Sulfonated Estolide Compositions Containing Magnesium Sulfate and Processes Employing Them

• US 20100017969A1
• 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: Alonso, Lourdes R., Bernhardt, Randal J., Dado, Gregory P., Murphy, Dennis S.
• Granted Patent: US 7,998,920 B2
• Time in Patent Office: Days
• US Class Current: 8/137
• 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 3/046 Salts
• CPC Class Codes: C11D 3/3788 Graft polymers

Abstract

Formulations of sulfo-estolides, sulfo-estolide derivatives and salts of sulfo-estolides that contain magnesium ions are described. Methods of manufacture and the various applications and/or processes of utilizing magnesium ion containing formulations of sulfo-estolides, sulfo-estolide derivatives and salts of sulfo-estolides are disclosed. 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×, 3×, 6×, or higher 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 liquid laundry detergent composition, comprising:

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

wherein n is an integer from 1-30;

one of X and Y is SO₃-Z, the other of X and Y is H, and X and Y are independently assigned in each repeating unit;

A¹ and A² are linear or branched, saturated or unsaturated, substituted or unsubstituted, alkyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of C₈ to C₂₂;

a is 0, 1, or 2, and is independently assigned in each repeating unit;

R is linear or branched, saturated or unsaturated, substituted or unsubstituted, wherein the total number of carbon atoms is from 1 to 24;

W is a monovalent or divalent metal cation, ammonium cation or substituted ammonium cation, H, or an alkyl or substituted alkyl group;

Z is H, or a monovalent or divalent metal cation, ammonium or substituted ammonium cation;

about 0.5% to about 5% by weight of magnesium sulfate;

0% to about 40% by weight of at least one additional surfactant; and

about 1% to about 99% by weight of water.

2. The composition of claim 1, wherein W is potassium or sodium and the total surfactant concentration is greater than about 40%.

3. The composition of claim 1, wherein W is potassium or sodium and the total surfactant concentration is greater than about 20%.

4. The composition of claim 1, wherein the formulation further comprises 0% to about 40% by weight of at least one additive.

5. The composition of claim 4, 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.

6. The composition of claim 1, 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.

7. The composition of claim 1, 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.

8. The composition of claim 1, wherein the at least one additional surfactant improves laundering of a material soiled with grass, or spaghetti sauce, or dust/sebum containing soil.

9. The composition of claim 8, 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.

10. The composition of claim 4, wherein the at least one additive improves laundering of a material soiled with grass, or spaghetti sauce, or dust/sebum containing soil.

11. The composition of claim 10, 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.

12. The composition of claim 7, wherein the anionic surfactant is alkyl ether sulfate.

13. The composition of claim 1, wherein the formulation is biodegradable.

14. The composition of claim 1, wherein the formulation can be a liquid, a powder, a gel, a single-dose pouch, a solid, or a semi-solid at ambient conditions.

15. The composition of claim 14, wherein the liquid is a pourable liquid.

16. The composition of claim 1, 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.

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

18. The composition of claim 1, wherein the formulation exhibits a pH of about 5 to about 13.5.

39. The composition of claim 1, wherein at least one of the compounds of Formula 1 is a potassium or sodium salt.

40. A method for laundering one or more fabric articles using the composition 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.

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

placing the one the 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.

42. A method for laundering one or more fabric articles using the 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.

43. The method for laundering one or more fabric articles using the composition of claim 1, wherein the composition contains magnesium sulfate in an amount effective to improve the cleanliness of the one or more fabric articles treated according to the method.

44. A method of increasing the viscosity of the composition of claim 1, the method comprising the step of including in the composition a sufficient amount of magnesium sulfate effective to increase the viscosity of the composition.

19. A laundry concentrate composition, comprising:

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

wherein n is an integer from 1-30;

one of X and Y is SO₃-Z, the other of X and Y is H (i.e., hydrogen atom), and X and Y are independently assigned in each repeating unit;

A¹ and A² are linear or branched, saturated or unsaturated, substituted or unsubstituted, alkyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of C₈ to C₂₂;

a is 0, 1, or 2, and is independently assigned in each repeating unit;

R is linear or branched, saturated or unsaturated, substituted or unsubstituted hydrocarbon wherein the total number of carbon atoms is 1 to 24;

W is a monovalent or divalent metal cation, ammonium cation, substituted ammonium cation, H, or an alkyl or substituted alkyl group;

Z is H, or a monovalent or divalent metal cation, ammonium or substituted ammonium cation;

about 0.5% to about 5% by weight of magnesium sulfate;

0% to about 40% by weight of at least one additional surfactant;

about 1% to about 99% by weight of water; and

0% to about 40% by weight of at least one additive.

20. The composition of claim 19, wherein the laundry concentrate comprises a total amount of surfactants of about 20% by weight or higher.

21. The composition of claim 20, wherein the laundry concentrate comprises a total amount of surfactants of about 40% by weight or higher.

22. The composition of claim 21, wherein the laundry concentrate comprises a total amount of surfactants of about 60% by weight or higher.

23. The composition of claim 19, wherein the laundry concentrate is capable of being used in a high efficiency or regular washing machine.

24. The composition of claim 19, wherein Formula 1 is formed from renewable carbon sources.

25. The composition of claim 19, 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.

26. The composition of claim 19, further comprising about 1% to about 90% by weight of at least one nonionic surfactant.

27. The composition of claim 19, wherein Formula 1 exhibits a pH value maintained in a range that enables a clear, homogeneous liquid product, free of substantial precipitation or other physical form instability.

28. The composition of claim 19, wherein the formulation exhibits a pH of about 5 to about 13.5

29. A laundry detergent composition, comprising:

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

wherein n is an integer from 1-30 or mixtures thereof;

one of X and Y is SO₃-Z, the other of X and Y is H, and X and Y are independently assigned in each repeating unit;

A¹ and A² are linear or branched, saturated or unsaturated, substituted or unsubstituted, alkyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of C₈ to C₂₂;

a is 0, 1, or 2, and is independently assigned in each repeating unit;

R is linear or branched, saturated or unsaturated, substituted or unsubstituted hydrocarbon wherein the total number of carbon atoms is from 1 to 24;

W is a monovalent or divalent metal cation, ammonium cation, substituted ammonium cation, H, or an alkyl or substituted alkyl group;

Z is H, or a monovalent or divalent metal cation, ammonium or substituted ammonium cation; and

about 0.5% to about 3% by weight of magnesium sulfate;

0% to about 50% by weight of at least one nonionic surfactant;

0% to about 25% by weight of at least one alcohol ether sulfate;

a sufficient amount of at least three enzymes selected from the group consisting of;

cellulases, hemicellulases, peroxidases, proteases, glucoamylases, amylases, lipases, cutinases, pectinases, xylanases, reductases, oxidases, phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, beta-glucanases, and arabinosidases;

derivatives thereof, and combinations thereof; and

wherein the composition has a pH value in the range of about 7 to about 10.

30. A laundry detergent composition, comprising:

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

wherein n is an integer from 1-30;

one of X and Y is SO₃-Z, the other of X and Y is H, and X and Y are independently assigned in each repeating unit;

A¹ and A² are linear or branched, saturated or unsaturated, substituted or unsubstituted, alkyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of C₈ to C₂₂;

a is 0, 1, or 2, and is independently assigned in each repeating unit;

R is linear or branched, saturated or unsaturated, substituted or unsubstituted hydrocarbon wherein the total number of carbon atoms is from 1 to 24.

W is a monovalent or divalent metal cation, ammonium cation, substituted ammonium cation, H, or an alkyl or substituted alkyl group;

Z is H, or a monovalent or divalent metal cation, ammonium or substituted ammonium cation;

about 0.5% to about 3% by weight of magnesium sulfate;

0% to about 50% by weight of at least one nonionic surfactant;

0% to about 25% by weight of at least one alcohol ether sulfate; and

a sufficient amount of one or two enzymes selected from the group consisting of cellulases, hemicellulases, peroxidases, proteases, gluco-amylases, amylases, lipases, cutinases, pectinases, xylanases, reductases, oxidases, phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, beta-glucanases, arabinosidases, derivatives thereof, and combinations thereof; and

wherein the composition has a pH value in the range of about 7 to about 10.

31. A laundry detergent composition, comprising:

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

wherein n is an integer from 1-30;

one of X and Y is SO₃-Z, the other of X and Y is H, and X and Y are independently assigned in each repeating unit;

A¹ and A² are linear or branched, saturated or unsaturated, substituted or unsubstituted, alkyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of C₈ to C₂₂;

a is 0, 1, or 2, and is independently assigned in each repeating unit;

R is linear or branched, saturated or unsaturated, substituted or unsubstituted hydrocarbon wherein the total number of carbon atoms is from about 1 to 24;

W is a monovalent or divalent metal cation, ammonium cation, substituted ammonium cation, H, or an alkyl or substituted alkyl group;

Z is H, or a monovalent or divalent metal cation, ammonium or substituted ammonium cation;

about 0.5% to about 3% by weight of magnesium sulfate;

0% to about 50% by weight of at least one nonionic surfactant;

0% to about 25% by weight of at least one alcohol ether sulfate, and

wherein the composition has a pH value in the range of about 7 to about 10 and is substantially free of enzymes.

32. A laundry detergent composition, comprising:

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

wherein n is an integer from 1-30;

one of X and Y is SO₃-Z, the other of X and Y is H, and X and Y are independently assigned in each repeating unit;

A¹ and A² are linear or branched, saturated or unsaturated, substituted or unsubstituted, alkyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of C₈ to C₂₂;

a is 0, 1, or 2, and is independently assigned in each repeating unit;

R is linear or branched, saturated or unsaturated, substituted or unsubstituted hydrocarbon wherein the total number of carbon atoms is from 1 to 24;

W is a monovalent or divalent metal cation, ammonium cation, substituted ammonium cation, H, or an alkyl or substituted alkyl group;

Z is H, or a monovalent or divalent metal cation, ammonium or substituted ammonium cation;

about 0.5% to about 3% by weight of magnesium sulfate;

0% to about 25% by weight of cocamide diethanolamine; and

wherein the composition has a pH value in the range of about 7 to about 10.

33. A laundry detergent composition, comprising:

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

wherein n is an integer from 1-30;

one of X and Y is SO₃-Z, the other of X and Y is H, and X and Y are independently assigned in each repeating unit;

A¹ and A² are linear or branched, saturated or unsaturated, substituted or unsubstituted, alkyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of C₈ to C₂₂;

a is 0, 1, or 2, and is independently assigned in each repeating unit;

R is linear or branched, saturated or unsaturated, substituted or unsubstituted hydrocarbon wherein the total number of carbon atoms is from 1 to 24;

W is a monovalent or divalent metal cation, ammonium cation, substituted ammonium cation, H, or an alkyl or substituted alkyl group;

Z is H, or a monovalent or divalent metal cation, ammonium or substituted ammonium cation;

about 0.5% to about 3% by weight of magnesium sulfate;

0% to about 50% by weight of at least one nonionic surfactant;

0% to about 25% by weight of at least one alcohol ether sulfate;

about 0.1% to about 5% by weight of metasilicate, and

wherein the composition has a pH value greater than about 10.

34. A laundry detergent composition, comprising:

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

wherein n is an integer from 1-30;

one of X and Y is SO₃-Z, the other of X and Y is H, and X and Y are independently assigned in each repeating unit;

A¹ and A² are linear or branched, saturated or unsaturated, substituted or unsubstituted, alkyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of C₈ to C₂₂;

a is 0, 1, or 2, and is independently assigned in each repeating unit;

R is linear or branched, saturated or unsaturated, substituted or unsubstituted hydrocarbon wherein the total number of carbon atoms is from about 1 to 24;

W is a monovalent or divalent metal cation, ammonium cation, substituted ammonium cation, H, or an alkyl or substituted alkyl group;

Z is H, or a monovalent or divalent metal cation, ammonium or substituted ammonium cation;

about 0.5% to about 3% by weight of magnesium sulfate;

0% to about 50% by weight of at least one nonionic surfactant;

0% to about 25% by weight of at least one alcohol ether sulfate;

0.1% to about 20% by weight of sodium carbonate; and

wherein the composition has a pH value greater than about 10.

35. A laundry detergent composition, comprising:

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

wherein n is an integer from 1-30;

one of X and Y is SO₃-Z, the other of X and Y is H, and X and Y are independently assigned in each repeating unit;

A¹ and A² are linear or branched, saturated or unsaturated, substituted or unsubstituted alkyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of C₈ to C₂₂;

a is 0, 1, or 2, and is independently assigned in each repeating unit;

R is a linear or branched, saturated or unsaturated, substituted or unsubstituted alkyl radical with from 1 to 24 carbon atoms;

W is a monovalent or divalent metal cation, ammonium or substituted ammonium cation, H, or an alkyl or substituted alkyl group;

Z is H, or a monovalent or divalent metal cation, ammonium or substituted ammonium cation;

about 0.5% to about 3% by weight of magnesium sulfate;

about 2% to about 40% by weight of at least one nonionic surfactant;

0% to about 32% by weight of at least one alcohol ether sulfate;

0% to about 6% by weight of lauryl dimethlyamine oxide;

0% to about 6% by weight of C₁₂EO₃;

0% to about 10% by weight of coconut fatty acid;

0% to about 3% by weight of borax pentahydrate;

0% to about 6% by weight of propylene glycol;

0% to about 10% by weight of sodium citrate;

0% to about 6% by weight of triethanolamine;

0% to about 6% by weight of monoethanolamine;

0% to about 1% by weight of at least one fluorescent whitening agent;

0% to about 1.5% by weight of at least one anti-redeposition agent;

0% to about 2% by weight of at least one thickener;

0% to about 2% by weight of at least one thinner;

0% to about 2% by weight of at least one protease;

0% to about 2% by weight of at least one amylase; and

0% to about 2% by weight of at least one cellulase.

36. The composition according to claim 35, wherein the thickener is a hydroxyethyl cellulose polymer having a molecular weight of greater than about 1 MM Daltons.

37. A laundry detergent composition, comprising:

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

wherein n is an integer from 1-30;

one of X and Y is SO₃-Z, the other of X and Y is H, and X and Y are independently assigned in each repeating unit;

A¹ and A² are linear or branched, saturated or unsaturated, substituted or unsubstituted alkyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of C₈ to C₂₂;

a is 0, 1, or 2, and is independently assigned in each repeating unit;

R is a linear or branched, saturated or unsaturated, substituted or unsubstituted alkyl radical with from 1 to 24 carbon atoms;

W is a monovalent or divalent metal cation, ammonium or substituted ammonium cation, H, or an alkyl or substituted alkyl group;

Z is H, or a monovalent or divalent metal cation, ammonium or substituted ammonium cation;

about 0.5% to about 3% by weight of magnesium sulfate;

about 2% to about 40% by weight of at least one nonionic surfactant;

0% to about 32% by weight of at least one or more alcohol ether sulfate;

0% to about 6% by weight of lauryl dimethlyamine oxide;

0% to about 6% by weight of C₁₂EO₃;

0% to about 10% by weight of coconut fatty acid;

0% to about 10% by weight of sodium metasilicate;

0% to about 10% by weight of sodium carbonate;

0% to about 1% by weight of at least one fluorescent whitening agent;

0% to about 1.5% by weight of at least one anti-redeposition agent;

0% to about 2% by weight of at least one thickener; and

0% to about 2% by weight of at least one thinner.

38. A green laundry detergent composition, comprising:

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

wherein n is an integer from 1-30;

one of X and Y is SO₃-Z, the other of X and Y is H, and X and Y are independently assigned in each repeating unit;

A¹ and A² are linear or branched, saturated or unsaturated, substituted or unsubstituted alkyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of C₈ to C₂₂;

a is 0, 1, or 2, and is independently assigned in each repeating unit;

R is a linear or branched, saturated or unsaturated, substituted or unsubstituted alkyl radical with from 1 to 24 carbon atoms;

W is a monovalent or divalent metal cation, ammonium or substituted ammonium cation, H, or an alkyl or substituted alkyl group;

Z is H, or a monovalent or divalent metal cation, ammonium or substituted ammonium cation;

about 0.5% to about 3% by weight of magnesium sulfate;

0% to about 30% by weight of sodium lauryl sulfate;

0% to about 30% by weight of sodium stearoyl lactylate;

0% to about 30% by weight of sodium lauroyl lactate;

0% to about 60% by weight of alkyl polyglucoside;

0% to about 60% by weight of polyglycerol monoalkylate;

0% to about 30% by weight of lauryl lactyl lactate;

0% to about 30% by weight of saponin;

0% to about 30% by weight of rhamnolipid;

0% to about 30% by weight of sphingolipid;

0% to about 30% by weight of glycolipid;

0% to about 30% by weight of at least one abietic acid derivative; and

0% to about 30% by weight of at least one polypeptide.