Patents Represented by Attorney Patricia J. Hogan
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Patent number: 4322565Abstract: 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: GrantFiled: January 12, 1981Date of Patent: March 30, 1982Assignee: Columbian Chemicals CompanyInventors: Anderson O. Dotson, Jr., Francis T. Wadsworth
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Patent number: 4262149Abstract: 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: GrantFiled: April 21, 1980Date of Patent: April 14, 1981Assignee: Columbian Chemicals CompanyInventors: Anderson O. Dotson, Jr., Francis T. Wadsworth
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Patent number: 4258223Abstract: 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: GrantFiled: August 8, 1978Date of Patent: March 24, 1981Assignee: Cities Service CompanyInventors: Ralph Levine, Jerome R. Olechowski
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Patent number: 4232140Abstract: 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: GrantFiled: October 23, 1978Date of Patent: November 4, 1980Assignee: Cities Service CompanyInventor: Morris R. Ort
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Patent number: 4165343Abstract: 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: GrantFiled: July 28, 1978Date of Patent: August 21, 1979Assignee: Cities Service ConmpanyInventors: Ralph Levine, Jerome R. Olechowski
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Patent number: 4140862Abstract: (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: GrantFiled: January 17, 1977Date of Patent: February 20, 1979Assignee: Cities Service CompanyInventors: Anderson O. Dotson, Jr., Francis T. Wadsworth, Lionel T. Wolford
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Patent number: 4127545Abstract: 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: GrantFiled: July 27, 1977Date of Patent: November 28, 1978Assignee: Cities Service CompanyInventors: John E. Callan, Eric L. Scheinbart
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Patent number: 4127559Abstract: 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: GrantFiled: August 18, 1972Date of Patent: November 28, 1978Assignee: Cities Service CompanyInventor: Jack Newcombe
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Patent number: 4125535Abstract: 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: GrantFiled: February 7, 1977Date of Patent: November 14, 1978Assignee: Cities Service CompanyInventor: Lionel T. Wolford
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Patent number: 4112020Abstract: 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: GrantFiled: August 10, 1977Date of Patent: September 5, 1978Assignee: Cities Service CompanyInventor: John E. Callan
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Patent number: 4092282Abstract: 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: GrantFiled: August 19, 1977Date of Patent: May 30, 1978Assignee: Cities Service CompanyInventor: John E. Callan
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Patent number: 4092345Abstract: (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: GrantFiled: July 30, 1976Date of Patent: May 30, 1978Assignee: Cities Service CompanyInventors: Lionel T. Wolford, Chien Yung Lee, Anderson O. Dotson, Jr.
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Patent number: 4087441Abstract: 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: GrantFiled: July 19, 1976Date of Patent: May 2, 1978Assignee: Cities Service CompanyInventor: Chien Yung Lee
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Patent number: 4067930Abstract: 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: GrantFiled: November 26, 1976Date of Patent: January 10, 1978Assignee: Cities Service CompanyInventors: John Versnel, Joseph Green
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Patent number: 4003864Abstract: 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: GrantFiled: July 2, 1976Date of Patent: January 18, 1977Assignee: Cities Service CompanyInventors: Shirley H. Roth, William S. Stoy
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Patent number: 4003863Abstract: 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: GrantFiled: July 2, 1976Date of Patent: January 18, 1977Assignee: Cities Service CompanyInventors: William S. Stoy, Shirley H. Roth
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Patent number: 3991021Abstract: 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: GrantFiled: March 8, 1976Date of Patent: November 9, 1976Assignee: Cities Service CompanyInventor: Shirley H. Roth
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Patent number: 3988266Abstract: 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: GrantFiled: March 8, 1976Date of Patent: October 26, 1976Assignee: Cities Service CompanyInventor: Shirley H. Roth
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Patent number: 3950456Abstract: 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: GrantFiled: July 25, 1975Date of Patent: April 13, 1976Assignee: Cities Service CompanyInventor: Jack Newcombe