Polyoxy Patents (Class 568/662)
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Patent number: 5292927Abstract: 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: GrantFiled: February 26, 1992Date of Patent: March 8, 1994Assignee: The United States of America as represented by the Secretary of the NavyInventors: James R. Griffith, Henry S. W. Hu
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Patent number: 5210322Abstract: A process for preparing ethers which comprises contacting a carboxylated ether with a metal oxide catalyst under conditions effective to produce the ether.Type: GrantFiled: September 20, 1990Date of Patent: May 11, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Kurt D. Olson
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Patent number: 5196569Abstract: 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: GrantFiled: October 10, 1991Date of Patent: March 23, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ming-Hong Hung
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Patent number: 5189204Abstract: 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: GrantFiled: June 25, 1991Date of Patent: February 23, 1993Assignee: Showa Shell Sekiyu Kabushiki KaishaInventors: Tomoya Kitazumo, Takashi Yamazaki, Hitoshi Iwatsubo
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Patent number: 5130435Abstract: 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: GrantFiled: August 9, 1990Date of Patent: July 14, 1992Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
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Patent number: 5130462Abstract: 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: GrantFiled: February 19, 1991Date of Patent: July 14, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: William A. Slusarchyk, Robert Zahler
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Patent number: 5107034Abstract: 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: GrantFiled: March 28, 1990Date of Patent: April 21, 1992Assignee: Hoechst Celanese CorporationInventors: Brad L. Smith, Werner H. Mueller, Heinz Strutz
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Patent number: 5106885Abstract: 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: GrantFiled: November 3, 1989Date of Patent: April 21, 1992Assignee: ISP Investments Inc.Inventors: Kou-Chang Liu, Fulvio J. Vara, James A. Dougherty
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Patent number: 5104987Abstract: This invention relates to a process for the alkoxylation of an active hydrogen-containing compound comprising contacting the active hydrogen-containing compound with an alkylene carbonate in the presence of a mixed metal oxide catalyst under conditions effective to alkoxylate the active hydrogen-containing compound.Type: GrantFiled: September 20, 1990Date of Patent: April 14, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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Patent number: 5095153Abstract: 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: GrantFiled: October 11, 1990Date of Patent: March 10, 1992Assignee: HIMONT IncorporatedInventors: Giovanni Agnes, Giampietro Borsotti, Giuliana Schimperna, Elisabetta Barbassa
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Patent number: 5011943Abstract: 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: GrantFiled: August 28, 1989Date of Patent: April 30, 1991Assignee: Merck Frosst Canada, Inc.Inventor: Zhaoyin Wang
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Patent number: 4981989Abstract: 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: GrantFiled: November 8, 1989Date of Patent: January 1, 1991Assignee: American Cyanamid CompanyInventors: Allan Wissner, Phaik E. Sum, Robert E. Schaub
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Patent number: 4971995Abstract: 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: GrantFiled: January 26, 1989Date of Patent: November 20, 1990Assignee: Delande S.A.Inventors: Alain R. Schoofs, Michel Langlois, Christian R. Jeanpetit, Maryse F. Masson
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Patent number: 4968836Abstract: 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: GrantFiled: January 30, 1990Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventors: Hans-Ruedi Kanel, John G. Dingwall
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Patent number: 4965376Abstract: 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: GrantFiled: April 18, 1989Date of Patent: October 23, 1990Assignee: BASF AktiengesellschaftInventors: Michael Huellmann, Rainer Becker, Gerald Lauterbach, Ernst Buschmann, Heinz Eckhardt, Walter Himmele, Christiane Brueckner
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Patent number: 4960884Abstract: 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: GrantFiled: August 28, 1989Date of Patent: October 2, 1990Assignee: FMC CorporationInventors: David M. Roush, Donald A. Shaw, Michael L. Jones, Jun H. Chang
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Patent number: 4959391Abstract: 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: GrantFiled: July 14, 1988Date of Patent: September 25, 1990Assignee: Gruenenthal GmbHInventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin O. Kiesewetter, Ulrich G. P. Seippl
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Patent number: 4952736Abstract: 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: GrantFiled: January 24, 1990Date of Patent: August 28, 1990Assignee: Idemitsu Petrochmeical Company, LimitedInventor: Masahiro Iwahara
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Patent number: 4918219Abstract: 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: GrantFiled: September 29, 1989Date of Patent: April 17, 1990Assignee: Warner-Lambert CompanyInventors: Jagadish C. Sircar, Charles F. Schwender, Mark J. Suto
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Patent number: 4915875Abstract: 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: GrantFiled: November 4, 1986Date of Patent: April 10, 1990Assignee: The Dow Chemical CompanyInventors: Timothy R. Diephouse, Robert M. Strom
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Patent number: 4916252Abstract: 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: GrantFiled: June 16, 1988Date of Patent: April 10, 1990Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 4895987Abstract: 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: GrantFiled: June 6, 1986Date of Patent: January 23, 1990Assignee: Sun Refining and Marketing CompanyInventors: D. Michael Duggan, James E. Lyons, Harry K. Myers, Robert E. Ledley
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Patent number: 4847303Abstract: 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: GrantFiled: November 23, 1987Date of Patent: July 11, 1989Assignee: The Procter & Gamble CompanyInventors: Maurice E. Loomans, Randall S. Matthews, Joseph A. Miller
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Patent number: 4835323Abstract: 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: GrantFiled: September 11, 1986Date of Patent: May 30, 1989Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4760087Abstract: 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: GrantFiled: May 13, 1986Date of Patent: July 26, 1988Assignee: Gruenenthal GmbHInventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin Kiesewetter, Ulrich G. P. Seipp
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Patent number: 4754077Abstract: 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: GrantFiled: March 31, 1986Date of Patent: June 28, 1988Assignee: Ethyl CorporationInventor: George L. Mina
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Patent number: 4708966Abstract: 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: GrantFiled: June 27, 1986Date of Patent: November 24, 1987Assignee: The Procter & Gamble CompanyInventors: Maurice E. Loomans, Randall S. Matthews, Joseph A. Miller
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Patent number: 4694111Abstract: 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: GrantFiled: July 9, 1986Date of Patent: September 15, 1987Assignee: Celanese CorporationInventor: Balaram B. G. Gupta
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Patent number: 4691048Abstract: 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: GrantFiled: May 10, 1985Date of Patent: September 1, 1987Assignee: Institut Francais du PetroleInventors: Francois Hugues, Dominique Commereuc, Yves Chauvin
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Patent number: 4663489Abstract: 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: GrantFiled: May 5, 1986Date of Patent: May 5, 1987Assignee: Sun Refining and Marketing CompanyInventors: D. Michael Duggan, Harry K. Myers, Jr., James E. Lyons
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Patent number: 4654327Abstract: 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: GrantFiled: December 3, 1985Date of Patent: March 31, 1987Assignee: Research Corp.Inventor: Lin-nar L. Teng
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Patent number: 4648984Abstract: 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: GrantFiled: May 29, 1986Date of Patent: March 10, 1987Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Horst-Jurgen Krause, Andreas Syldatk, Eric Sung
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Patent number: 4633023Abstract: 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: GrantFiled: January 2, 1986Date of Patent: December 30, 1986Assignee: Geo-Centers, Inc.Inventors: James R. Griffith, Jacques G. O'Rear
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Patent number: 4618627Abstract: 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: GrantFiled: May 11, 1984Date of Patent: October 21, 1986Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Kiyoshi Murase, Toshiyasu Mase, Hideki Arima, Kenichi Tomioka
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Patent number: 4593129Abstract: 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: GrantFiled: April 18, 1984Date of Patent: June 3, 1986Assignee: Ethyl CorporationInventors: R. Woodrow Wilson, Jr., Dustin H. Thomas
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Patent number: 4588521Abstract: 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: GrantFiled: May 11, 1984Date of Patent: May 13, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Joseph A. McGhie
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Patent number: 4564476Abstract: 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: GrantFiled: October 29, 1984Date of Patent: January 14, 1986Assignee: McNeilab, Inc.Inventor: Chih Y. Ho
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Patent number: 4508925Abstract: 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: GrantFiled: November 9, 1983Date of Patent: April 2, 1985Assignee: Givaudan CorporationInventors: Yvo Crameri, Paul A. Ochsner, Peter Schudel
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Patent number: 4501687Abstract: 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: GrantFiled: November 30, 1981Date of Patent: February 26, 1985Assignee: Roussel UclafInventors: Jacques Martel, Jean Buendia, Francois Nezot
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Patent number: 4484009Abstract: 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: GrantFiled: April 4, 1983Date of Patent: November 20, 1984Assignee: AtochemInventors: Elie Ghenassia, Andre Lakodey
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Patent number: 4476327Abstract: 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: GrantFiled: July 14, 1983Date of Patent: October 9, 1984Assignee: Anic S.p.A.Inventors: Carlo Neri, Franco Buonomo, Bartolomeo Anfossi
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Patent number: 4468527Abstract: 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: GrantFiled: March 15, 1982Date of Patent: August 28, 1984Assignee: Minnesota Mining and Manufacturing CompanyInventor: Kalyanji U. Patel
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Patent number: 4454330Abstract: 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: GrantFiled: March 22, 1982Date of Patent: June 12, 1984Assignees: Eisai Co., Ltd., General Director of the Agency of Industrial Science and TechnologyInventors: Akio Sato, Kenji Nakajima, Yoshimasa Takahara, Shizumasa Kijima, Noriaki Kuwana, Shinya Abe, Kouzi Yamada
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Patent number: 4433179Abstract: 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: GrantFiled: August 17, 1981Date of Patent: February 21, 1984Assignee: Ciba-Geigy CorporationInventors: Friedrich Lohse, Charles E. Monnier
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Patent number: 4431845Abstract: 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: GrantFiled: March 5, 1982Date of Patent: February 14, 1984Assignee: Minnesota Mining and Manufacturing CompanyInventors: Chung I. Young, Loren L. Barber, Jr.
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Patent number: 4385190Abstract: 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: GrantFiled: May 11, 1981Date of Patent: May 24, 1983Assignee: Nisso Petrochemical Industry Company LimitedInventors: Yu Ohashi, Norio Sone, Takashi Tobita
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Patent number: 4385185Abstract: 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: GrantFiled: March 20, 1981Date of Patent: May 24, 1983Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Helmut Gebauer, Walter Hafner
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Patent number: 4360698Abstract: 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: GrantFiled: July 22, 1981Date of Patent: November 23, 1982Assignee: The Dow Chemical CompanyInventor: James H. Sedon
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Patent number: 4357280Abstract: 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: GrantFiled: May 29, 1981Date of Patent: November 2, 1982Assignee: Ciba-Geigy AGInventors: Christoph Chylewski, Gerald Jan, Roland Kurzen, Max Meier, Matthias Schellenberg
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Patent number: 4338239Abstract: 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: GrantFiled: March 30, 1981Date of Patent: July 6, 1982Assignee: Celanese CorporationInventor: Laurence G. Dammann