Mixed Salts of Sulfonated Estolides and Other Derivatives of Fatty Acids, and Methods of Making Them

• US 20100022429A1
• Filed: 07/21/2009
• Published: 01/28/2010
• Est. Priority Date: 01/22/2008
• Status: Active Grant

• Current Assignee: Stepan Company
• Original Assignee: Stepan Company
• Inventors: Bernhardt, Randal J., Dado, Gregory P., Weitgenant, Jeremy Aaron, Filipovic, Eddie I.
• Granted Patent: US 7,879,790 B2
• Time in Patent Office: Days
• US Class Current: 510/321
• CPC Class Codes: C07C 303/06 by reaction with sulfuric acid or sulfur trioxide
• CPC Class Codes: C07C 303/22 from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
• CPC Class Codes: C07C 309/17 containing carboxyl groups bound to the carbon skeleton
• CPC Class Codes: C11D 1/123 derived from carboxylic acids, e.g. sulfosuccinates
• CPC Class Codes: C11D 1/28 Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
• CPC Class Codes: C11D 3/0026 Low foaming or foam regulating compositions
• CPC Class Codes: C11D 3/3788 Graft polymers

Abstract

Sulfo-estolides and methods of making them are described. Also described are phase-stable compositions formed from mixtures of different salts of sulfo-estolides, particularly mixtures of sodium and potassium salts of sulfo-estolides, and methods of obtaining phase-stable sulfo-estolide mixed salt compositions. The sulfo-estolide mixed salt compositions can be used in detergent formulations, such as laundry detergents, household, industrial and institutional cleaning formulations, and person care products.

Claims

1. A composition comprising a mixture of sodium and potassium salts of sulfo-estolides, which have the following Formula:

2. The composition of claim 1, wherein the potassium salt is present in the mixture in a weight fraction of about 0.1 to about 0.8 based on the total weight of the potassium and sodium salts in the mixture.

3. The composition of claim 2, wherein the potassium salt is present in the mixture in a weight fraction of about 0.5 to about 0.8 based on the total weight of the potassium and sodium salts in the mixture.

4. The composition of claim 2, wherein the potassium salt is present in the mixture in a weight fraction of about 0.1 to about 0.5 based on the total weight of the potassium and sodium salts in the mixture.

5. The composition of claim 2, wherein the potassium salt is present in the mixture in a weight fraction of about 0.3 to about 0.4 based on the total weight of the potassium and sodium salts in the mixture.

6. The composition of claim 1, wherein the potassium cation is present in the mixture in a molar fraction of about 0.08 to about 0.75 based on the total moles of sodium and potassium cations in the mixture.

7. The composition of claim 6, wherein the potassium cation is present in the mixture in a molar fraction of about 0.43 to about 0.75 based on the total moles of sodium and potassium cations in the mixture.

8. The composition of claim 6, wherein the potassium cation is present in the mixture in a molar fraction of about 0.08 to about 0.43 based on the total moles of sodium and potassium cations in the mixture.

9. The composition of claim 6, wherein the potassium cation is present in the mixture in a molar fraction of about 0.25 to about 0.34 based on the total moles of sodium and potassium cations in the mixture.

10. The composition of claim 1, further comprising about 3% by weight or less of inorganic sulfate.

11. The composition of claim 1, having a pH value of about 6 to about 8.5.

12. The composition of claim 1, wherein the composition is phase-stable, clear and homogeneous for at least 14 days at a temperature of about 22°

C.

13. The composition of claim 1 wherein the mixture of sodium and potassium sulfo-estolide salts is present in the composition in a concentration of at least 50% by weight actives.

14. The composition of claim 1, wherein the mixture of sodium and potassium sulfo-estolide salts is present in the composition in a concentration of at least 60% by weight actives.

15. A process for preparing a phase-stable sulfo-estolide composition comprising the steps of:

(a) providing at least one sulfonated intermediate made by sulfonating at least one unsaturated fatty carboxylic acid having 8 to 24 carbon atoms;

(b) reacting the sulfonated intermediate with a chain termination agent having 4 to 24 carbon atoms to form at least one sulfo-estolide;

(c) neutralizing the at least one sulfo-estolide by adding to the at least one sulfo-estolide a caustic agent selected from the group consisting of KOH, NaOH and mixtures thereof to obtain a neutralized sulfo-estolide salt;

(d) bleaching the neutralized sulfo-estolide salt with hydrogen peroxide at a pH level in the range of about 4.5 to about 7.5; and

(e) adding additional KOH, NaOH or mixtures thereof before, during or after the bleaching step in an amount sufficient to obtain a mixture of potassium and sodium sulfo-estolide salts that results in a phase-stable sulfo-estolide composition that is clear and homogeneous.

16. The process of claim 15, wherein the caustic agent for neutralization is KOH, and NaOH or a mixture of NaOH and KOH is added to the sulfo-estolide salt before, during or after the bleaching step to obtain the sulfo-estolide salt mixture.

17. The process of claim 15, wherein the caustic agent for neutralization is NaOH, and KOH or a mixture of KOH and NaOH is added to the sulfo-estolide salt before, during or after the bleaching step to obtain the sulfo-estolide salt mixture.

18. The process of claim 15, wherein the caustic agent for neutralization is a mixture of KOH and NaOH, and NaOH, KOH or a mixture thereof is added to the sulfo-estolide salt before, during or after the bleaching step to obtain the sulfo-estolide salt mixture.

19. The process of claim 15, wherein the bleaching step is carried out at a pH level of greater than about 6.0 to about 7.5.

20. The process of claim 15, wherein the additional KOH, NaOH or mixtures thereof is added in amount sufficient to obtain a pH in the range of greater than about 6.0 to about 8.5.

21. The process of claim 20, wherein the additional KOH, NaOH or mixtures thereof is added in an amount sufficient to obtain a weight fraction of potassium sulfo-estolide salt in the potassium and sodium sulfo-estolide salt mixture of about 0.1 to about 0.8 based on the total weight of potassium and sodium sulfo-estolide salts.

22. The process of claim 20, wherein the additional KOH, NaOH or mixtures thereof is added in an amount sufficient to obtain a weight fraction of potassium sulfo-estolide salt in the potassium and sodium sulfo-estolide salt mixture of about 0.5 to about 0.8, based on the total weight of the potassium and sodium sulfo-estolide salts.

23. The process of claim 20, wherein the additional KOH, NaOH or mixtures thereof is added in an amount sufficient to obtain a weight fraction of potassium sulfo-estolide salt in the potassium and sodium sulfo-estolide salt mixture of about 0.1 to about 0.5, based on the total weight of the potassium and sodium sulfo-estolide salts.

24. The process of claim 20, wherein the additional KOH, NaOH or mixtures thereof is added in an amount sufficient to obtain a weight fraction of potassium sulfo-estolide salt in the potassium and sodium sulfo-estolide salt mixture of about 0.3 to about 0.4, based on the total weight of the potassium and sodium sulfo-estolide salts.

25. The process of claim 20, wherein the additional KOH, NaOH or mixtures thereof is added in an amount sufficient to obtain a molar fraction of potassium cations in the potassium and sodium sulfo-estolide salt mixture of about 0.08 to about 0.75 based on the total moles of potassium and sodium cations.

26. The process of claim 20, wherein the additional KOH, NaOH or mixtures thereof is added in an amount sufficient to obtain a molar fraction of potassium cations in the potassium and sodium sulfo-estolide salt mixture of about 0.43 to about 0.75 based on the total moles of potassium and sodium cations.

27. The process of claim 20, wherein the additional KOH, NaOH or mixtures thereof is added in an amount sufficient to obtain a molar fraction of potassium cations in the potassium and sodium sulfo-estolide salt mixture of about 0.08 to about 0.43 based on the total moles of potassium and sodium cations.

28. The process of claim 20, wherein the additional KOH, NaOH or mixtures thereof is added in an amount sufficient to obtain a molar fraction of potassium cations in the potassium and sodium sulfo-estolide salt mixture of about 0.25 to about 0.34 based on the total moles of potassium and sodium cations.

29. A laundry detergent composition, comprising:

about 2% to about 90% by weight of a mixture of sodium and potassium salts of sulfo-estolides having the following Formula 1;

30. The laundry detergent composition of claim 29, wherein the mixture of sodium and potassium salts of sulfo-estolides is present in the composition in an amount of about 15% to about 46% by weight of the composition.

31. The laundry detergent composition of claim 30 wherein the mixture of sodium and potassium salts of sulfo-estolides provides better cleaning of grass stains on cotton than a similar detergent composition containing only a potassium sulfo-estolide salt or only a sodium sulfo-estolide salt in place of the mixture of sodium and potassium salts.

32. A laundry detergent composition, comprising:

about 2% to about 90% by weight of a mixture of sodium and potassium salts of sulfo-estolides having the following Formula 1;

33. The laundry detergent composition of claim 32, wherein the mixture of sodium and potassium salts of sulfo-estolides is present in the composition in an amount of about 15% to about 60% by weight of the composition.

34. A composition comprising a mixture of salts of sulfo-estolides, which have the following Formula: