Compositions Comprising Sulfonated Estolides And Alkyl Ester Sulfonates, Methods Of Making Them, And Compositions And Processes Employing Them

• US 20100016198A1
• Filed: 07/21/2009
• Published: 01/21/2010
• Est. Priority Date: 01/22/2008
• Status: Active Grant

• Current Assignee: Stepan Company
• Original Assignee: Stepan Company
• Inventors: Masters, Ronald A., Alonso, Lourdes R., Bernhardt, Randal J., Sajic, Branko, Dado, Gregory P., Weitgenant, Jeremy Aaron, Gariepy, Christopher A., Filipovic, Eddie I., Shapiro, Irene, Murphy, Dennis S., Pytel, Jacqueline Maas
• Granted Patent: US 8,129,328 B2
• Time in Patent Office: Days
• US Class Current: 510/127
• 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

Compositions comprising sulfo-estolides and alkyl ester sulfonates are described. Detergent formulations, such as laundry detergents, softeners, and other materials, containing any of these materials are disclosed, as well as personal care formulations, hard surface cleaner formulations, and automatic dishwasher detergent formulations. 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 laundry detergent composition, comprising:

at least one compound having the following general Formula 1;

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

one of X and Y is SO₃-Z, the other of X and Y is H (i.e., a 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 un-substituted, 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 un-substituted hydrocarbon wherein the total number of carbon atoms is from 1 to about 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;

at least one alkyl ester sulfonate;

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

2. The composition according to claim 1, wherein the composition comprises from about 2% to about 90% of the at least one compound having general Formula 1.

3. The composition according to claim 1, wherein the composition comprises from about 2% to about 50% of the at least one alkyl ester sulfonate.

4. The composition according to claim 1, wherein the at least one alkyl ester sulfonate is selected from the group consisting of C12 alpha methyl ester sulfonate, C16 alpha methyl ester sulfonate, and a blend of C12 to C18 alpha methyl ester sulfonates.

5. The composition according to claim 1, wherein the at least one alkyl ester sulfonate is sodium methyl-2 sulfo C12-C18 ester.

6. The composition according to claim 1, further comprising at least one nonionic surfactant.

7. The composition according to claim 1, further comprising cocoamide DEA.

8. The composition according to claim 1, further comprising borax pentahydrate.

9. The composition according to claim 1, further comprising glycerol.

10. The composition according to claim 1, further comprising a fluorescent whitening agent.

11. The composition according to claim 1, further comprising protease.

12. The composition according to claim 1, further comprising amylase.

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

14. A laundry detergent composition, comprising:

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

wherein n is an integer from 1-30 or a mixture 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 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 0.1% to about 30% by weight of at least one alkyl ester sulfonate;

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.

15. A green laundry detergent composition, comprising:

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

wherein n is an integer from 1-30 or a mixture 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 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 0.1% to about 30% by weight of at least one alkyl ester sulfonate;

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 rhammolipid;

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.

16. A light duty liquid detergent composition, comprising:

about 0.1% to about 90% active weight of the total composition of at least one sulfo-estolide surfactant having the following general Formula 1;

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

one of X and Y is SO₃-Z, the other of X and Y is H (i.e., a 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 un-substituted, 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 un-substituted hydrocarbon wherein the total number of carbon atoms is from 1 to 24;

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

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

about 0.1% to about 70% of at least one alkyl ester sulfonate; and

about 1% to about 99.8% of at least one carrier.

17. A laundry detergent composition, comprising:

about 5% to about 99% by weight of at least one compound having the following general Formula 1;

wherein n is an integer from 1-30 or a mixture 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 un-substituted, 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 un-substituted hydrocarbon wherein the total number of carbon atoms is from 1 to about 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 1% to about 500% by weight of at least one alkyl ester sulfonate;

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.

18. A laundry detergent composition, comprising:

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

wherein n is an integer from 1-30 or a mixture 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 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 0.1% to about 25% by weight of at least one alkyl ester sulfonate;

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.

19. A green laundry detergent composition, comprising:

about 2% to about 99.9% by weight of one or more compounds having the following general Formula 1;

wherein n is an integer from 1-30 or mixture 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 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 0.1% to about 30% by weight of at least one alkyl ester sulfonate;

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.

20. The composition of claim 19, wherein at least one of the compounds of Formula 1 is a potassium salt.

21. A liquid personal care composition, comprising:

about 0.1% to about 99% by weight of at least one surfactant having the following general Formula 1;

wherein n is an integer from 1-30 or a mixture 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 un-substituted, 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 about 24;

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

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

about 0.1% to about 85% by weight of at least one alkyl ester sulfonate; and

about 1% to about 99.9% by weight of at least one carrier.

22. The personal care composition of claim 21, further comprising at least one additive selected from the group consisting of viscosity modifiers, electrolytes, emollients, skin conditioning agents, emulsifier/suspending agents, fragrances, colors, herbal extracts, vitamins, builders, enzymes, pH adjusters, preservatives, antibacterial agents, antidandruff agents, derivatives thereof, and combinations thereof.

23. The personal care composition of claim 21, wherein the pH value is in the range of about 5 to about 7.

24. The personal care composition of claim 21, wherein the composition is a liquid hand soap.

25. The personal care composition of claim 21, wherein the formulation is a body wash.

26. The personal care composition of claim 21, wherein the formulation is a facial cleaner.

27. The personal care composition of claim 21, wherein the formulation is a shampoo, a 2-in-1 shampoo or an antidandruff shampoo.

28. The personal care composition of claim 21, the composition has a total surfactant concentration of about 20% by weight or more.

29. A low-foaming liquid machine dishwashing detergent composition comprising:

about 0.1% to about 20% by active weight of one or more surfactants of the general Formula 1;

wherein n is an integer from 1-30 or a mixture 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 un-substituted, 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 un-substituted, wherein the total number of carbon atoms is from 1 to about 24;

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

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

about 0.1% to about 20% by active weight of at least one alkyl ester sulfonate;

about 0.01% to about 10% by active weight of at least one enzyme;

about 1% to about 99.9% by weight of at least one carrier; and

wherein the low-foaming liquid machine dishwashing detergent composition has a pH from about 9 to about 14.

30. A hard surface cleaning composition, comprising:

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

wherein n is an integer from 1-30 or a mixture 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 un-substituted, 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 un-substituted hydrocarbo wherein the total number of carbon atoms is from 1 to 24;

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

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

about 0.1% to about 85% of at least one alkyl ester sulfonate; and

about 1% to about 99% of at least one carrier.

31. A laundry detergent composition, comprising:

a mixture of sodium and potassium salts of sulfo-estolides having the following general Formula 1;

wherein n is an integer from 1-30 or a mixture 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 a linear or branched, saturated or unsaturated, substituted or unsubstituted alkyl radical with from 1 to 24 carbon atoms;

W is a sodium or potassium cation, H, or an alkyl or substituted alkyl group;

Z is a sodium or potassium cation;

at least one alkyl ester sulfonate;

at least one carrier.