Esterified Phenolic Hydroxy Patents (Class 560/130)
  • Patent number: 5151546
    Abstract: A method for producing 4-acetoxystyrene by heating 4-acetoxyphenylmethylcarbinol, with an acid catalyst, at a temperature of from about 85.degree. C. to about 300.degree. C. under a pressure of from about 0.1 mm HgA to about 760 mm HgA for from about 0.2 minutes to about 10 minutes. The process also provides for the solventless (neat) hydrogenation of 4-acetoxyacetophenone to produce 4-acetoxyphenylmethylcarbinol. The reaction proceeds by heating at 54.degree. C. to 120.degree. C. with an excess of hydrogen in the presence of a Pd/C or activated nickel such as Raney Nickel catalyst in the absence of a solvent. The 4-acetoxyphenylmethylcarbinol may then be dehydrated to 4-acetoxystyrene. The later may be polymerized to poly(4-acetoxystyrene) and hydrolyzed to poly(4-hydroxystyrene).
    Type: Grant
    Filed: October 15, 1990
    Date of Patent: September 29, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Bakulesh N. Shah, Dung Q. Tran, Donna L. Keene
  • Patent number: 5142095
    Abstract: The present invention is novel diarylalkanoids having activity as lipoxygenase inhibitors, novel pharmaceutical compositions therefor, and novel methods of use in treating asthma, allergies, cardiovascular diseases, migraines, psoriasis and immunoinflammatory diseases for diarylalkanoids. The compounds of this invention are also useful as cytoprotective agents.
    Type: Grant
    Filed: August 17, 1989
    Date of Patent: August 25, 1992
    Assignee: Warner-Lambert Company
    Inventors: David T. Connor, Daniel L. Flynn
  • Patent number: 5136084
    Abstract: A novel process for the acetylation of a mono-substituted phenol or a mono-substituted naphthol is disclosed which comprises reacting the said mono-substituted phenol or the said mono-substituted naphthol respectively with vinyl acetate at a temperature of not more than 160.degree. C.
    Type: Grant
    Filed: June 14, 1991
    Date of Patent: August 4, 1992
    Assignee: San Fu Chemical Co., Ltd.
    Inventors: Shu-Chung Lin, Min-Hon Rei
  • Patent number: 5136083
    Abstract: The present invention relates to a process for the purification of 4-acetoxystyrene from a crude product mixture comprising 4-acetoxystyrene and typically 5 or more contaminants in substantial amount.The crude product mixture is purified by melt crystallization by cooling the mixture to a temperature ranging from about +8.degree. C. to about -50.degree. C., whereby at least a first portion of the mixture is crystallized; removing the liquid remaining from contact with the crystallized first portion of the mixture; and, subsequently slowly heating the crystallized first portion, while simultaneously removing liquid which forms due to the heating, whereby impurities contained in the liquid which forms are removed from the crystallized first portion.Surprisingly, despite the large number of contaminants present, and use of the process to purify crude product mixtures containing as little as 50% by weight 4-acetoxystyrene, purities as high as 99.
    Type: Grant
    Filed: August 30, 1990
    Date of Patent: August 4, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Jack Chosnek, George E. Beck, Donna L. Keene, Siegbert Rittner, Volker Hautzel
  • Patent number: 5117035
    Abstract: A novel fluorine-containing acrylic acid derivative of the invention is represented by the formula:(CH.sub.2 .dbd.CF--CO).sub.p --A (I)wherein A is a residue derived from an organic compound having at least two active hydrogen atoms derived by removing at least two active hydrogen atoms, and p is an integer corresponding to the valency of the residue A, which is easily cured.
    Type: Grant
    Filed: May 24, 1989
    Date of Patent: May 26, 1992
    Assignee: Daikin Industries, Ltd.
    Inventors: Shigeru Morita, Masahiko Oka
  • Patent number: 5096994
    Abstract: The present invention relates to polyisocyanates which contain ester groups and havea) a content of aliphatically bound isocyanate groups of 18 to 33% by weight,b) an average NCO functionality of 4.1 to 10, preferably from 4.5 to 10, andc) a viscosity of 200 to 2,5000 mPa.s at 22.degree. C.The present invention also relates to preferred polyisocyanates which contain ester groups and havea) a content of aliphatically bound isocyanate groups of 20 to 33% by weight,b) an average NCO functionality of 5 to 8 andc) a viscosity of 500 to 1,000 mPa.s at 22.degree. C.The present invention further relates to a process for the preparation of these preferred polyisocyanates by reacting isocyanatocarboxylic acid chlorides with O-silylated, polyhydric alcohols at a temperature of about 50.degree. to 150.degree. C. Finally, the present invention relates to the use of the polyisocyanates as the isocyanate component for two-component polyurethane coating compositions.
    Type: Grant
    Filed: August 2, 1990
    Date of Patent: March 17, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Lutz Schmalstieg, Josef Pedain, Klaus Nachtkamp, Lothar Kahl, Manfred Schonfelder
  • Patent number: 5073299
    Abstract: Compounds having the formula I: ##STR1## wherein M.sub.1, M.sub.2, M.sub.3 , independently, are hydrogen, C.sub.1 -C.sub.4 alkkyl, phenyl, a monovalent or an equivalent of a polyvalent metal atom, ammonium or a substituted ammonium ion; R.sub.1 is C.sub.1 -C.sub.4 alkyl substituted by one or more hydroxy or carboxyl groups; and p is an integer.The new compounds are useful in the treatment of aqueous systems, in particular to inhibit scale deposition from aqueous systems.
    Type: Grant
    Filed: September 19, 1989
    Date of Patent: December 17, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Barry Cook
  • Patent number: 5072025
    Abstract: 3-substituted-4-hydroxy- and 4-acetoxystyrene compounds, especially 3,5-di(methyl, bromo or chloro)-4-acetoxystyrene as well as a process for its preparation. 2,6-dimethylphenol is acylated with acetic anhydride and HF catalyzed to produce 3,5-dimethyl-4-hydroxy-acetophenone. After subsequent esterification with acetic anhydride and catalyzed hydrogenation to form 1-(3',5'-dimethyl-4'-acetoxyphenyl)ethanol, this intermediate is then dehydrated with an acid and a polymerization inhibitor to produce 3,5-dimethyl-4-acetoxystyrene.
    Type: Grant
    Filed: July 26, 1990
    Date of Patent: December 10, 1991
    Assignee: Hoechst Celanese Corporation
    Inventors: Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
  • Patent number: 5041614
    Abstract: A method for the preparation of 4-acetoxystyrene is disclosed. The method comprises heating 4'-acetoxyphenylmethylcarbinol in the presence of a suitable acid anhydride and a suitable dehydration catalyst in a continuous feed reaction mode to make the 4-acetoxystyrene.
    Type: Grant
    Filed: July 3, 1990
    Date of Patent: August 20, 1991
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Charles B. Hilton
  • Patent number: 5013854
    Abstract: An improved process for preparing trialkylsilyl ester and acid halide derivatives of carboxylic acids is provided along with novel trialkylsilyl ester intermediates of 2-(2-furyl)-2-methoximinoacetic acid.
    Type: Grant
    Filed: February 2, 1989
    Date of Patent: May 7, 1991
    Assignee: Eli Lilly and Company
    Inventor: Charles A. Bunnell
  • Patent number: 5001152
    Abstract: The invention is concerned with the new use of known catechol derivatives of the formula ##STR1## wherein R.sub.1 and R.sub.2 are each hydrogen, alkyl having 1 to 4 carbon atoms or alkanoyl having 2 to 5 carbon atoms; X is nitro, halogen or cyano and R.sub.3 is chlorine, nitro, cyano or a radical of the formula ##STR2## wherein R.sub.4 is hydrogen, cyano, alkyl having 1 to 4 carbon atoms or alkanoyl having 2 to 5 carbon atoms and R.sub.5 is cyano, alkanoyl having 2 to 5 carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms, carboxyl or phenylcarbonyl unsubstituted or substituted with one to three methoxy groups or pharmaceutically acceptable salt thereof. The new use is the treatment and prophylaxis of ulcers and lesions in the gastrointestinal tract.
    Type: Grant
    Filed: December 23, 1988
    Date of Patent: March 19, 1991
    Assignee: Orion Corporation Ltd.
    Inventors: Paivi A. Aho, Pentti Pohto, Inge-Britt Y. Linden, Reijo J. Backstrom, Erkki J. Honkanen, Erkki A. O. Nissenen
  • Patent number: 4990660
    Abstract: Aromatic hydroxycarboxylic acids of the formula(HO--).sub.n A--COOHwhere n is 1 or 2 and A is a radical from the benzene, naphthalene, biphenyl, diphenyl ether, diphenyl sulfide or diphenyl sulfone series, are prepared by a process in which an acylated aromatic compound of the formula(R.sup.1 --CO--O--).sub.n A--CO--R.sup.2where R.sup.1 and R.sup.2 independently of one another are each unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl and n and A each have the abovementioned meanings, is oxidized with oxygen in the presence of a catalyst and of a solvent at from 20.degree. to 250.degree. C. to give a carboxylic acid of the formula(R.sup.1 --CO--O--).sub.n A--COOHwhere R.sup.1, n and A have the abovementioned meanings, and the acyl group or groups is or are then eliminated.
    Type: Grant
    Filed: December 21, 1988
    Date of Patent: February 5, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Neumann, Ulrich Eichenauer
  • Patent number: 4990458
    Abstract: A process for forming derivatives of organic compounds as a step during their analysis. A macroreticular resin is used as both an adsorbent for the analyte and the derivatizing reagent and also as a catalyst for the derivatization reaction. Subsequent serial elution of the absorbed compounds leads to simple separation of the derivatized analyte from the starting materials. Further, the resin impregnated with derivatizing reagent can be used to combine the extraction and derivatization of the analyte. As macroreticular resins are relatively inexpensive, they result in reduced costs compared with conventional catalysts, and their ease of separation from liquid systems makes them easy to use and makes it possible to automate the procedure.
    Type: Grant
    Filed: September 22, 1987
    Date of Patent: February 5, 1991
    Assignee: McMaster University
    Inventor: Jack M. Rosenfeld
  • Patent number: 4985198
    Abstract: A tooth-adhesive compound is expressed in terms of the following general formula: ##STR1## wherein R.sub.1 is a hydrogen atom or a methyl group, andR.sub.2 may or may not be present; and if present, R.sub.2 is an alkylene group having 1 to 4 carbon atoms or a --CH.sub.2 --CH.sub.2).sub..eta. O--CH.sub.2 --CH.sub.2 -- group in which n=1 or 2, and a substituent containing R.sub.1 and R.sub.2 is located at the o-, m- or p-position with respect to the carboxyl group bonded to the phenyl group.
    Type: Grant
    Filed: March 7, 1989
    Date of Patent: January 15, 1991
    Assignee: G-C Dental Industrial Corp.
    Inventors: Tadashi Hirasawa, Ikuro Harashima
  • Patent number: 4985589
    Abstract: A method is provided for converting 4-substituted biphenyls, such as 4-hydroxybiphenyl, to the corresponding 3,4'-dihydroxybiphenyl utilizing mutant strains of Alcaligenes eutrophus or Pseudomonas putida. Hydroxylation of the unsubstituted biphenyl ring to the corresponding (1S-cis)-3-(4-hydroxyphenyl)-3,5-cyclohexadiene-1,2-diol and its conversion to the corresponding triacetate, followed by treatment in base to form 3,4'-dihydroxybiphenyl is also provided.
    Type: Grant
    Filed: August 1, 1990
    Date of Patent: January 15, 1991
    Assignee: General Electric Company
    Inventors: Bruce F. Johnson, Frank J. Mondello
  • Patent number: 4982006
    Abstract: The present invention involves process for the preparation of compounds having the chemical structure: ##STR1## wherein Ar--H is an aromatic compound which is activated to an electrophilic attack, and wherein --Y is an aliphatic group having a labile moiety, especially where the labile moiety is a terminally unsaturated moiety: --C.tbd.CH, ##STR2## or aldehydes in the form of their acetals. The process comprises the step of reacting Ar--H and ##STR3## wherein --X is --Cl or --Br, and where the reaction step is carried out in a solvent medium at a temperature of from about -40.degree. C. to about -100.degree. C. using stannic chloride as a catalyst.
    Type: Grant
    Filed: May 1, 1989
    Date of Patent: January 1, 1991
    Assignee: Norwich Eaton Pharmaceuticals, Inc.
    Inventor: Thomas T. Hudec
  • 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: 4965400
    Abstract: 3-substituted-4-hydroxy- and 4-acetoxystyrene compounds, especially 3,5-di(methyl, bromo or chloro)-4-acetoxystyrene as well as a process for its preparation. 2,6-dimethylphenol is acylated with acetic anhydride and HF catalyzed to produce 3,5-dimethyl-4-hydroxy-acetophenone. After subsequent esterification with acetic anhydride and catalyzed hydrogenation to form 1-(3',5'-dimethyl-4'-acetoxyphenyl)ethanol, this intermediate is then dehydrated with an acid and a polymerization inhibitor to produce 3,5-dimethyl-4-acetoxystyrene.
    Type: Grant
    Filed: August 2, 1988
    Date of Patent: October 23, 1990
    Inventors: Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
  • 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: 4959187
    Abstract: The invention provides novel bleaching compositions comprising peracid precursors with the general structure ##STR1## with R, R', R" and L as defined in the specification. Novel peracids and precursors are also herein disclosed. These peracid precursors provide new, proficient and cost-effective compounds for fabric bleaching.
    Type: Grant
    Filed: October 14, 1988
    Date of Patent: September 25, 1990
    Assignee: The Clorox Company
    Inventors: Ronald A. Fong, Sheldon N. Lewis, Richard J. Wiersema, Alfred G. Zielske
  • Patent number: 4927956
    Abstract: 3-substituted-4-hydroxy- and 4-acetoxystyrene compounds, especially 3,5-di(methyl, bromo or chloro)-4-acetoxystyrene as well as a process for its preparation. 2,6-dimethylphenol is acylated with acetic anhydride and HF catalyzed to produce 3,5-dimethyl-4-hydroxy-acetophenone. After subsequent esterification with acetic anhydride and catalyzed hydrogenation to form 1-(3',5'-dimethyl-4'-acetoxyphenyl)ethanol, this intermediate is then dehydrated with an acid and a polymerization inhibitor to produce 3,5-dimethyl-4-acetoxystyrene.
    Type: Grant
    Filed: June 2, 1989
    Date of Patent: May 22, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
  • Patent number: 4918213
    Abstract: An optically active, generally mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sub.1 denotes an alkyl group having 1-18 carbon atoms, R.sub.2 denotes an alkyl group having 1-12 carbon atoms; X denotes a single bond, --O--, ##STR2## Y denotes a single bond, ##STR3## --CH.sub.2 O-- or --OCH.sub.2 --; Z denotes --OCH.sub.2 --, ##STR4## respectively denotes ##STR5## C* denotes an asymmetric carbon atom; k, m and n are respectively 0, 1 or 2 with proviso that k+m+n amounts to 2 or 3; and p is 1 or 2.
    Type: Grant
    Filed: July 25, 1988
    Date of Patent: April 17, 1990
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Yoko Yamada, Yuko Etoh
  • Patent number: 4897420
    Abstract: Compounds of the formula: ##STR1## wherein l is an integer of 0 to 18, X is hydrogen, an alkyl having 1 to 4 carbon atoms or a carboxylic acyl having 2 to 4 carbon atoms and Y is a phenylene, a cycloalkylene having 3 to 7 carbon atoms or a group of the formula: ##STR2## in which m is an integer of 0 to 3, and R.sub.1 and R.sub.2 each is an alkyl having 1 to 4 carbon atoms, are novel compounds, possess circulatory disturbance-improving activity and inhibitory activity of the generation and release of SRS-A, and used for prophylactic or therapy of ischemic diseases such as cerebral apoplexy or allergic diseases.
    Type: Grant
    Filed: December 5, 1988
    Date of Patent: January 30, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Masazumi Watanabe, Isuke Imada
  • Patent number: 4873018
    Abstract: An optically active 2-fluoro-1-alkanol compound represented by the formula (Ia): ##STR1## wherein R is an alkyl group having 1-16 carbon atoms, and C* is an asymmetric carbon atom; and an optically active compound derived from the fluoroalkanol and represented by the formula (Ib): ##STR2## wherein R and C* are the same as above, m is 1 or 2, n is 0 or 1, and A is a releasable substitutent. Because of the fluorine atom directly attached to an asymmetric carbon atom, these compounds are particularly effective in increasing a spontaneous polarization, improving a electric field responsive characteristic of a liquid crystal composition, and controlling the liquid crystal state.
    Type: Grant
    Filed: October 27, 1987
    Date of Patent: October 10, 1989
    Assignees: Canon Kabushiki Kaisha, Yamakawa Yakuhin Kogyo Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuo Yoshinaga, Mariko Kai, Kazuharu Katagiri
  • Patent number: 4873361
    Abstract: A liquid-phase process is disclosed for oxidation of p-acetoxyacetophenone to p-acetoxybenzoic acid in high yield in a solvent in the presence of a catalyst and addition of a promoter comprising an acid anhydride of a lower aliphatic carboxytlic acid at an addition rate within specified mole ratio limits, a temperature within the range of from about 200.degree. F. to about 400.degree. F., and a pressure within the range of from about 1 atmosphere to 30 atmospheres. A first portion of the promoter is added at the start of the process, and a second portion of the promoter is added during the process.
    Type: Grant
    Filed: August 29, 1988
    Date of Patent: October 10, 1989
    Assignee: Amoco Corporation
    Inventor: Krisati A. Fjare
  • Patent number: 4868329
    Abstract: The instant invention involves a process for preparing carboxylic acid esters which comprises coreacting a carboxylic acid and an aliphatic mono or polyol by maintaining one of the reactants in a reactor at elevated temperatures and adding the other reactant to the reactor over a period of time. By employing this process esterification times are significantly reduced.
    Type: Grant
    Filed: March 7, 1988
    Date of Patent: September 19, 1989
    Assignee: Hoechst Celanese Corp.
    Inventors: Thomas M. Powanda, Robert H. Imes, George L. Collins
  • Patent number: 4776875
    Abstract: Compounds of the formula ##STR1## in which R.sub.1 and R.sub.2 denote alkyl, OH, CF.sub.3 or cyanoethyl, A preferably denotes --COOH, R.sub.3 denotes inter alia alkoxycarbonylalkoxy, fairly high-molecular (>C.sub.12) alkoxy, alkylcarbonylalkoxy or nitrobenzyloxy, are valuable herbicides and growth regulators.
    Type: Grant
    Filed: March 26, 1986
    Date of Patent: October 11, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinz J. Loher, Klaus Bauer, Hermann Bieringer
  • Patent number: 4772744
    Abstract: Compounds of the formula ##STR1## wherein X is a hydrogen atom, a halogen atom, a trihalomethyl group, an alkyl group, or a cyano group,Y is a hydrogen atom, a halogen atom, or a trihalomethyl group, andZ is a substituted alkoxy group,and compositions containing these compounds exhibit herbicidal activity.
    Type: Grant
    Filed: April 27, 1987
    Date of Patent: September 20, 1988
    Assignee: Rohm and Haas Company
    Inventors: Horst O. Bayer, Colin Swithenbank, Roy Y. Yih
  • 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: 4745212
    Abstract: Isocyanates containing ester and/or amide groups are produced by reacting (a) an isocyanatocarboxylic acid chloride with (b) an organic compound containing a silylated alcoholic group and/or silylated phenolic hydroxyl group and/or silylated amino group which compound contains no other group which is reactive with isocyanate and chlorocarbonyl groups under the reaction conditions. The reaction of (a) with (b) is carried out at a temperature of from -20.degree. to 150.degree. C. This process makes it possible to produce the desired isocyanates with a high degree of selectivity.
    Type: Grant
    Filed: October 8, 1987
    Date of Patent: May 17, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Mormann, Edith Hissmann
  • Patent number: 4740332
    Abstract: A process is provided for preparing phosphonous acids of the structure wherein R.sub.1 is lower alkyl or arylalkyl ##STR1## which are useful in preparing phosphinic and phosphonic acid ACE inhibitors, which process includes the steps of treating an olefin of the structure R.sub.1 --CH.dbd.CH.sub.2 wherein R.sub.2 is lower alkyl or arylalkyl with a phosphorus-containing reagent such as sodium hypophosphite or hypophosphorous acid in the presence of an organic alcohol solvent such as ethanol or methanol, and a radical initiator such as azobisisobutyronitrile, under acidic conditions, preferably at the reflux temperature of the organic solvent, to form the phosphonous acid without forming the alkyl ester.
    Type: Grant
    Filed: January 20, 1987
    Date of Patent: April 26, 1988
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: John K. Thottathil
  • Patent number: 4739110
    Abstract: A process for the carbonylation of an allenically unsaturated compound with CO in the presence of water, an alcohol and/or a carboxylic acid, which process is carried out in the presence of a catalyst formed by combining:(a) a compound of divalent palladium,(b) at least 15 mol of an organic phosphine per gram atom of divalent palladium, and(c) a protonic acid having a pK.sub.a greater than 1.5 and/or a carboxylic acid having a pK.sub.a not greater than 1.5, both measured at 18.degree. C. in aqueous solution.
    Type: Grant
    Filed: December 27, 1985
    Date of Patent: April 19, 1988
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4739109
    Abstract: Process for the carbonylation of an acetylenically unsaturated compound with CO in the presence of an alcohol and/or water and of a catalyst formed by combining a Pd(II) compound, an organic phosphine and a protonic acid, with the exception of hydrohalogenic acids.
    Type: Grant
    Filed: November 27, 1985
    Date of Patent: April 19, 1988
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • 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: 4709063
    Abstract: A method of preparing certain 2-halo-5-methylpyridines, useful as herbicide intermediates, is presented starting from acyclic pentenes. The pentene is difunctionalized, e.g., by making the epoxide, and is then reacted with a nitrogen source to close the ring. The nitrogen-containing 6-membered heterocycle may then be aromatized readily to produce the 2-halo-5-methylpyridine desired. Also part of the invention are novel acyclic and cyclic intermediates used in the process.
    Type: Grant
    Filed: August 8, 1986
    Date of Patent: November 24, 1987
    Assignee: ICI Americas Inc.
    Inventors: Richard V. Nelson, John F. Stephen
  • Patent number: 4695658
    Abstract: A process for replacing an aromatic carbon-thallium bond with a carbon-oxygen bond. The process is particularly suitable for producing specific aromatic isomers by thallating an aromatic compound and replacing the thallium with a carboxylate group which can be further hydrolyzed if desired to form an aromatic hydroxyl compound.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: September 22, 1987
    Assignee: FMC Corporation
    Inventors: Edward C. Taylor, Alan H. Katz, Randy A. Bull, Lance R. Byers, Richard A. Brown
  • Patent number: 4692546
    Abstract: Acyloxy aromatic carboxylic acids, e.g., 4-acetoxybenzoic acid, are prepared by oxidizing with oxygen an acyloxy aromatic ketone, e.g., 4-acetoxyacetophenone in the presence of manganese cations and a lower-carboxylic acid anhydride as catalyst and a co-reductant or promoter. The acyloxy aromatic ketone may be prepared by acylating a hydroxy aromatic ketone, e.g., 4-hydroxyacetophenone, which has the effect of "masking" the hydroxyl group of the ketone in a manner necessary to effect the subsequent transition-metal catalyzed oxidation of the ketone to the acyloxy aromatic carboxylic acid.
    Type: Grant
    Filed: September 25, 1985
    Date of Patent: September 8, 1987
    Assignee: Celanese Corporation
    Inventor: Kenneth G. Davenport
  • Patent number: 4665215
    Abstract: A process is provided for the production of 4-acetoxybenzoic acid by subjecting phenyl acetate to a Fries rearrangement or phenol and an acetylating agent to a Friedel-Crafts acetylation to form 4-hydroxyacetophenone which is then acetylated with an acetylating agent such as acetic anhydride to form 4-acetoxyacetophenone. The 4-acetoxyacetophenone is then oxidized with oxygen in the presence of manganese cations and acetic acid as catalysts and a co-reductant or promoter to form 4-acetoxybenzoic acid. The acetylation of the 4-hydroxyacetophenone has the effect of "masking" the hydroxyl group of the latter compound in a manner necessary to effect the subsequent oxidation of the ketone group of the 4-acetoxyacetophenone.
    Type: Grant
    Filed: September 25, 1985
    Date of Patent: May 12, 1987
    Assignee: Celanese Corporation
    Inventor: Kenneth G. Davenport
  • Patent number: 4647555
    Abstract: Ester analogues of boron analogues of amino acid are disclosed. Also disced is a method of forming the ester analogues in high yield by condensation of the corresponding acids and alcohols with dicylohexylcarbodiimide at room temperature in dichloromethane. The disclosed compounds have shown interesting biological activities, in particular, hypolipidemic activity as well as significant antitumor and antiarthritic activities.
    Type: Grant
    Filed: October 25, 1984
    Date of Patent: March 3, 1987
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: Bernard F. Spielvogel, Andrew T. McPhail, Iris H. Hall
  • Patent number: 4631151
    Abstract: A fluorine-containing aromatic derivative is produced by causing a di(haloacyl)peroxide to react upon benzene, a mono-substituted benzene, naphthalene, or a mono-substituted naphthalene thereby introducing an X(CF.sub.2).sub.n -group into the benzene ring or the naphthalene ring.
    Type: Grant
    Filed: February 19, 1985
    Date of Patent: December 23, 1986
    Assignee: Nippon Oil & Fars Co., Ltd.
    Inventors: Michio Kobayashi, Masato Yoshida, Hideo Sawada, Hidehiko Hagii, Kazuyoshi Aoshima
  • Patent number: 4624962
    Abstract: Compounds of the formula I ##STR1## in which n denotes 0-3,R.sup.1 and R.sup.1' are the same or different and denote hydrogen, alkyl or alkenyl, phenyl or benzyl, each substituted as desired;R.sup.2 denotes hydrogen, alkyl or alkenyl;R.sup.3 denotes hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl or aminoalkyl, alkanoylaminoalkyl, guanidinoalkyl, imidazolylalkyl, indolylalkyl, mercaptoalkyl or alkylthioalkyl, phenylalkyl, hydroxphenylalkyl, phenoxyalkyl or phenylthioalkyl, or R.sup.2 and R.sup.3, together with the C and N atoms carrying them, denote a saturated or unsaturated 4- to 8-membered monocyclic or 8- to 10-membered bicyclic isocycle or heterocycle, optionally monosubstituted or disubstituted by hydroxyl, alkoxy having 1 to 3 C atoms or alkyl,R.sup.4 denotes hydrogen, alkyl, alkenyl, alkadienyl, alkinyl, alkeninyl or alkadiinyl, cycloalkyl, phenyl, benzyl, phenethyl or phenylpropyl, each of which can be optionally monosubstituted or disubstituted;R.sup.5 denotes hydrogen or alkyl, hydroxyl or alkoxy andR.
    Type: Grant
    Filed: February 1, 1985
    Date of Patent: November 25, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rainer Henning, Hansjorg Urbach, Rolf Geiger, Volker Teetz, Bernward Scholkens
  • Patent number: 4610825
    Abstract: A phosphorous acid or mixture of phosphorous acids is used as catalyst in the esterification reaction of phenol and carboxylic acids. Water is removed from the reaction zone in an efficient manner. An ester product of high purity and excellent color with minimal by-products is characteristically produced.
    Type: Grant
    Filed: April 17, 1985
    Date of Patent: September 9, 1986
    Assignee: Stepan Company
    Inventor: Ned M. Rockwell
  • Patent number: 4572805
    Abstract: 2,3,5,6-Tetrafluorophenyl (meth)acrylates represented by the general formula I: ##STR1## wherein R is H or CH.sub.3 and X is H or CN are disclosed. These compounds are obtained by the reaction of 4-cyano-substituted or unsubstituted 2,3,5,6-tetrafluorophenols with (meth)acrylic acid chloride.
    Type: Grant
    Filed: March 5, 1985
    Date of Patent: February 25, 1986
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Osamu Kaieda, Koichi Hirota, Isao Okitaka, Toshiaki Nakamura
  • Patent number: 4559226
    Abstract: Novel self-emulsifying alkoxylate esters are described having a cloud point of less than about 15.degree. C. the structural formula: ##STR1## R.sub.1 contains from 2 to 20 carbon atoms and is selected from the group consisting of aliphatic and aromatic substituents and R.sub.3 is an alkyl or aryl substituent from 1 to 21 carbon atoms. One of R.sub.1 and R.sub.3 must contain greater than 8 carbon atoms.R.sub.2 is: ##STR2## x is from 1 to 10 and y is from 1 to 20 and the ratio of y to x is from 2:1 to 10:1.These alkoxylate esters are particularly useful in preventing the chalking of antiperspirant compositions containing volatile silicone oil by adding to the antiperspirant composition a chalking preventative amount of such ester. The compositions are also useful in a broad range of cosmetic compositions, and form stable oil-in-water emulsions at room temperature.
    Type: Grant
    Filed: September 6, 1983
    Date of Patent: December 17, 1985
    Assignees: Bernel Chemical Company Inc., Heterene Chemical Company, Inc.
    Inventors: Arnold W. Fogel, Ronald J. Smith
  • Patent number: 4540811
    Abstract: A carboxylic acid esters, such as methyl propionate, is prepared by carbonylation of an olefin, such as ethylene, in the presence of an alcohol by the use of a molybdenum-nickel-alkali metal, a tungsten-nickel-alkali metal or a chromium nickel-alkali metal co-catalyst and in the presence of a halide.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: September 10, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: Nabil Rizkalla
  • Patent number: 4536314
    Abstract: Detergent compositions, detergent additive products and bleaching compositions containing aliphatic peroxyacid bleach precursors of formula ##STR1## are provided, where L is a leaving group of defined formula whose conjugate acid has a pKa of from 6 to 13 and ##STR2## is a non linear acyl group, the carboxylic acid derivative of which has a logP.sub.OCT in the range from 1.9 to 4.0 (where P.sub.OCT is the partition coefficient between octanol and water). New precursor compounds are provided in which ##STR3## is a C.sub.7 -C.sub.17 branched aliphatic acyl group containing a linear chain of at least 5 carbon atoms extending from and including the carbonyl carbon wherein the branching is on at least the 2- and/or 3- carbon atom.
    Type: Grant
    Filed: February 22, 1984
    Date of Patent: August 20, 1985
    Assignee: The Procter & Gamble Company
    Inventors: Frederick E. Hardy, David J. Kitko, Cushman M. Cambre
  • Patent number: 4521614
    Abstract: Esters, e.g., alkyl adipates, are facilely prepared by carbonylation among an alcohol, carbon monoxide and a monoolefin, e.g., an alkyl pentenoate, in the presence of a catalytically effective amount of cobalt and a tertiary nitrogen base, and optionally hydrogen, said reaction being carried out in an aromatic hydrocarbon reaction medium bearing from 1 to 3 nuclear substituents, and said substituents comprising cyano or a radical of the formula R--Y-- having up to 20 carbon atoms, wherein Y is a direct valence bond, an oxygen atom, a sulfur atom, a carbonyl group or a carbonyloxy group (--CO--O--), with R being bonded to the oxygen of the group --CO--O--, and R is alkyl, aralkyl or or aryl, or a cyano substituted such R--Y-- radical, or a radical R--Y-- which includes one of the divalent bridges --O--, --CO-- or --CO--O-- along its skeletal carbon chain, with the proviso that at least one of said substituents is either cyano or a radical R--Y-- wherein Y is other than a direct valence bond.
    Type: Grant
    Filed: May 3, 1983
    Date of Patent: June 4, 1985
    Assignee: Rhone-Poulenc Chimie De Base
    Inventor: Jean Jenck
  • Patent number: 4515803
    Abstract: Compounds of the formula I ##STR1## in which n denotes 0-3,R.sup.1 and R.sup.1' are the same or different and denote hydrogen, alkyl or alkenyl, phenyl or benzyl, each substituted as desired;R.sup.2 denotes hydrogen, alkyl or alkenyl;R.sup.3 denotes hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl or aminoalkyl, alkanoylaminoalkyl, guanidinoalkyl, imidazolylalkyl, indolylalkyl, mercaptoalkyl or alkylthioalkyl, phenylalkyl, hydroxyphenylalkyl, phenoxyalkyl or phenylthioalkyl, or R.sup.2 and R.sup.3, together with the C and N atoms carrying them, denote a saturated or unsaturated 4- to 8-membered monocyclic or 8- to 10-membered bicyclic isocycle or heterocycle, optionally monosubstituted or disubstituted by hydroxyl, alkoxy having 1 to 3 C atoms or alkyl,R.sup.4 denotes hydrogen, alkyl, alkenyl, alkadienyl, alkinyl, alkeninyl or alkadiinyl, cycloalkyl, phenyl, benzyl, phenethyl or phenylpropyl, each of which can be optionally monosubstituted or disubstituted;R.sup.5 denotes hydrogen or alkyl, hydroxyl or alkoxy andR.
    Type: Grant
    Filed: September 1, 1982
    Date of Patent: May 7, 1985
    Assignee: Hoechst Aktiengesellschafat
    Inventors: Rainer Henning, Hansjorg Urbach, Rolf Geiger, Volker Teetz, Bernward Scholkens
  • Patent number: 4515983
    Abstract: A process for the preparation of phenyl esters and phenol in which a feed mixture of benzene, molecular oxygen, a lower carboxylic acid and optionally water is passed over a catalyst composed of a palladium carboxylate, an antimony carboxylate and a chromium carboxylate is described.
    Type: Grant
    Filed: June 30, 1983
    Date of Patent: May 7, 1985
    Assignee: Ashland Oil, Inc.
    Inventors: Anil B. Goel, Michael E. Pettiford
  • Patent number: 4504418
    Abstract: Biodegradable non-ionic surface-active agents containing carbonate groups or residues of carboxylic esters can be prepared by reacting hydrophilic polyoxyalkylene glycols derived from the same or different alkylene oxide glycols with monofunctional alcohols. The compositions of the invention contain both hydrophilic and hydrophobic groups in the molecule making them suitable for use as surface-active agents. The residues of the monofunctional alcohols provide hydrophobic groups in the molecule of the surface-active agent.
    Type: Grant
    Filed: January 9, 1981
    Date of Patent: March 12, 1985
    Assignee: BASF Wyandotte Corporation
    Inventor: William K. Langdon