Two Phenols Bonded Directly To The Same Carbon Patents (Class 568/722)
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Patent number: 5874644Abstract: Methods/systems for making a relatively high-purity bisphenol A product from phenol and acetone. Controlled turbulence is used to form bisphenol A adduct solids having improved physical properties. Phenol is separated from the bisphenol A product while inhibiting decomposition of bisphenol A.Type: GrantFiled: April 12, 1996Date of Patent: February 23, 1999Inventor: Ben Gammill
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Patent number: 5851837Abstract: A method for making bisphenol salt as the result of the reaction between bisphenol and an alkali metal hydroxide. The method comprising steps to obtain the anhydrous alkali metal bisphenoxide salt within about a 0.2 mol % stoichiometry relationship between bisphenol and alkali metal hydroxide. A method for determining stoichiometry error of a sample comprises determining variables and applying the variables to an equation to determine stoichiometry.Type: GrantFiled: February 6, 1997Date of Patent: December 22, 1998Assignee: General Electric CompanyInventors: Edward Brittain Stokes, Thomas Link Guggenheim, James Marshall Finan
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Patent number: 5777180Abstract: An improved process for the production of bisphenols is presented in which ketones and phenols are reacted in the presence of an acidic cationic exchange resin catalyst and a mercaptan cocatalyst. Prior to the reaction, alkyl alcohol is removed from the ketone stream. Cocatalyst is withdrawn from the reactor so that cocatalyst derivatives such as disulphide ions can be removed from the presence of the catalyst thereby reducing the possibility of catalyst poisoning.Type: GrantFiled: December 18, 1996Date of Patent: July 7, 1998Assignee: Shell Oil CompanyInventors: Raymond Lawrence June, Robert Lawrence Blackbourn, Edgar Donald Allan, James Laurel Buechele
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Patent number: 5756860Abstract: The invention relates to the preparation of a transparent crystalline adduct consisting of bisphenol A (75 parts) and bisphenol TMC (25 parts), which has a melting point of 144.degree. C. which is below the melting points of the pure starting compounds bisphenol A (157.degree. C.) and bisphenol TMC (208.degree. C.).Type: GrantFiled: August 2, 1996Date of Patent: May 26, 1998Assignee: Bayer AktiengesellschaftInventors: Kurt-Peter Meurer, Tony Van Osselaer, Claus Wulff, Jurgen Hinz
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Patent number: 5723689Abstract: A method for recovering substantially pure p,p-bisarylols from a mixture comprising the same by subjecting the mixture to vacuum distillation and melt crystallization in the absence of an adduct crystallization and the generation of a reaction recycle stream.Type: GrantFiled: January 16, 1996Date of Patent: March 3, 1998Assignee: General Electric CompanyInventors: Eric James Pressman, Sheldon Jay Shafer, Joseph Richard Wetzel, Martin Herke Oyevaar
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Patent number: 5710346Abstract: The present invention provides a 2,2-bis(3,5-disubstituted-4-hydroxyphenyl) propane derivative represented by general formula (1) ##STR1## wherein each R.sup.1 represents a hydrogen atom or a lower alkyl group; a process for producing such propane derivative; and a process for producing pyrogallol using such propane derivative. The compound of the present invention has by itself a periphyton-controlling activity required for the active ingredient used in a periphyton-controlling agent such as antifouling paint for ship's bottom, antifouling agent for fishing net, or the like. Further, by decomposing the above compound with an alkali or an acid, pyrogallol can be produced industrially without using any natural material.Type: GrantFiled: June 15, 1995Date of Patent: January 20, 1998Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Masakazu Takahashi, Tomonori Miyazaki, Chika Maejima, Yoshikazu Kimura
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Patent number: 5698600Abstract: The invention relates to the synthesis of bisphenols from monophenols and carbonyl compounds such as aldehydes and ketones with concentrated mineral acids such as hydrochloric acid and/or hydrogen chloride gas as acid catalysts and a mercaptan as cocatalyst, which is fixed by an ion-pair bond to a matrix insoluble in the reaction medium.Type: GrantFiled: October 15, 1996Date of Patent: December 16, 1997Assignee: Bayer AGInventors: Claus Wulff, Gerhard Fennhoff, Alfred Eitel
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Patent number: 5696295Abstract: The invention relates to a method for the purification by distillation of p,p-bisphenol A from the melt.The p,p-bisphenol A melt thus obtained is highly heat-stable, stable in storage and colour-stable, is free from high-boiling components and no longer contains any surface-active or non-distillable metal, salt, acid or polymer components and no sulphur-containing components; o,p-BPA and phenol are removed and the low-boiling components are scarcely detectable.Type: GrantFiled: April 6, 1995Date of Patent: December 9, 1997Assignee: Bayer AGInventors: Claus Wulff, Kaspar Hallenberger, Heinrich Steude, Kurt-Peter Meurer, Tony van Osselaer, Jurgen Hinz, Frank Quaeyhaegens, Johan Vaes, Ignace Hooftman
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Patent number: 5675044Abstract: A method of recovering dihydric phenol, particularly bisphenol-A, from compositions containing the reaction residue of bisphenol-A units which method comprises:a. granulating a bisphenol-A containing polymer;b. treating the particles with an alcohol, or any other organic swelling solvent miscible with water and easily distilled off from an aqueous solution, preferably a C.sub.1 -C.sub.10 alcohol for a time sufficient to swell the particles;c. contacting the swelled particles with a ammoniacal solution at a temperature of at least about 25.degree. C. depending on the swelling solvent employed in order to selectively sever the ester bonds of the bisphenol-A residue units;d. separating the liquid phase from the solid phase;e. distilling ammonia and swelling solvent from the liquid phase of d. above, thus obtaining an essentially aqueous solution with dissolved urea and partially precipitated bisphenol-A;f. adding sufficient water to the residue of e.Type: GrantFiled: July 1, 1996Date of Patent: October 7, 1997Assignee: General Electric CompanyInventors: Paul Eijsbouts, Jos De Heer, Gabrie Hoogland, Srikanth Nanguneri, Gert De Wit
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Patent number: 5585404Abstract: Use of a compound selected from the group consisting of 3,5-diiodo-4-(2-N,N-diethylaminoethoxy)phenyl-(2-butylbenzofur-3-yl)methan ol hydrochloride (001), 2-methyl-3-(3,5-diiodo-4-(2-N,N-diethylaminoethoxy)-benzoyl)benzofuran hydrochloride (003), 2-n-butyl-3-(3,5-diiodo-4-carboxymethoxybenzoyl)benzofuran (005), 2-methyl-3-(3,5-diiodo-4-hydroxy-benzoyl)benzofuran (011), 2-methyl-3-(3,5-diiodo-4-carboxymethoxybenzyl)benzofuran (015), 4'-hydroxy-3'-iodo-3,5-diiodo-4-(2-N,N-diethylaminoethoxy)benzophenon hydrochloride (024), 2-butyl-3-(3-iodo-4-hydroxybenzoyl)benzofuran (029), 4'4'-dihydroxy-3'3,5-triiododiphenylmethan (032), which compound is a 3,5,3'-triiodothyronine (T-3) receptor ligand, for the preparation of a medicament for the therapeutic or prophylactic treatment of a disorder which depends on the expression of T-3 regulated genes, and pharmaceutical preparations comprising said compounds, are disclosed.Type: GrantFiled: June 7, 1995Date of Patent: December 17, 1996Inventors: Ulf Norinder, Jurgen Bajorath, Jay F. Stearns
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Patent number: 5541282Abstract: The invention involves aromatic polyhydroxy compounds, including triaromatic bisphenols and tris-[1,1,1-(4-hydroxyphenyl)] toluenes, and a process for the preparation thereof by reacting a phenolic compound, e.g. phenol, with a suitable halo-compound, for instance 1,1-dichloroethylbenzene, 1-chlorostyrene, or mixtures thereof. The reaction may be conducted in the presence or absence of a solvent; an excess of the phenolic compound can serve as the solvent. The product is conveniently recovered by removing the by-product HCl, excess phenolic compound, excess solvent and cooling. Yields of bis-1,1-(4-hydroxyphenyl)-1-phenylethane which are greater than 90% of theoretical have been obtained by the reaction of phenol and 1,1-dichloroethylbenzene, and a large portion of the yield is para isomer.Type: GrantFiled: November 9, 1994Date of Patent: July 30, 1996Assignee: The Dow Chemical CompanyInventors: Marlin E. Walters, W. Frank Richey, Emmett L. Tasset
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Patent number: 5527971Abstract: This invention relates to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A, which process features: a water and water miscible solvent reaction medium; a relatively high reaction temperature; the presence, in the reaction medium, of unreacted Br.sub.2 during the feed of bisphenol-A to the reactor; and the oxidation of co-produced HBr to yield Br.sub.2.Type: GrantFiled: April 24, 1995Date of Patent: June 18, 1996Assignee: Albemarle CorporationInventor: Bonnie G. McKinnie
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Patent number: 5512700Abstract: A process for the purification of a crude bisphenol comprises the following steps:(1) preparing a mixture comprising from about 35 to about 70% of a crude bisphenol and from about 65 to about 30% of water, by the total weight of bisphenol and water, without addition of a substantial amount of an organic solvent or an alkaline compound, at a pressure above atmospheric and a temperature above about 100.degree. C.,(2) crystallizing bisphenol at a pressure below atmospheric,(3) separating crystalline bisphenol from the mother liquor,(4) dividing at least a portion of the mother liquor into a bisphenol-rich oil phase and a water-rich phase,(5) preparing a mixture comprising at least a portion of the bisphenol-rich oil phase, water and optionally an additional amount of crude bisphenol at a pressure above atmospheric and a temperature above about 100.degree. C.,(6) cooling the mixture and crystallizing bisphenol; and(7) separating crystalline bisphenol from the mother liquor.Type: GrantFiled: March 10, 1995Date of Patent: April 30, 1996Assignee: Dow Deutschland Inc.Inventors: Emil Patrascu, Karl Kraehling, Jochen Gressmann
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Patent number: 5475152Abstract: A method comprising purifying impure bisphenol-A by fractional melt crystallization in a falling film dynamic crystallizer.Type: GrantFiled: October 26, 1994Date of Patent: December 12, 1995Assignee: General Electric Company and Sulzer Canada, Inc.Inventors: Gaylord M. Kissinger, Nicholas P. Wynn
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Patent number: 5475155Abstract: 4,4'-Dihydroxy-alpha-alkylstilbenes of high purity are prepared by reacting at a temperature of from about -20.degree. C. to about 20.degree. C. a mixture of (1) at least one alpha-haloketone, (2) at least one phenolic hydroxyl-containing compound or alkoxy-containing aromatic compound, and (3) at least one strong protonic acid or Lewis acid; such that the mole ratio of phenolic hydroxyl-containing compound or alkoxy-containing aromatic compound:alpha-haloketone(s) is from 0.1:1 to 1.9:1, and the mole ratio of phenolic hydroxyl-containing compound or alkoxy-containing aromatic compound:alpha-haloketone(s):strong protonic acid or Lewis acid is from about 0.1:1:0.0026 to about 1.9:1:0.95. The high purity 4,4'-dihydroxy-alpha-alkylstilbenes are useful for the advancement of epoxy resins, for the preparation of phenoxy resins and for the preparation of epoxy resins.Type: GrantFiled: January 18, 1995Date of Patent: December 12, 1995Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Maria I. Villarreal, David A. Carr
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Patent number: 5463140Abstract: A process for the condensation of an aldehyde or ketone starting material with a phenol, unsubstituted in the 4-position, comprises reacting the aldehyde or ketone starting material with the phenol in a reaction mixture in the presence of a soluble or insoluble mercaptosulfonic acid compound under conditions sufficient to bring about formation of a geminal bisphenolic moiety at each aldehyde or ketone moiety in the starting material. A miscible mercaptosulfonic acid compound is characterized by the formula(HS).sub.a -.theta.-(SO.sub.3 H).sub.bor a precursor thereof, wherein .theta. is an alkylene, cycloaliphatic, arylene, alkylenearylene, alkylenecycloaliphatic, alkylenearyl, heterocyclic or alkyleneheterocyclic residue.Type: GrantFiled: August 31, 1994Date of Patent: October 31, 1995Assignee: The Dow Chemical CompanyInventors: Richard M. Wehmeyer, Marlin E. Walters, Emmett L. Tasset, Steven L. Brewster
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Patent number: 5455282Abstract: The invention relates to repeatedly regeneratable ion exchanger resins with a thin covering of alkyl-SH groups.Type: GrantFiled: January 30, 1995Date of Patent: October 3, 1995Assignee: Bayer AktiengesellschaftInventors: Klaus Berg, Georg Malamet, Franz Backes, Alfred Eitel, Claus Wulff
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Patent number: 5446212Abstract: A reduced methyl bromide process for making tetrabromobisphenol A in methanol, including: dissolving bisphenol-A in a methanol solvent to form a bisphenol-A methanol solution, adding bromine to the bisphenol-A methanol solution to brominate bisphenol-A and form tetrabromobisphenol A and hydrogen bromide, exposing the bisphenol-A methanol solution to an amount of a hydrogen peroxide agent to reduce the amount of methyl bromide co-product resulting from the bromination of bisphenol-A in methanol by reducing the amount of hydrogen bromide co-product available to react with the methanol, and collecting the resulting tetrabromobisphenol A product thus formed after the bromination is substantially complete.Type: GrantFiled: September 8, 1994Date of Patent: August 29, 1995Assignee: Great Lakes Chemical Corp.Inventors: Dave C. Sanders, Arthur G. Mack, Larry D. Timberlake
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Patent number: 5434316Abstract: Bisphenol-A produced by the condensation of acetone and phenol is freed of contaminant co-products by melting and crystallization in and from water. The final washing, in hot water, cleanses the crystal surfaces of remaining contaminants without the need for organic solvents.Type: GrantFiled: July 28, 1994Date of Patent: July 18, 1995Assignee: General Electric CompanyInventor: Gaylord M. Kissinger
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Patent number: 5430199Abstract: A method is provided for recovering phenol values from bisphenol A tar by treating the bisphenol A tar with an alkyl phenol, such as cresol in the presence of an acid catalyst. In addition to recovering phenol, there is obtained a variety of dialkyl 9,9-dimethylxanthenes which can be converted to dicarboxylic acids and their corresponding diesters which are useful polymer intermediates.Type: GrantFiled: March 28, 1994Date of Patent: July 4, 1995Assignee: General Electric CompanyInventors: Andrew J. Caruso, Julia L. Lee
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Patent number: 5414151Abstract: A method is provided for making bisphenol by condensing a ketone and a phenol in the presence of a sulfonated aromatic organic polymeric ion-exchange catalyst having aminoorganomercaptan groups using a phenol having less than 1 ppm of hydroxyacetone.Type: GrantFiled: May 2, 1994Date of Patent: May 9, 1995Assignee: General Electric CompanyInventors: Eric J. Pressman, Sheldon J. Shafer
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Patent number: 5414152Abstract: The addition of 3-mercaptopropionic acid or the organic ester thereof to the reaction mixture slows the rate of deactivation of cationic catalyst resins containing mercaptan promoter sites, during preparation of bisphenols by the condensation of a ketone with a phenol.Type: GrantFiled: May 10, 1994Date of Patent: May 9, 1995Assignee: General Electric CompanyInventor: Michael J. Cipullo
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Patent number: 5414149Abstract: Bisphenols, such as bisphenol-A are color-stabilized by the addition of an .alpha.-hydroxy polycarboxylic acid iron sequestrant.Type: GrantFiled: March 2, 1994Date of Patent: May 9, 1995Assignee: General Electric CompanyInventors: Dennis Garrett, Mitch Reynolds, John Vanbuskirk
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Patent number: 5399785Abstract: Disclosed is a chemically stable tyrosinase activity inhibitor having high tyrosinase activity inhibition effect and low toxicity. The tyrosinase activity inhibitor has a structure of the formula: ##STR1## wherein R.sub.1, R.sub.3 and R.sub.4 are a hydrogen atom or an alkyl or alkenyl group having 1 to 9 carbon atoms, and R.sub.2 is an alkyl or alkenyl group having 2 to 9 carbon atoms.Type: GrantFiled: August 4, 1993Date of Patent: March 21, 1995Assignee: Nippon Paint Co., Ltd.Inventors: Yasutaka Miura, Yasuhiro Kinoshita, Yoshikazu Yamamoto, Kunio Takahashi, Kiyotaka Koyama, Kaoru Takatori
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Patent number: 5399789Abstract: A process comprising the addition of a degradation inhibiting effective amount of an amine having a boiling point above that of the phenol used in the process to a composition comprising the said phenol and a bisphenol, the addition occurring prior to a procedure which subjects the bisphenol to substantial heat, said bisphenol produced from an acidic ion exchange resin catalyzed reaction of the said phenol and a ketone or aldehyde.Type: GrantFiled: May 18, 1994Date of Patent: March 21, 1995Assignee: General Electric CompanyInventors: Michael J. Cipullo, John W. Fulmer
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Patent number: 5395857Abstract: The invention relates to a process for increasing (improving) the volume/time yield of fixed-bed reactors in the production of bisphenol A.Type: GrantFiled: March 31, 1994Date of Patent: March 7, 1995Assignee: Bayer AktiengesellschaftInventors: Klaus Berg, Georg Malamet, Alfred Eitel, Claus Wulff
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Patent number: 5387725Abstract: Compounds having acidic protons and a molecular structure which can delocalize the electron density of the conjugate base (target compounds) are chlorinated by contacting such compounds with a perchloroalkane and aqueous base in the presence of a phase transfer catalyst which is an tetraalkylammonium hydroxide. Chlorinated products, preferably gem-dichloro compounds, are produced. The gem-dichloro compounds are useful for alkylation of aromatic compounds. For instance fluorene is chlorinated to form 9,9-dichlorofluorene which is reacted with such compounds as phenol or aniline to form such compounds as 9,9-bis(hydroxyphenyl)fluorene, 9,9-bis(aminophenyl)fluorene, or 9-aminophenyl-9-chlorofluorene.Type: GrantFiled: July 12, 1993Date of Patent: February 7, 1995Assignee: The Dow Chemical CompanyInventors: Marlin E. Walters, W. Frank Richey, Katherine S. Clement, Steven L. Brewster, Emmett L. Tasset, Paul M. Puckett, V. Rao Durvasula, Hong A. Nguyen
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Patent number: 5382711Abstract: High quality bisphenol A is produced from a neutral crystalline adduct of bisphenol A and phenol by fusing the adduct in an atmosphere having a maximum oxygen content of 0.005 % by volume, followed by evaporation of liberated phenol. The crystalline adduct may be mixed with an aliphatic carboxylic acid before the fusion to reduce the coloring of the product. When an acidic crystalline adduct is used, the use of a strong alkali salt of an aliphatic carboxylic acid is suitably used. Interior surfaces of the apparatuses for carrying out the fusion and evaporation are desirably washed with an organic solvent to remove oxygen therefrom. The evaporation of phenol is suitably performed by two stage steam stripping wherein a used stripping gas obtained in the second stage is employed as a stripping gas in the first stage while steam is used as the stripping gas in the second stage.Type: GrantFiled: April 18, 1994Date of Patent: January 17, 1995Assignee: Chiyoda CorporationInventors: Sachio Asaoka, Tetsuo Maejima, Kouji Sakashita, Noriyuki Yoneda, Makoto Yasui, Nobuhiro Onda, Tsuneo Watanabe, Nobuo Moriya, Akio Shindo, Hiroaki Nishijima, Athumi Kukidome, Ryuichi Inaba, Takashi Imazeki, Kaoru Shimogawara
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Patent number: 5382712Abstract: High quality bisphenol A is produced from a neutral crystalline adduct of bisphenol A and phenol by fusing the adduct in an atmosphere having a maximum oxygen content of 0.005% by volume, followed by evaporation of liberated phenol. The crystalline adduct may be mixed with an aliphatic carboxylic acid before the fusion to reduce the coloring of the product. When an acidic crystalline adduct is used, the use of a strong alkali salt of an aliphatic carboxylic acid is suitably used. Interior surfaces of the apparatuses for carrying out the fusion and evaporation are desirably washed with an organic solvent to remove oxygen therefrom. The evaporation of phenol is suitably performed by two stage steam stripping wherein a used stripping gas obtained in the second stage is employed as a stripping gas in the first stage while steam is used as the stripping gas in the second stage.Type: GrantFiled: April 18, 1994Date of Patent: January 17, 1995Assignee: Chiyoda CorporationInventors: Sachio Asaoka, Tetsuo Maejima, Kouji Sakashita, Noriyuki Yoneda, Makoto Yasui, Nobuhiro Onda, Tsuneo Watanabe, Nobuo Moriya, Akio Shindo, Hiroaki Nishijima, Athumi Kukidome, Ryuichi Inaba, Takashi Imazeki, Kaoru Shimogawara
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Patent number: 5382710Abstract: The invention involves aromatic polyhydroxy compounds, including triaromatic bisphenols and tris-1,1,1-(4-hydroxyphenyl)] toluenes, and a process for the preparation thereof by reacting a phenolic compound, e.g. phenol, with a suitable halo-compound, for instance 1,1-dichloroethylbenzene, 1-chlorostyrene, or mixtures thereof. The reaction may be conducted in the presence or absence of a solvent; an excess of the phenolic compound can serve as the solvent. The product is conveniently recovered by removing the by-product HCl excess phenolic compound, excess solvent and cooling. Yields of bis-1,1-(4-hydroxyphenyl)-1-phenylethane which are greater than 90% of theoretical have been obtained by the reaction of phenol and 1,1-dichloroethylbenzene, and a large portion of the yield is para isomer.Type: GrantFiled: July 30, 1992Date of Patent: January 17, 1995Assignee: The Dow Chemical CompanyInventors: Marlin E. Walters, W. Frank Richey, Emmett L. Tasset
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Patent number: 5371304Abstract: High quality bisphenol A is produced from a neutral crystalline adduct of bisphenol A and phenol by fusing the adduct in an atmosphere having a maximum oxygen content of 0.005% by volume, followed by evaporation of liberated phenol. The crystalline adduct may be mixed with an aliphatic carboxylic acid before the fusion to reduce the coloring of the product. When an acidic crystalline adduct is used, the use of a strong alkali salt of an aliphatic carboxylic acid is suitably used. Interior surfaces of the apparatuses for carrying out the fusion and evaporation are desirably washed with an organic solvent to remove oxygen therefrom. The evaporation of phenol is suitably performed by two stage steam stripping wherein a used stripping gas obtained in the second stage is employed as a stripping gas in the first stage while steam is used as the stripping gas in the second stage.Type: GrantFiled: April 18, 1994Date of Patent: December 6, 1994Assignee: Chiyoda CorporationInventors: Sachio Asaoka, Tetsuo Maejima, Kouji Sakashita, Noriyuki Yoneda, Makoto Yasui, Nobuhiro Onda, Tsuneo Watanabe, Nobuo Moriya, Akio Shindo, Hiroaki Nishijima, Athumi Kukudome, Ryuichi Inaba, Takashi Imazeki, Karou Shimogawara
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Patent number: 5349112Abstract: Novel cyclic anti-tumor promoter compounds and therapeutic compositions are disclosed, along with method for their production and use as anti-cancer and cancer-prevention agents.Type: GrantFiled: November 26, 1993Date of Patent: September 20, 1994Assignee: University of HawaiiInventor: Marcus A. Tius
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Patent number: 5349111Abstract: A novolac resin is prepared by reacting a phenolic compound, an aldehyde or a ketone, and a hydroxyl-substituted benzocyclobutene compound wherein the hydroxyl group is attached to an aromatic ring. The benzocyclobutenes are connected to the phenolic rings through an oxygen or oxyaryl bridge, or the cyclobutene is fused directly to a phenol ring. The novolac resin cures without evolution of volatiles and, when cured, provides a polymer which has a high glass transition temperature and which is essentially insoluble in organic solvents.Type: GrantFiled: April 23, 1993Date of Patent: September 20, 1994Assignee: The Dow Chemical CompanyInventor: Daniel M. Scheck
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Patent number: 5345000Abstract: High purity, crystalline adduct of bisphenol A and phenol is produced multi-stage crystallization of a phenolic slurry of bisphenol A with a crystal separation and washing step being interposed between each of the two stages. Each of the crystallization stage includes a series of crystallization towers operated at decreasing temperatures. The crystallization of the slurry is performed by continuously discharging a portion of the slurry from each of the crystallization towers, introducing the discharged slurry into one or more coolers and then recycling the cooled slurry to the tower. Another portion of the slurry in each crystallization slurry is continuously discharged, heated for dissolving fine crystals of the adduct and then recycled to the crystallization tower so that large crystals are grown in each of the crystallization steps. An apparatus having a plurality of coolers and suitable for effecting the above crystallization is also disclosed.Type: GrantFiled: March 3, 1993Date of Patent: September 6, 1994Assignee: Chiyoda CorporationInventors: Nobuo Moriya, Keiji Shimoda, Sachio Asaoka, Takao Kameda, Kouji Sakashita, Tetsuo Maejima, Makoto Yasui, Hiroaki Nishijima, Nobuhiro Onda, Takeshi Kouzaki
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Patent number: 5345001Abstract: An aqueous resol solution produced by an alkaline condensation of a phenolic compound with an aldehyde in a molar ratio of 1:1.5 to 2.5 with an alkali metal content of 1 to 5.0% by weight of the reaction solution, neutralizing the solution after the end of condensation at least partially with an aromatic hydroxy carboxylic acid at a temperature not greater than 50.degree. C. and then concentrating the reaction mixture which is readily dilutable with water.Type: GrantFiled: August 23, 1993Date of Patent: September 6, 1994Assignee: Rutgerswerke Aktiengesellschaft AGInventors: Stephan Schroter, Achim Hansen, Arno Gardziella, Peter Adolphs
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Patent number: 5315042Abstract: Product quality productivity of continuous bisphenol-A (BPA) are increased by increasing the flow rate of reactants through the reactor and decreasing % acetone conversion in the presence of an ion exchange resin catalyst and an optional free mercaptan promoter.Type: GrantFiled: March 22, 1993Date of Patent: May 24, 1994Assignee: General Electric CompanyInventors: Michael J. Cipullo, Gaylord M. Kissinger, Isabel M. Matos
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Patent number: 5306748Abstract: Fluorine-modified thermosetting reins are available as phenolic or epoxy resins having trifluoromethyl groups and a naphthalene skeleton in a molecule. They are useful as components of resin compositions or resin modifiers and cure to products having low water pickup, low coefficient of thermal expansion, and adhesion as well as heat resistance and mechanical strength. Thermosetting resin compositions having such a thermosetting resin blended therein are useful in semiconductor element packaging.Type: GrantFiled: July 29, 1992Date of Patent: April 26, 1994Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Toshio Shiobara, Hisashi Shimizu, Manabu Narumi
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Patent number: 5304688Abstract: A process for the preparation of bishydroxy aromatic compounds, such as 9,9-bis(4-hydroxyphenyl)fluorene, involving contacting a ketone, such as fluorenone, with phenol or substituted phenol in the presence of a mercaptan cocatalyst and a solid superacid catalyst of Hammett acid strength H.sub.0 greater than about -13.0. Solid superacid catalysts include the sulfates, sulfated oxides, sulfated oxyhydroxides, and sulfated oxysilicates of aluminum, tin, and the Group IVA metals, such as zirconium, as well as mixed metal oxides, such as tungsten-zirconium oxides. Isolated yields are high for 9,9-bis(4-hydroxyphenyl)fluorene.Type: GrantFiled: April 13, 1993Date of Patent: April 19, 1994Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, Muthiah N. Inbasekaran
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Patent number: 5302761Abstract: Single crystals of tetrabromobisphenol A having an average particle size of from 150 to 500 .mu.m, each having a polyhedral shape.Type: GrantFiled: May 19, 1993Date of Patent: April 12, 1994Assignee: Tosoh CorporationInventors: Hanzo Tamabayashi, Shinji Kakimoto, Tetsuto Mizui, Akihiko Nomura, Koji Kunimoto
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Patent number: 5302774Abstract: The invention relates to a process for the production of bisphenols from acetone and phenols in the presence of sulfonic acid ion exchanger resins modified with alkyl-SH groups, in which 0.6 to 5% by weight H.sub.2 O is added to the mixture of phenol and acetone before the reaction.Type: GrantFiled: August 9, 1993Date of Patent: April 12, 1994Assignee: Bayer AktiengesellschaftInventors: Klaus Berg, Hans-Josef Buysch, Alfred Eitel, Gerhard Fennhoff, Otto Immel, Ralf Pakull, Bernhard Wehrle, Claus Wulff
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Patent number: 5300700Abstract: The invention relates to a special process for the production of high-purity bisphenol A from acetone and phenol in the presence of acidic catalysts.Type: GrantFiled: April 20, 1993Date of Patent: April 5, 1994Assignee: Bayer AktiengesellschaftInventors: Georg Malamet, Hans-Peter Wirges, Claus Wulff, Alfred Eitel
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Patent number: 5300704Abstract: A process of using fast pyrolysis in a carrier gas to convert a plastic waste feedstream having a mixed polymeric composition in a manner such that pyrolysis of a given polymer to its high value monomeric constituent occurs prior to pyrolysis of other plastic components therein comprising: selecting a first temperature program range to cause pyrolysis of said given polymer to its high value monomeric constituent prior to a temperature range that causes pyrolysis of other plastic components; selecting a catalyst and support for treating said feed streams with said catalyst to effect acid or base catalyzed reaction pathways to maximize yield or enhance separation of said high value monomeric constituent in said temperature program range; differentially heating said feed stream at a heat rate within the first temperature program range to provide differential pyrolysis for selective recovery of optimum quantities of the high value monomeric constituent prior to pyrolysis of other plastic components; separating thType: GrantFiled: December 4, 1992Date of Patent: April 5, 1994Assignee: Midwest Research InstituteInventors: Robert J. Evans, Helena L. Chum
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Patent number: 5288926Abstract: Bisphenols are prepared bya) reacting a phenolic compound with a carbonyl compound in a reaction mixture, containing the carbonyl compound, a stoichiometric excess of the phenolic compound and a catalyst, to produce a product mixture containing a bisphenol,b) separating bisphenol from the product mixture to leave a mother liquor andc) recycling at least a portion of the mother liquor to the reaction mixture.At least a portion of the phenolic compound is contacted with a strongly acidic cation exchange resin and a strongly basic anion exchange resin before the phenolic compound is used in the reaction step a) and/or at least a portion of the product mixture and/or at least a portion or the mother liquor is contacted with a strongly acidic cation exchange resin and a strongly basic anion exchange resin before mother liquor is recycled to the reaction mixture.Type: GrantFiled: February 4, 1993Date of Patent: February 22, 1994Assignee: The Dow Chemical CompanyInventors: Emil Patrascu, Dieter Tank, Jochen Gressmann, Johann-Wilhelm Frey, Ulrich Wallbaum
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Patent number: 5283375Abstract: This invention relates to a process for preparing a flame retardant product predominant in tetrabromobisphenol-A. The process comprises: (a) dissolving bisphenol-A in a methanol solvent containing up to about 5 weight percent water, wherein the ratio of methanol to bisphenol-A ranges from about 25 to about 43 moles of methanol per mole of bisphenol-A based on the total amount of methanol used and the total amount of bisphenol-A to be brominated; (b) adding to the solution in (a) from about 3.9 to about 4.2 moles of bromine per mole of bisphenol-A to be brominated while maintaining a reaction temperature in the range of from about 0.degree. to about 40.degree. C.; (c) after the bromination is substantially complete, adding water to precipitate the tetrabromobisphenol-A thus formed; and (d) purifying the precipitated tetrabromobisphenol-A so as to obtain a product predominant in tetrabromobisphenol-A containing less than about 20 ppm total ionic impurity.Type: GrantFiled: December 15, 1992Date of Patent: February 1, 1994Assignee: Ethyl CorporationInventors: Bonnie G. McKinnie, Gary L. Sharp, Robert E. Williams
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Patent number: 5276213Abstract: Dihydroxydiphenyl bicycloalkanes characterized in that they contain 9 to 13 ring C atoms in the bicycloaliphatic component are disclosed. The disclosed compounds were found to be suitable for the preparation of high molecular weight, thermoplastic polycarbonate resins having favorable properties.Type: GrantFiled: February 10, 1993Date of Patent: January 4, 1994Assignee: Bayer AktiengesellschaftInventors: Volker Serini, Uwe Westeppe, Gerd Fengler, Manfred Hajek, Carl Casser, Helmut Waldmann
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Patent number: 5276214Abstract: A biphenyl compound having the formula (I) is newly separated into its optical active compound, and useful as an optically separating agent: ##STR1## wherein W, X and Y are each an atom or atomic group selected from among H, F, Cl, Br, I, CH.sub.3, CF.sub.3, OH, OCH.sub.3, NH.sub.2 and N(CH.sub.3).sub.2 and Z is an atom or atomic group selected from among Cl, Br, I, CH.sub.3 and OCH.sub.Type: GrantFiled: December 18, 1992Date of Patent: January 4, 1994Assignee: Daicel Chemical Industries, Ltd.Inventor: Fumio Toda
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Patent number: 5276217Abstract: Novel cyclic anti-tumor promoter compounds and therapeutic compositions are disclosed, along with method for their production and use as anti-cancer and cancer-prevention agents.Type: GrantFiled: March 19, 1992Date of Patent: January 4, 1994Assignee: University of HawaiiInventor: Marcus A. Tius
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Patent number: 5248839Abstract: A preparation process of high purity bisphenol A from phenol and acetone with a continuous or batch type reactor by on-line estimating with a computer the composition of the reaction mixture and saturated dissolving temperature of bisphenol A under the reaction conditions and by automatically controlling the reaction conditions and liquid transfer conditions of the reaction mixture to the next step. The process does not form crystals of bisphenol A-phenol adduct in the reactor and cooler. A maximum rate of reaction can be obtained. Consequently, fluctuation of reaction temperature can be prevented and the amount of impurities formed is small. The discharge operation of the reaction mixture from the reactor can be carried out steadily and with ease, and does not disturb the operation of successive steps.Type: GrantFiled: April 7, 1992Date of Patent: September 28, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Shigeru Iimuro, Akira Yamada, Kenichi Ohmura, Toshio Houri, Tsuguo Kawamura
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Patent number: 5245084Abstract: The mixture consists of at least one organic peroxide, at least one hydroquinone derivative of the general formulae I and/or II and/or III ##STR1## wherein R and R.sup.1, which may be identical or different, stand for H or t-alkyl, and X stands, for example, for C.sub.1-18 -alkylene, and a crosslinkage promoter, and permits the crosslinkage of polymers and at the same time extends the scorch time, which must be understood as the processing time.Type: GrantFiled: October 17, 1991Date of Patent: September 14, 1993Assignee: Luperox GmbHInventors: Jurgen Groepper, Harald Hofmann
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Patent number: RE34626Abstract: This invention relates to a process for the preparation of bisphenols and bisphenol mixtures by the isomerization of bisphenols on acid or alkaline catalysts in the presence of the corresponding phenols.Type: GrantFiled: February 1, 1993Date of Patent: May 31, 1994Assignee: Bayer AGInventors: Udo Rudolph, Claus Wulff