Nitrosamines (i.e., Compounds Containing Nitroso Bonded Directly To Amino Nitrogen) Patents (Class 564/112)
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Patent number: 9233931Abstract: The present invention relates to a compound of one of the formulas I to XXI; a pharmaceutical composition comprising at least one such compound; and the use of at least one such compound in preparing a drug to treat, in a subject, a genetic disease resulting from at least one splicing anomaly.Type: GrantFiled: November 4, 2013Date of Patent: January 12, 2016Assignees: CENTRE NATIONALE DE RECHERCHE SCIENTIFIQUE, INSTITUT CURIE, UNIVERSITE MONTPELLIER 2 SCIENCES ET TECHNIQUESInventors: Jamal Tazi, David Grierson, Florence Mahuteau-Betzer, Pierre Roux
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Patent number: 8816095Abstract: Disclosed are molecules and their synthesis, for use in blocking gated ion channels such as voltage-gated sodium channels (VGSCs) and prostate voltage sodium channels (PVSCs). These inhibitors have superior blocking efficacy, for instance in displacing the radioligand [3H]-Batrachotoxin-B ([3H]-BTX-B) that binds to site 2 of a VGSC. The molecules of the invention comprise a moiety which increases the binding affinity of molecules for the protein binding site in prostate cancer cells (PCs), and which is also fluorescent. In one embodiment the invention molecules are an inhibition system that can be used to target over-abundant or hyperactive VGSCs selectively in pain, epilepsy or prostate cancer, inhibiting the proliferation of PCs. The fluorescent moiety also facilitates screening, tracking, and pharmacodynamic studies of the drug in a biological system both in vitro and in vivo.Type: GrantFiled: August 17, 2009Date of Patent: August 26, 2014Assignee: Georgetown UniversityInventors: Milton L. Brown, Scott Grindrod, Thomas H. Walls, Todd Hansen, Simeng Suy, Mikell A. Paige
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Publication number: 20140024127Abstract: The objects of embodiments in the present disclosure are to provide a method capable of recovering two or more amine compounds at the same time from a gas or solution, and also to provide a method capable of analyzing the recovered amines. The amine-recovering method comprises the steps (A) and (B). In the step (A), the gas or solution is brought into contact with a solid adsorbent so that the adsorbent may retain the amines. In the step (B), the amines retained by the adsorbent in the step (A) are eluted out by use of a basic compound-containing organic solvent. The solid adsorbent has a substituent group represented by —SO3M (M is H or an alkali metal).Type: ApplicationFiled: July 16, 2013Publication date: January 23, 2014Applicant: KABUSHIKI KAISHA TOSHIBAInventors: Hiroko WATANDO, Takashi Kuboki
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Patent number: 7696247Abstract: Novel nitric-oxide releasing lipid molecules are provided which comprise a lipid molecule selected from (a) phosphoglycerides, (b) lipids having a sphingosine base as a backbone, (c) monoacylglyerols, (d) diacylglycerols, (e) glycosylacylglycerols, and (f) sterol compounds of the formula: where R is a branched aliphatic chain of eight or more carbon atoms, wherein the lipid molecule is provided with a nitric-oxide containing group which comprises (a) a —S—N?O moiety, (b) a —O—N?O moiety, or (c) a a moiety. Also provided are methods of forming such nitric oxide releasing lipid molecules. Various pharmaceutical compositions, topical liquids and drug delivery systems comprising the nitric-oxide releasing lipid molecules are also described.Type: GrantFiled: July 6, 2004Date of Patent: April 13, 2010Assignee: Boston Scientific Scimed, Inc.Inventors: Robert A. Herrmann, Wendy Naimark
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Patent number: 6780849Abstract: Novel nitric-oxide releasing lipid molecules are provided which comprise a lipid molecule selected from (a) phosphoglycerides, (b) lipids having a sphingosine base as a backbone, (c) monoacylglyerols, (d) diacylglycerols, (e) glycosylacylglycerols, wherein the lipid molecole is provided with a nitric-oxide contianing group which comprises a (a) a —S—N═O moiety, (b) a —O—N═O moiety, or (c) a moiety. Also provided are methods of forming such nitric oxide releasing lipid molecules. Various pharmaceutical compositions, topical liquids and drug delivery systems comprising the ntric-oxide releasing lipid molecules are also described. Further provided are methods for therapeutically administering nitric oxide to patients, methods for treating or preventing various conditions, methods for promoting wound healing and methods for reducing the cells present in an atherosclerotic lesion which methods utilize the nitric-oxide releasing lipid molecules.Type: GrantFiled: December 21, 2000Date of Patent: August 24, 2004Assignee: SciMed Life Systems, Inc.Inventors: Robert A. Herrmann, Wendy Naimark
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Patent number: 6653506Abstract: Methods to recover nitramines from energetic materials yielding useable by-products and producing zero waste. The methods are used on materials containing HMX and RDX.Type: GrantFiled: September 16, 2002Date of Patent: November 25, 2003Assignee: TPL, Inc.Inventors: Randall S. Phillips, Andrew W. Cain, Thomas J. Schilling, Michael Miks
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Publication number: 20020137968Abstract: Benzoic acid derivatives of the formula I 1Type: ApplicationFiled: October 10, 2001Publication date: September 26, 2002Inventors: John Lloyd, George C. Rovnyak, Philip D. Stein, Saleem Ahmad, Karnail S. Atwal, Thomas J. Caulfield, Michael A. Poss
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Patent number: 6452049Abstract: Methods to recover nitramines from energetic materials yielding useable by-products and producing zero waste. The methods are used on materials containing HMX and RDX.Type: GrantFiled: May 15, 2000Date of Patent: September 17, 2002Assignee: TPL, Inc.Inventors: Randall S. Phillips, Andrew W. Cain, Thomas J. Schilling, Michael W. Miks
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Publication number: 20010051146Abstract: The present invention is to provide an agent for preventing and/or treating multiple organ failure comprising Tumor cytotoxic factor-II (TCF-II) or Hepatocyte growth factor (HGF) as an effective ingredient.Type: ApplicationFiled: August 27, 1999Publication date: December 13, 2001Inventors: HIROHIKO ARISAWA, HIROAKI MASUNAGA, HIROMI OGAWA, KANJI HIGASHIO
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Patent number: 6210536Abstract: This invention is directed to certain N,N′-dinitroso phenylenediamines useful as polymerization inhibitors for acrylic acids and esters thereof. Also disclosed are compositions containing such compounds, and methods for inhibiting polymerization using such compounds and compositions.Type: GrantFiled: September 2, 1993Date of Patent: April 3, 2001Assignee: Uniroyal Chemical Company, Inc.Inventors: Anthony Vincent Grossi, Paul Edwin Stott
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Patent number: 6132985Abstract: The present invention describes methods for the detoxification of a mixture of nitrile compounds, or a mixture of nitrile and amide compounds by conversion of the nitrile compound(s) to the corresponding amide or acid compounds using a pure culture of an induced microorganism strain capable of converting a nitrile moiety to an amide or acid moiety. If an amide is formed or is present in the mixture, the amide can be further converted, using the present methods for detoxification, to the corresponding acid. The acid can then, if desired, be further degraded to CO.sub.2, H.sub.2 O and biomass. The induced pure cultures are able to detoxify a mixture of nitriles or a mixture of nitrites and amides which are typically present, in high concentration(s), in nitrile production waste streams.Type: GrantFiled: June 18, 1999Date of Patent: October 17, 2000Assignee: Cytec Technology CorporationInventor: George E. Pierce
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Patent number: 6068823Abstract: A direct fixation of NO.sub.2 and N.sub.2 O.sub.4 at room temperature and atmospheric pressure is described using bis(diorganoamino)magnesium compounds formed from reactions between donor-solvent free diorganomagnesium compounds and primary or secondary amines, yielding new compositions of matter having the general formulas [(R.sub.2 N).sub.i (R.sub.2 NN.sub.x O.sub.y)jMg].sub.m and [(R.sub.2 N).sub.i (R.sub.2 NN.sub.x O.sub.y).sub.j (N.sub.x O.sub.y).sub.k Mg].sub.m. Methods are also described to convert these new compositions of matter into useful organic compounds and nitrogen gas.Type: GrantFiled: January 15, 1999Date of Patent: May 30, 2000Assignee: The University of Houston SystemInventors: Ramiro Sanchez, Graciela Lubertino
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Patent number: 6063960Abstract: Methods to recover nitroamines from energetic pyrotechnic materials yielding useable by-products and producing zero waste. The methods are used on materials containing HMX and RDX.Type: GrantFiled: December 15, 1998Date of Patent: May 16, 2000Assignee: TPL, Inc.Inventors: Randall S. Phillips, Andrew W. Cain, Thomas J. Schilling, Michael W. Miks
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Patent number: 6057347Abstract: Nonsteroidal antiinflammatory drugs which have been substituted with a nitrogen monoxide group; compositions comprising (i) a nonsteroidal antiinflammatory drug, which can optionally be substituted with a nitrogen monoxide group and (ii) a compound that directly donates, transfers or releases a nitrogen monoxide group (preferably as a charged species, particularly nitrosonium); and methods of treatment of inflammation, pain, gastrointestinal lesions and/or fever using the compositions are disclosed. The compounds and compositions protect against the gastrointestinal, renal and other toxicities that are otherwise induced by nonsteroidal antiinflammatory drugs.Type: GrantFiled: September 16, 1997Date of Patent: May 2, 2000Assignee: NitroMed, Inc.Inventors: David S. Garvey, L. Gordon Letts, H. Burt Renfroe, Sang William Tam
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Patent number: 6018079Abstract: A simple and inexpensive process is described for reducing the concentration of N-nitroso-containing compounds in compositions comprising N-nitroso-containing compounds and other desired compounds wherein the N-nitroso-containing compounds thermally decompose at a temperature below the decomposition temperature of the desired compounds. For compositions comprising dinitroaniline herbicides wherein the N-nitroso compound is a N-nitroso derivative of a precursor in the manufacture of the herbicide, for example Flumetralin, N-ethyl-N-(2-chloro-6-fluorobenzyl)-2,6-dinitro-4-trifluoromethylaniline, the process requires heating the mixture to a temperature greater than about 120.degree. C., and holding the composition at that temperature for a time effective to decompose the N-nitroso compound present in the mixture. Volatile decomposition products are advantageously removed from the composition.Type: GrantFiled: May 10, 1999Date of Patent: January 25, 2000Assignee: SRM Chemical, Ltd, Co.Inventors: Lowell J. Lawrence, Stephan Kwiatkowski
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Patent number: 5863750Abstract: The present invention describes methods for the detoxification of a mixture of nitrile compounds, or a mixture of nitrile and amide compounds by conversion of the nitrile compound(s) to the corresponding amide or acid compounds using a pure culture of an induced microorganism strain capable of converting a nitrile moiety to an amide or acid moiety. If an amide is formed or is present in the mixture, the amide can be further converted, using the present methods for detoxification, to the corresponding acid. The acid can then, if desired, be further degraded to CO.sub.2, H.sub.2 O and biomass. The induced pure cultures are able to detoxify a mixture of nitrites or a mixture of nitriles and amides which are typically present, in high concentration(s), in nitrile production waste streams.Type: GrantFiled: December 18, 1996Date of Patent: January 26, 1999Inventor: George E. Pierce
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Patent number: 5789617Abstract: This invention relates to novel neopentyl difluoroamino compounds which are useful as plasticizers and oxidizers in energetic formulations, such as propellants, explosives, and gasifiers. These neopentyl difluoroamino compounds can be prepared either: (1) by the direct fluorination of amine derivatives containing energetic pendant groups; or (2) by first preparing NF.sub.2 -derivatives and then substituting these derivatives with energetic pendant groups. In particular, mono- and bis-(difluoroaminomethyl) oxetanes are synthesized and further reacted to yield the corresponding dinitrate esters. It has been discovered that these NF.sub.2 -dinitrate esters are very useful as energetic plasticizers in high-energy formulations.Type: GrantFiled: September 2, 1992Date of Patent: August 4, 1998Assignee: Aerojet-General CorporationInventors: Thomas G. Archibald, Gerald E. Manser
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Patent number: 5698738Abstract: Nitric oxide has proved to mediate many important physiological processes. The nitric oxide donors of the present invention have a NONOate anion linked to an ortho-substituted aryl, a heteroaromatic substituent, asteroid, or a catecholamine. Preferred ortho substituents are alkoxy, halo, and alkyl. The cation of the salt is an alkali metal, an alkaline-earth metal, an ammonium or substituted ammonium group. Nitric oxide donors provided herein are more stable than that of nitrogen-bonded NONOates described previously. The by product left after release of NO, and the nitric oxide donors themselves, are very probably less carcinogenic than the corresponding nitrogen-bonded NONOates.Type: GrantFiled: May 15, 1995Date of Patent: December 16, 1997Assignees: Board of Regents, The University of Texas System, The Texas A&M University SystemInventors: Robert E. Garfield, Alexandru T. Balaban, William A. Seitz, Douglas J. Klein, Melanie Lesko
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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: 5510534Abstract: The present invention is directed to a process for reducing the nitrosamine content in a herbicide derived from dinitroaniline. The herbicide is treated with an aqueous solution of alkaline or ammonium persulfate in a proportion of at least 0.5% w/w relative to the weight of the herbicide to form an aqueous suspension. The suspension is heated to at least 70.degree. C., and the herbicide is separated from the suspension.Type: GrantFiled: March 23, 1995Date of Patent: April 23, 1996Assignee: Atanor S.A.Inventors: Maria D. C. Breglia De Belcoure, Marta M. D. C. Ruiz
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Patent number: 5405999Abstract: A process for the preparation of the unsaturated dinitroaniline, ethalfluralin having a level of nitrosamines lower than 0.5 ppm and essentially free from the compound of addition of halogenhydric acid on the methallyl double bond, by treatment with aqueous halogenhydric acid, wherein crude ethalfluralin is treated under agitation with an aqueous solution of hydrobromic acid in the presence of sulfamic acid and a sulfur compound selected from the group consisting of bisulfites, metabisulfites, hydrosulfites, sulfurous acid and gaseous sulfur dioxide.Type: GrantFiled: November 29, 1993Date of Patent: April 11, 1995Assignee: Finchimica S.p.A.Inventor: Graziello Donadello
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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: 5306837Abstract: Novel intermediates useful in the preparation of the optically active antiviral compound [1R-(1.alpha.,2.beta.,3.alpha.)]-2-amino-9-[2,3-bis(hydroxymethyl)cyclobut yl]-1,9-dihydro-6H-purin-6-one are described.Type: GrantFiled: July 15, 1993Date of Patent: April 26, 1994Assignee: E. R. Squibb & Sons, Inc.Inventors: Gregory S. Bisacchi, Toomas Mitt
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Patent number: 5292920Abstract: Disclosed are salts of N-nitrosophenylhydroxylamine and their use as polymerization inhibitors.Type: GrantFiled: August 24, 1993Date of Patent: March 8, 1994Assignee: Rohm and Haas CompanyInventors: Rita K. Upmacis, William Bauer, Jr., Samuel F. Reed, Jr.
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Patent number: 5268468Abstract: Novel 2-(3-phenylpropyl)hydrazines, intermediates in and processes for the preparation thereof, and a method of treating personality disorders utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: May 24, 1993Date of Patent: December 7, 1993Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventors: Richard C. Effland, Joseph T. Klein
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Patent number: 5262569Abstract: Disclosed are salts of N-nitrosophenylhydroxylamine and their use as polymerization inhbitors.Type: GrantFiled: July 17, 1991Date of Patent: November 16, 1993Assignee: Rohm and Haas CompanyInventors: Rita K. Upmacis, William Bauer, Jr., Samuel F. Reed, Jr.
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Patent number: 5155137Abstract: There are disclosed novel complexes of nitric oxide and polyamines which are useful in treating cardiovascular disorders, including hypertension. The disclosed compounds release nitric oxide (endothelium-derived relaxing factor) under physiological conditions in a sustained and controllable fashion, and possess long mechanisms of action.Type: GrantFiled: September 20, 1990Date of Patent: October 13, 1992Assignee: The United States of America as represented by the Secretary of the Department of Health and Human ServicesInventors: Larry K. Keefer, Joseph A. Hrabie
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Patent number: 5008455Abstract: There is provided a method for the production of hydroxylamine derivatives or the salt thereof in which a salt of hydroxamic acid is reacted with an alkylating agent such as diethyl sulfate to form an ester of hydroxamic acid, which is reacted with mineral acid in an aqueous solution of lower alcohol so as to prepare hydroxylamine derivatives or the salt thereof. In this process, the incorporation of an oxidizing agent or aldehydes in the reaction system will significantly reduce the content of nitrosoamines in the resulting solution of hydroxylamine derivatives or the salt thereof. Therefore, the resulting hydroxylamine derivatives obtained with a lesser content of harmful compound will be useful as an intermediate for the production of drugs and pesticides.Type: GrantFiled: December 6, 1989Date of Patent: April 16, 1991Assignee: Nippon Soda Co., Ltd.Inventors: Masashi Nakajima, Nobuo Tomita, Kenji Suzaki, Akira Kaneko, Mikio Sawaki
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Patent number: 4990625Abstract: A process for synthesizing an N,N-disubstituted hydrazone comprises carrying out nitrozation by adding an aqueous solution of sodium nitrite to a solution having one part by weight of an N,N-disubstituted amine dissolved in 3 to 30 parts by weight of an organic acid, then reducing the nitrozated product to an N,N-disubstituted hydrazine by adding a reducing agent to the mixture containing the nitrozated product, and thereafter adding to the mixture containing the N,N-disubstituted hydrazine a carbonyl compound of the formula: ##STR1## wherein A represents an aromatic hydrocarbon group or an aromatic heterocyclic group which may have a substituent, B represents a hydrogen atom, an alkyl group, an aryl group or an aromatic heterocyclic group, which may have a substituent, thereby performing condensation of the N,N-disubstituted hydrazine with the carbonyl compound.Type: GrantFiled: December 5, 1989Date of Patent: February 5, 1991Assignee: Canon Kabushiki KaishaInventors: Tetsuo Arita, Minoru Mabuchi, Shoji Umehara, Kiyoshi Sakai
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Patent number: 4954526Abstract: A method of treating cardiovascular disorders in a mammal, by administering to said mammal an effective amount of a compound of the formula:[R--N(H)N(NO)O--].sub.y Xwherein R is loweralkyl, aryl, arylalkyl, or cycloalkyl, any of which R groups may be optionally substituted by one to three substituents selected from the group consisting of: halo, hydroxyl, alkoxy, amino, amido, formyl, carboxyl, or nitro; and wherein X is a pharmaceutically acceptable cation, a pharmaceutically acceptable metal center, or a pharmaceutically acceptable organic group selected from loweralkyl, acyl or amido, and Y is 1 to 3 consistent with the valence of X. Pharmaceutical compositions containing the compounds are also provided.Type: GrantFiled: February 28, 1989Date of Patent: September 4, 1990Assignee: The United States of America as represented by the Department of Health and Human ServicesInventor: Larry K. Keefer
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Patent number: 4898976Abstract: The ethanolamine salt of N-nitrosophenylhydroxylamine ("NPHA") is effective as a polymerization inhibitor for ethylenically unsaturated monomers. The ethanolamine salt can be prepared by reacting ethanolamine with the ammonium salt of NPHA. Advantageously, the ethanolamine salt is soluble in high concentrations in water and a variety of polar organic solvents.Type: GrantFiled: April 17, 1989Date of Patent: February 6, 1990Assignee: Mallinckrodt, Inc.Inventor: John W. Varwig
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Patent number: 4874895Abstract: The level of the nitrosamines which may be present in the unrefined trifluralin is reduced to a value below 0.5 ppm, by treating the unrefined trifluralin under agitation, at a temperature from 60.degree. to 90.degree. C., for a time between 10 minutes and 4 hours, with an aqueous solution containing from 15 to 50% by weight of hydrobromic acid in a ratio of 0.2 to 0.8 liters per kilogram of unrefined trifluralin, said aqueous solution of hydrobromic acid being added with an amount of sulfamic acid from 0.1 to 3 g per liter of solution and with an amount of bisulfite or an alkali metal corresponding to a content of sulphur dioxide from 0.3 to 1.2 g per liter of said hydrobromic acid aqueous solution.The so obtained refined trifluralin has a content of nitrosamines which is lower than 0.1 ppm.Type: GrantFiled: February 17, 1989Date of Patent: October 17, 1989Assignee: Finchimica S.p.A.Inventor: Donadello Graziello
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Patent number: 4772740Abstract: The ethanolamine salt of N-nitrosophenylhydroxylamine ("NPHA") is effective as a polymerization inhibitor for ethylenically unsaturated monomers. The ethanolamine salt can be prepared by reacting ethanolamine with the ammonium salt of NPHA. Advantageously, the ethanolamine salt is soluble in high concentrations in water and a variety of polar organic solvents.Type: GrantFiled: March 5, 1985Date of Patent: September 20, 1988Assignee: Mallinckrodt, Inc.Inventor: John W. Varwig
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Patent number: 4675445Abstract: A process for eliminating N-nitrosamines, particularly N,N-dialkyl-N-nitrosamines and N-alkyl-N-aryl-N-nitrosamines from N-nitrosamine containing compositions through the addition of organic carboxylic acid halides. The process eliminates N-nitroso compounds without rearrangement to C-nitroso compounds.Type: GrantFiled: November 12, 1985Date of Patent: June 23, 1987Assignee: BASF CorporationInventors: Pauls Davis, Donald C. Mente
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Patent number: 4643755Abstract: The invention is a novel method for the control of the relative stem growth of graminaceous crops, comprising applying to the foliage, stems, roots or seeds of said plants, or to the soil in which said plants are grown, a plant growth regulating amount of a substituted phenylnitramine.Type: GrantFiled: September 21, 1981Date of Patent: February 17, 1987Assignee: American Cyanamid CompanyInventors: Thomas D. O'Neal, Prithvi R. Bhalla, Barrington Cross
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Patent number: 4537992Abstract: A method for removal of nitrosoamine impurities from herbicides comprising contacting a nitrosoamine containing herbicide homogeneously with 0.001% to 1.0% of a compound having the formula: ##STR1## where X equals chlorine or bromine,R.sup.1 equals lower alkyl, anda equals zero or 1; provided that when a equals 1, then:R equals X.sub.n H.sub.(3-n) C(CH.sub.2).sub.p --, or ##STR2## or R.sup.2 COX, where R.sup.2 is selected from alkylene, alkenylene, alkynylene groups having 1 to 5 carbon atoms,n equals 1 to 3, andp equals zero, 1 or 2; and provided that when a equals zero, then:R equals aminophenyl,for a sufficient length of time to remove at least a substantial amount of the nitrosoamine.Type: GrantFiled: February 9, 1984Date of Patent: August 27, 1985Assignee: Agan Chemical Manufacturers, Ltd.Inventors: Michael Pikarski, Julian Gabe, Edmund Dykman
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Patent number: 4535154Abstract: A method for the reduction of nitrogen compounds containing an N--N or N.dbd.N bond, which are soluble in water or lower alcohols, particularly nitrosamines, hydrazines, nitramines, azo- and azoxy-compounds, to the corresponding amines; comprising contacting the nitrogen compounds with a hydroxide solution and a nickel-aluminum alloy in the absence of a hydrogen atmosphere, at room temperature and at atmospheric pressure, for a sufficient time to produce the corresponding amine in a single step.Type: GrantFiled: July 13, 1983Date of Patent: August 13, 1985Assignee: United States of AmericaInventors: Larry K. Keefer, George Lunn
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Patent number: 4415753Abstract: A process for the production of unsubstituted and lower alkyl substituted p-aminophenols. A charge mixture is prepared comprising an unsubstituted or lower alkyl substituted nitrobenzene substrate, a platinum catalyst and a sulfur compound. The sulfur compound may be a divalent sulfur compound in which sulfur is bonded to two other moieties or a compound reducible to such sulfur compound under catalytic hydrogenation conditions. Hydrogen is introduced into the mixture while it is agitated at a temperature of 0.degree.-40.degree. C., thereby reducing the substrate to an unsubstituted or alkyl substituted phenylhydroxylamine. The hydroxylamine is thereafter heated to a temperature of at least 70.degree. C. and agitated at at least 70.degree. C. in the presence of a highly dissociated acid, thereby effecting rearrangement of the hydroxylamine to the corresponding p-aminophenol.Type: GrantFiled: January 29, 1982Date of Patent: November 15, 1983Assignee: Mallinckrodt, Inc.Inventors: Douglas C. Caskey, Douglas W. Chapman
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Patent number: 4381408Abstract: A method and apparatus are disclosed for extracting amine compounds from air samples without loss due to formation of nitrosamine artifacts. The apparatus includes a cartridge having a separation zone between a first port and a second port. The separation zone contains an air pervious packing of a granular, solid phase amine complexing agent. The method includes a first step of driving an air sample through the separation zone of the cartridge from the first port to the second port, and a second step of driving an eluent through the separation zone from the second port to the first port, or backflushing the cartridge. To extract amine compounds, the eluent is a solvent for the amine complexing agent in the separation zone of the cartridge. The method may contain the further step of determining the amine compound concentration of at least a portion of the eluate which passes from the separation zone following the second step of the method.Type: GrantFiled: December 1, 1980Date of Patent: April 26, 1983Assignee: Thermo Electron CorporationInventors: David P. Rounbehler, John W. Reisch
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Patent number: 4288622Abstract: Diphenylamine of the formula ##STR1## wherein R.sub.1 and R.sub.4 each independently represent a member selected from the group consisting of hydrogen, halogen, lower alkyl having 1-6 carbon atoms, lower alkoxy having 1-6 carbon atoms, amino, lower alkyl amino wherein the alkyl moiety has 1-6 carbon atoms, acylamino, lower carbamylalkyl amino wherein the alkyl moiety has 1-6 carbon atoms, lower hydroxyalkyl amino wherein the alkyl moiety has 1-6 carbon atoms, lower carbalkoxy amino wherein the alkoxy moiety has 1-6 carbon atoms and ureido;R.sub.2 and R.sub.3 each independently represent a member selected from the group consisting of hydrogen, halogen, lower alkyl having 1-6 carbon atoms, lower alkoxy having 1-6 carbon atoms, acylamino and ureido;R.sub.5 and R.sub.8 each independently represent a member selected from the group consisting of hydrogen, halogen, lower alkyl having 1-6 carbon atoms and lower alkoxy having 1-6 carbon atoms; andR.sub.6 and R.sub.Type: GrantFiled: November 12, 1976Date of Patent: September 8, 1981Assignee: L'OrealInventors: Gregoire Kalopissis, Andree Bugaut, Francoise Estradier