One Double Bond Between The Ring Members Of The Oxazole Ring Patents (Class 548/237)
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Patent number: 4479888Abstract: Dispersing additives for lubricating fluids are disclosed, which contain the oxazoline function and are prepared by reacting amino alcohols with mono or bicarboxylic linear or branched chain aliphatic acids having from 2 to 51 carbon atoms. These additives are characterized by a very high dispersing power which makes them particularly suitable for engines used in stop-and-go service.Type: GrantFiled: June 4, 1980Date of Patent: October 30, 1984Assignee: Agip Petroli S.p.A.Inventors: Paolo Koch, Luciano Mattei, Giampaolo Gerbaz
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Patent number: 4477384Abstract: .alpha.-Substituted acrylic acids are prepared from carboxylic acids in high yield and high purity by novel process. The .alpha.-substituted acrylic acids are prepared by condensing a fatty acid with 2-amino-2-methylpropanol, neutralizing the resulting oxazoline reaction mixture, converting the oxazoline with paraformaldehyde to an intermediate which is heated with an azetrope such as cumene or xylene and the resulting methylene oxazoline hydrolyzed to obtain the desired product.Type: GrantFiled: February 20, 1981Date of Patent: October 16, 1984Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Samuel Serota, Warner M. Linfield
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Patent number: 4477465Abstract: This invention relates to substituted 4,10-dihydro-10-oxothieno benzoxepins of the formula, ##STR1## where R is hydrogen and lower alkyl; R.sub.1 is ##STR2## where R.sub.2 is hydrogen, lower alkyl and benzyl of the formula ##STR3## where X is hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, nitro, and amino; ##STR4## where R.sub.3 and R.sub.4 are the same or different and are hydrogen and lower alkyl; ##STR5## where R.sub.5 and R.sub.6 are the same or different and are lower alkyl; and the pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: March 10, 1983Date of Patent: October 16, 1984Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Lawrence L. Martin, Linda L. Setescak
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Patent number: 4468395Abstract: Compounds of Formula I ##STR1## wherein R.sub.1 is a prostaglandin or prostacyclin residue;Y is oxygen, sulfur, imino, or N-(C.sub.1 -C.sub.4 -alkyl) imino;Q is (CR.sub.6 R.sub.7).sub.p wherein p is an integer of 0 to 3;R.sub.2 is hydrogen; alkyl of 1-6 carbon atoms optionally substituted by hydroxy or amino; C.sub.1 -C.sub.4 -alkoxycarbonyl; benzyloxycarbonyl; cyano; or di-C.sub.1 -C.sub.4 -alkylaminocarbonyl;R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 each independently is hydrogen; alkyl of 1-6 carbon atoms optionally substituted by hydroxy or amino; or aryl; andR.sub.3 and R.sub.4 together form a trimethylene, tetramethylene, or 1,3-butadienylene group when R.sub.2 and R.sub.5 together represent a direct bond;have valuable pharmacological properties, e.g., as blood-pressure-lowering or abortive agents.Type: GrantFiled: May 20, 1982Date of Patent: August 28, 1984Assignee: Schering, AktiengesellschaftInventors: VorbruHelmut, Walter Elger, Michael-Harold Town, Ekkehard Schillinger
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Patent number: 4460596Abstract: A compound of the formula ##STR1## wherein Ring A is phenyl or halogenophenyl and R.sup.1 is hydrogen or lower alkyl, or a pharmaceutically acceptable salt thereof and processes for preparing the same are disclosed. Said compound is useful as a hypolipidemic agent.Type: GrantFiled: April 29, 1982Date of Patent: July 17, 1984Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Kazuo Matsumoto, Kohki Takashima
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Patent number: 4431551Abstract: Aqueous drilling muds are improved in lubricity by the presence of at least an effective amount of an oxazoline of a C.sub.6 to C.sub.50 2-(alkylthio)succinic acid or anhydride.Type: GrantFiled: September 30, 1982Date of Patent: February 14, 1984Assignee: Exxon Research & Engineering Co.Inventors: Antonio Gutierrez, Darrell W. Brownawell, Robert C. Portnoy, Stanley J. Brois
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Patent number: 4426529Abstract: A process comprising reacting a 2-methyloxazoline with a 3-methyl-2-buten-1-yl derivative of the formula ##STR1## in which X is halide, sulphonate or phosphate thereby to produce a 2-methyl-3-(3-methyl-2-butenyl)-2-oxazolinium salt of the formula ##STR2## reacting the oxazolinium salt with an alcoholate of the formulaR.sup.5 --O--M (V)in which M is one equivalent of an alkali metal or alkaline earth metal cation, to produce an oxazolidine of the formula ##STR3## pyrolyzing the oxazolidine to produce a 2-methyl-3-(3-methyl-2-butenyl)-oxazolindine of the formula ##STR4## and heating the 2-methylene-3-(3-methyl-2-butenyl)-oxazolidine to produce a 2-(2,2-dimethyl-3-buten-1-yl)-2-oxazoline.Type: GrantFiled: January 25, 1982Date of Patent: January 17, 1984Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Dieter Arlt
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Patent number: 4419255Abstract: Lubricating oil characterized by improved friction reduction contains friction reducing amounts of a keto amide prepared by the reaction of an amine and an unsaturated cyclic keto acid bearing pendant alkyl groups.Type: GrantFiled: February 1, 1982Date of Patent: December 6, 1983Assignee: Texaco Inc.Inventors: Benjamin J. Kaufman, Robert A. Sawicki, Stephen A. Levine
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Patent number: 4391814Abstract: Compounds of Formula I ##STR1## wherein R.sub.1 is the residue of an antiphlogistically effective carboxylic acid of the formula R.sub.1 COOH,n is an integer 1, 2, or 3, andX is oxygen, sulfur, or optionally alkylated nitrogenhave valuable antiinflammatory activity.Type: GrantFiled: December 23, 1981Date of Patent: July 5, 1983Assignee: Schering AktiengesellschaftInventor: Helmut Vorbruggen
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Patent number: 4376861Abstract: The process comprises the steps of:(A) reacting by contacting an anhydrous or substantially anhydrous 2-alkyl-2-oxazoline with formaldehyde in a molar ratio of at least about 1.5 moles of 2-alkyl-2-oxazoline per mole of formaldehyde, thereby forming 2-(.alpha.-hydroxymethylalkyl)-2-oxazoline,(B) recovering the 2-(.alpha.-hydroxymethylalkyl)-2-oxazoline from the reaction product of step (A), and(C) reacting by contacting the 2-(.alpha.-hydroxymethylalkyl)-2-oxazoline and step B with an alkali or alkaline earth metal hydroxide, thereby forming 2-alkenyl-2-oxazoline.As an example, step A was conducted by reacting 2-ethyl-2-oxazoline (4 moles) having less than 1,000 ppm of water with paraformaldehyde (1 mole) at a reaction temperature of 100.degree. C. for approximately 5.5 hours. The excess oxazoline reactant was removed along with water as "overheads" by fractional distillation of the reaction product, leaving the 2-(.alpha.-hydroxymethylethyl)-2-oxazoline in approximately 96 percent yield.Type: GrantFiled: December 3, 1981Date of Patent: March 15, 1983Assignee: The Dow Chemical CompanyInventors: James W. Lalk, Gerald C. Kolb, Donald A. Tomalia, Peter W. Owen
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Patent number: 4368309Abstract: Polymers of vinyl oxazoline drying oil ester which esters are made by a process which reacts drying oil fatty acids with tris(hydroxy methyl) amino methane to form an intermediate which intermediate is further reacted at about 175.degree.-195.degree. C. with a formaldehyde/alcohol solution to form the vinyl oxazoline drying oil ester; the improvement used with this process is the use of at least 3 moles of formaldehyde to one mole of intermediate and about 1-5% by weight, based on the weight of the intermediate, of methanol and adding after the reaction with formaldehyde about 5-25% by weight, based on the weight of the ester solution, of an alcohol, a ketone or a mixture of an alcohol and a ketone; coating compositions of these polymers are also disclosed.Type: GrantFiled: December 9, 1981Date of Patent: January 11, 1983Assignee: E. I. Du Pont de Nemours & Co.Inventor: Joseph A. Vasta
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Patent number: 4358598Abstract: A process comprising reacting a 2-methyloxazoline of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each independently is hydrogen, alkyl, aralkyl, optionally substituted aryl or two of them together form a ring,with a 3-methyl-2-buten-1-yl derivative of the formula ##STR2## in which X is halide, sulphonate or phosphate, thereby to produce a 2-methyl-3-(3-methyl-2-butenyl)-2-oxazolinium salt of the formula ##STR3## reacting the oxazolinium salt with an alcoholate of the formulaR.sup.5 --O--M (V)in whichM is one equivalent of an alkali metal or alkaline earth metal cation,to produce an oxazolidine of the formula ##STR4## pyrolyzing the oxazolidine to produce a 2-methylene-3-(3-methyl-2-butenyl)-oxazolidine of the formula ##STR5## and heating the 2-methylene-3-(3-methyl-2-butenyl)-oxazolidine to produce a 2-(2,2-dimethyl-3-buten-1-yl)-2-oxazoline of the formula ##STR6## The compounds (II), (III) and (IV) are new.Type: GrantFiled: December 1, 1980Date of Patent: November 9, 1982Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Dieter Arlt
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Patent number: 4357464Abstract: The level of residual 2-isopropenyl-2-oxazoline monomer in polymers prepared therefrom can be reduced by reaction of the protonated salt of the monomer with a variety of nucleophiles. The products of the reaction with the monomer are much less toxic than the 2-isopropenyl-2-oxazoline and the utility of the polymer is thereby enhanced. The reaction product of 2-isopropenyl-2-oxazoline and H.sub.2 SO.sub.3 is itself novel and useful.Type: GrantFiled: April 15, 1981Date of Patent: November 2, 1982Assignee: The Dow Chemical CompanyInventors: Donald A. Tomalia, Timothy J. Adaway
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Patent number: 4350519Abstract: Novel 2-nitro-5-phenoxyphenyloxazoles, -oxazines and -thiazoles are disclosed. These compounds have the formula ##STR1## wherein A is a C.sub.2 -C.sub.3 alkylene or C.sub.2 -C.sub.3 alkenylene radical which can be substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl, each of R.sub.1, R.sub.2 and R.sub.3 independently is hydrogen, halogen, trifluoromethyl, nitro or cyano, and X is oxygen, sulfur or an imino group. The novel compounds have herbicidal and plant growth-inhibiting properties. They are especially suitable for use as selective herbicides in crops of cereals.Type: GrantFiled: March 2, 1981Date of Patent: September 21, 1982Assignee: Ciba-Geigy CorporationInventor: Dieter Durr
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Patent number: 4345084Abstract: Unsaturated eicosanoic acids and derivatives thereof which inhibit the synthesis of SRS-A are useful for treating and preventing asthma and allergic responses caused by SRS-A as well as useful in inhibiting inflammation.Type: GrantFiled: June 29, 1981Date of Patent: August 17, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Ka-Kong Chan, George W. Holland, Perry Rosen
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Patent number: 4340741Abstract: An improved process for preparing a vinyl oxazoline drying oil ester by reacting drying oil fatty acids with tris(hydroxy methyl) amino methane to form an intermediate which is further reacted at about 175.degree.-190.degree. C. with a formaldehyde/alcohol solution to form the vinyl oxazoline drying oil ester; the improvement used with this process is the use of at least 3 moles of formaldehyde to one mole of intermediate and about 1-5% by weight, based on the weight of the intermediate, of methanol and adding after the reaction with formaldehyde about 5-25% by weight, based on the weight of the ester solution, of an alcohol, a ketone or a mixture of an alcohol and a ketone; polymers of this ester and coating compositions of these polymers are also disclosed.Type: GrantFiled: December 1, 1980Date of Patent: July 20, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Joseph A. Vasta
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Patent number: 4307237Abstract: This invention is directed toward pharmacologically active compound of the formula ##STR1## wherein A is ##STR2## R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, phenyl, alkoxy lower alkyl, halo lower alkyl, amino lower alkyl, substituted amino lower alkyl, substituted phenyl, pyridyl, aralkyl and the groups ##STR3## wherein R is hydrogen or lower alkyl and ROOC where R is lower alkyl; R.sub.2 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, alkoxy lower alkyl, halo lower alkyl, amino or substituted amino lower alkyl, amino, cyano, cyano lower alkyl, substituted amino, chloro, bromo and iodo, the group --COOR where R is hydrogen or lower alkyl, the group ##STR4## where R is hydrogen or lower alkyl, or derivatives thereof, e.g., the group R--C.dbd.Type: GrantFiled: August 14, 1980Date of Patent: December 22, 1981Assignee: Hoffmann-La Roche Inc.Inventors: Armin Walser, Rodney I. Fryer
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Patent number: 4292186Abstract: Fluid compositions containing a lubricant or liquid hydrocarbon fuel and a minor amount of a complex salt containing a 5- or 6-member ring are provided. These derivatives are made by complexing (1) the reaction product of an alcohol or an aminoalcohol with a succinic compound containing a long-chain hydrocarbon with (2) a metal salt. One such complex is one made by reacting a metal salt with the product of reaction between an alkylsuccinic acid or anhydride and said alcohol or aminoalcohol.Type: GrantFiled: July 3, 1980Date of Patent: September 29, 1981Assignee: Mobil Oil CorporationInventors: Sheldon Chibnik, Ferdinand P. Otto, deceased, Helen F. Otto, executrix
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Patent number: 4288437Abstract: Compounds of the formula ##STR1## wherein Ar is phenyl; mono- or di-substituted phenyl, where the substituents are one to two halogens, one to two alkyls of 1 to 3 carbon atoms, or one amino, nitro, cyano or trifluoromethyl; or pyridinyl;R is hydrogen, chlorine, methyl or methoxy;R.sub.1 is hydrogen or methyl;R.sub.2 is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, methyl-(cycloalkyl of 3 to 8 carbon atoms) or --A--R.sub.4,where A is alkylene of 2 to 3 carbon atoms, and R.sub.4 is hydroxyl, methylamino, dimethylamino, N-methyl-ethylamino, diethylamino, pyrrolidino, piperidino, hexamethyleneimino, morpholino or 4-methyl-1-piperazinyl; orR.sub.1 and R.sub.Type: GrantFiled: July 28, 1980Date of Patent: September 8, 1981Assignee: Boehringer Ingelheim GmbHInventors: Wolfhard Engel, Gunter Trummlitz, Ernst Seeger, Joachim Kahling
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Patent number: 4263153Abstract: A dispersant or dispersant mixture that is useful in fuel and lubricant compositions, and that is characterized by its derivation from a long chain dicarboxylic acid material and an amino alcohol, is stabilized against oxidation by sulfurization by reaction with sulfur or with a sulfur compound selected from the group consisting of carbon disulfide, sulfides of phosphorus including P.sub.2 S.sub.5 and P.sub.4 S.sub.3, and phosphosulfurized olefins. More particularly, the dispersant so treated will usually comprise a mono or bis-oxazoline prepared by reaction of a hydrocarbyl-substituted C.sub.4 -C.sub.10 dicarboxylic acid or anhydride or ester thereof, having at least 50 carbon atoms in the hydrocarbyl group, with a 2,2-disubstituted 2-amino-1-alkanol that has from two to three hydroxy groups and that contains from 4 to 8 total carbon atoms.Type: GrantFiled: October 11, 1979Date of Patent: April 21, 1981Assignee: Exxon Research & Engineering Co.Inventors: Rosemary O'Halloran, Esther D. Winans
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Patent number: 4258047Abstract: Pyrazole derivatives of the formula ##STR1## wherein R.sup.1 is H or Cl; R.sup.2 is 1-methyl-4-piperidyloxy-carbonyl, 2-(4-phenylpiperazino)-ethoxycarbonyl, benzoxazol-2-yl, benzthiazol-2-yl, tetrazol-5-yl or 3-R.sup.3 -4-R.sup.4 -thiazolidin-2-yl; R.sup.3 is H, alkanoyl of 1-7 carbon atoms or benzoyl; and R.sup.4 is H or COOH,or a physiologically acceptable salt thereof;possess valuable pharmacological activities.Type: GrantFiled: February 19, 1980Date of Patent: March 24, 1981Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Joachim Gante, Hans-Eckart Radunz, Dieter Orth, Klaus Minck, Albrecht Wild, Michael Klockow
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Patent number: 4247671Abstract: Novel oxazoline-containing monomers represented by the formula ##STR1## wherein: n is an integer of from 1 through 20:R.sub.1 is selected from the group consisting of hydrogen and methyl; andR.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are independently selected from the group consisting of hydrogen and alkyl of from 1 through 20 carbon atoms;polymers thereof, and methods for preparing the same are disclosed.The hydrocurable polymers of the invention, before hydrolysis, contain a plurality of units represented by the following formula: ##STR2## Polymers having such units may be obtained by addition polymerization of monomers of structure I, preferably with other ethylenically unsaturated monomers.Type: GrantFiled: April 11, 1979Date of Patent: January 27, 1981Assignee: Rohm and Haas CompanyInventors: R. Larry Reitz, Thomas W. Hutton, Sheldon N. Lewis
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Patent number: 4227914Abstract: Novel herbicidally active phenoxy-alkyloxazolines, of the formula ##STR1## are disclosed, wherein A is hydrogen, halogen, cyano, nitro and amido or thiamido radical,B is hydrogen, C.sub.1 -C.sub.4 alkyl,C is halogen, cyano, nitro or trifluoromethyl, amido or thiamido,D is halogen, cyano or nitro,n is 0, 1 or 2,R.sub.1, R.sub.2 and R.sub.3, independently are hydrogen or C.sub.1 -C.sub.4 alkyl andX is oxygen, sulfur, sulfinyl or sulfonyl.Type: GrantFiled: January 19, 1979Date of Patent: October 14, 1980Assignee: Ciba-Geigy CorporationInventors: Werner Fory, Beat Bohner, Dieter Durr, Georg Pissiotas, Otto Rohr, Henry Szczepanski
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Patent number: 4225336Abstract: Phenoxyalkyloxyzolines corresponding to the formula ##STR1## wherein R is hydrogen or methylZ is a Phenyl-or Pyridyl-radical ##STR2## R.sub.1 is halogen, trifluoromethyl, cyano or nitro R.sub.2 is hydrogen, halogen or cyanoR.sub.3 is halogen trifluoromethyl or cyano andn is 1 or 2.are effective herbicides which are tolerant towards cereal.Type: GrantFiled: July 30, 1979Date of Patent: September 30, 1980Assignee: Ciba-Geigy CorporationInventors: Werner Fory, Hermann Rempfler, Georg Pissiotas, Otto Rohr, Beat Bohner
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Patent number: 4221720Abstract: Lactone oxazoline reaction products of hydrocarbon substituted lactone carboxylic acids, for example, polybutyl lactone carboxylic acid, with 2,2-disubstituted-2-amino-1-alkanols, such as tris-(hydroxymethyl)aminomethane (THAM), and their derivatives are useful aditives in oleaginous compositions, such as sludge dispersants for lubricating oil, or anti-rust agents for gasoline.Type: GrantFiled: December 7, 1978Date of Patent: September 9, 1980Assignee: Exxon Research & Engineering Co.Inventors: Stanley J. Brois, Antonio Gutierrez
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Patent number: 4220778Abstract: 8-Aryl-1,2,3,4-tetrahydroisoquinoline and derivatives thereof having the formula ##STR1## and the non-toxic pharmacologically acceptable acid addition salts thereof; wherein R is hydrogen, benzyl, or an alkyl radical of 1 to 7 carbon atoms; R.sup.1 is hydrogen or an alkyl radical of 1 to 7 carbon atoms; R.sup.2 in each occurrence is hydrogen, an alkyl radical of 1 to 7 carbon atoms or alkoxy radical of 1 to 7 carbon atoms, alike or different; Ar is phenyl optionally substituted with one or more halogen, an alkyl radical of 1 to 7 carbon atoms, or alkoxy radical of 1 to 7 carbon atoms; and n is positive integer less than 4, are disclosed. These compounds are useful because of their anti-arrhythmic, antimicrobial and central nervous system activity.Type: GrantFiled: October 30, 1978Date of Patent: September 2, 1980Assignee: G. D. Searle & Co.Inventors: Charles R. Ellefson, Kathleen Prodan
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Patent number: 4216162Abstract: Novel 2-(2,2-dihalogenovinyl)-3,3-dimethylcyclopropanecarboxylic acid derivatives of the formula ##STR1## e.g. amides, thioamides, oxazolines, amidoximes and hydroxamic acids, are produced by reacting the new compounds ##STR2## with a base in the presence of a diluent.Type: GrantFiled: June 28, 1978Date of Patent: August 5, 1980Assignee: Bayer AktiengesellschaftInventors: Dieter Arlt, Manfred Jautelat
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Patent number: 4176073Abstract: A molybdenum complex of a lactone oxazoline dispersant, preferably an oil-soluble lactone oxazoline obtained as a reaction product of hydrocarbyl substituted lactone carboxylic acids, for example, polybutyl lactone carboxylic acid, with 2,2-disubstituted-2-amino-1-alkanols, such as tris-(hydroxymethyl) aminomethane (THAM), and their derivatives are useful additives in lubricating oils since both the sludge dispersant and antifriction properties of said oil are enhanced.Type: GrantFiled: September 18, 1978Date of Patent: November 27, 1979Assignee: Exxon Research & Engineering Co.Inventors: Jack Ryer, Esther D. Winans, Stanley J. Brois, Antonio Gutierre
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Patent number: 4174322Abstract: Lactone oxazoline reaction products of hydrocarbon substituted lactone carboxylic acids, for example, polybutyl lactone carboxylic acid, with 2,2-disubstituted-2-amino-1-alkanols, such as tris-(hydroxymethyl)aminomethane (THAM), and their derivatives are useful additives in oleaginous compositions, such as sludge dispersants for lubricating oil, or anti-rust agents for gasoline.Type: GrantFiled: July 20, 1977Date of Patent: November 13, 1979Assignee: Exxon Research & Engineering Co.Inventors: Stanley J. Brois, Antonio Gutierrez