Polyquaternary Ammonium Patents (Class 564/295)
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Patent number: 6716882Abstract: The present invention discloses highly packed polycationic ammonium, sulfonium and phosphonium lipid compounds useful for making lipid aggregates for delivery of macromolecules and other compounds into cells. They are especially useful for the DNA-dependent transformation of cells. Methods for their preparation and use as intracellular delivery agents are also disclosed.Type: GrantFiled: April 23, 2002Date of Patent: April 6, 2004Assignee: Invitrogen CorporationInventors: Alberto Haces, Valentina C. Ciccarone
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Patent number: 6706922Abstract: A method of forming polymers in the presence of nucleic acid using template polymerization. Also, a method of having the polymerization occur in heterophase systems. These methods can be used for the delivery of nucleic acids, for condensing the nucleic acid, for forming nucleic acid binding polymers, for forming supramolecular complexes containing nucleic acid and polymer, and for forming an interpolyelectrolyte complex.Type: GrantFiled: November 16, 2001Date of Patent: March 16, 2004Assignee: Mirus CorporationInventors: Jon A. Wolff, James E. Hagstrom, Vladimir G. Budker, Vladimir S. Trubetskoy, Paul M. Slattum, Lisa J. Hanson
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Publication number: 20040035293Abstract: One aspect of the present invention relates to ionic liquids comprising a pendant Bronsted-acidic group, e.g., a sulfonic acid group. Another aspect of the present invention relates to the use of an ionic liquid comprising a pendant Bronsted-acidic group to catalyze a Bronsted-acid-catalyzed chemical reaction. A third aspect of the present invention relates to ionic liquids comprising a pendant nucleophilic group, e.g., an amine. Still another aspect of the present invention relates to the use of an ionic liquid comprising a pendant nucleophilic group to catalyze a nucleophile-assisted chemical reaction. A fifth aspect of the present invention relates to the use of an ionic liquid comprising a pendant nucleophilic group to remove a gaseous impurity, e.g., carbon dioxide, from a gas, e.g., sour natural gas.Type: ApplicationFiled: April 4, 2003Publication date: February 26, 2004Inventor: James Hillard Davis
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Patent number: 6673890Abstract: A zwitterionic polyamine comprising a linear or branched hydrophobic polyamine backbone having 2 to 10 tertiary amino nitrogen atoms and a spacer between two tertiary nitrogen atoms wherein the spacer is, for example selected from C8-C16-alkylene, C5-C15-cyloalkylene, wherein in formula (IV) R═C1- to C22-alkyl or C7-C22-aralkyl and n=3 to 6, at least one tertiary amine end group of the polyamine backbone contains two groups having formula (V) or (VI), wherein A means an ethylene oxide unit, a propylene oxide unit, a unit of butylene oxides and a tetrahydrofuran unit, n is a number of from 1 to 50, X is an anionic group such as —SO3M, with the proviso that in formula (VI) one X may also be hydrogen and M is hydrogen, alkai metal or ammonium, or contains one group of formula (V) or (VI) and one group selected from radicals consisting of formula (VII), C1- to C22-alkyl and C7-C22-aralkyl the meaning of A and n is the same as in formula (V) or (VI), said zwitterionic polyetherpolyamine having aType: GrantFiled: January 16, 2002Date of Patent: January 6, 2004Assignee: BASF AktiengesellschaftInventors: Dieter Boeckh, Oliver Borzyk, Michael Ehle, Ralf Nöerenberg, Eugene P. Gosselink, Jeffrey S. DuPont, Robert H. Rohrbaugh, Kenneth N. Price, Randall S. Deinhammer
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Patent number: 6583234Abstract: Disclosed is a process which comprises (a) reacting allyl bromide with diethyl amine in a molar ratio of at least about 1 mole of allyl bromide per about 1.15 moles of diethyl amine and in a molar ratio of no more than about 1 mole of allyl bromide per about 2 moles of diethyl amine, thereby generating allyl diethyl amine in a monomer reaction mixture; (b) subsequently filtering the monomer reaction mixture to remove impurities; (c) subsequently reacting the allyl diethyl amine with allyl bromide, thereby generating solid diallyl diethyl ammonium bromide; (d) subsequently isolating the solid diallyl diethyl ammonium bromide; (e) subsequently dissolving the diallyl diethyl ammonium bromide in a solvent and adding thereto a polymerization initiator to form a polymerization reaction mixture; (f) subsequently heating the polymerization reaction mixture in a vessel equipped with a reflux condenser to a temperature of from about 90 to about 100° C.Type: GrantFiled: July 26, 2001Date of Patent: June 24, 2003Assignee: Xerox CorporationInventors: Sheau V. Kao, Daniel A. Foucher, Mohammad J. Hossain, Christine E. Bedford, George Liebermann
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Patent number: 6525012Abstract: The present invention relates to liquid laundry detergent compositions which provide enhance hydrophilic soil cleaning benefits, said compositions comprising: a) from about 0.01 to about 20% by weight, of a zwitterionic polymer which comprises a polyamine backbone, said backbone comprising two or more amino units wherein at least one of said amino units is quaternized and wherein at least one amino unit is substituted by one or more moieties capable of having an anionic charge wherein further the number of amino unit substitutions which comprise an anionic moiety is less than or equal to the number of quaternized backbone amino units; b) from about 0.1% to about 7% by weight, of a polyamine dispersant; c) from about 0.01% to about 80% by weight, of a surfactant system comprising one or more surfactants selected from the group consisting of nonionic, anionic, cationic, zwitterionic, ampholytic surfactants, and mixtures thereof; and d) the balance carriers and adjunct ingredients.Type: GrantFiled: February 21, 2001Date of Patent: February 25, 2003Assignee: The Procter & Gamble CompanyInventors: Kenneth Nathan Price, Axel Meyer
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Publication number: 20020156049Abstract: The present invention discloses highly packed polycationic ammonium, sulfonium and phosphonium lipid compounds useful for making lipid aggregates for delivery of macromolecules and other compounds into cells. They are especially useful for the DNA-dependent transformation of cells. Methods for their preparation and use as intracellular delivery agents are also disclosed.Type: ApplicationFiled: April 23, 2002Publication date: October 24, 2002Inventors: Alberto Haces, Valentina C. Ciccarone
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Patent number: 6426436Abstract: The present invention is related to a series of derivatives of novel ether diamine compounds prepared by the cynobutylation reaction of an alcohol having 3 to 22 carbon atoms with 2-pentenenitrile to form a branched alkyl ether nitrile. The etheraminonitriles formed by the process are hydrogenated to form alkylether amines. The resulting product can be reacted with 2-pentenenitrile and or acrylonitrile and in subsequent step, hydrogenated to yield a diamine. Specifically, the present invention deals with two types of tertiary amines one made by the reaction of novel ether diamines compounds with ethylene oxide, propylene oxide or butylene oxide or mixtures thereof, producing alkoxylated tertiary amines and the other made by the reaction of novel ether amine compounds with formaldehyde and hydrogen producing methylated tertiary amines. The invention also disclosed novel amine oxides, and quaternary compounds made from said tertiary amines.Type: GrantFiled: January 22, 2002Date of Patent: July 30, 2002Assignee: Nova Molecular Technologies Inc.Inventors: Thomas J. Daly, Michael Clumpner, Anthony J. O'Lenick, Jr.
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Patent number: 6399663Abstract: The present invention discloses highly packed polycationic ammonium, sulfonium and phosphonium lipid compounds useful for making lipid aggregates for delivery of macromolecules and other compounds into cells. They are especially useful for the DNA-dependent transformation of cells. Methods for their preparation and use as intracellular delivery agents are also disclosed.Type: GrantFiled: August 25, 2000Date of Patent: June 4, 2002Assignee: Invitrogen CorporationInventors: Alberto Haces, Valentina C. Ciccarone
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Patent number: 6384097Abstract: An amine catalyst for production of a polyurethane and a polyisocyanurate is provided which comprises a quaternary ammonium compound represented by General Formula (1): where R1 to R6 are independently a linear or branched saturated hydrocarbon group of 1 to 4 carbon atoms; R7 and R8 are independently a linear or branched, saturated or unsaturated hydrocarbon group of 2 to 12 carbon atoms; n is a number of 0 to 3, provided that at n=0 any one of R1, R2 and R3, and R5 and/or R6 may be linked together to form a heterocycle, or at n=1, 2, or 3, R5 or R6 and R4 may be linked together to form a heterocycle; A is a carbonate group or an organic acid group; and X is number of 1 to 2. The catalyst has high activity in formation of polyurethane foams and polyisocyanurate foams, having less odor, and producing foams of high fire retardance, having high curability, high retarding effect, and low corrosiveness.Type: GrantFiled: August 27, 2001Date of Patent: May 7, 2002Assignee: Tosoh CorporationInventors: Katsumi Tokumoto, Yutaka Tamano, Shuichi Okuzono
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Patent number: 6384177Abstract: An amine catalyst for production of a polyurethane and a polyisocyanurate is provided which comprises a quaternary ammonium compound represented by General Formula (1): where R1 to R6 are independently a linear or branched saturated hydrocarbon group of 1 to 4 carbon atoms; R7 and R8 are independently a linear or branched, saturated or unsaturated hydrocarbon group of 2 to 12 carbon atoms; n is a number of 0 to 3, provided that at n=o any one of R1, R2 and R3, and R5 and/or R6 may be linked together to form a heterocycle, or at n=1, 2, or 3, R5 or R6 and R4 may be linked together to form a heterocycle; A is a carbonate group or an organic acid group; and X is number of 1 to 2. The catalyst has high activity in formation of polyurethane foams and polyisocyanurate foams, having less odor, and producing foams of high fire retardance, having high curability, high retarding effect, and low corrosiveness.Type: GrantFiled: August 27, 2001Date of Patent: May 7, 2002Assignee: Tosoh CorporationInventors: Katsumi Tokumoto, Yutaka Tamano, Shuichi Okuzono
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Patent number: 6379294Abstract: A process for preparing an esterquat composition comprising (a) reacting a tertiary amine according to formula I: wherein R1 represents a C3-C6 hydrocarbon group, R2 represents a C3-C6 hydrocarbon group, a —R4—OH group or a —CH2[CH(OH)]nCH2OR5 group, if R2 represents a C3-C6 hydrocarbon group, R3 represents a —R4—OH group or a —CH2[CH(OH)]nCH2OR5 group, if R2 represents a —R4—OH group, R3 represents a —R4—OH group or a —CH2[CH(OH)]nCH2OR5 group, if R2 represents a —CH2[CH(OH)]nCH2OR5 group, R3 represents a —CH2[CH(OH)]nCH2OR5 group, R4 represents a C2-C4 hydrocarbon group, n is 1-4, and R5 represents H or a C1-C30 hydrocarbon group, with a C3-C6 hydrocarbyl halide or a di(C3-C6) hydrocarbyl sulfate, followed by (b) reaction with a C8-C30 acid halide, with the proviso that at least one hydroxy group is esterified.Type: GrantFiled: July 19, 2000Date of Patent: April 30, 2002Assignee: Akzo Nobel N.V.Inventors: Adrianus Buijs, Gerardus Van Gurp, Tjitte Nauta, Robert Smakman, Anne Marijke Wit-Van Grootheest
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Patent number: 6307102Abstract: An amine catalyst-for production of a polyurethane and a polyisocyanurate is provided which comprises a quaternary ammonium compound represented by General Formula (1): where R1 to R6 are independently a linear or branched saturated hydrocarbon group of 1 to 4 carbon atoms; R7 and R8 are independently a linear or branched, saturated or unsaturated hydrocarbon group of 2 to 12 carbon atoms; n is a number of 0 to 3 provided that at n=o any one of R1, R2 and R3, and R5 and/or R6 may be linked together to form a heterocycle, or at n=1, 2, or 3, R5 or R6 and R4 may be linked together to form a heterocycle; A is a carbonate group or an organic acid group; and X is number of 1 to 2. The catalyst has high activity in formation of polyurethane foams and polyisocyanurate foams, having less odor, and producing foams of high fire retardance, having high curability, high retarding effect, and low corrosiveness.Type: GrantFiled: October 14, 1998Date of Patent: October 23, 2001Assignee: Tosoh CorporationInventors: Katsumi Tokumoto, Yutaka Tamano, Shuichi Okuzono
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Patent number: 6177577Abstract: This invention relates to novel dicationic and polycationic monoprimary alcohol compounds and their derivatives, represented by the formula wherein each alk is independently alkyl of 1-8 carbon atoms; each ALK is independently alkyl of 1-8 carbon atoms; each R1, R2, R3, R4 or R5 is independently H or alkyl of 1-8 carbon atoms; n is 2-5; G is H, CR1R2CR3OHCR4R5X or X is Cl, Br or I; An− is an anion and p is 1-10; provided that the compound is soluble in water.Type: GrantFiled: November 15, 1991Date of Patent: January 23, 2001Assignee: The Dow Chemical CompanyInventors: Dorothy L. Roerden, R. Keith Frank
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Patent number: 5851982Abstract: To provide a liquid softener composition which is satisfactory in respects of softening effect, storage stability and water absorption properties, is excellent in biodegradability and is gentle with the environment. A liquid softener composition comprising 3 to 40% by weight of a quaternary ammonium salt (7-I) and water ##STR1## wherein R.sup.1 represents C.sub.20 -C.sub.44 alkyl or alkenyl group; R.sup.2, R.sup.3, and R.sup.4 are the same of different from each other and are C.sub.1 -C.sub.5 alkyl or hydroxyalkyl group; Y represents C.sub.2 -C.sub.4 alkylene group; m is a number of 0 to 20; n is an integer of 1 to 6; and X.sup.- represents an anion group.Type: GrantFiled: March 27, 1996Date of Patent: December 22, 1998Assignee: Kao CorporationInventors: Yuushi Sakata, Junichi Inokoshi, Osamu Tachizawa, Tohru Katoh, Uichiro Nishimoto, Yasuki Ohtawa, Akira Sakaguchi, Kohshiroh Sotoya, deceased, Noriko Yamaguchi
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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: 5824812Abstract: Amine containing compounds and their use in the generation of cytofectin:polynucleotide complexes for transfection of cells, formulations, counterions, and reaction conditions for maximizing the transfection include using cationic amine compounds that have the general structure: ##STR1## wherein R.sub.4 and R.sub.5 are a pair of same or different lipoyl moieties selected from a group consisting of an alkyl, alkenyl, alkynyl, alkanoyl, alkenoyl, or alkynoyl groups and for R.sub.1, R.sub.2, and R.sub.3 at least two are hydroxylated, ether containing, or acyloxy containing alkyl, alkenyl, or alkynyl groups or at least one amine bonded halogen containing moiety selected from a group consisting of a halogenated alkyl, alkenyl, or alkynyl group or a mixture of at least one halogen containing moiety selected from a group consisting of a halogenated alkyl, alkenyl, or alkynyl group and at least one hydroxylated, ether containing, or acyloxy containing alkyl, alkenyl, or alkynyl group, and X.sup.Type: GrantFiled: September 17, 1996Date of Patent: October 20, 1998Assignee: The Regents of the University of CaliforniaInventors: Michael H. Nantz, Michael J. Bennett, Rajiv P. Balasubramaniam, Alfred M. Aberle, Robert W. Malone
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Patent number: 5705695Abstract: The quaternary Zintl material (Et.sub.4 N).sub.4 ?Au(Ag.sub.1-x Au.sub.x).sub.2 Sn.sub.2 Te.sub.9 ! that contains 1-D semiconducting chains composed of four metallic elements is prepared by treating ethylenediamine extracts of a pentanary K--Au--Ag--Sn--Te alloy with Et.sub.4 NI.Type: GrantFiled: December 18, 1996Date of Patent: January 6, 1998Assignee: NEC Research Institute, Inc.Inventors: Robert C. Haushalter, Sandeep S. Dhingra
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Patent number: 5703131Abstract: A method for the detoxification of a mustard gas by reaction with a bis-tertiary diamine resulting in quaternary ammonium ionene polymers. Sulfur-containing quaternary ammonium ionene polymers which are useful as microbicides for controlling the growth of microorganisms in aqueous systems and on surfaces, as well as for inhibiting slime formation in aqueous systems and biocidal compositions contain effective amounts of the sulfur-containing quaternary ammonium ionene polymers.Type: GrantFiled: September 18, 1995Date of Patent: December 30, 1997Assignee: Buckman Laboratories International Inc.Inventors: Wallace E. Puckett, Mark L. Zollinger, Fernando Del Corral
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Patent number: 5674908Abstract: The present invention discloses highly packed polycationic ammonium, sulfonium and phosphonium lipid compounds useful for making lipid aggregates for delivery of macromolecules and other compounds into cells. They are especially useful for the DNA-dependent transformation of cells. Methods for their preparation and use as intracellular delivery agents are also disclosed.Type: GrantFiled: December 20, 1993Date of Patent: October 7, 1997Assignee: Life Technologies, Inc.Inventors: Alberto Haces, Valentina C. Ciccarone
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Patent number: 5650099Abstract: A dicationic surfactant for enhancing the chemiluminescence of chemiluminescent compounds particularly dioxetanes which are triggerable is described. The surfactant has the formulaX.sup.- (R.sub.1).sub.3 A.sup.+ CH.sub.2 -Link-CH.sub.2 A.sup.+ (R.sub.2).sub.3 X.sup.-wherein A is selected from the group consisting of phosphorus and nitrogen atoms separately or together, wherein X is an anionic counterion and R.sub.1 and R.sub.2 are selected from the group consisting of unsubstituted and substituted alkyl and aralkyl groups containing 1 to 20 carbon atoms and R.sub.1 and R.sub.2 can be the same or different, and wherein Link is a carbon chain group selected from the group consisting of dialkylenearyl, aryl, alkylene, alkenylene and alkynylene groups containing 4 to 20 carbon atoms. The surfactants are particularly useful in Western and Southern blot assays.Type: GrantFiled: May 16, 1995Date of Patent: July 22, 1997Assignee: Lumigen, Inc.Inventors: M. Hashem Akhavan-Tafti, Zahra Arghavani
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Patent number: 5623088Abstract: A method of producing 4-ADPA is disclosed wherein aniline or substituted aniline derivatives and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine or substituted derivatives thereof and/or 4-nitrosodiphenylamine or substituted derivatives thereof and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA or substituted derivatives thereof. The 4-ADPA or substituted derivatives thereof can be reductively alkylated to produce p-phenylenediamine products or substituted derivatives thereof which are useful as antiozonants.Type: GrantFiled: May 10, 1995Date of Patent: April 22, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, James K. Bashkin
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Patent number: 5606033Abstract: A method for the purification of proteins by displacement chromatography on ion exchange media using low molecular weight displacers is disclosed. Several classes of low molecular weight anionic species are exemplified, including aromatic rings having sulfonic acid or carboxylic acid moieties attached thereon, sulfated sugar derivatives, anionic antibiotics, and dendrimeric polymers. Novel compounds useful as displacers are dendrimers of formula ##STR1## wherein R.sup.1 is lower alkyl, n is 2 to 6 and similar dendritic polymers based thereon.Type: GrantFiled: October 19, 1995Date of Patent: February 25, 1997Inventors: Steven M. Cramer, James A. Moore, Amitava Kundu, Yufei Li, Guhan Jayaraman
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Patent number: 5576459Abstract: An optically-active or chiral compound is described which comprises(A) at least one quaternary nitrogen or phosphorus cation provided that if the cation is a quaternary nitrogen cation containing a hydroxyalkyl group, the hydroxyalkyl group is free of chlorine, and(B) at least one optically-active anion.In one embodiment, the optically-active anion is an optically-active carboxylic acid anion. The process for preparing such optically-active compounds also is described and such compounds may be prepared by reacting(A) at least one quaternary nitrogen or phosphorus salt with(B) at least one optically-active reactant capable of reacting with the salt provided that if the salt is a quaternary nitrogen salt containing a hydroxyalkyl group, the hydroxyalkyl group is free of chlorine.Type: GrantFiled: June 6, 1995Date of Patent: November 19, 1996Assignee: Sachem, Inc.Inventor: Morey E. Osborn
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Patent number: 5541230Abstract: Therapeutic polyamines useful as a cancer chemotherapeutic agents, including molecules having a formula R.sub.1 --NH--(CH.sub.2).sub.x --NH --(CH.sub.2).sub.x --NH--(CH.sub.2).sub.y --NH--(CH.sub.2).sub.z --NH--R, wherein R.sub.1 and R.sub.2 are hydrocarbon chains having 1 to 5 carbons and w, x, y and z are integers of 1 to 10, are disclosed. One such molecule is N.sup.1, N.sup.19 -bis(ethylamino)-5,10,15-triazanonadecane, which is longer than spermine. This preferred compound may be used alone or in combination with other therapeutic agents, such as 1,3-bis(2-chloroethyl)-1-nitrosourea or cis-Pt.Type: GrantFiled: November 5, 1993Date of Patent: July 30, 1996Inventors: Hirak S. Basu, Burt Feuerstein, Laurence Marton, Keijiro Samejima
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Patent number: 5478924Abstract: A method for the purification of proteins by displacement chromatography on ion exchange media using low molecular weight displacers is disclosed. Several classes of low molecular weight, charged species are exemplified, including aminoacids, peptides, antibiotics and dendrimeric polymers. Novel compounds useful as displacers are dendrimers of formula ##STR1## wherein R.sup.1 is lower alkyl, n is 2 to 6, and X is a common counter anion and similar dendritic polymers based thereon.Type: GrantFiled: February 16, 1994Date of Patent: December 26, 1995Inventors: Steven M. Cramer, James A. Moore, Amitava Kundu, Yufei Li, Guhan Jayaraman
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Patent number: 5401881Abstract: Sulfur-containing quaternary ammonium ionene polymers which are useful as microbicides for controlling the growth of microorganisms in aqueous systems and on surfaces, as well as for inhibiting slime formation in aqueous systems and biocidal compositions containing effective amounts of the sulfur-containing quaternary ammonium ionene polymers.Type: GrantFiled: August 12, 1992Date of Patent: March 28, 1995Assignee: Buckman Laboratories International, Inc.Inventors: Wallace E. Puckett, Mark L. Zollinger, Fernando D. Corral
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Patent number: 5387717Abstract: A method for the detoxification of a mustard gas by reaction with a bis-tertiary diamine resulting in quaternary ammonium ionene polymers. Sulfur-containing quaternary ammonium ionene polymers which are useful as microbicides for controlling the growth of microorganisms in aqueous systems and on surfaces, as well as for inhibiting slime formation in aqueous systems and biocidal compositions contain effective amounts of the sulfur-containing quaternary ammonium ionene polymers.Type: GrantFiled: December 18, 1992Date of Patent: February 7, 1995Assignee: Buckman Laboratories International, Inc.Inventors: Wallace E. Puckett, Mark L. Zollinger, Fernando D. Corral
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Patent number: 5352833Abstract: What is provided herein are active antimicrobial polymeric quaternary ammonium compounds which are capped with defined C.sub.12 /C.sub.14 alkyl groups optionally coprecipitated with polyvinylpyrrolidone (PVP). The compounds of the invention have the formula: ##STR1## where n is at least 2, e.g. 2-30, and C.sub.12 /C.sub.14 alkyl preferably is 50:50 wt. % of dodecyl/tetradecyl alkyl.Type: GrantFiled: October 26, 1992Date of Patent: October 4, 1994Assignee: ISP Investments Inc.Inventor: John J. Merianos
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Patent number: 5308363Abstract: A process for the preparation of a quaternary ammonium bisulfate which comprises the reaction of a quaternary ammonium alkylsulfate with sulfuric acid in a solvent mixture comprised of water and isopropyl alcohol, followed by the recovery of the solid quaternary ammonium bisulfate by crystallization from the reaction mixture.Type: GrantFiled: February 18, 1992Date of Patent: May 3, 1994Assignee: Xerox CorporationInventors: George Liebermann, H. Bruce Goodbrand, John L. Haack, John Abate
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Patent number: 5275744Abstract: A composition of polyalkylenepolyamine derivatives useful as a corrosion inhibitor in aqueous media produced by reacting a starting polyalkylenepolyamine composition comprising a mixture of:(i) at least one C-alkyl-ethylene diamine; and(ii) at least one di-(C-alkyl)-diethylenetriamine;wherein each C-alkyl group on the ethylene diamine and diethylenetriamine independently contain between 8-26 carbon atoms;with a derivatizing agent which is either an alkylating agent or an alkylene oxide. Methods for preparing this composition and using it to inhibit the corrosion of corrodible metal alloys are also disclosed.Type: GrantFiled: September 9, 1992Date of Patent: January 4, 1994Assignee: Chevron Research and Technology CompanyInventor: Andrew W. Ho
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Patent number: 5242684Abstract: An antimicrobial, low toxicity, non-irritating composition comprises a blend of several bis-quaternary ammonium compounds coprecipitated with a copolymer of vinylpyrrolidone and an acrylamido or vinyl quaternary ammonium monomer.Type: GrantFiled: October 25, 1991Date of Patent: September 7, 1993Assignee: ISP Investments Inc.Inventor: John J. Merianos
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Patent number: 5223626Abstract: Compounds of the formula ##STR1## where R.sub.1, R.sub.2 and R.sub.3 are each independently of the others hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen or C.sub.1 -C.sub.4 alkanoylamino,R is hydrogen or unsubstituted or C.sub.1 -C.sub.4 alkoxy substituted C.sub.1 -C.sub.12 alkyl or an --(alk)--NA.sup..sym. X.sup..crclbar. radical or,R forms together with an R.sub.1 in the ortho-position relative to the amino group a partially hydrogenated, substituted or unsubstituted 5- to 7-membered heterocyclic ring which may contain additional N, S or O atoms as ring members, (alk) is a substituted or unsubstituted C.sub.1 -C.sub.6 alkylene radical,--NA.sup..sym. is the radical of an amino compound of formula ##STR2## where R.sub.4, R.sub.5 and R.sub.6 are each independently of the others substituted or unsubstituted C.sub.1 -C.sub.6 alkyl, substituted or unsubstituted C.sub.7 -C.sub.12 aralkyl or substituted or unsubstituted aryl, R.sub.8 and R.sub.Type: GrantFiled: November 16, 1989Date of Patent: June 29, 1993Assignee: Ciba-Geigy CorporationInventors: Janos Vincze, Wilfried Herter
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Patent number: 5196135Abstract: An antimicrobial, low toxicity blend composition of several bis-quaternary ammonium compounds of defined structure, and in defined amounts of the composition, is described herein.Type: GrantFiled: October 7, 1991Date of Patent: March 23, 1993Assignee: ISP Investments Inc.Inventor: John J. Merianos
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Patent number: 5136095Abstract: Compounds and methods are disclosed for reversibly aggregating particles suspended in a liquid medium. The method comprises combining the liquid medium containing the particles with a polyionic polymer capable of aggregating the particles under conditions suitable for such aggregation. Thereafter, the particles are contacted with a chemical reagent capable of cleaving the polyionic polymer under conditions sufficient to reverse the aggregation. Optionally, magnetic particles are added to the liquid medium in the present method under conditions for non-specific binding and the medium including the aggregates is subjected to a magnetic field gradient to separate the aggregates from the medium. The compounds of the present invention are polyions. The aggregation of the particles is reversible upon contact with chemical agents which cleave at least some of the bonds within the polyionic polymer.Type: GrantFiled: December 1, 1988Date of Patent: August 4, 1992Assignee: Syntex (U.S.A.) Inc.Inventors: Thomas L. Tarnowski, Cheng-I Lin, Edwin F. Ullman
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Patent number: 5116921Abstract: The present invention provides crosslinked ampholytic copolymers that are highly absorbent to aqueous electrolyte solutions.Type: GrantFiled: October 28, 1991Date of Patent: May 26, 1992Assignee: Phillips Petroleum CompanyInventor: Henry L. Hsieh
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Patent number: 5087733Abstract: Processes for conditioning human hair by treatment with selected sulfur containing quaternary ammonium compounds, compositions useful for such processes and novel quaternary compounds useful in the processes.Type: GrantFiled: August 3, 1990Date of Patent: February 11, 1992Assignee: Clairol, Inc.Inventors: Thomas M. Deppert, Janusz Z. Jachowicz, Bryan P. Murphy
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Patent number: 5075399Abstract: The present invention provides crosslinked ampholytic copolymers that are highly absorbent to aqueous electrolyte solutions.Type: GrantFiled: November 15, 1990Date of Patent: December 24, 1991
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Patent number: 5015754Abstract: Quaternized condensation products useful as aftertreating agents for fixing reactive dyeings and prints on textile materials which contain cellulose fibers are formed fromA) a precondensate of one or more trialkanolamines I ##STR1## (R.sup.1 -R.sup.3 =C.sub.2 -C.sub.4 -1,2-alkylene), B) a) a carboxylic acid or a derivative thereof IIa ##STR2## [n=0, 1; R.sup.4, R.sup.5 =OH (except if n=0), C.sub.1 -C.sub.8 -alkoxy (possibly joined together to form a 5- or 6-membered ring if n=0), Cl, Br; R.sup.6 =C.sub.1 -C.sub.50 -alkylene (possibly interrupted by one or more nonadjacent oxygen atoms)],b) a carboxamide IIb ##STR3## [m, n, r=0, 1; R.sup.7 =H, C.sub.1 -C.sub.4 -alkyl; R.sup.8 =H, C.sub.1 -C.sub.25 -alkyl, C.sub.2 -C.sub.25 -alkenyl, Ph (possibly substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, F, Cl, Br)],c) an epihalohydrin IIc, ##STR4## d) a monofunctional compound IIdR.sup.9 --Y IId[R.sup.9 =C.sub.1 -C.sub.25 -alkyl, C.sub.2 -C.sub.25 -alkenyl, Ph (possibly substituted by C.sub.1 -C.sub.Type: GrantFiled: August 21, 1989Date of Patent: May 14, 1991Assignee: BASF AktiengesellschaftInventors: Johannes P. Dix, Rolf Fikentscher, Ingrid Steenken-Richter
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Patent number: 4812263Abstract: Described are bis-quaternary ammonium compounds of 2-hydroxypropylene, e.g., 2-hydroxy propylene-1,3-bis(dimethyl stearyl ammonium chloride).Type: GrantFiled: March 28, 1988Date of Patent: March 14, 1989Assignee: PPG Industries, Inc.Inventor: Robert B. Login
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Patent number: 4764306Abstract: A method of preparing certain bis-quaternary ammonium compounds and mixtures is disclosed. The method involves contacting a tertiary amine with a suitable amount of neutralizing acid, e.g. HCl, and subsequently contacting the resulting mixture with a suitable epoxide, e.g. epichlorohydrin, at an elevated temperature and in an amount that e.g. 2-hydroypropylene-bis-1,3-(dimethyl stearyl ammonium chloride) is obtained in almost stoichiometric yields. The resulting bis-quaternary ammonium compounds can be incorporated into a hair conditioner whereby a softer feel and better control of hair is obtained.The general structure for the resulting bis-quaternary ammonium compounds is as follows: ##STR1## wherein the R's are selected from the group consisting of alkyl, alkylamidoalkyl, aryalkyl, aryl, alkoxy, alkenyl, hydroxyalkyl, and carboxyalkyl and X is a negative radical from the epoxide used, e.g. epichlorohydrin.Type: GrantFiled: August 22, 1986Date of Patent: August 16, 1988Assignee: PPG Industries, Inc.Inventor: Robert B. Login
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Patent number: 4661288Abstract: Water-soluble zwitterionic compounds having clay soil removal/anti-redeposition properties. The zwitterionic compounds are selected from monozwitterionic compounds, dizwitterionic compounds, polyzwitterionic compounds, and zwitterionic polymers. These zwitterionic compounds are useful in detergent compositions at from about 0.05 to about 95% by weight. In addition to the zwitterionic compounds, the detergent compositions further comprise from about 1 to about 75% by weight of a nonionic, anionic, ampholytic, zwitterionic, or cationic detergent surfactant or mixture thereof.Type: GrantFiled: March 8, 1985Date of Patent: April 28, 1987Assignee: The Procter & Gamble CompanyInventors: Donn N. Rubingh, Eugene P. Gosselink
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Patent number: 4625064Abstract: An improved process for preparing a bis [.beta.-(N,N-dimethylamino)ethyl]ether by reacting a bismethohalide of bis [.beta.-(N,N-dimethylamino)ethyl]ether represented by the following general formula: ##STR1## (wherein X denotes a halogen atom), with an aliphatic amine having a boiling point of not lower than 220.degree. C. at atmospheric pressure and having a primary amino group in the molecule thereof. The process comprises the following two steps (a) and (b): (a) a step of distilling out water at a temperature of not more than 130.degree. C. under reduced pressure from a mixture of said bismethohalide aqueous solution and said aliphatic amine to provide a concentration of said bismethohalide to water of not less than 85% by weight, and (b) a step of reacting said bismethohalide and amine in a solid-liquid phase at a temperature of not lower than 140.degree. C.Type: GrantFiled: April 6, 1984Date of Patent: November 25, 1986Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Sadakatsu Kumoi, Keiji Mitarai, Yukihiro Tsutsumi
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Patent number: 4531012Abstract: There is disclosed an organic cation R.sup.+, designated Diquat-7, having the formula:(CH.sub.3).sub.3 --N.sup.+ --R.sub.1 --N.sup.+ --(CH.sub.3).sub.3wherein R.sub.1 is a saturated or unsaturated straight chain hydrocarbon group containing seven carbon atoms. There is also disclosed a method of preparing Diquat-7, and salts and hydroxide thereof.Type: GrantFiled: April 29, 1983Date of Patent: July 23, 1985Assignee: Mobil Oil CorporationInventor: Ernest W. Valyocsik
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Patent number: 4505833Abstract: Process for treating a clayey geological formation to prevent, inhibit or reduce swelling or migrating of clay particles in a formation by treating the formation with an effective amount of a quaternized oligomer which is the reaction product of a polyamine having a primary amino group and a tertiary amino group with a difunctional reactant to form a precondensate monomer which is then chain extended and quaternized by reaction with a dihalogenated hydrocarbon ether.A preferred oligomer is a product of:(I) about 1.0 mole of a precondensate which is the reaction product of(A) from about 2.0 to about 3.0 mole of a polyamine having a primary amino group and a tertiary amino group, the polyamine having a non-cyclic backbone containing between 1 and 6 carbon atoms, with(B) about 1.0 mole of a difunctional reactant which is a diester of a mixture of dicarboxylic acids such as adipic, glutaric and succinic acid, with(II) from about 1.0 to about 1.2 mole of a chain extender such as dichloroethylether.Type: GrantFiled: October 3, 1983Date of Patent: March 19, 1985Assignee: Diamond Shamrock Chemicals CompanyInventors: Stanley A. Lipowski, John J. Miskel, Jr., Martin J. Schick
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Patent number: 4492802Abstract: Process for the manufacture of quaternary ammonium compounds by reacting a compound having a terminal epoxide troup with a salt of a tertiary amine in the presence of a quaternary ammonium compound as catalyst.Type: GrantFiled: April 19, 1982Date of Patent: January 8, 1985Assignees: Henkel Kommanditgesellschaft auf Aktien, Degussa AktiengesellschaftInventors: Horst Rutzen, Peter Nikolaus, Martin Bischoff, Rudolf Lehmann
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Patent number: 4480126Abstract: Process for the preparation of quaternary ammonium compounds by reacting a tertiary amine with a vicinal halohydrin having at least 6 carbon atoms, and quaternary ammonium compounds prepared thereby.Type: GrantFiled: April 19, 1982Date of Patent: October 30, 1984Assignee: Henkel Kommanditgesellschaft auf AktienInventor: Horst Rutzen
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Patent number: 4401577Abstract: This disclosure relates to fabric softening compositions containing quaternary ammonium dihydroborates and to methods of softening textiles employing such compounds and compositions. Such softening compositions have unusually and unexpectedly favorable stabilities in 3% dispersions in water.Type: GrantFiled: February 23, 1982Date of Patent: August 30, 1983Assignee: Akzona IncorporatedInventor: James M. Richmond
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Patent number: 4310465Abstract: A synthesis of Vitamin E has the condensation of 2,4-pentanediene and 1,2-epoxy-2,6,10,14-tetramethylpentadecane including intermediates in this synthesis which uses base catalyzed condensations of aliphatic compounds to construct the Vitamin E molecule from aliphatic precursors.Type: GrantFiled: December 17, 1979Date of Patent: January 12, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Gary L. Olson, Gabriel Saucy
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Patent number: 4277350Abstract: A softening agent comprising a quaternary ammonium salt is effectively useful for garment fabrics made of natural fibers or synthetic fibers.Type: GrantFiled: November 29, 1979Date of Patent: July 7, 1981Assignee: Kao Soap Co., Ltd.Inventors: Yutaka Minegishi, Toshiro Nishimura