6.5 to 8.5, in combination with a coupling agent selected from the group consisting of sulfonated naphthalene formaldehyde condensates, polymeric condensates of linear alkyl benzene sulfonic acids, and condensates of naphthalene sulfonic acids with formaldehyde and, mixtures of (i) and (ii).

20. A method of reducing drag in a flowing hydrocarbon stream comprising:

introducing into said stream an effective amount of the drag reducing composition of claim 1 .

21. An aqueous drag reducing composition comprising:

from about 10 to about 45% by weight of a finely divided solid polyolefin, friction-reducing agent formed from mono-olefins containing from 2 to 30 carbon atoms;

from about 0.1 to about 8% by weight of a surfactant having an HLB of from about 6.5 to about 8.5, said surfactant being selected from the group consisting of:

a linear alcohol ethoxylate having the formula:

CH 3 (CH 2 ) n —O(C 2 H 4 O) f H  V

wherein n is 5 to 27, and f is the average number of ethoxy groups required to achieve an overall HLB of from 6.5 to 8.5,

a secondary alcohol ethoxylate having the formula:

wherein each R 7 and R 8 are independently alkyl groups having from 0 to 23 carbon atoms, e and t are each from 0 to 23 and f is the average number of ethoxy groups required to achieve an overall HLB of from 6.5 to 8.5,

and a nonylphenol alkoxylate having the formula:

wherein R g is a branched C 6 -C 18 alkyl group and h is the average number of ethoxy groups required to achieve an overall HLB in the range of 6.5 to 8.5, and mixtures thereof;

a polymeric coupling agent having neglible surface activity, said coupling agent being selected from the group consisting of partially sulfonated naphthalene formaldehyde condensates, polymeric condensates of linear alkyl benzene sulfonic acids, and naphthalene sulfonic acids with formaldehyde and mixtures thereof; and

an aqueous suspending medium.

22. The composition of claim 21 , wherein said coupling agent is present in an amount of from about 0.1 to about 4% by weight.

Assignments (15)
SECURITY INTEREST Recorded Mar 4, 2024
From: FLOWCHEM LLC
To: CADENCE BANK
Reel/Frame 066640/0850 →
RELEASE OF SECURITY INTEREST Recorded Mar 1, 2024
From: MORGAN STANLEY SENIOR FUNDING, INC., AS COLLATERAL AGENT
To: FLOWCHEM LLC
Reel/Frame 066617/0178 →
RELEASE OF SECURITY INTEREST Recorded Mar 1, 2024
From: TRUIST BANK
To: FLOWCHEM LLC
Reel/Frame 066624/0015 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 23, 2022
From: CMC MATERIALS, INC.
To: FLOWCHEM LLC
Reel/Frame 061866/0269 →
SECURITY INTEREST Recorded Jul 8, 2022
From: ENTEGRIS, INC.; ENTEGRIS GP, INC.; POCO GRAPHITE, INC.; CMC MATERIALS, INC.; INTERNATIONAL TEST SOLUTIONS, LLC; QED TECHNOLOGIES INTERNATIONAL, INC.
To: TRUIST BANK, AS NOTES COLLATERAL AGENT
Reel/Frame 060613/0072 →
SECURITY INTEREST Recorded Jul 8, 2022
From: CMC MATERIALS, INC.; INTERNATIONAL TEST SOLUTIONS, LLC; QED TECHNOLOGIES INTERNATIONAL, INC.
To: MORGAN STANLEY SENIOR FUNDING, INC., AS COLLATERAL AGENT
Reel/Frame 060615/0001 →
RELEASE OF SECURITY INTEREST Recorded Jul 6, 2022
From: JPMORGAN CHASE BANK, N.A.
To: CABOT MICROELECTRONICS CORPORATION; QED TECHNOLOGIES INTERNATIONAL, INC.; FLOWCHEM LLC; KMG ELECTRONIC CHEMICALS, INC.; KMG-BERNUTH, INC.; MPOWER SPECIALTY CHEMICALS LLC; SEALWELD (USA), INC.; INTERNATIONAL TEST SOLUTIONS, LLC; CMC MATERIALS, INC.
Reel/Frame 060592/0260 →
CHANGE OF NAME Recorded Jan 13, 2021
From: CABOT MICROELECTRONICS CORPORATION
To: CMC MATERIALS, INC.
Reel/Frame 054980/0681 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 17, 2020
From: FLOWCHEM LLC
To: CABOT MICROELECTRONICS CORPORATION
Reel/Frame 051834/0014 →
CHANGE OF NAME Recorded Nov 16, 2018
From: FLOWCHEM, LTD.
To: FLOWCHEM LLC
Reel/Frame 047524/0500 →
SECURITY AGREEMENT Recorded Nov 16, 2018
From: CABOT MICROELECTRONICS CORPORATION; QED TECHNOLOGIES INTERNATIONAL, INC.; FLOWCHEM LLC; KMG ELECTRONIC CHEMICALS, INC.; MPOWER SPECIALTY CHEMICALS LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 047588/0263 →
RELEASE OF SECURITY INTEREST Recorded Jun 20, 2017
From: KAYNE ANDERSON SENIOR CREDIT ADVISORS, LLC, AS ADMINISTRATIVE AGENT
To: FLOWCHEM LLC, SUCCESSOR BY MERGER TO FLOWCHEM, LTD.
Reel/Frame 042754/0846 →
SECURITY AGREEMENT Recorded Dec 6, 2013
From: FLOWCHEM, LTD.
To: KAYNE ANDERSON SENIOR CREDIT ADVISORS, LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 031768/0471 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 5, 2013
From: BUCHER, BRAD A.; COX, MICHAEL F.
To: FLOWCHEM, LTD.
Reel/Frame 031544/0233 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 12, 2013
From: WEATHERFORD, TOM M.
To: FLOWCHEM, LTD.
Reel/Frame 030989/0149 →
Continuity (3)
Provisional Application 61059876 · Jun 9, 2008
Provisional Application 61166269 · Apr 3, 2009
Related Publication 20110132466A1 · Jun 9, 2011