Halogen In Alcohol Moiety Patents (Class 560/111)
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Patent number: 4973735Abstract: There are described new trifluoroethyl esters of phenylacetic acid of general formula I ##STR1## in which R.sub.1 and R.sub.2 have the meanings given in the description and processes for their preparation. The compounds show insecticidal activity so that they can be used as pesticides.Type: GrantFiled: September 5, 1989Date of Patent: November 27, 1990Assignee: Schering AktiengesellschaftInventors: Ulrich Buhman, Ortrud Lammer, Hartmut Joppien, Harald von Keyserlingk
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Patent number: 4959187Abstract: The invention provides novel bleaching compositions comprising peracid precursors with the general structure ##STR1## with R, R', R" and L as defined in the specification. Novel peracids and precursors are also herein disclosed. These peracid precursors provide new, proficient and cost-effective compounds for fabric bleaching.Type: GrantFiled: October 14, 1988Date of Patent: September 25, 1990Assignee: The Clorox CompanyInventors: Ronald A. Fong, Sheldon N. Lewis, Richard J. Wiersema, Alfred G. Zielske
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Patent number: 4952580Abstract: Polyhaloalkene compounds of the formula: ##STR1## wherein X is sulfur, oxygen, or nitrogen, Y.sup.1 and Y.sup.2 are fluorine, Z is hydrogen or the same as Y.sup.1 and Y.sup.2, and n is 1-4; provided that:(A) when X is sulfur, Z is fluorine and R is thienyl or substituted thienyl, thianaphthyl or substituted thianaphthyl, thiazolinyl or substituted thiazolinyl, oxadiazolyl or substituted oxadiazolyl, 3,4,4-trifluoro-3-butenyloxycarbonylmethyl, thiadiazolyl substituted by halogen or R.sup.2 S, wherein R.sup.2 is 3,4,4-trifluoro-3-butenyl or R.sup.2 is phenylmethyl or phenylthiomethyl each optionally substituted by halogen or nitro; or R is thiadiazolyl substituted by R.sup.3, wherein R.sup.3 is substituted aryl, arylalkyl, aryloxyalkyl, alkylthio, haloalkylthio, haloarylthio, cyanoalkylthio, arylalkylthio, aryloxyalkylthio, arylthioalkylthio, heterocycloalkylthio, alkenylthio, haloalkenylthio, halocycloalkylalkenylthio, wherein said aryl or heterocyclic groups of R.sup.Type: GrantFiled: November 9, 1988Date of Patent: August 28, 1990Assignee: FMC CorporationInventors: Anthony J. Martinez, Thomas G. Cullen
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Patent number: 4939290Abstract: Quinolonecarboxylic acid intermediaes useful in the preparation of antibacterial 6-fluouro-7-substituted-quinolonecarboxylic acids are prepared from 2-(iodo, bromo or chloro)-3-fluoro-4-(fluoro or chloro)-phenyl carboxylic acid or ester.Type: GrantFiled: November 23, 1988Date of Patent: July 3, 1990Assignee: Pfizer Inc.Inventor: Brian T. O'Neill
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Patent number: 4917817Abstract: An optically active functional compound represented by the following formula (1) is disclosed: ##STR1## wherein R denotes an alkyl group having 1-14 carbon atoms; -X- denotes ##STR2## denotes a single bond, ##STR3## n=0, 1 or 2; and C* denotes an asymmetric carbon atom. The compound of the formula (1) may be produced through an optically active compound of the following formula (2) or (3): ##STR4## The compounds of the above formulas (1)-(3) are all characterized by a trifluoromethyl group providing a large spontaneous polarization attached to an asymmetric carbon atom.Type: GrantFiled: July 21, 1988Date of Patent: April 17, 1990Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Tetsuya Abe, Yoko Yamada, Yuko Etoh
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Patent number: 4898970Abstract: This invention relates to a process for producing a fluorinated ester containing a trifluoromethyl group by esterification in the presence of .gamma.-butyrolactone as a solvent, and more particularly a process or producing a fluorinated ester containing a trifluoromethyl group which is useful as a raw material of various fluorine containing compound.Type: GrantFiled: February 1, 1983Date of Patent: February 6, 1990Assignees: Onoda Cement Co., Ltd., Tosoh CorporationInventors: Eiji Ogura, Kunihiro Mito, Shoji Arai
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Patent number: 4886619Abstract: Compounds are provided which comprise a fluorocarbon terminal portion and a chiral hydrocarbon terminal portion, said terminal portions being connected by a central core, said compounds having tilted smectic mesophases or having latent tilted smectic mesophases which develop when said compounds having said latent mesophases are in admixture with said compounds having tilted smectic mesophases or said compounds having latent tilted smectic mesophases.Type: GrantFiled: May 29, 1987Date of Patent: December 12, 1989Assignee: Minnesota Mining and Manufacturing CompanyInventor: Eugene P. Janulis
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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: 4867903Abstract: A fluoroalkane derivative represented by the formula: ##STR1## wherein R denotes an alkyl group having 1-16 carbon atoms, C* denotes an asymmetric carbon atom, R.sup.1 denotes an alkyl or alkoxy group having 1-16 carbon atoms; ##STR2## respectively denote a phenylene group ##STR3## a cyclohexylene group ##STR4## or a pyrimidinylene group ##STR5## p is 0 or 1, q is 0 or 1 when p is 1, r is 0 or 1; and l, m and n are respectively 0 or a positive integer satisfying the relationship of l+m+n.gtoreq.1. The fluoroalkane derivative has a fluorine atom providing a large dipole moment and directly connected to an asymmetric carbon atom, so that it provides a high speed responsive characteristic through an increased spontaneous polarization when contained in a liquid crystal composition, especially a ferroelectric liquid crystal composition.Type: GrantFiled: March 6, 1987Date of Patent: September 19, 1989Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuharu Katagiri
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Patent number: 4841081Abstract: A method of optically resolving a racemate, or a diastereomeric mixture, of a substituted or unsubstituted glycidyl ester or ether compound having at least one glycidylic structure represented by the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3, independently from each other, represent H or CH.sub.3, and 1 to 3 asymmetric carbon atoms in the molecule, or a racemate of a beta-dihalohydrin ester compound, which comprises contacting said racemate or diastereomeric mixture with an optically active form of a compound having the following formula (I) ##STR2## wherein X represents a halogen atom, to form an inclusion complex compound having the optically active compound of formula (I) as a host, and separating the resulting complex compound.Type: GrantFiled: October 14, 1986Date of Patent: June 20, 1989Assignee: Osaka Soda Co., Ltd.Inventors: Fumio Toda, Koichi Tanaka, Tetsuya Nakata
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Patent number: 4835304Abstract: Esters having the general formula: ##STR1## where X is a halogen, n is 1-5, Y is an alkyl, ether, ester, or nitro substituent, m is 0-2, Z is an ester linkage --OCO-- or --CO.sub.2 --, R' is a haloalkyl group, and p is 1-3, constitute high density flotation fluids for inertial instruments such as gyroscopes and accelerometers. Synthetic methods are disclosed for production of such fluids from available starting materials.Type: GrantFiled: May 1, 1987Date of Patent: May 30, 1989Assignee: Charles Stark Draper LaboratoryInventor: John R. Williams
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Patent number: 4803230Abstract: Halogen- and/or phosphorus-containing polyols-polyesters obtained by esterification and transesterification of the residues from the process for producing dimethyl terephthalate with a polyol at least 5% by weight of which is constituted by a glycol having the formulaHO--R--OHwherein R is a halogen- and/or phosphorus-containing aliphatic, aromatic, cycloaliphatic or alkyl-aromatic radical. Said halogen- and/or phosphorus-containing polyesters-polyols are used for the production of fire-resistant polyurethane foams.Type: GrantFiled: November 23, 1987Date of Patent: February 7, 1989Assignee: Montedipe S.p.A.Inventors: Renato Moroni, Marino Brocci
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Patent number: 4789382Abstract: Textile polyester material is dyed with disperse dyes in the presence of specific benzophenone derivatives, some of which are novel, to improve the light fastness.Type: GrantFiled: July 10, 1987Date of Patent: December 6, 1988Assignee: BASF AktiengesellschaftInventors: Peter Neumann, Dieter Wegerle, Reinhold Krallmann
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Patent number: 4748253Abstract: Process for preparing esters of alkanoic acids via rearrangement of alpha-haloketals in the presence of a Lewis acid.The rection is preferably carried out in the presence of catalytic amounts of a Lewis acid and of a diluent at a temperature in the range from about 0.degree. to the reflux temperature of diluent.The esters thus obtained are useful as intermediate products for preparing drugs.The process involves the preparation of new alpha-haloketals.Type: GrantFiled: December 10, 1981Date of Patent: May 31, 1988Assignee: Blasinachim S.p.A.Inventors: Claudio Giordano, Aldo Belli, Fulvio Uggeri, Giovanni Villa
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Patent number: 4723005Abstract: New anisotropic compounds of the formula (1) are useful in liquid crystal mixtures for electrooptical displays; at least one of the end groups of the compounds (1) is an alkyl group which carries cyano or halogen in a terminal or non-terminal position. This offers advantages for longitudinal polarization and/or cross-polarization of the anisotropic compounds with the aid of the comparatively highly polarizing cyano or halogen substituents, in particular high clear points, low .DELTA..epsilon./.epsilon..perp. values and/or negative .DELTA..epsilon. values.Type: GrantFiled: September 10, 1984Date of Patent: February 2, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Tuong Huynh-Ba, Maged A. Osman
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Patent number: 4705650Abstract: Compounds halogenated in the .alpha.-position to an electron-attracting group of formula ##STR1## in which X denotes a halogen atom, R denotes a hydrogen atom or a hydrocarbon radical or a radical --(CH.sub.2).sub.3 --COOR.sub.1 and Z denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6, --NO.sub.2, --CO--(CH.sub.2)p--COO.sub.1 or --COO(CH.sub.2)p--COOR.sub.1 are made by a halogenating deacylation of a compound of formula ##STR2## in which R' denotes a hydrogen atom or a hydrocarbon radical, R" denotes a methyl radical and Z' denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6 or --NO.sub.2 or R' and R" may form a radical --(CH.sub.2)-- or R' and R" may form a radical --CO--(CH.sub.2)p-- or --COO(CH.sub.2)p--, using an alkali metal alcoholate or an alkali or alkaline-earth metal carbonate and a halogenating agent.Type: GrantFiled: July 10, 1985Date of Patent: November 10, 1987Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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Patent number: 4676604Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen or straight-chain alkyl; R.sup.2 is --CN, --R, --COR, --COOR or when R.sup.2 is positioned on an aromatic ring R.sup.2 also can be --OR, --OOCR or --F; R is alkyl; A is a group with 1 to 4 six-membered rings, these rings being linked directly with one another and with ring B in each case via a single covalent bond or being linked at one or two positions also via --COO--, --OOC-- or --CH.sub.2 CH.sub.Type: GrantFiled: March 5, 1984Date of Patent: June 30, 1987Assignee: Hoffmann-La Roche Inc.Inventor: Martin Petrzilka
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Patent number: 4664851Abstract: 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, 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 transistion metal or Group II metal iodides or bromides, and containing a trivalent nitrogen compound containing a group ##STR1## (X=O or S), such as an amide, a carbamate, a urea or a derivative thereof.Type: GrantFiled: July 19, 1982Date of Patent: May 12, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4650913Abstract: Reaction of a perfluorinated iodide with an olefin initiated by a sulfinate salt to prepare fluorinated iodide and diiodide monomers and surface active agents.Type: GrantFiled: November 29, 1984Date of Patent: March 17, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Andrew E. Feiring
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Patent number: 4647413Abstract: Perfluoropolyether oligomers or block polymers, having a backbone with one or a plurality of perfluoropolyether segments each consisting essentially of (1) at least one perfluoroisopropyleneoxy unit, (2) a bis(perfluoromethyleneoxy-terminated) unit, and (3) a perfluoroethylidene unit terminating each segment, the backbone of the perfluoropolyether being terminated with COF and/or a functional or nonfunctional derivative thereof, said perfluoropolyethers being made by reacting a perfluoroaliphatic diacid fluoride with hexafluoropropylene epoxide to produce an acid fluoride-terminated perfluoropolyether adduct or oligomer which then can be photopolymerized to yield an acid fluoride-terminated perfluoropolyether block polymer. These oligomers and block polymers are useful as high temperature lubricants, hydraulic fluids, gaskets, adhesives and coatings as well as co-reactants wtih urethane in forming propellant binders.Type: GrantFiled: January 20, 1984Date of Patent: March 3, 1987Assignee: Minnesota Mining and Manufacturing CompanyInventor: Patricia M. Savu
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Patent number: 4640802Abstract: 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: GrantFiled: July 7, 1982Date of Patent: February 3, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4613681Abstract: This invention relates to a process for the preparation of a fluorinated compound of the general formulaR.sub.F C.sub.2 H.sub.4 ORcomprising reacting an iodide of the general formula R.sub.F C.sub.2 H.sub.4 I with a percarboxylic acid of the general formula R.sup.1 CO.sub.3 H at a temperature and for a time sufficient to form said fluorinated compound; in said formulae R.sub.F is a straight or branched chain perfluorinated radical containing 1 to 20 C atoms, R is a hydrogen atom or --COR.sup.1, and R.sup.1 is a hydrogen atom or an aliphatic or aromatic hydrocarbon radical.Type: GrantFiled: June 30, 1980Date of Patent: September 23, 1986Assignee: Produits Chimiques Ugine KuhlmannInventors: Louis Foulletier, Andre Lantz
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Patent number: 4612386Abstract: Carboxylic acid esters are produced by the reaction of a carboxylic acid halide with a carbonate ester in the presence of an initiator. The reaction of a dicarboxylic acid dihalide and a bis(alkyl carbonate) ester produces a polymeric polyester.Type: GrantFiled: December 17, 1981Date of Patent: September 16, 1986Assignee: The Dow Chemical CompanyInventor: James M. Renga
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Patent number: 4578504Abstract: Polymerizable monomer compounds selected from the group having the formulae: ##STR1## wherein R is hydrogen or methyl;X is fluoro, chloro, bromo, iodo, hydroxyl, perfluoroalkylsulfonoxy of one to three carbon atoms, perfluoroacyloxy of one to three carbon atoms, benzoyloxy, or trichloroacetoxy;Y is trichloroacetyl, perfluoroacyl of the formula ##STR2## trialkylsilyl of the formula [CH.sub.3 (CH.sub.2).sub.m ].sub.3 Si-- or hydrogen,wherein n is zero to six; and m is zero to three, with the proviso that when Y in Formula I or II is hydrogen, X is selected from fluoro, chloro, bromo, iodo in Formulas I and II, and additionally from hydroxyl in Formula I, are disclosed. Polymers and copolymers of the invention are useful for preparing hydrogel processed articles such as contact lenses, and when dissolved in solvents they can be coated onto articles and then hydrolyzed to provide hydrogel coatings.Type: GrantFiled: June 3, 1983Date of Patent: March 25, 1986Assignee: Minnesota Mining and Manufacturing CompanyInventor: W. James Hammar
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Patent number: 4517376Abstract: Compounds having the formula: ##STR1## wherein R.sub.f is perfluorinated saturated aliphatic containing 3-20 carbons;R.sup.1 is optionally substituted alkyl, aryl, aralkyl or cycloalkyl; andn is a number from 1 to 4.Process for preparing compounds (I): ##STR2## The reaction can be carried out, e.g., by melting an iodine-substituted polyfluoroalkyl ester and contacting the molten ester with chlorine, or an iodine-substituted polyfluoroalkyl ester can be suspended or dissolved in a suitable liquid and reacted with chlorine. A suitable liquid is inert under the reaction conditions; e.g. alcohols or water should be avoided. Process of using compounds (I) to treat (a) textile materials so as to give them dry soil resistance and oil and water repellency, and (b) paper so as to make it repel water and oil.Type: GrantFiled: August 23, 1982Date of Patent: May 14, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventors: Stanley E. Krahler, William R. Remington
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Patent number: 4442123Abstract: 6-Chloro-6-deoxy-D-hexitols, a novel class of compounds, and their esters, possess male antifertility activity and are thus useful in antifertility compositions. They are prepared by reduction of 6-chloro-6-deoxy-D-hexoses.Type: GrantFiled: December 28, 1981Date of Patent: April 10, 1984Assignee: Tate & Lyle Public Limited CompanyInventors: Elner B. Rathbone, Geoffrey M. H. Waites, William C. L. Ford
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Patent number: 4419522Abstract: The invention relates to new hexitols having the general formula (I) and (II), ##STR1## wherein the hexitol skeleton is dulcitol, mannitol or iditol,X represents halogen, preferably bromine,R is a saturated or unsaturated C.sub.4-10 alkylcarbonyl group which also contains a free carboxy group, andR.sup.1 is hydrogen, a saturated or unsaturated C.sub.4-10 alkylcarbonyl group which also contains a free carboxy group, a saturated or unsaturated C.sub.2-10 alkylcarbonyl group, a saturated or unsaturated C.sub.4-10 alkylcarbonyl group which also contains an alkoxycarbonyl group, or a saturated or unsaturated C.sub.8-10 aralkylcarbonyl group,and salts of these compounds. The new compounds according to the invention have tumor-inhibiting affects.The above compounds are prepared according to the invention so that(a) a compound of the general formula (IX), whereinthe hexitol skeleton is dulcitol, mannitol or iditol,Q is a saturated or unsaturated C.sub.Type: GrantFiled: October 26, 1981Date of Patent: December 6, 1983Assignee: Chinoin Gyogyszer Vegyeszeti Termekek Gyara Rt.Inventors: Ilona Elekes, Laszlo Institoris, Kalman Medzihradsz, Laszlo tvos, Hedvig Medzihradszky-Schweiger, Katalin De Gleria, Janos Sugar, Somfai Relle, Sandor Eckhardt, Ivan Hidy, Sandor Kerpel-Fronius
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Patent number: 4352760Abstract: The present invention provides novel substituted heptadeca-5,9- and 5,10-dienoic acid and similar fatty acid compounds which are derivatives of certain prostaglandins and are potent thromboxane A.sub.2 inhibitors. By virtue of this pharmacological property, they represent useful pharmacological agents for a wide variety of purposes.Type: GrantFiled: December 29, 1980Date of Patent: October 5, 1982Assignee: The Upjohn CompanyInventor: Kirk M. Maxey
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Patent number: 4346141Abstract: Compounds having the formula: ##STR1## wherein R.sub.f is perfluoroalkyl containing 4-20 carbons;R.sup.1 is the hydrocarbon residue of either citric, phthalic (o, m or p isomer), benzoic, succinic, chlorendic, trimellitic or pyromellitic acid; andn is a number from 1 to 4, preferably 2 to 4.Process of using compounds (I) to treat (a) textile materials so as to give them dry soil resistance and oil and water repellency, and (b) paper so as to make it repel water and oil.Type: GrantFiled: March 30, 1981Date of Patent: August 24, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: William R. Remington
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Patent number: 4340749Abstract: An ester of a fluoroaliphatic radical- and aliphatic chlorine-containing alcohol and a mono or polycarboxylic acid useful in carpet treatment.Type: GrantFiled: December 8, 1980Date of Patent: July 20, 1982Assignee: Minnesota Mining and Manufacturing CompanyInventor: Kalyanji U. Patel
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Patent number: 4338316Abstract: The disclosure relates to 9.beta.-aryloxy prostane derivatives, for example 16-(3-chlorophenoxy)-11.alpha.,15.alpha.-dihydroxy-16-methyl-9.beta.-pheno xy-18,19,20-trinor-5-cis,13-trans-prostadienoic acid, which possess high activity as abortifacients, cervical softeners, inducers of parturition or inhibitors of gastric acid production in mammals. These properties are typical of prostaglandin analogues of the E series, but chemically the new 9.beta.-aryloxy prostane derivatives are prostaglandin F series analogues and are therefore more stable than the E series analogues previously used for the above purposes. The new derivatives are manufactured by known analogy processes, and are formulated in conventional manner.Type: GrantFiled: September 26, 1979Date of Patent: July 6, 1982Assignee: Imperial Chemical Industries LimitedInventor: Peter R. Marsham
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Patent number: 4310709Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.Type: GrantFiled: April 23, 1980Date of Patent: January 12, 1982Assignee: BASF AktiengesellschaftInventor: Walter Rebafka
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Patent number: 4304921Abstract: Beta-halo esters, such as .beta.-haloalkyl benzoates or terephthalates, are prepared by halogenative cleavage of cyclic acetals using trimethyl phosphate (TMP) or borate to mediate the reaction. The .beta.-halo esters, which are obtained in high yields, can be used to form polymers or plasticizers. Neuromuscular blocking agents such as succinylcholine and related compounds can also be prepared.Type: GrantFiled: August 8, 1980Date of Patent: December 8, 1981Assignee: Vanderbilt UniversityInventors: Donald E. Pearson, Sidhaghatta D. Venkataramu, James H. Cleveland, Jr.
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Patent number: 4283414Abstract: The invention concerns novel pesticidal esters of the pyrethrin or pyrethroid type in which the methylene group bonded to the ester carbonyl and/or ester oxygen bears a fluorine substituent. The compounds of the invention are active against insect pests including flies, moths, aphids and beetles and acarina pests including ticks.Type: GrantFiled: June 8, 1979Date of Patent: August 11, 1981Assignee: ICI Australia LimitedInventors: Donald W. G. Harney, Peter G. Lehman, Joseph C. Rundle
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Patent number: 4267360Abstract: Derivatives of hexafluoropropene dimer expressed by the following general formula ##STR1## in which R.sub.f represents (CF.sub.3).sub.2 C.dbd.C(CF.sub.2 CF.sub.3) or (CF.sub.3).sub.2 CH--CF(CF.sub.2 CF.sub.3) and R represents a hydrocarbon residue of a carboxylic acid having one free site capable of reacting with the dimer. A process for preparing the derivatives is also disclosed in which the dimer is contacted with the carboxylic acid in an inert solvent in the presence of a catalyst. Metal, amine or ammonium salts of the acid may be also used for the reaction, in which case the reaction is feasible in the absence of a catalyst.Type: GrantFiled: October 15, 1979Date of Patent: May 12, 1981Assignee: Central Glass Company, LimitedInventors: Masahiro Ozawa, Tadaaki Komatsu, Kimiaki Matsuoka
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Patent number: 4266080Abstract: Perfluoroalkyl compounds containing ether groups have the formulaR.sub.f R.sub.1 SCH.sub.2 CH.sub.2 O T Zwherein R.sub.f is a perfluoroalkyl, R.sub.1 is alkylene or alkyleneoxy or aminoalkylene, T is alkylene, and Z is hydrogen; hydroxy; NR.sub.3 R.sub.4, where R.sub.3 and R.sub.4 each is alkyl or together with nitrogen form a heterocyclic ring; N.sup.+ R.sub.3 R.sub.4 (R.sub.5)X.sub.z.sup.-y, where R.sub.5 is hydrogen, oxide, alkyl, or substituted alkyl, X is an anion, and y is 1 or 2; z is 0 or 1 or is --OCH.sub.2 CH.sub.2 SR.sub.1 R.sub.f ; can be prepared directly by free-radical catalyzed addition of a perfluoroalkylthiol to a vinyl ether or subsequent reaction. These compounds are useful as surfactants and oil spill collecting agents.Type: GrantFiled: February 2, 1978Date of Patent: May 5, 1981Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Karl F. Mueller
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Patent number: 4264775Abstract: A simple process for the preparation of .beta.-aminostyrenes proceeds from anilines by successively diazotizing, reacting with a vinyl ester, and reacting with a secondary amine without purification of the intermediate products. The compounds are reactive enamines useful in organic synthesis.Type: GrantFiled: October 27, 1976Date of Patent: April 28, 1981Assignee: Eli Lilly and CompanyInventor: William A. White
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Patent number: 4259350Abstract: Iodopropargyl derivatives of formula:IC.tbd.CCH.sub.2 OR[wherein R represents an alkanoyl group (which may be unsubstituted or have one or more halogen, cyano, substituted or unsubstituted .alpha.Type: GrantFiled: March 13, 1979Date of Patent: March 31, 1981Assignee: Sankyo Company LimitedInventors: Yasuhiro Morisawa, Kiyoshi Konishi, Mitsuru Kataoka
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Patent number: 4237312Abstract: In the oxidation of acyclic conjugated dienes, recovery and recycle of the oxidation catalyst is accomplished by distilling off the oxidation solvent, extraction of the oxidation product with a suitable solvent, and removal of the extraction solvent residue from the catalyst, and recycle of the catalyst to the oxidation step.Type: GrantFiled: April 2, 1979Date of Patent: December 2, 1980Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4233230Abstract: A process for preparing esters and halides is disclosed comprising the step of reacting a cyclic olefin having the formula I ##STR1## wherein R.sub.1 and R.sub.4 are the same or different from each other and each represents hydrogen, methyl, or ethyl;R.sub.2 and R.sub.3 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms; andn represents a whole number from 2 to 12, with an acyclic olefin having the formula II ##STR2## wherein R.sub.5 represents hydrogen, methyl, ethyl or the group ##STR3## wherein R.sub.12 and R.sub.13 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms;Y represents halogen; an acyloxy group R.sub.14 --CO--O wherein R.sub.14 represents alkyl containing 1-12 carbon atoms, phenyl or phenyl alkyl containing 7-12 carbon atoms, or an oxycarbonyl group R.sub.15 --O--CO wherein R.sub.Type: GrantFiled: May 4, 1978Date of Patent: November 11, 1980Assignee: Rhone-Poulenc IndustriesInventor: Jean Otton
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Patent number: 4230484Abstract: A method of controlling pollen formation in a hermaphrodite plant, the method comprising applying to the plant, to seed of the plant or to the locus surrounding the plant or seed, a compound of formula: ##STR1## wherein R.sup.1 is hydrogen or alkyl, R.sup.2 is hydrogen, alkyl, alkyl substituted with up to three halogens (e.g. trichloro- or trifluoro-methyl), cycloalkyl, alkoxyalkyl (e.g. 2-methoxy-ethyl), substituted or unsubstituted aryl or aralkyl or an alkali metal (e.g. sodium or potassium), alkaline earth metal or quaternary ammonium cation, R.sup.3 is halogen, nitro, alkyl, alkyl substituted with up to three halogens (e.g. trichloro- or trifluoro-methyl), cycloalkyl, alkoxy, alkylthio, amino, acylamino (e.g. acetylamino), mono- or di-alkylamino, acyl (e.g. acetyl), haloacyl (e.g. bromoacetyl), cyano, amido, hydroxy, carboxy, alkoxycarbonyl (e.g.Type: GrantFiled: April 25, 1978Date of Patent: October 28, 1980Assignee: Imperial Chemical Industries LimitedInventors: Jeremy J. Batch, Keith P. Parry, Colin F. Rowe, David K. Lawrence, Michael J. Brown
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Patent number: 4195916Abstract: Novel liquid crystal compounds are disclosed, which are chiral esters based upon the phenol ##STR1## Typical examples are: ##STR2## and mixtures of these compounds have a helical pitch such that the mixtures reflect light of a specific wavelength when illuminated with ordinary light and the pitch is temperature sensitive so that the mixtures can be used in temperature indicating devices. Specific examples are given as are samples of mixtures that can be used in phase change electro-optic display devices.Type: GrantFiled: April 5, 1978Date of Patent: April 1, 1980Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: David Coates, George W. Gray, Damien G. McDonnell
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Patent number: 4169720Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 are each hydrogen, chlorine or fluorine; andR.sub.3 is --CH.sub.2 OH, --CH.sub.2 --O--COR.sub.4, --CH.sub.2 --O--CONHR.sub.5, --COOH, --COOCat, --COOR.sub.6, --CONR.sub.7 R.sub.8 or --CO--SR.sub.9 ;where Cat is one equivalent of an inorganic or organic cation;R.sub.4 is hydrogen or alkyl of 1 to 10 carbon atoms;R.sub.5 is alkyl of 1 to 4 carbon atoms, phenyl or halo-substituted phenyl;R.sub.6 is alkyl of 1 to 10 carbon atoms which may optionally have a chloro, hydroxyl, lower alkoxy, lower alkoxy-lower alkoxy, lower alkylthio, amino, mono-lower alkyl-amino, di-lower alkyl-amino, allyloxy or phenoxy substituent attached thereto; phenyl; benzyl; monochloro-benzyl; dichloro-benzyl; cyclohexyl; 1-ethynyl-cyclohexyl; lower alkenyl; lower alkynyl; --N.dbd.C(CH.sub.3).sub.2 ; 2--(2',4',5'-trichloro-phenoxy)-ethyl, 2-(2', 5'-dichloro-4'-bromo-phenoxy)-ethyl; or ##STR2## R.sub.Type: GrantFiled: July 28, 1977Date of Patent: October 2, 1979Assignee: Celamerck GmbH & Co. KGInventors: Erich Schacht, Gunter Lauterbach, Werner Mehrhof, Jurgen Curtze, Gerbert Linden, Siegmund Lust, Klaus Thomas
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Patent number: 4164615Abstract: A catalyst comprising a titanium compound, an alkali metal ion, and a halide, is effective for the conversion of conjugated diolefins to diacyloxy olefins.Type: GrantFiled: August 25, 1977Date of Patent: August 14, 1979Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4162363Abstract: Conjugated dienes or monoolefins are converted to diesters in a process utilizing a catalyst system comprising an alkali metal compound and a sulfur source comprising elemental sulfur or a sulfur halide, optionally with a halide source, in carboxylic acid media.Type: GrantFiled: August 25, 1977Date of Patent: July 24, 1979Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4159991Abstract: .alpha.-Acyloxy-N,N'-diacylmalonamides of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are the same or different and are hydrogen, straight chain or branched alkyl radicals having from one to eleven carbon atoms, or hydrocarbon radicals with six to twelve carbon atoms and comprising at least one aromatic ring, are novel compounds prepared by the action of a mixture of carboxylic acids R.sub.3 COOH and R.sub.4 COOH upon an .alpha.-acyloxymalononitrile, R.sub.1 COO--C(CN).sub.2 --R.sub.2, in the presence of an acid catalyst and are useful as intermediates in organic synthesis and low temperature activators in bleaching or scouring compositions.Type: GrantFiled: August 22, 1977Date of Patent: July 3, 1979Assignee: Produits Chimiques Ugine KuhlmannInventors: Bernard Dubreux, Serve Y. Delavarenne, Jean-Pierre Schirmann
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Patent number: 4123552Abstract: Fungus and mold growth in crops and organic matter are inhibited by the use of bis-carboxylic acid esters and compositions thereof. In a preferred embodiment, crops and animal feedstuffs are preserved during storage by applying a microbiocidal amount of a mono-, di or trioxymethylene, or lower alkylidene bis-alkanoate, or a mixture thereof.Type: GrantFiled: October 17, 1975Date of Patent: October 31, 1978Assignee: Chevron Research CompanyInventors: Daniel L. Kensler, Jr., Gustave K. Kohn, David D. Walgenbach
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Patent number: 4091006Abstract: A new series of substituted esters of 3-hydroxyindone compounds have been found to have exceptional miticidal and herbicidal activity.Type: GrantFiled: October 1, 1975Date of Patent: May 23, 1978Assignee: Union Carbide CorporationInventors: John A. Durden, Jr., Anthony A. Sousa, John F. Stephen
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Patent number: 4086278Abstract: 1-Alkenyl thioethers of glycols are described. The alkenyl thioethers possess central nervous system activity and are useful as tranquilizers.Type: GrantFiled: March 15, 1976Date of Patent: April 25, 1978Assignee: Ortho Pharmaceutical CorporationInventor: Allen Frederick Hirsch
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Patent number: RE31715Abstract: Novel liquid crystal compounds are disclosed, which are chiral esters based upon the phenol ##STR1## Typical examples are: ##STR2## and mixtures of these compounds have a helical pitch such that the mixtures reflect light of a specific wavelength when illuminated with ordinary light and the pitch is temperature sensitive so that the mixtures can be used in temperature indicating devices. Specific examples are given as are samples of mixtures that can be used in phase change electro-optic display devices.Type: GrantFiled: March 27, 1981Date of Patent: October 30, 1984Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: David Coates, George W. Gray, Damien G. McDonnell