Phenolic Hydroxy Or Metallate Patents (Class 560/67)
  • 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: 4876381
    Abstract: The invention relates to a compound of the formula (II) ##STR1## and the corresponding isomers and salts, in which formula: a and b are integers which independently of one another can assume the values 0 or 1,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent, independently, a hydrogen atom, a linear or branched C.sub.1 -C.sub.6 -alkyl radical or a C.sub.1 -C.sub.4 -alkoxy radical,R.sub.6 represents a C.sub.1 -C.sub.6 -alkyl radical,R.sub.5 and R.sub.12 represent a hydrogen atom or a C.sub.1 -C.sub.4 -alkyl radical, with the proviso that R.sub.5 cannot represent hydrogen if a=b=0 andR.sub.11 has various meanings.These compounds have useful dermatological properties.
    Type: Grant
    Filed: August 18, 1987
    Date of Patent: October 24, 1989
    Assignee: L'Oreal
    Inventors: Gerard Lang, Jean Maignan, Serge Forestier, Serge Restle, Alain Lagrange, Braham Shroot
  • Patent number: 4874886
    Abstract: This invention relates to novel fluorinated bis(salicylates). The novel fluorinated bis(salicylates) of this invention are useful as monomers in the synthesis of polymers and copolymers themselves useful as gas separation membrane materials.
    Type: Grant
    Filed: November 7, 1988
    Date of Patent: October 17, 1989
    Assignee: The Dow Chemical Company
    Inventor: Charles B. Grant
  • Patent number: 4873018
    Abstract: An optically active 2-fluoro-1-alkanol compound represented by the formula (Ia): ##STR1## wherein R is an alkyl group having 1-16 carbon atoms, and C* is an asymmetric carbon atom; and an optically active compound derived from the fluoroalkanol and represented by the formula (Ib): ##STR2## wherein R and C* are the same as above, m is 1 or 2, n is 0 or 1, and A is a releasable substitutent. Because of the fluorine atom directly attached to an asymmetric carbon atom, these compounds are particularly effective in increasing a spontaneous polarization, improving a electric field responsive characteristic of a liquid crystal composition, and controlling the liquid crystal state.
    Type: Grant
    Filed: October 27, 1987
    Date of Patent: October 10, 1989
    Assignees: Canon Kabushiki Kaisha, Yamakawa Yakuhin Kogyo Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuo Yoshinaga, Mariko Kai, Kazuharu Katagiri
  • Patent number: 4853398
    Abstract: This invention provides benzene derivatives which are leukotriene antagonists, formulations of those derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.
    Type: Grant
    Filed: April 13, 1987
    Date of Patent: August 1, 1989
    Assignee: Eli Lilly and Company
    Inventors: F. P. Carr, Robert D. Dillard, Doris E. McCullough
  • Patent number: 4841093
    Abstract: A diallyl aromatic dicarboxylate derivative of the formula ##STR1## wherein Y is hydrogen atom or perfluoroalkenyl group having 6 to 14 carbon atoms, is a novel compound. The compound (1) is a starting material for a prepolymer containing a repeating unit derived from diallyl aromatic fluorine-containing dicarboxylate and represented by the formula ##STR2## wherein X is prefluoroalkenyl group having 6 to 14 carbon atoms.
    Type: Grant
    Filed: October 19, 1987
    Date of Patent: June 20, 1989
    Assignee: Daikin Industries, Ltd.
    Inventors: Sinji Tamaru, Motonobu Kubo
  • Patent number: 4814497
    Abstract: Particulate aluminum is intimately mixed with an aromatic material that contains at least one ar-halo substituent having an atomic number above 20 and at least one side-chain halo substituent having an atomic number below 20 in the presence of an aqueous alkali or alkaline earth metal hydroxide so as to effect selective removal of the ar-halo substituent.
    Type: Grant
    Filed: May 12, 1986
    Date of Patent: March 21, 1989
    Assignee: Ethyl Corporation
    Inventor: K. Pushpananda A. Senaratne
  • 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: 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: 4692552
    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: February 18, 1986
    Date of Patent: September 8, 1987
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis
  • Patent number: 4686235
    Abstract: Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophlic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: August 11, 1987
    Assignee: Merck & Co., Inc.
    Inventors: Michael N. Chang, Norman P. Jensen, Milton L. Hammond, Robert A. Zambias, John McDonald, Kathleen M. Rupprecht
  • Patent number: 4683327
    Abstract: A novel heat-curable acrylic-terminated monomer is provided which exhibits an optically anisotropic melt phase at a temperature which enables it to undergo melt processing in the formation of molded articles, etc. Subsequent to melt processing articles prepared from the monomer are capable of being cured to produce a thermoset self-reinforced composite which is soft and flexible relative to prior art monomers. The monomer may, for example, consist essentially of the reaction product of a methacrylic-substituted phenol and terephthalic acid.
    Type: Grant
    Filed: June 24, 1985
    Date of Patent: July 28, 1987
    Assignee: Celanese Corporation
    Inventor: Robert W. Stackman
  • 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: 4643763
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: m is an integer selected from 1 to 4;n is zero or an integer selected from 1 to 4;x are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, alkylthio, sulfamoyl, substituted sulfamoyl, amino, substituted amino, the group --(CH.sub.2).sub.p C(.dbd.A)Z in which p is zero or one A is oxygen or sulfur, and Z is hydrogen, hydroxy, alkoxy, alkylthio, alkyl, substituted alkyl, amino or substituted amino; the group --NHC(.dbd.B(NR.sup.7 R.sup.8 in which B is oxygen or sulfur and R.sup.7 and R.sup.8 are hydrogen or alkyl;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; andR.sup.4 is selected from hydrogen, halogen, alkyl, cyano and alkoxycarbonyl.
    Type: Grant
    Filed: September 10, 1985
    Date of Patent: February 17, 1987
    Assignee: ICI Australia Limited
    Inventors: Graeme J. Farquharson, Keith G. Watson, Graham J. Bird
  • Patent number: 4640708
    Abstract: Compounds of the formula ##STR1## wherein: R.sup.5 is a bicyclic aryl or nitrogen-containing heteroaryl ring system such as naphthyl, quinolyl, isoquinolyl or tetrahydroisoquinolyl, optionally substituted by a wide variety of groups;R.sup.4 and R.sup.1 are preferably hydrogen but may be other groups andR.sup.2 and R.sup.3 are selected from alkyl, haloalkyl, alkenyl, haloalkenyl and alkynyl, show high general grass-killing activity with good selectivity to many broad-leaf crops and in some instances selectivity to small-grain cereals. Processes for the preparation of compounds of formula I, intermediates in the preparation of compounds I and the herbicidal properties of compounds I are described.
    Type: Grant
    Filed: March 20, 1984
    Date of Patent: February 3, 1987
    Assignee: ICI Australia Limited
    Inventors: Graham J. Bird, Graeme J. Farquharson, Keith G. Watson
  • Patent number: 4624802
    Abstract: The process of scenting, comprising the steps of treating the material to be scented with an application of scenting-effective amount of a scenting agent, the improvement consisting of using a salicylic acid ester having the formula: ##STR1## wherein R is a member having from 5 to 9 carbon atoms selected from the group consisting of cycloalkyl, C.sub.1 -C.sub.4 -alkylcycloalkyl, cycloalkenyl and C.sub.1 -C.sub.4 -alkylcycloalkenyl, and n is an integer from 0 to 3, as said scenting agent; more particularly using cyclohexyl salicylate or cyclopentyl salicylate as said scenting agent; as well as perfumery compositions containing said scenting agents; and salicylic acid ester scenting agents selected from the group consisting of:(a) Cyclopentyl salicylate,(b) 2,2,4-(2,4,4-)trimethylcyclopentyl salicylate in the form of an isomer mixture,(c) 4-isopropylcyclohexyl salicylate,(d) cyclohexylmethyl salicylate,(e) cycloheptyl salicylate(f) cyclooctyl salicylate, and(g) cyclooct-4-enyl salicylate.
    Type: Grant
    Filed: January 2, 1985
    Date of Patent: November 25, 1986
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Ulf-Armin Schaper, Benno Streschnak, Siegfried Bloesl, Walter Sommer
  • 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: 4613683
    Abstract: C.sub.1 -C.sub.20 -alkyl gallates are prepared by reacting tannin-containing material with the corresponding alcohol R--OH and a strong acid.
    Type: Grant
    Filed: January 25, 1985
    Date of Patent: September 23, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Rebafka, Helmut Nickels
  • Patent number: 4613678
    Abstract: Esterification of aromatic dicarboxylic acids with cyclic alkylene carbonates in the presence of organic compounds containing at least one six-membered aromatic nitrogen-containing heterocyclic moiety.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: September 23, 1986
    Assignee: The Dow Chemical Company
    Inventor: Daniel J. Swart
  • Patent number: 4594460
    Abstract: Substituted phenols of formula ##STR1## in which R.sub.1 is in an ortho or para position relative to the phenol function and denotes ##STR2## R.sub.2 denotes an acyclic radical optionally substituted by alkyl, hydroxy, alkoxycarbonyl, cyano or formyl, or a phenyl or naphthyl radical, and R denotes hydrogen or 1 to 4 substituents chosen from halogen, OH optionally in the form of ether or ester, alkyl, NO.sub.2, CHO optionally in the form of acetal, CH.sub.3 CO--, C.sub.6 H.sub.5 CO--, NH.sub.2, alkylamino, dialkylamino or alkoxycarbonyl, it being understood that 2 symbols R may form with the phenyl nucleus a condensed aromatic ring, which comprises reacting a butadiene of formula ##STR3## with a phenol for formula ##STR4## in water in the presence of a rhodium-based catalyst, a water-soluble phosphine and optionally an inorganic or organic base. The products of formula (I) are intermediates for the synthesis of vitamin E, antioxidants, perfumes or insecticides.
    Type: Grant
    Filed: March 19, 1985
    Date of Patent: June 10, 1986
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel
  • 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: 4582855
    Abstract: Novel compounds of the general formula ##STR1## wherein Ar represents a substituted or unsubstituted aromatic or heterocyclic group; W represents alkylene of from 1 to about 10 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1, or R.sub.1 and R.sub.3 may together with N form a 5 to 7 momoered heterocyclic group; and the pharmaceutically acceptable salts thereof. These compounds exhibit .beta.-adrenergic blocking activity and are also useful in the treatment of glaucoma.
    Type: Grant
    Filed: November 12, 1981
    Date of Patent: April 15, 1986
    Assignee: American Hospital Supply Corporation
    Inventors: Sheung T. Kam, William L. Matier
  • 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: 4537970
    Abstract: This invention relates to the preparation of esters or salts of aromatic or etheroaromatic acids having formula Y--Ar--CO--OR (I), where:Ar represents an aromatic group constituted by one or more benzene rings, optionally condensed, or an etheroaromatic nucleus optionally condensed with one or more benzene rings;Y represents from zero to more substituents, equal or different, chosen among a halogen; an alkyl group having up to 6 carbon atoms; an alkoxy group having up to 5 carbon atoms; an ester group --COOR', where R' contains up to 5 carbon atoms; a hydroxyl group; a phenyloxy group, optionally substituted with groups inert under reaction conditions; a trifluoromethyl group; a nitrile group; an amidic group (--CONH.sub.2); an acetamidic group (--NH--CO--CH.sub.3); or an acyl group --CO--R", where R" represents a hydrocarbon group having up to 8 carbon atoms;R represents an alkyl group R.sub.1 having up to 5 carbon atoms or an alkali metal or alkaline earth metal M.
    Type: Grant
    Filed: December 12, 1983
    Date of Patent: August 27, 1985
    Assignee: Montedison S.p.A.
    Inventors: Marco Foa, Franco Francalanci, Andrea Gardano, Elena Bencini
  • 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: 4528395
    Abstract: A process for making C.sub.8 -C.sub.20 alkyl esters by esterification of 3,5-di-tert-butyl-4-hydroxybenzoic acid with a C.sub.8 -C.sub.20 alcohol. The esterification reaction is conducted at 110.degree.-150.degree. C. in the presence of 5-20 weight percent based on the weight of 3,5-di-tert-butyl-4-hydroxybenzoic acid, of a strongly acidic gel-type ion-exchange resin catalyst having less than about 8 percent cross-linking.
    Type: Grant
    Filed: August 15, 1983
    Date of Patent: July 9, 1985
    Assignee: American Cyanamid Co.
    Inventors: Richard F. Beidler, Philip R. Ruby
  • Patent number: 4501912
    Abstract: A method for the treatment of glaucoma or lowering intraocular pressure in a mammal, involving topically administering to the eye of such mammal a selectively metabolized beta-blocking compound of the formula ##STR1## wherein R may be lower alkyl, lower hydroxyalkyl, lower alkynyl, aralkyl, or an ester-containing group and Ar may be substituted or unsubstituted aromatic; or a pharmaceutically acceptable salt thereof. Because of a relatively long duration of action of such compounds in ocular fluids and a relatively short duration of action in the systemic circulation, such compounds are useful for the treatment of excessive intraocular pressure without substantial systemic effects.
    Type: Grant
    Filed: December 13, 1982
    Date of Patent: February 26, 1985
    Assignee: American Hospital Supply Corporation
    Inventors: William L. Matier, Sheung-Tsam Kam
  • Patent number: 4499295
    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: May 9, 1983
    Date of Patent: February 12, 1985
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis
  • Patent number: 4454338
    Abstract: Amidino compounds represented by the formula ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful antitrypsine, antiplasmin, antikallikrein and antithrombin agents. Having strong anti-C1 (C1r, C1s) 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 ##STR2## with 6-amidino-2-naphthol and, if necessary, can be transformed into pharmaceuticlly acceptable acid addition salts thereof.
    Type: Grant
    Filed: September 9, 1981
    Date of Patent: June 12, 1984
    Assignee: Torii & Co., Ltd.
    Inventors: Setsuro Fujii, Toshiyuki Okutome, Toyoo Nakayama, Takashi Yaegashi, Masateru Kurumi
  • Patent number: 4440945
    Abstract: Novel heat-curable acetylene-terminated monomers are provided which exhibit an optically anisotropic melt phase at a temperature which enables it to undergo melt processing in the formation of molded articles, etc. The monomers are capable of being heat-cured at temperatures in excess of the melt processing temperatures to produce a thermoset self-reinforced composite.
    Type: Grant
    Filed: July 19, 1982
    Date of Patent: April 3, 1984
    Assignee: Celanese Corporation
    Inventors: Anthony B. Conciatori, Eui W. Choe, Gerald Farrow
  • 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: 4408065
    Abstract: An adsorptive separation process for separating methylparaben from a feed mixture comprising methylparaben and wintergreen oil, which process comprises contacting the feed mixture with an adsorbent comprising a type X or type Y zeolite, selectively adsorbing substantially all of the methylparaben to the substantial exclusion of the wintergreen oil and thereafter recovering high-purity methylparaben. A desorption step may be used to desorb the adsorbed methylparaben. The process is carried out preferably in the liquid phase.
    Type: Grant
    Filed: March 23, 1981
    Date of Patent: October 4, 1983
    Assignee: UOP Inc.
    Inventors: Armand J. deRosset, James W. Priegnitz, Arthur M. Landis
  • Patent number: 4408059
    Abstract: Milbemycin and avermectin macrolides are synthesized by the cyclized linking of separately synthesized northern and southern hemisphere intermediates. The northern hemisphere intermediate is a spiroketal alkenyl aldehyde, and the southern hemisphere intermediate is an aryl alkenyl phosphine oxide anion.
    Type: Grant
    Filed: December 4, 1981
    Date of Patent: October 4, 1983
    Assignee: University Patents, Inc.
    Inventors: Amos B. Smith, III, Steven R. Schow
  • Patent number: 4402974
    Abstract: A method for the treatment of glaucoma or lowering intraocular pressure in a mammal, involving topically administering to the eye of such mammal a selectively metabolized beta-blocking compound of the formula ##STR1## wherein R may be lower alkyl, lower hydroxyalkyl, lower alkynyl, aralkyl, or an ester-containing group and Ar may be substituted or unsubstituted aromatic; or a pharmaceutically acceptable salt thereof. Because of a relatively long duration of action of such compounds in ocular fluids and a relatively short duration of action in the systemic circulation, such compounds are useful for the treatment of excessive intraocular pressure without substantial systemic effects.
    Type: Grant
    Filed: June 23, 1981
    Date of Patent: September 6, 1983
    Assignee: American Hospital Supply Corporation
    Inventors: William L. Matier, Sheung-Tsam Kam
  • Patent number: 4374262
    Abstract: A process for preparing hydroxy aromatic carboxylic acids, or the ester derivatives thereof, comprises carbonylating a hydroxy aromatic halide in the presence of a reactive alcohol solvent and a catalytic amount of a Group VIII metal catalyst. The process has particular applicability to the preparation of 6-hydroxy-2-naphthoic acid from 6-bromo-2-naphthol, which can be easily prepared from .beta.-naphthol, a readily available and inexpensive starting material.
    Type: Grant
    Filed: October 6, 1980
    Date of Patent: February 15, 1983
    Assignee: Celanese Corporation
    Inventors: James L. McGinnis, Anthony B. Conciatori
  • 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: 4346039
    Abstract: A simple, direct synthesis route is provided for Ochratoxin compounds, particularly Ochratoxin A, Ochratoxin B, and Ochratoxin C. The reaction involves treating the dimethyl ester of 2-hydroxy-4-methylbenzene-1,3-dioic acid with a deprotonating agent, followed by addition of acetaldehyde, to provide a precursor compound, which can conveniently be converted to Ochratoxins A, B or C. The synthesis route allows for the first time laboratory and industrial scale synthesis of ochratoxins A, B and C in large quantities and pure form making them available as toxins, for use as anti-toxin investigation works, and for biological activity investigations and residue studies.
    Type: Grant
    Filed: March 19, 1981
    Date of Patent: August 24, 1982
    Assignee: Iowa State University Research Foundation, Inc.
    Inventor: George A. Kraus
  • Patent number: 4338170
    Abstract: A cis-trans isomerization of a cis-.beta.-.gamma.-unsaturated alcohol or its ester having the formula ##STR1## wherein R.sub.1 represents hydrogen atom or a C.sub.1 -C.sub.5 alkyl group; X represents hydrogen atom or ##STR2## and R.sub.2 represents a hydrocarbon moiety or a hydroxyhydrocarbon moiety; R.sub.3 represents hydrogen atom or a hydrocarbon moiety into a transform, in the presence of a mercaptan as a catalyst, is provided. It can be also attained in the presence of a mercaptan and/or a disulfide as a catalyst in an inert gas environment with an initiator. It can be also attained in the presence of a mercaptan under an irradiation, if desired with a small amount of an initiator.
    Type: Grant
    Filed: May 23, 1980
    Date of Patent: July 6, 1982
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Atsuo Murata, Syuji Tsuchiya, Hideo Suzuki
  • Patent number: 4335250
    Abstract: A new compound is produced which has the general formula: ##STR1## wherein R represents hydrogen atom or a lower alkyl group and which exhibits an immunopotentiating activity. This new compound as well as its pharmaceutically acceptable salts and hydrates are useful for immunotherapy and treatment of immune diseases and disorders in living animals including human beings. The new compound can be produced by reduction of a hydroxyterephthalic acid alkyl ester or by esterification of the corresponding 3-hydroxy-4-(hydroxymethyl)-benzoic acid.
    Type: Grant
    Filed: July 12, 1979
    Date of Patent: June 15, 1982
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Hamao Umezawa, Tomio Takeuchi, Takaaki Aoyagi, Masaaki Ishizuka, Hajime Morishima, Takuzo Yamamoto, Junji Yoshizawa, Masaaki Hosoi, Ikuo Matsumoto
  • Patent number: 4310465
    Abstract: A synthesis of Vitamin E has the condensation of 2,4-pentanediene and 1,2-epoxy-2,6,10,14-tetramethylpentadecane including intermediates in this synthesis which uses base catalyzed condensations of aliphatic compounds to construct the Vitamin E molecule from aliphatic precursors.
    Type: Grant
    Filed: December 17, 1979
    Date of Patent: January 12, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Gary L. Olson, Gabriel Saucy
  • Patent number: 4309564
    Abstract: Novel methods of forming in situ eutectic mixtures of three or more lower alkyl esters of p-hydroxybenzoic acid are disclosed which avoid the prior art methods of forming the respective esters independently and blending them, for example, by melting. Such eutectic mixtures may be formed in situ by first reacting a p-hydroxybenzoic acid and a lower alkanol in the presence of an esterification catalyst to form a first lower alkyl ester of p-hydroxybenzoic acid, reacting the resulting mixture with two or more lower alkanols under heat to form a mixture of three or more lower alkyl esters of p-hydroxybenzoic acid, quenching the reaction when the ratio of the respective lower alkyl esters of p-hydroxybenzoic acid to each other is such that the mixture thereof is liquid at room temperature and isolating the resulting eutectic mixture. Other methods of preparing such eutectic mixtures in situ are also disclosed.
    Type: Grant
    Filed: October 23, 1980
    Date of Patent: January 5, 1982
    Assignee: Mallinckrodt, Inc.
    Inventors: Donald F. Loncrini, John J. Taylor
  • Patent number: 4305868
    Abstract: Novel phenolically substituted esterbisamides as antioxidants useful for the protection of organic materials such as synthetic and natural rubbers, plastics and petroleum products against oxidative degradation.
    Type: Grant
    Filed: May 30, 1979
    Date of Patent: December 15, 1981
    Assignee: Uniroyal, Inc.
    Inventors: Edward L. Wheeler, Elmar H. Jancis, Richard A. Gencarelli, Franklin H. Barrows
  • Patent number: 4276431
    Abstract: Alkali metal salts of hydroxybenzoates are claimed which are substantially anhydrous and free from hydrobenzoic acid and have the formula ##STR1## in which R.sup.1 denotes alkyl, alkenyl, cycloalkyl or aralkyl,R.sup.2 and R.sup.3 are identical or different and represent hydrogen, halogen, hydroxyl, amino, alkylamino, alkyl, alkoxy, aralkyl or aryl andMe denotes an alkali metal.Furthermore a process for the preparation of the said alkali metal salts of hydroxybenzoates, which are substantially anhydrous and free from hydrobenzoic acid, characterized in that a solution or suspension of a hydroxybenzoate of the formula ##STR2## in which R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meaning, is neutralized with an alkali metal hydroxide at -10.degree. to +50.degree. C. until the degree of neutralization is 0.95 to 1.05, a degree of neutralization of 1.
    Type: Grant
    Filed: September 20, 1979
    Date of Patent: June 30, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Schnegg, Walter Rapp, Bernhard Vosteen
  • Patent number: 4271310
    Abstract: Cholinesterase activity is determined by means of the choline and/or acid obtained by the action of cholinesterase on a compound of the formula: ##STR1## [wherein A represents a hydrogen atom or a C.sub.1-5 alkyl or alkoxy group and B represents a group of the formula --R-COO-- (in which --R-- represents an alkenyl group with 2 to 6 carbon atoms); or A represents a hydroxy group in either or both o-positions of the benzene ring or a C.sub.1-5 alkyl group and B represents a group of the formula --COO--; X represents a stabilizing anion and n represents the charge on the anion]. The method of the invention ensures a high resistance to saturation, good stability of the compounds used as substrates, a conveniently low reaction rate and a high degree of accuracy.Certain of the compounds of formula I as defined above are novel compounds which are claimed per se.Examples of the method of the present invention are given and the preparation of the novel compounds is described and exemplified.
    Type: Grant
    Filed: April 12, 1979
    Date of Patent: June 2, 1981
    Assignee: Kyowa Hakko Kogyo Kabushiki Kaisha
    Inventors: Katsuyuki Watanabe, Tadatoshi Hayashi, Hiroaki Hayashi, deceased, by Atsuko Hayashi, heir, by Yuko Hayashi, heir, Toshio Tatano, Yoshiaki Shmizu
  • Patent number: 4249015
    Abstract: Carboxylic acids and/or esters are prepared by converting the ##STR1## moiety in a 1-substituted 2,2-trihaloethanol, or derivative wherein X represents halogen and R is hydrogen or an acyl group to an organic acid and/or ester grouping of the formula ##STR2## wherein R' is hydrogen or alkyl of 1 to 6 carbon atoms, in the process which comprises reacting the 1-substituted 2,2,2-trihaloethanol or acylated derivative with molecular oxygen in the presence of a catalyst comprising a complex of a transition metal having an atomic number from 21-30, 39-48 or 57-80 and at least one molecule of a ligand containing trivalent nitrogen, phosphorus, arsenic or antimony. This reaction is carried out in a reaction medium comprising an alcohol or aqueous alcohol having 1 to 6 carbon atoms optionally containing an alkali metal, said alcoholic solvent also serving as a reactant source when carboxylic acid esters are formed.
    Type: Grant
    Filed: January 26, 1979
    Date of Patent: February 3, 1981
    Assignee: Shell Oil Company
    Inventors: John A. Schofield, John E. Hawes
  • Patent number: 4218567
    Abstract: A process for the preparation of aromatic ethers by the bromination of a compound of the formula ##STR1## wherein R.sub.1, independently, is hydrogen, hydroxy, lower alkoxy, lower alkyl; m is an integer from 1-4, and A is --CHO, --COOR.sub.3 or lower alkyl, and subsequently treating the reaction product of the bromination step with an alkali metal alkoxide in the presence of cuprous halide or oxide, is described.
    Type: Grant
    Filed: May 30, 1978
    Date of Patent: August 19, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Percy S. Manchand, John M. Townsend
  • Patent number: 4192949
    Abstract: Phenol ethers are prepared by reacting phenols with dialkyl carbonates in the presence of tertiary amines and/or phosphines. The aralkyl aryl ethers and alkyl aryl ethers obtained are starting materials for the manufacture of dyes, crop protection agents and scents.
    Type: Grant
    Filed: June 15, 1978
    Date of Patent: March 11, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Friedrich Towae, Ludwig Schroff, deceased
  • Patent number: 4185154
    Abstract: A synthesis of Vitamin E has the condensation of 2,4-pentanediene and 1,2-epoxy-2,6,10,14-tetramethylpentadecane including intermediates in this synthesis which uses base catalyzed condensations of aliphatic compounds to construct the Vitamin E molecule from aliphatic precursors.
    Type: Grant
    Filed: September 11, 1978
    Date of Patent: January 22, 1980
    Assignee: Hoffmann-La Roche, Inc.
    Inventors: Gary L. Olson, Gabriel Saucy
  • Patent number: 4142053
    Abstract: Synthetic oakmoss extracts of alkyl-substituted .beta.-resorcylic acid esters useful as perfume ingredients, are prepared by refluxing alkyl-substituted dihydro-.beta.-resorcylic acid esters with sulphuric acid and acetic anhydride, followed by saponifying the resultant diacetate.
    Type: Grant
    Filed: August 24, 1977
    Date of Patent: February 27, 1979
    Assignee: Dragoco Geberding & Co. GmbH
    Inventors: Erich Klein, Frank Thomel, Hartmut Struwe
  • Patent number: 4117042
    Abstract: New compounds are disclosed for obtaining novel polymeric flameproofing agents. The former are diphenols of the general formula: ##STR1## where n = 0 or 2. The latter are aromatic polyphenylphosphonates having recurring units of the general formula: ##STR2## in which n equals 0 or 2, and are obtained by reacting (I) with phenylphosphonyl chloride. The latter are especially useful for the flameproofing of polyester and finished or shaped articles based on polyester.
    Type: Grant
    Filed: April 26, 1977
    Date of Patent: September 26, 1978
    Assignee: Rhone-Poulenc-Textile
    Inventor: Paul Couchoud