Polycarboxylic Acid Patents (Class 560/180)
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Patent number: 4216337Abstract: A process for preparing esters which comprises reacting a polycarboxylic acid with an alcohol, removing the unreacted alcohol from the resultant esterification reaction mixture, heating the crude ester at a temperature of 160.degree. to 340.degree. C., contacting the heat-treated crude ester with an adsorbent, and recovering the ester of high purity. The ester obtained has superior electrical insulation, transparency and thermal stability.Type: GrantFiled: July 10, 1978Date of Patent: August 5, 1980Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Makoto Baba, Teruyuki Ninomiya, Chieko Ono
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Patent number: 4212989Abstract: In a process for producing a carboxylic acid or its ester by reacting an alcohol or an ether with carbon monoxide, the improvement wherein the reaction is performed in the presence of, as a solvent, an aryl ester of an aliphatic carboxylic acid represented by the formula ##STR1## wherein n is an integer of 1 to 5, R.sub.1 represents hydrogen or C.sub.1 -C.sub.4 alkyl or alkenyl, and R.sub.2 represents hydrogen, alkyl, aryl, alkenyl, hydroxymethyl, acyl, acyloxy, formyl, carboxy, hydroxy, halogen, sulfo, nitro, nitroso, amino, acid amide or cyano, and two or more R.sub.2 groups may be the same or different, and the substituents R.sub.2 may be bonded to each other to form a penta- or hexa-carbocyclic or heterocyclic ring.Type: GrantFiled: October 26, 1978Date of Patent: July 15, 1980Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomiya Isshiki, Yasuhiko Kijima, Yuh Miyauchi
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Patent number: 4208204Abstract: Disclosed as novel compounds are 3-hydroxy-3-methylglutaric acid monoamide and the lower alkyl esters and salts thereof, 3-hydroxy-3-methylglutaramide mononitrile and 3-hydroxy-3-methylglutaramide. 3-Hydroxy-3-methylglutaric acid monoamide and derivatives thereof exhibit anti-germination and anti-growth utility against a wide variety of perennial and annual weed grasses. 3-Hydroxy-3-methylglutaramide mononitrile and 3-hydroxy-3-methylglutaramide have utility as intermediates in the preparation of 3-hydroxy-3-methylglutaric acid monoamide.Type: GrantFiled: October 7, 1977Date of Patent: June 17, 1980Assignee: Calbiochem-Behring Corp.Inventor: Andre H. Yavrouian
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Patent number: 4204052Abstract: Copolymers of acetal carboxylates are provided which have the following empirical formula ##STR1## where Y is one or more comonomers randomly distributed in the copolymer; the product of n and q averages at least 4; p is at least 1; and M is selected from the group consisting of alkali metal, ammonium, alkyl groups having 1 to about 4 carbon atoms, and alkanol ammonium groups having 1 to about 4 carbon atoms in the alkyl chain. Such copolymers are useful as detergent builders to replace sodium tripolyphosphate (STP) in detergent formulations. The copolymers are stable under laundry use conditions, but depolymerize in acid media, making the fragments more readily biodegradable in waste streams.Type: GrantFiled: November 20, 1978Date of Patent: May 20, 1980Assignee: Monsanto CompanyInventors: Marvin M. Crutchfield, Victor D. Papanu, Craig B. Warren
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Patent number: 4182718Abstract: The disclosure relates to:(a) 1,3-dioxolane and 1,3-dioxane polycarboxylates and their precursors having the general formula: ##STR1## wherein X may be selected from the group consisting of H, CCl.sub.3, CO.sub.2 R, where R is H or lower alkyl, CO.sub.2 M, where M is alkali metal, preferably Na, NH.sub.Type: GrantFiled: October 25, 1977Date of Patent: January 8, 1980Assignee: Monsanto CompanyInventors: Marvin M. Crutchfield, Charles J. Upton
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Patent number: 4182908Abstract: This disclosure concerns:(a) Compounds having the molecular structure represented by the formula: ##STR1## wherein M is selected from the group consisting of --H, --CH.sub.3, --C.sub.2 H.sub.5, --NH.sub.4, --Na, --K and combinations thereof; R is selected from the group consisting of an alkyl radical (branched or straight chain) containing up to about C.sub.20, --CH(CO.sub.2 M).sub.2, and --CH.sub.2 CO.sub.2 M, and R' is selected from the group consisting of an alkyl radical (branched or straight chain) containing up to about C.sub.20, --H, and --OR;(b) a method for making the compounds of (a);(c) solid and liquid detergent compositions comprising compounds of (a), and(d) washing processes employing the compounds of (a) and/or the compositions of (c).Type: GrantFiled: August 15, 1977Date of Patent: January 8, 1980Assignee: Monsanto CompanyInventor: Kent P. Lannert
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Patent number: 4182900Abstract: Ether carboxylates represented by the formula: ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of alkyl containing up to 20 carbon atoms and M.sub.1 and M.sub.2 are individually selected from the group consisting of alkyl containing up to about 4 carbon atoms, are useful as intermediates to prepare the corresponding acid or alkali metal, ammonium and alkanol amine salts, which are useful as chelants, sequestrants and detergent builders.Type: GrantFiled: September 26, 1978Date of Patent: January 8, 1980Assignee: Monsanto CompanyInventors: Marvin M. Crutchfield, Victor D. Papanu, Charles J. Upton
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Patent number: 4172208Abstract: The compound of the formula: ##STR1## is useful as an intermediate to prepare a compound having the generic formula ##STR2## wherein X is selected from groups to provide tetrahydropyran type compounds, 1,4 dioxane type compounds or tetrahydrofuran type compounds, and R is selected from the group consisting of alkali metal, NH.sub.4.sup.+, NH(CH.sub.2 CH.sub.2 OH).sub.3.sup.+, and lower alkyl, branched or straight chain, with up to about C.sub.20 in the chain, useful as a detergent builder.Type: GrantFiled: July 27, 1978Date of Patent: October 23, 1979Assignee: Monsanto CompanyInventors: Marvin M. Crutchfield, Kent P. Lannert
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Patent number: 4169934Abstract: Copolymers of keto dicarboxylates are provided which have the following general formula ##STR1## WHERE Y is one or more comonomers; n averages at least 2; p is at least 1; and M is selected from the group consisting of alkali metal, ammonium, alkyl groups having 1 to about 4 carbon atoms, and alkanol amine groups having 1 to about 4 carbon atoms in the alkyl chain. Such copolymers are useful as detergent builders to replace sodium tripolyphosphate (STP) in detergent formulations. The copolymers are stable under laundry use conditions, but depolymerize in acid media, making the fragments more readily biodegradable in waste streams.Type: GrantFiled: April 3, 1978Date of Patent: October 2, 1979Assignee: Monsanto CompanyInventor: Victor D. Papanu
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Patent number: 4156093Abstract: The process comprises the hot treatment at a temperature of 80.degree. to 160.degree. C. by an amount of 5 to 50% of 85% of phosphoric acid, of the residues resulting from the distillation of reaction media containing hemiacetal-esters under substantially anhydrous conditions. These reaction media are selected from among those resulting from the reaction of alcohols and glyoxylic acid and those resulting from the treatment of glyoxylic hemiacetal-esters with P.sub.2 O.sub.5.Type: GrantFiled: March 13, 1978Date of Patent: May 22, 1979Assignee: Hoechst FranceInventor: Yani Christidis
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Patent number: 4147702Abstract: A compound of the formula ##STR1## wherein R' is lower alkyl is useful as an intermediate to prepare a compound of the formula ##STR2## wherein X is selected from the group consisting of: ##STR3## wherein R is selected from the group consisting of alkali metal, NH.sub.4.sup.+, NH(CH.sub.2 CH.sub.2 OH).sub.3.sup.+, and lower alkyl, branched or straight chain, with up to about C.sub.20 in the chain. The ester can be converted to the corresponding salt, useful as a detergent builder.Type: GrantFiled: July 27, 1978Date of Patent: April 3, 1979Assignee: Monsanto CompanyInventors: Marvin M. Crutchfield, Kent P. Lannert
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Patent number: 4146543Abstract: Novel polyfunctional compounds and a process for their preparation are disclosed. These compounds and their alkali metal salts are useful metal sequestrants and/or detergent builders. Selected compounds are also intermediates useful in the syntheses of aconitic acid as well as isocitric and alloisocitric acids and their lactones. The novel polyfunctional compounds are obtained from the reaction of maleic anhydride with selected active methylene or methine containing compounds.Type: GrantFiled: November 4, 1977Date of Patent: March 27, 1979Assignee: Lever Brothers CompanyInventor: Eddie N. Gutierrez
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Patent number: 4145558Abstract: Novel polyfunctional compounds which may be hydrolyzed to the corresponding salts, which in turn are metal sequestering agents, are disclosed, as well as a novel method for their preparation. The compounds are the reaction product obtained from the reaction of selected salts of monoalkyl esters of maleic acid with selected active hydrogen containing compounds. These products are prepared by a reaction of the starting materials in preferably a substantially anhydrous medium at an elevated temperature.Type: GrantFiled: July 7, 1977Date of Patent: March 20, 1979Assignee: Lever Brothers CompanyInventors: Eddie N. Gutierrez, Vincent Lamberti
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Patent number: 4144226Abstract: Ether and acetal carboxylates useful as detergent builders to replace sodium tripolyphosphate (STP) in detergent formulations are known to the art. According to the present invention, new and novel polymeric acetal carboxylates are provided which are stable under laundry use conditions, but depolymerize in acid media, making the polymer fragments more readily biodegradable in waste streams.Type: GrantFiled: August 22, 1977Date of Patent: March 13, 1979Assignee: Monsanto CompanyInventors: Marvin M. Crutchfield, Victor D. Papanu, Craig B. Warren
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Patent number: 4137269Abstract: The present disclosure relates to steroids. More particularly, the disclosure is concerned with D-homosteroids, a process for the manufacture thereof and pharmaceutical preparations containing same. The subject D-homosteroids have high endocrinal activity and are particularly active as anti-inflammatory agents.Type: GrantFiled: October 12, 1976Date of Patent: January 30, 1979Assignee: Hoffmann-La Roche Inc.Inventors: Leo Alig, Andor Furst, Marcel Muller, Ulrich Kerb, Klaus Kieslich, Rudolf Wiechert
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Patent number: 4132702Abstract: Compounds of the formula I ##STR1## in which R.sub.1 and R.sub.2 independently of one another denote alkyl, cycloalkyl or aralkyl, R.sub.3 denotes hydrogen or, conjointly with R.sub.1, denotes tetramethylene, R.sub.4 denotes hydrogen or lower alkyl or, conjointly with R.sub.2, denotes tetramethylene, R.sub.5 denotes hydrogen, alkyl, aralkyl, acyloxyalkyl, oxaalkyl or phenyl, R.sub.6 denotes hydrogen, alkhyl, phenyl or the group or, conjointly with R.sub.5, denotes alkylene, R.sub.7 denotes hydrogen, alkyl, phenyl, benzyl or alkylphenyl or, conjointly with R.sub.5 or R.sub.6, denotes alkylene or, conjointly with R.sub.5 and R.sub.6, denotes alkanetriyl, R.sub.5, R.sub.6 and R.sub.7 together containing at least one carbon atom, Y denotes --O-- or --NH--, P denotes 1, 2, 3 or 4 and A denotes hydrogen or a group which is derived from an organic or inorganic oxygen acid A-(OH).sub.p, are suitable for stabilizing organic material against thermo-oxidative degradation.Type: GrantFiled: July 27, 1976Date of Patent: January 2, 1979Assignee: Ciba-Geigy CorporationInventors: Andreas Schmidt, Kurt Schwarzenbach
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Patent number: 4131740Abstract: Alkyl perfluoro-.omega.-fluoroformyl esters are provided which have the formula: ##STR1## wherein R is alkyl of 1-6 carbon atoms, and n is 0-6 (preferably 0). Compounds where n is 0 are prepared by contacting SO.sub.3 with a compound of the formula ROOC--CF.sub.2 --CF.sub.2 --OR.sup.1. Compounds where n is 1-6 are prepared by contacting a compound where n is 0 with hexafluoropropylene oxide.Type: GrantFiled: April 20, 1977Date of Patent: December 26, 1978Assignee: E. I. Du Pont de Nemours and CompanyInventor: David C. England
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Patent number: 4123458Abstract: Novel polyfunctional compounds and a novel process for their preparation are disclosed. These compounds may be converted into the acid or salt forms of cis and trans aconitic acids as well as into a racemic mixture of isocitric acid, alloisocitric acid and the lactones of isocitric acid and alloisocitric acid and their salts. All of the acid and salt forms produced are useful as metal sequestrants and/or detergent builders. The novel polyfunctional compounds can also be saponified to their corresponding alkali metal salts which, in turn, are also metal ion seqestering agents and detergent builders. The polyfunctional compounds are the reaction products obtained from the reaction of selected salts of monoalkyl esters of maleic acid with selected active hydrogen containing compounds.Type: GrantFiled: December 22, 1975Date of Patent: October 31, 1978Assignee: Lever Brothers CompanyInventors: Eddie N. Gutierrez, Vincent Lamberti
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Patent number: 4120874Abstract: A compound of the formula ##STR1## wherein R' is lower alkyl, is useful as an intermediate in the preparation of a corresponding tricarboxylate, which is a useful detergent builder.Type: GrantFiled: January 5, 1977Date of Patent: October 17, 1978Assignee: Monsanto CompanyInventors: Marvin M. Crutchfield, Kent P. Lannert
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Patent number: 4104367Abstract: An improved immunoassay for methadone is disclosed. The subject radioimmunoassay utilizes a novel antigen, antibody and novel labelled methadone derivatives.Type: GrantFiled: October 13, 1976Date of Patent: August 1, 1978Assignee: Hoffmann-La Roche Inc.Inventors: Magdalena Usategui Gomez, Harvey Gurien, John Edward Heveran, Manfred Weigele
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Patent number: 4100358Abstract: This disclosure concerns:(a) Compounds having the molecular structure represented by the formula: ##STR1## wherein M is selected from the group consisting of --H, --CH.sub.3, --C.sub.2 H.sub.5, --NH.sub.4, --Na, --K and combinations thereof; R is selected from the group consisting of an alkyl radical (branched or straight chain) containing up to about C.sub.20, --CH(CO.sub.2 M).sub.2, and --CH.sub.2 CO.sub.2 M, and R' is selected from the group consisting of an alkyl radical (branched or straight chain) containing up to about C.sub.20, --H, and --OR;(b) a method for making the compounds of (a);(c) solid and liquid detergent compositions comprising compounds of (a), and(d) washing processes employing the compounds of (a) and/or the compositions of (c).Type: GrantFiled: October 29, 1976Date of Patent: July 11, 1978Assignee: Monsanto CompanyInventor: Kent P. Lannert
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Patent number: 4100200Abstract: A compound having the formulaR -- SO.sub.2 O -- CH.sub.2 -- O -- CH.sub.2 -- OSO.sub.2 -- Rwherein R is alkyl, is prepared by reacting a compound having the formula ##STR1## wherein R and R' are alkyl with a cyclic polyoxymethylene or a linear polyoxymethylene in a substantially humidity-free environment. The compound is useful as an oxydimethylating agent for organic compounds.Type: GrantFiled: February 11, 1977Date of Patent: July 11, 1978Assignee: Eastman Kodak CompanyInventors: Cataldo Aldino Maggiulli, Donald MacArthur Burness, William Clarence Perkins
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Patent number: 4097678Abstract: 3.alpha.-Hydroxy and 3.alpha.-acyloxy- .DELTA..sup.9(11) -5.alpha.-D-homo-20-ketopregnenes of the formula ##STR1## wherein R is hydrogen or acyl, R.sub.1 is hydrogen or methyl and R.sub.2 is methyl or ethyl, are produced by esterifying a corresponding 3.beta.-hydroxy-5.alpha.-20-keto pregnane of the formula ##STR2## wherein R.sub.1 and R.sub.2 have the values given above, with m-iodo-benzoic acid with inversion of the 3.beta.-oxy group to a 3.alpha.-oxy group; chlorinating the thus-produced 3.alpha.-m-iodobenzoyl ester with dichloroiodobenzene under irradiation; and treating the reaction product with a dehydrohalogenating silver salt. Optionally thereafter, the 3.alpha.-iodobenzoyl group is split off in a conventional manner to produce the corresponding 3.alpha.-hydroxy steroid and optionally the thus-produced 3.alpha.-hydroxy steroid is esterified to produce a desired 3-ester thereof.Type: GrantFiled: June 8, 1976Date of Patent: June 27, 1978Assignee: Schering AktiengesellschaftInventors: Ulrich Kerb, Rudolf Wiechert, Otto Engelfried
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Patent number: 4095035Abstract: The present invention relates to a novel class of oligomeric builders for use in detergent compositions. More particularly, the present invention relates to a biodegradable, oligomeric polyacrylate having a molecular weight of greater than about 500 and less than about 10,000, preferably less than about 5000. In the most desirable embodiments at least one end of the oligomer chain is terminated with either a sulfur containing moiety or an hydroxy containing moiety. Preferred cations are alkali metals, ammonium and substituted ammonium.Type: GrantFiled: June 27, 1975Date of Patent: June 13, 1978Assignee: Lever Brothers CompanyInventors: Vincent Lamberti, Chester R. Willis
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Patent number: 4091040Abstract: A process for the production of trimethylolmethane in high yields. Trimetolmethane is useful as the essential precurser to trimethylolmethane trinitrate, a high-energy plasticizer and explosive.Type: GrantFiled: July 21, 1977Date of Patent: May 23, 1978Assignee: The United States of America as represented by the Secretary of the NavyInventor: Arnold T. Nielsen
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Patent number: 4088674Abstract: This invention concerns novel ester isocyanates derived from acyloxyalkylamine hydrochlorides. The novel compounds may contain a hetero atom in either the acid or alkanolamine moiety and may contain oxalic acid as the acyl moiety.Type: GrantFiled: May 12, 1972Date of Patent: May 9, 1978Assignee: Rohm and Haas CompanyInventors: William D. Emmons, Jerome F. Levy
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Patent number: 4086294Abstract: Water insoluble polycaprolactone-epoxide adducts are produced comprising the reaction product of a polycaprolactone polyol, a diepoxide and an anhydride of a polycarboxylic acid. The polycaprolactone polyol reacted with the diepoxide and the anhydride of the polycarboxylic acid has at least two hydroxyl groups in the molecule, a hydroxyl number of from about 15 to about 600 and an average molecular weight of from about 290 to about 6,000. The carboxylic acid anhydride has at least one intramolecular carboxylic anhydride group. These water insoluble polycaprolactone-epoxide adducts on reaction with an inorganic or organic base produce water soluble, carboxyl modifier polycarprolactone-epoxide oligomer addition reaction products which are eminently suitable for the production of aqueous coatings compositions. Exceptionally good coatings compositions are obtained when a crosslinker is present in the coating composition.Type: GrantFiled: May 26, 1976Date of Patent: April 25, 1978Assignee: Union Carbide CorporationInventors: Joseph Victor Koleske, Oliver Wendell Smith
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Patent number: 4082788Abstract: Organic acids contained in aqueous solution are separated and/or recovered by a process comprising adding an alcohol to the aqueous solution to esterify the acids present, while preferably simultaneously contacting the alcoholic mixture with a water-immiscible solvent and separating layers into an aqueous phase and an organic phase, whereby extraction with the water-immiscible solvent shifts the equilibrium toward the formation of more esters. The esters of the acids may than be recovered as by distillation.Type: GrantFiled: August 19, 1969Date of Patent: April 4, 1978Assignee: El Paso Products CompanyInventor: Samuel S. Mims
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Patent number: 4079084Abstract: Novel fluorocarbon surfactants containing a non-ionic hydrophilic chain (preferably an oxyethylene chain) and at least two terminal perfluorocarbon groups of at least three carbon atoms, preferably branched perfluorocarbon groups derived from an oligomer of tetrafluoroethylene.Type: GrantFiled: July 25, 1974Date of Patent: March 14, 1978Assignee: Imperial Chemical Industries LimitedInventor: Leonard Eric Houghton
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Patent number: 4078147Abstract: Hydroxy diester compounds are obtained by esterification between malic acid or tartaric acid and a saturated, aliphatic alcohol of 16 or more carbon atoms having side chains. These compounds are a colorless, odorless synthetic oil with low cloud point, which have a wide range of from low viscosity to high viscosity depending on the starting materials. Said synthetic oils are useful for basic oils or emulsions in the fields of cosmetics, detergents and medicinal preparations.Type: GrantFiled: September 10, 1975Date of Patent: March 7, 1978Assignee: The Nisshin Oil Mills, Ltd.Inventors: Akitoshi Ukai, Yutaka Usui
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Patent number: 4059616Abstract: Polymers of esters of methacrylic acid having an average chain length of about 6 to about 50 mers are prepared by an anionic polymerization reaction, carried out in the presence of a chain-regulating alcohol and a catalytic amount of an alkoxide anion, in which control of the molecular weight and molecular weight distribution of the polymer are achieved by regulating the ratio of the total quantity of alcohol employed to the total monomer charge. These polymers, their hydrolysis products, and their derivatives having allyl functionality have a wide variety of applications, including use as components in films, coatings, fibers, impregnants, adhesives, printing inks, and binders, and use as modifiers, plasticizers, melt flow improvers, and leveling agents.Type: GrantFiled: October 23, 1974Date of Patent: November 22, 1977Assignee: Rohm and Haas CompanyInventors: Sheldon N. Lewis, Richard A. Haggard
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Patent number: 4058554Abstract: Novel polyfunctional compounds which may be hydrolyzed to the corresponding salts, which in turn are metal sequestering agents, are disclosed, as well as a novel method for their preparation. The compounds are the reaction product obtained from the reaction of selected salts of monoalkyl esters of maleic acid with selected active hydrogen containing compounds. These products are prepared by a reaction of the starting materials in preferably a substantially anhydrous medium at an elevated temperature.Type: GrantFiled: December 22, 1975Date of Patent: November 15, 1977Assignee: Lever Brothers CompanyInventors: Eddie N. Gutierrez, Vincent Lamberti
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Patent number: 4058553Abstract: Preparation of alkoxymethylene malonic acid ester of formula: ##STR1## wherein R and each R' is an alkyl group, by reaction of malonic acid diester and ortho formic acid triester. The reaction is performed in the presence of a carboxylic acid or a carboxylic acid anhydride and a Lewis acid. The ortho ester is initially present in amount of at least 1,4 mols per mole of the malonic acid ester starting material. Alcohol formed during the reaction is removed during the reaction.Type: GrantFiled: May 30, 1975Date of Patent: November 15, 1977Assignee: Dynamit Nobel AktiengesellschaftInventors: Otto Ackermann, Otto Bleh, deceased, Walter Rogler
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Patent number: 4055597Abstract: This invention relates to 10-aza-11,12-secoprostaglandins and processes for their manufacture. These compounds have prostaglandin-like biological activity and are particularly useful as renal vasodilators.Type: GrantFiled: June 2, 1975Date of Patent: October 25, 1977Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., John B. Bicking
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Patent number: 4048065Abstract: For inhibiting corrosion and scale on ferrous metal parts in a circulating water system there is added to the water in such system from 10 to 500 ppm of a partial ester of a polyfunctional acid having a free carboxylate, phosphonate or sulfonate group and another carboxyl group which is esterified with a polyoxyalkylated derivative of an alkyl, alkaryl, or alkenyl alcohol having a terminal hydrocarbon group of 8-20 carbon atoms. In some preferred embodiments there is added with the partial ester from 10 to 500 ppm of a dispersible enhancing agent which may also include a surface active agent for dispersing the agent in water. Preferred partial esters include partial esters of citric, malic, tartaric, maleic, adipic and phthalic acids partially esterified with an alkyl polyoxyethylene alcohol having 2 to 4 ethoxy groups.Type: GrantFiled: July 17, 1975Date of Patent: September 13, 1977Assignee: American Cyanamid CompanyInventors: Tzeng Jiueq Suen, Arthur James Begala, Jr., Martin Grayson
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Patent number: 4046817Abstract: A process for the synthesis of pyrogallol from glutaric ester and dialkoxymalonic ester.Type: GrantFiled: February 17, 1976Date of Patent: September 6, 1977Assignee: IMC Chemical Group, Inc.Inventor: Mohammed T. Shipchandler