Benzene Ring Containing Patents (Class 564/282)
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Publication number: 20040214867Abstract: In one aspect, the present invention concerns the use of certain quaternary ammonium compounds as active ingredient in the manufacture of a medicament for use in the treatment and/or prevention of cough in warm-blooded animals, including humans, such as compounds of the following formula (I): Y-J-E An− wherein J is independently selected from a group represented by one of formulae (II), (III) and (IV).Type: ApplicationFiled: February 14, 2003Publication date: October 28, 2004Inventors: Lewis Siu Leung Choi, Gregory N Beatch, Clive Page
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Publication number: 20040157344Abstract: Ultrasensitive detection of a chemical substance (analyte) by mass spectrometry is achieved by employing a molecular tag that yields an intense parent ion and then an intense daughter ion in a multi-stage mass spectrometer.Type: ApplicationFiled: December 19, 2003Publication date: August 12, 2004Inventors: Poguang Wang, Guodong Li, Jianxin Gao, Roger W. Giese
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Electrochemically stable onium salts and electrolytes containing such for electrochemical capacitors
Patent number: 6743947Abstract: Based on the discovery that the melting point and solubility of onium salts are affected by the asymmetry of the substitution on cation, and that the branched substituents effectively shield onium cations from electrochemical reduction, new onium salts are synthesized and high performance electrolytes based on these salts for electrochemical capacitor are provided. The composition of the new electrolyte comprises an onium salt or mixture of such onium salts dissolved in aprotic, non-aqueous solvents or mixture of such solvents. The electrolyte is able to perform at high rate of charge/discharge, at low ambient temperatures, and within wide operating voltage, due to the high solubility, low melting temperature, and the improved reduction stability of the new onium cations, respectively.Type: GrantFiled: May 10, 1999Date of Patent: June 1, 2004Assignee: The United States of America as represented by the Secretary of the ArmyInventors: Kang Xu, Shengping Ding, T. Richard Jow -
Patent number: 6727388Abstract: The present invention is a demulsifying and corrosion-inhibiting compound formed from the salt of an amphiphilic amine and an amphiphilic acid. In a preferred embodiment of the invention, the demulsifier may be a salt of an alkyl amine and an alkyl aryl sulfonic acid. Even more preferably, the demulsifier may be a salt of a methyl, di-cocoyl amine and an alkyl aryl sulfonic acid. According to another embodiment of the invention, an organic system may be demulsified by mixing the salt of an alkyl amine and an alkyl sulfonic acid with the system to be demulsified.Type: GrantFiled: February 4, 2003Date of Patent: April 27, 2004Assignee: Pilot Chemical Holdings, Inc.Inventor: Robert Golden
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Publication number: 20040067938Abstract: Novel quaternary amine containing compounds including their pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives having activity against mammalian factor Xa are described. Compositions containing such compounds are also described. The compounds and compositions are useful in vitro or in vivo for preventing or treating conditions in mammals characterized by undesired thrombosis.Type: ApplicationFiled: November 3, 2003Publication date: April 8, 2004Inventors: Penglie Zhang, Robert M. Scarborough, Bing-Yan Zhu
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Publication number: 20040054231Abstract: Ionic compounds having a freezing point of no more than 50° C., formed by the reaction of at least one amine salt of the formula R1R2R3R4N+X− (I) with at least one hydrated salt, which is a chloride, nitrate, sulphate or acetate of Li, Mg, Ca, Cr, Mn, Fe, Co, Ni, Cu, Zn, Cd, Pb, Bi, La or Ce; wherein R1, R2 and R3 are each independently a C1 to C5 alkyl or a C6 to C10 cycloalkyl group, or wherein R2 and R3 taken together represent a C4 to C10 alkylene group, thereby forming with the N atom of formula (I) a 5 to 11 membered heterocyclic ring, and wherein R4 is hydrogen, or phenyl, or C1 to C12 alkyl or cycloalkyl group, optionally substituted with at least one group selected from OH, Cl, Br, F, I, phenyl, NH2, CN, NO2, COOR5, CHO, COR5 and OR5, wherein R5 is a C1 to C10 alkyl or cycloalkyl group, and X− is an anion capable of being complexed by the said hydrated salt.Type: ApplicationFiled: August 11, 2003Publication date: March 18, 2004Inventors: Andrew Abbott, David L Davies, Glen Capper, Raymond K Rasheed, Vasuki Tambyrajah
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Publication number: 20040019043Abstract: The current invention provides novel thiomolybdate derivatives, methods of making novel thiomolybdate derivatives, pharmaceutical compositions of novel thiomolybdate derivatives, methods of using novel thiomolybdate derivatives to treat diseases associated with aberrant vascularization and methods of using pharmaceutical compositions of thiomolybdate derivatives to treat diseases associated with aberrant vascularization.Type: ApplicationFiled: July 23, 2002Publication date: January 29, 2004Inventors: Dimitri Coucouvanis, Robert J. Ternansky, Patricia L. Gladstone, Amy L. Allan, Melissa L.P. Price, Sean M. O'Hare
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Publication number: 20040019087Abstract: The current invention provides novel thiomolybdate derivatives, methods of making novel thiomolybdate derivatives, pharmaceutical compositions of novel thiomolybdate derivatives, methods of using novel thiomolybdate derivatives to treat diseases associated with aberrant vascularization, copper metabolism disorders, neurodegenerative disorders, obesity or NF-&kgr;B dysregulation and methods of using pharmaceutical compositions of thiomolybdate derivatives to treat diseases associated with aberrant vascularization, copper metabolism disorders, neurodegenerative disorders, obesity or NF-&kgr;B dysregulation.Type: ApplicationFiled: May 28, 2003Publication date: January 29, 2004Inventors: Robert J. Ternansky, Andrew Mazar, Patricia L. Gladstone, Dimitri Coucouvanis, Amy L. Allan, Sean M. O'Hare, Melissa L.P. Price, Steven Robert Pirie-Shepherd, Fernando Donate
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Patent number: 6670508Abstract: A compound of formula (I) is prepared alone or in combination with at least one monomer of formula (II): the quaternizing agents benzyl chloride is introduced into a solution, in a solvent selected from compounds of the formulae (I) and (II) and mixtures of these, of the compound of formula (III) at a temperature of from 35 to 60° C., and then water is added and the reaction is allowed to proceed to complete or substantially complete conversion of the compound (III), an aqueous solution of desired compound (I) is isolated where appropriate with at least one compound (II), if this or these have/has been used as solvent, and the water is removed where appropriate.Type: GrantFiled: April 26, 2002Date of Patent: December 30, 2003Assignee: AtofinaInventor: Alain Riondel
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Patent number: 6664224Abstract: The novel quaternary ammonium salt according to the invention has two quaternary ammonium groups connected to a benzene ring, wherein two C4-12 alkyl groups and one C1-2 alkyl group are connected per one nitrogen atom constituting the quaternary ammonium. The compound is used as an antimicrobial agent, exhibits a high safety to human as compared with known antimicrobial agents, exerts an excellent sterilizing effect itself and exhibits a wide sterilizing spectrum. In particular, the compound is used as a presevative for eye drop.Type: GrantFiled: May 15, 2001Date of Patent: December 16, 2003Assignee: Toagosei Co., Ltd.Inventors: Hiroki Kourai, Shigeyuki Shibata, Katsuyoshi Harada, Masayoshi Kume
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Patent number: 6638321Abstract: The invention relates to novel monobenzene oxidation bases containing at least one cationic group Z, Z being chosen from aliphatic chains containing at least one quaternized unsaturated ring, to their use for the oxidation dyeing of keratin fibers, to dye compositions containing them and to oxidation dyeing processes using them.Type: GrantFiled: June 7, 1999Date of Patent: October 28, 2003Assignee: L'OrealInventors: Alain Genet, Alain Lagrange
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Publication number: 20030181489Abstract: In one aspect, the present invention concerns the use of certain quaternary ammonium compounds as active ingredient in the manufacture of a medicament for use in the treatment and/or prevention of cough in warm-blooded animals, including humans, such as compounds of formula Y—J—E An− (I), wherein J is independently selected from a group represented by one of formulae (II), (III) and (IV).Type: ApplicationFiled: February 14, 2003Publication date: September 25, 2003Inventors: Lewis Siu Leung Choi, Gregory N Beatch, Clive Page
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Publication number: 20030138846Abstract: Embodiments of the present invention generally relate to carrying out organic chemistry on solid supports comprising derivatised functionalities, methods for synthesizing said supports, methods for synthesizing compounds comprising amine groups or N-containing heterocycles using said solid supports, intermediate compounds linked to said supports and uses thereof.Type: ApplicationFiled: September 17, 2002Publication date: July 24, 2003Inventors: David Gani, Friedrich Erich Karl Kroll, Michael John Plater, John Richard Morphy, David Rees
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Publication number: 20030130534Abstract: The present invention is a demulsifying and corrosion-inhibiting compound formed from the salt of an amphiphilic amine and an amphiphilic acid. In a preferred embodiment of the invention, the demulsifier may be a salt of an alkyl amine and an alkyl aryl sulfonic acid. Even more preferably, the demulsifier may be a salt of a methyl, di-cocoyl amine and an alkyl aryl sulfonic acid. According to another embodiment of the invention, an organic system may be demulsified by mixing the salt of an alkyl amine and an alkyl sulfonic acid with the system to be demulsified.Type: ApplicationFiled: February 4, 2003Publication date: July 10, 2003Applicant: Pilot Chemical Holdings, Inc.Inventor: Robert Golden
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Patent number: 6545181Abstract: The present invention is a demulsifying and corrosion-inhibiting compound formed from the salt of an amphiphilic amine and an amphiphilic acid. In a preferred embodiment of the invention, the demulsifier may be a salt of an alkyl amine and an alkyl aryl sulfonic acid. Even more preferably, the demulsifier may be a salt of a methyl, di-cocoyl amine and an alkyl aryl sulfonic acid. According to another embodiment of the invention, an organic system may be demulsified by mixing the salt of an alkyl amine and an alkyl sulfonic acid with the system to be demulsified.Type: GrantFiled: October 24, 2000Date of Patent: April 8, 2003Assignee: Pilot Chemical Holdings, Inc.Inventor: Robert Golden
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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: 6479697Abstract: A process for the preparation of &agr;-(2,4-disulfophenyl)-N-tert-butylnitrone diacids and pharmaceutically acceptable salts thereof by the reaction of the corresponding disulfophenyl aldehyde with N-tert-butylhydroxylammonium acetate is disclosed.Type: GrantFiled: April 5, 2001Date of Patent: November 12, 2002Assignee: AstraZeneca ABInventors: Henry Kruk, John McGinley, Sergei Pouhov, John Vajda, Jörgen Blixt
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Publication number: 20020165409Abstract: A quaternary ammonium hydroxycarboxylate is produced by quaternizing a tertiary amine with a hydroxycarboxylic ester represented by the following Formula 1: 1Type: ApplicationFiled: April 19, 2002Publication date: November 7, 2002Inventors: Yutaka Kanbara, Yasushi Higuchi, Tomoo Tsujimoto, Genki Nogami
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Patent number: 6469204Abstract: These compounds are represented by the formulae (Ia) and (Ib). To prepare them, in a first stage, p-xylylene dichloride is reacted with a compound (II) to produce a compound (III) and, in a second stage, the compound (III) thus obtained is reacted with a compound of formula (IVa) or (IVb), resulting in an aqueous solution of the compound (Ia) or (Ib) respectively, the water of which is removed, if appropriate.Type: GrantFiled: October 30, 2001Date of Patent: October 22, 2002Assignee: AtofinaInventors: Alain Riondel, Vladimir Chaplinski
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Patent number: 6399827Abstract: Disclosed is quaternary ammonium phosphate compound having formula (1) and which has an anticorrosive and a biocidal efffect to have a capability of preventing corrosion of various metals including corrosive metal substances, e.g. carbon steels, iron casts, stain steels, coppers, tinning steel plates or alumina and an efficient method of preparing the same. In formula (1), R1 is a straight or a branched alkyl or aryl radical with 1 to 27 carbon atom(s) free of —OH group and may contain hereto-atoms, and both R2 and R3 are methyl groups or R2 and R3 are combined to form a heterocyclic compound with 4 to 6 of carbon atoms containing oxygen and nitrogen.Type: GrantFiled: June 12, 2000Date of Patent: June 4, 2002Assignee: SK ChemicalsInventors: Soon-Jong Hahn, Jeong-Joo Shin, Jae-Min Ha, Chang-Mook Cho, Ki-Man Park, Kwang-Hee Yoo, Dong-Jin Choi, Jun-Weon Park
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Patent number: 6379398Abstract: Dibenzenic ortho-phenylenediamines comprising at least one cationic group Z, Z being chosen from quaternized aliphatic chains, aliphatic chains comprising at least one quaternized saturated ring, and aliphatic chains comprising at least one quaternized unsaturated ring, to their use as oxidation base, coupler or autooxidizable dye for the oxidation dyeing of keratin fibers, to dye compositions containing them, and to oxidation dyeing processes using them.Type: GrantFiled: September 1, 1999Date of Patent: April 30, 2002Assignee: L'OrealInventors: Alain Genet, Alain Lagrange
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Patent number: 6344529Abstract: Disclosed are compounds useful as catalyst activators for olefin polymerization, comprising structures of the following formulae: wherein: L+ is a protonated derivative of an element of Group 15 of the Periodic Table of the Elements, additionally bearing two hydrocarbyl substituents of from 1 to 50 carbons each, or a positively charged derivative of an element of Group 14 of the Periodic Table of the Elements, said Group 14 element being substituted with three hydrocarbyl substituents of from 1 to 50 carbons each; R1 is a divalent linking group of from 1 to 40 non-hydrogen atoms; R2 independently each occurrence is a ligand group of from 1 to 50 nonhydrogen atoms with the proviso that in a sufficient number of occurrences to balance charge in the compound, R2 is L+—R1—; M1 is boron, aluminum or gallium; Arf independently each occurrence is a monovalent, fluorinated organic group containing from 6 to 100 non-hydrogen atoms; Y is a Group 15 element; and Z is a GrouType: GrantFiled: December 6, 1999Date of Patent: February 5, 2002Assignee: The Dow Chemical CompanyInventors: Edmund M. Carnahan, Grant B. Jacobsen, Jerzy Klosin, Peter N. Nickias, David J. Schwartz, David R. Neithamer
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Patent number: 6340371Abstract: Monobenzenic ortho-phenylenediamines comprising at least one cationic group Z, Z being chosen from aliphatic chains, comprising at least one quaternized unsaturated ring, to their use for the oxidation dyeing of keratin fibers, to dye compositions containing them and to oxidation dyeing processes using them.Type: GrantFiled: September 1, 1999Date of Patent: January 22, 2002Assignee: L'Oreal S.A.Inventors: Alain Genet, Alain Lagrange
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Patent number: 6270533Abstract: The invention relates to novel dibenzene oxidation bases containing at least one cationic group Z, Z being chosen from quaternized aliphatic chains, aliphatic chains containing at least one quaternized saturated ring and aliphatic chains containing at least one quaternized unsaturated ring, to their use for the oxidation dyeing of keratin fibres, to dye compositions containing them and to oxidation dyeing processes using them.Type: GrantFiled: June 7, 1999Date of Patent: August 7, 2001Assignee: L'Oreal S.A.Inventors: Alain Genet, Alain Lagrange
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Patent number: 6255353Abstract: Certain simple chemical agents, referred to herein as nitrone related therapeutics or “NRTs”, when administered to a patient susceptible to neovascularization (angiogenesis), can intervene and inhibit the disease's progress. Methods for therapeutically and prophylactically inhibiting angiogenesis by administering one or more NRTs are disclosed as are pharmaceutical compositions for use in such methods of treating. NRTs useful in these compositions and therapeutic methods are also disclosed.Type: GrantFiled: March 12, 1999Date of Patent: July 3, 2001Assignee: Centaur Pharmaceuticals, Inc.Inventors: Lowell D. Waterbury, Kenneth W. Narducy, Allan L. Wilcox
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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: 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: 6083990Abstract: The present invention discloses the use of permanently charged steroid agonists or antagonists as potent anti-angiogenic compositions comprising as an active ingredient a compound of the general formulae I, II or III: ##STR1## wherein DRUG is any steroid agonist or antagonist, a mixed agonist-antagonist, or a partial agonist and the substituents are as defined in the specification.Type: GrantFiled: April 2, 1997Date of Patent: July 4, 2000Assignee: Pharmos CorporationInventors: Anat Biegon, Marcus E. Brewster
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Patent number: 6071908Abstract: A method of treating neoplastic disease wherein a patient in need of such treatment is administered an effective amount of a radiation-activated cytotoxin prodrug (RACP) which has low toxicity, which is reducible by reducing agents generated by the radiolysis of water and which, upon reduction, releases a sufficient amount of a cytotoxic effector of sufficient cytotoxic potency to kill tumor cells. The tumor cells are irradiated with ionizing radiation to reduce the prodrug which is present at the locus of the tumor cells to release the cytotoxic effector.Type: GrantFiled: May 7, 1998Date of Patent: June 6, 2000Assignee: Auckland Uniservices LimitedInventors: William A. Denny, Moena Tercel, William R. Wilson
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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: 6031135Abstract: The invention relates to trimethylsphingosine derivatives which have some or all of the activities of the parent compound.Type: GrantFiled: May 13, 1996Date of Patent: February 29, 2000Assignee: Oncomembrane, Inc.Inventors: Fuqiang Ruan, Yasuyuki Igarashi, Sen-Itiroh Hakomori
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Patent number: 6002001Abstract: Spin trapping compositions in general have now been discovered to be effective in treating a variety of disorders, including disorders such as those arising from ischemia, infection, inflammation, exposure to radiation or cytotoxic compounds, not just of the central and peripheral nervous systems but of peripheral organ disease having a wide variety of etiologies. In the preferred embodiment, the compositions for treating tissue damage from ischemia contain PBN, or active derivatives thereof, in a suitable pharmaceutical carrier for intravenous, oral, topical, or nasal/pulmonary administration. Other preferred spin-trapping agents include 5,5-dimethyl pyrroline N-oxide, (DMPO), .alpha.-(4-pyridyl-1-oxide)-N-tert-butylnitrone, (POBN), and (TEMPO) spin-trapping derivatives thereof. Examples of derivatives of PBN include halogenated derivatives, bifunctional derivatives, conjugates with drugs or targeting molecules, dimers and cyclodextran polymers of PBN.Type: GrantFiled: November 28, 1997Date of Patent: December 14, 1999Assignees: Oklahoma Medical Research Foundation, University of Kentucky Research FoundationInventors: John M. Carney, Robert A. Floyd
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Patent number: 5998496Abstract: A compound of the general formula:A-L.sup.+ D.sup.-where A is a moiety which absorbs radiation and enters an excited state in which it accepts an electron; D.sup.- is a moiety which donates an electron to the excited state A and releases a free radical; and L.sup.+ is a cationic linking group which tethers electron acceptor moiety A to electron donor moiety D.sup.-. Cationic linking moiety L.sup.+ has the formula:-L'-G-where L' is a moiety which forms a stable radical with acceptor moiety A upon transfer of an electron from donor moiety D.sup.- to electron acceptor moiety A, and G is a moiety which forms a leaving group upon transfer of the electron from donor moiety D.sup.- to acceptor moiety A.Type: GrantFiled: August 19, 1996Date of Patent: December 7, 1999Assignee: Spectra Group Limited, Inc.Inventors: Salah A. Hassoon, Ananda M. Sarker, Douglas C. Neckers
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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: 5780510Abstract: 2,4-disulfonyl .alpha.-phenyl-tert-butyl nitrone and its pharmaceutically acceptable salts are disclosed. These materials are useful as pharmaceutical agents for oral or parenteral, e.g. intravenous administration to patients suffering from acute central nervous system oxidation as occurs in a stroke or from gradual central nervous system oxidation which can exhibit itself as progressive central nervous system function loss. The materials are also used to ameliorate the side effects of oxidative-damage causing antineoplastic disease treatments.Type: GrantFiled: June 19, 1997Date of Patent: July 14, 1998Assignees: Oklahoma Medical Research Foundation, University of Kentucky Research FoundationInventor: John M. Carney
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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: 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: 5679874Abstract: Process for the preparation of dichloro-(2,2)-paracyclophane from p-methylbenzylhalide through 2(3)-chloro-p-methylbenzyltrimethylammonium halide by Hofmann elimination of 2(3)-chloro-p-methylbenzyl trimethylammonium hydroxide in an aqueous solution of alkali metal hydroxide, wherein the 2(3)-chloro-p-methylbenzyltrimethylammonium halide is prepared by chlorination of p-methylbenzyltrimethylammonium halide and the Hofmann elimination is conducted in the presence of dioxane.Type: GrantFiled: July 14, 1992Date of Patent: October 21, 1997Assignee: Daisan Kasei Kabushiki KaishaInventor: Hiroshi Maruyama
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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: 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: 5600035Abstract: Photoreactive compounds are synthesized from 2,5- or 2,6-dintrobenzyl groups. Also disclosed are methods of synthesizing reactive monomers containing 2,5- or 2,6-dintrobenzyl groups.Type: GrantFiled: July 13, 1994Date of Patent: February 4, 1997Assignee: PPG Industries, Inc.Inventors: Charles F. Kahle, II, Neil D. McMurdie, Raphael O. Kollah, Daniel E. Rardon, Gregory J. McCollum
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Patent number: 5599990Abstract: A quaternary ammonium halide is prepared by reacting a substituted or unsubstituted haloalkane with a tert-amine in a mol ratio not higher than 1.1/1 in the absence of a solvent and at a temperature such as to maintain the reaction mixture liquid.Type: GrantFiled: October 27, 1995Date of Patent: February 4, 1997Assignee: Albemarle CorporationInventors: Joseph H. Miller, Joe D. Sauer, Dru L. DeLaet
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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: 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: 5488145Abstract: 2,4-disulfonyl .alpha.-phenyl-tert-butyl nitrone and its pharmaceutically acceptable salts are disclosed. These materials are useful as pharmaceutical agents for oral or intravenous administration to patients suffering from acute central nervous system oxidation as occurs in a stroke or from gradual central nervous system oxidation which can exhibit itself as progressive central nervous system function loss.Type: GrantFiled: December 23, 1993Date of Patent: January 30, 1996Assignees: Oklahoma Medical Research Foundation, University of Kentucky Research FoundationInventor: John M. Carney
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Patent number: 5475032Abstract: 2,4-disulfonyl .alpha.-phenyl-tert-butyl nitrone and its pharmaceutically acceptable salts are disclosed. These materials are useful as pharmaceutical agents for oral or parenteral, e.g. intravenous administration to patients suffering from acute central nervous system oxidation as occurs in a stroke or from gradual central nervous system oxidation which can exhibit itself as progressive central nervous system function loss. The materials are also used to ameliorate the side effects of oxidative-damage causing antineoplastic disease treatments.Type: GrantFiled: April 24, 1995Date of Patent: December 12, 1995Assignees: Oklahoma Medical Research Foundation, University of Kentucky Research FoundationInventor: John M. Carney
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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: 5414124Abstract: 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: January 19, 1993Date of Patent: May 9, 1995Assignee: Huntington Laboratories, Inc.Inventors: Kim R. Smith, Frederick M. Boyd, Samih S. Abouhalkah
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Patent number: 5399762Abstract: A high yield method for the preparation of C.sub.1 -C.sub.20 alkyl or aryl-substituted alkyl, C.sub.8 -C.sub.16 alkyl quaternary ammonium-hydroxide is provided whereby two reactants, a corresponding quaternary ammonium chloride and a metal hydroxide, are reacted in a solvent comprising a C.sub.1 -C.sub.4 normal alcohol. The amount of metal hydroxide reactant is that amount sufficient to yield the quaternary ammonium hydroxide and a metal chloride.Also provided are wood preservative systems which include (a) a biocidal effective amount of at least one di C.sub.8 -C.sub.12 alkyl quaternary ammonium hydroxide and (b) a solvent, as well as a method for preserving a wood substrate whereby the substrate is treated with the preservative system.Type: GrantFiled: June 9, 1993Date of Patent: March 21, 1995Assignee: Lonza, Inc.Inventor: Leigh E. Walker
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Patent number: 5399695Abstract: Provided is a convenient method for synthesizing quaternary ammonium salts which are useful as curing catalysts for one-part thermosetting resin compositions which maintain storage stability at room temperature. The ammonium salts are synthesized by direct reaction of a benzyl alcohol or a benzyl alkyl ether optionally having on the benzene ring and/or at .alpha.-position one or more substituent groups inert to the intended reaction, with a corresponding strong-acid salt of a tertiary amine.Type: GrantFiled: April 9, 1993Date of Patent: March 21, 1995Assignee: Nippon Paint Co., Ltd.Inventors: Shinji Nakano, Takao Morimoto, Takeshi Endo