Isocyanate Esters (i.e., Compounds Containing The Isocyanate Group, -n=c=o, Bonded Directly To Carbon, Which Carbon May Be Single Bonded To Any Atom But May Be Multiple Bonded Only To Carbon) Patents (Class 560/330)
  • Patent number: 6177535
    Abstract: A process for preparing radiation-curable, urethane-functional prepolymers by reacting an isocyanate-functional component A with an OH-containing component B, wherein either component A embraces two different isocyanate compounds A1 or one isocyanate compound A1 and at least one isocyanate compound A2 or component B embraces at least two different compounds B1. Also, the prepolymers obtainable by the process and the radiation-curable formulations comprising them. Furthermore, the use of the radiation-curable formulations for coating substrates, a method of coating substrates, and the coated substrates themselves.
    Type: Grant
    Filed: September 21, 1998
    Date of Patent: January 23, 2001
    Assignee: BASF Aktiengesellchaft
    Inventors: Reinhold Schwalm, Rainer Königer, Wolfgang Paulus, Wolfgang Reich, Erich Beck, Matthias Lokai, Klaus Menzel
  • Patent number: 6111053
    Abstract: The invention relates to olefinically unsaturated polyisocyanates containing allophanate groups and having an NCO content of 6 to 20% by weight, an iodine value of 15 to 150, a content of hydrocarbon chains containing 12 to 30 carbon atoms of 100 to 700 mg/g and a content of allophanate groups of 10 to 300 mg/g, to a process for their production by reaction of a polyisocyanate component containing urethane groups with excess polyisocyanates, and to a one-component coating composition containing these olefinically unsaturated polyisocyanates as binders.
    Type: Grant
    Filed: May 8, 1995
    Date of Patent: August 29, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Martin Brahm, Eberhard Arning, Lutz Schmalstieg, Harald Mertes, Jurgen Schwindt
  • Patent number: 6051674
    Abstract: The present invention is directed to a polymeric vehicle, the formulated coating composition and a coating binder made from the polymeric vehicle and a method for making the polymeric vehicle where the polymeric vehicle includes a phenol blocked isocyanate having reactive aliphatic hydroxyl groups. The phenol blocked isocyanate may be made from a phenolic ester alcohol having at least one aliphatic hydroxyl group and one phenolic hydroxyl group.
    Type: Grant
    Filed: August 26, 1996
    Date of Patent: April 18, 2000
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: Albert I. Yezrielev, Frank N. Jones, Ramachandran P. Subrayan, Vijay Swarup
  • Patent number: 6036879
    Abstract: Polyoxyalkylene polyols containing double metal cyanide complexes or residues thereof as are produced during the preparation of polyoxyalkylene polyols by the double metal cyanide complex catalyzed oxyalkylation of a suitably functional hydric initiator are stable without catalyst removal. Isocyanate-terminated prepolymers prepared from such polyols are surprisingly viscosity-stable relative to similar prepolymers prepared from polyols not containing double metal cyanide complexes or residues thereof.
    Type: Grant
    Filed: February 9, 1999
    Date of Patent: March 14, 2000
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Bruce D. Lawrey, Stephen D. Seneker, Nigel Barksby
  • Patent number: 6022444
    Abstract: Isocyanate prepolymers which are useful as binders are made from a polyisocyanate mixture and a hydroxyl compound having at least about 1 hydroxyl group. The polyisocyanate mixture is made up of from about 50 to about 60% by weight of polyphenyl polymethylene polyisocyanate and from about 40 to about 50% by weight of an isomeric mixture of diphenylmethane diisocyanate (MDI). The isomeric mixture of MDI is made up of from about 4 to about 30% by weight of the 2,4'-isomer and from about 70 to about 96% by weight of the 4,4'-isomer. The binders of the present invention are advantageous in that they may be used in high moisture, low temperature conditions without a catalyst. Reduced MDI emissions are also achieved when the binders of the present invention are used to make composite materials.
    Type: Grant
    Filed: April 8, 1994
    Date of Patent: February 8, 2000
    Assignee: Bayer Corporation
    Inventors: Karl W. Haider, John W. Frink, Heber D. Layton, Peter H. Markusch, James W. Rosthauser, Bonnie L. Lawson, Michael A. Joseph
  • Patent number: 5990340
    Abstract: A di-hydroxy-functionalized linear non-crosslinked polyolefin is disclosed having no pendant chain-branched groups which is prepared by reacting 1,4-diacetoxy-2-butene with 1,5-cyclooctadiene in the presence of a catalyst comprising a ruthenium metal carbene complex, characterized in that the functionality number of said polyolefin as determined by NMR is 2.0 and the viscosity of said polyolefin ranges from about 800 to 16000 mPa.s @25.degree. C. at a number average molecular weight ranging from 2,600 to 6,500 g/mole. A prepolymer comprising the reaction of a polyisocyanate with the polyolefin is also disclosed.
    Type: Grant
    Filed: December 30, 1998
    Date of Patent: November 23, 1999
    Assignee: Bayer Corporation
    Inventors: Karl W. Haider, Jack C. Chan, E. Haakan Jonsson, Uli W. Franz, Mark A. Peters, Ronald P. Taylor
  • Patent number: 5973072
    Abstract: The present invention is directed to a polymeric vehicle, the formulated coating composition and a coating binder made from the polymeric vehicle and a method for making the polymeric vehicle where the polymeric vehicle includes a phenolic urethane reactive diluent. The phenolic urethane reactive diluent may be made from a phenolic ester alcohol having at least one aliphatic hydroxyl group.
    Type: Grant
    Filed: March 21, 1996
    Date of Patent: October 26, 1999
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: Frank N. Jones, Vijay Swarup, Ramachandran P. Subrayan, Suru Zhang
  • Patent number: 5955609
    Abstract: This invention relates to a novel trimerization catalyst system, and to a process for trimerizing organic polyisocyanates in the presence of thermally active catalyst systems. These catalyst systems comprise (A) compounds selected from the group consisting of (i) lithium salts of aliphatic or aromatic carboxylic acids, (ii) lithium salts of hydroxyl group containing compounds wherein the hydroxyl groups are directed attached to an aromatic ring, and (iii) lithium hydroxide; (B) an allophanate catalyst; and (C) an organic compound which contains at least one hydroxyl group.
    Type: Grant
    Filed: December 31, 1997
    Date of Patent: September 21, 1999
    Assignee: Bayer Corporation
    Inventors: William E. Slack, Hersel T. Kemp, II
  • Patent number: 5951911
    Abstract: The present invention relates to ethylenically unsaturated polyurethanes which are substantially free from isocyanate groups and havea) a content of .beta.,.gamma.-ethylenically unsaturated ether groups (calculated as C.dbd.C, MW 24) incorporated through allophanate groups of 0.5 to 10% by weight,b) an allophanate group content (calculated as N.sub.2 C.sub.2 HO.sub.3, MW 101) of 1 to 20% by weight andc) a total content of ethylenically unsaturated groups of (calculated as C.dbd.C, MW 24) of 1 to 15% by weight.The present invention also relates to ethylenically unsaturated polyisocyanates which contain allophanate groups and havei) an NCO content of 5 to 25% by weight,ii) a content of .beta.,.gamma.-ethylenically unsaturated ether groups (calculated as C.dbd.C, MW 24) incorporated through allophanate groups of 0.5 to 15% by weight andiii) an allophanate group content (calculated as N.sub.2 C.sub.2 HO.sub.3, MW 101) of 1 to 30%.
    Type: Grant
    Filed: January 9, 1998
    Date of Patent: September 14, 1999
    Assignee: Bayer Corporation
    Inventors: Lanny D. Venham, Arthur W. Mason, Michael K. Jeffries, Michael J. Dvorchak
  • Patent number: 5945531
    Abstract: A polyisocyanate composition, comprising:A) from 55 to 87% by weight of a polyisocyanate which contains uretdione groups;B) from 10 to 30% by weight of blocking agent,C) from 3 to 30% by weight of polyol having more than two hydroxyl groups and/or chain extender having more than two hydroxyl groups, wherein the polyisocyanate contains more than two terminal, partially or fully blocked isocyanate groups and has a molecular weight of from 1000 to 10,000.
    Type: Grant
    Filed: December 8, 1997
    Date of Patent: August 31, 1999
    Assignee: Huels Aktiengesellschaft
    Inventor: Rainer Gras
  • Patent number: 5925781
    Abstract: This invention relates to novel liquid, homogeneous toluene diisocyanate/polyether/polymethylene poly(phenylisocyanate) prepolymers having an NCO content of from about 2 to 16%, a viscosity or about 10,000 mPa.s or less at room temperature, and which contains about 1.0% or less of free monomeric TDI. This invention also relates to a process for the preparation of these liquid, homogeneous toluene diisocyanate/polyether/-polymethylene poly(phenylisocyanate) prepolymers.
    Type: Grant
    Filed: November 3, 1997
    Date of Patent: July 20, 1999
    Assignee: Bayer Corporation
    Inventors: Richard S. Pantone, Peter H. Markusch
  • Patent number: 5919888
    Abstract: Polyoxyalkylene polyols containing double metal cyanide complexes or residues thereof as are produced during the preparation of polyoxyalkylene polyols by the double metal cyanide complex catalyzed oxyalkylation of a suitably functional hydric initiator are stable without catalyst removal. Isocyanate-terminated prepolymers prepared from such polyols are surprisingly viscosity-stable relative to similar prepolymers prepared from polyols not containing double metal cyanide complexes or residues thereof.
    Type: Grant
    Filed: June 1, 1998
    Date of Patent: July 6, 1999
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Bruce D. Lawrey, Stephen D. Seneker, Nigel Barksby
  • Patent number: 5917083
    Abstract: The present invention relates to a process for preparing an isocyanate group-containing allophanate corresponding to formula (I) ##STR1## wherein R represents the residue obtained by removing the isocyanate groups from a (cyclo)aliphatic or araliphatic diisocyanate,Y represents the represents an m-valent residue obtained by removing the hydroxyl groups from a (poly)hydroxyl compound having m OH groups andn and m are the same or different and have a value of 1 to 5, by reacting an isocyanate group-containing oxadiazinetrione with a primary alcohol in the presence of a basic catalyst having a pKa value of >6.
    Type: Grant
    Filed: August 8, 1997
    Date of Patent: June 29, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Konig, Helmut Reiff, Christian Wamprecht, Harro Traubel
  • Patent number: 5905151
    Abstract: This invention relates to a process for trimerizing organic polyisocyanates in the presence of thermally active catalyst systems. The catalyst systems comprise (a) compounds selected from the group consisting of 1) lithium salts of aliphatic or aromatic carboxylic acids, 2) lithium salts of hydroxyl group containing compounds wherein the hydroxyl groups are directed attached to an aromatic ring, and 3) lithium hydroxide; used in conjunction with (b) an organic compound which contains at least one hydroxyl group.
    Type: Grant
    Filed: February 18, 1993
    Date of Patent: May 18, 1999
    Assignee: Bayer Corporation
    Inventors: William E. Slack, Hersel T. Kemp, II
  • Patent number: 5900441
    Abstract: Process for preparing a flexible foam by reacting a polyisocyanate composition having an NCO value of 11-24% by weight with an isocyanate-reactive compound having a number average molecular weight of 1000-12000 using water as blowing agent.
    Type: Grant
    Filed: October 29, 1996
    Date of Patent: May 4, 1999
    Assignee: Imperial Chemical Industries PLC
    Inventors: Mireille Berthine Albert De Witte, Eric Huygens, Luc Van Essche, Leo Franciscus Verstrepen
  • Patent number: 5883216
    Abstract: The present invention relates to polyisocyanates containingi) 0.5 to 10 wt. % of amide and/or imide structural units (calculated as --CO--N.dbd., MW=42),ii) 5 to 20 wt. % of isocyanate groups (calculated as --NCO, MW=42) blocked with blocking agents which are monofunctional in the context of the isocyanate addition reaction andiii) 0 to 30 wt. % of chemically incorporated urethane groups (calculated as --NH--CO--O--, MW=59) obtained from the reaction of isocyanate groups with the hydroxyl groups of organic polyhydroxyl compounds.The present invention also relates to a process for the production of these lacquer polyisocyanates, their use as a binder for stoving lacquers optionally in combination with organic polyhydroxyl compounds and to their use as a binder component containing free hydroxyl groups and optionally blocked isocyanate groups by reacting and/or blending the polyisocyanates with organic polyhydroxyl compounds having a molecular weight of 62 to 350.
    Type: Grant
    Filed: June 27, 1996
    Date of Patent: March 16, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Halpaap, Hans Schlegel, Jan Mazanek, Hans-Ulrich Meier-Westhues
  • Patent number: 5880312
    Abstract: Disclosed is a semicarbazide derivative represented by formula (1) or a terminal-blocked form thereof: ##STR1## wherein R.sup.1 represents a terminal isocyanate group-free polyisocyanate residue or a terminal isocyanate group-free triisocyanate residue; R.sup.2 represents an alkylene group, a cycloalkylene group, or an arylene group; each R.sup.3 independently represents a hydrogen atom or an alkyl group; n is zero or 1; and each of l and m is independently zero or a positive integer, provided that l and m satisfy the relationship 3.ltoreq.(l+m).ltoreq.20. Also disclosed is (.delta.) a composition comprising (.alpha.) at least one member selected from the group consisting of the semicarbazide derivative and a terminal-blocked form thereof and (.beta.) at least one member selected from the group consisting of a hydrophilic group-containing compound and a terminal-blocked form thereof. Also disclosed is a coating composition comprising (.gamma.) a polycarbonyl compound, and component (.alpha.) or composition (.
    Type: Grant
    Filed: December 23, 1996
    Date of Patent: March 9, 1999
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Akira Nakabayashi, Tetsuya Murakami
  • Patent number: 5849944
    Abstract: Elastomers exhibiting decreased demold times and improved green strength are prepared by reacting a di- or polyisocyanate with a monodisperse polyoxypropylene diol having ultra-low unsaturation, and preferably prepared by the double metal cyanide.t-butyl alcohol catalyzed polymerization of propylene oxide. Further improved demold times and elevated elastomer physical properties are made possible by the use of multidisperse polyoxyalkylene polyether polyol blends having an overall unsaturation of less than 0.010 meq/g and a polydispersity of about 1.4 or greater.
    Type: Grant
    Filed: May 27, 1997
    Date of Patent: December 15, 1998
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Gary L. Allen, Nigel Barksby, Stephen D. Seneker, Usama E. Younes
  • Patent number: 5821316
    Abstract: An isocyanate-terminated polyurethane prepolymer comprising the reaction product of a polyisocyanate and a polyol composition consisting essentially of a polyether polyol of 350-2000 equivalent weight and a low molecular weight polyol of 62 to<300 molecular weight, in an equivalent ratio of low molecular weight polyol to polyether polyol of 0.25-2.7:1. A polyurethane-urea elastomer having good dynamic properties can be prepared by reacting the isocyanate-terminated prepolymer with an aromatic amine chain extender at an equivalent ratio of 0.9-1.1:1.
    Type: Grant
    Filed: January 24, 1997
    Date of Patent: October 13, 1998
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Jeffrey Raymond Quay, Edwin Lee McInnis
  • Patent number: 5817860
    Abstract: A polyisocyanate prepolymer composition is comprised of the reaction product of (a) a polyisocyanate having an average functionality of at least 2 and containing at least about 20 percent by weight of a diisocyanate monomer, (b) a monohydric alcohol and (c) a polyol having an average hydroxyl functionality of at least about 1.8 to at most about 3.2 wherein the prepolymer composition has (i) an amount of isocyanate groups by weight sufficient to react with water in the absence of a supplemental blowing agent to make a foam, (ii) at most about 10.0 percent by weight of the diisocyanate monomer and (iii) an amount of the polyisocyanate that is capped by the monohydric alcohol sufficient to prevent gelling of the prepolymer composition. The prepolymer composition may be reacted with water to form a polyurethane foam.
    Type: Grant
    Filed: March 20, 1998
    Date of Patent: October 6, 1998
    Assignee: Essex Specialty Products, Inc.
    Inventors: Sidky D. Rizk, Jerry Lynn Spradling, Brad A. Pearson
  • Patent number: 5804648
    Abstract: A TDI residue generated from the phosgenation of toluene diamine having an ortho-isomer content of less than 0.5% is used to produce a urethane-filled hydroxyl compound. The TDI residues useful in this invention must contain at least 10% monomeric TDI and have a total NCO content of at least 20%. These TDI residues are reacted with a monofunctional alcohol in an amount such that the equivalent ratio of isocyanate groups to hydroxyl groups is from about 0.9:1 to about 1:0.9. The resultant composition may then be dissolved in a polyhydroxyl compound to produce a urethane-filled polyhydroxyl compound. This urethane-filled polyhydroxyl compound may then be reacted with a polyisocyanate to produce a polyurethane.
    Type: Grant
    Filed: December 27, 1996
    Date of Patent: September 8, 1998
    Assignee: Bayer Corporation
    Inventor: William E. Slack
  • Patent number: 5798409
    Abstract: The present invention relates to two-part reactive polyurethane compositons and the cured coatings prepared therefrom. The invention also relates to particular compositions and cured coatings therefrom that exhibit high damping character, excellent scratch-resistance, excellent mar-resistance, and self-healing characteristics. The invention also relates to a novel polyurethane prepolymer useful in some ofthe compositions. The invention also relates to method of making certain coatings of the invention.
    Type: Grant
    Filed: April 1, 1997
    Date of Patent: August 25, 1998
    Assignee: Minnesota Mining & Manufacturing Company
    Inventor: Chia-Tie Ho
  • Patent number: 5786438
    Abstract: The present invention relates to mixtures of cycloaliphatic diisocyanates corresponding to formula 1) ##STR1## wherein R represents a saturated, linear, aliphatic hydrocarbon residue having 8 to 15 carbon atoms.The present invention also relates to a process for the preparation of these diisocyanate mixtures and to their use for the production of polyisocyanate addition products.
    Type: Grant
    Filed: March 31, 1997
    Date of Patent: July 28, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Scholl, Bernhard Jansen, Klaus Jost, Rolf-Volker Meyer
  • Patent number: 5753750
    Abstract: TDI residue-based urethane-filled isocyanate compositions are produced by reacting a TDI residue satisfying specified criteria with a monofunctional alcohol in amounts such that the equivalent ratio of isocyanate groups to hydroxyl groups is from about 0.9:1 to about 1:0.9. This reaction product is then dissolved in a diisocyanate or polyisocyanate. These TDI residue-based urethane-filled isocyanate compositions are particularly useful in the production of polyurethanes.
    Type: Grant
    Filed: December 27, 1996
    Date of Patent: May 19, 1998
    Assignee: Bayer Corporation
    Inventors: William E. Slack, Jyothi S. Pisipati
  • Patent number: 5753749
    Abstract: Urethane-filled compositions are produced by reacting a dicyclohexylmethane diisocyanate residue or a dicyclohexylmethane diisocyanate residue containing mixture with a monofunctional alcohol containing at least one ether group in an amount such that the equivalent ratio isocyanate groups to hydroxyl groups is from about 0.9:1 to about 1:0.9. The diisocyanate residue or residue-containing mixture must contain at least 20% by weight monomeric diisocyanate and have a total NCO content of at least 10%. The diisocyanate residue is produced by phosgenating dicyclohexylmethane diamine in which less than 20% polymeric diamine is present. The urethane filled compositions produced in this manner may then be dissolved in either a polyol or a polyisocyanate and subsequently used to produce polyurethanes in known manner.
    Type: Grant
    Filed: December 27, 1996
    Date of Patent: May 19, 1998
    Assignee: Bayer Corporation
    Inventor: William E. Slack
  • Patent number: 5750727
    Abstract: A polyisocyanate composition, comprising:A) from 55 to 87% by weight of a polyisocyanate which contains uretdione groups;B) from 10 to 30% by weight of blocking agent,C) from 3 to 30% by weight of polyol having more than two hydroxyl groups and/or chain extender having more than two hydroxyl groups, wherein the polyisocyanate contains more than two terminal, partially or fully blocked isocyanate groups and has a molecular weight of from 1000 to 10,000.
    Type: Grant
    Filed: February 12, 1996
    Date of Patent: May 12, 1998
    Assignee: Huels Aktiengesellschaft
    Inventor: Rainer Gras
  • Patent number: 5739207
    Abstract: Urethane-filled polyisocyanates are produced by (a) reacting a hexamethylene diisocyanate-containing residue having less than 10% by weight monomeric hexamethylene diisocyanate and a total NCO content of at least 25% with an alcohol containing at least one ether linkage in an equivalent ratio of isocyanate to hydroxyl groups of from about 0.9:1 to about 1.0:0.9 and (b) dissolving the product of (a) in a polyisocyanate. These urethane-filled polyisocyanates are particularly useful in the production of polyurethanes.
    Type: Grant
    Filed: December 27, 1996
    Date of Patent: April 14, 1998
    Assignee: Bayer Corporation
    Inventor: William E. Slack
  • Patent number: 5728317
    Abstract: (Cyclo)aliphatic polyisocyanate compositions which have a long shelf life, are obtainable by phosgene-free methods, preferably by thermal cleavage of (cyclo)aliphatic polycarbamates, and, for stabilization, contain at least one primary stabilizer (2a), preferably a sterically hindered phenol and/or an aromatic amine, or at least one secondary stabilizer (2b), preferably an organic phosphite and/or a thioether, or at least one acidic stabilizer (2c), preferably a carboxylic acid, an acyl chloride, an inorganic acid, an inorganic acid chloride and/or a diester of phosphoric acid, or a stabilizer system comprising at least 2 of the stabilizers (2a) to (2c), a process for the preparation of the (cyclo)aliphatic polyisocyanate compositions and their preferred use for the preparation of isocyanurate-containing polyisocyanates.
    Type: Grant
    Filed: May 13, 1996
    Date of Patent: March 17, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Laqua, Franz Merger, Tom Witzel, Ursula Siebenhaar, David Agar
  • Patent number: 5703271
    Abstract: A method of synthesizing multitier cascade polymers and the polymers made thereby are formed by reacting at least one tier of a polymer with a functionalized isocyanate having the following formula:O.dbd.C.dbd.N--C(CH.sub.2 --R).sub.3with R being selected from the group including:--(CH.sub.2).sub.n --CH.sub.2 --COOR' a)with R' being selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl- polycycloalkyl, adamantyl, n=0-10;--O--(CH.sub.2).sub.n --CH.sub.2 --COOR'--O--(CH.sub.2).sub.n --CH.sub.2 --CN b)with R' being selected from the group consisting of alkyl (c-1 to C(20), cycloalkyl (C-3 to C-10), aryl heteroaryl, polycycloalkyl, adamantyl, n=0-10; and--CH.sub.2 --(CH.sub.2).sub.
    Type: Grant
    Filed: April 2, 1996
    Date of Patent: December 30, 1997
    Assignee: University of South Florida
    Inventors: George R. Newkome, Claus Weis
  • Patent number: 5696221
    Abstract: Elastomers with improved physical properties, particularly hardness and rebound, may be prepared by the diamine chain extension or moisture cure of low isocyanate group content, toluene diisocyanate-based prepolymers prepared from a polyol component comprising a high molecular weight, low unsaturation polyoxypropylene diol and a low molecular weight diol. The elastomers are useful for applications such as rollers and other applications where hardness and rebound are important.
    Type: Grant
    Filed: July 15, 1996
    Date of Patent: December 9, 1997
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Nigel Barksby, Bruce D. Lawrey, Susan M. Clift
  • Patent number: 5693686
    Abstract: A polyisocyanate having an acid value of at least 0.01% HCl is used to produce polyisocyanate, polyisocyanurate and polyurethane urea foams with an HCFC blowing agent. The use of such a polyisocyanate is advantageous because the polyisocyanate does not cause significant decomposition of the HCFC blowing agent.
    Type: Grant
    Filed: February 10, 1994
    Date of Patent: December 2, 1997
    Assignee: Bayer Corporation
    Inventors: John F. Szabat, Charles E. Mortimer, Joseph M. Sutej, Jeanne L. Beaumont, Steven L. Schilling, Harold R. Parsons, Robert P. Yeater
  • Patent number: 5691441
    Abstract: Substitution of from 5 to 50 equivalent percent of an ultra-low unsaturation polyoxypropylene diol for PTMEG in isocyanate-terminated prepolymers used in spandex production is found to lower considerably both prepolymer viscosity and hysteresis while substantially retaining other desirable physical properties. Such products may offer higher fiber production rates than are possible while employing an all PTMEG-derived polymer.
    Type: Grant
    Filed: October 11, 1996
    Date of Patent: November 25, 1997
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Stephen D. Seneker, Bruce D. Lawrey
  • Patent number: 5688989
    Abstract: A polyurethane composition for the production of single-component polyurethane foams on dry or wet substrates, wherein the composition is the reaction product of a polyol with a molar excess of difunctional or polyfunctional isocyanates and wherein 10% to 80% by weight of the polyol has been replaced by a nonionic surfactant containing at least one hydroxyl group.
    Type: Grant
    Filed: July 3, 1996
    Date of Patent: November 18, 1997
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Peter Daute, Roland Gruetzmacher, Johann Klein, Hermann Kluth, Rainer Hoefer
  • Patent number: 5677412
    Abstract: Poly(ether-urethanes) can be made from cyclic ethers and organic isocyanates by using selected metal compounds as catalysts. Polymers useful as thermoplastic elastomers, spandex fibers or urethane rubbers can be made by reacting diisocyanates containing functional groups with a tetrahydrofuran, especially tetrahydrofuran itself. The invention also discloses an improved process for the cationic polymerization of a cyclic ether by using an organic isocyanate.
    Type: Grant
    Filed: March 19, 1996
    Date of Patent: October 14, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Neville Everton Drysdale
  • Patent number: 5672736
    Abstract: The present invention relates to a process for preparing polyisocyanates containing allophanate groups by reacting compounds a), whichi) contain urethane groups, but which are substantially free of hydroxyl groups and isocyanate groups,ii) have an average of at least two urethane groups per molecule,iii) are prepared by reacting organic isocyanates a1) with organic hydroxyl compounds a2) andiv) have an average molecular weight of at most 2,500,with excess quantities, based on the urethane groups, of distillable organic polyisocyanates b) to form polyisocyanates containing allophanate groups and subsequently removing by distillation the unreacted excess of component b) to a residual content of less than 0.5 wt. %, provided that polyisocyanates a1) and polyisocyanates b) are different.The present invention also relates to the products obtained from this process and to their use as binders or binder components in coating compositions.
    Type: Grant
    Filed: November 8, 1995
    Date of Patent: September 30, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Martin Brahm, Lutz Schmalstieg, Josef Pedain
  • Patent number: 5648445
    Abstract: Allophanate-modified 1,3-phenylene diisocyanates or 1,1-biphenyl diisocyanates or 1,1'-oxy-bis-(isocyanato benzenes) which are storage stable liquid at 25.degree. C. are made by reacting the diisocyanate and a mono-alcohol to form an isocyanate containing urethane groups. The urethane groups in the diisocyanate are then converted to allophanate groups. The resultant product which has an isocyanate group content of from about 10 to about 40% may be further reacted with isocyanate-reactive compounds to produce an allophanate-modified diisocyanate prepolymer containing urethane or urea groups having an isocyanate group content of from about 5 to about 40.0%. The liquid, storage-stable, allophanate-modified diisocyanates produced by these processes are particularly useful in the production of elastomers and flexible foams.
    Type: Grant
    Filed: December 22, 1995
    Date of Patent: July 15, 1997
    Assignee: Bayer Corporation
    Inventors: William E. Slack, Rick L. Adkins
  • Patent number: 5645763
    Abstract: The use of esters--liquid at room temperature--of C.sub.6-22 fatty acids with monohydric alcohols and/or of C.sub.6-22 fatty alcohols with monocarboxylic acids as solvents for isocyanates and/or isocyanurates is provided. Because the ester reduces the viscosity of the isocyanates and/or isocyanurates, the mixture will be easy to pump and mix with other components prior to curing. Also provided is a process for reducing the viscosity of isocyanates and isocyanurates comprising adding to said isocyanate or isocyanurate one or more esters selected from the group consisting of C.sub.6-22 fatty acids with monohydric alcohols and C.sub.6-22 fatty alcohols with monocarboxylic acids, said esters being a liquid at room temperature.
    Type: Grant
    Filed: November 14, 1994
    Date of Patent: July 8, 1997
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Johann Klein, Peter Daute, Roland Gruetzmacher, Rainer Hoefer
  • Patent number: 5625026
    Abstract: An amide group-containing epoxy resin obtained by reacting an epoxy resin with an amide group-containing diisocyanate obtained by reacting a diisocyanate with a dicarboxylic acid gives a uniform cured article showing high adhesiveness and is usable as an adhesive, a coating composition, and the like.
    Type: Grant
    Filed: May 18, 1994
    Date of Patent: April 29, 1997
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Kenji Suzuki, Yoshiyuki Mukoyama, Toshihiko Ito
  • Patent number: 5574122
    Abstract: The present invention is directed to a polyisocyanate mixturei) having an NCO content of 5 to 35% by weight and prepared from an organic diisocyanate,ii) containing up to 25% by weight of isocyanurate groups (calculated as N.sub.3, C.sub.3, O.sub.3, MW 126),iii) containing allophanate groups in an amount such that there are more equivalents of allophanate groups than urethane or urea groups and such that the polyisocyanate mixture remains stable and homogeneous in storage for 3 months at 25.degree. C. andiv) containing siloxane groups (calculated as SiO, MW 44) in an amount of 0.002 to 50% by weight,wherein the preceding percentages are based on the solids content of the polyisocyanate mixture, excluding any unreacted organic diisocyanate, and wherein the siloxane groups are incorporated by reacting an isocyanate group with a compound containing one isocyanate-reactive group directly attached to a carbon atom and one or more siloxane groups.
    Type: Grant
    Filed: September 29, 1995
    Date of Patent: November 12, 1996
    Assignee: Bayer Corporation
    Inventors: Philip E. Yeske, Edward P. Squiller, William E. Slack
  • Patent number: 5574124
    Abstract: Isocyanate prepolymers having an NCO content of 1.5 to 5.0 wt. % and a monomeric diisocyanate content of less than 0.5 wt. % which are the reaction products ofA) aromatic or cycloaliphatic diisocyanates withB) mixtures ofB1) polyether polyols having a molecular weight of 1000 to 3000 andB2) polyester carbonate diols having a molecular weight of 700 to 3000,wherein components B1) and B2) are present in a weight ratio of 0.25:1 to 1.5:1;a process for the preparation of these isocyanate prepolymers by reacting the preceding starting materials at an NCO/OH equivalent ratio of at least 1.5:1 and optionally with subsequent removing unreacted monomeric diisocyanate by distillation; and the use of these isocyanate prepolymers as binders for sealing or coating compositions.
    Type: Grant
    Filed: August 3, 1995
    Date of Patent: November 12, 1996
    Assignees: Bayer Aktiengesellschaft, Bayer Corporation
    Inventors: Lutz Schmalstieg, Rainer Rettig, Ulrich Walter, Edwin R. Hortelano
  • Patent number: 5561172
    Abstract: A primary object of the invention is to provide a method of producing rigid polyurethane foams using 1,1-dichloro-1-fluoroethane (HCFC-141b) as the blowing agent while substantially avoiding the formation of decomposition products from HCFC-141b. The above object can be achieved by a method of producing rigid polyurethane foams which comprises reacting a polyol with an organic polyisocyanate for foaming in the presence of HCFC-141b and a stabilizer therefor and in the presence of an organic metal catalyst and/or an imidazole compound catalyst and by the thus-produced rigid polyurethane foams.
    Type: Grant
    Filed: November 12, 1994
    Date of Patent: October 1, 1996
    Assignee: Daikin Industries, Ltd.
    Inventors: Yukio Omure, Tatsumi Tsuchiya, Kiyohiro Yuge, Hitoshi Muramatsu
  • Patent number: 5552507
    Abstract: Diisocyanates containing carboxylic acid ester groups corresponding to the formula: ##STR1## in which R and R.sup.1 represent specified groups are produced by phosgenation of the corresponding diamines, optionally present in the form of an ammonium salt. These diisocyanates are useful as starting materials in the production of plastics containing urethane and/or urea groups and as starting materials for the production of intermediate products used for the production of such plastics.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: September 3, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christian Wamprecht, Klaus Jost, Stefan Penninger
  • Patent number: 5541279
    Abstract: The invention relates to a process for the preparation of totally or partially blocked polyisocyanates based on a blocking agent and on a polyisocyanate containing at least two free NCO groups, if desired in the presence of a chain extender, in which the totally or partially blocked polyisocyanates are prepared by a solvent-free and continuous procedure. This reaction is carried out in a static mixer or intensive kneading apparatus or extruder. The invention furthermore relates to the use of the totally or partially blocked polyisocyanates for PUR powder coatings and solvent-containing, one-component PUR stoving enamels.
    Type: Grant
    Filed: November 30, 1994
    Date of Patent: July 30, 1996
    Assignee: Huels Aktiengesellschaft
    Inventors: Rainer Gras, Siegfried Brandt
  • Patent number: 5530154
    Abstract: The invention relates to prepolymers containing isocyanate groups which can be prepared by reactinga) organic isocyanates withb) polyetherols containing at least 2 hydroxyl groups per molecule and having molecular weights of greater than 400 and/or polyesterols containing at least 2 hydroxyl groups per molecule and having molecular weights of greater than 400,c) isocyanate-reactive compounds which are at least difunctional and have molecular weights of from 18 to 399, and, if desired,d) Lewis and/or Bronsted acidic compounds ande) conventional auxiliaries and additives, such as antioxidants, light stabilizers or fillers,wherein at least one aromatic aminopolyether alcohol of the formula ##STR1## where R is aryl, alkylaryl containing one or more C.sub.1 - to C.sub.4 -alkyl groups, haloaryl, nitroaryl or cyanoaryl,R' and R" are identical or different and are, independently of one another, hydrogen, alkyl, aryl, aralkyl, alkoxyalkyl, alkoxyaryl or aroxyaryl,x and y are independent of one another andx+y.ltoreq.
    Type: Grant
    Filed: May 17, 1995
    Date of Patent: June 25, 1996
    Assignee: BASF Schwarzheide GmbH
    Inventors: Holger Seifert, Juergen Winkler, Regina Pretzsch, Robert O'Meara
  • Patent number: 5527925
    Abstract: Compounds of formula I: ##STR1## are disclosed. The compounds are photoinitiators which can be functionalized by means of ethylenic groups or can be bonded to H-active substances, in order, for example, to modify surfaces by means of photopolymerizable substances. The compounds are especially useful in the manufacture of contact lenses.
    Type: Grant
    Filed: June 24, 1994
    Date of Patent: June 18, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Chabrecek, Dieter Lohmann
  • Patent number: 5512603
    Abstract: A method for preparing a polyurethane foam which comprises reacting an organic polyisocyanate and a polyol in the presence of a blowing agent, cell stabilizer and a catalyst composition consisting essentially of a pyrrolizidine of the formula: ##STR1## where R.sub.1 and R.sub.2 independently are --H, --OH, ##STR2## or --NR.sub.4 R.sub.5, R.sub.3 is hydrogen, a C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.6 -C.sub.10 aryl, or C.sub.7 -C.sub.11 arylalkyl group, andR.sub.4 and R.sub.5 independently represent H, a C.sub.1 -C.sub.12 alkyl group, C.sub.5 -C.sub.10 cycloalkyl, C.sub.6 -C.sub.10 aryl, or C.sub.7 -C.sub.11 arylalkyl group, provided that at least R.sub.1 or R.sub.2 is not hydrogen.
    Type: Grant
    Filed: February 22, 1994
    Date of Patent: April 30, 1996
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Richard V. C. Carr, Kevin R. Lassila, Mark L. Listemann, Lisa A. Mercando, Kristen E. Minnich, Ann C. L. Savoca, Amy L. Wressell
  • Patent number: 5510443
    Abstract: The present invention relates to process for preparing a coated substrate having improved resistance to yellowing which comprises coating a substrate with a one-component coating composition containinga) a blocked polyisocyanate which is the reaction product of a polyisocyanate with an oxime or lactam blocking agent for isocyanate groups andb) a compound containing at least two isocyanate-reactive groups,provided that component a) and/or component b) contains the group, --CO--(R)N--N(R)--CO--, wherein R represents hydrogen or an optionally substituted hydrocarbon radical, in an amount of 0.01 to 5% by weight, based on the solids content of components a) and b),by applying the one-component coating composition wet-on-wet to a coating composition containing acid groups and/or melamine resins which has previously been applied to the substrate or by adding a melamine resin to the one-component coating composition prior to applying it to the substrate, which may optionally have been precoated.
    Type: Grant
    Filed: March 15, 1993
    Date of Patent: April 23, 1996
    Assignee: Bayer Corporation
    Inventors: Myron W. Shaffer, Terry A. Potter, Lanny D. Venham, Peter D. Schmitt
  • Patent number: 5504178
    Abstract: The present invention relates to a blocked polyisocyanate which is the reaction product of a polyisocyanate withi) 60 to 99.9 equivalent percent, based on the equivalents of isocyanate groups of the polyisocyanate prior to blocking, of an oxime or lactam blocking agent for isocyanate groups andii) 0.1 to 40 equivalent percent, based on the equivalents of isocyanate groups of the polyisocyanate prior to blocking, of hydrazine and/or a compound which is soluble in either the polyisocyanate, the blocking agent or an optional organic solvent for the polyisocyanate and contains the group, H(R)N--NR--CO--, wherein the carbonyl group is bound to carbon or nitrogen and R represents hydrogen or an optionally substituted hydrocarbon radical.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: April 2, 1996
    Assignee: Bayer Corporation
    Inventors: Myron W. Shaffer, Terry A. Potter, Lanny D. Venham, Peter D. Schmitt
  • Patent number: 5463081
    Abstract: The invention relates to novel intermediates for the preparation of a certain group of novel phenylsulfonylurea herbicides, which herbicides are particularly advantageous for use in crop protection. The novel intermediate compounds are of the formula II ##STR1## and of the formula VI, ##STR2## as defined in the specification and claims. The intermediate compounds may be used to prepare herbicidal and plant growth regulating compounds of the formula I or salts thereof: ##STR3## as defined in the specification. The herbicides so obtained are particularly suitable for selectively controlling weeds.
    Type: Grant
    Filed: September 21, 1993
    Date of Patent: October 31, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Oswald Ort, Klaus Bauer, Hermann Bieringer
  • Patent number: 5455374
    Abstract: The present invention relates to a liquid, storage-stable isocyanate having a viscosity of less than 100,000 mPa.s at 23.degree. C. and an isocyanate content of from about 9 to 20% by weight, and is prepared by reacting a solid 4,4'-methylene bis(cyclohexyl isocyanate) with a blocking agent. The 4,4'-methylene bis(cyclohexyl isocyanate) must contain at least 35 to 100% by weight of the trans,trans isomer. More generally, this liquid isocyanate is prepared by reacting the solid or semi-solid 4,4'-methylene bis (cyclohexyl isocyanate) with the blocking agent in quantities such that at least 22% but less than 60% of the isocyanate groups are blocked. Preferred blocking agents are the ketoximes, and mixtures thereof.
    Type: Grant
    Filed: June 30, 1993
    Date of Patent: October 3, 1995
    Assignee: Bayer Corporation
    Inventors: Stephen D. Seneker, Scott A. Kane