Two Substituent Nitrogens Bonded Directly To Two Carbons Of The Triazine Ring Patents (Class 544/204)
  • Patent number: 4659822
    Abstract: 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: Grant
    Filed: February 13, 1986
    Date of Patent: April 21, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Priesnitz, Hans-Jochem Riebel
  • Patent number: 4657908
    Abstract: 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: Grant
    Filed: February 12, 1985
    Date of Patent: April 14, 1987
    Assignees: ICI Americas, Inc., Imperial Chemical Industries PLC
    Inventors: Tobias O. Yellin, David J. Gilman, Philip N. Edwards, Michael S. Large, Derrick F. Jones, Keith Oldham
  • Patent number: 4621143
    Abstract: A number of novel amides were found to be highly effective as cockroach repellents.
    Type: Grant
    Filed: June 27, 1984
    Date of Patent: November 4, 1986
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Terrence P. McGovern, George S. Burden
  • Patent number: 4614818
    Abstract: 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: Grant
    Filed: January 18, 1983
    Date of Patent: September 30, 1986
    Assignee: Ciba Geigy Corporation
    Inventors: Rolf Deitz, Herbert Seiler
  • Patent number: 4586950
    Abstract: Herbicidal sulfonamides are useful as general or selective herbicides, both pre-emergence and post-emergence.
    Type: Grant
    Filed: September 20, 1983
    Date of Patent: May 6, 1986
    Assignee: E. I. Du Pont de Nemours & Company
    Inventor: Robert J. Pasteris
  • Patent number: 4576945
    Abstract: Hexaalkylmelamine-amino-oxy compounds having anti-tumor properties and pharmaceutical compositions for and therapeutic methods of treatment of tumors and employing same.
    Type: Grant
    Filed: January 3, 1984
    Date of Patent: March 18, 1986
    Inventor: Mark E. Sanders
  • Patent number: 4562188
    Abstract: 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: Grant
    Filed: January 13, 1984
    Date of Patent: December 31, 1985
    Assignee: William H. Rorer, Inc.
    Inventors: Donald E. Kuhla, William L. Studt, Henry F. Campbell, John Yelnosky
  • Patent number: 4559345
    Abstract: 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: Grant
    Filed: July 21, 1982
    Date of Patent: December 17, 1985
    Assignee: LBP Istituto Faraceutico S.p.A.
    Inventors: Piero Gomarasca, Carlo Scolastico, Cesare Sirtori
  • Patent number: 4544401
    Abstract: N-(heterocyclicaminocarbonyl)pyridinesulfonamides; are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.
    Type: Grant
    Filed: January 22, 1981
    Date of Patent: October 1, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: George Levitt
  • Patent number: 4544402
    Abstract: 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: Grant
    Filed: May 24, 1984
    Date of Patent: October 1, 1985
    Assignee: Chemische Werke Huls Aktiengesellschaft
    Inventors: Horst Schnurbusch, Helmut Baltruschat
  • Patent number: 4540782
    Abstract: 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: Grant
    Filed: July 26, 1984
    Date of Patent: September 10, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Willy Meyer
  • Patent number: 4485041
    Abstract: 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: Grant
    Filed: February 17, 1981
    Date of Patent: November 27, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Hoyer, Fritz Meininger, Rudolf Fass
  • Patent number: 4469828
    Abstract: 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: Grant
    Filed: November 22, 1982
    Date of Patent: September 4, 1984
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Tohru Haruna, Masayuki Takahashi
  • Patent number: 4459151
    Abstract: 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: Grant
    Filed: August 13, 1982
    Date of Patent: July 10, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Engelbert Kuhle, Bernd Baasner, Hermann Hagemann, Ludwig Eue, Robert R. Schmidt
  • Patent number: 4455424
    Abstract: 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: Grant
    Filed: February 24, 1977
    Date of Patent: June 19, 1984
    Assignee: Sandoz Ltd.
    Inventor: Bansi L. Kaul
  • Patent number: 4451463
    Abstract: 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: Grant
    Filed: March 1, 1982
    Date of Patent: May 29, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventor: Michael S. Large
  • Patent number: 4447441
    Abstract: 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: Grant
    Filed: March 1, 1982
    Date of Patent: May 8, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventors: Tobias O. Yellin, David J. Gilman
  • Patent number: 4435206
    Abstract: N-(heterocyclicaminocarbonyl)pyridinesulfonamides are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.
    Type: Grant
    Filed: January 22, 1981
    Date of Patent: March 6, 1984
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: George Levitt
  • Patent number: 4412856
    Abstract: 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: Grant
    Filed: May 22, 1981
    Date of Patent: November 1, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Georg Brunner, Rolf Schurter, Henry Szczepanski
  • Patent number: 4390538
    Abstract: 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: Grant
    Filed: August 31, 1981
    Date of Patent: June 28, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Wolfgang Wehner, Saleem Farooq, Hans-Gunter Kostler
  • Patent number: 4384102
    Abstract: 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: Grant
    Filed: January 4, 1982
    Date of Patent: May 17, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Rasshofer, Gerhard Grogler, Richard Kopp
  • Patent number: 4339383
    Abstract: 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: Grant
    Filed: July 2, 1980
    Date of Patent: July 13, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Wolfgang Wehner, Klaus-Peter Michaelis, Rainer Schneider
  • Patent number: 4338092
    Abstract: 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: Grant
    Filed: December 17, 1980
    Date of Patent: July 6, 1982
    Assignee: Sandoz Ltd.
    Inventor: Lukas Schneider
  • Patent number: 4294580
    Abstract: 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: Grant
    Filed: December 31, 1979
    Date of Patent: October 13, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hermann Henk, Klaus Wunderlich, Peter Wild
  • Patent number: 4288594
    Abstract: 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: Grant
    Filed: February 4, 1980
    Date of Patent: September 8, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Philip G. McCracken, Hal Myatt, Harris E. Petree
  • Patent number: 4275204
    Abstract: 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: Grant
    Filed: September 7, 1979
    Date of Patent: June 23, 1981
    Assignee: Rumianca S.p.A.
    Inventors: Vittorio Messori, Renato Francese, Roberto Esposito
  • Patent number: 4270918
    Abstract: 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: Grant
    Filed: December 22, 1978
    Date of Patent: June 2, 1981
    Assignee: Ciba-Geigy Corporation
    Inventor: Karl Seitz
  • Patent number: 4263434
    Abstract: 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: Grant
    Filed: April 28, 1978
    Date of Patent: April 21, 1981
    Assignee: Chimosa Chimica Organica S.p.A.
    Inventors: Paolo Cassandrini, Antonio Tozzi
  • Patent number: 4261889
    Abstract: 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: Grant
    Filed: October 19, 1978
    Date of Patent: April 14, 1981
    Assignee: Ciba-Geigy Corp.
    Inventors: Herbert Seiler, Gert Hegar
  • Patent number: 4260779
    Abstract: 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: Grant
    Filed: November 9, 1979
    Date of Patent: April 7, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Raymond Bernasconi, Pier G. Ferrini, Richard Goschke, Jacques Gosteli
  • Patent number: 4255570
    Abstract: 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: Grant
    Filed: August 3, 1978
    Date of Patent: March 10, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Grogler, Holger Meyborg
  • Patent number: 4246408
    Abstract: 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: Grant
    Filed: March 8, 1979
    Date of Patent: January 20, 1981
    Assignee: ICN Pharmaceuticals
    Inventors: Roland K. Robins, Ganapathi R. Revankar
  • Patent number: 4232153
    Abstract: 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: Grant
    Filed: July 7, 1978
    Date of Patent: November 4, 1980
    Assignee: Rumianca S.p.A.
    Inventors: Luciano Baldi, Renato Francese, Franco Collecchia
  • Patent number: 4230853
    Abstract: 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: Grant
    Filed: October 1, 1979
    Date of Patent: October 28, 1980
    Assignee: Rumianca S.p.A.
    Inventors: Vittorio Messori, Renato Francese
  • Patent number: 4224444
    Abstract: 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: Grant
    Filed: October 1, 1979
    Date of Patent: September 23, 1980
    Assignee: Rumianca S.p.A.
    Inventors: Luciano Baldi, Vittorio Messori, Renato Francese
  • Patent number: 4186265
    Abstract: 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: Grant
    Filed: December 20, 1978
    Date of Patent: January 29, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: Jay P. Davis, Henry C. Grace, James B. Nabors
  • Patent number: 4183929
    Abstract: Tri-substituted s-triazine di and triimino substituted alkyl and aryl mono and dicarboxylic acids and salts thereof useful as complement inhibitors.
    Type: Grant
    Filed: October 13, 1978
    Date of Patent: January 15, 1980
    Assignee: American Cyanamid Company
    Inventors: Ransom B. Conrow, Seymour Bernstein
  • Patent number: 4182874
    Abstract: 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: Grant
    Filed: October 20, 1978
    Date of Patent: January 8, 1980
    Assignee: Rumianca S.p.A.
    Inventors: Luciano Baldi, Giuliano Giorcelli, Renato Francese
  • Patent number: 4182875
    Abstract: 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: Grant
    Filed: October 20, 1978
    Date of Patent: January 8, 1980
    Assignee: Rumianca S.p.A.
    Inventors: Renato Francese, Roberto Esposito
  • Patent number: 4180664
    Abstract: 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: Grant
    Filed: June 9, 1977
    Date of Patent: December 25, 1979
    Assignee: Ciba-Geigy Corporation
    Inventors: Pierre Perrin, Gert Hegar, Gerald Siegrist, Herbert Seiler, Ulrich Horn
  • Patent number: 4166909
    Abstract: 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: Grant
    Filed: January 23, 1978
    Date of Patent: September 4, 1979
    Assignee: Shell Oil Company
    Inventors: Thomas H. Colby, Ernest R. Freitas, William R. Durland
  • Patent number: 4132850
    Abstract: Tri-substituted s-triazine di and triimino substituted alkyl and aryl mono and dicarboxylic acids and salts thereof useful as complement inhibitors.
    Type: Grant
    Filed: June 29, 1977
    Date of Patent: January 2, 1979
    Assignee: American Cyanamid Company
    Inventors: Ransom B. Conrow, Seymour Bernstein
  • Patent number: 4124763
    Abstract: 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 consisting
    Type: Grant
    Filed: December 10, 1976
    Date of Patent: November 7, 1978
    Assignee: Akzona Incorporated
    Inventors: Willem J. Mijs, Charles H. V. Dusseau, Hermannus J. M. Sinnige
  • Patent number: 4120855
    Abstract: 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: Grant
    Filed: October 18, 1976
    Date of Patent: October 17, 1978
    Inventors: 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
  • Patent number: 4112226
    Abstract: 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: Grant
    Filed: October 22, 1976
    Date of Patent: September 5, 1978
    Assignee: Lever Brothers Company
    Inventor: Philip Richard Norman Eymond
  • Patent number: 4108829
    Abstract: 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: Grant
    Filed: June 23, 1976
    Date of Patent: August 22, 1978
    Assignee: Chimosa Chimica Organica S.p.A.
    Inventors: Paolo Cassandrini, Antonio Tozzi
  • Patent number: 4099006
    Abstract: 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: Grant
    Filed: December 29, 1975
    Date of Patent: July 4, 1978
    Assignee: Rumianca S.p.A.
    Inventors: Luciano Baldi, Corrado Ferrari, Renato Francese
  • Patent number: 4082739
    Abstract: 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: Grant
    Filed: December 26, 1973
    Date of Patent: April 4, 1978
    Assignee: Ciba-Geigy AG
    Inventor: Karl Seitz
  • Patent number: 4058662
    Abstract: 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: Grant
    Filed: February 10, 1976
    Date of Patent: November 15, 1977
    Assignee: Deutsche Gold- und Silber-Scheideanstalt Vormals Roessler
    Inventors: Heinz Haschke, Gerd Schreyer, Werner Schwarze, Helmut Suchsland
  • Patent number: 4054739
    Abstract: 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: Grant
    Filed: February 10, 1976
    Date of Patent: October 18, 1977
    Assignee: Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler
    Inventors: Heinz Haschke, Gerd Schreyer, Werner Schwarze, Helmut Suchsland