Plural Amino Nitrogens Containing Patents (Class 564/511)
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Patent number: 5214215Abstract: This invention relates to a process for making amines having a high yield weight percent of aminoethylethanolamine (AEEA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in AEEA.Type: GrantFiled: March 30, 1990Date of Patent: May 25, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumaux, Jr.
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Patent number: 5210307Abstract: A process for reforming alkyleneamines to predominantly linearly-extended polyalkylenepolyamines comprising contacting an alkyleneamine or mixture thereof with a catalyst under conditions such that a mixture of polyalkylenepolyamines enriched in linearly-extended products is formed, said catalyst containing at least one compound selected from the group consisting of (a) Group VB metal oxides, (b) Group VB metal phosphates, (c) silicates of Groups IIA, IIIB, IVB, VB, and the lanthanide and actinide metals, and (d) tungsten oxides, with the proviso that the silicates and tungsten oxides are essentially free of aluminum. For example, ethylenediamine is contacted with a catalyst of niobium phosphate or niobic acid under reaction conditions to yield predominantly non-cyclic polyethylenepolyamines.Type: GrantFiled: January 31, 1992Date of Patent: May 11, 1993Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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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: 5202490Abstract: A continuously generated alkyleneamines producers composition comprising based on 100% of the moles of the compostion and exclusive of any MEA and water present,a) about 15 to about 35 mole % DETA,b) about 15 to about 55 mole % EDA (net generated),c) about 10 to about 35 mole % AEEA,d) about 3 to about 25 mole % of the combination of PIP, AEP and HEP,e) about 3 to about 10 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polyamines, andg) a DETA to AEEA mole ratio greater than about 0.77 to less than 1.35,and the process of producing the same, which comprises feeding hydrogen, ammonia, MEA and EDA, preferably provided from a recycle stream, to a reaction zone containing a fixed bed of a reductive amination catalyst in a tubular reactor, wherein the hydrogen comprises about 10 to about 50 mole percent of the feed in the reaction zone, the mole ratio of EDA to MEA is less than about 0.Type: GrantFiled: May 25, 1990Date of Patent: April 13, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
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Patent number: 5202491Abstract: A continuously generated alkyleneamines producers composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,a) about 20 to about 40 mole % DETA,b) about 15 to about 60 mole % EDA (net generated),c) about 5 to about 18 mole % AEEA,d) about 3 to about 25 mole % of the combination of PIP, AEP and HEP,e) less than about 1 to about 5 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polyamines,g) a DETA to AEEA mole ratio greater than about 1.35, andh) an EDA to DETA mole ratio less than 2.60,and the process of manufacturing it which comprises feeding hydrogen, ammonia, MEA and EDA, preferably provided from a recycle stream, to a reaction zone containing a fixed bed of a reductive amination catalyst in a tubular reactor, wherein the hydrogen comprises about 1 to about 30 mole percent of the feed in the reaction zone, the mole ratio of EDA to MEA is greater than 0.Type: GrantFiled: May 25, 1990Date of Patent: April 13, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
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Patent number: 5196589Abstract: The present invention relates to novel methods of stabilizing polymers of acrylonitrile. The polymers are stabilized by the inclusion of small amounts of stable free radicals compounds which act to inhibit the homopolymerization of the acrylonitrile while promoting the reaction of the acrylonitrile with nucleophilic species such as amines and alcohols.Type: GrantFiled: September 16, 1991Date of Patent: March 23, 1993Assignee: LCE PartnershipInventors: Anthony J. O'Lenick, Jr., J. Michael Clumpner
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Patent number: 5196588Abstract: A continuously generated alkyleneamines producers composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,a) about 14 to about 20 mole % DETA,b) about 45 to about 75 mole % EDA (net generated),c) about 4 to about 10 mole % AEEA,d) about 3 to about 25 mole % of the combination of PIP, AEP and HEP,e) about 0.5 to about 5 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polymines,g) an EDA to DETA mole ratio greater than about 2.60,h) a DETA to AEEA mole ratio greater than about 1.35, andi) an EDA to AEEA mole ratio greater than about 8,and a process of manufacturing it which comprises feeding hydrogen, ammonia, MEA and EDA, preferably provided from a recycle stream, to a reaction zone containing a fixed bed of a reductive amination catalyst in a tubular reactor, wherein the hydrogen comprises about 1 to about 30 mole percent of the feed in the reaction zone, the mole ratio of EDA to MEA is less than about 0.Type: GrantFiled: May 25, 1990Date of Patent: March 23, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
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Patent number: 5177102Abstract: There are given disclosures on a polyisoprene compound of the formula ##STR1## wherein Y is S, O, NH or ##STR2## .sub.l is an integer of 2-10, Z is a group of ##STR3## R.sup.1 and R.sup.2 are same or different and each means a hydrogen atom or an alkyl group having C.sub.1-4, m is an integer of 0 or 1, and .sub.n is an integer of 0, 1 or 2,a salt thereof, a process for the preparation of same, and use thereof.Type: GrantFiled: May 3, 1991Date of Patent: January 5, 1993Assignee: Sanwa Kagaku Kenkyusho Co., Ltd.Inventors: Masayasu Kurono, Yasuaki Kondo, Takuji Yamaguchi, Ryoichi Unno, Hiromoto Kimura, Noboru Kuboyama, Takashi Ito, Mitsuru Oka, Akira Tashita, Kazumasa Nakano, Kiichi Sawai
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Patent number: 5166415Abstract: This invention relates to a process for making amines having a high yield weight percent of diethylenetriamine (DETA) and aminoethylethanolamine (AEEA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in DETA and AEEA.Type: GrantFiled: March 30, 1990Date of Patent: November 24, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., Stephen W. King, Lloyd M. Burgess
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Patent number: 5166442Abstract: A process of reforming an alkyleneamine feedstock or a mixture of such feedstocks to an alkyleneamine or a mixture of alkyleneamines which is different from the feedstock or feedstock mixture. The process is catalyzed by one of the following: Group VB metal oxides, Group VB metal phosphates, Group IIA metal silicates, and tungsten oxides. For example, ethylenediamine is contacted with a catalyst of niobic acid or magnesium silicate to yield predominantly diethylenetriamine and non-cyclic triethylenetetramines; whereas high molecular weight polyethylenepolyamines are cracked by the same catalysts to mixtures of lower molecular weight linear and cyclic materials.Type: GrantFiled: July 16, 1991Date of Patent: November 24, 1992Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
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Patent number: 5162373Abstract: Disclosed are total parenteral nutrition formulations which include essential amino acids in combination with either arginine or ornithine, for use in detection of recurrent malignant disease in patients. Such formulations stimulate tumor-specific polyamine production to a greater extent than non-tumor related polyamine production. Additionally, such formulations were found to specifically promote an increase in red block cell putrescine levels of tumor-bearing rats. Nontumor-bearing rats were not found to be similarly reactive to these formulations. Methods for making and administering these formulations as well as their use in preventing DFMO-induced toxicity are also disclosed.The present invention also comprises formulations for use in the rejuvinati oBACKGROUND OF THE INVENTIONThe government may own certain rights in the present invention pursuant to NCI grant RDI CA3 4-465 and NCI grant ROI CA3 4-465.Type: GrantFiled: August 28, 1989Date of Patent: November 10, 1992Assignee: Board of Regents, The University of Texas SystemInventors: Jaffer Ajani, Bruce Grossie, Jr., Kenji Nishioka, David M. Ota
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Patent number: 5158974Abstract: A process is described for the preparation of an N-alkyl- or N,N-dialkyl-1,2-diaminoethane of the general formula I ##STR1## where R.sup.1 is hydrogen or methyl, R.sup.2 is C.sub.1 - to C.sub.5 -alkyl, and R.sup.3 is hydrogen or C.sub.1 - to C.sub.5 -alkyl, with the proviso that the total number of carbon atoms in R.sup.2 and R.sup.3 is an integer from 1 to 6, by reacting an imine of the general formula II ##STR2## with an amine of the general formula III ##STR3## where R.sup.1, R.sup.2 and R.sup.3 are as defined above, which comprises carrying out the reaction in the presence of carbon dioxide at from 10.degree. to 150.degree. C. and at from 0.5 to 50 bar.Type: GrantFiled: October 15, 1990Date of Patent: October 27, 1992Assignee: BASF AktiengesellschaftInventors: Andreas Hohmann, Wolfgang Reuther, Werner Bochnitschek
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Patent number: 5141676Abstract: Organic-solvent soluble magnesium hydrides of the formulas(MgH.sub.2).sub.n. MgQ.sub.2 (II)(MgH.sub.2).sub.n. RMgX (III) ##STR1## are prepared by catalytically hydrogenating finely powdered magnesium, optionally in the presence of a magnesium halide, in an organic solvent in the presence of their MgH.sub.2 -free counterparts in whichQ is an alkyl, alkenyl, alkoxy, dialkylamino, aralkyl, aryl or diarylamino group, each with up to 18 carbon atoms,R is an alkenyl, aralkyl or aryl group, each with up to 18 carbon atoms,X is chlorine, bromine, or iodine,--E D.fwdarw. is a chelating ligand,E is --CH.sub.2, --N(R)-- or --O--,is an alkylene radical of the formula --(CH.sub.2).sub.p,D is a dialkylamino, diarylamino or alkoxy group, each with up to 19 carbon atoms,M is aluminum or boron,m is 1, 2, or 3, and1<n.ltoreq.50.Type: GrantFiled: April 17, 1991Date of Patent: August 25, 1992Assignee: Studiengesellschaft Kohle mbHInventors: Borislav Bogdanovic, Manfred Schwickardi
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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: 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: 5105013Abstract: A process for the preparation of permethylated amines, particularly pentamethyldiethylenetriamine, by the reductive methylation of diethylenetriamine in the presence of hydrogen, a nickel-containing catalyst, aqueous formaldehyde and methanol, comprising feeding continuously the formalehyde to the reaction system in two phases. In the first phase, a sufficient amount of formaldehyde to mono-methylate the primary amine groups present, is fed to the reaction system at a high flow rate, and thereafter the flow rate of the formaldehyde is substantially reduced, for the reductive methylation of the secondary amine groups. By this method the production of by-products is substantially reduced and preparation times are significantly shorter in comparison to processes where the formaldehyde flow rate remains constantly high for the entirety of the reaction.Type: GrantFiled: December 19, 1988Date of Patent: April 14, 1992Assignee: The Dow Chemical CompanyInventors: Maarten Tanis, Govind Rauniyar
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Patent number: 5091536Abstract: Organic-solvent soluble magnesium hydrides of the formulas ##STR1## are prepared by catalytically hydrogenating finely powdered magnesium, optionally in the presence of a magnesium halide, in an organic solvent in the presence of their MgH.sub.2 -free counterparts in whichQ is an alkyl, alkenyl, alkoxy, dialkylamide, aralkyl, aryl or diarylamide group, each with up to 18 carbon atoms,R is an alkenyl, aralkyl or aryl group, each with up to 18 carbon atoms,X is chlorine, bromine, or iodine,--E D.fwdarw. is a chelating ligand,E is --CH.sub.2, --N(R)-- or --O--,is an alkylene radical of the formula --(CH.sub.2).sub.p,D is a dialkylamide, diarylamide or alkoxy group, each with up to 18 carbon atoms,M is aluminum or boron,m is 1, 2, or 3, and1<n.ltoreq.50.Type: GrantFiled: February 9, 1988Date of Patent: February 25, 1992Assignee: Studiengesellschaft Kohle mbhInventors: Borislav Bogdanovic, Manfred Schwickardi
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Patent number: 5089619Abstract: Certain dithiocarbamates are used as reverse demulsifiers, corrosion and scale inhibitors, flocculants, biocides, flotation aids, water clarifiers, interface control agents and antifoaming agents.Type: GrantFiled: June 30, 1989Date of Patent: February 18, 1992Assignee: Petrolite CorporationInventors: Neil E. S. Thompson, Robert G. Asperger
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Patent number: 5068329Abstract: A continuously generated alkyleneamines produces composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,a) about 50 to about 90 mole % AEEA,b) less than about 3 mole % EDA but more than 0.01 mole % EDA,c) less than about 2 mole % DETA but more than 0.01 mole % DETA,d) about 5 to about 18 mole % of the combination of PIP, AEP and HEP,e) about 5 to about 20 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polyamines,g) a mole ratio of AEEA to the combination of PIP, AEP, HEP, DETA and EDA is greater than about 2.Type: GrantFiled: September 4, 1990Date of Patent: November 26, 1991Assignee: Union Carbide Chemicals and Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson
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Patent number: 5068330Abstract: A continuously generated alkyleneamines producers composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,a) about 15 to about 50 mole % AEEA,b) about 15 to about 55 mole % EDA,c) about 10 to about 20 mole % DETA,d) about 5 to about 20 mole % of the combination of PIP,AEP and HEP,3) about 3 to about 10 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polyamines,g) an DETA to AEEA mole ratio less than 0.77, andh) an EDA to AEEA mole ratio less than 8;and a process of manufacturing the same, which comprises feeding hydrogen, ammonia and MEA to a reaction zone containing a fixed bed of a reductive amination catalyst, wherein the hydrogen comprises about 20 to about 60 mole percent of the feed in the reaction zone and the mole ratio of ammonia to MEA is about 1 to about 5, the temperature of the reaction zone is about 120.degree. C. to about 300.degree. C.Type: GrantFiled: September 4, 1990Date of Patent: November 26, 1991Assignee: Union Carbide Chemicals and Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson
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Patent number: 5030763Abstract: A method of making ethylenediamine dinitrate comprising:(a) reacting ethylenediamine with aqueous nitric acid to form ethylenediamine dinitrate solution; and(b) adding said ethylenediamine dinitrate solution to a non-aqueous liquid, miscible with water in amounts of at least about 50 percent by weight, and in which ethylenediamine dinitrate is insoluble, to form solid ethylenediamine dinitrate with an average particle size of about 30 microns in diameter.Type: GrantFiled: February 13, 1990Date of Patent: July 9, 1991Assignee: Aerojet-General CorporationInventors: Robert E. Olsen, George D. Homer, James C. Barnard
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Patent number: 4996363Abstract: A process for reforming alkyleneamines to predominantly linearly-extended polyalkylenepolyamines comprising contacting an alkyleneamine or mixture thereof with a catalyst under conditions such that a mixture of polyalkylenepolyamines enriched in linearly-extended products is formed, said catalyst containing at least one compound selected from the group consisting of (a) Group VB metal oxides, (b) Group VB metal phosphates, (c) silicates of Groups IIA, IIIB, IVB, VB, and the lanthanide and actinide metals, and (d) tungsten oxides, with the proviso that the silicates and tungsten oxides are essentially free of aluminum. For example, ethylenediamine is contacted with a catalyst of niobium phosphate or niobic acid under reaction conditions to yield predominantly non-cyclic polyethylenepolyamines.Type: GrantFiled: December 20, 1988Date of Patent: February 26, 1991Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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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: 4983736Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a metallic polyphosphate condensation catalyst having a condensed structure. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentatethylenehexamine (PEHA).Type: GrantFiled: August 8, 1989Date of Patent: January 8, 1991Assignee: Union Carbide Chemicals and Plastic Company Inc.Inventors: Arthur R. Doumaux, Jr., David J. Schreck
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Patent number: 4967008Abstract: The present invention is directed to polyamines represented by the following general structure: ##STR1## where R is an organic group, R' is H or CH.sub.3, andx=0-3Tri, tetra, penta, and hexa amines, accordingly, are disclosed.The method for making the novel polyamines comprises a multi-step reaction that commences in step (a) with the cyanoethylation of a primary amine, R--NH.sub.2, with acrylonitrile under cyanoethylation conditions to form an aminonitrile of the structure R--NH--CH.sub.2 --CH.sub.2 --CN. The aminonitrile in step (b) is methylated by reaction with formic acid and formaldehyde under Leuckart reaction conditions to form a monomethyl aminonitrile of the structure R--N(CH.sub.3)--CH.sub.2 --CH.sub.2 --CN. The monomethyl aminonitrile then in step (c) is reduced, preferably by hydrogenation under hydrogenation conditions, to form a monomethyl diamine of the structure R--N(CH.sub.3)--CH.sub.2 --CH.sub.2 --CH.sub.2 --NH.sub.2.Type: GrantFiled: January 12, 1990Date of Patent: October 30, 1990Assignee: Sherex Chemical Company, Inc.Inventors: Floyd E. Friedli, Robert M. Gilbert
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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: 4931595Abstract: Polyamines containing primary amino groups are prepared in a single stage process by hydrolyzing an isocyanate in the presence of a catalyst incorporable through an NCO reactive group and a water-miscible aprotic-dipolar solvent. This hydrolysis is carried out at from 20.degree. to 210.degree. C. with the reactants being in substantially homogeneous phase. The isocyanate starting material has an NCO content of from 0.5 to 40% by weight. The catalyst is used in a quantity of at least 0.0001% by weight, based on 100% by weight of isocyanate compound. The water-miscible solvent is used in a quantity of at least 10% by weight, based on 100% by weight of isocyanate compound. The polyamines thus produced are particularly useful in the production of polyurethanes.Type: GrantFiled: August 2, 1989Date of Patent: June 5, 1990Assignee: Bayer AktiengesellschaftInventor: Werner Rasshofer
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Patent number: 4918190Abstract: Disclosed are a crystalline complex compound of a propargyl alcohol represented by Formula (I): ##STR1## wherein each of R.sub.1 and R.sub.2 represents a substituent which is different from each otherand a tertiary diamine represented by Formula (II): ##STR2## wherein A represents a group having two carbon atoms as a chain member which may be branched; each of R.sub.3, R.sub.4, R.sub.5 and R.sub.6 may be the same or different and represents an aralkyl group or an alkyl group having 1 to 6 carbon atoms; and A, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 may be bonded to each other,and a process of separation and purification of the propargyl alcohol using the crystalline complex compound described above.Type: GrantFiled: July 30, 1987Date of Patent: April 17, 1990Assignee: Ube Industries, Ltd.Inventors: Fumio Toda, Koichi Tanaka, Kikuo Ataka
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Patent number: 4918233Abstract: This invention relates to a process for producing ethylene diamine in high selectivity and high conversion by reacting monoethanolamine with ammonia in the presence of a catalyst. The catalyst which permits the production of ethylenediamine in high selectivity and high conversion is a hydrogen mordenite catalyst that has been treated in such a manner as to raise the silicon to aluminum ratio of the mordenite, such treatment, then being referred to as partial dealumination.Type: GrantFiled: July 8, 1986Date of Patent: April 17, 1990Assignee: Air Products and Chemicals, Inc.Inventors: Michel Deeba, Michael E. Ford, Thomas A. Johnson
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Patent number: 4900458Abstract: A corrosion inhibiting polyalkylenepolyamine composition comprising a mixture of(a) at least one C-alkyl-ethylene diamine, and(b) at least one di-(C-alkyl)-diethylenetriamine or at least one di-(C-alkyl)-piperazine or a mixture thereof;wherein each C-alkyl group on the ethylene diamine, diethylenetriamine and piperazine independently contains from 10 to 28 carbon atoms. Methods for preparing this composition are also disclosed, as well as methods for its use in inhibiting corrosion of corrodible metals.Type: GrantFiled: January 11, 1988Date of Patent: February 13, 1990Assignee: Chevron Research CompanyInventors: Albert H. Schroeder, Ta Y. Ching, Shigeto Suzuki, Kiyoshi Katsumoto
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Patent number: 4886915Abstract: Water soluble biocidal water treatment perhalides of the formula: ##STR1## where R.sub.1 and R.sub.2 are independently hydrogen, hydroxyethyl, alkyl, cyclic alkyl, (alpha, omega)-alkyl, alkyl ether, polyether, heterocyclic ring-substituted alkyl, and halogenated alkyl; X is chlorine, bromine or iodine; and only one of R.sub.1 and R.sub.2 may be hydrogen.Type: GrantFiled: June 24, 1988Date of Patent: December 12, 1989Assignee: Great Lakes Chemical CorporationInventor: Nicolai A. Favstritsky
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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: 4874600Abstract: The invention relates to a new radiolabeled imaging agent, no-carrier-added [1-.sup.11 C]putrescine, and to the use of this very pure material as a radiotracer with positron emission tomography for imaging brain tumors. The invention further relates to the synthesis of no-carrier-added [1-.sup.11 C]putrescine based on the Michael addition of potassium .sup.11 C-labeled cyanide to acrylonitrile followed by reduction of the .sup.11 C-labeled dinitrile. The new method is rapid and efficient and provides radiotracer with a specific activity greater than 1.4 curies per millimol and in a purity greater than 95%.Type: GrantFiled: April 17, 1986Date of Patent: October 17, 1989Assignee: The United States of America as Represented by the United States Department of EnergyInventors: Daniel W. McPherson, Joanna S. Fowler, Alfred P. Wolf
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Patent number: 4871844Abstract: Novel diazepinium compounds having the structural formula: ##STR1## wherein R.sup.2 and R.sup.4 are individually alkyl of 3 to 7 carbon atoms R.sup.5, R.sup.6 and R.sup.7 are individually H or alkyl; and X.crclbar. is an anion. The compounds are of the class of amidiniums, useful as dyes. The compounds are particularly useful in antireflective layers having unexpected thermal resistance for use in photoresist applications.Type: GrantFiled: April 28, 1987Date of Patent: October 3, 1989Assignee: Eastman Kodak CompanyInventors: Thap DoMinh, Donald R. Diehl
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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: 4822483Abstract: A collector composition for use in froth flotation processes comprises two collectors. One of the collectors is preferably an N-(hydrocarbyl)-alpha, omega-alkanediamine, an (omega-aminoalkyl) hydrocarbon amide or mixture thereof. The second collector is a thiocarbonate, a thionocarbamate, a thiophosphate, thiocarbinilide, thiophosphinate, mercaptan, xanthogen formate, xanthic ester or mixture thereof. The collector composition floats a broad range of metal-containing minerals.Type: GrantFiled: March 23, 1987Date of Patent: April 18, 1989Assignee: The Dow Chemical CompanyInventors: Richard R. Klimpel, Robert D. Hansen
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Patent number: 4749792Abstract: Analgesic activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein R.sub.1, R.sub.2 and R.sub.4 are each independently hydrogen, alkyl, carboxyalkyl, halosubstituted alkyl, hydroxyalkyl, aminoalkyl, mercaptoalkyl, alkylthioalkyl, (cycloalkyl)alkyl, (heteroaryl)alkyl, arylalkyl, carbamoylalkyl, guanidinylalkyl, or heteroaryl, and R.sub.3 is hydroxymethylene or carbonyl.Type: GrantFiled: September 26, 1984Date of Patent: June 7, 1988Assignee: E. R. Squibb & Sons, Inc.Inventors: Sesha I. Natarajan, Eric M. Gordon
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Patent number: 4745207Abstract: Reaction products of hydrogen cyanide are prepared by a process in which hydrogen cyanide prepared in a conventional manner by pyrolysis at from 250.degree. to 650.degree. C. over a solid under from 5 to 200 mbar is cooled to a temperature of from 200.degree. to -10.degree. C. together with the other pyrolysis products, the hydrogen cyanide is then fed to a chemisorption reaction with a base or with a carbonyl compound, and the reaction products of hydrogen cyanide which are formed therein are removed from the system and brought to atmospheric pressure. In this process, the handling of large amounts of hydrogen cyanide is avoided.Type: GrantFiled: November 25, 1985Date of Patent: May 17, 1988Assignee: BASF AktiengesellschaftInventors: Fritz Brunnmueller, Karlheinz Stecher, Michael Kroener, Rolf Schneider
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Patent number: 4718918Abstract: Polymeric compounds (A) obtained by the reaction of epihalo-hydrin with a polyalkylene polyamine are useful as textile treatment agents. As pretreatment agents they improve the color yield of the subsequent dyeing, as aftertreatment agents they improve fastness properties. Certain of the products (A) are novel.Type: GrantFiled: June 16, 1986Date of Patent: January 12, 1988Assignee: Sandoz Ltd.Inventors: Jurg Heller, Bruno Kissling, Tibor Robinson, Salvatore Valenti
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Patent number: 4663331Abstract: This invention relates to Mannich-alkynyl aminothiadiazole oxides having histamine H.sub.2 -antagonist activity. A particular compound of this invention is 3-amino-4-[7-piperidinohept-5-ynylamino]-1,2,5-thiadiazole-1-oxide.Type: GrantFiled: January 16, 1986Date of Patent: May 5, 1987Assignee: SmithKline & French Laboratories LimitedInventors: Thomas H. Brown, Peter Blurton
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Patent number: 4658066Abstract: Novel diamines of the formula ##STR1## are described, in which R.sub.1 is C.sub.1-12 -alkyl, R.sub.2 is H or C.sub.1-12 -alkyl, R.sub.3 is C.sub.1-12 -alkyl, cycloalkyl having 4-12 ring C atoms, C.sub.7-8 -aralkyl, substituted or unsubstituted aryl or, if R.sub.4 =H, is also --CH.dbd.CH--alkyl or --C(alkyl).dbd.CH-- alkyl each having 1-4 C atoms in the alkyl groups, and R.sub.4 is H, C.sub.1-12 -alkyl, cycloalkyl having 4-12 ring C atoms, C.sub.7-8 -aralkyl or substituted or unsubstituted aryl, or R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 together are C.sub.3-11 -alkylene. The diamines (I) are valuable intermediates and are suitable especially for the preparation of transparent crosslinkable polyamides.Type: GrantFiled: August 7, 1985Date of Patent: April 14, 1987Assignee: Ciba-Geigy CorporationInventors: Dieter Reinehr, Josef Pfeifer
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Patent number: 4654443Abstract: Liquid distillation residue formed in the phosgenation of polyamines to form polyisocyanates are hydrolyzed to reform the polyamine. The process comprises forming an adduct of the distillation residue with additional polyamine and then hydrolyzing the resulting adduct to convert the adduct to said polyamine.Type: GrantFiled: March 11, 1985Date of Patent: March 31, 1987Assignee: The Dow Chemical CompanyInventors: Maurice J. Marks, James R. Porter, Raymond A. Plepys
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Patent number: 4650906Abstract: Ethyleneamines are recovered from an aqueous solution of carbonates of ethyleneamines by distilling an aqueous solution of carbonates of ethyleneamines including ethylenediamine, in which the molar ratio of the carbon dioxide component to the ethyleneamines including ethylenediamine is 0.01 to 0.5, whereby ethylenediamine is distilled out together with water. The aqueous solution to be distilled is advantageously prepared by heating an aqueous solution of carbonates of ethyleneamines including ethylenediamine to effect decarboxylation.Type: GrantFiled: February 29, 1984Date of Patent: March 17, 1987Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Tsugio Murakami, Taizo Kawamoto
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Patent number: 4645837Abstract: In the transalkylation of tertiary amines, unexpected higher yields are achieved requiring substantially less catalyst and much shorter reaction times at lower reaction temperatures using a homogeneous catalyst in the presence of an alcohol solvent and carbon monoxide. The process may be exemplified by reacting triethylamine and tripropylamine in the presence of a homogeneous triosmiumdodecacarbonyl catalyst, ethanol, and carbon monoxide to prepare diethylpropylamine and ethyldipropylamine.Type: GrantFiled: November 5, 1984Date of Patent: February 24, 1987Assignee: SRI InternationalInventors: Richard M. Laine, Youval Shvo
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Patent number: 4625064Abstract: An improved process for preparing a bis [.beta.-(N,N-dimethylamino)ethyl]ether by reacting a bismethohalide of bis [.beta.-(N,N-dimethylamino)ethyl]ether represented by the following general formula: ##STR1## (wherein X denotes a halogen atom), with an aliphatic amine having a boiling point of not lower than 220.degree. C. at atmospheric pressure and having a primary amino group in the molecule thereof. The process comprises the following two steps (a) and (b): (a) a step of distilling out water at a temperature of not more than 130.degree. C. under reduced pressure from a mixture of said bismethohalide aqueous solution and said aliphatic amine to provide a concentration of said bismethohalide to water of not less than 85% by weight, and (b) a step of reacting said bismethohalide and amine in a solid-liquid phase at a temperature of not lower than 140.degree. C.Type: GrantFiled: April 6, 1984Date of Patent: November 25, 1986Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Sadakatsu Kumoi, Keiji Mitarai, Yukihiro Tsutsumi
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Patent number: 4605770Abstract: A process for preparing predominantly noncyclic polyalkylene polyamine compounds is disclosed wherein an alkanolamine compound and an alkyleneamine compound in a molar ratio of alkanolamine compound:alkyleneamine compound of 1:5 to 3:1, preferably less than 1, is reacted in the presence of a catalytically effective amount of a Group IIA or Group IIIB metal acid phosphate at a temperature from about 200.degree. to 400.degree. C. under a pressure sufficient to maintain the reaction mixture substantially in liquid phase.Type: GrantFiled: December 22, 1983Date of Patent: August 12, 1986Assignee: Air Products and Chemicals, Inc.Inventors: Michael E. Ford, Thomas A. Johnson
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Patent number: 4599087Abstract: Polymeric compounds (A) obtained by the reaction of epihalohydrin with a polyalkylene polyamine are useful as textile treatment agents. As pretreatment agents they improve the color yield of the subsequent dyeing, as aftertreatment agents they improve fastness properties. Certain of the products (A) are novel.Type: GrantFiled: December 24, 1984Date of Patent: July 8, 1986Assignee: Sandoz Ltd.Inventors: Jurg Heller, Bruno Kissling, Tibor Robinson, Salvatore Valenti
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Patent number: 4582937Abstract: Ethyleneamines are efficiently recovered from an aqueous solution thereof by extracting them from the aqueous solution into an organic phase with an extractant selected from carbonyl group-containing organic solvents, benzyl alcohol, carboxylic acids and salts thereof, alkylphosphoric acids and salts thereof, and mixed solvents containing at least one of these extractants. The ethyleneamines in the organic phase is recovered preferably from the organic phase to the aqueous phase by incorporating an acid therein, followed by phase separation.Type: GrantFiled: April 12, 1985Date of Patent: April 15, 1986Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Yoichi Hiraga, Tsugio Murakami, Hiroyuki Saito, Osamu Fujii
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Patent number: 4578517Abstract: A process for preparing polyalkylene polyamine compounds is disclosed wherein ammonia or a primary or secondary amine and an alkanolamine compound are reacted in the presence of an effective amount of a Group IIIB metal acid phosphate at a temperature from about 175.degree. to 400.degree. C. under a pressure sufficient to maintain a substantial amount of the ammonia or amine in the reaction zone. The polyalkylene polyamines thus formed are recovered from the reaction mixture.Type: GrantFiled: September 16, 1983Date of Patent: March 25, 1986Assignee: Air Products and Chemicals, Inc.Inventors: Thomas A. Johnson, Michael E. Ford
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Patent number: 4570019Abstract: A process is provided which may be run continuously for producing polyethylene polyamines having improved color characteristics which comprises treating discolored polyethylene polyamines with polyethylene polyamine hydrochloride in the presence of water at elevated temperatures for the time necessary to reduce the color of said polyethylene polyamines and then flash evaporating the decolorized polyethylene polyamines from the treating mixture.Type: GrantFiled: February 8, 1984Date of Patent: February 11, 1986Assignee: Union Carbide CorporationInventors: Charles A. Gibson, John W. Crandall