Lactic Acid Per Se Or Salt Thereof Patents (Class 562/589)
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Patent number: 5510526Abstract: A process for the production of lactic acid and for the separation and/or recovery of lactic acid from a lactate feed solution. A lactate feed solution preferably obtained from a fermentation broth is combined with and extracted by a water immiscible trialkyl amine in the presence of carbon dioxide. Lactic acid is recovered from the resulting organic phase. Recovered carbonate or bicarbonate from the aqueous phase is preferably recycled to the fermentor and regenerated extractant is preferably recycled for use in the extraction.Type: GrantFiled: March 8, 1994Date of Patent: April 23, 1996Assignee: Cargill, IncorporatedInventors: Abraham M. Baniel, Aharon M. Eyal, Joseph Mizrahi, Betty Hazan, Rod R. Fisher, Jeffrey J. Kolstad, Brenda F. Stewart
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Patent number: 5488156Abstract: Lactic acid formed via fermentation generally is susceptible to the development of color bodies when heated to temperatures of approximately 180.degree. C. and above. Color development appears to result from carbonization of small amounts of carbohydrates. Consequently a heat-stable lactic acid may be produced by subjecting an aqueous solution of lactic acid to temperatures between about 180 and 230.degree. C. for a time sufficient to carbonize the carbohydrates, with subsequent removal of the color bodies using standard decolorants such as activated charcoal. Heat treatment may be applied either directly to the broth or to an aqueous solution resulting from one or more processing steps applied to the fermentation broth.Type: GrantFiled: December 23, 1994Date of Patent: January 30, 1996Assignee: UOPInventors: Santi Kulprathipanja, Gregory F. Maher, Thomas W. Lorsbach
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Patent number: 5464739Abstract: A composition and method for determining the presence of leukocyte cells, esterase or protease in a test sample are disclosed. The composition contains a lactate ester having the structure ##STR1## wherein A is an alcohol blocking group, and wherein B-O- is a residue of compound B-OH and provides a detectable response when the lactate ester is hydrolyzed; and a buffer. One class of lactate ester has the structure ##STR2## wherein X is O, S or NR.sup.2, R is aryl or lower alkyl, R.sup.1 is hydrogen or lower alkyl, and R.sup.2 is hydrogen, lower alkyl or aryl.Type: GrantFiled: August 22, 1994Date of Patent: November 7, 1995Assignee: Bayer CorporationInventors: Gary M. Johnson, Robert J. Schaeper
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Patent number: 5426219Abstract: An organic acid can be recovered from a fermentation broth by clarifying the broth to remove at least a substantial portion of the impurities therein, producing a clarified feed; acidulating the clarified feed by adding a quantity of a mineral acid effective to lower the pH of the feed to between about 1.0 and about 4.5, producing an acidulated feed which is substantially saturated with respect to at least one electrolyte selected from the group consisting of MHSO.sub.4, M.sub.2 SO.sub.4, M.sub.3 PO.sub.4, M.sub.2 HPO.sub.4, MH.sub.2 PO.sub.4, and MNO.sub.3, where M is selected from the group consisting of Na, NH.sub.4, and K; extracting the acidulated feed with an extraction mixture which includes (a) water, (b) a mineral acid, in a quantity effective to maintain the pH of the feed between about 1.0 and about 4.Type: GrantFiled: July 26, 1993Date of Patent: June 20, 1995Assignee: A.E. Staley Manufacturing Co.Inventors: William F. Lehnhardt, Robert V. Schanefelt, Lori L. Napier
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Method for the dissolution of calcium carbonate solids in the presence of aqueous chlorine solutions
Patent number: 5411727Abstract: A process for dissolving calcium carbonate solids in the presence of an aqueous chlorine-containing solution without the formation of chlorine gas comprising adding a sufficient amount of lactic acid to the solution dissolving said solids.Type: GrantFiled: August 10, 1994Date of Patent: May 2, 1995Assignee: Olin CorporationInventors: Richard M. Mullins, Jeffrey J. Glen -
Patent number: 5409822Abstract: A fluidized bed reactor system utilizes a fluid phase, a retained fluidized primary particulate phase, and a migratory second particulate phase. The primary particulate phase is a particle such as a gel bead containing an immobilized biocatalyst. The secondary particulate phase, continuously introduced and removed in either cocurrent or countercurrent mode, acts in a secondary role such as a sorbent to continuously remove a product or by-product constituent from the fluid phase. Introduction and removal of the sorbent phase is accomplished through the use of feed screw mechanisms and multivane slurry valves.Type: GrantFiled: June 29, 1993Date of Patent: April 25, 1995Assignee: Martin Marietta Energy Systems, Inc.Inventors: Charles D. Scott, Joseph A. Marasco
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Patent number: 5371287Abstract: This invention relates to a composition which has an alkali(ne earth) metal hydroxycarboxylate and an aliphatic carboxylic acid which has a lower pKa than that of the hydroxycarboxylic acid. The hydroxycarboxylate salt, when used e.g. in an aqueous medium which allows dissociation of the salt and the aliphatic carboxylic acid into anions and cations, dissociates into the metal ions and hydroxycarboxylate ions, and the acid into the corresponding carboxylate ions and hydrogen ions. The relative pKa values of the two acids ensure that the aliphatic acid forms the alkali(ne earth metal salt thereby liberating the free hydroxycarboxylic acid in situ. This method masks the unpleasant odors of acids for ensiling etc without causing distress to operatives during storage and use.Type: GrantFiled: January 11, 1994Date of Patent: December 6, 1994Assignee: BP Chemicals LimitedInventor: Johannes A. C. Van Ooijen
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Patent number: 5349084Abstract: The present invention relates to a process for inexpensively and effectively recovering a high-purity organic acid, according to which a crude organic acid is subjected to extraction treatment with an organic solvent to obtain an organic solvent extract containing an organic acid; the organic solvent extract is mixed with a high-pressure gas to precipitate and separate impurities thereby obtaining a solution containing a high-purity organic acid; and the organic acid is separated from the solution to obtain a high-purity organic acid.Type: GrantFiled: September 25, 1991Date of Patent: September 20, 1994Assignee: Idemitsu Petrochemical Co., Ltd.Inventors: Akihiro Shishikura, Hiroshi Kimbara, Katsuhisa Yamaguchi, Kunio Arai
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Patent number: 5340646Abstract: A breathable, hydrolyzable, porous film which is obtained by the process comprising adding from 40 to 250 parts by weight of a finely-powdered filler having an average particle size of from 0.3 to 4 .mu.m to 100 parts by weight of a polylactic acid-based resin composition comprising from 80 to 100% by weight of polylactic acid or a lactic acid-hydroxycarboxylic acid copolymer and from 0 to 20% by weight of a plasticizer, melting and film-forming the resultant mixture, and successively stretching the thus-obtained film 1.1 times or more at least in the direction of the axis; and which is consequently useful as a material for leakproof films of sanitary materials such as a paper diaper and packaging materials, and does not accumulate as wastes because of hydrolyzability in the natural environment in the case of being abandoned after use.Type: GrantFiled: April 21, 1992Date of Patent: August 23, 1994Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Kenji Morita, Kohichi Uchiki, Hosei Shinoda
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Patent number: 5324856Abstract: Disclosed is a process for making an .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid which comprises (1) hydrocarboxylating an enol acylate, which has a chiral C atom that is essentially all L or all D, with CO and water or an organic hydroxyl compound, thereby producing a reaction mixture containing diastereomeric .alpha.-acyloxy acids or esters having two chiral centers and having essentially no enantiomeric pairs, (2) separating the diastereomers by conventional physical means and (3) hydrolyzing at least one of said separated diastereomers to make at least the .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid.Also disclosed is a process for making an .alpha.Type: GrantFiled: August 17, 1992Date of Patent: June 28, 1994Inventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
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Patent number: 5278256Abstract: The depolymerization of poly(hydroxyacids) in a liquid medium is enhanced by the presence of a quaternary ammonium compound. Poly(hydroxyacid) polymers containing a quaternary ammonium salt are more readily depolymerized.Type: GrantFiled: September 16, 1992Date of Patent: January 11, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventor: Harold E. Bellis
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Patent number: 5276181Abstract: A catalytic method of hydrogenating glycerol is directed essentially towards the production of oxygenated compounds having from 1 to 3 carbon atoms, particularly 1,2-propandiol and lactic acid. It provides for glycerol to be placed in contact with hydrogen and made to react therewith in the presence of a ruthenium catalyst modified with sulphides and of a base, at a temperature of at least 200.degree. C.Type: GrantFiled: July 9, 1992Date of Patent: January 4, 1994Inventors: Bruno Casale, Ana Maria Gomez
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Patent number: 5270189Abstract: A fluidized bed reactor system which utilizes a fluid phase, a retained fluidized primary particulate phase, and a migratory second particulate phase. The primary particulate phase is a particle such as a gel bead containing an immobilized biocatalyst. The secondary particulate phase, continuously introduced and removed in either cocurrent or countercurrent mode, acts in a secondary role such as a sorbent to continuously remove a product or by-product constituent from the fluid phase. Introduction and removal of the sorbent phase is accomplished through the use of feed screw mechanisms and multivane slurry valves.Type: GrantFiled: November 21, 1991Date of Patent: December 14, 1993Assignee: Martin Marietta Energy Systems, Inc.Inventor: Charles D. Scott
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Patent number: 5264626Abstract: Rapid recovery from waste of high molecular weight polyhydroxyacid content by depolymerizing the PHA in acidic water.Type: GrantFiled: November 22, 1991Date of Patent: November 23, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Loren D. Brake, Narayanan S. Subramanian
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Patent number: 5264614Abstract: Polyhydroxyacid (PHA) is recovered by heating under pressure in the presence of a C.sub.1 -C.sub.6 alcohol, and optionally also water.Type: GrantFiled: November 22, 1991Date of Patent: November 23, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Loren D. Brake
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Patent number: 5264617Abstract: Depolymerizing polyhydroxy acid by heating with the alcohol of 1-6 carbon atoms in the presence of an acid catalyst to produce an alkyl ester.Type: GrantFiled: November 22, 1991Date of Patent: November 23, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Loren D. Brake
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Patent number: 5229528Abstract: Recovery of polyhydroxy acids (PHAs) from waste containing high molecular weight polyhydroxy acid polymer by depolymerizing the PHA in water at elevated temperature and pressure.Type: GrantFiled: November 22, 1991Date of Patent: July 20, 1993Assignee: E. I. du Pont de Nemours and CompanyInventors: Loren D. Brake, Narayanan S. Subramanian
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Patent number: 5210294Abstract: Purified lactic acid aqueous solutions obtained by percolating fermentation broths through columns of appropriate ion-exchange resins.Type: GrantFiled: June 3, 1992Date of Patent: May 11, 1993Assignee: Himont IncorporatedInventors: Giorgio Mantovani, Giuseppe Vaccari, Anna L. Campi
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Patent number: 5210296Abstract: The production of high purity lactate ester or lactic acid from a concentrated fermentation broth by continuous acidification in the presence of an alcohol diluent with sequential or simultaneous esterification, distillation off of high purity ester, and, if desired, hydrolysis of the ester to high purity lactic acid.Type: GrantFiled: June 20, 1991Date of Patent: May 11, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Michael C. M. Cockrem, Pride D. Johnson
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Patent number: 5136057Abstract: Processes are described for recovering lactic acid from impure lactide and the residue produced in the depolymerization of polylactic acid to lactide. Lactic acid is recovered from the impure lactide by a dual solvent extraction process and, from the polylactic acid residue by hydrolysis. The lactic acid recovered from the impure lactide and the depolymerization residue is recycled to provide for a high yield lactide process.Type: GrantFiled: October 22, 1991Date of Patent: August 4, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Kamlesh K. Bhatia
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Patent number: 5084480Abstract: Salts of pentamidine, formulations containing such salts and the use of such salts of treatment or prophylaxis of pneumocystis carinii. Pentamidine gluconate and lactate has been discovered and found to have high water solubility while providing potentially less toxic alternatives to pentamidine isethionate, especially for aerosolized administration to patients suffering from acquired immunodeficiency syndrome, AIDS, or AIDS related complex, ARC.Type: GrantFiled: July 19, 1989Date of Patent: January 28, 1992Assignee: Fujisawa USA, Inc.Inventors: Sadanand Pai, Abu S. Alam, John N. Kapoor
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Patent number: 5081150Abstract: Calcium lactate-glycerol adduct, a molecular compound of 1 mole of calcium lactate and 2 moles of glycerol, and a process for its preparation are described. The adduct can be used as a calcium donor or auxiliary in pharmacy, cosmetics and the production of foodstuffs.Type: GrantFiled: April 12, 1990Date of Patent: January 14, 1992Assignee: Hoechst AktiengesellschaftInventors: Bernhard Reul, Walter Petri
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Patent number: 5068418Abstract: Lactic acid is separated from a fermentation broth by using an adsorbent comprising a water-insoluble macroreticular or gel weakly basic anionic exchange resin possessing tertiary amine or pyridine functional groups or a strongly basic anionic exchange resin possessing quaternary amine fuctional groups. The resins are in sulfate form and have a cross-linked acrylic or styrene resin matrix. Lactic acid is desorbed with water or dilute inorganic acid, e.g., sulfuric. The pH of the feed is maintained below the ionization constant (pKa) of lactic acid to obtain high selectivity.Type: GrantFiled: May 8, 1989Date of Patent: November 26, 1991Assignee: UOPInventors: Santi Kulprathipanja, Anil R. Oroskar
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Patent number: 5026821Abstract: The present invention provides polyamides produced by the condensation of diamines with citric acid through the carboxyl groups attached to the carbon atoms in positions 1 and 3.These polyamides can be used for the preparation of controlled-release forms of drugs.Type: GrantFiled: March 2, 1989Date of Patent: June 25, 1991Assignee: SanofiInventors: Mahfoud Boustta, Jovanka Huquet, Michel Vert
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Patent number: 5001245Abstract: A preparation of metallic salt of ethercarboxylic acid in a pure form by restraining the formation of fumaric acid likely to occur when maleic acid and/or maleic anhydride react with oxycarboxylic acid. The ethercarboxylic product is a useful chelating agent.Type: GrantFiled: February 13, 1989Date of Patent: March 19, 1991Assignee: Nippon Shokubai Kagaku Kogyo Company, Ltd.Inventors: Masao Nakano, Miaki Asakawa, Yusei Nagamura, Akio Fukui, Yoichi Nakagawa
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Patent number: 4771001Abstract: The disclosure describes a method for producing lactic acid from carbohydrate-containing media by continuous fermentation utilizing particular methods of media pretreatment, cell-recycle fermentation, fermentation broth acidification, and lactic acid separation.Type: GrantFiled: September 24, 1986Date of Patent: September 13, 1988Assignee: Neurex Corp.Inventors: Richard B. Bailey, Dilip K. Joshi, Stephen L. Michaels, Richard A. Wisdom
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Patent number: 4749811Abstract: In the process of hydrocarboxylating an enol acylate with CO and an organic hydroxyl compound to produce an .alpha.-acyloxy acid ester, the improvement comprising using as the organic hydroxyl compound reactant, an organic hydroxyl compound which has a chiral center that is essentially all L or D, thereby producing a reaction mixture having essentially no enantiomeric pairs and containing diastereomeric .alpha.-acyloxy acid esters having two chiral centers.Type: GrantFiled: October 29, 1985Date of Patent: June 7, 1988Assignee: The Standard Oil CompanyInventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
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Patent number: 4720577Abstract: The invention relates to a process for the extraction of carboxylic acids from aqueous solutions with a carboxylic acid content below 8% by weight. A mixture of an aliphatic amine with a total carbon number of at least 10 and a phenol or naphthol is used as extracting agent. The molar ratio of phenol:amine or alkylated phenol:amine or naphthol:amine is in the range from 0.1:1 to around 1.1:1.Type: GrantFiled: October 2, 1985Date of Patent: January 19, 1988Assignee: Hoechst AktiengesellschaftInventors: Bernhard Wojtech, Walter Steppich, Dieter Freudenberger, Knut Riedel
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Patent number: 4698303Abstract: The invention provides a method for producing lactic acid by continuous fermentation utilizing particular methods of media pretreatment, cell-recycle fermentation, fermentation broth acidification, and lactic acid separation.Type: GrantFiled: March 27, 1986Date of Patent: October 6, 1987Assignee: Engenics, Inc.Inventors: Richard B. Bailey, Dilip K. Joshi, Stephen L. Michaels, Richard A. Wisdom
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Patent number: 4691055Abstract: An improved process is provided for concentrating organic compounds from dilute aqueous solutions such as fermentation liquors. Conventional distillation of the compounds to remove the bulk of the water is eliminated by selective adsorption on adsorbent carbon. The compounds are eluted from the carbon with the vapors of a volatile solvent and then the volatile solvent is evaporated from the eluate to give a concentrated aqueous solution containing at least 30% by weight of the organic compounds.Type: GrantFiled: December 7, 1981Date of Patent: September 1, 1987Assignee: CPC International Inc.Inventor: Branko Urbas
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Patent number: 4528384Abstract: Novel polymers having high activity as cationic surface-active agents are prepared by the addition polymerization of ethylenically unsaturated aromatic sulfonium salts, e.g., ##STR1## When such polymers are heated and/or dried, they are irreversibly converted to inert, nonionic residues without the elimination of odorous by-products.The novel sulfonium salt polymers having relatively low molecular weight and low charge density are particularly useful as surfactants or emulsifiers in the emulsion polymerization of ethylenically unsaturated monomers such as styrene, butadiene, alkyl acrylates and the like. The polymers having high molecular weight and high charge density are useful as thickeners and flocculants.Type: GrantFiled: June 30, 1980Date of Patent: July 9, 1985Assignee: The Dow Chemical CompanyInventors: Donald L. Schmidt, Thomas C. Klingler, Ritchie A. Wessling
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Patent number: 4457850Abstract: Flotation aids and a process for the flotation of non-sulfidic minerals. The flotation aids have the formula ##STR1## wherein R repesents an aliphatic, cyclic, or alicyclic C.sub.7 -C.sub.23 radical, optionally substituted with one or more hydroxyl, sulfhydryl, carbonyl, ether, or thioether groups; X.sup.n+ is hydrogen or a water-solubilizing, salt-forming cation; and n is the valence of X. The invention also relates to ore suspensions and mineral concentrates in association with the above flotation aids.Type: GrantFiled: May 6, 1983Date of Patent: July 3, 1984Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Holger Tesmann, Helmut Kachel
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Patent number: 4444881Abstract: A process is provided for the recovery of organic acids from dilute aqueous solutions. The acid in the form of its calcium salt is treated with a tertiary amine carbonate and the resulting trialkylammonium salt of the acid is isolated and heated to give the acid plus a tertiary amine.Type: GrantFiled: June 27, 1983Date of Patent: April 24, 1984Assignee: CPC International Inc.Inventor: Branko Urbas
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Patent number: 4420636Abstract: Crystalline calcium ammonium lactate dihydrate, a constituent formed from fermented ammoniated condensed whey, and is useful as a nutrient for ruminant animals.Type: GrantFiled: October 27, 1981Date of Patent: December 13, 1983Assignee: Calor Agriculture Research, Inc.Inventors: Fred W. Juengst, Jr., John A. Dika
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Patent number: 4377708Abstract: Vinyl esters such as vinyl acetate are hydrocarboxylated with tertiary organo-phosphine stabilized palladium catalysts utilizing low water concentration; the ready hydrolysis of the .alpha.-acetoxypropionic acid affords a convenient route to lactic acid.Type: GrantFiled: October 14, 1977Date of Patent: March 22, 1983Assignee: Monsanto CompanyInventor: Donald E. Morris
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Patent number: 4351955Abstract: Acetone cyanohydrin is converted to alpha-hydroxyisobutyric acid by contacting the cyanohydrin with alpha-hydroxymethanesulfonic acid and water at a temperature of about 70.degree.-125.degree. C. The alpha-hydroxymethanesulfonic acid is an equilibrium product of the reaction of water, sulfur dioxide and formaldehyde.Type: GrantFiled: November 5, 1980Date of Patent: September 28, 1982Assignee: Shell Oil CompanyInventors: Carl L. Willis, Lynn H. Slaugh
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Patent number: 4334095Abstract: Organic acids, such as citric acid, malic acid and lactic acid, can be extracted from aqueous solutions thereof by contacting such solutions with a mixture of a water immiscible amine and a water immiscible organic acid dissolved in a suitable water immiscible solvent.Type: GrantFiled: October 6, 1980Date of Patent: June 8, 1982Assignee: Miles Laboratories, Inc.Inventor: Avraham M. Baniel
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Patent number: 4283349Abstract: Novel oxiodinium and thiaiodinium compounds having a superior inhibitory effect against micro-organisms coupled with outstanding stability and low toxicity are described.Type: GrantFiled: May 21, 1979Date of Patent: August 11, 1981Assignee: Eli Lilly and CompanyInventor: William N. Cannon
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Patent number: 4282385Abstract: Novel hyperacid solid metal lactates containing up to about twenty moles of lactic acid per mole a neutral metal lactate are produced by reacting an aqueous solution of lactic acid containing up to about 0.5 percent polylactic acids with a suitable metal compound. Such lactates have the formula Me(C.sub.3 H.sub.5 O.sub.3).sub.x (C.sub.3 H.sub.6 O.sub.3).sub.n wherein n represents a number from 4 to 12 and x corresponds to the valence of the metal Me, and are useful in the food industry as substitutes for liquid lactic acids in the making of bread and beverages.Type: GrantFiled: April 25, 1979Date of Patent: August 4, 1981Assignee: SKW Trostberg AktiengesellschaftInventors: Ulrich Metz, Horst Michaud