Hydroxy, Bonded Directly To Carbon, Or Ether Containing (h Of -oh May Be Replaced By A Substituted Or Unsubstituted Ammonium Ion Or A Group Ia Or Iia Light Metal) Patents (Class 564/503)
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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: 5196583Abstract: The invention provides a novel class of propargyl compounds represented by the formula: ##STR1## wherein R is an C.sub.1 -C.sub.20 alkyl group, C.sub.1 -C.sub.20 alkylene group, C.sub.1 -C.sub.20 alkylene group interrupted by --NH-- group(s), C.sub.6 -C.sub.7 alicyclic group and an aromatic group; R.sub.1 comprises 1-100% --CH.sub.2 --C.tbd.CH group and 99-0% hydrogen atom and n is an integer of 1 to 4, and preparation thereof.These compounds are useful as coating material or sealer or rim-injection molding material.Type: GrantFiled: December 4, 1990Date of Patent: March 23, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Kei Aoki
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Patent number: 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: 5162048Abstract: The present invention relates to an additive to hydrocarbon fuels which includes nitrate of ethanolamine as an additive to reduce the quantity of smoke and improve the efficiency of combustion. The invention also relates to a process for the preparation of this additive and of the fuels improved by the addition of the additive.Type: GrantFiled: August 20, 1990Date of Patent: November 10, 1992Assignee: Kirsten, Inc.Inventor: Samuel Diaz-Valdes
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Patent number: 5137919Abstract: The invention relates to a novel compound, compositions and medicaments thereof and a method of inhibiting cell proliferation, platelet aggregation (induced by various factors), and inhibiting malignant phenotypes of tumor cells such as those having a metastatic property, using said compound, composition or medicament. N,N,N-trimethylsphingosine shows superior cell proliferation inhibitory and anti-metastatic activity over related compounds.Type: GrantFiled: December 31, 1990Date of Patent: August 11, 1992Assignee: Biomembrane InstituteInventors: Yasuyuki Igarashi, Mahammad N. Ahmad, Hirofumi Okoshi, Sen-Itiroh Hakomori
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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: 5099070Abstract: A process for producing neopentyldiamine is provided. This process entails contacting a feedstream containing neopentanolamine with ammonia and hydrogen in the presence of a support nickel catalyst under amination conditions.Type: GrantFiled: December 7, 1990Date of Patent: March 24, 1992Assignee: Eastman Kodak CompanyInventors: Garrett C. Luce, Anthony W. McCollum
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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: 5087753Abstract: Process for recovering .alpha.-aminoalcohols by extraction from aqueous solutions, in which process an aromatic aldehyde is added at elevated pH to an aqueous solution of an aminoalcohol in an at least equimolar amount in respect of the aminoalcohol, the resulting mixture is converted with formation of the Schiff base of the aldehyde and the aminoalcohol and the aqueous solution is subsequently extracted using a water-immiscible organic solvent, upon which the Schiff base in the resulting extract is hydrolized and the .alpha.-aminoalcohol or a salt thereof is recovered.Type: GrantFiled: September 19, 1990Date of Patent: February 11, 1992Assignee: Stamicarbon B.V.Inventors: Wilhelmus H. J. Boesten, Catharina H. M. Schepers, Mathieu J. A. Roberts
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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: 5068397Abstract: Tris-perfluoroalkyl terminated neopentyl alcohols of the formula (R.sub.f --E.sub.n --X--CH.sub.2).sub.3 CCH.sub.2 OH prepared from halogenated neopentyl alcohols and thiols of the formula R.sub.f --E.sub.n --SH, amines of the formula R.sub.f --E.sub.n --NH--R, alcohols of the formula R.sub.f --E.sub.n --OH, perfluoro-acids or amides, are described. The alcohols react with isocyanates to prepare urethanes; with acids or derivatives, to prepare esters or carbonates; with epoxides to form ethers. Further, they may be converted to halide intermediates. The products all contain the residue of at least one R.sub.f -neopentyl alcohol containing three perfluoroalkyl hetero groups.Type: GrantFiled: August 15, 1990Date of Patent: November 26, 1991Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Kirkland P. Clark, Michael Jacobson, Athanasios Karydas, Juliana Rodgers
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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: 5066815Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a carbonyl compound in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: May 8, 1990Date of Patent: November 19, 1991Assignee: Takasago International CorporationInventors: Noboru Sayo, Hidenori Kumobayashi, Susumo Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 4970307Abstract: A process for formation of a base from a base precursor, which comprises decomposing the base precursor in the presence of a catalyst. The base precursor has the following formula (I) or (II):(R.sup.1 --C.tbd.C--CO.sub.2 H).sub.x .multidot.B (I)R.sup.2 (--C.tbd.C--CO.sub.2 H).sub.2 .multidot.B.sub.y (II)wherein R.sup.1 is a monovalent group selected from the group consisting of hydrogen, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, an aralkyl group, an acyl group, an alkoxycarbonyl group, carbamoyl, --CO.sub.2 M (M is an alkali metal) and --CO.sub.2 H.B, each of which may have one or more substituent groups; R.sup.Type: GrantFiled: August 13, 1987Date of Patent: November 13, 1990Assignee: Fuji Photo Film Co., Ltd.Inventors: Keiji Takeda, Jiro Tsukahara, Kozo Sato
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Patent number: 4931596Abstract: Hydroxylated primary amines corresponding to the formula:R--X--CH.sub.2 --CH(OH)--CH.sub.2 NH.sub.2 (I)in which R is a saturated or unsaturated straight chain C.sub.5 -C.sub.18 aliphatic radical and X represents --O--, --S--, --NH-- or --CH.sub.2 -- are prepared by reacting an epoxide of the formula: ##STR1## in which R and X are as defined previously and R.sub.1 and R.sub.2 together represent an epoxy radical with ammonium carbamate to form the corresponding substituted ammonium carbamate of the formula: ##STR2## in which R and X are as defined previously and thereafter heating the substituted ammonium carbamate thus formed at a temperature and for a length of time sufficient to form the corresponding hydroxylated primary amine of formula (I).The hydroxylated primary amines of formula (I) and the salts of these compounds, particularly the hydrohalide, acetate and quaternary alkyl ammonium salts thereof are useful as medicaments, anticeptics, sterilizing agents and preservatives.Type: GrantFiled: January 3, 1989Date of Patent: June 5, 1990Assignee: Ethyl CorporationInventor: Kathleen S. Laurenzo
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Patent number: 4918235Abstract: The present invention is directed to a new chemical compound, 1,5-diaminoheptanol-6, which corresponds to the formula ##STR1## The present invention is additionally directed to a process for the preparation of 1,5-diaminoheptanol-6 by reacting L-lysine in its free form and/or in the form of its HCl salt, with acetic acid anhydride in the presence of a tertiary organic amino base and with the addition of a 4-aminopyridine derivative, hydrogenating the resulting 1,5-bisacetaminohepthanone-6 to 1,5-bisacetaminoheptanol-6, forming a salt of 1,5-diaminoheptanol-6 by treating 1,5-bisacetaminoheptanone-6 with a mineral acid and isolating the free amine by treating the 1,5-diaminoheptanol-6 salt of a mineral acid with a strong base.Finally, the present invention is directed to the use of 1,5-diaminoheptanol-6 as at least a portion of the chain lengthening agent for the preparation of polyurethane plastics by the isocyanate polyaddition process.Type: GrantFiled: August 2, 1988Date of Patent: April 17, 1990Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Scholl, Josef Pedain
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Patent number: 4904788Abstract: Hydrocarbon-soluble complexes of magnesium alkoxides with magnesium amides are described. The magnesium amide moiety is derived from an amine (e.g., an N-heterocyclic amine). The complexes can be formed by reaction between a magnesium alkyl and a mixture of aliphatic alcohols and an amine.Type: GrantFiled: June 7, 1988Date of Patent: February 27, 1990Assignee: Texas Alkyls, Inc.Inventors: Andrzej M. Piotrowski, Dennis B. Malpass
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Patent number: 4888138Abstract: Compounds corresponding to the formula: ##STR1## in which R is a saturated or unsaturated straight chain C.sub.5 -C.sub.18 aliphatic radical and X represents --O--, --S--, --NH-- or --CH.sub.2 -- are provided by reacting compounds corresponding to the formula: ##STR2## in which R and X are as defined above and R.sub.1 and R.sub.2 together represent an epoxy radical with ammonium carbamate.These compounds may be used as intermediates in the preparation of the hydrohalide salts, particularly the hydrochloride and hydrobromide salts, and acetates of hydroxylated primary amines corresponding to the formula:R--X--CH.sub.2 --CH(OH)--CH.sub.2 NH.sub.2 (III)in which R and X are as defined above which are useful as medicaments, antiseptics, sterilizing agents and preservatives.Type: GrantFiled: November 10, 1988Date of Patent: December 19, 1989Assignee: Ethyl CorporationInventor: Kathleen S. Laurenzo
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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: 4885392Abstract: Polyamines based on derivatives of 1,3-bissubstituted 2-propanol containing a multiplicity of amino groups, the latter containing at least one primary amino group and additionally further N-basic groupings, prepared by reacting 1,2,3-trisubstituted propane compounds with bis(primary amines or with monoamines and bis(primary amines).The polyamines according to the invention are clear to yellowish or yellow products which, at room temperature, form viscous to highly viscous liquids or may be paste-like or wax-like. They may be used, inter alia, advantageously as starting products for the preparation of thermosetting, in particular water-dispersible and cataphoretically depositable binders based on aminourethanes for coating solid substrates, in particular metals.Type: GrantFiled: December 22, 1987Date of Patent: December 5, 1989Assignee: Hoechst AGInventors: Rudiger Lenz, Gerd Walz, Michael Honel, Peter Ziegler
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Patent number: 4873370Abstract: N,N-dialkyl-N'-(beta substituted) alkyl alkylene diamines of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are C.sub.1-4 hydrocarbon groups or H, but both R.sub.1 and R.sub.2 are not H, R.sub.4 is a saturated or unsaturated C.sub.14-24 hydrocarbon group, n=1-4 and X is OH or SH are adapted for use as friction and wear reducing additives in friction and wear reducing compositions.Type: GrantFiled: March 3, 1987Date of Patent: October 10, 1989Assignee: Pennzoil Products CompanyInventor: I-Ching Chiu
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Patent number: 4859357Abstract: The invention relates to new polyfluorinated compounds which are usable as anti-wear additives for lubricants.These compounds are of general formula: ##STR1## in which R.sub.F is a perfluorinated radical, X denotes a divalent linkage--(CH.sub.2 CF.sub.2).sub.a (CH.sub.2).sub.b --, --CF.dbd.CH--CH.sub.2 -- or --CFH--CH.sub.2 CH.sub.2 --, a is an integer ranging from 0 to 10, b is an integer ranging from 1 to 4 but equal to 2 if a is other than zero, R.sub.1 denotes a hydrogen atom or an alkyl radical, R.sub.2 denotes a hydrogen atom or a methyl radical and R.sub.3 denotes an alkyl radical. They are prepared by condensing an amino alcohol, R.sub.F --X--NH--CH.sub.2 CH(R.sub.1)OH, with an alkyl ester of an unsaturated carboxylic acid, CH.sub.2 .dbd.C(R.sub.2)--COOR.sub.3.Type: GrantFiled: June 9, 1988Date of Patent: August 22, 1989Assignee: Societe AtochemInventors: Laurent Germanaud, Marc Hermant
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Patent number: 4853141Abstract: The invention relates to new polyfluorinated compounds which are usable as anti-wear additives for lubricants.These compounds are of general formula: ##STR1## in which R.sub.F is a perfluoroalkyl radical, R.sub.1 and R.sub.3 each denote a hydrogen atom or an alkyl, cycloalkyl or aryl radical, R.sub.2 and R.sub.4 each denote a hydrogen atom or an acyl residue, m equals 0 or 1 and X denotes a hydrogen atom or a 2-hydroxy-1-phenylethyl group. They are prepared by hydrogenation of amino alcohols of formula:R.sub.F --CF.dbd.CH--CH.sub.2 --NH--CH.sub.2 CH(R.sub.1)--OHfollowed, where appropriate, by a reaction with an epoxide and/or an esterification.Type: GrantFiled: June 10, 1988Date of Patent: August 1, 1989Assignee: Societe ATOCHEMInventors: Pierre Durual, Marc Hermant, Charles Laviron
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Patent number: 4845292Abstract: There are disclosed compounds of the formula ##STR1## R is --CH.sub.2 OH or --CO.sub.2 R.sup.3 ; R.sup.1 is hydrogen, lower alkyl, lower alkoxy or hydroxybenzyl;R.sup.2 is hydroxyloweralkyl or diloweralkoxyalkyl;R.sup.3 is hydrogen or lower alkyl;R.sup.4 is alkyl of 10-20 carbons atoms, phenylalkyl of 11-18 carbon atoms or phenoxyalkyl of 11-18 carbon atoms; orn is 1-3;or a pharmaceutically acceptable salt thereof, and their use in the prevention and/or treatment of conditions such as allergic rhinitis, allergic bronchial asthma and other naso-bronchial obstructive air-passageway conditions, other immediate hypersensitivity reactions such as allergic conjunctivitis and various inflammatory conditions.Type: GrantFiled: January 13, 1988Date of Patent: July 4, 1989Assignee: American Home Products CorporationInventors: William H. McGregor, Lisa A. Marshall, John H. Musser
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Patent number: 4795627Abstract: The present invention describes novel tritium labelled nitrogen mustard type compounds, and their aziridinium type analog, and a process for the production of same. The compounds are of value in medical research and development and also as active ingredients of pharmaceutical compositions. The compounds can be used to develop analogs of human disease states and can also be used to evaluate the mechanism of neurotransmitter regulation and function, both in vitro and in vivo.Type: GrantFiled: October 18, 1984Date of Patent: January 3, 1989Assignee: University of PittsburghInventors: Abraham Fisher, Israel Hanin, Donald J. Abraham
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Patent number: 4760189Abstract: The present invention relates to a new process for the preparation of diamine-alcohols.The process according to the present invention relates to the preparation of compounds of the formula:R--NH--CH.sub.2 --CH(OH)--CH.sub.2 NH.sub.2in which R is a C.sub.1 to C.sub.30 alkyl radical, characterized in that ammonia is reacted with the compound of the formula: ##STR1## in which R has the meaning given above and X is a halogen atom.Type: GrantFiled: September 3, 1986Date of Patent: July 26, 1988Assignee: Laboratories PharmascienceInventors: Martine Mercier, Alain Rancurel
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Patent number: 4760377Abstract: Disclosed is a decompaction system for reading compacted paralled data from a memory and providing in real time uncompacted serial data therefrom. The decompaction system is especially suited to be utilized in pin electronics automatic test equipment for real time testing of units such as integrated circuits, circuit boards, etc. The decompaction system includes a separate channel for each pin of the unit under test (UUT) and is capable of decoding a number of types of compacted parallel data and providing serail data to each pin of the UUT in the most prevalently used test patterns. The data is compacted by software algorithms according to these patterns, stored in a memory and retrieved and decoded by the decompaction system during real-time testing of the UUT. In a specific embodiment, compacted parallel data is stored in 16-bit words in a separate memory for each channel, and is decompacted into serial data sequences of from 8 to 4096 bits per channel for each access of the respective memory.Type: GrantFiled: March 29, 1985Date of Patent: July 26, 1988Assignee: Giordano Associates, Inc.Inventor: Philip C. Jackson
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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: 4731481Abstract: Polyalkanolamines of controlled molecular weights and their uses as demulsifiers and/or flotation agents.Type: GrantFiled: November 30, 1984Date of Patent: March 15, 1988Assignee: Petrolite CorporationInventors: Thomas J. Bellos, Eva G. Lovett
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Patent number: 4695631Abstract: A process for the preparation of enamines or imines by isomerization of allylamine derivatives is described. Allylamine derivatives represented by formula (I): ##STR1## are isomerized using as a catalyst a rhodium complex represented by formula (IV):[Rh(olefin)L].sup.+ X.sup.- (IV)to form enamines or imines represented by, respectively, formula (II) or formula (III): ##STR2## All of the symbols in the above formulae are as described. These enamines or imines are useful intermediates for the preparation of a number of organic compounds.Type: GrantFiled: June 30, 1982Date of Patent: September 22, 1987Assignee: Takasago Perfumery Co., Ltd.Inventors: Seinosuke Otsuka, Kazuhide Tani, Tsuneaki Yamagata, Susumu Akutagawa, Hidenori Kumobayashi, Misao Yagi
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Patent number: 4680393Abstract: The present invention is a process for the synthesis of tertiary alkanolamines by reacting a secondary amine with an alkanediol. High selectivity for the production of alkanolamines is achieved by carrying out the reaction in the presence of a compound or complex of ruthenium in chemical combination or in admixture with an organic phosphine ligand. The organic phosphine ligand is present in an amount such that the ratio of gram mole ligand/gram atom ruthenium is greater than 5.Type: GrantFiled: May 8, 1986Date of Patent: July 14, 1987Assignee: Air Products and Chamicals, Inc.Inventor: John A. Marsella
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Patent number: 4670470Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.Type: GrantFiled: August 29, 1985Date of Patent: June 2, 1987Assignee: Merck & Co., Inc.Inventor: Raymond A. Firestone
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Patent number: 4661288Abstract: Water-soluble zwitterionic compounds having clay soil removal/anti-redeposition properties. The zwitterionic compounds are selected from monozwitterionic compounds, dizwitterionic compounds, polyzwitterionic compounds, and zwitterionic polymers. These zwitterionic compounds are useful in detergent compositions at from about 0.05 to about 95% by weight. In addition to the zwitterionic compounds, the detergent compositions further comprise from about 1 to about 75% by weight of a nonionic, anionic, ampholytic, zwitterionic, or cationic detergent surfactant or mixture thereof.Type: GrantFiled: March 8, 1985Date of Patent: April 28, 1987Assignee: The Procter & Gamble CompanyInventors: Donn N. Rubingh, Eugene P. Gosselink
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Patent number: 4642303Abstract: The present invention is directed to catalyst compositions containing nickel, copper, chromium and iron which are useful for promoting reductive amination reactions, such as the conversion of feedstocks containing one or more hydroxyl groups to corresponding amine compounds including acyclic, cyclic and heterocyclic amines. For example, the catalyst compositions of the present invention may be utilized to convert monoethanolamine to ethylenediamine and piperazine, for the conversion of diethylene glycol to morpholine and diglycolamine, etc.Type: GrantFiled: December 27, 1985Date of Patent: February 10, 1987Assignee: Texaco Inc.Inventor: Terry L. Renken
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Patent number: 4624980Abstract: An N-t-alkyl-N-sec-alkyl secondary amine compound of the formula: ##STR1## wherein X, Y and Z are each independently selected from --H, --OH, or an alkyl group having from 1 to about 15 carbon atoms; and n is an integer of from 3 to about 6.Type: GrantFiled: March 28, 1985Date of Patent: November 25, 1986Assignee: Milliken Research CorporationInventors: John W. Rekers, Edward W. Kluger
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Patent number: 4621095Abstract: The invention relates to bis-azolyl-substituted t-butanol derivatives defined herein under formula (I) and their use as antimycotic agents. Included in the invention are compositions containing said t-butanol derivatives and methods for using said derivatives and compositions containing them for their antimycotic activity.Type: GrantFiled: August 11, 1983Date of Patent: November 4, 1986Assignee: Bayer AktiengesellschaftInventors: Erik Regel, Karl H. Buchel, Manfred Plempel
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Patent number: 4618481Abstract: An alkaline absorbent composition comprising a severely hindered amino compound and an amine salt is provided. A process for the removal of H.sub.2 S from fluid mixtures using this absorbent composition to produce a very low level of H.sub.2 S in the treated fluid is also provided. The process is also suited for the selective removal of H.sub.2 S from fluid mixtures comprising H.sub.2 S and CO.sub.2.Type: GrantFiled: August 30, 1985Date of Patent: October 21, 1986Assignee: Exxon Research and Engineering Co.Inventors: Fred J. Heinzelmann, Noah S. Rothblatt, James P. Glass, Jr., Geoffrey R. Say, George R. Chludzinski, Guido Sartori, W. S. Winston Ho
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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: 4605772Abstract: N-alkane-N-alkanolamines are prepared by (a) contacting an N-alkane-N-alkanolamine having more N-alkanolamine moieties than the product compound, with a haloalkane; (b) contacting the product of step (a) with a strong base; and (c) deprotonating the product of step (b). The method of the invention produces relatively pure compounds in high yield, from low-value starting materials. The compounds produced by the invention are useful for the absorption of sulfur compounds from gases produced by the combustion of sulfur-containing hydrocarbon materials.Type: GrantFiled: December 24, 1984Date of Patent: August 12, 1986Assignee: The Dow Chemical CompanyInventors: Nicholas Darby, Gordon C. Dunmore
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Patent number: 4588843Abstract: It has been discovered that when reaction is effected between an alkali metal omega-amino-alkoxide and an alkyl halide, nucleophilic attack of the alkoxide on the alkyl halide occurs so that an (alkoxyalkyl)amine is formed. The conventional Hofmann displacement reaction (elimination of CH.sub.3 Br) does not occur to any significant extent. Nor does the common olefin elimination reaction occur to any significant extent when using alkali metal omega-aminoalkoxides having one or two C.sub.2 or higher alkyl substituents on the nitrogen atom.Type: GrantFiled: April 26, 1984Date of Patent: May 13, 1986Assignee: Ethyl CorporationInventor: Everett M. Marlett
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Patent number: 4582938Abstract: This invention relates to a polyamine composition suited for catalytically effecting reaction between organic polyisocyanate and an active hydrogen compound as measured by the Zerewitinoff method e.g. a polyol, a polyester polyol of polyether in the manufacture of urethane compositions.Type: GrantFiled: October 24, 1983Date of Patent: April 15, 1986Assignee: Air Products and Chemicals, Inc.Inventor: Howard L. Harwell
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Patent number: 4581178Abstract: Low valent transition metal complexes containing small cone angle phosphine or arsine ligands efficiently catalyze addition of aldehydes to compounds or groups having a C--H bond activated by a nitro or nitrile group, to provide nitroalcohols or cyanohydrins, respectively.Type: GrantFiled: February 28, 1985Date of Patent: April 8, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: David Milstein
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Patent number: 4560798Abstract: This invention pertains to the production of aminoethylethanolamine in high selectivity by the intermolecular condensation of monoethanolamine with itself. Selective intermolecular condensation is achieved by reacting monoethanolamine with itself at a temperature from 175.degree.-275.degree. C., and a pressure from 50-400 psig, said reaction being carried out in the presence of a rare earth metal or a strontium metal hydrogen phosphate.Type: GrantFiled: October 25, 1984Date of Patent: December 24, 1985Assignee: Air Products and Chemicals, Inc.Inventors: Michael E. Ford, Thomas A. Johnson
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Patent number: 4558071Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.Type: GrantFiled: February 25, 1983Date of Patent: December 10, 1985Assignee: Merck & Co., Inc.Inventor: Raymond A. Firestone
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Patent number: 4536347Abstract: Ruthenium-on-charcoal and ruthenium-on-carbon black catalysts, containing from 0.1 to 5% by weight of iron, for the preparation of olefinically unsaturated alcohols by selective hydrogenation of the corresponding .alpha., .beta.-unsaturated carbonyl compounds in the liquid phase are prepared by modifying the catalyst with iron only after it has been impregnated with the ruthenium compound, and reducing the catalyst with hydrogen at from 400.degree. to 600.degree. C., with thorough mixing.The catalysts according to the invention are particularly useful for improving the industrially difficult hydrogenation of citral to give the soughtafter fragrances geraniol and nerol.Type: GrantFiled: March 19, 1984Date of Patent: August 20, 1985Assignee: BASF AktiengesellschaftInventors: Michael Horner, Matthias Irgang
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Patent number: 4521626Abstract: 5-Methyl-2-oxazolidinone and 5-methyl-3-(2-hydroxypropyl)-2-oxazolidinone are prepared by contacting urea and propylene carbonate in the presence of an initiator at a temperature from about 120.degree. C. to about 200.degree. C.Type: GrantFiled: April 19, 1984Date of Patent: June 4, 1985Assignee: The Dow Chemical CompanyInventor: Larry D. Kershner
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Patent number: 4500717Abstract: The invention is a process for the preparation of 2-oxazolidinones which comprises contacting a 2-hydroxyalkyl carbamate with an alkylene oxide or alkylene carbonate in the presence of a catalytic amount of a quaternary ammonium halide, quaternary phosphonium halide, a group I metal carbonate, hydroxide, oxide or halide, or a group II metal carbonate, hydroxide, oxide or halide under conditions such that a 2-oxazolidinone is prepared.Type: GrantFiled: March 28, 1983Date of Patent: February 19, 1985Assignee: The Dow Chemical CompanyInventors: Frank T. Cook, Michael O. Nutt, Hsin H. Hsieh
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Patent number: 4491583Abstract: A process for inducing the production of endogenous interferon in a vertebrate animal which comprises parenterally, intranasally or topically adminstering to the animal an interferon-inducing effective amount of composition containing as the essential active ingredient a compound of the formula ##STR1## or a non-toxic acid addition salt thereof wherein R.sub.7 and R.sub.8 are each alkyl of from 12 to 30 carbon atoms and Z is selected from the group consisting of N-(lower alkyl)-piperazino and N-(W-hydroxy-lower alkyl)-piperazino, said lower alkyl groups having from 1 to 4 carbon atoms.Type: GrantFiled: July 18, 1983Date of Patent: January 1, 1985Assignee: Pfizer Inc.Inventors: Timothy H. Cronin, Hermann Faubl, William W. Hoffman, James J. Korst
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Patent number: 4450246Abstract: A process for producing a polyurethane foam by reacting an organic polyisocyanate with an organic polyester polyol or polyether polyol in the presence of a catalytic amount of specific amine compounds of the formula: ##STR1## wherein R.sup.1 is a methyl or ethyl and R.sup.2 is hydrogen or methyl such that when R.sup.1 is methyl, R.sup.2 is methyl and when R.sup.1 is ethyl, R.sup.2 is hydrogen, X is an organic mono or dicarboxylic acid and n is an integer from 0 to 1.Type: GrantFiled: October 26, 1982Date of Patent: May 22, 1984Assignee: W. R. Grace & Co.Inventor: Felek Jachimowicz