WO2009094336A4 - Sulfonated estolides and other derivatives of fatty acids, methods of making them, and compositions and processes employing them - Google Patents

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

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Publication number
WO2009094336A4
WO2009094336A4 PCT/US2009/031455 US2009031455W WO2009094336A4 WO 2009094336 A4 WO2009094336 A4 WO 2009094336A4 US 2009031455 W US2009031455 W US 2009031455W WO 2009094336 A4 WO2009094336 A4 WO 2009094336A4
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Prior art keywords
composition
substituted
weight
surfactant
unsaturated
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Application number
PCT/US2009/031455
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French (fr)
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WO2009094336A3 (en
WO2009094336A2 (en
Inventor
Randal J. Bernhardt
Greg P. Dado
Dennis S. Murphy
Lourdes R. Alonso
Christopher A. Gariepy
Eddie I. Filipovic
Original Assignee
Stepan Company
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Publication date
Priority to MX2010007991A priority Critical patent/MX2010007991A/en
Priority to EP09703929.1A priority patent/EP2247574B1/en
Priority to BRPI0907444-9A priority patent/BRPI0907444A2/en
Priority to AU2009206542A priority patent/AU2009206542B2/en
Priority to CA2712955A priority patent/CA2712955C/en
Priority to CN200980110511.6A priority patent/CN101981002B/en
Application filed by Stepan Company filed Critical Stepan Company
Priority to US12/507,011 priority patent/US8129328B2/en
Publication of WO2009094336A2 publication Critical patent/WO2009094336A2/en
Publication of WO2009094336A3 publication Critical patent/WO2009094336A3/en
Publication of WO2009094336A4 publication Critical patent/WO2009094336A4/en
Priority to ZA2010/05575A priority patent/ZA201005575B/en
Priority to US13/359,266 priority patent/US8338358B2/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
    • C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof 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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0026—Low foaming or foam regulating compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3788—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, 2X or 3X and up to 6X concentrates, low foaming, and/or effective in a high efficiency washing machine. Methods for laundering fabrics with the compositions are also disclosed.

Claims

AMENDED CLAIMS received by the International Bureau on 26 August 2009 (26.08.2009)What is claimed is:
1. A composition comprising one or more compounds having the following
Formula 1 :
Formula 1
Figure imgf000002_0001
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 un-substituted, alkyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of Cg to C22; a is O5 1 , or 2, and is independently assigned in each repeating unit;
R is linear or branched, saturated or unsaturated, substituted or uπ- substituted hydrocarbon wherein the total number of carbon atoms is from I to about 24;
W is a monovalent or divalent metal cation, ammonium cation, substituted ammonium cation, H, or an alky! or substituted alkyl group; and
Z is H, or a monovalent or divalent metal cation, ammonium or substituted ammonium cation.
2. The composition of claim 1, wherein a is 0.
3. The composition of claim 1 or 2, wherein n is 1 , 2, or 3.
4. The composition of any preceding claim, wherein R is about 8 to about 16 carbon atoms.
5. The composition of any preceding claim, wherein R is derived from a saturated fatty carboxylic acid.
6. The composition of any preceding claim, 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 any of claims 1 to 6, 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. 121
8. A method for hand laundering fabrics using one or more compositions of any of claims 1 to 6, 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 any of claims 1 to 6, 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 any of claims 1 to 6, effective to reduce the viscosity of the composition. 122
1 1. At least one surfactant composition comprising at least one surfactant, water, and a sufficient amount of one or more compositions of any of claims 1 to 6, effective to reduce the viscosity of the surfactant composition.
12. Λ 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 any of claims 1 to 6, 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 any of claims 1 to 6, effective to reduce the foam production of the surfactant composition.
14. 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 any of claims 1 to 6, 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.
15. The method of claim 14, 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.
16. The method of claim 14 or 15, 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 123
of dewatering, by increasing the amount of water removed from the substrate during the washing machine spin cycle.
17. The method of claims 14 to 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.
18. A liquid laundry detergent composition, comprising: about 1% to about 99% by weight of at least one compound having the following Formula 1:
Formula 1
Figure imgf000006_0001
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 un-substituted, alkyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of Ce 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 about 1 to about 24;
W is a monovalent or divalent metal cation, ammonium cation or substituted ammonium cation, H, or an alkyl or substituted alkyl group; 124
Z is H, or a monovalent or divalent metal cation, ammonium or substituted ammonium cation; and
0% lo about 40% by weight of at least one additional surfactant; and about 1% to about 99% by weight of water.
19. The composition of claim 18, wherein W is potassium and the total surfactant concentration is greater than about 40%.
20. The composition of claim 18 or 19, wherein W is potassium and the total surfactant concentration is greater than about 20%.
21. The composition of any of claims 18 to 20, wherein the formulation further comprises 0% to about 40% by weight of at least one additive.
22. The composition of claim 21, 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.
23. The composition of any of claims 18 to 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.
24. The composition of any of claims 18 to 23, 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 catioπic surfactant, at least 125 one ampholylic surfactant, at least one zwitterionic surfactant, derivatives thereof, and combinations thereof.
25. The composition of any of claims 18 to 24, 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.
26. The composition of claim 25, 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 .
27. The composition of claim 24, wherein the anionic surfactant is alkyl ether sulfate.
28. The composition of any of claims 18 to 27, wherein the formulation is biodegradable.
29. The composition of any of claims 18 to 28, wherein the formulation can be a liquid, a powder, a gel, a single-dose pouch, a solid, or a semi-solid at ambient conditions.
30. The composition of claim 29, wherein the liquid is a pourable liquid.
31. The composition of any of claims 18 to 30, wherein the formulation has a viscosity of about 10 to about 1000 cps, measured at a temperature of 250C, with a Brookfleld model LV viscometer, using a #2 spindle rotated at 5 rpm.
32. The composition of any of claims 18 to 31, wherein Formula 1 is effective to reduce the pour point of the formulation. 126
33. The composition of any of claims 18 to 32, wherein the formulation exhibits a pH of about 5 to about 13.5.
34. Λ laundry concentrate composition, comprising: about 1% to about 99% by weight of at least one compound having the following Formula 1 :
Formula 1
Figure imgf000009_0001
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;
A* 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 Cg 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 caiion, H, or an alkyl or substituted alkyl group;
Z is H, or a monovalent or divalent metal cation, ammonium or substituted ammonium cation; and
0% to about 40% by weight of at least one additional surfactant; about 1% to about 99% by weight of water; and 127
0% to about 40% by weight of at least one additive.
35. The composition of claim 34, wherein the laundry concentrate comprises surfactants in a total amount of about 20% by weight or higher,
36. The composition of claim 34, wherein the laundry concentrate comprises surfactants in a total amount of about 40% by weight or higher.
37. The composition of claim 34, wherein the laundry concentrate comprises surfactants in a total amount of about 60% by weight or higher.
38. The composition of any of claims 34 to 37, wherein the laundry concentrate is capable of being used in a high efficiency or regular washing machine,
39. The composition of any of claims 34 to 38, wherein Formula 1 is formed from all renewable carbon sources.
40. The composition of any of claims 34 to 39, 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.
41. The composition of any of claims 34 to 40, comprising about 1 % to about 90% by weight of at least one nonionic surfactant.
42. The composition of any of claims 34 to 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. 128
43. The composition of any of claims 34 to 42, having a pH value greater than about 8 or less than about 6.
44. The composition of claim 42, 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 fatly acid, and is maintained at a temperature in the range of about 400F to about 2000F,
45. A process of making at least one sulfo-estoHde 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,
46. The process of claim 45, 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 esterifϊcation of the carboxylic acid moieties is at least about 5% after the treating step.
47. The process of claim 45 or 46, further comprising the step of neutralizing the sulfo-cstolide mixture to form a neutralized material comprising at least one sulfonate salt, at least one sulfonate/carboxylate salt, derivatives thereof, or combinations thereof, 129
48. The process of claim 47, wherein the neutralization is carried out using potash,
49. The process of claim 47 or 48, 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.
50. The process of any of claims 45 to 49, further comprising the step of bleaching the sulfo-estolide mixture with hydrogen peroxide.
51. The process of claim 49, wherein the pH level is in the range of about 5 to about 7,
52. The process of any of claims 45 to 51, wherein the unsaturated fatty carboxylic acid comprises a monounsaturated fatty acid and a saturated fatty acid.
53. The process of any of claims 45 to 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.
54. The process of any of claims 45 to 53, further comprising the step of treating the sulfo-estolide mixture under conditions that reduce the carboxylic acid ester content.
55. The process of claim 47, 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 any of claims 45 to 55, wherein the unsaturated fatty carboxylic acid and the chain termination agent together comprise less than 65% monounsaturated fatty carboxylic acid. 130
57. The process of any of claims 45 to 56, wherein the unsaturated fatty carboxylic acid and the chain termination agent together comprise more than 20% saturated fatty acid.
58. The process of any of claims 45 to 57, 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.
59. Λ 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.
60. A laundry detergent composition, comprising: about 5% to about 90% by weight of at least one compound having the following Formula 1 :
Formula 1
Figure imgf000013_0001
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 un-substituted, alkyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of Cg 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;
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, gluco-amylases, amylases, lipases, cutinases, pectinases, xylaπases, reductases, oxidases, phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, beta-glucanases, and arabinosidases; derivatives thereof, and wherein the composition has a pH value in the range of about 7 to about 10.
61. A laundry detergent composition, comprising: about 5% to about 90% by weight of at least one compound having the following Formula 1 : Formula I
Figure imgf000015_0001
wherein n is an integer from 1-30; one of X and Y is SOa-Z5 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 Cg to C^, 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 caiion;
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, cuiinases, pectinases, xylanases, reductases, oxidases, phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, beta- 133
glucanases, arabinosidases, and derivatives thereof; and wherein the composition has a pH value in the range of about 7 to about 10.
62. A laundry detergent composition, comprising: about 5% to about 90% by weight of at least one compound having the following Formula 1 :
Formula 1
Figure imgf000016_0001
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 un-substituted, alkyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of Cg 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 about 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;
0% to about 50% by weight of at least one nonionic surfactant; 134
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 lo about 10 and is substantially free of enzymes.
63. A laundry detergent composition, comprising: about 5% to about 90% by weight of at least one compound having the following Formula 1:
Formula 1
Figure imgf000017_0001
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 un-substituted, a)kyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of Cg to C22; a is O5 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; 135
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.
64. A laundry detergent composition, comprising: about 5% to about 90% by weight of at least one compound having the following Formula 1 :
Formula 1
Figure imgf000018_0001
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 un-substituted, alkyl diradicals wherein the total number of carbons for each repeating unit is independent and in the range of Cg 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- substitutcd hydrocarbon wherein the total number of carbon atoms is from about 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; 136
Z is H, or a monovalent or divalent metal cation, ammonium or substituted ammonium cation;
0% to about 50% by weight of at least one nonionJc 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.
65. A laundry detergent composition, comprising: about 2% to about 90% by weight of one or more compounds having the following Formula 1 :
Formula 1
Figure imgf000019_0001
wherein n is an integer from 1-30; one of X and Y is SCh-Z1 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 repealing unit is independent and in the range of Ce to C2Ϊ, 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; 137
Z is H, or a monovalent or divalent metal cation, ammonium or substituted ammonium cation; 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 Ci2ECh.
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.
66. The composition of any one of claims 60 to 65, wherein at least one of the compounds of Formula 1 is a potassium salt.
67. The method of claim 14, wherein the soiled substrate is contacted with the composition at a temperature at or lower than about 70° F.
68. The method of claim 14, wherein the first surfactant is present in an amount effective to improve the ability of suspending soils once they are removed from the substrate.
69. The composition of claim 18, 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.
70. The composition of claim 18, 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 alkylbcnzene 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.
71. The composition of claim 18, wherein at least one of the compounds of Formula 1 is a potassium salt.
72. 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.
73. The composition of claim 72, wherein the incorporated Formula 1 is an ester of a triglyceride.
PCT/US2009/031455 2008-01-22 2009-01-20 Sulfonated estolides and other derivatives of fatty acids, methods of making them, and compositions and processes employing them WO2009094336A2 (en)

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EP09703929.1A EP2247574B1 (en) 2008-01-22 2009-01-20 Sulfonated estolides and other derivatives of fatty acids, methods of making them, and compositions and processes employing them
BRPI0907444-9A BRPI0907444A2 (en) 2008-01-22 2009-01-20 Sulfonated solids and other fatty acid derivatives, methods of making them, and compositions and processes employ them
AU2009206542A AU2009206542B2 (en) 2008-01-22 2009-01-20 Sulfonated estolides and other derivatives of fatty acids, methods of making them, and compositions and processes employing them
CA2712955A CA2712955C (en) 2008-01-22 2009-01-20 Sulfonated estolides and other derivatives of fatty acids, methods of making them, and compositions and processes employing them
CN200980110511.6A CN101981002B (en) 2008-01-22 2009-01-20 Sulfonated estolides and other derivatives of fatty acids, methods of making them, and compositions and processes employing them
MX2010007991A MX2010007991A (en) 2008-01-22 2009-01-20 Sulfonated estolides and other derivatives of fatty acids, methods of making them, and compositions and processes employing them.
US12/507,011 US8129328B2 (en) 2008-01-22 2009-07-21 Compositions comprising sulfonated estolides and alkyl ester sulfonates, methods of making them, and compositions and processes employing them
ZA2010/05575A ZA201005575B (en) 2008-01-22 2010-08-04 Sulfonated estolides and other derivatives of fatty acids,methods of making them,and compositions and processes employing them
US13/359,266 US8338358B2 (en) 2008-01-22 2012-01-26 Compositions comprising sulfonated estolides and alkyl ester sulfonates, methods of making them, and compositions and processes employing them

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US7879790B2 (en) * 2008-01-22 2011-02-01 Stepan Company Mixed salts of sulfonated estolides and other derivatives of fatty acids, and methods of making them
US7998920B2 (en) * 2008-01-22 2011-08-16 Stepan Company Sulfonated estolide compositions containing magnesium sulfate and processes employing them
US7884064B2 (en) * 2009-01-21 2011-02-08 Stepan Company Light duty liquid detergent compositions of sulfonated estolides and other derivatives of fatty acids
US8058223B2 (en) * 2009-01-21 2011-11-15 Stepan Company Automatic or machine dishwashing compositions of sulfonated estolides and other derivatives of fatty acids and uses thereof
US8119588B2 (en) * 2009-01-21 2012-02-21 Stepan Company Hard surface cleaner compositions of sulfonated estolides and other derivatives of fatty acids and uses thereof
US8124577B2 (en) * 2009-01-21 2012-02-28 Stepan Company Personal care compositions of sulfonated estolides and other derivatives of fatty acids and uses thereof

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CN101981002B (en) 2015-06-24
MX2010007991A (en) 2010-12-21
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EP2258817A3 (en) 2011-01-26
WO2009094336A3 (en) 2009-10-15
BRPI0907444A2 (en) 2015-07-14
CA2712955A1 (en) 2009-07-30
EP2258817B1 (en) 2015-01-07
AU2009206542A1 (en) 2009-07-30
EP2258679B1 (en) 2015-01-07
CA2712955C (en) 2014-04-22
EP2258679A2 (en) 2010-12-08
US20100016198A1 (en) 2010-01-21
EP2270122A2 (en) 2011-01-05
US7666828B2 (en) 2010-02-23
US20090188055A1 (en) 2009-07-30
ZA201005575B (en) 2011-04-28
EP2258679A3 (en) 2011-01-26
US8338358B2 (en) 2012-12-25
EP2258817A2 (en) 2010-12-08
WO2009094336A2 (en) 2009-07-30
US20120129955A1 (en) 2012-05-24
EP2270122B1 (en) 2015-01-07
EP2247574A2 (en) 2010-11-10
US8129328B2 (en) 2012-03-06
AU2009206542B2 (en) 2014-01-16
EP2270122A3 (en) 2011-01-26

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