Acyclic Carbon To Carbon Unsaturation Containing Patents (Class 564/288)
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Publication number: 20130225409Abstract: Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amines, wherein the fatty amine is made by reducing the amide reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and a secondary amine, are disclosed. Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amidoamines, wherein the amidoamine is made by reacting of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and an aminoalkyl-substituted tertiary amine, are also disclosed. The quaternized compositions are advantageously sulfonated or sulfated. In one aspect, the ester derivative of the C10-C17 monoun-saturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin.Type: ApplicationFiled: October 25, 2011Publication date: August 29, 2013Applicant: Stepan CompanyInventors: Dave R. Allen, Marcos Alonso, Randal J. Bernhardt, Aaron Brown, Sangeeta Ganguly-Mink, Andrew D. Malec, Teresa Manuel, Ronald A. Masters, Lawrence A. Munie, Dennis S. Murphy, Patti Skelton, Brian Sook, Michael R. Terry, Jeremy Aaron Weitgenant, Laura Lee Whitlock, Michael Wiester, Patrick Shane Wolfe
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Publication number: 20130137011Abstract: Ionomers comprising ionic groups such as, for example, tetraalkylammonium groups and methods of making such ionomers. For example, the ionomers can be produced by ring opening metathesis polymerization of alkene-containing monomers with tetraalkylammonium groups and, optionally, alkene-containing monomers without tetraalkylammonium groups. The ionomers can be used in applications such as, for example, fuel cell applications.Type: ApplicationFiled: May 31, 2010Publication date: May 30, 2013Applicant: Cornell UniversityInventors: Geoffrey W. Coates, Henry A. Kostalik, IV, Timothy J. Clark, Nicholas J. Robertson
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Publication number: 20120310022Abstract: The present invention relates to a composition and method for inhibiting the formation of naphthenate solids in a liquid hydrocarbon. The method includes contacting a composition including a rosin amine having a formula (I): or (II): where formula (AA): represents a single or double bond; R1, R2 and R5 each independently represent H, alkyl, alkenyl or an alkynyl group each having between one and ten carbon atoms, —(R3O)nR4 wherein R3 is an alkyl group having 1 to 3 carbon atoms and R4 is H, alkyl, alkenyl or an alkynyl group each having between one and ten carbon atoms; n is an integer between 5 and 50; X is a halide, sulphate, phosphate or acetate ion; and a demulsifier intermediate with the liquid hydrocarbon.Type: ApplicationFiled: November 25, 2010Publication date: December 6, 2012Inventors: Chandrashekhar Khandekar, Suguna Gopal, James Smith
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Publication number: 20110201598Abstract: A class of compounds useful in pharmaceutical compositions and methods for treating or preventing cancer is described. The compounds' ability to inhibit RET kinase is quantified, i.e., their respective RET IC50 and EC50 values are described. One such compound, known as cyclobenzaprine and herein as SW-01, has been identified as RET-specific with an IC50 of 300 nM. SW-01 inhibits RET autophosphorylation and blocks the growth and transformation of thyroid cancer cell lines. It has been further tested in pancreatic cancer, breast cancer, and SCLC cell lines. The compounds show utility for inhibition of survival and proliferation of tumour cells.Type: ApplicationFiled: July 14, 2009Publication date: August 18, 2011Inventors: Taranjit S. Gujral, Lois M. Mulligan, Vinay K. Singh
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Publication number: 20110202942Abstract: An aspect of the present invention relates to an optical information recording medium comprising a recording layer, wherein the recording layer comprises a cationic dye and a polynuclear azo metal complex dye comprising an azo dye and a metal ion, and a method of recording information comprising recording information on the recording layer comprised in the optical recording medium, and conducting the recording by irradiation of a laser beam having a wavelength of equal to or shorter than 440 nm onto the optical information recording medium. Another aspect of the present invention relates to a photo sensitizer.Type: ApplicationFiled: October 9, 2009Publication date: August 18, 2011Applicant: FUJIFILM CORPORATIONInventors: Taisuke Fujimoto, Kousuke Watanabe, Taro Hashizume
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Patent number: 7893302Abstract: The present invention relates to novel cationic lipids, transfection agents, microparticles, nanoparticles, and short interfering nucleic acid (siNA) molecules. The invention also features compositions, and methods of use for the study, diagnosis, and treatment of traits, diseases and conditions that respond to the modulation of gene expression and/or activity in a subject or organism. Specifically, the invention relates to novel cationic lipids, microparticles, nanoparticles and transfection agents that effectively transfect or deliver biologically active molecules.Type: GrantFiled: November 12, 2009Date of Patent: February 22, 2011Assignee: Sirna Therapeutics, Inc.Inventors: Tongqian Chen, Chandra Vargeese, Kurt Vagle, Weimin Wang, Ye Zhang
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Patent number: 7863485Abstract: An environmentally safe additive and vehicle system are provided for water-based and oil-based printing inks, paints, coatings and adhesives which can be rapidly transferred, dispersed, dispensed, spread, dried and cured. The low cost, stable additive and vehicle system enhance multiple color, high speed printing with sharp, highly defined images and superior quality, and can be used on many different types of substrates, such as paper, paperboard, cardboard, clay coated board, foil, plastic, glass, metal, wood and composites. The additive may be formed by the reaction product of a photoinitiator, such as an UV-activated polyelectrolyte, and a monomer, such as an acrylate or a methacrylate in an aqueous solution. In other embodiments, the additive is formed from a carboxylic acid or anhydride and alkylalkanolamine monomer or a dialkylaminoalkyl acrylate or methacrylate monomer in an aqueous solution.Type: GrantFiled: December 10, 2004Date of Patent: January 4, 2011Assignee: Omnitech Environmental, LLCInventors: Leroy John Cook, Richard T. Skov
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Publication number: 20100168068Abstract: The invention provides novel compounds of formulae I and II: that are monoamine oxidase-B inhibitors, which can be useful in treating obesity, diabetes, and/or cardiometabolic disorders (e.g., hypertension, dyslipidemias, high blood pressure, and insulin resistance).Type: ApplicationFiled: December 31, 2009Publication date: July 1, 2010Applicant: JENRIN DISCOVERYInventors: John Francis McElroy, Robert J. Chorvat, Parthasarathi Rajagopalan
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Patent number: 7598420Abstract: The subject invention provides a pharmaceutical composition comprising N-propargyl-1(R)-aminoindan mesylate; a pharmaceutically acceptable carrier; and greater than 0.7 ppm but less than 30 ppm in total of a compound having the structure: and any salts of the compound.Type: GrantFiled: September 8, 2008Date of Patent: October 6, 2009Assignee: Teva Pharmaceutical Industries, Ltd.Inventors: Jeffrey Sterling, David Lerner, Harel Rosen, Leonid Bronov, Dalia Medini-Green, Berta Iosefzon, Tirtsah Berger-Peskin, Ramy Lidor-Hadas, Eliezer Bahar
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Publication number: 20090074709Abstract: A method of applying a biocidal polymer to a surface including applying a solution of the biocidal polymer to the surface, wherein the biocidal polymer includes biocidal groups and the biocidal polymer is insoluble in water. The biocidal groups can be selected from the group consisting of quaternary salt groups or haloamino groups.Type: ApplicationFiled: September 12, 2008Publication date: March 19, 2009Inventors: RICHARD R. KOEPSEL, ALAN J. RUSSELL, THANGAPPAN RAVIKUMAR
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Patent number: 7371887Abstract: Amphiphilic oligo(p-phenylene vinylene) compounds and methods of use en route to self-assembled composites and device fabrication.Type: GrantFiled: December 6, 2004Date of Patent: May 13, 2008Assignee: Northwestern UniversityInventors: Samuel I. Stupp, James F. Hulvat, Marina Sofos, Keisuke Tajima
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Patent number: 7300747Abstract: The photobase generator of the invention is represented by the following formula 1: wherein Ar, R, A+ and X? are as defined in the specification. Since the photobase generator of the formula 1 absorbs ultraviolet lights of relatively long wavelength and is photolyzed to generate a strong base efficiently, a composition containing the photobase generator and an episulfide compound is easily cured by polymerization under ultraviolet irradiation.Type: GrantFiled: February 7, 2005Date of Patent: November 27, 2007Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hitoshi Okazaki, Junya Hayakawa, Motoharu Takeuchi, Masahiro Jono, Kenji Ishii
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Patent number: 7045139Abstract: An efficient, simple, high yielding, eco-friendly process for the manufacture of tosylates quaternary ammonium salts of cinnamidoalkylamines and/or benzamidoalkylamines (Formula I) has been described. These compounds are substantive UV-absorbers. They are useful in making fabric care products and personal care products. The scope of this methodology has been demonstrated by converting water soluble organic sunscreen quaternary halides to their corresponding tosylates of Formula VI.Type: GrantFiled: October 8, 2003Date of Patent: May 16, 2006Assignee: Galaxy Surfactants LimitedInventors: Nirmal Madhukar Koshti, Shubhangi Dattaram Naik, Bharat Bhikaji Parab, Tanaji Shamrao Jadhav, Subhash Shivling Nashte
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Patent number: 6967258Abstract: A quaternary ammonium hydroxycarboxylate is produced by quaternizing a tertiary amine with a hydroxycarboxylic ester represented by the following Formula 1: wherein R1 to R3 are as defined in the disclosure. By using only one tertiary amine having at least one substituent different from R1 of the ester moiety of the hydroxycarboxylic ester and by controlling the reaction conditions, a mixture of quaternary ammonium hydroxycarboxylates having different quaternary ammonium ions is produced. By reacting an inorganic acid with the quaternary ammonium hydroxycarboxylate or its mixture, a quaternary ammonium salt of inorganic acid or its mixture is produced.Type: GrantFiled: May 7, 2004Date of Patent: November 22, 2005Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yutaka Kanbara, Yasushi Higuchi, Tomoo Tsujimoto, Genki Nogami
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Patent number: 6784317Abstract: A quaternary ammonium hydroxycarboxylate is produced by quaternizing a tertiary amine with a hydroxycarboxylic ester represented by the following Formula 1: wherein R1 to R3 are as defined in the disclosure. By using only one tertiary amine having at least one substituent different from R1 of the ester moiety of the hydroxycarboxylic ester and by controlling the reaction conditions, a mixture of quaternary ammonium hydroxycarboxylates having different quaternary ammonium ions is produced. By reacting an inorganic acid with the quaternary ammonium hydroxycarboxylate or its mixture, a quaternary ammonium salt of inorganic acid or its mixture is produced.Type: GrantFiled: April 19, 2002Date of Patent: August 31, 2004Assignee: Mitsubishi Gas Chemical Company, IncInventors: Yutaka Kanbara, Yasushi Higuchi, Tomoo Tsujimoto, Genki Nogami
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Patent number: 6613340Abstract: Substantive UV absorbing organic-soluble quaternary salts of cinnamidoalkylamine are described. Hair, skin and fabric care compositions containing the compounds of formula I. wherein R1 is a substituent, selected from H, halo, —OH, —NH2, —NO2, —OCH3, —N(CH3)2, alkyl groups containing from 1 to 6 carbon atoms, alkoxy groups containing from 1 to 6 carbon atoms, alkylamino or N,N-dialkylamino groups containing from 1 to 6 carbon atoms; R2 is selected from hydrogen, alkyl group containing from 1 to 12 carbon atoms; R3 and R4 are independently selected from benzyl, alkyl group containing from 1 to 12 carbon atoms; n is an integer from 1 to 6; R5 is selected from an alkyl group containing from 8 to 22 carbon atoms; alkenyl groups containing from 8 to 22 carbon atoms; R7 is selected from bromo, chloro, nitro, methyl and ethyl groups.Type: GrantFiled: July 31, 2001Date of Patent: September 2, 2003Assignee: Galaxy Surfactants Ltd.Inventors: Nirmal Madhukar Koshti, Arun Harchandra Jawale, Bharat Bhikaji Parab, Shubhangi Dattaram Naik, Manasi Dattatraya Moghe, Tanaji Shamrao Jadhav, Subhash Shivling Nashte
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Patent number: 6521782Abstract: The present invention relates to a process for the manufacture of aqueous solutions of unsaturated quaternary ammonium salts. The salts can correspond to the following formula (I): in which R represents a methyl or benzyl radical, by reaction, in the presence of water, of N,N-dimethyl-amninoethyl acrylate (DAMEA) with a quaternizing agent of formula (II): R—Cl (II) in which R is as defined above. Generally, the reaction is carried out in a closed reactor, which includes all the DAMEA and has been pressurized by air or depleted air to 0.5 to 3 bar, by continuously introducing, at a temperature of 35 to 65° C., the quatenlizing agent (II) and the water, until a concentration of salt (I) in the water is obtained. The water starts to be introduced beginning when 0-20% of the amount by weight of the quaternizing agent (II) necessary for the reaction has been added and it being possible for the pressure at the end of the reaction to reach 9 bar.Type: GrantFiled: September 27, 2001Date of Patent: February 18, 2003Assignee: AtofinaInventors: Alain Riondel, Gilles Herbst, Marc Esch, Eric Delaunay, Peter Meyer
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Patent number: 6303723Abstract: A process for preparing polymers of allylic amine compounds comprising: a) preparing a reaction mixture comprising: i) a polar reaction solvent; ii) at least one salt of an allylic amine compound; and iii) a free radical initiator comprising a water soluble non-ionic diazo compound represented by: wherein: R1, R2, R3 and R4 are the same or different lower alkyl groups; R5 and R6 are each independently selected from the group consisting of hydroxyalkyl amide or hydroxyalkyl ester; and b) polymerizing the reaction mixture.Type: GrantFiled: October 27, 1999Date of Patent: October 16, 2001Assignee: Penn State Research FoundationInventors: Ayusman Sen, Shengsheng Liu
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Patent number: 6087303Abstract: Wood preservative systems comprising (a) a biocidal effective amount of (i) at least one di C.sub.8 -C.sub.12 alkyl quaternary ammonium carboxylate having the formula ##STR1## wherein R.sup.1 and R.sup.2 are a C.sub.8 -C.sub.l2 alkyl group; R.sup.3 is a substituted or unsubstituted, interrupted or uninterrupted C.sub.1 -C.sub.100 group; l and q independently are 1, 2 or 3 and (l) (q) is 1, 2, or 3; and n is 0 or an integer from 1 to 50; (ii) at least one di C.sub.8 -C.sub.12 alkyl quaternary ammonium borate having the formula ##STR2## wherein R.sup.1 and R.sup.2 are defined as above, and a is 2 or 3, but when a is 2, b is 0 or 1, and when a is 3, b is 0, 1, or 2; or (iii) a combination of (i) and (ii); and (b) a solvent are provided. These carboxylate quats as well as carboxylate quats wherein R.sup.1 is a C.sub.1 -C.sub.20 alkyl or aryl-substituted alkyl group and R.sup.2 is a C.sub.8 -C.sub.20 alkyl group are preferably prepared by an indirect or a direct synthesis.Type: GrantFiled: July 10, 1997Date of Patent: July 11, 2000Assignee: Lonza, Inc.Inventor: Leigh E. Walker
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Patent number: 5846907Abstract: Pyrazol-4-ylbenzoyl compounds of the formula I ##STR1## where Z is a 5- or 6-membered heterocyclic saturated or unsaturated radical, Q is a pyrazole ring and L and M are as defined in the specification, their use as herbicidal compounds and to processes for preparing the compounds.Type: GrantFiled: July 30, 1997Date of Patent: December 8, 1998Assignee: BASF AktiengesellschaftInventors: Wolfgang von Deyn, Regina Luise Hill, Uwe Kardorff, Stefan Engel, Martina Otten, Marcus Vossen, Peter Plath, Harald Rang, Albrecht Harreus, Hartmann Konig, Helmut Walter, Karl-Otto Westphalen, Ulf Misslizt
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Patent number: 5763610Abstract: A composition comprising a nitrogen-containing olefinic compound and a process for using the nitrogen-containing olefinic compound to produce a water-soluble polymer which has applications in a subterranean formation are provided. The nitrogen-containing olefinic compound can be made from an amine and an alkylating agent. The polymer produced can be used in drilling fluids, workover fluids, completion fluids, permeability corrections, water or gas coning prevention, fluid loss prevention, matrix acidizing, fracture acidizing, and combinations of any two or more thereof.Type: GrantFiled: February 21, 1997Date of Patent: June 9, 1998Assignee: Phillips Petroleum CompanyInventors: Iqbal Ahmed, Ahmad Moradi-Araghi, Odd Ivar Eriksen
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Patent number: 5696292Abstract: Process for the preparation of quaternary ammonium compounds, by preparing a mixture of a tertiary amine and a liquid reaction vehicle and adding an alkyl halide to the mixture to produce a quaternary ammonium halide, the liquid reaction medium being a liquid, low volatility, substantially non-toxic diluent having a vapor pressure not greater than about 1 mm. Hg at a temperature of 25.degree. C. and preferably being a fatty acid or a fatty acid mono-, di-, or triglyceride, a mineral oil, or 2-ethylhexanol wherein the alkyl groups comprising the fatty acids or the triglycerides have from about 10 to about 24 carbon atoms, the quaternary ammonium compounds being particularly suited for uses such as deinking of paper in conjunction with appropriate clays, surfactants, flotation agents, anti-static agents and biocides.Type: GrantFiled: February 10, 1995Date of Patent: December 9, 1997Assignees: Witco Corporation, Rheox, Inc.Inventors: Charles Cody, N. Ben Martin
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Patent number: 5625089Abstract: Anilines of the formula ##STR1## where rings A and B may each be benzofused,X is a bridge member,R.sup.1 and R.sup.2 are each hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, hydroxysulfonyl, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl or C.sub.1 -C.sub.4 -alkylsulfonyl,R.sup.3 is hydrogen, amino, C.sub.1 -C.sub.4 -alkanoylamino or nitro, andY is vinyl or a radical of the formula C.sub.2 H.sub.4 --Q, where Q is a group detachable under alkaline reaction conditions.Type: GrantFiled: February 28, 1996Date of Patent: April 29, 1997Assignee: BASF AktiengesellschaftInventor: Manfred Patsch
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Patent number: 5574054Abstract: Novel quaternary ammonium salts having utility in the medical field for treating gastrointestinal disorders.Type: GrantFiled: January 12, 1995Date of Patent: November 12, 1996Assignee: Zeria Pharmaceutical Co., Ltd.Inventors: Osamu Kitagawa, Katsuyuki Ishii, Seiichi Niwa, Sigeru Ueki, Masao Seiki
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Patent number: 5550163Abstract: A method for reducing filtrate waste in a manufacturing process of a pharmaceutical product containing benzalkonium chloride as a preservative generally includes the steps of mixing the non-benzalkonium chloride components with benzalkonium chloride to formulate the product and thereafter sterilizing the product by passing same through a microfiltration membrane. In processes in which the product has a time dependent benzalkonium chloride content due to benzalkonium chloride adsorption on a microfiltration membrane, an amount of benzalkonium chloride wasted can be reduced by maintaining a selected temperature of the microfiltration membrane and the product therein.Type: GrantFiled: August 3, 1994Date of Patent: August 27, 1996Assignee: Allergan, Inc.Inventors: Shulin Ding, Robert J. Pallo, Walter L. Tien, Orest Olejnik
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Patent number: 5510532Abstract: Conductive polymers having repeating units of formula (II) ##STR1## formed by chemical or electrochemical oxidation of aniline derivatives of formula (I) ##STR2## wherein R.sub.1 denotes --(CH.sub.2).sub.n --; n is an integer between 2 and 12; R.sub.2, R.sub.3, R.sub.4 and R.sub.5 denote hydrogens or one or two of them can be a halogen atom, methyl, methoxy or nitro groups; and X denotes hydrogen an alkali metal ion, an ammonium ion, an alkyl ammonium ion or an anilinium ion. The conductive polymers have excellent stability toward electrochemical redox cyclization and good processibility.Type: GrantFiled: December 7, 1993Date of Patent: April 23, 1996Assignee: Korea Research Institute of Chemical TechnologyInventors: Suh B. Rhee, Myong-Hoon Lee, Chang-Jin Lee, Bong S. Moon
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Patent number: 5373025Abstract: A sanitizer composition comprising a bactericidal effective amount of the combination of (a) a quaternary ammonium compound selected from the group consisting of (hydrogenated tallow) 2-ethylhexyl dimethyl ammonium salt, dicoco dimethyl ammonium salt, and mixtures thereof; and (b) a copper (II) ion source.Type: GrantFiled: June 14, 1993Date of Patent: December 13, 1994Assignee: Olin CorporationInventor: Walter A. Gay
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Patent number: 5362910Abstract: A germicidal and fungicidal agent can solve the problems of conventional germicidal and fungicidal agents comprising quaternary ammonium salts or amphoteric surface active agents that fungicidal activity is insufficient and metals such as parts of medical instruments are corroded. Furthermore, it has higher germicidal and fungicidal activity against Gram-negative bacteria and filamentous fungi than benzalkonium chloride and excellent safety for human health. It is advantageously applied as a disinfectant for medical uses, a disinfectant for environment, a germicidal and fungicidal agent for fibers, a germicidal and fungicidal agent for cycling cooling water and the like. It has excellent resistance against discoloration, heat resistance, corrosion preventing property and compatibility with anionic surface active agents and can be used for providing all kinds of fibers with the germicidal and fungicidal activity to replace silicone type quaternary ammonium salts.Type: GrantFiled: July 24, 1992Date of Patent: November 8, 1994Assignee: Nicca Chemical Co., Ltd.Inventors: Masahiro Makino, Mikihiko Kurose, Yoshihiro Sasada
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Patent number: 5349106Abstract: A process for reducing the residual content of free alkylating agent in aqueous solutions of cationic surfactants comprising aftertreating the solutions with at least one of the following amine compounds:a) ammonia;b) tertiary amine corresponding to the general formula (I) ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 independently of one another represents linear or branched, optionally hydroxy-substituted alkyl radicals containing 1 to 18 carbon atoms or an alkenyl radical containing 8 to 18 carbon atoms;c) amino acids containing 2 to 8 carbon atoms; andd) oligopeptides having an average molecular weight of about 500 to about 5000,at an elevated temperature.Type: GrantFiled: February 18, 1993Date of Patent: September 20, 1994Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Ansgar Behler, Uwe Ploog, Hermann Hensen, Guenter Uphues
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Patent number: 5290806Abstract: 4-4(tert-butylphenyl)-cyclohexylamines and quaternary ammonium salts thereof of the formulae ##STR1## where R.sup.1 is hydrogen, alkyl or alkenyl,R.sup.2 is alkyl, haloalkyl, hydroxyalkyl, cycloalkyl, alkylcycloalkyl, bicycloalkyl, alkenyl, unsubstituted or mon- to trisubstituted phenyl, or unsubstituted or mono- to trisubstituted phenylalkyl,X.crclbar. is a plant-tolerated acid anion,and their plant-tolerated acid addition salts, and fungicides containing these compounds.Type: GrantFiled: July 2, 1993Date of Patent: March 1, 1994Assignee: BASF AktiengesellschaftInventors: Bernhard Zipperer, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5258409Abstract: A sanitizing composition for aqueous solutions comprising an dialiphatic dimethylammonium salt having an effective bactericidal activity at a concentration below about 50 ppm by weight in the medium to be sanitized during a maximum contact time not exceeding 60 seconds.Type: GrantFiled: February 24, 1992Date of Patent: November 2, 1993Assignee: Olin CorporationInventor: Walter A. Gay
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Patent number: 4982006Abstract: The present invention involves process for the preparation of compounds having the chemical structure: ##STR1## wherein Ar--H is an aromatic compound which is activated to an electrophilic attack, and wherein --Y is an aliphatic group having a labile moiety, especially where the labile moiety is a terminally unsaturated moiety: --C.tbd.CH, ##STR2## or aldehydes in the form of their acetals. The process comprises the step of reacting Ar--H and ##STR3## wherein --X is --Cl or --Br, and where the reaction step is carried out in a solvent medium at a temperature of from about -40.degree. C. to about -100.degree. C. using stannic chloride as a catalyst.Type: GrantFiled: May 1, 1989Date of Patent: January 1, 1991Assignee: Norwich Eaton Pharmaceuticals, Inc.Inventor: Thomas T. Hudec
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Patent number: 4871874Abstract: Alkadienes are produced by reacting alkenyltrialkylammonium halide in which the double bond is allylic or homoallylic relative to the nitrogen atom with a strong inorganic base under phase transfer conditions. In this reaction trialkylamine is eliminated from the quaternary ammonium halide thereby resulting in the concurrent formation of the alkadiene. Long chain (e.g., C.sub.6 -C.sub.20) conjugated alkadienes, can readily be prepared from the corresponding alkenes in good yields on an economical basis by a three-stage process involving:(a) allylically monobrominating an alkene in the liquid phase;(b) converting the allylically monobrominated alkene into alkenyl quaternary ammonium bromide by reaction with a trialkyl amine; and(c) reacting the alkenyl quaternary ammonium bromide with a strong inorganic base under phase transfer conditions so that conjugated alkadiene and trialkylamine are formed.Type: GrantFiled: June 15, 1987Date of Patent: October 3, 1989Assignee: Ethyl CorporationInventor: Joachim W. Wolfram
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Patent number: 4725602Abstract: Acetylenes of the following formula (I): ##STR1## wherein Y, m, R.sup.1, R.sup.2, R.sup.3, n and R.sup.4 are defined herein and R.sup.5 is hydrogen, alkyl, cycloalkyl or substituted alkyl are useful vasodilators and antihypertensives.Type: GrantFiled: October 24, 1985Date of Patent: February 16, 1988Assignee: McNeilab, Inc.Inventor: John R. Carson
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Patent number: 4705860Abstract: Quaternary ammonium salts of the formulaR.sub.1 --K.sup..sym. A.sup..crclbar.in whichR.sub.1 denotes C.sub.12 -C.sub.26 -alkyl or C.sub.12 -C.sub.26 -alkenyl,K.sup..sym. denotes a group of the formula ##STR1## or --.sup..sym. N(R.sub.2).sub.3, R.sub.2 denotes C.sub.1 -C.sub.3 -alkyl, preferably methyl, and A.sup..crclbar. denotes an anion of one of the following formulae: R.sub.3 SO.sub.3.sup..crclbar., in which R.sub.3 is C.sub.6 -C.sub.9 -alkyl or alkenyl and the sum of C atoms in R.sub.1 and R.sub.3 should be at least 21; ##STR2## in which Hal is fluorine, chlorine, bromine or iodine, R.sub.4 is C.sub.1 -C.sub.5 -alkyl, C.sub.2 -C.sub.5 -alkenyl or C.sub.1 -C.sub.5 -alkoxy in positions 3, 4, 5 or 6, R.sub.5 is hydrogen or hydroxyl in positions 2 or 3, R.sub.6 is COO.sup.- or SO.sub.3.sup.- and R.sub.7 is hydrogen or methyl, with the exception of the salicylate and m-halogenobenzoate ions when combined with C.sub.16 -alkylpyridinium and C.sub.16 -alkyltrimethylammonium.Type: GrantFiled: March 11, 1986Date of Patent: November 10, 1987Assignee: Hoechst AktiengesellschaftInventors: Dieter Ohlendorf, Heinz Hoffmann, Werner Interthal, Ulrich Pintschovius
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Patent number: 4602087Abstract: The distyrylbiphenyls of the formula ##STR1## in which X and X' independently of one another are a direct bond, oxygen, sulfur, --O--C.sub.1-3 -alkylene-CON(R.sub.4)--CON(R.sub.4)--, --O--C.sub.1-3 alkylene-COO--, OCO or --COO--, with the proviso that if n+n'=O, X and X' may not be --CON(R.sub.4)-- or O--C.sub.1-3 -alkylene-CON(R.sub.4)--, and if n+n'=2 and X and X' are --CON(R.sub.4)-- or --COO--, A.sup..crclbar. may not be a phosphite or phosphonate anion, and Y and Y' independently of one another are C.sub.1-20 -alkyene, R.sub.1 and R.sub.1 ' independently of one another are unsubstituted or substituted C.sub.1-8 -alkyl or C.sub.3-4 -alkenyl, R.sub.1 together with R.sub.2, or R.sub.1 ' together with R.sub.2 ', is a heterocyclic ring, R.sub.2 and R.sub.2 ' independently of one another are unsubstituted or substituted C.sub.1-8 -alkyl or C.sub.3-4 -alkenyl, or R.sub.2 together with R.sub.1, or R.sub.2 ' together with R.sub.1 ', is a heterocyclic ring, or R.sub.1 and R.sub.2, or R.sub.1 ' and R.sub.Type: GrantFiled: May 18, 1984Date of Patent: July 22, 1986Assignee: Ciba-Geigy CorporationInventors: Christian Luthi, Hans R. Meyer, Kurt Weber
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Patent number: 4599335Abstract: Diamine derivatives of the formula ##STR1## where R.sup.1 is unsubstituted or substituted alkyl, unsubstituted or substituted aryl or aralkyl, bicycloalkyl, alkoxy, acyl or halogen, n is 0, 1, 2 or 3, R.sup.2 is alkyl, alkenyl or alkoxy, A is unsubstituted or substituted alkylene or unsubstituted or substituted cycloalkylene, R.sup.3, R.sup.4 and R.sup.5 are each unsubstituted or substituted alkyl, alkenyl, alkynyl or unsubstituted or substituted benzyl, or R.sup.3 and R.sup.4, together with A and the two nitrogen atoms bonded to A, form an unsubstituted or substituted piperazine or perhydrodiazepine ring, or R.sup.4 and R.sup.5, together with the nitrogen atom, form an unsubstituted or substituted heterocyclic ring, R.sup.6 is alkyl, alkenyl, alkynyl or unsubstituted or substituted aralkyl or aryloxyalkyl, and Z is an anion of an acid, and fungicides containing these compounds.Type: GrantFiled: July 31, 1985Date of Patent: July 8, 1986Assignee: BASF AktiengesellschaftInventors: Costin Rentzea, Ernst Buschmann, Norbert Meyer, Eberhard Ammermann, Ernst-Heinrich Pommer
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Patent number: 4545995Abstract: The novel unsaturated arylalkyl ammonium salts described herein are useful as antiarrhythmic agents. A method of treating arrhythmia by increasing the refractoriness of cardiac tissue is provided, as well as pharmaceutical formulations containing such ammonium salts.Type: GrantFiled: July 12, 1983Date of Patent: October 8, 1985Assignee: Schering A.G.Inventors: William C. Lumma, Jr., Ronald A. Wohl
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Patent number: 4521412Abstract: The present invention relates to iodopropargyl-ammonium salts of the formula (I) ##STR1## in which R, R.sup.1, R.sup.2 and X.sup..phi. have the meanings given in the description.They are obtained, for example, by reacting tertiary amines with an iodopropargyl halide. In a second reaction step, the halogen anion can be exchanged for other anions, such as phosphate and sulphate. The iodopropargylammonium salts of the formula (I) are distinguished by high activity as pest-combating agents, in particular by a fungicidal as well as bactericidal activity.Type: GrantFiled: May 2, 1983Date of Patent: June 4, 1985Assignee: Bayer AktiengesellschaftInventors: Hans-Georg Schmitt, Paul Reinecke, Wilfried Paulus, Hermann Genth, Walter Radt
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Patent number: 4476323Abstract: The invention relates to new surface-active quaternary ammonium compounds having the general formula: ##STR1## wherein: R.sub.1 and R.sub.2 are each hydrocarbon groups having from about twelve to about forty carbon atoms;R.sub.3 and R.sub.4 are selected from the group consisting of methyl, ethyl and hydroxyethyl;A is an oxyalkylene group derived from both ethylene oxide and propylene oxide, having a ratio of oxyethylene units to the total number of oxyalkylene groups within the range from about 1:6 to about 5:6;m is a number corresponding to the valence of X;n.sub.1 and n.sub.2 represent the average number of oxyalkylene units and are within the range from about 6 to about 30; andX is an anion.The compounds impart to the treated textiles and cellulosic materials a reduced tendency to retain an electrostatic charge and/or improved softness and/or reduced mechanical strength due to a reduction in interfiber bonding, and at the same time preserve good hydrophilic properties.Type: GrantFiled: February 24, 1981Date of Patent: October 9, 1984Inventors: Karl M. E. Hellsten, Jan G. Emanuelsson, Svante L. Wahlen, Axel I. Thebrin
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Patent number: 4468352Abstract: The distyrylbiphenyls of the formula ##STR1## in which X and X' independently of one another are a direct bond, oxygen, sulfur, --O--C.sub.1-3 -alkylene-CON(R.sub.4)----CON(R.sub.4)--, --O--C.sub.1-3 -alkylene-COO--, OCO or --COO--, with the proviso that if n+n'=O, X and Y' may not be --CON(R.sub.4)-- or O--C.sub.1-3 -alkylene-CON(R.sub.4)--, and if n+n'=2 and X and X' are --CON(R.sub.4)-- or --COO--, A.sup..crclbar. may not be a phosphite or phosphonate anion, and Y and Y' independently of one another are C.sub.1-20 -alkylene, R.sub.1 and R.sub.1 ' independently of one another are unsubstituted or substituted C.sub.1-8 -alkyl or C.sub.3-4 -alkenyl, or R.sub.1 together with R.sub.2, or R.sub.1 ' together with R.sub.2 ', is a heterocyclic ring, R.sub.2 and R.sub.2 ' independently of one another are unsubstituted or substituted C.sub.1-8 -alkyl or C.sub.3-4 -alkenyl, or R.sub.2 together with R.sub.1, or R.sub.2 ' together with R.sub.1 ', is a heterocyclic ring, or R.sub.1 and R.sub.2, or R.sub.1 ' and R.sub.Type: GrantFiled: April 28, 1982Date of Patent: August 28, 1984Assignee: Ciba-Geigy CorporationInventors: Christian Luthi, Hans R. Meyer, Kurt Weber
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Patent number: 4400380Abstract: Compounds of the formula ##STR1## wherein R is H, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, 3,4-methylenedioxy, CF.sub.3, NO.sub.2, NH.sub.2, N(C.sub.1-4 alkyl).sub.2, CN, OH, --S(C.sub.1-4 alkyl) or --SO.sub.2 (C.sub.1-4 alkyl); R.sub.1 and R.sub.2 are independently each H or C.sub.1-4 alkyl or taken together with the attached N atom are morpholino, piperidino, pyrrolidino, piperazino, or N-- C.sub.1-4 -alkyl piperazino; and, when R is halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, x is 0-3 and, otherwise, is 0 or 1;or a pharmaceutically acceptable salt thereof with an acid or for the compounds wherein R.sub.1 and R.sub.2 are both not H, a quaternary ammonium salt thereof with a C.sub.1-4 alkyl halidehave valuable antiviral activity, e.g., for treatment of infections caused by a herpes virus.Type: GrantFiled: June 22, 1981Date of Patent: August 23, 1983Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Harry W. Ritter, Michael L. Edwards
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Patent number: 4399076Abstract: 2-Vinyl- and 2-ethylcyclopropanes having an aryl group and a nitrogen-containing radical substituted at the 1-position on the ring are provided. The novel 1,1-disubstituted 2-vinylcyclopropane and 2-ethylcyclopropane compounds of this invention have utility in herbicidal applications and are useful reactants. The 2-vinylcyclopropane derivatives are useful monomers for anionic and radical polymerizations.Type: GrantFiled: February 22, 1982Date of Patent: August 16, 1983Assignee: National Distillers and Chemical CorporationInventors: Richard G. Fayter, Jr., Allen L. Hall
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Patent number: 4366036Abstract: Novel alkylated hydroxyl aryl compounds, such as vanillin which has been alkylated with 3-chloro-2-hydroxypropyltrimethylammonium chloride, are useful as additives in alkaline zinc electroplating baths.Type: GrantFiled: September 8, 1981Date of Patent: December 28, 1982Assignee: Occidental Chemical CorporationInventors: Ronald J. Lash, Roy W. Herr
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Patent number: 4343647Abstract: Compounds are prepared which correspond to the formula ##STR1## wherein R represents hydrogen, chloro, bromo or trifluoromethyl; n represents an integer of from 1 or 2 with the proviso that when R is trifluoromethyl, n is 1; R.sup.1, R.sup.2 and R.sup.3 each independently represent ethyl, n-propyl, n-butyl, isobutyl, ethynyl, vinyl or ethoxymethyl or R.sup.2 and R.sup.3 taken together form an alkylene bridge of 2 to 4 carbon atoms and X represents a non-phytotoxic anion. The compounds have been found to be active plant growth regulatory control agents.Type: GrantFiled: June 9, 1980Date of Patent: August 10, 1982Assignee: The Dow Chemical CompanyInventors: Joseph Dunbar, Theodore W. Holmsen, Herman O. Senkbeil
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Patent number: 4339393Abstract: The distyrylbiphenyls of the formula ##STR1## in which X and X' independently of one another are a direct bond, oxygen, sulfur, --O--C.sub.1--3 --alkylene--CON(R.sub.4)--, --CON(R.sub.4)--,--O--C.sub.1--3 --alkylene--COO--, OCO or --COO--, with the proviso that if n+n'=O, X and X' may not be --CON(R.sub.4)--or O--C.sub.1--3 --alkylene--CON(R.sub.4)--, and if n+n'=2 and X and X' are --CON(R.sub.4)--or --COO--, A.crclbar. may not be a phosphite or phosphonate anion, and Y and Y' independently of one another are C.sub.1--20 --alkylene, R.sub.1 and R.sub.1' independently of one another are unsubstituted or substituted C.sub.1--8 --alkyl or C.sub.3--4 --alkenyl, or R.sub.1 together with R.sub.2, or R.sub.1' together with R.sub.2', is a heterocyclic ring, R.sub.2 and R.sub.2' independently of one another are unsubstituted or substituted C.sub.1--8 --alkyl or C.sub.3--4 -- alkenyl, or R.sub.2 together with R.sub.1, or R.sub.2' together with R.sub.1', is a heterocyclic ring, or R.sub.1 and R.sub.2, or R.sub.1' and R.Type: GrantFiled: April 4, 1980Date of Patent: July 13, 1982Assignee: Ciba-Geigy CorporationInventors: Christian Luthi, Hans R. Meyer, Kurt Weber
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Patent number: 4297296Abstract: The present invention relates to quaternized polyamines having the basic structure of formula I, ##STR1## in which each R independently, is (C.sub.10-22)alkyl, (C.sub.10-22)alkenyl, phenyl(C.sub.1-3)alkyl or naphthyl(C.sub.1-3)alkyl,each R.sub.1, independently, is phenyl(C.sub.1-3)alkyl or naphthyl (C.sub.1-3)alkyl, z, is 1 to 5,each y.sub.1, independently is an integer from 2 to 8,y.sub.2, is an integer from 2 to 8, with the proviso that when z=1,y.sub.1 .noteq.y.sub.2 and when z>1 and the y.sub.1 's are the same y.sub.2 .noteq.y.sub.1and wherein an average of 0.5 to 2.0 nitrogen atoms are quaternized with alkyl radicals containing from 1 to 6 carbon atoms and mixtures of such quaternized polyamines with further quaternized polyamines, such polyamines and mixtures being useful as dye retarders/levelling agents.Type: GrantFiled: June 21, 1979Date of Patent: October 27, 1981Assignee: Sandoz Ltd.Inventor: Hans-Peter Baumann
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Patent number: 4275235Abstract: Quaternary ammonium halides in powder or granular form are prepared by reacting tertiary amines and excess alkyl halides in the absence of solvent at elevated temperature and pressure and conducting the hot, pressurized reaction mixture into an area under lower pressure where the excess alkyl halides vaporize and the quaternary ammonium halides are recovered in powder or granular form.Type: GrantFiled: November 16, 1979Date of Patent: June 23, 1981Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Wolfgang Giede, Horst Rutzen
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Patent number: 4265810Abstract: Zwitterionic diazonium salts, derived from aromatic amines, are aggregated by: (a) diazotizing said amine to a zwitterionic diazonium salt in the presence of a cationic surfactant or (b) diazotizing said amine and thereafter treating the resulting zwitterionic diazonium salt with a cationic surfactant, so as to give particles of the diazonium salts which are readily separable from the liquid mass in which they are formed.Type: GrantFiled: June 6, 1980Date of Patent: May 5, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventors: Donald L. Bauman, Masuo Toji
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Patent number: 4248797Abstract: This invention relates to vinylbenzyl and crosslinking bis-(vinylbenzyl) monomers for use in the preparation of polymers, especially ion exchange resins, and to methods for the preparation of the monomers and polymers. It is particularly concerned with the preparation, polymerization, and use of new nitrogenous monomers as crosslinking agents and/or function-introducing agents.Type: GrantFiled: September 18, 1978Date of Patent: February 3, 1981Assignee: Rohm and Haas CompanyInventors: Frank J. Glavis, David H. Clemens