Sulfonated estolides and other derivatives of fatty acids, methods of making them, and compositions and processes employing them

• US 7,666,828 B2
• Filed: 01/14/2009
• Issued: 02/23/2010
• Est. Priority Date: 01/22/2008
• Status: Active Grant

• Current Assignee: Stepan Company
• Original Assignee: Stepan Company
• Inventors: Alonso, Lourdes R., Bernhardt, Randal J., Dado, Gregory P., Gariepy, Christopher A., Filipovic, Eddie I., Murphy, Dennis S.
• Primary Examiner(s): Hardee; John R
• Application Number:
  US12/353,751
• Publication Number:
  US 20090188055A1
• Time in Patent Office: 405 Days
• Field of Search: 510/495, 554/96
• US Class Current: 510/495
• 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. Useful methods include acid side bleaching, partial hydrogenation of the fatty acid, pretreatment of the fatty acid to provide color inhibition, acid side hydrolysis of the sulfo-estolides, or conversion of SHP to an essentially fully hydrolyzed product (HSHP) or a partially hydrolyzed product (PHSHP). Detergent formulations, such as laundry detergents, softeners, and other materials, containing any of these materials are disclosed. Laundry methods employing these formulations are also disclosed. These formulations are useful as laundry detergents and can be biodegradable, heavy duty liquids, 2× or 3× and up to 6× concentrates, low foaming, and/or effective in a high efficiency washing machine. Methods for laundering fabrics with the compositions are also disclosed.

Claims

1. A composition comprising one or more compounds having the following Formula 1:

2. The composition of claim 1, wherein a is 0.

3. The composition of claim 1, wherein n is 1, 2, or 3.

4. The composition of claim 1, wherein R is about 8 to about 16 carbon atoms.

5. The composition of claim 1, wherein R is derived from a saturated fatty carboxylic acid.

6. The composition of claim 1, further comprising:

0% to about 95% by weight of at least one internal hydroxy sulfonates of fatty acid or salt;

0% to about 95% by weight of at least one internal unsaturated sulfonates of fatty acid or salt; and

0% to about 95% by weight of at least one non-sulfonated estolide acid or salt.

7. A method for laundering one or more fabric articles using one or more compositions of claim 1, comprising the steps of:

placing the one or more fabric articles to be laundered into a high efficiency or regular washing machine;

placing a sufficient amount of the composition or mixture into the high efficiency or regular washing machine to provide a concentration of the composition in water of about 0.001% by weight to about 5% by weight when the high efficiency or regular washing machine is operated during a wash cycle; and

actuating the wash cycle of the high efficiency or regular washing machine to launder the one or more fabric articles.

8. A method for hand laundering fabrics using one or more compositions of claim 1, or mixtures thereof, comprising the steps of:

placing one or more fabric articles to be hand laundered into a receptacle;

placing a sufficient amount of the composition or mixture into the receptacle to provide a concentration of the composition or mixture in water of about 0.001% by weight to about 5% by weight; and

hand washing the fabric article in the receptacle to launder the fabric article.

9. A method for laundering one or more fabric articles using at least one composition of claim 1, comprising the steps of:

placing one or more fabric articles to be laundered in a high efficiency or regular washing machine that uses a washing medium to launder clothes;

providing the composition or mixture comprising about 1% to about 99% by weight of a sulfo-estolide;

placing into the high efficiency or regular washing machine a sufficient amount of the composition or mixture to provide a concentration of the composition in the washing medium of about 0.001% by weight to about 5% by weight when the machine is operated during a wash cycle; and

actuating the wash cycle of the high efficiency or regular washing machine to launder the one or more fabric articles.

10. A method of reducing the viscosity of at least one composition comprising at least one surfactant in water, the method comprising the step of including in the composition a sufficient amount of one or more compounds of claim 1, effective to reduce the viscosity of the composition.

11. At least one surfactant composition comprising at least one surfactant, water, and a sufficient amount of one or more compositions of claim 1, effective to reduce the viscosity of the surfactant composition.

12. A method of reducing the foam production of at least one composition comprising at least one surfactant in water, the method comprising the step of including or incorporating in the composition a sufficient amount of one or more compositions of claim 1, effective to reduce the foam production of the composition.

13. At least one surfactant composition comprising one or more surfactants, water, and a sufficient amount of one or more compositions of claim 1, effective to reduce the foam production of the surfactant composition.

14. The composition of claim 1, wherein W is a substituted C3 alkyl group where the structure of Formula 1 is incorporated one or more times as an ester in a monoglyceride, a diglyceride, or a triglyceride.

15. The composition of claim 14, wherein the incorporated Formula 1 is an ester of a triglyceride.

16. A method of cleaning at least one substrate, comprising the steps of:

providing at least one composition comprising a first surfactant comprising one or more compounds of claim 1, or mixtures thereof, and a second surfactant comprising at least one anionic, cationic, nonionic, ampholytic, zwitterionic surfactant, or combinations thereof;

contacting at least one soiled substrate with the composition; and

removing the composition and soil from the substrate.

17. The method of claim 16, wherein the composition and soil are removed from the substrate by rinsing the substrate with water, and the first surfactant is present in an amount effective to improve the efficiency of rinsing, by reducing the amount of water needed to remove the composition to a specific residual concentration.

18. The method of claim 16, wherein the composition and soil are removed from the substrate by dewatering the substrate during a washing machine spin cycle, and the first surfactant is present in an amount effective to improve the efficiency of dewatering, by increasing the amount of water removed from the substrate during the washing machine spin cycle.

19. The method of claim 16, wherein the substrate is one or more laundry articles and the first surfactant is present in an amount effective to improve the cleanliness of the one or more laundry articles treated according to the method.

20. The method of claim 16, wherein the soiled substrate is contacted with the composition at a temperature at or lower than about 70°

F.

21. The method of claim 16, wherein the first surfactant is present in an amount effective to improve the ability of suspending soils once they are removed from the substrate.

22. A liquid laundry detergent composition, comprising:

about 1% to about 99% by weight of at least one compound having the following Formula 1;

23. The composition of claim 22, wherein W is potassium and the total surfactant concentration is greater than about 40%.

24. The composition of claim 22, wherein W is potassium and the total surfactant concentration is greater than about 20%.

25. The composition of claim 22, wherein the formulation further comprises 0% to about 40% by weight of at least one additive.

26. The composition of claim 25, wherein the at least one additive is a member selected from the group consisting of at least one builder, at least one alkaline agent, at least one enzyme, at least one chelating agent, at least one polymeric dispersing agent, at least one suds suppressor, at least one alkyl polyglucoside, at least one polymeric suds enhancer, at least one antimicrobial agent, at least one softener, at least one odor control agent, at least one thickener, derivatives thereof, and combinations thereof.

27. The composition of claim 22, having improved anti-redeposition properties as compared to an analogous heavy duty detergent based on at least one linear alkylbenzene sulfonate, at least one alcohol ether sulfate, or a mixture thereof that does not contain at least one compound of Formula 1.

28. The composition of claim 22, wherein the at least one additional surfactant is a member selected from the group consisting of at least one anionic surfactant, at least one nonionic surfactant, at least one cationic surfactant, at least one ampholytic surfactant, at least one zwitterionic surfactant, derivatives thereof, and combinations thereof.

29. The composition of claim 28, wherein the anionic surfactant is alkyl ether sulfate.

30. The composition of claim 22, wherein the at least one additional surfactant or at least one additional additive improves laundering of a material soiled with grass, or spaghetti sauce, or dust/sebum containing soil.

31. The composition of claim 30, wherein the material is at least one cotton fabric, at least one polyester cotton blend, at least one polyester fabric, at least one silk material, at least one nylon material, at least one wool material, or a combination thereof.

32. The composition of claim 22, wherein the formulation is biodegradable.

33. The composition of claim 22, wherein the formulation can be a liquid, a powder, a gel, a single-dose pouch, a solid, or a semi-solid at ambient conditions.

34. The composition of claim 33, wherein the liquid is a pourable liquid.

35. The composition of claim 22, wherein the formulation has a viscosity of about 10 to about 1000 cps, measured at a temperature of 25°

C., with a Brookfield model LV viscometer, using a #2 spindle rotated at 5 rpm.

36. The composition of claim 22, wherein Formula 1 is effective to reduce the pour point of the formulation.

37. The composition of claim 22, wherein the formulation exhibits a pH of about 5 to about 13.5.

38. The composition of claim 22, having an improved rinsability as compared to an analogous heavy duty detergent based on at least one linear alkylbenzene sulfonate, at least one alcohol ether sulfate, or a mixture thereof that does not contain at least one compound of Formula 1, or mixtures thereof.

39. The composition of claim 22, wherein the at least one compound of Formula 1 is present in an amount sufficient to enable the composition to dissolve into a solution faster than an analogous heavy duty detergent based on at least one linear alkylbenzene sulfonate, at least one alcohol ether sulfate, or a mixture thereof that does not contain at least one compound of Formula 1, or mixtures thereof.

40. The composition of claim 22, wherein at least one of the compounds of Formula 1 is a potassium salt.

41. A laundry concentrate composition, comprising:

about 1% to about 99% by weight of at least one compound having the following Formula 1;

42. The composition of claim 41, wherein the laundry concentrate comprises surfactants in a total amount of about 20% by weight or higher.

43. The composition of claim 41, wherein the laundry concentrate comprises surfactants in a total amount of about 40% by weight or higher.

44. The composition of claim 41, wherein the laundry concentrate comprises surfactants in a total amount of about 60% by weight or higher.

45. The composition of claim 41, wherein the laundry concentrate is capable of being used in a high efficiency or regular washing machine.

46. The composition of claim 41, wherein Formula 1 is formed from all renewable carbon sources.

47. The composition of claim 46, wherein Formula 1 is made by the process comprising the steps of:

sulfonating one or more fatty acids obtained from at least one animal fat, vegetable fat, or oil source, or combinations thereof, to form a secondary sulfonate reaction; and

condensing the secondary sulfonate reaction product to form one or more estolide components.

48. The composition of claim 41, comprising about 1% to about 90% by weight of at least one nonionic surfactant.

49. The composition of claim 41, having a pH value maintained in a range that enables a clear, homogeneous liquid product, free of substantial precipitation or other physical form instability.

50. The composition of claim 49, having a pH value greater than about 8 or less than about 6.

51. The composition of claim 49, wherein the homogenous liquid product contains one or more of at least one inorganic salt, at least one non-sulfonated-estolide, or at least one fatty acid, and is maintained at a temperature in the range of about 40°

F. to about 200°

F.

52. A process of making at least one sulfo-estolide mixture comprising the steps of:

providing at least one unsaturated fatty carboxylic acid having about 8 to about 24 carbon atoms;

providing at least one chain termination agent having about 4 to about 24 carbon atoms;

sulfonating the unsaturated fatty carboxylic acid to form at least one sulfonated intermediate; and

reacting the chain termination agent with the sulfonated intermediate to form at least one sulfo-estolide mixture.

53. The process of claim 52, further comprising the step of treating the sulfo-estolide mixture under conditions effective to at least reduce the concentrations of sultone moieties, in which the degree of esterification of the carboxylic acid moieties is at least about 5% after the treating step.

54. The process of claim 52, further comprising the step of neutralizing the sulfo-estolide mixture to form a neutralized material comprising at least one sulfonate salt, at least one sulfonate/carboxylate salt, derivatives thereof, or combinations thereof.

55. The process of claim 54, further comprising the step of reducing the color of at least one reaction component, at least one reaction intermediate, or at least one reaction end product, before, during, or after the neutralization step.

56. The process of claim 54, wherein the neutralization is carried out using potash.

57. The process of claim 54, further comprising the step of bleaching the neutralized material with hydrogen peroxide at a pH level in the range of about 4.5 to about 7.5.

58. The process of claim 52, further comprising the step of bleaching the sulfo-estolide mixture with hydrogen peroxide.

59. The process of claim 57, wherein the pH level is in the range of about 5 to about 7.

60. The process of claim 52, wherein the unsaturated fatty carboxylic acid comprises a monounsaturated fatty acid and a saturated fatty acid.

61. The process of claim 52, wherein the chain termination agent is a saturated or unsaturated, substituted or unsubstituted, aliphatic or aromatic carboxylic acid, and derivative thereof, or a combination thereof.

62. The process of claim 52, further comprising the step of treating the sulfo-estolide mixture under conditions that reduce the carboxylic acid ester content.

63. The process of claim 52, wherein the unsaturated fatty carboxylic acid and the chain termination agent together comprise less than about 65% monounsaturated fatty carboxylic acid.

64. The process of claim 52, wherein the unsaturated fatty carboxylic acid and the chain termination agent together comprise more than about 20% saturated fatty acid.

65. The process claim 52, wherein the unsaturated fatty carboxylic acid comprises at least about 5% by weight polyunsaturated fatty acid and at least about 15% by weight monounsaturated fatty acid.

66. A process of making at least one sulfo-estolide mixture comprising the steps of:

providing at least one unsaturated fatty acyl containing triglyceride having about 27 to about 75 carbon atoms;

providing at least one chain termination agent having about 4 to about 24 carbon atoms;

sulfonating the unsaturated fatty acyl to form a sulfonated intermediate;

and

reacting the chain termination agent with the sulfonated intermediate to form at least one sulfo-estolide mixture.

67. A laundry detergent composition, comprising:

about 5% to about 90% by weight of at least one compound having the following Formula 1;

76. The composition of any one of claims 67, 68, 69, 70, 71, 72, 74, or 75, wherein at least one of the compounds of Formula 1 is a potassium salt.

68. A laundry detergent composition, comprising:

about 5% to about 90% by weight of at least one compound having the following Formula 1;

69. A laundry detergent composition, comprising:

about 5% to about 90% by weight of at least one compound having the following Formula 1;

70. A laundry detergent composition, comprising:

about 5% to about 90% by weight of at least one compound having the following Formula 1;

71. A laundry detergent composition, comprising:

about 5% to about 90% by weight of at least one compound having the following Formula 1;

72. A laundry detergent composition, comprising:

about 2% to about 90% by weight of one or more compounds having the following Formula 1;

73. The composition according to claim 72, wherein the thickener is a hydroxyethyl cellulose polymer of MW>

1 MM Daltons.

74. A laundry detergent composition, comprising:

about 2% to about 90% by weight of one or more compounds having the following Formula 1;

75. A green laundry detergent composition, comprising:

about 2% to about 90% by weight of one or more compounds having the following Formula 1;