Alicyclic Ring And Plural Amino Nitrogens Containing Patents (Class 564/461)
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Patent number: 6114392Abstract: 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: GrantFiled: April 16, 1996Date of Patent: September 5, 2000Inventors: Gad M. Gilad, Varda H. Gilad
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Patent number: 6100430Abstract: 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: GrantFiled: September 10, 1998Date of Patent: August 8, 2000Assignee: Daicel Chemical Industries, Ltd.Inventors: Kenichi Yamamoto, Kazuyuki Matsuoka, Hiroshi Yagihara
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Patent number: 6054065Abstract: 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: GrantFiled: July 19, 1999Date of Patent: April 25, 2000Inventors: Biing-Jiun Uang, Chyuan-Der Hwang
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Patent number: 5905170Abstract: 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: GrantFiled: March 11, 1998Date of Patent: May 18, 1999Assignee: Bayer AktiengesellschaftInventors: Konrad Fischer, Oswald Wilmes, Dieter Arlt, Carl Casser, Peter Maas, Pierre Woestenborghs, Theo Van der Knaap
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Patent number: 5902897Abstract: 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: GrantFiled: July 19, 1996Date of Patent: May 11, 1999Assignee: Bayer AktiengesellschaftInventors: Christian Wamprecht, Theodor Engbert, Holger Casselmann, Josef Pedain, Jurgen Meixner
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Patent number: 5773617Abstract: 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: GrantFiled: February 22, 1996Date of Patent: June 30, 1998Assignee: Rhone-Poulenc ChimieInventors: Jean-Marie Bernard, Errol Blart, Jean-Pierre Genet, Sandrine Lemaire-Audoire, Monique Savignac
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Patent number: 5760157Abstract: 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: GrantFiled: December 20, 1996Date of Patent: June 2, 1998Assignee: Elf Atochem, S.A.Inventors: Martine Cerf, Stephane Fouquay, Joel Perthuis
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Patent number: 5741928Abstract: 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: GrantFiled: September 19, 1995Date of Patent: April 21, 1998Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Shoichi Kobayashi, Susumu Naito
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Patent number: 5679860Abstract: 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: GrantFiled: October 28, 1996Date of Patent: October 21, 1997Assignee: Degussa AktiengesellschaftInventors: Thomas Haas, Roland Burmeister, Dietrich Arntz, Karl-Ludwig Weber, Monika Berweiler
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Patent number: 5679861Abstract: 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: GrantFiled: June 7, 1995Date of Patent: October 21, 1997Assignee: Industrial Technology Research InstituteInventors: Tung-Ying Kuo, Jih-Ru Hwu, Tsong-Ming Chang
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Patent number: 5627215Abstract: 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: GrantFiled: August 18, 1995Date of Patent: May 6, 1997Assignee: Ciba-Geigy CorporationInventors: Jorg Frei, Jaroslav Stanek
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Patent number: 5554656Abstract: 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: GrantFiled: February 25, 1994Date of Patent: September 10, 1996Assignee: Reckitt & Colman Inc.Inventors: Bernd L ower, Heinz Eggensperger, Peter Goroncy-Bermes, Michael Mohr, Andreas Dettmann
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Patent number: 5541321Abstract: A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: ##STR1##Type: GrantFiled: March 30, 1995Date of Patent: July 30, 1996Assignee: Abbott LaboratoriesInventors: William R. Baker, John K. Pratt, Daniel W. Norbeck, Chen Zhao
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Patent number: 5541320Abstract: A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: ##STR1##Type: GrantFiled: March 30, 1995Date of Patent: July 30, 1996Assignee: Abbot LaboratoriesInventors: William R. Baker, John K. Pratt, Daniel W. Norbeck, Chen Zhao
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Patent number: 5504254Abstract: 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: GrantFiled: December 22, 1994Date of Patent: April 2, 1996Assignee: Degussa AktiengesellschaftInventors: Thomas Haas, Dietrich Arntz, Dieter Most
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Patent number: 5436339Abstract: A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: ##STR1##Type: GrantFiled: July 14, 1992Date of Patent: July 25, 1995Assignee: Abbott LaboratoriesInventors: William R. Baker, John K. Pratt, Daniel W. Norbeck, Chen Zhao
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Methods for regenerating a sulfur scavenging compound from a product of a sulfur scavenging reaction
Patent number: 5347003Abstract: 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: GrantFiled: March 5, 1993Date of Patent: September 13, 1994Assignee: Quaker Chemical CorporationInventors: Edward A. Trauffer, Robert D. Evans -
Patent number: 5319143Abstract: 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: GrantFiled: July 31, 1992Date of Patent: June 7, 1994Assignee: Polaroid CorporationInventors: David Messersmith, David P. Waller
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Patent number: 5306316Abstract: 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: GrantFiled: April 1, 1993Date of Patent: April 26, 1994Assignee: Chevron Research and Technology CompanyInventor: Richard E. Cherpeck
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Patent number: 5306315Abstract: 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: GrantFiled: April 1, 1993Date of Patent: April 26, 1994Assignee: Chevron Research and Technology CompanyInventor: Richard E. Cherpeck
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Patent number: 5283367Abstract: 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: GrantFiled: May 16, 1991Date of Patent: February 1, 1994Assignee: Ciba-Geigy CorporationInventors: Joseph E. Babiarz, Glen T. Cunkle, Werner Rutsch
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Patent number: 5270471Abstract: 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: GrantFiled: October 27, 1992Date of Patent: December 14, 1993Assignee: The B. F. Goodrich CompanyInventors: John T. Lai, Pyong-Nae Son
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Patent number: 5268509Abstract: 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: GrantFiled: June 11, 1990Date of Patent: December 7, 1993Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Dietrich Liebsch, Hans-H. Schwarz, Stephan Wendel, Peter Fischer
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Patent number: 5243044Abstract: 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: GrantFiled: February 17, 1989Date of Patent: September 7, 1993Assignee: International Therapeutics, Inc.Inventors: Walter B. Dandliker, W. Keith R. Watson, Thomas C. Drees
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Patent number: 5239120Abstract: 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: GrantFiled: March 27, 1991Date of Patent: August 24, 1993Assignee: BASF AktiengesellschaftInventors: Franz Merger, Claus-Ulrich Priester, Gerhard Koppenhoefer, Wolfgang Harder, Tom Witzel, Helmut Lermer, Ulrich Koehler
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Patent number: 5232526Abstract: 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: GrantFiled: July 10, 1992Date of Patent: August 3, 1993Assignee: Thiokol CorporationInventors: Rodney L. Willer, Alfred G. Stern
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Patent number: 5225597Abstract: 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: GrantFiled: March 13, 1992Date of Patent: July 6, 1993Assignee: UOPInventor: Paul R. Kurek
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Patent number: 5214212Abstract: 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: GrantFiled: February 27, 1992Date of Patent: May 25, 1993Assignee: Olin CorporationInventor: Peter J. Whitman
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Patent number: 5212173Abstract: 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: GrantFiled: December 19, 1991Date of Patent: May 18, 1993Assignee: Kali-Chemie Pharma GmbHInventors: Herman Kraehling, Samuel David, Insa Hell, Ulf Preuschoff, Ivan Ban, Marie-Odile Christen
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Patent number: 5208379Abstract: 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: GrantFiled: May 14, 1992Date of Patent: May 4, 1993Assignee: Arco Chemical Technology, L.P.Inventors: Lau S. Yang, Diane A. Macarevich
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Patent number: 5196583Abstract: 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: GrantFiled: December 4, 1990Date of Patent: March 23, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Kei Aoki
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Patent number: 5192798Abstract: 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: GrantFiled: August 16, 1990Date of Patent: March 9, 1993Assignee: The Upjohn CompanyInventors: James W. Aiken, Charles H. Spilman, Edward W. Thomas
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Patent number: 5189173Abstract: 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: GrantFiled: March 2, 1989Date of Patent: February 23, 1993Assignee: The BFGoodrich CompanyInventors: John T. Lai, Pyong-nae Son
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Patent number: 5152826Abstract: 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: GrantFiled: October 16, 1991Date of Patent: October 6, 1992Assignee: Imperial Chemical Industries PLCInventor: Christopher G. Knudsen
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Patent number: 5145874Abstract: 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: GrantFiled: February 25, 1991Date of Patent: September 8, 1992Assignee: The Upjohn CompanyInventors: Roy A. Johnson, Gordon L. Bundy, Gilbert A. Youngdale, Douglas R. Morton, Donald P. Wallach, deceased, by Vera M. Wallach, legal representative
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Patent number: 5131945Abstract: Compounds of formula I ##STR1## are useful as herbicides, effective against dicotyledonous weeds.Type: GrantFiled: July 13, 1990Date of Patent: July 21, 1992Assignee: Shell Research LimitedInventors: Hans-Joachim Bissinger, Ludwig Schoeder, Helmut Baltruschat, Manfred Garrecht, Erich Raddatz, Wolfgang Fruhstorfer
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Patent number: 5128471Abstract: 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: GrantFiled: April 10, 1990Date of Patent: July 7, 1992Assignee: Bayer AktiengesellschaftInventor: Hans J. Scholl
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Patent number: 5126426Abstract: 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: GrantFiled: April 19, 1990Date of Patent: June 30, 1992Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Ryuji Haseyama, Masatoshi Takagi, Kouzou Hayashi, Katsuyoshi Sasagawa, Kazuyuki Kuroda, Taisaku Kano, Kiyoshi Shikai
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Patent number: 5117055Abstract: 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: GrantFiled: February 22, 1990Date of Patent: May 26, 1992Assignees: Agency of Industrial Science and Technology, Ministry of International Trade & IndustryInventors: Takashi Abe, Eiji Hayashi, Haruhiko Fukaya
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Patent number: 5101032Abstract: 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: GrantFiled: October 22, 1990Date of Patent: March 31, 1992Assignee: BASF AktiengesellschaftInventors: Hans-Dieter Martin, Bernhard Albert, Knut Kessel
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Patent number: 5091583Abstract: 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: GrantFiled: May 9, 1991Date of Patent: February 25, 1992Assignee: Air Products and Chemicals, Inc.Inventors: Jeremiah P. Casey, Richard V. C. Carr, George J. Wasilczyk, Robert G. Petrella
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Patent number: 4990633Abstract: New fluorinated bisaryloxy-substituted alkenes are prepared by reaction of substituted phenols with perhaloalkenes and can be used as electrical insulating agents.Type: GrantFiled: May 4, 1989Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Michael Negele, Dietmar Beilefeldt, Thomas Himmler, Albrecht Marhold
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Patent number: 4933470Abstract: 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: GrantFiled: October 5, 1987Date of Patent: June 12, 1990Assignee: NeoRx CorporationInventor: David S. Jones
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Patent number: 4914241Abstract: 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: GrantFiled: June 15, 1988Date of Patent: April 3, 1990Assignee: BASF AktiengesellschaftInventors: Michael Hesse, Wolfgang Hoelderich, Matthias Schwarzmann
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Patent number: 4885391Abstract: 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: GrantFiled: January 14, 1988Date of Patent: December 5, 1989Assignee: E. I. Du Pont De Nemours and CompanyInventor: Frank E. Herkes
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Patent number: 4879414Abstract: 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: GrantFiled: February 17, 1988Date of Patent: November 7, 1989Assignee: Henkel CorporationInventors: Grannis S. Johnson, Reuben H. Grinstein, Stuart J. Hartman, Raymond P. Dallago
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Patent number: 4879327Abstract: 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: GrantFiled: March 31, 1988Date of Patent: November 7, 1989Assignee: AtochemInventors: Pierre Poisson, Nadine Rivas, Pierre Deloy
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Patent number: 4849544Abstract: 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: GrantFiled: April 13, 1988Date of Patent: July 18, 1989Assignee: Ethyl CorporationInventors: Scott A. Culley, Kestutis A. Keblys, Christopher J. Nalepa
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Patent number: 4835224Abstract: 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: GrantFiled: March 24, 1988Date of Patent: May 30, 1989Assignee: Bayer AktiengesellschaftInventors: Andreas Ruckes, Werner Rasshofer, Klaus Konig, Richard Kopp
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Patent number: 4806648Abstract: 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: GrantFiled: December 18, 1986Date of Patent: February 21, 1989Assignee: Ohio State University Research FoundationInventors: Howard Rosenzweig, Gideon Fraenkel