Patents Represented by Attorney Carl G. Ries
  • Patent number: 5093382
    Abstract: Foamed reaction products of organic polyisocyanates containing an average of at least 2 isocyanate groups per molecule with equivalent weights of carbon dioxide-generating, carboxyl group terminated addition reaction products of a polyoxyalkylene polyamine or polyoxyalkylene polyol reactant with a polycarboxylic acid reactant,the polyoxyalkylamine and polyoxyalkyl polyol reactant having an average molecular weight of about 200 to about 5,000 and being selected from the group consisting of polyoxypropylene diamines, polyoxypropylene/oxyethylene diamines, poly(oxytetramethylene) diamines and polyoxypropylene triamines, polyoxypropylene diols, polyoxypropylene/oxyethylene diols, poly(oxytetramethylene) diols and polyoxypropylene triols,the polycarboxylic acid reactant containing 2 to about 45 carbon atoms and being selected from the group consisting of aromatic and aliphatic dicarboxylic acids and anhydrides thereof.
    Type: Grant
    Filed: August 8, 1991
    Date of Patent: March 3, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Donald H. Champion
  • Patent number: 5091572
    Abstract: Liquid amine terminated polyamide addition products having an average molecular weight of about 3,000 to about 10,000 are prepared by the non-catalytic reaction of a dicarboxylic acid having a molecular weight within the range of about 130 to about 700 with a higher molecular weight polyoxypropylene diamine having an average molecular weight within the range of about 1,500 to about 6,000 and with a lower molecular weight polyoxypropylene diamine having an average molecular weight within the range of about 200 to about 700, the reaction conditions including a temperature within the range of about 150.degree. to about 280.degree. C., a pressure of about 0.1 to 20 atmospheres and a reaction time of about 2 to about 5 hours.
    Type: Grant
    Filed: December 11, 1989
    Date of Patent: February 25, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Wei-Yang Su
  • Patent number: 5091574
    Abstract: Tetrafunctional amine derivatives of digyclidyl ethers of Bisphenol A that are liquid at ambient temperatures and that are useful as curing agents for epoxy resins are disclosed together with the method by which they are prepared which comprises the steps of:dissolving the diglycidyl ether in a solvent (acetone or methyl ethyl ketone) and adding a polyoxyalkylene diamine in the mole ratio of about 4 to about 5 moles of the diglycidyl ether per mole of said polyoxyalkylene diamine to provide an initial reaction mixture,heating the initial reaction mixture with agitation at a temperature of about 80.degree. to about 160.degree. C.
    Type: Grant
    Filed: February 25, 1991
    Date of Patent: February 25, 1992
    Assignee: Texaco Chemical Company
    Inventors: Jiang-Jen Lin, George P. Speranza
  • Patent number: 5066804
    Abstract: A 4-alkyl-2-morpholinone is prepared by reacting glyoxal with a C.sub.1 -C.sub.18 N-alkylmonoethanolamine in solution in a solvent that azeotropes with water at a temperature of about -10.degree. to 20.degree. C. for about 1 to 5 hours and by then heating the reaction mixture to a temperature of at least about 110.degree. C. to remove an azeotrope of water and solvent from the mixture to thereby substantially selectively convert the C.sub.1 -C.sub.18 N-alkylmonoethanolamine to the corresponding 4-alkyl-2-morpholinone.
    Type: Grant
    Filed: October 12, 1990
    Date of Patent: November 19, 1991
    Assignee: Texaco Chemical Company
    Inventor: Wei-Yang Su
  • Patent number: 5059247
    Abstract: A foundry sand composition that is self-hardening after a working life of about 10-20 minutes that is composed of a foundry sand, a sodium silicate binder and a specifically defined polyester polycarbonate hardener is prepared by:a) mixing a foundry sand with about 2-6 wt. %, based on the foundry sand, of an aqueous solution containing about 40-60 wt. % of sodium silicate, the ratio of SiO.sub.2 /Na.sub.2 O of the sodium silicate about 2.2 to 3, to form an initial sand mixture, andb) then adding about 5-15 wt. % of the polyester polycarbonate hardener, based on the weight of the aqueous solution of sodium silicate, to provide the foundry sand composition.
    Type: Grant
    Filed: August 20, 1990
    Date of Patent: October 22, 1991
    Assignee: Texaco Chemical Company
    Inventors: Wheeler C. Crawford, Michael Cuscurida
  • Patent number: 5037838
    Abstract: N-hydroxyethyl piperazine is converted to triethylenediamine using a titania-supported tungstopyrophosphate catalyst.
    Type: Grant
    Filed: April 26, 1990
    Date of Patent: August 6, 1991
    Assignee: Texaco Chemical Company
    Inventors: Robert L. Zimmerman, John F. Knifton
  • Patent number: 5030754
    Abstract: Hydroxy-terminated substituted diurea derivatives of hydroxy-terminated polyurea derivatives of secondary monoalkylamines and organic diisocyanates and hydroxy-terminated polyurea derivatives of secondary monalkylamines and prepolymers of organic diisocyanates with polyoxyalkylene polyols, such as hydroxy-terminated polyurea derivatives of secondary monoalkylamines and organic diisocyanates having the formula: ##STR1## wherein: R represents an aliphatic or an aromatic group containing from 6 to about 20 carbon atoms,R' represents H or an alkyl group containing 1 to 6 carbon atoms, andn is a positive integer having a value of 1 to 4.
    Type: Grant
    Filed: November 19, 1990
    Date of Patent: July 9, 1991
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Jiang-Jen Lin
  • Patent number: 5025100
    Abstract: Tetrafunctional amine derivatives of digyclidyl ethers of Bisphenol A that are liquid at ambient temperatures and that are useful as curing agents for epoxy resins are disclosed together with the method by which they are prepared which comprises the steps of:dissolving the diglycidyl ether in a solvent (acetone or methyl ethyl ketone) and adding a polyoxyalkylene diamine in the mole ratio of about 4 to about 5 moles of the diglycidyl ether per mole of said polyoxyalkylene diamine to provide an initial reaction mixture,heating the initial reaction mixture with agitation at a temperature of about 80.degree. to about 160.degree. C.
    Type: Grant
    Filed: February 6, 1990
    Date of Patent: June 18, 1991
    Assignee: Texaco Chemical Company
    Inventors: Jiang-Jen Lin, George P. Speranza
  • Patent number: 5003107
    Abstract: Poly(oxytetramethylene) diamines useful in the preparation of polyamide and polyurea elastomers are prepared by the catalytic reductive amination of a poly(oxytetramethylene) glycol feedstock under reductive amination conditions in the presence of ammonia and hydrogen using a hydrogenation/dehydrogenation catalyst composed of, on an oxide-free basis, about 70 to 75 wt. % of nickel, about 20 to about 25 wt. % of copper, about 0.5 to 5 wt. % of chromium and about 1 to 5 wt. % of molybdenum.
    Type: Grant
    Filed: December 18, 1989
    Date of Patent: March 26, 1991
    Assignee: Texaco Chemical Company
    Inventors: Robert L. Zimmerman, John M. Larkin
  • Patent number: 5001267
    Abstract: Secondary alkyl amine derivatives of ethylenediamine are formed in a one-step reaction when ethylenediamine is substantially simultaneously continuously mixed with a methyl alkyl ketone to form a reaction mixture which is continuously hydrogenated in the presence of a hydrogenation catalyst and hydrogen, the alkyl group containing 1 to 4 carbon atoms.
    Type: Grant
    Filed: March 13, 1989
    Date of Patent: March 19, 1991
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Jiang-Jen Lin, James H. Templeton, Wei-Yang Su
  • Patent number: 4994627
    Abstract: A feedstock selected from the group consisting of polyoxyethylene glycols, polyoxypropylene glycols and monoalkyl ethers thereof having molecular weights of about 200 to about 5,000 and contaminated with more than about 100 ppm of alkali metal or alkaline earth metal ions is purified by bringing said feedstock into contact with a basic ion exchange resin in the presence of about 2 to about 10 wt. % of water, based on the weight of the feedstock at a temperature of about 25.degree. to about 100.degree. C. and a pressure of about 0 to about 100 psig. for a period of time sufficient to lower the impurity level of said ions by at least about 90% to a level of less than about 100 ppm,the basic ion exchange resin being a fully hydrated boron specific basic styrene-divinyl benzene ion exchange resin in the free base form having an apparent density of about 40 to 45 lbs. per cubic foot.
    Type: Grant
    Filed: March 16, 1990
    Date of Patent: February 19, 1991
    Assignee: Texaco Chemical Company
    Inventors: Michael Cuscurida, Arthur J. Faske
  • Patent number: 4992566
    Abstract: Tertiary butyl hydroperoxide and tertiary butyl alcohol are recovered from the reaction product formed by reacting excess propylene with tertiary butyl hydroperoxide in solution in tertiary butyl alcohol in the presence of a soluble molybdenum catalyst, by fractionating the reaction produce to provide distillate propylene, propylene oxide, and tertiary butyl alcohol fractions and a heavy distillation fraction comprising tertiary butyl hydroperoxide, tertiary butyl alcohol and impurities, including dissolved molybdenum catalyst, the tertiary butyl hydroperoxide and tertiary butyl alcohol being recovered from the heavy distillation fraction by vacuum evaporation under evaporation conditions including a temperature of about 25.degree. to about 160.degree. C. and a pressure of about 2 to about 200 mm Hg. in order to provide a lighter condensate fraction comprising about 60 to about 95 wt. % of the heavy distillation fraction and containing from about 70 to about 95 wt.
    Type: Grant
    Filed: August 31, 1989
    Date of Patent: February 12, 1991
    Assignee: Texaco Chemical Company
    Inventors: Edward T. Marquis, Kenneth P. Keating, John R. Sanderson, Robert A. Meyer
  • Patent number: 4992602
    Abstract: Tertiary butyl alcohol is prepared by the catalytic decomposition of tertiary butyl hydroperoxide in solution in a monocyclic aromatic solvent in the presence of a metal phthalocycnaine catalyst.
    Type: Grant
    Filed: January 29, 1990
    Date of Patent: February 12, 1991
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, Edward T. Marquis
  • Patent number: 4983565
    Abstract: This invention is directed to novel phosphorus-free catalyst compositions based on titania pellets on which a minor amount of a tungstosilicic acid or a molybdosilicic acid is deposited. Also, the invention is directed to a process for preparing predominantly linear polyethylenepolyamines from ethylenediamine and monoethanolamine using the novel catalyst compositions.
    Type: Grant
    Filed: December 19, 1988
    Date of Patent: January 8, 1991
    Assignee: Texaco Chemical Company
    Inventors: John F. Knifton, Wei-Yang Su
  • Patent number: 4980503
    Abstract: It has been surprisingly discovered in accordance with the present invention that glycol formates and their alkyl ether derivatives can be substantially selectively converted to monocarboxylic acids by bringing a glycol formate or an alkyl ether derivative thereof into contact with a bed of activated carbon in the presence of carbon monoxide and a halide promoted group VIII soluble transition metal catalyst optionally in the presence of a solvent.
    Type: Grant
    Filed: August 15, 1986
    Date of Patent: December 25, 1990
    Assignee: Texaco Inc.
    Inventors: John M. Larkin, George P. Speranza
  • Patent number: 4980514
    Abstract: Diketones useful as intermediates for reaction with carboxylic acids to provide surfactants and for reaction with amine adducts to provide fuel additives are prepared from polyoxyalkylene glycols having a molecular weight of about 200 to about 2,000 and having the formula: ##STR1## wherein R is hydrogen or methyl and wherein n is a positive number having a value of 1 to about 50,The polyoxyalkylene polyol is oxidized in the presence of a halogenated alkane solvent and a ruthenium catalyst with an alkali metal or alkaline earth metal hypochlorite at a temperature of about 10.degree. to about 50.degree. C. and a pressure of about 0 to 1,000 psig. over a period of about 10 to about 20 hours to provide the corresponding diketone having the formula: ##STR2## wherein R and n have the meaning given above.
    Type: Grant
    Filed: December 1, 1989
    Date of Patent: December 25, 1990
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, Edward T. Marquis
  • Patent number: 4978785
    Abstract: Carboxylic acid derivatives and methyl ketone derivatives of polyoxypropylene glycols are prepared by the selective nitric acid oxidation of a polyoxypropylene glycol in the presence of an alkali metal nitrite. If the alkali metal nitrite is added to an aqueous solution of nitric acid and the polyoxypropylene glycol is thereafter added, carboxylic acid derivatives of the polyoxypropylene glycol are provided. If a mixture of an alkali metal nitrite and a polyoxypropylene glycol is added to an aqueous solution of nitric acid, a reaction product containing a predominant amount of methyl ketone derivatives of the polyoxypropylene glycol is provided.
    Type: Grant
    Filed: December 11, 1989
    Date of Patent: December 18, 1990
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, John M. Larkin
  • Patent number: 4977285
    Abstract: A heavy distillation fraction comprising tertiary butyl hydroperoxide, tertiary butyl alcohol, impurities and dissolved molybdenum catalyst resulting from the removel of propylene, propylene oxide and tertiary butyl alcohol from an epoxidation reaction product is mixed with about 5 to about 10 wt. %, based on the weight of the heavy liquid distilation fraction, of a lower aliphatic alcohol containing from 1 to 3 carbon atoms to provide a charge mixture, and the charge mixture is:charged to a falling film evaporator and separator therein, under evaporator operating conditions including a temperature within the range of about 20.degree. to about 150.degree. C. and a pressure of about 1 to about 200 mm Hg., into an overhead vaporized fraction comprising substantially all of the aliphatic alcohol and from about 80 to about 95 wt. % of the heavy distillation fraction charged to the falling film evaporator.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: December 11, 1990
    Assignee: Texaco Chemical Company
    Inventors: Edward T. Marquis, Kenneth P. Keating, Robert A. Meyer, John R. Sanderson
  • Patent number: 4971661
    Abstract: An impure propylene oxide feedstock contaminated with from about 50 to about 1000 ppm of methanol and from about 0 to about 1 wt. % of acetone is charged to the lower half of an extractive distillation column containing at least about 25 theoretical plates and an extractive distillation agent consisting essentially of a blend of acetone and water (acetone/water blend) containing about 20 to about 30 wt. % of acetone and, correspondingly, about 80 to about 70 wt. % of water is charged to the tower at a point 4 to 7 theoretical stages above the impure propylene oxide feed point; the extractive distillation agent being introduced into the extractive distillation column in the ratio of said feedstock to said extractive distillation agent of from about 5:1 to about 20:1, whereby an overhead distillate fraction is obtained consisting essentially of propylene oxide contaminated with not more than about 60 ppm of methanol, not more than about 0.02 wt. % of acetone and not more than about 0.3 wt. % of water.
    Type: Grant
    Filed: October 20, 1989
    Date of Patent: November 20, 1990
    Assignee: Texaco Chemical Company
    Inventors: Robert A. Meyer, Kenneth P. Keating, William A. Smith, Robert M. Steinberg
  • Patent number: 4960948
    Abstract: Polyoxypropylene diketones are prepared by initially adding predetermined amounts of glacial acetic acid, a polyoxypropylene glycol and, optionally, water, to a reaction zone and thereafter adding an aqueous solution of an alkali metal or an alkaline earth metal hypochlorite oxidant to the reaction zone with agitation under reaction conditions including a temperature of about 10.degree. to about 50.degree. C., a pressure of about 0 to 1,000 psig. and a total reaction time of about 0.5 to 20 hours, whereby said polyoxypropylene glycol will be substantially selectively converted to the said corresponding diketone, and recovering said diketone.
    Type: Grant
    Filed: December 26, 1989
    Date of Patent: October 2, 1990
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, Edward T. Marquis