Alicyclic Ring And Plural Amino Nitrogens Containing Patents (Class 564/461)
  • Patent number: 6114392
    Abstract: The invention relates to the use of agmatine, in the treatment of acute neurotrauma (such as stroke) and degenerative disorders of the central and peripheral nervous system (such as dementia).The invention further provides novel compounds of general formula I (which are quinuclidine derivatives), formula II (which are norbornane derivatives), formula III (which are adamantane derivatives), and formula IV (which are phenothiazine derivatives): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are each independently hydrogen, hydroxy, substituted or unsubstituted C.sub.1-4 alkyl, substituted or unsubstituted C.sub.1-4 alkoxy, halogeno, amino, phenyl, or R.sub.4 NR.sub.5 ; R.sub.4 and R.sub.5 are each independently hydrogen, or (CH.sub.2)n--[NH(CH.sub.2)x]y--NHR.sub.6, or (CH.sub.2)n--[NH(CH.sub.2)x]y--NH--NHR.sub.6, or (CH.sub.2)n--[NH(CH.sub.2)x]y--(NR.sub.7 .dbd.)CNHR.sub.6, or (CH.sub.2)n--[NH(CH.sub.2)x]y--NH(NR.sub.7 .dbd.)CNHR.sub.6 wherein n is from 0-5, y is from 0-5 and each x is independently from 1-5; R.
    Type: Grant
    Filed: April 16, 1996
    Date of Patent: September 5, 2000
    Inventors: Gad M. Gilad, Varda H. Gilad
  • Patent number: 6100430
    Abstract: An alicyclic polyamine of the formula (1) ##STR1## wherein Y.sub.1 represents a saturated aliphatic hydrocarbon group and R.sub.1 through R.sub.4 are the same or different and each represents hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group. The alicyclic polyamine can be obtained by subjecting a 3-formylcycloalkanone or 3-formylcycloalkenone to reductive amination reaction.
    Type: Grant
    Filed: September 10, 1998
    Date of Patent: August 8, 2000
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Kenichi Yamamoto, Kazuyuki Matsuoka, Hiroshi Yagihara
  • Patent number: 6054065
    Abstract: A chiral ligand of the formula (I) or formula (I'), ##STR1## was synthesized. The chiral ligand (I) or formula (I') can chelate to metals to form a catalytic complex to catalyze the addition of trimethylsilyl cyanide to aldehydes to give optically active cyanohydrin, each individually.
    Type: Grant
    Filed: July 19, 1999
    Date of Patent: April 25, 2000
    Inventors: Biing-Jiun Uang, Chyuan-Der Hwang
  • Patent number: 5905170
    Abstract: The present invention relates to a process for the production of 1-amino-1-methyl-3(4)-aminomethylcyclohexane bya) simultaneously reacting 4(5)-aminomethyl-1-methylcyclohexene (CMA), hydrocyanic acid and aqueous sulphuric acid at temperatures of 60.degree. C. to 120.degree. C., preferably 80.degree. C. to 120.degree. C. to form 1-formamido-1-methyl-3(4)-aminomethylcyclohexane (FMA) in a first stage,b) adding water and hydrolyzing 1-formamido-1-methyl-3 (4)-aminomethylcyclohexane (FMA) and unreacted hydrocyanic acid in a second stage andc) adding a base and isolating 1-amino-1-methyl-3 (4)-aminomethylcyclohexane (AMCA) by extraction from the reaction mixture obtained in the second stage of the reaction, optionally after removing of formic acid.
    Type: Grant
    Filed: March 11, 1998
    Date of Patent: May 18, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Konrad Fischer, Oswald Wilmes, Dieter Arlt, Carl Casser, Peter Maas, Pierre Woestenborghs, Theo Van der Knaap
  • Patent number: 5902897
    Abstract: The present invention relates to polyamines which are prepared by reactinga) unsaturated oligoesters having an average of 2 to 4 double bonds per molecule andb) optionally other unsaturated compounds suitable as Michael addition acceptors and having an average of 1 to 4 double bonds per molecule withc) (cyclo)aliphatic diamines having two primary amino groups andd) optionally other amino-functional compounds suitable as Michael addition donors.The present invention also relates to the use of these polyamines as a binder component in lacquers and coating compositions, particularly as reactants for blocked polyisocyanates in one-component stoving lacquers.
    Type: Grant
    Filed: July 19, 1996
    Date of Patent: May 11, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christian Wamprecht, Theodor Engbert, Holger Casselmann, Josef Pedain, Jurgen Meixner
  • Patent number: 5773617
    Abstract: The present invention relates to a reagent and to a process which are useful, when carrying out an organic synthesis, for cleaving an allylic group from a function which is protected with the latter.This reagent is defined in that it contains:a) a solvent system;b) a catalyst containing at least one element from column VIII of the Periodic Table of the Elements, the said element from column VIII of the Periodic Table being coordinated with at least one coordination agent which is soluble in the said solvent system;c) a compound which is at least partially soluble in the said solvent system and which contains at least one nucleophilic function.Application to organic synthesis.
    Type: Grant
    Filed: February 22, 1996
    Date of Patent: June 30, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Marie Bernard, Errol Blart, Jean-Pierre Genet, Sandrine Lemaire-Audoire, Monique Savignac
  • Patent number: 5760157
    Abstract: Compounds of the formula?P!(ACH.sub.2 NH.sub.2).sub.xin which P denotes a partially hydrogenated 1,3-diene oligomer residue, x is practically equal to 2 and A denotes a divalent residue such as ##STR1## are obtained by selective hydrogenation of compounds of formula ?P.sub.1 !(ACN)x in which P.sub.1 denotes a 1,3-diene oligomer residue.
    Type: Grant
    Filed: December 20, 1996
    Date of Patent: June 2, 1998
    Assignee: Elf Atochem, S.A.
    Inventors: Martine Cerf, Stephane Fouquay, Joel Perthuis
  • Patent number: 5741928
    Abstract: Disclosed is a process for producing bis(aminomethyl)cyclohexane, which comprises hydrogenating a xylylenediamine in the presence of a catalyst and at least one solvent selected from the group consisting alkylamines and alkylenediamines.
    Type: Grant
    Filed: September 19, 1995
    Date of Patent: April 21, 1998
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shoichi Kobayashi, Susumu Naito
  • Patent number: 5679860
    Abstract: A process for producing 3-aminomethyl-3,5,5-trimethylcyclohexyl amine (isophorone diamine) from isophorone nitrile. Isophorone nitrile is iminated in a first stage and then the reaction mixture is subjected to aminating hydrogenation in a second stage in the presence of a fixed bed hydrogenation catalyst based on Raney cobalt. The fixed bed hydrogenation catalyst is produced in a special manner by mixing a powdery Co--containing Raney alloy with powdery cobalt, sintering the powdery mixture to shaped moldings and then activating by leaching with alkali hydroxide solution. The yield and/or space-time yield in isophorone diamine production can be increased.
    Type: Grant
    Filed: October 28, 1996
    Date of Patent: October 21, 1997
    Assignee: Degussa Aktiengesellschaft
    Inventors: Thomas Haas, Roland Burmeister, Dietrich Arntz, Karl-Ludwig Weber, Monika Berweiler
  • Patent number: 5679861
    Abstract: The present invention is directed to C.sub.60 diamine adducts, processes for preparing them and polymers prepared from them. C.sub.60 diamine adducts is a symmetrical icosahegron which is composed of 12 pentagons and 20 hexagons and links to 2 to 4 diamines. The processes for preparing the product comprises the steps of: adding C.sub.60 in benzene or toluene of a constant concentration to a certain amount of linear aliphatic diamine having the structural formula H.sub.2 N--(CH.sub.2)n--NH.sub.2 wherein n=2, 4 or 6 for reaction, or adding a definite amount of C.sub.60 directly to linear diamine of a definite concentration to produce C.sub.60 diamine adducts. Elemental analysis shows that the product contain about 5.9% nitrogen, about 72.6% carbon and about 3.84% hydrogen, and the number of diamine linked to C.sub.60 is in the range of 2 to 4. C.sub.60 diamine is useful as a polymerization monomer for the preparation of polyamides or relevant polymers.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: October 21, 1997
    Assignee: Industrial Technology Research Institute
    Inventors: Tung-Ying Kuo, Jih-Ru Hwu, Tsong-Ming Chang
  • Patent number: 5627215
    Abstract: The invention relates to compounds of formula (I), R.sub.1 and R.sub.2, each independently of the other, are selected from lower alkyl that is unsubstituted or substituted by one or more fluorine atoms which are not linked to the carbon atom of R.sub.1 or R.sub.2 bonding the nitrogen; from lower alkenyl wherein the double bond does not originate from the carbon atom that is bonded to a nitrogen bonding R.sub.1 or R.sub.2 ; from lower alkynyl wherein the triple bond does not originate from the carbon atom that is bonded to a nitrogen bonding R.sub.1 or R.sub.2 ; from cycloalkyl; and from cycloalkyl-lower alkyl; with the proviso that not more than one of the two radicals R.sub.1 and R.sub.2 is methyl; or salts thereof. The mentioned compounds are pharmacologically active against disorders that are responsive to a recuction in intracellular polyamines, such as tumours or protozoal diseases.
    Type: Grant
    Filed: August 18, 1995
    Date of Patent: May 6, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Jorg Frei, Jaroslav Stanek
  • Patent number: 5554656
    Abstract: The invention relates to a disinfectant concentrate which contains amine and alcohol wherein the alcohol component includes at least one glycol ether of limited miscibility with water and the amine component includes at least one secondary and/or tertiary alkyl amine free from hydroxyl groups. It also relates to a disinfectant producabile from the disinfectant concentrate, the use of the disinfectant concentrate and of the disinfectant as bactericide, in particular mycobactericide, fungicide or virucide.
    Type: Grant
    Filed: February 25, 1994
    Date of Patent: September 10, 1996
    Assignee: Reckitt & Colman Inc.
    Inventors: Bernd L ower, Heinz Eggensperger, Peter Goroncy-Bermes, Michael Mohr, Andreas Dettmann
  • Patent number: 5541321
    Abstract: A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: ##STR1##
    Type: Grant
    Filed: March 30, 1995
    Date of Patent: July 30, 1996
    Assignee: Abbott Laboratories
    Inventors: William R. Baker, John K. Pratt, Daniel W. Norbeck, Chen Zhao
  • Patent number: 5541320
    Abstract: A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: ##STR1##
    Type: Grant
    Filed: March 30, 1995
    Date of Patent: July 30, 1996
    Assignee: Abbot Laboratories
    Inventors: William R. Baker, John K. Pratt, Daniel W. Norbeck, Chen Zhao
  • Patent number: 5504254
    Abstract: A process is disclosed for the continuous preparation of 3-aminomethyl-3,5,5-trimethylcyclohexylamine (isophoronediamine) in high yield and high purity from 3-cyano-3,5,5-trimethylcyclohexanone (isophoronenitrile) by aminating hydrogenation with hydrogen and ammonia in the presence of a fixed bed catalyst. The aminating hydrogenation is carried out by allowing a mixture of isophoronenitrile, ammonia and a C.sub.1 -C.sub.3 -alcohol, in the presence of hydrogen, to trickle over a trickle bed reactor provided with a Co and/or Ru fixed bed catalyst, at 3 to 8 MPa and at a temperature of 40.degree. to 150.degree. C., preferably 90 to 130.degree. C., and working up the reaction mixture by distillation. Preferably, a high-boiling by-product fraction, containing a bicyclic amidine, is added to the mixture to be hydrogenated, thereby appreciably increasing the yield.
    Type: Grant
    Filed: December 22, 1994
    Date of Patent: April 2, 1996
    Assignee: Degussa Aktiengesellschaft
    Inventors: Thomas Haas, Dietrich Arntz, Dieter Most
  • Patent number: 5436339
    Abstract: A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: ##STR1##
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: July 25, 1995
    Assignee: Abbott Laboratories
    Inventors: William R. Baker, John K. Pratt, Daniel W. Norbeck, Chen Zhao
  • Patent number: 5347003
    Abstract: Methods are provided whereby an N-C-N compound is regenerated from a product of a sulfur scavenging reaction, in which said N-C-N compound removes a sulfur atom from a sulfur compound, to form the original N-C-N compound. The N-C-N compound is represented by the formula (I): ##STR1## The product includes a hetero compound having sulfur, carbon and nitrogen atoms in its backbone. In one embodiment, the product is mixed with (1) a nitrogen compound represented by the formula (II): ##STR2## and (2) an alkaline compound selected from alkali metal, alkaline earth metal and transition metal compounds, to form a solution, slurry or dispersion. The hetero compound is reacted with the nitrogen compound in the presence of the alkaline compound, such that a sulfur atom of the hetero compound is replaced by a nitrogen atom of the nitrogen compound. If necessary, the pH of the solution may be adjusted to about 8 to about 13 to facilitate the reaction. In alternative embodiments, the product also includes an amine complex.
    Type: Grant
    Filed: March 5, 1993
    Date of Patent: September 13, 1994
    Assignee: Quaker Chemical Corporation
    Inventors: Edward A. Trauffer, Robert D. Evans
  • Patent number: 5319143
    Abstract: There are disclosed certain bis(aminoethanethiols) and the salts thereof which find utility as intermediates in the preparation of certain dye-providing compounds useful in photographic imaging systems.
    Type: Grant
    Filed: July 31, 1992
    Date of Patent: June 7, 1994
    Assignee: Polaroid Corporation
    Inventors: David Messersmith, David P. Waller
  • Patent number: 5306316
    Abstract: Poly(alkylene ether) amines having the formula: ##STR1## wherein A is an amine moiety having at least one basic nitrogen atom; R.sub.1 is a hydrocarbyl group having a sufficient number of carbon atoms to render the poly(vinyl ether) amine soluble in hydrocarbons boiling in the gasoline or diesel fuel range; R.sub.2 is an alkylene group having 2 to about 8 carbon atoms; R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are each independently hydrogen or a lower alkyl group having 1 to about 4 carbon atoms; R.sub.9 is an alkyl group having 1 to about 10 carbon atoms; m is 0 or 1; n is an integer from 5 to 99; and W is a hydroxy(oxypropylene) group having the formula: ##STR2## or mixtures thereof. The poly(vinyl ether) amines of formula I are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: April 1, 1993
    Date of Patent: April 26, 1994
    Assignee: Chevron Research and Technology Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5306315
    Abstract: Poly(alkylene ether) amines having the formula: ##STR1## wherein A is an amine moiety having at least one basic nitrogen atom; R.sub.1 is a hydrocarbyl group having a sufficient number of carbon atoms to render the poly(vinyl ether) amine soluble in hydrocarbons boiling in the gasoline or diesel fuel range; R.sub.2 is an alkylene group having 2 to about 8 carbon atoms; R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are each independently hydrogen or a lower alkyl group having 1 to about 4 carbon atoms; R.sub.9 is an alkyl group having 1 to about 10 carbon atoms; m is 0 or 1; and n is an integer from 5 to 99. The poly(vinyl ether) amines of formula I are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: April 1, 1993
    Date of Patent: April 26, 1994
    Assignee: Chevron Research and Technology Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5283367
    Abstract: N,N,N',N'-Tetrasubstituted 1,4-diamino-2-butenes where the substituents are alkyl, cycloalkyl, aralkyl, aryl or mixtures thereof provide effective antioxidant protection to lubricants and/or synthetic polymers.
    Type: Grant
    Filed: May 16, 1991
    Date of Patent: February 1, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Joseph E. Babiarz, Glen T. Cunkle, Werner Rutsch
  • Patent number: 5270471
    Abstract: A branched chain polyalkylene polyamine ("PAPA") having plural amine groups, including a secondary amine group intermediate terminal primary amine groups one of which is hindered, and having at least two carbon atoms between each group, is selectively reductively alkylated with a ketone. The reaction provides a convenient method for selectively reductively alkylating a PAPA having a hindered primary amine group, the method comprising contacting the PAPA with hydrogen and the ketone in the presence of a catalytically effective amount of a Group VIII metal on a catalyst support, at a pressure in the range from about 500-1000 psi and a temperature in the range from about 50.degree. C. to about 200.degree. C. for a period of time sufficient to preferentially alkylate the unhindered amine primary terminal amine group. The alkylation proceeds essentially without alkylating either the sterically hindered terminal primary amine group or the intermediate unhindered secondary amine group.
    Type: Grant
    Filed: October 27, 1992
    Date of Patent: December 14, 1993
    Assignee: The B. F. Goodrich Company
    Inventors: John T. Lai, Pyong-Nae Son
  • Patent number: 5268509
    Abstract: This invention relates to a process for the preparation of an iron catalyst used for the hydrogenation of organic compounds comprising partially oxidizing iron or an iron alloy in particulate form at an elevated temperature in the presence of gaseous oxygen until a weight gain of from 5% to 32% is obtained; and then reducing the partially oxidized iron or iron alloy at an elevated temperature in a stream of hydrogen.The invention also relates to a process for the preparation of primary amines comprising catalytically hydrogenating nitriles corresponding to said primary amines in the presence of an iron catalyst of the invention.
    Type: Grant
    Filed: June 11, 1990
    Date of Patent: December 7, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Dietrich Liebsch, Hans-H. Schwarz, Stephan Wendel, Peter Fischer
  • Patent number: 5243044
    Abstract: A blood substitute employs combinations of fluoro or perfluorochemicals capable in the presence of emulsifying agents of forming emulsions stable at room temperature and possessing enhanced oxygen carrying capacity; the invention enables preparation of an improved blood substitute, with improved O.sub.2 carrying capacity and stability, as well as lessened anaphylactoid reaction.
    Type: Grant
    Filed: February 17, 1989
    Date of Patent: September 7, 1993
    Assignee: International Therapeutics, Inc.
    Inventors: Walter B. Dandliker, W. Keith R. Watson, Thomas C. Drees
  • Patent number: 5239120
    Abstract: A process for the preparation of a 2-(3-aminopropyl)-cycloalkylamine of the general formula I ##STR1## in which the subscript n is an integer from 1 to 4, from a 2-(2-cyanoethyl)-cycloalkanone of the general formula II ##STR2## in which the subscript n has the meaning stated, wherein the following stages are carried out in discrete reaction chambers:a) the 2-(2-cyanoethyl)-cycloalkanone of formula II is reacted in a first reaction chamber with excess ammonia over an acidic heterogeneous catalyst at a temperature from 20.degree. to 150.degree. C. and a pressure of from 15 to 500 bar, andb) in a second reaction chamber, the reaction product from stage a) is hydrogenated at a temperature of from 60.degree. to 150.degree. C. and a pressure of from 50 to 300 bar in the presence of excess ammonia over a catalyst containing cobalt, nickel, ruthenium, and/or some other noble metal, which catalyst optionally contains a basic component or is supported on neutral or basic supporting material.
    Type: Grant
    Filed: March 27, 1991
    Date of Patent: August 24, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Claus-Ulrich Priester, Gerhard Koppenhoefer, Wolfgang Harder, Tom Witzel, Helmut Lermer, Ulrich Koehler
  • Patent number: 5232526
    Abstract: This invention is for new compounds, namely, diethanolammoniummethylcubane nitrates, a composition of diethanolammonium methylcubyl nitrates - hydroxylammonium nitrate (HAN) solutions and their method of use as aqueous liquid gun propellant ingredients.
    Type: Grant
    Filed: July 10, 1992
    Date of Patent: August 3, 1993
    Assignee: Thiokol Corporation
    Inventors: Rodney L. Willer, Alfred G. Stern
  • Patent number: 5225597
    Abstract: A continuous method of preparing N-monoalkyl alkylenediamines, uncontaminated by the N,N'-dialkyl alkylenediamine, is based on the observation that the disubstituted material selectively precipitates from aqueous media. A scheme is presented where an aqueous alkylenediamine is reacted with a suitable carbonyl component and hydrogen over a supported platinum catalyst. Where the alkylenediamine forms an azeotrope with water it can be conveniently recycled to the reactor.
    Type: Grant
    Filed: March 13, 1992
    Date of Patent: July 6, 1993
    Assignee: UOP
    Inventor: Paul R. Kurek
  • Patent number: 5214212
    Abstract: A process for increasing the rate of catalytic hydrogenation of aromatic amines by reacting aromatic amines with hydrogen in the presence of a noble metal catalyst, an organic solvent or a mixture of solvents, and at least one salt of a transition or lanthanide metal as a promoter, in an effective amount to increase the rate of the hydrogenation reaction, decrease the induction period, and decrease the amount of higher boiler by-products.
    Type: Grant
    Filed: February 27, 1992
    Date of Patent: May 25, 1993
    Assignee: Olin Corporation
    Inventor: Peter J. Whitman
  • Patent number: 5212173
    Abstract: Pharmacologically active compounds corresponding to the formula I ##STR1## in which n represents 2-5,m represents 2-6,R.sup.1 denotes hydrogen or lower alkyl,R.sup.2 represents an OR.sup.4 group in which R.sup.4 denotes lower alkyl or a phenyl or phenyl-lower alkyl group which is optionally substituted in the phenyl ring, orR.sup.2 represents a ##STR2## group in which R.sup.5 and R.sup.6 independently of one another each denote hydrogen, lower alkyl or a phenyl or phenyl-lower alkyl group which is optionally substituted in the phenyl ring, orR.sup.5 and R.sup.6, together with the nitrogen atom to which they are bonded, represent a saturated 5- or 6-membered heterocycle,R.sup.3 represents a saturated monocyclic or bicyclic hydrocarbon group which is derived from terpenes and has 10 or 11 carbon atoms, andZ represents oxygen or, if R.sup.3 is a dihydronopyl group, Z may also represent sulfur,and salts thereof.
    Type: Grant
    Filed: December 19, 1991
    Date of Patent: May 18, 1993
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Herman Kraehling, Samuel David, Insa Hell, Ulf Preuschoff, Ivan Ban, Marie-Odile Christen
  • Patent number: 5208379
    Abstract: Waste or scrap polyurethane may be conveniently and economically converted to useful active-hydrogen containing polyethers and polyamines by contacting the polyurethane with water, strong base, and an activating agent such as a quaternary ammonium compound containing at least 15 carbon atoms or an organic sulfonate containing at least 7 carbon atoms. The activating agent helps to accelerate the rate of base catalyzed hydrolysis.
    Type: Grant
    Filed: May 14, 1992
    Date of Patent: May 4, 1993
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Lau S. Yang, Diane A. Macarevich
  • Patent number: 5196583
    Abstract: The invention provides a novel class of propargyl compounds represented by the formula: ##STR1## wherein R is an C.sub.1 -C.sub.20 alkyl group, C.sub.1 -C.sub.20 alkylene group, C.sub.1 -C.sub.20 alkylene group interrupted by --NH-- group(s), C.sub.6 -C.sub.7 alicyclic group and an aromatic group; R.sub.1 comprises 1-100% --CH.sub.2 --C.tbd.CH group and 99-0% hydrogen atom and n is an integer of 1 to 4, and preparation thereof.These compounds are useful as coating material or sealer or rim-injection molding material.
    Type: Grant
    Filed: December 4, 1990
    Date of Patent: March 23, 1993
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Mitsuo Yamada, Kei Aoki
  • Patent number: 5192798
    Abstract: This invention relates to novel lipophilic polyamines of formula I, the method of using these compounds to treat hypercholesterolemia, and intermediates thereto.Z.sub.1 --(CH.sub.2).sub.n --Y.sub.1 --X.sub.1 --R.sub.
    Type: Grant
    Filed: August 16, 1990
    Date of Patent: March 9, 1993
    Assignee: The Upjohn Company
    Inventors: James W. Aiken, Charles H. Spilman, Edward W. Thomas
  • Patent number: 5189173
    Abstract: A branched chain polyalkylene polyamine ("PAPA") having plural amine groups, including a secondary amine group intermediate terminal primary amine groups one of which is hindered, and having at least two carbon atoms between each group, is selectively reductively alkylated with a ketone. The reaction provides a convenient method for selectively reductively alkylating a PAPA having a hindered primary amine group, the method comprising contacting the PAPA with hydrogen and the ketone in the presence of a catalytically effective amount of a Group VIII metal on a catalyst support, at a pressure in the range from about 500-1000 psi and a temperature in the range from about 50.degree. C. to about 200.degree. C. for a period of time sufficient to preferentially alkylate the unhindered amine primary terminal amine group. The alkylation proceeds essentially without alkylating either the sterically hindered terminal primary amine group or the intermediate unhindered secondary amine group.
    Type: Grant
    Filed: March 2, 1989
    Date of Patent: February 23, 1993
    Assignee: The BFGoodrich Company
    Inventors: John T. Lai, Pyong-nae Son
  • Patent number: 5152826
    Abstract: An herbicide compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are oxo;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.
    Type: Grant
    Filed: October 16, 1991
    Date of Patent: October 6, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: Christopher G. Knudsen
  • Patent number: 5145874
    Abstract: Provided are cyclic hydrocarbons of Formula I ##STR1## with an aminoalkyl sidechain that are useful for treating phospholipase A2 mediated conditions, diabetes, and obesity.
    Type: Grant
    Filed: February 25, 1991
    Date of Patent: September 8, 1992
    Assignee: The Upjohn Company
    Inventors: Roy A. Johnson, Gordon L. Bundy, Gilbert A. Youngdale, Douglas R. Morton, Donald P. Wallach, deceased, by Vera M. Wallach, legal representative
  • Patent number: 5131945
    Abstract: Compounds of formula I ##STR1## are useful as herbicides, effective against dicotyledonous weeds.
    Type: Grant
    Filed: July 13, 1990
    Date of Patent: July 21, 1992
    Assignee: Shell Research Limited
    Inventors: Hans-Joachim Bissinger, Ludwig Schoeder, Helmut Baltruschat, Manfred Garrecht, Erich Raddatz, Wolfgang Fruhstorfer
  • Patent number: 5128471
    Abstract: The present invention relates to a process for the production of primary amines containing aliphatically or cycloaliphatically bound amino groups, characterized in that the isocyanate groups of organic isocyanates containing aliphatically and/or cycloaliphatically bound isocyanate groups are formylated with formic acid in a first reaction step and the N-formyl groups are subsequently converted into amino groups.The present invention also relates to polyamine mixtures obtained by this process and containinga) about 40 to 90% by weight, based on the total weight of components a) and b), of N,N',N"-tris-(6-aminohexyl)-isocyanurate andb) about 10 to 60% by weight, based on the total weight of components a) and b), of higher homologs of this triamine containing more than one isocyanurate ring.Finally, the present invention relates to the use of these polyamine mixtures as hardeners for polymer precursors containing epoxide or isocyanate groups.
    Type: Grant
    Filed: April 10, 1990
    Date of Patent: July 7, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans J. Scholl
  • Patent number: 5126426
    Abstract: Herein disclosed are an .alpha.-(aminocyclohexyl)alkylamine represented by the following general formula (II): ##STR1## wherein R represents hydrogen atom or a lower alkyl group having 1 to 5 carbon atoms, provided that the amino group bonded to the cyclohexyl group may be in either of the 2-, 3- and 4-positions and a method for preparing it; an .alpha.-(isocyanatocyclohexyl)alkylisocyanate of Formula (II) wherein the amino groups are replaced with isocyanato groups and a method for preparing it; polyisocyanato-isocyanurate represented by the following general formula (IV): ##STR2## wherein R.sub.1, R.sub.2 and R.sub.
    Type: Grant
    Filed: April 19, 1990
    Date of Patent: June 30, 1992
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Ryuji Haseyama, Masatoshi Takagi, Kouzou Hayashi, Katsuyoshi Sasagawa, Kazuyuki Kuroda, Taisaku Kano, Kiyoshi Shikai
  • Patent number: 5117055
    Abstract: A perfluoroalkyl halogenide represented by the formula: ##STR1## wherein X stands for one element selected from the group consisting of iodine and bromine, R.sub.f for a perfluorohydrocarbon group, n for an integer in the range of 1 to 3, and m for an integer in the range of 1 to 3, provided that n and m satisfy the relationship, n.gtoreq.m, is produced by a method which consists essentially in subjecting a perfluorocarboxylic acid fluoride represented by the formula, ##STR2## wherein R.sub.f and n have the same meanings as defined above, to a thermal reaction with a lithium halogenide represented by XI, wherein X has the same meaning as defined above.
    Type: Grant
    Filed: February 22, 1990
    Date of Patent: May 26, 1992
    Assignees: Agency of Industrial Science and Technology, Ministry of International Trade & Industry
    Inventors: Takashi Abe, Eiji Hayashi, Haruhiko Fukaya
  • Patent number: 5101032
    Abstract: Cycloalkylidene dyes have the formula ##STR1## where m is 0 or 1,L is a chemical bond or C.sub.1 -C.sub.2 -alkylene, which may be substituted,R.sup.1 is hydrogen, C.sub.1 -C.sub.20 -alkyl, which may be phenyl-substituted, substituted or unsubstituted phenyl, naphthyl or C.sub.3 -C.sub.7 -cycloalkyl,Y is oxygen or two hydrogens,X.sup.1 is oxygen andX.sup.2 is C.sub.1 -C.sub.8 -alkanoyloxy, substituted or unsubstituted benzoyloxy, C.sub.1 -C.sub.6 -trialkylsilyloxy or a radical of the formula OR.sup.1 or NR.sup.2 R.sup.3, where R.sup.1 is as defined above and R.sup.2 and R.sup.3 are identical or different and each is independently of the other C.sub.1 -C.sub.20 -alkyl, which may be phenyl-substituted, substituted or unsubstituted phenyl, naphthyl, or C.sub.3 -C.sub.7 -cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom joining them are saturated heterocyclyl, or else one of R.sup.2 and R.sup.3 is hydrogen, or X.sup.1 and X.sup.
    Type: Grant
    Filed: October 22, 1990
    Date of Patent: March 31, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Dieter Martin, Bernhard Albert, Knut Kessel
  • Patent number: 5091583
    Abstract: The invention pertains to tertiary amines used as catalysts for the preparation of polyurethane foams prepared via the catalytic reaction of a polyisocyanate with a polyol in the presence of blowing agents, etc. The tertiary amine catalysts are prepared by reacting an olefinic nitrile with aliphatic polyol having at least secondary hydroxyl functionality in a ratio less than stoichiometric for providing cyanoalkylated polyol having residual hydroxyl functionality. The resulting cyanoalkylated polyol then is reacted with a secondary amine under conditions for effective reductive alkylation.The tertiary amine catalysts, because of residual secondary hydroxyl functionality, provide for uniform dispersion within a polyurethane, formulation; they provude for additional or extended pot life in polyurethane formulations at temperature below reaction condition, and they are bound by reaction on cure.
    Type: Grant
    Filed: May 9, 1991
    Date of Patent: February 25, 1992
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Jeremiah P. Casey, Richard V. C. Carr, George J. Wasilczyk, Robert G. Petrella
  • Patent number: 4990633
    Abstract: New fluorinated bisaryloxy-substituted alkenes are prepared by reaction of substituted phenols with perhaloalkenes and can be used as electrical insulating agents.
    Type: Grant
    Filed: May 4, 1989
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Negele, Dietmar Beilefeldt, Thomas Himmler, Albrecht Marhold
  • Patent number: 4933470
    Abstract: A method is described for producing vicinal diamines comprising the steps of converting a compound, possessing a leaving group on a carbon atom interposed between carbon atoms containing amino groups, to an aziridine-containing compound and reacting the latter compound with a nucleophile to form a vicinal diamine. The compound chosen for the rearrangement reaction may be selected from a wide range of compounds, including those with halide, heteroatom and aryl substituents. The amino groups may be blocked or unblocked. A variety of functional groups, including those which extend the carbon backbone, may be incorporated via opening of the aziridine-containing compound by addition of a selected nuclepohile. Aziridine-containing compositions and vicinal diamine compositions are disclosed. Functionalized vicinal diamines have numerous uses, including as intermediates for radionuclide-chelating ligands for use in the diagnosis and therapy of cancer.
    Type: Grant
    Filed: October 5, 1987
    Date of Patent: June 12, 1990
    Assignee: NeoRx Corporation
    Inventor: David S. Jones
  • Patent number: 4914241
    Abstract: Diamines of the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, alkyl, aryl, alkoxy, aralkyl or cycloalkyl and X is a group of the formula(CR.sup.4 R.sup.5).sub.m (II)where R.sup.4 and R.sup.5 have the meanings given above for R.sup.1 and m is from 1 to 12, are prepared by a process in which a diamine of the formula ##STR2## where R.sup.1, R.sup.2 and X are the groups described above, is reacted with an olefin of the formula ##STR3## where R.sup.6 and R.sup.9 are each hydrogen or alkyl which is straight-chain in the .alpha.-position, in the presence of a zeolite as a catalyst.
    Type: Grant
    Filed: June 15, 1988
    Date of Patent: April 3, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Hesse, Wolfgang Hoelderich, Matthias Schwarzmann
  • Patent number: 4885391
    Abstract: A process for the hydrogenation of C.sub.4 to C.sub.12 nitriles using a Raney cobalt catalyst promoted with chromium in which the catalyst activity is maintained by the addition of water. The process is particularly attractive to produce diamines by the hydrogenation of dinitriles.
    Type: Grant
    Filed: January 14, 1988
    Date of Patent: December 5, 1989
    Assignee: E. I. Du Pont De Nemours and Company
    Inventor: Frank E. Herkes
  • Patent number: 4879414
    Abstract: Polythiols prepared by the reaction of hydrogen sulfide or organic dithiols with polyglycidyl substituted amines have been found to be outstanding curing agents for epoxy resins. Epoxy resins cured with these polythiols are characterized by not only improved gel times, but also improved cure rates, better heat resistance and greater resistance to absorption of water.A useful polythiol is the reaction product of N,N,N',N'-tetraglycidyl-m-xylylenediamine with hydrogen sulfide.
    Type: Grant
    Filed: February 17, 1988
    Date of Patent: November 7, 1989
    Assignee: Henkel Corporation
    Inventors: Grannis S. Johnson, Reuben H. Grinstein, Stuart J. Hartman, Raymond P. Dallago
  • Patent number: 4879327
    Abstract: The invention relates to amine salts of phosphorous acid having a structure of the s-triazine, 1,2,4-triazole, benzimidazole, heptazine, pyrimidine, or piperazine type which may be combined with a polyhydroxylated compound as fireproofing agents for plastics, particularly polyamides and polyolefins, the process of fireproofing said plastics, and the resultant fireproofed plastics.
    Type: Grant
    Filed: March 31, 1988
    Date of Patent: November 7, 1989
    Assignee: Atochem
    Inventors: Pierre Poisson, Nadine Rivas, Pierre Deloy
  • Patent number: 4849544
    Abstract: Sterically hindered 1,3-diaminocyclohexanes which can be used in the preparation of polyurethane, polyurea, polyurethaneurea, and epoxy resins are prepared by hydrogenating a metaphenylenediamine having alkyl substituents of 1-6 carbons in the 4- and 6-positions and optionally also in the 2-position, at least one of the alkyl substituents containing at least two carbons, and the total number of carbons in the alkyl substituents being at least five, at a temperature of about 170.degree.-200.degree. C. and a pressure of at least about 6.9 MPa, preferably about 20-30 MPa, in the presence of a supported ruthenium catalyst and an activating amount of a modifier selected from alkali metal hydroxides and alkoxides and alkali metal amide salts of the meta-phenylenediamine to form the corresponding 1,3-diaminocyclohexane.
    Type: Grant
    Filed: April 13, 1988
    Date of Patent: July 18, 1989
    Assignee: Ethyl Corporation
    Inventors: Scott A. Culley, Kestutis A. Keblys, Christopher J. Nalepa
  • Patent number: 4835224
    Abstract: Polyamines are produced by hydrolyzing an isocyanate compound in the presence of at least one of a selected group of catalysts and a water miscible polar organic solvent in substantially homogeneous phase at 40.degree.-170.degree. C. The catalyst employed is selected from potassium hydroxide, rubidium hydroxide, cesium hydroxide, potassium alcoholates, rubidium alcoholates, cesium alcoholates, potassium carboxylates, rubidium carboxylates and cesium carboxylates. These polyamines are useful in the production of polyurethane(urea)s.
    Type: Grant
    Filed: March 24, 1988
    Date of Patent: May 30, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Andreas Ruckes, Werner Rasshofer, Klaus Konig, Richard Kopp
  • Patent number: 4806648
    Abstract: The one aspect of this invention relates to a process for making cis-vicinal tertiary diamines of general formula: ##STR1## wherein n is from 2-8, and NR.sub.21 is selected from a group including N-piperidino, N-pyrrolidino, dialkylamino containing C.sub.1 -C.sub.12 straight or branched alkyl groups optionally substituted by C.sub.3 -C.sub.7 cycloalkyl groups. The process comprises the formation of a cyclic aminoenamine and the stereospecific catalytic hydrogenation of cyclic aminoenamine to a cis diamine. Another aspect of this invention involves the uses of cis-vicinal tertiary diamines as catalysts of organolithium initiated anionic polymerization of 1,3-dienes, as anti-neoplastic agents and as bacteriacides.
    Type: Grant
    Filed: December 18, 1986
    Date of Patent: February 21, 1989
    Assignee: Ohio State University Research Foundation
    Inventors: Howard Rosenzweig, Gideon Fraenkel