Patents Represented by Attorney Patricia J. Hogan
  • Patent number: 4322565
    Abstract: An alkyl t-alkyl ether corresponding to the formula R--O--R', wherein R is a methyl or ethyl group and R' is a t-butyl or t-amyl group, is separated from the alkanol in a reactor effluent comprising a mixture of the ether, unreacted C.sub.1 -C.sub.2 alkanol, and unreacted hydrocarbon by (1) alternately passing effluent from the reactor through first and second absorption vessels containing fixed beds of solid calcium chloride to complex the unreacted alkanol with the calcium chloride while the ether and unreacted hydrocarbon pass through the vessel, (2) while one absorption vessel is being used to complex unreacted alkanol, regenerating the other absorption vessel by passing a liquid C.sub.4 or C.sub.5 hydrocarbon feed comprising an isoolefin therethrough at a temperature of about 80.degree.-120.degree. C. to desorb the alkanol and provide a desorption effluent of liquid C.sub.4 or C.sub.5 hydrocarbon feed and alkanol, and (3) feeding the desorption effluent to the reactor.
    Type: Grant
    Filed: January 12, 1981
    Date of Patent: March 30, 1982
    Assignee: Columbian Chemicals Company
    Inventors: Anderson O. Dotson, Jr., Francis T. Wadsworth
  • Patent number: 4262149
    Abstract: A C.sub.1 -C.sub.2 alkanol is separated from aqueous calcium chloride by adding a C.sub.4 or C.sub.5 hydrocarbon feed comprising an isoolefin to an aqueous solution of a calcium chloride-alkanol complex wherein the alkanol is methanol or ethanol at a temperature of about 80.degree.-120.degree. C. and a pressure of about 20-180 psig to provide an upper phase comprising the hydrocarbon feed and alkanol and a lower phase comprising aqueous calcium chloride. The invention is particularly useful as a step in a process for preparing and purifying methyl t-butyl ether by (1) reacting an excess of methanol with isobutylene or a C.sub.4 hydrocarbon stream containing isobutylene to form a crude reaction product comprising methyl t-butyl ether and excess methanol, (2) intimately mixing the crude reaction product with aqueous calcium chloride to complex the methanol and separate it from the ether, and (3) adding the hydrocarbon stream to extract the methanol from the aqueous calcium chloride-methanol complex solution.
    Type: Grant
    Filed: April 21, 1980
    Date of Patent: April 14, 1981
    Assignee: Columbian Chemicals Company
    Inventors: Anderson O. Dotson, Jr., Francis T. Wadsworth
  • Patent number: 4258223
    Abstract: A process for the recovery of isobutylene as tertiary butyl alcohol from a stream of C.sub.4 hydrocarbons comprising contacting the stream with an aqueous acid solution comprising from 50 to 80 wt % hydrocarbyl sulfonic acid, recovering from the resultant mixture an aqueous acid phase containing tertiary butyl alcohol and recovering from the acid phase the product tertiary butyl alcohol.
    Type: Grant
    Filed: August 8, 1978
    Date of Patent: March 24, 1981
    Assignee: Cities Service Company
    Inventors: Ralph Levine, Jerome R. Olechowski
  • Patent number: 4232140
    Abstract: Trichlorofluoromethane is used as a promoter in the polymerization and copolymerization of ethylene with supported Ziegler-type vanadium compound/alkylaluminum compound catalysts in the presence of hydrogen. The use of the promoter leads to the formation of non-rubbery, semi-crystalline polymers in high yields, does not alter the basic molecular weight distribution of the polymers, permits independent control of molecular weight by hydrogen, and imparts no significant level of halogen to the product.
    Type: Grant
    Filed: October 23, 1978
    Date of Patent: November 4, 1980
    Assignee: Cities Service Company
    Inventor: Morris R. Ort
  • Patent number: 4165343
    Abstract: Tertiary butyl alcohol is dehydrated in the presence of para-toluene sulfonic acid catalyst and xylene which forms an azeotrope with the water of hydration. Isobutylene and water, formed by the dehydration reaction, along with xylene, are removed as a vapor fraction. Xylene serves a dual purpose, acting as a solvent for paratoluene sulfonic acid so that this catalyst can contact the tertiary butyl alcohol feed, and also acting as an azeotrope forming agent to remove water as it is formed and to promote the dehydration reaction.
    Type: Grant
    Filed: July 28, 1978
    Date of Patent: August 21, 1979
    Assignee: Cities Service Conmpany
    Inventors: Ralph Levine, Jerome R. Olechowski
  • Patent number: 4140862
    Abstract: (Cyclo)alkylenediammonium compounds corresponding to the formula: ##STR1## wherein X is halogen, R is an alkylene or cycloalkylene group containing 2-15 carbon atoms, each R' alone is an alkyl, cycloalkyl, or aralkyl group, and R'---R' together represent an alkylene, cycloalkylene, or aralkylene group are prepared by esterifying a tetrahalophthalic anhydride with a mono- or dihydroxyalkane, -cycloalkane, or -aralkane having a boiling point below 250.degree. C. to form a half-ester and then reacting the half-ester with a stoichiometric amount of a diaminoalkane or diaminocycloalkane containing 2-15 carbon atoms.The (cyclo)alkylenediammonium compounds of the invention are useful as flame retardants for normally flammable organic polymers and also have utility as intermediates for the preparation of N,N'-(cyclo)alkylene-bis-tetrahalophthalimides, which are also useful as flame retardants. The imides are prepared simply by heating the diammonium compounds.
    Type: Grant
    Filed: January 17, 1977
    Date of Patent: February 20, 1979
    Assignee: Cities Service Company
    Inventors: Anderson O. Dotson, Jr., Francis T. Wadsworth, Lionel T. Wolford
  • Patent number: 4127545
    Abstract: Hot melt sealant compositions having improved adhesive bonding properties comprise a slightly crosslinked butyl rubber and critically-controlled amounts of a crystalline polymeric resin and a tackifying resin.
    Type: Grant
    Filed: July 27, 1977
    Date of Patent: November 28, 1978
    Assignee: Cities Service Company
    Inventors: John E. Callan, Eric L. Scheinbart
  • Patent number: 4127559
    Abstract: A normally flammable organic polymer is rendered flame retardant by the incorporation of a compound corresponding to the formula: ##STR1## wherein X is chloro or bromo, Q is halo, hydrogen, or a hydrocarbyl or hydrocarbyloxy group, and Z is a divalent saturated polybromocycloalkylene group containing 5-16 carbon atoms and 2-6 bromine atoms. Such flame retardants include, e.g., 5,6-dibromo-1,10,11,12,13,13-hexachlorotricyclo[8.2.1.0.sup.2,9 ]tridecene-11, i.e., the dibrominated 1:1 Diels-Alder adduct of hexachlorocyclopentadiene and cyclooctadiene-1,5. If desired, the flame retardant may be employed in conjunction with a synergist, such as antimony trioxide.
    Type: Grant
    Filed: August 18, 1972
    Date of Patent: November 28, 1978
    Assignee: Cities Service Company
    Inventor: Jack Newcombe
  • Patent number: 4125535
    Abstract: White N,N'-alkylene-bis-tetrabromophthalimides are prepared by reacting about two molar proportions of tetrabromophthalic anhydride with about one molar proportion of a diaminoalkane containing 2-6 carbon atoms in a solvent mixture having a boiling point of at least about 125.degree. C. and comprising about 50-97.5% by weight of a liquid aromatic hydrocarbon or halohydrocarbon having a boiling point of at least about 80.degree. C. and about 50-2.5% by weight of an alkanoic or aralkanoic acid having a dissociation constant not higher than about 6 .times. 10.sup.-5 at 25.degree. C. A preferred solvent is a mixture of about 70% by weight of xylenes and about 30% by weight of propionic acid having a boiling point of about 130.degree. C. The products are particularly useful as flame retardants.
    Type: Grant
    Filed: February 7, 1977
    Date of Patent: November 14, 1978
    Assignee: Cities Service Company
    Inventor: Lionel T. Wolford
  • Patent number: 4112020
    Abstract: Intermediate compositions useful for the preparation of improved hot melt butyl sealants are obtained by partially grafting a mixture of a butyl rubber, a different elastomer and/or a crystalline polymeric resin, and an elastomeric resin. Preferred compositions are (1) partially grafted mixtures of butyl rubber, epichlorohydrin rubber, and a block copolyester elastomeric resin, (2) partially grafted mixtures of butyl rubber, ethylene-vinyl acetate copolymer, and a block copolyester elastomeric resin, and (3) partially grafted mixtures of butyl rubber, styrene-ethylene-butylene-styrene block copolymer rubber, and a block copolyester elastomeric resin.
    Type: Grant
    Filed: August 10, 1977
    Date of Patent: September 5, 1978
    Assignee: Cities Service Company
    Inventor: John E. Callan
  • Patent number: 4092282
    Abstract: Hot melt sealant compositions having superior adhesive bonding properties comprise butyl rubber, plasticizing or tackifying resins, and a reacted mixture of an alkaline earth metal hydroxide and a solid polyamide resin having a high amine value.
    Type: Grant
    Filed: August 19, 1977
    Date of Patent: May 30, 1978
    Assignee: Cities Service Company
    Inventor: John E. Callan
  • Patent number: 4092345
    Abstract: (Cyclo)alkylenediammonium-bis-tetrahalophthalates corresponding to the formula: ##STR1## wherein X is halogen and R is an alkylene or cycloalkylene group containing 2-15 carbon atoms are prepared by hydrolyzing a tetrahalophthalic anhydride to the corresponding tetrahalophthalic acid and then reacting the tetrahalophthalic acid in the resultant reaction mixture with a diaminoalkane or diaminocycloalkane containing 2-15 carbon atoms in a molar ratio of about two molar proportions of the acid per molar proportion of the diamine.The (cyclo)alkylenediammonium-bis-tetrahalophthalates of the invention are useful as flame retardants for normally flammable organic polymers and also have utility as intermediates for the preparation of N,N'-(cyclo)alkylene-bis-tetrahalophthalimides, which are also useful as flame retardants. The imides are prepared simply by heating the salts until an acid number of substantially 0 is obtained.
    Type: Grant
    Filed: July 30, 1976
    Date of Patent: May 30, 1978
    Assignee: Cities Service Company
    Inventors: Lionel T. Wolford, Chien Yung Lee, Anderson O. Dotson, Jr.
  • Patent number: 4087441
    Abstract: N,N'-alkylene-bis-tetrahalophthalimides, such as N,N'-ethylene-bis-tetrabromophthalimide, are prepared by reacting about two molar proportions of a tetrahalophthalic anhydride, such as tetrabromophthalic anhydride, with one molar proportion of a diaminoalkane containing 2-6 carbon atoms, such as 1,2-diaminoethane, in an aqueous medium.
    Type: Grant
    Filed: July 19, 1976
    Date of Patent: May 2, 1978
    Assignee: Cities Service Company
    Inventor: Chien Yung Lee
  • Patent number: 4067930
    Abstract: Flame-retardant compositions having an excellent balance of properties are obtained by flame-retarding rubber-modified polystyrenes with a mixture of about 55-95% by weight of a first flame retardant corresponding to the formula: ##STR1## AND ABOUT 45-5% BY WEIGHT OF A SECOND FLAME RETARDANT CORRESPONDING TO THE FORMULA: ##STR2## wherein X is bromo or chloro, Y is halo, hydrogen, or an alkyl, haloalkyl, alkoxy, or haloalkoxy group, and Z is a tetravalent hydrocarbon group containing 4-20 carbon atoms.
    Type: Grant
    Filed: November 26, 1976
    Date of Patent: January 10, 1978
    Assignee: Cities Service Company
    Inventors: John Versnel, Joseph Green
  • Patent number: 4003864
    Abstract: Intumescent amine-aldehyde copolymer compositions having improved UV stability are obtained by incorporating about 0.5-75% by weight of a polyol polyacrylate or polyol polymethacrylate into an intumescent composition comprising a low molecular weight, water-insoluble amine-aldehyde copolymer consisting essentially of repeating units which correspond to the formula: wherein Q is the residue of an alkanal containing 1-5 carbon atoms and R is hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, halo, nitro, acetamido, or sulfonamido. The preferred compositions are those in which the amine-aldehyde copolymer is a sulfanilamide-formaldehyde copolymer and the polyol ester is a liquid ester.
    Type: Grant
    Filed: July 2, 1976
    Date of Patent: January 18, 1977
    Assignee: Cities Service Company
    Inventors: Shirley H. Roth, William S. Stoy
  • Patent number: 4003863
    Abstract: Intumescent amine-aldehyde copolymer/epoxy resin compositions having improved UV stability are obtained by incorporating about 0.5-75% by weight of a polyol polyacrylate or polyol polymethacrylate into an intumescent composition comprising (A) a low molecular weight, water-insoluble amine-aldehyde copolymer consisting essentially of repeating units which correspond to the formula: wherein Q is the residue of an alkanal containing 1-5 carbon atoms and R is hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, halo, nitro, acetamido, or sulfonamido and (B) an epoxy resin. The preferred compositions are those in which the amine-aldehyde copolymer is a sulfanilamide-formaldehyde copolymer, the epoxy resin is a liquid glycidyl ether epoxy resin, and the polyol ester is a liquid ester.
    Type: Grant
    Filed: July 2, 1976
    Date of Patent: January 18, 1977
    Assignee: Cities Service Company
    Inventors: William S. Stoy, Shirley H. Roth
  • Patent number: 3991021
    Abstract: A water-insoluble amine-aldehyde copolymer intumescent agent having a number average molecular weight of about 350-2000 and consisting essentially of repeating units corresponding to the formula: ##SPC1##Wherein Q is the aldehyde residue and R is hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, halo, nitro, acetamido, or sulfonamido is mixed with about 10-100% by weight of 1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane as a synergist to increase the foam volume obtainable from the intumescent agent. The compositions comprising the intumescent agent and synergist may be applied to substrates by conventional techniques.
    Type: Grant
    Filed: March 8, 1976
    Date of Patent: November 9, 1976
    Assignee: Cities Service Company
    Inventor: Shirley H. Roth
  • Patent number: 3988266
    Abstract: A water-insoluble amine-aldehyde copolymer intumescent agent having a number average molecular weight of about 350-2000 and consisting essentially of repeating units corresponding to the formula: ##SPC1##Wherein Q is the aldehyde residue and R is hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, halo, nitro, acetamido, or sulfonamido is mixed with about 10-50% by weight of a synergist corresponding to the formula: ##SPC2##Wherein X is chloro or bromo, T is halo, hydrogen, or a hydrocarbyl or hydrocarbyloxy group, and Z is a monocyclic divalent saturated polybromocycloalkylene group containing 5-16 carbon atoms and 2-6 bromine atoms: said valences being on adjacent carbon atoms; to increase the foam volume obtainable from the intumescent agent. The compositions comprising the intumescent agent and synergist may be applied to substrates by conventional techniques.
    Type: Grant
    Filed: March 8, 1976
    Date of Patent: October 26, 1976
    Assignee: Cities Service Company
    Inventor: Shirley H. Roth
  • Patent number: 3950456
    Abstract: A normally flammable organic polymer is rendered flame retardant by the incorporation of a compound corresponding to the formula: ##SPC1##Wherein X is chloro or bromo, Q is halo, hydrogen, or a hydrocarbyl or hydrocarbyloxy group, and Z is a divalent saturated polybromocycloalkylene group containing 5-16 carbon atoms and 2-6 bromine atoms. Such flame retardants include, e.g., 5,6-dibromo-1,10,11,12,13,13-hexachlorotricyclo[8.2.1.0.sup.2,9 ]tridecene-11, i.e., the dibrominated 1:1 Diels-Alder adduct of hexachlorocyclopentadiene and cyclooctadiene-1,5. If desired, the flame retardant may be employed in conjunction with a synergist, such as antimony trioxide.
    Type: Grant
    Filed: July 25, 1975
    Date of Patent: April 13, 1976
    Assignee: Cities Service Company
    Inventor: Jack Newcombe