Halogen Containing Patents (Class 568/713)
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Patent number: 8535577Abstract: The present invention relates to photochromic materials that include certain indeno-fused naphthopyrans. The indeno-fused naphthopyrans have an amino group (e.g., a piperidino or morpholino group) bonded to the 6-position and hydrogen or a halo group (e.g., fluoro) bonded to the 11-position thereof. The photochromic materials of the present invention can have a closed-form electromagnetic radiation absorption spectrum that is shifted to longer wavelengths (e.g., wavelengths of greater than 390 nm), relative to comparable photochromic materials. The present invention also relates to optical elements, such as eyeglasses, that include the photochromic materials of the present invention.Type: GrantFiled: October 7, 2011Date of Patent: September 17, 2013Assignee: Transitions Optical, Inc.Inventors: Anu Chopra, David B. Knowles, Huayun Yu
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Patent number: 8277699Abstract: The present invention relates to photochromic materials that include certain indeno-fused naphthopyrans. The indeno-fused naphthopyrans have an amino group (e.g., a piperidino or morpholino group) bonded to the 6-position and an optional halo group (e.g., fluoro) bonded to the 11-position thereof. The photochromic materials of the present invention may have a closed-form electromagnetic radiation absorption spectrum that is shifted to longer wavelengths (e.g., wavelengths of greater than 390 nm), relative to comparable photochromic materials. The present invention also relates to optical elements, such as eyeglasses, that include the photochromic materials of the present invention.Type: GrantFiled: April 28, 2011Date of Patent: October 2, 2012Assignee: Transistions Optical, Inc.Inventors: Anu Chopra, David B. Knowles, Huayun Yu
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Patent number: 7655819Abstract: A polymer that contains an antimicrobial, bioresistant and fungal resistant moiety that is linked into the backbone of the polymer. The moiety is a bromine atom and a nitro group linked to one or more of the carbon atoms forming the backbone. The moiety can appear in the polymer chain in various levels of occurrence from 5 ppm to has high as 100% with a normal occurrence of between 1000 ppm to 20,000 ppm. Polymer types that can be created with this moiety to display these properties include, but are not limited to, polyurethane, polyurea, polyamide, polyester, polycarbonate, polyether, polysiloxane, epoxy, polyacrylic, polyacrylate, polyvinyl.Type: GrantFiled: July 29, 2005Date of Patent: February 2, 2010Assignee: TPAT IP LLCInventor: Thomas Daly
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Patent number: 7557208Abstract: Described are naphthols useful in the manufacture of novel indeno-fused photochromic naphthopyran materials.Type: GrantFiled: November 11, 2008Date of Patent: July 7, 2009Assignee: Transitions Optical, Inc.Inventors: Robert W. Walters, Anil Kumar, Clara E. Nelson, Anu Chopra
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Patent number: 7517982Abstract: Described are naphthols useful in the manufacture of novel indeno-fused photochromic naphthopyran materials.Type: GrantFiled: March 1, 2007Date of Patent: April 14, 2009Assignee: Transitions Optical, Inc.Inventors: Robert W. Walters, Anil Kumar, Clara E. Nelson, Anu Chopra
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Patent number: 7273938Abstract: This invention relates to a new process for the preparation of novel substituted haloarene compounds of the formula I or IV: respectively, wherein R1, R2, R3, R4, R5, X, and Y are as defined herein, that comprises a novel and efficient selective mono-lithiation of a dihaloarene of the formula II or V: respectively, by an organo-lithium compound in the presence of a carbonyl reactant of the formula III: wherein R1 and R2 are as defined herein. In the process of the instant invention, the newly formed lithiated haloarene is sequentially quenched in situ by the carbonyl reactant to form said substituted haloarene. The process is suitable for batch or continuous flow systems.Type: GrantFiled: July 13, 2005Date of Patent: September 25, 2007Assignee: Pfizer Inc.Inventors: Jennifer L. Rutherford, Joel M. Hawkins
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Patent number: 6255522Abstract: The present invention has its objects to provide a method for reducing &agr;-aminoketone derivatives under mild conditions with high stereoselectivity.Type: GrantFiled: September 29, 1999Date of Patent: July 3, 2001Assignee: Kaneka CorporationInventors: Kazuhiko Matsuo, Shingo Matsumoto, Kenji Inoue
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Patent number: 5929284Abstract: Processes for efficiently producing .alpha.-halo ketones, .alpha.-halohydrins and epoxides on an industrial scale. The prosesses include one for producing an .alpha.-halo ketone of general formula (3) by decarboxylating a product of reaction between a carboxilic acid derivative of general formula (1) and a metal enolate prepared from an .alpha.-haloacetic acid of general formula (2) or an acceptable salt thereof, one for producing an by reducing the .alpha.-halo ketone (3), and one for producing an epoxide (13) by treating the .alpha.-halohydrin (11) with a base to effect ring closure. The above prosesses are particularly suitable for producing optically active .alpha.-halo ketones, .alpha.-halohydrins and epoxides from the corresponding .alpha.-amino acid derivatives.Type: GrantFiled: December 18, 1996Date of Patent: July 27, 1999Assignee: Kaneka CorporationInventors: Akira Nishiyama, Tadashi Sugawa, Hajime Manabe, Kenji Inoue, Noritaka Yoshida
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Patent number: 5907068Abstract: The invention concerns pharmaceutically useful trifluoromethyl ketone substituted di-, tri- and tetra-peptide derivatives of the formulae Ia, Ib, Ic set out hereinafter, and salts thereof which are inhibitors of human leukocyte elastase. Also described herein are pharmaceutical compositions containing a peptide derivative and processes and intermediates for use in the manufacture of the peptide derivatives.Type: GrantFiled: September 4, 1992Date of Patent: May 25, 1999Assignee: Zeneca Inc.Inventors: Mark Morris Stein, Diane Amy Trainor
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Patent number: 5874654Abstract: Environmentally-polluting nitrocresol values are removed from admixtures of nitroaromatic compounds comprised thereof, notably the media of nitration of aromatic compounds by reacting same with aqueous HNO.sub.3 /H.sub.2 SO.sub.4, by first intimately contacting such nitroaromatic compound admixtures with an oxidizing agent comprising hydrogen peroxide, javelle water, or mixture thereof, and thereafter with a neutralizing agent; the nitroaromatic aromatic compounds thus purified are conveniently catalytically hydrogenated into aromatic amines.Type: GrantFiled: September 19, 1997Date of Patent: February 23, 1999Assignee: Rhone Poulenc ChimieInventors: Antoinette Gacon-Camoz, Pascal Metivier
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Patent number: 5292967Abstract: According to a process for producing isomer-free 2,3-difluoro-6-nitrophenol, 2,3,4-trifluoronitrobenzene is reacted with an aqueous solution of alkali metal or alkaline earth metal hydroxide in the absence of organic solvent, at temperatures between about 20.degree. C. and 100.degree. C., the pH value of the reaction mixture is set at about 1 to 6 by acid addition, the resulting product is stream distilled and the 2,3-difluoro-6-nitrophenol is isolated after cooling. No organic solvents are used during any of the steps of the process.Type: GrantFiled: March 23, 1993Date of Patent: March 8, 1994Assignee: Hoechst AktiengesellschaftInventors: Theodor Papenfuhs, Joachim Hackenbruch, Ralf Pfirmann
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Patent number: 5292966Abstract: 2-Nitro-3,6-dichlorophenol is prepared by sulfonation of 2,5-dichlorophenol and subsequent nitration and desulfonation, in which the nitration is carried out by metering in a nitrating acid composed of 98 to 100% strength nitric acid and 96 to 100% strength sulfuric acid at temperatures from -15.degree. to 35.degree. C. and a metering time of at least 1 hour.Type: GrantFiled: March 16, 1993Date of Patent: March 8, 1994Assignee: Hoechst AktiengesellschaftInventors: Michael Meier, Heinz-Georg Kautz
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Patent number: 5243092Abstract: There is disclosed a method for producing,2,2-dibromo-2-nitroethanol. The method comprises first reacting tris(hydroxymethyl)nitromethane in aqueous solution with an alkali and then reacting the product of said first reaction with bromine.Type: GrantFiled: July 21, 1992Date of Patent: September 7, 1993Assignee: K.multidot.I Chemical Industry Co., Ltd.Inventors: Koichi Iwabuchi, Hisatake Ogura, Tetsuo Horii
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Patent number: 5232836Abstract: Vitamin D derivatives corresponding to the following formula I ##STR1## in which R.sub.1 denotes a substituted alkyl group having 1 to 15 carbon atoms, in particular the side chains of vitamin D.sub.2 (C.sup.20 to C.sup.28) or D.sub.3 (C.sup.20 to C.sup.Type: GrantFiled: February 18, 1992Date of Patent: August 3, 1993Assignee: Ire-Medgenix S.A.Inventors: Roger Bouillon, Pierre J. De Clerco, Pierre Eliard, Maurits Vanderwalle
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Patent number: 5144087Abstract: A process for preparing dibromonitro-alcohols, and mixtures thereof with bromonitro-alcohols, is disclosed in which dibromonitromethane, and optionally bromonitroethane, is reacted with a C.sub.1 -C.sub.3 aldehyde in aqueous solution at an acid pH, preferably between about 4.0 and about 7.0. An aqueous solution of the aldehyde is prepared and the pH adjusted to the desired acid range by addition of sodium bicarbonate, and the dibromonitromethane, which may include bromonitromethane, is added thereto. The dibromonitro-alcohol product is isolated as a separate phase from the reaction mixture.Type: GrantFiled: October 16, 1991Date of Patent: September 1, 1992Assignee: Great Lakes Chemical Corp.Inventors: James E. Williams, Scott Thornburgh
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Patent number: 5136109Abstract: 2-4-Dichloro-3-alkyl-6-nitrophenols which are useful as intermediate of cyan couplers in color photography are prepared by sulfonating 4-chloro-3-alkyl-phenols to obtain 5-chloro-4-alkylhydroxybenzenesulfonic acids, chlorinating the acids in an aqueous phase to obtain 3,5-dichloro-4-alkyl-2-hydroxybenzenesulfonic acids and nitrating the sulfonic acids.Type: GrantFiled: May 29, 1991Date of Patent: August 4, 1992Assignee: Taoka Chemical Company, Ltd.Inventors: Osamu Kimura, Yasuhiko Horikawa, Masaya Yamashita, Kazutaka Morino, Shinichi Koyama
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Patent number: 5112871Abstract: A bromo-nitro compound of the general formula ##STR1## where R, R.sup.1 and R.sup.2 can be hydrogen, or a hydrocarbyl group and R can also be R.sup.3 CO or R.sup.3 NHCO and n has a value of at least one. R and R.sup.1 can both be hydrogen. The value of n is typically one. Compounds of this type have anti-microbial properties, expecially anti-bacterial properties. The compounds can be used as industrial biocides, especially in water treatment.Type: GrantFiled: October 31, 1989Date of Patent: May 12, 1992Assignee: Imperial Chemical Industries PLCInventor: Peter W. Austin
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Patent number: 5075510Abstract: A process for preparing bromonitro-alcohols is disclosed in which bromonitromethane is reacted with a C.sub.1 -C.sub.3 aldehyde in aqueous solution at an acid pH, preferably between about 4.0 and about 7.0. An aqueous solution of the aldehyde is prepared and the pH adjusted to the desired acid range by addition of sodium bicarbonate, and the bromonitromethane is added thereto. The bromonitro-alcohol product is isolated as a separate phase from the reaction mixture.Type: GrantFiled: December 20, 1990Date of Patent: December 24, 1991Assignee: Great Lakes Chemical CorporationInventors: James E. Williams, Scott Thornburgh
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Patent number: 5012015Abstract: 2,4-Dichloro-3-alkyl-6-nitrophenol, which is a precursor of 2,4-dichloro-3-alkyl-6-aminophenol useful for the production of a cyan coupler to be used with a sensitive material in the field of a photography in color, is industrially advantageously produced by (a) nitration of 2,4,5-trichloro-3-alkylbenzene, followed by hydrolysis of the resulting 2,4,5-trichloro-3-alkyl-6-nitrobenzene, or (b) hydrolysis of 2,4,5-trichloro-3-alkylbenzene-6-sulfonic acid or a salt thereof, followed by nitration of the resulting 2,4-dichloro-3-alkylphenol-6-sulfonic acid or a salt thereof, the starting material usable for these processes being 4-alkylbenzenesulfonic acid or a salt thereof, which is easily available.Type: GrantFiled: March 7, 1989Date of Patent: April 30, 1991Assignees: Daiei Chemical Co., Ltd., Sumitomo Chemical Co., Ltd.Inventors: Masanobu Terao, Yuzo Maegawa, Yasuyoshi Ueda, Kiyoyasu Hashimoto, Takashi Omura
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Patent number: 5001279Abstract: The displacement of halogen from a 1,2,3-trihalo-4,6-dinitroresorcinol can be carried out in an aqueous medium using alkali metal hydroxide to form 2-halo-4,6,-dinitroresorcinol. The product is a useful intermediate in the synthesis of 4,6-diaminoresorcinol, which is a monomer for polybenzoxazole polymers. The process from part of a useful aqueous process for synthesizing 4,6-diaminoresorcinol.Type: GrantFiled: November 17, 1989Date of Patent: March 19, 1991Assignee: The Dow Chemical CompanyInventor: Tyze-Kuan T. Yin
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Patent number: 4978808Abstract: Disclosed herein is a method of producing 2,2-bis(3-nitro-4-hydroxphenyl)hexafluoropropane, which comprises (a) preparing 2,2-bis(4-hydroxyphenyl)hexafluoropropane and a lower fatty acid; and (b) allowing the 2,2-bis(4-hydroxyphenyl)hexafluoropropane to react with nitric acid in the lower fatty acid.Type: GrantFiled: May 31, 1989Date of Patent: December 18, 1990Assignee: Central Glass Company, LimitedInventors: Masamichi Maruta, Tetsuo Wada
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Patent number: 4960955Abstract: The process of making 4-chloro-2-methyl-5-nitro phenol (I) ##STR1## comprises nitrating a 4-chloro-2-methyl-phenyl sulfonate of the formula (II) at the 5 position ##STR2## in which R is a residue selected from the group consisting of methyl-, ethyl-, trifluoromethyl-, phenyl- and tolyl and the sulfonyl residue comprises --SO.sub.2 R at the position 5 to form 4-chloro-2-methyl-5-nitro-phenyl-sulfonate and then cleaving the sulfonyl residue of the 4-chloro-2-methyl-5-nitro-phenyl-sulfonate to form the 4-chloro-2-methyl-5-nitro-phenyl. The process uses technically available and economical starting materials and allows an isomerically pure product to be made in very good yield.Type: GrantFiled: May 17, 1989Date of Patent: October 2, 1990Assignee: Wella AktiengesellschaftInventors: Thomas Clausen, David Rose
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Patent number: 4943666Abstract: An improved industrial process for producing a compound of the general formula: ##STR1## wherein R is an alkyl group having 1 to 4 carbon atoms which comprises reacting a compound of the general formula: ##STR2## wherein R is as defined above with nitrous acid in a mixed solvent of water and a water-insoluble or slightly soluble organic solvent.Type: GrantFiled: April 14, 1989Date of Patent: July 24, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Taiiti Okada, Toru Ishida
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Patent number: 4922030Abstract: A method of preparing bromonitroalcohols of the formula ##STR1## where R.sub.1 is H, lower alkyl or R.sub.2, R.sub.2 is R.sub.3 CHOH in which R.sub.3 is H, alkyl or aryl, and X is a halogen, which comprises reacting a halonitroalkane with a substantially nonaqueous solutioln of an aldehyde of the formula R.sub.3 CHO where R.sub.3 is as noted above, in the presence of an alkaline catalyst. R.sub.3 preferably is lower alkyl or monocyclic aryl such as phenyl.Type: GrantFiled: December 5, 1988Date of Patent: May 1, 1990Assignee: Angus Chemical CompanyInventors: Vincent Nocito, Louis J. Bedell, Matthew I. Levinson
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Patent number: 4851588Abstract: A process of forming 2-bromo-2-nitro-1,3-propanediol by contacting a 5-nitro-1,3-dioxane with bromine under alkaline conditions and hydrolyzing the brominated product.Type: GrantFiled: June 23, 1988Date of Patent: July 25, 1989Assignee: W. R. Grace & Co.-Conn.Inventors: Robert J. Kupper, Felek Jachimowicz, Jennifer M. Quirk, Christer L. Hakansson
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Patent number: 4778935Abstract: Fluorinated nitroalcohols of the formula (I) ##STR1## process for their preparation by reaction of fluoronitroalkane of the formula (II) ##STR2## with a carbonyl compound of the formula (III) ##STR3## fluorinated aminoalcohols of the formula (IV) ##STR4## and a process for their preparation by hydrogentation of compounds of the formula (I).Type: GrantFiled: November 6, 1986Date of Patent: October 18, 1988Assignee: Bayer AktiengesellschaftInventors: Albert K. Beck, Dieter Seebach
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Patent number: 4723044Abstract: A process for producing a dibromonitro compound represented by the general formula ##STR1## wherein R represents a hydrogen atom or a methyl group, which comprises condensing nitromethane with formaldehyde or acetaldehyde in the presence of an alkali, the amount of the aldehyde being at least 1.5 moles per mole of nitromethane; and thereafter without isolating the product, treating the reaction mixture with bromine to brominate the product.Type: GrantFiled: June 13, 1986Date of Patent: February 2, 1988Assignee: Permachem Asia, Ltd.Inventors: Michio Watanabe, Kiyoshi Ishii, Mie Namiki, Takeshi Fukuda
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Patent number: 4636476Abstract: A tablet for use in preserving samples of milk for analysis comprises bronopol (2-bromo-2-nitropropane-1,3-diol) and a water-soluble solid organic carboxylic acid, the amount of the organic acid being within the range 0.002-0.07 milli-equivalents per milligram of bronopol. The presence of the organic acid stabilizes the bronopol, thereby providing a tablet with an adequate shelf life. Suitable organic acids include citric acid, tartaric acid, malic acid, adipic acid, succinic acid and fumaric acid.Type: GrantFiled: April 15, 1985Date of Patent: January 13, 1987Assignee: The Boots Company PlcInventors: Keith D. Brunt, Frederick R. Higton
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Patent number: 4581178Abstract: Low valent transition metal complexes containing small cone angle phosphine or arsine ligands efficiently catalyze addition of aldehydes to compounds or groups having a C--H bond activated by a nitro or nitrile group, to provide nitroalcohols or cyanohydrins, respectively.Type: GrantFiled: February 28, 1985Date of Patent: April 8, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: David Milstein
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Patent number: 4469902Abstract: Novel 1-iodoprop-1-yn-3-ols of the formula ##STR1## in which R.sup.1 represents optionally substituted aryl andR.sup.2 represents alkyl or cycloalkyl, which may be used as plant protection agents, especially as fungicides, are obtained when 1-iodoprop-1-yn-3-ols are reacted with iodine in the presence of a basic compound.Type: GrantFiled: May 14, 1982Date of Patent: September 4, 1984Assignee: Bayer AktiengesellschaftInventors: Gerhard Jager, Wilhelm Brandes, Paul-Ernst Frohberger
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Patent number: 4347148Abstract: Nitro phenols of the general formula ##STR1## wherein R is an aliphatic substituent of at least about 40 carbon atoms, a, b and c are, for example, each 1, 2 or 3, and Ar is an aromatic moiety such as a benzene nucleus, naphthalene nucleus or linked benzene nuclei, are useful additives for fuels and lubricants and intermediates to such additives. These nitro phenols can be conveniently prepared by nitrating appropriate phenols. Typically nitro phenols are formed by nitration of alkyl phenols having an alkyl group of at least about 50 carbon atoms.Type: GrantFiled: November 19, 1979Date of Patent: August 31, 1982Assignee: The Lubrizol CorporationInventor: Kirk E. Davis
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Patent number: 4322442Abstract: 1-Halo-1-propyn-3-ols of the formula ##STR1## in which R is optionally substituted phenyl, pyridyl, furyl, thienyl or pyrazolyl,R' is optionally substituted phenyl, andX is halogen,which possess fungicidal properties.Type: GrantFiled: September 8, 1980Date of Patent: March 30, 1982Assignee: Bayer AktiengesellschaftInventors: Gerhard Jager, Erich Klauke, Wilhelm Brandes, Paul-Ernst Frohberger
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Patent number: 4283565Abstract: There is described an essentially two step process for the preparation of benzylalcohols including those benzylalcohols having substituents on the benzyene ring by reaction of a substituted or unsubstituted benzyl halide with a formate typically an alkali or alkaline earth metal formate to form the corresponding substituted or unsubstituted benzyl formate. In the second step of the process the benzyl formate is contacted with an alcohol whereby the same is converted into the desired benzylalcohol. Both steps can be performed employing catalysts. Described in the specification is the realization of the desired product in exceptionally high yields in a short period of time whereby the process is characterized by high space-time yields.Type: GrantFiled: December 29, 1978Date of Patent: August 11, 1981Assignee: Dynamit Nobel AGInventors: Gunther Bernhardt, Gerhard Daum
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Patent number: 4278816Abstract: Phenols and thiophenols are produced by reacting the corresponding diphenyl ether compound with hydrogen sulfide in contact with an absorptive catalyst, such as charcoal, activated carbon, calcined petroleum coke, etc. Temperatures in the range of from about 300.degree. to about 900.degree. C. are employed.Type: GrantFiled: August 26, 1977Date of Patent: July 14, 1981Assignee: Stauffer Chemical CompanyInventor: Kyung-sup Shim
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Patent number: RE34589Abstract: The displacement of halogen from a 1,2,3-trihalo-4,6-dinitroresorcinol can be carried out in an aqueous medium using alkali metal hydroxide to form 2-halo-4,6-dinitroresorcinol. The product is a useful intermediate in the synthesis of 4,6-diaminoresorcinol, which is a monomer for polybenzoxazole polymers. The process from part of a useful aqueous process for synthesizing 4,6-diaminoresorcinol.Type: GrantFiled: October 26, 1992Date of Patent: April 19, 1994Assignee: The Dow Chemical CompanyInventor: Tyze-Kuan T. Yin
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Patent number: RE34745Abstract: High purity 4,6-dinitro-1,3-benzenediol is prepared by (a) contacting a 1,2,3-trihalobenzene with a nitrating agent and an acid under reaction conditions such that a 1,2,3-trihalo-4,6-dinitrobenzene is produced, (b) contacting the 1,2,3-trihalo-4,6-dinitrobenzene prepared in (a) with an alkanol and a base under reaction conditions such that as 4,6-dinitro-2-halo-1,3-benzendiol is produced, and (c) contacting the 4,6-dinitro-2-halo-1,3-benzenediol prepared in (b) with a hydrogenating agent in the presence of a solvent and a catalyst under reaction conditions such that a 4,6-diamino-1,3-benzendiol is produced. This 4,6-diamino-1,3-benzene diol is useful in the preparation of high molecular weight polybenzoxazoles.Type: GrantFiled: November 9, 1992Date of Patent: September 27, 1994Assignee: The Dow Chemical CompanyInventor: Zenon Lysenko