Phenolic Hydroxy Or Metallate Patents (Class 560/67)
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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
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Patent number: 4876381Abstract: 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: GrantFiled: August 18, 1987Date of Patent: October 24, 1989Assignee: L'OrealInventors: Gerard Lang, Jean Maignan, Serge Forestier, Serge Restle, Alain Lagrange, Braham Shroot
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Patent number: 4874886Abstract: 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: GrantFiled: November 7, 1988Date of Patent: October 17, 1989Assignee: The Dow Chemical CompanyInventor: Charles B. Grant
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Optically active compound, process for producing same and liquid crystal composition containing same
Patent number: 4873018Abstract: 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: GrantFiled: October 27, 1987Date of Patent: October 10, 1989Assignees: Canon Kabushiki Kaisha, Yamakawa Yakuhin Kogyo Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuo Yoshinaga, Mariko Kai, Kazuharu Katagiri -
Patent number: 4853398Abstract: 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: GrantFiled: April 13, 1987Date of Patent: August 1, 1989Assignee: Eli Lilly and CompanyInventors: F. P. Carr, Robert D. Dillard, Doris E. McCullough
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Patent number: 4841093Abstract: 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: GrantFiled: October 19, 1987Date of Patent: June 20, 1989Assignee: Daikin Industries, Ltd.Inventors: Sinji Tamaru, Motonobu Kubo
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Patent number: 4814497Abstract: 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: GrantFiled: May 12, 1986Date of Patent: March 21, 1989Assignee: Ethyl CorporationInventor: K. Pushpananda A. Senaratne
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Patent number: 4733002Abstract: 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: GrantFiled: May 23, 1985Date of Patent: March 22, 1988Assignee: Green Cross CorporationInventors: Kazumasa Yokoyama, Chikara Fukaya, Masanori Sugiura, Youichiro Naito, Youichiro Nishida, Tadakazu Suyama
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Patent number: 4716244Abstract: 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: GrantFiled: April 21, 1986Date of Patent: December 29, 1987Assignee: Ciba-Geigy CorporationInventor: Ivan Orban
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Patent number: 4692552Abstract: 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: GrantFiled: February 18, 1986Date of Patent: September 8, 1987Assignee: G. D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 4686235Abstract: 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: GrantFiled: August 12, 1985Date of Patent: August 11, 1987Assignee: Merck & Co., Inc.Inventors: Michael N. Chang, Norman P. Jensen, Milton L. Hammond, Robert A. Zambias, John McDonald, Kathleen M. Rupprecht
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Patent number: 4683327Abstract: 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: GrantFiled: June 24, 1985Date of Patent: July 28, 1987Assignee: Celanese CorporationInventor: Robert W. Stackman
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Patent number: 4661616Abstract: 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: GrantFiled: September 2, 1986Date of Patent: April 28, 1987Assignee: Dow Corning, Ltd.Inventor: Michael P. Hill
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Patent number: 4643763Abstract: 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: GrantFiled: September 10, 1985Date of Patent: February 17, 1987Assignee: ICI Australia LimitedInventors: Graeme J. Farquharson, Keith G. Watson, Graham J. Bird
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Patent number: 4640708Abstract: 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: GrantFiled: March 20, 1984Date of Patent: February 3, 1987Assignee: ICI Australia LimitedInventors: Graham J. Bird, Graeme J. Farquharson, Keith G. Watson
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Patent number: 4624802Abstract: 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: GrantFiled: January 2, 1985Date of Patent: November 25, 1986Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Ulf-Armin Schaper, Benno Streschnak, Siegfried Bloesl, Walter Sommer
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Patent number: 4618700Abstract: 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: GrantFiled: December 12, 1984Date of Patent: October 21, 1986Assignee: Ciba-Geigy CorporationInventors: Erich Gubler, Max Siegrist
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Patent number: 4613683Abstract: 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: GrantFiled: January 25, 1985Date of Patent: September 23, 1986Assignee: BASF AktiengesellschaftInventors: Walter Rebafka, Helmut Nickels
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Patent number: 4613678Abstract: 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: GrantFiled: June 30, 1980Date of Patent: September 23, 1986Assignee: The Dow Chemical CompanyInventor: Daniel J. Swart
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Patent number: 4594460Abstract: 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: GrantFiled: March 19, 1985Date of Patent: June 10, 1986Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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Patent number: 4594444Abstract: 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: GrantFiled: December 12, 1984Date of Patent: June 10, 1986Assignee: Ciba-Geigy CorporationInventor: Ivan Orban
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Patent number: 4582855Abstract: 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: GrantFiled: November 12, 1981Date of Patent: April 15, 1986Assignee: American Hospital Supply CorporationInventors: Sheung T. Kam, William L. Matier
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Patent number: 4547583Abstract: 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: GrantFiled: October 3, 1984Date of Patent: October 15, 1985Assignee: Hoechst AktiengesellschaftInventor: Hans J. Nestler
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Patent number: 4537970Abstract: 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: GrantFiled: December 12, 1983Date of Patent: August 27, 1985Assignee: Montedison S.p.A.Inventors: Marco Foa, Franco Francalanci, Andrea Gardano, Elena Bencini
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Patent number: 4536593Abstract: 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: GrantFiled: July 5, 1983Date of Patent: August 20, 1985Assignee: Ciba-Geigy CorporationInventors: Ivan Orban, Eduard Troxler
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Patent number: 4528395Abstract: 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: GrantFiled: August 15, 1983Date of Patent: July 9, 1985Assignee: American Cyanamid Co.Inventors: Richard F. Beidler, Philip R. Ruby
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Patent number: 4501912Abstract: 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: GrantFiled: December 13, 1982Date of Patent: February 26, 1985Assignee: American Hospital Supply CorporationInventors: William L. Matier, Sheung-Tsam Kam
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Patent number: 4499295Abstract: 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: GrantFiled: May 9, 1983Date of Patent: February 12, 1985Assignee: G. D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 4454338Abstract: 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: GrantFiled: September 9, 1981Date of Patent: June 12, 1984Assignee: Torii & Co., Ltd.Inventors: Setsuro Fujii, Toshiyuki Okutome, Toyoo Nakayama, Takashi Yaegashi, Masateru Kurumi
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Patent number: 4440945Abstract: 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: GrantFiled: July 19, 1982Date of Patent: April 3, 1984Assignee: Celanese CorporationInventors: Anthony B. Conciatori, Eui W. Choe, Gerald Farrow
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Patent number: 4417071Abstract: 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: GrantFiled: March 11, 1982Date of Patent: November 22, 1983Assignee: Ciba-Geigy CorporationInventor: Siegfried Rosenberger
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Patent number: 4408065Abstract: 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: GrantFiled: March 23, 1981Date of Patent: October 4, 1983Assignee: UOP Inc.Inventors: Armand J. deRosset, James W. Priegnitz, Arthur M. Landis
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Patent number: 4408059Abstract: 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: GrantFiled: December 4, 1981Date of Patent: October 4, 1983Assignee: University Patents, Inc.Inventors: Amos B. Smith, III, Steven R. Schow
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Patent number: 4402974Abstract: 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: GrantFiled: June 23, 1981Date of Patent: September 6, 1983Assignee: American Hospital Supply CorporationInventors: William L. Matier, Sheung-Tsam Kam
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Patent number: 4374262Abstract: 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: GrantFiled: October 6, 1980Date of Patent: February 15, 1983Assignee: Celanese CorporationInventors: James L. McGinnis, Anthony B. Conciatori
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Patent number: 4374263Abstract: 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: GrantFiled: October 24, 1980Date of Patent: February 15, 1983Assignee: The British Petroleum Company LimitedInventors: Ronald D. Hancock, Robert Mackison
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Patent number: 4346039Abstract: 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: GrantFiled: March 19, 1981Date of Patent: August 24, 1982Assignee: Iowa State University Research Foundation, Inc.Inventor: George A. Kraus
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Patent number: 4338170Abstract: 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: GrantFiled: May 23, 1980Date of Patent: July 6, 1982Assignee: Nissan Chemical Industries, Ltd.Inventors: Atsuo Murata, Syuji Tsuchiya, Hideo Suzuki
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Patent number: 4335250Abstract: 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: GrantFiled: July 12, 1979Date of Patent: June 15, 1982Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Hamao Umezawa, Tomio Takeuchi, Takaaki Aoyagi, Masaaki Ishizuka, Hajime Morishima, Takuzo Yamamoto, Junji Yoshizawa, Masaaki Hosoi, Ikuo Matsumoto
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Patent number: 4310465Abstract: 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: GrantFiled: December 17, 1979Date of Patent: January 12, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Gary L. Olson, Gabriel Saucy
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Patent number: 4309564Abstract: 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: GrantFiled: October 23, 1980Date of Patent: January 5, 1982Assignee: Mallinckrodt, Inc.Inventors: Donald F. Loncrini, John J. Taylor
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Patent number: 4305868Abstract: 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: GrantFiled: May 30, 1979Date of Patent: December 15, 1981Assignee: Uniroyal, Inc.Inventors: Edward L. Wheeler, Elmar H. Jancis, Richard A. Gencarelli, Franklin H. Barrows
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Patent number: 4276431Abstract: 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: GrantFiled: September 20, 1979Date of Patent: June 30, 1981Assignee: Bayer AktiengesellschaftInventors: Peter Schnegg, Walter Rapp, Bernhard Vosteen
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Patent number: 4271310Abstract: 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: GrantFiled: April 12, 1979Date of Patent: June 2, 1981Assignee: Kyowa Hakko Kogyo Kabushiki KaishaInventors: Katsuyuki Watanabe, Tadatoshi Hayashi, Hiroaki Hayashi, deceased, by Atsuko Hayashi, heir, by Yuko Hayashi, heir, Toshio Tatano, Yoshiaki Shmizu
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Patent number: 4249015Abstract: 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: GrantFiled: January 26, 1979Date of Patent: February 3, 1981Assignee: Shell Oil CompanyInventors: John A. Schofield, John E. Hawes
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Patent number: 4218567Abstract: 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: GrantFiled: May 30, 1978Date of Patent: August 19, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Percy S. Manchand, John M. Townsend
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Patent number: 4192949Abstract: 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: GrantFiled: June 15, 1978Date of Patent: March 11, 1980Assignee: BASF AktiengesellschaftInventors: Franz Merger, Friedrich Towae, Ludwig Schroff, deceased
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Patent number: 4185154Abstract: 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: GrantFiled: September 11, 1978Date of Patent: January 22, 1980Assignee: Hoffmann-La Roche, Inc.Inventors: Gary L. Olson, Gabriel Saucy
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Patent number: 4142053Abstract: 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: GrantFiled: August 24, 1977Date of Patent: February 27, 1979Assignee: Dragoco Geberding & Co. GmbHInventors: Erich Klein, Frank Thomel, Hartmut Struwe
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Patent number: 4117042Abstract: 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: GrantFiled: April 26, 1977Date of Patent: September 26, 1978Assignee: Rhone-Poulenc-TextileInventor: Paul Couchoud