IP Library Granted Patent US 11,268,007
Granted Patent B2
US 11,268,007 · App. 16/572,190 · Granted Mar 8, 2022

Lignin derivatives based drilling fluid additive

Inventor: Shadaab S. Maghrabi (Summerville, SC)
Assignee: INGEVITY SOUTH CAROLINA, LLC
C09K8/36
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Quick Facts
Patent No.
US 11,268,007
App. No.
16/572,190
Granted
Mar 8, 2022
Kind
B2
Abstract

A composition containing a blend, reaction product, or mixture thereof, of (A) one or more hydrophobizing component or agent (e.g., an amine or amide containing compound), and (B) one or more phenolic material or composition comprising phenolic polymers or salts thereof (e.g., lignin, a lignin derivative, or mixture thereof), which may be utilized as a drilling fluid additive or as a component of a drilling fluid additive, is described. A method of making the composition or drilling fluid additive is also described. Further, a drilling fluid containing the drilling fluid additive or composition is described.

Claims (102)

1. A composition comprising:

a blend, reaction product, or a mixture thereof, of:

one or more hydrophobizing component or agent, and

one or more phenolic material or composition comprising a sulfonated lignin that has a degree of sulfonation between about 0.1 and about 4.0, and that includes at least one of (1) a first sulfonated lignin having a sulfonate group located on aliphatic part of the lignin, (2) a second sulfonated lignin having a sulfonate group located on aromatic part of the lignin, and (3) a third sulfonated lignin having a sulfonate group located on aromatic part of the lignin and another sulfonate group located on aliphatic part of the lignin.

2. The composition of claim 1 , wherein the hydrophobizing component or agent is an amine or amide containing compound.

3. The composition of claim 1 , wherein the phenolic material or composition further includes at least one of: alkoxylated lignin; esterified lignin; hydroxypropylated lignin; phenolated lignin; alkylated lignin; urethanized lignin; hydroxyalkylated lignin; sulfomethylated lignin; nitrated lignin; azo coupled lignin; and a combination thereof.

4. The composition of claim 1 , wherein the blend, reaction product, or mixture thereof, further comprises formaldehyde.

5. The composition of claim 2 , wherein the blend, reaction product, or mixture thereof, includes at least one of:

the first sulfonated lignin is a sulfonated Kraft lignin,

the second sulfonated lignin compound a sulfomethylated Kraft lignin; and

the third sulfonated lignin is a Kraft lignin that has been sulfonated and sulfomethylated.

6. The composition of claim 1 , wherein the phenolic material or composition includes at least one of: Organosolv lignin, milled wood lignin, cellulotic enzyme lignin, enzymatic mild acidolysis lignin, lignin extracted with ionic liquids, black liquor, Kraft lignosulfonates, Kraft lignin, sulfite lignin, sulfomethylated Kraft lignin, derivatives thereof, and salts thereof.

7. The composition of claim 2 , wherein the hydrophobizing component or agent includes at least one of a fatty amine or amidoamine, a fatty imidazoline, a fatty quaternary amine compound, a fatty imidazolinium compound, and salts thereof.

8. The composition of claim 7 , wherein the fatty amine or amidoamine is prepared by reacting tall oil fatty acid with an amine having at least two secondary amine groups.

9. The composition of claim 2 , wherein the hydrophobizing component or agent includes a fatty quaternary amine compound that includes at least one of a diamidoamine quaternary amine compound and an ester of quaternary amine compound.

10. The composition of claim 2 , wherein the hydrophobizing component or agent includes at least one of diethylenetriamine (DETA), Bis-(isostearic acid amidoethyl)-N-polyethoxy-N-methyl ammonium methosulfate, N, N-bis (tallow amidoethyl) N-polyethoxy N-methylammonium methosulfate, Di (nortallowyloxyethyl) dimethyl Ammonium Chloride, tallow amine, amidoamine, and combinations thereof.

11. The composition of claim 1 , wherein the composition comprises at least one of:

about 5 to about 75 percent by weight of the hydrophobizing component or agent; and

about 25 to about 95 percent by weight of the phenolic material or composition.

12. The composition of claim 1 , wherein the composition comprises at least one of:

about 25 to about 45 percent by weight of the hydrophobizing component or agent; and

about 55 to about 75 percent by weight of the phenolic material or composition.

13. The composition of claim 1 , wherein the blend, reaction product, or mixture thereof, further comprises formalin that comprises at least one of: about 30 to about 40% by weight of formaldehyde, and about 10 to about 15% by weight of methanol.

14. The composition of claim 1 , wherein the composition is a liquid or a particulate.

15. A drilling fluid comprising an invert emulsion of a hygroscopic liquid, an oil, mineral oil, internal olefin and a drilling fluid additive that comprises the composition of claim 1 .

16. The drilling fluid of claim 15 , wherein at least one of:

the hygroscopic liquid is CaCl 2 brine;

the oil is diesel; and

the drilling fluid comprises about 0.25 to about 20 pounds per barrel (lbs/bbl) by weight of the drilling fluid additive.

17. A method of making a drilling fluid additive, the method comprising:

blending:

one or more hydrophobizing component or agent; and

one or more phenolic material or composition comprising a sulfonated lignin that has a degree of sulfonation between about 0.1 and about 4.0, and that includes at least one of: a first sulfonated lignin having a sulfonate group located on aliphatic part of the lignin and; a second sulfonated lignin having a sulfonate group located on aromatic part of the lignin; and a third sulfonated lignin having a sulfonate group located on aromatic part of the lignin and another sulfonate group located on aliphatic part of the lignin.

18. The method according to claim 17 , wherein at least one of:

the blending is performed under conditions that results in a reaction product of the blended components; and

the hydrophobizing component or agent is an amine or amide containing compound.

19. The method of claim 18 , wherein at least one of:

the phenolic material or composition includes at least one of: alkoxylated lignin, esterified lignin, hydroxypropylated lignin, phenolated lignin, alkylated lignin, urethanized lignin, hydroxyalkylated lignin, sulfomethylated lignin, nitrated lignin, azo coupled lignin, and combinations thereof; and

the phenolic material or composition includes at least one of: Organosolv lignin, milled wood lignin, cellulotic enzyme lignin, enzymatic mild acidolysis lignin, lignin extracted with ionic liquids, black liquor, Kraft lignosulfonates, Kraft lignin, sulfite lignin, sulfomethylated Kraft lignin, derivatives thereof, and salts thereof.

20. The method of claim 19 , wherein the method comprises at least one of:

the sulfonated lignin includes the first sulfonated lignin having a degree of sulfonation between 0.1 and 2.2;

preparing an aqueous solution of the phenolic material or composition, wherein the sulfonated lignin is about 5 to about 55 percent by weight of the aqueous solution;

the blending includes formaldehyde;

heating the blended mixture to a temperature of 25° C. to 120° C.

21. The method of claim 17 , wherein the method further comprises spray drying the blend, reaction product, or mixture thereof, to obtain a powder from the blend, reaction product, or mixture thereof.

22. The method of claim 19 , wherein the sulfonated lignin includes the second sulfonated lignin having a degree of sulfonation between about 0.1 and about 2.9.

23. A composition comprising:

a blend, reaction product, or a mixture thereof, of:

formalin that comprises at least one of: about 30 to about 40% by weight of formaldehyde, and about 10 to about 15% by weight of methanol;

one or more hydrophobizing component or agent, and

one or more phenolic material or composition comprising phenolic polymers or salts thereof.

24. The composition of claim 23 , wherein at least one of:

the phenolic polymers are cross-linked; and

the hydrophobizing component or agent is an amine or amide containing compound.

25. The composition of claim 23 , wherein the phenolic material or composition includes at least one of: lignin, lignin derivative, and salts thereof.

26. The composition of claim 25 , wherein the lignin derivative includes at least one of: a first sulfonated lignin having a sulfonate group located on aliphatic part of the lignin; a second sulfonated lignin having a sulfonate group located on aromatic part of the lignin; a third sulfonated lignin having a sulfonate group located on aromatic part of the lignin and another sulfonate group located on aliphatic part of the lignin; alkoxylated lignin; esterified lignin; hydroxypropylated lignin; phenolated lignin; alkylated lignin; urethanized lignin; hydroxyalkylated lignin; sulfomethylated lignin; nitrated lignin; azo coupled lignin; and a combination thereof.

27. The composition of claim 26 , wherein the blend, reaction product, or mixture thereof, includes at least one of:

the first sulfonated lignin that is a sulfonated Kraft lignin,

the second sulfonated lignin that is a sulfomethylated Kraft lignin; and

the third sulfonated lignin is a Kraft lignin that has been sulfonated and sulfomethylated.

28. The composition of claim 26 , wherein the blend, reaction product, or mixture thereof, includes at least one of:

the first sulfonated lignin has a degree of sulfonation between about 0.1 and about 4.0,

the second sulfonated lignin has a degree of sulfonation between about 0.1 and about 4.0, and

the third sulfonated lignin has a degree of sulfonation between about 0.1 and about 4.0.

29. The composition of claim 23 , wherein the phenolic material or composition includes at least one of Organosolv lignin, milled wood lignin, cellulotic enzyme lignin, enzymatic mild acidolysis lignin, lignin extracted with ionic liquids, black liquor, Kraft lignosulfonates, Kraft lignin, sulfite lignin, sulfomethylated Kraft lignin, derivatives thereof, and salts thereof.

30. The composition of claim 23 , wherein the hydrophobizing component or agent includes at least one of a fatty amine or amidoamine, a fatty imidazoline, a fatty quaternary amine compound, a fatty imidazolinium compound, and salts thereof.

31. The composition of claim 30 , wherein the fatty amine or amidoamine is prepared by reacting tall oil fatty acid with an amine having at least two secondary amine groups.

32. The composition of claim 23 , wherein the hydrophobizing component or agent includes a fatty quaternary amine compound that includes at least one of a diamidoamine quaternary amine compound and an ester of quaternary amine compound.

33. The composition of claim 23 , wherein the hydrophobizing component or agent includes at least one of diethylenetriamine (DETA), Bis-(isostearic acid amidoethyl)-N-polyethoxy-N-methyl ammonium methosulfate, N, N-bis (tallow amidoethyl) N-polyethoxy N-methylammonium methosulfate, Di (nortallowyloxyethyl) dimethyl Ammonium Chloride, tallow amine, amidoamine, and combinations thereof.

34. The composition of claim 23 , wherein the composition comprises at least one of:

about 5 to about 75 percent by weight of the hydrophobizing component or agent; and

about 25 to about 95 percent by weight of the phenolic material or composition.

35. The composition of claim 23 , wherein the composition comprises at least one of:

about 25 to about 45 percent by weight of the hydrophobizing component or agent; and

about 55 to about 75 percent by weight of the phenolic material or composition.

36. The composition of claim 23 , wherein the blend, reaction product, or mixture thereof, further comprises formalin that comprises at least one of: about 30 to about 40% by weight of formaldehyde, and about 10 to about 15% by weight of methanol.

37. The composition of claim 23 , wherein the composition is a liquid or a particulate.

38. A drilling fluid comprising an invert emulsion of a hygroscopic liquid, an oil, mineral oil, internal olefin and a drilling fluid additive that comprises the composition of claim 23 .

39. The drilling fluid of claim 38 , wherein at least one of:

the hygroscopic liquid is CaCl 2 brine;

the oil is diesel; and

the drilling fluid comprises about 0.25 to about 20 pounds per barrel (lbs/bbl) by weight of the drilling fluid additive.

40. A method of making a drilling fluid additive, the method comprising:

blending:

one or more hydrophobizing component or agent;

one or more phenolic material or composition comprising phenolic polymers or salts thereof; and

formalin that comprises at least one of: about 30 to about 40% by weight of formaldehyde, and about 10 to about 15% by weight of methanol.

41. The method according to claim 40 , wherein at least one of:

the blending is performed under conditions that results in a reaction product of the blended components;

the phenolic polymers are cross-linked;

the hydrophobizing component or agent is an amine or amide containing compound;

the phenolic material or composition includes lignin, lignin derivative, or salts thereof.

42. The method of claim 41 , wherein at least one of:

the lignin derivative is selected from the group consisting of: a first sulfonated lignin having a sulfonate group located on aliphatic part of the lignin, a second sulfonated lignin having a sulfonate group located on aromatic part of the lignin, a third sulfonated lignin having a sulfonate group located on aromatic part of the lignin and another sulfonate group located on aliphatic part of the lignin, alkoxylated lignin, esterified lignin, hydroxypropylated lignin, phenolated lignin, alkylated lignin, urethanized lignin, hydroxyalkylated lignin, sulfomethylated lignin, nitrated lignin, azo coupled lignin, and combinations thereof; and

the phenolic material or composition includes at least one of Organosolv lignin, milled wood lignin, cellulotic enzyme lignin, enzymatic mild acidolysis lignin, lignin extracted with ionic liquids, black liquor, Kraft lignosulfonates, Kraft lignin, sulfite lignin, sulfomethylated Kraft lignin, derivatives thereof, and salts thereof.

43. The method of claim 42 , wherein the method comprises at least one of:

the lignin derivative is a first sulfonated lignin having a sulfonate group located on aliphatic part of the lignin and having a degree of sulfonation between 0.1 and 2.2;

preparing an aqueous solution of the phenolic material or composition, wherein the phenolic material or composition includes at least one of the lignin, the lignin derivative, or salts thereof, and is about 5 to about 55 percent by weight of the aqueous solution;

the blending includes formaldehyde; and

heating the blended mixture to a temperature of 25° C. to 120° C.

44. The method of claim 40 , wherein the method further comprises spray drying the blend, reaction product, or mixture thereof, to obtain a powder from the blend, reaction product, or mixture thereof.

45. The method of claim 42 , wherein the lignin derivative includes a second sulfonated lignin having a sulfonate group located on aromatic part of the lignin, and having a degree of sulfonation between about 0.1 and about 2.9.

Assignments (2)
SECOND SUPPLEMENTAL SECURITY AGREEMENT Recorded Oct 28, 2020
From: INGEVITY SOUTH CAROLINA, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 054417/0821 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 19, 2019
From: MAGHRABI, SHADAAB S.
To: INGEVITY SOUTH CAROLINA, LLC
Reel/Frame 050434/0584 →
Continuity (2)
Provisional Application 62731834 · Sep 15, 2018
Related Publication 20200087562A1 · Mar 19, 2020