Acyclic Carbon Chain Containing Carbon To Carbon Unsaturation Attached Directly To The Sulfate Group By Nonionic Bonding Patents (Class 558/36)
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Patent number: 11760889Abstract: Sulfate and sulfonate derivatives of unsaturated fatty alcohols, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester. The fatty alcohol composition is then converted to a sulfate or sulfonate derivative by one or more of alkoxylation, sulfation, sulfonation, and sulfitation. Of particular interest are the sulfate and ether sulfate derivatives. Microscopy studies indicate that the unsaturated sodium sulfates in particular have a lamellar phase that should enable formulation at high actives levels. Sulfate compositions comprising 40 to 60 wt. % of a monounsaturated fatty primary alcohol sulfate and 40 to 60 wt. % of a secondary hydroxyalkyl primary alcohol sulfate are also disclosed.Type: GrantFiled: July 15, 2020Date of Patent: September 19, 2023Assignee: Stepan CompanyInventors: David R. Allen, Marcos Alonso, Mary Beddaoui, Randal J. Bernhardt, Aaron Brown, Scott Dillavou, Xue Min Dong, Wilma Gorman, John C. Hutchison, Gary Luebke, Renee Luka, Franz Luxem, Andrew D. Malec, Ronald A. Masters, Dennis S. Murphy, Nicholas Pendleton, Irma Ryklin, Patti Skelton, Brian Sook, Chris Spaulding, Krista Turpin, Gregory Wallace, Michael Wiester, Patrick Shane Wolfe
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Patent number: 10745347Abstract: Sulfate and sulfonate derivatives of unsaturated fatty alcohols, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester. The fatty alcohol composition is then converted to a sulfate or sulfonate derivative by one or more of alkoxylation, sulfation, sulfonation, and sulfitation. Of particular interest are the sulfate and ether sulfate derivatives.Type: GrantFiled: March 13, 2013Date of Patent: August 18, 2020Assignee: STEPAN COMPANYInventors: David R. Allen, Marcos Alonso, Mary Beddaoui, Randal J. Bernhardt, Aaron Brown, Scott Dillavou, Xue Min Dong, Wilma Gorman, John C. Hutchison, Gary Luebke, Renee Luka, Franz Luxem, Andrew D Malec, Ronald A. Masters, Dennis S. Murphy, Nicholas Pendleton, Irma Ryklin, Patti Skelton, Brian Sook, Chris Spaulding, Krista Turpin, Gregory Wallace, Michael Wiester, Patrick Shane Wolfe
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Publication number: 20100240616Abstract: Omega-3 lipid compounds of the general formula (I): wherein R1 and R2 are the same or different and are chosen from a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, a carboxy group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; P represents a hydrogen atom, (Formula II) wherein P2, P3, and P4 are chosen from a hydrogen atom, an alkyl group, and a C14-C22 alkenyl group, wherein the alkyl and alkenyl groups are optionally substituted with a hydroxy group, (Formula III), (Formula IV), or (Formula V); and Y is a C14-C22 alkenyl group with at least one double bond, having E and/or Z configuration; or any pharmaceutically acceptable complex, solvate, salt or pro-drug thereof, with the proviso that R1 and R2 are not simultaneously a hydrogen atom.Type: ApplicationFiled: November 1, 2007Publication date: September 23, 2010Inventors: Anne Kristin Holmeide, Jenny Rosman
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Patent number: 7799859Abstract: A surfactant composition has good emulsifiability for monomer(s), and can provide a polymer emulsion (herein after simply called “the emulsion”) of good stability while decreasing coagulations of polymer particles in the emulsion. The surfactant composition contains the following components (A) and (B): (A) a reactive surfactant containing at least one polymerizable double-bond group and at least one ionic group in a molecule, and (B) a nitrogen compound insoluble or slightly soluble in ethanol. A weight ratio (A:B) of the component (A) to the component (B) is from 100:0.03 to 100:1.0.Type: GrantFiled: September 9, 2005Date of Patent: September 21, 2010Assignee: Adeka CorporationInventors: Kazushi Kobayashi, Koji Beppu
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Publication number: 20100010251Abstract: A process for the preparation of alkoxysulfates from organic compounds containing one or more nucleophilic groups by reacting said organic compound, in a water-miscible solvent selected from the group consisting of sulfur-containing solvents such as dimethylsulfoxide (DMSO) or sulfolane, or polar solvents such as tetrahydrofuran (THF), dimethylformamide (DMF), dimethylacetamide (DMA) and hexamethylphosphoric triamide (HMPT), with an alkylene sulfate, in a non-water-miscible solvent selected from the group consisting of chlorinated solvents such as methylene chloride, chloroform, carbon tetrachloride, trichloroethane or chlorinated aromatics, such as chlorobenzene or dichlorobenzene, and non-chlorinated aromatics, such as toluene or xylenes, in the presence of a base selected from the group consisting of hydroxides, carbonates and hydrogen carbonates of alkali metals or alkaline earth metals.Type: ApplicationFiled: July 9, 2009Publication date: January 14, 2010Inventors: Jan Hermen Hendrik MEURS, Jasper Roelf Smit, Arie Van Zon
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Patent number: 7423167Abstract: Disclosed are ethylenically unsaturated amine salts of sulfonic, phosphoric and carboxylic acids. The salts are surface active agents which are useful in a variety of applications as primary and/or secondary surfactants. The salts are especially useful as surfactants in emulsion polymerization reactions.Type: GrantFiled: November 1, 2004Date of Patent: September 9, 2008Assignee: Stepan CompanyInventor: Alfred K. Schultz
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Patent number: 7335787Abstract: The invention provides a high-yield method for producing onium salt derivatives useful as agents, such as acid-generators, employed in chemically amplified resists; and to provide novel onium salt derivatives. Reaction of an onium salt derivative containing a halide anion or a carboxylate anion with a sulfonic acid ester derivative or a phosphoric acid derivative provides an onium sulfate derivative or an onium phosphate derivative at high yield.Type: GrantFiled: September 11, 2003Date of Patent: February 26, 2008Assignee: Toyo Gosei Kogyo Co., Ltd.Inventors: Kyoichi Tomita, Shinji Ishii
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Patent number: 6620957Abstract: The invention provides a high-yield method for producing onium salt derivatives useful as agents, such as acid-generators, employed in chemically amplified resists; and to provide novel onium salt derivatives. Reaction of an onium salt derivative containing a halide anion or a carboxylate anion with a sulfonic acid ester derivative or a phosphoric acid derivative provides an onium sulfate derivative or an onium phosphate derivative at high yield.Type: GrantFiled: August 3, 2001Date of Patent: September 16, 2003Assignee: Toyo Gosei Kogyo Co., Ltd.Inventors: Kyoichi Tomita, Shinji Ishii
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Patent number: 6482860Abstract: The invention provides methods and compositions relating to novel pentafluorophenylsulfonamide derivatives and analogs and their use as pharmacologically active agents. The compositions find particular use as pharmacological agents in the treatment of disease states, particularly cancer, vascular restenosis, microbial infections, and psoriasis, or as lead compounds for the development of such agents.Type: GrantFiled: July 18, 1997Date of Patent: November 19, 2002Assignee: Tularik Inc.Inventors: John A. Flygare, Julio Cesar Medina, Bei Shan, David Louis Clark, Terry J. Rosen
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Patent number: 5446188Abstract: A process for the production of a highly concentrated fatty alcohol sulfate paste comprising the steps of: (1) forming a crude sulfonation product by reacting a mixture of an inert gas and sulfur dioxide with a mixture comprised of: (a) an unsaturated fatty alcohol of the formula IR.sup.1 --OH (I)wherein R.sup.1 is a linear unsaturated hydrocarbon radical having from 16 to 22 carbon atoms and 1, 2, or 3 double bonds, (b) a saturated fatty alcohol of the formula IIR.sup.2 --OH (II)wherein R.sup.2 is a linear or branched saturated hydrocarbon radical having from 12 to 22 carbon atoms; wherein the molar ratio of sulfur trioxide/fatty alcohol mixture is from 0.95:1 to 1.3:1 and (2) neutralizing, at a temperature of from 50.degree. C. to 90.degree. C., said crude sulfonation product with a quantity of aqueous base sufficient to form a water-containing fatty alcohol sulfate paste product having a solids content of from 60% to 70% by weight and a viscosity of less than 10 Pa.s at 60.degree. C.Type: GrantFiled: November 22, 1993Date of Patent: August 29, 1995Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Bert Gruber, Hermann Anzinger, Guenter Hendricks
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Patent number: 5349101Abstract: This invention relates to solid secondary alkyl sulfate-containing surface active compositions which are formed by crystallization and which contain at least about 80 percent by weight of secondary alkyl sulfate. These compositions are substantially free of unreacted organic matter and water. The invention further relates to a process for preparing these solid secondary alkyl sulfate-containing compositions.Type: GrantFiled: December 21, 1992Date of Patent: September 20, 1994Assignee: Shell Oil CompanyInventors: Eugene F. Lutz, David K. Schisla, Robert S. Tomaskovic, Timothy D. Hoewing
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Patent number: 5322957Abstract: Processes for the production of partial glyceride sulfates comprising the steps of:A) reacting a mixture containing glycerol and at least one triglyceride with gaseous sulfur trioxide to produce at least one acidic reaction product;B) ageing the at least one acidic reaction product at an elevated temperature; andC) neutralizing the at least one aged acidic reaction product with an aqueous base in the presence of a buffer.Type: GrantFiled: June 2, 1993Date of Patent: June 21, 1994Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Bernd Fabry, Uwe Ploog, Ansgar Behler, Dieter Feustel
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Patent number: 5037992Abstract: The present invention is directed to a process for sulfating unsaturated alcohols using inexpensive reagents and mild reaction conditions. The process comprises reacting an unsaturated alcohol of the formula R--OH, wherein R is a C.sub.8 -C.sub.22 alkenyl group, with an ether sulfate of the formula R.sup.1 (OCH.sub.2 CH.sub.2).sub.n OSO.sub.3 M, wherein R.sup.1 is a C.sub.1 -C.sub.18 hydrocarbyl group, n is an integer from 1 to 10, and M is an alkali metal, to form an unsaturated sulfate; said reaction being carried out in the presence of a catlaytically effective amount of an acid catalyst. The mole ratio of unsaturated alcohol reactant to ether sulfate ranges from about 0.5:1 to about 2:1. In this process the sulfation occurs primarily at the hydroxyl group of the unsaturated alcohol, with minimal sulfation at the olefinic moiety of said alcohol.Type: GrantFiled: December 18, 1989Date of Patent: August 6, 1991Assignee: The Procter & Gamble CompanyInventors: James F. Ward, Randall S. Matthews