Three Or More Amino Nitrogens Containing Patents (Class 564/512)
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Patent number: 5976202Abstract: Reaction products of polyolefins having predominantly a terminal double bond and a number average molecular weight of from 250 to 10,000, which possess an aliphatic hydrocarbon skeleton which is straight-chain or carries C.sub.1 -C.sub.4 -alkyl side chains, with from 1 to 10 mol, per equivalent of double bond, of one or more vinyl esters I ##STR1## are obtainable by reacting the stated polyolefins with the vinyl esters I in the presence of a free radical initiator at from 80 to 200.degree. C., it being possible for these reaction products subsequently to have been hydrolyzed to the corresponding alcohols or converted into the corresponding amines by reductive amination with amines II ##STR2## .Type: GrantFiled: July 20, 1995Date of Patent: November 2, 1999Assignee: BASF AktiengesellschaftInventors: Hans Peter Rath, Helmut Mach, Harald Schwahn, Hans-Joachim Muller, Wolfgang Reif, Thomas Ruhl
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Patent number: 5929283Abstract: The present invention relates to an amine derivative represented by the following general formula (1): ##STR1## wherein R.sup.2 and R.sup.3 mean individually an alkyl or alkenyl group which may have --OH and has 1-24 carbon atoms, A denotes an alkylene or alkenylene group which may have at least one --OH, --COOH or --SO.sub.3 H and has 1-6 carbon atoms, y.sup.1 is --COOH, --SO.sub.3 H or --OSO.sub.3 H, y.sup.2 means --OH, --OSO.sub.3 H or --OCO--A--COOH, n stands for a number of 0 or 1, and p is an integer of 1-8, or a salt or quaternized product thereof, and a detergent composition containing such a compound. This compound is low in irritativeness to the skin and hair and excellent in foamability, and can give a pleasant feeling to the user's skin and the like.Type: GrantFiled: September 23, 1997Date of Patent: July 27, 1999Assignee: Kao CorporationInventors: Mitsuru Uno, Tomohito Kitsuki, Katsumi Kita, Yoshiaki Fujikura, Akiko Okutsu
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Patent number: 5919934Abstract: Disclosed are bisaminothiol and amino compounds with appended pharmacophores, complexes of these compounds with .sup.99m Tc(V)0, Re(V)0, In.sup.+3, .sup.67 Ga.sup.+3, .sup.90 Y.sup.+3, .sup.109 Pd.sup.+2 or .sup.105 Rh.sup.+3, and pharmaceutical compositions containing the complexes. Also disclosed are methods of diagnosing a mammal for the presence of a mammalian tumor, methods for in vitro detection of a cancer cell in a mammalian tissue sample, and methods of treating a mammal having a tumor.Type: GrantFiled: February 19, 1997Date of Patent: July 6, 1999Assignee: The George Washington UniversityInventors: Christy Seith John, Benjamin Byung-Duk Lim
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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: 5874627Abstract: A process for preparing polyamines of the formula ##STR1## by selective introduction of the groups Z--CH.sub.2 -- at the terminal nitrogens from a polyamine having no nitrogen substituents by formation of bis-hexahydropyrimidine derivative, acylation, reduction of acyl group to give Z--CH.sub.2 --, and solvolysis.Type: GrantFiled: September 11, 1997Date of Patent: February 23, 1999Assignee: Merrell Pharmaceuticals Inc.Inventors: Paul T. Angell, John Martin, Peter B. Anzeveno
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Patent number: 5866613Abstract: A polyamine and pharmaceutical composition containing an effective amount of the polyamine useful for administration to a human or non-human animal afflicted with neoplastic cells, the polyamine having the formula:R.sub.1 --NH--(CH.sub.2).sub.3 --NH--(CH.sub.2).sub.3 --NH--(CH.sub.2).sub.3 --NH--R.sub.2wherein R.sub.1 and R.sub.2 are both ethyl; or a salt thereof with a pharmaceutically acceptable acid, as well as a method of treatment comprising administering to such animals an effective amount of a polyamine of the above formula wherein R.sub.1 and R.sub.2 are each lower alkyl of 1-4 carbon atoms.Type: GrantFiled: June 7, 1995Date of Patent: February 2, 1999Assignee: University of Florida Research Foundation, Inc.Inventor: Raymond J. Bergeron
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Patent number: 5834439Abstract: The present invention discloses highly packed polycationic ammonium, sulfonium and phosphonium lipid compounds useful for making lipid aggregates for delivery of macromolecules and other compounds into cells. They are especially useful for the DNA-dependent transformation of cells. Methods for their preparation and use as intracellular delivery agents are also disclosed.Type: GrantFiled: January 13, 1997Date of Patent: November 10, 1998Assignee: Life Technologies, Inc.Inventors: Alberto Haces, Valentina C. Ciccarone
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Patent number: 5696071Abstract: Described are a tris(3-aminopropyl)amine derivative represented by the following formula (1): ##STR1## wherein R represents a C.sub.1-24 alkyl or alkenyl group which may have --OH, A represents a C.sub.1-6 alkylene or alkenylene group which may have --OH, --COOH or --SO.sub.3 H, Y.sup.1 represents --COOH, --SO.sub.3 H or --OSO.sub.3 H , Y.sup.2 represents --OH, --OSO.sub.3 H or --OCO--A--COOH and n stands for 0 or 1, or a salt or quaternized product thereof; and a detergent composition containing the same. The compound according to the present invention has low skin or hair irritation, has excellent foaming power and imparts favorable touch feeling to the skin or the like.Type: GrantFiled: January 7, 1997Date of Patent: December 9, 1997Assignee: Kao CorporationInventors: Akiko Okutsu, Tomohito Kitsuki, Katsumi Kita
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Patent number: 5677351Abstract: Polyamines having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are alkyl, aralkyl or aryl having up to 10 carbon atoms; anda and b may be the same or different and are integers from 1 to 8; or a salt thereof with a pharmaceutically acceptable acid. Anti-neoplastic, anti-diarrheal, anti-peristaltic, gastrointestinal anti-spasmodic, anti-viral, anti-retroviral, anti-psoriasis and insecticidal compositions comprising biologically effective amounts of the above-described amines and biologically acceptable carriers therefor are also disclosed, as well as methods of treatment, administration or application of biologically effective amounts of the polyamines of the invention. Also disclosed are methods for preparing the polyamines of the invention.Type: GrantFiled: June 7, 1995Date of Patent: October 14, 1997Assignee: University of Florida Research Foundation, Inc.Inventor: Raymond J. Bergeron, Jr.
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Patent number: 5674908Abstract: The present invention discloses highly packed polycationic ammonium, sulfonium and phosphonium lipid compounds useful for making lipid aggregates for delivery of macromolecules and other compounds into cells. They are especially useful for the DNA-dependent transformation of cells. Methods for their preparation and use as intracellular delivery agents are also disclosed.Type: GrantFiled: December 20, 1993Date of Patent: October 7, 1997Assignee: Life Technologies, Inc.Inventors: Alberto Haces, Valentina C. Ciccarone
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Patent number: 5672636Abstract: The invention relates to a process for the production of polyurethane foams by reactinga) at least one organic polyisocyanate withb) at least one polyalkylene-polyol (b1) having a hydroxyl number of from 30 to 500, obtainable by alkoxylation of at least one initiator molecule from the group consisting of N,N'-bis(3-aminopropyl)ethylenediamine, tripropylenetetramine and tetrapropylenepentamine using at least one alkylene oxide, preferably ethylene oxide and/or 1,2-propylene oxide, or mixtures of the polyoxyalkylene polyols (b1) and other polyhydroxyl compounds having a functionality of from 2 to 8 and a hydroxyl number of from 15 to 500, andc) if desired, chain extenders and/or crosslinking agents, in the presence ofd) blowing agents and, if desired,e) catalysts andf) additives,and to the novel polyoxyalkylene-polyols (b1) which can be used for this purpose.Type: GrantFiled: October 16, 1995Date of Patent: September 30, 1997Assignee: BASF AktiengesellschaftInventors: Peter Horn, Ludwig Jung, Harald Larbig, Rolf Lebkucher, Gerhard Lehr
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Patent number: 5654484Abstract: The present invention relates to a method for the treatment of patients suffering from certain neoplastic disease states which comprises administering a therapeutically effective amount of a compound of the formula: ##STR1## wherein m is an integer 6 to 9, Z is a saturated (C.sub.2 -C.sub.6) alkylene moiety, each R group independently is hydrogen, methyl, ethyl, or n-propyl except that both R groups cannot be hydrogen when Z is a straight chain; or a pharmaceutically acceptable acid addition salt thereof. Said treatment can optionally comprise conjunctive therapy with a polyamine oxidase inhibitor. The invention also relates to certain novel polyamine derivatives.Type: GrantFiled: June 1, 1995Date of Patent: August 5, 1997Assignee: Merrell Pharmaceuticals Inc.Inventors: Nellikunja J. Prakash, David M. Stemerick, Michael L. Edwards
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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: 5559270Abstract: An improved process of synthesizing gasoline soluble polyolefinic amines or polyether amines comprising the steps of reacting polyolefinic halides or polyether halides with polyamines in a specific sequence of reactions; distilling off non-reactive polyamine; neutralizing the reaction mixture; recovering polyamine(s) and water; and separating polyolefinic amines from the solids with simple filtration or centrifuge or decanting.Type: GrantFiled: December 15, 1994Date of Patent: September 24, 1996Assignee: Petrokleen, Ltd.Inventors: Donald E. Koehler, William J. Claffey
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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: 5554793Abstract: 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: December 19, 1994Date of Patent: September 10, 1996Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
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Patent number: 5541230Abstract: Therapeutic polyamines useful as a cancer chemotherapeutic agents, including molecules having a formula R.sub.1 --NH--(CH.sub.2).sub.x --NH --(CH.sub.2).sub.x --NH--(CH.sub.2).sub.y --NH--(CH.sub.2).sub.z --NH--R, wherein R.sub.1 and R.sub.2 are hydrocarbon chains having 1 to 5 carbons and w, x, y and z are integers of 1 to 10, are disclosed. One such molecule is N.sup.1, N.sup.19 -bis(ethylamino)-5,10,15-triazanonadecane, which is longer than spermine. This preferred compound may be used alone or in combination with other therapeutic agents, such as 1,3-bis(2-chloroethyl)-1-nitrosourea or cis-Pt.Type: GrantFiled: November 5, 1993Date of Patent: July 30, 1996Inventors: Hirak S. Basu, Burt Feuerstein, Laurence Marton, Keijiro Samejima
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Patent number: 5462970Abstract: Anti-diarrheal, anti-secretory, nitric oxide agonist, nitric oxide synthase activating or gastrointestinal anti-spasmodic compounds of the formula: ##STR1## wherein: R.sub.1 and R.sub.6 may be the same or different and are H, alkyl or aralkyl having from 1 to 12 carbon atoms;R.sub.2 -R.sub.5 may be the same or different and are H, R.sub.1 or R.sub.6 ;R.sub.7 is H, alkyl, aryl or aralkyl having from 1 to 12 carbon atoms;m is an integer from 3 to 6, inclusive; andn is an integer from 3 to 6, inclusive; or(IV) a salt thereof with a pharmaceutically acceptable acid; and a pharmaceutically acceptable carrier therefor. Methods of treatment utilizing the composition are also disclosed.Type: GrantFiled: January 3, 1995Date of Patent: October 31, 1995Assignee: University of Florida Research Foundation, Inc.Inventors: Raymond J. Bergeron, Jr., Charles A. Sninsky
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Patent number: 5455277Abstract: A mosquito insecticidal composition and method for controlling the growth of mosquitos employing a mosquito insecticidally effective amount of a compound having one of the formulae: ##STR1## wherein: R.sub.1 and R.sub.6 may be the same or different and are alkyl having from 1 to 12 carbon atoms or hydrocarbyl aralkyl having up to 12 carbon atoms;R.sub.2 -R.sub.5 may be the same or different and are H, R.sub.1 or R.sub.6 ;R.sub.7 is H, alkyl having from 1 to 12 carbon atoms, hydrocarbyl aryl or hydrocarbyl aralkyl each having up to 12 carbon atoms;m is an integer from 3 to 6, inclusive;n is an integer from 3 to 6, inclusive; or(IV) a salt thereof with an acid and a carrier therefor.Type: GrantFiled: December 8, 1993Date of Patent: October 3, 1995Assignee: University of Florida Research Foundation, Inc.Inventor: Raymond J. Bergeron
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Patent number: 5441716Abstract: A chemisorption reaction process is carried out under conditions in which the volumetric expansion of the complex compound reaction product is restricted, and at half-cycle reaction periods of less than 30 minutes each, and/or in a reaction chamber having a maximum mean mass diffusion path length of less than about 15 mm, and/or a maximum heat diffusion path length of less than 1.5 mm.Type: GrantFiled: August 9, 1993Date of Patent: August 15, 1995Assignee: Rocky ResearchInventor: Uwe Rockenfeller
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Patent number: 5440060Abstract: The demands on the properties of pigments, in particular in the areas of emulsion paints and printing inks, which are continuously becoming more specific made it necessary to develop selective and environmentally safe dispersing and emulsifying agents and coupling auxiliaries.The compounds according to the invention are alkoxylation products prepared from fatty amine dialkylenediamines which, if desired, are linked to give recurring structural units by means of esterification with dicarboxylic acids and in which, preferably, the hydroxyl end groups of these fatty amine alkylenediamine alkoxylates have been esterified with fatty acids, aromatic carboxylic acids and/or resin acids and any hydroxyl groups still present have been converted to the corresponding mono-ester-containing anionic radicals by means of dicarboxylic acids and sulfites.Type: GrantFiled: August 30, 1993Date of Patent: August 8, 1995Assignee: Hoechst AGInventors: Heinz Uhrig, Albert Munkel
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Patent number: 5434145Abstract: The present invention relates to certain polyamine thiols which are useful as radioprotective agents.Type: GrantFiled: October 14, 1994Date of Patent: July 18, 1995Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Michael L. Edwards, Ronald D. Snyder
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Patent number: 5432202Abstract: Methods for regulating cation transport across cellular membranes possessing cation channels are provided. The cell membrane possessing a specific ion channel is exposed to a non-aromatic polyamine compound having a lysine- or arginine-based moiety (or a guanidine moiety) coupled to a straight chain polyamine.These polyamines as well as a method for regulating NMDA through a spermidine-like effect on NMDA receptors by exposing a cell membrane to selected polyamines are also provided.Type: GrantFiled: June 9, 1993Date of Patent: July 11, 1995Assignee: New York UniversityInventors: Bruce D. Cherksey, Rodolfo R. Llinas, Mutsuyuki Sugimori
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Patent number: 5430190Abstract: A one-pot reaction process for the coproduction of two polyurethane catalysts which comprises reacting excess diethylenetriamine (DETA) in a reaction vessel with propylene oxide in the presence of a hydrogenation catalyst under conditions and for a period of time to essentially completely react the propylene oxide to give a mixture of DETA and N-2-hydroxypropyldiethylenetriamine (HPDETA), adding formaldehyde and hydrogen to the reaction vessel, reacting the DETA and HPDETA with the formaldehyde and hydrogen under conditions to effect permethylation of the DETA and HPDETA to afford N,N,N',N',N"-pentamethyldiethylenetriamine (PMDETA), a polyurethane catalyst, and N-2-hydroxypropyl-N,N',N',N"-tetramethyldiethylenetriamine (HPTMDETA) a nonfugitive polyurethane catalyst.Type: GrantFiled: June 14, 1994Date of Patent: July 4, 1995Assignee: Air Products and Chemicals, Inc.Inventors: Richard V. C. Carr, Craig R. Williams
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Patent number: 5428116Abstract: New synthesis and analysis procedures for novel crosslinked polyamines and ampholytes. Polyamines are crosslinked with tartaric acid ester, malonic acid ester, or polycarboxylic acid esters of the citric acid cycle. The resulting crosslinked polyamine may further react with other compounds such as an .alpha.,.beta.-unsaturated or .alpha.-halo unsaturated carboxylic acids to prepare new ampholyte mixtures. The resulting novel ampholytes exhibit greater heterogeneity and complexity than presently prepared ampholytes, and can be used in analytical and preparative isoelectric focusing processes.Novel ampholyte analysis process entails analyzing chemical compounds, usually ampholytes, used in isoelectric focusing processes. The ampholyte is isoelectrically focused on an immobilized pH gradient, and then immersed in a picric acid solution to cause precipitation and visualization of amphoteric species.Type: GrantFiled: March 11, 1994Date of Patent: June 27, 1995Assignee: Board of Regents, The University of Texas SystemInventors: L. Scott Rodkey, Philip R. DeShong
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Patent number: 5410087Abstract: 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: November 17, 1993Date of Patent: April 25, 1995Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, David C. Molzahn, Robert G. Bowman
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Patent number: 5393441Abstract: Briefly stated, the present invention comprises novel compounds useful as two-cycle oil additives obtained by reacting an alkyl acrylamide with a compound selected from the group consisting of polyalkylenepolyamines, polyalkylenepolyamines functionalized with polyalkyl acid anhydrides and polyalkylenepolyamines and a polyalkyl acid anhydride.Type: GrantFiled: November 23, 1993Date of Patent: February 28, 1995Assignee: Exxon Research and Engineering CompanyInventors: Warren A. Thaler, Stephen Zushma, Richard H. Schlosberg
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Patent number: 5364971Abstract: The present invention relates to a process for the reduction of the color of polyamines by reacting at elevated temperature, e.g. 120.degree.-170.degree. C., and pressure, e.g. 500 to 6000 psig. the colored polyamines, e.g. triethylenetetramine and tetraethylenepentamine, in the presence of a ruthenium on alumina hydrogenation catalyst. The catalyst for the polyamine decolorization process preferably has at least 0.5 wt. % Ru. In the process of the present invention, the polyamines can either be distilled into a narrow product composition and then hydrogenareal, or a crude polyamine product can be hydrogenated and then distilled to produce the desired product composition.Type: GrantFiled: August 25, 1993Date of Patent: November 15, 1994Assignee: Texaco Chemical Inc.Inventor: Wei-Yang Su
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Patent number: 5362914Abstract: The present invention relates to a process for the reduction of the color of polyamines by reacting at elevated temperature, e.g. 120.degree.-170.degree. C., and pressure, e.g. 500 to 6000 psig. the colored polyamines, e.g. triethylenetetramine and tetraethylenepentamine, in the presence of a cobalt on alumina hydrogenation catalyst promoted with copper and chromium. In the process of the present invention, the polyamines can either be distilled into a narrow product composition and then hydrogenated, or a crude polyamine product can be hydrogenated and then distilled to produce the desired product composition.Type: GrantFiled: August 25, 1993Date of Patent: November 8, 1994Assignee: Texaco Chemical Inc.Inventor: Wei-Yang Su
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Patent number: 5342945Abstract: The present invention realates to anti-neoplastic and anti-psoriasis pharmaceutical bis-hexahydropyrimidinylalkyl compounds, compositions and methods of treatment and to insecticidal compositions and methods of controlling the growth of insects.Type: GrantFiled: February 12, 1992Date of Patent: August 30, 1994Assignee: University of Florida Research Foundation, Inc.Inventor: Raymond J. Bergeron
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Patent number: 5331102Abstract: Color-containing alkanolamines or alkyleneamines, having color numbers of up to 100 PtCo or higher, can be treated with inorganic solid acidic catalysts. Inorganic support materials having bonded inorganic acid functionalities may be used as the inorganic solid acidic catalysts. In the presence of water, these inorganic solid acidic catalysts produce decolorized alkanolamines or alkyleneamines having color numbers of 20 PtCo or less. The process of decolorization can be carried out in batch or continuous mode processes thus providing low cost, high quality and high purity end products.Type: GrantFiled: June 28, 1993Date of Patent: July 19, 1994Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Charles A. Gibson
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Patent number: 5298231Abstract: Reaction rates in chemisorption reactions involving solid reactants and gaseous ligands are improved by maintaining optimized solid density throughout the reaction. Methods and apparatus which restrict volumetric solid expansion, compression of the solid reactant, and mixture with inert solid porous or particulate materials are disclosed.Type: GrantFiled: November 13, 1992Date of Patent: March 29, 1994Assignee: Rocky ResearchInventor: Uwe Rockenfeller
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Patent number: 5296632Abstract: Nitro polyamines, and especially dinitro polyamines, can be readily reduced by a catalyst of zerovalent nickel on silica where the silica contains not more than 10% alumina and where the nickel content of the finished catalyst may be as high as 85%. The reductions can be performed under relatively low temperatures between 40.degree. and 120.degree. C. to avoid the problem of heat lability of the reactant nitro polyamines. Hydrogenations proceed with good conversion as well as good selectivity and the method offers a means of continuous hydrogenation of nitro polyamines.Type: GrantFiled: July 2, 1992Date of Patent: March 22, 1994Assignee: UOPInventors: Dusan J. Engel, Thomas P. Malloy, Steven R. Paeschke
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Patent number: 5296633Abstract: The methylated tertiary amines are selectively prepared by reacting a primary or secondary amine, or a nitrile or aminonitrile, including an aminoalcohol, etheramine, a polyamine or fatty polyamine or amidoamine, or amidopolyamine or dinitrile, with hexamethylenetetramine ("HMTA"), under hydrogen pressure at a temperature no greater than about 160.degree. C. and in the presence of a catalytically effective amount of a hydrogenation catalyst, e.g., nickel deposited onto appropriate support substrate therefor.Type: GrantFiled: December 30, 1992Date of Patent: March 22, 1994Inventor: Stephane Fouquay
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Patent number: 5288909Abstract: 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: August 19, 1992Date of Patent: February 22, 1994Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
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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: 5256786Abstract: A process of reforming cyclic alkyleneamines to amine-extended cyclic alkyleneamines involving contacting a cyclic alkyleneamine or mixture of cyclic alkyleneamines in the liquid phase with a catalyst under reaction conditions. The catalyst is selected from the group consisting of (a) Group VB metal oxides, (b) Group VB metal phosphates, (c) silicates of Groups IIA, IIIB, IVB and VB, and (d) specified tungsten oxides. For example, piperazine or a mixture of piperazine and aminoethylpiperazine is contacted with magnesium silicate to yield a mixture of amine-extended piperazines, including 1,2-bis(piperazinyl)-ethane and N,N'-bis(2-piperazinylethyl)piperazine.Type: GrantFiled: March 2, 1992Date of Patent: October 26, 1993Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5254199Abstract: Disclosed herein is an adhesive and a process for bonding with the adhesive containing an isocyanate prepolymer a), an isocyanate reactive component b) and a catalyst for the reaction of a) and b), characterized in that the catalyst comprises a compound corresponding to the following formula ##STR1## wherein R.sup.1 and R.sup.2 may be identical of different and denote an alkyl group having 1 to 4 carbon atoms,R.sup.3 denotes a CHO group or H or alkyl group having 1 to 4 carbon atoms, optionally substituted with a CHO group,n stands for an integer from 2 to 4,o stands for 1 or 2,p stands for 0 or 1 ando+p=2.Type: GrantFiled: March 11, 1992Date of Patent: October 19, 1993Assignee: Bayer AktiengesellschaftInventors: Horst Stepanski, Jose Colinas-Martinez, Rainer Trinks, Bernhard Jansen, Hanns-Peter Muller, Otto Ganster
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Patent number: 5248827Abstract: A process for producing an ethylenamine, which comprises reacting ammonia and/or an ethylenamine with an ethanolamine in the presence of hydrogen to obtain an ethylenamine having an increased number of ethylene chains over the ammonia and/or the ethyelenamine used as the starting material, wherein a catalyst comprising Ni and M elements wherein M is at least one rare earth element selected from the group consisting of scandium, yttrium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium and lutetium, is used for the reaction.Type: GrantFiled: September 17, 1991Date of Patent: September 28, 1993Assignee: Tosoh CorporationInventors: Yasushi Hara, Toshio Hironaka, Noritaka Nagasaki, Nobuyuki Kanai, Nobumasa Suzuki, Yukio Ito, Takanori Miyake
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Patent number: 5231230Abstract: This invention relates to a process for making amines having a high yield weight percent of diethylenetriamine (DETA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a metallic phosphate having a cyclic structure or an acyclic structure which is transformed into a cyclic structure during the process, a metallic polyphosphate having a condensed structure, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in DETA.Type: GrantFiled: March 30, 1990Date of Patent: July 27, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Arthur R. Doumaux, Jr., Stephen W. King, David J. Schreck
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Patent number: 5227528Abstract: A process for decolorizing polyalkylene polyamines, which comprises contacting one or more polyalkylene polyamines having an average molecular weight of greater than about 200 and less than about 1000 with carbon at a temperature greater than or equal to about 100.degree. C. and less than or equal to about 300.degree. C. under conditions effective to reduce the color rating of the one or more polyalkylene polyamines.Type: GrantFiled: April 30, 1992Date of Patent: July 13, 1993Assignee: The Dow Chemical CompanyInventors: Stephen J. Webster, John H. Mitchell
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Patent number: 5225598Abstract: This invention relates to a process for making amines having a high yield weight percent of linear pentaethylenehexamine (L-PEHA) and hydroxyethyldiethylenetriamine (HEDETA) 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 L-PEHA and HEDETA.Type: GrantFiled: March 30, 1990Date of Patent: July 6, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., Stephen W. King, Lloyd M. Burgess
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Patent number: 5225599Abstract: This invention relates to a process for making amines having a high yield weight percent of linear triethylenetetramine (L-TETA) 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 L-TETA and AEEA.Type: GrantFiled: March 30, 1990Date of Patent: July 6, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumax, Jr.
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Patent number: 5225561Abstract: Metal organic chemical vapor deposition (MOCVD) formation of copper oxide superconductor materials. Various source reagents of Group II elements suitable for high temperature superconductor (HTSC) material formation are described, including beta-diketonates, cyclopentadienyls, alkyls, perfluoroalkyls, alkoxides, perfluoroalkoxides, and Schiff bases, as well as complexes of such Group II compounds, utilizing monodentate or multidentate ligands to provide additional coordination to the Group IIA atom, so that the resulting complex is of enhanced volatility characteristics, and enhanced suitability for MOCVD applications. Also disclosed are methods of synthesizing such compounds and complexes, including a method of making Group II metal beta-diketonate compounds having enhanced thermal stability characteristics. Further disclosed are a vertical inverted reactor for chemical vapor deposition, and various methods of processing applied metal oxide films for enhanced HTSC character.Type: GrantFiled: September 12, 1990Date of Patent: July 6, 1993Assignee: Advanced Technology Materials, Inc.Inventors: Peter S. Kirlin, Duncan W. Brown, Robin A. Gardiner
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Patent number: 5225600Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a Group VIB metal-containing condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentaethylenehexamine (PEHA).Type: GrantFiled: August 26, 1992Date of Patent: July 6, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Arthur R. Doumaux, Jr., David J. Schreck
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Patent number: 5220071Abstract: This invention relates to a process for making amines having a high yield weight percent of pentaethylenehexamine (PEHA) and hydroxyethyltriethylenetetramine (HETETA) 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 PEHA and HETETA.Type: GrantFiled: March 30, 1990Date of Patent: June 15, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Arthur R. Doumaux, Jr., Stephen W. King, David J. Schreck
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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: 5214213Abstract: This invention relates to a process for making amines having a high yield weight percent of linear tetraethylenepentamine (L-TEPA) and hydroxyethyldiethylenetriamine (HEDETA) 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 L-TEPA and HEDETA.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