Polyoxy Patents (Class 568/662)
  • Patent number: 5292927
    Abstract: A highly fluorinated benzene compound is reacted with acryloyl chloride to ield a fluorinated liquid product which is used to impregnate a reinforcing structure. Upon impregnation, the liquid material is polymerized at about 55.degree.C. to produce a reinforced polymeric structure, which can be a circuit board. The polymer has dielectric constant of about 2.1, which is very low compared to the polymers used presently.
    Type: Grant
    Filed: February 26, 1992
    Date of Patent: March 8, 1994
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: James R. Griffith, Henry S. W. Hu
  • Patent number: 5210322
    Abstract: A process for preparing ethers which comprises contacting a carboxylated ether with a metal oxide catalyst under conditions effective to produce the ether.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: May 11, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stephen W. King, Kurt D. Olson
  • Patent number: 5196569
    Abstract: Trifluorovinyl ethers containing selected functional groups, and homo- and copolymers prepared from them, are disclosed, as well as intermediates useful in the preparation of the ethers.
    Type: Grant
    Filed: October 10, 1991
    Date of Patent: March 23, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Ming-Hong Hung
  • Patent number: 5189204
    Abstract: 3-(2-Trifluoro-1-hydroxyethyl)propenyl benzyl ether or derivatives thereof having the formula ##STR1## wherein R is a substituted or not substituted phenyl group and a mark * shows an asymmetric carbon atom, and derivatives thereof are provided, which are useful as a material for preparing liquid crystal compound.
    Type: Grant
    Filed: June 25, 1991
    Date of Patent: February 23, 1993
    Assignee: Showa Shell Sekiyu Kabushiki Kaisha
    Inventors: Tomoya Kitazumo, Takashi Yamazaki, Hitoshi Iwatsubo
  • Patent number: 5130435
    Abstract: Vinyl ethers of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are identical to or different from one another, each being hydrogen, straight-chain or branched alkyl or alkenyl of up to 12 carbon atoms, cycloalkyl or cycloalkylene of from 5 to 8 carbon atoms, aryl, alkylaryl, alkenylaryl, aralkyl and aralkenyl of from 6 to 16 carbon atoms, halogen-substituted aryl or heterocyclyl, and in addition the radicals R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3, together with the carbon atom to which they are bonded, can form a cycloalkane, cycloalkene or a heterocycle, and R.sup.4 is alkyl, alkylaryl or aralkyl, are prepared by eliminating an alcohol from an acetal/ketal of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: August 9, 1990
    Date of Patent: July 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
  • Patent number: 5130462
    Abstract: Cyclobutane derivatives of the formulas ##STR1## wherein P is a hydroxy protecting group and X is a leaving group are useful intermediates in the preparation of antiviral compounds.
    Type: Grant
    Filed: February 19, 1991
    Date of Patent: July 14, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: William A. Slusarchyk, Robert Zahler
  • Patent number: 5107034
    Abstract: The invention provides a method for producing 4-(2'-methoxyethyl)phenol by brominating 4-hydroxyacetophenone to produce alpha-bromo-5-hydroxyacetophenone, and then causing a methoxide-bromide exchange to thereby produce alpha-methoxy-4-hydroxyacetophenone; and then conducting a single step reduction of alpha-methoxy-4-hydroxyacetophenone with at least two equivalents of hydrogen per equivalent of alpha-methoxy-4-hydroxyacetophenone in the presence of a hydrogenation catalyst to thereby directly produce 4-(2'-methoxyethyl)phenol.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: April 21, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Brad L. Smith, Werner H. Mueller, Heinz Strutz
  • Patent number: 5106885
    Abstract: What is provided herein are radiation curable compositions containing(a) multifunctional vinyl ether monomers having the formula:X--R.sub.1 --Y.sub.1 --R.sub.2 --Y.sub.2).sub.n CH.dbd.CH.sub.2 ].sub.mwhereX is a 5-8 membered ring, saturated or unsaturated;R.sub.1 is a direct bond or C.sub.1 -C.sub.10 straight or branched chain alkylene;Y.sub.1 and Y.sub.2 are independently oxygen or sulfur;R.sub.2 is C.sub.2 -C.sub.10 straight or branched chain alkylene;n is 0-10; andm is 3-5;(b) a cationic initiator, and, optionally,(c) a polymerizable vinyl ether, epoxide, or acrylate oligomer.
    Type: Grant
    Filed: November 3, 1989
    Date of Patent: April 21, 1992
    Assignee: ISP Investments Inc.
    Inventors: Kou-Chang Liu, Fulvio J. Vara, James A. Dougherty
  • Patent number: 5104987
    Abstract: 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: Grant
    Filed: September 20, 1990
    Date of Patent: April 14, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Stephen W. King
  • Patent number: 5095153
    Abstract: Diethers of general formula: ##STR1## where R, R.sup.I, R.sup.II, R.sup.III, R.sup.IV and R.sup.V are the same or different and are H, C.sub.1-18 linear or branched alkyl, C.sub.5-18 cycloalkyl, C.sub.6.about. aryl, C.sub.7-18 alkylaryl or C.sub.7-18 arylalkyl radicals, provided that when R is alkyl, R.sup.I is other than H or alkyl and when R.sup.I is alkyl, R is other than H or alkyl; R.sup.VI and R.sup.VIII are the same or different and are C.sub.1-18 linear or branched alkyl, C.sub.5-18 cycloalkyl, C.sub.6-18 aryl, or C.sub.7-18 arylalkyl radicals; and two or more of R to R.sup.V may be bonded to form a cyclic structure having 5 to 18 carbon atoms.The diethers are particularly useful in the preparation of Ziegler-Natta catalysts.
    Type: Grant
    Filed: October 11, 1990
    Date of Patent: March 10, 1992
    Assignee: HIMONT Incorporated
    Inventors: Giovanni Agnes, Giampietro Borsotti, Giuliana Schimperna, Elisabetta Barbassa
  • Patent number: 5011943
    Abstract: A process is described for the improved synthesis of the optically pure C.sub.10 -C.sub.24 fragment of the macrolide structure of the immunosuppressant FK-506. This compound is also useful as an intermediate for preparing FK-506 derivatives.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: April 30, 1991
    Assignee: Merck Frosst Canada, Inc.
    Inventor: Zhaoyin Wang
  • Patent number: 4981989
    Abstract: Antihypertensive phosphate derivatives having the following formula are described: ##STR1## wherein X is selected from one or more of: (a) C.sub.1 -C.sub.24 branched or straight chain alkyl; (b) C.sub.1 -C.sub.24 branched or straight chain alkoxy; (c) ##STR2## wherein n and m are integers from 0 to 25 and the sum of n and m is less than or equal to 25; phenyl; substituted phenyl wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.20 branched or straight chain alkyl, C.sub.1 -C.sub.20 branched or straight chain alkoxy, halogen, trifluoromethyl, phenyl, and substituted phenyl, phenoxy; and substituted phenoxy, wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.20 branched or straight chain alkyl, halogen, trifluoromethyl, phenyl and substituted phenyl; Q is selected from the group consisting of: ##STR3## wherein R.sub.1 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 branched or straight chain alkyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: November 8, 1989
    Date of Patent: January 1, 1991
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Phaik E. Sum, Robert E. Schaub
  • Patent number: 4971995
    Abstract: Pharmaceutical or veterinary preparations containing (a) at least one compound with the formula: ##STR1## where:R.sub.o represents a C.sub.3 -C.sub.6 alkyl group or a benzyl group with the formula: ##STR2##in which R.sub.3 =H, a halogen, a C.sub.1 -C.sub.4 alkyl, a C.sub.1 -C.sub.4 alkoxy, CF.sub.3, NO.sub.2 or a CN group; andR.sub.2 represents:a C.sub.1 -C.sub.4 alkoxy group, in which case the pair (X, R.sub.1)=(O, OH), (O, C.sub.1 -C.sub.4 alkoxy), (CHOH, H), (O, H), (CH.sub.2, H) or (CO, H);and OH group, in which case the pair (X, R.sub.1)=(O, OH), (O, C.sub.1 -C.sub.4 alkoxy), (O, H) or (CH.sub.2, H), with the reservation that when (X, R.sub.1)=(O, OH), R.sub.o is different from a C.sub.3 -C.sub.6 alkyl or a benzyl group; ora CN or C.sub.1 -C.sub.4 alkyl-NH group, in which case the pair (X, R.sub.1)=(O, H) or (CH.sub.2, H), together with (b) a carrier or vehicle which is physiologically acceptable and appropriate for the compound used.
    Type: Grant
    Filed: January 26, 1989
    Date of Patent: November 20, 1990
    Assignee: Delande S.A.
    Inventors: Alain R. Schoofs, Michel Langlois, Christian R. Jeanpetit, Maryse F. Masson
  • Patent number: 4968836
    Abstract: The invention relates to a process for the preparation of cyclopropanecarbaldehydes of formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl, which comprises (a) reacting a tetrahydrofuran of formula ##STR2## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 -cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, with a halogenating agent to form a 1,2,4-trihalobutyl ether of formula ##STR3## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 cycloalkyl that is unsubstituted or substituted by halogen C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: January 30, 1990
    Date of Patent: November 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ruedi Kanel, John G. Dingwall
  • Patent number: 4965376
    Abstract: 3,9-Dihydroxynonyne and its derivatives protected at the 9-OH function, of the general formula I ##STR1## where R is hydrogen or a conventional alcohol protective group, and processes for the preparation of the compounds I.
    Type: Grant
    Filed: April 18, 1989
    Date of Patent: October 23, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Huellmann, Rainer Becker, Gerald Lauterbach, Ernst Buschmann, Heinz Eckhardt, Walter Himmele, Christiane Brueckner
  • Patent number: 4960884
    Abstract: Pesticidal mono-, di-, and tri-2-fluoroethyl ethers of the formula R.sup.1 R.sup.2.sub.m Ar(OCH.sub.2 CH.sub.2 F).sub.n, compositions thereof and their insecticidal, acaricidal and nematicidal uses are described and claimed.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: October 2, 1990
    Assignee: FMC Corporation
    Inventors: David M. Roush, Donald A. Shaw, Michael L. Jones, Jun H. Chang
  • Patent number: 4959391
    Abstract: Phenol derivatives of the formula ##STR1## wherein A and B have the same or different meanings and each represent one of the groups --C.tbd.C--, cis--CH.dbd.CH-- or trans--CH.dbd.CH--, R.sub.1 is hydrogen, an optionally substituted alkyl or phenyl group or a cycloalkyl group, R.sub.2 is hydrogen, methyl or ethyl, R.sub.3 represents hydrogen, acetyl or propionyl, R.sub.4 has the same meaning as R.sub.3 or represents an alkyl group, R.sub.5 is a carboxylic or a hydroxy group or a functional derivative of such groups or R.sub.5 is a nitrile group and R.sub.6 is hydrogen, an alkyl group or the group OR.sub.4 which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds are prepared by reacting suitable acetylene compounds or metal derivatives thereof with alkyl or aryl halides or by means of Wittig reactions optionally followed by transforming the member R.sub.
    Type: Grant
    Filed: July 14, 1988
    Date of Patent: September 25, 1990
    Assignee: Gruenenthal GmbH
    Inventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin O. Kiesewetter, Ulrich G. P. Seippl
  • Patent number: 4952736
    Abstract: This invention is a process for production of an alkoxyalkyl group substituted phenol represented by the following formula (1) in high yields and at high selectivity: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 each represents a hydrogen atom or an alkyl group; and R.sup.4 represents an alkyl group by reacting a phenol, an alcohol and an aldehyde in the presence of a catalyst selected from the group consisting of a tertiary alkylamine, a tertiary unsubstituted benzylamine, a mixture of a tertiary alkylamine and a tertiary unsubstituted benzylamine, a carbonate of alkali metal, a hydrogencarbonate of alkali metal and a mixture of a carbonate of alkali metal and a hydrogencarbonate of alkali metal, and recovering said alkoxyalkyl substituted phenol from said reaction product.
    Type: Grant
    Filed: January 24, 1990
    Date of Patent: August 28, 1990
    Assignee: Idemitsu Petrochmeical Company, Limited
    Inventor: Masahiro Iwahara
  • Patent number: 4918219
    Abstract: Novel purine derivatives are described as agents for treating autoimmune diseases as well as a method of manufacture and pharmaceutical compositions as well as novel intermediates in the manufacture thereof.
    Type: Grant
    Filed: September 29, 1989
    Date of Patent: April 17, 1990
    Assignee: Warner-Lambert Company
    Inventors: Jagadish C. Sircar, Charles F. Schwender, Mark J. Suto
  • Patent number: 4915875
    Abstract: Paramethyl-substituted hindered phenols are selectively oxidized by contacting with an oxidizing agent at elevated temperatures in the presence of a heterogeneous oxidative coupling catalyst. In the absence of an optional nucleophile the products comprise carbon-carbon oxidative coupling products. In the presence of a nucleophile, addition products result that may be further oxidized by continued exposure to the oxidizing agent to yield substituted p-hydroxybenzaldehydes.
    Type: Grant
    Filed: November 4, 1986
    Date of Patent: April 10, 1990
    Assignee: The Dow Chemical Company
    Inventors: Timothy R. Diephouse, Robert M. Strom
  • Patent number: 4916252
    Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a 1,3-diketone in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.
    Type: Grant
    Filed: June 16, 1988
    Date of Patent: April 10, 1990
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
  • Patent number: 4895987
    Abstract: Ruthenium-cobalt- or cobalt-containing catalysts which have been promoted with phosphonites or phosphinites effectively catalyze the dealkoxyhydroxymethylation of aldehyde acetals to form glycol monoethers. Methylal, for example, may be reacted with syngas, i.e., CO and H.sub.2, in the presence of these phosphonite- or phosphinite-promoted cobalt or ruthenium- cobalt catalysts to form the monomethyl ether of ethylene glycol. In a like manner acetaldehyde may be converted to the corresponding propylene glycol monoether. The process may advantageously be carried out with high yields and selectivities in the presence of a polar or non-polar organic solvent in combination with the catalyst system of this invention.The invention is also directed to the phosphonite- or phosphonite-promoted cobalt and ruthenium-cobalt catalyst system per se.
    Type: Grant
    Filed: June 6, 1986
    Date of Patent: January 23, 1990
    Assignee: Sun Refining and Marketing Company
    Inventors: D. Michael Duggan, James E. Lyons, Harry K. Myers, Robert E. Ledley
  • Patent number: 4847303
    Abstract: The present invention involves compounds having the structure: ##STR1## wherein: (a) --A.sup.1 is selected from the group consisting of --OH, --H, and --O.sub.2 CR;(b) --A.sup.2 is selected from the group consisting of unsubstituted or substituted, saturated or unsaturated, straight, branched and cyclic alkyl having from 1 to about 10 carbon atoms;(c)--A.sup.3 is selected from --C(CH.sub.3).sub.3, --Si(CH.sub.3).sub.3, and --CF.sub.3 ; and(d) --Y is selected from certain low molecular weight alkyl chains which terminate in specific unsaturated functional groups: ##STR2## and aldehydes in the form of their acetals; pharmaceutical compositions comprising such compounds; and methods for treating inflammation by administering such compounds.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: July 11, 1989
    Assignee: The Procter & Gamble Company
    Inventors: Maurice E. Loomans, Randall S. Matthews, Joseph A. Miller
  • Patent number: 4835323
    Abstract: New hydroquinones have the formula: ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2; R is a residue of formula: ##STR2## wherein Q is (i) -OX or (ii) -PO(OR.sub.11)((O).sub.x R.sub.11); and salts thereof with organic or inorganic acid bases.The groups X and R.sub.11 and x are defined hereinafter.The compounds of formula I are useful as stabilisers in photographic materials.
    Type: Grant
    Filed: September 11, 1986
    Date of Patent: May 30, 1989
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4760087
    Abstract: Phenol derivatives of the formula ##STR1## wherein A and B have the same or different meanings and each represent one of the groups --C.tbd.C--, cis--CH.dbd.CH-- or trans--CH.dbd.CH--, R.sub.1 is hydrogen, an optionally substituted alkyl or phenyl group or a cycloalkyl group, R.sub.2 is hydrogen, methyl or ethyl, R.sub.3 represents hydrogen, acetyl or propionyl, R.sub.4 has the same meaning as R.sub.3 or represents an alkyl group, R.sub.5 is a carboxylic or a hydroxy group or a functional derivative of such groups or R.sub.5 is a nitrile group and R.sub.6 is hydrogen, an alkyl group or the group OR.sub.4 which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds are prepared by reacting suitable acetylene compounds or metal derivatives thereof with alkyl or aryl halides or by means of Wittig reactions optionally followed by transforming the member R.sub.
    Type: Grant
    Filed: May 13, 1986
    Date of Patent: July 26, 1988
    Assignee: Gruenenthal GmbH
    Inventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin Kiesewetter, Ulrich G. P. Seipp
  • Patent number: 4754077
    Abstract: A process for making a 2,6-di-hydrocarbyl-4-alkoxyalkylphenol, e.g. 2,6-di-tert-butyl-4-methoxymethylphenol, by reacting a 2,6-dihydrocarbylphenol with formaldehyde in a stoichiometric excess of alcohol and in the presence of a Mannich base catalyst preferably formed in situ by adding a catalyst-forming amount of a secondary amine, e.g. dimethylamine, to the mixture of 2,6-di-hydrocarbylphenol, formaldehyde and alcohol. Unreacted alcohol and amine are distilled out and the 2,6-di-hydrocarbyl-4-alkoxyalkylphenol is reacted with a benzene-type compound, e.g. mesitylene, to make a hindered phenolic antioxidant, e.g. 1,3,5-trimethyl-2,4,6-tri-(3,5-di-tert-butyl-4-hydroxybenzyl)benzene.
    Type: Grant
    Filed: March 31, 1986
    Date of Patent: June 28, 1988
    Assignee: Ethyl Corporation
    Inventor: George L. Mina
  • Patent number: 4708966
    Abstract: The present invention relates to novel specifically-substituted phenyl compounds, especially substituted di-tert-butyl phenol derivatives, which are effective as anti-inflammatory, analgesic and/or antipyretic agents. These phenyl compounds are substituted with a low molecular weight alkyl chain which terminates in a specific unsaturated functional group. These unsaturated functionalities are --C.tbd.CH, C.dbd.CH.sub.2, C.dbd.C.dbd.CH.sub.2, and aldehydes in the form of their acetals.The present invention further relates to pharmaceutical compositions which contain an anti-inflammatory agent of the present invention and a pharmaceutically-acceptable carrier.Finally, the present invention relates to methods for treating diseases characterized by inflammation, such as rheumatoid arthritis and osteoarthritis, in humans or lower animals.
    Type: Grant
    Filed: June 27, 1986
    Date of Patent: November 24, 1987
    Assignee: The Procter & Gamble Company
    Inventors: Maurice E. Loomans, Randall S. Matthews, Joseph A. Miller
  • Patent number: 4694111
    Abstract: The production of a 1-hydroxy-2-lower alkoxyalkyl benzene, e.g. 2-(1'-methoxyethyl) phenol, is carried out by reacting phenol with a lower acetal or ketal, e.g., 1,1-dimethoxyethane at an elevated temperature in the presence of an H-ZSM-5 zeolite, as catalyst.
    Type: Grant
    Filed: July 9, 1986
    Date of Patent: September 15, 1987
    Assignee: Celanese Corporation
    Inventor: Balaram B. G. Gupta
  • Patent number: 4691048
    Abstract: The invention concerns a process for reducing carbonylation of an aldehyde wherein the aldehyde is used as hemiacetalester, the reaction being conducted in the presence of a catalyst consisting of a cobalt carbonyl complex.The hemiacetal-ester may be formed in situ by reacting an acetal with an anhydride of acid.The process preferentially yields alkylene-glycol mono-esters, free of esterified, for a ratio H.sub.2 /CO ranging from 1:1 to 3:1 and preferentially 2-alkoxy aldehydes, for a ratio H.sub.2 /CO ranging from 0.1:1 to 0.5:1.
    Type: Grant
    Filed: May 10, 1985
    Date of Patent: September 1, 1987
    Assignee: Institut Francais du Petrole
    Inventors: Francois Hugues, Dominique Commereuc, Yves Chauvin
  • Patent number: 4663489
    Abstract: The cobalt carbonyl catalyst R.sup.5 CCo.sub.3 (CO).sub.9, desirably with Ru.sub.3 (CO).sub.12, wherein R.sup.5 is hydrogen; alkyl, preferably C.sub.1-5 lower alkyl; cycloalkyl or substituted cycloalkyl; cycloalkenyl, such as cyclohexenyl or cyclooctenyl; C.sub.1-12 alkoxy, such as methoxy or propoxy; aryl or alkyl-, cycloalkyl-, alkoxy-, halo-, or cyano-substituted aryl; cyano; or a silyl carbyne moiety of the formula R.sub.3.sup.6 Si, wherein R.sup.6 is alkyl or aryl, effectively catalyzes the dealkoxyhydroxymethylation of aldehyde acetals to form glycol monoethers. Methylal, for example, may be reacted with syngas; i.e., CO and H.sub.2, in the presence of this catalyst system to form the corresponding ethylene glycol monomethyl ether.The novel catalyst combination of R.sup.5 CCo.sub.3 (CO).sub.9 and Ru.sub.3 (CO).sub.12 is likewise claimed herein.
    Type: Grant
    Filed: May 5, 1986
    Date of Patent: May 5, 1987
    Assignee: Sun Refining and Marketing Company
    Inventors: D. Michael Duggan, Harry K. Myers, Jr., James E. Lyons
  • Patent number: 4654327
    Abstract: A complex of a therapeutic agent is disclosed in which the therapeutic agent is complexed to an ammonium ion selected from the group consisting of ##STR1## where R.sup.1 and R.sup.2 are the same or different and are alkyl or hydroxy substituted alkyl containing 1 to 6 carbon atoms; andR, R' and R" are the same or different and are saturated or unsaturated aliphatics containing at least 10 carbon atoms, ##STR2## where R.sup.1, R.sup.2 and R" are as defined above, ##STR3## where R.sup.3 is independently alkyl or hydroxy substituted alkyl containing at least 10 carbon atoms; and R.sup.1, R.sup.2, R.sup.3 and R and R' have the meanings given above; and ##STR4## where R.sup.1, R.sup.2 and R.sup.3 have the meanings given above. The therapeutic agent is heparin, a biologically active peptide or protein or an antineoplastic drug. The therapeutic agent may also be covalently bonded to a triglyceride type backbone to form a compound.
    Type: Grant
    Filed: December 3, 1985
    Date of Patent: March 31, 1987
    Assignee: Research Corp.
    Inventor: Lin-nar L. Teng
  • Patent number: 4648984
    Abstract: 2-benzyl-1-alkanol polyglycol ethers having the formula: ##STR1## in which R.sup.1 is a C.sub.6 to C.sub.22 alkyl group; R.sup.2 is a C.sub.2 -C.sub.6 alkylene group; and n is an integer from 1 to about 100.The products are produced by heating a mixture of a ratio of an alcohol having the formula:R.sup.1 --CH.sub.2 --CH.sub.2 OHwherein the symbol R.sup.1 has the same meaning as above with a ratio of from about 1 mole to about 10 moles, preferably 1 to 3 moles, of benzyl alcohol to a temperature of from about 180.degree. C. to 250.degree. C. in the presence of an alkali metal compound, and optionally a hydrogenation catalyst; separating the excess benzyl alcohol from the mixture and alkoxylating the alcohol thus obtained.The polyglycol ether are used as wetting agents, dispersants, emulsifiers and detergents.
    Type: Grant
    Filed: May 29, 1986
    Date of Patent: March 10, 1987
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Horst-Jurgen Krause, Andreas Syldatk, Eric Sung
  • Patent number: 4633023
    Abstract: A fluoroacrylate ester monomer having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are independently selected from the group consisting of saturated aliphatic hydrocarbons having from 1 to about 3 carbon atoms and R.sub.3 is selected from the group consisting of hydrogen and methyl. The monomer has a water-repellent "umbrella" of 3 gem bis trifluoromethyl groups around the acrylate monomer which do not interfere with the acrylate properties. Polymerization of the monomer results in a stable, exceptionally hydrophobic, linear thermoplastic polymer. The invention also includes processes for making the monomer from a diether halide and certain novel intermediates.
    Type: Grant
    Filed: January 2, 1986
    Date of Patent: December 30, 1986
    Assignee: Geo-Centers, Inc.
    Inventors: James R. Griffith, Jacques G. O'Rear
  • Patent number: 4618627
    Abstract: A catechol derivative represented by the formula ##STR1## The compounds of this invention are useful for the prophylaxis and treatment for various allergic diseases, ischemic heart diseases and inflammations caused by slow reacting substance of anaphylaxis (SRS-A), since the compounds inhibit very potently the formation and release of SRS-A.
    Type: Grant
    Filed: May 11, 1984
    Date of Patent: October 21, 1986
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Kiyoshi Murase, Toshiyasu Mase, Hideki Arima, Kenichi Tomioka
  • Patent number: 4593129
    Abstract: A process for making an alkali metal alkoxide (e.g. sodium alkoxide) of a halogen-substituted alcohol (e.g. fluorine-substituted alcohols) by dispersing an alkali metal (e.g. sodium) in a cycloalkane (e.g. cyclohexane) containing a phenol (e.g. o-allylphenol) and adding the resultant dispersion to an ether (e.g. THF) solution of a halogen-substituted alcohol. The resultant alkali metal haloalkoxide solution contains phenoxides and can be reacted with a phosphonitrilic chloride polymer to introduce haloalkoxide and phenoxide substituents.
    Type: Grant
    Filed: April 18, 1984
    Date of Patent: June 3, 1986
    Assignee: Ethyl Corporation
    Inventors: R. Woodrow Wilson, Jr., Dustin H. Thomas
  • Patent number: 4588521
    Abstract: Described is the compound having the structure: ##STR1## as well as mixtures thereof with the compounds having the structures: ##STR2## and ##STR3## and a method for preparing same involving the reaction of the compound having the structure: ##STR4## with beta-phenylethyl alcohol having the structure: ##STR5## as well as uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders, hair preparations and perfumed polymers.
    Type: Grant
    Filed: May 11, 1984
    Date of Patent: May 13, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Joseph A. McGhie
  • Patent number: 4564476
    Abstract: Aryl fatty acid compounds of the formula (I) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, X, and Y are as defined herein are novel and useful in the treatment of allergic and inflammatory disorders.
    Type: Grant
    Filed: October 29, 1984
    Date of Patent: January 14, 1986
    Assignee: McNeilab, Inc.
    Inventor: Chih Y. Ho
  • Patent number: 4508925
    Abstract: There is disclosed a novel process for preparing a number of cinnamaldehyde derivatives. These cinnamaldehyde derivatives can be reduced to dihydrocinnamaldehyde derivatives, a number of which are commercially important in the preparation of fragrances. The invention is also directed to a number of novel intermediates and their preparation.
    Type: Grant
    Filed: November 9, 1983
    Date of Patent: April 2, 1985
    Assignee: Givaudan Corporation
    Inventors: Yvo Crameri, Paul A. Ochsner, Peter Schudel
  • Patent number: 4501687
    Abstract: Novel cyclopentanols of the formula ##STR1## wherein R.sub.1 and R.sub.2 are identical and are selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R.sub.3 is selected from the group consisting of --OH, alkoxy of 1 to 8 carbon atoms and acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms, R.sub.4 is selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms, R.sub.5 and R.sub.8 are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and alkenyl and alkynyl of 2 to 8 carbon atoms and R.sub.6 and R.sub.7 are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, --CN, --COCH.sub.3 and --COOAlK.sub.2 and AlK.sub.2 is alkyl of 1 to 8 carbon atoms useful as perfumery agents and their preparation and novel intermediates.
    Type: Grant
    Filed: November 30, 1981
    Date of Patent: February 26, 1985
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Buendia, Francois Nezot
  • Patent number: 4484009
    Abstract: A process for the manufacture of the monoether of monoethylene glycol by the hydrogenolysis of a 2-alkyl-1,3-dioxolane, with a co-catalytic system of palladium and an acid of phosphorus or a phosphoric ester of ethylene glycol and in the presence of ethylene glycol.
    Type: Grant
    Filed: April 4, 1983
    Date of Patent: November 20, 1984
    Assignee: Atochem
    Inventors: Elie Ghenassia, Andre Lakodey
  • Patent number: 4476327
    Abstract: A process for the synthesis of glycol monomethylethers consisting of reacting an olefin compound, methanol and hydrogen peroxide in aqueous solution in the presence of synthetic zeolites containing titanium atoms, of general formula:xTiO.sub.2.(1-x)SiO.sub.2,where x lies between 0.0001 and 0.04.
    Type: Grant
    Filed: July 14, 1983
    Date of Patent: October 9, 1984
    Assignee: Anic S.p.A.
    Inventors: Carlo Neri, Franco Buonomo, Bartolomeo Anfossi
  • Patent number: 4468527
    Abstract: A fluoroaliphatic radical- and aliphatic chlorine-containing alcohol containing more than 25 weight percent carbon-bonded fluorine in the form of fluoroaliphatic radicals and at least one aliphatic chlorine, an ester of said alcohol and a carboxycylic acid being useful in the treatment of carpet.
    Type: Grant
    Filed: March 15, 1982
    Date of Patent: August 28, 1984
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Kalyanji U. Patel
  • Patent number: 4454330
    Abstract: A process for the preparation of a two-functional-group-containing terpenoid having the general formula: ##STR1## in which n is an integer of from 1 to 5, R represents a hydroxymethyl, formyl or carboxyl group, and A represents the hydrogen atom, or a 2-tetrahydropyranyl, benzyl, methoxymethol or methoxyethoxymethyl group comprising the oxidation with a microorganism belonging to the genus Nocardia. Some of the terpenoids are of value as anti-ulcer agents, while others are useful as intermediates.
    Type: Grant
    Filed: March 22, 1982
    Date of Patent: June 12, 1984
    Assignees: Eisai Co., Ltd., General Director of the Agency of Industrial Science and Technology
    Inventors: Akio Sato, Kenji Nakajima, Yoshimasa Takahara, Shizumasa Kijima, Noriaki Kuwana, Shinya Abe, Kouzi Yamada
  • Patent number: 4433179
    Abstract: A process for the preparation of allyl ethers of the formulaR--O--CH.sub.2 --CH.dbd.CH.sub.2).sub.nin which R and n are as defined in claim 1, by reacting hydroxy compounds of the formulaR--OH).sub.nwith allyl chloride or allyl bromide by phase transfer catalysis, 0.8 to 5 mols of allyl chloride or allyl bromide, 1 to 6 mols of aqueous or solid sodium hydroxide and, as the phase transfer catalyst, 2 to 20 mol % of a quaternary ammonium salt, a quaternary ammonium base or a crown ether being employed per hydroxyl equivalent of the compound of the formula II, and the reaction being carried out in the temperature range from 20.degree. to 100.degree. C.
    Type: Grant
    Filed: August 17, 1981
    Date of Patent: February 21, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Friedrich Lohse, Charles E. Monnier
  • Patent number: 4431845
    Abstract: A method for the preparation of hydroxyl-terminated poly(haloalkylene ethers) is disclosed wherein a catalyst system comprising a fluorinated acid and a polyvalent tin compound is utilized.
    Type: Grant
    Filed: March 5, 1982
    Date of Patent: February 14, 1984
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Chung I. Young, Loren L. Barber, Jr.
  • Patent number: 4385190
    Abstract: A process for the production of a mono- or poly-alkylene glycol diether which consists of reacting an ether having at least one lower alkyl group with alkylene oxide in the presence of a heteropoly acid or a heteropoly acid acidic salt. Heteropoly acids and their acidic salts whose ratio of the hetero and coordinate atom is 1:6 and 1:12 are preferably used.
    Type: Grant
    Filed: May 11, 1981
    Date of Patent: May 24, 1983
    Assignee: Nisso Petrochemical Industry Company Limited
    Inventors: Yu Ohashi, Norio Sone, Takashi Tobita
  • Patent number: 4385185
    Abstract: Compounds of the general formula I: ##STR1## wherein R.sub.1 and R.sub.2 are equal or different alkyl-, alkoxyalkyl-, or aryl groups, or together form a ring; R.sub.3 is an allyl or benzyl radical; and R.sub.4 and R.sub.5 represent hydrogen, alkyl, alkoxyalkyl, alkenyl or further compounds of the formula II: ##STR2## wherein R.sub.1, R.sub.2, R.sub.4 and R.sub.5 have the meaning indicated above and R.sub.6 stands for hydrogen or methyl or to compounds which are modified by the addition of hydrogen to at least one olefinic or carbonylic double bond of compounds of the general formula I or II. The invention also relates to a process for preparing the new compounds. The compounds of the general formula II are obtained by thermal treatment of a selection of compounds of formula I, for which R.sub.3 stands for the allyl or methallyl radical. The compounds according to the invention are used as fragrant and flavoring substances.
    Type: Grant
    Filed: March 20, 1981
    Date of Patent: May 24, 1983
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Helmut Gebauer, Walter Hafner
  • Patent number: 4360698
    Abstract: A process to form glycol ethers by reacting an organic compound (A) having at least one aliphatic hydroxyl group with an oxirane compound (B) under reaction conditions in the presence of a catalytic amount of a polymeric material that is substantially insoluble in the reaction mixture, said polymeric material having a plurality of pendant sulfonate moieties with divalent metal counterions. Preferential formation of the mono adduct of glycol ethers is noted.
    Type: Grant
    Filed: July 22, 1981
    Date of Patent: November 23, 1982
    Assignee: The Dow Chemical Company
    Inventor: James H. Sedon
  • Patent number: 4357280
    Abstract: A method of processing photographic silver dye bleach materials which have been exposed imagewise is provided. The process steps are (1) silver developing, (2) dye bleaching, (3) silver bleaching and (4) fixing. The treatment baths for the process steps (2), (3) and (4), or the combined treatment baths useful for process step (3) with at least one the process steps (2) or (4) contain water-soluble tertiary phosphines as silver ligands. These phosphines effect an acceleration of the dye and silver bleaching and they are further suitable stabilizers and optionally antioxidants which yield stable treatment baths.
    Type: Grant
    Filed: May 29, 1981
    Date of Patent: November 2, 1982
    Assignee: Ciba-Geigy AG
    Inventors: Christoph Chylewski, Gerald Jan, Roland Kurzen, Max Meier, Matthias Schellenberg
  • Patent number: 4338239
    Abstract: This invention provides a novel polyacrylate thickening agent which is composed of monomers comprising (1) (meth)acrylic acid, (2) glyceryl allyl ether derivative, and optionally (3) one or more other polymerizable monomers.In another embodiment, this invention provides a print paste containing the defined novel polyacrylate thickening agent.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: July 6, 1982
    Assignee: Celanese Corporation
    Inventor: Laurence G. Dammann