Reactant Contains A Single -n=c=x Group Patents (Class 528/69)
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Patent number: 4482691Abstract: Air-drying fatty acid-modified acrylic resins and oxidizable resinous vehicles containing same, and a novel drier system comprising a coordination complex of titanium and cobalt are herein disclosed.Type: GrantFiled: September 22, 1983Date of Patent: November 13, 1984Assignee: PPG Industries, Inc.Inventors: John B. Saunders, Jr., Karl F. Schimmel, Rostyslaw Dowbenko
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Patent number: 4451627Abstract: An addition polymerizable adhesive is prepared by using the reaction product of (1) an isocyanate compound (such as 2-isocyanatoethyl methacrylate) and (2) an active hydrogen compound (such as a poly(ethylene glycol)) wherein the reaction between (1) and (2) is catalyzed with a tin (II) organoester (such as stannous octoate). The adhesives of the invention have surprisingly long shelf lives compared to similar adhesives made with other catalysts.Type: GrantFiled: September 7, 1982Date of Patent: May 29, 1984Assignee: The Dow Chemical CompanyInventors: Kurt C. Frisch, Jr., Michele R. Lock, Gregory J. Stuk
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Patent number: 4448938Abstract: Isocyanate compositions derived from diphenylmethane diisocyanate (MDI) which are a mixture of A) the reaction product of MDI with a polyether polyol or amine of molecular weight from 600 to 10,000 and B) a uretonimine modified MDI, the weight ratio of A to B being from 19:1 to 1:1. Also polyurethanes, especially elastomers prepared therefrom.Type: GrantFiled: December 6, 1979Date of Patent: May 15, 1984Assignee: Imperial Chemical Industries PLCInventors: Alphonse E. Bruyninckx, Martin F. Brooks, David Thorpe
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Patent number: 4426485Abstract: A water-soluble, thermoplastic, organic polymer is disclosed having segments of bunched monovalent hydrophobic groups. These polymers provide superior thickening and leveling in aqueous systems, through micelle-like associations, and aid suspension of particulate materials in non-aqueous systems.Type: GrantFiled: June 14, 1982Date of Patent: January 17, 1984Assignee: Union Carbide CorporationInventors: Kenneth L. Hoy, Richard C. Hoy
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Patent number: 4408008Abstract: The present invention relates to a process for the preparation of stable, colloidal, aqueous dispersions of cross-linked urea-urethanes which comprises reacting(a) an aqueously dispersed, substantially linear, isocyanate-terminated prepolymer having a molecular weight of up to about 25,000 and containing(i) about 0 to 120 milliequivalents of ionic groups per 100 grams of prepolymer, and(ii) about 0.35 to 10% by weight, based on the weight of the prepolymer, of lateral and/or terminal, hydrophilic ethylene oxide units wherein components (i) and (ii) are present in an amount sufficient to provide a stable dispersion of the prepolymer in the aqueous medium, with(b) polyfunctional amine chain extenders having an average functionality between about 2.2 and 6.0.The present invention additionally relates to the aqueous dispersions produced by the above process and to the films, coatings or adhesives produced from these dispersions.Type: GrantFiled: July 24, 1981Date of Patent: October 4, 1983Assignee: Mobay Chemical CorporationInventor: Peter Markusch
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Patent number: 4383070Abstract: The present invention is directed to an organic polyurethane composition having a solids content of about 10 to 100 weight percent which comprises(1) isocyanate-terminated prepolymers which are prepared by reacting reaction products of the phosgenation of aniline-formaldehyde condensates containing specific ratios of isomers and homologues with polyether polyols containing at least two hydroxyl groups and at least one tertiary nitrogen atom and, optionally, an additional polyol which does not contain a tertiary nitrogen atom and optionally,(2) a monoisocyanate comprising a member selected from para-toluenesulfonyl isocyanate and the reaction product of 2,4- or 2,6-toluene diisocyanate or mixtures thereof with specific monoalcohols.The present invention is also directed to the coatings produced from the polyurethane compositions, optionally containing pigments.Type: GrantFiled: May 27, 1982Date of Patent: May 10, 1983Assignee: Mobay Chemical CorporationInventors: Peter H. Markusch, Terry A. Potter, Kenneth P. Yonek, James W. Rosthauser
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Patent number: 4383091Abstract: Curable polymeric products are the reaction product of a polymer containing secondary hydroxyl groups and an aliphatic unsaturated isocyanate.Type: GrantFiled: July 1, 1982Date of Patent: May 10, 1983Assignee: The Dow Chemical CompanyInventor: Bruce L. Burton
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Patent number: 4374969Abstract: The reaction product of an ethylenically unsaturated, monofunctional isocyanate, such as isocyanatoethyl methacrylate and a polyamine, is useful as an anaerobic adhesive.Type: GrantFiled: April 2, 1982Date of Patent: February 22, 1983Assignee: The Dow Chemical CompanyInventor: Kurt C. Frisch, Jr.
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Patent number: 4373083Abstract: Rheology modifiers useful in water and organic solvent-based compositions are derived from the reaction of polyalkylene oxide, polyfunctional material, diisocyanate, water and end-capping compounds in an organic solvent. The organic solvent is compatible with latex coating compositions.Type: GrantFiled: December 29, 1980Date of Patent: February 8, 1983Assignee: PPG Industries, Inc.Inventors: Jerome A. Seiner, Karl F. Schimmel
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Patent number: 4366274Abstract: Auto-crosslinkable, cathodically depositable aqueous coating compositions which are the reaction product of 2 moles of a diepoxide, 1 mole of a secondary-secondary or primary-tertiary diamine, 0-1 moles of a saturated and/or unsaturated monocarboxylic acid, and 2-1 moles of a secondary amine with optional subsequent partial or total reaction of the hydroxy groups of the reaction product with an alpha,beta-unsaturated monoisocyanate. The binders are rendered water-soluble by neutralization with inorganic and/or organic acids. The binders are capable of being neutralized with low levels of neutralizing acids to provide a component of a coating composition which will cure at low temperatures to give films having excellent surface qualities.Type: GrantFiled: December 15, 1980Date of Patent: December 28, 1982Assignee: Vianova Kunstharz, A.G.Inventors: Georg Pampouchidis, Helmut Honig
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Patent number: 4356276Abstract: Binder combinations for the formulation of cathodic paints comprising blends of epoxy resins as follows: (A) 40 to 80% by weight of reaction products of epoxy acrylates with basic monoisocyanates; (B) 5 to 30% by weight of reaction products of epoxy amine adducts with unsaturated monoisocyanates, and (C) an epoxy resin modified with a semi-ester of a dicarboxylic acid anhydride and an N-hydroxyalkyloxazolidin and an amine, rendered water soluble through neutralization of the basic groups. The binder combinations as defined have enhanced throwing power and improved stability of the paint tank.Type: GrantFiled: September 15, 1981Date of Patent: October 26, 1982Assignee: Vianova Kunstharz, A.G.Inventors: Helmut Honig, Wolfgang Leitner, Georg Pampouchidis
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Patent number: 4338242Abstract: Curable polymeric products are the reaction product of a polymer containing secondary hydroxyl groups and an aliphatic unsaturated isocyanate.Type: GrantFiled: September 19, 1980Date of Patent: July 6, 1982Assignee: The Dow Chemical CompanyInventor: Bruce L. Burton
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Patent number: 4327008Abstract: Rheology modifiers useful in water-based and organic solvent-based compositions are derived from the reaction of polyalkylene oxide, polyfunctional material, diisocyanate, water and a monofunctional active hydrogen-containing compound or monoisocyanate. The modifiers are characterized by having a branched structure, urea linkages and terminal hydrophobic groups.Type: GrantFiled: December 29, 1980Date of Patent: April 27, 1982Assignee: PPG Industries, Inc.Inventors: Karl F. Schimmel, Jerome A. Seiner, Roger M. Christenson, Rostyslaw Dowbenko
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Patent number: 4320221Abstract: The reaction product of an ethylenically unsaturated, monofunctional isocyanate, such as isocyanatoethyl methacrylate and a difunctional active hydrogen containing compound such as a polyol is useful as an anaerobic adhesive.Type: GrantFiled: December 12, 1980Date of Patent: March 16, 1982Assignee: The Dow Chemical CompanyInventor: Dwight K. Hoffman
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Patent number: 4320220Abstract: Self-crosslinking coating compositions which are cathodically deposited on electrodeposition of paints containing the coating compositions and a process for producing aqueous solutions of the self-crosslinking coating compositions by acid neutralization are described. The coating compositions are the reaction products of a resin carrying amine groups and hydroxyl or carboxyl groups, and the reaction product carrying one free isocyanate group of a polyisocyanate and at least one ethylenically unsaturated monomer having at least one isocyanate reactive hydrogen atom and the group ##STR1## The cathodically depositable electrodeposition paints cure rapidly at relatively low temperatures to provide films which are highly resistant to corrosive influences.Type: GrantFiled: July 20, 1977Date of Patent: March 16, 1982Assignee: Vianova Kunstharz, A.G.Inventor: Georgios Pampouchidis
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Patent number: 4314924Abstract: Thixotropic compositions comprising a solution of a urea urethane having the formula as hereinafter set out dissolved in a polar aprotic solvent containing 0.1-2.0 mol LiCl per urea group:R--O--CO--NH--R'--NH--CO--NH--R"--NH--CO--NH--R'--NH--CO--ORwherein R represents C.sub.n H.sub.2n+1 -- or C.sub.m H.sub.2m+1 (C.sub.p H.sub.2p O).sub.r --; n represents an integer having a value of from 4 to 22; m represents an integer having a value of from 1 to 18; p represents an integer having a value of from 2 to 4; and r represents an integer having a value of from 1 to 10. ##STR1## The solids content in the aprotic solvent amounts to 10-75 wt. % and preferably to from 40-60 wt. %.Type: GrantFiled: May 25, 1979Date of Patent: February 9, 1982Assignee: Byk-Mallinckrodt Chemische Produkte GmbHInventors: Karlheinz Haubennestel, Rainer Mehren
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Patent number: 4307203Abstract: Organic polyisocyanates are reacted chemically with aldehyde-broken down alkali metal cellulose silicate polymers to produce polyurethane products.Type: GrantFiled: March 26, 1981Date of Patent: December 22, 1981Inventor: David H. Blount
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Patent number: 4286080Abstract: The present invention relates to a process for the preparation of polyurethane ureas from relatively high molecular weight polyols, diisocyanates, water as chain lengthening agent and optionally short chain glycols in a multishaft extruder equipped with kneading elements.Type: GrantFiled: June 20, 1980Date of Patent: August 25, 1981Assignee: Bayer AktiengesellschaftInventors: Bernd Quiring, Wolfgang Wenzel, Georg Niederdellmann, Hans Wagner, Wilhelm Goyert
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Patent number: 4260696Abstract: Organic polyisocyanates are reacted chemically with aldehyde-broken down alkali metal cellulose silicate polymers to produce polyurethane products.Type: GrantFiled: June 9, 1980Date of Patent: April 7, 1981Inventor: David H. Blount
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Patent number: 4250292Abstract: The present invention relates to an improved continuous process for the preparation of polyurethane elastomers which are distinguished from the products produced by known processes by increased elasticity, reduced shrinkage, higher rigidity (limit bending stress), improved cold notched bar impact resistance and good thermal stability.Type: GrantFiled: September 13, 1979Date of Patent: February 10, 1981Assignee: Bayer AktiengesellschaftInventors: Georg Niederdellmann, Wilhelm Goyert, Ernst Meisert, Alfred Eitel, Hans Wagner, Hans Hespe
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Patent number: 4248753Abstract: Resinous compositions which are the Michael adducts of primary and/or secondary amines and polymers containing alpha, beta-ethylenically unsaturated moieties in conjugation with carbonyl moieties are disclosed. The compositions are depositable on substrates to form films. The films are amenable to oxidative and aminoplast cures and cure with light color. The compositions are desirable for use in cationic electrodeposition.Type: GrantFiled: August 28, 1978Date of Patent: February 3, 1981Assignee: PPG Industries, Inc.Inventors: Stephen L. Buchwalter, Joseph F. Bosso, Roger M. Christenson
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Patent number: 4246369Abstract: An ungelled composition of matter comprising a compound containing groups reactive with isocyanate, a compound containing groups reactive with mercaptan, and a carbamothioate curing agent adapted to generate a plurality of curing units upon being subjected to heating above about critical temperature. The generated curing units contain isocyanate groups, mercaptan groups, or combinations thereof. In preferred embodiments of this invention, the ungelled composition is adapted for use in powder coatings, anodic electrocoating, and cathodic electrocoating.Type: GrantFiled: September 18, 1978Date of Patent: January 20, 1981Assignee: SCM CorporationInventors: Vincent D. McGinniss, Donald R. Stevenson
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Patent number: 4242489Abstract: The present invention relates to a new organic heterocyclic isocyanate which is the reaction product of an organic diisocyanate and an amino or hydroxy nitrile. The invention also relates to a process of producing such isocyanates by reacting an excess of the diisocyanate with the nitrile under conditions under which the nitrile will not decompose and then maintaining the reaction mixture at an elevated temperature until the isocyanate nitrile adduct cyclizes. The reaction may be carried out in the presence of a catalyst for isocyanate addition reactions. Additionally, the invention relates to a process for the production of polyurethane by the reaction of the heterocyclic isocyanates with compounds carrying at least two isocyanate reactive hydrogen atoms per molecule.Type: GrantFiled: June 11, 1979Date of Patent: December 30, 1980Assignee: Bayer AktiengesellschaftInventors: Kurt Findeisen, Kuno Wagner, Walter Uerdingen
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Patent number: 4238378Abstract: The instant invention is directed to novel polyurethane cationic electrolyte-stable dispersions characterized by lateral or terminal polyalkylene oxide polyether chains containing from 2 to 10%, by weight, of ethylene oxide units, based on the total weight of the polyurethane; a content of ##STR1## groups of from 16 to 100 milliequivalents per 100 g of polyurethane; an average particle size of from 50 to 300 m.mu.; and a solids content of from 10 to 45%.Type: GrantFiled: November 8, 1977Date of Patent: December 9, 1980Assignee: Bayer AktiengesellschaftInventors: Peter Markusch, Klaus Noll, Dieter Dieterich
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Patent number: 4238594Abstract: Self-crosslinking coating compositions which are cathodically deposited on electrodeposition of paints containing the coating composition and a process for producing aqueous solutions of the self-crosslinking coating compositions by acid neutralization are described. The coating compositions are the reaction products of an unsaturated copolymer or a polycondensation product or a polyaddition product or mixture thereof carrying at least 0.5 double bonds on a side chain or at the end of a chain for each 1000 molecular weight units and the reaction product carrying one free isocyanate group of a polyisocyanate with an amine of the general formula -- ##STR1## wherein R is an alkanol or hydroxyphenyl radical and R.sub.1 and R.sub.2 are alkyl, aryl or cycloalkyl radicals. The cathodically depositable electrodeposition paints cure rapidly at relatively low temperatures to provide films which are highly resistant to corrosive influences.Type: GrantFiled: July 19, 1977Date of Patent: December 9, 1980Assignee: Vianova Kunstharz, A.G.Inventor: Georgios Pampouchidis
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Patent number: 4237264Abstract: The instant invention is directed to novel polyurethanes which have a substantially linear molecular structure and which are dispersible in water, and the method of producing such polyurethanes. The polyurethanes of the present invention are characterized by an ethylene oxide unit content of from 0.5 to 10%, by weight, and by an ionic content of from 0.1 to 15 milliequivalents per 100 grams of polyurethane.Type: GrantFiled: November 8, 1977Date of Patent: December 2, 1980Assignee: Bayer AktiengesellschaftInventors: Klaus Noll, Klaus Nachtkamp, Josef Pedain
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Patent number: 4233425Abstract: Addition polymerizable polyethers having pendant ethylenically unsaturated urethane groups are usefully employed as flooring materials and in other applications utilizing radiation curable or chemically curable materials. Such urethane polyethers are advantageously prepared by reacting a polyether polyol such as a hydroxy terminated polypropylene glycol with an isocyanatoalkyl ester of an ethylenically unsaturated acid such as 2-isocyanatoethyl methacrylate.Type: GrantFiled: November 15, 1978Date of Patent: November 11, 1980Assignee: The Dow Chemical CompanyInventors: Nancy B. Tefertiller, Kenneth A. Burdett, Robert F. Harris
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Patent number: 4224418Abstract: The instant invention is directed to compounds having an average molecular weight of from 300 to 12,000, containing: at least one hydroxyl group and at least one urethano-aryl-sulfonic acid group and a method for their preparation. The process is characterized as a process for the preparation of compounds having a number average molecular weight of from 300 to 12,000 having at least one hydroxyl group and at least one urethano-aryl-sulfonic acid group, comprising: reacting at from 0.degree. to 190.degree. C.(A) compounds having a molecular weight of from 62 to 10,000 having at least two hydroxyl groups; with(B) aromatic isocyanato sulfonic acids, wherein the equivalent ratio of the total quantity of isocyanate groups (including any isocyanate groups present in dimerized form) to sulfonic acid groups is from 0.5:1 to 50:1 and the equivalent ratio of the sum of hydroxyl groups in (A) to NCO groups is from 1.5:1 to 30:1. The invention is also directed to the product by the process.Type: GrantFiled: June 15, 1979Date of Patent: September 23, 1980Assignee: Bayer AktiengesellschaftInventors: Dieter Dieterich, Gerhard Balle, Hans G. Schmelzer
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Patent number: 4211847Abstract: This invention relates to urethane forming compositions and a method of forming polyurethanes having low residual potentially carcinogenic aromatic amines by adding scavengers from the group comprising cyclohexyl monoisothiocyanate and hindered aliphatic monoisocyanates of the general formula: ##STR1## wherein R.sub.1 - R.sub.7 are H, alkyl, cycloalkyl, aryl, alkaryl, aralkyl or mixtures thereof and x is 1 to 7.Type: GrantFiled: November 20, 1978Date of Patent: July 8, 1980Assignee: W. R. Grace & Co.Inventors: Clifton L. Kehr, Louis L. Wood, James L. Guthrie
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Patent number: 4182828Abstract: This invention relates to a process for the production of new, non-foamed urethane and/or urea group-containing polyisocyanate polyaddition products which contain both cationic and also anionic groups chemically bound into the same molecule of said polyisocyanate polyaddition products, to the polyaddition products obtainable by this process and to the use thereof for coating flexible and non-flexible sheet-form materials.Type: GrantFiled: April 27, 1978Date of Patent: January 8, 1980Assignee: Bayer AktiengesellschaftInventors: Artur Reischl, Wolfgang Wenzel
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Patent number: 4181789Abstract: A polyparabanic acid derivative having a recurrent structural unit of the formula ##STR1## wherein X is O or S; each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, when taken separately is hydrogen or an aliphatic, aromatic or aliphatic-aromatic group; R.sup.1 and R.sup.2 when taken together complete a cycloaliphatic ring and R.sup.3 and R.sup.4 when taken together complete a cycloaliphatic ring and each of R.sup.5, R.sup.6 and R.sup.7, which may be the same or different, is an aliphatic, aromatic or aliphatic-aromatic residue of an organic isocyanate after removal of at least one isocyanate group and method of producing same by reacting a compound of the formula ##STR2## with at least one organic isocyanate having at least two isocyanate groups at a temperature of from -20.degree. to 400.degree. C.Type: GrantFiled: September 22, 1978Date of Patent: January 1, 1980Assignee: Bayer AktiengesellschaftInventors: Henning Giesecke, Jurgen Hocker, Rudolf Merten
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Patent number: 4174434Abstract: The instant invention is directed to compounds having an average molecular weight of from 300 to 12,000, containing: at least one hydroxyl group and at least one urethano-aryl-sulfonic acid group and a method for their preparation. The process is characterized as a process for the preparation of compounds having a number average molecular weight of from 300 to 12,000 having at least one hydroxyl group and at least one urethano-aryl-sulfonic acid group, comprising: reacting at from 0.degree. to 190.degree. C.(A) compounds having a molecular weight of from 62 to 10,000 having at least two hydroxyl groups; with(B) aromatic isocyanato sulfonic acids, wherein the equivalent ratio of the total quantity of isocyanate groups (including any isocyanate groups present in dimerized form) to sulfonic acid groups is from 0.5:1 to 50:1 and the equivalent ratio of the sum of hydroxyl groups in (A) to NCO groups is from 1.5:1 to 30:1. The invention is also directed to the product by the process.Type: GrantFiled: July 31, 1978Date of Patent: November 13, 1979Assignee: Bayer AktiengesellschaftInventors: Dieter Dieterich, Gerhard Balle, Hans G. Schmelzer
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Patent number: 4163096Abstract: An epoxy resin mixture of compounds of the formula ##STR1## wherein Alk--represents a defined alkylene group,Ar--represents a defined arylene group, each Z independently of the other represents hydrogen or the group ##STR2## (derived from the reaction of a hydroxyl group with a monoisocyanate) and 50-500% of all Zs represent the group ##STR3## This mixture is suitable for the manufacture of flexible moulded articles having a high tear growth resistance.Type: GrantFiled: October 30, 1978Date of Patent: July 31, 1979Assignee: Ciba-Geigy CorporationInventors: Wolfgang Seiz, Roland Moser
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Patent number: 4162274Abstract: A crosslinkable, especially photopolymerizable urethane resin soluble in organic solvent, suitable as starting materials for photoresist lacquers and for the production of photopolymer printing plates comprising a reaction product of a polyepoxide having more than one 1,2-epoxide group per molecule with acrylic and/or methacrylic acid so that from 60 to 100 mole % of the 1,2-epoxide groups are converted into .beta.-hydroxy acrylic or methacrylic ester groups; 30 to 90 mole % of said .beta.-hydroxy ester groups having been reacted with an isocyanate and subsequently 10 to 70 mole % of said .beta.-hydroxy ester groups having been converted into acid semiester groups with a cyclic dicarboxylic acid anhydride.Type: GrantFiled: December 10, 1976Date of Patent: July 24, 1979Assignee: Bayer AktiengesellschaftInventor: Hans J. Rosenkranz
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Patent number: 4129716Abstract: A novel polyether containing urea-aldehyde resin useful in plastics, sealants, molds, foams and coatings. The novel composition comprises the condensation product of a ureido-terminated polyoxyalkylene and an aldehyde. The ureido terminated polyoxyalkylene compound is prepared by reacting a primary amine terminated polyoxyalkylene with urea at temperatures in the range of about 120.degree. C to about 160.degree. C in a molar ratio of about 1 molecule of urea for each primary amino group.Type: GrantFiled: June 6, 1977Date of Patent: December 12, 1978Assignee: Texaco Development CorporationInventor: Heinz Schulze
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Patent number: 4111914Abstract: The reaction of isocyanates with substances containing isocyanate groups or active hydrogen groups, such as hydroxyl groups, amino groups and the like, are initiated by sulfonium zwitterions such as the ar-cyclic sulfonium areneoxides. Accordingly, partially trimerized isocyanates, polyurethanes and other useful materials can be made.Type: GrantFiled: June 14, 1976Date of Patent: September 5, 1978Assignee: The Dow Chemical CompanyInventors: Jiri Kresta, Chen S. Shen
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Patent number: 4105643Abstract: Homopolymers of the diacrylates, dimethacrylates, di(2-haloacrylates) and di(2-cyanoacrylates) of 1-dialkanolaminophospholene-1-oxides and the copolymers of the above esters with lower-alkyl acrylates, meth-acrylates, 2-chloroacrylates and 2-cyanoacrylates are described. These polymers are useful as catalysts in the conversion of organic isocyanates to the corresponding carbodiimides.Type: GrantFiled: November 1, 1977Date of Patent: August 8, 1978Assignee: The Upjohn CompanyInventor: Curtis P. Smith
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Patent number: 4105642Abstract: Modified polystyrenes are described which are catalysts for the conversion of organic isocyanates to the corresponding carbodiimides. The modified polystyrenes are characterized by the presence of recurring units of the formula: ##STR1## WHEREIN THE BROKEN LINES IN THE PHOSPHOLENE NUCLEUS INDICATE A DOUBLE BOND LOCATED BETWEEN THE CARBON ATOM AT POSITION 3 AND ONE OF THE CARBON ATOMS AT POSITIONS 2 AND 4, THE H atom is attached to whichever carbon atom at positions 2 and 4 is not part of said double bond, R is halogen, alkoxy (C.sub.1-6), phenoxy, hydrocarbyl (C.sub.1-18), halohydrocarbyl (C.sub.1-18), m = 0-3; n = 0, 1; R.sub.1 is hydrogen or methyl; and R.sub.2 is hydrocarbyl free from substituents reactive with isocyanate.Type: GrantFiled: October 31, 1977Date of Patent: August 8, 1978Assignee: The Upjohn CompanyInventor: Curtis P. Smith