Polyether Patents (Class 564/504)
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Patent number: 6005146Abstract: The present invention provides improved adhesion promoters for latex paints. The adhesion promoters are enamines of acetoacetate esters, or substituted acetoacetate esters. The invention also provides two new compounds which are useful as adhesion promoters: 2-butyl-2-ethyl-1,3-propanediol bis(3-amino-2-butenoate) and trimethyl propane tris(3-amino-2-butenoate), and which are stable to hydrolysis on prolonged storage.Type: GrantFiled: November 20, 1998Date of Patent: December 21, 1999Assignee: Eastman Chemical CompanyInventors: Douglas Grant Atkins, Jonathan Stewart Witzeman
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Patent number: 5886227Abstract: Disclosed is an improved process for the catalytic hydrogenation of cyanopropionaldehyde alkyl acetals (CPAA) to form the aminobutyraldehyde alkyl acetals. The basic process comprises hydrogenating the cyanopropionaldehyde alkyl acetals by contacting said cyanopropionaldehyde alkyl acetals with hydrogen in the presence of a nickel or cobalt catalyst under conditions for reducing the nitrile group to the primary amine. The improvement resides in effecting the hydrogenation of a cyanopropionitrile dialkyl acetal feedstock containing contaminating levels of cyanopropionaldehyde in the presence of a secondary alkanol or water.Type: GrantFiled: October 28, 1997Date of Patent: March 23, 1999Assignee: Air Products and Chemicals, Inc.Inventors: Gamini Ananda Vedage, Kathryn Sue Hayes
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Patent number: 5801202Abstract: Disclosed is an amine derivative represented by the following formula (1) or an acid addition salt thereof: ##STR1## wherein R.sup.1 represents a group ##STR2## a cyclopentyl group, cyclohexyl group, or a cycloheptyl group, R.sup.2 is a hydrogen atom or C1-C3 alkyl group which may be substituted by one or more hydroxyl groups, m is an integer falling in the range from 3 to 5 inclusive, and n is an integer falling in the range from 9 to 11 inclusive. Also, intermediates useful in the manufacture of the amine derivative (1), compositions for external application to the skin containing the amine derivative, and keratinization improvers containing the amine derivative as an active component are described. The compound (1) has excellent keratinization improving action, pigmentation preventing action, etc.Type: GrantFiled: May 30, 1997Date of Patent: September 1, 1998Assignee: Kao CoprorationInventors: Taketoshi Fujimori, Hiroshi Kusuoku, Akira Yamamuro, Yukihiro Yada, Kazuhiko Higuchi, Genji Imokawa, Naoki Kondo, Yoshinori Masukawa, Hajime Tokuda, Hisashi Tsujimura
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Patent number: 5786405Abstract: Clear, amine-initiated polyether polyols are made by epoxidizing an amine in the presence of an alkali metal hydroxide catalyst. After the desired degree of epoxidation has been achieved, a hydroxy-carboxylic acid is added to the epoxidized mixture in an amount sufficient to neutralize any remaining alkali metal hydroxide. The polyols produced in this manner are particularly useful for the production of polyurethane and apolyisocyanurate foams.Type: GrantFiled: November 1, 1996Date of Patent: July 28, 1998Assignee: Bayer CorporationInventors: Steven L. Schilling, Herman P. Doerge, Lotar H. Hanusa
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Patent number: 5693864Abstract: Disclosed herein is a process for preparing an amine terminated polyether comprising reacting a polyether containing a leaving group with a primary amine or ammonia at a temperature of about 70 to 250 degrees Centigrade.Type: GrantFiled: October 7, 1992Date of Patent: December 2, 1997Assignee: Bayer CorporationInventors: William E. Slack, Rick L. Adkins, Hans Georg Schmelzer
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Patent number: 5672599Abstract: Compounds of the formula ##STR1## wherein X is O or S--(O).sub.t ; n is one; m is zero or one; Y is CH.sub.2, O, or S--(O).sub.t provided that Y is O or S--(O).sub.t only when m is one; and A is ##STR2## are dual inhibitors of NEP and ACE. Compounds wherein A is ##STR3## are selective ACE inhibitors. Also disclosed are methods of preparation and intermediates.Type: GrantFiled: November 22, 1995Date of Patent: September 30, 1997Assignee: Bristol-Myers Squibb Co.Inventor: Jeffrey A. Robl
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Patent number: 5637772Abstract: The present invention provides fluorinated diamines and polymers formed therefrom, such as polyureas, polyurethane ureas, polyamides, polyimides, etc. The fluorinated diamines of the present invention are highly nucleophilic and are structured to provide polymeric materials having optimum surface properties. In the fluorinated diamines of the present invention, the end groups are primary amino groups which are substantially removed from the perfluoroalkyl groups. Moreover, the fluorine is present in the side chains which allows the fluorocarbon segments to migrate to the polymer/air interface, thereby providing polymer surfaces with high fluorine concentrations. As such, the polymers formed from the fluorinated diamines of the present invention have a variety of commercial applications as stain and oil resistant coatings, fouling release coatings, encapsulants for electrical devices, curing agents for epoxies, etc.Type: GrantFiled: September 22, 1995Date of Patent: June 10, 1997Assignee: Aerojet General CorporationInventors: Aslam A. Malik, Roland P. Carlson
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Patent number: 5629452Abstract: A process for the preparation of polyoxyalkylated compounds comprising at least one primary or secondary amine function is provided comprising reacting at least one amino-alcoholate (B) produced from an amino-alcohol (A) including at least one OH group and at least one primary or secondary amine function, by replacing a fraction or all the OH groups by OM groups, M being selected from sodium, potassium, rubidium and cesium, with an oxirane, a mixture of oxiranes or a sequence of oxiranes, in an aprotic and anhydrous solvent, in an anhydrous atmosphere and at a temperature of between about 0.degree. C. and 200.degree. C.Type: GrantFiled: December 5, 1994Date of Patent: May 13, 1997Assignee: ChrysoInventors: Martin Mosquet, Jean-Pierre Guicquero, Pierre Le Perchec, Yves Chevalier
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Patent number: 5616811Abstract: Etheramine alkoxylates are described which have the formula: ##STR1## where R.sup.1 is a straight or branched alkyl, aryl or alkylaryl group of 6 to 22 carbon atoms; R.sup.3 are independently hydrogen or C.sub.1 to C.sub.3 alkyl; m averages from about 1 to about 20; and x and y each independently average from about 0 to 30, where x+y averages from about 2 to about 60. These etheramine alkoxylates have surfactant properties. Further, they may be quaternized to make other compounds which will have useful surfactant properties.Type: GrantFiled: June 6, 1995Date of Patent: April 1, 1997Assignee: Huntsman Petrochemical CorporationInventors: Jeffrey J. Vipond, John M. Larkin, Terry L. Renken, Howard M. Stridde
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Patent number: 5600001Abstract: Azines of formula (I): ##STR1## in which R and R' either are identical and represent an alkyl radical containing 1 to 4 carbon atoms or an alkenyl radical containing 3 to 5 carbon atoms, or together form a radical of formula (II):--CHR.sub.1 --(CR.sub.2 R.sub.3).sub.n --CHR.sub.4 -- (II)in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4, identical or different, represent a hydrogen atom or an alkyl radical containing 1 to 4 carbon atoms and n represents 0 or 1, in their different stereoisomer forms, their preparation process and their use.Type: GrantFiled: February 22, 1996Date of Patent: February 4, 1997Assignee: Societe Francaise HoechstInventors: Alain Schouteeten, Yani Christidis
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Patent number: 5554793Abstract: A process of reforming an alkyleneamine feedstock or a mixture of such feedstocks to an alkyleneamine or a mixture of alkyleneamines which is different from the feedstock or feedstock mixture. The process is catalyzed by one of the following: Group VB metal oxides, Group VB metal phosphates, Group IIA metal silicates, and tungsten oxides. For example, ethylenediamine is contacted with a catalyst of niobic acid or magnesium silicate to yield predominantly diethylenetriamine and non-cyclic triethylenetetramines; whereas high molecular weight polyethylenepolyamines are cracked by the same catalysts to mixtures of lower molecular weight linear and cyclic materials.Type: GrantFiled: December 19, 1994Date of Patent: September 10, 1996Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
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Patent number: 5508272Abstract: Compounds of the formula ##STR1## wherein X is O or S--(O).sub.t ; n is one or two; m is zero or one; Y is CH.sub.2, O, or S--(O).sub.t provided that Y is O or S--(O).sub.t only when m is one; and A is ##STR2## are dual inhibitors of NEP and ACE. Compounds wherein A is ##STR3## are selective ACE inhibitors. Also disclosed are methods of preparation and intermediates.Type: GrantFiled: May 5, 1994Date of Patent: April 16, 1996Assignee: Bristol-Myers Squibb CompanyInventor: Jeffrey A. Robl
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Patent number: 5491261Abstract: Di-, tri- and poly-perfluoroalkyl-substituted alcohols and acids and derivatives thereof are described which are prepared from perfluoroalkyl iodides and di-, tri- or polyallyl alcohols or acids. These compounds contain two or more perfluoroalkyl-iodoalkyl or perfluoroalkyl-alkenyl groups and one or two alcohol or acid groups or derivatized alcohol or acid functions. They can be reacted with isocyanates, epoxy compounds, anhydrides, acids or acid derivatives to prepare a great variety of oil- and water-repellent compositions which are useful for oil- and water-repellent treatment of textiles, glass, paper, leather and other substrates.Type: GrantFiled: July 1, 1994Date of Patent: February 13, 1996Assignee: Ciba-Geigy CorporationInventors: Marlon Haniff, Robert Falk, Ted Deisenroth, Karl F. Mueller
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Patent number: 5488168Abstract: A tertiary amino alcohol, being useful as an emulsifier, is defined by the formula (1) or (2): ##STR1## where R is a C.sub.2 to C.sub.24 straight-chain or branched alkylene group, an alicyclic alkylene group, an aralkylene group or --CH.sub.2 CH.sub.2 O).sub.p (CH.sub.2 CH.sub.2).sub.q (where p is 0 or a positive integer and q is a positive integer), R' is a C.sub.1 to C.sub.24 straight-chain or branched alkyl group or an aralkyl group and n is a positive integer of 2 to 50.Type: GrantFiled: April 14, 1993Date of Patent: January 30, 1996Assignee: Kao CorporationInventors: Kohshiro Sotoya, Hiroshi Abe, Jun Aikawa, Hideki Taniguchi, Uichiro Nishimoto
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Patent number: 5475119Abstract: Ionic monomeric diallylammonium compounds having a targeted combination of diallylammonium cations with selected anions have particularly high and constant charge control properties and very good heat stabilities and dispersibilities.The compounds according to the invention are outstandingly suitable for use as colorless charge control agents in toners and developers for electrophotographic recording processes and for use as charge-improving agents in powders and paints for surface coating, in particular in triboelectrically or electrokinetically sprayed powder paints.Type: GrantFiled: December 17, 1992Date of Patent: December 12, 1995Assignee: Hoechst AktiengesellschaftInventors: Rudiger Baur, Hans-Tobias Macholdt
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Patent number: 5468841Abstract: The present invention provides an improved method of carrying out cationic polymerization of cyclic ether monomers substituted with high-energy, electron-withdrawing pendant groups (e.g., BAMO and NMMO). Such cyclic ether monomers are polymerized with an initiator precursor (i.e., an alcohol) and boron trifluoride tetrahydrofuranate (BF.sub.3 .cndot.THF). It has been discovered that when boron trifluoride tetrahydrofuranate is used as a catalyst in the cationic polymerization of cyclic ether monomers substituted with high-energy, electron-withdrawing pendant groups (e.g., BAMO and NMMO), polymers are produced that have improved functionality and low poly-dispersity. The polymers formed using the method of the present invention are useful for forming cross-linked elastomers which, in turn, are useful for forming elastomeric binders for high-energy compositions, such as propellants, explosives, gasifiers or the like.Type: GrantFiled: April 13, 1994Date of Patent: November 21, 1995Assignee: Aerojet General CorporationInventors: Aslam A. Malik, Thomas G. Archibald, Roland P. Carlson, Gerald E. Manser
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Patent number: 5446027Abstract: Amino derivatives represented by the following general formula (1): ##STR1## and external skin care preparations containing such an amide derivative, are useful for preventing or curing skin roughness. Intermediates useful for the preparation of such amides are also disclosed.Type: GrantFiled: November 2, 1993Date of Patent: August 29, 1995Assignee: Kao CorporationInventors: Taketoshi Fujimori, Yukihiro Ohashi, Akira Kawamata
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Patent number: 5444099Abstract: A tertiary aminoalcohol having a tert-amino group(s) in the main chain and hydroxyl groups at the terminals. The use of this compound for purposes different from that of ordinary amines and amine derivatives is expected.A process for producing the tertiary aminoalcohol wherein a catalyst comprising copper, a transition metal element of the fourth period and a platinum group element of the group VIII, and further optionally containing an alkali metal or an alkaline earth metal is used.A process for producing polyurethane using the above-mentioned tertiary aminoalcohol which can solve the problems occurring in the production of a polyurethane using a tertiary amine which has a strong irritating odor and is highly irritant to the skin as a catalyst, for example, deteriorations of working atmosphere and sales appeal of the polyurethane.Type: GrantFiled: September 20, 1993Date of Patent: August 22, 1995Assignee: Kao CorporationInventors: Hiroshi Abe, Tetsuaki Fukushima, Kohshiro Sotoya, Shoichiro Harada, Hiroshi Kitagawa, Masayoshi Morii, Yasutoshi Isayama
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Patent number: 5410087Abstract: A process of reforming an alkyleneamine feedstock or a mixture of such feedstocks to an alkyleneamine or a mixture of alkyleneamines which is different from the feedstock or feedstock mixture. The process is catalyzed by one of the following: Group VB metal oxides, Group VB metal phosphates, Group IIA metal silicates, and tungsten oxides. For example, ethylenediamine is contacted with a catalyst of niobic acid or magnesium silicate to yield predominantly diethylenetriamine and non-cyclic triethylenetetramines; whereas high molecular weight polyethylenepolyamines are cracked by the same catalysts to mixtures of lower molecular weight linear and cyclic materials.Type: GrantFiled: November 17, 1993Date of Patent: April 25, 1995Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, David C. Molzahn, Robert G. Bowman
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Patent number: 5391476Abstract: Water-soluble, non-ionic surface active compounds are provided having the formula ##STR1## wherein R.sup.1 and R.sup.2 are each independently hydrogen or an alkyl group having from 1 to 4 carbon atoms;X is a hydrophobic substituted or unsubstituted arylene group or a hydrophobic substituted or unsubstituted alkylene group;Y.sup.1 and Y.sup.2 are each independently a chemical bond, --CO-- or --(CH.sub.2).sub.m NR.sup.3 CO--;m is an integer from 1 to 6;R.sup.3 is as defined for R.sup.1 and R.sup.2 ; and,Z.sup.1 and Z.sup.2 are each independently a hydrophilic polyhydroxyalkyl group. The compounds are particularly useful as coating aids for the coating of hydrophilic colloid layers in the preparation of photographic materials.Type: GrantFiled: September 17, 1993Date of Patent: February 21, 1995Assignee: Eastman Kodak CompanyInventors: Alan R. Pitt, Ian M. Newington
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Patent number: 5362913Abstract: Highly saturated, highly aminated alkoxylated polymers may be reliably made by an improved process involving the steps of (1) polymerizing one or more unsaturated hydrocarbons to form a liquid polymer, where at least one of the unsaturated hydrocarbons is butadiene; (2) providing the liquid polymer with terminal hydroxyl groups; (3) alkoxylating the hydroxylated liquid polymer with one or more alkylene oxides having at least three carbon atoms to provide secondary terminal hydroxyl groups; (4) simultaneously aminating and hydrogenating the alkoxylated liquid polymer to produce an essentially saturated, aminated, alkoxylated liquid polymer in the presence of hydrogen and ammonia and a catalyst. The catalyst preferably contains nickel as the single greatest component, with smaller amounts of copper, chromium and molybdenum. Excesses of hydrogen and ammonia are used in the final step.Type: GrantFiled: November 16, 1992Date of Patent: November 8, 1994Assignee: Huntsman CorporationInventors: John F. Knifton, Michael Cuscurida
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Patent number: 5334761Abstract: The present invention discloses cationic lipids useful for making lipid aggregates for delivery of macromolecules and other compounds into cells. They are especially useful for the DNA-dependent transformation of cells. Also disclosed are lipids useful both for the delivery of macromolecules and also useful as intermediates for making other such lipids.Type: GrantFiled: August 28, 1992Date of Patent: August 2, 1994Assignee: Life Technologies, Inc.Inventors: Gulilat Gebeyehu, Joel A. Jessee, Valentina C. Ciccarone, Pamela Hawley-Nelson, Anna Chytil
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Patent number: 5326911Abstract: Ortho-amides of the formula ##STR1## can be prepared by reacting salts of the formula ##STR2## with alcoholates of the formulaM.sup.1 OR.sup.1 (III)where the radicals R.sup.1 to R.sup.4, M.sup.1 and X.sup..crclbar. have the meaning given in the description. The alcoholates are employed in highly active form with an effective content of 98-100% M.sup.1 OR.sup.1.Type: GrantFiled: July 20, 1992Date of Patent: July 5, 1994Assignee: Bayer AktiengesellschaftInventors: Heinz-Ulrich Blank, Helmut Kraus, Gerhard Marzolph, Nikolaus Muller
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Patent number: 5315041Abstract: A tertiary aminoalcohol having a tert-amino group(s) in the main chain and hydroxyl groups at the terminals. The use of this compound for purposes different from that of ordinary amines and amine derivatives is expected.A process for producing the tertiary aminoalcohol wherein a catalyst comprising copper, a transition metal element of the fourth period and a platinum group element of the group VIII, and further optionally containing an alkali metal or an alkaline earth metal is used.A process for producing polyurethane using the above-mentioned tertiary aminoalcohol which can solve the problems occurring in the production of a polyurethane using a tertiary amine which has a strong irritating odor and is highly irritant to the skin as a catalyst, for example, deteriorations of working atmosphere and sales appeal of the polyurethane.Type: GrantFiled: March 4, 1992Date of Patent: May 24, 1994Assignee: Kao CorporationInventors: Hiroshi Abe, Tetsuaki Fukushima, Kohshiro Sotoya, Shoichiro Harada, Hiroshi Kitagawa, Masayoshi Morii, Yasutoshi Isayama
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Patent number: 5274054Abstract: Adducts which are obtainable by reacting cycloaliphatic or heterocycloaliphatic polyamines containing at least two primary groups with polyfunctional epoxides containing more than two epoxy groups per molecule in such amounts as to supply 10-100 equivalents of active hydrogen atoms bound to amino nitrogen per one epoxide equivalent, are suitable hardeners for epoxy adhesives, especially adhesives for metals and thermosetting plastics.Type: GrantFiled: April 1, 1992Date of Patent: December 28, 1993Assignee: Ciba-Geigy CorporationInventors: Roland Moser, Hans Lehmann, Daniel Bar
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Patent number: 5270161Abstract: Water-soluble, non-ionic surface active compounds are provided having the formula ##STR1## wherein R.sup.1 and R.sup.2 are each independently hydrogen or an alkyl group having from 1 to 4 carbon atoms;X is a hydrophobic substituted or unsubstituted arylene group or a hydrophobic substituted or unsubstituted alkylene group;Y.sup.1 and Y.sup.2 are each independently a chemical bond, --CO-- or --(CH.sub.2).sub.m NR.sup.3 CO--;m is an integer from 1 to 6;R.sup.3 is as defined for R.sup.1 and R.sup.2 ; and,Z.sup.1 and Z.sup.2 are each independently a hydrophilic polyhydroxyalkyl group. The compounds are particularly useful as coating aids for the coating of hydrophilic colloid layers in the preparation of photographic materials.Type: GrantFiled: July 29, 1991Date of Patent: December 14, 1993Assignee: Eastman Kodak CompanyInventors: Alan R. Pitt, Ian M. Newington
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Patent number: 5264006Abstract: Distillate fuel compositions containing an alkyl ether mono amine having the formulaRO[C.sub.4 H.sub.8 O].sub.(9-18) CH.sub.2 CH.sub.2 CH.sub.2 NH.sub.2whereR is a highly branched alkyl group derived from a Guerbet alcohol containing between 12 and 40 carbon atomsare effective in reducing the formation of intake valve deposits in internal combustion engines.Type: GrantFiled: December 20, 1991Date of Patent: November 23, 1993Assignee: Exxon Research and Engineering Co.Inventors: Alan M. Schilowitz, James A. Krogh, Anita R. Mokadam, J. Michael Clumpner, Paul J. Berlowitz
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Patent number: 5252706Abstract: A peptide derivative amphiphatic compound or N-terminal salt thereof represented by formula (I): ##STR1## wherein R.sup.1 and R.sup.2 each represents a straight-chain or branched alkyl or acyl group having 8 to 24 carbon atoms optionally having a substituent or an unsaturated group; X represents --O--or --NH--; R.sup.3n and R.sup.3(n+1) each represents an .alpha.--amino acid side chain; n is an integer of from 0 to 5; the compound may be a racemic compound or an optically active compound when the compound has an asymmetric carbon atom; and the N-terminal salt of the compound optionally forms with an acid component; an intermediate thereof, a liposome comprising said peptide derivative amphiphatic compound and a film consisting of a monolayer or multilayers comprising the peptide derivative amphiphatic compound are disclosed.Type: GrantFiled: April 8, 1991Date of Patent: October 12, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Hiroshi Kitaguchi, Ryoichi Nemori
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Patent number: 5213584Abstract: A formal compound is represented by formula (1): wherein R.sup.1 is a hydrogen atom or a hydrocarbon group having 1 to 26 carbon atoms, A.sup.1 is an alkylene group having 2 to 18 carbon atoms, a is 1 to 100, A.sup.2 is an alkylene group having 2 to 4 carbon atoms, b is 1 to 5, R.sup.2 is an alkylene group having 2 to 8 carbon atoms, c is 0 to 5, R.sup.3 is an alkylene group having 2 to 8 carbon atoms, d is 0 to 5, A.sup.3 is an alkylene group having 2 to 4 carbon atoms, e is 0 to 5, and R.sup.4 is a hydrogen atom or CH.sub.2 (OA.sup.4).sub.f OR.sup.5, in which A.sup.4 is an alkylene group having 2 to 18 carbon atoms, f is 1 to 100, and R.sup.5 is hydrogen atom or a hydrocarbon group having 1 to 26 carbon atoms, and wherein each of (A.sup.1 O).sub.a, (OA.sup.2).sub.b, (NR.sup.2).sub.c, (R.sup.3 NH).sub.d, (A.sup.3 O).sub.e, and (OA.sup.4).sub.Type: GrantFiled: July 10, 1990Date of Patent: May 25, 1993Assignee: Nippon Oil and Fats Co., Ltd.Inventors: Hiroumi Izaiku, Shin-ichi Akimoto, Takaharu Ishizaki, Yoshifumi Kubo, Tohru Yasukohchi
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Patent number: 5196595Abstract: New perfluoroaminoether polymers and a process for preparing them which comprises copolymerizing fluorinated olefins with oxaziridines in the presence of ultra-violet radiations or of chemical initiators.Type: GrantFiled: April 28, 1992Date of Patent: March 23, 1993Assignee: Ausimont S.R.L.Inventors: Walter Navarrini, Darryl D. Desmarteau
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Patent number: 5103048Abstract: The new compounds have the formula below ##STR1## in which R.sub.f is a perfluoroalkyl radical having 4 to 20 carbon atoms,x is 1 to 4,y is 1 to 10,X is Br, Cl or I, andR.sup.1 and R.sup.2 are hydrogen or a C.sub.1 to C.sub.4 -alkyl radical or a water-solubilizing aliphatic radical, with the proviso that at least one of the two substituents R.sup.1 and R.sup.2 is a water-solubilizing aliphatic radical.The surface-active compounds described are prepared by reacting a suitable epoxide with a suitable amine. They are used in particular for the preparation of foaming agents.Type: GrantFiled: December 26, 1990Date of Patent: April 7, 1992Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Knaup, Frank Wehowsky, Norbert Schmitt
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Patent number: 5094667Abstract: Distillate fuel compositions containing an alkyl ether mono amine derived from a Guerbet alcohol are effective in reducing the formation of intake valve deposits in internal combustion engines. A preferred alkyl ether mono amine is derived from a highly branched butoxylated Guerbet alcohol containing 20 carbon atoms and having the formulaRO[C.sub.4 H.sub.8 O].sub.(4-8) CH.sub.2 CH.sub.2 CH.sub.2 NH.sub.2where R is a highly branched alkyl group having 20 carbon atoms that is derived from a Guerbet condensation reaction.Type: GrantFiled: March 20, 1990Date of Patent: March 10, 1992Assignee: Exxon Research and Engineering CompanyInventors: Alan M. Schilowitz, James A. Krogh, Anita R. Mokadam, J. Michael Clumpner, Paul J. Berlowitz
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Patent number: 5091583Abstract: The invention pertains to tertiary amines used as catalysts for the preparation of polyurethane foams prepared via the catalytic reaction of a polyisocyanate with a polyol in the presence of blowing agents, etc. The tertiary amine catalysts are prepared by reacting an olefinic nitrile with aliphatic polyol having at least secondary hydroxyl functionality in a ratio less than stoichiometric for providing cyanoalkylated polyol having residual hydroxyl functionality. The resulting cyanoalkylated polyol then is reacted with a secondary amine under conditions for effective reductive alkylation.The tertiary amine catalysts, because of residual secondary hydroxyl functionality, provide for uniform dispersion within a polyurethane, formulation; they provude for additional or extended pot life in polyurethane formulations at temperature below reaction condition, and they are bound by reaction on cure.Type: GrantFiled: May 9, 1991Date of Patent: February 25, 1992Assignee: Air Products and Chemicals, Inc.Inventors: Jeremiah P. Casey, Richard V. C. Carr, George J. Wasilczyk, Robert G. Petrella
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Patent number: 5057623Abstract: An organic fluorine compound represented by the general formulaR.sub.f -(X).sub.h -R-Mwherein R.sub.f is a group selected from the following (a) and (b); ##STR1## X denotes a linking group selected from --O--, --S--, and --COO--, h denotes 0 or 1, R is a hydrocarbon chain comprising a phenylene group having an alkylene group with a total carbon number of 10 or more, or the derivative thereof, or an aliphatic alkylene group of a carbon number of 10 or more, and M is a group selected from --OH, --COOH, --SH, and --CONH.sub.2.The organic fluorine compound of the present invention greatly improves the dispersibility of magnetic powders in magnetic coating materials, has also an excellent rust prevention effect on metallic magnetic powders, and exhibits a marked dispersing effect even on fluorocarbon resin fine powders, which can be difficultly dispersed with conventional dispersing agents.Type: GrantFiled: October 13, 1989Date of Patent: October 15, 1991Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Yoshiaki Kai, Takashi Suzuki
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Patent number: 4902818Abstract: The manufacture of optically active bifunctional compounds of the general formula ##STR1## wherein R represents protected hydroxymethyl, protected formyl or alkoxycarbonyl and R.sup.1 represents a group of the formula ##STR2## in which R.sup.2 and R.sup.3 represents lower alkyl or cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom represent a heterocyclic ring, by isomerizing compounds of the general formula ##STR3## wherein R, R.sup.2 and R.sup.3 have the above significance and R.sup.3 can additionally signify hydrogen, is described.The compounds of formula I are potential intermediates in the manufacture of, interalia, natural vitamin E and natural vitamin K.sub.1.Type: GrantFiled: October 5, 1988Date of Patent: February 20, 1990Assignee: Hoffmann-La Roche Inc.Inventors: Hans-Jurgen Hansen, Rudolf Schmid, Max Schmid
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Patent number: 4886915Abstract: Water soluble biocidal water treatment perhalides of the formula: ##STR1## where R.sub.1 and R.sub.2 are independently hydrogen, hydroxyethyl, alkyl, cyclic alkyl, (alpha, omega)-alkyl, alkyl ether, polyether, heterocyclic ring-substituted alkyl, and halogenated alkyl; X is chlorine, bromine or iodine; and only one of R.sub.1 and R.sub.2 may be hydrogen.Type: GrantFiled: June 24, 1988Date of Patent: December 12, 1989Assignee: Great Lakes Chemical CorporationInventor: Nicolai A. Favstritsky
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Patent number: 4885392Abstract: Polyamines based on derivatives of 1,3-bissubstituted 2-propanol containing a multiplicity of amino groups, the latter containing at least one primary amino group and additionally further N-basic groupings, prepared by reacting 1,2,3-trisubstituted propane compounds with bis(primary amines or with monoamines and bis(primary amines).The polyamines according to the invention are clear to yellowish or yellow products which, at room temperature, form viscous to highly viscous liquids or may be paste-like or wax-like. They may be used, inter alia, advantageously as starting products for the preparation of thermosetting, in particular water-dispersible and cataphoretically depositable binders based on aminourethanes for coating solid substrates, in particular metals.Type: GrantFiled: December 22, 1987Date of Patent: December 5, 1989Assignee: Hoechst AGInventors: Rudiger Lenz, Gerd Walz, Michael Honel, Peter Ziegler
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Patent number: 4857663Abstract: N-(3-Dialkylamino-2-propenylidene)-N-alkylalkanaminium salts substituted in the 2-position with an ether or thioether and having the formula ##STR1## are active as hypoglycemic agents.Type: GrantFiled: November 16, 1988Date of Patent: August 15, 1989Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Eugene R. Wagner, Donald P. Matthews, Charlotte L. Barney
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Process for producing higher molecular weight amino compounds having reduced monomeric amine content
Patent number: 4855504Abstract: High molecular weight amines having reduced low molecular weight amine contents are obtained by reacting a mixture of (1) a high molecular weight amine and (2) a low molecular weight amine with (3) an isocyanate in quantities such that from 0.5 to 10 equivalents of isocyanate are present for each equivalent of low molecular weight amine. The product of high molecular weight amines is particularly useful in the production of isocyanate addition products such as polyurethane plastics and foams.Type: GrantFiled: September 23, 1985Date of Patent: August 8, 1989Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Ernst Grigat, Gerhard Grogler, Heinrich Hess, Richard Kopp -
Patent number: 4788339Abstract: Perfluoroaminoethers are provided. The perfluoroaminoethers have two or more tertiary amino nitrogen atoms each of which is connected to the other(s) adjacent thereto by (1) a catenary, ether oxygen-containing, perfluoroalkylene linking group the catenary carbon atoms of which are in the form of segments of vicinal carbon atoms that are 2 to 4 in number, said segments having up to 5 carbon atoms, a catenary ether oxygen-containing perfluorocyclohexylene linking group, or (3) a catenary ether oxygen-containing linking group having perfluoroalkylene and perfluorocyclohexylene moieties, the sum of the catenary ether oxygen atoms being 1 to 6.Type: GrantFiled: August 14, 1986Date of Patent: November 29, 1988Assignee: Minnesota Mining and Manufacturing CompanyInventors: George G. I. Moore, John C. Hansen
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Patent number: 4705834Abstract: Crosslinked oxyalkylated polyalkylenepolyamines which can be obtained by reacting polyalkylenepolyamines, which are completely oxyalkylated at the nitrogen atoms, in each case by from 10 to 300 groups, and possess from 50 to 2,000 repeating alkyleneimine units in the molecule, with from 0.5 to 10% by weight, based on the oxyalkylated polyalkylenepolyamines, of a crosslinking compound which possesses two or more functional groups which are capable of reacting with the terminal alcohol groups of the oxyalkylated polyalkylenepolyamines, and a process for breaking water-in-oil emulsions.Type: GrantFiled: December 24, 1984Date of Patent: November 10, 1987Assignee: BASF AktiengesellschaftInventors: Richard Baur, Knut Oppenlaender, Klaus Barthold
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Patent number: 4650865Abstract: The invention relates to a process for preparing tertiary ether amines corresponding to the following general formula: ##STR1## by reacting in the presence of a strong base a tertiary amine corresponding to the following formula: ##STR2## with a sulfuric acid semi-ester salt corresponding to the following formula:R.sup.1 --(OC.sub.n H.sub.2n).sub.x --OSO.sub.3 M. (III)Preferably, each mole of the tertiary amine corresponding to formula (II) is reacted under substantially anhydrous conditions at a temperature of 140.degree. to 230.degree. C. with from about 0.2 to 3.0 moles of the sulfuric acid semi-ester salt of formula (III) in the presence of from about 1 to 1.5 moles of a strong base preferably an alkali metal hydroxide or an alkali metal alcoholate.Type: GrantFiled: February 7, 1986Date of Patent: March 17, 1987Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Fritz Lange, Alfred Meffert
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Patent number: 4650907Abstract: Novel nonaromatic fluoroallylamines are potent MAO inhibitors and at low dose selectively inhibit MAO-B. They are useful in the treatment of depression and coadministered with L-dopa, in the treatment of Parkinsonism.Type: GrantFiled: December 5, 1985Date of Patent: March 17, 1987Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Philippe Bey, Michael G. Palfreyman, Ian A. McDonald
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Patent number: 4636568Abstract: There are disclosed certain aminoether compounds which are useful as intermediates in the preparation of photographic image dye providing materials. The aminoethers are represented either by the formula ##STR1## wherein R is hydrogen or an alcohol protecting group and R.sub.1 is hydrogen, alkyl or aralkyl such as benzyl or phenethyl; or the formula ##STR2## wherein R.sub.2 and R.sub.3 are alkyl having from 1 to 6 carbon atoms or R.sub.2 and R.sub.3 together represent the carbon atoms necessary to form, together with the oxygen atoms to which they are bonded and >CH, a five or six member saturated heterocyclic moiety which may include substituted rings and fused rings.Type: GrantFiled: August 27, 1984Date of Patent: January 13, 1987Assignee: Polaroid CorporationInventors: Myron S. Simon, David P. Waller
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Patent number: 4629815Abstract: Polychlorobenzenes are isomerized/rearranged, by reacting (i) at least one tetrachlorobenzene, or at least one tetrachlorobenzene in admixture with at least one trichlorobenzene, pentachlorobenzene and/or hexachlorobenzene, or (ii) pentachlorobenzene, or pentachlorobenzene in admixture with at least one trichlorobenzene and/or hexachlorobenzene, or (iii) hexachlorobenzene, or hexachlorobenzene in admixture with at least one trichlorobenzene and/or dichlorobenzene, with at least one alkali metal amide, or at least one alkali metal alcoholate, or admixture thereof, said reaction being conducted in the presence of an agent which complexes the cation of the amide, alcoholate, or admixture thereof.Type: GrantFiled: June 23, 1981Date of Patent: December 16, 1986Assignee: Rhone-Poulenc IndustriesInventor: Gerard Soula
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Patent number: 4570018Abstract: A novel chemical, fluorochlorocyclopropane (I) of the following formula: ##STR1## is prepared by the addition of fluorochlorocarbene to the corresponding olefin (II) of the following formula:CH.sub.2 .dbd.CR.sup.1 -R.sup.2The compound is a useful intermediate for synthesizing some chemicals, e.g., some cephalosporins.(wherein R.sup.1 is hydrogen, halogen, 1 to 8C alkylamino, alkoxy, or alkylthio andR.sup.2 is halogen, 1 to 8C alkylamino, alkoxy, or alkylthio).Type: GrantFiled: May 16, 1984Date of Patent: February 11, 1986Assignee: Shionogi & Co., Ltd.Inventors: Tsutomu Aoki, Hiromi Takahashi, Toshiro Konoike, Teruji Tsuji, Wataru Nagata
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Patent number: 4564382Abstract: Compounds of the formula I ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 independently of one another denote hydrogen, F, Cl, Br or (C.sub.1 -C.sub.4)-alkyl, and R.sup.1 also denotes CF.sub.3, CN, NO.sub.2 or alkoxycarbonyl, A denotes a direct bond, --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--, X denotes O, S or N--R.sup.8, R.sup.4 denotes H or alkyl, R.sup.5 and R.sup.6 denote alkyl, R.sup.7 denotes alkyl, (substituted) benzyl and/or (substituted) phenethyl and R.sup.8 denotes H or alkyl or, together with NR.sup.7, denotes a heterocyclic ring, are active herbicides and antidotes.Type: GrantFiled: November 8, 1984Date of Patent: January 14, 1986Assignee: Hoechst AktiengesellschaftInventors: Rainer Liebl, Reinhard Handte, Hilmar Mildenberger, Klaus Bauer, Hermann Bieringer
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Patent number: 4542202Abstract: An addition product obtained by reacting (a) a polyfunctional epoxy compound and (b) a compound having at least one functional group of OH group, SH group, COOH group and CONHNH.sub.2 group together with a tertiary amino group in the molecule, and an addition product obtained (a), (b) and (c) an organic compound having two or more active hydrogen atoms in the molecule (excluding a compound having an epoxy group or tertiary amino group) are good curing agents for epxoy resin. The curing agents are useful in formulating novel storable one-package, heat-curable epoxy resin-based compositions.Type: GrantFiled: September 16, 1983Date of Patent: September 17, 1985Assignee: Ajinomoto Co., Inc.Inventors: Koji Takeuchi, Masahiro Abe, Nobuo Ito, Kiyomiki Hirai
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Patent number: 4460789Abstract: The invention relates to a new process for preparing alkoxylates containing primary amine functions comprising reacting a monoalkanolamine or a polyamine compound with a carbonyl compound to form an amide- or carbamate-type condensation product, reacting said condensation product with an alkylene oxide compound to form an alkylene oxide adduct of said condensation product, and salifying the so-formed adduct under mild, acidic conditions.Type: GrantFiled: June 10, 1982Date of Patent: July 17, 1984Assignee: Sandoz, Inc.Inventor: Robert V. Casciani
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Patent number: 4389526Abstract: Novel methods are provided for synthesizing 2-amino-2-tetritol, by positive halogen addition to protected 1,4-dioxybutene-2 in the presence of a nitrile, resulting in addition of a halo functionality and the nitrile functionality across the double bond. Upon hydrolysis, the desired erythro-product can be obtained in stereochemically good yield.Type: GrantFiled: August 3, 1981Date of Patent: June 21, 1983Assignee: The Regents of the University of CaliforniaInventors: Milos Sovak, Ramachandran Ranganathan