WO2013162737A1 - Unsaturated fatty alcohol alkoxylates from natural oil metathesis - Google Patents

Unsaturated fatty alcohol alkoxylates from natural oil metathesis Download PDF

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Publication number
WO2013162737A1
WO2013162737A1 PCT/US2013/031060 US2013031060W WO2013162737A1 WO 2013162737 A1 WO2013162737 A1 WO 2013162737A1 US 2013031060 W US2013031060 W US 2013031060W WO 2013162737 A1 WO2013162737 A1 WO 2013162737A1
Authority
WO
WIPO (PCT)
Prior art keywords
fatty alcohol
alkoxylate
ethoxylate
monounsaturated
metathesis
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2013/031060
Other languages
English (en)
French (fr)
Inventor
David R. Allen
Marcos Alonso
Mary BEDDAOUI
Randal J. Bernhardt
Aaron Brown
Xue Min Dong
Wilma GORMAN
John C. Hutchison
Gary Luebke
Renee Luka
Franz Luxem
Andrew D. Malec
Ronald A. Masters
Dennis S. Murphy
Patti Skelton
Brian Sook
Chris SPAULDING
Michael Wiester
Patrick Shane Wolfe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Stepan Co
Original Assignee
Stepan Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to NZ701296A priority Critical patent/NZ701296A/en
Priority to CN201380033586.5A priority patent/CN104583248B/zh
Priority to ES13781311T priority patent/ES2824106T3/es
Priority to CA2871109A priority patent/CA2871109C/en
Priority to MX2014012908A priority patent/MX375230B/es
Priority to AU2013252874A priority patent/AU2013252874B2/en
Priority to IN2369KON2014 priority patent/IN2014KN02369A/en
Priority to EP13781311.9A priority patent/EP2841468B1/en
Priority to BR112014026542-9A priority patent/BR112014026542B1/pt
Priority to SG11201406872XA priority patent/SG11201406872XA/en
Application filed by Stepan Co filed Critical Stepan Co
Priority to US14/395,829 priority patent/US9708251B2/en
Publication of WO2013162737A1 publication Critical patent/WO2013162737A1/en
Priority to ZA2014/07749A priority patent/ZA201407749B/en
Priority to PH12014502388A priority patent/PH12014502388B1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/45—Anti-settling agents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B38/00—Porous mortars, concrete, artificial stone or ceramic ware; Preparation thereof
    • C04B38/10—Porous mortars, concrete, artificial stone or ceramic ware; Preparation thereof by using foaming agents or by using mechanical means, e.g. adding preformed foam
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • 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
    • C07C303/14—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 sulfoxidation, i.e. by reaction with sulfur dioxide and oxygen with formation of sulfo or halosulfonyl groups
    • 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
    • C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/08—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
    • C07C309/10—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/02—Preparation of ethers from oxiranes
    • C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
    • C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • C09K23/018—Mixtures of two or more different organic oxygen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
    • 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
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/143—Sulfonic acid esters
    • 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
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146—Sulfuric acid esters
    • 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
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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
    • C11D1/37—Mixtures of compounds all of which are anionic
    • 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
    • C11D1/66—Non-ionic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use

Definitions

  • Suitable metathesis-derived monounsaturated esters derive from carboxylic acids.
  • the esters derive from C5-C35 carboxylic acids, more preferably from C10-C17 carboxylic acids.
  • Example include esters derived from 9-decylenic acid (9- decenoic acid), 9-undecenoic acid, 9-dodecylenic acid (9-dodecenoic acid), 9- tridecenoic acid, 9-tetradecenoic acid, 9-pentadecenoic acid, 9-hexadecenoic acid, 9- heptadecenoic acid, and the like.
  • R is H or C2-C 7 alkyl
  • AO is an oxyalkylene group, preferably oxyethylene
  • n which is the average number of oxyalkylene groups, has a value within the range of
  • the alkoxylates are used as solvents, dispersants, surfactants, emulsifiers, wetting agents, formulation inerts, or adjuvants.
  • inventive alkoxylates are exceptionally useful as solvents and as nonionic emulsifiers for agricultural compositions.
  • the monounsaturated compositions are less likely to have the more troublesome gel phases (hexagonal, cubic, and paste); when they are present in the monounsaturated compositions, the ranges tend to be narrower.
  • A10-16 is isotropic and clear up to about 93% actives, with no cubic component, while its saturated analog exhibits a cubic phase at intermediate actives levels (37-55%); this should translate into a substantial advantage in handling and formulating for the unsaturated composition.
  • A12-13 and its saturated analog both have a hexagonal phase, but A12-13 has more generous isotropic regions (0-35%, 57-100%) and no lamellar component.
  • a neutral, dilutable all-purpose cleaner is prepared from propylene glycol n- propyl ether (4.0 g), butyl carbitol (4.0 g), sodium citrate (4.0 g), Stepanol® WA-Extra PCK (sodium lauryl sulfate, Stepan, 1 .0 g), test sample (0.90 g if 100% active material), and deionized water (to 100.0 g solution).
  • the control sample for nonionic/amphoteric testing replaces the test sample with Bio-Soft® EC-690 (ethoxylated alcohol, nominally 90% active material, Stepan, 1 .0 g).
  • the initiator shot is charged to the 83°C reaction kettle dropwise over 1 min, then held for 10 min.
  • the monomer emulsion is then fed to the kettle at 2.1 mL/min. for 10 min.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Toxicology (AREA)
  • Ceramic Engineering (AREA)
  • Structural Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
PCT/US2013/031060 2012-04-24 2013-03-13 Unsaturated fatty alcohol alkoxylates from natural oil metathesis Ceased WO2013162737A1 (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
BR112014026542-9A BR112014026542B1 (pt) 2012-04-24 2013-03-13 alcoxilato de álcool graxo, composição surfactante líquida, mistura, etoxilato de álcool graxo, emulsificador aniônico para composições agrícolas, solvente agrícola, limpador aquoso de superfície rígida, composição aditiva de revestimento ou de pintura, formulação de detergente de lavagem de roupa, espumificador, aditivo de espuma ou dispersante para uso em aplicações de gesso, concreto ou de combate a incêndios e composição surfactante para uso em recuperação aprimorada de petróleo
ES13781311T ES2824106T3 (es) 2012-04-24 2013-03-13 Alcoxilatos de alcoholes grasos insaturados a partir de la metátesis de aceites naturales
CA2871109A CA2871109C (en) 2012-04-24 2013-03-13 Unsaturated fatty alcohol alkoxylates from natural oil metathesis
MX2014012908A MX375230B (es) 2012-04-24 2013-03-13 Alcoxilatos de alcoholes grasos insaturados a partir de metátesis de aceites naturales.
AU2013252874A AU2013252874B2 (en) 2012-04-24 2013-03-13 Unsaturated fatty alcohol alkoxylates from natural oil metathesis
IN2369KON2014 IN2014KN02369A (cg-RX-API-DMAC7.html) 2012-04-24 2013-03-13
EP13781311.9A EP2841468B1 (en) 2012-04-24 2013-03-13 Unsaturated fatty alcohol alkoxylates from natural oil metathesis
NZ701296A NZ701296A (en) 2012-04-24 2013-03-13 Unsaturated fatty alcohol alkoxylates from natural oil metathesis
CN201380033586.5A CN104583248B (zh) 2012-04-24 2013-03-13 来自天然油歧化的不饱和脂肪醇烷氧基化物
SG11201406872XA SG11201406872XA (en) 2012-04-24 2013-03-13 Unsaturated fatty alcohol alkoxylates from natural oil metathesis
US14/395,829 US9708251B2 (en) 2012-04-24 2013-03-13 Unsaturated fatty alcohol alkoxylates from natural oil metathesis
ZA2014/07749A ZA201407749B (en) 2012-04-24 2014-10-23 Unsaturated fatty alcohol alkoxylates from natural oil metathesis
PH12014502388A PH12014502388B1 (en) 2012-04-24 2014-10-24 Unsaturated fatty alcohol alkoxylates from natural oil metathesis

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201261637607P 2012-04-24 2012-04-24
US61/637,607 2012-04-24

Publications (1)

Publication Number Publication Date
WO2013162737A1 true WO2013162737A1 (en) 2013-10-31

Family

ID=49483729

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2013/031060 Ceased WO2013162737A1 (en) 2012-04-24 2013-03-13 Unsaturated fatty alcohol alkoxylates from natural oil metathesis

Country Status (17)

Country Link
US (1) US9708251B2 (cg-RX-API-DMAC7.html)
EP (1) EP2841468B1 (cg-RX-API-DMAC7.html)
CN (1) CN104583248B (cg-RX-API-DMAC7.html)
AR (1) AR090329A1 (cg-RX-API-DMAC7.html)
AU (1) AU2013252874B2 (cg-RX-API-DMAC7.html)
BR (1) BR112014026542B1 (cg-RX-API-DMAC7.html)
CA (1) CA2871109C (cg-RX-API-DMAC7.html)
CO (1) CO7131392A2 (cg-RX-API-DMAC7.html)
ES (1) ES2824106T3 (cg-RX-API-DMAC7.html)
IN (1) IN2014KN02369A (cg-RX-API-DMAC7.html)
MX (2) MX375230B (cg-RX-API-DMAC7.html)
MY (1) MY169208A (cg-RX-API-DMAC7.html)
NZ (1) NZ701296A (cg-RX-API-DMAC7.html)
PH (1) PH12014502388B1 (cg-RX-API-DMAC7.html)
SG (1) SG11201406872XA (cg-RX-API-DMAC7.html)
WO (1) WO2013162737A1 (cg-RX-API-DMAC7.html)
ZA (1) ZA201407749B (cg-RX-API-DMAC7.html)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016169734A1 (de) * 2015-04-24 2016-10-27 Henkel Ag & Co. Kgaa Kosmetische mittel enthaltend alkoxylierte fettalkohole mit trans-ständigen doppelbindungen

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Publication number Priority date Publication date Assignee Title
CN103649293A (zh) * 2011-07-10 2014-03-19 艾勒旺斯可再生科学公司 多用途的金属皂组合物
EP4063761A1 (en) * 2015-03-30 2022-09-28 Carrier Corporation Low-oil refrigerants and vapor compression systems
WO2016178840A1 (en) * 2015-05-04 2016-11-10 Elevance Renewable Sciences, Inc. Olefin compositions and their use as cleaning agents
EP3969555A1 (en) 2019-06-21 2022-03-23 Ecolab USA, Inc. Solid nonionic surfactant compositions
US20230173074A1 (en) * 2020-04-23 2023-06-08 Pleryon Therapeutics (Shenzhen) Limited Biocompatible material and methods for making and using the same
AU2021268691A1 (en) * 2020-05-05 2022-12-22 Oxiteno S.A. Indústria E Comércio Alkylphenol-free reactive nonionic surfactant, process to obtain the alkylphenol-free reactive nonionic surfactant, latexes obtained by emulsion polymerization, water-based coating composition with high water resistance, and use of water-based coating composition
CN112143579B (zh) * 2020-09-15 2021-07-27 广州玮弘祺生物科技有限公司 一种沥青清洗剂及其制备方法
CN112646168A (zh) * 2020-12-22 2021-04-13 赞宇科技集团股份有限公司 一种提升脂肪醇聚氧乙烯醚硫酸钠溶解性能的方法及设备

Citations (27)

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US2865968A (en) 1955-05-06 1958-12-23 Nat Distillers Chem Corp Production of fatty alcohols
US3193586A (en) 1955-08-22 1965-07-06 Dehydag Gmbh Process for the production of unsaturated fatty alcohols
US4545941A (en) 1983-06-20 1985-10-08 A. E. Staley Manufacturing Company Co-metathesis of triglycerides and ethylene
US4804790A (en) 1983-07-14 1989-02-14 Henkel Kommanditgesellschaft Auf Aktien Process for obtaining fatty alcohols from free fatty acids
US5124491A (en) 1987-07-22 1992-06-23 Henkel Kommanditgesellschaft Auf Aktien Process for the hydrogenation of fatty acid methyl esters
US5312940A (en) 1992-04-03 1994-05-17 California Institute Of Technology Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization
US5482908A (en) 1994-09-08 1996-01-09 Arco Chemical Technology, L.P. Highly active double metal cyanide catalysts
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