Polycyclo Ring System Patents (Class 568/719)
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Patent number: 4994628Abstract: 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: GrantFiled: September 25, 1989Date of Patent: February 19, 1991Assignee: Ethyl CorporationInventors: Lloyd E. Goddard, George L. Mina
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Patent number: 4992597Abstract: 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: GrantFiled: September 25, 1989Date of Patent: February 12, 1991Assignee: Ethyl CorporationInventors: George L. Mina, Gary D. Heidebrecht
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Patent number: 4987269Abstract: 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: GrantFiled: June 26, 1989Date of Patent: January 22, 1991Assignee: Enichem Tecnoresine S.p.A.Inventor: Alberto Petri
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Patent number: 4978810Abstract: 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: GrantFiled: September 18, 1989Date of Patent: December 18, 1990Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Kaoru Kanayama, Shuji Ichikawa
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Patent number: 4939306Abstract: 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: GrantFiled: April 14, 1989Date of Patent: July 3, 1990Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Tohru Miura, Teruyuki Nagata, Koju Okazaki, Masayuki Furuya, Emiko Nishida
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Patent number: 4894181Abstract: 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: GrantFiled: May 16, 1988Date of Patent: January 16, 1990Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Klaus Praefcke, Bernd Kohne, Eike Poetsch
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Patent number: 4877907Abstract: 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: GrantFiled: April 14, 1989Date of Patent: October 31, 1989Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Tohru Miura, Teruyuki Nagata, Koju Okazaki, Masayuki Furuya, Emiko Nishida
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Patent number: 4847011Abstract: 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: GrantFiled: October 9, 1987Date of Patent: July 11, 1989Assignee: Shell Oil CompanyInventors: Kenneth C. Dewhirst, Thomas G. Stewart, Jr.
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Patent number: 4791234Abstract: 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: GrantFiled: October 10, 1986Date of Patent: December 13, 1988Assignee: General Electric CompanyInventors: Gary R. Faler, Jerry C. Lynch
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Patent number: 4723046Abstract: 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: GrantFiled: June 16, 1987Date of Patent: February 2, 1988Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Teruyuki Nagata, Tohru Miura
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Patent number: 4705847Abstract: 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: GrantFiled: December 7, 1983Date of Patent: November 10, 1987Assignee: Akzo N.V.Inventors: Jan C. Hummelen, Egbert W. Meijer, Hans Wynberg
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Patent number: 4701567Abstract: 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: GrantFiled: June 26, 1986Date of Patent: October 20, 1987Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Yoshimitsu Tanabe, Keizaburo Yamaguchi, Yukihiro Yoshikawa, Kenichi Sugimoto, Akihiro Yamaguchi
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Patent number: 4701566Abstract: 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: GrantFiled: October 10, 1986Date of Patent: October 20, 1987Assignee: General Electric CompanyInventors: Gary R. Faler, Jerry C. Lynch
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Patent number: 4675458Abstract: 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: GrantFiled: October 3, 1985Date of Patent: June 23, 1987Assignee: Ronm GmbHInventors: Achim Riemann, Werner Ude
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Patent number: 4605789Abstract: 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: GrantFiled: December 23, 1985Date of Patent: August 12, 1986Assignee: The Dow Chemical CompanyInventors: H. Craig Silvis, Ted A. Morgan
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Patent number: 4548976Abstract: 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: GrantFiled: May 18, 1984Date of Patent: October 22, 1985Assignee: The Dow Chemical CompanyInventors: Pierre DeRoche, Neil V. Kirby
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Patent number: 4540829Abstract: 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: GrantFiled: June 18, 1984Date of Patent: September 10, 1985Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4503266Abstract: 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: GrantFiled: June 7, 1984Date of Patent: March 5, 1985Assignee: Isovolta Osterreichische Isolierstoffwerke AktiengesellschaftInventor: Otto Szabolcs
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Patent number: 4496773Abstract: 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: GrantFiled: March 28, 1983Date of Patent: January 29, 1985Assignee: The Dow Chemical CompanyInventors: Robert C. Clouse, R. Garth Pews
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Patent number: 4446298Abstract: 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: GrantFiled: December 17, 1982Date of Patent: May 1, 1984Assignee: General Electric CompanyInventors: Victor Mark, Charles V. Hedges
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Patent number: 4438284Abstract: Self-condensation products are obtained by the oxidative coupling of substituted phenols in the presence of a heterogeneous cobalt-containing catalyst.Type: GrantFiled: May 17, 1982Date of Patent: March 20, 1984Assignee: The Dow Chemical CompanyInventor: Robert M. Strom
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Patent number: 4408086Abstract: 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: GrantFiled: December 3, 1980Date of Patent: October 4, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Shunsuke Matsushima, Kazuhiko Hata, Kentaro Mashita, Shuichi Kanagawa, Shinji Nakao, Kiyoshi Nakai, Kunimasa Kamio
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Patent number: 4354048Abstract: 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: GrantFiled: May 22, 1981Date of Patent: October 12, 1982Assignee: The Dow Chemical CompanyInventor: Robert M. Strom
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Patent number: 4354047Abstract: 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: GrantFiled: May 22, 1981Date of Patent: October 12, 1982Assignee: The Dow Chemical CompanyInventor: Robert M. Strom
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Patent number: 4334106Abstract: 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: GrantFiled: February 5, 1981Date of Patent: June 8, 1982Assignee: The Upjohn CompanyInventor: Shenghong A. Dai
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Patent number: 4324925Abstract: 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: GrantFiled: June 30, 1980Date of Patent: April 13, 1982Assignee: Bayer AktiengesellschaftInventors: Christoph Jupe, Helmut Waldmann, Hermann Seifert
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Patent number: 4310657Abstract: 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: GrantFiled: June 25, 1979Date of Patent: January 12, 1982Assignee: Standard Oil Company (Indiana)Inventor: Carl Serres, Jr.
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Patent number: 4301306Abstract: 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: GrantFiled: March 27, 1980Date of Patent: November 17, 1981Assignee: The B. F. Goodrich CompanyInventor: Robert W. Layer
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Patent number: 4301311Abstract: 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: GrantFiled: July 20, 1979Date of Patent: November 17, 1981Assignee: Chemische Werke Lowi GmbHInventors: Rolf Muller, Werner Hartmann, Zdenek Kuca
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Patent number: 4277600Abstract: Novel tetraphenolic compounds are disclosed. These compounds have utility as branching agents in the production of novel, randomly branched polycarbonates.Type: GrantFiled: September 20, 1979Date of Patent: July 7, 1981Assignee: General Electric CompanyInventors: Victor Mark, Charles V. Hedges
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Patent number: 4260831Abstract: 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: GrantFiled: March 27, 1979Date of Patent: April 7, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Shunsuke Matsushima, Kazuhiko Hata, Kentaro Mashita, Shuichi Kanagawa, Shinji Nakao, Kiyoshi Nakai, Kunimasa Kamio
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Patent number: 4211715Abstract: 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: GrantFiled: May 26, 1978Date of Patent: July 8, 1980Assignee: Sumitomo Chemical Company, LimitedInventors: Shuichi Kanagawa, Shinji Nakao, Kiyoshi Nakai, Kunimasa Kamio, Shunsuke Matsushima, Kazuhiko Hata, Kentaro Mashita
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Patent number: 4210765Abstract: An improved process for obtaining halogenated diphenols which can be pure dihalodiphenols or predetermined, statistical mixtures comprising unreacted diphenol, monohalodiphenols and dihalodiphenols.Type: GrantFiled: February 28, 1978Date of Patent: July 1, 1980Assignee: General Electric CompanyInventor: Victor Mark
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Patent number: 4168218Abstract: 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: GrantFiled: February 13, 1978Date of Patent: September 18, 1979Assignee: Eastman Kodak CompanyInventor: Jonas Dedinas
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Patent number: 4149015Abstract: 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: GrantFiled: February 13, 1978Date of Patent: April 10, 1979Assignee: Eastman Kodak CompanyInventor: Jonas Dedinas
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Patent number: 4147806Abstract: 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: GrantFiled: November 24, 1975Date of Patent: April 3, 1979Assignee: Laboratoires CreatInventor: Jean-Pierre Poupelin
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Patent number: 4139544Abstract: 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: GrantFiled: November 26, 1976Date of Patent: February 13, 1979Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4108908Abstract: 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: GrantFiled: February 18, 1977Date of Patent: August 22, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4100206Abstract: 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: GrantFiled: February 18, 1977Date of Patent: July 11, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4100204Abstract: 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: GrantFiled: February 18, 1977Date of Patent: July 11, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4100202Abstract: 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: GrantFiled: February 18, 1977Date of Patent: July 11, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4100203Abstract: 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: GrantFiled: February 18, 1977Date of Patent: July 11, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4100205Abstract: 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: GrantFiled: February 18, 1977Date of Patent: July 11, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4098830Abstract: 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: GrantFiled: February 18, 1977Date of Patent: July 4, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4096190Abstract: 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: GrantFiled: November 26, 1976Date of Patent: June 20, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge