Patents Assigned to Commercial Solvents Corporation
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Patent number: 3997568Abstract: (10'R)-Zearalanone is prepared from (10'S)-zearalenone by opening the lactone ring of the zearalenone in an alkaline medium to provide a hydroxy acid, esterifying the hydroxy acid to provide a hydroxy ester, tosylating the hydroxy ester, reacting the tosyl ester with a tetraalkyl ammonium alkyl ester to invert the (S) structure to the (R) structure, and reforming and hydrogenating the lactone to provide (10'R)-zearalanone. (10'R)-Zearalanone, when present in admixture with (10'S)-zearalanone, enhances the uterotropic activity of the latter compound.Type: GrantFiled: March 18, 1974Date of Patent: December 14, 1976Assignee: Commercial Solvents CorporationInventors: Charles Allan Peters, Richard Nelson Hurd
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Patent number: 3967015Abstract: A process for dyeing fiberglass by the steps of applying thereto a combination consisting of a substituted oxazoline and a thermosetting epoxy resin, heating at about 270.degree.-300.degree.F and applying a disperse, or an acid dye or a vat dye thereto.Type: GrantFiled: April 1, 1974Date of Patent: June 29, 1976Assignee: Commercial Solvents CorporationInventor: Jerry H. Hunsucker
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Patent number: 3966699Abstract: Reduced bacitracin and pharmaceutically acceptable salts thereof obtained by treating bacitracin with a reducing agent. The resulting product has improved stability.Type: GrantFiled: February 7, 1975Date of Patent: June 29, 1976Assignee: Commercial Solvents CorporationInventor: Mohammed T. Shipchandler
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Patent number: 3965082Abstract: An improved process for emulsion polymerization by using as the initiator and the surfactant an oxazoline corresponding to the formula: ##EQU1## where R is an alkyl group of 1-19 carbons, and R.sup.1 and R.sup.2 are methyl, ethyl, hydroxymethyl, or the group RCH.sub.2 COOCH.sub.2 -.Type: GrantFiled: September 2, 1975Date of Patent: June 22, 1976Assignee: Commercial Solvents CorporationInventor: Louis A. Jurisch
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Patent number: 3965275Abstract: A process, and the composition used therein, for estrogenic therapy which comprises administering daily to the patient from about 0.2 to 2000 milligrams of a compound having the formula: ##EQU1## wherein R is selected from the group consisting of hydrogen, lower alkyl and a lower saturated acyclic acyl; Z is selected from the group consisting of >CH.sub.2, >CHOH and >C=O; and A is selected from the group consisting of --CH.sub.2 --CH.sub.2 -- and --CH=CH--.Type: GrantFiled: May 12, 1975Date of Patent: June 22, 1976Assignee: Commercial Solvents CorporationInventors: Phil H. Hidy, Robert S. Baldwin
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Patent number: 3965274Abstract: A method for inhibiting pregnancy in female mammals which comprises administering an effective amount of a compound having the formulae: ##SPC1##The compound is administered for at least one full estrus cycle to insure prevention of pregnancy and thereafter as long as it is desired.Type: GrantFiled: June 7, 1974Date of Patent: June 22, 1976Assignee: Commercial Solvents CorporationInventors: Phil H. Hidy, Robert S. Baldwin
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Patent number: 3960816Abstract: An improved process for the preparation of sand cores for foundry use in metal casting by mixing sand with a binder, and packing into a mold to harden. The improvement in the process resides in using as the binder an oxazoline or condensation product thereof.Type: GrantFiled: January 6, 1975Date of Patent: June 1, 1976Assignee: Commercial Solvents CorporationInventor: Louis A. Jurisch
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Patent number: 3960835Abstract: Compounds of the formula: ##SPC1##Wherein --A-- is either --CH.sub.2 --CH.sub.2 -- or --CH=CH--, >Z is either >CH.sub.2, >C=O or >CH--OH, Y is --H or --OR' wherein R' can be hydrogen, alkyl, alkanoyl, aryl, or aryl alkyl, and Gly is a glycosyl group, which exhibit anabolic and estrogenic activity, are provided, as well as processes for their preparation and compositions containing them which are useful as ruminant growth promoters.Type: GrantFiled: January 18, 1974Date of Patent: June 1, 1976Assignee: Commercial Solvents CorporationInventor: Donald E. Robertson
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Patent number: 3960898Abstract: The high-melting diastereoisomer of zearalanol or derivative thereof is prepared by heating its corresponding low-melting diastereoisomer under dehydrogenating conditions in the presence of a Raney nickel catalyst and under an oxygen-free atmosphere, and then subjecting the solution to reducing conditions under a hydrogen atmosphere at elevated pressure.Type: GrantFiled: February 5, 1974Date of Patent: June 1, 1976Assignee: Commercial Solvents CorporationInventor: Edward B. Hodge
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Patent number: 3957864Abstract: An improved process for recovering 1-glutamic acid from an aqueous solution containing it by the steps of adjusting the pH of the solution to about 4.5, at ambient temperature, holding at that pH until crystals of 1-glutamic acid begin to appear, heating to from 47.degree. to about 55.degree.C, adjusting the pH to 3.2, cooling, and recovering the crystals resulting therefrom.Type: GrantFiled: March 31, 1975Date of Patent: May 18, 1976Assignee: Commercial Solvents CorporationInventor: John S. Gallagher
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Patent number: 3957825Abstract: This invention provides a new synthesis for zearalanone and for related compounds having more or fewer carbon atoms in the non-aromatic ring than does zearalanone, which related compounds and zearalanone are represented by the formula ##SPC1##Wherein X is an integer having a value from 2 to 6 inclusive and Y is an integer having a value from 2 to 8 inclusive. It also provides for new methods of making compounds useful in the synthesis of zearalanone and related compounds.The new compounds useful as intermediates are 2,7-octadienoic acid; methyl 2,7-octadienoate; sodium ethyl 6-(4-pentenyl)-.beta.-dihydroresorcylate; ethyl 6-(4-pentenyl)-.beta.-dihydroresorcylate; sodium methyl 6-(4-pentenyl)-.beta.-dihydroresorcylate; methyl 6-(4-pentenyl)-.beta.-dihydroresorcylate; methyl 3-bromo-6-(4-pentenyl)-.beta.-dihydroresorcylate; methyl 6-(4-pentenyl)-.beta.-resorcylate; ethyl 6-(4-pentenyl)-.beta.-resorcylate; ethyl 6-(4-pentenyl)-.beta.-resorcylate dibenzyl ether; and 4-penten-2-yl 6-(4-pentenyl)-.beta.Type: GrantFiled: November 27, 1974Date of Patent: May 18, 1976Assignee: Commercial Solvents CorporationInventors: Wilbert Herbert Urry, Guy Towns Mullenbach
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Patent number: 3956305Abstract: Phosphated derivatives of 4,4-bis(hydroxymethyl) oxazolines and process for preparation. The compounds are represented by the formula ##EQU1## where R is alkyl or alkenyl of from 11 to 21 carbon atoms and R' is lower alkyl of 1 to about 5 carbon atoms. The products have utility as corrosion inhibitors in lube oils.Type: GrantFiled: May 8, 1975Date of Patent: May 11, 1976Assignee: Commercial Solvents CorporationInventor: Daniel G. Mudd
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Patent number: 3954805Abstract: Zearalene type compounds are prepared by treating zearalenone type compounds in a solvent selected from the group consisting of acetic anhydride, propionic anhydride, dioxane, ethyl acetate, ethyl ether, and tetrahydrofurane, under reducing conditions in the presence of reducing amounts of zinc and hydrogen halide.Type: GrantFiled: March 25, 1975Date of Patent: May 4, 1976Assignee: Commercial Solvents CorporationInventor: Frank Kavka
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Patent number: 3953432Abstract: Tranquilizing agents for warm-blooded animals corresponding to the formula ##EQU1## where n can be 1 or 2; Y can be ##EQU2## where R.sup.2 can be hydrogen or an alkyl, alkenyl, alkoxy, phenyl or methoxyphenyl radical. Z can be thienyl, furyl, phenyl; or mono-, di-, or trimethoxyphenyl; mono-, or dichlorophenyl, or dichlorophenoxy. R and R.sup.1 can be hydrogen, methyl, or ethyl and can be the same or different.Type: GrantFiled: December 4, 1972Date of Patent: April 27, 1976Assignee: Commercial Solvents CorporationInventor: Herbert L. Wehrmeister
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Patent number: 3951916Abstract: An improved epoxy resin composition comprising an epoxy resin suitable for adhesive, potting or laminating use mixed with from about 0.1% to about less than 3% of an oxazolidine ester represented by the formula: ##EQU1## where R is an alkyl or alkenyl group of from 5 to 21 carbon atoms.Type: GrantFiled: May 14, 1974Date of Patent: April 20, 1976Assignee: Commercial Solvents CorporationInventor: David K. Sausaman
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Patent number: 3946534Abstract: A process for substantially eliminating dissolved oxygen from a liquid and from a shipping container therefor by purging the container with inert gas, pressuruzing with the gas to about at least 10 psig and then releasing the pressure, repeating the pressurizing and releasing steps for a plurality of times, introducing the liquid while maintaining flow of inert gas until the container is filled, and closing said container securely.Type: GrantFiled: January 16, 1975Date of Patent: March 30, 1976Assignee: Commercial Solvents CorporationInventor: Richard S. Egly