Halogen Containing Patents (Class 568/726)
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Patent number: 12098238Abstract: A curable resin represented by General Formula (1). In General Formula (1), R1 each independently represent a monovalent substituent (an alkyl group, an alkoxy group, a fluorine atom, and the like), m is 0 to 4, n is 0 to 40, and R2's are each independently a monovalent group including a polymerizable functional group.Type: GrantFiled: February 24, 2021Date of Patent: September 24, 2024Assignee: Central Glass Company, LimitedInventors: Kensuke Hirotaki, Hirokatsu Nagura, Kenji Hosoi, Yukari Hara
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Patent number: 8969629Abstract: Disclosed are: a cyclic compound which has high solubility in a safe solvent, is highly sensitive, enables the formation of a resist pattern having a good shape, and rarely causes resist pattern collapse; a process for producing the cyclic compound; a radiation-sensitive composition containing the cyclic compound; and a resist pattern formation method using the composition. Specifically disclosed are: a cyclic compound having a specific structure; a process for producing the cyclic compound; a radiation-sensitive composition containing the compound; and a resist pattern formation method using the composition.Type: GrantFiled: November 25, 2010Date of Patent: March 3, 2015Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masaaki Takasuka, Masatoshi Echigo, Yu Okada
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Patent number: 8889744Abstract: Compounds, pharmaceutical compositions including the compounds, and methods of preparation and use thereof are disclosed. The compounds are hexafluoro-honokiol analogs. The compounds and compositions can be used to treat and/or prevent a wide variety of cancers, including drug resistant cancers. Representative hexafluoro-honokiol analogs include hexafluoro-honokiol, analogs in which one or both hydroxy groups are replaced with dichloroacetate esters, and analogs with increased fluorination. The compounds are believed to function, at least, by inhibiting angiogenesis and/or inducing apoptosis. Thus, the compounds are novel therapeutic agents for a variety of cancers.Type: GrantFiled: June 22, 2010Date of Patent: November 18, 2014Inventor: Jack L. Arbiser
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Patent number: 8846292Abstract: A radiation-sensitive composition containing a resist compound having a high sensitivity, a high resolution, a high etching resistance, and a low outgas which forms a resist pattern with good shape and a method of forming a resist pattern and novel compositions for forming a photoresist under coat film which is excellent in optical properties and etching resistance and contains substantially no sublimable substance and an under coat film formed by the composition. Radiation-sensitive composition containing a solvent and a cyclic compound having, e.g., a cyclic compound (A) having a molecular weight of 700 to 5000 which is synthesized by the condensation reaction of a compound having 2 to 59 carbon atoms and 1 to 4 formyl groups with a compound having 6 to 15 carbon atoms and 1 to 3 phenolic hydroxyl groups, and a cyclic compound for use in the radiation-sensitive composition.Type: GrantFiled: December 29, 2011Date of Patent: September 30, 2014Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masatoshi Echigo, Dai Oguro
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Patent number: 8748078Abstract: A cyclic compound represented by formula (1): wherein L, R1, R?, and m are as defined in the specification. The cyclic compound of formula (1) is highly soluble to a safety solvent, highly sensitive, and capable of forming resist patterns with good profile. Therefore, the cyclic compound is useful as a component of a radiation-sensitive composition.Type: GrantFiled: August 30, 2010Date of Patent: June 10, 2014Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hiromi Hayashi, Masatoshi Echigo, Dai Oguro
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Publication number: 20130035304Abstract: This invention relates to compounds which selectively bind to the survival protein MCL-1 with high affinity and selectivity, pharmaceutical compositions containing such compounds and the use of those compounds or compositions for modulating MCL-1 activity and for treating hyperproliferative disorders, angiogenesis disorders, cell cycle regulation disorders, autophagy regulation disorders, inflammatory disorders, and/or infectious disorders and/or for enhancing cellular engraftment and/or wound repair, as a sole agent or in combination with other active ingredients.Type: ApplicationFiled: January 31, 2011Publication date: February 7, 2013Inventors: Loren D. Walensky, Michelle L. Stewart, Nicole Cohen
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Patent number: 8357701Abstract: Therapeutic agents for treatment of Galactosemia and disorders thereof, and other enzyme related disorders thereof are identified. The compounds inhibit galactokinase (GALK) and other kinase activity and are identified by a high throughput screening assay.Type: GrantFiled: August 14, 2008Date of Patent: January 22, 2013Assignee: University of MiamiInventors: Kent Lai, Klass Jan Wierenga, Manshu Tang
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Patent number: 8350096Abstract: A radiation-sensitive composition containing 1 to 80% by weight of a solid component and 20 to 99% by weight of a solvent. The solid component contains a compound B which has (a) a structure derived from a polyphenol compound A by introducing an acid-dissociating group to at least one phenolic hydroxyl group of the polyphenol compound A which is synthesized by a condensation between a di- to tetrafunctional aromatic ketone or aromatic aldehyde each having 5 to 36 carbon atoms with a compound having 1 to 3 phenolic hydroxyl groups and 6 to 15 carbon atoms, and (b) a molecular weight of 400 to 2000. The composition containing the compound B is useful as an acid-amplified, non-polymeric resist material, because it is highly sensitive to radiation such as KrF excimer lasers, extreme ultraviolet rays, electron beams, and X-rays, and provides resist patterns with a high resolution, high heat resistance, and high etching resistance.Type: GrantFiled: March 18, 2011Date of Patent: January 8, 2013Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masatoshi Echigo, Dai Oguro
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Publication number: 20120165406Abstract: Compounds, pharmaceutical compositions including the compounds, and methods of preparation and use thereof are disclosed. The compounds are hexafluoro-honokiol analogs. The compounds and compositions can be used to treat and/or prevent a wide variety of cancers, including drug resistant cancers. Representative hexafluoro-honokiol analogs include hexafluoro-honokiol, analogs in which one or both hydroxy groups are replaced with dichloroacetate esters, and analogs with increased fluorination. The compounds are believed to function, at least, by inhibiting angiogenesis and/or inducing apoptosis. Thus, the compounds are novel therapeutic agents for a variety of cancers.Type: ApplicationFiled: June 22, 2010Publication date: June 28, 2012Applicant: Jack L. ArbiserInventor: Jack L. Arbiser
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Patent number: 8110334Abstract: A radiation-sensitive composition containing a resist compound having a high sensitivity, a high resolution, a high etching resistance, and a low outgas which forms a resist pattern with a good shape is described. Further described is a method of forming a resist pattern using the radiation-sensitive composition. Still further described are a novel composition for forming a photoresist under coat film which is excellent in optical properties and etching resistance and contains substantially no sublimable substance and an under coat film formed by the composition.Type: GrantFiled: November 1, 2007Date of Patent: February 7, 2012Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masatoshi Echigo, Dai Oguro
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Publication number: 20110251236Abstract: Therapeutic agents for treatment of Galactosemia and disorders thereof, and other enzyme related disorders thereof are identified. The compounds inhibit galactokinase (GALK) and other kinase activity and are identified by a high throughput screening assay.Type: ApplicationFiled: August 14, 2008Publication date: October 13, 2011Applicant: University of MiamiInventors: Kent Lai, Klass Jan Wierenga, Manshu Tang
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Publication number: 20110110886Abstract: Autotaxin (ATX) is a prometastatic enzyme initially isolated from the conditioned media of human melanoma cells that stimulates a myriad of biological activities including angiogenesis and the promotion of cell growth, survival, and differentiation through the production of lysophosphatidic acid (LPA). ATX increases the aggressiveness and invasiveness of transformed cells, and ATX levels directly correlate with tumor stage and grade in several human malignancies. To study the role of ATX in the pathogenesis of malignant melanoma, we developed antibodies and small molecule inhibitors against recombinant human protein. Immunohistochemistry of paraffin embedded human tissue demonstrates that ATX levels are markedly increased in human primary and metastatic melanoma relative to benign nevi. Chemical screens identified several small molecule inhibitors with binding constants ranging from nanomolar to low micromolar.Type: ApplicationFiled: June 15, 2009Publication date: May 12, 2011Inventor: Demetrios Braddock
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Patent number: 7932014Abstract: A photosensitive compound has two or more structural units, in a molecule, represented by the following general formula (1): wherein R1 to R8 are selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an acetoxy group, a phenyl group, a naphthyl group, and an alkyl group in which some or all of the hydrogen atoms are optionally replaced by fluorine atoms; R9 is a hydrogen atom or a hydroxyl group; X is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene group; and Y is an oxygen atom or a single bond.Type: GrantFiled: February 14, 2008Date of Patent: April 26, 2011Assignee: Canon Kabushiki KaishaInventor: Toshiki Ito
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Patent number: 7834221Abstract: A process for preparing tetrabromobisphenol A, which comprises: i) reacting bisphenol A and bromine in dichloromethane in the presence of aqueous hydrogen peroxide at a temperature in the range of room temperature to the reflux temperature, wherein said dichloromethane is present in an amount sufficient for substantially dissolving brominated derivatives of said bisphenol A formed thereby, ii) separating the substantially solid-free reaction mixture obtained in step i) into aqueous and organic phases, precipitating tetrabromobisphenol A from the organic phase and isolating said precipitated tetrabromobisphenol A from said organic phase.Type: GrantFiled: July 3, 2006Date of Patent: November 16, 2010Assignee: Bromine Compounds Ltd.Inventor: Joseph Zilberman
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Publication number: 20100010274Abstract: A process for preparing tetrabromobisphenol A, which comprises: i) reacting bisphenol A and bromine in dichloromethane in the presence of aqueous hydrogen peroxide at a temperature in the range of room temperature to the reflux temperature, wherein said dichloromethane is present in an amount sufficient for substantially dissolving brominated derivatives of said bisphenol A formed thereby, ii) separating the substantially solid-free reaction mixture obtained in step i) into aqueous and organic phases, precipitating tetrabromobisphenol A from the organic phase and isolating said precipitated tetrabromobisphenol A from said organic phase.Type: ApplicationFiled: July 3, 2006Publication date: January 14, 2010Inventor: Joseph Zilberman
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Publication number: 20090221702Abstract: The present invention provides the use of a compound of the Formula: (I) wherein R1 is C1-5 alkoxy, OCOC1-3Alkyl, O(CH2)2O(CH2)2O(CH2)2OMe, O(CH2)2O(CH2)2O(CH2)2OH or OH; R2 is H, (CH2)nOH, OCH3, Hal or (II) or (III) R3 is H or (CH2)nOH; and R4 is C1-6 alkyl, optionally substituted by one or more of Hal, OH, COCH3, NH2, NHCH3, NHMe, NMe2, OCOCH3, CO2H or esters or amides thereof where n is 1-5; and pharmaceutically acceptable salts thereof, in the manufacture of a medicament for use in modulating PKB activity.Type: ApplicationFiled: March 17, 2006Publication date: September 3, 2009Inventors: Rudiger Woscholski, Helen Hailes, Macba Numbere, Erika Rosivatz
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Patent number: 6906226Abstract: Hydroxymethyl-substituted polyfunctional phenols, expressed by the following structure: General structure (I) (wherein X represents: bivalent group (a) expressed by the following structure: General structure (II) (wherein R1, R2, R3 and R4 each independently represent a hydrogen atom or an alkyl group with a carbon atom number of 1 through 4); quadrivalent group (b) expressed by the following structure: General structure (III) (wherein R5 and R6 each independently represent a hydrogen atom or an alkyl group with a carbon atom number of 1 through 4); or bivalent group (c) expressed by the following structure: General structure (IV) (wherein R7 and R8 each independently represent a hydrogen atom or a monofluoromethyl, difluoromethyl or trifluoromethyl group; however, R7 and R8 cannot be both hydrogen atoms); wherein n takes 2 when X is bivalent group (a), takes 4 when X is quadrivalent group (b), or takes 2 when X is bivalent group (c)).Type: GrantFiled: April 3, 2003Date of Patent: June 14, 2005Assignee: Honshu Chemical Industry Co., Ltd.Inventors: Kazuya Matsuishi, Takayuki Ohno, Taiichi Shiomi
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Patent number: 6740253Abstract: The present invention relates to a non-hazardous brominating reagent from an aqueous alkaline bromine byproduct solution obtained from bromine recovery plant and containing 25 to 35% bromine dissolved in aqueous lime or sodium hydroxide containing alkali bromide and alkali bromate mixture having bromide to bromate stoichiometric ratio in the range of 5:1 to 5.1:1 or 2:1 to 2.1:1 and a pH ranging between 8-12 and also relates to a method for borminating aromatic compounds by using the above brominating agent.Type: GrantFiled: January 23, 2002Date of Patent: May 25, 2004Assignee: Council of Scientific and Industrial ResearchInventors: Rajinder Nath Vohra, Pushpito Kumar Ghosh, Maheshkumar Ramniklal Gandhi, Himanshu Labhshanker Joshi, Hasina Hajibhai Deraiya, Rohit Harshadray Dave, Koushik Halder, Kishorkumar Manmohandas Majeethia, Sohan Lal Daga, Vadakke Puthoor Mohandas, Rahul Jasvantrai Sanghavi
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Patent number: 6613947Abstract: A high purity 4,4′-isopropylidine-bis-(2,6-dibromophenol) characterised by ionic bromides less than 10 ppm, colour in alkaline solution from 60-100 HU, HPLC purity about 99.9%, APHA of 20% MeOH solution less than 10.0 HU, Fe less than 1.0 ppm, turbidity of 20% MeOH solution less than 5 NTU, pH of 10% slurry 6.0-7.0, size of the crystal particles, 250 to 280 microns with angle of repose lower than 30°.Type: GrantFiled: October 21, 2002Date of Patent: September 2, 2003Assignee: Solaris Chemtech LimitedInventors: Shantaram Narayan Naik, Dharma Ratnakar Ramdas Naik, M. Madhusudan Rao
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Patent number: 6610890Abstract: Medicaments for treating diabetic complications contain a compound of formula (A), wherein at least one Y or one Y′ is OH, and the remainder are selected from H, Hal, OH, OMe and NO2; X is O, S, keto or a direct linkType: GrantFiled: January 7, 2002Date of Patent: August 26, 2003Assignee: O.N.C.E.-(Organizacion Nacional De Cicgos)Inventors: Teresa Garcia de Quesada Fort, Jesús A De La Fuente Blanco, Ma Jesús Martin Lopez, Isabel Reymundo Cuesta
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Patent number: 6365786Abstract: A highly pure and colorless tetrabromobisphenol-A (TBBPA) possessing melting point in the range of 178-182° C. is prepared in yields of 50-70% in first batch and 90-100% when the spent organic layer is recycled. In this method, the corrosive liquid bromine is displaced by sodium bromide/hydrobromic acid as brominating agent. Further, sodium bromate is used as an oxidizing as well as brominating agent to utilize the hydrobromic acid that is produced during the bromination of bisphenol-A (BPA). The reaction is conducted at 10-15° C. in a mixture of methylene chloride-water or carbon tetrachloride-water in the presence of hydrochloric acid and sodium lauryl sulfate. The crystalline product settled at the bottom of the reaction vessel is filtered, washed, dried and weighed. The spent organic layer is recycled in subsequent batches to maximize the overall yield of product recovered directly as solid and to minimize generation of organic effluent.Type: GrantFiled: January 22, 2001Date of Patent: April 2, 2002Assignee: Council of Scientific and Industrial ResearchInventors: Gadde Ramachandraiah, Pushpito Kumar Ghosh, Aditya Shantilal Mehta, Rajesh Popatlal Pandya, Ashok Dahyabhai Jethva, Sanjay Shambhubhai Vaghela, Sudhindra Nath Misra
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Patent number: 6313355Abstract: Tetrabromobisphenol-A is produced in a bromination process where no bromine or only a very small proportion of bromine is fed to the reactor. In the process aqueous hydrobromic acid, is the sole source or a major source of the bromine. In the process there are at least three concurrent continuous feeds to the reactor. One is composed of bisphenol-A and/or underbrominated bisphenol-A and a water-miscible organic solvent. The second is gaseous hydrogen bromide or preferably, aqueous hydrobromic acid, and the third is aqueous hydrogen peroxide. Optionally a small additional continuous feed of bromine can be employed. The feeds are proportioned to maintain a liquid phase containing (i) from above about 15 to about 85 wt % water, based upon the amount of water and water-miscible organic solvent in such liquid phase, and (ii) an amount of unreacted bromine that is in excess over the stoichiometric amount theoretically required to convert the bisphenol-A and/or underbrominated bisphenol-A to tetrabromobisphenol-A.Type: GrantFiled: July 12, 2000Date of Patent: November 6, 2001Inventors: Thanikavelu Manimaran, Richard A. Holub, Randall S. Barton
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Patent number: 6300527Abstract: This invention relates, inter alia, to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A and/or underbrominated bisphenol-A, which process features: a water and water-miscible organic solvent reaction medium; a relatively high reaction temperature; and the presence, in the reaction medium, of both (i) excess unreacted Br2 during the feed of bisphenol-A to the reactor, and (ii) sufficient HBr to protect the tetrabromobisphenol-A produced against undesirable color formation. Tetrabromobisphenol-A precipitates from the reaction mass and is easily recovered. Product of high purity (97% or more) and very low color (APHA of 50 or less) can be produced, even when using large excesses of bromine in the reaction.Type: GrantFiled: July 12, 2000Date of Patent: October 9, 2001Assignee: Albemarle CorporationInventors: Thanikavelu Manimaran, Hassan Y. Elnagar, Richard A. Holub, Alvin E. Harkins, Jr., Bonnie G. McKinnie
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Patent number: 6245950Abstract: The invention relates to a process for the preparation of high quality tetrabromobisphenol-A by reacting bisphenol-A with bromine and hydrogen peroxide as an oxidant in the presence of a heterogeneous catalyst in a biphase system consisting of water and water immiscible organic solvents.Type: GrantFiled: March 30, 2000Date of Patent: June 12, 2001Assignee: Council of Scientific and Industrial ResearchInventors: Mannepalli Lakshmi Kantam, Katuri Jeevaratnam, Boyapati Manoranjan Choudary, Chinta Reddy Venkat Reddy, Kondapuram Vijaya Raghavan, Lanka Venkata Sivaji, Thumma Someshwar
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Patent number: 6235946Abstract: Tetrabromobisphenol-A is produced in a bromination process where no bromine or only a very small proportion of bromine is fed to the reactor. In the process aqueous hydrobromic acid, is the sole source or a major source of the bromine. In the process there are at least three concurrent continuous feeds to the reactor. One is composed of bisphenol-A and/or underbrominated bisphenol-A and a water-miscible organic solvent. The second is gaseous hydrogen bromide or preferably, aqueous hydrobromic acid, and the third is aqueous hydrogen peroxide. Optionally a small additional continuous feed of bromine can be employed. The feeds are proportioned to maintain a liquid phase containing (i) from above about 15 to about 85 wt % water, based upon the amount of water and water-miscible organic solvent in such liquid phase, and (ii) an amount of unreacted bromine that is in excess over the stoichiometric amount theoretically required to convert the bisphenol-A and/or underbrominated bisphenol-A to tetrabromobisphenol-A.Type: GrantFiled: October 12, 1999Date of Patent: May 22, 2001Assignee: Albemarle CorporationInventors: Thanikavelu Manimaran, Richard A. Holub, Randall S. Barton
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Patent number: 6218584Abstract: This invention relates, inter alia, to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A and/or underbrominated bisphenol-A, which process features: a water and water-miscible organic solvent reaction medium; a relatively high reaction temperature; and the presence, in the reaction medium, of both (i) excess unreacted Br2 during the feed of bis-phenol-A to the reactor, and (ii) sufficient HBr to protect the tetrabromobisphenol-A produced against undesirable color formation. Tetrabromobisphenol-A precipitates from the reaction mass and is easily recovered. Product of high purity (97% or more) and very low color (APHA of 50 or less) can be produced, even when using large excesses of bromine in the reaction.Type: GrantFiled: June 10, 1999Date of Patent: April 17, 2001Assignee: Albemarle CorporationInventors: Thanikavelu Manimaran, Hassan Y. Elnagar, Richard A. Holub, Alvin E. Harkins, Jr., Bonnie G. McKinnie
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Patent number: 6162953Abstract: This invention relates to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A, which process features the addition of bisphenol-A to a reaction mass containing unreacted Br.sub.2 and 30 to 85 wt % water and an alcohol solvent, the reaction mass being at a relatively high temperature.Type: GrantFiled: September 28, 1999Date of Patent: December 19, 2000Assignee: Albemarle CorporationInventors: Bonnie G. McKinnie, Richard A. Holub, Hassan Y. Elnagar
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Patent number: 6147264Abstract: Bisphenol-A or preferably, a mixture of bisphenol-A and underbrominated bisphenol-A, is brominated in a liquid phase reaction medium in which tetrabromobisphenol-A is relatively insoluble, using a stoichiometric deficiency of bromine to thereby form in the reaction mass a precipitate (i.e., a solids phase) composed of 50-95 wt % of tetrabromobisphenol-A and 50-5 wt % of underbrominated bisphenol-A. The precipitate is separated from the reaction mass, preferably during the bromination, and tetrabromobisphenol-A is recovered from the precipitate. Preferably underbrominated bisphenol-A is recycled as feed to the bromination. The process technology of this invention has the capability of producing high quality tetrabromobisphenol-A (high purity, good color, low ionic halide content) with efficient raw material utilization, minimized waste product formation, and minimized waste disposal costs.Type: GrantFiled: April 8, 1999Date of Patent: November 14, 2000Assignee: Albemarle CorporationInventors: Thanikavelu Manimaran, Richard A. Holub, Randall S. Barton
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Patent number: 6084137Abstract: This invention relates to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A, which process features the addition of bisphenol-A to a reaction mass containing unreacted Br.sub.2 and 30 to 85 wt. % water and an alcohol solvent, the reaction mass being at a relatively high temperature.Type: GrantFiled: October 21, 1997Date of Patent: July 4, 2000Assignee: Albemarle CorporationInventors: Bonnie G. McKinnie, Richard A. Holub, Hassan Y. Elnagar
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Patent number: 6084136Abstract: This invention relates to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A, which process features: (a) feeding to a reaction mass (i) bisphenol-A and (ii) a stream of gaseous bromine, the gaseous stream having a Reynold's No. .gtoreq.40,000; (b) the reaction mass containing from about 50 to about 20,000 ppm unreacted bromine and less than 20 wt % HBr; and (c) the reaction mass having precipitated therefrom tetrabromobisphenol-A, all of (a)(ii), (b) and (c) occurring during the bisphenol-A feed.Type: GrantFiled: June 11, 1998Date of Patent: July 4, 2000Assignee: Albmarle CorporationInventors: Richard A. Holub, Steven R. Alferi, Bonnie G. McKinnie, Hassan Y. Elnagar
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Patent number: 6049014Abstract: A process for producing n-propyl bromide during the bromination of bis- or trisphenols uses non-aqueous n-propanol as the bromination solvent, providing salable yields of n-propyl bromide to accompany the brominated bisphenol or trisphlenol.Type: GrantFiled: February 19, 1998Date of Patent: April 11, 2000Assignee: Great Lakes Chemical CorporationInventors: Anne P. Noonan, Stephen C. Scherrer
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Patent number: 6002050Abstract: This invention relates to a process for the production of tetrabromobisphenol-A, which process features: a water and water miscible solvent reaction medium; a relatively high reaction temperature; and the presence, in the reaction medium, of unreacted Br.sub.2 during the feed of bisphenol-A to the reactor.Type: GrantFiled: September 8, 1998Date of Patent: December 14, 1999Assignee: Albemarle CorporationInventor: Bonnie G. McKinnie
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Patent number: 5986149Abstract: The present invention provides processes for recovering alkanols from fluids comprising the alkanol and aqueous hydrobromic acid without forming excessive amounts of alkyl bromide. In certain aspects of the invention, there are provided distillation systems wherein a fluid comprising an alkanol and aqueous hydrobromic acid is introduced into a distillation column at a point between the bottom and the top of the column to thereby separate the alkanol and the hydrobromic acid without causing the production of a significant amount of alkyl bromide.Type: GrantFiled: April 3, 1998Date of Patent: November 16, 1999Assignee: Great Lakes Chemical CorporationInventors: Richard J. DeGroot, James T. Ayers, Karl E. Reineke
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Patent number: 5847232Abstract: This invention relates to a process for the production of tetrabromobisphenol-A, which process features: a water and water miscible solvent reaction medium; a relatively high reaction temperature; and the presence, in the reaction medium, of unreacted Br.sub.2 during the feed of bisphenol-A to the reactor.Type: GrantFiled: June 27, 1997Date of Patent: December 8, 1998Assignee: Albemarle CorporationInventor: Bonnie G. McKinnie
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Patent number: 5817888Abstract: A bromination process for organic compounds employs stabilized bromine chloride solutions as the brominating agent. Activated aromatic compounds such as anisole can be selectively monobrominated in the para-position in high purity and yield.Type: GrantFiled: June 9, 1997Date of Patent: October 6, 1998Assignee: Albemarle CorporationInventors: Hassan Y. Elnagar, Robert L. Davis, Mahmood Sabahi
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Patent number: 5723690Abstract: 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: October 30, 1995Date of Patent: March 3, 1998Assignee: Albemarle CorporationInventor: Bonnie G. McKinnie
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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: 5475153Abstract: A process for the preparation of 4,4'-isopropylidene bis(2,6-dibromophenol), also known as tetrabrombisphenol A, that dramatically reduces the formation of alkyl bromide by-products. Bisphenol A is brominated with a C.sub.3 to C.sub.5 n-alcohol in a water mixture to suppress the formation of alkyl bromides. The bisphenol A is brominated between 15.degree. C. and 25.degree. C. and then heated at a 55.degree. C. to 70.degree. C. to insure bromination is complete. The tetrabrombisphenol A is then filtered from the reaction mixture and dried. Tetrabromobisphenol A produced from this process typically has a melting point of 180.degree. C. or higher, and is typically greater than 98% pure. Hydrogen peroxide is optionally combined with the reactants to reduce the amount of added bromine necessary for the bromination of the tetrabromobisphenol A.Type: GrantFiled: January 4, 1995Date of Patent: December 12, 1995Assignee: Great Lakes Chemical Corp.Inventor: Stuart Armstrong
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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: 5395994Abstract: This invention provides an environmentally acceptable method for recovery of phenolic and brominated phenolic compounds, alcohol solvent, and bromide values from the a reaction medium liquid mixture formed in the production of a tetrabromobisphenol-A predominant product. The process comprises (a) separating the tetrabromobisphenol-A predominant product and alkyl bromide from the reaction medium thereby forming a liquid mixture containing alcohol, phenolic and brominated phenolic compounds, HBr, and water; (b) treating the liquid mixture with a sufficient amount of alkaline or alkaline earth metal hydroxide so as to form a treated aqueous mixture having a pH in the range of from about 9.5 to about 14.0, and containing MBr.sub.Type: GrantFiled: May 19, 1994Date of Patent: March 7, 1995Assignee: Albemarle CorporationInventors: Robert E. Williams, William J. Cranston, III
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Patent number: 5313008Abstract: The invention relates to a process for the conversion of 8-hydroxymenthenes into 8-hydroxycymenes by treating the 8-hydroxymenthenes in the vapour phase with an alkaline dehydrogenation catalyst, e.g. palladium on an alkaline support. The process is carried out above 145.degree. C. The hydroxymenthene vapour is preferably passed through the catalyst system at a pressure below 8 kPa and/or with the aid of an inert gas or vapour. Oxygen may be present as a hydrogen acceptor. The process is particularly suitable for converting 8-hydroxy-p-menth-1-ene into 8-hydroxy-p-cymene. The reaction products are of value as intermediates in the preparation of musk fragrance chemicals.Type: GrantFiled: April 6, 1993Date of Patent: May 17, 1994Assignee: Unilever Patent Holdings B.V.Inventor: Christopher P. Newman
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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: 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: 5237112Abstract: This invention relates to a process for preparing tetrabromobisphenol-A in high yield and high purity comprising: (a) forming a reaction solvent from at least one non-polar solvent and an amount of aqueous hydrogen peroxide; (b) charging an amount of alkylidenediphenol to the reaction solvent to form a reaction mass; (c) feeding an amount of bromine to the reaction mass at a temperature and for a period of time sufficient to tetra-brominate substantially all of the alkylidenediphenol thus charged; (d) maintaining during step (c) the amount of hydrogen peroxide less than an amount required to convert substantially all of the HBr which forms to elemental bromine; and (e) heat treating the formed product whereby a product having less than about 20 ppm ionic impurities is produced.Type: GrantFiled: August 31, 1992Date of Patent: August 17, 1993Assignee: Ethyl CorporationInventor: David E. LaRose
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Patent number: 5208389Abstract: The quality of a product predominant in tetrabromobisphenol-A is enhanced by contacting the product with a quality enhancing amount of treated water and heat treating the product for a period of time and at a temperature which are sufficient to obtain a TBBPA predominant product having less than about 20 ppm of ionic impurities.Type: GrantFiled: April 1, 1992Date of Patent: May 4, 1993Assignee: Ethyl CorporationInventors: Bonnie G. McKinnie, Gary L. Sharp
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Patent number: 5177268Abstract: A process for hydrodehalogenating halogenated aromatics present in a contaminated aqueous environmental source in which the halogenated aromatics are reacted with hydrogen gas or a source of hydrogen gas in the presence of a basic proton acceptor and a catalyst of palladium on carbon.Type: GrantFiled: April 6, 1992Date of Patent: January 5, 1993Assignee: Engelhard CorporationInventors: Edward N. Balko, Jeffrey B. Hoke, Gary A. Gramiccioni
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Patent number: 5138103Abstract: A process for producing tetrabromobisphenol A of high quality, which comprises brominating bisphenol A with bromine, wherein a solvent mixture comprising a hydrohalogenic acid and an alcohol, is used as the solvent for reaction. Also disclosed is a process for producing tetrabromobisphenol A of high quality, which comprises brominating bisphenol A with bromine in an alcohol, wherein the reaction temperature is set at a level of from -10.degree. to +20.degree. C., and water is added in an aging step.Type: GrantFiled: August 16, 1991Date of Patent: August 11, 1992Assignee: Tosoh CorporationInventors: Hisao Eguchi, Masashige Kubo, Noritaka Nagasaki, Koji Kunimoto
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Patent number: 5136110Abstract: The invention is a process for the preparation of triaromatic bisphenols 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: December 12, 1990Date of Patent: August 4, 1992Assignee: The Dow Chemical CompanyInventors: Marlin E. Walters, W. Frank Richey, Emmett L. Tasset
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Patent number: 5107035Abstract: The quality of a product predominant in tetrabromobisphenol-A is enhanced by heat treating the product for a period of time and at a temperature which are sufficient to obtain a TBBPA predominant product having less than about 50 ppm of hydrohalide impurities.Type: GrantFiled: November 15, 1990Date of Patent: April 21, 1992Assignee: Ethyl CorporationInventors: Harold W. Hines, Daniel A. Wood
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Patent number: 5068463Abstract: A process for the production of tetrabromo-4,4'-alkylidenediphenols, especially tetrabromobisphenol A (TBBA), from the corresponding alkylidenediphenols by oxidative bromination with Br.sub.2, HBr.sub.3 or HBr and aqueous hydrogen peroxide in the presence of an organic solvent. The process is characterized by washing the organic phase containing dissolved tetrabromo-4,4'-alkylidenediphenol with an aqeuous alkali sulphite solution, preferably at 50.degree. to 90.degree. C. Through this washing treatment, the tetrabromo compound is obtained in higher purity; in addition, the mother liquor can be recycled without difficulty.Type: GrantFiled: October 5, 1990Date of Patent: November 26, 1991Inventor: Eberhard Walter