Patents Examined by P. J. Killos
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Patent number: 4013714Abstract: Compounds represented by the formula ##EQU1## wherein Rx is ##EQU2## AND A is hydrogen, methyl, ethyl, CH.sub.2 OH or RxOH; M being alkali metal, ammonium, alkyl ammonium, or alkanol ammonium and Rz being hydrogen, alkyl, phenyl, phenyl alkyl, alkoxy alkyl, alkoxy phenyl or alkoxy phenyl alkyl are useful as complexing agents and/or detergency builders. The ester and acid forms of these compounds are useful as intermediates for their preparation.Type: GrantFiled: December 19, 1973Date of Patent: March 22, 1977Assignee: Monsanto CompanyInventor: Kent P. Lannert
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Patent number: 3966802Abstract: The present invention relates to a process for preparing acrylic acid by oxidizing acrolein and to an oxidation catalyst.More particularly, the present invention relates to a catalyst and a process for preparing acrylic acid by oxidizing acrolein or a mixed acrolein gas obtained by vapor phase oxidation of propylene with molecular oxygen in the presence of an oxidation catalyst of the empirical formula:Mo.sub.a V.sub.b T.sub.c A.sub.d O.sub.ewherein Mo, V and O represent molybdenum, vanadium and oxygen, respectively, T represents tungsten or antimony, A represents an alkali metal, and a, b, c, d and e represent number of atoms of Mo, V, T, A and O, respectively, and when a is 12, b is 0.5 to 6, c is 0 to 6, d is 0.01 to 1.5, preferably, 0.15 to 1.2 and e is naturally determined by the valence requirements of the other elements present.Type: GrantFiled: April 19, 1974Date of Patent: June 29, 1976Assignee: Nippon Kayaku Kabushiki KaishaInventors: Shigeo Takenaka, Hitoshi Shimizu, Masanobu Ogawa
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Patent number: 3966797Abstract: Dinorbornene compounds, many of them novel, have been found to form polymers having a ladder structure. The dinorbornene compounds and dinorbornene polymers with other polymers such as the polyolefins, vinyl polymers, acrylic polymers, polyesters, polyamides, polyethers, polyureas, polyurethanes, natural polymers, etc., are readily crosslinked by irradiation.Type: GrantFiled: May 26, 1971Date of Patent: June 29, 1976Assignee: Union Carbide CorporationInventors: Henry Octave Colomb, Jr., David John Trecker, Thomas Kemper Brotherton
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Patent number: 3965149Abstract: A method for recovering methyl methacrylate from a mixture of polymeric materials containing poly (methyl methacrylate) which comprises contacting the mixture with a boiling C.sub.5 - C.sub.8 alkane, separating an insoluble residue containing poly (methyl methacrylate) from the alkane and its extract, extracting poly (methyl methacrylate) from such insoluble residue with boiling acetone, separating the poly (methyl methacrylate) from the acetone, and recovering the methyl methacrylate monomer from such poly (methyl methacrylate) by pyrolysis. In a preferred embodiment, the poly (methyl methacrylate) containing solid obtained after the acetone extraction is compressed under elevated temperatures and pressures prior to pyrolysis. The method can be stopped prior to the pyrolysis step when it is desired to recover only the poly (methyl methacrylate).Type: GrantFiled: November 4, 1974Date of Patent: June 22, 1976Assignee: Ford Motor CompanyInventor: Lee R. Mahoney
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Patent number: 3956382Abstract: A process for the production of ether polycarboxylic acids comprising reacting alkali metal salts of ether carboxylic acids with carbon dioxide in the presence of (1) an alkaline compound selected from the group of alkali metal carbonates, bicarbonates and hydroxides and (2) optionally, heavy metal catalysts and inert diluents at temperatures of 200.degree.C to 350.degree.C under pressure, acidify the resulting alkali metal salt of an ether polycarboxylic acid and recovering said ether polycarboxylic acid.Type: GrantFiled: October 21, 1974Date of Patent: May 11, 1976Assignee: Henkel & Cie G.m.b.H.Inventor: Horst-Jurgen Krause
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Patent number: 3956381Abstract: A process for the production of ether polycarboxylic acids comprising reacting alkali metal salts of ether carboxylic acids with carbon dioxide in the presence of (1) an alkali metal alkyl carbonate and (2) optionally, heavy metal catalysts and inert diluents at temperatures of 200.degree.C to 350.degree.C under pressure, acidify the resulting alkali metal salt of an ether polycarboxylic acid and recovering the ether polycarboxylic acid.Type: GrantFiled: October 21, 1974Date of Patent: May 11, 1976Assignee: Henkel & Cie G.m.b.H.Inventor: Horst-Jurgen Krause
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Patent number: 3956366Abstract: A process for making N-monochloro or bromo monosubstituted urea where a urea RNH--CO--NH.sub.2 is suspended in liquid water at 0.degree.C-60.degree.C and reacted with free chlorine or free bromine, at least 2 g. atoms per mole of urea, preferably in the presence of an acid acceptor such as zinc oxide; R may be alkyl having 3 carbon atoms, cycloalkyl, aralkyl, alkoxycarbonyl, aryloxycarbonyl or acyl.New compounds of the formula R.sub.d --NX--CO--NX'H where X and X' are different and are (1) chloro or bromo and (2) hydrogen and R.sub.d is alkyl or cycloalkyl, 3-15 carbon atoms, or R.sub.1 C(O)--, where R.sub.1 is aliphatic, cycloaliphatic, aryl, alkoxy or aryloxy, each of not more than 10 carbon atoms and when X is H, X' is Cl or Br and R.sub.d is alkyl or cycloalkyl and when X is Cl or Br, X' is H and R.sub.d is R.sub.1 C(O)--.Type: GrantFiled: June 28, 1973Date of Patent: May 11, 1976Assignee: Pennwalt CorporationInventors: Chester Stephen Sheppard, Leonard Earnest Korczykowski
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Patent number: 3954749Abstract: Provided as catalysts for the formation of cellular urethane polymers ranging from flexible to rigid foams, are beta-amino carbonyl compounds wherein carbonyl is present as an amido or carboxylic acid ester group and the beta-amino group is present as dialkylamino or an N-morpholino or N,N'-piperazino heterocyclic nucleus. Effective in the catalysis of the water-isocyanate reaction, these beta-amino amides and beta-amino esters are used with particular advantage in the manufacture of water-blown flexible foams, both molded and free-rise, including high-resilience and flame-retarded foam. The beta-amino carbonyl catalysts allow for the formation of foam products essentially free of the odor associated with amines such as N-ethylmorpholine. In view of this highly desirable characteristic and their other beneficial properties, the catalysts of the invention are advantageously employed as direct replacements for N-ethylmorpholine in high-resilience and other foam formulations.Type: GrantFiled: April 23, 1974Date of Patent: May 4, 1976Assignee: Union Carbide CorporationInventors: David Charles Priest, Michael Ray Sandner, David John Trecker
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Patent number: 3953504Abstract: An optically active enantiomer of tartaric acid or a salt thereof is racemized by mixing meso-tartaric acid or a salt thereof with a solution of an optically active enantiomer of tartaric acid or a salt thereof in a molar ratio of 0.2 - 0.5 and thereafter heating the mixture.Type: GrantFiled: March 18, 1975Date of Patent: April 27, 1976Assignees: Nippon Peroxide Co., Ltd., Showa Chemical Co., Ltd.Inventors: Minoru Saotome, Yoshikazu Yamamoto, Nobuo Watani, Ryuichi Kayama
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Patent number: 3952034Abstract: Olefins and acetylenes are carbonylated to a carboxylic acid or ester using a homogenous catalyst system comprising palladium together with iron or a metal of Groups IVA, VA or IIIB, the catalyst being either a polynuclear complex incorporating both metals, or a mixture of a soluble palladium salt and metal halide. Starting with cyclic di-olefins, such as cyclo-octadiene, the product cycloalkenyl carboxylic acid or ester may be cleaved to give acyclic dicarboxylic acids, such as azelaic acid.Type: GrantFiled: December 3, 1973Date of Patent: April 20, 1976Assignee: Imperial Chemical Industries LimitedInventors: David Thomas Thompson, Reginald Jackson
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Patent number: 3951969Abstract: Plant growth regulating compounds are N-substituted-P-(2-chloroethyl)-phosphonamidic esters of the formula: ##EQU1## wherein R is cycloalkyl, R.sub.1 is hydrogen or cycloalkyl or R and R.sub.1 together form a heterocyclic ring such as morpholine, piperidine or pyrrolidine and R.sub.2 is alkyl or haloalkyl. They are prepared by the reaction of 2-chloroethylphosphonohalidic esters with the appropriate secondary amine.Type: GrantFiled: February 12, 1974Date of Patent: April 20, 1976Assignee: GAF CorporationInventors: David I. Randall, Robert W. Wynn
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Patent number: 3952054Abstract: Diglycolic acid is prepared by oxidation of p-dioxanone.Type: GrantFiled: December 5, 1974Date of Patent: April 20, 1976Assignee: Monsanto CompanyInventor: Chung Y. Shen
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Patent number: 3950332Abstract: N-substituted amino-N-nitroso-aminoacetamides, e.g., .alpha.-(N-morpholino-N-nitrosoamino)acetamide, are prepared by hydrolyzing the corresponding 3-N-substituted amino-sydnonimines and have been found to be useful as hypotensive/anti-hypertensive and anti-anginal agents.Type: GrantFiled: February 14, 1973Date of Patent: April 13, 1976Assignee: Sandoz, Inc.Inventor: Paul L. Anderson
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Patent number: 3950410Abstract: In the oxidation of a liquid alcohol and/ketone with nitric acid to a carboxylic acid, especially of a mixture of cyclohexanol and cyclohexanone to adipic acid, temperature is controlled during the reaction in which gas is evolved by contacting the reaction mixture with a plurality of cooling surfaces vertically spaced from each other in such a way that the turbulence induced by the reaction inhibits the formation of bubbles upon the cooling surfaces. The cooling surfaces may be horizontally disposed banks of tubes through which water is passed.Type: GrantFiled: March 13, 1974Date of Patent: April 13, 1976Assignee: Imperial Chemical Industries LimitedInventor: Jose Lopez-Merono
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Patent number: 3950399Abstract: A new compound, 1,4-diacyloxy-2,3-butanediol, having the general formula ##EQU1## where R is hydrogen atom or methyl group. The compound can be used above all as a crosslinking agent in the preparation of crosslinked hydrophilic polymeric gels. This compound can be prepared by opening the epoxy ring in such a way, that 1 mole of 1,2-3,4-diepoxybutane is treated with 2 moles of unsaturated acid of the general formula ##EQU2## where R has the aforementioned meaning.Type: GrantFiled: January 30, 1974Date of Patent: April 13, 1976Assignee: Ceskoslovenska akademie vedInventors: Jiri Labsky, Josef Exner
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Patent number: 3950405Abstract: A trans isomer of 4-cyanoncyclohexane-1-carboxylic acid or its lower alkyl ester is reduced in a solvent in the presence of a hydrogenating catalyst, and hydrolyzing the produced ester in case the starting trans-isomer is a lower alkyl ester, then the trans-4-aminomethyl-cyclohexane-1-carboxylic acid is recovered from the reaction mixture.Type: GrantFiled: June 4, 1969Date of Patent: April 13, 1976Assignee: Mitsubishi Chemical Industries Ltd.Inventors: Atsuji Okano, Shizuo Kadoya, Takeo Naito, Takaaki Aoyagi, Masao Shimizu
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Patent number: 3950388Abstract: Organic compounds having a substituent represented by the formula ##EQU1## wherein M is alkali metal or ammonium which are useful complexing agents for metal and/or alkaline earth metal ions are prepared by reaction of a conjugate base of a hemiketal of a ketomalonic acid diester and an alcohol with a bromo or iodo acetate ester and saponifying the resulting product.Type: GrantFiled: May 24, 1974Date of Patent: April 13, 1976Assignee: Monsanto CompanyInventor: Kent P. Lannert
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Patent number: 3950397Abstract: A process is provided for making a triester of citric acid wherein the cyanohydrin of an acetone dicarboxylic acid diester is reacted with 1 to 3 molar equivalents of an aliphatic alcohol having 1 to 4 carbon atoms and at least two molar equivalents of anhydrous hydrogen chloride in an inert halogenated organic solvent for the cyanohydrin diester at not above 50.degree.C. to form an imino ether, removing excess hydrogen chloride, adding water to form a two-phase system, separating the organic and water phases and recovering the resulting triester from the organic phase. The triester may be hydrolyzed into citric acid or a salt of citric acid in an acid or alkaline medium.Type: GrantFiled: December 6, 1974Date of Patent: April 13, 1976Assignee: Akzona IncorporatedInventor: Jan Gerardus Batelaan
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Patent number: 3948985Abstract: Carboxymethyloxysuccinic acid is prepared by acidifying the calcium salt of carboxymethyloxysuccinic acid with sulfuric acid at a temperature of 40.degree.C to 80.degree.C; filtering off the CaSO.sub.4 .2H.sub.2 O by-product and concentrating the filtrate to give the purified acid. The calcium salt of carboxymethoxysuccinic acid is formed by reacting maleic acid and glycolic acid in aqueous media containing excess calcium hydroxide.Type: GrantFiled: October 11, 1974Date of Patent: April 6, 1976Assignee: FMC CorporationInventors: John H. Blumbergs, Michael J. McCarthy, Joseph H. Finley, John M. Polkowski
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Patent number: 3948986Abstract: A process for producing an alpha-hydroxy carboxylic acid which comprises contacting carbon monoxide with a saturated C.sub.2 -C.sub.16 aldehyde, water, and a catalyst comprising hydrogen fluoride in a reaction zone and under conditions effective to form an alpha-hydroxy carboxylic acid, including a temperature between 0.degree.C and 100.degree.C and a carbon monoxide partial pressure between 10 and 4000 psig.An alpha-alkoxy acid can be produced in the above reaction by using an alcohol instead of water.Type: GrantFiled: January 20, 1975Date of Patent: April 6, 1976Assignee: Chevron Research CompanyInventor: Shigeto Suzuki