Halogen Containing Patents (Class 568/713)
  • Patent number: 8535577
    Abstract: 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: Grant
    Filed: October 7, 2011
    Date of Patent: September 17, 2013
    Assignee: Transitions Optical, Inc.
    Inventors: Anu Chopra, David B. Knowles, Huayun Yu
  • Patent number: 8277699
    Abstract: 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: Grant
    Filed: April 28, 2011
    Date of Patent: October 2, 2012
    Assignee: Transistions Optical, Inc.
    Inventors: Anu Chopra, David B. Knowles, Huayun Yu
  • Patent number: 7655819
    Abstract: 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: Grant
    Filed: July 29, 2005
    Date of Patent: February 2, 2010
    Assignee: TPAT IP LLC
    Inventor: Thomas Daly
  • Patent number: 7557208
    Abstract: Described are naphthols useful in the manufacture of novel indeno-fused photochromic naphthopyran materials.
    Type: Grant
    Filed: November 11, 2008
    Date of Patent: July 7, 2009
    Assignee: Transitions Optical, Inc.
    Inventors: Robert W. Walters, Anil Kumar, Clara E. Nelson, Anu Chopra
  • Patent number: 7517982
    Abstract: Described are naphthols useful in the manufacture of novel indeno-fused photochromic naphthopyran materials.
    Type: Grant
    Filed: March 1, 2007
    Date of Patent: April 14, 2009
    Assignee: Transitions Optical, Inc.
    Inventors: Robert W. Walters, Anil Kumar, Clara E. Nelson, Anu Chopra
  • Patent number: 7273938
    Abstract: 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: Grant
    Filed: July 13, 2005
    Date of Patent: September 25, 2007
    Assignee: Pfizer Inc.
    Inventors: Jennifer L. Rutherford, Joel M. Hawkins
  • Patent number: 6255522
    Abstract: The present invention has its objects to provide a method for reducing &agr;-aminoketone derivatives under mild conditions with high stereoselectivity.
    Type: Grant
    Filed: September 29, 1999
    Date of Patent: July 3, 2001
    Assignee: Kaneka Corporation
    Inventors: Kazuhiko Matsuo, Shingo Matsumoto, Kenji Inoue
  • Patent number: 5929284
    Abstract: 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: Grant
    Filed: December 18, 1996
    Date of Patent: July 27, 1999
    Assignee: Kaneka Corporation
    Inventors: Akira Nishiyama, Tadashi Sugawa, Hajime Manabe, Kenji Inoue, Noritaka Yoshida
  • Patent number: 5907068
    Abstract: 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: Grant
    Filed: September 4, 1992
    Date of Patent: May 25, 1999
    Assignee: Zeneca Inc.
    Inventors: Mark Morris Stein, Diane Amy Trainor
  • Patent number: 5874654
    Abstract: 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: Grant
    Filed: September 19, 1997
    Date of Patent: February 23, 1999
    Assignee: Rhone Poulenc Chimie
    Inventors: Antoinette Gacon-Camoz, Pascal Metivier
  • Patent number: 5292967
    Abstract: 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: Grant
    Filed: March 23, 1993
    Date of Patent: March 8, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Theodor Papenfuhs, Joachim Hackenbruch, Ralf Pfirmann
  • Patent number: 5292966
    Abstract: 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: Grant
    Filed: March 16, 1993
    Date of Patent: March 8, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Michael Meier, Heinz-Georg Kautz
  • Patent number: 5243092
    Abstract: 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: Grant
    Filed: July 21, 1992
    Date of Patent: September 7, 1993
    Assignee: K.multidot.I Chemical Industry Co., Ltd.
    Inventors: Koichi Iwabuchi, Hisatake Ogura, Tetsuo Horii
  • Patent number: 5232836
    Abstract: 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: Grant
    Filed: February 18, 1992
    Date of Patent: August 3, 1993
    Assignee: Ire-Medgenix S.A.
    Inventors: Roger Bouillon, Pierre J. De Clerco, Pierre Eliard, Maurits Vanderwalle
  • Patent number: 5144087
    Abstract: 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: Grant
    Filed: October 16, 1991
    Date of Patent: September 1, 1992
    Assignee: Great Lakes Chemical Corp.
    Inventors: James E. Williams, Scott Thornburgh
  • Patent number: 5136109
    Abstract: 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: Grant
    Filed: May 29, 1991
    Date of Patent: August 4, 1992
    Assignee: Taoka Chemical Company, Ltd.
    Inventors: Osamu Kimura, Yasuhiko Horikawa, Masaya Yamashita, Kazutaka Morino, Shinichi Koyama
  • Patent number: 5112871
    Abstract: 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: Grant
    Filed: October 31, 1989
    Date of Patent: May 12, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: Peter W. Austin
  • Patent number: 5075510
    Abstract: 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: Grant
    Filed: December 20, 1990
    Date of Patent: December 24, 1991
    Assignee: Great Lakes Chemical Corporation
    Inventors: James E. Williams, Scott Thornburgh
  • Patent number: 5012015
    Abstract: 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: Grant
    Filed: March 7, 1989
    Date of Patent: April 30, 1991
    Assignees: Daiei Chemical Co., Ltd., Sumitomo Chemical Co., Ltd.
    Inventors: Masanobu Terao, Yuzo Maegawa, Yasuyoshi Ueda, Kiyoyasu Hashimoto, Takashi Omura
  • Patent number: 5001279
    Abstract: 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: Grant
    Filed: November 17, 1989
    Date of Patent: March 19, 1991
    Assignee: The Dow Chemical Company
    Inventor: Tyze-Kuan T. Yin
  • Patent number: 4978808
    Abstract: 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: Grant
    Filed: May 31, 1989
    Date of Patent: December 18, 1990
    Assignee: Central Glass Company, Limited
    Inventors: Masamichi Maruta, Tetsuo Wada
  • Patent number: 4960955
    Abstract: 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: Grant
    Filed: May 17, 1989
    Date of Patent: October 2, 1990
    Assignee: Wella Aktiengesellschaft
    Inventors: Thomas Clausen, David Rose
  • Patent number: 4943666
    Abstract: 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: Grant
    Filed: April 14, 1989
    Date of Patent: July 24, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Taiiti Okada, Toru Ishida
  • Patent number: 4922030
    Abstract: 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: Grant
    Filed: December 5, 1988
    Date of Patent: May 1, 1990
    Assignee: Angus Chemical Company
    Inventors: Vincent Nocito, Louis J. Bedell, Matthew I. Levinson
  • Patent number: 4851588
    Abstract: 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: Grant
    Filed: June 23, 1988
    Date of Patent: July 25, 1989
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Robert J. Kupper, Felek Jachimowicz, Jennifer M. Quirk, Christer L. Hakansson
  • Patent number: 4778935
    Abstract: 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: Grant
    Filed: November 6, 1986
    Date of Patent: October 18, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albert K. Beck, Dieter Seebach
  • Patent number: 4723044
    Abstract: 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: Grant
    Filed: June 13, 1986
    Date of Patent: February 2, 1988
    Assignee: Permachem Asia, Ltd.
    Inventors: Michio Watanabe, Kiyoshi Ishii, Mie Namiki, Takeshi Fukuda
  • Patent number: 4636476
    Abstract: 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: Grant
    Filed: April 15, 1985
    Date of Patent: January 13, 1987
    Assignee: The Boots Company Plc
    Inventors: Keith D. Brunt, Frederick R. Higton
  • Patent number: 4581178
    Abstract: 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: Grant
    Filed: February 28, 1985
    Date of Patent: April 8, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: David Milstein
  • Patent number: 4469902
    Abstract: 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: Grant
    Filed: May 14, 1982
    Date of Patent: September 4, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Jager, Wilhelm Brandes, Paul-Ernst Frohberger
  • Patent number: 4347148
    Abstract: 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: Grant
    Filed: November 19, 1979
    Date of Patent: August 31, 1982
    Assignee: The Lubrizol Corporation
    Inventor: Kirk E. Davis
  • Patent number: 4322442
    Abstract: 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: Grant
    Filed: September 8, 1980
    Date of Patent: March 30, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Jager, Erich Klauke, Wilhelm Brandes, Paul-Ernst Frohberger
  • Patent number: 4283565
    Abstract: 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: Grant
    Filed: December 29, 1978
    Date of Patent: August 11, 1981
    Assignee: Dynamit Nobel AG
    Inventors: Gunther Bernhardt, Gerhard Daum
  • Patent number: 4278816
    Abstract: 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: Grant
    Filed: August 26, 1977
    Date of Patent: July 14, 1981
    Assignee: Stauffer Chemical Company
    Inventor: Kyung-sup Shim
  • Patent number: RE34589
    Abstract: 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: Grant
    Filed: October 26, 1992
    Date of Patent: April 19, 1994
    Assignee: The Dow Chemical Company
    Inventor: Tyze-Kuan T. Yin
  • Patent number: RE34745
    Abstract: 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: Grant
    Filed: November 9, 1992
    Date of Patent: September 27, 1994
    Assignee: The Dow Chemical Company
    Inventor: Zenon Lysenko