Polycyclo Ring System Patents (Class 568/719)
  • Patent number: 4994628
    Abstract: 3,5-dialkyl-4-hydroxybenzyl-substituted benzene compounds are made by reacting 2,6-dialkyl-4-methoxymethyl phenols with a benzene compound having an unsubstituted nuclear position in an inert solvent and in the presence of sulfuric acid catalyst while distilling methanol by-product from the reaction mixture as it forms.
    Type: Grant
    Filed: September 25, 1989
    Date of Patent: February 19, 1991
    Assignee: Ethyl Corporation
    Inventors: Lloyd E. Goddard, George L. Mina
  • Patent number: 4992597
    Abstract: 3,5-dialkyl-4-hydroxybenzyl-substituted benzene compounds are made by reacting 2,6-dialkyl-4-methoxymethyl phenols with a benzene compound having an unsubstituted nuclear position in an inert solvent and in the presence of an organic sulfonic acid catalyst while distilling methanol by-product from the reaction mixture as it forms.
    Type: Grant
    Filed: September 25, 1989
    Date of Patent: February 12, 1991
    Assignee: Ethyl Corporation
    Inventors: George L. Mina, Gary D. Heidebrecht
  • Patent number: 4987269
    Abstract: Thermoplastic, branched, high-molecular-weight polycarbonates endowed with flame-proof properties (self-extinguishing properties) are characterized in that they contain in their macromolecule carbonate units, units deriving from a di-hydroxy-aromatic compound having the formula: ##STR1## wherein: R is a single bond; orR is a linear or branched, either substituted or non-substituted, alkylene radical of from 1 to 5 carbon atoms; orR is selected from the group consisting of O, S, SO.sub.2, CO;X, Y which may be either equal to, or different from, each other, are either H or CH.sub.3 ;m, n which may be either equal to, or different from, each other, are integers comprised within the range of from 1 to 4;and units deriving from a halogenated macrocyclic compound having the formula: ##STR2## wherein: R.sub.1 is H or OH or chlorine or bromine, andR.sub.2 is chlorine or bromine.
    Type: Grant
    Filed: June 26, 1989
    Date of Patent: January 22, 1991
    Assignee: Enichem Tecnoresine S.p.A.
    Inventor: Alberto Petri
  • Patent number: 4978810
    Abstract: A polyalkenylphenol compound represented by formula (I): ##STR1## wherein R represents a hydrogen atom or a methyl group; X represents a hydrogen atom or a halogen atom; and n represents 0 or an integer of from 1 to 10. The compound is useful as a curing agent for epoxy resins or maleimide resins or a starting material for epoxy resins.
    Type: Grant
    Filed: September 18, 1989
    Date of Patent: December 18, 1990
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Kaoru Kanayama, Shuji Ichikawa
  • Patent number: 4939306
    Abstract: A novel compound, 4-(4-hydroxyphenyl)-3-cyclohexene-1-ol, and a novel preparation process of 4,4'-biphenol by using the novel compound as the raw material.4-(4-Hydroxyphenyl)-3-cyclohexene-1-ol can be obtained by conducting a thermal decomposition reaction of 4,4-bis(4-hydroxyphenyl)cyclohexanol. 4,4'-Biphenol can be industrially manufactured by conducting a dehydrogenation reaction of 4-(4-hydroxyphenyl)-3-cyclohexene-1-ol.
    Type: Grant
    Filed: April 14, 1989
    Date of Patent: July 3, 1990
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Tohru Miura, Teruyuki Nagata, Koju Okazaki, Masayuki Furuya, Emiko Nishida
  • Patent number: 4894181
    Abstract: Carbocyclic compounds of the formula I ##STR1## wherein Q is a benzene or cyclohexane ring or a naphthalene system, X is in each case --CH.sub.2 --(CH.sub.2).sub.p -- where it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O-- or --CH.dbd.CH--,p is 0, 1 or 2,A.sup.1 and A.sup.2 independently of one another are each a 1,4-phenylene group which is unsubstituted or monosubstituted or polysubstituted by halogen atoms and/or CH.sub.3 groups and/or CN groups and in which it would also be possible for one or more CH groups to be replaced by N atoms, a 1,4-cyclohexylene group wherein it would also be possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O-- and/or --S--, a piperidine-1,4-diyl group or a 1,4-bicyclo[2.2.2]octylene group,Z is --CO--O--, --O--CO--, --O--, --CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CHCN--CH.sub.2 --, --CH.sub.2 --CHCN--, --CH.dbd.CH--, --CH.dbd.N--, --N.dbd.CH--, --NO.
    Type: Grant
    Filed: May 16, 1988
    Date of Patent: January 16, 1990
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Klaus Praefcke, Bernd Kohne, Eike Poetsch
  • Patent number: 4877907
    Abstract: A novel compound, 4-(4-hydroxyphenyl)-3-cyclohexene-1-ol, and a novel preparation process of 4,4'-biphenol by using the novel compound as the raw material.4-(4-Hydroxyphenyl)-3-cyclohexene-1-ol can be obtained by conducting a thermal decomposition reaction of 4,4-bis(4-hydroxyphenyl)cyclohexanol. 4,4'-Biphenol can be industrially manufactured by conducting a dehydrogenation reaction of 4-(4-hydroxyphenyl)-3-cyclohexene-1-ol.
    Type: Grant
    Filed: April 14, 1989
    Date of Patent: October 31, 1989
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Tohru Miura, Teruyuki Nagata, Koju Okazaki, Masayuki Furuya, Emiko Nishida
  • Patent number: 4847011
    Abstract: Certain bis-anthrols and bis-naphthols and their diglycidyl ethers are novel and useful in the preparation of new polyether thermoplastic compositions. The compounds have the formulae: ##STR1## (or its keto tautomer) or ##STR2## where A is as defined in the claims.
    Type: Grant
    Filed: October 9, 1987
    Date of Patent: July 11, 1989
    Assignee: Shell Oil Company
    Inventors: Kenneth C. Dewhirst, Thomas G. Stewart, Jr.
  • Patent number: 4791234
    Abstract: Spirobiindane bisphenols of high purity, suitable for conversion to high molecular weight polycarbonates, are prepared by reacting a bisphenol or 4-isopropenylphenol with a metal halide Lewis acid or an alkanesulfonic acid, followed by removing impurities including phenols, 1-(4-hydroxyphenyl)indanols and the like. A step of purification by precipitation with water from a methanol-methylene chloride solution is included.
    Type: Grant
    Filed: October 10, 1986
    Date of Patent: December 13, 1988
    Assignee: General Electric Company
    Inventors: Gary R. Faler, Jerry C. Lynch
  • Patent number: 4723046
    Abstract: A process for preparing 4,4'-biphenol comprising subjecting 4,4-bis(4-hydroxyphenyl)cyclohexanol to decomposition and dehydrogenation in the presence of a dehydrogenation catalyst.4,4-Bis(4-hydroxyphenyl)cyclohexanol is a novel compound which can be prepared by reacting 4-hydroxycyclohexanone with phenol.
    Type: Grant
    Filed: June 16, 1987
    Date of Patent: February 2, 1988
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Teruyuki Nagata, Tohru Miura
  • Patent number: 4705847
    Abstract: The invention relates to a process for preparing substituted polycyclo-alkylidene polycyclo-alkanes, such as substituted adamantylidene adamantanes, and the corresponding epidioxy compounds, in which polycyclo-alkylidene polycyclo-alkanes are halogenated with an N-halosuccinimide, tert.-butylhypohalite or sodium hypohalite/CH.sub.3 COOH, the halogenation product is optionally subjected to a substitution reaction, and the substituted polycycloalkylidene polycyclo-alkanes are converted to the corresponding epidioxy compounds in a way known per se.Further, the invention relates to compounds of formula 44 ##STR1## in which A and B represent alkylene radicals, which alkylene radicals may be attached to each other via an alkylene radical C, and R.sub.1 represents a substituent, which, in case of 4-eq.-R.sub.1 -2,2'-adamantylidene adamantane cannot be chloro, hydroxy, oxo, D or a group of formula 1: ##STR2## as well as to compounds of formula 45: ##STR3## in which A, B and C are as defined above, and R.sub.
    Type: Grant
    Filed: December 7, 1983
    Date of Patent: November 10, 1987
    Assignee: Akzo N.V.
    Inventors: Jan C. Hummelen, Egbert W. Meijer, Hans Wynberg
  • Patent number: 4701567
    Abstract: A novel process for producing 6,6'-dihydroxy-3,3,3',3'-tetramethyl-1,1'-spirobiindane of the formula (1) ##STR1## which comprises heat-treating 2,2-bis(4-hydroxyphenyl)propane in the presence of a superacid-type resin or a perfluoroalkanesulfonic acid.
    Type: Grant
    Filed: June 26, 1986
    Date of Patent: October 20, 1987
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Yoshimitsu Tanabe, Keizaburo Yamaguchi, Yukihiro Yoshikawa, Kenichi Sugimoto, Akihiro Yamaguchi
  • Patent number: 4701566
    Abstract: Spirobiindane bisphenols are prepared by contacting a mixture of a bisphenol or a 4-isopropenylphenol and a 1-(4-hydroxyphenyl)indanol with a metal halide Lewis acid or an alkanesulfonic acid. High purity spirobiindane bisphenols may be prepared by employing a purification sequence, which preferably includes a step of precipitation of the product with water from a methanol-methylene chloride solution.
    Type: Grant
    Filed: October 10, 1986
    Date of Patent: October 20, 1987
    Assignee: General Electric Company
    Inventors: Gary R. Faler, Jerry C. Lynch
  • Patent number: 4675458
    Abstract: A method for making 9,9-bis-(4-hydroxyphenyl)-fluorene by reacting fluorenone with phenol at a temperature from 20.degree. to 100.degree. C. in the presence of sulfuric acid of a concentration higher than 70 percent and of a mercaptan, and particularly beta-mercaptopropionic acid, as acidic condensing agents.
    Type: Grant
    Filed: October 3, 1985
    Date of Patent: June 23, 1987
    Assignee: Ronm GmbH
    Inventors: Achim Riemann, Werner Ude
  • Patent number: 4605789
    Abstract: A new process for preparing spirobiindanols, comprising refluxing the corresponding alkylaryl bisphenyl derivative in the presence of a dry heterogeneous acid catalyst in toluene, is disclosed.
    Type: Grant
    Filed: December 23, 1985
    Date of Patent: August 12, 1986
    Assignee: The Dow Chemical Company
    Inventors: H. Craig Silvis, Ted A. Morgan
  • Patent number: 4548976
    Abstract: Bis-(norbornyl or substituted norbornyl) derivatives of a phenol or phenylamine of the following formula: ##STR1## wherein each A is O or NH; M is a bivalent radical such as the residue of an aldehyde, ammonia, water or H.sub.2 S; each R is a hydrocarbyl or an inertly substituted hydrocarbyl group; each R.sub.1 is independently a hydrocarbyl or an inertly substituted hydrocarbyl group and each n is independently an integer from 0 to 3 are useful as antioxidants for a variety of materials including latex compositions for preparing latex foam backed carpets.
    Type: Grant
    Filed: May 18, 1984
    Date of Patent: October 22, 1985
    Assignee: The Dow Chemical Company
    Inventors: Pierre DeRoche, Neil V. Kirby
  • Patent number: 4540829
    Abstract: New compositions of matter are disclosed which are allylated di and polycyclopentadiene diphenols. These new compositions are useful in thermoset resin compositions comprising styrene, a dicyclopentadiene-modified unsaturated polyesteramide and said allylated di and polycyclopentadiene diphenol(s).
    Type: Grant
    Filed: June 18, 1984
    Date of Patent: September 10, 1985
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4503266
    Abstract: In a process for the preparation of phenol-aromatic ketone condensation products by reaction of phenols and ketones in the presence of a gaseous hydrogen halide, the improvement comprising adding in catalytic amounts up to less than molar amounts based on the ketone as an additional condensation agent at least one bivalent, trivalent or tetravalent metal halide, introducing the gaseous hydrogen halide and after termination of the condensation reaction, adding water to the reaction mixture and recovering the purified condensation product and to the novel monomers of 9,9-bis-(4-hydroxyphenyl)-fluorene with a melting point of at least 226.degree. C. and 1,1-bis-(4-hydroxyphenyl)-1-phenylethene with a melting point of at least 189.degree. C. which are useful for the preparation of improved polyester resins.
    Type: Grant
    Filed: June 7, 1984
    Date of Patent: March 5, 1985
    Assignee: Isovolta Osterreichische Isolierstoffwerke Aktiengesellschaft
    Inventor: Otto Szabolcs
  • Patent number: 4496773
    Abstract: The invention is a process for coupling 2-naphthols which comprises contacting 2-naphthols dissolved in a polar acidic solvent in the presence of a catalytic amount of a catalyst which comprises a readily reducible form of a Group IB, Group VIII or manganese metal in the further presence of oxygen or a source of oxygen, under conditions such that 1,1'-bi-2-naphthol is prepared.
    Type: Grant
    Filed: March 28, 1983
    Date of Patent: January 29, 1985
    Assignee: The Dow Chemical Company
    Inventors: Robert C. Clouse, R. Garth Pews
  • Patent number: 4446298
    Abstract: Novel triphenolic compounds having utility as branching agents and randomly branched polycarbonates useful for blow molding. The triphenolic compounds are reaction products of phenols and diketones. The triphenols can be unsubstituted, or substituted with alkyl groups, alkoxy groups or halogen radicals, or mixtures thereof.
    Type: Grant
    Filed: December 17, 1982
    Date of Patent: May 1, 1984
    Assignee: General Electric Company
    Inventors: Victor Mark, Charles V. Hedges
  • Patent number: 4438284
    Abstract: Self-condensation products are obtained by the oxidative coupling of substituted phenols in the presence of a heterogeneous cobalt-containing catalyst.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: March 20, 1984
    Assignee: The Dow Chemical Company
    Inventor: Robert M. Strom
  • Patent number: 4408086
    Abstract: m-Isopropenylphenol oligomer which is useful for the production of synthetic resins such as epoxy resins is produced by polyermizing m-isopropenylphenol at a temperature of 135.degree. to 230.degree. C. using a catalytic amount of an acid catalyst in the presence or absence of a solvent, or freezing m-isopropenylphenol in the presence or absence of an acid catalyst.
    Type: Grant
    Filed: December 3, 1980
    Date of Patent: October 4, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shunsuke Matsushima, Kazuhiko Hata, Kentaro Mashita, Shuichi Kanagawa, Shinji Nakao, Kiyoshi Nakai, Kunimasa Kamio
  • Patent number: 4354048
    Abstract: Carbon-to-carbon coupled self-condensation products are obtained by the oxidative coupling of substituted phenols in the presence of a heterogeneous dehydrogenation catalyst comprising copper chromite.
    Type: Grant
    Filed: May 22, 1981
    Date of Patent: October 12, 1982
    Assignee: The Dow Chemical Company
    Inventor: Robert M. Strom
  • Patent number: 4354047
    Abstract: Carbon-to-carbon coupled self-condensation products are obtained by the oxidative coupling of substituted phenols in the presence of a heterogeneous dehydrogenation catalyst comprising nickel.
    Type: Grant
    Filed: May 22, 1981
    Date of Patent: October 12, 1982
    Assignee: The Dow Chemical Company
    Inventor: Robert M. Strom
  • Patent number: 4334106
    Abstract: An improved process is provided for the preparation of a certain class of hydroxyphenyl-indanol compounds by the cyclization of a phenol selected from the group consisting of an isopropenylphenol, oligomers thereof, and mixtures of any of said group in any combination and proportion, by dissolving said phenol in a stoichiometric excess of an organic acid selected from the group consisting of trifluoroacetic acid, trichloroacetic acid, difluoroacetic acid, dichloroacetic acid, fluoroacetic acid, chloroacetic acid, formic acid, and mixtures thereof at a temperature falling within a range of from about 0.degree. C. to about 90.degree. C. to form a solution; and maintaining said solution at a temperature falling within the above said range until the formation of said indanol is substantially complete.The dihydroxy compounds produced by the present method are useful in the preparation of epoxy, alkyd, and urethane resins in particular.
    Type: Grant
    Filed: February 5, 1981
    Date of Patent: June 8, 1982
    Assignee: The Upjohn Company
    Inventor: Shenghong A. Dai
  • Patent number: 4324925
    Abstract: An improved process for the preparation of a polyhydric phenol by hydroxylation of a phenol with a peroxidic hydroxylating agent, is disclosed. The improvement resides in that before the hydroxylation, all or some of the mixture to be hydroxylated is treated with a cation exchanger.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: April 13, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christoph Jupe, Helmut Waldmann, Hermann Seifert
  • Patent number: 4310657
    Abstract: Compositions of oxidizable organic materials having stabilizing amounts of polymeric monohydroxybenzenoid hydroquinoid antioxidants of from about 500 to about 10,000 molecular weight, and the said polymers which are the reaction products of an alpha, alpha' alkyl aromatic compound containing a benzenoid ring, a hydroquinone compound and a monohydroxy benzenoid compound.
    Type: Grant
    Filed: June 25, 1979
    Date of Patent: January 12, 1982
    Assignee: Standard Oil Company (Indiana)
    Inventor: Carl Serres, Jr.
  • Patent number: 4301306
    Abstract: Novel norbornenyl phenolics useful as antioxidants are defined by the following structural formula: ##STR1## where R.sup.1, R.sup.2, and R.sup.3 are individually selected from hydrogen and alkyl groups of 1 to 3 carbon atoms; R.sup.4 is selected from hydrogen, alkyl groups containing 1 to 12 carbon atoms, and substituted and unsubstituted alicyclic groups of 4 to 8 carbon atoms; R.sup.5 is selected from alkyl groups containing 1 to 6 carbon atoms, and substituted and unsubstituted alicyclic groups of 4 to 8 carbon atoms; R.sup.7 is selected from alkylene and alkenylene groups containing 1 to 8 carbon atoms; and R.sup.8 is selected from hydrogen, alkyl and alkenyl groups containing 1 to 8 carbon atoms.
    Type: Grant
    Filed: March 27, 1980
    Date of Patent: November 17, 1981
    Assignee: The B. F. Goodrich Company
    Inventor: Robert W. Layer
  • Patent number: 4301311
    Abstract: The invention concerns a process for the preparation of dicyclopentylene [2,2'-bis(4-alkyl-6-t-butylphenols)] of the formula I ##STR1## wherein R.sub.1 is tertiary butyl andR.sub.2 is methyl or ethyl,by the reaction of 1.5 to 2.5 moles of a 4-alkyl-6-t-butyl-phenol of the formula II ##STR2## wherein R.sub.1 and R.sub.2 are as defined above, with 0.8 to 1.2 moles dicyclopentadiene at a temperature between 20.degree. and 120.degree. C. in the presence of an organic solvent and borontrifluoride or a complex thereof as catalyst, characterised by employment of specially selected solvents and reaction under practically anhydrous conditions.
    Type: Grant
    Filed: July 20, 1979
    Date of Patent: November 17, 1981
    Assignee: Chemische Werke Lowi GmbH
    Inventors: Rolf Muller, Werner Hartmann, Zdenek Kuca
  • Patent number: 4277600
    Abstract: Novel tetraphenolic compounds are disclosed. These compounds have utility as branching agents in the production of novel, randomly branched polycarbonates.
    Type: Grant
    Filed: September 20, 1979
    Date of Patent: July 7, 1981
    Assignee: General Electric Company
    Inventors: Victor Mark, Charles V. Hedges
  • Patent number: 4260831
    Abstract: m-Isopropenylphenol oligomer which is useful for the production of synthetic resins such as epoxy resins is produced by polymerizing m-isopropenylphenol at a temperature of 135.degree. to 230.degree. C. using a catalytic amount of an acid catalyst in the presence or absence of a solvent, or freezing m-isopropenylphenol in the presence or absence of an acid catalyst.
    Type: Grant
    Filed: March 27, 1979
    Date of Patent: April 7, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shunsuke Matsushima, Kazuhiko Hata, Kentaro Mashita, Shuichi Kanagawa, Shinji Nakao, Kiyoshi Nakai, Kunimasa Kamio
  • Patent number: 4211715
    Abstract: An epoxy resin of the formulae (I) and/or (II), ##STR1## wherein R and R' are each hydrogen atom or an alkyl group having 1 to 3 carbon atoms and n is a mean value satisfying the equation, 0<n.ltoreq.2, which is excellent in heat resistance, flexibility, curability and the like, and is useful in paints, adhesives, civil engineering and construction industry, electric appliances and the like.
    Type: Grant
    Filed: May 26, 1978
    Date of Patent: July 8, 1980
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shuichi Kanagawa, Shinji Nakao, Kiyoshi Nakai, Kunimasa Kamio, Shunsuke Matsushima, Kazuhiko Hata, Kentaro Mashita
  • Patent number: 4210765
    Abstract: An improved process for obtaining halogenated diphenols which can be pure dihalodiphenols or predetermined, statistical mixtures comprising unreacted diphenol, monohalodiphenols and dihalodiphenols.
    Type: Grant
    Filed: February 28, 1978
    Date of Patent: July 1, 1980
    Assignee: General Electric Company
    Inventor: Victor Mark
  • Patent number: 4168218
    Abstract: Benzopinacol compounds can be prepared by an improved process comprising irradiating a diarylketone with UV radiation in a non-polar hydrocarbon solvent mixed with an alcohol. The volume ratio of the non-polar hydrocarbon solvent to alcohol is between 3:1 and 8:1. The benzopinacols are useful, for example, in imaging materials, such as with certain dyes that are reactive with the ketyl radicals that can be released from the benzopinacols upon heating.
    Type: Grant
    Filed: February 13, 1978
    Date of Patent: September 18, 1979
    Assignee: Eastman Kodak Company
    Inventor: Jonas Dedinas
  • Patent number: 4149015
    Abstract: Benzopinacols represented by the formula: ##STR1## wherein R.sup.1 is hydrogen, alkyl or aryl;R.sup.2 and R.sup.6 independently are selected from the group consisting of hydrogen, halogen or trifluoromethyl;R.sup.3 and R.sup.5 independently, are selected from the group consisting of hydrogen, halogen and alkyl or, when taken together with R.sup.4, represent a tetramethylene group; andR.sup.4 is selected from the group consisting of hydrogen, halogen, alkyl, alkoxy and phenoxy;With the proviso that when both of the ortho positions of the phenyl groups to which R.sup.2 and R.sup.6 are attached are substituted, the substituent is fluorine. These benzopinacol compounds can be prepared by an improved process comprising irradiating a diarylketone with UV radiation in a non-polar hydrocarbon solvent mixed with an alcohol. The volume ratio of the non-polar hydrocarbon solvent to alcohol is between 3:1 and 8:1.
    Type: Grant
    Filed: February 13, 1978
    Date of Patent: April 10, 1979
    Assignee: Eastman Kodak Company
    Inventor: Jonas Dedinas
  • Patent number: 4147806
    Abstract: The active constituents of these medicaments are compounds of the general formula: ##STR1## in which R represents a sulfur or oxygen atom or a >SO or >SO.sub.2 radical or even a ##STR2## IN WHICH R.sub.1 and R.sub.2 which can be the same or different, represent a hydrogen atom or a hydroxyl, aryl, alkyl, arylalkyl, alkylaryl possibly halogenated or a heterocyclic radical, said radicals being substituted or unsubstituted, while R' and R", which may be the same or different, represent a hydrogen atom, a metal such as an alkali or alkaline-earth metal or magnesium, or the ammonium ion or an alkyl radical, an aliphatic or aromatic acyl radical or a heterocyclic radical, which radicals may be substituted or unsubstituted. The process enables the products to be prepared in sufficiently pure form for therapeutic use. .beta.-naphthol is reacted with a suitable aldehyde in an acetic medium, in the presence of hydrochloric acid added dropwise at between 5.degree. and 10.degree. C.
    Type: Grant
    Filed: November 24, 1975
    Date of Patent: April 3, 1979
    Assignee: Laboratoires Creat
    Inventor: Jean-Pierre Poupelin
  • Patent number: 4139544
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of phenols and naphthols are prepared by contacting an aqueous mixture of phenol or naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 8.5-9.5 during the oxidative coupling reaction and a catalyst system comprising a copper, cobalt, nickel, iron, chromium, cerium, or manganese chelate of a polyimino acid containing more than two nitrogen atoms.
    Type: Grant
    Filed: November 26, 1976
    Date of Patent: February 13, 1979
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge
  • Patent number: 4108908
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 7.0-9.0 during the oxidative coupling reaction and a catalyst system comprising a cupric, cobaltous, manganous or chromic chelate of a thio-acid compound.The mixture may optionally contain a surfactant.
    Type: Grant
    Filed: February 18, 1977
    Date of Patent: August 22, 1978
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge
  • Patent number: 4100206
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkyl phenol or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 7.0-9.5 during the oxidative coupling reaction and a catalyst system comprising a cupric or manganous chelate of a keto alcohol compound.The mixture may optionally contain a surfactant.
    Type: Grant
    Filed: February 18, 1977
    Date of Patent: July 11, 1978
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge
  • Patent number: 4100204
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 7.0-9.5 during the oxidative coupling reaction and a catalyst system comprising a cupric, cobaltous or manganous chelate of a hydroxy- or keto- acid compound.The mixture may optionally contain a surfactant.
    Type: Grant
    Filed: February 18, 1977
    Date of Patent: July 11, 1978
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge
  • Patent number: 4100202
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 8.5-9.5 during the oxidative coupling reaction and a catalyst system comprising a cupric chelate of a compound selected from the group consisting of quanidines, amides, salens, dihydrazides, triazenes, dihydroxy substituted aromatics, macrocylic polyamines and alpha, delta-polyketones.The mixture may optionally contain a surfactant.
    Type: Grant
    Filed: February 18, 1977
    Date of Patent: July 11, 1978
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge
  • Patent number: 4100203
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 8.0-9.5 during the oxidative coupling reaction and a catalyst system comprising a cupric, cobaltous or manganous chelate of an oxime of a keto or aldehyde compound.The mixture may optionally contain a surfactant.
    Type: Grant
    Filed: February 18, 1977
    Date of Patent: July 11, 1978
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge
  • Patent number: 4100205
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol or 1-naphtol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 7.5-10 during the oxidative coupling reaction and a catalyst system comprising a cupric, cobaltous, nickelous, ferric, manganous or chromic chelate of an aminoketone compund.The mixture may optionally contain a surfactant.
    Type: Grant
    Filed: February 18, 1977
    Date of Patent: July 11, 1978
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge
  • Patent number: 4098830
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol, alkoxyphenyl, or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 7.0-9.5 during the oxidative coupling reaction and a catalyst system comprising a cupric, cobaltous, manganous, nickelous, chromic or ferric chelate of a dicarboxylic acid compound.The mixture may optionally contain a surfactant.
    Type: Grant
    Filed: February 18, 1977
    Date of Patent: July 4, 1978
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge
  • Patent number: 4096190
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols are prepared by contacting an aqueous mixture of an alkyl phenol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 6-9.5 during the oxidative coupling reaction and a catalyst system comprising an ammonia complex of monovalent copper; divalent copper, cobalt, nickel or manganese; or trivalent chromium or iron. The mixture may optionally contain a surfactant.
    Type: Grant
    Filed: November 26, 1976
    Date of Patent: June 20, 1978
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge