Three Or More Amino Nitrogens Containing Patents (Class 564/512)
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Patent number: 4582937Abstract: Ethyleneamines are efficiently recovered from an aqueous solution thereof by extracting them from the aqueous solution into an organic phase with an extractant selected from carbonyl group-containing organic solvents, benzyl alcohol, carboxylic acids and salts thereof, alkylphosphoric acids and salts thereof, and mixed solvents containing at least one of these extractants. The ethyleneamines in the organic phase is recovered preferably from the organic phase to the aqueous phase by incorporating an acid therein, followed by phase separation.Type: GrantFiled: April 12, 1985Date of Patent: April 15, 1986Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Yoichi Hiraga, Tsugio Murakami, Hiroyuki Saito, Osamu Fujii
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Patent number: 4578519Abstract: This invention is directed to thermally activated pelletted catalyst compositions comprising titania having phosphorous derived from polyphosphoric acid deposited thereon and to their use in the production of predominatly linear polyethylenepolyamines from ethylenediamine and monoethanolamine.Type: GrantFiled: December 22, 1983Date of Patent: March 25, 1986Assignee: Texaco Inc. (Parent)Inventors: John M. Larken, Steven H. Vanderpool
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Patent number: 4578518Abstract: This invention is directed to thermally activated pelletted calcined catalyst compositions comprising titania having phosphorous derived from phosphoric acid deposited thereon and their use in the production of predominatly linear polyethylenepolyamines from ethylenediamine and monoethanolamine.Type: GrantFiled: December 22, 1983Date of Patent: March 25, 1986Assignee: Texaco Inc.Inventors: Steven H. Vanderpool, Lewis W. Watts, Jr.
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Patent number: 4578517Abstract: A process for preparing polyalkylene polyamine compounds is disclosed wherein ammonia or a primary or secondary amine and an alkanolamine compound are reacted in the presence of an effective amount of a Group IIIB metal acid phosphate at a temperature from about 175.degree. to 400.degree. C. under a pressure sufficient to maintain a substantial amount of the ammonia or amine in the reaction zone. The polyalkylene polyamines thus formed are recovered from the reaction mixture.Type: GrantFiled: September 16, 1983Date of Patent: March 25, 1986Assignee: Air Products and Chemicals, Inc.Inventors: Thomas A. Johnson, Michael E. Ford
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Patent number: 4570019Abstract: A process is provided which may be run continuously for producing polyethylene polyamines having improved color characteristics which comprises treating discolored polyethylene polyamines with polyethylene polyamine hydrochloride in the presence of water at elevated temperatures for the time necessary to reduce the color of said polyethylene polyamines and then flash evaporating the decolorized polyethylene polyamines from the treating mixture.Type: GrantFiled: February 8, 1984Date of Patent: February 11, 1986Assignee: Union Carbide CorporationInventors: Charles A. Gibson, John W. Crandall
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Patent number: 4555582Abstract: This invention is directed to thermally activated pelletted catalyst compositions comprising zirconium silicate having phosphorous deposited thereon and their use in the production of predominately linear polyethylenepolyamines from ethylenediamine and monoethanolamine.Type: GrantFiled: November 23, 1984Date of Patent: November 26, 1985Assignee: Texaco Inc.Inventor: Steven H. Vanderpool
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Patent number: 4550209Abstract: Essentially linear polyethylenepolyamines are prepared by reacting monoethanolamine with ethylenediamine in the presence of an intercalatively catalytically active tetravalent zirconium polymeric reaction product of an organo phosphonic acid or an ester thereof with a compound of tetravalent zirconium reactive therewith, such as zirconium trimethylene diphosphonate prepared by reacting trimethylenediphosphonic acid wth zirconyl chloride.Type: GrantFiled: July 26, 1984Date of Patent: October 29, 1985Assignee: Texaco Inc.Inventors: Susan D. Unvert, Steven H. Vanderpool, John F. Knifton
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Patent number: 4547591Abstract: Disclosed is a process for preparing predominantly linear polyethylenepolyamines from the catalyzed reaction of (1) an ethyleneamine and an alkanolamine, (2) ethyleneamines or (3) an alkanolamine and ammonia. The catalyst employed is a silica-alumina catalyst. An acidic phosphorus cocatalyst may be used in conjunction with the silica-alumina catalyst.Type: GrantFiled: December 16, 1983Date of Patent: October 15, 1985Assignee: Texaco Inc.Inventors: Michael E. Brennan, James H. Templeton, Ernest L. Yeakey
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Regenerative process for the preparation of linear polyethylenepolyamines using a supported catalyst
Patent number: 4540822Abstract: This invention is directed to a regenerative process for preparing predominantly linear polyethylenepolyamines from ethylenediamine and monoethanolamine using a catalyst comprising a phosphorous compound deposited on a group IVb transition metal oxide support.Type: GrantFiled: November 22, 1983Date of Patent: September 10, 1985Assignee: Texaco, Inc.Inventor: Steven H. Vanderpool -
Patent number: 4539430Abstract: Method for the preparation of ethylenediamine dinitrate. Ethylenediamine dinitrate, a useful explosive, may readily be prepared by solvent extraction of nitrate ion from an acidic aqueous solution thereof using a high-molecular-weight, water-insoluble amine dissolved in an organic solvent, and reacting the resulting organic solution with ethylenediamine. The process of the instant invention avoids the use of concentrated nitric acid, as is currently practiced, resulting in a synthesis which is far less hazardous especially for large quantities of the explosive, and more efficient.Type: GrantFiled: May 17, 1984Date of Patent: September 3, 1985Assignee: The United States of America as represented by the United States Department of EnergyInventor: Kien-yin Lee
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Patent number: 4532266Abstract: Polyether-based urethane-group-containing polyamines containing polymers and/or copolymers of unsaturated monomers and, optionally, urea and/or biuret and/or allophanate groups are produced by (a) reacting an NCO-prepolymer in aqueous alkaline solution at 0.degree. to 40.degree. C. to form a carbamate; (b) converting this carbamate to an amine by adding an ion exchanger to the reaction mixture; and (c) separating the polyamine from the reaction mixture. The NCO-prepolymers used as starting materials are prepolymers of (i) polyalkylene ether polyols having a molecular weight of from 1,000 to 10,000 containing from 1 to 60 wt. % of graft (co)polymers of unsaturated monomers; and (ii) excess molar quantities of organic polyisocyanate; and optionally, (iii) a low molecular weight chain-extending agent. The product polyamines have a molecular weight of from 1,000 to 10,000 and contain from 0.65 to 59.3 wt. % graft (co)polymer and from 0.11 to 2.9 wt. % terminal NH.sub.Type: GrantFiled: March 19, 1982Date of Patent: July 30, 1985Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Gerhard Balle, Dieter Dieterich, Holger Meyborg
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Patent number: 4532317Abstract: Aromatic polyamines containing aromatic primary amino groups as well as urethane and polyester groups are made by hydrolyzing an isocyanate in the presence of a basic material and water to form a carbamate and then converting the carbamate groups to amino groups. The isocyanate starting material contains aromatic isocyanate groups (as well as urethane and polyester groups) and has an NCO content of from 0.5 to 11.5 wt %. The basic compound is selected from alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal silicates, alkali metal sulfides, alkali metal cyanides, tetraalkylammonium hydroxides and mixtures thereof. Water is used in a quantity such that at least one mole of water is present for each equivalent of NCO groups. The carbamate groups may be converted to amino groups by treating the carbamate-containing mixture with a proton donor or with heat or with a solvent. The product polyamines are particularly useful in the production of polyurethanes.Type: GrantFiled: June 21, 1983Date of Patent: July 30, 1985Assignee: Bayer AktiengesellschaftInventor: Werner Rasshofer
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Patent number: 4505861Abstract: Novel azadinitriles and a method for their hydrogenation to produce spermidine, homospermidine and norspermidine.Type: GrantFiled: July 23, 1982Date of Patent: March 19, 1985Assignee: University of FloridaInventor: Raymond J. Bergeron, Jr.
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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: 4481048Abstract: Applicants have discovered a new composition of matter which is an explosive addition compound of ammonium nitrate (AN) and diethylenetriamine trinitrate (DETN) in a 50:50 molar ratio. The compound is stable over extended periods of time only at temperatures higher than 46.degree. C., decomposing to a fine-grained eutectic mixture (which is also believed to be new) of AN and DETN at temperatures lower than 46.degree. C. The compound of the invention has an x-ray density of 1.61 g/cm.sup.3, explodes to form essentially only gaseous products, has higher detonation properties (i.e., detonation velocity and pressure) than those of any mechanical mixture having the same density and composition as the compound of the invention, is a quite insensitive explosive material, can be cast at temperatures attainable by high pressure steam, and is prepared from inexpensive ingredients. Methods of preparing the compound of the invention and the fine-grained eutectic composition of the invention are given.Type: GrantFiled: February 3, 1982Date of Patent: November 6, 1984Assignee: The United States of America as represented by the United States Department of EnergyInventors: Howard H. Cady, Kien-yin Lee
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Patent number: 4467115Abstract: The present invention relates to the chemistry of polymers and, more specifically, to a method for preparing of branched polyethylenimine.The method of this invention resides in that a 2-aryl (alkyl)-2-oxazoline is subjected to an isomerizing polymerization with the formation of a poly-N-aroyl(acyl)ethylenimine which is then hydrolyzed and the resulting linear polyethylenimine is alkylated in the presence of .beta.-chlorethylene or .beta.-aminoethylsulphate at a molar ratio of the alkylation agent to the linear polyethylenimine equal to at least 0.5:1 respectively.Type: GrantFiled: October 12, 1982Date of Patent: August 21, 1984Assignee: Institut Neftekhimicheskogo Sinteza Imeni A.V. Toncheva Akademii Nauk SSSRInventors: David S. Zhuk, Vera A. Keppen, Nikolai A. Sivov, Gennady F. Tereschenko, Igor M. Golubkov, Valery E. Timofeev
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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: 4402842Abstract: The invention provides products of reaction formed by reacting an amine, a mercaptan and an aldehyde. The invention also provides liquid fuel and lubricant compositions.Type: GrantFiled: August 7, 1981Date of Patent: September 6, 1983Assignee: Mobil Oil CorporationInventors: Andrew G. Horodysky, Joan M. Kaminski
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Patent number: 4399308Abstract: A process for selectively preparing predominantly non-cyclic polyalkylene polyamine compounds is disclosed wherein an alkylene polyamine compound is contacted with an alkanolamine compound in the presence of a catalytically effective amount of a Lewis acid halide substance at a temperature of from 200.degree. to 350.degree. C. under a pressure sufficient to maintain the reaction mixture essentially in liquid phase. The polyalkylene polyamine thus formed is recovered from the reaction mixture.Type: GrantFiled: April 28, 1981Date of Patent: August 16, 1983Assignee: Air Products and Chemicals, Inc.Inventors: Michael E. Ford, Thomas A. Johnson
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Patent number: 4387249Abstract: The present invention provides a selective process for the manufacture of diethylenetriamine from ethylenediamine, ethanolamine, and urea. The process comprises a reaction cycle in which ethylenediamine, ethanolamine, and urea are first reacted in step (a) to form aminoethylethyleneurea and ethyleneurea, which in turn are hydrolyzed in a second reaction step (b) to diethylenetriamine and ethylenediamine. The ethylenediamine made in the second reaction step (b) may be recycled to the first reaction step (a).Type: GrantFiled: December 18, 1981Date of Patent: June 7, 1983Assignee: The Dow Chemical CompanyInventors: Robert M. Harnden, Donald W. Calvin
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Patent number: 4386218Abstract: A compound having a terminal isocyanate group is hydrolyzed to produce a polyamine having a urethane and/or a urea and/or a biuret group. More particularly, a carbamate is made by mixing an isocyanate prepolymer having urethane and/or urea and/or biuret groups present with aqueous base solutions at a temperature of from 0.degree. to 0.degree. C. and in quantities such that the equivalent ratio of hydroxyl to isocyanate groups is between from 0.3:1 to .gtoreq.1.01 to 1. The carbamate is then treated with an acid ion exchanger to form an amine. The amine is then removed from any other material which may be present. A preferred polyamine thus-produced corresponds to the general formula: ##STR1## in which each R radical may represent a divalent straight or branched-chain aliphatic radical; a divalent cycloaliphatic radical; a 4,4'- and/or a 2,4'-dicyclohexylmethane radical; or a 2,4- and/or 2,6-methyl cyclohexane radical.Type: GrantFiled: October 5, 1981Date of Patent: May 31, 1983Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Dieter Dieterich, Holger Meyborg
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Patent number: 4362894Abstract: Poly-(-2-aminoalkyl)polyamine compounds are provided having the following formula: ##STR1## wherein: n is an integer of from 3 to about 12;R.sub.1 is selected from H and an alkyl group containing from 1 to about 10 carbon atoms;R.sub.2 and R.sub.3 are each independently selected from H and a lower alkyl group containing from 1 to about 6 carbon atoms;R.sub.4 is selected from H and ##STR2## and R.sub.5 is selected from an alkyl group containing from about 6 to about 25 carbon atoms.Type: GrantFiled: May 4, 1981Date of Patent: December 7, 1982Assignee: Milliken Research CorporationInventor: Edward W. Kluger
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Patent number: 4331778Abstract: The present invention relates to a process for the production of polyurethane plastics by reacting compounds containing at least two isocyanate-reactive hydrogen atoms and having a molecular weight in the range of from 400 to 10,000, polyisocyanates and, optionally, chain extenders having a molecular weight of from 32 to 400, foam stabilizers, water and/or organic blowing agents in the presence of catalysts containing tertiary nitrogen. These catalysts are characterized in that mixtures of (a) one or more cross-linking catalysts corresponding to the following general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different, represent C.sub.1 -C.sub.5 -alkyl radicals, preferably CH.sub.3 -- or C.sub.2 H.sub.5 radicals,R' and R" represent hydrogen or the same or different C.sub.1 -C.sub.3 -alkyl radicals, preferably CH.sub.3 -- or C.sub.2 H.sub.Type: GrantFiled: December 10, 1979Date of Patent: May 25, 1982Assignee: Bayer AktiengesellschaftInventors: Claus-Dieter Sommerfeld, Peter Haas, Kuno Wagner, Manfred Kapps
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Patent number: 4316840Abstract: Process for production of polyalkylene polyamines, preferably non-cyclic polyalkylene polyamines, by reforming of other polyalkylene polyamines. The reforming process is effected by reacting the polyalkylene polyamine starting material in the presence of a metal nitrate or sulfate, preferably a sulfate, catalyst at elevated temperature and pressure and in the presence of sufficient water and sufficient catalyst, for a reaction period and under reaction conditions otherwise adapted to bring about the desired reforming reaction.Type: GrantFiled: November 25, 1980Date of Patent: February 23, 1982Assignee: Air Products and Chemicals, Inc.Inventors: Michael E. Ford, Thomas A. Johnson
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Patent number: 4316841Abstract: Process for production of polyalkylene polyamines, preferably non-cyclic polyalkylene polyamines, by reforming of other polyalkylene polyamines. The reforming process is effected by reacting the polyalkylene polyamine starting material in the presence of a phosphate, preferably a boron phosphate, catalyst at elevated temperature and pressure and in the presence of sufficient water and sufficient catalyst, for a reaction period and under reaction conditions otherwise adapted to bring about the desired reforming reaction.Type: GrantFiled: December 8, 1980Date of Patent: February 23, 1982Assignee: Air Products and Chemicals, Inc.Inventors: Michael E. Ford, Thomas A. Johnson
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Patent number: 4297443Abstract: A method of catalyzing the curing of polyurethane foams formed by reacting a polyol with a diisocyanate in the presence of a blowing agent and a catalyst comprising using as the catalyst a compound of the formula ##STR1## where n is 0 or 1, R is methyl or ethyl and R' is hydrogen, methyl of dimethylamino.Type: GrantFiled: August 28, 1980Date of Patent: October 27, 1981Assignee: International Minerals & chemical CorporationInventors: Paul E. Eckler, William A. Summers, Ollie W. Chandler
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Patent number: 4293682Abstract: Nitrogen-containing compounds are provided which may be represented structurally as: ##STR1## wherein R.sub.1 and R.sub.2 are each independently selected from hydrogen and lower alkyl and R.sub.3 is selected from hydrogen, lower alkyl, aryl and ##STR2## wherein R.sub.4 is selected from H and lower alkyl.Type: GrantFiled: May 12, 1980Date of Patent: October 6, 1981Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Tien-Kuei Su
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Patent number: 4288625Abstract: Unsaturated dinitriles are reacted with an aromatic compound such as benzene in the presence of a Lewis acid such as aluminum chloride to yield novel aralkylenedinitriles, such as 5-methyl-5-phenylnonanedinitrile and isomers thereof. The aralkylenedinitriles can be reduced to novel aralkylenediamines or novel cycloalkylalkylenediamines. Polymerization of the aralkylenediamines or cycloalkylalkylenediamines with polycarboxylic acids provides novel polyamides of tough, clear, colorless character.Type: GrantFiled: August 23, 1976Date of Patent: September 8, 1981Assignee: Phillips Petroleum Co.Inventors: Charles A. Drake, Stanley D. Turk
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Patent number: 4279621Abstract: Hydrocarbon-containing materials having a low amount of unsaturation e.g., paraffinic and napththenic hydrocarbons having less than about 10 weight percent unsaturation are stabilized or made more resistant to oxidation employing a polyamines mixture obtained as a heavy by-product residue from the recovery by distillation of a polyamine obtained in the hydrogenation of branched aliphatic dinitriles. In one embodiment an isoparaffinic hydrocarbon obtained by alkylation of an isoparaffin with an olefin is rendered resistant to oxidation.Type: GrantFiled: September 14, 1978Date of Patent: July 21, 1981Assignee: Phillips Petroleum CompanyInventor: Robert E. Reusser
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Patent number: 4277622Abstract: A process for producing 1,17-diamino-9-azaheptadecane, which comprises adding nitric acid, hydrochloric acid, p-toluenesulfonic acid or sulfanilic acid to octamethylenediamine, and heating the mixture to eliminate ammonia therefrom.Type: GrantFiled: December 26, 1979Date of Patent: July 7, 1981Assignee: Dainippon Ink & Chemicals Inc.Inventors: Touru Asada, Yasuhisa Miura, Tsutomu Yoshino
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Patent number: 4275237Abstract: Heavy reaction product after separation as by distillation of light reaction product or diadduct from a reaction mixture obtained by reaction of olefinically unsaturated nitriles with monoolefinic hydrocarbons containing an allylic hydrogen atom is hydrogenated to produce a polyamine mixture useful as an epoxy resin hardener yielding cured resins exhibiting low water absorption.Type: GrantFiled: August 6, 1979Date of Patent: June 23, 1981Assignee: Philips Petroleum CompanyInventors: Charles A. Drake, Ralph P. Williams
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Patent number: 4268455Abstract: Chelating tertiary amino metal amides selected from compounds having the formulae: Mg.sup. ++ [Chel N].sub.2.sup..crclbar. wherein [Chel N].sup..crclbar. is not ##STR1## [Chel N].sup..crclbar. M.sup..sym., [Chel N].sup..crclbar. M.sup..sym. M'H.sub.m R.sub.n X.sub.p, Z Mg.sup..sym. [Chel N--M'H.sub.m R.sub.n X.sub.p ].sup..crclbar., Mg.sup. ++ --[Chel N--M'H.sub.m R.sub.n X.sub.p ].sup..crclbar. [M'H.sub.m R.sub.n X.sub.p Z].sup..crclbar., Chel N-Mg.sym.[N--Mg.sup..sym. H.sub.m R.sub.n X.sub.p Z].sup..crclbar. and Mg.sup. ++ [Chel N--M'H.sub.m R.sub.n X.sub.p ].sub.2 .sup..crclbar., wherein M is a Group IA metal, M' is a metal selected from the group consisting of Li, Na, Mg, Be, Zn, Cd, B, Al, Ga, In, Zr, Ti, Sn and Cu and m and n=0 to 4, p=0 to 3 and (m+n+ p)=the valence of M' and (m+n)= at least 1 and X is a nonreactive group selected from the group consisting of chlorine, bromine, iodine, C.sub.1 to C.sub.20 alkoxide, C.sub.1 to C.sub.20 thioalkoxide, C.sub.2 to C.sub.40 hydrocarbyl secondary amide and C.Type: GrantFiled: August 12, 1976Date of Patent: May 19, 1981Assignee: Exxon Research & Engineering Co.Inventors: Arthur W. Langer, Jr., Thomas A. Whitney
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Patent number: 4264480Abstract: Stable, pumpable, aqueous suspensions of water-insoluble, calcium-binding aluminosilicates suitable as stock suspensions comprising (A) from 20% to 55% by weight of at least one finely-divided, water-insoluble silicate compound having a calcium-binding power of at least 50 mg CaO/gm of anhydrous active substance and having the formula, combined water not shown(M.sub.2/n O).sub.x.Me.sub.2 O.sub.3.(SiO.sub.2).sub.ywhere M is a cation of the valence n, exchangeable with calcium, x is a number of from 0.7 to 1.5, Me is aluminum or boron, and y is a number from 0.8 to 6, (B) from 0.2% to 5% by weight of at least one organic dispersing agent as follows:lower alkylene oxide or glycide adducts of the reaction product of .epsilon.-caprolactam with an N-mono- or di-higher alkyl/alkenyl-alkylenediamine.Type: GrantFiled: June 28, 1979Date of Patent: April 28, 1981Assignee: Henkel Kommanditgesellschaft auf Aktien (Henkel KGaA)Inventors: Hans Andree, Dieter Jung, Martin Bischoff, Jens Conrad, Josef Huppertz, Gunter Jakobi, Peter Krings, Dieter Kuhling, Herbert Reuter, Wolfgang Rupilius, Horst Rutzen, Harald Schnegelberger
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Patent number: 4257984Abstract: The present invention relates to epoxy resin compositions and in particular to curing agents for such resin compositions. The present invention thus embraces monotertiarymonosecondarydiprimarytetramines and the precursor from which this amine is manufactured namely monotertiarymonosecondarydinitrilodiamines.Type: GrantFiled: April 4, 1977Date of Patent: March 24, 1981Assignee: Henkel CorporationInventor: Stuart A. Harrison
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Patent number: 4255548Abstract: Copolymers of ethylene and vinylamine are disclosed as are methods for their production. The disclosed copolymers find application primarily as flocculants.Type: GrantFiled: January 7, 1980Date of Patent: March 10, 1981Assignee: DynapolInventors: Robert E. Wingard, Jr., Eric R. Larson
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Patent number: 4235821Abstract: In the process of hydrogenating aliphatic nitriles to primary amines whereby the nitrile is hydrogenated in a solvent system containing added ammonia using a cobalt or ruthenium catalyst, the improvement of employing an ether as solvent and carrying out the hydrogenation in the presence of water in an amount of from about 5% to about 15% by volume of the ether solvent whereby the rate of reaction is increased, and selectivity to primary amine products is increased.Type: GrantFiled: February 1, 1979Date of Patent: November 25, 1980Assignee: Suntech, Inc.Inventors: Walter A. Butte, Jr., William J. Murtaugh, Richard E. Mitchell