Of An Alkylene Oxide Patents (Class 564/475)
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Patent number: 4987271Abstract: A method for purifying a polyoxyalkylene alcohol, which comprises treating with a treating agent consisting essentially of a pH buffer, a polyoxyalkylene alcohol containing a double metal cyanide complex catalyst, synthesized by ring-opening polymerization of an alkylene oxide in the presence of said catalyst, and then removing the catalyst and the treating agent from the polyoxyalkylene alcohol.Type: GrantFiled: February 14, 1990Date of Patent: January 22, 1991Assignee: Asahi Glass Company, Ltd.Inventors: Takashi Watabe, Hiromitsu Takeyasu, Takao Doi, Nobuaki Kunii
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Patent number: 4985546Abstract: A substituted colorant which may be copolymerized with a condensation polymer to provide a covalently bound, nonextractable coloring, having the formula ##STR1## wherein R and R.sub.1 are independently selected from hydrogen or lower alkyl; R.sub.4 is selected from hydrogen or lower alkyl; x is 0 or 1; N and M are each integers of from 1 to about 100 and the sum of N and M is from 3 to about 100. The hydroxyl groups are protected by formation of a ring structure during alkoxylation and amination of the substituent.Type: GrantFiled: June 19, 1989Date of Patent: January 15, 1991Assignee: Milliken Research CorporationInventors: John W. Miley, John W. Rekers
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Patent number: 4983778Abstract: Alkoxylation products of organic compounds containing active H atoms with a narrow homolog distribution range is produced by using as a catalyst in the alkoxylation process a catalyst composition comprising:a. Esters of titanic and/or zirconic acid with monoalkanols containing 1 to 4 carbon atoms in combination with,b. sulfuric acid and/or alkanesulfonic acid containing 1 to 6 carbon atoms and/or hydroxyarylsulfonic acids as catalysts for the ethoxylation or propoxylation of compounds containing active H atoms provide the alkoxylation products with a narrow homolog distribution range.Type: GrantFiled: May 2, 1989Date of Patent: January 8, 1991Assignee: Henkel Kommanditgesellschaft auf AktienInventor: Uwe Ploog
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Patent number: 4983736Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a metallic polyphosphate condensation catalyst having a condensed structure. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentatethylenehexamine (PEHA).Type: GrantFiled: August 8, 1989Date of Patent: January 8, 1991Assignee: Union Carbide Chemicals and Plastic Company Inc.Inventors: Arthur R. Doumaux, Jr., David J. Schreck
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Patent number: 4977281Abstract: Primary amino polyoxyalkylene 1,3-dioxane or 1,3-dioxolane compounds are provided of the formula: ##STR1## wherein R and R.sub.1 are independently selected from hydrogen or a lower alkyl group; R.sub.2 and R.sub.3 are independently selected from hydrogen, phenyl or lower alkyl groups; R.sub.4 is selected from hydrogen or a lower alkyl group; x is 0 or 1; N and M are each integers of from 1 to about 100 and the sum of N an M is from 2 to about 100; also disclosed are polyoxyalkylene amino alcohol compounds which may be derived from the compounds of Formula I above having the formula: ##STR2## wherein R, R.sub.1, R.sub.4, x, N and M all have the values given above. Also provided is a process for preparing a primary amino polyoxyalkylene 1,3-dioxane or 1,3-dioxolane.Type: GrantFiled: December 21, 1987Date of Patent: December 11, 1990Assignee: Milliken Research CorporationInventors: John W. Miley, John W. Rekers
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Patent number: 4973761Abstract: Aminomono- or di-[(poly-n-butoxy)-n-butylamino]-(poly-n-butoxy)-n-butylamines of the general formula IH.sub.2 N--[(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 O).sub.x --(CH.sub.2).sub.4 --NH].sub.y --(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 O).sub.x --(CH.sub.2).sub.4 --NH.sub.2 (I)where x is from 1 to 150 and y is 1 or 2, are prepared by a process in which a hydroxy-(poly-n-butoxy)-butanol of the formula IIHO--(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 O).sub.x --(CH.sub.2).sub.4 --OH (II)where x is from 1 to 150, is reacted with from 1.01 to 300 mole equivalents of ammonia per hydroxyl group in the presence of a hydrogenation/dehydrogenation catalyst and hydrogen at from 150.degree. to 300.degree. C. and under from 20 to 400 bar.Type: GrantFiled: July 21, 1989Date of Patent: November 27, 1990Assignee: BASF AktiengesellschaftInventors: Willibald Schoenleben, Herbert Mueller
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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: 4967005Abstract: A process is described for the conversion of oxyalkylated alcohols to the corresponding alkoxylated tertiary amines, such as aminated ethoxylated amines, by reaction with a secondary amine at ambient pressure and at above ambient temperature in the presence of hydrogen and a reductive amination catalyst using, as a reductive amination catalyst, metallic iridium.Type: GrantFiled: October 20, 1988Date of Patent: October 30, 1990Assignee: Ethyl CorporationInventor: Kim R. Smith
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Patent number: 4962237Abstract: A catalytic process for polymerizing epoxides using active hydrogen initiators forming polyols having low unsaturation levels and high primary hydroxyl levels. The catalysts useful in this process are prepared from catalyst precursors exemplified by hydrotalcite. This process is more reactive with less acidic active hydrogen initiators. The polyols can be used in urethanes without removal of the catalyst.Type: GrantFiled: January 2, 1990Date of Patent: October 9, 1990Assignee: The Dow Chemical CompanyInventor: David E. Laycock
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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: 4939301Abstract: A process for preparing monoalkanolamines from ammonia and alkylene oxide using a catalyst which allows for high selectivity and high productivity which comprises an acid modified montmorillonite clay.Type: GrantFiled: December 23, 1988Date of Patent: July 3, 1990Assignee: Texaco Chemical CompanyInventors: Neal J. Grice, John F. Knifton
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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: 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: 4888446Abstract: The invention concerns a method for the preparation of polyoxyalkylene compounds wherein each compound has one primary amine group and one primary hydroxyl group. The method comprises alkoxylating a t-butyl ethylene, propylene or butylene glycol then aminating the product. Finally the t-butyl group is cleaved by an acid. The compounds of the method of this invention are useful in urethane/urea plastics including foams, elastomers and coatings.Type: GrantFiled: April 11, 1988Date of Patent: December 19, 1989Assignee: Texaco Chemical Co.Inventors: Howard P. Klein, Michael Cuscurida
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Patent number: 4885390Abstract: Novel amino polyols made by alkoxylating ethylene glycol diamine bottoms products, such as triethylene glycol diamine bottoms products, and tetraethylene glycol diamine bottoms products are described. For example, these bottoms products, alone or together, maybe propoxylated in a non-catalytic reaction to give amino polyols that are useful in producing rigid polyurethane foams. The resultant foams have better K-factors and a higher percentage of closed cells than comparable foams made with conventional amino polyols.Type: GrantFiled: October 30, 1987Date of Patent: December 5, 1989Assignee: ARCO Chemical Technology, Inc.Inventors: George P. Speranza, Michael E. Brennan, Jiang-Jen Lin
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Patent number: 4855403Abstract: Capped connected branch copolymers are provided comprising a core segment, branched polymer segments attached to the core segment, linear polymer segments attached to the terminals of the branched polymer segments, and cap segments, which comprise residues of an alkylene oxide containing at least 4 carbon atoms and which are attached to the free terminals of the linear polymer segments. These capped copolymers are less water-soluble than the uncapped connected branched copolymers from which they are derived, and are useful in carbonless copying systems as carriers for the color precursor microcapsules. The microcapsules can be applied to the carbonless copying sheet by dispersing the microcapsules in the capped copolymer, heating the copolymer above its transition temperature and spreading the melted copolymer over the sheet. After cooling, the copolymer forms a coherent layer on the sheet.Type: GrantFiled: August 22, 1985Date of Patent: August 8, 1989Assignee: Union Carbide CorporationInventors: Debra J. Meschke, Kenneth L. Hoy
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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: 4847418Abstract: A continuous process is provided for preparing alkanolamines having a high yield of monoalkanolamine, which comprises continuously reacting a flowing stream of a homogeneous mixture of an alkylene oxide having from two to four carbon atoms and ammonia in a molar ratio of ammonia to alkylene oxide within the range from about 15:1 to about 50:1 at temperatures above the critical temperature of the mixture and at pressures above the critical pressure of the mixture and maintaining the mixture in a single phase having a density of at least 15 lbs./cu.ft. for the time necessary to form an alkanolamine product mixture containing at least about 65% by weight monoalkanolamine.Type: GrantFiled: May 16, 1988Date of Patent: July 11, 1989Assignee: Union Carbide CorporationInventors: Charles A. Gibson, Moinuddin Ahmed, James R. Nelson
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Patent number: 4847417Abstract: A method for converting a bis(polyalkoxy)-N-alkylamine to a bis(diaminopolyalkoxy)-N-alkylamine has been discovered. The method comprises alkoxylating an alkylamine to a bis(polyalkoxy)-N-alkylamine. The alkylamine is selected to sterically hinder the resulting tertiary amine. The alkoxylate is then catalytically aminated according to well known procedures with a high yield of the diamine resulting.Compounds prepared by this method are of the formula:R--N--(PO.sub.x --NH.sub.2).sub.2wherein:PO is propylene oxide,x ranges from 2 to 40, andR is a sterically hindering alkyl such as isopropyl or tertiary butyl.The compounds are useful for curing epoxy thermoset resins. They are uniquely suited to reactions with polyisocyanates to prepare plastic parts, such as automobile body panels, by reaction injection molding.Type: GrantFiled: October 26, 1988Date of Patent: July 11, 1989Assignee: Texaco Inc.Inventors: John M. Larkin, George P. Speranza
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Patent number: 4845296Abstract: A process is provided for preparing alkanolamines having a high yield of monoalkanolamine which comprises reacting in a reaction mixture an alkylene oxide having from two to four carbon atoms with ammonia in a molar ratio of ammonia to alkylene oxide within the range from about 15.1 to about 50.1 at temperatures above the critical temperature of the reaction mixture and at pressures above the critical pressure of the reaction mixture and high enough to maintain the reaction mixture at sufficiently high fluid densities.Type: GrantFiled: May 12, 1988Date of Patent: July 4, 1989Assignee: Union Carbide CorporationInventors: Moinuddin Ahmed, James R. Nelson, Charles A. Gibson
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Patent number: 4827038Abstract: A method for converting a bis(polyalkoxy)-N-alkylamine to a bis(diaminopolyalkoxy)-N-alkylamine has been discovered. The method comprises alkoxylating an alkylamine to a bis(polyalkoxy)-N-alkylamine. The alkylamine is selected to sterically hinder the resulting tertiary amine. The alkoxylate is then catalytically aminated according to well known procedures with a high yield of the diamine resulting.Compounds prepared by this method are of the formula:R--N--(PO.sub.x --NH.sub.2).sub.2wherein:PO is propylene oxide,x ranges from 2 to 40, andR is a sterically hindering alkyl such as isopropyl or tertiary butyl.The compounds are useful for curing epoxy thermoset resins. They are uniquely suited to reactions with polyisocyanates to prepare plastic parts, such as automobile body panels, by reaction injection molding.Type: GrantFiled: August 3, 1987Date of Patent: May 2, 1989Assignee: Texaco Inc.Inventors: John M. Larkin, George P. Speranza
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Patent number: 4827039Abstract: The invention is an amine terminated polyether of the formula:N--[(CH.sub.2 CH(CH.sub.3)O).sub.x --CH.sub.2 CH(CH.sub.3)NH.sub.2 ].sub.3of 3000 to 7000 molecular weight.The polyamines are particularly suited for reaction with isocyanates to manufacture articles such as automobile body panels by reaction injection molding (RIM).Type: GrantFiled: August 3, 1987Date of Patent: May 2, 1989Assignee: Texaco Inc.Inventors: John M. Larkin, Michael Cuscurida
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Patent number: 4767555Abstract: Aqueous fluids are thickened with epoxide modified polyoxyalkylene diamines. The polyoxyalkylene diamines are of the formula:H.sub.2 NCH(CH.sub.3)CH.sub.2 O(CH.sub.2 CH(R)O).sub.x CH.sub.2 CH(CH.sub.3)NH.sub.2wherein:R is methyl or hydrogen andx is a number selected to give the diamine a molecular weight of 3000 to 9000.The epoxide is a hydrophobic monoepoxide, diepoxide or mixture thereof.The aqueous fluid optionally incorporate ethylene glycol. They are useful for water/glycol base hydraulic fluids, cosmetics and surfactants.Type: GrantFiled: April 10, 1987Date of Patent: August 30, 1988Assignee: Texaco Inc.Inventor: Edward C. Y. Nieh
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Patent number: 4766245Abstract: An improved method for the manufacture of high molecular weight polyoxyalkylene amines wherein a hydroxy-terminated polyoxyalkylene compound having a molecular weight of at least 500 is reacted with ammonia in the presence of hydrogen and Raney nickel/aluminum under anhydrous reductive amination conditions to provide the corresponding polyoxyalkylene amine in good yield and selectivity.The Raney nickel/aluminum is a nickel/aluminum alloy treated with a base, such as sodium hydroxide, so as to only partially leach the aluminum from the alloy, such that the final product contains from about 60 wt. % to about 75 wt. % of nickel and, correspondingly, from about 25 wt. % to about 40 wt. % of aluminum and is preferably used in nugget form.Type: GrantFiled: March 1, 1985Date of Patent: August 23, 1988Assignee: Texaco Inc.Inventors: John M. Larkin, Terry L. Renken
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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: 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: 4621141Abstract: A telomeric acid, a tertiary amine, and an epoxide are reacted in the absence of added water. The product recovered is effective in improving the filterability and reducing the pour point of diesel fuel. Alternatively the product can be prepared by reacting a quaternary ammonium hydroxide and a telomeric acid.Type: GrantFiled: April 26, 1984Date of Patent: November 4, 1986Assignee: Mobil Oil CorporationInventor: Sheldon Chibnik
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Patent number: 4618717Abstract: A process for the conversion of oxyethylene glycol monoalkyl ethers to the corresponding primary amines by reaction with ammonia in the presence of a nickel-copper-chromium-containing catalyst.Type: GrantFiled: September 17, 1984Date of Patent: October 21, 1986Assignee: Texaco Inc.Inventors: Terry L. Renken, John F. Knifton
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Patent number: 4605773Abstract: Alkylamine polyether surface active agent compositions and methods for using are described. The instant compositions are low foaming, and pH sensitive and are generally of the structure: ##STR1## in which (a) R.sub.1 may be hydrogen or alkyl;if R.sub.1 is hydrogen then R.sub.2, R.sub.3 and R.sub.4 must be alkyl having a total number of carbon atoms falling in the range of 7 to 23;if R.sub.1 is alkyl, then R.sub.2, R.sub.3 and R.sub.4 may be alkyl or hydrogen, the total number of carbon atoms in R.sub.1 +R.sub.2 +R.sub.3 +R.sub.4 falling in the range of 7 to 36 (preferably about 10 to 20);(b) The --(C.sub.2 H.sub.4 O).sub.m --segment must be a poly(oxyethylene) homogeneous chain or "block" polymer (i.e., a homopolymer), m having an average value in the range of 1 to 15, preferably 5 to 13; and(c) Y is selected from the group consisting of:(1) homogeneous poly(oxypropylene) chain (PO) "block" polymer or residue (i.e., a homopolymer), of the structure--(C.sub.3 H.sub.6 O).sub.Type: GrantFiled: May 10, 1984Date of Patent: August 12, 1986Assignee: Diamond Shamrock Chemicals CompanyInventors: James E. Maloney, James A. McDonell
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Patent number: 4568774Abstract: Catalysts producing a sharply peaked alkoxylation distribution during the alkoxylation of organic materials comprise mixtures of BF.sub.3 and metal alkyls or metal alkoxides, SiF.sub.4 and metal alkyls or metal alkoxides, or mixtures of these catalysts.Type: GrantFiled: October 1, 1984Date of Patent: February 4, 1986Assignee: Vista Chemical CompanyInventor: Kang Yang
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Patent number: 4567303Abstract: In preparing or reacting alkanolamines, especially at high temperatures, the use of substantially nickel-free alloy steels prevents corrosion and discoloration.Type: GrantFiled: August 6, 1984Date of Patent: January 28, 1986Assignee: BASF AktiengesellschaftInventors: Guenter Boettger, Hans Hammer, Otto Hertel, Gerhard Jeschek, Herbert Mueller, Emil Scharf, Willibald Schoenleben
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Patent number: 4540828Abstract: Catalysts and a method of using said catalysts for the alkoxylation of a variety of materials is disclosed. Catalysts so described produce alkoxylates having a very sharp alkoxylate distribution. The catalysts are supported and unsupported dialkoxy and dialkyl metal fluorides and halides and alkyl metal difluorides and dihalides.Type: GrantFiled: February 25, 1983Date of Patent: September 10, 1985Assignee: Vista Chemical CompanyInventor: Kang Yang
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Patent number: 4511516Abstract: Boron-containing heterocyclic compounds of the chemical formula: ##STR1## wherein at least one of R.sub.1, R.sub.2, R.sub.3, or R.sub.4 is an aryl, alkylaryl, or arylalkyl radical having from 1 to about 30 carbon atoms have been found useful as extreme pressure, anti-wear and friction-reducing additives for lubricating oils. The boron-containing heterocyclic compounds of the present invention are the reaction product of boric acid with the intermediate reaction product of a primary amine and an aromatic oxide. Metal derivatives of the boron-containing heterocyclic compounds are obtained by chemical reaction with a metal or compound thereof, particularly a first row transition metal or a Group IVA metal, or a compound thereof.Type: GrantFiled: September 15, 1982Date of Patent: April 16, 1985Assignee: Union Oil Company of CaliforniaInventors: Richard A. Holstedt, Kenneth Baron, Peter Jessup
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Patent number: 4507475Abstract: A process for purifying crude polyether polyols which are prepared by anionic polymerization of alkylene oxides in the presence of basic catalysts. The polyols are mixed with water and ortho-phosphoric acid in certain quantity ratios, an adsorption agent is incorporated in the reaction mixture, the mixture is filtered and the water is removed from the polyether polyol by distillation.Type: GrantFiled: July 22, 1983Date of Patent: March 26, 1985Assignee: BASF AktiengesellschaftInventors: Wolfgang Straehle, Raymond Denni, Matthias Marx
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Patent number: 4499264Abstract: An improved method is disclosed for producing amino polyols useful in preparing polyurethane foams. The improvement concerns charging ammonia, a primary amine or a secondary amine to the reaction vessel at the end of the oxide digestion step. The amine or ammonia scavenges the residual oxide and the resulting alkanol amine becomes one of the components of the polyol mixture. Alkanol amines are beneficial components of urethane polyols.In prior art industrial practice, residual oxide is vented to a scrubber system and then stripped to a low concentration.Type: GrantFiled: June 27, 1983Date of Patent: February 12, 1985Assignee: Texaco Inc.Inventor: Kenneth G. McDaniel
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Patent number: 4464488Abstract: The alkylene oxide adduct of bis(aminoethyl)ether may be reacted with formaldehyde in the presence of hydrogen and a hydrogenation-dehydration catalyst to produce compounds of the formula ##STR1## where R is hydrogen or lower alkyl of 1 to 4 carbon atoms and R" is methyl or ##STR2## where R is as above. Monocarboxylic acid salts of these compounds show unexpectedly high efficiency as polyurethane catalysts. Smaller amounts of this amine are required to produce foams having the same reaction profile as foams made with prior art amine salt catalysts.Type: GrantFiled: August 11, 1983Date of Patent: August 7, 1984Assignee: Texaco Inc.Inventors: Robert L. Zimmerman, Bruce W. Peterson
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Patent number: 4438281Abstract: The selective production of monoalkanolamines from alkylene oxides and ammonia over acidic inorganic catalysts such as acidic silica-aluminas, natural zeolites, acid clays and others is described. These catalysts have the advantage of providing good selectivity to the monoalkanolamine together with high alkylene oxide conversion and anhydrous operation which lowers operating costs. The catalysts are also relatively low cost and have high relative heat stability.Type: GrantFiled: January 24, 1983Date of Patent: March 20, 1984Assignee: Texaco Inc.Inventor: Fred L. Johnson, Jr.
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Patent number: 4433170Abstract: The alkylene oxide adduct of bis(aminoethyl)ether may be reacted with formaldehyde in the presence of hydrogen and a hydrogenation-dehydrogenation catalyst to produce new compounds of the formula ##STR1## where R is hydrogen or lower alkyl and R" is methyl or ##STR2## These compounds show unexpectedly high efficiency as polyurethane catalysts. Fewer equivalents of this amine are required to produce foams having the same reaction profile as foams made with piror art amine catalysts.Type: GrantFiled: July 20, 1981Date of Patent: February 21, 1984Assignee: Texaco Inc.Inventors: Robert L. Zimmerman, Ernest L. Yeakey
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Patent number: 4404405Abstract: There is disclosed a continuous process for making polyethylene polyamines such as diethylenetriamine, triethylenetetramine, etc. comprising the reaction of ethylene oxide with ammonia to produce a mixture of alkanolamines, the amination of the alkanolamines to ethyleneamines, and the reaction of at least a portion of the ethyleneamines thus produced with ethylene dichloride optionally in the presence of ammonia and/or water.Type: GrantFiled: September 30, 1981Date of Patent: September 13, 1983Assignee: Union Carbide CorporationInventor: John R. Winters
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Patent number: 4360697Abstract: The production of 1-amino-propanediol-2,3 is attained with good yields and in an industrially simple manner by reacting liquid ammonia with glycidol under pressure in the presence of a small amount of an organic solvent.Type: GrantFiled: April 9, 1981Date of Patent: November 23, 1982Assignee: Degussa AktiengesellschaftInventors: Axel Kleemann, Robert Nygren, Rudolf Wagner
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Patent number: 4358615Abstract: The yield of 1-amino-propanediol-2,3 is greatly increased and the process is carried out in an industrially simple manner by reacting liquid ammonia with glycidol under pressure and in the presence of a small amount of water.Type: GrantFiled: April 9, 1981Date of Patent: November 9, 1982Assignee: Degussa AktiengesellschaftInventors: Axel Kleemann, Robert Nygren, Rudolf Wagner
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Patent number: 4356323Abstract: The production of 1-amino-propanediol-2,3 is attained with good yields and in an industrially simple manner by reacting liquid ammonia with glycidol under pressure.Type: GrantFiled: April 9, 1981Date of Patent: October 26, 1982Inventors: Axel Kleemann, Robert Nygren, Rudolf Wagner
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Patent number: 4355181Abstract: In a process of making ethanolamines by reacting ethylene and ammonia and wherein ammonia is used in excess of the stoichiometric amount, the improvement comprising flashing and liquification at least part of the excess ammonia in the effluent prior to recycling. This moderates the operating conditions and simplifies the equipment needed to recycle the balance of the ammonia.Type: GrantFiled: February 27, 1981Date of Patent: October 19, 1982Assignee: The Dow Chemical CompanyInventors: Stephen B. Willis, Jr., Joseph D. Henry
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Patent number: 4341716Abstract: Polyether polyamines of the formula 1 ##STR1## in which R.sub.1 and R.sub.2 are identical or different and denote C.sub.8 -C.sub.30 -alkyl, -2-hydroxyalkyl or -alkenyl or C.sub.8 -C.sub.24 -alkoxypropyl, m and n are 2 or 3, R.sub.3 is hydrogen or methyl and the sum of o+p+q+r is an integer from 4 to 600, process for their manufacture and their use as dispersing agents, corrosion inhibitors, demulsifiers and acid retarders.Type: GrantFiled: September 22, 1980Date of Patent: July 27, 1982Assignee: Hoechst AktiengesellschaftInventors: Helmut Diery, Wolfgang Wagemann, Joachim Weide, Reinhold Deubel, Martin Hille
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Patent number: 4338408Abstract: The alkylene oxide adduct of bis(aminoethyl)ether may be reacted with formaldehyde in the presence of hydrogen and a hydrogenation-dehydration catalyst to produce new compounds of the formula ##STR1## where R is hydrogen or lower alkyl and R" is methyl or ##STR2## These compounds show unexpectedly high efficiency as polyurethane catalysts. Fewer equivalents of this amine are required to produce foams having the same reaction profile as foams made with prior art amine catalysts.Type: GrantFiled: July 20, 1981Date of Patent: July 6, 1982Assignee: Texaco Inc.Inventors: Robert L. Zimmerman, Ernest L. Yeakey
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Patent number: 4335045Abstract: An N-alkenyl-2-aminomethyl-pyrrolidine is prepared by firstly reacting tetrahydrofurfurylamine with gaseous hydrochloric acid and thionyl chloride to produce 2,5 dichloropentylamine hydrochloride. This is acetylized, possibly by acetyl chloride in dichloroethane in the presence of triethylamine, into N-acetyl-2,5-dichloropentylamine which is condensed with an alkenylamine into an N-alkenyl-2-acetylaminomethyl pyrrolidine from which the acetyl group is separated, for example by boiling with concentrated hydrochloric acid.Type: GrantFiled: March 24, 1976Date of Patent: June 15, 1982Assignee: Sachim S.A.Inventor: Eric-Alain Denzler
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Patent number: 4321271Abstract: Compounds of formula (I) ##STR1## wherein: R.sup.1 is C.sub.1-6 alkyl or C.sub.5-7 cycloalkyl;R.sup.2 is hydrogen or C.sub.1-6 alkyl; orNR.sup.1 R.sup.2 represents a heterocyclic ring having 5 to 7 ring atoms and only one hetero-atom; andR.sup.3 is C.sub.1-4 alkyl, one carbon atom of which is di- or tri-halogenatedor salts thereof are useful in promoting growth of ruminants. Processes for their production, veterinary formulations and treatments are described.Type: GrantFiled: June 30, 1980Date of Patent: March 23, 1982Assignee: Beecham Group LimitedInventor: Brian G. McDonald
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Patent number: 4309532Abstract: The modification of rigid amino polyols by their reaction with epoxy resin and alkylene oxides is described. The modified polyols produce rigid polyurethane foams that have higher heat distortion temperatures and better low temperature properties than foams made with nonmodified polyols. The viscosities of the epoxy resin-modified amino polyols are not significantly different than those of the prior art amino polyols although they are of a higher functionality.Type: GrantFiled: September 2, 1980Date of Patent: January 5, 1982Assignee: Texaco Inc.Inventors: Michael Cuscurida, Neal J. Grice, George P. Speranza
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Patent number: 4291147Abstract: Polyadducts, free from epoxide groups, are obtained from ammonia and epoxide compounds by reacting 1 mole of ammonia with from 1.2 to 2.0 equivalents of epoxide, so that if diepoxide compounds are used products of the general formula (I) ##STR1## are obtained, while if triepoxides and/or tetraepoxide compounds are used, by themselves, or together with diepoxide compounds, products of the general formula II ##STR2## are produced; in these formulae, the E.sup.1 's are identical or different hydroxyl-containing divalent radicals and the E.sup.2 's are identical or different hydroxyl-containing trivalent or tetravalent radicals, resulting from the opening of the oxirane rings of epoxide compounds containing two, three or four epoxide groups in the molecule, n.sup.1, n.sup.3 and n.sup.5 are from 0 to 3, n.sup.2 and n.sup.4 are from 1 to 3 and X is 0 or 1, and one or more of the divalent radicals E.sup.1 in the general formula (II) may or may not be replaced by polyvalent radicals E.sup.2.Type: GrantFiled: April 7, 1980Date of Patent: September 22, 1981Assignee: BASF AktiengesellschaftInventors: Fritz E. Kempter, Eberhard Schupp, Hans-Uwe Schenck, Erich Gulbins