Alicyclic Carbamates Patents (Class 560/115)
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Patent number: 4801644Abstract: Aqueous polyurethane dispersions useful as coating compositions wherein the polyurethane comprises the reaction product of(a) an isocyanate-terminated polyurethane prepolymer containing carboxylic acid salt groups formed by reacting:(i) a polyisocyanate component containing at least 1% by weight of diphenylmethane-2,4'-diisocyanate, and(ii) an active hydrogen containing component containing a polyol and a carboxy group containing diol or triol, and(b) an active hydrogen containing chain extender.Type: GrantFiled: October 3, 1986Date of Patent: January 31, 1989Assignee: Polyvinyl Chemicals Inc.Inventor: Richard G. Coogan
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Patent number: 4788322Abstract: Process comprising coupling of an acylimidazole-activated derivative of a reduced and protected phenylalanine with the magnesium salt of malonic acid monoethyl ester to produce the beta-ketoester, which is subsequently reduced with NaCNBH.sub.3 /THF in glacial acetic acid to afford a separable mixture of 3-S and 3-R 3-hydroxy-(4S)-4-(N-.alpha.-BOC)amino-5-cyclohexylpentanoic acid, such that large-scale, high yield production of optically-active ACHPA is significantly improved.Type: GrantFiled: July 31, 1987Date of Patent: November 29, 1988Assignee: Merck & Co., Inc.Inventors: Paul F. Schuda, William J. Greenlee, Prasun K. Chakravarty, Philip Escola
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Patent number: 4788329Abstract: A process is disclosed whereby mono- and diurethane cyclohexyl derivatives are obtained corresponding to the Lewis acid-catalyzed addition reaction of dipentene and methyl carbamate at a temperature of from about 40.degree. to about 150.degree.C. The mono- and diurethane cyclohexyl derivatives are pyrolytically converted to other corresponding mono- and diisocyanate cyclohexyl derivatives. Novel vinyl unsaturated monoisocyanate cyclohexyl derivatives useful as reactants for polyfunctional compounds to produce cured compositions are disclosed.Type: GrantFiled: November 3, 1986Date of Patent: November 29, 1988Assignee: American Cyanamid CompanyInventor: Laurence J. Nummy
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Patent number: 4788287Abstract: A high performance water and oil repellant composed of a compound comprising at least two terminal segments and an intermediate segment connecting the terminal segments and having a molecular weight of from 800 to 20,000, each terminal segment containing at least one polyfluoroalkyl group connected by a --CONH-- linking group, said intermediate segment being a urethane oligomer containing at least two --CONH-- linking groups in one molecule, and said terminal segments and intermediate segment being connected by a --CONH-- linking group.Type: GrantFiled: September 3, 1986Date of Patent: November 29, 1988Assignee: Asahi Glass Company Ltd.Inventors: Masashi Matsuo, Masayuki Tamura, Katsuji Ito
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Patent number: 4786652Abstract: Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein: R.sup.1 is lower alkoxy or optionally substituted phenoxy,R.sup.2 is the same as R.sup.1, or R.sup.2 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenylalkyl,R.sup.3 is hydrogen, lower alkyl, lower alkoxy, halo, optionally substituted phenyl, optionally substituted phenyl-lower-alkyl or optionally substituted phenyl-lower-alkoxy, and m is 1 or 2;X is the same and is either --C(O)OR.sup.4 or --C(O)NR.sup.5 R.sup.6,whereinR.sup.4 is alkyl, phenyl or benzyl optionally substituted with one or two lower alkyl groups, lower alkoxy groups or halo; andR.sup.5 and R.sup.6 are independently hydrogen, lower alkyl, cycloalkyl or phenyl optionally substituted with one or two lower alkyl groups, lower alkoxy groups or halo.Type: GrantFiled: March 9, 1987Date of Patent: November 22, 1988Assignee: Syntex (U.S.A.) Inc.Inventor: Michael C. Venuti
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Patent number: 4781947Abstract: A sizing agent for a carbon fiber comprized mainly of an unsaturated urethane compound produced by a reaction of an unsaturated alcohol with an isocyanate which is able to couple the carbon fiber with an unsaturated polyester resin or vinylester resin is disclosed. The preferably unsaturated alcohols are allylalcohols and reaction products of an unsaturated carboxylic acids with an alkyleneoxides.Type: GrantFiled: August 12, 1987Date of Patent: November 1, 1988Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Makoto Saito, Hiroshi Toki, Makoto Miyazaki, Hiroshi Inoue
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Patent number: 4782175Abstract: The molecule of the new urethanes contains an aliphatic fluoroalcohol, an isocyanate and an aromatic dihydroxy, diamino, aminohydroxy, aminocarboxy or hydroxycarboxy compound. They are prepared by reacting an aliphatic fluoroalcohol with a diisocyanate or triisocyanate to give the fluoroalcohol/isocyanate adduct and by reacting this adduct with said aromatic compound to give the desired urethanes composed of an aliphatic fluoroalcohol, an isocyanate and the bifunctional aromatic compound mentioned, and also be reacting a urethane of this type which also carries an active hydrogen atom on the bifunctional aromatic compound, with an isocyanate compound containing one or more isocyanate groups. The new urethanes are preferably used for imparting an oleophobic and hydrophobic finish to textiles and leather.Type: GrantFiled: July 1, 1987Date of Patent: November 1, 1988Assignee: Hoechst AktiengesellschaftInventors: Frank Wehowsky, Rolf Kleber, Lothar Jaeckel
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Patent number: 4778915Abstract: The invention relates to fluoroacrylic monomers of formula: ##STR1## in which R.sub.f denotes a perfluoroalkyl radical, R is hydrogen or a methyl radical, R' denotes an alkyl or cycloalkyl radical, or --NR'-- denotes a 1, 4-piperazinylene radical, W and Z denote divalent connecting groups, Q is oxygen or sulphur or an --NR"-- group, R" denoting hydrogen an alkyl radical, and A is a C.sub.2 or C.sub.3 alkylene group. The polymers (homo- or copolymers) derived from these monomers may be used for the water-repellency and oil-repellency treatment of various substrates, particularly leather.Type: GrantFiled: October 16, 1986Date of Patent: October 18, 1988Assignee: AtochemInventors: Marie-Jose Lina, Andre Dessaint
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Patent number: 4776875Abstract: Compounds of the formula ##STR1## in which R.sub.1 and R.sub.2 denote alkyl, OH, CF.sub.3 or cyanoethyl, A preferably denotes --COOH, R.sub.3 denotes inter alia alkoxycarbonylalkoxy, fairly high-molecular (>C.sub.12) alkoxy, alkylcarbonylalkoxy or nitrobenzyloxy, are valuable herbicides and growth regulators.Type: GrantFiled: March 26, 1986Date of Patent: October 11, 1988Assignee: Hoechst AktiengesellschaftInventors: Heinz J. Loher, Klaus Bauer, Hermann Bieringer
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Patent number: 4775732Abstract: There are described vinyl ether terminated ester and urethane oligomers which cure or polymerize particularly rapidly, especially by cationic polymerization which is radiation induced in the presence of an onium salt. The oligomeric units arise most often from the reaction of a dicarboxylic acid or diisocyanate with a diol. The carboxyl-terminated oligomeric esters are esterified with vinyl ether terminated alcohols which can be thought of as the adducts of alkynes and diols which are bis(hydroxyalkyl)cycloalkanes where the cycloalkane is of ring size 5 through 8.Type: GrantFiled: January 11, 1988Date of Patent: October 4, 1988Assignee: Allied-Signal Inc.Inventor: Stephen C. Lapin
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Patent number: 4772695Abstract: A process for the preparation of vinyl carbamates of formula I ##STR1## is described which comprises heating an .alpha.-halogeno-carbamate of formula II ##STR2## in which X is a halogen atom at a temperature between 70.degree. and 250.degree. C. for a period of time between several minutes up to several hours. R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are the same or different. The process is applicable to a great variety of products in which R.sub.1, R.sub.2, R.sub.3, and R.sub.4 have different meanings. The process permits to prepare in a simple and economical fashion, vinyl carbamates, which have industrial value and novel vinyl carbamates.Type: GrantFiled: September 19, 1983Date of Patent: September 20, 1988Assignee: Societe Nationale des Poudres et ExplosifsInventors: Roy A. Olofson, Gary P. Wooden, Jonathan T. Martz
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Patent number: 4766234Abstract: The novel urethanes, in addition to at least one perfluoroalkyl group, also contain epichlorohydrin groups and dialcohol radicals in the molecule. They are prepared by reacting a fluorine-containing alcohol with epichlorohydrin to give the perfluoroalkyl-epichlorohydrin adduct, reacting this adduct with a di- or triisocyanate to give the perfluoroalkyl-epichlorohydrin-isocyanate adduct and by reacting this adduct with a dialcohol or a monoetherified dialcohol to give the desired urethanes having a perfluoroalkyl group and having epichlorohydrin groups and dialcohol radicals, and by reacting a suitable urethane compound of this type with a perfluoroalkyl-containing di- or triisocyanate to give the desired urethanes having a plurality of perfluoroalkyl groups and having epichlorohydrin groups and dialcoholradicals. The novel urethanes are preferably used for the oleophobic and hydrophobic finishing of textiles.Type: GrantFiled: November 12, 1986Date of Patent: August 23, 1988Assignee: Hoechst AktiengesellschaftInventors: Frank Wehowsky, Rolf Kleber, Lothar Jaeckel
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Patent number: 4759832Abstract: Biscarbamates, including novel one, of the general formula ##STR1## where R is alkyl of 1 to 8 carbon atoms and X is a hydrocarbon radical of 2 to 60 carbon atoms in which one or more carbon atoms may be replaced by hetero atoms and which may contain halogen atoms or ester, carbonyl or nitrile groups are prepared by electrochemically oxidizing formamides of the general formula ##STR2## in the presence of an alkanol of the formula ROH and of an ionic halide.Type: GrantFiled: February 13, 1987Date of Patent: July 26, 1988Assignee: BASF AktiengesellschaftInventors: Dieter Degner, Heinz Hannebaum
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Patent number: 4758587Abstract: Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein: R.sup.1 is lower alkoxy or optionally substituted phenoxy;R.sup.2 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenylalkyl;R.sup.3 is hydrogen, lower alkyl, lower alkoxy, halo, optionally substituted phenyl, optionally substituted phenyl-lower-alkyl or optionally substituted phenyl-lower-alkoxy, and m is 1 or 2;X and Y are different and are either R.sup.4 or --C(O)W whereinR.sup.4 is lower alkyl or optionally substituted phenyl-lower-alkyl;W is --OR.sup.5 or --NR.sup.6 R.sup.7,whereinR.sup.5 is alkyl, optionally substituted phenyl or optionally substituted benzyl; andR.sup.6 and R.sup.7 are independently hydrogen, lower alkyl, cycloalkyl or optionally substituted phenyl.Type: GrantFiled: March 9, 1987Date of Patent: July 19, 1988Assignee: Syntex (U.S.A.) Inc.Inventor: Michael C. Venuti
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Patent number: 4751273Abstract: Vinyl ether terminated urethane resins may be prepared by reacting the product obtained by the addition of acetylene to an organic polyol with an isocyanate-containing compound at temperatures ranging from about ambient to about 125.degree. C. The thus prepared resin may then be cured by irradiation from an electron beam, thermally or by exposure to an ultraviolet light to cure the resin and form a coating material.Type: GrantFiled: July 6, 1987Date of Patent: June 14, 1988Assignee: Allied-Signal, Inc.Inventors: Stephen C. Lapin, David W. House
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Patent number: 4749806Abstract: The present invention relates to a process for the synthesis of isocyanates and of isocyanate derivatives. Isocyanates are obtained by reacting an organic halide with a metal cyanate in an organic medium in the presence of a catalyst consisting of a complex of nickel with at least one organic ligand, in which complex the nickel is in the zero oxidation state.A carbamate or a urea, respectively, are obtained by a subsequent reaction with a hydroxy compound or a primary or secondary amine.Isocyanates and their derivatives are used especially either as refined synthesis agents for the production of pesticides and medications, or as monomers or comonomers for the preparation of many macromolecular compounds.Type: GrantFiled: August 25, 1987Date of Patent: June 7, 1988Assignee: Societe Nationale des Poudres et ExplosifsInventors: Igor Tkatchenko, Rabih Jaouhari, Michel Bonnet, Gordon Dawkins, Serge Lecolier
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Patent number: 4744827Abstract: (Meth)-acrylic acid derivatives of tricyclodecanes of the formula ##STR1## in which R.sup.1 and R.sup.2 are identical or different and denote hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and R.sup.3 and R.sup.4 are identical or different and represent the group ##STR2## wherein X denotes a divalent bridge member from the group ##STR3## and Y denotes a divalent bridge member from the group ##STR4## and wherein R.sup.5 represents hydrogen or methyl and R.sup.6 represents lower alkyl or phenyl, have been found. Dental compositions in which the present (meth)-acrylic acid derivatives of tricyclodecanes are used, exhibit considerably less polymerization shrinkage.Type: GrantFiled: June 4, 1986Date of Patent: May 17, 1988Assignee: Bayer AktiengesellschaftInventors: Jens Winkel, Bruno Bomer, Robert Schmitz-Josten, Gerhard Klein, Carlhans Suling, Dieter Arlt
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Patent number: 4744828Abstract: The invention relates to novel (meth)-acrylic acid derivatives of tricyclodecanes of the formula ##STR1## in which R.sup.1 and R.sup.2 are identical or different and denote hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and R.sup.3 and R.sup.4 are identical or different and represent the groups. ##STR2## in which X is a divalent bridge member comprising the group ##STR3## and Y is a linear or branched hydrocarbon chain which has 2 to 10 carbon atoms and can optionally contain oxygen bridges and is optionally substituted by 1 to 4 acrylate or methacrylate radicals, andR.sup.5 represent hydrogen or methyl andR.sup.6 represents hydrogen, lower alkyl or phenyland to their use in dental compositions.Type: GrantFiled: June 4, 1986Date of Patent: May 17, 1988Assignee: Bayer AktiengesellschaftInventors: Jens Winkel, Bruno Bomer, Carlhans Suling, Jurgen Reiners, Wolfgang Podszun
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Patent number: 4742169Abstract: The invention is a process for the preparation of halohydroxyalkyl carbamates which comprises contacting an epihalohydrin carbonate with a secondary amine-containing compound, wherein the secondary amine has a pKa at which the secondary amine will react with the epihalohydrin carbonate and which does not catalyze the formation of unwanted by-products in the further presence of an acid scavenger capable of forming a salt with the hydrogen halide by-product formed, in an amount sufficient to prevent the formation of unwanted by-products, in a polar organic solvent under conditions such that a halohydroxyalkyl carbamate, wherein the carbamate nitrogen is tertiary, is prepared.Type: GrantFiled: April 5, 1985Date of Patent: May 3, 1988Assignee: The Dow Chemical CompanyInventors: Marsha A. Paul, George A. Doorakian
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Patent number: 4740531Abstract: Polyaminohydroxyl compounds having molecular weights of from 200 to 20,000 and a functionality greater than 1 but less than or equal to 8 containing 0.165-16.5 wt. % amino and hydroxyl groups and 0.295-29.5 wt. % urethane and/or urea groups are produced by hydrolyzing the corresponding NCO prepolymer containing OH groups. The equivalent ratio of amino groups to hydroxyl groups in these polyaminohydroxyl compounds is from 99:1 to 0.1:99.9. Groups which are inert with respect to amines and isocyanates may optionally be present in the polyaminohydroxyl compounds in quantities such that the equivalent ratio of amine groups to inert groups is from 100:0 to 33.3:66.6 and the equivalent ratio of hydroxyl groups to inert groups is from 100:0 to 33.3:66.6. These polyaminohydroxyl compounds are useful in the production of polyurethanes. The polyaminohydroxyl compounds in which the difference between the sum of amino groups plus hydroxyl groups plus inert groups and the sum of hydroxyl groups plus inert groups is 2.+-.Type: GrantFiled: July 23, 1987Date of Patent: April 26, 1988Assignee: Bayer AktiengesellschaftInventor: Werner Rasshofer
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Patent number: 4739106Abstract: A process for preparing a 2-carbamoyloxyalkyl-1,4-dihydropyridine derivative represented by the general formula: ##STR1## which comprises: (a) reacting a 3-amino-3-carbamoyloxyalkylacrylic acid derivative represented by the general formula: ##STR2## with a benzylidene compound represented by the general formula: ##STR3## (b) reacting the 3-amino-3-carbamoyloxyalkylacrylic acid derivative of the general formula II with an aldehyde compound represented by the general formula: ##STR4## and a .beta.-keto-ester compound represented by the general formula:R.sup.4 --CO--CH.sub.2 --COOR.sup.2 (V)(c) reacting a 3-carbamoyloxyalkylpropiolic acid derivative represented by the general formula: ##STR5## with the benzylidene compound of the general formula III and ammonia or its salt; or(d) reacting the 3-carbamoyloyalkylpropiolic acid derivative of the general formula VI with the aldehyde compound of the general formula IV, the .beta.-keto-ester compound of the general formula V and ammonia or its salt.Type: GrantFiled: May 16, 1986Date of Patent: April 19, 1988Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Tetsuji Miyano, Kunio Suzuki, Nobuo Harada
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Patent number: 4734520Abstract: Crosslinking components for hydroxy and/or primary and/or secondary amino group containing paint binders for the crosslinking of synthetic resins carrying at least two groups capable of ester or amide formation with carboxylic acids. In particular there is disclosed the use of the crosslinking components in compositions for electrodeposition (ED) whereby at 120.degree. C. and above coatings with extraordinary paint performance are obtained. The use of methyl or ethyl esters gives extremely low condensation losses. The crosslinking components are obtained through reaction of one mole of a diisocyanate, preferably at room temperature, in the presence of sodium, or preferably sodium phenolate, as catalyst, with at least one mole of a CH-active alkyl ester of the general formula X--CH.sub.2 --COOR, wherein X is --COOR, --CN or CH.sub.3 --CO-- and R is an alkyl radical with 1 to 8 C-atoms and subsequent reaction of the free isocyanate groups with polyamines of the general formula H.sub.2 N--(R--NH).sub.n --R--NH.Type: GrantFiled: May 29, 1986Date of Patent: March 29, 1988Assignee: Vianova Kunstharz, A.G.Inventors: Helmut Plum, Willibald Paar
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Patent number: 4728670Abstract: Biphenyl hydroxamic acids are provided having the structure ##STR1## wherein m is 1 to 7, X is S, O or NH, R is H, lower alkyl, aryl, aralkyl or cycloalkyl and R.sup.1 is H, lower alkyl, aryl, aralkyl, cycloalkyl, alkanoyl or aroyl.These compounds are inhibitors of .DELTA..sup.5 -lipoxygenase and as such are useful as antiallergy agents.Type: GrantFiled: June 4, 1986Date of Patent: March 1, 1988Assignee: E. R. Squibb & Sons, Inc.Inventors: Martin F. Haslanger, Ravi K. Varma, Eric M. Gordon
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Patent number: 4724252Abstract: Polyamines containing aromatically bound primary amino groups are prepared in a single stage process by hydrolyzing an isocyanate in the presence of a compound containing an amidine and/or guanidine group and a water-miscible, aprotic-dipolar solvent. This hydrolysis is carried out at from 20.degree. to 210.degree. C. with the reactants being in substantially homogeneous phase. The isocyanate starting material contains aromatically bound NCO groups and has NCO content of from 0.5 to 40 wt. %. The compound containing amidine and/or guanidine groups functions as a catalyst and is used in a quantity of at least 0.001 parts by weight for every 100 parts by weight of isocyanate. The water-miscible solvent is used in a quantity of at least 10 parts by weight for every 100 parts by weight of polyisocyanate. The polyamines thus-produced are particularly useful in the production of polyurethanes.Type: GrantFiled: August 11, 1986Date of Patent: February 9, 1988Assignee: Bayer AkitengesellschaftInventor: Werner Rasshofer
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Patent number: 4723032Abstract: Modified polyamines containing carbamates, urethane and/or urea and/or thiourethane groups and having a primary amine content of from 0.1 to 20.2 wt % are produced by (a) mixing an organic isocyanate with a base in the presence of at least one hydrogen-active compound and water and (b) converting the carbamate, urethane and/or urea and/or thiourethane groups to amino groups. The isocyanate starting material has an isocyanate content of from 0.5 to 40 wt. %. The hydrogen-active compound contains a hydroxy and/or amino and/or thiol group. Water is used in a quantity such that one mol of water is present for each isocyanate equivalent. Conversion to form the amino groups is accomplished by treatment with a proton donor and/or thermal decomposition and/or solvent extraction. The polyamines thus-produced are particularly useful in the production of polyurethanes.Type: GrantFiled: October 29, 1982Date of Patent: February 2, 1988Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Dieter Dieterich
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Patent number: 4720569Abstract: A polycarbamic acid ester-type curing agent for thermosetting resin paints, said curing agent containing per molecule at least two groups represented by the following formula ##STR1## wherein Y represents ##STR2## --O--, or --S--; R.sub.1 represents a direct bond, or a divalent aliphatic hydrocarbon group having 1 to 6 carbon atoms which may be substituted by a hydroxyl group or an alkoxy group, provided that when Y is ##STR3## R.sub.1 represents a direct bond; R.sub.2 and R.sub.4, independently from each other, represent a hydrogen atom, or an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may be substituted by an amino group, a hydroxyl group or an alkoxy group, or a group of the formula ##STR4## and R.sub.3 represents a hydrogen atom or a monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms which may be substituted by a hydroxyl group or an alkoxy group.Type: GrantFiled: July 30, 1985Date of Patent: January 19, 1988Assignee: Kansai Paint Co., Ltd.Inventor: Akira Tominaga
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Patent number: 4717740Abstract: An aqueous alkaline developable UV curable urethane acrylate compound and composition are used for making flexible solder mask coatings, characterized by rapid development in an aqueous, alkaline medium, and advantageous performance properties.Type: GrantFiled: May 17, 1985Date of Patent: January 5, 1988Assignee: M&T Chemicals Inc.Inventors: Paul L. K. Hung, Kenneth K. S. Tseng
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Patent number: 4713476Abstract: A process for the preparation of aliphatic, cycloaliphatic, arylaliphatic and aliphatic-cycloaliphatic di- and polyurethanes wherein primary aliphatic, cycloaliphatic, arylaliphatic or aliphatic-cycloaliphatic di- or polyamines are reacted with urea and a primary or secondary aliphatic alcohol at temperatures of above 190.degree. C. to 300.degree. C., following which ammonia and other by-products are separated from the aliphatic, cycloaliphatic, arylaliphatic or aliphatic-cycloaliphatic di- or polyurethane product.Type: GrantFiled: June 26, 1986Date of Patent: December 15, 1987Assignee: BASF AktiengesellschaftInventors: Franz Merger, Friedrich Towae
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Patent number: 4704420Abstract: Highly functional fluorinated polyisocyanates of the formula: ##STR1## wherein Z.sub.1 represents the functional group --O--CO--NH--R--NCO;Z.sub.2 represents the difunctional group --O--CO--NH--R--NH--CO--O--;R.sub.f is a radical derived from fluoropolyethers having a molecular weight between 500 and 7000;T represents a trivalent or tetravalent radical derived from a polyol;q is zero or 1; ands is 1 or 2.Also, varnishes containing said highly functional fluorinated polyisocyanates of formula (I).Type: GrantFiled: December 5, 1986Date of Patent: November 3, 1987Assignee: Montedison S.p.A.Inventors: Franco Federici, Giorgio Pin, Ennio Cozzi
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Patent number: 4697033Abstract: Certain novel derivatives of carbamates and their use for the control of pests.Type: GrantFiled: December 24, 1985Date of Patent: September 29, 1987Assignee: Sandoz Ltd.Inventor: Clive A. Henrick
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Patent number: 4694097Abstract: Carbamate esters are produced by reacting at ambient or elevated temperature an amine with carbon monoxide and an alcohol in the presence of a protonic acid, a dehydrating agent, for example a molecular sieve, and a catalyst comprising (a) at least one metal selected from the group palladium, rhodium, ruthenium, iridium and cobalt, and (b) at least one of the metals copper, molybdenum and iron, the components (a) and (b) being in the form of elemental metals or compounds thereof. The presence of the dehydrating agent reduces the formation of by-product carbon dioxide.Type: GrantFiled: April 25, 1986Date of Patent: September 15, 1987Assignee: The British Petroleum Company p.l.c.Inventors: Howard Alper, David J. H. Smith
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Patent number: 4692455Abstract: Compounds of the formula ##STR1## wherein Y is oxygen or sulfur are disclosed. These compounds are useful as hypotensive agents due to their angiotensin converting enzyme inhibition activity and depending upon the definition of R.sub.1 may also be useful as analgesics due to their enkepahlinase inhibition activity.Type: GrantFiled: January 25, 1985Date of Patent: September 8, 1987Assignee: E. R. Squibb & Sons, Inc.Inventor: Eric M. Gordon
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Patent number: 4687872Abstract: A process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a catalyst comprising rhodium, as a metal or compound, is disclosed. In the process of this invention, the rate of conversion and selectivity to urethane is increased by providing a rhodium catalyst comprising a polyamino ligand having at least two tertiary amino groups capable of coordinating with rhodium.Type: GrantFiled: December 9, 1985Date of Patent: August 18, 1987Assignees: Catalytica Associates, Haldor Topsoe A/SInventors: John H. Grate, David R. Hamm
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Patent number: 4681972Abstract: The S,S-isomers of Boc-benztine and Boc-cyclotine can be produced via the fractional crystallization of R-(+)-alpha-methylbenzylamine salt(s). The products are useful in the production of renin inhibitors.Type: GrantFiled: September 16, 1986Date of Patent: July 21, 1987Assignee: Warner-Lambert CompanyInventors: James S. Kaltenbronn, Michael A. Stier
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Patent number: 4677221Abstract: The present invention relates to a process for the production of aliphatic and/or cycloaliphatic diisocyanates which are color stable to heat, which is characterized in that a diisocyanate with aliphatically-and/or cycloaliphatically-bound isocyanate groups is heated in the presence of about 0.1 to 3% by weight, based on the diisocyanate, of at least one compound which is soluble in the diisocyanate and contains at least 3% by weight of structural units corresponding to the formula: ##STR1## for up to about 5 hours at a temperature of about 100.degree. to 220.degree. C. and the diisocyanate which has been treated in this way is subsequently purified by distillation.The present invention also relates to the use of the products of the present process for the production of modified polyisocyanates having improved coloration.Type: GrantFiled: October 29, 1985Date of Patent: June 30, 1987Assignee: Bayer AktiengesellschaftInventors: Hanns P. Muller, Werner Clarenz, Heinrich Grave
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Patent number: 4672137Abstract: 1,3-Di(alkoxycarbonylamino)propanes of the general formula I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 can be identical or different and each is hydrogen, or an aliphatic, cycloaliphatic, araliphatic or aromatic radical, and R.sup.4 is an aliphatic, cycloaliphatic or araliphatic radical, are prepared by reacting an .alpha.,.beta.-unsaturated aldehyde with a carbamic acid ester by reacting in a first stage as the .alpha.,.beta.-unsaturated aldehyde a compound of the general formula II ##STR2## where R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meanings, with a carbamic acid ester of the general formula III ##STR3## where R.sup.4 has the abovementioned meanings, at 0.degree.-150.degree. C. to give a 1,1,3-tri(alkoxycarbonylamino)propane of the general formua IV ##STR4## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the abovementioned meanings, and in a second stage heating the compound of the general formula (IV) in the presence of a hydrogenation catalyst and hydrogen under 1-300 bar at 100.Type: GrantFiled: April 29, 1986Date of Patent: June 9, 1987Assignee: BASF AktiengesellschaftInventors: Franz Merger, Joerg Liebe
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Patent number: 4668710Abstract: Included are trihalovinyl polyol ethers. The compositions have pendant 1,2,2-trihaloethenyl moieties. The compositions may be low viscosity oils or highly polymeric such as incorporated with a urethane or other polymers. One of the uses of the compositions is as flame retardants which may have high thermal stability and scorch resistance.Type: GrantFiled: December 23, 1985Date of Patent: May 26, 1987Assignee: The Dow Chemical CompanyInventors: Chester E. Pawloski, William J. Kruper, Jr.
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Patent number: 4665193Abstract: Compounds of the formula ##STR1## wherein A is ##STR2## intervene in the conversion of angiotensinogen to angiotensin II by inhibiting renin and thus are useful as anti-hypertensive agents.Type: GrantFiled: June 27, 1986Date of Patent: May 12, 1987Assignee: E. R. Squibb & Sons, Inc.Inventors: Denis E. Ryono, Edward W. Petrillo, Jr.
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Patent number: 4663472Abstract: A process for the transesterification of urethanes comprises reacting a urethane with an alcohol at elevated temperature in the presence of a Lewis base containing catalyst.The process is particularly useful when the alcohol used is a polyol since the product of the transesterification is a polyurethane. Since urethanes can be generated from amines and organic carbonates using the methods of the prior art, the present invention provides processes for the manufacture of polyurethanes from amines which avoid the use of either phosgene or isocyanates both of which are extremely toxic.Type: GrantFiled: January 30, 1985Date of Patent: May 5, 1987Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4661217Abstract: Carbamic acid esters (I)R.sup.1 NHCOOR.sup.2 (I)wherein R.sup.1 is H, alkyl, cycloalkyl or alkylaryl and R.sup.2 is alkyl, are prepared by electro-oxidation of a formamide (II)R.sup.1 NHCHO (II)in the presence of an alcohol R.sup.2 OH and of an ionic halide.Type: GrantFiled: August 11, 1986Date of Patent: April 28, 1987Assignee: BASF AktiengesellschaftInventors: Dieter Degner, Heinz Hannebaum, Michael Steiniger
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Patent number: 4634791Abstract: Compounds of the formula ##STR1## are suitable as curing accelerators which can be incorporated into ethylenically unsaturated, cold-curable resins.Type: GrantFiled: November 29, 1984Date of Patent: January 6, 1987Assignee: Bayer AktiengesellschaftInventors: Helmut-Martin Meier, Rolf Dhein, Jens Winkel, Gerhard Klein, Werner Kloker
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Patent number: 4629804Abstract: This invention relates to a process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a ruthenium catalyst. The selectivity of this process is increased by the use of methanol instead of various other alkanols, e.g. ethanol. Preferably the catalyst is a halide-free ruthenium catalyst, e.g. a ruthenium carbonyl complex.Type: GrantFiled: March 4, 1985Date of Patent: December 16, 1986Assignee: Catalytica AssociatesInventors: John H. Grate, David R. Hamm, Donald H. Valentine, Jr.
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Patent number: 4622408Abstract: The novel reagent, vinyl phenylthiocarbonate, is prepared. It is useful for the introduction of the vinyloxycarbonyl protecting group which is a valuable protecting group for amines, amino acids, peptides, proteins and phenols.Type: GrantFiled: October 22, 1981Date of Patent: November 11, 1986Assignee: Merck & Co., Inc.Inventor: Angelina J. Duggan
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Patent number: 4621149Abstract: A process for producing a urethane compound which comprises reacting at least one compound selected from the group consisting of a primary amine, a secondary amine and a urea compound with carbon monoxide and an organic hydroxyl compound in the presence of a catalyst system comprising:(a) at least one member selected from the group consisting of platinum group metals and compounds containing at least one platinum group element; and(b) at least one halogen-containing compound selected from the group consisting of alkali or alkaline earth metal halides, onium halides, compounds capable of forming onium halides in the reaction, oxo acids of halogen atoms and their salts, complex compounds containing halogen ions, organic halides and halogen molecules,in the presence of molecular oxygen and/or an organic nitro compound as an oxidizing agent at a temperature of from about 80.degree. C. to about 300.degree. C. under a pressure of from about 1 Kg/cm.sup.2 to about 500 Kg/cm.sup.2.Type: GrantFiled: December 10, 1984Date of Patent: November 4, 1986Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Shinsuke Fukuoka, Masazumi Chono
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Patent number: 4603216Abstract: This invention relates to a process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a ruthenium catalyst comprising a bis phosphine ligand.Type: GrantFiled: September 16, 1983Date of Patent: July 29, 1986Assignees: Catalytica Associates, Haldor Topsoe A/SInventors: John H. Grate, David R. Hamm, Donald H. Valentine, Jr.
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Patent number: 4600793Abstract: A process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a halide-free ruthenium catalyst is disclosed. In the process of this invention, the rate of conversion and selectivity to urethane is increased by providing a primary amine in the reaction solution.Type: GrantFiled: September 16, 1983Date of Patent: July 15, 1986Assignees: Catalytica Associates, Haldor Topsoe A/SInventors: John H. Grate, David R. Hamm, Donald H. Valentine
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Patent number: 4594441Abstract: A process for the preparation of urethanes. Urethanes having the general formula R.sub.1 (NHCOOR.sub.2).sub.n are reacted with an alcohol at a temperature of 120.degree. to 400.degree. C. in amounts such that, for every mol of the urethane, at least one mol of the alcohol is present. R.sub.1 is a radical obtained by removing the isocyanate groups from an n-functional organic isocyanate, which isocyanate has a boiling point greater than 100.degree. C. at atmospheric pressure. R.sub.2 is a radical obtained by removing the hydroxyl group from a monohydric alcohol which has a boiling point greater than 140.degree. C. at atmospheric pressure.Type: GrantFiled: May 14, 1984Date of Patent: June 10, 1986Assignee: Bayer AktiengesellschaftInventors: Kurt Findeisen, Klaus Konig, Rudolf Fauss, Peter Heitkamper
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Patent number: 4593118Abstract: 2,3-Diaminocarboxylic acid compounds are prepared by (A) nitrosating a .beta.-keto ester to form a 3-keto-2-oximino ester, (B) converting the resultant oxime to a protected 2-amine, (C) reductively aminating the 3-position of the protected 2-amine to form a 2,3-diaminocarboxylic acid ester wherein the 2-amino group is protected, and (D) when desired, treating the 2,3-diaminocarboxylic acid ester to deprotect one or more of the amino and carboxyl groups.Type: GrantFiled: March 6, 1985Date of Patent: June 3, 1986Assignee: Ethyl CorporationInventor: Beverly A. Bauer
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Patent number: 4593116Abstract: Urethanes are made by reacting an organic nitro compound with an organic compound containing at least one hydroxyl group in the presence of carbon monoxide, hydrogen and a catalyst system. The carbon monoxide and hydrogen are used in quantities such that the molar ratio of CO to H.sub.2 is from 0.3:1 to 3:1. The catalyst system is made up of at least one noble metal or compound of a noble metal from Group VIIIB of the Periodic System of Elements, at least one organic nitrogen base and a co-catalyst combination of iron or copper oxidic or hydroxidic compound and a chloride compound. The product urethanes are useful in the production of isocyanates and pesticides.Type: GrantFiled: June 13, 1984Date of Patent: June 3, 1986Assignee: Bayer AktiengesellschaftInventors: Gunter Stammann, Johann Grolig, Robert Becker, Helmut Waldmann
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Patent number: 4593117Abstract: Low molecular weight N- and O-substituted diurethanes and/or polyurethanes are prepared by reacting a diamine and/or polyamine containing a primary amino group with an N-aryl-0-alkyl urethane in the presence of at least one high boiling alcohol. This reaction may be carried out at a temperature of from 180.degree. to 350.degree. C. and a pressure of approximately 0.1 to 1,500 mbar. The arylamine corresponding to the N-ary-0-alkyl urethane which forms during this reaction is continuously removed from the reaction mixture.Type: GrantFiled: December 5, 1984Date of Patent: June 3, 1986Assignee: Bayer AktiengesellschaftInventors: Hartmut Knofel, Stefan Penninger, Gunther Hammen, Peter Heitkamper