Of Ether Or Alkylene Oxide Patents (Class 564/399)
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Patent number: 5288910Abstract: 4-amino-2-buten-1-ol is formed by the regioselective addition of primary amines or ammonia to 3,4-epoxy-1-butene. A quantity of a the primary amine or ammonia is reacted with 3,4-epoxy-1-butene in a reaction medium in the presence of a catalyst. The reaction medium is a liquid which has an E.sub.T (30) no less than about 32. The catalyst is a complex of palladium and phosphine ligands.Type: GrantFiled: September 4, 1992Date of Patent: February 22, 1994Assignee: Eastman Kodak CompanyInventor: Yann Hung
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Patent number: 5210325Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalyst which comprises one or more compounds comprising a rare earth element and phosphorus supported on an inert porous support. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: August 10, 1992Date of Patent: May 11, 1993Assignee: Shell Oil CompanyInventors: Richard A. Kemp, Paul R. Weider
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Patent number: 5166440Abstract: Aromatic amines, alkylated on the N-atom, can be prepared by catalytic alkylation of aromatic amines with alcohols or the corresponding ethers or by transalkylation with aromatic amines alkylated on the N-atom, whereby niobic acid or tantalic acid is used as the catalyst.Type: GrantFiled: December 12, 1990Date of Patent: November 24, 1992Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Helmut Waldmann, Rudolf Braden
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Patent number: 5162589Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of sodium barium phosphate or potassium barium phosphate. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvent, and chemical intermediates.Type: GrantFiled: June 8, 1992Date of Patent: November 10, 1992Assignee: Shell Oil CompanyInventors: Rudolf J. Wijngaarden, Kees Latjes
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Patent number: 5159115Abstract: Described are processes for the gas-phase mono N-alkylation of an aniline or an aminonaphthalene using a C.sub.1 to C.sub.5 aliphatic alcohol or ether over certain catalyst compositions based upon crystalline molecular sieves or amorphous silica-aluminas.Type: GrantFiled: August 18, 1989Date of Patent: October 27, 1992Assignee: Amoco CorporationInventors: Peter G. Pappas, Judith B. Melville
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Patent number: 5141968Abstract: The present invention relates to polyether polyols having OH numbers of about 300 to 630 obtained by sequentially reacting 2,4- and/or 2,6-tolylenediamine or mixtures of 2,4-and/or 2,6-tolylenediamine and one or more other aromatic amines with from about 1 to 2.5 moles of ethylene oxide for each NH.sub.2 group, and then with from about 0.5 to 5 moles of propylene oxide for each NH.sub.2 group, wherein said polyether polyols contain secondary amino groups comprising from about 2 to 20% of the isocyanate-reactive groups in said polyols and a free aromatic amine content of less than about 0.2% by weight. The present invention further relates to a process for preparing the polyether polyols of the invention, as well as to a method of using the polyether polyols for the preparation of polyurethane plastics.Type: GrantFiled: August 15, 1989Date of Patent: August 25, 1992Assignee: Bayer AktiengesellschaftInventors: Manfred Dietrich, Reinhard Kaufung
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Patent number: 5142052Abstract: Aryl- and heterocyclic-methanamines are prepared by reacting a hydroxy-aryl carbinol or a heterocyclic carbinol with a primary or a secondary amine in the presence of a cationic effect reagent.Type: GrantFiled: October 21, 1988Date of Patent: August 25, 1992Assignee: Laboratoires SyntexInventors: Serge Beranger, Bruno Francois
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Patent number: 5118870Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of a xerogel comprising one or more compounds comprising a rare earth element and phorphorus. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: April 23, 1990Date of Patent: June 2, 1992Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 5117064Abstract: A method for synthesizing an aromatic amine, an aromatic alcohol or an aromatic thiol by an aromatic nucleophilic substitution reaction is disclosed, which comprises reacting a compound represented by formula (I): ##STR1## wherein Q.sup.1 represents an aromatic ring; EWG represents a group having a positive Hammett's .sigma..sub.p value; m represents an integer of 1 to 5; n represents an integer of 1 to 3; and X represents a group represented by formula (III): ##STR2## wherein R.sup.4 represents hydrogen atom, an aryl group or an alkyl group; Q.sup.2 represents an atomic group for forming an aromatic ring; and Z.sup.1 and Z.sup.2 each represents an oxygen atom or a sulfur atom with a nucleophilic reagent represented by formula (II):M--Y (II)wherein M represents a hydrogen atom, a metal atom or an ammonium; Y represents a --NHR.sup.1 group, an --OR.sup.1 group, or a --SR.sup.1 group; R.sup.1 represents a hydrogen atom, an alkyl group, an aryl group, a residue of a heterocyclic ring, a --NR.sup.2 R.sup.Type: GrantFiled: January 25, 1991Date of Patent: May 26, 1992Assignee: Fuji Photo Film Co., Ltd.Inventors: Takayuki Ito, Koki Nakamura
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Patent number: 5097071Abstract: The novel copper catalyst on an Al.sub.2 O.sub.3 -containing carrier which is impregnated with compounds of manganese and of one or more rare earth metals, having a Cu content of 0.1-5% by weight, a total content of compounds of manganese and of the rare earth metal or metals of 0.05 to 8% by weight, calculated as metals, is described, the weight ratio of rare earth metal(s) to manganese being 5:1-1:5, calculated as metal, and all percentages being relative to the total weight of the catalyst. Such catalyst is prepared by first impregnating the carrier with compounds of manganese and of the rare earth metal or metals, then fixing the copper salt on the impregnated carrier and activating the catalyst in a preferred manner by treatment with H.sub.2 at 150.degree. to 350.degree. C. Such a catalyst is suitable, for example, for the N-alkylation of aromatic amines with alkanols, where the aromatic amines can be prepared from the parent nitro compounds in an alkylation reactor with simultaneous addition of H.sub.2.Type: GrantFiled: September 20, 1990Date of Patent: March 17, 1992Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Hans-Helmut Schwarz, Rudolf Braden
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Patent number: 5093526Abstract: N-n-propyl-N-2-(2,4,6-trichlorophenoxy) ethyl amine is prepared by reacting 2-phenoxy ethanol with thionyl chloride in the presence of a catalytic amount of tetra-alkyl ammonium halide optionally in the presence of a solvent to form 2-phenoxy ethyl chloride; reacting the 2-phenoxy ethyl chloride with n-propylamine at a temperature of from 50.degree. C. to 150.degree. C. optionally in the presence of a solvent to form N-n-propyl-N-2-phenoxy-ethyl amine; selectively chlorinating N-n-propyl-N-2-phenoxyethyl amine with chlorine in the presence of a solvent; and recovering the N-n-propyl-N-2-(2,4,6-trichlorophenoxy) ethyl amine formed.Type: GrantFiled: June 14, 1990Date of Patent: March 3, 1992Assignee: Makhteshim Chemical Works Ltd.Inventors: Joseph Sharvit, Abraham A. Pereferkovich
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Patent number: 5091577Abstract: N-n-propyl-N-(2,4,6-trichlorophenoxy)-ethyl amine is prepared by reacting 2-phenoxy ethanol with thionyl chloride in the presence of a catalytic amount of tetraalkyl ammonium halide optionally in the presence of a solvent to form 2-phenoxy ethyl chloride; selectively chlorinating the 2-phenoxy ethyl chloride with chlorine at a temperature from 0.degree. C. to 60.degree. C. in the presence of a catalytic amount if urea to form 2-(2,4,6-trichlorophenoxy)-ethyl chloride; reacting the 2-(2,4,6-trichlorophenoxy)-ethyl chloride with n-propyl amine at a temperature of from 20.degree. C. to 150.degree. C., optionally in the presence of water; and recovering the N-n-propyl-N-2-(2,4,6-trichlorophenoxy)-ethyl amine formed.Type: GrantFiled: June 14, 1990Date of Patent: February 25, 1992Assignee: Makhteshim Chemical Works Ltd.Inventors: Joseph Sharvit, Abraham A. Pereferkovich
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Patent number: 5091578Abstract: N-n-propyl-N-2-(2,4,6-trichlorophenoxy)-ethylamine is prepared by selectively chlorinating 2-phenoxy ethanol by reacting it with chlorine either in the presence of hydrogen chloride at a temperature of from -10.degree. C. to 50.degree. C. or in the presence of urea at a temperature of from 20.degree. C. to 55.degree. C. in a water/carbon tetrachloride solvent mixture to form 2-(2,4,6-trichlorophenoxy)ethanol; reacting the 2-(2,4,6-trichlorophenoxy)ethanol with thionyl chloride in the presence of a catalytic amount of tetraalkyl ammonium chloride, optionally in the presence of a solvent to form 2-(2,4,6-trichlorophenoxy)ethyl chloride; and reacting the 2-(2,4,6-trichlorophenoxy) ethyl chloride with n-propylamine at a temperature of from 20.degree. C. to 150.degree. C., optionally in the presence of water to form N-n-propyl-N-2-(2,4,6-trichlorophenoxy) ethyl amine.Type: GrantFiled: June 14, 1990Date of Patent: February 25, 1992Assignee: Makhteshim Chemical Works Ltd.Inventors: Joseph Sharvit, Abraham A. Pereferkovich, Daniel Shohat
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Patent number: 5087754Abstract: N,N-dialkylanilines can be prepared by reacting the anilines on which they are based with lower alcohols or with the corresponding ethers, at an increased temperature in the gas phase in the presence of a proton-containing zeolite catalyst of the pentasil type having an SiO.sub.2 /Al.sub.2 O.sub.3 ratio of >60, it being advantageous to carry out the alkylation process under a pressure of 2-30 bar.Type: GrantFiled: August 13, 1990Date of Patent: February 11, 1992Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Heinrich Pelster, Lothar Puppe, Peter Wimmer
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Patent number: 5068434Abstract: N-alkylated anilines can be prepared by reaction of anilines with lower alcohols or dialkyl ethers at elevated temperature and in the presence of zeolite catalysts of the pentasil type containing protons and having an SiO.sub.2 /Al.sub.2 O.sub.3 ratio of at least 60.Type: GrantFiled: January 25, 1989Date of Patent: November 26, 1991Assignee: Bayer AktiengesellschaftInventors: Gunter Klug, Hans-Josef Buysch, Lothar Puppe
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Patent number: 5059719Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more C.sub.2 to C.sub.4 vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more soluble basic compounds of one or more elements of the lanthanum series (atomic numbers 57-71, inclusive). The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates. When the process is applied to the preparation of alkylene oxide, particularly ethylene oxide, adducts of alkanols, particularly primary alkanols in the C.sub.6 to C.sub.24 range, the product is a valuable narrow range nonionic surfactant, characterized by relatively narrow distribution of alkylene oxide adducts.Type: GrantFiled: March 23, 1990Date of Patent: October 22, 1991Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 5057627Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more of the phosphate salts of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: February 20, 1990Date of Patent: October 15, 1991Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 5057628Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more compounds of one or more of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: February 20, 1990Date of Patent: October 15, 1991Assignee: Shell Oil CompanyInventors: Charles L. Edwards, Richard A. Kemp
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Patent number: 5055617Abstract: Anilines or N-alkyl-anilines are advantageously reacted with alkyl alcohols or the associated dialkyl ethers at elevated temperature in the gas phase, if a .gamma.-Al.sub.2 O.sub.3 is used that is prepared by dehydration of an aluminum oxide/hydroxide hydrate and has a BET surface area from 50 to 400 m.sup.2 /g and a surface acidity of 5 to 600 mmol H.sup.+ /kg.Type: GrantFiled: July 12, 1990Date of Patent: October 8, 1991Assignee: Bayer AktiengesellschaftInventors: Peter Wimmer, Hans-Josef Buysch, Lothar Puppe, Christian Froehlich
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Patent number: 5030758Abstract: This invention relates to o-tolylenediamine-based polyether polyols having an OH number of about 400 to 630, in which about 5 to 20% of the isocyanate-reactive groups of the polyether polyols are secondary amino groups and which contain less than about 0.2% by weight free o-tolylenediamine. The polyether polyols of the invention are formed by sequential reaction of o-tolylenediamine first with about 2 to 5 mol of ethylene oxide and then with about 1 to 5 mol of propylene oxide per mol of o-tolylenediamine. This invention also relates to the process for the production of polyether polyols using said sequential reaction at a temperature of about 90.degree. to 125.degree. C. and in the presence of an amine catalyst.Type: GrantFiled: November 29, 1988Date of Patent: July 9, 1991Assignee: Bayer AktiengesellschaftInventors: Manfred Dietrich, Reinhard Kaufung
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Patent number: 5026923Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more of the borate salts of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: May 29, 1990Date of Patent: June 25, 1991Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 5015773Abstract: An amine is produced by reacting in the presence of hydrogen at elevated temperature a first reactant which is a compound substantially involatile at the elevated temperature employed and having either one, two or more hydroxyl functions, each of which is independently either a primary or secondary hydroxyl function, with a second reactant which is either ammonia or a primary or a secondary amine in the presence of a reductive amination catalyst wherein the reaction is effected in either a continuously or periodically open system.Type: GrantFiled: August 4, 1989Date of Patent: May 14, 1991Assignee: BP Chemicals LimitedInventor: Ian D. Dobson
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Patent number: 5015769Abstract: New 3-amino-4-nitrophenols, the process for preparation thereof and their use in dyeing keratinous fibers, and new intermediate 4,5-dinitrophenols.The present invention relates to a 3-amino-4-nitrophenol of formula: ##STR1## where Z denotes --CH.sub.2 --W, W denoting hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.6 polyhydroxyalkyl, (C.sub.1 -C.sub.3)alkoxy(C.sub.1 -C.sub.6)alkyl or (C.sub.1 -C.sub.3)hydroxyalkoxy(C.sub.1 -C.sub.6)alkyl and R denotes hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.6 polyhydroxyalkyl or (C.sub.1 -C.sub.3)alkoxy(C.sub.1 -C.sub.6)alkyl, the process for preparation thereof and the intermediate compound of formula: ##STR2## in which Z' denotes CH.sub.2 --W, W denoting C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.6 polyhydroxyalkyl, (C.sub.1 -C.sub.3)alkoxy-(C.sub.1 -C.sub.6)alkyl or (C.sub.1 -C.sub.3)hydroxyalcoxy(C.sub.1 -C.sub.6)alkyl.Type: GrantFiled: June 19, 1990Date of Patent: May 14, 1991Assignee: L'OrealInventors: Alex Junino, Gerard Lang, Alain Genet
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Patent number: 4997987Abstract: Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) from 3,5-dichloroanisole. Nitration of 3,5-dichloroanisole under relatively mild conditions gave 3,5-dichloro-2,4,6-trinitroanisole in high yield and purity. Ammonolysis of this latter compound gave the desired TATB. Another route to TATB was through the treatment of the 3,5-dichloro-2,4,6-trinitroanisole with thionyl chloride and dimethylformamide to yield 1,3,5-trichloro-2,4,6-trinitrobenzene. Ammonolysis of this product produced TATB.Type: GrantFiled: June 8, 1990Date of Patent: March 5, 1991Assignee: The United States of America as represented by the United States Department of EnergyInventors: Donald G. Ott, Theodore M. Benziger
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Patent number: 4967016Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of the compound barium phosphate. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: January 29, 1990Date of Patent: October 30, 1990Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 4960952Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more lanthanum compounds comprising silicate, metasilicate and mixtures thereof. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: August 31, 1989Date of Patent: October 2, 1990Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 4929764Abstract: By reacting a primary aromatic amine with a dialkyl ether in the presence of a titanium dioxide alkylation catalyst having a surface area below about 130 square meters per gram, preferably in the anatase crystallographic form, at a suitably elevated temperature above about 300.degree. C., the amount of exclusively ring-alkylated product formed exceeds the amount of exclusively N-alkylated product formed.Type: GrantFiled: September 16, 1985Date of Patent: May 29, 1990Assignee: Ethyl CorporationInventor: Duane C. Hargis
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Patent number: 4902834Abstract: A process is disclosed for the preparation of capped polyoxyalkylene block polyethers with exceptionally low hydroxyl numbers and correspondingly high capping efficiency. This improvement is accomplished through the use of cesium hydroxide catalysis during oxyethylation.Type: GrantFiled: August 30, 1988Date of Patent: February 20, 1990Assignee: BASF CorporationInventors: Jay G. Otten, Roger A. Ott
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Patent number: 4888445Abstract: The invention relates to a compound of formula ##STR1## in which: X denotes a branched or unbranched alkylene radical containing 2 to 6 carbon atoms, optionally being able to be substituted with one or more hydroxyl radicals;R denotes a hydrogen atom, an alkyl or a mono- or polyhydroxyalkyl radical or an aminoalkyl radical in which the amine group can be mono- or disubstituted with an alkyl radical or with a mono- or polyhydroxyalkyl radical, the nitrogen atom also being able to form part of a heterocyclic system and the alkyl radicals containing 1 to 4 carbon atoms;R' denotes a hydrogen atom or a C.sub.1 to C.sub.4 alkyl radical;Y and Z denote a nitro and/or --NHR.sub.1 radical, R.sub.Type: GrantFiled: November 10, 1987Date of Patent: December 19, 1989Assignee: L'OrealInventors: Alex Junino, Gerard Lang, Nicole Jehanno
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Patent number: 4855505Abstract: The invention relates to a ruthenium promoted nickel and/or cobalt dehydrogenation-hydrogenation catalyst. The ruthenium on the catalyst is applied from a solution containing a ruthenium halide compound. The catalyst use in organic reactions and a process performed in its presence are also described. Preferably, the catalyst is used to aminate alkylene oxides, alcohols, phenols, alkanolamines, aldehydes, and ketones.Type: GrantFiled: December 8, 1986Date of Patent: August 8, 1989Assignee: Berol Kemi ABInventor: Juhan Koll
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Patent number: 4806686Abstract: N-(D)-ribitylxylidine (I) is prepared by reacting (D)-ribose (II) with 3,4-dimethylaniline (III) or 3,4-dimethyl-1-nitrobenzene (IV) in aqueous or aqueous/organic solution or in solution in a water-soluble organic solvent under an elevated hydrogen pressure and in the presence of a hydrogenation catalyst and of a boric acid compound,(a) using the boric acid compound in a catalytic amount of from about 6 to 35 mmol, preferably from 6 to 20 mmol, per mol of ribose,(b) carrying out the reaction under a hydrogen pressure of from 1 to 20, preferably from 2 to 9, bar and(c) carrying out the hydrogenation at from 40.degree. to 80.degree. C. over Raney nickel as hydrogenation catalyst.Type: GrantFiled: April 27, 1987Date of Patent: February 21, 1989Assignee: BASF AktiengesellschaftInventors: Hansgeorg Ernst, Hartmut Leininger, Joachim Paust
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Patent number: 4762950Abstract: The subject invention relates to compositions prepared by oxyalkylation of N-(2-hydroxyalkyl)-aniline as the initiator compound with one or more alkylene oxides at elevated temperatures and in the presence of an alkali metal hydroxide. The resulting compositions have an unsymmetric structure with two functional groups, a secondary amino nitrogen and a hydroxyl group. The initiator compound reacts completely and removal of any residual initiator from the polyol is not required. When the subject invention polyol composition is reacted with an isocyanate, both urea and urethane groups form. The subject polyols may be used in the preparation of polyurethane products as well as nonionic and ionic surfactants.Type: GrantFiled: December 16, 1985Date of Patent: August 9, 1988Assignee: BASF CorporationInventors: Alexander Korczak, William W. Levis, Jr.
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Patent number: 4728555Abstract: Process for the preparation of .beta.-hydroxypolyamines by reaction of polyepoxide compounds with ammonia, in which at least one polyepoxide compound is treated in a first stage with liquid ammonia at temperatures below 50.degree. C., a homogeneous phase being formed, after which the reaction between the polyepoxide compound and ammonia is carried out in a second stage at 60.degree. to 130.degree. C., and when the reaction is complete, the excess ammonia is removed from the reaction mixture.The resulting .beta.-hydroxypolyamines are used as binders or--in protonated form--as binders which can be diluted with water, by themselves or in combination with suitable crosslinking agents.Type: GrantFiled: August 15, 1986Date of Patent: March 1, 1988Assignee: Hoechst AGInventors: Hans-Joachim Kiessling, Wilhelm Riemenschneider
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Patent number: 4721810Abstract: Aromatic amines are alkylated by reaction with an acyclic ether or an unstrained cyclic ether in the presence of a B-subgroup metal oxide alkylation catalyst, preferably a Group IV-B metal oxide with or without a minor proportion of a Group VI-B or Group VIII metal oxide, so that alkylation of the aromatic amine occurs. Under most reaction conditions ether alkylating agents such as diethyl ether not consumed in the alkylation reaction pass through the reaction zone undecomposed and thus can be readily recovered for recycle or other use.Type: GrantFiled: June 6, 1984Date of Patent: January 26, 1988Assignee: Ethyl CorporationInventor: Duane C. Hargis
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Patent number: 4670557Abstract: This invention relates to the reaction of aliphatic epoxides and primary amines to form hydroxymorpholines or morpholines by a process comprising reacting said epoxide and primary amine in the presence of a ruthenium-containing compound plus a tertiary phosphine.Type: GrantFiled: September 2, 1986Date of Patent: June 2, 1987Assignee: Texaco Inc.Inventor: Wei-Yang Su
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Patent number: 4665239Abstract: Polyethers having molecular weights of about 1000 to about 75,000 modified with alpha-olefin oxides having about 12 to about 18 carbon atoms exhibit increased thickening efficiency in aqueous systems. About 1 to about 20 percent by weight based upon the weight of the polyether is required, the proportion of alpha-olefin oxide modifier varying inversely with the molecular weight of the polyether. Modified polyethers, processes for the preparation of thickened aqueous systems, and thickened aqueous compositions are disclosed. The modified polyether thickening agents of the invention are particularly useful for thickening water or water-glycol mixtures which are useful as hydraulic fluids.Type: GrantFiled: May 31, 1984Date of Patent: May 12, 1987Assignee: BASF CorporationInventors: Edward J. Panek, Pauls Davis
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Patent number: 4562290Abstract: The subject invention relates to adducts of vicinal toluenediamine prepared by:(a) reacting from one to three moles of ethylene oxide with vicinal toluenediamine at a temperature of 125.degree. C., and(b) reacting the product of (a) with four to eight moles of propylene oxide at a temperature of at least 140.degree. C. in the present of at least 1.0 part of an alkali metal hydroxide catalyst.The adducts generally have a hydroxyl number of 300 to 500 and are particularly useful for the preparation of rigid polyurethane foams.Type: GrantFiled: December 1, 1981Date of Patent: December 31, 1985Assignee: BASF Wyandotte CorporationInventors: Alexander Korczak, William W. Levis, Jr.
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Patent number: 4526608Abstract: Substituted phenoxyphenylhydroxyamines and pyridyloxyphenylhydroxyamines, and the use thereof for the control of weeds.Type: GrantFiled: March 31, 1983Date of Patent: July 2, 1985Assignee: Zoecon CorporationInventor: Shy-Fuh Lee
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Patent number: 4506039Abstract: Polymer-containing polyether polyamines containing terminal aromatically-bound amino groups are produced by in situ polymerization of a polyether polyamine with an olefinically unsaturated monomer. The polyether polyamine starting material must have terminal aromatic amino groups, a molecular weight of from 800 to 10,000 and an aromatic amino group content of from 0.3 to 16 wt. %. Suitable olefinically unsaturated monomers include .alpha.,.beta.-unsaturated nitriles, aromatic vinyl compounds, .alpha.,.beta.-unsaturated carboxylic acids and esters thereof, vinyl esters, vinyl halides, vinylidene halides, .alpha.,.beta.-unsaturated carboxylic acid amides and aminoalkyl esters of unsaturated carboxylic acids. Acrylonitrile/styrene mixtures are preferred monomers. The starting materials are employed in quantities such that the product modified polyether polyamine contains from 1 to 60 wt. % polymer or graft-polymer. The product polyamines are particularly useful in the production of polyurethanes.Type: GrantFiled: December 20, 1982Date of Patent: March 19, 1985Assignee: Bayer AktiengesellschaftInventors: Gerhard Balle, Werner Rasshofer, Winfried Schoberth
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Patent number: 4469822Abstract: The subject invention relates to polyol compositions which are alkylene oxide adducts of a mixture of initiators comprising vicinal toluenediamine and an initiator selected from the group consisting of glycerin, pentaerythritol, sucrose, sorbitol, trimethylolpropane, and mixtures thereof. Low molecular weight diols may also be used as a co-initiator in combination with the glycerin, pentaerythritol, sucrose, sorbitol, trimethylolpropane, and mixtures thereof.The subject polyol compositions are particularly useful in the preparation of rigid polyurethane foams.Type: GrantFiled: July 14, 1983Date of Patent: September 4, 1984Assignee: BASF Wyandotte CorporationInventors: Theodore O. Stolz, Richard A. Moore, James P. Lutz
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Patent number: 4397966Abstract: The subject invention relates to polyol compositions which are alkylene oxide adducts of a mixture of initiators comprising vicinal toluenediamine and an initiator selected from the group consisting of ammonia, an aliphatic amine having a molecular weight of from 20 to 120, an alkanolamine having a molecular weight of from 50 to 120, and mixtures thereof. Low molecular weight diols may also be used as a co-initiator in combination with ammonia, an aliphatic amine, an alkanolamine, or mixtures thereof.The subject polyol compositions are particularly useful in the preparation of rigid polyurethane foams.Type: GrantFiled: December 1, 1981Date of Patent: August 9, 1983Assignee: BASF Wyandotte CorporationInventors: Theodore O. Stolz, Richard A. Moore, James P. Lutz
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Patent number: 4395572Abstract: This invention relates to a process of preparing N-alkyl-nitroanilines selected from the group consisting of N-alkyl-mononitroanilines and N-alkyl-dinitroanilines by the O-alkylation of a nitrophenol to produce the corresponding alkoxy derivative, followed by reaction of the alkoxy derivative with alkylamine to produce the desired N-alkyl-nitroaniline.Type: GrantFiled: April 20, 1981Date of Patent: July 26, 1983Assignee: Union Carbide CorporationInventor: John K. Chan
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Patent number: 4391728Abstract: The subject invention relates to polyol compositions comprising the reaction product prepared by reacting from 4 to 9 moles of propylene oxide per mole of toluenediamine by weight at temperatures greater than 140.degree. C. in the presence of at least 0.6 parts of alkali metal hydroxide per 100 parts by weight of toluenediamine, with the proviso that at least 0.8 part by weight of alkali metal hydroxide is used if the toluenediamine is 2,4-toluenediamine, or 2,6-toluenediamine, or mixtures thereof.Type: GrantFiled: December 1, 1981Date of Patent: July 5, 1983Assignee: BASF Wyandotte CorporationInventors: Alexander Korczak, William W. Levis, Jr.
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Patent number: 4386939Abstract: Aminophenols and analogous aromatic compounds, especially those containing a hydrocarbon-based substituent preferably having about 10 to about 750 aliphatic carbon atoms, react with 3- or 4-membered ring heterocyclic compounds, preferably epoxides, to form compositions useful as dispersants and detergents in lubricants and fuels.Type: GrantFiled: April 1, 1982Date of Patent: June 7, 1983Assignee: The Lubrizol CorporationInventor: Richard M. Lange
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Patent number: 4364875Abstract: The method of preparing a compound of the formula ##STR1## wherein R.sub.1 is hydrogen, halogen, alkyl of 1 to 8 carbon atoms, trifluoromethyl or acetyl;n is 1 when R.sub.1 has all the defined meanings, or 2 or 3 when R.sub.1 is halogen or alkyl;R.sub.2 is hydrogen; alkyl of 1 to 16 carbon atoms; alkenyl of 2 to 16 carbon atoms; alkinyl of 2 to 16 carbon atoms; monosubstituted alkyl of 2 to 6 carbon atoms, where the substituent is hydroxyl, alkoxy of 1 to 4 carbon atoms, phenoxy, halo-phenoxy, (alkyl of 1 to 4 carbon atoms) phenoxy, (alkoxy of 1 to 4 carbon atoms)phenoxy, nitro-phenoxy, cyano-phenoxy, amino or (alkyl of 1 to 4 carbon atoms)thio; benzyl; halo-benzyl; --NR.sub.3 R.sub.4 ; --CHR.sub.3 --COOR.sub.4 ; or --CHR.sub.3 --CONR.sub.4 R.sub.5, whereR.sub.3, R.sub.4 and R.sub.5 are each hydrogen or alkyl of 1 to 8 carbon atoms; andX.sub.1 and X.sub.2 are each hydrogen or halogen,which comprises reacting a compound of the formula ##STR2## wherein n, R.sub.1, X.sub.1 and X.sub.Type: GrantFiled: July 7, 1981Date of Patent: December 21, 1982Assignee: Celamerck GmbH & Co. KGInventors: Richard Sehring, Wolfgang Buck
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Patent number: 4322530Abstract: A process for alkylating a polyamine by contacting, in a liquid media, a polyamine, an olefinic compound, carbon monoxide, and a hydrogen source in the presence of a catalytic amount of a rhodium atom containing compound selected from metallic rhodium, rhodium salts, rhodium oxides, rhodium carbonyls and ligands thereof at a temperature of from about 50.degree. C. to 250.degree. C. and at a pressure of from about 30 to about 300 atmospheres.Type: GrantFiled: February 22, 1980Date of Patent: March 30, 1982Assignee: W. R. Grace & Co.Inventor: Felek Jachimowicz
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Patent number: 4317932Abstract: A process for forming amines by contacting, in a liquid media, an olefinic compound, carbon monoxide, water, and ammonia in the presence of a rhodium atom containing compound selected from metallic rhodium, rhodium salts, rhodium oxides, and rhodium carbonyls and ligands thereof at a temperature of from 50.degree. to 250.degree. C. and at a pressure of from about 10 to about 300 atmospheres.Type: GrantFiled: February 22, 1980Date of Patent: March 2, 1982Assignee: W. R. Grace & Co.Inventor: Felek Jachimowicz
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Patent number: 4289907Abstract: This invention relates to a process of preparing N-alkyl-nitroanilines selected from the group consisting of N-alkyl-mononitroanilines and N-alkyl-dinitroanilines by the O-alkylation of a nitrophenol to produce the corresponding alkoxy derivative, followed by reaction of the alkoxy derivative with alkylamine to produce the desired N-alkyl-nitroaniline.Type: GrantFiled: December 27, 1979Date of Patent: September 15, 1981Assignee: Union Carbide CorporationInventor: John K. Chan
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Patent number: 4252824Abstract: New compounds of the formula ##STR1## are disclosed wherein R.sub.1 =H, linear or branched alkyl-radical with from 1 to 6 carbon atoms, cycloalkyl radical with from 3 to 6 carbon atoms, alkylphenyl radical where the phenyl group may be in turn substituted with a hydroxy or methoxy group;R.sub.2 =hydroxy, hydromethylR.sub.3 =H, alkyl with 1-4 carbon atoms, formyl, carboalkyl where the alkyl groups have 1-3 carbon atoms, carbomido group simple or mono- or di-substituted on the nitrogen atom with alkyl radicals containing 1-3 carbon atoms.The new compounds are useful in the treatment of bronchial affections. They are endowed with unique properties in that they provide the desired bronchial dilation effect without any concomitant cardiac stimulation.Type: GrantFiled: November 10, 1976Date of Patent: February 24, 1981Assignee: Valeas S.R.L., Industria Chimica e FarmaceuticaInventors: Virgilio Bernareggi, Giuseppe Crespi, Giuseppe Bugada