Acyclic Patents (Class 564/291)
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Publication number: 20030013769Abstract: A compound of formula I: 1Type: ApplicationFiled: May 6, 2002Publication date: January 16, 2003Inventors: Ravindranath Mukkamala, Rajiv Manohar Banavali
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Patent number: 6489495Abstract: This invention relates to the synthesis of novel cationic, amphiphilic lipids and their application as gene transfer vehicles in vitro and in vivo. For this a series of different lipids (diglycerides, steroids) were synthesized by modification with variable cationic molecules (amino acids, biogenic amines). Compounds of this kind are, due to their capability of producing complexes with polynucleotides (DNA, RNA, Antisense oligonucleotides, ribozymes etc) suitable as vectors for gene transfer (transfection).Type: GrantFiled: July 3, 2001Date of Patent: December 3, 2002Assignee: Max-Delbrück-Centrum für Molekulare MedizinInventors: Manfred Schneider, Oliver Keil, Regina Reszka, Detlef Groth
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Patent number: 6458381Abstract: The invention concerns novel lipid compounds suitable for the transport of biologically active substances or molecules in cells. A preferred compound according to the invention is L-lysine-bis-(O,O′-cis-9-octadecenoyl-&bgr;-hydroxyethyl)-amide dihydrochloride or one of its optical isomers. In addition, the invention concerns complexes of the novel lipid compounds with polyanions such as DNA and RNA, and ternary complexes of the novel lipid compounds with polyanion and polycations. Finally, the invention concerns liposome formulations made from biologically active substances and the novel lipid compounds, as well as methods of transporting polyanions, polycations or biologically active substances through biological membranes by means fo the novel lipid compounds.Type: GrantFiled: October 14, 1998Date of Patent: October 1, 2002Inventors: Andrej Sourovoi, Guenther Jung
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Patent number: 6414170Abstract: The present invention relates to a method for preparing a cationic surfactant in which physical chemical characteristics such as softness, antistatic properties, etc. as well as biodegradability are quite excellent due to having an ester group and a hydrophilic hydroxyl group in its molecules. A cationic surfactant of the present invention is prepared by reacting tertiary amine drivatives, fatty acid, and epihalohydrin, and prepared simply by reacting esterification and quaternary reactions in one step with a high yield. The above cationic surfactant is a high grade alkyl quaternary ammonium compound as represented in General Formula (1), wherein R1 is a C1-C4 alkyl group; R2 is a C7-C21 linear or branched alkyl or alkenyl group; A is OCOR3, NHCOR3 or OH; R3 is a C7-C21 linear or branched alkyl or alkenyl group; X is a halogen atom; and n is an integral number from 2 to 6.Type: GrantFiled: January 23, 2001Date of Patent: July 2, 2002Assignee: LG Chemical Ltd.Inventors: Dong-Il Kim, Jeong-Wook Ha, Tae-Seong Kim, Moon-Jeong Rang
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Publication number: 20020061287Abstract: 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: ApplicationFiled: December 5, 2001Publication date: May 23, 2002Inventors: Jon A. Wolff, James E. Hagstrom, Vladimir G. Budker, Vladimir S. Trubetskoy, Paul M. Slattum, Lisa J. Hanson
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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: 6362370Abstract: Wood preservatives having biocidal properties which include quaternary ammonium compounds of general formula (I): wherein R1 is a C8-18-alkyl group or an optionally substituted benzyl group, R2 is a C8-18-alkyl group, R3 is a C1-4-alkyl group or a group of the formula —[CH2—CH2—O]n—H, R4 is a C1-4-alkyl group, n is a number from 0.5 to 8, preferably from 1 to 5, and A31 is the anion of an organic carboxylic acid which contains 2 to 12 C atoms and carries at least one hydroxyl, amino or sulfonic acid group. The wood preservatives also penetrate deeply into the wood without the use of pressure, and have only a mild corrosive action on metals. Furthermore, a process for treating timbers with these compositions, concentrates for the preparation thereof, the use of new and known quaternary ammonium compounds in wood preservatives and new quaternary ammonium compounds and their use as biocides.Type: GrantFiled: September 6, 2000Date of Patent: March 26, 2002Assignee: Lonza AGInventors: Florian Lichtenberg, Joachim Fritschi, Volker Ranft
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Publication number: 20020026078Abstract: An amine catalyst for production of a polyurethane and a polyisocyanurate is provided which comprises a quaternary ammonium compound represented by General Formula (1): 1Type: ApplicationFiled: August 27, 2001Publication date: February 28, 2002Applicant: Tosoh CorporationInventors: Katsumi Tokumoto, Yutaka Tamano, Shuichi Okuzono
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Publication number: 20020009650Abstract: The invention concerns ionic compounds in which the anionic load has been delocalized. A compound disclosed by the invention is comprised of an amide or one of its salts, including an anionic portion combined with at least one cationic portion M+m in sufficient numbers to ensure overall electronic neutrality; the compound is further comprised of M as a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation with the valence m, an organic cation with the valence m, or an organometallic cation with the valence m. The anionic portion matches the formula RF—SOx—N−Z, wherein RF is a perfluorinated group, x is 1 or 2, and Z is an electroattractive substituent. The compounds can be used notably for ionic conducting materials, electronic conducting materials, colorants, and the catalysis of various chemical reactions.Type: ApplicationFiled: May 16, 2001Publication date: January 24, 2002Inventors: Christophe Michot, Michel Armand, Michel Gauthier, Yves Choquette
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Publication number: 20010047112Abstract: This invention relates to stable aromatic amine compositions. These compositions comprise a) an organic compound containing at least one carboxylic acid group,, and b) an aromatic amine. This invention also relates to a process for stabilizing the color of aromatic amines, and to the use of these aromatic amines as initiators for the preparation of polyether polyols.Type: ApplicationFiled: September 17, 1999Publication date: November 29, 2001Inventor: RICK L. ADKINS
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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: 6235914Abstract: A process for making a tertiary amine ester of the following formula (I): the process comprising: (a) reacting a ketone or an aldehyde having the formula with a glycol to form a ketal or an acetal; (b) reacting the ketal or the acetal with acrylonitrile to form an ether nitrile; (c) reducing the ether nitrile to a tertiary amine ketal or a tertiary amine acetal; (d) hydrolyzing the tertiary amine ketal or the tertiary amine acetal to a tertiary amine diol; and (e) esterifying the tertiary amine diol to the tertiary amine ester of formula (I), wherein R1 and R2 are each independently a hydrogen atom or a linear, branched, or cyclic alkyl, alkylene, alkaryl, or aryl-containing group containing 1 to 18 carbon atoms; and each R3 are each independently of one another fatty acid radicals having 6-22 carbon atoms.Type: GrantFiled: August 18, 2000Date of Patent: May 22, 2001Assignee: Goldschmidt Chemical CompanyInventors: Philip Howard Steiger, Christopher Joseph Toney
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Patent number: 6198000Abstract: A process for preparing a compound of the formula wherein R1, m, o and p are described below, which comprises adding a base of the formula wherein R2, R3 and R4 are as described below, to a solution comprising a compound of the formula wherein R1, m, o and p are as described below, and a halonitromethane of the formula O2NCH2X, wherein X is a halogen atom dissolved in a non-aqueous inert solvent. The compounds of formula III are useful as intermediates in the syntheses of azabicyclo quinoline carboxylic acids, and their pharmaceutically acceptable salts and prodrugs, having antibacterial activity. This invention also relates to the base of formula IV wherein each R2 is butyl, R3 is hydrogen and each R4 is t-butyl.Type: GrantFiled: September 21, 1999Date of Patent: March 6, 2001Assignee: Pfizer Inc.Inventor: Joel M. Hawkins
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Patent number: 6194606Abstract: The present invention provides compounds having the formula: in which R is hydrogen or C1-C4alkyl, preferably hydrogen and Y is hydrogen, C1-C4alkyl, C1-C4alkoxy, CF3, halogen (F, Cl, Br or I) or SO3M in which M is H, Na, K, Ca, Mg, ammonium, mono-, di-, tri- or tetra-C1-C4alkylammonium, mono-, di- or tri-hydroxyalkylammonium or ammonium that is di- or tri-substituted with a mixture of C1-C4alkyl and C1-C4hydroxyalkyl groups; a process for their production; and their use as intermediates in the production of asymmetric or symmetric fluorescent whitening agents.Type: GrantFiled: September 22, 1998Date of Patent: February 27, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Bernd Siebenhaar, Bruno Casagrande, Victor Eliu
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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: 6072063Abstract: Ester quats of the formula (1) below are described: ##STR1## where RCO is an aliphatic acyl radical having 6 to 22 carbon atoms, R.sup.1 is a methyl radical, R.sup.2 is a C.sub.1 -C.sub.6 -alkyl radical, R.sup.3 is a C.sub.3 -C.sub.6 -alkyl radical and X.sup.- is a halogen anion. They are prepared by quaternizing the corresponding carboxylic acid ethanolamine ester compound with a methyl halide in the absence or presence of solvents. The ester quats of the invention have a low melting point. Furthermore, even in high concentration they are highly water soluble and, on account of their preparation, are obtained in high purity and free from toxic contents. These ester quats can be used in many ways and are suitable, for example, for preparing solid or aqueous formulations having a high surfactant effect.Type: GrantFiled: February 26, 1997Date of Patent: June 6, 2000Assignee: Clariant GmbHInventors: Oliver Eyrisch, Rudolf Aigner
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Patent number: 6057455Abstract: A process for preparing a compound of the formula ##STR1## wherein R.sup.1, m, o and p are described below, which comprises adding a base of the formula ##STR2## wherein R.sup.2, R.sup.3 and R.sup.4 are as described below, to a solution comprising a compound of the formula ##STR3## wherein R.sup.1, m, o and p are as described below, and a halonitromethane of the formula O.sub.2 NCH.sub.2 X, wherein X is a halogen atom dissolved in a non-aqueous inert solvent. The compounds of formula III are useful as intermediates in the syntheses of azabicyclo quinoline carboxylic acids, and their pharmaceutically acceptable salts and prodrugs, having antibacterial activity. This invention also relates to the base of formula IV wherein each R.sup.2 is butyl, R.sup.3 is hydrogen and each R.sup.4 is t-butyl.Type: GrantFiled: July 7, 1997Date of Patent: May 2, 2000Assignee: Pfizer, Inc.Inventor: Joel M. Hawkins
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Patent number: 6054615Abstract: Selected quaternary ammonium salts containing fluoroalkyl, preferably perfluoroalkyl, groups that are stable to bases are described. They are useful as phase transfer reaction catalysts, especially in basic media.Type: GrantFiled: May 27, 1999Date of Patent: April 25, 2000Assignee: E.I. du Pont de Nemours and CompanyInventor: Weiming Qiu
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Patent number: 6051611Abstract: The invention relates to polymeric quaternary ammonium compounds which are useful as disinfectants and/or preservatives in ophthalmic compostions.Type: GrantFiled: December 22, 1998Date of Patent: April 18, 2000Assignee: Alcon Laboratories, Inc.Inventors: Evan P. Kyba, Joonsup Park
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Patent number: 6031137Abstract: This invention relates to stable aromatic amine compositions. These compositions comprise a) an organic compound containing at least one carboxylic acid group, and b) an aromatic amine. This invention also relates to a process for stabilizing the color of aromatic amines, and to the use of these aromatic amines as initiators for the preparation of polyether polyols.Type: GrantFiled: May 29, 1998Date of Patent: February 29, 2000Assignee: Bayer CorporationInventor: Rick L. Adkins
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Patent number: 5962709Abstract: Process for the aftertreatment of betaine and amphoteric surfactants comprising adjusting the pH to the range of from 11 to 14 by addition of an alkali metal hydroxide, followed by a thermal aftertreatment if the surfactant contains dichloroacetic acid residues.Type: GrantFiled: September 12, 1995Date of Patent: October 5, 1999Assignee: Henkel Kommanditgesellschaft auf Aktien (KGaA)Inventors: Gunter Uphues, Uwe Ploog, Rainer Jeschke, Renate Schick
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Patent number: 5945082Abstract: Novel cyanophosphorus compounds are disclosed. The preparation, purification, and characterization of dicyanophosphinate, cyanopolyphosphates, tricyanocyclotriphosphonate and tetracyanocyclotetraphosphate are presented.Type: GrantFiled: December 23, 1997Date of Patent: August 31, 1999Assignee: Monsanto CompanyInventors: Patrick J. Lennon, Sergey G. Vulfson
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Patent number: 5935542Abstract: The novel cyanophosphonate compounds of the present invention include cyanophosphonate salts, cyanophosphonate monoacid salts, cyanophosphonate monoacid esters, cyanophosphonate monoester salts and cyanophosphonate methylester salts.Type: GrantFiled: December 23, 1997Date of Patent: August 10, 1999Assignee: Monsanto CompanyInventors: Patrick J. Lennon, Sergey G. Vulfson
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Patent number: 5902909Abstract: The present invention provides compounds having the formula: ##STR1## in which R is hydrogen or C.sub.1 -C.sub.4 alkyl, preferably hydrogen and Y is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, CF.sub.3, halogen (F, Cl, Br or I) or SO.sub.3 M in which M is H, Na, K, Ca, Mg, ammonium, mono-, di-, tri- or tetra-C.sub.1 -C.sub.4 alkylammonium, mono-, di- or tri-hydroxyalkylammonium or ammonium that is di- or tri-substituted with a mixture of C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 hydroxyalkyl groups; a process for their production; and their use as intermediates in the production of asymmetric or symmetric fluorescent whitening agents.Type: GrantFiled: December 19, 1997Date of Patent: May 11, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Bernd Siebenhaar, Bruno Casagrande, Victor Eliu
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Patent number: 5892116Abstract: Gelators gel a variety of nonpolar and polar liquids. Moreover, gelation of various monomers with subsequent polymerization of the gelled monomers forms organic zeolites and membrane materials. An ionic gelator includes salts of compounds of the formula (I):?R.sup.1 R.sup.2 R.sup.3 X-R.sup.4 !.+-.Y.-+. (I)where R.sup.1, R.sup.2 and R.sup.3 are the same or different hydrogen or organic groups including alkyl groups, alkenyl groups, alkynyl groups, aryl groups, arylalkyl groups, alkoxy groups, aryloxy groups; X is a Group IIIA or Group VA element; R.sup.4 is a steroidal group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an arylalkyl group, an alkoxy group or an aryloxy group; and Y is a Group IA or Group VIIA element or one-half of a Group IIA or VIA element, that is, a divalent counterion. The gelling agent composition may include a single isomer or mixtures of isomers of the formula (I). A non-ionic gelator also includes compounds of the formula:R.sup.1 R.sup.2 R.sup.3 X (II)where R.Type: GrantFiled: January 2, 1997Date of Patent: April 6, 1999Assignee: Georgetown UniversityInventors: Richard G. Weiss, Liangde Lu
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Patent number: 5880299Abstract: The invention relates to new esterquats which are obtained by reacting trialkanolamines with a mixture of fatty acids and dicarboxylic acids and quaternizing the resulting esters in known manner, optionally after alkoxylation. Cationic surfactants are obtained which show particularly high ecotoxicological compatibility, provide synthetic and natural fibers with a pleasant feel and, at the same time, reduce electrostatic charging between the filaments.Type: GrantFiled: October 24, 1996Date of Patent: March 9, 1999Assignee: Henkel CorporationInventors: Oriol Ponsati Obiols, Nuria Bonastre, Joaquim Bigorra Llosas
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Patent number: 5869715Abstract: For use in transporting biologically active species into and through membrane barriers, a cationic amine compound is utilized that has 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.- is an anion.Type: GrantFiled: September 27, 1995Date of Patent: February 9, 1999Assignee: The Reagents of the University of CaliforniaInventors: Michael H. Nantz, Michael J. Bennett, Rajiv P. Balasubramaniam
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Patent number: 5869716Abstract: Esterquats based on natural fats and oils can be directly produced by subjecting fatty acid glyerine ester to ester interchange, in the presence of alkaline and/or alkaline earth boron hydrides and hypophosphoric acid or their alkaline and/or alkaline earth salts and possibly free fatty acid, with hydroxy-functionalised tertiary amines and quaternising the resultant products in the manner known per se.Type: GrantFiled: September 16, 1996Date of Patent: February 9, 1999Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Rafael Pi Subirana, Joaquim Bigorra Llosas, Antonio Trius Oliva
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Patent number: 5858317Abstract: A process for preparing cyanophosphonate derivatives involves contacting phosphoric anhydride (P.sub.4 O.sub.10) and a cyanide, preferably in the presence of a Lewis base, in a reaction mixture under sufficient conditions to produce a cyanophosphonate derivative. The cyanophosphonate derivative can be subsequently hydrogenated to produce an aminomethylphosphonate derivative.Type: GrantFiled: December 23, 1997Date of Patent: January 12, 1999Assignee: Monsanto CompanyInventors: Patrick J. Lennon, Sergey G. Vulfson
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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: 5763639Abstract: A process for preparing quaternized glycine nitriles of formula I ##STR1## comprising reaction of the corresponding precursor amine, aldehyde, hydrocyanic acid or alkali metal cyanide, and subsequent quaternization with an alkylating agent, wherein the reaction and quaternization are carried out successively in aqueous medium without isolation of an intermediate.Type: GrantFiled: March 3, 1997Date of Patent: June 9, 1998Assignee: BASF AktiengesellschaftInventors: Ulrich Annen, Hans-Peter Seelmann-Eggebert, Rudi Widder, Reinhard Muller
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Patent number: 5705696Abstract: Quaternary (e.g., tetraalkylammonium and tetraalkylphosphonium) salts containing non-halide anions are prepared by performing an anion exchange reaction by liquid-liquid extraction with a chlorinated solvent of a mixture of an aqueous solution an alkali metal salt of the anion and a corresponding quaternary halide.Type: GrantFiled: August 1, 1996Date of Patent: January 6, 1998Assignee: General Electric CompanyInventor: Joseph Anthony King, Jr.
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Patent number: 5705663Abstract: The invention relates to quaternized triethanolamine difatty acid esters prepared from triethanolamine, fatty acid, fatty acid ester and a quaternizing agent and to a process for their preparation and to their use. The quaternized triethanolamine difatty acid esters thus prepared can be used to produce particularly storage-, temperature- and viscosity-stable rinse cycle laundry softeners having a high active content.Type: GrantFiled: December 7, 1995Date of Patent: January 6, 1998Assignee: Servo Delden B.V.Inventors: Michael Brock, Meinolf Enneking, Kurt Kosswig
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Patent number: 5641726Abstract: 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.12 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: June 9, 1993Date of Patent: June 24, 1997Assignee: Lonza, Inc.Inventor: Leigh E. Walker
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Patent number: 5639840Abstract: Described are novel fluoride ion-releasing acrylic or methacrylic acid-based monomers, fluoride ion-releasing dental resin materials prepared from the monomers, and processes for preparing the monomers and dental resin materials. The monomers of the invention are prepared in good yield from readily available starting materials. Dental resin materials of the invention exhibit excellent sustained fluoride ion release.Type: GrantFiled: January 26, 1995Date of Patent: June 17, 1997Assignee: Indiana University FoundationInventors: Wilmer K. Fife, Martel Zeldin, Slawomir Rubinsztajn
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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: 5614548Abstract: Quaternary amine-containing ether lipid analogs of the formulaR.sub.1 --X--R.sub.2 --N.sup.+ (R.sub.3) (R.sub.4) (R.sub.5) Z.sup.-are disclosed. R.sub.1 represents a hydrophobic group and R.sub.2 represents the backbone of the molecule, with the quaternary amine being linked directly to the backbone. Pharmaceutical compositions including these compounds and methods of combating tumors with these compounds are disclosed. Also disclosed is a method of combating viral infections with both these compounds and ET-18-OMe and its analogs.Type: GrantFiled: September 8, 1994Date of Patent: March 25, 1997Assignee: Wake Forest UniversityInventors: Claude Piantadosi, Khalid S. Ishaq, Canio J. Marasco, Jr., Larry W. Daniel, Louis S. Kucera, Edward J. Modest, Barry P. Goz
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Patent number: 5578234Abstract: The present invention relates to dryer-activated fabric softening compositions and articles, having improved antistatic and/or softening effects, for use in an automatic clothes dryer, especially those comprising, as essential ingredients: (A) fabric softener consisting essentially of: (1) from about 5% to about 95% of preferably biodegradable quaternary ammonium compound selected from the group consisting of the compounds of Formulas I, II, III, and mixtures thereof; (2) from 0% to about 95% highly ethoxylated and/or propoxylated, preferably at least 5 ethylene oxide (EO) and/or propylene oxide (PO) groups per molecule, sugar derivative containing at least one long hydrophobic moiety per molecule; and (3) from 0% to about 95% of carboxylic acid salt of tertiary amine; and (B) from about 1% to about 15%, unsaturated fatty acid having an IV of from about 3 to about 60. The amount of (A) present is at least sufficient to provide softening and/or antistatic effects.Type: GrantFiled: October 10, 1995Date of Patent: November 26, 1996Assignee: The Procter & Gamble CompanyInventors: Alessandro Corona, III, Clyde D. Palmer, John R. Rusche, Stephanie Lin-Lin Sung
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Patent number: 5574179Abstract: The present invention relates to softening compounds; stable, homogeneous, preferably concentrated, aqueous liquid and solid textile treatment compositions; and intermediate compositions and/or processes for making said compositions.The compositions of the present invention contain diester quaternary ammonium compounds wherein the fatty acyl groups have an Iodine Value of from greater than about 5 to less than about 100, a cis/trans isomer weight ratio of greater than about 30/70 when the Iodine Value is less than about 25, the level of unsaturation being less than about 65% by weight, wherein said compounds are capable of forming concentrated aqueous compositions with concentrations greater than about 13% by weight at an Iodine Value of greater than about 10 without viscosity modifiers other than normal polar organic solvents present in the raw material of the compound or added electrolyte.Type: GrantFiled: February 28, 1995Date of Patent: November 12, 1996Assignee: The Procter & Gamble CompanyInventors: Errol H. Wahl, Dennis R. Bacon, Ellen S. Baker, Jean-Francois Bodet, Michael E. Burns, Hugo J. M. Demeyere, Charles A. Hensley, Robert Mermelstein, John C. Severns, John H. Shaw, Jr., Michael P. Siklosi, Alice M. Vogel, Jeffrey W. Watson
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Patent number: 5545749Abstract: A quaternary ammonium compound solution comprising from about 50% to about 80% of a quaternary ammonium compound and from about 20% to about 50% of a solvent. The solvent being from about 25% to about 100% of alkylene glycol with the remainder being water. The method of making quaternary ammonium compounds comprises reacting methyl chloride and/or benzyl chloride and dialkylmethylamine and/or alkyldimethylamine in an alkylene glycol to completion and diluting the same with sufficient water to a solution in which the alkylene glycol is from about 25% to about 100% of the solvent component of the total solution and the quaternary ammonium compound is from about 50% weight to about 80% weight of the quaternary ammonium compound solution.Type: GrantFiled: October 5, 1994Date of Patent: August 13, 1996Assignee: Huntington Laboratories, Inc.Inventors: Kim R. Smith, Frederick M. Boyd, Samih S. Abouhalkah
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Patent number: 5543522Abstract: There are disclosed a process for preparing an ambient temperature molten salt, which comprises treating an ambient temperature molten salt consisting essentially of 20 to 50 mole % of an aluminum halide and 80 to 50 mole % of an onium halide, containing oxygen-containing impurities originating from water with thionyl chloride anda process for preparing an ambient temperature molten salt for effecting aluminum electroplating, which comprises treating mixed ambient temperature molten salts consisting essentially of 30 to 50 mole % of an aluminum halide and 70 to 50 mole % of an onium halide, containing oxygen-containing impurities originating from water with thionyl chloride, and then adding aluminum halide to the molten salt to prepare an ambient temperature molten salt composition consisting essentially of 50 to 80 mole % of an aluminum halide and 50 to 20 mole % of an onium halide.Type: GrantFiled: August 25, 1994Date of Patent: August 6, 1996Assignees: Mitsubishi Chemical Corporation, Nisshin Steel Co., Ltd.Inventors: Takayuki Kawahara, Hitoshi Suzuki, Asao Kominato
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Patent number: 5534192Abstract: Antistatic agents and their use in processing textiles or formed plastic substrates. The antistatic agent comprises a compound having a fluorocarbon moiety and an ethoxylated quaternary ammonium moiety. The antistatic composition increases the electrolytic conductivity of textile or plastic materials treated therewith, thereby increasing the rate of electrostatic charge dissipation thereof. The coatings remain effective after exposure of the treated substrate to an aqueous environment.Type: GrantFiled: February 22, 1995Date of Patent: July 9, 1996Assignee: Henkel CorporationInventors: Michael J. Incorvia, Stephen A. Fischer
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Patent number: 5516438Abstract: A method of preparing a fabric softening material which comprises a quaternary ammonium material and at least one C.sub.8-28 alkyl or alkenyl group connected to the molecule via an ester linkage. The process comprises the step of reacting a base material with an alkyl or alkenyl group continuing material, such that at least one alkyl or alkenyl group is connected to the base material via an ester linkage. The reaction between the base material and the alkyl or alkenyl group containing material is carried out in the presence of more than 10 mole percentage excess of the alkyl or alkenyl group containing material to the base material. The excess material being effective to lower the pour point of the softener material.Type: GrantFiled: March 30, 1995Date of Patent: May 14, 1996Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventor: Graham A. Turner
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Patent number: 5512597Abstract: The invention relates to polymeric quaternary ammonium compounds which are useful as disinfectants and/or preservatives in ophthalmic compositions.Type: GrantFiled: January 13, 1995Date of Patent: April 30, 1996Assignee: Alcon Laboratories, Inc.Inventors: Evan P. Kyba, Joon S. Park
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Patent number: 5478486Abstract: Antistatic agents and their use in processing textiles or formed plastic substrates. The antistatic agent comprises a compound having a fluorocarbon moiety and an ethoxylated quaternary ammonium moiety. The antistatic composition increases the electrolytic conductivity of treated textile or plastic materials, thereby increasing the rate of electrostatic charge dissipation thereof. The antistatic agents remain effective after exposure of the treated substrate to an aqueous environment.Type: GrantFiled: November 18, 1993Date of Patent: December 26, 1995Assignee: Henkel CorporationInventor: Michael J. Incorvia
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Patent number: 5475119Abstract: Ionic monomeric diallylammonium compounds having a targeted combination of diallylammonium cations with selected anions have particularly high and constant charge control properties and very good heat stabilities and dispersibilities.The compounds according to the invention are outstandingly suitable for use as colorless charge control agents in toners and developers for electrophotographic recording processes and for use as charge-improving agents in powders and paints for surface coating, in particular in triboelectrically or electrokinetically sprayed powder paints.Type: GrantFiled: December 17, 1992Date of Patent: December 12, 1995Assignee: Hoechst AktiengesellschaftInventors: Rudiger Baur, Hans-Tobias Macholdt
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Patent number: 5438034Abstract: Quaternary ammonium carbonates having the formula ##STR1## 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 have been synthesized.These compounds and compositions further comprising the corresponding quaternary ammonium bicarbonate ##STR2## wherein R.sup.1 is the same or a different C.sub.1 -C.sub.20 alkyl or aryl-substituted alkyl group and R.sup.2 is the same or a different C.sub.8 -C.sub.20 alkyl group and/or the corresponding quaternary ammonium metal carbonate ##STR3## wherein R.sup.1 is the same or a different C.sub.1 -C.sub.20 alkyl or aryl-substituted alkyl group; R.sup.2 is the same or a different C.sub.8 -C.sub.20 alkyl group and M is a non-coupler metal, are prepared by reacting two reactants, a C.sub.1 -C.sub.20 alkyl or aryl-substituted alkyl, C.sub.8 -C.sub.20 alkyl quaternary ammonium chloride and a metal hydroxide, in a solvent comprising a C.sub.1 -C.sub.4 normal alcohol.Type: GrantFiled: June 9, 1993Date of Patent: August 1, 1995Assignee: Lonza, Inc.Inventor: Leigh E. Walker
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Patent number: RE37555Abstract: The invention relates to a method of producing a mixture of a quaternary ammonium compound, fatty acid, fatty acid ester and tertiary amine salt in situ which is a highly functional mixture that is manufactured in a single step reaction whereby quaternization is completed without the aid of solvents, especially flammable solvents. The single step reaction process eliminates separate blending of individual components. The compositions obtained can be used as fabric softeners, in modified clays, as hair treating compounds and as disinfectants.Type: GrantFiled: June 11, 1999Date of Patent: February 19, 2002Assignee: Goldschmidt Chemical CompanyInventors: Jeannene A. Ackerman, Michael Miller, David E. Whittlinger