Benzene Ring Containing Patents (Class 568/17)
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Patent number: 5723678Abstract: Acetylenic compounds of the general formula IR.sup.1 --C.tbd.C--CHR.sup.2 --CH.sub.2 --X Iwhere the substituents have the following meanings:R.sup.1 hydrogen, unsubstituted or substituted alkyl or aryl;R.sup.2 hydrogen or C.sub.1 -C.sub.4 -alkyl;X CN; COOR.sup.3 where R.sup.3 is C.sub.1 -C.sub.6 -alkyl or benzyl; C(O)R.sup.4 where R.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl,are prepared by reacting an alkyne of the formula IIR.sup.1 --C.tbd.C--H IIwith an .alpha.,.beta.-unsaturated compound of the formula IIIR.sup.2 HC.dbd.CH--X IIIin the presence of a homogeneous rhodium-phosphine catalyst, in a process wherein a catalyst with a bidentate or tridentate phosphine compound is used.Type: GrantFiled: April 12, 1996Date of Patent: March 3, 1998Assignee: BASF AktiengesellschaftInventors: Thomas Ruhl, Jochem Henkelmann, Marc Heider, Peter Hofmann
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Patent number: 5723642Abstract: Optically active phosphines of the general formula I or II ##STR1## where the variables have the following meanings: X is an optically active terpene radical,R is an unsubstituted or substituted phenyl radical,Y is a bridge member having 1-10 C atoms in the formula In is 1,2 or 3 andm is 0,1 or 2 with the proviso that n+m=3 in the formula IIn is 1 or 2 andm is 0 or 1 with the proviso that n+m=2, their preparation and use are described.Type: GrantFiled: May 6, 1996Date of Patent: March 3, 1998Assignee: BASF AktiengesellschaftInventors: Rainer Sturmer, Lothar Laupichler, Paul Knochel, Falk Langer
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Patent number: 5721292Abstract: Compounds of formula (I), in which X is oxygen or sulfur, R.sub.1, R.sub.2 and R.sub.3 independently of one another are a group (a), C.sub.2 -C.sub.8 alkenyl, phenyl which is unsubstituted or is substituted from one to four times with C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.6 alkylthio and/or halogen, or are naphthyl which is unsubstituted or is substituted from one to four times with C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.6 alkylthio and/or halogen, or are biphenyl which is unsubstituted or is substituted from one to four times with C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.6 -alkylthio and/or halogen, or R.sub.1, R.sub.2 and R.sub.3 independently of one another are an O-, S- or N-containing 5- or 6-membered heterocyclic ring, R.sub.1 is in addition a group of formula (II), or R.sub.1 and R.sub.2 are linked to form a ring containing 4 to 10 carbon atoms which is unsubstituted or substituted by 1 to 6 C.sub.1 -C.sub.Type: GrantFiled: March 5, 1997Date of Patent: February 24, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: David George Leppard, Manfred Kohler, Gebhard Hug
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Patent number: 5712403Abstract: A method for producing an unsaturated alcohol having a chain structure formed by oligomerization of a conjugated alkadiene, which comprises reacting a conjugated alkadiene and water in the presence of carbon dioxide by means of a palladium compound and a phosphorus compound having at least one trivalent phosphorus-oxygen single bond, as catalyst.Type: GrantFiled: October 8, 1996Date of Patent: January 27, 1998Assignee: Mitsubishi Chemical CorporationInventors: Keiichi Sato, Yoko Seto, Iwao Nakajima
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Patent number: 5710338Abstract: Hydroformylation of alkenes to aldehydes in the presence of a rhodium complex catalyst is improved by the addition of a novel bidentate ligand of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.1 ' and R.sub.2 ' are organic radicals selected from alicyclic, aliphatic and aromatic groups of which at least one is preferably substituted with at least one electronegative moiety and the methylene groups are present at the trans-2,3 positions on the norbornane moiety. The invention also provides a novel method for producing the bidentate ligand and novel intermediate phosphine oxide and phosphinous acid compounds.Type: GrantFiled: April 10, 1996Date of Patent: January 20, 1998Assignee: Hoechst Celanese CorporationInventors: Jerry D. Unruh, Brigitte E. Segmuller, Gabriel R. Chapa, Kent E. Pryor
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Patent number: 5710339Abstract: The invention relates to enantiomerically pure bisphosphines of the general formula (I) ##STR1## where R is as defined in the description,a process for their preparation and their use in metal complexes as catalysts for asymmetric reactions, in particular asymmetric hydrogenations.Type: GrantFiled: June 13, 1996Date of Patent: January 20, 1998Assignee: Bayer AktiengesellschaftInventors: Christian Laue, Georg Schroder, Dieter Arlt
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Patent number: 5710340Abstract: Phosphines having two aryl groups and one alkyl-substituted cycloalkyl group bonded to a phosphorus atom are formed by reacting an alkali metal diarylphosphide with a monoalkyl- or polyalkyl-substituted cycloalkyl mesylate or tosylate in which an alkyl group is in the 2-position, in a liquid reaction medium in which these reactants are soluble. This process avoids complications associated with prior known process technology for producing such phosphines. The phosphines are useful as ligands for making noble metal catalysts.Type: GrantFiled: April 29, 1996Date of Patent: January 20, 1998Assignee: Albemarle CorporationInventor: K. Pushpananda A. Senaratne
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Patent number: 5710337Abstract: Hydroformylation of alkenes to aldehydes in the presence of a rhodium complex catalyst is improved by the addition of a novel bidentate ligand of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.1 ' and R.sub.2 ' are organic radicals selected from alicyclic, aliphatic and aromatic groups of which at least one is preferably substituted with at least one electronegative moiety and the methylene groups are present at the trans-2,3 positions on the norbornane moiety. The invention also provides a novel method for producing the bidentate ligand and novel intermediate phosphine oxide and phosphinous acid compounds.Type: GrantFiled: April 10, 1996Date of Patent: January 20, 1998Assignee: Hoechst Celanese CorporationInventors: Jerry D. Unruh, Brigitte E. Segmuller, Gabriel R. Chapa, Kent E. Pryor
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Patent number: 5698743Abstract: Preparation of methylene-bridged compounds of the formula I ##STR1## where R.sup.1 to R.sup.4 are identical or different and are each saturated C.sub.1 -C.sub.30 -hydrocarbyl, unsubstituted phenyl, phenyl substituted by substituents inert under the reaction conditions, or hydrogen, E.sup.1 and E.sup.2 are identical or different and are each phosphorus, arsenic or antimony, and X is a chemical bond or oxygen by reacting a tin compound of the general formula IIR.sub.3.sup.5 Sn--CH.sub.2 M, IIwhere R.sup.5 is C.sub.1 --C.sub.20 -hydrocarbyl and M is an alkali metal, with a compound of the general formula III ##STR2## where Y is halogen, metallating the thus-obtained tin compound of the general formula IV ##STR3## with an alkali organometallic, and reacting the product with a compound of the general formula V ##STR4## to give a methylene-bridged compound of the formula I. And novel bis(diorganophosphino)methanes.Type: GrantFiled: November 26, 1996Date of Patent: December 16, 1997Assignee: BASF AktiengesellschaftInventors: Arthur Hohn, Justin Wolf
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Patent number: 5696296Abstract: A diphosphine of the formula (I) ##STR1## in which Ar--Ar is a biphenyl radical, a 1-phenyl-naphthyl radical or a 1,1'-binaphthyl radical, the CH.sub.2 groups am each located in the ortho-position relative to the Ar--Ar bond, R is F or an alkyl radical or alkoxy radical having in each case 1 to 8 carbon atoms, n is an integer from 0 to 4, the radicals PR.sup.1 R.sup.2 and PR.sup.3 R.sup.4 differ from one another, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another are each an alkyl radical having 1 to 10 carbon atoms, a cycloaliphatic radical having 5 to 10 carbon atoms, or a radical Ar.sup.1 --(R.sup.5).sub.m, in which AR.sup.1 is a phenyl radical, R.sup.5 is F, CF.sub.3, or an alkyl radical having 1 to 4 carbon atoms and m is 0 to 1, or R.sup.1, R.sup.2, R.sup.3 and R.sup.Type: GrantFiled: September 27, 1995Date of Patent: December 9, 1997Assignee: Hoechst AktiengesellschaftInventors: Christoph Naumann, Dieter Regnat
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Patent number: 5693868Abstract: The present invention provides a method for producing novel optically active diphosphine compounds ?2,2'-bis(di-substituted phosphino)-1,1'-binaphthyl compounds! having a selectivity (chemoselectivity or enantioselectivity) and catalytic activity different from those of conventional BINAP compounds. In a method of the present invention for producing an optically active diphosphine compound (i.e., 2,2-bis(di-substituted phosphino)-1,1'-binaphthyl), 2,2'-bis(trifluoromethanesulfonyloxy)-1,1'-binaphthyl is reacted, in the presence of a transition metal-phosphine complex, with a phosphineoxide compound represented by the following general formula:A.sub.Type: GrantFiled: October 30, 1996Date of Patent: December 2, 1997Assignee: Takasago International CorporationInventors: Noboru Sayo, Xiaoyong Zhang, Tatsuya Ohmoto, Akifumi Yoshida, Tohru Yokozawa
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Patent number: 5693627Abstract: A method of inhibiting the proliferation of B cells by using inhibitors of phosphotyrosine phosphatase can be used to regulate the immune response and to treat diseases such as leukemias or lymphomas marked by malignant proliferation of B cells. The use of such inhibitors can be combined with radiation, which produces a synergistic effect. Several types of inhibitors can be used, including: (1) compounds comprising a metal coordinate-covalently bound to an organic moiety that can form a five- or six-membered ring; (2) compounds in which vanadium (IV) is coordinate-covalently bound to an organic moiety such as a hydroxamate, .alpha.-hydroxypyridinone, .alpha.-hydroxypyrone, .alpha.-amino acid, hydroxycarbonyl, or thiohydroxamate; (3) coordinate-covalent complexes of vanadyl and cysteine or a derivative thereof; (4) nonhydrolyzable phosphotyrosine phosphatase analogues; (5) phostatin; and (6) 4-(fluoromethyl)phenyl phosphate and esterified derivatives.Type: GrantFiled: May 25, 1995Date of Patent: December 2, 1997Assignee: Bristol-Myers Squibb CompanyInventor: Gary L. Schieven
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Patent number: 5693807Abstract: The invention relates to substituted hydroquinone derivatives of the general formula I ##STR1## wherein R.sub.4 is lower alkyl and either R.sub.1 is hydroxy, halogen, a group of the formula --P(=O)(R.sub.5)R.sub.6 (Ia), a group of the formula --P.sup.+ (R.sub.7)(R.sub.8)R.sub.9 X.sup.- (Ib) or a group of the formula --Si(R.sub.7)(R.sub.8)R.sub.9 (Ic), M is methylene, R.sub.2 is hydrogen or a group of the formula ##STR2## and R.sub.3 is hydrogen or halogen, or .sub.1 is hydroxy or lower alkoxy, M is carbonyl, R.sub.2 is hydrogen and R.sub.3 is halogen, each of R.sub.5 and R.sub.6, independently of the other, is lower alkyl, lower alkoxy Or N,N-di-lower alkylamino, or is benzyl, benzyloxy, phenyl or phenoxy, each of which is unsubstituted or mono- or di-substituted at the phenyl ring, to a process for the preparation of those compounds and to the use of those compounds, and to a process in which those compounds are used.Type: GrantFiled: June 5, 1995Date of Patent: December 2, 1997Assignee: Ciba-Geigy CorporationInventors: Gottfried Sedelmeier, Gerhard Fischer
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Patent number: 5689005Abstract: A process for the deoxygenation of organic oxo compounds, in particular phosphine oxides to phosphines and nitrobenzene to aniline, with reduced redox catalysts in a non-steady-state reaction with decoupled reductive regeneration of the redox catalyst entails the redox catalyst being reduced to a lower oxidation state and being reused for the deoxygenation.Type: GrantFiled: November 28, 1995Date of Patent: November 18, 1997Assignee: BASF AktiengesellschaftInventors: Alfred Hagemeyer, Christopher William Rieker, Thomas Lautensack, Dieter Hermeling
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Patent number: 5679863Abstract: The preparation of .alpha.-carbonylphosphine oxides by oxidizing an .alpha.-hydroxyalkyl phosphine oxide with an organic hydroperoxide or of an organic peroxy acid in the presence of a compound of a Group IV to Group VIII metal in the periodic table, and novel .alpha.-hydroxybenzyl phosphine oxides. .alpha.-Carbonylphosphine oxides are used as photoinitiators for polymerizable compositions.Type: GrantFiled: October 16, 1995Date of Patent: October 21, 1997Assignee: BASF AktiengesellschaftInventors: Martin Fischer, Eckhard Hickmann, Rudolf Kropp, Jochen Schroeder, Beate Trentmann
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Patent number: 5654485Abstract: By reacting certain partially sterically-hindered chloro-substituted cycloalkanes with sodium and/or potassium diarylphosphides in an ether reaction medium, not only are useful cycloalkyldiarylphosphines produced, but in addition the chloro-substituted cycloalkane does not undergo any appreciable reaction with the coproduced aryl sodium and/or aryl potassium as it is formed. Moreover, the process makes it possible to avoid or at least to greatly reduce interaction with or cleavage of cyclic ether reaction media such as tetrahydrofuran. Thus the process makes possible improvements both in yield and quality of the cycloalkyldiarylphosphite product. A two-stage process conducted in an ether reaction medium is also described. In the first stage the sodium and/or potassium diarylphosphine reactant is produced by reaction between sodium and/or potassium and triarylphosphine.Type: GrantFiled: March 25, 1996Date of Patent: August 5, 1997Assignee: Albemarle CorporationInventors: K. Pushpananda A. Senaratne, Arcelio J. Malcolm, Felix M. Orihuela, Hassan Y. Elnagar
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Patent number: 5654486Abstract: Partially sterically-hindered cycloalkyl chlorides are reacted with lithium diarylphosphides in inert liquid hydrocarbon reaction media to form cycloalkyldiarylphosphines. Aryl lithium is coproduced. The process makes it possible to avoid, or at least substantially eliminate, the interaction with or cleavage of cyclic ether reaction media such as tetrahydrofuran, previously the solvent of choice for conducting this type of reaction. Also during the conduct of the present process the chloro-substituted cycloalkane does not undergo any appreciable reaction with the coproduced aryl lithium as it is formed. Thus improvements both in yield and quality of the cycloalkyldiarylphosphine product are made possible. A comprehensive three-step process for converting triarylphosphine to cycloalkyldiarylphosphine is also described.Type: GrantFiled: March 25, 1996Date of Patent: August 5, 1997Assignee: Albemarle CorporationInventors: K. Pushpananda A. Senaratne, Arcelio J. Malcolm, Felix M. Orihuela, Hassan Y. Elnagar
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Patent number: 5650099Abstract: A dicationic surfactant for enhancing the chemiluminescence of chemiluminescent compounds particularly dioxetanes which are triggerable is described. The surfactant has the formulaX.sup.- (R.sub.1).sub.3 A.sup.+ CH.sub.2 -Link-CH.sub.2 A.sup.+ (R.sub.2).sub.3 X.sup.-wherein A is selected from the group consisting of phosphorus and nitrogen atoms separately or together, wherein X is an anionic counterion and R.sub.1 and R.sub.2 are selected from the group consisting of unsubstituted and substituted alkyl and aralkyl groups containing 1 to 20 carbon atoms and R.sub.1 and R.sub.2 can be the same or different, and wherein Link is a carbon chain group selected from the group consisting of dialkylenearyl, aryl, alkylene, alkenylene and alkynylene groups containing 4 to 20 carbon atoms. The surfactants are particularly useful in Western and Southern blot assays.Type: GrantFiled: May 16, 1995Date of Patent: July 22, 1997Assignee: Lumigen, Inc.Inventors: M. Hashem Akhavan-Tafti, Zahra Arghavani
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Patent number: 5648548Abstract: An optically active 2-diphenylphosphinomethyl-2'-diphenylphosphinyl-1,1'-binaphthalene derivative represented by the following general formula (I) ##STR1## wherein R represents a phenyl group, a tolyl group, an anisyl group or a chlorophenyl group, and a process for the production of optically active substances in which the above compound and a transition metal compound are used. The asymmetric diphosphine of the present invention is related to the creation of novel compounds, which is excellent as a ligand for asymmetric synthesis use. When the above compound is used together with a transition metal compound such as of ruthenium, rhodium or the like, it shows markedly excellent properties as the catalyst of asymmetric hydrogenation and the like reactions, in terms of selectivity, conversion ratio, catalytic activity and the like.Type: GrantFiled: March 13, 1996Date of Patent: July 15, 1997Assignee: Takasago International CorporationInventors: Hidemasa Takaya, deceased, Tetsuo Ota, Koji Inagaki
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Patent number: 5648549Abstract: The invention relates to a process for the preparation of secondary phosphines of the formula (I) ##STR1## in which R.sup.1 to R.sup.6 independently of one another are hydrogen, halogen, (C.sub.1 -C.sub.6)-alkyl or (C.sub.1 -C.sub.6)-alkoxy, wherein secondary phosphine oxides of the formula (II) ##STR2## are reacted with Lewis acids as catalysts, at elevated temperature, and the secondary phosphines of the formula (I) formed are distilled off under reduced pressure.Type: GrantFiled: July 15, 1996Date of Patent: July 15, 1997Assignee: Hoechst AktiengesellschaftInventor: Hans-Jerg Kleiner
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Patent number: 5635158Abstract: The peptides described are modified with the phosphine group and are useful for marking with .sup.99m Tc and .sup.186-188 Re or paramagnetic agents for use in diagnosis and radiotherapy; in particular chelating compounds having the co-ordinating sets PN.sub.2 X, where X is --S, --O, COO--, PN.sub.3, P.sub.2 N.sub.3 and P.sub.2 N.sub.2 are described.Type: GrantFiled: June 23, 1995Date of Patent: June 3, 1997Assignee: Sorin Radiofarmaci SRLInventors: Ulderico Mazzi, Fabio Lunghi
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Patent number: 5627174Abstract: Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acarids that prey on agricultural crops, these compounds having the general structure: ##STR1## These Polar compounds are particularly useful for systemic control of pests.Type: GrantFiled: May 23, 1995Date of Patent: May 6, 1997Assignee: Monsanto CompanyInventors: Dennis P. Phillion, Peter G. Ruminski, Gopichand Yalamanchili
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Patent number: 5621128Abstract: Compounds of the formula I ##STR1## in which the phenyl rings of the biphenyl molecule can be substituted with up to 8 fluorine and/or chlorine atoms are suitable as catalysts.Type: GrantFiled: June 28, 1995Date of Patent: April 15, 1997Assignee: Hoechst AktiengesellschaftInventor: Joachim-Heiner Jendralla
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Patent number: 5621129Abstract: A tertiary phosphine compound of the formula (1): ##STR1## in which R.sup.1 and R.sup.1' are hydrogen atoms or together form --CH.dbd.CH--CH.dbd.CH--; R.sup.2 and R.sup.3 together form a group of the formula (a): ##STR2## in which --.circle-solid. represent a bond to be bonded to the R.sup.3 group, and --.smallcircle. represents a bond to be bonded to the R.sup.2 group when R.sup.1 and R.sup.1 ' together form --CH.dbd.CH--CH.dbd.CH--, or when R.sup.1 is a hydrogen atom, R.sup.2 and R.sup.3 together form --CH.dbd.CH--CH.dbd.CH-- or R.sup.2 is a hydrogen atom and R.sup.3 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group; A.sup.1 is a 3-trifluoromethylphenyl group or a 3,5-bis(trifluoromethyl)phenyl group when R.sup.1 is a hydrogen atom and R.sup.2 and R.sup.3 together form --CH.dbd.CH--CH.dbd.CH--, or a substituted or unsubstituted phenyl group when R.sup.1 is not a hydrogen atom or when R.sup.2 and R.sup.3 do not together form --CH.dbd.CH--CH.dbd.CH--.Type: GrantFiled: March 7, 1996Date of Patent: April 15, 1997Assignee: Sumitomo Chemical Co., Ltd.Inventors: Tamio Hayashi, Masayoshi Minai, Kazunori Iwakura
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Patent number: 5600006Abstract: The invention relates to novel 2,2'-bis [bis(aryl)phosphinomethyl]-1,1'-binaphthyls of the formula ##STR1## in which Ar.sup.2 is a phenyl radical, R' is an alkyl radical having 1 to 4 carbon atoms, CF.sub.3, fluorine, chlorine or bromine, and n is 1 or 2.Type: GrantFiled: November 10, 1994Date of Patent: February 4, 1997Assignee: Hoechst A.G.Inventors: Dieter Regnat, Hans-Jerg Kleiner
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Patent number: 5580991Abstract: The disclosure describes a method for separating a ruthenium complex, which comprises removing an objective hydrogenation reaction product from a hydrogenation reaction solution of an organic carbonyl compound in the presence of a ruthenium complex having a tertiary organic phosphorus compound as ligand to obtain a catalyst solution, contacting said catalyst solution with a polar solvent, and carrying out a phase-separation into a liquid phase substantially composed of the polar solvent and an another liquid phase substantially containing the ruthenium complex.Type: GrantFiled: April 4, 1995Date of Patent: December 3, 1996Assignee: Mitsubishi Chemical CorporationInventors: Hitoshi Sugiyama, Kazunari Takahashi, Haruhiko Kusaka
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Patent number: 5569800Abstract: An electrophotographic photoconductor which is composed of an electroconductive support and a photoconductive layer formed thereon comprising a novel pyrene-ring-containing olefin compound having formula [I]: ##STR1## wherein R.sup.1 and R.sup.2 each represent hydrogen or an alkyl group which may have a substituent; Y is an aliphatic hydrocarbon group which may have a substituent, a cyclic hydrocarbon group which may have a substituent, or an aromatic group which may have a substituent; n is an integer of 0 or 1, and m is an integer of 1 to 3, provided that when n is 0, m is 1, R.sup.1 is hydrogen, and Y is an aromatic group with a substituent ##STR2## R.sup.2 and R.sup.3 each represent hydrogen, and Y and R.sup.1 may be bonded to form a ring, a method of synthesizing the pyrene-ring-containing olefin compound and an intermediate therefor are disclosed.Type: GrantFiled: May 2, 1995Date of Patent: October 29, 1996Assignee: Ricoh Company, Ltd.Inventors: Tamotsu Aruga, Masaomi Sasaki, Tomoyuki Shimada, Hiroshi Adachi
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Patent number: 5556998Abstract: The present invention provides a novel transition metal complex which catalyzes asymmetric hydrogenation reaction. The present invention also provides a process for the preparation of the foregoing novel complex. The present invention further provides an asymmetric hydrogenation catalyst comprising the foregoing novel complex.Type: GrantFiled: March 13, 1995Date of Patent: September 17, 1996Assignee: Takasago International CorporationInventors: Akira Miyashita, Takeshi Chiba, Hiroyuki Nohira, Hidemasa Takaya
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Patent number: 5554795Abstract: In accordance with the present invention there is provided a cyclopentadienyl-type ligand represented by the formula ZA, wherein Z is a cyclopentadienyl-type group, wherein A is --YPR.sub.2, --YNR.sub.2, or --NR.sub.2, wherein Y is an alkylene group containing 1 to 24 carbon atoms, wherein each R is individually selected from alkyl groups containing 1 to 20 carbon atoms. Another aspect of the invention is to provide a metallocene represented by the formula ZAMX.sub.3, wherein Z and A are as described above, M is a Group IVB or VB transition metal, and X is a halide. Other aspects of the present invention include catalyst systems comprising the metallocenes and an organoaluminoxane, processes for preparing the above defined ligands, metallocenes and catalyst systems, and polymerization processes employing the catalyst systems.Type: GrantFiled: May 19, 1995Date of Patent: September 10, 1996Assignee: Phillips Petroleum CompanyInventors: Krisztina Frey, Gabriele von Massow, Helmut G. Alt, M. Bruce Welch
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Patent number: 5550295Abstract: Arylalkyl phosphines, phosphine oxides or phosphine sulfides are prepared by reacting an alkyl phosphine, phosphine oxide or phosphine sulfide with an arylhalide in the presence of a zero valence palladium catalyst.Type: GrantFiled: May 3, 1995Date of Patent: August 27, 1996Assignee: Cytec Technology Corp.Inventor: John H. Hillhouse
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Patent number: 5530150Abstract: A phosphine compound represented by one of the formulas: ##STR1## wherein R.sup.1 and R.sup.2, which may be the same or different, each represent a phenyl group or a phenyl group substituted with a halogen atom or a lower alkyl group or taken together form a divalent hydrocarbon group; and R.sup.3 and R.sup.4, which may be the same or different, each represent a lower alkyl group, a phenyl group or a phenyl group substituted with a halogen atom, a lower alkyl group or a lower alkoxy group or taken together form a divalent hydrocarbon group, and wherein R.sup.6 and R.sup.6' which may be the same or different, each represent a hydrogen atom, a lower alkyl group or a lower alkoxy group; R.sup.5, R.sup.5', R.sup.11 and R.sup.11' which may be the same or different, each represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom; or a pair of R.sup.5 and R.sup.6 or a pair of R.sup.5' and R.sup.6' may form a ring; R.sup.7 and R.sup.Type: GrantFiled: October 12, 1994Date of Patent: June 25, 1996Assignee: Takasago International CorporationInventors: Hidemasa Takaya, Nozomu Sakai, Kyoko Tamao, Satoshi Mano, Hidenori Kumobayashi, Tetsuo Tomita, Takao Saito, Kazuhiko Matsumura, Yasushi Kato, Noboru Sayo
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Patent number: 5527966Abstract: Triphenylphosphine (TPP) is prepared by reacting triphenylphosphine dichloride (TPPCl.sub.2) with magnesium, aluminum and/or iron in the presence of an inert solvent, employing a TPPCl.sub.2 solution whose content of phosgene, chlorine, diphosgene, hydrogen chloride, thionyl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus oxychloride and/or aliphatic halogen compounds (active chlorine compounds) totals less than 1000 ppm Cl.Type: GrantFiled: August 3, 1994Date of Patent: June 18, 1996Assignee: BASF AktiengesellschaftInventors: Dieter Hermeling, Peter Bassler, Peter Hammes, Randolf Hugo, Peter Lechtken, Hardo Siegel
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Patent number: 5527967Abstract: The invention relates to a process for preparing phosphines ##STR1## where, for example R.sup.1 is (C.sub.1 -C.sub.10)alkyl, (C.sub.3 -C.sub.10)cycloalkyl, C(YZ)aryl Y, Z is (C.sub.1 -C.sub.4)alkyl, hydrogen, Aryl is phenyl, naphthyl, anthracenyl, phenanthrenyl, or biphenyl, binaphthylandR.sup.2, R.sup.3 are, independently of one another, phenyl, naphthyl or anthracenyl,by reacting a diarylphosphine ##STR2## where X is bromine, chlorine, fluorine, (C.sub.1 -C.sub.4)alkoxy, O-phenyl, with a reducing agent and a quaternary ammonium compound ##STR3## where A is an anion of an organic or inorganic acid.Type: GrantFiled: May 24, 1995Date of Patent: June 18, 1996Assignee: Hoechst AktiengesellschaftInventor: Hans Millauer
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Patent number: 5525580Abstract: Compounds represented by general formula (I), herbicides or selective herbicides for paddy field containing said compounds as active ingredients, method of controlling growth of undesirable plants by applying the herbicides on places where control is desired. ##STR1## wherein A represents a --S(O)nR.sup.1 in which n is 0 or 2 and R.sup.1 represents a (substituted) lower alkyl; a cycloalkyl; a (substituted) benzyl; a (substituted) phenyl; or a --OR.sup.2 in which R.sup.2 represents a (substituted) phenyl;B represents a halogen, a nitro, a lower alkyl, or a lower alkylsulfonyl;D represents a hydrogen, a lower alkyl, a lower alkoxy, a lower alkoxymethyl, or a lower alkoxycarbonyl;E represents a halogen, a (substituted) lower alkoxy, a lower alkylthio, a (substituted) lower alkylsulfonyl, or a lower alkylsulfonyloxy.The herbicides of the present invention can prevent a wide variety of noxious weeds and further selectively prevent weeds on paddy field with considerably reduced phytotoxicities on rice plant.Type: GrantFiled: January 14, 1994Date of Patent: June 11, 1996Assignee: SDS Biotech K.K.Inventors: Kenichi Komatsubara, Tadashi Sato, Kenji Mikami, Yuji Yamada
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Patent number: 5523437Abstract: A tertiary phosphine compound of the formula (1): ##STR1## wherein R.sup.1 and R.sup.2 represent independently from each other a hydrogen atom or a methyl group, or together form --CH.dbd.CH--CH.dbd.CH--; R.sup.3 is a hydrogen atom or a cycloalkyl group having 5 to 7 carbon atoms or a lower alkyl group which may be substituted with a halogen atom, a lower alkoxy group, a lower alkoxyalkoxy group or a phenyl group; X.sup.1 is a halogen atom when both R.sup.1 and R.sup.2 are hydrogen atoms, or a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group when at least one of R.sup.1 and R.sup.2 is not a hydrogen atoms; and m is an integer of 1 to 5, which is useful as a ligand of a transition metal complex that can catalyze various reactions.Type: GrantFiled: July 26, 1994Date of Patent: June 4, 1996Assignee: Sumitomo Chemical Co., Ltd.Inventors: Tamio Hayashi, Yasuhiro Uozumi, Kazunori Iwakura, Isao Kurimoto, Masayoshi Minai
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Patent number: 5516944Abstract: The present invention is concerned with novel optically active phosphorus compounds of the general formula ##STR1## wherein R and R.sup.1 each independently signify hydroxy, a protected hydroxy group, lower alkyl or lower alkoxy andR.sup.2 to R.sup.5 each independently signify alkyl with 3 to 7 carbon atoms, cycloalkyl or aryl or R.sup.2 and R.sup.3 or R.sup.4 and R.sup.5 together with the phosphorus form a group of the formula ##STR2## wherein R2 and R3 are different when R4 and R5 are the same, and R4 and R5 are different when R2 and R3 are the same,the manufacture of such compounds, their use for enantioselective reactions, such as, e.g., asymmetric hydrogenations, enantioselective hydrogen displacements in prochiral allylic systems and the like, as well as complexes of the compounds of formula I with Group VIII metals.Type: GrantFiled: September 30, 1994Date of Patent: May 14, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Marco Cereghetti, Alain Rageot
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Patent number: 5510503Abstract: The invention relates to novel enantiomerically pure bisphosphines of the general formula (I) ##STR1## in which R, R.sup.1 and R.sup.2 have the meanings given in the description, a process for the preparation thereof and the use thereof in metal complexes as catalysts for asymmetric hydrogenations.Type: GrantFiled: September 2, 1994Date of Patent: April 23, 1996Assignee: Bayer AktiengesellschaftInventors: Christian Laue, Georg Schroder, Dieter Arlt, Rolf Grosser
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Patent number: 5508438Abstract: Novel, racemic and optically active phosphorus compounds of the formula ##STR1## wherein R signifies lower alkyl, lower alkoxy, hydroxy or a protected hydroxy group, R.sup.1 and R.sup.2 are different from each other and represent lower alkyl, cycloalkyl, aryl, a five-membered heteroaromatic or a group of the formula ##STR2## are described. The compounds of formula I are useful in the form of complexes with a metal of Group VIII as catalysts for asymmetric hydrogenations and for enantioselective hydrogen displacements in prochiral allylic systems.Type: GrantFiled: September 24, 1993Date of Patent: April 16, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Marco Cereghetti
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Patent number: 5502083Abstract: The composition of the present invention is excellent in compatibility, transparency and curability and give a cured coat of excellent gloss and of less smell, and cured products of excellent properties can be obtained by curing the composition.The present invention relates to an onium salt represented by the following formula (1): ##STR1## wherein Ar is a mono- to tetra-valent aromatic group, X is a bisphenylsulfonio group which may have a substituent, a is 1-4, b is 0 or 1-3, a+b is 1-4, n is 1-4, and Z is a halide represented by the following formula (3):MQ.sub.m (OH).sub.l (3)where M is a boron atom, a phosphorus atom, an arsenic atom or an antimony atom, Q is a halogen atom, m is 3-6, l is 0 or 1, and m+l is 4-6; a photopolymerization initiator containing the onium salt as an active ingredient; an energy ray-curable composition containing the initiator; and a cured product.Type: GrantFiled: June 8, 1994Date of Patent: March 26, 1996Assignee: Nippon Kayaku Kabushiki KaishaInventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
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Patent number: 5481041Abstract: A process for isolating triphenylphosphine (TPP) from a triphenylphosphine/aluminum chloride complex dissolved in chlorobenzene by decomplexation, hydrolysis and extraction using water and subsequent separation of the liquid/liquid dispersion, which is composed of a TPP-containing chlorobenzene phase and of an containing Al and Cl compounds aqueous phase, into a TPP-containing chlorobenzene phase and into a TPP-free, aqueous phase, containing Al and Cl compounds, whereinwater is dispersed in the chlorobenzene phase in a ratio of 0.6-0.95 kg of water per kg of chlorobenzene solution in a 1st mixing apparatus in such a way that the temperature resulting from the hydrolysis is in the range from 60.degree. to 90.degree. C., the dispersion being carried out with residence times of 5-30 minutes and energy densities of 2-10 kW/m.sup.3,a second dispersion is carried out in a 2nd mixing apparatus with residence times of 5-60 minutes and energy densities of 0.05-0.5 kW/m.sup.Type: GrantFiled: August 3, 1994Date of Patent: January 2, 1996Assignee: BASF AktiengesellschaftInventors: Peter Lechtken, Friedrich Sauer, Matthias Fankhaenel, Dieter Hermeling
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Patent number: 5468890Abstract: The invention concerns iodonium salts of the general formula A-I.sup.+ --B X.sup.-, in which A is a group of the general formula ##STR1## in which C is a monovalent aromatic hydrocarbon group with 6 to 14 carbon atoms or a monovalent aromatic hydrocarbon group containing at least one oxygen and/or sulphur atom and with 5 to 14 atoms in the aromatic ring, D, E and F are each substituents of C, D being a group of the formula --(O).sub.x --(R).sub.y --SiR1/3, E being a group of the formula --OR.sup.2, F being a group of the formula --R.sup.3, a being 1, 2, or 3, b being 0, 1 or 2, c being 0, 1 or 2, x being 0 or 1 and y being 0 or 1, and R, R.sup.1, R.sup.2 and R.sup.3 are as defined in claim 1; B is a group of the formula ##STR2## in which E and F, which are as defined above, may each be bound to the 2, 3, 4, 5 or 6 position in the benzene ring, d is 0, 1 or 2, e is 0, 1 or 2 and X.sup.- is a tosylate anion or a weakly nucleophilic or non-nucleophilic anion Y.sup.- selected from the group comprising CF.sub.Type: GrantFiled: June 8, 1994Date of Patent: November 21, 1995Assignee: Wacker-Chemie GmbHInventors: Christian Herzig, Silke Scheiding
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Patent number: 5457219Abstract: Novel, racemic and optically active phosphorus compounds of the formula ##STR1## wherein R signifies lower alkyl or lower alkoxy and R.sup.1 represents lower alkyl, cycloalkyl or substituted phenyl, are described.The compounds of formula I are useful in the form of complexes with a metal of Group VIII as catalysts for asymmetric hydrogenations and for enantioselective hydrogen displacements in prochiral allylic systems.Type: GrantFiled: September 27, 1993Date of Patent: October 10, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Joseph Foricher, Rudolf Schmid
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Patent number: 5414134Abstract: Bisphosphine oxide monomers and homologs thereof may be incorporated into polycarbonates in order to obtain a flame retardant polymer. More particularly, bis[2,5-(diphenylphosphine oxide)]-1,4-hydroquinone and homologs thereof may be used to prepare flame retardant polycarbonates that retain high glass transition temperature and high impact resistances.Type: GrantFiled: December 20, 1993Date of Patent: May 9, 1995Assignee: General Electric CompanyInventor: Gary C. Davis
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Patent number: 5399771Abstract: A process of synthesizing a compound of the formula 1: ##STR1## is disclosed, which comprises reacting a compound of the formula 2: ##STR2## with diphenylphosphine in the presence of an amine base and a nickel catalyst to produce a compound of formula 1.Type: GrantFiled: June 1, 1994Date of Patent: March 21, 1995Assignee: Merck & Co., Inc.Inventors: Dongwei Cai, Joseph F. Payack, Thomas R. Verhoeven
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Patent number: 5354894Abstract: Disclosed is a process for the preparation of alkali metal diarylphosphide compounds wherein at least one of the aryl radicals is substituted with an alkyl group. Also disclosed is the preparation of alkyl(diaryl)phosphine compounds which are obtained by the reaction of the alkali metal diarylphosphide compounds with alkyl halide alkylating agents.Type: GrantFiled: October 14, 1993Date of Patent: October 11, 1994Assignee: Eastman Chemical CompanyInventor: Thomas J. Devon
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Patent number: 5352813Abstract: An improved process is provided for the carbonylation of methanol to acetic acid and/or its derivatives, especially methyl acetate, under mild reaction conditions using a novel catalyst precursor. The precursor is a transition metal complex having a heterodifunctional bidentate phosphorus--nitrogen ligand attached to the metal. The carbonylation reaction can now typically be carried out at 80.degree. C. and CO pressure of 40 p.s.i.g.Type: GrantFiled: September 3, 1991Date of Patent: October 4, 1994Assignee: University of AlbertaInventors: Ronald G. Cavell, Kattesh V. Katti
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Patent number: 5352822Abstract: The present invention discloses pesticidally active compounds of formula (II) ##STR1## or a salt thereof, wherein Q is an monocyclic aromatic ring, or fused bicyclic ring system of which at least one ring is aromatic containing 9 or 10 atoms of which one may be nitrogen and the rest carbon each ring system being optionally substituted, or Q is a dihalovinyl group or a group R.sup.6 --C.tbd.C-- where R.sup.6 is C.sub.1-4 alkyl, tri C.sub.1-4 alkylsilyl, halogen or hydrogen; R.sup.2, R.sup.3 , R.sup.4 and R.sup.5 are the same or different with at least one being hydrogen and the others being independently selected from hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 haloalkyl; and R.sup.1 is selected from hydrogen and C.sub.1-8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C.sub.1-6 alkoxy and X.sup.1 is hydrogen, fluoro or chloro.Type: GrantFiled: April 7, 1993Date of Patent: October 4, 1994Assignee: Roussel UclafInventors: Robert J. Blade, George S. Cockerill, John E. Robinson
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Patent number: 5312939Abstract: Novel 2,2'-bis(dicyclopentylphosphino)-1,1'-binaphthyl represented by formula (I): ##STR1## and a transition metal complex using the same as a ligand, are disclosed. The transition metal complex is industrially excellent as a catalyst for various asymmetric synthesis reactions.Type: GrantFiled: July 10, 1991Date of Patent: May 17, 1994Assignee: Takasago International CorporationInventors: Yoji Hori, Hidenori Kumobayashi
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Patent number: 5306835Abstract: A method for producing octadienols, which comprises reacting 1,3-butadiene with water in the presence of a palladium compound, a phosphine compound and carbon dioxide, wherein a compound of the formula (I): ##STR1## wherein each of R.sup.1, R.sup.5 and R.sup.9 which may be the same or different, is a hydrocarbon group, and each of R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7, R.sup.8, R.sup.10, R.sup.11 and R.sup.12 which may be the same or different, is hydrogen or a substituent, provided that at least one of them is an electron donative substituent, is used as the phosphine compound.Type: GrantFiled: September 3, 1993Date of Patent: April 26, 1994Assignee: Mitsubishi Kasei CorporationInventors: Keiichi Sato, Iwao Nakajima, Yoko Misu
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Patent number: 5300686Abstract: Organophosphorus dihalides can have one of their halogen substituents substituted with an alkyl group from a trialkylaluminum by gradual addition of the latter reagent to the former.Type: GrantFiled: January 19, 1990Date of Patent: April 5, 1994Assignee: Akzo nvInventor: Jeffrey E. Telschow