Two Substituent Nitrogens Bonded Directly To Two Carbons Of The Triazine Ring Patents (Class 544/204)
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Patent number: 4659822Abstract: The novel process ##STR1## in which R.sup.1 is alkyl, andR.sup.2 is alkoxy, alkylamino or dialkylamino.Compounds II and III are new, while (I) is a known intermediate for herbicides.Type: GrantFiled: February 13, 1986Date of Patent: April 21, 1987Assignee: Bayer AktiengesellschaftInventors: Uwe Priesnitz, Hans-Jochem Riebel
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Patent number: 4657908Abstract: The invention relates to carbonyl derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention where is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 and R.sup.2, same or different, are hydrogen or 1-10C alkyl, 3-8C cycloalkyl or 4-14C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R.sup.1 and R.sup.2 is halogen substituted, or R.sup.2 is hydrogen and R.sup.1 is R.sup.5 -E-W in which W is 2-6C alkylene optionally substituted by 1 or 2 1-4C alkyls, E is O, S, SO, SO.sub.2 or NR.sup.6 in which R.sup.6 is H or 1-6C alkyl, R.sup.5 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R.sup.5 and R.sup.6 are joined to form a pyrrolidine, piperidine, morpholine, piperazine or N-methylpiperazine ring, or R.sup.2 is H and R.sup.Type: GrantFiled: February 12, 1985Date of Patent: April 14, 1987Assignees: ICI Americas, Inc., Imperial Chemical Industries PLCInventors: Tobias O. Yellin, David J. Gilman, Philip N. Edwards, Michael S. Large, Derrick F. Jones, Keith Oldham
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Patent number: 4621143Abstract: A number of novel amides were found to be highly effective as cockroach repellents.Type: GrantFiled: June 27, 1984Date of Patent: November 4, 1986Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Terrence P. McGovern, George S. Burden
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Patent number: 4614818Abstract: A process for the preparation of dyes of the formula ##STR1## in which D is a dye radical and R.sub.1 and R.sub.2 independently of one another is hydrogen or C.sub.1-4 -alkyl, which comprises reacting cyanuric fluoride of the formula ##STR2## simultaneously with a dye of the formula ##STR3## and with an ammonium salt of an amine of the formulaH.sub.2 N--R.sub.2 (4)in a neutral to alkaline medium, to give dyes of the formula (1) as single compounds in good yields in one operation. The novel process has the advantage of being able to be carried out as a "one-pot process" in a closed reaction vessel so that the apparatus is simple and immission by cyanuric fluoride is excluded.Type: GrantFiled: January 18, 1983Date of Patent: September 30, 1986Assignee: Ciba Geigy CorporationInventors: Rolf Deitz, Herbert Seiler
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Patent number: 4586950Abstract: Herbicidal sulfonamides are useful as general or selective herbicides, both pre-emergence and post-emergence.Type: GrantFiled: September 20, 1983Date of Patent: May 6, 1986Assignee: E. I. Du Pont de Nemours & CompanyInventor: Robert J. Pasteris
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Patent number: 4576945Abstract: Hexaalkylmelamine-amino-oxy compounds having anti-tumor properties and pharmaceutical compositions for and therapeutic methods of treatment of tumors and employing same.Type: GrantFiled: January 3, 1984Date of Patent: March 18, 1986Inventor: Mark E. Sanders
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Patent number: 4562188Abstract: A method for the treatment of irritable bowel syndrome using a 1,3,5-triazin-2-one and a class of 6-amino and 6-mercaptyl-1,3,5-triazin-2-one compounds.Type: GrantFiled: January 13, 1984Date of Patent: December 31, 1985Assignee: William H. Rorer, Inc.Inventors: Donald E. Kuhla, William L. Studt, Henry F. Campbell, John Yelnosky
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Patent number: 4559345Abstract: Pyrimidine and s-triazine derivatives of formula (I) ##STR1## in which X=CH or N; Y=for example halogen, alkoxy; W=for example --S--CH.sub.2 --COOH, --O--CH.sub.2 --COO alkyl, --NH--CH.sub.2 --CONHCH.sub.2 CH.sub.2 OH; Z=for example 2,3-xylidino, and methods for the preparation thereof are described. The compounds show high antilipemic activity.Type: GrantFiled: July 21, 1982Date of Patent: December 17, 1985Assignee: LBP Istituto Faraceutico S.p.A.Inventors: Piero Gomarasca, Carlo Scolastico, Cesare Sirtori
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Patent number: 4544401Abstract: N-(heterocyclicaminocarbonyl)pyridinesulfonamides; are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.Type: GrantFiled: January 22, 1981Date of Patent: October 1, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: George Levitt
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Patent number: 4544402Abstract: 4-DL-alkylester-.gamma.-alaninyl-6-chloro-S-triazines having the formula (I): ##STR1## wherein R.sub.1 is a straight or branched chain alkyl, alkoxy, alkoxyalkyl or alkylol radical which is unsubstituted or substituted by a cyclopentyl or cyclohexyl group, which is, itself, unsubstituted or substituted by up to 5 methyl groups; R.sub.2 is a radical from the group of alkyl radicals of 1 to about 3 carbon atoms, or a hydrogen atom; and R is a radical from the group of alkyl radicals of 1 to about 3 carbon atoms.Type: GrantFiled: May 24, 1984Date of Patent: October 1, 1985Assignee: Chemische Werke Huls AktiengesellschaftInventors: Horst Schnurbusch, Helmut Baltruschat
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Patent number: 4540782Abstract: There are described novel intermediates for herbicides of the sulfonylurea class, which have the general formula I ##STR1## wherein E is nitrogen or the methine group,R.sub.1 is halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, --NR.sub.3 R.sub.4 or alkoxyalkyl having at most 4 carbon atoms, andR.sub.2 is a group --G--CF.sub.2 --T, where G is oxygen or sulfur, T is hydrogen, --CHClF, --CHBrF, --CHF.sub.2 or --CHF--CF.sub.3, R.sub.3 is hydrogen, methyl or ethyl, and R.sub.4 is hydrogen, methyl, ethyl, methoxy, ethoxy or methoxymethyl, with the proviso that R.sub.1 is not C.sub.1 -C.sub.4 -alkyl when simultaneously E is nitrogen and G is oxygen.Type: GrantFiled: July 26, 1984Date of Patent: September 10, 1985Assignee: Ciba-Geigy CorporationInventor: Willy Meyer
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Patent number: 4485041Abstract: The novel water-soluble disazo dyestuffs consist of two monoazo dyestuff moieties each containing as diazo component an amine of the benzene or naphthalene series and as coupling component an amino-naphthol-mono- or disulfonic acid. The two moieties are bonded to each other via a triazine radical which carries a halogen atom, and is bound to the amino groups of the coupling components and the diazo components contain a fiber-reactive radical of the vinyl sulfone series. To produce the dyestuffs 2 mols of the diazo compound carrying the fiber-reactive radical of the vinyl sulfone series is coupled with 1 mol of a bivalent coupling component consisting of 2 radicals of the aminonaphthol bound to the triazine ring via the amino groups, or two monoazo dyestuffs each synthesized from the aforesaid diazo component and an aminonaphthol-disulfonic acid coupling component are reacted with a 1,3,5-trihalogeno-triazine.Type: GrantFiled: February 17, 1981Date of Patent: November 27, 1984Assignee: Hoechst AktiengesellschaftInventors: Ernst Hoyer, Fritz Meininger, Rudolf Fass
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Patent number: 4469828Abstract: Alkylthiopropionyl hydrazino triazines are provided having the formula: ##STR1## wherein: R is alkyl having from one to about fifty carbon atoms;X is ##STR2## where R.sub.1 is selected from the group consisting of hydrogen, alkyl having from one to about fifty carbon atoms; and ##STR3## where R.sub.2 is selected from the group consisting of hydrogen, O and alkyl hydroxyalkyl, epoxy alkyl and acyloxy alkyl having from one or two to about eight carbon atoms;when X is O, A is selected from the group consisting of alkylene having from two to about twenty carbon atoms, cycloalkylene having from about five to about eight carbon atoms and phenylene;when X is ##STR4## A is selected from the group consisting of a direct linkage, alkylene having from one to about twenty carbon atoms, cycloalkylene having from five to about eight carbon atoms; phenylene; and ##STR5## where R.sub.Type: GrantFiled: November 22, 1982Date of Patent: September 4, 1984Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Motonobu Minagawa, Tohru Haruna, Masayuki Takahashi
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Patent number: 4459151Abstract: Fluorine-containing 4,6-diamino-s-triazines of the formula ##STR1## wherein X is a chlorine atom, an alkoxy radical having 1 to 4 carbon atoms, an alkylthio radical having 1 to 4 carbon atoms or the azide radical,R.sup.1, R.sup.2 and R.sup.3 each independently is a hydrogen atom or an aliphatic radical, andR.sup.4 is a fluoroalkyl or fluorochloroalkyl radical,which possess herbicidal activity. Intermediates wherein X is chlorine and --NR.sup.1 R.sup.2 is replaced by chlorine are also new.Type: GrantFiled: August 13, 1982Date of Patent: July 10, 1984Assignee: Bayer AktiengesellschaftInventors: Engelbert Kuhle, Bernd Baasner, Hermann Hagemann, Ludwig Eue, Robert R. Schmidt
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Patent number: 4455424Abstract: The present invention relates to naphthoquinone derivatives of formula I, ##STR1## in which R.sub.1 signifies a halogen atom, a nitro group or an unsubstituted or substituted alkoxy or amino group,R.sub.2 signifies the atoms necessary to form an unsaturated ring system, which ring system has 1 or 2 nuclei and is unsubstituted or substituted,R.sub.3 signifies an unsubstituted or substituted s-triazinyl or pyrimidyl radical, andn is 0, 1 or 2,which compounds are free from sulphonic acid groups are useful as pigments or disperse dyes.Type: GrantFiled: February 24, 1977Date of Patent: June 19, 1984Assignee: Sandoz Ltd.Inventor: Bansi L. Kaul
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Patent number: 4451463Abstract: This invention relates to alcohol derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 and R.sup.2, same or different, are hydrogen or 1-10C alkyl, 3-8C cycloalkyl or 4-14C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R.sup.1 and R.sup.2 is halogen-substituted, or R.sup.2 is hydrogen and R.sup.1 is R.sup.5 --E--W-- in which W is 2-6C alkylene optionally substituted by 1 or 2 1-4C alkyl, E is O, S, SO, SO.sub.2 or NR.sup.6 in which R.sup.6 is H or 1-6C alkyl, R.sup.5 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R.sup.5 and R.sup.6 are joined to form a pyrrolidine, piperidine, morpholine, piperazine or N-methylpiperazine ring, or R.sup.2 is hydrogen and R.sup.Type: GrantFiled: March 1, 1982Date of Patent: May 29, 1984Assignee: Imperial Chemical Industries PLCInventor: Michael S. Large
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Patent number: 4447441Abstract: The invention relates to guanidine derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I:- ##STR1## in which R.sup.1 and R.sup.2, same or different, are hydrogen or 1-10C alkyl, 3-8C cycloalkyl or 4-14C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R.sup.1 and R.sup.2 is halogen substituted, or R.sup.2 is hydrogen and R.sup.1 is R.sup.5 --E--W in which W is 2-6C alkylene optionally substituted by 1 or 2 1-4C alkyls, E is O,S or NR.sup.6 in which R.sup.6 is H or 1-6C alkyl, R.sup.5 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R.sup.5 and R.sup.Type: GrantFiled: March 1, 1982Date of Patent: May 8, 1984Assignee: Imperial Chemical Industries PLCInventors: Tobias O. Yellin, David J. Gilman
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Patent number: 4435206Abstract: N-(heterocyclicaminocarbonyl)pyridinesulfonamides are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.Type: GrantFiled: January 22, 1981Date of Patent: March 6, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: George Levitt
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Patent number: 4412856Abstract: The novel compounds of the formula I are useful selective herbicides for postemergence application in crops of cereals, maize and rice.In formula I, ##STR1## A is an unsubstituted or substituted amino group, Q is a C.sub.2 -C.sub.6 alkylene bridge, Y is an oxygen or sulfur atom or an unsubstituted or substituted nitrogen atom, and Z is an unsubstituted or substituted phenyl, naphthyl or heterocyclic radical, which phenyl radical, containing the bridge member Y, can additionally carry one to four further substituents.Type: GrantFiled: May 22, 1981Date of Patent: November 1, 1983Assignee: Ciba-Geigy CorporationInventors: Hans-Georg Brunner, Rolf Schurter, Henry Szczepanski
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Patent number: 4390538Abstract: The invention relates to triorgano-tin triazine compounds of the formula ##STR1## wherein X' is --S--Y--COOSn(R').sub.3, --O--Y--COOSn(R').sub.3 or --NH--Y--COOSn(R').sub.3, each of X" and X'" has the same meaning as X' or is halogen, (C.sub.1 -C.sub.6 alkyl).sub.2 N--, (C.sub.1 -C.sub.6 alkyl)--NH--, (C.sub.1 -C.sub.6 alky)--O-- or (C.sub.1 -C.sub.6 alkyl)--S--, Y is C.sub.1 -C.sub.6 alkylene, and the radicals R' can be the same or different and are C.sub.1 -C.sub.6 alkyl, bennzyl, phenyl or cycohexyl, each of which is unsubstituted or substituted.A process for the production of thee compounds, starting compounds suitable for this process, and the use of the compounds of formula I in pest control are also described.Type: GrantFiled: August 31, 1981Date of Patent: June 28, 1983Assignee: Ciba-Geigy CorporationInventors: Wolfgang Wehner, Saleem Farooq, Hans-Gunter Kostler
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Patent number: 4384102Abstract: Compounds having both s-triazine units and epoxide groups present are prepared by reacting an epoxide containing an isocyanate-reactive group with a triisocyanate corresponding to the formula: ##STR1## in which X is as defined herein. These reactants are used in quantities such that the equivalent ratio of isocyanate groups to isocyanate-reactive groups is maintained at less than or equal to 1 to 1. The compounds thus produced are particularly useful as reactive cross-linkers in the production of polyurethanes and polyepoxides.Type: GrantFiled: January 4, 1982Date of Patent: May 17, 1983Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Gerhard Grogler, Richard Kopp
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Patent number: 4339383Abstract: The invention relates to alkanolamido-.beta.-carboxylic acid esters of the formula I ##STR1## A full definition of the above formula will be found in claim 1 of the specification. These compounds are useful stabilizers for chlorinated thermoplastics.Type: GrantFiled: July 2, 1980Date of Patent: July 13, 1982Assignee: Ciba-Geigy CorporationInventors: Wolfgang Wehner, Klaus-Peter Michaelis, Rainer Schneider
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Patent number: 4338092Abstract: Compounds of the formula ##STR1## in which each of R.sub.1 and R.sub.3, independently, is hydrogen, methyl, methoxy or --NHCOR.sub.6,each of R.sub.2 and R.sub.4, independently, is hydrogen, methyl or methoxy, with the proviso that at least one of R.sub.1 to R.sub.4 is hydrogen,R.sub.5 is hydrogen, 2-, 3- or 4-hydroxy-C.sub.2-4 alkyl, carboxy-C.sub.1-4 alkyl, sulpho-C.sub.1-4 alkyl, sulphophenyl or carboxyphenyl andR.sub.6 is methyl or NH.sub.2, salts thereof,and mixtures of such compounds which compounds and mixtures are useful as reactive dyes for nitrogen-containing and hydroxy group-containing organic substrates such as leather and textile materials comprising or consisting of natural or synthetic polyamides such as wool, silk and nylon and natural or regenerated cellulose such as cotton, viscose and spun rayon.Type: GrantFiled: December 17, 1980Date of Patent: July 6, 1982Assignee: Sandoz Ltd.Inventor: Lukas Schneider
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Patent number: 4294580Abstract: Dyestuffs of the formula ##STR1## wherein Fb, W, R.sub.1, R.sub.2, R.sub.3, n and m have the meaning given in the description,and their use for dyeing and printing materials containing hydroxyl groups or nitrogen, such as textile fibres, filaments and fabrics of wool, silk or synthetic polyamide or polyurethane fibres, and for washfast dyeing and printing natural or regenerated cellulose.The dyeings obtained are distinguished by good fastness to wet processing.Type: GrantFiled: December 31, 1979Date of Patent: October 13, 1981Assignee: Bayer AktiengesellschaftInventors: Hermann Henk, Klaus Wunderlich, Peter Wild
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Patent number: 4288594Abstract: A new and improved process is provided for preparing monochloro-diamino-s-triazines which are useful as herbicides.The process comprises reacting in a first stage cyanuric chloride and a selected monoalkylamine hydrochloride at elevated temperature to give a dichloro-monoalkylamino-s-triazine and reacting in a second stage this dichloro-monoalkylamino-s-triazine with an excess of a different monoalkylamine which may be introduced as a pure liquid, as gas or as a solution in water. The third stage of the process consists of an exchange whereby the monoalkylamine hydrochloride of the first stage and the free monoalkylamine of the second stage are generated. The process gives consistent yields in excess of 97% of monochloro-diamino-s-triazines. Because the process is caustic-free and due to the feasibility of recycling the excess of monoalkylamines employed, no serious effluent problems arise.Type: GrantFiled: February 4, 1980Date of Patent: September 8, 1981Assignee: Ciba-Geigy CorporationInventors: Philip G. McCracken, Hal Myatt, Harris E. Petree
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Patent number: 4275204Abstract: Chloro-bis(alkylamino)-s-triazines are prepared by step-wise replacement of two chlorine atoms of cyanuric chloride by reaction with amines and alkali metal hydroxide in a medium comprising water and a liquid organic compound which is a solvent for cyanuric chloride and is substantially immiscible with water, the first step being carried out by contacting a first amine with a reaction medium containing the cyanuric chloride and the whole of the alkali metal hydroxide used for the step-wise replacement.Type: GrantFiled: September 7, 1979Date of Patent: June 23, 1981Assignee: Rumianca S.p.A.Inventors: Vittorio Messori, Renato Francese, Roberto Esposito
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Patent number: 4270918Abstract: Reactive dyes of the formula ##STR1## wherein one Y is hydrogen and the other Y is sulfo, R.sub.1 and R.sub.2 are hydrogen or the group --N(R.sub.1)--A--N(R.sub.2)-- is a piperazine radical, A is an alkylene or arylene radical, and Z is an amino, alkoxy or alkylthio group, and the benzene ring B can contain further substituents in addition to the --SO.sub.3 H--group.Type: GrantFiled: December 22, 1978Date of Patent: June 2, 1981Assignee: Ciba-Geigy CorporationInventor: Karl Seitz
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Patent number: 4263434Abstract: Novel piperidyl triazine derivatives are produced by reacting a substituted halogentriazine with a polyalcohol, a polymercaptan or a polyamine. The compounds are valuable light stabilizers for synthetic polymers, such as polyolefins, and fast to extraction in aqueous surfactant solutions.Type: GrantFiled: April 28, 1978Date of Patent: April 21, 1981Assignee: Chimosa Chimica Organica S.p.A.Inventors: Paolo Cassandrini, Antonio Tozzi
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Patent number: 4261889Abstract: Dyestuffs of the formula ##STR1## wherein R.sub.1 is hydrogen or a low-molecular alkyl group, R.sub.2 is hydrogen, a low-molecular alkyl group, an aryl radical or the radical of an organic dyestuff containing sulpho groups, and R.sub.1 and R.sub.2 together with the nitrogen atom can form a ring, X.sub.1 and X.sub.2 are hydrogen, a sulpho group or the --N.dbd.N--K radical, wherein K is the radical of a coupling component and, if one X is the --N.dbd.N--K radical, the other X is a sulpho group, and the benzene ring A can contain further substituents.Type: GrantFiled: October 19, 1978Date of Patent: April 14, 1981Assignee: Ciba-Geigy Corp.Inventors: Herbert Seiler, Gert Hegar
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Patent number: 4260779Abstract: Oxothia compounds, especially 2-oxo-2,3-dihydro-benzo[b]thiophene compounds of the formula ##STR1## in which Ph represents an optionally substituted 1,2-phenylene radical, X represents oxygen or sulphur, R.sub.1 represents an organic radical bonded via a carbon atom and R.sub.2 denotes hydrogen or an optionally substituted hydrocarbon radical of aliphatic character, and their salts are useful as peripheral analgetics and/or as antiphlogistic uricosuric and/or thrombolytic agents.Type: GrantFiled: November 9, 1979Date of Patent: April 7, 1981Assignee: Ciba-Geigy CorporationInventors: Raymond Bernasconi, Pier G. Ferrini, Richard Goschke, Jacques Gosteli
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Polyisocyanate reaction products of diisocyanates and s-triazine derivatives containing amino groups
Patent number: 4255570Abstract: The invention relates to polyisocyanates corresponding to the following general formula: ##STR1## wherein X represents a radical of the type obtained by removing the more reactive isocyanate group from an organic diisocyanate containing isocyanate groups of different reactivity; andY represents a chlorine, bromine, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, C.sub.6 -C.sub.10 aryl, C.sub.6 -C.sub.10 aroxy radical or a radical corresponding to the general formula: --NH--CO--NH--X.Type: GrantFiled: August 3, 1978Date of Patent: March 10, 1981Assignee: Bayer AktiengesellschaftInventors: Gerhard Grogler, Holger Meyborg -
Patent number: 4246408Abstract: Imidazo[1,2-a]-s-triazines including the base, the nucleoside, derivatives of the nucleoside, and the 5' nucleotide are prepared and are useful as antiviral Agents against RNA viruses.Type: GrantFiled: March 8, 1979Date of Patent: January 20, 1981Assignee: ICN PharmaceuticalsInventors: Roland K. Robins, Ganapathi R. Revankar
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Patent number: 4232153Abstract: Chloro-bis(alkylamino)-s-triazines are prepared by step-wise replacement of two chlorine atoms of cyanuric chloride with alkylamino groups.Cyanuric chloride, an inorganic base and an alkylamine are continuously fed to a first tubular zone in stoichiometric proportions and reacted therein under turbulent conditions, at an elevated temperature not exceeding 90.degree. C., and for a short reaction time, and the reaction product is continuously fed to a second tubular reaction zone together with stoichiometric quantities of inorganic base and of a second alkylamine, and reacted therein with the latter at an elevated temperature not exceeding 100.degree. C., under turbulent conditions and for a short reaction time.Type: GrantFiled: July 7, 1978Date of Patent: November 4, 1980Assignee: Rumianca S.p.A.Inventors: Luciano Baldi, Renato Francese, Franco Collecchia
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Patent number: 4230853Abstract: In the commercial process for preparing chloro-bis(alkylamino)-s-triazines by step-wise replacement of two chlorine atoms of cyanuric chloride by means of alkylamino groups in which a molar excess of alkylamine is used in the second replacement step, the formation of tris(alkylamino)-s-triazines is suppressed by adding to the reaction mixture, after the second chlorine atom has been replaced with an alkylamino group, an oxidizing agent selected from the group consisting of hydrogen peroxide and alkali metal hypochlorites, persulphates and permanganates, in an amount of at least 1 equivalent for every mole of unreacted alkylamine present in the said reaction mixture.Type: GrantFiled: October 1, 1979Date of Patent: October 28, 1980Assignee: Rumianca S.p.A.Inventors: Vittorio Messori, Renato Francese
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Patent number: 4224444Abstract: Chloro-bis(alkylamino)-s-triazine is prepared by means of the step-wise replacement of two chlorine atoms of cyanuric chloride with alkylamino groups in an alkaline medium comprising water and a liquid organic compound which is a solvent for cyanuric chloride and forms a two-phase system with water, in which a molar excess of alkylamine is used in the second replacement step. Upon completion of the second replacement step the reaction mixture is freed from its aqueous phase and the residual suspension or solution of triazine in the organic compound is admixed with water added in a volumetric quantity of from 30 to 150% with respect to that of said aqueous phase.The chloro-bis(alkylamino)-s-triazine thus produced has high characteristics of handling and formulability.Type: GrantFiled: October 1, 1979Date of Patent: September 23, 1980Assignee: Rumianca S.p.A.Inventors: Luciano Baldi, Vittorio Messori, Renato Francese
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Patent number: 4186265Abstract: A method is provided for separating tris(alkylamino)-s-triazine by-product from chloro-bis(alkylamino)-s-triazines by extracting tris(alkylamino)-s-triazine from an organic solution containing a mixture of tris(alkylamino)-s-triazine and chlorobis(alkylamino)-s-triazine with an aqueous acid solution in the pH-range of 5.4-0.5 and according to a further embodiment of the present invention, treating an alkaline aqueous effluent containing a mixture of chloro-bis(alkylamino)-s-triazine and tris(alkylamino)-s-triazine with an agent capable of reducing the pH value below 5.4 and extracting the chloro-bis(alkylamino)-s-triazine with a water immiscible solvent, the tris(alkylamino)-s-triazine remaining in the aqueous phase.Type: GrantFiled: December 20, 1978Date of Patent: January 29, 1980Assignee: Ciba-Geigy CorporationInventors: Jay P. Davis, Henry C. Grace, James B. Nabors
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Patent number: 4183929Abstract: Tri-substituted s-triazine di and triimino substituted alkyl and aryl mono and dicarboxylic acids and salts thereof useful as complement inhibitors.Type: GrantFiled: October 13, 1978Date of Patent: January 15, 1980Assignee: American Cyanamid CompanyInventors: Ransom B. Conrow, Seymour Bernstein
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Patent number: 4182874Abstract: The commercial method of preparing chloro-bis(alkylamino)-s-triazine by step-wise replacement of two chlorine atoms of cyanuric chloride by means of alkylamino groups in an alkaline medium comprising water and a liquid organic compound is improved by adding to the reaction product, upon completion of the second replacement step, or during or after the distillation of the organic compound, at least 0.5% by weight with respect to the weight of the chloro-bis(alkylamino)-s-triazine, of minerals chosen from the groups of montmorillonite, paligorskite, vermiculite and chlorite and having a base-exchange capacity of at least 10 milli-equivalents for each 100 grams of said solid, thus deactivating the unreacted alkylamine and the tris(alkylamino)-s-triazines present in the reaction product.Type: GrantFiled: October 20, 1978Date of Patent: January 8, 1980Assignee: Rumianca S.p.A.Inventors: Luciano Baldi, Giuliano Giorcelli, Renato Francese
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Patent number: 4182875Abstract: In the commercial process for preparing chloro-bis(aklylamino)-s-triazines by step-wise replacement of two chlorine atoms of cyanuric chloride with alkylamino groups in which a molar excess of alkylamine is used in the second replacement step, the formation of tris-(alkylamino)-s-triazines is suppressed by submitting the reaction mixture, after the second replacement step is completed, to a pressure not exceeding 400 mm Hg, at a temperature not exceeding about 55.degree. C. and for a period not exceeding about 15 minutes, thereby removing the excess alkylamine from said reaction mixture by volatilization without substantially removing the other components of the reaction mixture.Type: GrantFiled: October 20, 1978Date of Patent: January 8, 1980Assignee: Rumianca S.p.A.Inventors: Renato Francese, Roberto Esposito
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Patent number: 4180664Abstract: A process for improving the color yield and the wetfastness properties of dyeings produced on cellulose fibre material with anionic dyes, which process comprises treating the cellulose material before, during or after dyeing, with a cationic fibre-reactive compound of the formula ##STR1## wherein B represents a mono- or polynuclear heterocyclic radical,Hal represents a reactive halogen atom,X represents halogen, lower alkoxy, lower alkylthio, phenoxy, phenylthio, ##STR2## or the group of the formula ##STR3## each of W.sub.1 and W.sub.2 independently represents the direct bond, ##STR4## Z represents hydrogen, lower alkyl or hydroxy-lower alkyl, each of Q.sub.1 and Q.sub.2 independently represents an aliphatic or cycloaliphatic radical,each ofR.sub.1, R.sub.2, V.sub.1, V.sub.2, Y.sub.1 and Y.sub.2 independently represents lower alkyl, or lower alkyl or benzyl each of which is substituted by halogen, hydroxy or cyano, or each of the pair of substituents R.sub.1 and R.sub.2 and Y.sub.1 and Y.sub.Type: GrantFiled: June 9, 1977Date of Patent: December 25, 1979Assignee: Ciba-Geigy CorporationInventors: Pierre Perrin, Gert Hegar, Gerald Siegrist, Herbert Seiler, Ulrich Horn
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Patent number: 4166909Abstract: An improved process is disclosed for the preparation of 2-chloro-4-ethylamino-6-isopropylamino-s-triazine wherein two of the three chlorine atoms on cyanuric chloride are replaced with ispropylamino and ethylamino substituents by sequential reaction of cyanuric chloride in a mixed acetone/water solvent system with isopropylamine and ethylamine, respectively, in the presence of an alkali metal hydroxide acid acceptor.Type: GrantFiled: January 23, 1978Date of Patent: September 4, 1979Assignee: Shell Oil CompanyInventors: Thomas H. Colby, Ernest R. Freitas, William R. Durland
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Patent number: 4132850Abstract: Tri-substituted s-triazine di and triimino substituted alkyl and aryl mono and dicarboxylic acids and salts thereof useful as complement inhibitors.Type: GrantFiled: June 29, 1977Date of Patent: January 2, 1979Assignee: American Cyanamid CompanyInventors: Ransom B. Conrow, Seymour Bernstein
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Patent number: 4124763Abstract: Novel 1,2-diaryl-1,2-dicyano-ethane compounds having the following formula: ##STR1## wherein (1) M, N, P, AND Q INDEPENDENTLY ARE 0 OR 1, PROVIDED THAT IF M = 0, THEN N = 0; AND IF P = 0, THEN Q = 0;(2) the groups Y and C, X and D, or both, being capable of forming a heterocyclic ring having 2 to 5 carbon atoms;(3) X, Y, C, and D are independently selected from the group consisting of substituted and unsubstituted alkyl groups having from 1 to about 20 carbon atoms, alkenyl groups having from 2 to about 20 carbon atoms, cycloalkyl groups having from 3 to 6 carbon atoms, and phenyl;(4) if m = 0, X may also be chlorine;(5) if p = 0, Y may also be chlorine;(6) if m = 1, X and D independently may also be hydrogen;(7) if p = 1, Y and C independently may also be hydrogen;(8) if m = 1 and n = 1, A is nitrogen;(9) if m = 1 and n = 0, A is one member selected from the group consisting of oxygen and sulfur;(10) if p = 1 and q = 1, B is nitrogen;(11) if p = 1 and q = 0, B is one member selected from the group consistingType: GrantFiled: December 10, 1976Date of Patent: November 7, 1978Assignee: Akzona IncorporatedInventors: Willem J. Mijs, Charles H. V. Dusseau, Hermannus J. M. Sinnige
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Patent number: 4120855Abstract: A method and composition for producing a bactericidal active monochlorotriazine dye, by reacting active dichlorotriazine dye with a bactericidal compound containing hydroxyl or amino groups. The reaction is run in an aqueous, organic, or water-organic medium at 20.degree.-40.degree. C. The monochlorotriazine dye thus formed is active and possesses bactericidal properties. On dyeing fibres, it endows them with high bactericidal properties retained after repeated wet treatments.Type: GrantFiled: October 18, 1976Date of Patent: October 17, 1978Inventors: Vladimir Leibovich Liverant, Lev Moiseevich Yagupolsky, Andrei Yakovlevich Ilichenko, Faina Borisovna Timashpolskaya, Elena Alexeevna Fedorovskaya, Lidia Ivanovna Petrik, Iosif Yakubovich Kalantarov, Mira Semenovna Kopylova, Idima Evgenievna Meitus
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Patent number: 4112226Abstract: A method for removing non-fluorescent triazine derivative impurities having the structural formula: ##STR1## wherein R.sub.1 is a hydroxy group or a halogen atom,R.sub.2 is a hydroxy group or the group --NR.sub.4 R.sub.5, each ofR.sub.4 and R.sub.5 being a hydrogen atom, alkyl, substituted alkyl, aryl or substituted aryl group, or R.sub.4 or R.sub.5 being combined in a heterocyclic ring, andR.sub.3 is an alkyl, substituted alkyl, aryl or substituted aryl group,From fluorescent agents belonging to the class of compounds of 4,4'-di(sym-triazinylamino) stilbene-2,2'- disulphonic acids and salts thereof, by washing said fluorescent agent with a dilute aqueous solution of an alkali metal hydroxide under atmospheric pressure and at a temperature not exceeding 75.degree. C.Type: GrantFiled: October 22, 1976Date of Patent: September 5, 1978Assignee: Lever Brothers CompanyInventor: Philip Richard Norman Eymond
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Patent number: 4108829Abstract: Novel piperidyl triazine derivatives are produced by reacting a substituted halogentriazine with a polyalcohol, a polymercaptan or a polyamine. The compounds are valuable light stabilizers for synthetic polymers, such as polyolefins, and fast to extraction in aqueous surfactant solutions.Type: GrantFiled: June 23, 1976Date of Patent: August 22, 1978Assignee: Chimosa Chimica Organica S.p.A.Inventors: Paolo Cassandrini, Antonio Tozzi
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Patent number: 4099006Abstract: 2-CHLORO-S-TRIAZINE SUBSTITUTED IN AT LEAST ONE OF THE POSITIONS 4,6 OF THE TRIAZINE RING WITH AN AMINO GROUP IS OBTAINED BY FEEDING SEPARATELY AN AQUEOUS AMINE SOLUTION AND AN AQUEOUS NaOH solution into a water-organic liquid reaction medium containing cyanuric chloride, delivering to said medium per unit of time from 1.05 to 1.30 moles of amine for each mole of sodium hydroxide, feeding the amine solution until an amount of from 1 to 2 moles of amine per mole of cyanuric chloride is reached in the medium and the NaOH solution until an amount in moles equal to or slightly higher than the amount of amine moles fed in is reached in the medium. The temperature of the reaction medium is maintained at a value of from 5.degree.-15.degree. C to 60.degree.-70.degree. C during the feeding period.Type: GrantFiled: December 29, 1975Date of Patent: July 4, 1978Assignee: Rumianca S.p.A.Inventors: Luciano Baldi, Corrado Ferrari, Renato Francese
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Patent number: 4082739Abstract: A dyestuff of the formula ##STR1## wherein F.sub.1 represents a dyestuff radical, particularly an azo dyestuff radical, R.sub.1 and R.sub.2 represent hydrogen, lower alkyl, or aryl, X.sub.1 and X.sub.2 each represent halogen, and X.sub.3 represents halogen, amino, lower alkyl amino, di-lower alkyl amino, lower alkoxy, phenoxy, lower alkylthio, or a group of the formula --N(R.sub.3)--F.sub.2 in which R.sub.3 represents hydrogen, lower alkyl, or aryl and F.sub.2 represents a dyestuff radical, particularly an azo dyestuff radical.Type: GrantFiled: December 26, 1973Date of Patent: April 4, 1978Assignee: Ciba-Geigy AGInventor: Karl Seitz
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Patent number: 4058662Abstract: There is provided a process, preferably continuous and in a given case successive, substitution of one or two chlorine atoms of cyanuric chloride by one or two amines, which may be the same or different, in the presence of an acid acceptor and in the presence of an organic solvent, particularly for the production of 2-alkylamino-4,6-dichloro and preferably for the production of 2,4-di(alkylamino)-6-chloro-s-triazines wherein there is added 1.00 to 1.05 mole, preferably 1.00 to 1.03 mole of a first amine to a 4.5 to 50 weight % suspension or solution of cyanuric chloride in a mixture of 65 to 85 weight % of xylene, toluene, ethylbenzene, benzene and/or an aliphatic or cycloaliphatic hydrocarbon with 5 to 10 carbon atoms (toluene being preferred) and 35 to 15 weight % of a ketone with 3 to 8 carbon atoms, preferably acetone, while maintaining the temperature between about 0 and about 20.degree. C, preferably about 10 to 18.degree. C.Type: GrantFiled: February 10, 1976Date of Patent: November 15, 1977Assignee: Deutsche Gold- und Silber-Scheideanstalt Vormals RoesslerInventors: Heinz Haschke, Gerd Schreyer, Werner Schwarze, Helmut Suchsland
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Patent number: 4054739Abstract: There is provided a process for the substitution of one or for the successive substitution of two chlorine atoms of cyanuric chloride by one or two amines whch may be the same or different in the presence of an acid binding agent and in the presence of an organic solvent, particularly for the production of 2-alkylamino-4,6-dichloro-, s-triazines and more preferably for the production of 2,4-di-(alkylamino)-6-chloro-s-triazines wherein there is used a 4 to 60 weight % solution or suspension of cyanuric chloride in a mixture of 65 to 85 weight % of one or more aliphatic hydrocarbons or cycloaliphatic hydrocarbons hving 5 to 10 carbon atoms and/or one or more aromatic hydrocarbons and 35 to 15 weight % of one or more ketones having 3 to 8 carbon atoms.Type: GrantFiled: February 10, 1976Date of Patent: October 18, 1977Assignee: Deutsche Gold- Und Silber-Scheideanstalt Vormals RoesslerInventors: Heinz Haschke, Gerd Schreyer, Werner Schwarze, Helmut Suchsland