Phosphonium Derivative Patents (Class 568/9)
  • Patent number: 6169209
    Abstract: An improved process for preparing an organic phosphonium chloride is performed by bringing an organic phosphonium bromide into contact with a chloride ion in a heterogeneous mixture solution of water and an organic solvent.
    Type: Grant
    Filed: November 23, 1998
    Date of Patent: January 2, 2001
    Assignee: Ube Industries, Ltd.
    Inventors: Katsumasa Harada, Ryoji Sugise, Koichi Kashiwagi, Sadao Niida
  • Patent number: 6124508
    Abstract: A process for the preparation of alkylene glycols by reacting an alkylene oxide with water in the presence of at least one ionic composition of a quaternary phosphonium cation of the general formulaR.sub.1 R.sub.2 R.sub.3 R.sub.4 P.sup.+Whereby each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4, independently, may be an alkyl, cycloalkyl, aryl, alkylaryl or arylalkyl group having from 1 to 10 carbon atoms, each of which may carry one or more substituents, or be attached to a polymer and an anion other than metalate or halogen.
    Type: Grant
    Filed: December 9, 1999
    Date of Patent: September 26, 2000
    Assignee: Shell Oil Company
    Inventor: Eugene Marie Godfried Andre Van Kruchten
  • Patent number: 6103940
    Abstract: Preparing (3R, 3'R)-zeaxanthin of the formula I ##STR1## starting from (4-hydroxy-2,2,6-trimethylcyclohexanone of the formula II ##STR2## via the novel intermediates (4R,6R)-1-formyl-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptane of the formula IV ##STR3## (4R,6R)-1-(3-oxo-1-butenyl)-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptane of the formula V ##STR4## (4R,6R)-1-(3- hydroxy-3-methyl-1,4-pentadienyl)-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptan e of the formula VI ##STR5## [5-(4R,6R)-(4-hydr oxy-2,2,6-trimethyl-1-cyclohexylidene)-3-methyl-1,3-pentadienyl]triarylphos phonium salt of the formula iso-III ##STR6## where Ar is aryl and X is one equivalent of an anion of a strong acid. The (4R,6R)-1-formyl-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptane of formula IV is obtained by reacting the ketone of the formula II with dichloromethyllithium, which can be prepared by metallation of dichloromethane with butyllithium or lithium diisopropylamide.
    Type: Grant
    Filed: June 4, 1998
    Date of Patent: August 15, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Paust, Wolfgang Kriegl
  • Patent number: 6096904
    Abstract: Synthetic methods for lactone-containing compounds such as the discodermolides are provided, as are compounds which mimic the chemical and/or biological activity thereof, and methods and intermediates useful in their preparation.
    Type: Grant
    Filed: July 23, 1998
    Date of Patent: August 1, 2000
    Assignee: The Trustees of the University of Pennsylvania
    Inventors: Amos B. Smith, III, Yuping Qiu, Michael Kaufman, Hirokazu Arimoto, David R. Jones, Kaoru Kobayashi, Thomas J. Beauchamp
  • Patent number: 6080885
    Abstract: A phosphonium salt compound having an acryl group which is represented by the following general formula (3) can be made in simple operations: ##STR1## (wherein A represents a alkylene group, Y represents Cl, Br or I, R.sup.1 represents H or CH.sub.3, and R.sup.2, R.sup.3 and R.sup.4 represent a alkyl group having 1-8 carbon atoms, cycloalkyl, aryl, alkaryl or aralkyl group) by reacting an unsaturated aliphatic carboxylic acid halide of the following general formula (1):CH.sub.2 .dbd.CR.sup.1 --COX (1)(wherein R.sup.1 represents H or CH.sub.3 and X represents Cl, Br or I) with a hydroxyalkyl phosphonium salt compound of the following general formula (2):[HO--A--P.sup.+ R.sup.2 R.sup.3 R.sup.4 ]Y.sup.- (2)(wherein A, Y, R.sup.2, R.sup.3 and R.sup.4 have the same meanings as defined above). The present invention is industrially advantageous since the product can have a very high purity and be obtained in high yield by an easy operation.
    Type: Grant
    Filed: September 15, 1998
    Date of Patent: June 27, 2000
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventors: Masashi Sugiya, Tsutomu Watanabe
  • Patent number: 5973174
    Abstract: A method is provided to prepare a cationic transition metal catalyst, the method including the steps of: providing a disubstituted phosphine selected from the group consisting of RPH and R.sub.1 R.sub.2 PH wherein R is a divalent group selected from substituted and nonsubstituted hydrocarbon groups, R.sub.1 and R.sub.2 are independently selected from substituted and nonsubstituted hydrocarbon groups; combining the disubstituted phosphine with a salt of the formula R.sub.3 X.sub.n wherein X is a good leaving group and is a weakly coordinating anion and R.sub.3 is a substituted or nonsubstituted aliphatic hydrocarbon and n is 1, 2, or 3 to form a phosphonium salt of a formula selected from R.sub.3 (RP.sup.+ H).sub.n nX.sup.- and R.sub.3 (R.sub.1 R.sub.2 P.sup.+ H).sub.n nX.sup.- ; and combining the phosphonium salt with a transition metal salt of the formula MY.sub.m wherein M is a transition metal, and Y is the anion of a weak acid thereby forming a cationic transition metal catalyst.
    Type: Grant
    Filed: November 24, 1998
    Date of Patent: October 26, 1999
    Assignee: Shell Oil Company
    Inventors: Pui Kwan Wong, Manuel Soler Rodriguez, Andrew Allison Moxey
  • Patent number: 5945082
    Abstract: Novel cyanophosphorus compounds are disclosed. The preparation, purification, and characterization of dicyanophosphinate, cyanopolyphosphates, tricyanocyclotriphosphonate and tetracyanocyclotetraphosphate are presented.
    Type: Grant
    Filed: December 23, 1997
    Date of Patent: August 31, 1999
    Assignee: Monsanto Company
    Inventors: Patrick J. Lennon, Sergey G. Vulfson
  • Patent number: 5942637
    Abstract: Compounds containing a tetradecachlorocyclohexasilane dianion are prepared by contacting trichlorosilane with a reagent composition comprising a tertiary polyamine. The compound ?pedeta.SiH.sub.2 Cl.sup.+1 !.sub.2 ?Si.sub.6 Cl.sub.14.sup.-2 ! wherein pedeta is N,N,N',N",N"-pentaethyldiethylenetriamine is prepared by contacting trichlorosilane with pedeta. The compound ?Ph.sub.4 P.sup.+1 !.sub.2 ?Si.sub.6 Cl.sub.14.sup.-2 ! is prepared by contacting trichlorosilane with a mixture of N,N,N',N'-tetraethylethylenediamine and triphenylphosphonium chloride. The tetradecachlorocyclohexasilane dianion can be chemically reduced to cyclohexasilane, a compound useful in the deposition of amorphous silicon films. The tetradecachlorcyclohexasilane dianion can also be contacted with a Grignard reagent to form a dodecaorganocyclohexasilane.
    Type: Grant
    Filed: March 30, 1998
    Date of Patent: August 24, 1999
    Assignee: North Dakota State University Research Foundation
    Inventors: Philip Raymond Boudjouk, Beon-Kyu Kim, Michael Perry Remington, Bhanu Chauhan
  • Patent number: 5935542
    Abstract: The novel cyanophosphonate compounds of the present invention include cyanophosphonate salts, cyanophosphonate monoacid salts, cyanophosphonate monoacid esters, cyanophosphonate monoester salts and cyanophosphonate methylester salts.
    Type: Grant
    Filed: December 23, 1997
    Date of Patent: August 10, 1999
    Assignee: Monsanto Company
    Inventors: Patrick J. Lennon, Sergey G. Vulfson
  • Patent number: 5883277
    Abstract: Metallocene complexes having a cationic bridge of the formula ##STR1## where the substituents have the following meanings: M is a metal of transition group III, IV, V or VI of the Periodic Table of the Elements or a metal of the lanthanide group,X is fluorine, chlorine, bromine, iodine, hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.15 -aryl or --OR.sup.5,R.sup.1 to R.sup.12, Y, Z and n having the meanings set out in the specification, said complexes can be prepared via ligand systems of the formula II ##STR2## as intermediates.
    Type: Grant
    Filed: August 14, 1997
    Date of Patent: March 16, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: David Fischer, Franz Langhauser, Gunther Schweier, Hans-Herbert Brintzinger, Nadine Leyser
  • Patent number: 5858317
    Abstract: A process for preparing cyanophosphonate derivatives involves contacting phosphoric anhydride (P.sub.4 O.sub.10) and a cyanide, preferably in the presence of a Lewis base, in a reaction mixture under sufficient conditions to produce a cyanophosphonate derivative. The cyanophosphonate derivative can be subsequently hydrogenated to produce an aminomethylphosphonate derivative.
    Type: Grant
    Filed: December 23, 1997
    Date of Patent: January 12, 1999
    Assignee: Monsanto Company
    Inventors: Patrick J. Lennon, Sergey G. Vulfson
  • Patent number: 5849954
    Abstract: The present invention relates to a process for forming an N-.alpha.-amino protected amino acid fluoride in situ by reacting an N-.alpha.-amino protected amino acid with an ionic fluoride salt in the presence of a peptide coupling agent. It is also directed to the use of the amino acid fluoride thus formed in peptide synthesis.
    Type: Grant
    Filed: January 18, 1996
    Date of Patent: December 15, 1998
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, Dumitru Ionesou
  • Patent number: 5834588
    Abstract: The invention is directed to systematic synthetic and testing strategies for .alpha.-keto acids, esters and amides. The method of synthesis comprises (A) reacting (cyanomethylene)triphenylphosphorane with a carbonyl compound selected from carboxylic acids (RCOOH) and acyl chlorides (RCOCl) to make a cyano keto phosphorane, (B) oxidizing said phosphorane and (C) reacting the oxidized product with a nucleophile (NuH) to make the product .alpha.-keto acid, ester or amide. Systematic synthesis and testing are achieved by a modular approach in which arrays of molecules are generated by variation of R and Nu.
    Type: Grant
    Filed: July 14, 1995
    Date of Patent: November 10, 1998
    Assignee: Yale University
    Inventors: Harry H. Wasserman, Wen-Bin Ho
  • Patent number: 5756843
    Abstract: Quaternary salts having a double helix structure are prepared by the reaction of dihydroxyaromatic compound, preferably a bisphenol, with an alkali metal hydroxide and a quaternary salt, such as a tetraalkylammonium or hexaalkylguanidinium chloride. The quaternary salts and their alkaline hydrolysis products are useful as catalysts in various reactions, including imide formation from bisphenol salts and halo- or nitro-substituted phthalimides and redistribution and equilibration of polycarbonates.
    Type: Grant
    Filed: December 17, 1996
    Date of Patent: May 26, 1998
    Assignee: General Electric Company
    Inventors: Jimmy Lynn Webb, Matthew Hal Littlejohn, Joseph John Caringi, Thomas Link Guggenheim, Robert Joseph Nick, Patrick Joseph McCloskey, Joseph Anthony King, Jr.
  • Patent number: 5744461
    Abstract: Lipid-containing prodrugs are provided for treating viral infections due to herpes, influenza, hepatitis B, Epstein-Barr, and varicella zoster viruses, as well as cytomegalovirus and derivatives of antiviral agents. The compounds comprise phosphonoacids having antiviral activity which are linked, either through the phosphate group or carboxyl group of the phosphonoacid, to one of a selected group of lipids. Phosphonoacetic acid and phosphonoformic acid are thus linked to phospholipids, glycerolipids, sphingolipids, glycolipids, or fatty acids. The compounds persist, after intracellular hydrolysis, as the antiviral phosphonoacids. The lipid prodrugs are effective in improving the efficacy of antiviral phosphonoacids by prolonging their antiviral activity following administration.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: April 28, 1998
    Assignee: NeXstar Pharmaceuticals, Inc.
    Inventors: Karl Y. Hostetler, Raj Kumar
  • Patent number: 5741931
    Abstract: Phosphepinium Salts ThereofThe present invention relates to phosphonium salts of the formula (I) ##STR1## in which Ar--Ar is a biphenyl radical, a 1-phenylnaphthyl radical or a 1,1'-binaphthyl radical, each CH.sub.2 group is arranged in the ortho position to the Ar--Ar bond, R is F, an alkyl radical or an alkoxy radical respectively having 1 to 8 carbon atoms, n is an integer from 0 to 4, R.sup.1 and R.sup.2 are identical or different and, independently of each other, are an alkyl radical having 1 to 10 carbon atoms, a cycloaliphatic radical having 5 to 10 carbon atoms, or are a radical Ar.sup.1 --(R.sup.3).sub.m, where Ar.sup.1 is a phenyl or naphthyl radical, R.sup.3 is F, Cl, CF.sub.3, SO.sub.3 H, SO.sub.3 Me (Me.dbd.Li, Na or K), a dialkylamino radical having 2 to 8 carbon atoms, an alkyl radical or an alkoxy radical respectively having 1 to 8 carbon atoms and m is an integer from 0 to 5, or R.sup.1 and R.sup.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: April 21, 1998
    Assignee: Hoechst AG
    Inventors: Christoph Naumann, Dieter Regnat
  • Patent number: 5705696
    Abstract: Quaternary (e.g., tetraalkylammonium and tetraalkylphosphonium) salts containing non-halide anions are prepared by performing an anion exchange reaction by liquid-liquid extraction with a chlorinated solvent of a mixture of an aqueous solution an alkali metal salt of the anion and a corresponding quaternary halide.
    Type: Grant
    Filed: August 1, 1996
    Date of Patent: January 6, 1998
    Assignee: General Electric Company
    Inventor: Joseph Anthony King, Jr.
  • Patent number: 5693807
    Abstract: 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: Grant
    Filed: June 5, 1995
    Date of Patent: December 2, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Gottfried Sedelmeier, Gerhard Fischer
  • Patent number: 5554795
    Abstract: 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: Grant
    Filed: May 19, 1995
    Date of Patent: September 10, 1996
    Assignee: Phillips Petroleum Company
    Inventors: Krisztina Frey, Gabriele von Massow, Helmut G. Alt, M. Bruce Welch
  • Patent number: 5543522
    Abstract: There are disclosed a process for preparing an ambient temperature molten salt, which comprises treating an ambient temperature molten salt consisting essentially of 20 to 50 mole % of an aluminum halide and 80 to 50 mole % of an onium halide, containing oxygen-containing impurities originating from water with thionyl chloride anda process for preparing an ambient temperature molten salt for effecting aluminum electroplating, which comprises treating mixed ambient temperature molten salts consisting essentially of 30 to 50 mole % of an aluminum halide and 70 to 50 mole % of an onium halide, containing oxygen-containing impurities originating from water with thionyl chloride, and then adding aluminum halide to the molten salt to prepare an ambient temperature molten salt composition consisting essentially of 50 to 80 mole % of an aluminum halide and 50 to 20 mole % of an onium halide.
    Type: Grant
    Filed: August 25, 1994
    Date of Patent: August 6, 1996
    Assignees: Mitsubishi Chemical Corporation, Nisshin Steel Co., Ltd.
    Inventors: Takayuki Kawahara, Hitoshi Suzuki, Asao Kominato
  • Patent number: 5525580
    Abstract: 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: Grant
    Filed: January 14, 1994
    Date of Patent: June 11, 1996
    Assignee: SDS Biotech K.K.
    Inventors: Kenichi Komatsubara, Tadashi Sato, Kenji Mikami, Yuji Yamada
  • Patent number: 5504230
    Abstract: A process for preparing 9-(Z)-retinoic acid from mother liquors from the industrial preparation of C.sub.15 -triarylphosphonium salts of the general formula I ##STR1## where R.sup.1 to R.sup.3 are each aryl and X.sup..crclbar. is halogen or (HSO.sub.4).sup..crclbar., in an organic solvent, which comprisesA. increasing the proportion of 9-(Z)-C.sub.15 -triarylphosphonium salt in the C.sub.15 -triarylphosphonium salts isolated from the mother liquor by treatment with isopropanol at elevated temperature, cooling and separating off the all-(E)-C.sub.15 -triarylphosphonium salt which has crystallized out,B. subjecting the resulting C.sub.15 -triarylphosphonium salt to a Wittig reaction with an alkyl .beta.-formylcrotonate of the general formula ##STR2## and C. hydrolyzing the resulting oily retinoic ester mixture in a C.sub.3 -C.sub.
    Type: Grant
    Filed: December 16, 1994
    Date of Patent: April 2, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael John, Joachim Paust
  • Patent number: 5481040
    Abstract: A process for the preparation of phosphonium salts by the use of chlorides, which is useful in the course of synthesis of olefin compounds by the Wittig reaction, and which comprises reacting a phosphine compound of the general formulaR.sup.1.sub.3 Pwherein R.sup.1 is a phenyl group or a straight-chain alkyl group having 2 to 8 carbon atoms, with a primary or secondary chloride of the general formula ##STR1## wherein R.sup.2 and R.sup.3 are hydrocarbon radicals, in a solvent selected from the group consisting of N,N-dimethylformamide, N,N-dimethylacetamide and N,N-1,3-dimethyl-2-imidazolidinone, and in the presence of an alkali metal salt of the general formula MBr or MI.
    Type: Grant
    Filed: March 29, 1995
    Date of Patent: January 2, 1996
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takehiko Fukumoto, Kazushi Hirokawa, Kurao Okada
  • Patent number: 5474716
    Abstract: Disclosed are processes for the preparation of new bridged cyclopentadienylmagnesium compounds of the general formula Q(CpR.sub.a)(Cp'R'.sub.a ')Mg, and the use thereof for preparing bridged metallocenes.
    Type: Grant
    Filed: February 22, 1995
    Date of Patent: December 12, 1995
    Assignee: Witco GmbH
    Inventor: Richard Lisowsky
  • Patent number: 5453221
    Abstract: Disclosed are new bridged cyclopentadienylmagnesium compounds of the general formula Q(CpR.sub.a) (Cp'R'.sub.a')Mg, processes for the preparation thereof, and the use thereof for preparing bridged metallocenes.
    Type: Grant
    Filed: February 22, 1995
    Date of Patent: September 26, 1995
    Assignee: Witco GmbH
    Inventor: Richard Lisowsky
  • Patent number: 5360886
    Abstract: The reaction between epoxy compounds and active hydrogen-containing compounds or anhydrides is catalyzed with a phosphine or phosphonium compound containing at least three C.sub.1 to C.sub.4 alkyl phenyl groups attached to the phosphorous atom per molecule.
    Type: Grant
    Filed: October 27, 1993
    Date of Patent: November 1, 1994
    Assignee: The Dow Chemical Company
    Inventors: Ha Q. Pham, Michael B. Cavitt, Pamela A. Hardcastle
  • Patent number: 5310853
    Abstract: The reaction between epoxy compounds and active hydrogen-containing compounds or anhydrides is catalyzed with a phosphine or phosphonium compound containing at least three C.sub.1 to C.sub.4 alkyl phenyl groups attached to the phosphorous atom per molecule.
    Type: Grant
    Filed: January 21, 1993
    Date of Patent: May 10, 1994
    Assignee: The Dow Chemical Company
    Inventors: Ha Q. Pham, Michael B. Cavitt, Pamela A. Hardcastle
  • Patent number: 5276189
    Abstract: A process for the treatment of a quaternary onium salt is described. The process comprises the steps of (i) contacting an organic phase soaringly miscible in water containing a quaternary onium fluorine-containing carboxylate of RfCO.sub.2.sup.-+ AR.sup.1 R.sup.2 R.sup.3 R.sup.4 as defined in the present Specification with an aqueous phase containing a thiocyanate ion to form a quaternary onium thiocyanate in the organic phase and (ii) contacting the organic phase containing the quaternary onium thiocyanate with an aqueous solution containing a water-soluble oxidizing agent to decompose the thiocyanate ion and to form an easily ion exchangeable quaternary onium salt. Also, applications of this treatment to a process for preparing hexafluoropropylene oxide from hexafluoropropylene in a two-phase system of an aqueous phase and an organic phase by using a hypochlorite as an oxidizing agent in the presence of a quaternary onium salt as a catalyst are described.
    Type: Grant
    Filed: May 11, 1992
    Date of Patent: January 4, 1994
    Assignee: Asahi Kasei Kogyo K.K.
    Inventors: Masanori Ikeda, Yoshio Suzuki, Atsushi Aoshima
  • Patent number: 5250736
    Abstract: Allylphosphines and vinylphosphines are prepared by reaction of a phosphine with an allylhalide or a vinylhalide, respectively. Preferably the phosphine is a secondary phosphine, so that there is formed an allyldialkylphosphine or a dialkylvinylphosphine. The allyldialkylphosphine can be reacted further with dialkylphosphine under free radical conditions to yield a 1,3-bis-(dialkylphosphino)propane. The dialkylvinylphosphine can be reacted further with dialkylphosphine under free radical conditions to yield a 1,2 bis-(dialkylphosphino)ethane. These compounds are useful as bidentate ligands.
    Type: Grant
    Filed: August 11, 1992
    Date of Patent: October 5, 1993
    Assignee: Cyanamid Canada Inc.
    Inventors: Colleen E. Micklethwaite, Allan J. Robertson
  • Patent number: 5202407
    Abstract: The reaction between epoxy compounds and active hydrogen-containing compounds or anhydrides is catalyzed with a phosphine or phosphonium compound containing at least three C.sub.1 to C.sub.4 alkyl phenyl groups attached to the phosphorus atom per molecule.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: April 13, 1993
    Assignee: The Dow Chemical Company
    Inventors: Ha Q. Pham, Michael B. Cavitt, Pamela A. Hardcastle
  • Patent number: 5166445
    Abstract: Phosphonium salts of the formula ##STR1## wherein A signifies aryl and Y.sup.- signifies C.sub.1 -C.sub.6 -alkanoate or hydroxytrifluoroborate, as well as their manufacture from 3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-ol with a triarylphosphine and with a C.sub.1 -C.sub.6 -alkanoic acid or a boron trifluoride etherate and, if desired after conversion into the phosphonium salt of a strong acid, further reaction to give lycopene.
    Type: Grant
    Filed: January 11, 1990
    Date of Patent: November 24, 1992
    Assignee: Hoffman-La Roche Inc.
    Inventor: Karl Meyer
  • Patent number: 5118346
    Abstract: Compounds of the formulaR.sup.1 3Y.sup..sym. R.sup.2 X.sup..crclbar. (I)in which the radicals R.sup.1 are identical or different and are C.sub.2 -C.sub.6 alkyl, phenyl, C.sub.1 -C.sub.2 alkyl-substituted phenyl or C.sub.5 -C.sub.7 cycloalkyl, benzyl, tolyl, or hydroxy-C.sub.1 -C.sub.4 alkyl and R.sup.2 is straight-chain or branched C.sub.8 -C.sub.2 alkyl, and Y is P or N, or R.sup.1 3Y.sup..sym. R.sup.2 is ##STR1## in which R.sup.4 is H or --CH.sub.3, or ##STR2## and X is BF.sub.4 or PF.sub.6, which are used as biocides, in particular in industrial solutions, in paints or in solid materials.
    Type: Grant
    Filed: January 23, 1991
    Date of Patent: June 2, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Wolfgang Wehner, Joachim Lorenz, Reinhardt Grade
  • Patent number: 5116481
    Abstract: An anion-selective electrode of the present invention comprises, as anion sensitive substance, a tetraalkyl type, quaternary phosphonium salt having four alkyl radicals, each having 8 to 24 carbon atoms; a combination of a tetraalkyl onium salt having four alkyl radicals each having 10 to 24 carbon atoms, and an onium salt having one alkyl radical with 1 to 20 carbon atoms and three alkyl radicals with the proviso that the number of carbon atoms contained in the three alkyl radicals each is larger than that contained in the one alkyl radical; or a tetraalkyl type, quaternary onium salt having an asymmetrical molecular structure. The anion-selective electrode has good properties including selectivity and measurement accuracy. An anion-selective, field effect transistor or a chemical analysis apparatus, provided with the anion-selective sensitive substance, is suitable for measuring an anion concentration with a high accuracy.
    Type: Grant
    Filed: April 5, 1990
    Date of Patent: May 26, 1992
    Assignee: Hitachi, Ltd.
    Inventors: Satoshi Ozawa, Naoto Oki, Yasuhisa Shibata, Hiroyuki Miyagi
  • Patent number: 5102874
    Abstract: Antimicrobial mixtures contain quaternary ammonium compounds and quaternary phosphonium compounds in a ratio by weight of from 1:9 to 9:1.
    Type: Grant
    Filed: August 20, 1990
    Date of Patent: April 7, 1992
    Assignee: Ecolab Inc.
    Inventors: Karl Lintner, Reinhard Orth, Rudolf Lehmann, Hans-Juergen Mueller
  • Patent number: 5070214
    Abstract: Disclosed is an organic material with a very narrow electronic spin resonance (ESR) line. This material is formed by a 1, 2, 7, 8-tetrahydrocyclopentataperylene salt which may have, advantageously, undergone a heat treatment. The material can be applied to the fabrication of probes for gaussmeters and magnetometers.
    Type: Grant
    Filed: May 30, 1989
    Date of Patent: December 3, 1991
    Assignee: Thomson CSF
    Inventors: Paul Penven, Philippe Michel, Denis Jerome, Alexandre Moradpour
  • Patent number: 5055619
    Abstract: Phosphonium compounds of formula (I): ##STR1## in which at least one of the radicals R.sub.1 to R.sub.4 is a fluorine-substituted, saturated alkyl radical having 1 to 30 carbon atoms and 3 to 50 fluorine atoms, which can contain further substituents, or at least one of the radicals R.sub.1 to R.sub.4 is a fluorine-substituted aryl radical or an aralkyl radical substituted by fluorine on the aromatic ring, it being possible for the aryl or aralkyl radical to be further substituted on the aromatic ring, and the alkyl bridge between the phosphorus atom and the aromatic ring, in the case of an aralkyl radical, containing 1 to 30 carbon atoms, and at most three of the radicals R.sub.1 to R.sub.4 independently of the others are hydrogen atoms, unsaturated or saturated, substituted or unsubstituted C.sub.1 -C.sub.30 alkyl radicals or aryl or aralkyl radicals which can be substituted on the aromatic ring, and R.sub.5 to R.sub.
    Type: Grant
    Filed: April 12, 1990
    Date of Patent: October 8, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jorg Gitzel, Hans-Tobias Macholdt, Wolfgang Knaup
  • Patent number: 4943380
    Abstract: An antistatic resin composition with transparency contains 90-99.9 wt % of a synthetic resin selected from polycarbonate or polymethyl methacrylate and 0.1-10 wt % of a heat-resistant antistat containing phosphonium sulfonate shown by the general formula (I) below: ##STR1## where A is alkyl group with 1-36 carbon atoms, alkenyl group with 4-24 carbon atoms, phenyl group, phenyl group substituted by alkyl group with 1-18 carbon atoms, naphthyl group or naphthyl group substituted by alkyl group with 1-18 carbon atoms, R.sup.1, R.sup.2 and R.sup.3 are identical, each being an aliphatic hydrocarbon group with 1-8 carbon atoms or aromatic hydrocarbon group, and R.sup.4 is a hydrocarbon group with 1-18 carbon atoms.
    Type: Grant
    Filed: February 27, 1989
    Date of Patent: July 24, 1990
    Assignee: Takemoto Yushi Kabushiki Kaisha
    Inventors: Masato Sugiura, Hideo Shimizu, Shigeru Imamura, Fumitoshi Sugiura
  • Patent number: 4927960
    Abstract: Novel phosphonium salts of the general formula ##STR1## wherein R.sup.1 and R.sup.2 each is a hydrogen atom or a hydrocarbon group of 1 to 12 carbon atoms which may optionally be substituted; R.sup.3 is a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms which may optionally be substituted; R.sup.4, R.sup.5 and R.sup.6 each is a hydrocarbon group of 1 to 8 carbon atoms which may optionally be substituted; X is a hydroxyl group, a hydroxycarbonyloxy group or a lower alkylcarbonyloxy group, and processes for production of the salts are described. Telomerization catalysts containing said phosphonium salts and processes for production of straight-chain alkadienyl compounds using the same catalysts are also provided.
    Type: Grant
    Filed: June 24, 1988
    Date of Patent: May 22, 1990
    Assignee: Kuraray Company, Ltd.
    Inventors: Toshihiko Maeda, Yasuo Tokitoh, Noriaki Yoshimura
  • Patent number: 4900854
    Abstract: Process for the preparation of asymmetrical alkaline earth metal organoborates and organoaluminates represented by the formula I: ##STR1## and asymmetrical alkaline earth metal organoarsenates and organophosphates represented by the formula II: ##STR2## wherein Z is selected from the group consisting of boron and aluminum; X is selected from the group consisting of phosphorus and arsenic; M is an alkaline earth metal; and in which R.sub.1 -R.sub.6 are independently selected from alkyl, aryl, alkaryl, aralkyl, alkenyl, cycloalkyl, and cyano with the proviso that R.sub.1 -R.sub.6 are not all the same.
    Type: Grant
    Filed: December 8, 1988
    Date of Patent: February 13, 1990
    Assignee: The Dow Chemical Company
    Inventors: Richard C. Winterton, Ronald J. Hoffman, Thomas D. Gregory
  • Patent number: 4892944
    Abstract: A process for producing quaternary salts of high purity is disclosed, comprising reacting a tertiary amine or phosphine with a carbonic acid diester to form a corresponding quaternary carbonate and further mixing it with an acid to perform decarboxylation. The quaternary salts thus obtained are useful compounds which can be used in wide fields as various catalysts, electrolytes, additives, medicaments, etc.
    Type: Grant
    Filed: May 11, 1988
    Date of Patent: January 9, 1990
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Shoichiro Mori, Kazuhiko Ida, Makoto Ue
  • Patent number: 4806620
    Abstract: An aqueous, resinous solution of a curable, polymeric reaction product, the cured polymeric flame resistant coating and methods for producing them are provided. The solution is formed by direct reaction or prepolymer reaction and chain extension reaction of a methylol and/or hydroxyl-containing quaternary phosphonium compound, divalent nitrogen-containing compound and a heteroatom-containing compound. A nitrogen-containing compound has at least 2 active hydrogen and/or methylol radicals. The direct or prepolymer reaction has present a tertiary amine.
    Type: Grant
    Filed: March 30, 1987
    Date of Patent: February 21, 1989
    Assignee: PPG Industries, Inc.
    Inventors: Michael W. Klett, Balbhadra Das
  • Patent number: 4743466
    Abstract: For use in magnetic recording tapes and for other purposes, iron and iron alloy materials are passivated and protected against oxidative corrosion by treatment with a solution of a non-hygroscopic salt of bis(triphenylphosphoranylidene) ammonium cation with an anion such as nitrate or chromate.
    Type: Grant
    Filed: June 5, 1987
    Date of Patent: May 10, 1988
    Assignee: Eastman Kodak Company
    Inventors: Henry J. Gysling, Joseph S. Yudelson
  • Patent number: 4656310
    Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid,- tetraenal or tetraenol derivatives useful as anti-tumor agents.
    Type: Grant
    Filed: May 13, 1985
    Date of Patent: April 7, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
  • Patent number: 4595783
    Abstract: The invention relates to intermediate compounds having the general formula I ##STR1## in which R.sup.1 is H, an alkyl, arylalkyl or an aliphatic acyl radical, preferably a benzyl or acetyl group and wherein X and Y together span an additional bond between the X and Y carrying C atoms (Ia) or in which Y is OH and X is H (Ib) and in which the dotted line can represent an additional bond particularly[2R,1'Z,3'E,7'E]-6-benzyloxy-2,5,7,8-tetramethyl-2-(4',8',12'-trimethyl-tri deca-1',3',7'-trien-1'-yl)chroman and6-benzyloxy-2,5,7,8-tetramethyl-2-(1'-hydroxy-4',8',12'-trimethyl-trideca-3 ',7'-diene-1'-yl)chroman, as well as compounds and methods of preparing compounds having the general formula II ##STR2## in which Z is one of the groups ##STR3## wherein R.sup.2 is an alkyl group with 1 to 4 carbon atoms preferably CH.sub.3 or C.sub.2 H.sub.
    Type: Grant
    Filed: August 31, 1984
    Date of Patent: June 17, 1986
    Inventors: Friedrich Vogel, Joachim Paust, Axel Nuerrenbach
  • Patent number: 4544770
    Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is a 2,6,6-trimethyl-1-cyclohexen-1-yl or 2,3,6-trimethylphenyl group, either of which may be unsubstituted or substituted by a hydroxy group or a protected hydroxy group, R.sup.2 is aryl, and X.sup.- is an anionare manufactured by hydrogenating a compound of the formula: ##STR2## wherein R.sup.1, R.sup.2 and X.crclbar. are as above, in an organic solvent or aqueous-organic solvent in the presence of a nickel-, palladium-, platinum-, cobalt-, rhodium-, iridium-, or ruthenium-containing catalyst.The process is suitable as an intermediate step in carotenoid and retinoid syntheses.
    Type: Grant
    Filed: July 11, 1983
    Date of Patent: October 1, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Emil A. Broger
  • Patent number: 4540823
    Abstract: Novel advanced epoxy resins are prepared using phosphine or phosphonium salt initiators bearing at least one hydroxyphenyl or thiophenyl groups. These phosphonium salt initiators are novel compositions of matter. The resulting resins contain reduced quantities of extractable phosphorus containing moieties.
    Type: Grant
    Filed: June 15, 1984
    Date of Patent: September 10, 1985
    Assignee: The Dow Chemical Company
    Inventors: George A. Doorakian, Joseph W. Hanafin
  • Patent number: 4537985
    Abstract: A process for the manufacture of 1,4-bis[2-(4'-carbomethoxystyrenyl)] benzene is disclosed. This process comprises reacting, at a temperature of about 0.degree. C. to about 100.degree. C., in a highly polar anhydrous organic solvent or solvent mixture, or in liquid ammonia, a p-xylylene-bis-(trialkylphosphonium halide) or p-xylylene-bis-(triarylphosphonium halide) with 4-carbomethoxybenzaldehyde, initiated by the slow introduction of an organometallic compound or an inorganic base. Polyesters, such as polyethylene terephthalate, are copolymerized with about 5 to about 20 parts per million of 1,4-bis[2-(4'-carbomethoxystyrenyl)] benzene. 1,4-bis[2-(4'-carbomethoxystyrenyl)] benzene is useful to provide permanent whiteness to polyesters and polyamides and other synthetic or natural polymers. Polyesters are useful for the manufacture of fibers, films, and related industrial products.
    Type: Grant
    Filed: July 18, 1983
    Date of Patent: August 27, 1985
    Assignee: Standard Oil Company (Indiana)
    Inventors: Imre Puskas, Marshall Schmitt
  • Patent number: 4532355
    Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid,-tetraenal or tetraenol derivatives useful as anti-tumor agents.
    Type: Grant
    Filed: September 13, 1982
    Date of Patent: July 30, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
  • Patent number: 4507247
    Abstract: There are provided novel sulfonated Group Va ylides defined by the following Formula I: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.
    Type: Grant
    Filed: February 25, 1983
    Date of Patent: March 26, 1985
    Assignee: Gulf Research & Development Company
    Inventors: David L. Beach, James J. Harrison
  • Patent number: 4487698
    Abstract: A process for removing onium salts from aqueous solutions comprising adding a phenolic compound to an onium salt containing aqueous solution, contacting the solution with a water-immiscible organic material whereby the onium salt migrates into the water-immiscible organic material and separating the aqueous hase from the onium salt in the water-immiscible organic material.
    Type: Grant
    Filed: April 20, 1983
    Date of Patent: December 11, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karsten Idel, Dieter Freitag, Edgar Ostlinning