IP Library Granted Patent US 9,701,791
Granted Patent B2
US 9,701,791 · App. 15/240,905 · Granted Jul 11, 2017

Poly alkanolamine emulsion breakers

Inventors: David Jay Rose (Lyons, KS); Thomas Joseph Fortune (Sterling, KS); Thomas W. Burgoyne (Sterling, KS); Kim Brashear (Sterling, KS); Beth Ann Wolf (Hutchinson, KS); Gene H. Zaid (Sterling, KS)
Assignee: Jacam Chemical Company 2013, LLC
C08G73/024B01D17/047C02F1/68C07C213/06C07C217/08C07C227/16C07C229/12C09K8/588C10G33/04C02F2101/325C02F2103/365
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,701,791
App. No.
15/240,905
Granted
Jul 11, 2017
Kind
B2
Abstract

Poly alkanolamines formed as the reaction products of secondary or tertiary alkanolamines, C8-C24 fatty acids, and shorter chain organic acids are provided, which serve as excellent petroleum/water emulsion breakers for water-in-oil emulsions and reverse oil-in-water emulsions. The polymers are preferably prepared using a reaction mixture of triethanolamine, tall oil fatty acids, and acetic acid.

Claims (55)

1. A polymer produced by the reaction of at least three different reactants, said reactants including:

a secondary or tertiary alkanolamine of the Formula

where the R1, R2, and R3 groups are independently selected from the group consisting of H and groups of the Formula

where each y of each of R1, R2, and R3 group is independently from about 1-4, and at least two of the R1, R2, and R3 groups are of Formula II;

a fatty acid of the Formula

where R is a straight or branched chain alkyl group having from about 8-24 carbon atoms; and

acetic acid; and

where the alkanolamine reactant is present in a molar excess as compared with the combined number of moles of said fatty acid and organic acid components.

2. The polymer of claim 1 , said alkanolamine being a tertiary alkanolamine.

3. The polymer of claim 2 , said tertiary alkanolamine being selected from the group consisting of trimethylanolamine, triethylanolamine, tripropylanolamine, and mixtures thereof.

4. The polymer of claim 1 , where R has from about 12-24 carbon atoms.

5. The polymer of claim 4 , where said fatty acid is tall oil fatty acid.

6. The polymer of claim 1 , where said organic acid is selected from the group consisting of methanoic, ethanoic, propanoic, butanoic, pentanoic, and hexanoic acids, and mixtures thereof.

7. The polymer of claim 1 , said polymer having a molecular weight of from about 500-10,000.

8. The polymer of claim 7 , said molecular weight being from about 3000-5000.

9. The polymer of claim 1 , said polymer being in aqueous dispersion and having a viscosity of from about 35-85 cps.

10. A polymer comprising a plurality of moieties of the Formula

where Z ranges from about 3-75, Q is selected from the group consisting of H and groups of the Formulas

where each y of each Formula VI-VIII is independently from about 1-4, R is a straight or branched chain alkyl group having from about 8-24 carbon atoms, and m ranges from 0 to about 6, and

said polymer including at least two separate moieties where Q is of Formula VI, VII, or VIII.

11. The polymer of claim 10 , where R is from about 12-24.

12. The polymer of claim 10 , said organic acid being acetic acid.

13. The polymer of claim 10 , said molecular weight being from about 3000-5000.

14. The polymer of claim 10 , wherein the number of said moieties where Q is in accordance with Formula VI is greater than the number of said moieties where Q is in accordance with either of Formula VII or Formula VIII.

15. The polymer of claim 14 , wherein the number of said moieties where Q is in accordance with Formula VI is at least two times greater than the number of said moieties where Q is in accordance with either of Formula VII or Formula VIII.

16. The polymer of claim 14 , wherein the number of said moieties where Qu is in accordance with Formula VI is greater than the combined number of moieties where Q is in accordance with either of Formula VII and Formula VIII.

17. The polymer of claim 10 , wherein Z ranges from about 18-27.

18. A polymer comprising a plurality of moieties of the Formula

where Q is selected from the group consisting of groups of the Formulas

where each y of each Formula VI-VIII is independently from about 1-4, R is a straight or branched chain alkyl group having from about 8-24 carbon atoms, and m ranges from 0 to about 6, and

said polymer having a molecular weight of from about 3000-5000.

19. The polymer of claim 18 , wherein the number of said moieties where Q is in accordance with Formula VI is greater than the number of said moieties where Q is in accordance with either of Formula VII or Formula VIII.

20. The polymer of claim 19 , wherein the number of said moieties where Q is in accordance with Formula VI is at least two times greater than the number of said moieties where Q is in accordance with either of Formula VII or Formula VIII.

21. The polymer of claim 19 , wherein the number of said moieties where Q is in accordance with Formula VI is greater than the combined number of moieties where Q is in accordance with either of Formula VII and Formula VIII.

22. The polymer of claim 1 , said three reactants comprising triethanolamine, tall oil fatty acid, and acetic acid.

23. A polymer produced by the reaction of at least three different reactants, said reactants including:

a secondary or tertiary alkanolamine of the Formula

where the R1, R2, and R3 groups are independently selected from the group consisting of H and groups of the Formula

where each y of each of R1, R2, and R3 group is independently from about 1-4, and at least two of the R1, R2, and R3 groups are of Formula II;

a fatty acid of the Formula

where R is a straight or branched chain alkyl group having from about 8-24 carbon atoms; and

an organic acid of the Formula

where m ranges from 0 to about 6, and

where the alkanolamine reactant is present in a molar excess as compared with the combined number of moles of said fatty acid and organic acid component,

said polymer having a molecular weight of from about 3000-5000.

24. A polymer produced by the reaction of at least three different reactants, said reactants including:

a secondary or tertiary alkanolamine of the Formula

where the R1, R2, and R3 groups are independently selected from the group consisting of H and groups of the Formula

where each y of each of R1, R2, and R3 group is independently from about 1-4, and at least two of the R1, R2, and R3 groups are of Formula II;

a fatty acid of the Formula

where R is a straight or branched chain alkyl group having from about 8-24 carbon atoms; and

an organic acid of the Formula

where m ranges from 0 to about 6, and

where the alkanolamine reactant is present in a molar excess as compared with the combined number of moles of said fatty acid and organic acid components,

said polymer being in aqueous dispersion and having a viscosity of from about 35-85 cps.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 23, 2024
From: CESH INTERNATIONAL TECHNOLOGY KFT
To: CES GLOBAL OPERATIONS AG
Reel/Frame 066212/0722 →
CORRECTIVE ASSIGNMENT TO CORRECT THE RECEIVING PARTY'S NAME PREVIOUSLY RECORDED ON REEL 054786 FRAME 0486. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Mar 4, 2023
From: CES INTERNATIONAL OPERATIONS S.À R.L.
To: CESH INTERNATIONAL TECHNOLOGY KFT
Reel/Frame 062956/0260 →
SECURITY INTEREST Recorded Oct 21, 2021
From: CESH INTERNATIONAL TECHNOLOGY KFT
To: THE BANK OF NOVA SCOTIA
Reel/Frame 057871/0032 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 31, 2020
From: CES INTERNATIONAL OPERATIONS S.À R.L.
To: CESH INTERNATIONAL FINANCING KFT
Reel/Frame 054786/0486 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 9, 2020
From: JACAM CHEMICAL COMPANY 2013, LLC
To: CES INTERNATIONAL OPERATIONS S.À R.L.
Reel/Frame 054587/0248 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 18, 2016
From: ROSE, DAVID JAY; FORTUNE, THOMAS JOSEPH; BURGOYNE, THOMAS W.; BRASHEAR, KIM; WOLF, BETH ANN; ZAID, GENE H.
To: JACAM CHEMICAL COMPANY 2013, LLC
Reel/Frame 039479/0248 →
Continuity (2)
Continuation In Part 14848046 · Sep 8, 2015
Related Publication 20170066881A1 · Mar 9, 2017