Processes Patents (Class 560/336)
  • Publication number: 20090312451
    Abstract: The present invention relates to an ethylenically unsaturated prepolymer comprising at least one ending X which reacts by condensation chosen from hydroxyl and/or amine or free isocyanate groups and optionally an ending X? having ethylenic unsaturation, the prepolymer being the reaction product of the following components A and B: A) a first component A comprising the following mixture: i) at least one first ethylenically unsaturated resin carrying specific hydroxyl and/or amine reactive endings, and/or ii) optionally at least one second resin, other than the resin i), chosen from: ethylenically unsaturated hydroxylated resins, and/or hydroxylated and/or aminated saturated resins, and/or iii) optionally at least one third reactive saturated resin, iv) optionally at least one unsaturated monoalcohol up to 30% in equivalents of the OH+NH2 total, B) a second component B comprising at least one polyisocyanate with a functionality equal to 2 or greater than 2, A and B being in proportions which make it pos
    Type: Application
    Filed: July 4, 2007
    Publication date: December 17, 2009
    Inventors: Patrick Belliard, Jérôme Mazajczyk, Roland Delory, Guillaume Cledat, Francis Verdiere, Serge Herman
  • Publication number: 20090277356
    Abstract: The present invention provides products of isocyanate functional material(s) and compound(s) selected from the group of compounds represented by structural Formula (I): wherein X, Y and R1 are as described herein, use of such compounds as anaerobic cure accelerators, and compositions including such compounds.
    Type: Application
    Filed: May 7, 2008
    Publication date: November 12, 2009
    Applicant: HENKEL CORPORATION
    Inventors: Anthony F. Jacobine, Andrew Messana, David M. Glaser, Steven Thomas Nakos
  • Patent number: 7579066
    Abstract: There are provided a novel ethylenically unsaturated group-containing isocyanate compound, a process for producing the same, and a reactive monomer produced from the isocyanate compound, a reactive polymer and its use. The ethylenically unsaturated group-containing isocyanate compound according to the present invention is represented by formula (I).
    Type: Grant
    Filed: October 31, 2005
    Date of Patent: August 25, 2009
    Assignee: Showa Denko K.K.
    Inventors: Kaneo Nozawa, Katsutoshi Morinaka, Toru Sasaki, Katsumi Murofushi
  • Patent number: 7553963
    Abstract: This invention relates to storage-stable, liquid, partially trimerized and allophanized polyisocyanates having an NCO group content of 15 to 41% by weight, and comprising 5 to 85% by weight of toluene diisocyanate, 5 to 85% by weight of a polyisocyanate of the diphenyl-methane series and an organic compound or mixture thereof. The present invention also relates to a process for the preparation of the storage-stable, liquid, partially trimerized and allophanized polyisocyanates; to storage-stable, liquid urethane prepolymers of these partially trimerized and allophanized polyisocyanates; and to a process for the production of these storage-stable, liquid, urethane prepolymers.
    Type: Grant
    Filed: October 29, 2003
    Date of Patent: June 30, 2009
    Assignee: Bayer MaterialScience LLC
    Inventors: William E. Slack, Hersel T. Kemp, II
  • Publication number: 20090082588
    Abstract: The invention relates to a process for producing fluorinated carbamates comprising the reaction between an amine or polyamine and a fluorinated carbonate, in the presence of a catalyst which does not contain metals and comprises at least one tertiary amine group. The process can also comprise an additional step in which the carbamates are transformed into the corresponding isocyanates.
    Type: Application
    Filed: September 12, 2008
    Publication date: March 26, 2009
    Inventors: Ana Padilla Polo, Valentin Ruiz Santa Quiteria, Avelino Corma Canos, Hermenegildo Garcia Gomez, Raquel Juarez Marin
  • Publication number: 20090036630
    Abstract: Polyurethane resin compositions include a urethane prepolymer with an active hydrogen group and a polyisocyanate, or a urethane prepolymer with an isocyanate group and an active hydrogen compound. The urethane prepolymers having an active hydrogen group or an isocyanate group are obtained by reacting an allophanate group-containing polyisocyanate with a side-chain hydrocarbon group of 5 or more carbon atoms and a bifunctional or polyfunctional active hydrogen compound. Particularly preferably, the allophanate group-containing polyisocyanate is obtained by reacting a C5 or higher carbon number compound having an alcoholic hydroxyl group and an organic diisocyanate, in the presence of an organic bismuth carboxylate and an organic phosphite triester. The polyurethane resin compositions are suited for use as adhesives for bonding low-polarity resin bases such as polyolefin films.
    Type: Application
    Filed: December 26, 2006
    Publication date: February 5, 2009
    Inventors: Shigetoshi Sasano, Takeshi Oosaki, Mitsuhiro Nishimura, Hiroyuki Washizu
  • Publication number: 20080262262
    Abstract: The invention provides a process for isocyanate dimerization (uretdione formation) and a process for preparing polyisocyanates having a high content of uretdione groups, using specific phosphines as catalysts. The phosphines have one or two tertiary alkyl radicals bound directly to phosphorus.
    Type: Application
    Filed: April 14, 2008
    Publication date: October 23, 2008
    Inventors: Frank Richter, Reinhard Halpaap
  • Patent number: 7420080
    Abstract: The invention relates to a multistage process for continuous and phosgene-free preparation of cycloaliphatic diisocyanates.
    Type: Grant
    Filed: April 8, 2005
    Date of Patent: September 2, 2008
    Assignee: Degussa AG
    Inventors: Stephan Kohlstruk, Manfred Kreczinski, Hans-Werner Michalczak
  • Patent number: 7414145
    Abstract: A method of an enantioselective nucleophilic addition reaction to carbonyl, which enables an asymmetric synthesis of an optically active ?-hydroxy-?-keto acid ester, an optically active ?-hydroxy-?-amino acid ester, hydroxydiketone compounds, etc. being useful as a raw material or synthesis intermediate for producing a pharmaceutical preparation, an agricultural chemical, a fragrance, a functional polymer or the like. In this method, the nucleophilic addition reaction of enamide compound accompanied by hydroxyl (—OH) formation to carbonyl is carried out in the presence of a chiral catalyst with copper or nickel.
    Type: Grant
    Filed: January 24, 2005
    Date of Patent: August 19, 2008
    Assignee: Japan Science and Technology Agency
    Inventor: Shu Kobayashi
  • Publication number: 20080132724
    Abstract: This invention relates to a novel liquid, storage-stable diphenylmethane diisocyanate which contains allophanate and reactive unsaturation. These novel storage-stable liquids comprise the reaction product of diphenylmethane diisocyanate with an ethylenically unsaturated alcohol, in the presence of an allophanate catalyst and a suitable inhibitor.
    Type: Application
    Filed: December 4, 2006
    Publication date: June 5, 2008
    Inventor: Rick L. Adkins
  • Patent number: 7371891
    Abstract: The invention relates to a multistage process for continuous and phosgene-free preparation of cycloaliphatic diisocyanates.
    Type: Grant
    Filed: July 21, 2005
    Date of Patent: May 13, 2008
    Assignee: Degussa AG
    Inventors: Stephan Kohlstruk, Manfred Kreczinski, Hans-Werner Michalczak
  • Patent number: 7368595
    Abstract: The invention relates to an improved process for the production of isocyanates by the reaction of an amine or a mixture of two or more amines with phosgene, the improvement involving the phosgene containing less than about 100 ppm of sulfur in elemental or bound form. The inventive process yields light-colored isocyanates that are suitable for the production of polyurethanes or their precursors (e.g. prepolymers) without the treatment processes heretofore required.
    Type: Grant
    Filed: January 10, 2007
    Date of Patent: May 6, 2008
    Assignee: Bayer MaterialScience AG
    Inventors: Stefan Wershofen, Torsten Hagen, Christian Steffens, Jeffrey Bolton
  • Patent number: 7361782
    Abstract: A process for preparing fluorochemical monoisocyanates comprises reacting at least one fluorochemical alcohol represented by the formula CnF2n+1SO2NCH3(CH2)mOH, wherein n=2 to 5, and m=2 to 4, with 4,4?-diphenylmethane diisocyanate (MDI) in a solvent in which the resulting fluorochemical monoisocyanate is not soluble; wherein the molar ratio of fluorochemical alcohol:MDI is from about 1:1 to about 1:2.5.
    Type: Grant
    Filed: July 12, 2006
    Date of Patent: April 22, 2008
    Assignee: 3M Innovative Properties Company
    Inventors: Thomas P. Klun, Alan R. Kirk, George G. I. Moore, John C. Clark, Zai-Ming Qiu
  • Patent number: 7339020
    Abstract: High-functionality polyisocyanates are prepared by a process which comprises (i) preparation of an addition product (A) which contains one group which is reactive toward isocyanate and at least two isocyanate groups by reacting (a) a diisocyanate or polyisocyanate I with (b1) compounds having at least three groups which are reactive toward isocyanate or (b2) compounds containing two groups which are reactive toward isocyanate or mixtures of (b1) and (b2), where at least one of the components (a) or (b) has functional groups having differing reactivities toward the functional groups of the other component and the reaction ratio is selected so that the addition product (A) contains an average of one group which is reactive toward isocyanate, (ii) if desired, intermolecular addition reaction of the addition product (A) to form a polyaddition product (P) containing an average of one group which is reactive toward isocyanate and an average of more than two isocyanate groups, and (iii) reaction of the addition
    Type: Grant
    Filed: March 19, 2001
    Date of Patent: March 4, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Bruchmann, Hans Renz, Rainer Königer, Ulrike Ehe, Ulrich Treuling, Rudolf Müller-Mall
  • Patent number: 7323532
    Abstract: The present invention concerns a process for producing low-viscosity polyisocyanates or secondary products thereof, which carry activated, radiation-curable double bonds and can optionally also cure thermally, and low-viscosity polyisocyanate mixtures or secondary products thereof and their use in coating compounds.
    Type: Grant
    Filed: September 29, 2003
    Date of Patent: January 29, 2008
    Assignee: Bayer MaterialScience AG
    Inventors: Thomas Fäcke, Jan Weikard, Wolfgang Fischer
  • Patent number: 7288213
    Abstract: A method is described for preparing a tricondensate polyfunctional isocyanate composition, preferably having at least an isocyanurate and/or biuret group, which includes adding to a tricondensate polyfunctional isocyanate, or a mixture of different tricondensate polyfunctional isocyantes, obtained by (cyclo)condensation, in particular (cyclo)trimerization of one or several identical or different isocyanate monomers and optionally of another monomer, an allophanate of one or several identical or different isocyanates, or a mixture of different allophanates. The isocyanates or isocyanate monomer mixtures used for preparing the polyfunctional isocyanate(s) may be identical to or different from the isocyanate(s) or isocyanate mixture used for preparing the allophanate(s).
    Type: Grant
    Filed: April 21, 1999
    Date of Patent: October 30, 2007
    Assignee: Rhodia Chimie
    Inventors: Eugénie Charriere, Jean-Marie Bernard, Denis Revelant
  • Patent number: 7179935
    Abstract: A process for the preparation of isocyanates from carbamic esters.
    Type: Grant
    Filed: February 28, 2003
    Date of Patent: February 20, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Eckhard Stroefer, Michael Ochse, Volker Krase, Andreas Schmidt, Matthias Kloetzer, Imbridt Murrar, Gisbert Franzke
  • Patent number: 7129312
    Abstract: Polyurethane compositions are produced in a two-stage method. In a first step, a diol component with a molecular weight of less than 2000 is reacted with a monomeric diisocyanate with a molecular weight of less than 500 and the unreacted monomeric diisocyanate is removed from this reaction product. In a second step, the resulting high-molecular diisocyanate is reacted with a polyol to produce a reactive prepolymer with isocyanate and groups. The addition of polyisocyanates which are capable of migration and which have a substantially lower vapor pressure than diphenylmethanediisocyanate, improves the addition behavior of the invention polyurethane compositions. Reactive polyurethane compositions of this type are suitable for using as binding agents for reactive one or two component adhesives/sealants, which may optionally contain solvents. These compositions are also suitable for producing reactive hot melt adhesives when suitable polyols are selected.
    Type: Grant
    Filed: November 25, 2000
    Date of Patent: October 31, 2006
    Assignee: Henkel Kommanditgesellschaft Auf Aktien (Henkel KGAA)
    Inventors: Michael Krebs, Christoph Lohr, Andreas Brenger
  • Patent number: 7081545
    Abstract: A process for preparing fluorochemical monoisocyanates comprises reacting at least one fluorochemical alcohol represented by the formula CnF2n+1SO2NCH3(CH2)mOH, wherein n=2 to 5, and m=2 to 4, with 4,4?-diphenylmethane diisocyanate (MDI) in a solvent in which the resulting fluorochemical monoisocyanate is not soluble; wherein the molar ratio of fluorochemical alcohol:MDI is from about 1:1 to about 1:2.5.
    Type: Grant
    Filed: December 31, 2003
    Date of Patent: July 25, 2006
    Assignee: 3M Innovative Properties Company
    Inventors: Thomas P. Klun, Alan R. Kirk, George G.I. Moore, John C. Clark, Zai-Ming Qiu
  • Patent number: 7071353
    Abstract: The present invention relates to a process for preparing polyisocyanates containing acylurea groups by reacting isocyanates corresponding to formula (I) R—(NCO)n,??(I) wherein R represents an n-valent linear or branched aliphatic group or cycloaliphatic group having 4 to 30 carbon atoms or an aromatic group having 6 to 24 carbon atoms and n is 1, 2, 3 or 4, with aliphatic and/or aromatic carboxylic acids in the presence of a metal salt catalyst at a temperature of 20 to 220° C. The present invention also relates to the reaction products (polyisocyanates) prepared by this process and to their use as binders for polyurethane coating compositions.
    Type: Grant
    Filed: February 28, 2002
    Date of Patent: July 4, 2006
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christoph Gürtler, Martin Brahm
  • Patent number: 7038003
    Abstract: A process for preparing polyisocyanate prepolymers containing allophanate structural units that includes reacting a) one or more polyisocyanates with b) one or more polyetherpolyols containing less than or equal to 0.02 milliequivalent of unsaturated end groups per gram of polyol and having a polydispersity of from 1.0 to 1.5 and/or an OH functionality of greater than or equal to 1.9 ?to provide an NCO-functional polyurethane prepolymer containing urethane groups that are partly or fully allophanatized by further reaction with c) polyisocyanates, which may be different from those from a), and d) catalysts and optionally adding e) acidic additives before, during and/or after the allophanatization. The polyisocyanate prepolymers can be used to produce coatings, adhesive bonds and/or seals. The coatings include one or more of the polyisocyanate prepolymers, and at least one diol or polyol and/or at least one linear and/or cyclic, aliphatic, araliphatic and/or aromatic diamine or polyamine.
    Type: Grant
    Filed: March 23, 2005
    Date of Patent: May 2, 2006
    Assignee: Bayer MaterialScience AG
    Inventors: Michael Mager, Joachim Simon, Malte Homann
  • Patent number: 7030266
    Abstract: The invention relates to a method for making oligomeric isocyanates by reacting diisocyanates in the presence of a catalyst, wherein the catalyst comprises a saline compound prepared from a five-membered N-heterocycles and the N-heterocycle comprises at least one N—H function in the five-membered ring, to the products produced in this way and to polymers prepared from these products.
    Type: Grant
    Filed: May 13, 2002
    Date of Patent: April 18, 2006
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jürgen Köcher, Frank Richter, Hans-Josef Laas, Matthias Wintermantel
  • Patent number: 7022874
    Abstract: A process for the preparation of polyisocyanates which contain one or more biuret groups, by reacting a) an aliphatic or cycloaliphatic isocyanate containing two or more isocyanate groups (isocyanate a) with b) a tertiary alcohol or a mixture of water and a tertiary alcohol (biuretizing agent b) at from 100 to 250° C.
    Type: Grant
    Filed: February 1, 1996
    Date of Patent: April 4, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Bruchmann, Stefan Wolff, Wolfgang Heider, Joachim Jähme, Werner Langer, Hans Renz
  • Patent number: 7019164
    Abstract: The present invention relates to a process for the production of an isocyanate corresponding to the formula R(NCO)n wherein R represents a (cyclo)aliphatic or aromatic hydrocarbon residue having up to 15 carbon atoms, preferably 4 to 13 carbon atoms, provided that there are at least 2 carbon atoms arranged between each of the nitrogens and n represents the number 2 or 3, by a) separately heating an amine corresponding to the formula R(NH2)n, wherein R and n are as previously defined, in vapor form, optionally diluted with an inert gas or the vapors of an inert solvent, and phosgene to temperatures of 200° C. to 600° C.
    Type: Grant
    Filed: December 11, 2002
    Date of Patent: March 28, 2006
    Assignee: Bayer Aktiengesellschaft
    Inventors: Martin Friedrich, Herbert Stutz
  • Patent number: 6991746
    Abstract: The present invention relates to a new high functionality MDI. In particular, this invention relates to polymeric allophanates based on diphenylmethane diisocyanate having an NCO group content of 12 to 30%, prepolymers thereof, and processes for the production of these compositions. The prepolymers are stable liquids having NCO group contents of about 10 to about 28%.
    Type: Grant
    Filed: March 4, 2005
    Date of Patent: January 31, 2006
    Assignee: Bayer MaterialScience LLC
    Inventors: William E. Slack, Hersel T. Kemp, II, William E. Miller
  • Patent number: 6974880
    Abstract: The present invention relates to a process for the manufacture of diisocyanates by phosgenation of the corresponding diamines in which the vaporous diamines, optionally rarefied with an inert gas or with the vapors of an inert solvent, and phosgene are heated separately to temperatures of about 200° C. to about 600° C. and mixed and reacted in a tube reactor characterized in that a number n?2 of nozzles directed parallel to the axis of the tube reactor are arranged in the tube reactor, the diamine-containing stream being fed into the tube reactor through the n nozzles and the phosgene stream being fed into the tube reactor through the remaining free space.
    Type: Grant
    Filed: February 17, 2004
    Date of Patent: December 13, 2005
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Biskup, Peter Keldenich, Peter Fuhrmann, Christian Six
  • Patent number: 6916953
    Abstract: Process for preparing organic isocyanates, which comprises the steps (a) making available a first partial amount of chlorine, with the chlorine of this first partial amount having a content of free and bound bromine and iodine of <400 ppm; (b) making available a second partial amount of chlorine; (c) reacting the first and second partial amounts of chlorine with carbon monoxide to form phosgene; (d) reacting the phosgene from step (c) with one or more primary amines to form the corresponding isocyanates and hydrogen chloride; (e) separating off and, if necessary, purifying the isocyanates formed in step (d); (f) separating off and, if necessary, purifying the hydrogen chloride formed in step (d); (g) catalytically oxidizing at least part of the hydrogen chloride separated off in step (e) by means of oxygen to form chlorine; (h) separating off the chlorine formed in step (g) and using at least a partial amount of the chlorine which has been separated off as second partial amount of chlorine in step (b).
    Type: Grant
    Filed: August 27, 2002
    Date of Patent: July 12, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Christian Walsdorff, Martin Fiene, Eckhard Ströfer, Klaus Harth, Jan D. Jacobs, Filip Deberdt
  • Patent number: 6887399
    Abstract: The present invention relates to a new high functionality MDI. In particular, this invention relates to polymeric allophanates based on diphenylmethane diisocyanate having an NCO group content of 12 to 30%, prepolymers thereof, and processes for the production of these compositions. The prepolymers are stable liquids having NCO group contents of about 10 to about 28%.
    Type: Grant
    Filed: September 9, 2002
    Date of Patent: May 3, 2005
    Assignee: Bayer MaterialScience LLP
    Inventors: William E. Slack, Hersel T. Kemp, II, William E. Miller
  • Patent number: 6867324
    Abstract: Starting material streams are mixed in a mixer (13) for the phosgenation of amines by a process in which the reaction product (3) is removed in a closed loop and the starting material streams (1.2) contain organic solvents. The main streams (1.1, 2.1) and/or part-streams (1.2, 2.2) of the starting materials (1, 2) come into contact with one another according to the countercurrent principle.
    Type: Grant
    Filed: May 21, 2001
    Date of Patent: March 15, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Wölfert, Ulrich Penzel
  • Patent number: 6852823
    Abstract: Polyurethanes or polyurethane-ureas prepared from: (a) polytrimethylene ether glycol having a number average molecular weight in the range of about 1,000 to about 4,000 and unsaturated end groups in the range of about 0.003 to about 0.015 meq/g; (b) diisocyanate; and (c) diol or diamine chain extender; and their manufacture, intermediates and use.
    Type: Grant
    Filed: August 9, 2002
    Date of Patent: February 8, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Hari B. Sunkara, Edwin L. McInnis
  • Publication number: 20040167354
    Abstract: The present invention relates to a process for the manufacture of diisocyanates by phosgenation of the corresponding diamines in which the vaporous diamines, optionally rarefied with an inert gas or with the vapors of an inert solvent, and phosgene are heated separately to temperatures of about 200° C. to about 600° C. and mixed and reacted in a tube reactor characterized in that a number n≧2 of nozzles directed parallel to the axis of the tube reactor are arranged in the tube reactor, the diamine-containing stream being fed into the tube reactor through the n nozzles and the phosgene stream being fed into the tube reactor through the remaining free space.
    Type: Application
    Filed: February 17, 2004
    Publication date: August 26, 2004
    Inventors: Klaus Biskup, Peter Keldenich, Peter Fuhrmann, Christian Six
  • Publication number: 20040133036
    Abstract: A process for preparing hydroxyalkyl carboxylates comprises reacting a carboxylic acid with an alkylene oxide in the presence of a multimetal cyanide compound of the formula I
    Type: Application
    Filed: October 6, 2003
    Publication date: July 8, 2004
    Inventors: Michael Zirstein, Georg Heinrich Grosch, Edward Bohres, Alfred Oftring, Stefan Birnbach, Werner Bochnitschek, Oliver Borzyk, Rainer Corell, Harald Wurz, Thomas Heidemann, Marcus Sigl
  • Patent number: 6750367
    Abstract: The present invention relates to novel aromatic isocyanates obtained by partially hydrogenating naphthalene as well as the processes for preparing the same, and to their use as an isocyanate component in the production of polyurethanes.
    Type: Grant
    Filed: May 9, 2002
    Date of Patent: June 15, 2004
    Assignee: Bayer Polymers LLC
    Inventors: Rick L. Adkins, Harold R. Parsons
  • Patent number: 6743374
    Abstract: A self-emulsifiable polyisocyanate with high functionality, having the average number of functional groups in 4.3 or more and a viscosity of 8,000 mPa·s (at 25° C.) or less, which is obtained by subjecting a modified polyisocyanate containing allophanate bonds and a poly(oxyalkylene)glycol monoalkyl ether (e) having oxyethylene bonds in a total amount of 30 mole % or more in its molecule to a urethanization reaction, said modified polyisocyanate being obtained by reacting a polyol (a) having the average number of functional groups in an amount of 2 or more with an organic polyisocyanate (b) in the presence of an allophanate-forming catalyst (c) comprising a zirconium carboxylate; and a process for producing the same.
    Type: Grant
    Filed: July 31, 2002
    Date of Patent: June 1, 2004
    Assignee: Nippon Polyurethane Industry Co., Ltd.
    Inventors: Motomu Kita, Mitsushige Ikemoto, Toshiaki Sasahara
  • Patent number: 6710151
    Abstract: The end-blocked isocyanate prepolymer having an oxadiazine ring according to the present invention is characterized in that at least one of isocyanate groups of a NCO-terminated isocyanate prepolymer, which has NCO groups at the ends and comprises units derived from an oxadiazinetrione compound (A) represented by the following formula (1) and units derived from an active hydrogen compound (B) represented by the following formula (2), is blocked with a unit derived from an end-blocking agent (C) having at least one active hydrogen in one molecule, and that the end-blocked isocyanate prepolymer has a softening point of not lower than 50° C.
    Type: Grant
    Filed: November 12, 2002
    Date of Patent: March 23, 2004
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Toshiaki Kuwatsuka, Hideaki Ogata, Manabu Shimoda, Ryuuji Haseyama, Izumi Mega
  • Publication number: 20040014970
    Abstract: The invention concerns a method for preparing polyisocyanates by cyclodimerization of isocyanate functions borne by initial monomer isocyanates. The invention is characterised in that it comprises steps which consist in: a) providing a reaction medium comprising initial monomer isocyanates, optionally in the presence of a solvent; b) adding to said reaction mixture a (cyclo)dimerization catalyst comprising a compound of the family of super acids; c) heating the reaction medium to a temperature ranging between 0° C. and 300° C., advantageously between 20° C. and 200° C. until the desired rate of transformation is obtained; d) optionally inactivating or eliminating the reaction catalyst; and e) optionally eliminating the unreacted monomer.
    Type: Application
    Filed: May 19, 2003
    Publication date: January 22, 2004
    Inventor: Jean-Marie Bernard
  • Patent number: 6639102
    Abstract: Polyisocyanates of the diphenyl methane series having reduced color values are obtained by a) reacting aniline and formaldehyde in the presence of an acid catalyst to form a polyamine, b) neutralizing the reaction mixture containing polyamine with a base, c) separating the neutralized mixture into the aqueous and the organic phases, d) adding a base to the organic phase and then e) phosgenating the resulting polyamine to produce the corresponding polyisocyanate.
    Type: Grant
    Filed: March 10, 2003
    Date of Patent: October 28, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Torsten Hagen, Friedhelm Kämper, Daniel Koch, Rudolf Uchdorf, Stefan Wershofen
  • Patent number: 6590098
    Abstract: The invention relates to a method of preparing an aliphatic polyisocyanate by conversion of an aliphatic diisocyanate to a polyisocyanates in the presence of a catalyst, wherein the catalyst contains a saline compound having 5 to 97.1 wt. % of a 1,2,3- and/or a 1,2,4-triazolate (calculated as C2N3, molecular weight 66) in the anion, the isocyanates thus prepared and the polyurethane paints and coatings containing them.
    Type: Grant
    Filed: May 13, 2002
    Date of Patent: July 8, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Frank Richter, Reinhard Halpaap, Jürgen Köcher, Hans-Josef Laas
  • Patent number: 6569352
    Abstract: Disclosed are polyester-ether polyols and their use in urethane prepolymers, urethane foams and non-foam urethane coatings, adhesives, sealants and/or elastomers. Methods for producing such polyester-ether polyols are disclosed, along with methods for producing urethane prepolymers. The polyester-ether polyols of the instant invention are preferably the reaction product of phthalic anhydride, diethylene glycol, and propylene oxide. These polyester-ether polyols are useful as either the primary polyol in urethane compositions or in combination with conventional auxiliary polyester- and/or polyether-based polyols. The polyester-ether polyols impart greatly improved solubility and compatibility to mixtures of either polyether and/or polyester polyols. The polyester-ether polyols of the instant invention are desirably of lower viscosity than their precursor intermediate polyester polyols and are generally soluble in either polyester- and/or polyether-based polyols.
    Type: Grant
    Filed: October 25, 1999
    Date of Patent: May 27, 2003
    Assignee: Stepan Company
    Inventors: Douglas K. Hillshafer, George Magnus
  • Patent number: 6559264
    Abstract: The present invention relates to blocked polyisocyanate crosslinking agents, to the production thereof and to the use thereof in single-component stoving lacquers, particularly OEM clear lacquers (original equipment material, initial lacquer coating).
    Type: Grant
    Filed: August 2, 2001
    Date of Patent: May 6, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Eberhard König, Hans-Ulrich Meier-Westhues, Thomas Klimmasch
  • Publication number: 20030065124
    Abstract: The invention is directed to polyurethane prepolymers having a reduced amount of unreacted monomeric diisocyanate, particularly diphenylmethane diisocyanate (MDI), prepared by distilling the prepolymer reaction product in the presence of at least one inert solvent whose boiling point is slightly below that of the monomeric diisocyanate; and to high performance cast polyurethane elastomers from the thus obtained prepolymers using diamine and/or diol chain extenders.
    Type: Application
    Filed: August 2, 2001
    Publication date: April 3, 2003
    Inventors: Ronald O. Rosenberg, Rui Xie, Ajaib Singh
  • Patent number: 6541532
    Abstract: New, useful and surprisingly effective antiscorch compositions for utilization within polyurethane foam production methods which utilize very popular tertiary amine catalysts are provided. Such compositions require the presence of nominal yet effective amounts of organic cyclic ester materials. The ring systems of such materials appear to open during exposure to heat (during the curing process) and release carboxylic acids into the curing formulation. The tertiary amines become quenched by the carboxylic acids and thus do not exhibit heat destabilization. The resultant foams exhibit extremely low, if no, areas of excessive heating (i.e., scorch) and thus are substantially uniformly colored throughout. The processes and resultant foams are also contemplated within this invention.
    Type: Grant
    Filed: June 2, 2000
    Date of Patent: April 1, 2003
    Assignee: Milliken & Company
    Inventors: Mark E. Ragsdale, Sandy G. Belue
  • Patent number: 6515125
    Abstract: This invention relates to storage-stable, liquid, partially trimerized polyisocyanates having an NCO group content of 24 to 40% by weight, and comprising 20 to 88% by weight of toluene diisocyanate and 12 to 80% by weight of a polyisocyanate of the diphenylmethane series. The present invention also relates to a process for the preparation of the storage-stable, liquid, partially trimerized polyisocyanates; to storage-stable, liquid urethane prepolymers of these partially trimerized polyisocyanates; and to a process for the production of these storage-stable, liquid, urethane prepolymers.
    Type: Grant
    Filed: March 9, 2001
    Date of Patent: February 4, 2003
    Assignee: Bayer Corporation
    Inventors: William E. Slack, Hersel T. Kemp, II, Kenneth P. Yonek
  • Patent number: 6515164
    Abstract: A low-monomer PU prepolymer containing free NCO groups which is obtained from polyhydric alcohols and diisocyanates differing in their reactivity and which is distinguished by the ratio of the NCO groups of the partly slower-reacting diisocyanate to the NCO groups of the faster-reacting diisocyanate. It is greater than 6:1. Nevertheless the prepolymer according to the invention cures more quickly than a known prepolymer predominantly containing fast-reacting NCO groups. In a preferred embodiment, TDI is used as the partly slower-reacting diisocyanate while MDI is used as the faster-reacting diisocyanate. The prepolymer is produced in two stages. The prepolymer according to the invention is suitable for bonding plastic articles, metals and paper, especially films. The accelerated absence of migration is particularly noticeable in this regard.
    Type: Grant
    Filed: July 2, 1999
    Date of Patent: February 4, 2003
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Gerd Bolte, Guenter Henke, Markus Kruedenscheidt, Astrid Omoruyi
  • Patent number: 6509433
    Abstract: The present invention relates to blocked fluorine-containing polyisocyanates which have a fluorine content, calculated as F=19, of 1.0 to 20.0 wt. %, preferably 4.0 to 10.0 wt. %, and are suitable for preparing stoving coatings having a water- and soil-repellent surface, wherein the fluorine-containing polyisocyanates are based on the reaction product of aliphatic polyisocyanates or polyisocyanate mixtures having an NCO content of 10 to 25 wt. % and a functionality of at least 2.5 with monofunctional isocyanate blocking agents and a fluorinated monoalcohols wherein i) 75 to 95 equivalent-% of the isocyanate groups are reacted with isocyanate blocking agents, ii) 5 to 25 equivalent-% of the isocyanate groups are reacted with fluorinated monoalcohols and iii) the equivalents of i) and ii) add up to 100%.
    Type: Grant
    Filed: September 14, 2001
    Date of Patent: January 21, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Eberhard Koenig, Beate Baumbach, Christian Füssel, Juan Gonzalez-Blanco
  • Patent number: 6489503
    Abstract: The present invention provides a liquid methylene bis(phenylisocyanate) composition including a high concentration of methylene bis(phenylisocyanate) which has an improved storage stability. The invention further provides a method of making the liquid methylene bis(phenylisocyanate) compositions of the present invention.
    Type: Grant
    Filed: November 9, 1999
    Date of Patent: December 3, 2002
    Assignee: BASF Corporation
    Inventors: Thirumurti Narayan, Anthony Lunato, Jon S. Speier, David D. Peters, Cynthia Loop, Filip Nevejans
  • Publication number: 20020133042
    Abstract: Highly functional aromatic polyisocyanates are prepared by reacting aromatic polyisocyanates, if required as a mixture with further mono- and/or polyisocyanates, with addition of catalytic acidic substances and water, by a process wherein the aromatic polyisocyanates used comprise at least one tolylene diisocyanate and the catalytic acidic substance used is at least one alkyl and/or aralkyl phosphate, and the process is carried out in such a way that the water is added with a temperature/time gradient increase from 5 to 60°/hour and until an isocyanate modification of the starting NCO terminal groups from 1 to 80% is established.
    Type: Application
    Filed: December 17, 2001
    Publication date: September 19, 2002
    Inventors: Imbridt Murrar, Heinz Plaumann, Jurgen Winkler, Marita Schuster
  • Patent number: 6426414
    Abstract: The present invention relates to water dispersible polyisocyanate mixtures prepared from aliphatic, cycloaliphatic, araliphatic and/or aromatic diisocyanates and having a) an average isocyanate functionality of at least 2.0, b) a content of 5.0 to 25.0 wt. %, based on resin solids, of isocyanate groups (calculated as NCO; molecular weight=42) and c) a content of 2 to 50 wt. %, based on resin solids, of ethylene oxide units calculated as C2H2O; molecular weight 44) incorporated within polyether chains containing an average of 5 to 35 ethylene oxide units, wherein at least 60 mole % of the polyether chains are connected via allophanate groups to two polyisocyanate molecules which are each prepared from at least two diisocyanate molecules. The present invention also relates to a process for the preparation of these water dispersible polyisocyanate.
    Type: Grant
    Filed: May 14, 1999
    Date of Patent: July 30, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Laas, Reinhard Halpaap, Christian Wamprecht
  • Patent number: 6420508
    Abstract: The present invention relates to polyisocyanate mixtures prepared from aliphatic and/or cycloaliphatic diisocyanates and having a) an average isocyanate functionality of at least 2.0, b) a content of isocyanate groups (calculated as NCO; molecular weight=42) of 4.0 to 28.0 wt. % and c) a content of alkoxy groups having up to 36 carbon atoms of 2.0 to 37.5 wt. %, wherein the alkoxy groups are constituents of allophanate groups or optionally urethane groups, provided that >50 mol % of the alkoxy groups are a constituent of allophanate groups that are connected to at least two polyisocyanate molecules which are each prepared from at least two diisocyanates. The present invention also relates to a process for preparing these polyisocyanate mixtures and to coating compositions, which are highly diluted or dilutable with non-polar solvents and contain these polyisocyanate mixtures and lacquer binders or binder components optionally containing isocyanate-reactive groups.
    Type: Grant
    Filed: June 8, 2000
    Date of Patent: July 16, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karsten Danielmeier, Lutz Schmalstieg, Hans-Josef Laas, Harald Mertes, Reinhard Jahn
  • Patent number: 6417313
    Abstract: Low-monomer, NCO-containing prepolymers based on 1,4-diisocyanato-2,2,6-trimethylcyclohexane, a process for their preparation, and their use.
    Type: Grant
    Filed: March 29, 2001
    Date of Patent: July 9, 2002
    Assignee: Degussa AG
    Inventor: Emmanouil Spyrou