Three Or More Amino Nitrogens Containing Patents (Class 564/512)
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Patent number: 5206394Abstract: Disclosed is a process for the manufacture of alkali metal salt complexes of the formula (M.sub.x X.nL).sub.y, where M is an alkali metal, e.g. lithium, X is an anion, e.g. halide or thiocyanate, L is an organic electron-donating ligand (Lewis base), x is the valency of the anion X, n is usually 1,2 or 4 and y is an integer, by the in situ reaction of an alkali metal or an alkali metal hydride or alkyl, for example lithium, lithium hydride or butyl lithium, and an anhydrous ammonium salt comprising the anion X, e.g. an anhydrous ammonium halide, the reaction being performed in solution in an anhydrous solvent in the presence of the ligand (L).Type: GrantFiled: August 18, 1989Date of Patent: April 27, 1993Assignee: The Associated Octel Company LimitedInventors: Ronald Snaith, Dominic S. Wright
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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: 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: 5202489Abstract: Process of making amines by inter alia the (i) intramolecular condensation of an amino compound to an amine having a lower molecular weight or (ii) the intermolecular condensation of an amino compound with one or more of another amino compound or a compound containing an alcoholic hydroxyl group using a Group IVB metal oxide condensation catalyst. The preferred process involves the manufacture of alkyleneamines, most desirably polyalkylenepolyamines, by such condensation reactions utilizing catalysts containing titanium oxide, zirconium oxide or mixtures of them.Type: GrantFiled: August 8, 1989Date of Patent: April 13, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., David J. Schreck, George A. Skoler, Stephen W. King
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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: 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: 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: 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: 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: 5132427Abstract: A process for the preparation of amines of the formula ##STR1## in which R.sup.1 is the radical H.sub.2 N-CH.sub.2 and R.sup.2 is hydrogen, or R.sup.1 and R.sup.2 together form a bridging group --CH.sub.2 --, by reacting 1,3,6-tricyanohexane at elevated temperature and pressure with hydrogen in contact with a catalyst containing, in addition to cobalt oxide, and oxide of an alkali metal, an oxide of an alkaline earth metal, an oxide of a rare earth or an oxide of scandium or yttrium.Type: GrantFiled: October 22, 1990Date of Patent: July 21, 1992Assignee: BASF AktiengesellschaftInventors: Ulrich Koehler, Hardo Siegel, Peter Jaeger, Matthias Irgang
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Patent number: 5118850Abstract: 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 oxdies, 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: November 9, 1990Date of Patent: June 2, 1992Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5109024Abstract: The present invention relates to certain novel polyamine compounds of the formula: ##STR1## wherein Z is a saturated (C.sub.2 -C.sub.6) alkylene moiety, each R group independently is hydrogen, methyl, ethyl, or n-propyl with the provisos that both R groups cannot be hydrogen and that R is hydrogen or methyl when Z is a branched chain alkylene; or a pharmaceutically acceptable acid addition salt thereof.Type: GrantFiled: February 8, 1991Date of Patent: April 28, 1992Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Nellikunja Prakash, David M. Stemerick, Michael L. Edwards, Terry L. Bowlin
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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: 5103056Abstract: Disclosed is a method for selective formation of amidoamines which comprises reacting a carboxylic acid group, such as, for example, a diacid or an aliphatic acid terminated amide with an aminopropylated disecondary amine which contains a secondary amine terminus in the same molecule at a temperature of about 150.degree. C. to about 260.degree.0 C.Type: GrantFiled: January 31, 1991Date of Patent: April 7, 1992Assignee: Texaco Chemical CompanyInventors: George P. Speranza, Donald H. Champion
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Patent number: 5101074Abstract: This invention relates to vicinal di(hetero)alkylene organometalate compounds comprising one or more metal oxides in association with an alkanolamine, an alkyleneamine, an alkylene glycol or mixtures thereof. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentaethylenehexamine (PEHA), and to processes for the preparation thereof using the vicinal di(hetero)alkylene organometalates.Type: GrantFiled: August 8, 1989Date of Patent: March 31, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Arthur R. Doumaux, Jr., David J. Schreck, George A. Skoler
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Patent number: 5091576Abstract: The present invention relates to anti-neoplastic and anti-psoriasis pharmaceutical compositions and methods of treatment and to insecticidal compositions and methods of controlling the growth of insects.Type: GrantFiled: June 23, 1988Date of Patent: February 25, 1992Assignee: University of FloridaInventor: Raymond J. Bergeron
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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: 5082972Abstract: At least one of ammonia and ethylenediamine is reacted with monoethanolamine in the presence of a catalyst containing phosphoric acid or its condensate in order to prepare acyclic ethyleneamines, and the catalyst can be improved in performance and the life of the catalyst can be prolonged by feeding a phosphorus-containing material to a reaction system during the reaction. In addition, the catalyst having a deteriorated performance can be reactivated by adding the phosphorus-containing material to the catalyst.Type: GrantFiled: July 11, 1990Date of Patent: January 21, 1992Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tadashi Komiyama, Hisaharu Kuboyama, Takashi Jimbo, Hiroyoshi Watanabe, Shuichi Tokumoto, Yumiko Endoh, Eiichi Sugiyama, Yoshitaro Naganuma
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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: 5053152Abstract: Improved additives/dispersants for lubricant and fuel compositions are obtained by condensing a hydroxyalkyl or hydroxyaryl compound with an amine compound. The condensates according to the present invention are produced by the acid catalyzed condensation of the amine reactant with the hydroxy reactant.Type: GrantFiled: August 3, 1989Date of Patent: October 1, 1991Assignee: The Lubrizol CorporationInventor: Thomas F. Steckel
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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: 4939300Abstract: Aminic orthoester derivatives of the formulae ##STR1## are effective in stabilizing organic materials against oxidative, thermal and actinic degradation.Type: GrantFiled: November 16, 1987Date of Patent: July 3, 1990Assignee: Ciba-Geigy CorporationInventors: Linda A. Benjamin, Joseph E. Barbiarz, Stephen D. Pastor
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Patent number: 4927971Abstract: There is disclosed a desensitizing ink comprising an adduct produced by the addition of 4 to 70 mols of an alkylene oxide to 1 mol of an amine represented by the general formula (I) where 40 mol % or more of said alkylene oxide are butylene oxide: ##STR1##Type: GrantFiled: May 8, 1989Date of Patent: May 22, 1990Assignee: Mitsubishi Paper Mills Ltd.Inventors: Mitsuru Fuchigami, Shingo Tachizawa, Mamoru Ishiguro
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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: 4888425Abstract: Enhanced production of predominantly linearly extended polyalkylene polyamines from alkylenediamines reacted with alkylene glycols or alkanolamines using a phosphorus-containing catalyst is achieved by removing water during the reaction.Type: GrantFiled: February 7, 1984Date of Patent: December 19, 1989Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: William B. Herdle
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Patent number: 4864062Abstract: A process for producing dioctamethylene triamine is disclosed which comprises dimerizing octamethylene diamine in the presence of a zeolite catalyst, characterized in that the catalyst is represented by the formula:Na.sub.2 O.cndot.xSiO.sub.2 .cndot.yAl.sub.2 O.sub.3wherein x and y are so selected that the molar ratio of Na.sub.2 O to Al.sub.2 O.sub.3 is in the range of 0.02 to 0.05 and the molar ratio of SiO.sub.2 to Al.sub.2 O.sub.3 is in the range of 1 to 10.Type: GrantFiled: September 23, 1988Date of Patent: September 5, 1989Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masao Saito, Koichiro Yamada
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Process for producing higher molecular weight amino compounds having reduced monomeric amine content
Patent number: 4855504Abstract: High molecular weight amines having reduced low molecular weight amine contents are obtained by reacting a mixture of (1) a high molecular weight amine and (2) a low molecular weight amine with (3) an isocyanate in quantities such that from 0.5 to 10 equivalents of isocyanate are present for each equivalent of low molecular weight amine. The product of high molecular weight amines is particularly useful in the production of isocyanate addition products such as polyurethane plastics and foams.Type: GrantFiled: September 23, 1985Date of Patent: August 8, 1989Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Ernst Grigat, Gerhard Grogler, Heinrich Hess, Richard Kopp -
Patent number: 4827037Abstract: Process for the improvement of the quality of polyalkylene polyamines prepared by the reaction of (i) ammonia and/or an alkyleneamine compound having at least two amino groups and an alkanolamine compound having at least one amino group in the presence of a catalytically effective amount of a metal acid phosphate and at a temperature and pressure sufficient to form the polyalkylene polyamine.Type: GrantFiled: April 4, 1985Date of Patent: May 2, 1989Assignee: Union Carbide CorporationInventor: Arthur R. Doumaux, Jr.
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Patent number: 4803304Abstract: Recovery of bis(hexamethylene)triamine from still heels of hexamethylenediamine by extraction using an aliphatic hydrocarbon having a boiling point between about 34.degree. C. and 210.degree. C.Type: GrantFiled: April 15, 1987Date of Patent: February 7, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Robert A. Smiley
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Patent number: 4795828Abstract: Procainamide and N-acetylprocainamide (NAPA) immunogens, antibodies prepared therefrom, labeled conjugates, synthetic intermediates, and the use of such antibodies and labeled conjugates in immunoassays for determining the respective drugs. The immunogens comprise the drugs coupled at the .alpha.-position of the amide side chain to an immunogenic carrier material. The labeled conjugates and synthetic intermediates similarly are .alpha.-position derivatives of the drugs or precursors thereof. The antibodies and labeled conjugates are particularly useful in homogeneous nonradioisotopic immunoassays for measuring the respective drugs in biological fluids such as serum.Type: GrantFiled: September 25, 1986Date of Patent: January 3, 1989Assignee: Miles Inc.Inventors: Robert T. Buckler, Frederick E. Ward
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Patent number: 4720588Abstract: This invention pertains to an improved process for preparing noncyclic polyalkylene polyamine compounds in high selectivity by reacting an alkanolamine and an alkylene amine in the presence of an inert gas and an acidic catalyst. The improvement resides in effecting the reaction under fixed bed catalytic conditions and maintaining the reaction conditions such that a vapor phase condition exists for the reaction mixture comprising both reactants and products. To accomplish the formation of vapor phase conditions sufficient inert gas is injected into the feedstream along with alkanolamine and alkylene amine so that the dew point temperature of the reaction product mix is below the reaction temperature at reaction pressure.Type: GrantFiled: January 16, 1986Date of Patent: January 19, 1988Assignee: Air Products and Chemicals, Inc.Inventors: Michael G. Turcotte, Cawas A. Cooper, Michael E. Ford, Thomas A. Johnson
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Patent number: 4719313Abstract: Gem-dihalo and gem-tetrahalo-1,12-diamino-4,9-diaza-dodecane derivatives useful as antiproliferative or antitumor agents.Type: GrantFiled: February 12, 1986Date of Patent: January 12, 1988Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Fritz Gerhart, Pierre Mamont
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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: 4698428Abstract: It has been surprisingly discovered in accordance with the present invention that N-methylethanolamine may be converted to N,N'-dimethylpiperazine when using a catalyst composed of titania to which from about 0.5 to about 7 wt. % of phosphorus has been thermally chemically bonded in the form of phosphate linkages.Type: GrantFiled: June 9, 1986Date of Patent: October 6, 1987Assignee: Texaco Inc.Inventors: Robert L. Zimmerman, Steven H. Vanderpool
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Patent number: 4698427Abstract: Ethylenediamine and diethanolamine and/or hydroxyethyldiethylenetriamine can be converted to N-aminoethylpiperazine and tetraethylenepenetamine when using a catalyst composed of titania to which from about 0.5 to about 7 wt. % of phosphorus has been thermally chemically bonded in the form of phosphate linkages.Type: GrantFiled: June 9, 1986Date of Patent: October 6, 1987Assignee: Texaco Inc.Inventor: Steven H. Vanderpool
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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: 4647701Abstract: Ethanolamine is subjected to reductive amination in a continuous process to produce diethylenetriamine with less than 10 weight percent piperazine contained in the reaction products. The reductive amination conditions include the use of a catalyst, an ethanolamine feed rate of at least about 400 kilograms of ethanolamine per hour per cubic meter of catalyst, and a temperature sufficient to react between about 35 and 60 percent of the ethanolamine fed.Type: GrantFiled: May 23, 1984Date of Patent: March 3, 1987Assignee: Union Carbide CorporationInventor: Charles A. Gibson
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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: 4631337Abstract: Dense star polyamines having terminal group densities greater than extended conventional star polyamines exhibit greater and more uniform reactivity than their corresponding extended conventional star polyamines. For example, a second generation, amine-terminated polyamine dense star polyamine prepared from tri(2-aminoethyl)amine and aziridine has 4.7.times.10.sup.-3 amine moieties per unit volume (cubic Angstrom units) in contrast to the 1.7.times.10.sup.-3 amine moieties per unit volume contained by an extended conventional star polyamine. Such dense star polyamines are useful as calibration standards, high efficiency proton scavengers and in making size selective membranes.Type: GrantFiled: July 15, 1985Date of Patent: December 23, 1986Assignee: The Dow Chemical CompanyInventors: Donald A. Tomalia, James R. Dewald
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Patent number: 4617418Abstract: This invention pertains to an improved process for preparing noncyclic polyalkylene polyamine compounds in high selectivity by reacting ammonia, an alkanolamine and an alkylene amine in the presence of an acidic catalyst. The improvement resides in effecting the reaction under fixed bed catalytic conditions and maintaining the reaction conditions such that a vapor phase condition exists for the reaction mixture comprising both reactants and products. To accomplish the formation of vapor phase conditions, sufficient ammonia is injected into the feedstream along with alkanolamine and alkylene amine so that the dew point temperature of the reaction product mix is below the reaction temperature at reaction pressure.Type: GrantFiled: November 26, 1984Date of Patent: October 14, 1986Assignee: Air Products and Chemicals, Inc.Inventors: Michael E. Ford, Thomas A. Johnson
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Patent number: 4612397Abstract: This invention is directed to thermally activated pelletted catalyst compositions comprising titania having phosphorous derived from a diaminohydrogen phosphate deposited thereon and to their preparation and their use in the production of predominantly linear polyethylenepolyamines from ethylenediamine and monoethanolamine.Type: GrantFiled: April 25, 1985Date of Patent: September 16, 1986Assignee: Texaco, Inc.Inventor: Terry L. Renken
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Patent number: 4609761Abstract: This invention is directed to pelletted thermally activated catalyst compositions comprising titania having phosphorous derived from a trialkyl phosphate or phosphite deposited thereon and to their use in the production of predominantly linear polyethylenepolyamines from ethylenediamine and monoethanolamine.Type: GrantFiled: April 16, 1985Date of Patent: September 2, 1986Assignee: Texaco Inc.Inventors: Lewis W. Watts, Jr., Steven H. Vanderpool
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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: 4588842Abstract: This invention is directed to thermally activated pelletted catalyst compositions comprising phosphorous compounds deposited on group IVb transition metal oxides and their use in the production of predominately linear polyethylenepolyamines from ethylenediamine and monoethanolamine.Type: GrantFiled: December 22, 1983Date of Patent: May 13, 1986Assignee: Texaco Inc.Inventor: Steven H. Vanderpool
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Patent number: 4584406Abstract: This invention is directed to pelletted catalyst compositions supported on group IVb transition metal oxides that contain phosphorous derived from phosphoryl chloride or phosphorous bromide and their use in the production of predominantly linear polyethylenepolyamines from ethylenediamine and monoethanolamine.Type: GrantFiled: December 6, 1984Date of Patent: April 22, 1986Assignee: Texaco Inc.Inventors: Steven H. Vanderpool, Terry L. Renken