IP Library Granted Patent US 9,868,891
Granted Patent B2
US 9,868,891 · App. 14/461,460 · Granted Jan 16, 2018

Methods for producing emulsifiers for oil-based drilling fluids

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Quick Facts
Patent No.
US 9,868,891
App. No.
14/461,460
Granted
Jan 16, 2018
Kind
B2
Abstract

Methods for making emulsifiers, emulsified drilling fluids, and methods for using the same are provided. In one or more embodiments, the method for making an emulsifier can include mixing a tall oil and a triamide. The triamide can have the chemical formula: where: x, y, and z are integers independently selected from 1 to 10, R 1 is a C 8 -C 20 alkyl, a C 8 -C 20 alkenyl, a C 8 -C 20 dialkenyl, or a C 8 -C 20 alkynyl, R 2 is H or independently selected for each [(CH 2 ) x NR 2 (CH 2 ) y ] unit, where R 4 is a C 1 -C 3 alkylene or a C 1 -C 3 alkylene alcohol, and where at least one R 2 is and R 3 is a C 8 -C 20 alkyl, a C 8 -C 20 alkenyl, a C 8 -C 20 dialkenyl, or a C 8 -C 20 alkynyl.

Claims (26)

1. A method for making an emulsifier, comprising:

mixing a tall oil and a triamide to provide a mixture, wherein the triamide is prepared by reacting a diamidoamine with a saturated dicarboxylic acid, a saturated acid anhydride, or a mixture thereof at a temperature of about 120° C. to about 175° C.;

reacting the tall oil and the triamide with a base to provide a neutralized mixture, wherein the base comprises an alkali metal hydroxide, an alkaline earth metal hydroxide, an alkali metal oxide, an alkaline earth metal oxide, or a mixture thereof, and

spray drying the neutralized mixture to provide a spray dried emulsifier.

2. The method of claim 1 , wherein the mixture of the tall oil and the triamide has a triamide to tall oil weight ratio of about 1:4 to about 2:3.

3. The method of claim 1 , wherein the saturated dicarboxylic acid is succinic acid or the saturated acid anhydride is succinic anhydride.

4. The method of claim 1 , wherein the spray dried emulsifier has an average particle size of about 1 μm to about 75 μm.

5. The method of claim 4 , wherein the neutralized mixture is diluted with an aqueous diluent to provide a solids content of about 35 wt % to about 50 wt % prior to spray drying.

6. The method of claim 1 , wherein the tall oil comprises crude tall oil, distillate tall oil, tall oil bottoms, or any mixture thereof.

7. The method of claim 4 , wherein the spray dried emulsifier has a bulk density of about 0.24 g/mL to about 0.56 g/mL.

8. The method of claim 1 , wherein the tall oil comprises a reaction product of at least tall oil and an α,β unsaturated carboxylic acid or an α,β unsaturated acid anhydride.

9. The method of claim 1 , wherein the tall oil comprises a mixture of a first tall oil distillate fraction comprising predominantly fatty acids and a second tall oil distillate fraction comprising predominantly rosin acids, and wherein the mixture of the first tall oil distillate fraction and the second tall oil distillate fraction comprises about 45 wt % to about 90 wt % of fatty acids and about 10 wt % to about 55 wt % of rosin acids, based on the combined weight of the first tall oil distillate fraction and the second tall oil distillate fraction.

10. A method for making an emulsifier, comprising:

mixing a triamide and a tall oil to provide a mixture, wherein the triamide is prepared by reacting a diamidoamine with a saturated dicarboxylic acid, a saturated acid anhydride, or a mixture thereof at a temperature of about 120° C. to about 200° C.; and

spray drying the mixture to provide a spray dried emulsifier.

11. The method of claim 10 , wherein the triamide and the tall oil are mixed at a weight ratio of about 1:4 to about 2:3.

12. The method of claim 10 , wherein the saturated dicarboxylic acid is succinic acid or the saturated anhydride is succinic anhydride.

13. The method of claim 10 , wherein the saturated dicarboxylic acid is glutaric acid or the saturated anhydride is glutaric anhydride.

14. The method of claim 10 , wherein the diamidoamine is a reaction product from one or more fatty acids and one or more polyamines.

15. The method of claim 10 , further comprising reacting the tall oil and the triamide with a base to provide a neutralized mixture, wherein the base comprises an alkali metal hydroxide, an alkaline earth metal hydroxide, an alkali metal oxide, an alkaline earth metal oxide, or a mixture thereof; and wherein the neutralized mixture is spray dried at a temperature of about 160° C. to about 250° C. to provide the spray dried emulsifier.

16. The method of claim 10 , wherein the tall oil comprises a mixture of a first tall oil distillate fraction comprising predominantly fatty acids and a second tall oil distillate fraction comprising predominantly rosin acids, and wherein the mixture of the first tall oil distillate fraction and the second tall oil distillate fraction comprises about 45 wt % to about 90 wt % of fatty acids and about 10 wt % to about 55 wt % of rosin acids, based on the combined weight of the first tall oil distillate fraction and the second tall oil distillate fraction.

17. The method of claim 10 , wherein the tall oil comprises a reaction product of at least tall oil and an α,β unsaturated carboxylic acid or an α,β unsaturated acid anhydride.

18. A method for making a drilling fluid, comprising:

mixing an oil phase, an aqueous phase, and a spray dried emulsifier to produce a drilling fluid, wherein the spray dried emulsifier comprises a mixture of a tall oil and a triamide, and wherein the triamide is prepared by reacting a diamidoamine with a saturated dicarboxylic acid, a saturated acid anhydride, or a mixture thereof at a temperature of about 120° C. to about 200° C.

19. The method of claim 18 , wherein the spray dried emulsifier is present in the drilling fluid in an amount of about 1 wt % to about 5 wt %, based on the weight of the oil phase, the aqueous phase, and the spray dried emulsifier.

20. The method of claim 18 , wherein the saturated dicarboxylic acid comprises succinic acid or the saturated anhydride comprises succinic anhydride.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2026
From: INGEVITY SOUTH CAROLINA, LLC
To: MAINSTREAM PINE PRODUCTS, LLC
Reel/Frame 073626/0470 →
NOTICE OF SUCCESSION OF AGENCY Recorded Nov 23, 2020
From: WELLS FARGO BANK, N.A.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 054501/0049 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 30, 2018
From: GEORGIA-PACIFIC CHEMICALS LLC
To: INGEVITY SOUTH CAROLINA, LLC
Reel/Frame 045665/0452 →
SUPPLEMENTAL SECURITY AGREEMENT Recorded Apr 12, 2018
From: INGEVITY SOUTH CAROLINA, LLC
To: WELLS FARGO BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 045917/0978 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 15, 2014
From: HURD, PHILLIP W.; HINES, JOHN B.; JOHNSON, ROGER SCOTT; MPOFU, DAVID T.; RIFE, NATHAN P.; COTHRAN, ANNE M.
To: GEORGIA-PACIFIC CHEMICALS LLC
Reel/Frame 033953/0654 →