Phenolic Hydroxy Or Metallate Patents (Class 560/75)
  • Patent number: 4733002
    Abstract: A lipoxygenase inhibitor comprising as active ingredient a substituted styrene derivative having a radical of the general formula ##STR1## wherein X denotes a hydroxyl group or a lower alkoxy group and q is an integer of 2 or 3, and containing carbon atoms in total of at least 8.
    Type: Grant
    Filed: May 23, 1985
    Date of Patent: March 22, 1988
    Assignee: Green Cross Corporation
    Inventors: Kazumasa Yokoyama, Chikara Fukaya, Masanori Sugiura, Youichiro Naito, Youichiro Nishida, Tadakazu Suyama
  • Patent number: 4731466
    Abstract: The invention concerns compounds having the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 can mean identical or different radicals in any desired position on the benzene ring, namely fluoro, chloro, bromo, iodo, cyano, or nitro radicals, alkyl radicals having from 1 to 4 carbon atoms, cyclo alkyl radicals having from 3 to 7 carbon atoms, phenyl, phenylsulfonyl and phenoxy radicals and hydrogen;n can mean a number with the value of 1 or 2 andx can mean CH.sub.2, and where n=1, O--CH.sub.2 as well.The named componds show efficiency as fungicides.
    Type: Grant
    Filed: April 30, 1987
    Date of Patent: March 15, 1988
    Assignee: The Dow Chemical Company
    Inventors: Gerhard Staiger, Peter Kinzel
  • Patent number: 4716244
    Abstract: If the transesterification of esters of formula II ##STR1## with alcohols of formula III A--OH).sub.m is catalysed by treatment with catalytic amounts of an organic or inorganic zinc salt and the resultant melt is subsequently distilled in a short-time distillation apparatus under specific conditions, then compounds of the formula ##STR2## are obtained in virtually quantitative yield, in which formulae I, II and III n is a number from 0 to 2, m is 1 or 2, A is a radical derived from an m-valent aliphatic alcohol, which radical contains 2 to 18 carbon atoms, B is methyl or tert-butyl and R is methyl or ethyl. The products thus obtained contain no troublesome by-products and do not have to be additionally purified.
    Type: Grant
    Filed: April 21, 1986
    Date of Patent: December 29, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Ivan Orban
  • Patent number: 4713475
    Abstract: Long chain (4-hydroxyphenyl) propanoate derivatives of the formula ##STR1## are effective in stabilizing organic materials against oxidative and thermal degradation.
    Type: Grant
    Filed: June 12, 1986
    Date of Patent: December 15, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: John D. Spivack, David H. Steinberg, Paul A. Odorisio
  • Patent number: 4695648
    Abstract: A compound having a potentially inhibitory effect on 15-hydroxy-prostaglandin dehydrognase (PGDH) and having the formula ##STR1## in which R.sub.1 and R.sub.2 are hydrogen or lower alkyl;R.sub.3 is hydrogen, lower alkyl or substituted or unsubstituted phenyl;R.sub.4, R.sub.5, and R.sub.6 are hydrogen, halogen, lower alkyl, lower alkoxy, cyano, carboxy or nitro; at least one of the groups R.sub.4 to R.sub.6 being hydrogen;R.sub.7 to R.sub.11 are hydrogen, halogen, cyano, lower alkyl, trifluoromethyl, lower alkoxy, hydroxy, lower acyl, lower alkoxycarbonyl, N,N,-diloweralkyl-aminocarbonyl or N,N-loweralkylene-aminocarbonyl; and R.sub.8 and R.sub.10 may in addition be carboxy; at least two of R.sub.7 to R.sub.11 always being hydrogen; and--A-- is --CO--, --CH.sub.2 --CO--, --CH.dbd.CH--, --CH.dbd.CH--CO-- or corresponding groups in which a hydrogen atom is replaced by a lower alkyl group.The invention comprises also lactones of those compounds in which R.sub.
    Type: Grant
    Filed: August 29, 1985
    Date of Patent: September 22, 1987
    Assignee: Pharmacia AB
    Inventors: Karl H. Agback, Tamara Agback, Alf S. Nygren
  • Patent number: 4694099
    Abstract: A procedure for producing stearyl-.beta.-(3,5-dibutyl-4-hydroxyphenyl)propionate and bis-(.beta.-(3,5-dibutyl-4-hydroxybenzyl)-methylcarboxyethyl)sulphide. In the procedure, a titanate-catalysis exchange esterification reaction is carried out with propionic acid ester conforming to formula (IV) and stearyl alcohol or thiodiglycol. ##STR1## where Bu is an n-butyl, secondary butyl, isobutyl or tertiary butyl group and R.sub.2 is a methyl, ethyl, propyl or butyl group.
    Type: Grant
    Filed: February 20, 1986
    Date of Patent: September 15, 1987
    Assignee: Neste Oy
    Inventors: Matts Ahlfors, Salme Koskimies, Leila Lahtinen, Peter Idelman
  • Patent number: 4690948
    Abstract: Ring opened halogenated Resorcyclic Acid Lactone (RAL) derivatives having the structure: ##STR1## are used to increase rumen fermentation efficiency.
    Type: Grant
    Filed: December 1, 1986
    Date of Patent: September 1, 1987
    Assignee: International Minerals & Chemical Corp.
    Inventor: Jing-Jong Lu
  • Patent number: 4691044
    Abstract: Mixtures of substances which are obtainable by reacting elementary sulfur with compounds of the formula I ##STR1## are described. The radical X contains an olefinic double bond. R is a hydrocarbon radical, p is 0, 1 or 2 and t is 1, 2 or 3. The mixtures of substances according to the invention can be employed as antioxidants in organic polymers and in lubricants. They can also be used as high-pressure additives or anti-wear additives.
    Type: Grant
    Filed: August 28, 1985
    Date of Patent: September 1, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Samuel Evans
  • Patent number: 4686305
    Abstract: A novel compound useful as a component of liquid crystal compositions, for lowering their melting point without lowering so much the clearing point in the mesomorphic range of the compositions, and a liquid crystal composition containing the same are provided, which compound is expressed by the general formula ##STR1## wherein R.sup.1 is alkyl or alkoxy each of 1-15 C; n is 1 or 2; and X is ##STR2## wherein R.sup.2 is alkyl or alkoxy each of 1-15 C, when n is 1, or F, Cl, CN, alkyl or alkoxy each of 1-15 C when n is 2.
    Type: Grant
    Filed: March 7, 1985
    Date of Patent: August 11, 1987
    Assignee: Chisso Corporation
    Inventor: Shigeru Sugimori
  • Patent number: 4683326
    Abstract: Seeding a melt of pentaerythritol tetrakis-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] with a small amount of the crystalline .beta.-, .delta.- or .lambda.-modification of this compound in an extruder, kneader or internal mixer at 70.degree.-130.degree. C. gives, within a few minutes, pure crystalline product without the use of a hitherto mandatory and environmentally undesirable solvent.Also described is a novel crystalline thermostable .lambda.-modification of pentaerythritol tetrakis-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate].
    Type: Grant
    Filed: July 10, 1986
    Date of Patent: July 28, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Ivan Orban, Werner Fussenegger
  • Patent number: 4675418
    Abstract: Process for preparing alkanoic acid or their esters by rearrangement of alpha-halo-ketones in protic medium and in the presence of a non-noble metal salt.The protic medium is preferably an aliphatic alcohol having low molecular weight or water and the reaction is carried out at a temperature from 0.degree. C. to the boiling-point of the diluent or of the diluents mixture.
    Type: Grant
    Filed: July 15, 1982
    Date of Patent: June 23, 1987
    Assignee: Blaschim S.p.a.
    Inventors: Claudio Giordano, Giovanni Villa, Fulvio Uggeri, Graziano Castaldi
  • Patent number: 4670495
    Abstract: Novel o-bridged polynuclear polyphenols of the formula I ##STR1## which contain at least one organic radical, such as alkyl, cycloalkyl or aryl, per phenyl nucleus and are formed by condensation of the monomeric phenolic components with customary bridging reagents, such as formaldehyde, acetone or sulfur dichloride, or by oxidative coupling of the monomeric phenolic components, and which, depending on the reaction procedure, can contain between 2 and 50 monomer units, are described.The substances according to the invention can be used for stabilizing plastics from oxidative degradation and have a good resistance to extraction.
    Type: Grant
    Filed: June 20, 1986
    Date of Patent: June 2, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Samuel Evans
  • Patent number: 4668725
    Abstract: Organic compounds of phenolic nature for stabilizing organic polymers are described together with the process for preparing said stabilizing compounds. Stabilized polymer compositions incorporating said stabilizing compounds are also described.
    Type: Grant
    Filed: October 16, 1985
    Date of Patent: May 26, 1987
    Assignees: Enichem Sintesi S.p.A., Bozzetto Industrie Chimiche S.p.A.
    Inventors: Fabio Broussard, Carlo Busetto
  • Patent number: 4661601
    Abstract: New compounds having the formula 1 ##STR1## wherein W is hydrogen, halogen, n-alkyl, --NHCOR.sup.1, --COR.sup.1, or phenoxyacetylamino optionally substituted by one or two C.sub.1-12 straight- or branched chain alkyl, X is a substituent in the coupling position and is selected from hydrogen, chlorine, bromine, --SR.sup.11 or a nitrogen-containing heterocyclic residue attached at a ring nitrogen atom, and Y is a group having the formula 2 ##STR2## wherein Q is selected from the residues: --COOR.sup.4 or --CONR.sup.4 R.sup.5, --OM, --NR.sup.7 R.sup.8, --PO(OR.sup.9)[O].sub.x R.sup.10 with X=0 or 1, --SO.sub.2 OH, --SO.sub.2 NR.sup.4 R.sup.5 or CN. The groups R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, M, k and n are defined hereinafter.These compounds are used as black color couplers in photographic materials.
    Type: Grant
    Filed: April 3, 1985
    Date of Patent: April 28, 1987
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4661616
    Abstract: Compounds represented by the general formula ##STR1## when a and b are each 0 or 1 and R represents OH or lower alkoxy when a is 1, or OH or -NR'.sub.2 when a is zero. They can be prepared by the reaction of allyl glycidly ether with the appropriate organic acid e.g. salicylic acid.Useful as ultra-violet absorbent substances and as intermediates for the preparation of other such substances, for example by polymerization and copolymerization and by reaction with organosilicon compounds having silicon-bonded hydrogen atoms.
    Type: Grant
    Filed: September 2, 1986
    Date of Patent: April 28, 1987
    Assignee: Dow Corning, Ltd.
    Inventor: Michael P. Hill
  • Patent number: 4659863
    Abstract: A process which enhances conversion and speeds the reaction rate for the preparation of esters. Methyl acrylate and a hindered phenol are reacted (i) in the presence of an alkali metal alkaline catalyst that provides a phenolate anion and (ii) in the presence of an agent which solubilizes the phenolate to enhance the reaction rate. Excellent yields of methyl ester are obtained in a rapid reaction and by-products are minimal. The invention includes a preparation of methyl .beta.-(3,5-dialkyl-4-hydroxyphenyl)propionates by reaction of a hindered phenol with methyl acrylate in the presence of an alkaline catalyst and dimethyl sulfoxide present in an amount sufficient to advance the reaction rate.
    Type: Grant
    Filed: September 12, 1985
    Date of Patent: April 21, 1987
    Assignee: Ethyl Corporation
    Inventor: Lester P. J. Burton
  • Patent number: 4640802
    Abstract: Process for the co-production of carboxylic acids of the general formula R.sup.1 --COOH and R.sup.2 --COOH and carboxylic acid esters of the general formula R.sup.1 --COOCH.sub.2 R.sup.2 and R.sup.2 --COOCH.sub.2 R.sup.1 from carboxylic acid esters of the general formula R.sup.1 --COOR.sup.2 and/or ethers of the general formula R.sup.3 OR.sup.4 (R.sup.1, R.sup.2, R.sup.3, R.sup.4 representing (substituted) alkyl or (substituted) aryl, alkaryl or aralkyl, R.sup.1 also representing H), carbon monoxide and hydrogen at elevated temperature and pressure in the presence of a ruthenium compound, a further Group VIII metal compound, a phosphine oxide and a compound R.sup.5 Hal or R.sup.5 COHal where R.sup.5 has one of the meanings given for R.sup.2 and Hal is iodine or bromine, the reaction mixture being substantially free from other transition metal or Group II metal iodides or bromides, and containing a tertiary phosphine oxide.
    Type: Grant
    Filed: July 7, 1982
    Date of Patent: February 3, 1987
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4625053
    Abstract: A process for preparing an optically active 2-(4-hydroxyphenoxy)propionic acid compound, which comprises reacting an optically active compound having the formula: ##STR1## wherein X is a chlorine atom or a bromine atom, and M is a hydrogen atom or an alkali metal atom, with hydroquinone or an alkali metal salt of hydroquinone, in the presence of an alkali metal hydroxide and water, and precipitating optically active disodium 2-(4-hydroxyphenoxy)propionate.
    Type: Grant
    Filed: November 6, 1985
    Date of Patent: November 25, 1986
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Shoji Fujinawa, Isao Hashiba, Kenji Suzuki, Syuzi Tsuchiya, Yasuo Takakuwa
  • Patent number: 4620027
    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 a combination of a palladium (II) compound, an alkali metal carboxylate and a copper salt.
    Type: Grant
    Filed: December 21, 1984
    Date of Patent: October 28, 1986
    Assignee: Sun Refining and Marketing Company
    Inventor: Chao-Yang Hsu
  • Patent number: 4618700
    Abstract: Pentaerythrityl tetrakis-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] is prepared by transesterifying a lower alkyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate with pentaerythritol in the presence of a basic catalyst, without addition of an inert solvent and in a 15 to 50% excess of lower alkyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate over the stoichiometric amount of 4 moles per 1 mole of pentaerythritol.An extremely good yield of pure crystalline product is obtained by the process of the invention.
    Type: Grant
    Filed: December 12, 1984
    Date of Patent: October 21, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Erich Gubler, Max Siegrist
  • Patent number: 4617336
    Abstract: Acylated calixarene derivatives of the formula ##STR1## are prepared by the reaction of the appropriate hydroxyphenyl alkanoate and paraformaldehyde and are useful stabilizers of organic materials.
    Type: Grant
    Filed: November 22, 1985
    Date of Patent: October 14, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Stephen D. Pastor, Paul Odorisio
  • Patent number: 4616082
    Abstract: New hydroquinone ether compounds of formula I are described: ##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 II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification,The new compounds are useful e.g. as stabilizers in photographic material.
    Type: Grant
    Filed: June 7, 1985
    Date of Patent: October 7, 1986
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4606931
    Abstract: A lift-off process for depositing a metallurgy layer on a substrate wherein the improvement is the use of a sacrificial masking layer that is substantially unaffected by exposure to high intensity radiation. The process includes the steps of (1) preparing a resin mixture of a polyaryl sulfone polymer, and a compound of the following: ##STR1## wherein R.sub.1 is a methyl ethyl or an .alpha. branched alkyl group from 3 to 10 atoms, R.sub.2 is a hydrogen, methyl, ethyl or a branched alkyl group of from 3 to 10 carbon atoms, and X has a value of 1 to 6, and Z is an aliphatic hydrocarbon of the formula C.sub.5 H.sub.8 the compound being present in the amount of from 0.5 to 3.
    Type: Grant
    Filed: June 27, 1983
    Date of Patent: August 19, 1986
    Assignee: International Business Machines Corporation
    Inventors: Beverly L. Olsen, Augustus C. Ouano
  • Patent number: 4594444
    Abstract: If the transesterification of esters of the formula II ##STR1## with alcohols of the formula III ##STR2## is catalyzed by treatment with catalytic amounts of an oxide or an organo-metallic compound of a metal of the fourth main group or subgroup of the periodic system, and if the resulting melt is then distilled in a flash distillation apparatus under specific conditions, compounds of the formula ##STR3## are obtained in a virtually quantitative yield. In the above formulae, R is methyl or ethyl, A is a radical of an m-hydric aliphatic alcohol, E is methyl or tert-butyl, m is 1 to 4 and n is 0 to 2. The products thus obtained do not contain any interfering by-products and do not have to be additionally purified.
    Type: Grant
    Filed: December 12, 1984
    Date of Patent: June 10, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Ivan Orban
  • Patent number: 4591651
    Abstract: The invention concerns a process for directly converting an aldehyde into an ethylene ester, of the type wherein the aldehyde is placed in the presence of an alkaline carbonate or bicarbonate and of a phosphonate into a solvent with an alcohol function. In the invention, an ethyl phosphonate or a methyl phosphonate is used and the solvent is an alcohol or a polyol including a hydrocarbon radical other than ethyl or methyl, this radical being that of the ethylenic ester to be produced. The process of the invention makes it possible to directly convert furan aldehyde or tetrahydrofuran aldehyde to produce an ethylenic ester with a furan ring or a tetrahydrofuran ring.
    Type: Grant
    Filed: September 26, 1984
    Date of Patent: May 27, 1986
    Assignee: Agrifurane S.A.
    Inventors: Michel Delmas, Antoine Gaset, Yves Le Bigot
  • Patent number: 4584397
    Abstract: This invention relates to methods of preventing or reducing the degradation of elastin and other proteins and thereby preventing or retarding the disease states caused by said degradation by administering compounds of the formula: ##STR1## or their pharmacologically acceptable salts.
    Type: Grant
    Filed: October 24, 1984
    Date of Patent: April 22, 1986
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis
  • Patent number: 4582526
    Abstract: Carbamic acid ester compounds of the formula ##STR1## wherein A represents the group (a) or (b) ##STR2## wherein R.sup.1 -R.sup.8, X and Y are as defined hereinafter, processes for their preparation, herbicidal compositions containing these compounds and methods for the use of the compounds and the herbicidal compositions are disclosed.
    Type: Grant
    Filed: December 9, 1983
    Date of Patent: April 15, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Jean Wenger, Rene Zurfluh
  • Patent number: 4576734
    Abstract: A stabilizer for synthetic resins containing as an effective component a mixture comprising a phenol type compound (I) represented by the formula (I), ##STR1## wherein R.sub.1 represents a C.sub.1 -C.sub.3 alkyl group, and at least one sulfur type compound (II) selected from the group consisting of compounds represented by the formula (II-1), ##STR2## wherein R.sub.2 represents a C.sub.4 -C.sub.20 alkyl group, and compounds represented by the formula (II-2), ##STR3## wherein R.sub.3 represents a C.sub.3 -C.sub.18 alkyl group, and R.sub.4 and R.sub.5 independently represent a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group, the weight ratio of phenol type compound (I) to sulfur type one (II) being 1 to 0.5-15.
    Type: Grant
    Filed: March 15, 1985
    Date of Patent: March 18, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tamaki Ishii, Shinichi Yachigo, Manji Sasaki, Masahisa Shionoya, Haruki Okamura
  • Patent number: 4570006
    Abstract: Amidino compounds represented by the formula ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful anti-trypsine, anti-plasmin, anti-kallikrein and anti-thrombin agents. Having strong anti-Cl (Clr, Cls) activities and an anticomplement activity, they are also useful as anticomplement agents. These amidino compounds are prepared by usual esterification of carboxylic acid compounds represented by the formula (II)R.sub.1 --COOH (II)with amidinophenol compound (III) and, if necessary, can be transformed into pharmaceutically acceptable acid addition salts thereof.
    Type: Grant
    Filed: October 24, 1984
    Date of Patent: February 11, 1986
    Assignee: Torii & Co. Ltd.
    Inventors: Setsuro Fujii, Takashi Yaegashi, Toyoo Nakayama, Yojiro Sakurai, Shigeki Nunomura, Toshiyuki Okutome
  • Patent number: 4549015
    Abstract: New hydroquinone ether compounds of formula I are described: ##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 II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification.The new compounds are useful e.g. as stabilizers in photographic material.
    Type: Grant
    Filed: June 14, 1983
    Date of Patent: October 22, 1985
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4547583
    Abstract: Carboxylic acids containing phenol groups are esterified by means of (C.sub.1 -C.sub.3)-alcohols in the presence of acid catalysts without the phenolic hydroxyl groups being esterified at the same time by continuously metering an excess of a water-containing (C.sub.1 -C.sub.3)-alcohol into a boiling hot solution or suspension of the phenol-containing carboxylic acid and of the catalyst in a non-water-miscible solvent (for example xylene) and at the same time distilling off a ternary solvent/alcohol/water mixture via a water separator, the metering rate being such that an aqueous bottom phase separates out in the receiving flask and the water content of the alcohol being so apportioned as not to breach the bottom limit of 0.1% or the upper limit of 1% (based on the contents of the reaction vessel) at any time in the course of the reaction. In this process, the esterification products are obtained free of major impurities and frequently can be used further without further purification.
    Type: Grant
    Filed: October 3, 1984
    Date of Patent: October 15, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hans J. Nestler
  • Patent number: 4547585
    Abstract: Tetrakis [3-(3,5-dibutyl-4-hydroxyphenyl)propionyloxymethyl] methane having a high purity and excellent whiteness is prepared. In this process, an ester exchange reaction between a propionic acid ester having the general formula: ##STR1## wherein Bu is an n-, sec-, iso-, or tert-butyl group and R.sup.1 is an alkyl group having 1 to 4 carbon atoms, and pentaerythritol in the presence of an alkaline catalyst is effected by adding 0.2 through 1.8 mol of water based on 1 mol of the alkaline catalyst by the substantial completion of the ester exchange reaction.
    Type: Grant
    Filed: May 25, 1982
    Date of Patent: October 15, 1985
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Toru Yamanaka, Tadatoshi Yoshimura
  • Patent number: 4544766
    Abstract: This invention relates to a process for preparing an aryl acetic acid derivative represented by the formulaAr--CH.sub.2 COY).sub.ncomprising hydrolyzing in an alkaline substance a dichloroethenyl compound represented by the formulaAr--CH.dbd.CCl.sub.2).sub.n.
    Type: Grant
    Filed: February 26, 1982
    Date of Patent: October 1, 1985
    Assignee: Otsuka Kagaku Yakuhin Kabushiki Kaisha
    Inventor: Tatsuya Shono
  • Patent number: 4537988
    Abstract: An integrated process for the preparation of 2-(4-hydroxyphenyl)-3-methylbutyric acid from the corresponding 2-(4-chlorophenyl)-3-methylbutyronitrile through hydrolysis of the nitrile by strong base to the corresponding carboxylic acid followed by formation of the corresponding phenol by nucleophilic displacement of the chlorine with a strong base in the presence of copper salts, and if so desired metallic copper, is described.
    Type: Grant
    Filed: June 6, 1983
    Date of Patent: August 27, 1985
    Assignee: American Cyanamid Company
    Inventor: Charles P. Grasso
  • Patent number: 4536593
    Abstract: If the transesterification of esters of the formula ##STR1## with alcohols of the formula III A--(OH).sub.m is catalyzed by successive treatment with catalytic amounts (a) of a tin compound of a metal of the fourth main group or the fourth sub-group of the periodic system and (b) of an acid earth, compounds of the formula I ##STR2## are obtained in virtually quantitative yield. The products thus obtained contain no troublesome by-products and do not have to be additionally purified.R is methyl or ethyl, A is a radical derived from an m-hydric aliphatic alcohol, n is 0 to 2, and m is 1 to 4.
    Type: Grant
    Filed: July 5, 1983
    Date of Patent: August 20, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Ivan Orban, Eduard Troxler
  • Patent number: 4529809
    Abstract: A method for producing high yields of aryl substituted esters of the formula ##STR1## by reacting sterically hindered phenols with a stoichiometric excess of an olefinic ester in the presence of a base catalyst at a temperature in the range of 150.degree. to 250.degree. C.
    Type: Grant
    Filed: August 29, 1983
    Date of Patent: July 16, 1985
    Assignee: General Electric Company
    Inventors: William H. Irving, Arnold Factor
  • Patent number: 4514416
    Abstract: Amidino compounds represented by the formula (I) ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful antitrypsine, antiplasmin, antikallikrein and anti-thrombin agents. Having strong anti-Cl (Clr, Cls) activities and an anticomplement activity, they are also useful as anticomplement agents. These amidino compounds are prepared by usual esterification of carboxylic acid compounds represented by the formula (II)R.sub.1 --COOH (II)with amidinophenol compound (III) and, if necessary, can be transformed into pharmaceutically acceptable acid addition salts thereof.
    Type: Grant
    Filed: May 21, 1984
    Date of Patent: April 30, 1985
    Assignee: Torii & Co. Ltd.
    Inventors: Setsuro Fujii, Takashi Yaegashi, Toyoo Nakayama, Yojiro Sakurai, Shigeki Nunomura, Toshiyuki Okutome
  • Patent number: 4511491
    Abstract: Phenolic compounds and methods of producing such phenolic compounds are disclosed, said compounds being of the formula: ##STR1## wherein n' is an integer from 1 to 3, and R.sub.1 is a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms.These compounds are suitable as stabilizers for synthetic resins with at least one sulfur compound of the following formulas: ##STR2## wherein R.sub.2 is an alkyl group having 4 to 20 carbon atoms, and ##STR3## wherein R.sub.3 is an alkyl group having 3 to 18 carbon atoms, and R.sub.4 and R.sub.5 each independently is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,in the ratio (I):(II) of 1:0.5-15 by weight.
    Type: Grant
    Filed: July 15, 1983
    Date of Patent: April 16, 1985
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Tamaki Ishii, Shinichi Yachigo, Yukoh Takahashi
  • Patent number: 4484000
    Abstract: New hydroquinones having 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 selected from the residues --COZR.sub.4 wherein Z is 0 or NR.sub.5, --OX wherein X is R.sub.5 or --COR.sub.7, --NR.sub.8 R.sub.9, --PO(OR.sub.10)[O].sub.x R.sub.11 wherein x is 0 or 1, --SO.sub.2 R.sub.12 or --CN, and salts thereof with organic or inorganic acid bases.The groups, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, k and n are defined hereafter.These compounds are used as stabilizers in photographic materials.
    Type: Grant
    Filed: June 18, 1982
    Date of Patent: November 20, 1984
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4474806
    Abstract: Sulfonyl or carbonyl derivatives of inositols are found to be effective phospholipase C inhibitors and thereby potent anti-inflammatory and analgesic agents. These inositol derivatives are prepared by condensation of a protected inositol with a substituted sulfonic or carboxylic acid derivative followed by removal of protecting groups.
    Type: Grant
    Filed: May 10, 1982
    Date of Patent: October 2, 1984
    Assignee: Merck & Co., Inc.
    Inventors: Thomas R. Beattie, Shu S. Yang
  • Patent number: 4467106
    Abstract: A process for making polyether/polyester glycols and the products formed thereby. Polyether/polyester glycols having a molecular weight of about 200 to 2,200 are formed by heating any of various glycols at about 150.degree. to 250.degree. C. under carbon monoxide pressure in the presence of a halide promoter. Preferably, iodide or bromide and a transition metal-containing catalyst are used to produce polyether/polyester glycols having a molecular weight in the range of 900 to 1,200.
    Type: Grant
    Filed: April 15, 1982
    Date of Patent: August 21, 1984
    Assignee: Ethyl Corporation
    Inventors: Sundar J. Rajan, Edmund F. Perozzi
  • Patent number: 4448730
    Abstract: Di, tri and tetrahydroxybenzohydroxamic acids, amides and the corresponding di, tri and tetrahydroxy substituted phenylalkanohydroxamic acids, amides and phenyl esters, ribonucleotide reductase inhibitors.
    Type: Grant
    Filed: April 20, 1982
    Date of Patent: May 15, 1984
    Inventors: Bartholomeus van't Riet, Howard L. Elford, Galen L. Wampler
  • Patent number: 4417071
    Abstract: A process for the manufacture of phenols of the formula I ##STR1## wherein R.sub.1 is alkyl of 1 to 18 carbon atoms, cycloalkyl, phenyl, aralkyl or chlorine, R.sub.2 is hydrogen or has the same meaning as R.sub.1, R.sub.3 is hydrogen or alkyl of 1 to 12 carbon atoms, R.sub.4 is alkylene of 2 to 18 carbon atoms which is unsubstituted or substituted by aryl or hydroxyl, and n is an integer from 0 to 4, which process comprises transesterifying a compound of the formula II ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined for formula (I) and R.sub.5 is alkyl of 1 to 4 carbon atoms with a mercapto alcohol of the formulaHO--R.sub.4 --SHwherein R.sub.4 is as defined for formula (I), in the presence of a catalyst of the formula (R.sub.6 O).sub.4 M, wherein R.sub.6 represents alkyl radicals of 1 to 18 carbon atoms which can be the same or different, aryl or alkaryl, and M is an element selected from the group consisting of Ti, Ge, Zr, Sn or V.
    Type: Grant
    Filed: March 11, 1982
    Date of Patent: November 22, 1983
    Assignee: Ciba-Geigy Corporation
    Inventor: Siegfried Rosenberger
  • Patent number: 4405807
    Abstract: Novel tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxymethyl)methane having a novel crystal structure characterized by the fact that its X-ray diffraction pattern obtained by X-ray analysis using Cu-K.sub..alpha. rays shown a sharp peak at a diffraction angle 2.theta.=10.90.degree.. The above compound can be prepared by (a) transesterifying methyl or ethyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate with pentaerythritol in the presence of a compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 each represent an alkyl group having 1 to 6 carbon atoms,(b) treating the resulting tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxymethyl)methane with a lower alkanol capable of forming a molecular adduct compound therewith to convert it into the corresponding molecular adduct compound, and (c) recrystallizing the molecular adduct compound from ethanol as a solvent.
    Type: Grant
    Filed: January 13, 1981
    Date of Patent: September 20, 1983
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Hiroshi Hasui, Toshikazu Furihata, Kazuko Takanashi, Masahiko Ohmori
  • Patent number: 4396552
    Abstract: Metal mercaptides of the formula ##STR1## wherein Me is a metal, oxometal, alkoxymetal or organo-metal cation from the 1st-5th group of the periodic system, n is 0, 1 or 2, m is an integer from 1 to 4, R.sup.1 is hydrogen, alkyl, acyloxymethyl or alkoxymethyl, R.sup.2 is a sterically hindered phenol group, and R.sup.3 is a monovalent organic radical, are stabilizers for organic materials which are sensitive to heat and oxygen. They can be used in particular as stabilizers for chlorine-containing thermoplasts, for elastomers and for lubricants. Preferred cations are organotin cations.
    Type: Grant
    Filed: January 28, 1981
    Date of Patent: August 2, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Gerrit Knobloch, Wolfgang Wehner, Hermann O. Wirth
  • Patent number: 4385143
    Abstract: Synthetic resins, particularly polyolefins, are markedly improved in their resistances to heat and oxidation by the incorporation of a 2-methyl-4-t-butyl-5-hydroxyphenylalkanoic acid ester alone or in combination with a thioether-type antioxidant represented by the general formula ##STR1## wherein R represents an alkyl group of 12 to 20 carbon atoms, or by the general formula ##STR2## wherein R represents an alkyl group of 4 to 20 carbon atoms.
    Type: Grant
    Filed: August 31, 1981
    Date of Patent: May 24, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shinichi Yachigo, Yuko Takahashi, Tsutomu Mitsuda, Mitsuhisa Nakatani
  • Patent number: 4374263
    Abstract: The invention relates to an esterification process employing as a heterogeneous catalyst an inorganic oxide, e.g. silica, to which there is bonded by reaction with surface hydroxyl groups a sulphonic acid-functionalized silane.
    Type: Grant
    Filed: October 24, 1980
    Date of Patent: February 15, 1983
    Assignee: The British Petroleum Company Limited
    Inventors: Ronald D. Hancock, Robert Mackison
  • Patent number: 4353836
    Abstract: 4-(2,5-Dihydroxyphen-1-yl)-crotonic acid and its derivative (I) ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each H or C.sub.1 -C.sub.8 -alkyl, R.sup.5 is H, C.sub.1 -C.sub.30 -alkyl or C.sub.2 -C.sub.30 -alkenyl, and R' is H or an organic radical which can be split off hydrogenolytically, and a process for the preparation of the compounds I, wherein a hydroquinone II ##STR2## is reacted, in the presence of from 0.1 to 2 moles of a Lewis acid per mole of II, with(a) a vinylglycolic acid derivative IIIa ##STR3## or (b) a crotonic acid derivative IIIb ##STR4## where X is halogen, hydroxyl or C.sub.1 -C.sub.4 -alkoxy or acyloxy.
    Type: Grant
    Filed: February 26, 1981
    Date of Patent: October 12, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Horner, Axel Nissen
  • Patent number: 4354035
    Abstract: The present invention is related to a new process for producing rosmarinic acid by extraction of certain plants, and in particular of plants of balmmint (Melissa officinalis).
    Type: Grant
    Filed: March 11, 1981
    Date of Patent: October 12, 1982
    Assignee: A. Nattermann & Cie GmbH
    Inventors: Bruno Christ, Kurt Kesselring
  • Patent number: 4339594
    Abstract: Phenylacetic acid and the simple derivatives thereof are prepared by catalytic hydrogenation of mandelic acid and its appropriate derivatives in the presence of a noble metal catalyst in aqueous solution which is free from mineral acid, especially free from hydrochloric acid.
    Type: Grant
    Filed: October 31, 1980
    Date of Patent: July 13, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Werner Spielmann, Georg Schaeffer