Phenolic Hydroxy Or Metallate Patents (Class 560/75)
  • Patent number: 5274170
    Abstract: Compounds of the formula ##STR1## in which R is hydrogen or hydroxyl, R.sub.1 is alkyl, alkoxy, amino or aryl, and R.sub.2 is hydrocarbylcarbonyl or hydrocarbylsulfonyl, are highly suitable for stabilizing magenta couplers in photographic materials.
    Type: Grant
    Filed: June 15, 1992
    Date of Patent: December 28, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: David G. Leppard, David H. Steinberg, Henri Dubas
  • Patent number: 5264612
    Abstract: Disclosed is a process for the preparation of aryl-substituted propionic acid esters having the formula: ##STR1## wherein R and R.sup.1 are a C.sub.1 -C.sub.12 linear or branched alkyl, a C.sub.5 -C.sub.12 cycloalkyl, a C.sub.6 -C.sub.12 aryl or a C.sub.7 -C.sub.12 alkaryl or aralkyl, R.sup.2 is hydrogen or a C.sub.1 -C.sub.20 linear or branched alkyl and R.sup.3 is a C.sub.1 -C.sub.20 linear or branched alkyl, a C.sub.5 -C.sub.12 cycloalkyl, a C.sub.6 -C.sub.12 aryl or a C.sub.7 -C.sub.20 alkaryl or aralkyl, and may be the same or different, or R.sup.1 is hydrogen, which comprises forming a reaction mixture of a phenol, at least one base catalyst and an acrylate, in the presence of 1,2-dimethoxybenzene, wherein the acrylate is added at once or over a period of time from 5 to 60 minutes at atmospheric pressure. The process results in excellent yields of the desired product with good rates of conversion.
    Type: Grant
    Filed: September 28, 1992
    Date of Patent: November 23, 1993
    Assignee: Himont Incorporated
    Inventors: Eric J. Evain, Krishna Raman
  • Patent number: 5260475
    Abstract: The hydroxybenzoic acids, e.g., salicylic acid and parahydroxybenzoic acid, are esterified by reacting same with a halocarbon, advantageously a halogenated derivative of an aliphatic, cycloaliphatic, cyclo- or arylaliphatic hydrocarbon, in essentially homogeneous liquid phase and in the presence of a nonquaternizable tertiary amine.
    Type: Grant
    Filed: June 24, 1991
    Date of Patent: November 9, 1993
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Roger Desmurs, Serge Ratton
  • Patent number: 5248807
    Abstract: The present invention provides triterpene derivatives of the following formula: ##STR1## wherein, R.sup.1 is hydrogen or metabolic ester-residue; R.sup.3 is optionally substituted aryl or optionally substituted aromatic heterocycle; X is hydrogen and Y is hydroxy or X and Y may form together oxo; Z is an oxygen or two hydrogen atoms, or the salts thereof, which have anti-endothelin activities and are useful for preventing or treating cardiovascular failure, and pharmaceutical compositions thereof.
    Type: Grant
    Filed: July 8, 1992
    Date of Patent: September 28, 1993
    Assignee: Shionogi & Co., Ltd.
    Inventors: Masafumi Fujimoto, Kensuke Sakurai, Shinichi Mihara, Miharu Nakamura, Toshiro Konoike
  • Patent number: 5216185
    Abstract: Polymerizable calixarene and oxacalixarene derivates wherein at least one aryl group of the macrocyclic ring has a phenolic side chain of the formula VII: ##STR1## wherein Z is a group containing an acrylate or methacrylate functional group. Linear polymers may be formed from these compounds by free radical polymerization at the (meth)acrylate group. Such compounds and their polymers are capable of sequestering metals.
    Type: Grant
    Filed: December 10, 1990
    Date of Patent: June 1, 1993
    Assignee: Loctite Limited
    Inventors: Stephen J. Harris, John Guthrie, Maureen MacManus, Michael A. McKervey
  • Patent number: 5216024
    Abstract: The present invention discloses new and useful compounds including methyl p-hydroxyphenyllactate, its analogues, chemical derivatives and chemically related compounds and their use as antitumor agents, as inhibitors of proliferative cell growth and as prophylactic agents to inhibit and prevent cancer and non-malignant cell growth.
    Type: Grant
    Filed: July 15, 1988
    Date of Patent: June 1, 1993
    Assignee: Baylor College of Medicine
    Inventors: Barry M. Markaverich, James H. Clark, Rebecca Gregory, Mary Alejandro, Brian S. Middleditch, Gregory A. Johnson, Rajender S. Varma
  • Patent number: 5212201
    Abstract: A pharmaceutical composition inhibiting xanthine oxidase containing as an active component a compound of the formula: ##STR1## wherein R is 4'-OH or 5'-OH, or a pharmaceutically acceptable salt or ester thereof is disclosed. The compound wherein R is 5'-OH is a novel compound.
    Type: Grant
    Filed: November 13, 1990
    Date of Patent: May 18, 1993
    Assignee: Gunze Limited
    Inventors: Michio Wakashiro, Shiro Abe, Nobukazu Tanabe, Hiroshi Obata
  • Patent number: 5206414
    Abstract: A process for the preparation of compounds of the general formula ##STR1## where R.sub.1 and R.sub.2 are identical or different and are hydrogen, C.sub.1 -C.sub.18 alkyl, phenyl, C.sub.1 -C.sub.4 alkyl-substituted phenyl, C.sub.7 -C.sub.9 phenylalkyl, C.sub.5 -C.sub.12 cycloalkyl or C.sub.1 -C.sub.4 alkyl-substituted C.sub.5 -C.sub.12 cycloalkyl,R.sub.3 is hydrogen or methyl,m is 0, 1, 2 or 3, andn is a number from 1 to 4 or 6, andA is as defined in the description,by reacting a compound of the formula II ##STR2## where m, R.sub.1 and R.sub.2 are as defined above, with a compound of the formula III ##STR3## where A and n are as defined in the description, which comprises carrying out the reaction in the presence of a catalyst which contains, as active material, an alkali metal compound of the formula IVM.sub.m An (IV)in whichM is Li, Na, K, Rb or Cs,m is the valency of An, andAn is a fluoride, hydroxide, phosphate, formate, acetate or --OR.sub.5 radical, andR.sub.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: April 27, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Samuel Evans, Paul Dubs, Milos Rusek, Zdenek Mazour, Arpad Major
  • Patent number: 5202458
    Abstract: Compounds of the formula I or II ##STR1## in which R, R.sup.0, R.sup.1 and R.sup.2 are as defined in claim 1. The compounds, some of which are novel, are light stabilizers for color photographic recording materials.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: April 13, 1993
    Assignee: Ciba-Geigy AG
    Inventor: David G. Leppard
  • Patent number: 5177246
    Abstract: The novel compounds of the formulae Ia and Ib ##STR1## in which the radicals R are identical or different and are a group of the formula II ##STR2## in which X is a direct bond, methylene, ethylene or a group ##STR3## and Y is C.sub.1 -C.sub.8 alkyl, R.sub.1 and R.sub.2 independently of one another are C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.7 cycloalkyl which is substituted by C.sub.1 -C.sub.4 alkyl, or are phenyl or C.sub.7 -C.sub.10 phenylalkyl, and R.sub.2 is additionally hydrogen, are suitable for stabilizing organic material against thermal, oxidative or actinic degradation.
    Type: Grant
    Filed: August 23, 1991
    Date of Patent: January 5, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Rita Pitteloud
  • Patent number: 5177247
    Abstract: Hydroxyphenylpropionates of formula ##STR1## wherein R.sub.1 to R.sub.4 are as defined in claim 1, are prepared by reacting the appropriate phenol and acrylate components in the presence of the sodium and potassium salt of said phenol component.
    Type: Grant
    Filed: March 22, 1991
    Date of Patent: January 5, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Franz Brogli, Guido Kalin
  • Patent number: 5155244
    Abstract: A method of solubilizing a first compound in a second medium where the first compound has a limited solubility in the second medium. In particular, the method comprises reacting the first compound with the second medium. By this reaction, a product is formed whereby an active component of the first compound is covalently incorporated into the second medium.The first compound and second medium each contain at least one reactive group which will react with a reactive group of the other. In addition, the first compound comprises at least one antioxidant which will be covalently bonded to and thus effectively solubilized in the second medium by the reaction.The second medium comprises glyceride derivatives, silicones, fluorocarbons and alkoxylates containing reactive groups such as hydroxy, amino, carboxyl, ester, or amides.
    Type: Grant
    Filed: February 28, 1990
    Date of Patent: October 13, 1992
    Assignee: Karlshamns AB
    Inventors: George H. Greene, James C. Phillips, Jerry F. Stults, Jan P. E. Tellings
  • Patent number: 5144058
    Abstract: Tetrakis [3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxymethyl]methane in the form of grained alpha-form crystals having improved coloration. The above compound is prepared by transesterifying low-alkyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate with pentaerythritol in the presence of catalyst and aliphatic hydrocarbons as reaction solvent.
    Type: Grant
    Filed: June 15, 1990
    Date of Patent: September 1, 1992
    Assignee: International Chemical Consultant, Ltd.
    Inventor: Atsushi Nishimura
  • Patent number: 5136082
    Abstract: Disclosed is a process for the preparation of organic esters and amides by reacting (a) a 5 to 60 mole % excess of an ester of (substituted-4-hydroxyphenyl) alkanoic acid with (b) (i) a C.sub.4 -C.sub.20 aliphatic alcohol or thioether alcohol having one or more hydroxyl groups or (ii) an amine of the formula, (R"').sub.2 N(CH.sub.2).sub.n R"" wherein R"' is hydrogen, C.sub.1-7 alkyl, C.sub.5-12 cycloalkyl, or C.sub.6-12 aryl, provided that one R"' is hydrogen, and R"" is hydrogen or N(R"').sub.2 wherein R"' is a defined above, in the presence of a catalyst system comprising a basic inorganic compound and a polar aprotic organic compound. The process provides higher yields of the desired product, shorter reaction times, and reduces the production of undesirable side-products.
    Type: Grant
    Filed: August 3, 1990
    Date of Patent: August 4, 1992
    Assignee: Himont Incorporated
    Inventors: Vu A. Dang, Gleason O. Cookson, Krishna Raman
  • Patent number: 5130465
    Abstract: Hydroxyphenylpropionates are prepared by Michael addition of an acrylic acid component to a phenol component. The compounds are purified by vacuum rectification after separation of the basic catalyst.
    Type: Grant
    Filed: March 22, 1991
    Date of Patent: July 14, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Kalman Kovasy, Zdenek Mazour
  • Patent number: 5124474
    Abstract: A process for the commercial-scale crystallization and purification of tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxymethyl]methane which comprises melt-blending the reaction mixture resulting from the transesterification between pentaerythritol and a lower alkyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate and containing tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxymethyl]methane with a water-soluble solvent under reflux, then blending the resulting melt-blend with a cooled, mixed solvent composed of 0.2-1.5 parts by weight, per part by weight of the above-mentioned reaction mixture, of a water-soluble solvent and 0.06-0.09 part by weight, per part by weight of the water-soluble solvent, of water to thereby cause crystallization, and further adding water for stabilizing the resulting beta crystal structure.
    Type: Grant
    Filed: November 29, 1989
    Date of Patent: June 23, 1992
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Noritsugu Narita, Makoto Maruno
  • Patent number: 5117040
    Abstract: The invention provides alpha crystals of tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxymethyl]methane that occur as round granular crystals with high purity, uniform grain size, narrow grain size distribution and good flowability.
    Type: Grant
    Filed: June 5, 1990
    Date of Patent: May 26, 1992
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Masayoshi Marutani, Fumihide Izumi, Kunihide Oka
  • Patent number: 5114613
    Abstract: An optically active lactic acid derivative represented by the following formula (I): ##STR1## wherein R represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 1 to 18 carbon atoms; C* represents an asymmetric carbon atom; l is 0 or 1; m is 1 or 2; A represents a group selected from the following groups (a) and (b):(a) hydroxyl group, halogen, benzyloxy group, phenoxy group, toluenesulfonic acid group, acetyloxy group, trifluoroacetyloxy group; ##STR2## (wherein R' is an alkyl group or alkoxy group having 4 to 18 carbon atoms, n is 0 or 1, ##STR3## with proviso that when A is selected from the groups in the above group (a), l is 1 and m is 1 or 2; and when A is selected from the groups in the above group (b), m=n=1 when l is 0, or m and n are 0, 1 or 2 and m+n is 1 or 2 when l is 1, and ##STR4##
    Type: Grant
    Filed: September 13, 1989
    Date of Patent: May 19, 1992
    Assignee: Canon Kabushiki Kaisha
    Inventors: Kazuo Yoshinaga, Kazuharu Katagiri, Akira Tsuboyama, Hiroyuki Kitayama, Kenji Shinjo, Chieko Hioki
  • Patent number: 5089655
    Abstract: Novel individual .alpha.-form particle crystals of tetrakis[3-(3,5,-di-t-butyl-4-hydroxyphenyl)propionyloxymethyl]methane and process for its production are disclosed.
    Type: Grant
    Filed: September 6, 1989
    Date of Patent: February 18, 1992
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Takanori Miura, Masanori Kohara, Kunihide Oka
  • Patent number: 5089656
    Abstract: Disclosed is a process for the preparation of aryl-substituted propionic acid esters having the formula: ##STR1## wherein R and R.sup.1 are a C.sub.1 -C.sub.12 linear or branched alkyl, a C.sub.5 -C.sub.12 cycloalkyl, a C.sub.6 -C.sub.12 aryl or a C.sub.7 -C.sub.12 alkaryl or aralkyl, R.sup.2 is hydrogen or a C.sub.1 -C.sub.20 linear or branched alkyl and R.sup.3 is a C.sub.1 -C.sub.20 linear or branched alkyl, a C.sub.5 -C.sub.12 cycloalkyl, a C.sub.6 -C.sub.12 aryl or a C.sub.7 -C.sub.20 alkaryl or aralkyl, and may be the same or different, which comprises forming a reaction mixture of a phenol, at least one base catalyst and an acrylate, in the presence of a complexing agent effective in increasing the rate of reaction, wherein (i) substantially all of the side-product is removed from said reaction mixtrue prior to the addition of the complexing agent and (ii) all or substantially all of the acrylate is added at once to the reaction mixture.
    Type: Grant
    Filed: July 18, 1990
    Date of Patent: February 18, 1992
    Assignee: Himont Incorporated
    Inventor: Lin-Chen Yu
  • Patent number: 5081280
    Abstract: In producing ester compound useful as an antioxidant for organic materials which are represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and represent hydrogen or straight or branched chain alkyl radicals containing 1-8 carbon atoms, Z is an organic radical derived from an n-hydroxy alcohol, and n denotes an integer of 1 to 4, by transesterification, monoalkyltin compounds are used as a catalyst, whereby the ester compounds can be produced with high quality and in high yields.
    Type: Grant
    Filed: March 7, 1989
    Date of Patent: January 14, 1992
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Koichi Takee, Masayoshi Gohbayashi, Kunihide Oka
  • Patent number: 5066675
    Abstract: There are described new phenylacetic acid derivatives of general formula I ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 have the meanings given in the description, processes for their preparation and insecticidal and acaricidal compositions containing these compounds.
    Type: Grant
    Filed: August 31, 1990
    Date of Patent: November 19, 1991
    Assignee: Schering Aktiengesellschaft
    Inventors: Ulrich Buhmann, Hartmut Joppien, Dietrich Baumert
  • Patent number: 5051506
    Abstract: Chiral, nonracemic compounds of the general formula: ##STR1## wherein m and n are either both zero, both equal one or n is equal to one and m is equal to zero, X and Y and Z are halogens, R' is an alkyl or alkoxy group having three to fifteen carbons, R is an alkyl group having one to fifteen carbons, and Ar is a 4,4'-substituted phenylvenzoate, 4,4'-substituted biphenylbenzoate, 5,4-substituted 2-phenylpyrimidine or 4,4'-substituted biphenyl core, and wherein * indicates a chiral center, which are useful as ferroelectric liquid crystal components having high polarization are described.
    Type: Grant
    Filed: March 4, 1988
    Date of Patent: September 24, 1991
    Assignee: Displaytech, Inc.
    Inventors: Michael D. Wand, David M. Walba
  • Patent number: 5049696
    Abstract: Novel 3-hydroxy-3-methylglutaryl-Coenzyme A(HMG-CoA) reductase inhibitors, which are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) and (II) ##STR1## and pharmaceutically acceptable salts of the compound (II) in which Z is hydrogen are disclosed.
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: September 17, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Ta J. Lee, Clarence S. Rooney, William F. Hoffman
  • Patent number: 5025017
    Abstract: Seco-mevinic acid derivatives are provided which has the structure ##STR1## including all stereoisomers thereof, wherein Z is ##STR2## R is H, alkali metal or lower alkyl, R.sup.1 is H, lower alkyl, aryl, lower alkoxy, cycloalkyl, heteroaryl, aralkyl, heteroaralkyl or heterocyclic; R.sup.2 is lower alkyl, cycloalkyl or aralkyl, and X is O or NR.sup.5 wherein R.sup.5 is H or lower alkyl, and are HMG CoA reductase inhibitors and thus are useful as antihypercholesterolemic agents and in treating atherosclerosis. New intermediates for preparing the above seco-mevinic acid derivatives are also provided.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: June 18, 1991
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Donald S. Karanewsky
  • Patent number: 5021450
    Abstract: The present invention relates to a new class of compounds having a variable spectrum of activities for capsaicin-like responses, compositions thereof, processes for preparing the same, and uses thereof. Compounds of the invention are prepared by combining phorbol related diterpenses and homovanillac acid analogs via esterification at the exocyclic hydroxy group of the diterpene. Examples of these compounds include 20-homovanillyl-mezerein and 20-homovanillyl-12-deoxyphorbol-13-phenylacetate.
    Type: Grant
    Filed: May 30, 1989
    Date of Patent: June 4, 1991
    Assignee: The United States of America as represented by the Secretary of the Department of Health and Human Services
    Inventor: Peter M. Blumberg
  • Patent number: 5008441
    Abstract: The invention relates to a compound having the structure: ##STR1##wherein R comprises a phenethyl, butyl, hexyl or ethyl group.The invention also related to methods of isolating and producing the compound, methods of treating inflammation in a subject and methods of substantially inhibiting the growth of transformed cells in a population of normal and transformed cells.
    Type: Grant
    Filed: June 20, 1989
    Date of Patent: April 16, 1991
    Assignee: The Trustees of Columbia University in the City of New York
    Inventors: Koji Nakanishi, Eugene M. Oltz, Dezider Grunberger
  • Patent number: 4950780
    Abstract: Novel crystalline form of n-octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate with improved transportability, measurability and workability is disclosed.
    Type: Grant
    Filed: September 5, 1989
    Date of Patent: August 21, 1990
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Masaya Tanaka, Masayoshi Gohbayashi, Kunihide Oka
  • Patent number: 4917817
    Abstract: An optically active functional compound represented by the following formula (1) is disclosed: ##STR1## wherein R denotes an alkyl group having 1-14 carbon atoms; -X- denotes ##STR2## denotes a single bond, ##STR3## n=0, 1 or 2; and C* denotes an asymmetric carbon atom. The compound of the formula (1) may be produced through an optically active compound of the following formula (2) or (3): ##STR4## The compounds of the above formulas (1)-(3) are all characterized by a trifluoromethyl group providing a large spontaneous polarization attached to an asymmetric carbon atom.
    Type: Grant
    Filed: July 21, 1988
    Date of Patent: April 17, 1990
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Tetsuya Abe, Yoko Yamada, Yuko Etoh
  • Patent number: 4912249
    Abstract: Useful for the stabilization of polymers, especially polypropylene and polyethylene are esters of 3-tert-butyl or 3-tert-butyl-5-alkyl-4-hydroxyphenyl(alkane) carboxylic acids with oxethylates of bis-(4- or 2-hydroxyphenyl) alkanes, oxides, sulfides or sulfones, with oxethylates of tris-(4-hydroxyphenyl) alkanes, or with oxethylates of 1,3,5-tris-(4-hydroxyphenyl isopropylidene) aryls, the oxethylate preferably comprising a hydroxyethoxy group substituted for each hydroxyl group.
    Type: Grant
    Filed: November 18, 1987
    Date of Patent: March 27, 1990
    Assignee: Huels Aktiengesellschaft
    Inventors: Friedrich-Wilhelm Kupper, Heinz-Werner Voges, Werner Patzold, Richard Schaaf
  • Patent number: 4906662
    Abstract: Disclosed are phenol derivatives of the formula ##STR1## wherein R.sup.1 is a substituted phenyl group, R.sup.2 and R.sup.3 are C.sub.1 -C.sub.6 alkyl group and of the formula ##STR2## wherein R.sup.8, R.sup.9 and R.sup.10 are C.sub.1 -C.sub.6 alkyl and the like and A is H, C.sub.1 -C.sub.6 alkylsulfonyl and the like substituents. These compounds and some related compounds have anti-inflammatory activity and lipoxygenase inhibitory activity.
    Type: Grant
    Filed: January 27, 1987
    Date of Patent: March 6, 1990
    Assignee: Otsuka Pharmaceutical Factory, Inc.
    Inventors: Kinji Hashimoto, Kiyoto Goto, Ken-ichi Kanai, Yoshiaki Tsuda
  • Patent number: 4906775
    Abstract: Esters of 3-tert-butyl- and 3-tert-butyl-5-alkyl-4-hydroxyphenyl (alkane) carboxylic acids with oxyethylates of polythiols are useful as stabilizers for polymers, especially for polyethylene and polypropylene.
    Type: Grant
    Filed: November 18, 1987
    Date of Patent: March 6, 1990
    Assignee: Huels Aktiengesellschaft
    Inventors: Friedrich-Wilhelm Kupper, Heinz-Werner Voges, Hans-Jurgen Haage
  • Patent number: 4904815
    Abstract: New phenols are described containing an alkyl substituent containing a functional group; as well as a process for the production of such phenols. The new phenols are useful e.g. as stabilizers in organic or aqueous systems.
    Type: Grant
    Filed: October 13, 1987
    Date of Patent: February 27, 1990
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4886900
    Abstract: Tetrakis[3,5-di-tert.butyl-4-hydroxyphenyl)-propionyl-oxymethyl]methane with amorphous structure, with glass transition temperature T.sub.g comprised within the range of from about 40.degree. C. to 50.degree. C. and free from endothermic melting peaks at temperatures higher than 50.degree. C. and of up to 200.degree. C. is obtained by means of the melting of crystalline tetrakis[3-(3,5-di-tert.butyl-4-hydroxyphenul)-propionyl-oxymethyl]methane and sudden cooling of the molten material.
    Type: Grant
    Filed: July 17, 1987
    Date of Patent: December 12, 1989
    Assignee: Enichem Sintesi S.p.A.
    Inventors: Carlo Neri, Nereo Nodari, Giovanni Sandre
  • Patent number: 4885382
    Abstract: A method for producing tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxymethyl]methane by ester exchange between a 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid alkyl ester and pentaerythritol in the presence of a basic catalyst, which comprises carrying out the reaction in the presence of a 3-(3-tert-butyl-4-hydroxyphenyl)propionic acid alkyl ester.According to the method of the invention, tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxymethyl]methane can be obtained in high yields as fine granules having good properties without coloration, with certainty and good reproducibility.
    Type: Grant
    Filed: September 28, 1988
    Date of Patent: December 5, 1989
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Masayoshi Gohbayashi, Noritsugu Narita, Makoto Maruno
  • Patent number: 4883902
    Abstract: A method of producing tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxymethyl]methane by ester exchange between a 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid alkyl ester and pentaerythritol in the presence of a basic catalyst, which comprises carrying out the reaction in the presence of bis[2,2,2-tris(hydroxymethyl)ethoxylmethane.According to the method of the invention, tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxymethyl]methane can be obtained in high yields and in high purity without using an excessively large amount of a 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid alkyl ester which is an expensive compound, while controlling the formation of the byproduct to a minimum level.
    Type: Grant
    Filed: September 28, 1988
    Date of Patent: November 28, 1989
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Masayoshi Gohbayashi, Noritsugu Narita, Makoto Maruno
  • Patent number: 4882449
    Abstract: Novel nitrogen-containing calixarene derivatives which are useful for sequestration of transition metals are represented by the formulae ##STR1## wherein m+n=4,6 or 8n=an integer 1-8m=an integer 0-7x=4, 6 or 8R.sup.1 is H, alkyl, aralkyl, alkoxy, aroyl, or alkoyl,R is aliphatic or aromatic, unsubstituted or substituted hydrocarbyl containing nitrogen,R.sup.4 is unsubstituted or substituted hydrocarbyl, carbonyl or aryl;R.sup.5 and R.sup.6 (which may be the same or different) are hydrogen, or unsubstituted or substituted hydrocarbyl.A process for separating transition metals from mixtures containing such metals comprises treating such a mixture with a calixarene derivative of formula I or II as defined above and separating therefrom a complex of the calixarene derivative and the transition metal. The complex may then be broken down, the transition metal recovered and the calixarene derivative recycled for further use in the process.
    Type: Grant
    Filed: March 2, 1987
    Date of Patent: November 21, 1989
    Assignee: Loctite Corporation
    Inventor: Stephen J. Harris
  • Patent number: 4859790
    Abstract: Esters of 3-tert-butyl- and 3-tert-butyl-5-alkyl-4-hydroxyphenyl(alkane) carboxylic acids of Formula I ##STR1## with oxethylates of polyhydroxyaromatics of 2-6 hydroxy groups of general Formulae II and III, containing 1-6 oxethylate units, ##STR2## with X=(CH.sub.2).sub.q OHX'=(CH.sub.2).sub.r OHwherein q, r, s can be 0 or 1, preferably 0,X"=(CH.sub.2).sub.s OHR,R', R"=H, alkyl, halogen, ##STR3## preferably 4-hydroxyphenyl, n=2 to 6 for z or z'=0, preferably 2 or 3, andn=1 to 5 for z or z'.noteq.0, preferably 2 or 3,o+p=n0.ltoreq.a, z.ltoreq.a+z.ltoreq.6-n (in Formula II)0.ltoreq.b, c, z'.ltoreq.4.ltoreq.8-n (in Formula III).are useful for the stabilization of polymers.
    Type: Grant
    Filed: November 18, 1987
    Date of Patent: August 22, 1989
    Assignee: Huels Aktiengesellschaft
    Inventors: Friedrich-Wilhelm Kupper, Heinz-Werner Voges, Werner Patzold, Richard Schaaf
  • Patent number: 4855073
    Abstract: Disclosed are a lubricant composition comprising a major amount of one or more lubricant fluids and at least one polyvalent metal salt of the formaldehyde condensation products of C.sub.12 -C.sub.22 alkyl hydroxy benzoic acid, and a method of preparation of same. Because of the methylenebis structure of the polyvalent metal salts, engine properties such as detergency/dispersancy, thermal stability, hydrolytic stability, oil solubility and especially compatibility with other additives are improved by the use of the composition.
    Type: Grant
    Filed: May 27, 1988
    Date of Patent: August 8, 1989
    Inventors: Mitsuhiro Murakami, Takahiro Mikami, Hiroyuki Nagamatsu, Mitsuji Tokuno
  • 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: 4827845
    Abstract: Hydroxy aryl carboxylic acids are formed by reacting a hydroxy aryl compound, such as phenol, with a ketone, such as acetone and carbon monoxide in the presence of a strong acid. The preferred embodiment is the one step formation of 2-methyl-2-(p-hydroxyphenyl) propionic acid from phenol, acetone and carbon monoxide in the presence of hydrofluoric acid. When this reaction is conducted in the presence of methanol the corresponding methyl ester is formed.
    Type: Grant
    Filed: September 23, 1987
    Date of Patent: May 9, 1989
    Assignee: Ashland Oil, Inc.
    Inventors: Dace Grote, William L. Embry, Kenneth W. Barnett
  • Patent number: 4806675
    Abstract: Pentaerythritol co-esters derived from pentaerythritol, (3-alkyl-4-hydroxyphenyl)-alkanoic acids and alkylthioalkanoic acids or lower alkyl esters of such acids are useful as stabilizers of organic material normally susceptible to oxidative and/or thermal deterioration. The co-esters are advantageously prepared by transesterification of such esters with pentaerythritol. Preferred co-esters are (I) pentaerythritol tris[3,5-di-tert-butyl-4-hydroxyphenyl)propionate]-mono[3-n-dodecylthiopro pionate] and (II) pentaerythritol bis[-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]-bis[3-n-dodecylthiopro pionate]. The co-esters are especially useful in stabilizing applications for which physical mixtures of (i) (3-alkyl-4-hydroxyphenylalkanoic acid esters of polyols with (ii) polyalkanol esters of alkylthioalkanoic acids have heretofore been proposed.
    Type: Grant
    Filed: October 19, 1987
    Date of Patent: February 21, 1989
    Assignee: Mallinckrodt, Inc.
    Inventors: Neil Dunski, Ali A. Bazzi
  • Patent number: 4801735
    Abstract: Compounds are described of the following formula ##STR1## in which R.sup.1 and R.sup.2 are each hydrogen, C.sub.1-12 alkyl or C.sub.2-12 alkenyl, at least one of R.sup.1 and R.sup.2 being C.sub.1-12 alkyl or C.sub.2-12 alkenyl; X.sup.1 and X.sup.2 are each hydrogen or a protecting group; and Y is(a) --(CH.dbd.CH).sub.n Z in which n is 1, 2 or 3 and Z is --CHO, --CH.sub.2 OH, --COR.sup.3, --(CH.sub.2).sub.m --COR.sup.3 or --(CH.sub.2).sub.p CH.dbd.CH(CH.sub.2).sub.q --COR.sup.3 in which m is an integer of 1 to 12, p is an integer of 1 to 4, q is an integer of 1 to 10 and R.sup.3 is (i) --OH or (ii) --NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are each hydrogen, C.sub.1-4 alkyl or optionally substituted phenyl, or R.sup.4 and R.sup.5 together with the nitrogen atom to which they are attached form a morpholino, pyrrolidinyl or piperidino ring,(b) --CH.dbd.NR.sup.6 in which R.sup.6 is (i) --OH, (ii) C.sub.1-12 alkyl optionally substituted by --OH, --COOH or --NR.sup.7 R.sup.8 where R.sup.7 and R.sup.
    Type: Grant
    Filed: November 25, 1985
    Date of Patent: January 31, 1989
    Assignee: Lilly Industries Limited
    Inventors: Mark A. W. Finch, John R. Harris
  • Patent number: 4794138
    Abstract: Pentaerythritol co-esters derived from pentaerythritol, (3-alkyl-4-hydroxyphenyl)-alkanoic acids and alkylthioalkanoic acids or lower alkyl esters of such acids are useful as stabilizers of organic material normally susceptible to oxidative and/or thermal deterioration. The co-esters are advantageously prepared by transesterification of such esters with pentaerythritol. Preferred co-esters are (I) pentaerythritol tris[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]-mono[3-n-do-decylthi opropionate] and (II) pentaerythritol bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]-bis[3-n-dodecylthiopr opionate]. The co-esters are especially useful in stabilizing applications for which physical mixtures of (i) (3-alkyl-4-hydroxyphenyl)alkanoic acid esters of polyols with (ii) polyalkanol esters of alkylthioalkanoic acids have heretofore been proposed.
    Type: Grant
    Filed: August 28, 1987
    Date of Patent: December 27, 1988
    Assignee: Mallinckrodt, Inc.
    Inventors: Neil Dunski, Ali A. Bazzi
  • Patent number: 4790963
    Abstract: A process for producing an ester is disclosed comprising contacting a gaseous reactant containing at least one organic hydroxy compound and a mixture of carbon monoxide and hydrogen with an ester synthesis catalyst of the formulaM.sub.a A.sub.b RuCu.sub.c N.sub.z O.sub.xwhereinM is selected from the group consisting of Ce, Cr, Fe, Mn and mixtures thereof,A is an alkali metal, alkaline earth metal or mixture thereof,a is from 0 to about 1,b is from 0.002 to about 10,c is from 0.2 to about 20,z is from 0 to about 196 by weight,x is the number of oxygens needed to fulfill the valence requirements of the other elements.The organic hydroxy compound can be provided separately or formed by contacting a mixture of carbon monoxide and hydrogen with an alcohol synthesis catalyst at an elevated temperature and pressure. The alcohol synthesis catalyst and ester synthesis catalyst can be in tandem or mixed.
    Type: Grant
    Filed: August 20, 1984
    Date of Patent: December 13, 1988
    Assignee: The Standard Oil Company
    Inventors: Thomas G. Attig, Anne M. Graham, Frederick A. Pesa
  • Patent number: 4772741
    Abstract: Pentaerythritol co-esters derived from pentaerythritol, (3-alkyl-4-hydroxyphenyl)-alkanoic acids and alkylthioalkanoic acids or lower alkyl esters of such acids are useful as stabilizers of organic material normally susceptible to oxidative and/or thermal deterioration. The co-esters are advantageously prepared by transesterification of such esters with pentaerythritol. Preferred co-esters are (I) pentaerythritol tris[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]-mono[3-n-dodecylthio propionate]and (II) pentaerythritol bis [3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]-bis[3-n-dodecylthiopropi onate]. The co-esters are especially useful in stabilizing applications for which physical mixtures of (i) (3-alkyl-4-hydroxyphenyl)alkanoic acid esters of polyols with (ii) polyalkanol esters of alkylthioalkanoic acids have heretofore been proposed.
    Type: Grant
    Filed: August 31, 1987
    Date of Patent: September 20, 1988
    Assignee: Millinckrodt, Inc.
    Inventors: Neil Dunski, Ali A. Bazzi
  • Patent number: 4767782
    Abstract: Cinnamates of the formula I ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the meanings stated in the description, processes for their preparation, and their use for pest control.
    Type: Grant
    Filed: February 20, 1987
    Date of Patent: August 30, 1988
    Assignee: Basf Aktiengesellschaft
    Inventors: Wolfgang Seppelt, Hans-Juergen Neubauer, Heinrich Adolphi, Peter Hofmeister
  • Patent number: 4739102
    Abstract: A new crystal form of tetrakis-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxymethyl]-methane is disclosed. It is an individual .beta.-modification crystal form in substantially parallelepipedal to cubic shape. A method of preparation of this new crystal form is likewise disclosed.
    Type: Grant
    Filed: April 29, 1987
    Date of Patent: April 19, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Mitsukuni Tokunaga
  • Patent number: 4737591
    Abstract: A method of preparing esters of cinnamic acid comprising catalytically reacting a styrene compound with carbon monoxide, oxygen, and an aliphatic alcohol. The catalyst is essentially a combination of a palladium (II) compound and a copper salt. A catalytic amount of a dehydrating agent may be present to increase the selectivity of the reaction.
    Type: Grant
    Filed: December 21, 1984
    Date of Patent: April 12, 1988
    Assignee: Sun Refining and Marketing Company
    Inventor: Chao-Yang Hsu
  • Patent number: 4734519
    Abstract: Pentaerythritol co-esters derived from pentaerythritol, (3-alkyl-4-hydroxyphenyl)-alkanoic acids and alkylthioalkanoic acids or lower alkyl esters of such acids are useful as stabilizers of organic material normally susceptible to oxidative and/or thermal deterioration. The co-esters are advantageously prepared by transesterification of such esters with pentaerythritol. Preferred co-esters are (I) pentaerythritol tris[3-(3,5-di-tert-butyl-4-hydroxylphenyl)propionate]-mono[3-n-dodecylthi opropionate] and (II) pentaerythritol bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]-bis[3-n-dodecylthiopr opionate]. The co-esters are especially useful in stabilizing applications for which physical mixtures of (i) (3-alkyl-4-hydroxyphenyl)alkanoic acid esters of polyols with (ii) polyalkanol esters of alkylthioalkanoic acids have heretofore been proposed.
    Type: Grant
    Filed: June 5, 1986
    Date of Patent: March 29, 1988
    Assignee: Mallinckrodt, Inc.
    Inventors: Neil Dunski, Ali A. Bazzi