Patents Assigned to Commercial Solvents Corporation
  • Patent number: 3997568
    Abstract: (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: Grant
    Filed: March 18, 1974
    Date of Patent: December 14, 1976
    Assignee: Commercial Solvents Corporation
    Inventors: Charles Allan Peters, Richard Nelson Hurd
  • Patent number: 3967015
    Abstract: 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: Grant
    Filed: April 1, 1974
    Date of Patent: June 29, 1976
    Assignee: Commercial Solvents Corporation
    Inventor: Jerry H. Hunsucker
  • Patent number: 3966699
    Abstract: Reduced bacitracin and pharmaceutically acceptable salts thereof obtained by treating bacitracin with a reducing agent. The resulting product has improved stability.
    Type: Grant
    Filed: February 7, 1975
    Date of Patent: June 29, 1976
    Assignee: Commercial Solvents Corporation
    Inventor: Mohammed T. Shipchandler
  • Patent number: 3965082
    Abstract: 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: Grant
    Filed: September 2, 1975
    Date of Patent: June 22, 1976
    Assignee: Commercial Solvents Corporation
    Inventor: Louis A. Jurisch
  • Patent number: 3965275
    Abstract: 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: Grant
    Filed: May 12, 1975
    Date of Patent: June 22, 1976
    Assignee: Commercial Solvents Corporation
    Inventors: Phil H. Hidy, Robert S. Baldwin
  • Patent number: 3965274
    Abstract: 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: Grant
    Filed: June 7, 1974
    Date of Patent: June 22, 1976
    Assignee: Commercial Solvents Corporation
    Inventors: Phil H. Hidy, Robert S. Baldwin
  • Patent number: 3960816
    Abstract: 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: Grant
    Filed: January 6, 1975
    Date of Patent: June 1, 1976
    Assignee: Commercial Solvents Corporation
    Inventor: Louis A. Jurisch
  • Patent number: 3960835
    Abstract: 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: Grant
    Filed: January 18, 1974
    Date of Patent: June 1, 1976
    Assignee: Commercial Solvents Corporation
    Inventor: Donald E. Robertson
  • Patent number: 3960898
    Abstract: 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: Grant
    Filed: February 5, 1974
    Date of Patent: June 1, 1976
    Assignee: Commercial Solvents Corporation
    Inventor: Edward B. Hodge
  • Patent number: 3957864
    Abstract: 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: Grant
    Filed: March 31, 1975
    Date of Patent: May 18, 1976
    Assignee: Commercial Solvents Corporation
    Inventor: John S. Gallagher
  • Patent number: 3957825
    Abstract: 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: Grant
    Filed: November 27, 1974
    Date of Patent: May 18, 1976
    Assignee: Commercial Solvents Corporation
    Inventors: Wilbert Herbert Urry, Guy Towns Mullenbach
  • Patent number: 3956305
    Abstract: 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: Grant
    Filed: May 8, 1975
    Date of Patent: May 11, 1976
    Assignee: Commercial Solvents Corporation
    Inventor: Daniel G. Mudd
  • Patent number: 3954805
    Abstract: 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: Grant
    Filed: March 25, 1975
    Date of Patent: May 4, 1976
    Assignee: Commercial Solvents Corporation
    Inventor: Frank Kavka
  • Patent number: 3953432
    Abstract: 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: Grant
    Filed: December 4, 1972
    Date of Patent: April 27, 1976
    Assignee: Commercial Solvents Corporation
    Inventor: Herbert L. Wehrmeister
  • Patent number: 3951916
    Abstract: 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: Grant
    Filed: May 14, 1974
    Date of Patent: April 20, 1976
    Assignee: Commercial Solvents Corporation
    Inventor: David K. Sausaman
  • Patent number: 3946534
    Abstract: 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: Grant
    Filed: January 16, 1975
    Date of Patent: March 30, 1976
    Assignee: Commercial Solvents Corporation
    Inventor: Richard S. Egly