Acyclic Patents (Class 564/301)
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Patent number: 6455706Abstract: A polymerizable composition, comprising a) at least one ethylenically unsaturated monomer or oligomer, and b) an initiator compound of formula (I) wherein n is 0 or 1. The compounds of formula (I) are prepared from a free radical and a compound of formula R10NO or Further aspects of the present invention are a process for polymerizing ethylenically unsaturated monomers, novel initiator compounds and their use for polymerization, intermediate compounds and also the polymer or copolymer produced by this process.Type: GrantFiled: April 9, 2001Date of Patent: September 24, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Peter Nesvadba, Andreas Kramer, Alfred Steinmann, Werner Stauffer
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Publication number: 20020082453Abstract: This invention relates to a process for preparing N-substituted hydroxylamines from N-substituted aryl- or heteroaryloxaziridines by acid hydrolysis and isolation of the N-substituted hydroxylamines in the form of their salts.Type: ApplicationFiled: December 7, 2001Publication date: June 27, 2002Inventors: Michael Dockner, Wolfgang Eymann, Bernd-Michael Konig, Helmut Holzem
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Publication number: 20020058772Abstract: The present invention concerns the preparation of polymers of low polydispersity and/or controlled molecular weight and architecture employing living free radical polymerization initiated by an alkoxyamine initiator or nitroxide plus, optionally, a free radical initiator, the polymer produced thereby; selected nitroxide and alkoxyamine initiators; and a process for making the initiators; the polymeric products being useful in protective coatings.Type: ApplicationFiled: May 9, 2001Publication date: May 16, 2002Inventors: Albert G. Anderson, Alexei Gridnev
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Patent number: 6359182Abstract: A C-nitroso compound having a molecular weight ranging from about 225 to about 1,000 (from about 225 to about 600 for oral administration) on a monomeric basis wherein a nitroso group is attached to a tertiary carbon, which is obtained by nitrosylation of a carbon acid having a pKa less than about 25, is useful as an NO donor. When the compound is obtained from a carbon acid with a pKa less than about 10, it provides vascular relaxing effect when used at micromolar concentrations and this activity is potentiated by glutathione to be obtained at nanomolar concentrations. When the compound is obtained from a carbon acid with a pKa ranging from about 15 to about 20, vascular relaxing effect is obtained at nanomolar concentrations without glutathione. The compound is preferably water-soluble and preferably contains a carbon alpha to the nitrosylated carbon which is part of a ketone group.Type: GrantFiled: October 26, 2000Date of Patent: March 19, 2002Assignee: Duke UniversityInventors: Jonathan S. Stamler, Eric J. Toone
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Patent number: 6348629Abstract: An aqueous phase inhibitor for quenching free radical polymerization comprising a free radical quenching agent having a hydrophilic tail is disclosed, as well as a coating and related methods. In one embodiment, the free radical quenching agent can either be an N-hydroxylamine or an N-nitrosonamine, the hydrophilic tail can be a polyhydric alcohol tail and the inhibitor can be a concentrate in a liquid medium such as water, alcohol and mixture thereof.Type: GrantFiled: August 9, 2001Date of Patent: February 19, 2002Assignee: Sun Drilling Products Corp.Inventor: Robert Albright
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Patent number: 6300518Abstract: An aqueous hydroxylamine solution containing hydroxylamine in an amount of 30 wt. % or more, which contains iron in an amount of not more than 10 ppb, metal components other than iron in an amount of not more than 5 ppb for each metal component and trans-1,2-diaminocyclohexane-N,N,N′,N′-tetraacetic acid in an amount of 0.0005 to 0.5 wt. % is obtained by distillation of a concentrated aqueous crude hydroxylamine solution using a specifically surface treated distilling apparatus.Type: GrantFiled: March 26, 2001Date of Patent: October 9, 2001Assignee: Nissin Chemical Co., Ltd.Inventors: Naoshi Imai, Kouzou Toguro
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Patent number: 6288246Abstract: The present invention relates to a process for preparing hydroxamic acids from hydroxylic acid intermediates wherein the carboxylic acid intermediate does not possess reactive substituents such as hydroxy or amino groups.Type: GrantFiled: April 7, 1999Date of Patent: September 11, 2001Assignee: Pfizer IncInventor: Joel M. Hawkins
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Patent number: 6258979Abstract: The invention pertains to chiral ferrocene phosphine derivatives and their use with transition metals as asymmetric catalysts in asymmetric hydrogenation.Type: GrantFiled: November 22, 1999Date of Patent: July 10, 2001Inventors: Henri Kagan, Gilles Argouarch, Odile Samuel
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Patent number: 6258983Abstract: The present invention comprises a process of producing HAN by slowly adding nitric acid to an alcoholic solution of hydroxylamine. This forms a precipitate of solid HAN. However, if more nitric acid is added, the precipitate dissolves before the stoichiometric amount of acid has been added. Therefore, sufficient nitric acid is added to form a maximum amount of solid HAN precipitate. The solid HAN is then isolated by conventional means such as filtration or centrifugation, possibly preceded by chilling this solution. The excess alcoholic solution of unreacted hydroxylamine may be recycled and used as starting material in the process.Type: GrantFiled: October 12, 2000Date of Patent: July 10, 2001Assignee: The United States of America as represented by the Secretary of the NavyInventor: Kerry L. Wagaman
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Patent number: 6239183Abstract: A method for controlling the rheology of aqueous systems, particularly for those intended for underground use, includes injecting an aqueous fluid containing a surfactant gelling agent into the system. The surfactant gelling agents are, for example, fatty aliphatic amidoamine oxides, salts of an alkoxylated monoamine with an aromatic dicarboxylic acid, and salts of an alkyldiamine with an aromatic dicarboxylic acid. The surfactant gelling agents can be adsorbed onto particulate supports to facilitate delivery of the gelling agent. The additives may be incorporated in the viscoelastic fluid to tailor its use in hydraulic fluids, drilling muds, fracture fluids, and in applications such as permeability modification, gravel packing, cementing, and the like.Type: GrantFiled: December 19, 1997Date of Patent: May 29, 2001Assignee: Akzo Nobel NVInventors: Robert F. Farmer, Andress K. Doyle, Glenda Del Carmen Vale, James F. Gadberry, Michael D. Hoey, Randy E. Dobson
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Patent number: 6229048Abstract: A method for treating cancer comprising administering a 1,3,4,6-tetrahydroxy-helianthrone derivative. The compounds can be used in the absence of light irradiation or for photodynamic therapy of solid tumors wherein the tumor site is subjected to light irradiation after administration of the active ingredient. A preferred compound is 10,13-dimethyl-1,3,4,6-tetrahydroxy-helianthrone.Type: GrantFiled: January 31, 2000Date of Patent: May 8, 2001Assignees: Yeda Research and Development Co. Ltd. at the Weizmann Institute of Science, New York UniversityInventors: Yehuda Mazur, Gad Lavie
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Patent number: 6218536Abstract: 1,2-Bis-adducts of stable hindered nitroxide compounds with substituted ethylenes are prepared by reacting two equivalents of nitroxyl compound with an ethylenically unsaturated compound such as styrene or an acrylate ester. These adducts are very effective inhibitors to prevent the premature polymerization of ethylenically unsaturated monomers when such monomers are distilled, processed or stored.Type: GrantFiled: October 7, 1998Date of Patent: April 17, 2001Assignee: Ciba Specialty Chemcials CorporationInventors: Glen Thomas Cunkle, Thomas F. Thompson, Volker H. von Ahn, Roland A. E. Winter
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Patent number: 6211410Abstract: According to the inventive method for producing organic hydroxylamines, at least one organic nitro compound is partially hydrogenated in the presence of an organic base or ammonia, a trivalent phosphor compound and a hydrogenation catalyst. The invention is characterised in that quantities of the nitrogen base of more than 10 wt. % in relation to the organic nitro compound are used.Type: GrantFiled: May 22, 2000Date of Patent: April 3, 2001Assignee: Consortium für elektrochemische Industrie GmbHInventors: Johannes Freudenreich, Jürgen Stohrer
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Patent number: 6162807Abstract: This invention is directed to monocyclic N-heterocyclics which are substituted by acyclic or cyclic thio derivatives which are useful as anti-coagulants. This invention is also directed to pharmaceutical compositions containing the compounds of the invention, and methods of using the compounds to treat disease-states characterized by thrombotic activity.Type: GrantFiled: January 11, 2000Date of Patent: December 19, 2000Assignee: Berlex Laboratories, Inc.Inventors: Monica J. Kochanny, Michael M. Morrissey, Howard P. Ng
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Patent number: 6121490Abstract: A process for producing tertiary amine oxide having two methyl or ethyl groups and one long chain primary aliphatic group in a stable, solid form is described. Aqueous 65-90% hydrogen peroxide and tertiary amine having two methyl or ethyl groups and one primary aliphatic hydrocarbyl group of 8-24 carbon atoms are mixed in proportions of ca. 1.1-1.3 moles of hydrogen peroxide per mole of tertiary amine in the presence of carbon dioxide and in the absence of organic solvent. When the conversion of the tertiary amine to tertiary amine oxide in the reaction mass has reached ca. 60-90%, the reaction mass is transferred to a separate vessel and the reaction mass is then allowed to solidify at a temperature of ca. 20-60.degree. C. The process makes possible the production of highly pure solid product without formation of any appreciable amounts of undesirable by-products.Type: GrantFiled: April 14, 1999Date of Patent: September 19, 2000Assignee: Albemarle CorporationInventor: Hassan Y. Elnagar
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Patent number: 6106797Abstract: The present invention relates to a gauze catalyst based on titanium or vanadium zeolites and inert gauze fabrics which is suitable for accelerating oxidation reactions such as epoxidation of olefins, hydrogen peroxide production or hydroxylamine synthesis.Type: GrantFiled: August 26, 1998Date of Patent: August 22, 2000Assignee: BASF AktiengesellschaftInventors: Ulrich Muller, Franz Josef Brocker, Georg Heinrich Grosch, Hermann Putter, Michael Schulz, Norbert Rieber, Wolfgang Harder
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Patent number: 6037497Abstract: A process is described in which tertiary amine is oxidized with hydrogen peroxide in the presence of carbon dioxide until the reaction mass contains (i) about 0.5 to about 6.5%, and preferably about 1 to about 2.5%, of unreacted free amine, (ii) carbon dioxide, and (iii) unreacted hydrogen peroxide. At this point individual portions of the reaction mass are dispensed into a plurality of shipping containers, or alternatively, the reaction mass is transferred to a cooling vessel, cooled therein, and then dispensed into a plurality of shipping containers. Thereafter the reaction is allowed to slowly continue to completion at ambient temperature in the shipping containers with venting of off-gases, as required. The process makes it possible to produce amine oxides with increased plant throughput without need for additional plant reaction equipment such as glass-lined reactors, and the consequent substantial additional capital investment.Type: GrantFiled: September 29, 1998Date of Patent: March 14, 2000Assignee: Albemarle CorporationInventors: Dustin H. Thomas, Douglas H. Krzystowczyk, Luc G. Six
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Patent number: 6031130Abstract: A method for preparing N,N-disubstituted hydroxylamine compounds represented by the formula (II): HO--N(R.sup.1)(R.sup.2) wherein R.sup.1 and R.sup.2 may be the same or different, and independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group, which comprises the step of adding a rhenium catalyst and aqueous hydrogen peroxide to a mixture containing a secondary amine compound represented by the formula (I): HN(R.sup.1)(R.sup.2) wherein R.sup.1 and R.sup.2 have the same meanings as those defined above and a dehydrating agent.Type: GrantFiled: May 21, 1998Date of Patent: February 29, 2000Assignee: Fuji Photo Film Co., Ltd.Inventors: Masuji Motoki, Tadahisa Sato
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Patent number: 6002002Abstract: The present invention provides novel hydroxylamine derivatives represented by the general formula: wherein:X is O, --NH, or a group of formula NR', wherein R and R' are independently selected from alkyl, cycloalkyl, phenylalkyl, phenyl optionally substituted with halo, haloalkyl,alkyl, alkoxy or nitro; and a N-containing heterocyclic ring;R.sup.1 is H or alkanoyl,R.sup.2 is H or hydroxy optionally acylated with alkanoyl, andR.sup.3 is a group of the formula --NR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently selected fromH, alkyl, and a group of the formula --CO--NH--R wherein R is as defined above, orwherein R.sup.4 and R.sup.5 when taken together form a 5- to 7-membered heterocyclic ring which may optionally contain one additional hetero atom selected from nitrogen, oxygen and sulfur and which is optionally substituted with alkyl or phenylalkyl.Type: GrantFiled: May 13, 1998Date of Patent: December 14, 1999Assignee: Biorex Research & Development Co.Inventors: Laszlo Urogdi, Ede Marvanyos, Mihaly Barabas, Laszlo Jaszlits, Katalin Biro, Andrea Jednakovits, Erzsebet Radvanyne, Maria Kurthy, Istvanne Udvardy Nagy
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Process for producing substituted amines and a method for purifying synthetic intermediates therefor
Patent number: 5932759Abstract: The present invention relates to a process for producing a substituted amine represented by the general formula (IV):R.sup.2 NHOR.sup.3 (IV)(wherein R.sup.2 represents a hydrogen atom, a hydrocarbon group or a heteroatom-containing hydrocarbon group, and R.sup.3 represents a hydrocarbon group or a heteroatom-containing hydrocarbon group), which comprises the steps of:(b) reacting a hydroxamic acid represented by the general formula (II):R.sup.1 CONHOH (II)(wherein R.sup.1 represents a hydrogen atom or a hydrocarbon group) in the presence of a base with a reaction reagent capable of introducing a hydrocarbon or a heteroatom-containing hydrocarbon group to an oxygen atom and/or a nitrogen atom to form a substituted hydroxamic acid represented by the general formula (III): ##STR1## (wherein R.sup.1, R.sup.2 and R.sup.Type: GrantFiled: February 13, 1997Date of Patent: August 3, 1999Assignee: Mitsui Chemicals, Inc.Inventors: Yoshio Motoyama, Naoshi Nagai, Takeshi Ishitoku, Noriaki Kihara -
Patent number: 5872295Abstract: The invention provides a method for purification of hydroxylamine so as to have a substantial reduction of cations and anions. The method involves passing a solution of hydroxylamine through at least one strong acid ion exchange bed which has been pretreated with dilute hydrochloric acid and then through at least one strong base anion exchange resin bed which has been pretreated or regenerated with a non-metal amino or hydroxide base solution.Type: GrantFiled: February 13, 1998Date of Patent: February 16, 1999Assignee: Concept Sciences, Inc.Inventors: Francis Michelotti, Irl E. Ward
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Patent number: 5840984Abstract: Odor formation during storage of (hydrocarbylthio)aromatic amines due to formation and release of odoriferous sulfur-containing species such as dihydrocarbyldisulfides, is suppressed. To accomplish this, a small amount of N,N-dihydrocarbylhydroxylamine odor-inhibitor (e.g., N,N-diethylhydroxylamine) is blended with the (hydrocarbylthio)aromatic amine. This enables products such as a mixture of 3,5-di(methylthio)-2,4-diaminotoluene and 3,5-di(methylthio)-2,6-diaminotoluene) to be stored for long periods of time with significantly reduced formation and release of odoriferous sulfur-containing species.Type: GrantFiled: June 23, 1997Date of Patent: November 24, 1998Assignee: Albemarle CorporationInventors: Gregory H. Lambeth, Paul L. Wiggins, William R. Brown
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Patent number: 5824804Abstract: Method for the preparation of N-alkoxy-(tetra- or hexahydro)-phthalimide according to formula I ##STR1## R.sub.1 being methyl or ethyl and R.sub.2 and R.sub.3 being each independently of one another hydrogen or alkyl with 1-4 C atoms or R.sub.2 and R.sub.3 together with the carbon atom to which they are bonded forming a ring with 5 or 6 C atoms, wherein the salt of the corresponding N-hydroxy-(tetrahydro- or hexahydro)-phthalimide according to formula II: ##STR2## with R.sub.2 and R.sub.3 as defined above and M being an alkali metal, is brought into contact with R.sub.1 Cl as alkylating agent, wherein R.sub.1 has the aforementioned meaning.The N-alkoxy-(tetra- or hexahydro)-phthalimide can afterwards be converted with the aid of hydroxylamine sulphate into the corresponding alkoxyamine after which the alkoxyamine obtained can be isolated. In this manner a simple and commercially attractive process for the preparation of O-(m)ethylhydroxylamine can be implemented.Type: GrantFiled: September 12, 1997Date of Patent: October 20, 1998Assignee: DSM N.V.Inventors: Joannes M. C. A. Mulders, Dominique M. C. Callant, Anna M. C. F. Castelijns
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Patent number: 5808150Abstract: The invention provides a stabilized aqueous, semi-aqueous, or non-aqueous solution of hydroxylamine or a partially neutralized hydroxylamine salt and a process therefore. The invention utilizes as a stabilizing agent a specific acetic acid compound.Type: GrantFiled: August 14, 1997Date of Patent: September 15, 1998Assignee: Concept Sciences, Inc.Inventor: Frank Michelotti
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Patent number: 5777163Abstract: Hydroxylamines are prepared from ammonia or the corresponding amines, hydrogen and oxygen by a process in which the starting materials are reacted under heterogeneous catalysis using an oxidation catalyst based on a titanium or vanadium silicalite having a zeolite structure and containing from 0.01 to 20% by weight of one or more platinum metals selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium and platinum, the platinum metals each being present in at least two different bond energy states.Type: GrantFiled: April 4, 1997Date of Patent: July 7, 1998Assignee: BASF AktiengesellschaftInventors: Ulrich Muller, Daniel Heineke
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Patent number: 5777164Abstract: The present invention discloses a method comprising the steps of;a) forming in an aqueous solution a hydroxamic acid from a hydroxylamine free base and anhydride having the formula (RCO).sub.2 O wherein R is H or a substituted or unsubstituted C.sub.2-6 alkyl, C.sub.2-6 alkenyl, C.sub.6-10 aryl, or C.sub.4-10 heteroaryl; andb) treating said hydroxamic acid with an alkylating agent in the presence of at least one proton scavenger under conditions sufficient to consume substantially all of said alkylating agent to form an O-substituted hydroxamate.The protection and alkylation are readily effected in water (with no alcohol co-solvent) without the need for phase-transfer catalysis and with little hydrolysis of the alkylating agent.Type: GrantFiled: April 14, 1997Date of Patent: July 7, 1998Assignee: Eastman Chemical CompanyInventor: Neil Warren Boaz
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Patent number: 5736526Abstract: A method and composition for inhibiting the spread of a retrovirus such as HIV in a human cell population in which a retrovirus such as HIV is present has been found. The spread of the retrovirus is inhibited by treatment of the cells with a synergistic combination mixture of a dideoxy-ribonucleoside excluding AZT and hydroxycarbamide.Type: GrantFiled: December 22, 1995Date of Patent: April 7, 1998Assignee: Compagnie de Development Aguettant S.A.Inventors: Serge D. Malley, Jorge R. Vila
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Patent number: 5734032Abstract: The present invention discloses a photo-induced DNA-cleaving agent composition comprises N-aryl-N-(alkyl or arylalkyl)hydroxylamine having the following formula: ##STR1## wherein R is C.sub.1 -C.sub.6 alkyl, phenyl, C.sub.1 -C.sub.6 alkoxy, phenoxy, C.sub.1 -C.sub.6 alkoxycarbonyl, halogen or halo(C.sub.1 -C.sub.6 alkyl)wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxycarbonyl, halogen or halo(C.sub.1 -C.sub.6 alkyl); R.sub.2 is hydrogen; R.sub.3 is hydrogen or phenyl; R.sub.4 is hydrogen, phenyl, hydroxylphenyl, methoxyphenyl, dimethoxyphenyl, dimethylaminophenyl or naphthyl. The present N-aryl-N-(alkyl or arylalkyl)hydroxylamine is stable in dark, but it can react with O.sub.2 to form HO.multidot. radicals under irradiation of UV light for a period of 2-3 hours. The HO.multidot. radicals then react with DNA to accomplish cleavage of DNA.Type: GrantFiled: December 29, 1995Date of Patent: March 31, 1998Assignee: National Science CouncilInventors: Jih Ru Hwu, Shwu-Chen Tsay, Buh-Luen Chen, Himatkumar V. Patel, Wan-Lin Chen, Chun Chieh Lin, Ching-Tai Chou
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Patent number: 5731462Abstract: The subject of the present invention is a new process for obtaining nitrones. It more particularly relates to a process for obtaining N-monosubstituted hydroxylamine comprising a stage in which a nitrone is formed from a secondary amine in the presence of an oxidizing agent and of at least one C.dbd.O containing species chosen from the group consisting of carbon dioxide, hydrogencarbonates and carbonates.Type: GrantFiled: December 18, 1996Date of Patent: March 24, 1998Assignee: Elf Atochem S.A.Inventors: Christophe Calais, Remy Teissier
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Patent number: 5709982Abstract: Substituted hydroxylamine antioxidants can be prepared by reacting hydroxylamine or a mono-substituted hydroxylamine with an epoxide. The antioxidant reaction product is not removed from the reaction mixture, but is used without separation after combination with a color developer to provide a photographic color developer composition. The antioxidants are highly water soluble and thus exhibit no objectionable odor.Type: GrantFiled: August 16, 1996Date of Patent: January 20, 1998Assignee: Eastman Kodak CompanyInventors: Carl Anthony Marrese, Paul Anthony Zielinski
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Patent number: 5646327Abstract: Substituted hydroxylamines useful in photographic processing solution can be prepared by reacting a hydroxylamine with a vinylic compound having an electron withdrawing substituent in a suitable solvent, in the absence of a neutralizing base. The resulting products can be used without isolation from the reaction solution.Type: GrantFiled: December 8, 1995Date of Patent: July 8, 1997Assignee: Eastman Kodak CompanyInventors: Elizabeth Gertrude Burns, Lynda Woedy McGarry, Gary Stephen Proehl, Lee Hamilton Latimer
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Patent number: 5620835Abstract: Substituted hydroxylamine antioxidants can be prepared by reacting hydroxylamine or a mono-substituted hydroxylamine with an epoxide. The antioxidant reaction product is not removed from the reaction mixture, but is used without separation after combination with a color developer to provide a photographic color developer composition. The antioxidants are highly water soluble and thus exhibit no objectionable odor.Type: GrantFiled: December 11, 1995Date of Patent: April 15, 1997Assignee: Eastman Kodak CompanyInventors: Carl A. Marrese, Paul A. Zielinski
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Patent number: 5610195Abstract: Compounds of formula (I) in which (a) four of the radicals R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are hydrogen and the others independently of one another are in each case C.sub.1 -C.sub.2 alkyl, these groups being bonded to the same carbon atom or to two different carbon atoms, or (b) five of the radicals R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are hydrogen and the other radical is C.sub.1 -C.sub.2 alkyl or hydroxymethyl, or salts thereof, are described. The compounds of formula (I) and their salts are ornithine decarboxylase inhibitors.Type: GrantFiled: December 12, 1994Date of Patent: March 11, 1997Assignee: Ciba-Geigy CorporationInventors: J org Frei, Jaroslav Stanek
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Patent number: 5597466Abstract: Salt-free aqueous solutions of bisaminoxyalkanes (I) are prepared by a process in whicha) a dihaloalkane (II) is converted with a ketoxime (III) in an aqueous solution of a strong mineral base into the alkylene bisoxime ether (IV),b) the alkylene bisoxime ether (IV) is cleaved with a strong mineral acid and water to give the ketone and the salt of the mineral acid with the bisaminoxyalkane (I), and the ketone is separated off in a conventional manner,c) an alkali metal hydroxide is added to the remaining aqueous solution to liberate the bisaminoxyalkane (I) andd) the ionic components are removed from the resulting aqueous solution by electrodialysis.Type: GrantFiled: July 26, 1994Date of Patent: January 28, 1997Assignee: BASF AktiengesellschaftInventors: Gerhard Bauer, Roland Baumstark, Kaspar Bott, Hartwig Voss
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Patent number: 5578744Abstract: A catalytically active gel is described consisting of a silica matrix with uniform porosity, monomodal pore distribution and high surface area, within which one or metal oxides possessing catalytic activity are dispersed. A process for preparing this catalytic gel is also described.Type: GrantFiled: May 19, 1995Date of Patent: November 26, 1996Assignees: Eniricerche S.p.A., Snamprogetti S.p.A.Inventors: Angela Carati, Enrico Davini, Mario G. Clerici, Giuseppe Bellussi
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Patent number: 5557013Abstract: Preparation of O-substituted hydroxylammonium salts of the formula IH.sub.2 NOR x HX Iwhere R is a C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.6 -alkenyl radical, each of which may be halogen-substituted, and X is chlorine or bromine, by reacting in an integrated process, without isolation of intermediatesa) acetone with hydroxylammonium sulfate and sodium hydroxide solution to give acetone oxime;b) treating the solution of acetone oxime thus obtained with sodium hydroxide solution and completely removing water,c) reacting the suspension of the acetone oxime Na salt thus obtained with alkylating agents at from 0.5 to 15 bar and at up to 140.degree. C. to give acetone oxime ethers; andd) cleaving the acetone oxime ethers with acids HX to give the products I,a homogeneous, nonpolar aprotic solvent being used in all process steps a) to d).Type: GrantFiled: October 19, 1995Date of Patent: September 17, 1996Assignee: BASF AktiengesellschaftInventors: Michael Keil, Josef Wahl, Ulrich Klein, Wolfgang Will
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Patent number: 5516909Abstract: A method for producing amine-boranes, specifically pyridine-borane which is highly stable and of good color is described.Type: GrantFiled: February 15, 1994Date of Patent: May 14, 1996Assignee: Boulder Scientific CompanyInventor: Jeffrey M. Sullivan
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Patent number: 5510511Abstract: A process for preparing N,O-dialkylhydroxycarbamic acid ester which comprises reacting hydroxylamine or its salt with dihydrocarbyl carbonate in the presence of a basic compound to prepare hydroxycarbamic acid ester and subsequently alkylating this compound with an alkylating agent; a process for recovering N,O-dialkylhydroxycarbamic acid ester which comprises azeotropically distilling the ester with water from a solution containing the ester; a process for preparing N,O-dialkylhydroxylamine which comprises hydrolyzing N,O-dialkylhydroxycarbamic acid ester in an aqueous solution or a hydrous solvent in the presence of an alkali; a process for purifying N,O-dialkylhydroxylamine hydrochloride which comprises adding aldehyde or ketone to a solution of N,O-dialkylhydroxylamine hydrochloride containing O-alkylhydroxylamine hydrochloride as impurities to convert the O-alkylhydroxylamine hydrochloride into O-alkyl aldoxime or O-alkyl ketoxime and subsequently separating the N,O-dialkylhydroxylamine hydrochloride froType: GrantFiled: July 27, 1993Date of Patent: April 23, 1996Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Satoshi Inoki, Mitsuyuki Takesue, Isao Hashimoto, Noriaki Kihara, Kiyoaki Sugi
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Patent number: 5488162Abstract: This invention relates to a process for preparing aqueous solutions of O-alkylhydroxylamine salts. The process involves converting hydroxylamine salts to their O-alkyl derivatives without the isolation of intermediates. More specifically, the process involves three steps. The first step, Step (A), involves forming a ketoxime. The second step, Step (B), involves adding an alkylating agent to the ketoxime formed in Step (A). The third step, Step (C), involves hydrolysing the alkylated ketoxime formed in Step (B) to yield an O-alkylhydroxylamine salt. O-alkylhydroxylamine salts are important intermediates in the preparation of herbicides.Type: GrantFiled: January 3, 1994Date of Patent: January 30, 1996Inventor: Paul R. Buckland
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Patent number: 5412082Abstract: Oxidation of primary amines to primary hydroxylamines using a dialkyl dioxirane is described. This new method is utilized to prepare aliphatic non-axial hydroxylamines from corresponding primary amino-substituted sugar derivatives and hydroxylamino acid derivatives.Type: GrantFiled: August 31, 1993Date of Patent: May 2, 1995Assignee: Yale UniversityInventors: Mark D. Wittman, Samuel J. Danishefsky, Randall L. Halcomb
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Patent number: 5393921Abstract: A process for synthesizing O-substituted oxime compounds, which includes (a) reacting an alkali metal or alkaline earth metal hydroxide compound and a solution of an oxime compound to form a first mixture including the alkali metal or alkaline earth metal salt of the oxime compound and water; and (b) adding an organohalide compound while stirring to the first mixture to form a second mixture including an O-substituted oxime compound, the alkali metal or alkaline earth metal salt of the oxime compound, water, unreacted organohalide compound and excess oxime compound. The second mixture is heated in the presence of an amount of water sufficient to react hydroxide with the unreacted organohalide compound to obtain an O-substituted oxime compound substantially free of unreacted organohalide compound.In a further embodiment, the O-substituted oxime compound can be hydrolyzed to the corresponding O-substituted hydroxylamine.Type: GrantFiled: July 7, 1993Date of Patent: February 28, 1995Assignee: The Gillette CompanyInventor: Harvey A. Lazar
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Patent number: 5384405Abstract: The present invention relates to a composition comprising an antimicrobial effective amount of a biocide selected from the group consisting of aromatic 2-N-hydroxy-thiourea and N-hydroxy-quinazolinone, and derivatives and combinations thereof, and at least one component selected from the group consisting of soaps, shampoos, skin-care medicaments, cosmetics, plastics and paints. Also disclosed is a novel process for making the biocide.Type: GrantFiled: January 10, 1994Date of Patent: January 24, 1995Assignee: Olin CorporationInventors: Rahim Hani, Phillip T. Berkowitz, John L. Peterson
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Patent number: 5382685Abstract: O-substituted hydroxylammonium salts are prepared by hydrolysis of acetone oxime ethers with acid in the presence of an additive, removing acetone and water by distillation with the aid of the additive.Type: GrantFiled: October 5, 1993Date of Patent: January 17, 1995Assignee: BASF AktiengesellschaftInventors: Ulrich Klein, Ernst Buschmann, Michael Keil, Norbert Goetz, Horst Hartmann
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Patent number: 5324857Abstract: Reaction of amine-containing substrates with hydrogen peroxide can suffer from certain problems, especially in the presence of transition metals. These problems include both in situ generation of impurities and particularly nitrosamines, which are allegedly carcinogenic, and also impaired product formation. The problems can be ameliorated by employing in the reaction mixture free radical scavengers, including in particular phenols and polyhydroxy-substituted aromatic compounds. The scavengers are advantageously employed in conjunction with a metal chelating agent such as polycarboxylic acid or an organopolyphosphonic acid.Type: GrantFiled: April 28, 1992Date of Patent: June 28, 1994Assignee: Solvay InteroxInventor: Noel S. Shehad
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Patent number: 5318762Abstract: A process for treating solutions of a hydroxylammonium salt containing excess acid which comprises:a) mixing the hydroxylammonium salt containing excess acid with a hydroxylammonium solution containing free hydroxylamine to produce a solution of the hydroxylammonium salt substantially free of excess acid,b) contacting a portion of the solution of the hydroxylammonium salt substantially free of excess acid with a weak base ion exchange resin to produce the hydroxylammonium solution containing free hydroxylamine, and,c) recycling the hydroxylammonium solution containing free hydroxylamine to step a).The process minimizes the decomposition of the hydroxylammonium salt solution and produces high purity hydroxylammonium nitrate solutions without directly contacting excess nitric acid with ion exchange resins. In addition to hydroxylammonium salts, the process can be used to treat any nitrate salt of an anine weak base which contains excess nitric acid.Type: GrantFiled: December 9, 1992Date of Patent: June 7, 1994Assignee: Olin CorporationInventors: David W. Cawlfield, Donald B. Loftis, Sanders H. Moore, Elizabeth K. Walter
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Patent number: 5292950Abstract: A composition of an N,N-dialkylaminoalkyl(meth)acrylamide of the following formula (II), which has an improved storageability and which contains an N,N-dialkylhydroxylamine of the following formula (I) in an amount of from 10 to 10,000 ppm: ##STR1## where R.sub.1 and R.sub.2 each independently represent an alkyl group having ##STR2## where R.sub.3 represents a hydrogen atom or a methyl group, R.sub.4 and R.sub.5 each independently represent an alkyl group having from 1 to 4 carbon atoms; andn represents an integer of from 2 to 4.Type: GrantFiled: November 13, 1990Date of Patent: March 8, 1994Assignees: Kohjin Co., Ltd., Sumitomo Chemical Co., Ltd.Inventors: Hiroshi Oka, Yasutaka Doi, Takashi Maruyama
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Patent number: 5288907Abstract: Catalytic hydrogenation of nitroalkane to N-alkylhydroxylamine free base in the absence of transition metal ions, and omission of acid and the resultant free base is storage stable, permitting shipment and storage of 15% aqueous solution for use as oxygen scavenger in boiler feed water treatment.Type: GrantFiled: October 30, 1991Date of Patent: February 22, 1994Assignee: W. R. Grace & Co.-Conn.Inventors: Martin B. Sherwin, Puvin Pichaichanarong
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Patent number: 5284851Abstract: 1-Alkoxy-1,3-diazacycloalkane derivatives of the formula I ##STR1## where: n is 0 or 1;R.sup.1 is substituted or unsubstituted alkyl, alkylcarbonyl, cycloalkylcarbonyl, alkenyl or alkynyl, a substituted or unsubstituted heterocyclic radical or a group --C(.dbd.O)--R, where R is substituted or unsubstituted phenyl or a substituted or unsubstituted aliphatic or aromatic heterocyclic structure,X ishydrogen; halogen; alkoxy; alkylthio; alkylcarbonyl; haloalkylcarbonyl; alkoxycarbonyl;substituted or unsubstituted alkyl, phenyl, phenoxy, phenylthio, benzoyl or phenyloxycarbonyl; andR.sup.2 ishydrogen or alkyl,processes and intermediates for their manufacture, and their use in pesticides.Type: GrantFiled: April 10, 1992Date of Patent: February 8, 1994Assignee: BASF AktiengesellschaftInventors: Wolfgang Von Deyn, Albrecht Harreus, Uwe Kardorff, Christoph Kuenast
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Patent number: 5264629Abstract: A process for preparing fluorinated compounds belonging to the classes:XH--Y--CZ.sub.1 Z.sub.2 --(CF.sub.2).sub.n F (I)andYH--X--(CF.sub.2).sub.n --CZ.sub.1 Z.sub.2 F (II)wherein:X is NR.sub.x, O, S, CFR.sub.x, C(R.sub.x).sub.2, or CF.sub.2 ;Y is NR.sub.x, O, S, CFR.sub.x, C(R.sub.x).sub.2, or CF.sub.2 ;X is different from Y;R.sub.x is a perhalogenated alkyl group, containing from 1 to 4 carbon atoms;n is either 0 or 1;Z.sub.1 and Z.sub.2, which may be either equal to, or different from, each other, represent F, Cl, Br, H or R.sub.x.The process is characterized in that a fluorinated cyclic compound of the formula: ##STR1## is reacted, at a temperature within the range of from -80.degree. to +300.degree., with HF in the presence of a Lewis acid. Some of the so-obtained compounds per se are novel.Type: GrantFiled: March 27, 1991Date of Patent: November 23, 1993Assignee: Ausimont S.r.l.Inventors: Darryl D. DesMarteau, Stefan P. Kotun, Alessandro Malacrida
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Patent number: RE36115Abstract: A method for producing amine-boranes, specifically pyridine-borane which is highly stable and of good color is described.Type: GrantFiled: February 14, 1997Date of Patent: February 23, 1999Assignee: Boulder Scientific CompanyInventor: Jeffrey M. Sullivan