Alicyclic Carbamates Patents (Class 560/115)
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Patent number: 4337349Abstract: Dimethacrylates are provided having the following chemical structure: ##STR1## where n represents a number of 2 to 8;R.sub.1 and R.sub.2 are the same or different and are hydrogen or groups of the formula: ##STR2## where R.sub.3 is an aliphatic, aromatic or cycloaliphatic group having 1 to 14 carbon atoms. These compounds are useful in dental material which cures to form polymers having high mechanical strength, low water sorption, resistance to staining, good color stability when exposed to short-wave radiation (e.g., sunlight) and good chemical resistance to the oral environment. Also provided are a method for polymerizing these compounds in situ on teeth and a tooth comprising polymers of these compounds.Type: GrantFiled: June 2, 1980Date of Patent: June 29, 1982Assignee: Scientific Pharmaceuticals, Inc.Inventors: Jan A. Orlowski, David V. Butler, Patrick D. Kidd
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Patent number: 4337262Abstract: Hydantoins of formula (I) ##STR1## have biological properties related to those of naturally occurring prostaglandins and may be used in medicine, for example in the treatment of thrombosis.Type: GrantFiled: November 30, 1978Date of Patent: June 29, 1982Assignee: Burroughs Wellcome Co.Inventors: Norman Whittaker, Albert G. Caldwell
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Patent number: 4335219Abstract: The reaction of an isocyanate such as toluene diisocyanate with itself to form an isocyanurate or with an active hydrogen compound such as diethylene glycol to form a urethane is catalyzed by the presence of an ar-ammonium areneoxide such as 4-dodecyl-2-trimethylammonium phenoxide.Type: GrantFiled: April 6, 1981Date of Patent: June 15, 1982Assignee: The Dow Chemical CompanyInventors: Donald H. Clarke, George J. Pomranky, Donald L. Schmidt
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Patent number: 4335138Abstract: Novel carbamates derived from substituted cyclic .beta.-keto-alcohols, their preparation, and pharmaceutical formulations which contain these compounds and which may be used as hypnotics in the treatment of sleep disturbance and as sedatives.Type: GrantFiled: September 15, 1980Date of Patent: June 15, 1982Assignee: BASF AktiengesellschaftInventors: Walter-Wielant Wiersdorff, Karl-Heinz Geiss, Harald Weifenbach, Wolfgang Worstmann, Dieter Lenke, Rolf Kretzschmar
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1H-Inden-1-one derivatives, their use in microbicidal compositions, and for combating microorganisms
Patent number: 4333949Abstract: 2,3-Dichloro-7-hydroxy-1H-inden-1-one derivatives of the formula I ##STR1## wherein R.sub.1 is hydrogen or one of the groups ##STR2## R.sub.2 and R.sub.3 independently of one another are each hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl or nitro,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.4 -alkenyl, each of which is unsubstituted or substituted by halogen, or R.sub.4 is phenyl which is unsubstituted or is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, trifluoromethyl, cyano or nitro, or it is a C.sub.3 -C.sub.6 -cycloalkyl group, andR.sub.5 is C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkenyl.These compounds exhibit a microbicidal action against in particular phytopathogenic fungi and bacteria.Type: GrantFiled: June 5, 1981Date of Patent: June 8, 1982Assignee: Ciba-Geigy CorporationInventors: Elmar Sturm, Robert Nyfeler -
Patent number: 4327034Abstract: Sulfamic acid halides and processes for the preparation of sulfamic acid halides by reaction of monosubstituted sulfamic acid halides with halogen compounds in the presence of specific amounts of a basic compound and in the presence of an organic solvent, if desired with subsequent treatment with water at a pH of at most 7. The compounds obtainable by the process of the invention, some of which are new, are valuable starting materials for the preparation of crop protection agents, dyes and drugs.Type: GrantFiled: June 25, 1979Date of Patent: April 27, 1982Assignee: BASF AktiengesellschaftInventors: Gerhard Hamprecht, Adolf Parg, Karl-Heinz Koenig
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Patent number: 4324739Abstract: (Dimethylaminoalkyl)carboxylic and -carbamic acid esters and (dimethylaminoalkyl) ethers and ureas are compounds which are especially suitable for use as amine curing agents for polyepoxide compounds. They impart longer curing times to the curable mixtures and thus good processing properties, especially when the mixtures are used as adhesives. In addition, the mechanical properties are often improved. Further, these compounds afford advantages when used as curing agents on account of their low volatility.Type: GrantFiled: March 31, 1980Date of Patent: April 13, 1982Assignee: Ciba-Geigy CorporationInventors: Helmut Zondler, Roland Moser
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Patent number: 4321404Abstract: Radiation curable coating compositions for providing solvent-resistant abhesive coatings comprise polyfluorinated acrylates and methacrylates, polyethylenically unsaturated crosslinking agents and a film-forming organic polymer. The compositions can be used after radiation curing to render substrates oil, soil, and water repellent. The cured compositions have particular use as release coatings in image transfer systems wherein a fused xerographic image is transferred from the release coated surface, to another surface due to the particular characteristics of the coatings. Novel poly(fluorooxyalkylene)urethane acrylate compounds are also disclosed.Type: GrantFiled: May 20, 1980Date of Patent: March 23, 1982Assignee: Minnesota Mining and Manufacturing CompanyInventors: Brian H. Williams, Chung-I Young
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Patent number: 4315861Abstract: A process is disclosed for preparing a carbamic acid phenyl ester of the formula (I) ##STR1## wherein R is alkyl having 1 to 8 carbon atoms, aryl, cycloalkyl having 5 or 6 carbon atoms, or aralkyl having 7 to 16 carbon atoms, wherein the aryl, cycloalkyl or aralkyl is unsubstituted or substituted by at least one alkyl group having 1 to 8 carbon atoms;R.sub.1 is hydrogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, cyanomethyl, 1,3-dioxolan-2-yl, or carboalkoxyamino wherein the alkoxy group contains 1 to 4 carbon atoms;R.sub.2 is hydrogen, halogen, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms; orR.sub.1 and R.sub.2 form together a carbocyclic ring or a heterocyclic ring fused to the phenyl ring wherein the carbocyclic ring of the heterocyclic ring is unsubstituted or substituted by at least one alkyl having 1 to 8 carbon atoms, which comprises acylating a phenol of the formula (II) ##STR2## with a compound of the formula (IV) ##STR3## in the presence of a base.Type: GrantFiled: March 23, 1981Date of Patent: February 16, 1982Assignee: Chinoin Gyogyszer RTInventors: Gyorgy Lugosi, Antal Simay, Janos Bodnar, Istvan Turcsan, Istvan Jelinek, Eva Somfai, Laszlo Simandi
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Patent number: 4316042Abstract: Compounds of the formula II: ##STR1## are produced by reacting a compound of the formula III ##STR2## with a compound of the formula IV: ##STR3## wherein R.sub.1 is hydrogen, alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by cycloalkyl of 3 to 6 carbon atoms, polyhaloalkyl of 1 to 5 carbon atoms, allyl, propargyl, enzyl or aryl,R.sub.2 is hydrogen, halogen, alkyl or alkoxy, each of 1 to 4 carbon atoms, trifluoromethyl, nitro, alkylamino or dialkylamino, wherein the alkyl groups have 1 to 4 carbon atoms, or aryl,R.sub.3 is hydrogen, halogen, alkyl or alkoxy, each of 1 to 4 carbon atoms, or aryl,R.sub.4 is hydrogen, nitro, halogen, alkyl or alkoxy each of 1 to 4 carbon atoms or aryl,R.sub.5 is hydrogen, halogen, alkyl, alkylthio or alkoxy each of 1 to 4 carbon atoms, nitro, trifluoromethyl or aryl,R.sub.6 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, benzyl or aryl, andR is alkyl of 1 to 4 carbon atoms.Type: GrantFiled: August 15, 1979Date of Patent: February 16, 1982Assignee: Sandoz Ltd.Inventor: Peter Funfschilling
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Patent number: 4309561Abstract: Acrylate monomers useful as a component of U.V. curable resin compositions and anaerobic adhesive compositions are provided and have the structure: ##STR1## where the phenanthrene ring contains up to three (3) double bonds, where R.sub.1 is a divalent radical, where R.sub.2 is a divalent radical, and where R.sub.3 is a hydrogen atom or an alkyl group.Type: GrantFiled: June 20, 1980Date of Patent: January 5, 1982Assignee: Gulf Oil CorporationInventors: Thomas F. Huemmer, Pallavoor R. Lakshmanan
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Patent number: 4304922Abstract: Production of urethanes by the oxycarbonylation reaction of N,N'-disubstituted ureas and organic compounds containing at least one hydroxyl group with carbon monoxide in the presence of molecular oxygen and/or organic nitro compounds and a catalyst system comprising (a) a noble metal and/or noble metal compound of the eighth subgroup of the periodic system of elements and (b) a compound of an element and/or elements of the third to fifth main group and/or first to eighth subgroup of the periodic system of elements characterized in that said compounds are capable of undergoing Redox reactions under the reaction conditions.Type: GrantFiled: February 27, 1980Date of Patent: December 8, 1981Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp, Gunter Stammann
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Patent number: 4304923Abstract: Ethylenically unsaturated polymerizable oligomers, which are particularly useful in printing plate compositions, comprise backbones formed by the removal of hydrogen from hydroxyl groups and having bonded thereto both carboxylic acid groups and ethylenically unsaturated, free radical polymerizable groups, these last two groups bonded to the backbone through the reaction of isocyanate groups.Type: GrantFiled: January 2, 1980Date of Patent: December 8, 1981Assignee: Minnesota Mining and Manufacturing CompanyInventor: Alan D. Rousseau
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Patent number: 4297489Abstract: Certain 7-acylamido-3-(1-carboxy-loweralkyl-tetrazol-5-ylthiomethyl)-3-cephem-4-ca rboxylic acids and their salts and easily hydrolyzed esters of the 4-carboxyl group were synthesized and found to be potent antibacterial agents which exhibited good aqueous solubility. In a preferred embodiment the 7-substituent was 2'-aminomethylphenylacetamido.Type: GrantFiled: June 27, 1975Date of Patent: October 27, 1981Assignee: Bristol-Myers CompanyInventors: William J. Gottstein, Murray A. Kaplan, Alphonse P. Granatek
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Patent number: 4297501Abstract: A process for producing urethanes by reacting primary amines, carbon monoxide and organic hydroxyl compounds in the presence of molecular oxygen and/or organic nitro compounds as oxidizing agents and a catalyst system comprising a noble metal and/or a compound of a noble metal of the 8th subgroup of the Periodic System of Elements and a compound capable of undergoing Redox reactions under reaction conditions of the 3rd to 5th main group and/or 1st to 8th subgroup of the Periodic System of Elements.Type: GrantFiled: February 27, 1980Date of Patent: October 27, 1981Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp
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Patent number: 4293470Abstract: A polyurea polymer polyol with improved storage stability is made by the reaction of a hydroxyl-containing amine, a polyether polyol of about 3,000 to 8,000 molecular weight and an organic polyisocyanate followed by quenching with a secondary amine. This stable polyurea polymer polyol may be used in the manufacture of flexible polyurethane foams which are firmer and stronger than similar products using conventional polyols.Type: GrantFiled: July 11, 1980Date of Patent: October 6, 1981Assignee: Texaco Inc.Inventor: Michael Cuscurida
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Patent number: 4291061Abstract: 2,3-Dichloro-7-hydroxy-1H-inden-1-one derivatives of the formula I ##STR1## wherein R.sub.1 is hydrogen or one of the groups ##STR2## R.sub.2 and R.sub.3 independently of one another are each hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl or nitro,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.4 -alkenyl, each of which is unsubstituted or substituted by halogen, or R.sub.4 is phenyl which is unsubstituted or is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, trifluoromethyl, cyano or nitro, or it is a C.sub.3 -C.sub.6 -cycloalkyl group, andR.sub.5 is C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkenyl.These compounds exhibit a microbicidal action against in particular phytopathogenic fungi and bacteria.Type: GrantFiled: October 31, 1979Date of Patent: September 22, 1981Assignee: Ciba-Geigy CorporationInventors: Elmar Sturm, Robert Nyfeler
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Patent number: 4289892Abstract: Active hydrogen-containing fluorochemical is used as a foam stabilizer for polyurethane foams. For example, rigid or flexible polyurethane foams with high or low density and uniform cellular structure are prepared using fluoroaliphatic radical-substituted poly(oxyalkylene) polyols as foam stabilizers.Type: GrantFiled: April 30, 1979Date of Patent: September 15, 1981Assignee: Minnesota Mining and Manufacturing CompanyInventor: Fredrich A. Soch
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Patent number: 4288612Abstract: Deposit control additives for internal combustion engines are provided which maintain cleanliness of intake systems withcut contributing to combustion chamber deposits. The additives are hydrocarbylpoly(oxyalkylene) aminocarbamates comprising a hydrocarbyl-terminated poly(oxyalkylene) chain of 2-5 carbon oxyalkylene units bonded through an oxycarbonyl group to a nitrogen atom of a diamine.Type: GrantFiled: April 28, 1980Date of Patent: September 8, 1981Assignee: Chevron Research CompanyInventors: Robert A. Lewis, Lewis R. Honnen
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Patent number: 4287083Abstract: Acyloin urethans can be employed to effect photopolymerization of free radical-polymerizable compositions in inert and oxygen-containing atmospheres.Type: GrantFiled: June 18, 1979Date of Patent: September 1, 1981Assignee: Lord CorporationInventors: John R. McDowell, Dennis D. Howard, Vincent J. Pascarella
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Patent number: 4283422Abstract: Novel 3-amino-4-homoisotwistane derivatives of the formula, ##STR1## wherein R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group or a C.sub.3 -C.sub.5 alkenyl group, and R.sub.2 is a C.sub.1 -C.sub.4 alkyl group or a C.sub.3 -C.sub.5 alkenyl group, or non-toxic pharmaceutically acceptable salts thereof, which are very valuable as medicines for the treatment of virus-caused diseases and as antiviral agents for animals and useful for the treatment of parkinsonean disease.Type: GrantFiled: February 12, 1980Date of Patent: August 11, 1981Assignees: Sumitomo Chemical Company, Limited, Kao Soap Company, LimitedInventors: Toshio Atsumi, Yoshiaki Takebayashi, Hideki Okajima
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Patent number: 4279833Abstract: Acrylic monomers containing a carbamate (urethane) functionality having the general formula: ##STR1## and difunctional carbamate monomers having the general formula: ##STR2## are prepared from 2-(1-hydroxyalkyl)-acrylates, acrylamides, acrylonitriles, vinyl ketones and nitroethylenes.Type: GrantFiled: December 17, 1979Date of Patent: July 21, 1981Assignee: Ashland Chemical CompanyInventors: Billy M. Culbertson, Larry K. Post
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Patent number: 4275223Abstract: A process is disclosed for selectively making trans-cyclohexane-1,4-diisocyanate, trans-cyclohexane-1,4-diamine, a trans-cyclohexane-1,4-diurethane, a trans-cyclohexane-1,4-diurea and trans-cyclohexane-1,4-disulphonyl urea by reacting ammonia with a mixture of cis and trans cyclohexane-1,4-dicarboxylic acid, a lower alkyl ester, a glycol ester, an oligomeric ester or a polyester to make a solid trans-dicarboxylic acid diamide in a first step. The diamide is chlorinated to form trans-cyclohexane-1,4-dicarboxylic acid-bis-N-chloramide.Type: GrantFiled: June 18, 1979Date of Patent: June 23, 1981Assignee: Akzona IncorporatedInventors: Hans Zengel, Manfred Bergfeld
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Patent number: 4266070Abstract: A process for the production of urethanes is provided in which an organic primary or secondary amine is contacted, in the substantial absence of reactive oxygen, with a source of carbon monoxide and an organic compound containing at least one hydroxyl group in the presence of a catalyst comprising a member selected from the group consisting of carbonyls of Co, Mo, Ti, Rh, Fe, Ni and mixtures thereof. Urethane yields and selectivities are further improved by conducting the reaction in the additional presence of an organic compound containing at least one C.dbd.N or C.dbd.C group. When such unsaturated organic compounds are employed, the catalyst can additionally comprise iridium carbonyl.Type: GrantFiled: May 25, 1979Date of Patent: May 5, 1981Assignee: Halcon Research and Development Corp.Inventor: David Moy
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Patent number: 4261897Abstract: N-chlorosulfinylcarbamate esters are produced by the reaction of thionyl chloride with carbamate esters having one unsubstituted hydrogen on the carbamate nitrogen atom, preferably in the presence of a hydrogen chloride acceptor. The resulting N-chlorosulfinylcarbamate esters are useful intermediates in the preparation of pesticides having relatively low mammalian toxicity.Type: GrantFiled: March 7, 1979Date of Patent: April 14, 1981Assignee: The Regents of the University of CaliforniaInventors: Mohamed A. H. Fahmy, Tetsuo R. Fukuto
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Patent number: 4262130Abstract: The present invention relates to an improved process for the production of urethanes (carbamic acid esters) by the reaction of organic nitro compounds with carbon monoxide and organic compounds containing at least one hydroxy group in the presence of palladium and/or palladium compounds and a cocatalyst which consists of a mixture of one or more iron oxides and/or iron hydroxides and activating chloride-containing additives.Type: GrantFiled: January 17, 1980Date of Patent: April 14, 1981Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp
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Patent number: 4260781Abstract: A process for the production of carbamates is provided in which an organic primary or secondary amine is contacted, in the substantial absence of reactive oxygen, with a source of carbon monoxide, an organic compound containing at least one hydroxyl group, and a metal reactant comprising at least one member selected from the group consisting of compounds and complexes of Group VIII of the Periodic Table.Type: GrantFiled: May 25, 1979Date of Patent: April 7, 1981Assignee: Halcon Research and Development Corp.Inventor: Robert J. Harvey
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Patent number: 4259511Abstract: A process for separating selenium, selenium compounds, sulfur and/or sulfur compounds from urethanes containing these elements and/or compounds by reacting said urethanes with an aqueous permanganate solution and then separating the resulting phase system.Type: GrantFiled: January 25, 1980Date of Patent: March 31, 1981Assignee: Bayer AktiengesellschaftInventor: Hans-Joachim Scholl
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Patent number: 4258201Abstract: A process for the production of carbamates is provided in which an organic primary or secondary amine is contacted, in the substantial absence of reactive oxygen, with a source of carbon monoxide, an organic compound containing at least one hydroxyl group and a source of sulfur, selenium or tellurium, in the presence of an effective amount of a catalyst selected from the group consisting of non-halide compounds and complexes of metals of Groups IVB, VB, VIB, VIIB, VIII, IB and IIIA of the Periodic Table. Further improved results are obtained by employing in the reaction zone at least one promoter selected from the group consisting of metals of Group IA and IIA of the Periodic Table.Type: GrantFiled: January 29, 1979Date of Patent: March 24, 1981Assignee: Halcon Research and Development Corp.Inventor: David Moy
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Patent number: 4257804Abstract: Carbamic acid ester of the formula ##STR1## in which R and R.sub.1 are the same or different and are hydrogen, an aliphatic hydrocarbon residue which may also be substituted, a cycloaliphatic hydrocarbon residue which may also be substituted, an aromatic hydrocarbon residue which may also be substituted or a heterocyclic residue or wherein R and R.sub.1 together with the adjoining nitrogen atom form a heterocyclic residue.The compounds of the invention are herbicidal agents of particularly strong activity.Type: GrantFiled: April 10, 1979Date of Patent: March 24, 1981Assignee: Schering AktiengesellschaftInventors: Friedrich Arndt, Ludwig Nusslein
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Patent number: 4254136Abstract: Compounds of the formula I ##STR1## wherein R.sub.1 and R.sub.2 are each C.sub.1 -C.sub.4 -alkyl, R.sub.3 is C.sub.1 -C.sub.10 -alkyl or C.sub.3 -C.sub.6 -cycloalkyl and R.sub.4 is 2-isopropoxyphenyl; 2-(1,3-dioxolan-2-yl)-phenyl; 2-methylthiomethylphenyl; 2-ethylthiomethylphenyl; 2-isopropylphenyl; 3,5-dimethyl-4-methylthiophenyl or 2,2-dimethyl-(2H,3H)-dihydrobenzofuran-7-yl having valuable pesticidal in particular insecticidal properties.Type: GrantFiled: August 20, 1979Date of Patent: March 3, 1981Assignee: Ciba-Geigy CorporationInventors: Jozef Drabek, Manfred Boger
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Patent number: 4250322Abstract: A method for preparing oligourethanacrylates having the general formula ##STR1## where ##STR2## is a radical of a telogen; X is H, CH.sub.Type: GrantFiled: August 10, 1979Date of Patent: February 10, 1981Inventors: Alexei V. Efimov, Alfred A. Berlin, Tamara Y. Kefeli, Nina V. Varlamova, Grigory M. Strongin, Judif M. Altshuler, Boris I. Kolomazov
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Patent number: 4247653Abstract: A process is disclosed for preparing mixtures of low molecular weight polyhydroxyl compounds and hydroxyaldehydes and hydroxyketones by condensing formaldehyde hydrate with itself in the presence of (I) as catalyst a soluble or insoluble compound of a metal of the first to eighth sub-group or second to fourth main group of the Periodic System of Elements, optionally bound to a high molecular weight carrier, and (II) more than 10% by weight, based on formaldehyde, of one or more dihydric or higher hydric low molecular weight alcohols and/or higher molecular weight polyhydroxyl compounds. The pH of the reaction mixture is held at 5.5 to 9.0 until 5-40% conversion has occurred and is then lowered to between 4.5 and 8.0 (0.5-2.0 pH units lower). The reaction is then stopped by inactivating the catalyst.Type: GrantFiled: August 30, 1977Date of Patent: January 27, 1981Assignee: Bayer AktiengesellschaftInventor: Kuno Wagner
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Patent number: 4246391Abstract: Radiation-curable acrylated urethanes having a lower viscosity than heretofore achievable without dilution are produced by an improved process that involves first reacting a monohydroxy-functional acrylate with a polyisocyanate followed by the reaction of the product mixture produced with a polyol. The acrylated urethanes so produced are useful in radiation-curable coatings.Type: GrantFiled: June 26, 1979Date of Patent: January 20, 1981Assignee: Union Carbide CorporationInventor: Stuart L. Watson, Jr.
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Patent number: 4242520Abstract: A process for the production of carbamates is provided which comprises contacting an organic primary or secondary amine with a source of carbon monoxide, an organic compound containing at least one hydroxyl group and a source of sulfur, selenium or tellurium, in the presence of a catalyst for the reaction and in the presence of at least one member selected from the group consisting of disulfides of the formulaR.sup.1 --S--S--R.sup.2wherein R.sup.1 and R.sup.2 comprise members selected from the group consisting of alkyl, aryl, cycloalkyl, alkaryl, aralkyl, heterocyclic, alkenyl, alkynyl, alkanoyl, aranoyl, halogenated derivatives of the foregoing groups, and derivatives of the foregoing groups in which one or more carbon atoms is replaced by an oxygen atom.Type: GrantFiled: January 29, 1979Date of Patent: December 30, 1980Assignee: Halcon Research & Development CorporationInventor: David Moy
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Patent number: 4239904Abstract: A process for the preparation of urethanes by reacting a tertiary amine, an alcohol and carbon monoxide in the presence of a catalytic quantity of a copper salt, oxygen and a dehydrating agent is disclosed. The reaction is preferably carried out using a copper halide catalyst and dehydrating agents which combine with water to release the alcohol used in the preparation of the urethane product.Type: GrantFiled: June 6, 1979Date of Patent: December 16, 1980Assignee: Atlantic Richfield CompanyInventor: Haven S. Kesling, Jr.
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Patent number: 4234738Abstract: Salicylate esters have been found to be suitable blocking agents for polyisocyanates, enabling preparation of hydroxy terminated polybutadiene based polyurethane bound propellant grains having extended pot life. Unblocking occurs readily at normal propellant cure temperatures, allowing normal cure rates.Type: GrantFiled: November 17, 1978Date of Patent: November 18, 1980Assignee: Thiokol CorporationInventors: William H. Graham, Inella G. Shepard
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Patent number: 4234714Abstract: A process is described for the preparation of urethane prepolymers from hydroxy-terminated diene polymers and normally liquid, relatively non-volatile, aromatic polyisocyanates. The prepolymers are made at a temperature above about 150.degree. C. to provide urethane prepolymer products that resist the tendency to form multiple phases or layers upon storage at room temperature.Type: GrantFiled: March 29, 1979Date of Patent: November 18, 1980Assignee: Textron Inc.Inventors: Mason H. Earing, Leonard H. Gielinski, Paul F. Martin, Glenn H. Petschke
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Patent number: 4227980Abstract: Novel photoreactive coating compositions based on urethane modified acrylates which may be employed alone or in mixtures with other photoreactive acrylates are disclosed.Type: GrantFiled: September 13, 1978Date of Patent: October 14, 1980Assignee: Whittaker CorporationInventors: Siegfried A. Pregitzer, Jay K. Laufer, John J. Marino, James W. Hancock
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Patent number: 4224417Abstract: The invention relates to new polyamines, preferably containing polyether segments, a process for their preparation and their use as starting components for the production of polyurethane resins. The process involves producing ketimines, aldimines or enamines containing hydroxyl groups by reacting a hydroxyl amine with an aldehyde or ketone and removing the water by product. The ketimine, aldimine, or enamine is then reacted with an NCO prepolymer wherein the hydroxyl group of the material reacts with the isocyanate group without disturbing the blocked amine. This polyaddition product is then hydrolyzed to unblock the high molecular weight polyamine.Type: GrantFiled: January 2, 1979Date of Patent: September 23, 1980Assignee: Bayer AktiengesellschaftInventors: Manfred Hajek, Kuno Wagner, Friedrich Moller, Peter Vehlewald
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Patent number: 4224454Abstract: Acyloin urethans can be employed to effect photopolymerization of free radical-polymerizable compositions in inert and oxygen-containing atmospheres.Type: GrantFiled: October 13, 1978Date of Patent: September 23, 1980Assignee: Lord CorporationInventors: John R. McDowell, Dennis D. Howard, Vincent J. Pascarella
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Patent number: 4219661Abstract: This invention relates to an improved process for the production of urethanes (i.e. carbamic acid esters) by reacting organic nitro compounds with carbon monoxide and organic compounds containing at least one hydroxy group in the presence of a unique catalyst system. The catalyst system consists of palladium or a palladium compound and iron oxychloride or a mixture of iron compounds containing iron oxychloride.Type: GrantFiled: April 23, 1979Date of Patent: August 26, 1980Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp, Gerhard Scharfe
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Patent number: 4217439Abstract: Crosslinked acrylate-acetoacetamide polymers are disclosed. These polymers are prepared by the reaction of at least one polyfunctional acrylate with at least one diacetoacetamide in the presence of a catalyst capable of promoting the reaction between the polyfunctional acrylate and the diacetoacetamide. In a preferred embodiment, the polymers are employed to produce wear layer compositions for surface coverings.Type: GrantFiled: June 19, 1978Date of Patent: August 12, 1980Assignee: Armstrong Cork CompanyInventor: John S. Heckles
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Patent number: 4216224Abstract: Compositions and methods for treating the symptoms of psoriasis consisting of topical application of a solution, gel, lotion, cream or ointment containing as a principal active ingredient one or more retinoyl compounds is disclosed. The active ingredient consists of one or more compounds which are retinoyl esters of a hydroxy acid, a hydroxy amide, or a hydroxy acid ester, or a retinoyl carbamic or thiocarbamic acid derivative. The composition of this invention may include a single member of the above active ingredients present in a total amount of from 0.01 to 5% by weight of the total composition, or a plurality thereof present in a preferred concentration of from 0.02 to 2% by weight of the total composition.Type: GrantFiled: September 22, 1978Date of Patent: August 5, 1980Inventors: Ruey J. Yu, Eugene J. Van Scott
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Patent number: 4210750Abstract: Alcohols are reacted with certain isocyanate compounds to produce the N-substituted carbamoyloxy derivatives which are cleaved to obtain the carbamate.Type: GrantFiled: November 17, 1976Date of Patent: July 1, 1980Assignee: Merck & Co., Inc.Inventors: Stephen Marburg, Janos Kollonitsch
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Patent number: 4209632Abstract: Sulfonyl carbazates containing at least one group of:--SO.sub.2 --NHNH--COO--wherein the oxygen and the sulfur atoms attach to various organic groups are useful as high temperature blowing agents for gas-expandable polymers. Additionally, novel polyfunctional and secondary-alkyl substituted sulfonyl carbazates have been discovered.Type: GrantFiled: December 30, 1977Date of Patent: June 24, 1980Assignee: Uniroyal, Inc.Inventor: Byron A. Hunter
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Patent number: 4203916Abstract: A process is disclosed for selectively making trans-cyclohexane-1,4-diisocyanate, trans-cyclohexane-1,4-diamine, a trans-cyclohexane-1,4-diurethane, a trans-cyclohexane-1,4-diurea and trans-cyclohexane-1,4-disulphonyl urea by reacting ammonia with a mixture of cis and trans-cyclohexane-1,4-dicarboxylic acid, a lower alkyl ester, a glycol ester, an oligomeric ester or a polyester to make a solid trans-dicarboxylic acid diamide in a first step. The diamide is chlorinated to form cyclohexane-1,4-dicarboxylic acid-bis-N-chloramide.Type: GrantFiled: March 6, 1978Date of Patent: May 20, 1980Assignee: Akzona IncorporatedInventors: Hans Zengel, Manfred Bergfeld
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Patent number: 4196302Abstract: Novel quaternary phosphonium salts, bearing one or more carbamate groups attached through nitrogen, are prepared by condensing a hydroxymethyl phosphonium salt having the formula [R.sub.4-n P(CH.sub.2 OH).sub.n ].sup.+ X.sup.- with an alkyl carbamate having the formula NH.sub.2 CO.sub.2 R'. The products, which have the general formula [R.sub.4-n P(CH.sub.2 NHCO.sub.2 R').sub.n ].sup.+ X.sup.-, are useful as finishing agents for imparting flame retardant or durable press properties to cotton fabrics.Type: GrantFiled: March 6, 1979Date of Patent: April 1, 1980Assignee: The United States of America as represented by the Secretary of AgricultureInventor: Arlen W. Frank
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Patent number: 4192926Abstract: New polyols modified by acyl urea groups, process for the preparation thereof and use thereof as starting component for the preparation of preferably foamed polyurethane plastics. The process involves (A) reacting diisocyanatocarbodiimides corresponding to :OCN--R.sup.2 --N.dbd.C.dbd.N .sub.M --R.sup.2 --NCOwith polyhydroxyl compounds corresponding to:A--OH).sub.nto form a polyhydroxyl compound containing carbodiimide groups and (B) completely or partially reacting, the carbodiimide groups remaining in the product of step (A), with a carboxylic acid corresponding to the following general formula: ##STR1## to form acyl urea groups, and (C) distilling off the inert solvent, if used; whereinm represents a number of from 1 to 10;s represents an integer of from 1 to 3; andR.sup.1 represents hydrogen or a monofunctional or--in the form of a bridge to further acyl groups--a di- or trifunctional C.sub.1 -C.sub.18 aliphatic, C.sub.4 -C.sub.15 cycloaliphatic, C.sub.6 -C.sub.Type: GrantFiled: April 16, 1979Date of Patent: March 11, 1980Assignee: Bayer AktiengesellschaftInventors: Walter Schafer, Kuno Wagner, Kurt Findeisen
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Patent number: RE30772Abstract: Radiation curable compounds are disclosed comprising an amide moiety, a urethane moiety and an ethylenically unsaturated functional group, typically an acrylate functional group. The compounds comprise the reaction products of an amide-containing compound having at least one hydroxy functional group, a polyisocyanate and a polyfunctional compound having a hydroxy functional group reactive with an isocyanato group of the polyisocyanate, which polyfunctional compound provides an ethylenic functional group in the reaction product. Coating compositions containing these radiation curable reaction products cure at relatively high rates to form films having high abrasion resistance and improved tensile strength and elongation properties as compared to conventional urethane acrylate coating compositions.Type: GrantFiled: June 2, 1980Date of Patent: October 13, 1981Assignee: PPG Industries, Inc.Inventors: Charles B. Friedlander, Gerald W. Gruber, Rostyslaw Dowbenko