Purification Or Recovery Patents (Class 568/868)
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Patent number: 4665241Abstract: Crude product substituted 1,3-diols obtained by aldolization and subsequent hydrogenation are treated at elevated temperatures with at least sufficient basic additives to reduce the saponification number to zero. Thereupon, the saponified product is reacted with 5 to 30% water and possibly cooled to 1.degree. to 30.degree. C. The aqueous phase is separated mechanically, and following the separation and addition of 5 to 30% water the organic phase is adjusted to a pH of 8.0 to 10.5. A second aqueous phase is removed and, thereupon, the monovalent alcohol is removed by distillation from the second organic phase. Again the pH value of the second organic phase is set at 8.0 to 10.5 and the 1,3-diol is recovered by fractionation.Type: GrantFiled: May 9, 1986Date of Patent: May 12, 1987Assignee: Huls AktiengesellschaftInventor: Walter K. Homann
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Patent number: 4661646Abstract: 1-Butene-3,4-diol is prepared by heat treatment of 2-butene-1,4-diol in the presence of catalytically active substances under acid conditions.Type: GrantFiled: November 21, 1985Date of Patent: April 28, 1987Assignee: Bayer AktiengesellschaftInventors: Rolf Schalenbach, Helmut Waldmann
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Patent number: 4661647Abstract: The invention relates to a granular mannitol directly compressible and free from binder, characterized by the fact that its granulometric fraction from 400 to 500 .mu.m has a friability less than 65% in a test A.Type: GrantFiled: October 11, 1985Date of Patent: April 28, 1987Assignee: Roquette FreresInventors: Michel Serpelloni, Patrick Lemay
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Patent number: 4647705Abstract: This invention relates to a process for improving the ultraviolet light transmittance of ethylene glycol by treating industrial grade ethylene glycol with an aluminum-nickel alloy in the presence of an alkali compound.Type: GrantFiled: August 15, 1985Date of Patent: March 3, 1987Assignee: BASF CorporationInventors: Thomas M. Schmitt, George M. Allen, Pauls Davis
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Patent number: 4622104Abstract: A process for the separation of ethylene glycol from glycolated water obtained from the bottom of an ethylene oxide desorption column in a process for the manufacture of ethylene oxide by catalytic oxidation of ethylene by oxygen in the vapor phase, comprising feeding said glycolated water directly from the bottom of said ethylene oxide desorption column into the top of a separation column having therebelow up to 12 theoretical plates and adding sufficient indirect heat to said glycolated water to form two streams; a first gaseous stream consisting essentially of steam which is removed from the top of said separation column and introduced into said ethylene oxide desorption column to serve therein as the desorption fluid, and a second aqueous stream containing from about 40% to 90% by weight of ethylene glycol which is removed from the bottom of said separation column.Type: GrantFiled: July 16, 1984Date of Patent: November 11, 1986Assignee: AtochemInventors: Henri Neel, Francis Delannoy
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Patent number: 4605783Abstract: An adsorptive method of separating alcohols and aldehydes or ketones and alcohols of monoterpenes is disclosed. The method uses an X-type zeolite containing sodium and potassium cations to selectively adsorb the alcohols thereby allowing recovery of an aldehyde or ketone raffinate stream and, after desorption, an alcohol extract stream. The method is suitable for feed mixtures containing individual or multiple monoterpenoid components.Type: GrantFiled: March 21, 1985Date of Patent: August 12, 1986Assignee: UOP Inc.Inventor: Hermann A. Zinnen
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Patent number: 4605762Abstract: A process for the neutral hydrolytic depolymerization of condensation polymers is described. The process is conducted in a continuous manner and comprises introducing condensation polymer waste material into an aqueous hydrolysis zone at a temperature of between 200.degree. C. and 300.degree. C. and superatmospheric pressure of at least 15 atmospheres. High pressure steam is introduced into the lower portion of the hydrolysis zone underneath the level of the condensation polymer waste material. The steam serves as the principal source of heat for the hydrolysis zone. By being introduced underneath the level of the condensation polymer waste material, the steam agitates the waste material to provide heat transfer to accelerate the hydrolysis reaction. Further, a portion of the steam condenses to provide water which is a reactant in the hydrolysis reaction. An aqueous solution of the product(s) of the hydrolysis reaction is withdrawn from an upper portion of the hydrolysis zone.Type: GrantFiled: December 21, 1983Date of Patent: August 12, 1986Assignee: Celanese Mexicana S.A.Inventor: Jorge W. Mandoki
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Patent number: 4605794Abstract: A modified sorbitol with improved tableting properties, viz, has a melting point of about 96.degree. C., a bulk density of 0.3-0.6 g/ml, a .gamma.-sorbitol content of at least 90%, a purity of at least 98%, a specific surface area of 0.7-1.5 m.sup.2 /g, a bending strength of at least 7 N/mm.sup.2 at a compressive force of at least 10,000 N, and a friability of less than 1% at a compressive force of at least 10,000 N, can be prepared by obtaining a sorbitol solution by hydrogenation of crystallized glucose at a temperature below 170.degree. C., and spray-drying this solution at a temperature of 140.degree. to 170.degree. C. The sorbitol thus obtained has a water content of less than 1%.The sorbitol is useful for the production of compressed formulations.Type: GrantFiled: January 23, 1985Date of Patent: August 12, 1986Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Friedrich Reiff, Hartmut Hartner, Arno Basedow, Hans-Wolfgang Hugenbusch, Peter C. Schmidt, Hans Bardonner
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Patent number: 4599467Abstract: A process is provided for production of vicinal alkylene glycols by hydrolysis of an epoxyalkane having from 6 to 24 carbon atoms in the presence of water and a basic catalyst and under carbon dioxide pressures of from 100 to 300 bars and temperatures of from about 200.degree. C. to 350.degree. C. Also disclosed are homogeneous mixtures of epoxyalkanes and/or vicinal alkylene glycols having from 6 to 24 carbon atoms, water, a basic catalyst and carbon dioxide in an amount corresponding to a carbon dioxide partial pressure of from about 100 to 300 bars, provided at temperatures from about 200.degree. C. to 350.degree. C. The process provides high yields, selectivities and reaction velocities and the resulting products are of high purity.Type: GrantFiled: April 10, 1985Date of Patent: July 8, 1986Assignee: AKZO NVInventors: Hilde Kersten, Gerhard Meyer
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Patent number: 4594462Abstract: Butane-1,4-diol is prepared by catalytic hydrogenation of dibutyl succinate by a process in which hydrogenation is terminated before complete conversion is reached, butanol is distilled off from the reaction mixture, the liquid distillation residue is cooled to below 108.degree. C., the upper phase, which is formed as a result of phase separation and essentially consists of dibutyl succinate, is recycled to the hydrogenation, and the butane-1,4-diol is obtained from the lower phase, which essentially consists of this compound, by fractional distillation under reduced pressure.Type: GrantFiled: June 26, 1985Date of Patent: June 10, 1986Assignee: BASF AktiengesellschaftInventors: Rolf Schnabel, Hans-Martin Weitz
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Patent number: 4542239Abstract: Terephthalic acid (TPA) is recovered from used polyethylene terephthalate beverage containers by reacting comminuted containers in a reaction zone with an aqueous medium containing ammonium hydroxide at elevated temperatures and pressures to form a water soluble diammonium salt of TPA, separating any undissolved solids from the reaction product, acidifying the remaining reaction product to liberate TPA, and separating the precipitated TPA. A portion of the liquid remaining after separation of TPA can be mixed with lime or slaked lime, the resulting mixture treated in an ammonia stripper to remove ammonia therefrom and the ammonia overheads from the stripper blended with another portion of the liquid remaining after separation of TPA to form a stream containing ammonium hydroxide which is recycled to the reaction zone. Ethylene glycol can be recovered from the bottoms from the ammonia stripper by distillation.Type: GrantFiled: June 7, 1983Date of Patent: September 17, 1985Assignee: Board of Control of Michigan Technological UniversityInventors: Richard A. Lamparter, Bruce A. Barna, David R. Johnsrud
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Patent number: 4507511Abstract: A modified sorbitol with improved tableting properties, viz, has a melting point of about 96.degree. C., a bulk density of 0.3-0.6 g/ml, a .gamma.-sorbitol content of at least 90%, a purity of at least 98%, a specific surface area of 0.7-1.5 m.sup.2 /g, a bending strength of at least 7 N/mm.sup.2 at a compressive force of at least 10,000 N, and a friability of less than 1% at a compressive force of at least 10,000 N, can be prepared by obtaining a sorbitol solution by hydrogenation of crystallized glucose at a temperature below 170.degree. C., and spray-drying this solution at a temperature of 140.degree. to 170.degree. C. The sorbitol thus obtained has a water content of less than 1%.The sorbitol is useful for the production of compressed formulations.Type: GrantFiled: December 7, 1983Date of Patent: March 26, 1985Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Friedrich Reiff, Hartmut Hartner, Arno Basedow, Hans-Wolfgang Hugenbusch, Peter C. Schmidt, Hans Bardonner
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Patent number: 4484012Abstract: A method for hydrolyzing coffee extraction residue materials to produce manno-saccharides having a degree of polymerization from 1 to 10 and subsequently neutralizing and reducing said mixture of manno-saccharides to their corresponding alcohols. The coffee material, preferably spent coffee grounds from a commercial percolation system, is hydrolyzed in a Plug Flow tubular reactor in the presence of an acid catalyst, such as sulfuric acid. Depending on the time, temperature, pressure and catalyst concentration selected, manno-saccharides or mannose is produced. The manno-saccharides or mannose produced are separated from coffee residue material in the form of a syrup and neutralized with calcium hydroxide. The neutralized mixture of manno-saccharides or mannose is reduced to their corresponding alcohols or mannitol.Type: GrantFiled: February 29, 1984Date of Patent: November 20, 1984Assignee: General Foods CorporationInventors: Howard Stahl, Renee Bayha, Charles V. Fulger, Evan J. Turek
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Patent number: 4482765Abstract: An improved process for the preparation of hydroxycitronellol by an addition reaction of water with citronellol. This reaction takes place directly on heating a homogeneous solution of citronellol in a mixture of water and an inert solvent selected from the group consisting of acetone, methyl ethyl ketone, glymes, and tetrahydrofuran. The reaction is catalyzed with a cation exchange resin.Type: GrantFiled: June 24, 1983Date of Patent: November 13, 1984Assignee: Union Camp CorporationInventor: Mark S. Pavlin
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Patent number: 4479021Abstract: There is described a continuous process for producing 1,2-alkanediols of the formula ##STR1## in which R is an alkyl group having 3-6 carbon atoms, by reaction of a 1-alkene of the formulaR--CH.dbd.CH.sub.2in which R is as defined above, with formic acid and hydrogen peroxide, and subsequent saponification of the formed alkanediol monoformate, which process is performed in several consecutive reaction stages.The 1,2-alkanediols of the above formula obtainable by the process are intermediates for the production of pesticides.Type: GrantFiled: August 30, 1983Date of Patent: October 23, 1984Assignee: Ciba-Geigy CorporationInventors: Heinz Issler, Rudolf Maul
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Patent number: 4465873Abstract: A process is disclosed for obtaining butanediols by distilling the same from an aqueous solution obtained by hydrogenation, carried out in the presence of a nickel catalyst, of a hydroformylated allyl alcohol. The invention process is characterized in that 2-methyl-1,3-propanediol, 1,4-butanediol and a high-boiling fraction are separated by distillation from a butanediol mixture obtained using the following steps:(1) the aqueous solution is treated such that the pH of the aqueous solution is adjusted to 8.5 or above, and precipitates thus formed are removed;(2) the aqueous solution is treated such that residual 4-hydroxybutyraldehyde and water are distilled off at a temperature of up to 100.degree. C.; and(3) the resulting mixture is heated at a temperature of up to 180.degree. C. to obtain a distillate consisting of 2-methyl-1,3-propanediol and 1,4-butanediol, free of the high-boiling fraction.Type: GrantFiled: July 6, 1983Date of Patent: August 14, 1984Assignees: Daicel Chemical Industried, Ltd., Kuraray Co., Ltd.Inventor: Yoshiyuki Harano
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Patent number: 4450294Abstract: An oxygenated organic compound, such as ethanol, is recovered from a dilute aqueous stream thereof by contacting said stream with crosslinked polyvinylpyridine resin or nuclear substituted derivative thereof to effect selective sorption of the compound by said resin. The sorbed compound is thereafter removed from the resin by stripping with an inert gas such as carbon dioxide.Type: GrantFiled: November 1, 1982Date of Patent: May 22, 1984Assignee: National Distillers and Chemical CorporationInventor: Julian Feldman
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Patent number: 4447643Abstract: A thermally efficient process for recovering an oxygenated organic material, such as ethanol, present in dilute aqueous solution is disclosed which comprises contacting said dilute aqueous solution with at least one inert extractant which is liquid at ambient temperature and pressure, said extractant being selected from the group consisting of unsubstituted and substituted cyclic secondary amines and unsubstituted and substituted aromatic cyclic amines having a distribution coefficient of at least about 0.70 or a separation factor of at least about 1.0.Type: GrantFiled: August 11, 1982Date of Patent: May 8, 1984Assignee: National Distillers and Chemical CorporationInventor: Julian Feldman
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Patent number: 4419189Abstract: Excess water and color-forming materials present in crude 1,4-butanediol are reduced by subjecting the crude 1,4-butanediol to distillation under conditions wherein substantially all the water present in the crude 1,4-butanediol is first removed and then the 1,4-butanediol with reduced water content is further refined by flash evaporation under vacuum.Type: GrantFiled: January 11, 1982Date of Patent: December 6, 1983Assignee: E. I. Du Pont de Nemours & Co.Inventor: Vincent P. Caracciolo
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Patent number: 4413140Abstract: A solvent comprising at least one aromatic hydrocarbon and/or halogenated paraffin is used in a liquid extraction process for extracting diesters from mixtures comprising diesters, the corresponding monoesters and acids, diols and water.Type: GrantFiled: April 26, 1977Date of Patent: November 1, 1983Assignee: Phillips Petroleum CompanyInventor: George B. Fozzard
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Patent number: 4383895Abstract: Color-forming materials or their precursors present in crude 1,4-butanediol are reduced more efficiently by subjecting the crude 1,4-butanediol to distillation under conditions wherein substantially all the water present in the crude 1,4-butanediol is first removed and then the 1,4-butanediol with reduced water content is further distilled to remove the color-forming materials.Type: GrantFiled: September 21, 1981Date of Patent: May 17, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventors: Richard E. Ernst, Donald C. Paul
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Patent number: 4355175Abstract: Polyester scrap such as film (plain or silver-bearing), fabric, yarn or bottles, based primarily on polyethylene terephthalate, is depolymerized at room temperature and atmospheric pressure with a mixture of concentrated sulfuric acid and water to form crude terephthalic acid which is purified by dissolving in alkali solution, filtering to remove impurities, acidifying the filtrate to recover terephthalic acid in high yield with a purity of at least 99%.Type: GrantFiled: April 6, 1981Date of Patent: October 19, 1982Inventor: Stephen F. Pusztaszeri
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Patent number: 4349417Abstract: Ethylene oxide and water are reacted in a reactor and the reaction product is subjected to distillation in a plurality of distillation columns, in the first columns water and components having a boiling point below that of monoethylene glycol and higher ethylene glycols, if any, being distilled off. To obtain extremely pure monoethylene glycol alkali metal compounds are added at a point between the reactor and the monoethylene glycol distillation column in an amount to adjust the pH of the product entering the latter column to a value of from 7 to 10. The monoethylene glycol obtained in this manner is especially pure and has very low UV absorption values. It is, therefore, especially suitable for the manufacture of polyester fibers.Type: GrantFiled: January 9, 1981Date of Patent: September 14, 1982Assignee: Hoechst AktiengesellschaftInventors: Siegfried Rebsdat, Sigmund Mayer, Josef Alfranseder, Iwo Schaffelhofer
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Patent number: 4294998Abstract: A process for the purification of crude 1,4-butanediol by crystallizing said crude in a solution comprising tetrahydrofuran at a temperature of from 10.degree. to -10.degree. C. and a pressure of from 16-26 mm of mercury to form a slurry of crystallized 1,4-butanediol in a liquid, and then separating the crystallized 1,4-butanediol from the liquid.Type: GrantFiled: July 31, 1980Date of Patent: October 13, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Harry B. Copelin
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Patent number: 4293570Abstract: An apparatus and process for the preparation of cryptocrystalline sweeteners, such as sorbitol, by the spraying of a heated, aqueous, low-viscosity, high-solids, sweetener solution, employing a cool, compressed, inert gas, through a nozzle into a fine spray and into a cooler atmosphere, to form very fine particles of the sprayed sweetener product.Type: GrantFiled: April 2, 1979Date of Patent: October 6, 1981Assignee: Chimicasa GmbHInventor: Kalman Vadasz
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Patent number: 4280867Abstract: A system for regeneration of a liquid disiccant which utilizes a reboiler and still column to remove a major portion of absorbed water and then exposes the hot, partially dehydrated desiccant to a flow of dry, inert flue gas and a partial vacuum, in order to remove additional water from the desiccant.Type: GrantFiled: June 11, 1979Date of Patent: July 28, 1981Assignee: Maloney-Crawford CorporationInventor: Robert A. Hodgson
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Patent number: 4276126Abstract: Mixtures containing ethylene glycol and N-methylpyrrolidone can be separated by azeotropic distillation by employing a C.sub.7 -C.sub.10 hydrocarbon, having a boiling point between 110.degree. and 190.degree. C. as the azeotroping agent. An azeotrope of the hydrocarbon and ethylene glycol constitutes the overhead product while the bottoms product comprises N-methylpyrrolidone.Type: GrantFiled: November 30, 1979Date of Patent: June 30, 1981Assignee: National Distillers and Chemical CorporationInventor: Bernard A. Saffer
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Patent number: 4243560Abstract: Scrap foam of flexible or semi-rigid polyurethane is pyrolized at 450.degree.-800.degree. C., preferably 600.degree. C., in the absence of air and of any added reactive agents or catalysts. The residence time may be from 3 minutes to one hour, preferably about 5 minutes. A distillate is obtained comprising an aqueous phase and an organic phase. The latter essentially consists of alcohols and polyols and may be re-used as such for preparing polyurethane resins.Type: GrantFiled: April 4, 1979Date of Patent: January 6, 1981Assignee: Centro Ricerche Fiat S.p.A.Inventor: Augusto Balestrini
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Patent number: 4228094Abstract: There is described a process of extracting ethylene glycol from admixture with tetraglyme containing rhodium values therein using glycerine as the extraction solvent.Type: GrantFiled: August 19, 1976Date of Patent: October 14, 1980Assignee: Union Carbide CorporationInventor: David R. Bryant
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Patent number: 4225394Abstract: Ethylene glycol is recovered from spent glycol containing impurities, such as dimethyl terephthalate, by subjecting the spent glycol to a sequential flash evaporation-distillation or distillation-flash evaporation-distillation procedure. Dimethyl terephthalate impurities are rendered non-volatile by the addition of a small amount of alkali metal hydroxide prior to flash evaporation. Dewatering of spent glycol and separation of ethylene glycol from impurities rendered non-volatile by alkali metal hydroxide is also performed in one or two distillation steps. Sufficient ethylene glycol is recovered to make use of flash evaporation an optional step.Type: GrantFiled: April 14, 1976Date of Patent: September 30, 1980Assignee: PPG Industries, Inc.Inventors: Jerry W. Cox, Mulkey C. Wilkes
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Patent number: 4213000Abstract: 1,4-Butynediol is catalytically hydrogenated under conventional conditions to produce a reaction product containing 1,4-butanediol. This reaction product is then hydrogenated under acid conditions, i.e., pH 1-6 and temperatures of 120.degree.-150.degree. C., to produce a 1,4-butanediol product. Upon further separation, the 1,4-butanediol is practically free from compounds that would produce color when the diol is used to make polyesters.Type: GrantFiled: May 29, 1979Date of Patent: July 15, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: John S. Coates
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Patent number: 4200501Abstract: Silicate fouling on the reboilers and trays and the distillation train used for the production of dihydric alcohols is arrested by the addition of caustic to the feed stream.Type: GrantFiled: March 24, 1978Date of Patent: April 29, 1980Assignee: BASF Wyandotte CorporationInventors: Edward J. Panek, Werner O. Moll, Lee H. Bergman, Siegfried P. Kersten
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Patent number: 4187153Abstract: According to the present invention an impure liquid containing ethylene glycol or propylene glycol, lower carboxylate esters of the glycol, water, carboxylic acid and glycol-azeotroping agent is treated for removal of substantially all of said glycol-azeotroping agent by a process which comprises distilling the impure liquid in a distillation zone to form an overheads product comprising water and glycol-azeotroping agent and a bottoms product comprising the glycol, esters and carboxylic acid, which is substantially free of said glycol-azeotroping agent, said bottoms product containing water in an amount of at least about 1 weight percent of the amount of water passed to said distillation zone with said impure liquid.Type: GrantFiled: November 14, 1977Date of Patent: February 5, 1980Assignee: Halcon Research & Development CorporationInventors: Alan Peltzman, Charles C. Yang
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Patent number: 4182659Abstract: Water-containing glycol is heated first at atmospheric or superatmospheric pressure to partially remove water and concentrate the glycol and is then heated at subatmospheric pressure to further concentrate the glycol.Type: GrantFiled: October 31, 1977Date of Patent: January 8, 1980Assignee: Davy International AktiengesellschaftInventors: Jamil Anwer, Kuldip K. Sud, Karl Wintrup
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Patent number: 4154970Abstract: A process for treating butanediol obtained as a condensate during the manufacture of polybutylene terephthalate, wherein an alkali metal alcoholate or alkali metal hydride is added to the condensate at an elevated temperature. After purification, the butanediol obtained is re-used for the manufacture of polybutylene terephthalate.Type: GrantFiled: June 8, 1978Date of Patent: May 15, 1979Assignee: BASF AktiengesellschaftInventors: Ludwig Beer, Heinrich Mandel
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Patent number: 4151048Abstract: Ethylene glycol or 1,2-propylene glycol contained in mixtures with lower carboxylate esters of glycol, e.g. as produced by hydrolysis of the esters, is recovered by distillation of the mixtures with a hydrocarbon forming a minimum boiling azeotrope with the ethylene dlycol or 1,2-propylene glycol, the hydrocarbon being maintained in an inert atmosphere in the system.Type: GrantFiled: June 6, 1977Date of Patent: April 24, 1979Assignee: Halcon Research and Development CorporationInventors: Mitchell Becker, Howard M. Sachs
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Patent number: 4127730Abstract: A non-swellable three-dimensional polymer having a component which is a residue of an optically active compound, which residue is chemically removable from said polymer to leave behind in the physical structure of said polymer a void corresponding to the size and shape of said residue of optically active compound, and a particular steric arrangement of functional groups within the void of said polymer corresponding to the chemical structure of said residue of optically active compound, the original polymer having recurring units of the formulas ##STR1## wherein A, C and D are residues bonded to B of compounds which residues are polymerizable or polycondensable and B is a residue of an optically active compound; a process for preparing such polymer and the form of such polymer containing such void and free of the residue of optically active compounds.Type: GrantFiled: March 10, 1978Date of Patent: November 28, 1978Assignee: Dynamit Nobel AktiengesellschaftInventors: Gunter Wulff, Ali Sarhan
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Patent number: 4105701Abstract: A liquid contaminated with a carbonyl compound, especially an aldehyde, is purified by being contacted with a bed of solid polyvinyl alcohol particles or fibers. The carbonyl compound is adsorbed or chemisorbed onto the solid polyvinyl alcohol surface with resulting reaction in the carbonyl content of the liquid.Type: GrantFiled: April 28, 1975Date of Patent: August 8, 1978Assignee: Celanese CorporationInventor: Donald R. Larkin
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Patent number: 4096036Abstract: A method is disclosed for the separation of water soluble polyols. A solution containing the polyols is passed cyclically at different temperatures through a column containing ion exchange materials to separate the polyols.Type: GrantFiled: April 7, 1977Date of Patent: June 20, 1978Assignee: Standard Brands IncorporatedInventors: Victor S. H. Liu, Norman E. Lloyd, Khaja Khaleeluddin
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Patent number: 4096175Abstract: Covers a method of separating a nonionic surfactant from an anionic surfactant by use of methylal.Type: GrantFiled: December 1, 1976Date of Patent: June 20, 1978Assignee: Texaco Development CorporationInventors: Carter G. Naylor, Simon P. Burns