Phenolic Hydroxy Or Metallate Patents (Class 560/75)
-
Patent number: 5274170Abstract: 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: GrantFiled: June 15, 1992Date of Patent: December 28, 1993Assignee: Ciba-Geigy CorporationInventors: David G. Leppard, David H. Steinberg, Henri Dubas
-
Patent number: 5264612Abstract: 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: GrantFiled: September 28, 1992Date of Patent: November 23, 1993Assignee: Himont IncorporatedInventors: Eric J. Evain, Krishna Raman
-
Patent number: 5260475Abstract: 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: GrantFiled: June 24, 1991Date of Patent: November 9, 1993Assignee: Rhone-Poulenc ChimieInventors: Jean-Roger Desmurs, Serge Ratton
-
Patent number: 5248807Abstract: 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: GrantFiled: July 8, 1992Date of Patent: September 28, 1993Assignee: Shionogi & Co., Ltd.Inventors: Masafumi Fujimoto, Kensuke Sakurai, Shinichi Mihara, Miharu Nakamura, Toshiro Konoike
-
Patent number: 5216185Abstract: 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: GrantFiled: December 10, 1990Date of Patent: June 1, 1993Assignee: Loctite LimitedInventors: Stephen J. Harris, John Guthrie, Maureen MacManus, Michael A. McKervey
-
Patent number: 5216024Abstract: 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: GrantFiled: July 15, 1988Date of Patent: June 1, 1993Assignee: Baylor College of MedicineInventors: Barry M. Markaverich, James H. Clark, Rebecca Gregory, Mary Alejandro, Brian S. Middleditch, Gregory A. Johnson, Rajender S. Varma
-
Patent number: 5212201Abstract: 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: GrantFiled: November 13, 1990Date of Patent: May 18, 1993Assignee: Gunze LimitedInventors: Michio Wakashiro, Shiro Abe, Nobukazu Tanabe, Hiroshi Obata
-
Patent number: 5206414Abstract: 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: GrantFiled: April 29, 1992Date of Patent: April 27, 1993Assignee: Ciba-Geigy CorporationInventors: Samuel Evans, Paul Dubs, Milos Rusek, Zdenek Mazour, Arpad Major
-
Patent number: 5202458Abstract: 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: GrantFiled: August 5, 1991Date of Patent: April 13, 1993Assignee: Ciba-Geigy AGInventor: David G. Leppard
-
Patent number: 5177246Abstract: 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: GrantFiled: August 23, 1991Date of Patent: January 5, 1993Assignee: Ciba-Geigy CorporationInventor: Rita Pitteloud
-
Patent number: 5177247Abstract: 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: GrantFiled: March 22, 1991Date of Patent: January 5, 1993Assignee: Ciba-Geigy CorporationInventors: Franz Brogli, Guido Kalin
-
Patent number: 5155244Abstract: 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: GrantFiled: February 28, 1990Date of Patent: October 13, 1992Assignee: Karlshamns ABInventors: George H. Greene, James C. Phillips, Jerry F. Stults, Jan P. E. Tellings
-
Patent number: 5144058Abstract: 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: GrantFiled: June 15, 1990Date of Patent: September 1, 1992Assignee: International Chemical Consultant, Ltd.Inventor: Atsushi Nishimura
-
Patent number: 5136082Abstract: 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: GrantFiled: August 3, 1990Date of Patent: August 4, 1992Assignee: Himont IncorporatedInventors: Vu A. Dang, Gleason O. Cookson, Krishna Raman
-
Patent number: 5130465Abstract: 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: GrantFiled: March 22, 1991Date of Patent: July 14, 1992Assignee: Ciba-Geigy CorporationInventors: Kalman Kovasy, Zdenek Mazour
-
Patent number: 5124474Abstract: 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: GrantFiled: November 29, 1989Date of Patent: June 23, 1992Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Noritsugu Narita, Makoto Maruno
-
Patent number: 5117040Abstract: 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: GrantFiled: June 5, 1990Date of Patent: May 26, 1992Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Masayoshi Marutani, Fumihide Izumi, Kunihide Oka
-
Patent number: 5114613Abstract: 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: GrantFiled: September 13, 1989Date of Patent: May 19, 1992Assignee: Canon Kabushiki KaishaInventors: Kazuo Yoshinaga, Kazuharu Katagiri, Akira Tsuboyama, Hiroyuki Kitayama, Kenji Shinjo, Chieko Hioki
-
Patent number: 5089655Abstract: 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: GrantFiled: September 6, 1989Date of Patent: February 18, 1992Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Takanori Miura, Masanori Kohara, Kunihide Oka
-
Patent number: 5089656Abstract: 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: GrantFiled: July 18, 1990Date of Patent: February 18, 1992Assignee: Himont IncorporatedInventor: Lin-Chen Yu
-
Patent number: 5081280Abstract: 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: GrantFiled: March 7, 1989Date of Patent: January 14, 1992Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Koichi Takee, Masayoshi Gohbayashi, Kunihide Oka
-
Patent number: 5066675Abstract: 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: GrantFiled: August 31, 1990Date of Patent: November 19, 1991Assignee: Schering AktiengesellschaftInventors: Ulrich Buhmann, Hartmut Joppien, Dietrich Baumert
-
Patent number: 5051506Abstract: 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: GrantFiled: March 4, 1988Date of Patent: September 24, 1991Assignee: Displaytech, Inc.Inventors: Michael D. Wand, David M. Walba
-
Patent number: 5049696Abstract: 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: GrantFiled: June 14, 1989Date of Patent: September 17, 1991Assignee: Merck & Co., Inc.Inventors: Ta J. Lee, Clarence S. Rooney, William F. Hoffman
-
Patent number: 5025017Abstract: 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: GrantFiled: September 28, 1989Date of Patent: June 18, 1991Assignee: E. R. Squibb & Sons, Inc.Inventor: Donald S. Karanewsky
-
Patent number: 5021450Abstract: 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: GrantFiled: May 30, 1989Date of Patent: June 4, 1991Assignee: The United States of America as represented by the Secretary of the Department of Health and Human ServicesInventor: Peter M. Blumberg
-
Patent number: 5008441Abstract: 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: GrantFiled: June 20, 1989Date of Patent: April 16, 1991Assignee: The Trustees of Columbia University in the City of New YorkInventors: Koji Nakanishi, Eugene M. Oltz, Dezider Grunberger
-
Patent number: 4950780Abstract: Novel crystalline form of n-octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate with improved transportability, measurability and workability is disclosed.Type: GrantFiled: September 5, 1989Date of Patent: August 21, 1990Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Masaya Tanaka, Masayoshi Gohbayashi, Kunihide Oka
-
Patent number: 4917817Abstract: 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: GrantFiled: July 21, 1988Date of Patent: April 17, 1990Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Tetsuya Abe, Yoko Yamada, Yuko Etoh
-
Patent number: 4912249Abstract: 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: GrantFiled: November 18, 1987Date of Patent: March 27, 1990Assignee: Huels AktiengesellschaftInventors: Friedrich-Wilhelm Kupper, Heinz-Werner Voges, Werner Patzold, Richard Schaaf
-
Patent number: 4906662Abstract: 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: GrantFiled: January 27, 1987Date of Patent: March 6, 1990Assignee: Otsuka Pharmaceutical Factory, Inc.Inventors: Kinji Hashimoto, Kiyoto Goto, Ken-ichi Kanai, Yoshiaki Tsuda
-
Patent number: 4906775Abstract: 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: GrantFiled: November 18, 1987Date of Patent: March 6, 1990Assignee: Huels AktiengesellschaftInventors: Friedrich-Wilhelm Kupper, Heinz-Werner Voges, Hans-Jurgen Haage
-
Patent number: 4904815Abstract: 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: GrantFiled: October 13, 1987Date of Patent: February 27, 1990Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
-
Patent number: 4886900Abstract: 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: GrantFiled: July 17, 1987Date of Patent: December 12, 1989Assignee: Enichem Sintesi S.p.A.Inventors: Carlo Neri, Nereo Nodari, Giovanni Sandre
-
Patent number: 4885382Abstract: 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: GrantFiled: September 28, 1988Date of Patent: December 5, 1989Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Masayoshi Gohbayashi, Noritsugu Narita, Makoto Maruno
-
Patent number: 4883902Abstract: 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: GrantFiled: September 28, 1988Date of Patent: November 28, 1989Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Masayoshi Gohbayashi, Noritsugu Narita, Makoto Maruno
-
Patent number: 4882449Abstract: 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: GrantFiled: March 2, 1987Date of Patent: November 21, 1989Assignee: Loctite CorporationInventor: Stephen J. Harris
-
Patent number: 4859790Abstract: 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: GrantFiled: November 18, 1987Date of Patent: August 22, 1989Assignee: Huels AktiengesellschaftInventors: Friedrich-Wilhelm Kupper, Heinz-Werner Voges, Werner Patzold, Richard Schaaf
-
Patent number: 4855073Abstract: 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: GrantFiled: May 27, 1988Date of Patent: August 8, 1989Inventors: Mitsuhiro Murakami, Takahiro Mikami, Hiroyuki Nagamatsu, Mitsuji Tokuno
-
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
-
Patent number: 4827845Abstract: 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: GrantFiled: September 23, 1987Date of Patent: May 9, 1989Assignee: Ashland Oil, Inc.Inventors: Dace Grote, William L. Embry, Kenneth W. Barnett
-
Patent number: 4806675Abstract: 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: GrantFiled: October 19, 1987Date of Patent: February 21, 1989Assignee: Mallinckrodt, Inc.Inventors: Neil Dunski, Ali A. Bazzi
-
Patent number: 4801735Abstract: 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: GrantFiled: November 25, 1985Date of Patent: January 31, 1989Assignee: Lilly Industries LimitedInventors: Mark A. W. Finch, John R. Harris
-
Patent number: 4794138Abstract: 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: GrantFiled: August 28, 1987Date of Patent: December 27, 1988Assignee: Mallinckrodt, Inc.Inventors: Neil Dunski, Ali A. Bazzi
-
Patent number: 4790963Abstract: 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: GrantFiled: August 20, 1984Date of Patent: December 13, 1988Assignee: The Standard Oil CompanyInventors: Thomas G. Attig, Anne M. Graham, Frederick A. Pesa
-
Patent number: 4772741Abstract: 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: GrantFiled: August 31, 1987Date of Patent: September 20, 1988Assignee: Millinckrodt, Inc.Inventors: Neil Dunski, Ali A. Bazzi
-
Patent number: 4767782Abstract: 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: GrantFiled: February 20, 1987Date of Patent: August 30, 1988Assignee: Basf AktiengesellschaftInventors: Wolfgang Seppelt, Hans-Juergen Neubauer, Heinrich Adolphi, Peter Hofmeister
-
Patent number: 4739102Abstract: 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: GrantFiled: April 29, 1987Date of Patent: April 19, 1988Assignee: Ciba-Geigy CorporationInventor: Mitsukuni Tokunaga
-
Patent number: 4737591Abstract: 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: GrantFiled: December 21, 1984Date of Patent: April 12, 1988Assignee: Sun Refining and Marketing CompanyInventor: Chao-Yang Hsu
-
Patent number: 4734519Abstract: 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: GrantFiled: June 5, 1986Date of Patent: March 29, 1988Assignee: Mallinckrodt, Inc.Inventors: Neil Dunski, Ali A. Bazzi