Laundry detergents based on compositions derived from natural oil metathesis

• US 9,249,373 B2
• Filed: 10/25/2011
• Issued: 02/02/2016
• Est. Priority Date: 10/25/2010
• Status: Active Grant

• Current Assignee: Stepan Company
• Original Assignee: Stepan Company
• Inventors: Allen, Dave R., Alonso, Marcos, Bernhardt, Randal J., Murphy, Dennis S., Wolfe, Patrick Shane, Brown, Aaron
• Primary Examiner(s): Delcotto, Gregory R
• Application Number:
  US13/880,024
• Publication Number:
  US 20130217608A1
• Time in Patent Office: 1,561 Days
• Field of Search: 510/350, 510/351, 510/356, 510/500, 510/505, 510/506, 510/492, 510/494, 510/495, 510/501, 510/503
• US Class Current: 1/1
• CPC Class Codes: A01N 25/02 containing liquids as carriers, diluents or solvents
• CPC Class Codes: A01N 25/04 Dispersions, emulsions, suspoemulsions, suspension concentrates or gels foams A01N25/16
• CPC Class Codes: A01N 25/30 characterised by the surfactants
• CPC Class Codes: A01N 33/12 Quaternary ammonium compounds
• CPC Class Codes: A01N 33/18 Nitro compounds
• CPC Class Codes: A01N 37/18 containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
• CPC Class Codes: A01N 37/44 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
• CPC Class Codes: A01N 39/04 Aryloxy-acetic acids; Derivatives thereof
• CPC Class Codes: A01N 41/04 Sulfonic acids; Derivatives thereof
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: A01N 43/653 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• CPC Class Codes: A01N 51/00 Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
• CPC Class Codes: A01N 53/00 Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
• CPC Class Codes: A01N 57/20 containing acyclic or cycloaliphatic radicals
• CPC Class Codes: A61K 8/416 Quaternary ammonium compounds A61K8/35 takes precedence
• CPC Class Codes: A61K 8/42 Amides
• CPC Class Codes: A61K 8/44 Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
• CPC Class Codes: A61K 8/466 containing sulfonic acid derivatives; Salts
• CPC Class Codes: A61K 8/92 Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
• CPC Class Codes: A61Q 19/10 : Washing or bathing preparations
• CPC Class Codes: A61Q 5/12 : Preparations containing hair conditioners
• CPC Class Codes: A62D 1/0071 : Foams
• CPC Class Codes: C07C 209/12 : with formation of quaternary ammonium compounds
• CPC Class Codes: C07C 209/14 : by substitution of hydroxy groups or of etherified or esterified hydroxy groups
• CPC Class Codes: C07C 211/21 : Monoamines
• CPC Class Codes: C07C 211/63 : having quaternised nitrogen atoms bound to acyclic carbon atoms
• CPC Class Codes: C07C 211/64 : having quaternised nitrogen atoms bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07C 219/08 : having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
• CPC Class Codes: C07C 231/12 : by reactions not involving the formation of carboxamide groups
• CPC Class Codes: C07C 233/38 : having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
• CPC Class Codes: C07C 237/16 : the carbon skeleton being acyclic and unsaturated
• CPC Class Codes: C07C 303/18 : by reaction of sulfides with compounds having functional groups with formation of sulfo or halosulfonyl groups
• CPC Class Codes: C07C 309/14 : containing amino groups bound to the carbon skeleton
• CPC Class Codes: C07C 69/533 : Monocarboxylic acid esters having only one carbon-to-carbon double bond
• CPC Class Codes: C07C 69/593 : Dicarboxylic acid esters having only one carbon-to-carbon double bond
• CPC Class Codes: C08G 65/2615 : the other compounds containing carboxylic acid, ester or anhydride groups
• CPC Class Codes: C08K 5/01 : Hydrocarbons C08K5/0091 takes precedence
• CPC Class Codes: C08K 5/20 : Carboxylic acid amides
• CPC Class Codes: C09K 15/28 : containing nitrogen, oxygen and sulfur
• CPC Class Codes: C09K 23/00 : Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
• CPC Class Codes: C09K 8/00 : Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
• CPC Class Codes: C11C 3/00 : Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom sulfonated fats or oils C07C309/62; factice C08H; drying oils C09F
• CPC Class Codes: C11C 3/08 : with fatty acids
• CPC Class Codes: C11D 1/002 : Surface-active compounds containing sulfur SO3 and SO4, C11D1/12; sulfonium compounds C11D1/60; sulfoxides C11D1/755; sulfobetaines C11D1/92
• CPC Class Codes: C11D 1/04 : Carboxylic acids or salts thereof soap C11D9/00
• CPC Class Codes: C11D 1/28 : Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
• CPC Class Codes: C11D 1/29 : Sulfates of polyoxyalkylene ethers
• CPC Class Codes: C11D 1/62 : Quaternary ammonium compounds
• CPC Class Codes: C11D 1/652 : Mixtures of anionic compounds with carboxylic amides or alkylol amides
• CPC Class Codes: C11D 1/72 : Ethers of polyoxyalkylene glycols
• CPC Class Codes: C11D 1/74 : Carboxylates or sulfonates esters of polyoxyalkylene glycols
• CPC Class Codes: C11D 1/75 : Amino oxides
• CPC Class Codes: C11D 1/83 : Mixtures of non-ionic with anionic compounds
• CPC Class Codes: C11D 1/86 : Mixtures of anionic, cationic, and non-ionic compounds
• CPC Class Codes: C11D 1/88 : Ampholytes; Electroneutral compounds C11D1/002, C11D1/004, C11D1/008 take precedence
• CPC Class Codes: C11D 1/90 : Betaines
• CPC Class Codes: C11D 1/92 : Sulfobetaines ; Sulfitobetaines
• CPC Class Codes: C11D 1/94 : Mixtures with anionic, cationic or non-ionic compounds
• CPC Class Codes: C11D 3/30 : Amines; Substituted amines ; Quaternized amines
• CPC Class Codes: C11D 3/32 : Amides; Substituted amides
• CPC Class Codes: C11D 3/48 : Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions

Abstract

Laundry detergents useful for cold-water cleaning and boosted bargain detergents are disclosed. The detergents include a surfactant composition derived from a metathesis-derived C₁₀-C₁₇ monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives. For fatty alkyl ester sulfonate-containing detergents, the composition is selected from C₁₀ betaines, C₁₂ or C₁₆ amidoamines, C₁₂ ethanolamine amides, C₁₆ amidoamine sulfonates, C₁₈ diamidoamine dioxides, quaternized C₁₈ diamidoamine betaines, sulfonated C₁₈ low-EO fatty ester alkoxylates, C₁₈ amidoamine carboxylates, and amidoamine oxides and sulfobetaines derived from cross-metathesis of palm or soybean oil. The bargain detergents include a performance booster selected from C₁₂ low-EO fatty ester alkoxylate sulfonates, C₁₈ amidoamine oxide esters, C₁₈ amidoamine oxide carboxylates, and amidoamine sulfobetaines made from self metathesized palm or soybean oil.

Claims

1. A laundry detergent useful for cold-water cleaning, comprising 1 to 70 wt. % of an anionic surfactant, 5 to 70 wt. % of a nonionic surfactant, 3 to 25 wt. % of a fatty alkyl ester sulfonate, and 0.5 to 10 wt. % of a metathesis-based surfactant composition selected from the group consisting of

(a) a C₁₀ betaine having the structure:

2. The detergent of claim 1 wherein the nonionic surfactant is a fatty alcohol ethoxylate.

3. The detergent of claim 1 wherein the acid or ester metathesis-based surfactant composition has at least 1 mole % of trans-Δ

⁹ unsaturation.

4. A liquid, powder, paste, granule, tablet, molded solid, water-soluble sheet, or water-soluble sachet comprising the detergent of claim 1.

5. The detergent of claim 1 further comprising water.

6. A storage-stable liquid detergent of claim 5.

7. The detergent of claim 1 that is a liquid at 20°

C. and exhibits a phase transition below 5°

C.