Processes Patents (Class 564/61)
  • Patent number: 4749806
    Abstract: The present invention relates to a process for the synthesis of isocyanates and of isocyanate derivatives. Isocyanates are obtained by reacting an organic halide with a metal cyanate in an organic medium in the presence of a catalyst consisting of a complex of nickel with at least one organic ligand, in which complex the nickel is in the zero oxidation state.A carbamate or a urea, respectively, are obtained by a subsequent reaction with a hydroxy compound or a primary or secondary amine.Isocyanates and their derivatives are used especially either as refined synthesis agents for the production of pesticides and medications, or as monomers or comonomers for the preparation of many macromolecular compounds.
    Type: Grant
    Filed: August 25, 1987
    Date of Patent: June 7, 1988
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Igor Tkatchenko, Rabih Jaouhari, Michel Bonnet, Gordon Dawkins, Serge Lecolier
  • Patent number: 4740618
    Abstract: Monocyclohexylurea can be prepared particularly selectively if 100 parts by weight of cyclohexylamine are reacted with 70 to 300 parts by weight of urea in the presence of water in the boiling range of water.
    Type: Grant
    Filed: September 19, 1983
    Date of Patent: April 26, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rudolf Fauss, Kurt Findelsen, Uwe Dobereiner
  • Patent number: 4725680
    Abstract: The invention relates to a process for preparing carbamic acid derivatives of formula: ##STR1## in which R.sup.1 or R.sup.2 denotes a hydrogen atom or a substituted or unsubstituted, saturated or unsaturated aliphatic, cycloaliphatic or heterocyclic radical, or R.sup.1 and R.sup.2 together form a ring, and Y denotes OR, SR, ##STR2## groups, R being a substituted or unsubstituted, saturated or unsaturated aliphatic or cycloaliphatic radical, or a substituted or unsubstituted aromatic radical, R.sup.3 and R.sup.4 denote a hydrogen atom or an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical or together form a ring, and R.sup.6 and R.sup.7 denote a saturated or unsaturated, substituted or unsubstituted aliphatic or cycloaliphatic radical, a hydrogen atom, an alkylthio radical or an alkyloxy radical.According to the process, a compound of formula ##STR3## is reacted with an .alpha.-halogenated derivative of formula ##STR4## at a temperature of -5.degree. to 150.degree. C.
    Type: Grant
    Filed: February 14, 1985
    Date of Patent: February 16, 1988
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Gerard Barcelo, Jean-Pierre Senet, Gerard Sennyey
  • Patent number: 4533499
    Abstract: A process for the production of a compound of formula ##STR1## which comprises reacting a compound of formula ##STR2## or a mixture of the compounds (2a) and (2b) with a compound ZH or a compound of formula ##STR3## or a mixture of the compounds (2c) and (2d) with a compound YH, both reactions under acidic conditions, wherein X and Y are the same or different and each represents an aromatic carbocyclic radical having an unsubstituted or substituted amino group in the para position to the indicated bond, or a heterocyclic group, and Z represents an aryl radical of formula ##STR4## wherein R.sub.1 and R.sub.2 independently of one another represent hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.8 -alkoxyalkyl, cycloalkyl, aralkyl, aryl, or substituted alkyl, cycloalkyl, aralkyl or aryl, or R.sub.1 and R.sub.
    Type: Grant
    Filed: April 6, 1984
    Date of Patent: August 6, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Malcolm C. Clark, John B. Henshall, Derrick A. Hart
  • Patent number: 4532266
    Abstract: Polyether-based urethane-group-containing polyamines containing polymers and/or copolymers of unsaturated monomers and, optionally, urea and/or biuret and/or allophanate groups are produced by (a) reacting an NCO-prepolymer in aqueous alkaline solution at 0.degree. to 40.degree. C. to form a carbamate; (b) converting this carbamate to an amine by adding an ion exchanger to the reaction mixture; and (c) separating the polyamine from the reaction mixture. The NCO-prepolymers used as starting materials are prepolymers of (i) polyalkylene ether polyols having a molecular weight of from 1,000 to 10,000 containing from 1 to 60 wt. % of graft (co)polymers of unsaturated monomers; and (ii) excess molar quantities of organic polyisocyanate; and optionally, (iii) a low molecular weight chain-extending agent. The product polyamines have a molecular weight of from 1,000 to 10,000 and contain from 0.65 to 59.3 wt. % graft (co)polymer and from 0.11 to 2.9 wt. % terminal NH.sub.
    Type: Grant
    Filed: March 19, 1982
    Date of Patent: July 30, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Rasshofer, Gerhard Balle, Dieter Dieterich, Holger Meyborg
  • Patent number: 4532317
    Abstract: Aromatic polyamines containing aromatic primary amino groups as well as urethane and polyester groups are made by hydrolyzing an isocyanate in the presence of a basic material and water to form a carbamate and then converting the carbamate groups to amino groups. The isocyanate starting material contains aromatic isocyanate groups (as well as urethane and polyester groups) and has an NCO content of from 0.5 to 11.5 wt %. The basic compound is selected from alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal silicates, alkali metal sulfides, alkali metal cyanides, tetraalkylammonium hydroxides and mixtures thereof. Water is used in a quantity such that at least one mole of water is present for each equivalent of NCO groups. The carbamate groups may be converted to amino groups by treating the carbamate-containing mixture with a proton donor or with heat or with a solvent. The product polyamines are particularly useful in the production of polyurethanes.
    Type: Grant
    Filed: June 21, 1983
    Date of Patent: July 30, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventor: Werner Rasshofer
  • Patent number: 4515923
    Abstract: Polyamines containing aromatically bound primary amino groups having an NH.sub.2 -content of from 0.19 to 20.3 wt % are produced by a single stage process. A compound containing aromatically bound NCO-groups and having an isocyanate content of from 0.5 to 40 wt % is hydrolyzed with an excess of water in the presence of a water-miscible polar solvent and optionally a catalyst. The hydrolysis is carried out at a temperature of from -10.degree. to 150.degree. C. in a manner such that the reaction mixture is substantially homogeneous. The water-miscible polar solvent generally has a boiling point of from 56.degree. to 250.degree. C. and a dielectric constant of at least 10. This polar solvent is used in a quantity of at least 5 parts solvent for every 100 parts of isocyanate. Tertiary amines are the preferred catalysts. These polyamines are particularly useful in the production of polyurethanes.
    Type: Grant
    Filed: June 21, 1983
    Date of Patent: May 7, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rudolf Fauss, Hans J. Meiners, Werner Rasshofer, Holger Meyborg
  • Patent number: 4514571
    Abstract: A process for the preparation of a urea derivative having the formula: ##STR1## in which A represents a straight- or branched-chain alkyl group having 1-20 carbon atoms, an aryl group, or a heterocyclic group, and each of R.sup.1 and R.sup.2 represents hydrogen, a straight- or branched-chain alkyl group having 1-20 carbon atoms, an alicyclic group, or an aryl groups, which comprises:reacting sodium salt of an N-halogenamide with a quaternary ammonium salt to obtain its addition salt and then,reacting said addition salt with an amine derivative in the absence or presence of an organic solvent.
    Type: Grant
    Filed: May 19, 1983
    Date of Patent: April 30, 1985
    Assignee: UBE Industries, Ltd.
    Inventors: Mamoru Nakai, Fumio Iwata, Teruhiko Inoue
  • Patent number: 4467114
    Abstract: A process is disclosed for selectively making trans-cyclohexane-1,4-diisocyanate, trans-cyclohexane-1,4-diamine, a trans-cyclohexane-1,4-diurethane, a trans-cyclohexane-1,4-diurea and trans-cyclohexane-1,4-disulphonyl urea by reacting ammonia with a mixture of cis and trans-cyclohexane-1,4-dicarboxylic acid, a lower alkyl ester, a glycol ester, an oligomeric ester or a polyester to make a solid trans-dicarboxylic acid diamide in a first step. The diamide is chlorinated to form cyclohexane-1,4-dicarboxylic acid-bis-N-chloramide.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: August 21, 1984
    Assignee: Akzona Incorporated
    Inventors: Hans Zengel, Manfred Bergfeld
  • Patent number: 4435567
    Abstract: A process for the preparation of substituted urea derivatives, and compositions and concentrates for the same purpose are disclosed. According to the process the substituted urea derivatives of formula (I) ##STR1## wherein R is hydrogen, alkyl, aryl, cycloalkyl or aralkyl, R.sup.1 and R.sup.2 are hydrogen, alkyl, alkenyl, alkinyl, alkoxy, oxyalkyl, cycloalkyl, aralkyl, alkoxycarbonylalkyl, aryl or heteroaryl, or R.sup.1 and R.sup.
    Type: Grant
    Filed: December 28, 1981
    Date of Patent: March 6, 1984
    Assignee: Chinoin Gyogyszer es Vesgyeszeti Termekek Gyara R. T.
    Inventors: Gyorgy Lugosi, Antal Simay, Janos Bodnar, Laszlo Simandi, Eva Somfai
  • Patent number: 4386218
    Abstract: A compound having a terminal isocyanate group is hydrolyzed to produce a polyamine having a urethane and/or a urea and/or a biuret group. More particularly, a carbamate is made by mixing an isocyanate prepolymer having urethane and/or urea and/or biuret groups present with aqueous base solutions at a temperature of from 0.degree. to 0.degree. C. and in quantities such that the equivalent ratio of hydroxyl to isocyanate groups is between from 0.3:1 to .gtoreq.1.01 to 1. The carbamate is then treated with an acid ion exchanger to form an amine. The amine is then removed from any other material which may be present. A preferred polyamine thus-produced corresponds to the general formula: ##STR1## in which each R radical may represent a divalent straight or branched-chain aliphatic radical; a divalent cycloaliphatic radical; a 4,4'- and/or a 2,4'-dicyclohexylmethane radical; or a 2,4- and/or 2,6-methyl cyclohexane radical.
    Type: Grant
    Filed: October 5, 1981
    Date of Patent: May 31, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Rasshofer, Dieter Dieterich, Holger Meyborg
  • Patent number: 4380665
    Abstract: A method is disclosed for removing methyl isocyanate from gaseous effluent streams by contacting the gaseous effluent stream with activated alumina.
    Type: Grant
    Filed: September 8, 1981
    Date of Patent: April 19, 1983
    Assignee: FMC Corporation
    Inventor: John W. Ager
  • Patent number: 4349526
    Abstract: Tetra substituted ureas wherein at least one substituent is an aryl group have proven very oxidation resistant in the anthraquinone process for making hydrogen peroxide. The urea nitrogen is directly attached to the aryl group. These ureas can be used as a single solvent or as a component of a mixture of solvents.
    Type: Grant
    Filed: July 14, 1981
    Date of Patent: September 14, 1982
    Assignee: Degussa Aktiengesellschaft
    Inventors: Gustaaf Goor, Wolfgang Kunkel
  • Patent number: 4346233
    Abstract: This disclosure relates to a process for preparing long-chain hydrocarbon substituted ureas by reacting a long chain fatty acid N-chloramide in isopropanol and/or tertiary butanol with an aliphatic or araliphatic primary or secondary amine in the presence of an alkali or alkaline earth hydroxide at a temperature of from 20.degree. to 100.degree. C. The process of this disclosure is particularly useful in preparing long-chain hydrocarbon substituted ureas wherein one of the aliphatic hydrocarbon substituents contains one or more hydroxyl and/or carboxyl groups, as well as the salts of such substituted ureas.
    Type: Grant
    Filed: March 31, 1981
    Date of Patent: August 24, 1982
    Assignee: Akzona Incorporated
    Inventors: Hans G. Zengel, Manfred F. Bergfeld, Rainer Zielke
  • Patent number: 4310692
    Abstract: The instant invention is directed to a process for the preparation of an alkyl-substituted urea of the formula ##STR1## wherein R and R', which may be the same or different, represents hydrogen or a saturated hydrocarbon radical, provided that at least one represents a saturated aliphatic hydrocarbon radical, comprising reacting, unpressurized, at from 110.degree. to 170.degree. C., urea with an amine having a boiling point, under normal pressure, at least 10.degree. C.
    Type: Grant
    Filed: September 11, 1980
    Date of Patent: January 12, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Reinhard Freimuth, Kuno Wagner
  • Patent number: 4293454
    Abstract: A flame retardant composition is prepared by reacting chloral with a nitrogen compound having the formula: ##STR1## wherein: (a) X= ##STR2## or, --SO.sub.2 --; (b) Z is selected from O or S;(c) R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are selected from the group consisting of H, alkyl of 1 to 6 carbons, and substituted or unsubstituted hydroxyalkyl of 2 to 4 carbons and mixtures thereof in a temperature range of 25.degree. to 100.degree. C., in the absence of a solvent and in an apparatus that provides efficient mixing. These compositions are useful for preparing flame retardant polyurethane foams.
    Type: Grant
    Filed: February 4, 1980
    Date of Patent: October 6, 1981
    Assignee: Pennwalt Corporation
    Inventors: Harold G. Monsimer, Stanley R. Sandler
  • Patent number: 4288592
    Abstract: There is provided a process for preparing amides which comprises reacting an amine, or an amide, and an acid halide, or anhydride, in suitable molecular proportions, in an inert organic diluent, in the presence of an effective amount of a molecular sieve, until the reaction is completed, separating the molecular sieve, and recovering the amide from the organic mother liquor.
    Type: Grant
    Filed: April 30, 1979
    Date of Patent: September 8, 1981
    Assignee: American Cyanamid Company
    Inventors: Michael M. Rauhut, Shin-Shyong Tseng
  • Patent number: 4276387
    Abstract: A compound of Formula I: ##STR1## is useful as flame retardants for polyurethane foams. It is added directly to the reaction mixture for the preparation of the polyurethane foam.
    Type: Grant
    Filed: April 28, 1980
    Date of Patent: June 30, 1981
    Assignee: Pennwalt Corporation
    Inventors: Jeffrey D. Miano, Stanley R. Sandler
  • Patent number: 4238404
    Abstract: A process for the preparation of derivatives of aliphatic, cycloaliphatic, and araliphatic compounds containing from 1 to 3 isocyanate groups bonded to from 1 to 3 secondary or tertiary carbon atoms, or a combination thereof, is disclosed. The process comprises reacting a compound of the formula R--(CO--NHCl).sub.n, wherein R represents an aliphatic, cycloaliphatic, or araliphatic radical, with a tertiary amine having a pK.sub.a greater than 7, at a temperature from about 20.degree. to about 180.degree. C., in an inert solvent, to form a compound of the formula R--(N.dbd.C.dbd.O).sub.n, wherein the isocyanate groups are bonded to secondary or tertiary carbon atoms.
    Type: Grant
    Filed: May 18, 1979
    Date of Patent: December 9, 1980
    Assignee: Akzona Incorporated
    Inventors: Hans Zengel, Manfred Bergfeld, Rainer Zielke, Erich Klimesch