Hard surface cleaners based on compositions derived from natural oil metathesis

• US 9,303,234 B2
• Filed: 10/25/2011
• Issued: 04/05/2016
• Est. Priority Date: 10/25/2010
• Status: Active Grant

• Current Assignee: Stepan Company
• Original Assignee: Stepan Company
• Inventors: Allen, Dave R., Bernhardt, Randal J., Brown, Aaron, Masters, Ronald A., Wolfe, Patrick Shane, Titievsky, Lena
• Primary Examiner(s): WEBB, GREGORY E
• Application Number:
  US13/879,792
• Publication Number:
  US 20130225469A1
• Time in Patent Office: 1,624 Days
• 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 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 41/03 : by reaction of oxirane rings with hydroxy groups
• CPC Class Codes: C07C 43/11 : Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
• CPC Class Codes: C07C 6/04 : at a carbon-to-carbon double bond
• CPC Class Codes: C07C 67/26 : with an oxirane ring
• 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 1/62 : Quaternary ammonium compounds
• CPC Class Codes: C11D 1/652 : Mixtures of anionic compounds with carboxylic amides or alkylol amides
• CPC Class Codes: C11D 1/74 : Carboxylates or sulfonates esters of polyoxyalkylene glycols
• CPC Class Codes: C11D 1/83 : Mixtures of non-ionic with anionic compounds
• 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 3/48 : Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions

Abstract

Aqueous hard surface cleaner compositions derived from metathesized natural oil feedstocks are disclosed. In one aspect, the compositions comprise at least one anionic surfactant derived from a metathesis-derived C10-C17 monounsaturated acid, 5 octadecene-1,18-dioic acid, or their ester derivatives. In another aspect, aqueous hard surface cleaners comprising at least one nonionic or amphoteric surfactant derived from a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives are disclosed. The aqueous cleaners noted above rival or outperform commercial baselines in a Gardner straight-line washability test. Industrial degreasers comprising a C10 or C12 amide solvent and derived from a metathesis-derived C10-C17 monounsaturated acid are superior to commercial standards.

Claims

1. A hard surface cleaner comprising 0.1 to 10 wt. % of at least one metathesis-based anionic surfactant selected from the group consisting of:

(a) C₁₀, C₁₂, C₁₆, or C₁₈ sulfonates having the structure;

2. The cleaner of claim 1 further comprising 0.1 to 10 wt. % of a nonionic or amphoteric surfactant.

3. The cleaner of claim 1 wherein the anionic surfactant is produced from an ester or acid reactant having at least 1 mole % of trans-Δ

⁹ unsaturation.

4. The cleaner of claim 1 further comprising 50 to 99 wt. % of water.

5. The cleaner of claim 1 further comprising 0.5 to 20 wt. % of an organic solvent.

6. The cleaner of claim 1 further comprising one or more additives selected from the group consisting of builders, buffers, abrasives, electrolytes, bleaching agents, fragrances, dyes, foaming control agents, antimicrobial agents, thickeners, pigments, gloss enhancers, enzymes, detergents, surfactants, cosolvents, dispersants, polymers, silicones, and hydrotropes.

7. A hard surface cleaner comprising 0.1 to 10 wt. % of at least one metathesis-based nonionic or amphoteric surfactant selected from the group consisting of:

(a) C₁₀ or C₁₂ amides having the structure;

8. The cleaner of claim 7 further comprising 0.1 to 10 wt. % of an anionic surfactant.

9. The cleaner of claim 7 further comprising 50 to 99 wt. % of water.

10. The cleaner of claim 7 further comprising 0.5 to 20 wt. % of an organic solvent.

11. An industrial degreaser comprising at least one metathesis-based solvent selected from the group consisting of C₁₀ or C₁₂ amides having the structure:

12. The degreaser of claim 11 comprising 2 to 20 wt. % of the C₁₀ or C₁₂ amide, 3 to 25 wt. % of a fatty amine oxide, and 55 to 95 wt. % of water.

13. The cleaner of claim 11 or the degreaser of claim 11 further comprising one or more additives selected from the group consisting of builders, buffers, abrasives, electrolytes, bleaching agents, fragrances, dyes, foaming control agents, antimicrobial agents, thickeners, pigments, gloss enhancers, enzymes, detergents, surfactants, cosolvents, dispersants, polymers, silicones, and hydrotropes.