Halogen Containing Patents (Class 568/610)
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Patent number: 9173939Abstract: Compounds having a structure of Structure I: or a pharmaceutically acceptable salt, tautomer, or stereoisomer thereof, wherein R1, R2, R3, R4, R5, J1, J2, X, Z, n1 and n2 are as defined herein, and wherein at least one of R1, R2 or R3 is an alkyl, alkenyl, aryl or aralkyl ester, are provided. Uses of such compounds for treatment of various indications, including prostate cancer, as well as methods of treatment involving such compounds are also provided.Type: GrantFiled: May 9, 2014Date of Patent: November 3, 2015Assignees: The University of British Columbia, British Columbia Cancer Agency BranchInventors: Raymond J. Andersen, Marianne D. Sadar, Javier Garcia Fernandez, Nasrin R. Mawji, Jun Wang, Carmen Adriana Banuelos
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Publication number: 20140318626Abstract: The present invention provides a high-conductivity hole transport material for reducing a photoelectron recombination reaction, and a solid-state dye-sensitized solar cell. The hole transport material is formed by using a compound having the structure of chemical formula (1) or (2) according to the present invention. The solid-state dye-sensitized solar cell comprises a hole transport material layer, which is formed by coating the compound on an inorganic oxide layer by means of photoelectrochemical polymerization or by means of thermal polymerization.Type: ApplicationFiled: January 31, 2012Publication date: October 30, 2014Applicant: POSTECH ACADEMY-INDUSTRY FOUNDATIONInventors: Taiho Park, In Young Song
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Publication number: 20140135518Abstract: A compound of formula (I) wherein Rf is —CF3, —C2F5, or —CF2CFXCF3; X is —F, or —OC3F7; Y is —H, —Cl, or —Br; R is —OH, —(CH2)nOH, —(OCH2CH2)mOH, —(CH2)n(OCH2CH2)mOH, —O—C(O)—R1, —(CH2)nO—C(O)R1, —(OCH2CH2)mOC(O)—R1, —C(O)NHw(CH2CH2OH)2-w, —C?N, —C?CH, or —C(O)R2; n is 1 to 10; m is 1 to 10; R1 is C1 to C10 alkyl; R2 is —H, C1 to C10 alkyl, —Cl, or —OCH2CH2OH; a is 1 to 5; b is 1 to 5; and w is 0, 1 or 2.Type: ApplicationFiled: October 31, 2013Publication date: May 15, 2014Applicant: E I DU PONT DE NEMOURS AND COMPANYInventor: Neville Everton Drysdale
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Patent number: 8293947Abstract: The present invention concerns a method for the preparation of therapeutically valuable triphenylbutene derivatives, especially ospemifene or fispemifene.Type: GrantFiled: September 16, 2010Date of Patent: October 23, 2012Assignee: Hormos Medical Ltd.Inventors: Marja Sodervall, Maire Eloranta, Arja Kalapudas
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Patent number: 8058481Abstract: Described is a process for the alkoxylation of alcohols with I, Cl, or CH3CO2 endgroups, using alkylene epoxides in the presence of boron based catalysts.Type: GrantFiled: April 30, 2009Date of Patent: November 15, 2011Assignee: E.I. du Pont de Nemours and CompanyInventors: Kenneth Gene Moloy, James A. Schultz
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Patent number: 7091270Abstract: The present invention provides novel pentabromobenzyl alkyl ethers serving as highly effective flame retardants in polymers. The invention further provides a fire retarded polymer composition comprising said pentabromobenzyl alkyl ethers.Type: GrantFiled: January 23, 2000Date of Patent: August 15, 2006Assignee: Bromine Compounds Ltd.Inventors: Joseph Zilberman, Alon Tavor, Dorit Canfi, David Ioffe, Grigory Titelman, Samuel Bron, Olga Weinberg
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Patent number: 7019177Abstract: A process for preparing (per)fluorohalogenethers having general formula (II): R?CF2OCFA-CA?F2??(II) wherein:— A and A?, equal to or different from each other, are H, Cl or Br but they cannot be both H; R? has the following meanings: RO—, wherein R is a (per)fluorinated substituent, selected from the following groups: linear or branched C1–C20 alkyl; C3–C7 cycloalkyl; aromatic, C6–C10 arylalkyl or alkylaryl; C5–C10 heterocyclic or alkylheterocyclic; or a perfluoropolyether substituent T-Rf— wherein T=—OCF2OCFA-CA?F2, —OCF2XI, wherein XI=F, CF3, Cl; Rf is a perfluorooxyalkylene chain; by reaction of carbonyl compounds having formula R?COF (III) wherein R?=RO—, or R?=Q-Rf— wherein Q=—OCOF, —OCF2XI; in liquid phase with elemental fluorine and with olefinic compounds having formula CAF=CA?F (IV), at temperatures from ?120° C. to ?20° C.Type: GrantFiled: January 29, 2004Date of Patent: March 28, 2006Assignee: Solvay Solexis, S.p.A.Inventors: Vito Tortelli, Pierangelo Calini
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Patent number: 6891070Abstract: A new method for the preparation of a selective estrogen receptor modulator and its isomers. Also disclosed is the preparation of new intermediates and their use in the preparation of the selective estrogen receptor modulator.Type: GrantFiled: March 21, 2002Date of Patent: May 10, 2005Assignee: Hormos Medical CorporationInventors: Arja Kalapudas, Marja Södervall
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Patent number: 6881868Abstract: Compounds of formula (I), wherein R1 and R2 are, independently of one another, H,C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxyl, C1-C6alkoxy-C1-C6alkyl, or C1-C6alkoxy-C1-C6alkyloxy, and R3 is C1-C6alkyl, are obtainable in high yiedls by stereoselective addition of R3-substituted propionic acid esters to R1- and R2-substituted benzaldehydes of formula R—CHO to form corresponding 3-R-3-hydroxy-2-R3-propionic acid esters, conversion of the OH group to a leaving group, subsequent regioselective elimination to form 3-R-2-R3-propenic acid esters, and reduction to corresponding 3-R-2-R3-allyl alcohols and their enantioselective hydrogenation, wherein R is (a).Type: GrantFiled: June 26, 2001Date of Patent: April 19, 2005Assignee: Speedel Pharma AGInventors: Stefan Stutz, Peter Herold, Felix Spindler, Walter Weissensteiner, Thomas Sturm
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Patent number: 6756512Abstract: The invention relates to a novel process for preparing 2-alkyl-3-chlorophenols.Type: GrantFiled: October 30, 2002Date of Patent: June 29, 2004Assignee: Bayer AktiengesellschaftInventors: Walter Hübsch, Reinhard Lantzsch, Thorsten Müh, Holger Weintritt
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Patent number: 6646166Abstract: The present invention provides an improved process for the preparation of 1,4-diaryl-2-fluoro-1,3-butadiene compounds of the structural formula I In addition, the present invention provides an improved process for the preparation of 1,4-diaryl-2-fluoro-2-butadiene compounds of the structural formula IVType: GrantFiled: October 1, 2001Date of Patent: November 11, 2003Assignee: BASF AktiengesellschaftInventors: Yulin Hu, David Allen Hunt, Keith Douglas Barnes
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Patent number: 6429341Abstract: The present invention is a novel class of compounds useful in useful in thermally-responsive record material of the type comprising a substrate having provided thereon in substantially contiguous relationship an electron donating dye precursor, and an acidic developer material. The novel compound of the invention is a compound of the formula wherein P is selected from wherein R1, is selected from hydrogen, alkoxy, and aralkoxy; wherein R2 is aralkoxyalkoxy when P is phenyl, and R2 is selected from aralkoxyalkoxy or alkoxyalkoxy when P is naphthyl. Said alkyl moieties are each independently from one to eight carbons, said aryl moieties each independently being unsubstituted or substituted by alkyl (C1-C8), alkoxy (C1-C8) or halogen. The compounds of the invention enable manufacture of thermally responsive record material of the invention having the unexpected and remarkable properties of enhanced image intensity or density, and/or improved thermal response.Type: GrantFiled: January 4, 2001Date of Patent: August 6, 2002Assignee: Appleton Papers Inc.Inventor: Ponnampalam Mathiaparanam
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Publication number: 20020007091Abstract: The present invention is a novel class of compounds useful in useful in thermally-responsive record material of the type comprising a substrate having provided thereon in substantially contiguous relationship an electron donating dye precursor, and an acidic developer material.Type: ApplicationFiled: January 4, 2001Publication date: January 17, 2002Applicant: Appleton Papers Inc.Inventor: Ponnampalam Mathiaparanam
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Publication number: 20010036965Abstract: Mono- and di-iodinated nonoxynol-9-derivatives and methods for their use are disclosed.Type: ApplicationFiled: April 3, 2001Publication date: November 1, 2001Applicant: The Medical College of Hampton Roads, Eastern Virginia Medical SchoolInventors: George Digenis, Philip Fowler, Kazuya Matsumoto, Gustavo Doncel
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Patent number: 6281251Abstract: Mono- and di-iodinated nonoxynol-9-derivatives and methods for their use are disclosed.Type: GrantFiled: March 22, 1999Date of Patent: August 28, 2001Assignees: University of Kentucky Research Foundation, The Medical College of Hampton Roads, Eastern Virginia Medical SchoolInventors: George Digenis, Philip Fowler, Kazuya Matsumoto, Gustavo Doncel
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Patent number: 6171664Abstract: The invention relates to tolan derivatives of the formula I in which R1, R2, A, Z, L1, L2, L3, L4, L5, L6, Q, m and n are as defined herein.Type: GrantFiled: June 17, 1999Date of Patent: January 9, 2001Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Matthias Bremer, Detlef Pauluth, Harald Hirschmann
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Patent number: 5910617Abstract: The process according to the invention consists in preparing chlorides of aliphatic or cycloaliphatic hydrocarbons by reacting the corresponding mono- or polyalcohol with phosgene or thionyl chloride in the presence of at least one catalyst chosen from hexasubstituted guanidinium halides and their hydrohalides, optionally grafted via one of their radicals to a silica-based support.The chlorides are quickly obtained with good yields and contain few by-products such as carbonates or chloroformates.Type: GrantFiled: June 18, 1998Date of Patent: June 8, 1999Assignee: Societe Nationale Des Poudres Et ExploisfsInventors: Loic Lecomte, Serge Metge, Denis Souyri
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Patent number: 5880162Abstract: A pesticidal compound of formula I: ##STR1## in which formula: either R.sup.1 is hydrogen and R.sup.2 represents a cyclopropyl group or R.sup.1 and R.sup.2 each represent an alkyl group, which alkyl groups may be the same or different;Ar.sub.A represents an optionally substituted phenyl or naphthyl group;Ar.sub.B represents a phenoxy, phenyl, benzyl or benzoyl-substituted phenyl group which is optionally further substituted;the configuration of the groups Ar.sub.A --CR.sup.1 R.sup.2 and --CH.sub.2 Ar.sub.B about the double bond being mutually trans.Preferably Ar.sub.A is a substituted phenyl group; more preferably being substituted at the 4-(para) position by halogen, alkoxy or haloalkyl.Further provided is a process for the preparation of a pesticidal compound of formula I in which a compound comprising a moiety ##STR2## and a compound comprising a moiety Ar.sub.B -- are reacted together forming a link --CH.dbd.C(F)CH.sub.2 -- between ##STR3## and Ar.sub.B in the compound of formula I.Type: GrantFiled: October 21, 1996Date of Patent: March 9, 1999Assignee: British Technology Group, Ltd.Inventors: Bhupinder Pall Singh Khambay, Mu-Guang Liu
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Patent number: 5366517Abstract: A fuel additive composition comprising:(a) a poly(oxyalkylene) hydroxyaromatic ether having the formula: ##STR1## or a fuel-soluble salt thereof; where R.sub.1 and R.sub.2 are each independently hydrogen, hydroxy, lower alkyl having 1 to 6 carbon atoms, or lower alkoxy having 1 to 6 carbon atoms; R.sub.3 and R.sub.4 are each independently hydrogen or lower alkyl having 1 to 6 carbon atoms; R.sub.5 is hydrogen, alkyl having 1 to 30 carbon atoms, phenyl, aralkyl or alkaryl having 7 to 36 carbon atoms, or an acyl group of the formula: ##STR2## where R.sub.6 is alkyl having 1 to 30 carbon atoms, phenyl, or aralkyl or alkaryl having 7 to 36 carbon atoms; n is an integer from 5 to 100; and x is an integer from 0 to 10; and(b) a poly(oxyalkylene) amine having at least one basic nitrogen atom and a sufficient number of oxyalkylene units to render the poly(oxyalkylene) amine soluble in hydrocarbons boiling in the gasoline or diesel fuel range.Type: GrantFiled: December 18, 1992Date of Patent: November 22, 1994Assignee: Chevron Research and Technology CompanyInventor: Richard E. Cherpeck
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Patent number: 5210322Abstract: A process for preparing ethers which comprises contacting a carboxylated ether with a metal oxide catalyst under conditions effective to produce the ether.Type: GrantFiled: September 20, 1990Date of Patent: May 11, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Kurt D. Olson
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Patent number: 5198570Abstract: Highly fluorinated aryloxyfluoroether esters, acids and alcohols, which are intermediates in the production of vinyl monomers, are provided. Also provided is a process for making aryloxyfluoroether esters by the base catalyzed addition of hydroxyaromatic compounds to perfluorovinylether esters.Type: GrantFiled: January 31, 1990Date of Patent: March 30, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Andrew E. Feiring
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Patent number: 5104987Abstract: This invention relates to a process for the alkoxylation of an active hydrogen-containing compound comprising contacting the active hydrogen-containing compound with an alkylene carbonate in the presence of a mixed metal oxide catalyst under conditions effective to alkoxylate the active hydrogen-containing compound.Type: GrantFiled: September 20, 1990Date of Patent: April 14, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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Patent number: 5080827Abstract: An optically active compound particularly useful as a component of liquid crystal compositions having a high response rate and a chiral liquid crystal composition containing the same are provided, which optically active compound is expressed by the formula (I) ##STR1## wherein R.sup.1 represents alkyl or alkoxy each of 1-20 C, H, halogen or CN; ##STR2## and ##STR3## each represent a specified six-membered ring; R.sup.2 represents alkyl of 1-20 C; the asterisk designates an asymmetric carbon atom; and m and n each represents 0 or 1.Type: GrantFiled: August 24, 1990Date of Patent: January 14, 1992Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Shinichi Saito, Kouji Ohno, Hiromichi Inoue, Makoto Ushioda
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Patent number: 5068458Abstract: A process for the preparation of a compound of formula (I): ##STR1## in which X and Y are identical and represent halogen, or X is halogen and Y is hydrogen, which comprises halogenating 2-methyl-6-methoxynaphthalene, of formula (II): ##STR2## in the presence of a free radical initiator.Type: GrantFiled: June 28, 1990Date of Patent: November 26, 1991Assignee: Beecham Group p.l.c.Inventors: John R. M. Dales, Sidney E. Callander
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Patent number: 5012011Abstract: This invention relates to fluorinated vinyl ethers having the formula ##STR1## wherein t has a value of from 1 to 22; R' is C.sub.2 to C.sub.20 alkylene, alkoxyalkylene, arylene or aryloxyalkylene which radicals are optionally fluorinated; R" is a divalent radical having from 1 to 100 carbon atoms and is selected from the group of alkylene, arylene, alkarylene, aralkylene which groups are optionally substituted with lower alkyl or the radical ##STR2## wherein R is a polyvalent linear, branched or cyclic hydrocarbon radical having from 2 to 20 carbon atoms, optionally substituted with alkyleneoxy; A is a divalent radical selected from the group of ##STR3## where each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is independently hydrogen or ##STR4## B is lower alkyl; m has a value of from 0 to 4 and n has a value of from 0 to 20. The invention also relates to the manner of synthesizing the present fluorinated vinyl ethers and to their uses as release agents and stain protective coatings.Type: GrantFiled: October 20, 1989Date of Patent: April 30, 1991Assignee: GAF Chemicals CorporationInventors: Kou-Chang Liu, Paul D. Taylor
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Patent number: 4994601Abstract: Herbicidal .alpha.-(5-aryloxy-naphthalen-1-yl-oxy)-propionic acid derivatives of the formula ##STR1## in which R.sup.1 stands for hydrogen, halogen, cyano or trifluoromethyl,R.sup.2 stands for hydrogen or halogen,R.sup.3 stands for halogen, cyano, trifluoromethyl or trifluoromethoxy,R.sup.4 stands for hydrogen or halogen,R.sup.5 stands for hydrogen or halogen andZ stands for halogen, hydroxyl, amino, alkylamino, alkenylamino, alkinylamino, arylamino, aralkylamino, alkoxycarbonylalkylamino, cyanamino, dialkylamino, dialkenylamino, alkylsulphonylamino, arylsulphonylamino, hydroxylamino, alkoxyamino, hydrazino, alkylsulphonylhydrazino, arylsulphonylhydrazino, alkylthio, arylthio, aralkylthio, alkoxycarbonylalkylthio or for the --O--R.sup.6 group, wherein R.sup.6 can be various organic radicals.The starting material naphthol of the formula ##STR2## is also new.Type: GrantFiled: September 22, 1988Date of Patent: February 19, 1991Assignee: Bayer AktiengesellschaftInventors: Michael Haug, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
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Patent number: 4946984Abstract: This invention relates to the use of calcium sulfate as a catalyst in the preparation of alkoxylation products, i.e., condensation reaction products of alkylene oxides and organic compounds having at least one active hydrogen, that have beneficial, narrow molecular weight ranges.Type: GrantFiled: September 30, 1988Date of Patent: August 7, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: Charles F. Hauser
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Patent number: 4918242Abstract: A process for producing the optically pure (+)- or (-)-isomer of a phenyl- or substituted-phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.Type: GrantFiled: June 12, 1989Date of Patent: April 17, 1990Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 4877548Abstract: A liquid crystalline compound and a liquid crystal composition containing the compound usable for liquid crystal display devices are provided, which liquid crystalline compound is expressed by the formulaR.sup.1 --A.sup.1 --B.sup.1 --A.sup.2 --B.sup.2 --A.sup.3.sub.n (CH.sub.2).sub.m CH.dbd.CF.sub.2wherein R.sup.1 is H or 1-20C alkyl or alkenyl wherein one --CH.sub.2 --group or two --CH.sub.2 -- groups not adjacent to each other may be substituted by --O--; the position and number of the double bond may be optionally chosen; A.sup.1, A.sup.2 and A.sup.3 each are ##STR1## and the H of the ##STR2## may be substituted by F, Cl or methyl; B.sup.1 and B.sup.2 each are --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond; n is 0 or 1; and m is 0-20.Type: GrantFiled: December 27, 1988Date of Patent: October 31, 1989Assignee: Chisso CorporationInventors: Kisei Kitano, Makoto Ushioda, Manabu Uchida, Toshiharu Suzuki
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Patent number: 4814524Abstract: Organic haloformate, e.g., chloroformate, compounds are converted to their corresponding halides, e.g., chlorides, by heating the haloformate, e.g., between 90.degree. C. and 150.degree. C., in the presence of a catalytic amount of an organic quaternary salt, e.g., quaternary ammonium or phosphonium salts, for a time sufficient to convert the haloformate to the corresponding halide.Type: GrantFiled: July 31, 1986Date of Patent: March 21, 1989Assignee: PPG Industries, Inc.Inventors: Robert G. Briody, James A. Manner
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Patent number: 4798906Abstract: Alkyl-, aryl- or alkylaryl-alkoxy halides are prepared by reacting the corresponding alcohol, phenol or alkyl phenol with ethylene oxide and/or propylene oxide in the presence of an amine catalyst to form an alkoxy alcohol, and directly reacting the latter with a halogenating agent in the continuing presence of the amine catalyst.Neutralization of the product and/or catalyst removal from the first stage is no longer necessary and reaction rates and yields are increased in the second stage.Type: GrantFiled: July 29, 1987Date of Patent: January 17, 1989Assignee: The British Petroleum Company p.l.c.Inventors: Philip K. G. Hodgson, Nevin J. Stewart
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Patent number: 4757145Abstract: Compounds suitable for being used as lubricants, having general formula:(I) RO--(C.sub.3 F.sub.6 O).sub.m --(CFXO).sub.n --CFX--L,or(II) R"CFXO--(C.sub.3 F.sub.6 O).sub.x (CFXO).sub.y --(C.sub.2 F.sub.4 O).sub.z --CFX--L,whereR=--CF.sub.3, --C.sub.2 F.sub.5, --C.sub.3 F.sub.7X=F, --CF.sub.3R"=F, --CF.sub.3, --C.sub.2 F.sub.5m=an integer from 3 to 100n=a finite integer, or=zero, wherefore m+n ranges from 3 to 100, provided that, if n is finite, m/n ranges from 5 to 20 and R is preferably=CF.sub.3, if n=zero, R is preferably --C.sub.2 F.sub.5 or --C.sub.3 F.sub.7x=a finite integer, or=zeroy, z=finite integers, such that x+y+z ranges from 5 to 200, while (x+z)/y ranges from 5 to 0.5, provided that when x=zero, z/y ranges from 1 to 0.5 and y+z ranges from 5 to 200 n while X is is preferably F, and R"=LL=group Y-Z,where:Y=--CH.sub.2 O--, --CH.sub.2 --OCH.sub.2, --CF.sub.2, --CF.sub.Type: GrantFiled: March 26, 1987Date of Patent: July 12, 1988Assignee: Montedison S.p.A.Inventors: Gerardo Caporiccio, Ezio Strepparola, Mario A. Scarati
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Patent number: 4755503Abstract: Fragrance compositions prepared by adding thereto an olfactorily effective amount of substantially pure 2,4,6-tribromo-3-methylanisole are disclosed.Type: GrantFiled: October 21, 1987Date of Patent: July 5, 1988Assignee: Givaudan CorporationInventors: Joachim E. Freudewald, Kenneth L. Purzycki, Joseph A. Virgilio
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Patent number: 4734535Abstract: Aliphatic chlorine compounds of the formulaX--R.sup.1 --Cl Iwhere R.sup.1 is alkylene which may be interrupted by one or more oxygen atoms and which may be substituted by halogen, alkyl or aryl, and X is hydrogen, chlorine or OR.sup.2, where R.sup.2 is alkyl, cycloalkyl, aryl or aralkyl, are prepared by decarboxylating chloroformic acid esters or diesters at elevated temperatures by decarboxylating in the presence of a quaternary ammonium or phosphonium salt as catalyst.Type: GrantFiled: March 25, 1987Date of Patent: March 29, 1988Assignee: BASF AktiengesellschaftInventors: Norbert Greif, Knut Oppenlaender
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Patent number: 4714785Abstract: Organic haloformate, e.g., chloroformate, compounds are converted to their corresponding halides, e.g., chlorides, by heating the haloformate, e.g., between 90.degree. C. and 150.degree. C., in the presence of a catalytic amount of a carbon catalyst for a time sufficient to convert the haloformate to the corresponding halide.Type: GrantFiled: September 15, 1986Date of Patent: December 22, 1987Assignee: PPG Industries, Inc.Inventor: James A. Manner
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Patent number: 4649160Abstract: Substituted phenoxy-aminopropanols of the formula ##STR1## wherein R is a branched-chain alkyl of 3 or 4 carbon atoms, R.sup.1 is hydrogen, halogen or lower alkyl and R.sup.2 and R.sup.3, independently, are hydrogen, halogen, lower alkyl, lower alkoxy or lower alkylthio, and pharmaceutically acceptable acid addition salts thereof, are described. A process for their preparation, as well as pharmaceutical preparations containing them are also described. The compounds of formula I and their salts possess cardioselective .beta.-adrenergic blocking activity and antihypertensive activity.Type: GrantFiled: September 6, 1985Date of Patent: March 10, 1987Assignee: Hoffmann-La Roche Inc.Inventor: Peter J. Machin
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Patent number: 4622431Abstract: Organic chloroformate compounds are decomposed to their corresponding chlorides by heating the chloroformate, e.g., between 100.degree. and 175.degree. C., in the presence of a catalytic amount of solid poly(vinylpyridine), e.g., poly(4-vinylpyridine), for a time sufficient to convert the chloroformate to the corresponding chloride.Type: GrantFiled: April 4, 1985Date of Patent: November 11, 1986Assignee: PPG Industries, Inc.Inventors: Robert G. Briody, Henry C. Stevens
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Patent number: 4605784Abstract: Disclosed is a process for the preparation of ether-containing chlorides by reacting an ether-alcohol, ether-glycol or ether-polyglycol with a chlorinating agent such as thionyl chloride in the presence of a catalytic amount of a quaternary ammonium salt, the reaction being conducted at a temperature of about 25.degree. C. to about 90.degree. C.Type: GrantFiled: July 18, 1985Date of Patent: August 12, 1986Assignee: Eastman Kodak CompanyInventors: Robert J. I. Eubanks, James G. Pacifici
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Patent number: 4559179Abstract: A fluorine-containing vinyl compound of the formula: ##STR1## wherein Rf is fluoroalkyl of 4 to 20 carbon atoms, R.sub.1 is hydrogen or acyl of 1 to 3 carbon atoms, one of R.sub.2 and R.sub.3 is hydrogen and the other is methyl, R.sub.4 is hydrogen or methyl, A is a divalent organic group, and l, m and n are each an integer of 0 to 40 and satisfy 0<l+m+n.ltoreq.40, which can modify surface properties of resins.Type: GrantFiled: April 5, 1984Date of Patent: December 17, 1985Assignee: Daikan Kogyo Co., Ltd.Inventors: Iwao Hisamoto, Chiaki Maeda, Masaru Hirai
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Patent number: 4460486Abstract: The process and polyoxyalkylene compound prepared by reacting 4,4'-thiodiphenol with at least one alkylene oxide in the presence of a base catalyst.Type: GrantFiled: November 1, 1982Date of Patent: July 17, 1984Assignee: BASF Wyandotte CorporationInventor: David D. Newkirk
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Patent number: 4391994Abstract: Oxyalkylene group of an alkylene oxide is inserted into a chain-type ether compound having at least one lower alkyl group by reacting the latter with the alkylene oxide in the presence of a catalyst prepared by mixing boron trifluoride and/or stannic chloride with an active-hydrogen compound exemplified by water or a lower aliphatic alcohol. The reaction results reduced formation of by-product dimer of the alkylene oxide even under an increased charging ratio of the alkylene oxide to the chain-type ether.Type: GrantFiled: October 19, 1981Date of Patent: July 5, 1983Assignee: Nisso Petrochemical Industrie Co., Ltd.Inventors: Kiyoshi Kogoma, Yu Ohashi, Jiro Niizeki, Norio Sone, Takashi Tobita
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Patent number: 4376868Abstract: Cresylic acid ethoxylation is catalyzed by basic compounds and salts of alkaline earth metals. Ethoxylates from such reactions have narrow ethylene oxide distributions, lower pour points and lower by-products as compared to alkali base catalyzed ethoxylation. Suitable catalysts include strontium-containing and barium-containing materials. The catalyst also includes co-catalyst combinations using these materials with one or more promoters including polyols, amines, amides, carboxylic acids and phenols. The co-catalyst combinations can be preformed prior to introduction into the reaction mixture.Type: GrantFiled: February 14, 1980Date of Patent: March 15, 1983Assignee: Conoco Inc.Inventors: Gerald L. Nield, Kang Yang, Paul H. Washecheck
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Patent number: 4251385Abstract: A polyol composition consisting essentially of a homogeneous liquid or low melting solid admixture of propylene glycol and a diol obtained by alkoxylating a propylene glycol dispersion of 3,3',5,5' tetrabromobisphenol A with ethylene oxide, propylene oxide or mixtures thereof. These polyol compositions are useful in preparing fire and chemical resistant thermosetting resinous compositions.Type: GrantFiled: September 11, 1978Date of Patent: February 17, 1981Assignee: Sherex Chemical Company, Inc.Inventors: Jack W. Sigan, James G. Fuller
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Patent number: 4249024Abstract: The present invention discloses an improved method for the in situ end point determination of the oxyethylation of phenols. In the present invention, the oxyethylation reactions occur in the presence of catalysts and at temperatures in excess of 100.degree. C. The reaction end point is monitored by continuous measurements of the electrical conductivity of the reaction mixture and the reaction is terminated when a preselected rate of change of conductance is attained.The method of the present invention may be used with complex phenolic systems wherein alkali metal hydroxides, quarternary ammonium salts, or alkali metal alkoxides are used as oxyethylation catalysts.Type: GrantFiled: August 22, 1979Date of Patent: February 3, 1981Assignee: Great Lakes Chemical Corp.Inventor: David C. Sanders
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Patent number: 4182727Abstract: Sulfo- and aminosulfonyl-substituted aryloxyalkyl diketones, useful as anti-viral agents, are prepared, respectively, by reacting a phenoxyalkyl diketone with sulfuric acid; or by reacting a haloalkyl diketone with an alkali metal salt of a hydroxybenzenesulfonamide.Type: GrantFiled: June 7, 1978Date of Patent: January 8, 1980Assignee: Sterling Drug Inc.Inventors: Joseph C. Collins, Guy D. Diana
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Patent number: 4170711Abstract: Monomeric and polymeric halogenated organic compounds derived from 2,2',6,6'-tetrabromo-3,3',5,5' -tetraalkyl-4,4'-biphenols are described. The derivatives are useful in their monomeric and polymeric form as flame retardant additives and/or concentrates for normally flammable resinous materials. The thermal stability at elevated temperatures of the brominated biphenol derivatives advantageously benefits polymeric compositions containing the brominated biphenol derivatives especially when the polymeric compositions are molded into three dimensional articles, or formed into films, sheeting or shaped into fibers, laminates or reinforced plastics by conventional techniques.Type: GrantFiled: September 27, 1976Date of Patent: October 9, 1979Assignee: General Electric CompanyInventors: Charles M. Orlando, Francois A. Lavallee
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Patent number: 4169151Abstract: A new class of alkyl-aryl diethers having juvenile hormone activity (hereinafter designated JHA) and capable of retarding the metamorphosis of pupae or larvae into adult insects is disclosed. The new alkyl-aryl diethers are characterized in that one of the end groups is a phenyl group and the other end group is a halogenated group.Type: GrantFiled: January 30, 1978Date of Patent: September 25, 1979Assignee: Montedison S.p.A.Inventors: Pietro Massardo, Angelo Longoni, Paolo Piccardi
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Patent number: 4149987Abstract: An oxyalkylated, halogenated product useful in making polyurethane foams is prepared by reacting an epoxide compound with a halogenated aromatic hydroxyl-containing compound (phenol) which is either a monohydroxy or polyhydroxy compound. Said aromatic hydroxyl compound has a hydroxy group attached directly to the aromatic nucleus. By the process of the invention, hydroxyalkylation occurs in the presence of a catalyst selectively active in the predominant oxyalkylation of aromatic hydroxyl groups, said catalyst selected from the group consisting of zinc, magnesium and a zinc or magnesium salt as defined. The reaction mixture can include an aliphatic hydroxyl-containing compound, a neutral phosphorus compound, and aliphatic or aromatic anhydrides or mixtures thereof to enhance the flame-retardant properties of the oxyalkylated product.Type: GrantFiled: March 1, 1978Date of Patent: April 17, 1979Assignee: BASF Wyandotte CorporationInventors: Arthur L. Austin, William W. Levis, Jr.
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Patent number: 4146736Abstract: Oxalkylene groups of oxacycloalkanes are inserted into chain-type ethers by reacting the latter with the oxacycloalkanes in the presence of Lewis acids. The ethers or ether mixtures obtained can be used for many purposes owing to their hydrophilic-hydrophobic character, for example as absorption and extraction agents, as solvents and as additives to hydraulic fluids.Type: GrantFiled: August 26, 1977Date of Patent: March 27, 1979Assignee: Hoechst AktiengesellschaftInventors: Gunter Scheffel, Reinhold Obermeier