Processes Patents (Class 560/336)
  • Patent number: 6410095
    Abstract: The present invention relates to substantially solvent-free binder compositions containing a) a polyisocyanate component containing heteroallophanate groups and having aromatically-bound isocyanate groups, i) an NCO content of 3 to 16%, ii) an average functionality of 1.8 to 4, iii) an allophanate group content (calculated as C2N2O3, MW: 101) of 5 to 35% and iv) a hydrocarbon chain content of 10 to 65%, wherein the hydrocarbon chains are attached to allophanate groups via oxygen and have an average of 2 to 23 carbon atoms and b) an isocyanate-reactive component. The present invention also relates to the use of these binder compositions in one- and two-component coating compositions.
    Type: Grant
    Filed: September 6, 1996
    Date of Patent: June 25, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Martin Brahm, Gerhard Ruttmann, Lutz Schmalstieg
  • Patent number: 6376567
    Abstract: This invention relates to novel polyisocyanate compositions, to a process for these polyisocyanate compositions, to a process for the production of cold cure flexible molded foams wherein this novel polyisocyanate composition comprises the polyisocyanate component, and to the cold cure flexible molded foams produced by this process.
    Type: Grant
    Filed: December 7, 2000
    Date of Patent: April 23, 2002
    Assignee: Bayer Corporation
    Inventors: Joachim Werner, Ronald Zibert
  • Publication number: 20020035232
    Abstract: The invention concerns an isocyanate composition at least partially masked, characterized in that it is masked by at least two agents, one of which at least has a non-carbon carboxylic function. The invention is applicable to organic synthesis.
    Type: Application
    Filed: October 9, 2001
    Publication date: March 21, 2002
    Inventor: Jean-Marie Bernard
  • Publication number: 20020007036
    Abstract: High-functionality polyisocyanates are prepared by a process which comprises
    Type: Application
    Filed: March 19, 2001
    Publication date: January 17, 2002
    Inventors: Bernd Bruchmann, Hans Renz, Rainer Koniger, Ulrike Ehe, Ulrich Treuling, Rudolf Muller-Mall
  • Publication number: 20010041810
    Abstract: The present invention relates to a process for preparing a low boiling monoisocyanate having a boiling point of between 70 and 320° C.
    Type: Application
    Filed: April 30, 2001
    Publication date: November 15, 2001
    Inventors: Martin Brahm, Lutz Schmalstieg, Ulrich Geron, Hans-Gunter Behr, Jorg Morawski
  • Patent number: 6316573
    Abstract: An adhesive paste, free of water, based on a reaction product of a polyisocyanate component and a co-reactant selected from the group consisting of a polyol, a monofunctional fatty derivative component and mixtures thereof, wherein the reaction product contains moisture reactive isocyanate groups.
    Type: Grant
    Filed: August 24, 1998
    Date of Patent: November 13, 2001
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Wolfgang Klauck, Wolfgang Maier
  • Publication number: 20010039325
    Abstract: Unique masked isocyanates well suited for formulation into a variety of coating compositions, for example paint powders, are prepared by condensing an isocyanate with a ring-hydroxylated aromatic compound bearing at least one substituent which comprises a carbonyl or nitrile functional group and the apparent melting point of which being at least 30° C.
    Type: Application
    Filed: October 29, 1997
    Publication date: November 8, 2001
    Inventors: PIERRE ARDAUD, JEAN-MARIE BERNARD
  • Publication number: 20010034429
    Abstract: Polyisocyanates of the formula (I) (polyisocyanate I),
    Type: Application
    Filed: January 26, 2001
    Publication date: October 25, 2001
    Applicant: BASF Aktiengesellschaft
    Inventors: Bernd Bruchmann, Hans Renz, Gunter Mohrhardt, Hubert Baumgart, Simone Bitter
  • Publication number: 20010027242
    Abstract: Low-monomer, NCO-containing prepolymers based on 1,4-diisocyanato-2,2,6-trimethylcyclohexane, a process for their preparation, and their use.
    Type: Application
    Filed: March 29, 2001
    Publication date: October 4, 2001
    Applicant: Degussa AG
    Inventor: Emmanouil Spyrou
  • Patent number: 6284811
    Abstract: A polyester-polyol being liquid at 40° C. and having a viscosity of not more than 10,000 mPa·s at 60° C., prepared by polycondensation of an acid component including at least one phthalic acid component selected from phthalic anhydride and o-phthalic acid, and an aliphatic polybasic acid, with a polyhydric alcohol; a process for preparing a polyurethane foam including reacting a polyisocyanate component with a polyol component including the polyester-polyol; a process for preparing an isocyanate prepolymer from a polyisocyanate component and a polyol component including the polyester-polyol; and a process for preparing a polyurethane foam including reacting an isocyanate prepolymer prepared from a polyisocyanate component and a polyol component including the polyester-polyol, with a polyol component. The resulting polyurethane foam shows remarkably improved physical properties such as tensile strength and tear strength, while having low density, acceptable appearance and texture.
    Type: Grant
    Filed: May 17, 2000
    Date of Patent: September 4, 2001
    Assignee: Kao Corporation
    Inventors: Minoru Sawai, Makoto Okubo, Kenichi Miyamoto, Kazunari Takemura, Masahiro Mori
  • Patent number: 6274759
    Abstract: Diisocyanates of the formula (I) where R1 is a C1-C10-hydrocarbon radical and R3 is a C1-Cl2-hydrocarbon group and n is an integer from 1 to 10, are described.
    Type: Grant
    Filed: January 21, 1999
    Date of Patent: August 14, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Hermann Graf, Udo Rotermund, Günter Mohrhardt
  • Patent number: 6271414
    Abstract: A process is described for obtaining pure isocyanate isomers from a mixture of isocyanate isomers by suspension crystallization and the isolation of isomerically pure crystals, which is characterized in that, prior to the isolation of the crystals, 5 to 40% by weight of the crystals produced are remelted while simultaneously increasing the temperature of the crystal slurry by 4.5 to 9° C.
    Type: Grant
    Filed: April 29, 1999
    Date of Patent: August 7, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rüdiger Drope, Dieter Grenner, Hartmut Hetzel, Hans-Peter Schal, Gerhard Wegener
  • Patent number: 6242641
    Abstract: The present invention relates to compounds selected from formula I wherein R1, R2, R3 and R4 are the same or different and represent hydrogen, C1, to C6-alkyl, C5 to C6-cycloalkyl, phenyl and halogen, m and n are the same or different and represent the 2, 3, 4 or 5, X, A and B represent carbon and Y1, Y2, Z1 and Z2 are the same or different and represent hydrogen, hydroxyl (OH), amino (NH2), isocyanato (NCO) or 4-hydroxyphenyl.
    Type: Grant
    Filed: March 22, 1999
    Date of Patent: June 5, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Jautelat, Carl Casser, Hanns-Peter Müller, Manfred Hajek
  • Patent number: 6127463
    Abstract: The present invention relates to an improved process for the production of light colored polymethylene polyphenyl polyisocyanates. This process comprises adding a compound that contains an epoxide group to the process at any point prior to quench cooling the formed polyisocyanates.
    Type: Grant
    Filed: March 23, 1999
    Date of Patent: October 3, 2000
    Assignee: Bayer Corporation
    Inventors: Rick L. Adkins, Clarence D. Blue
  • Patent number: 6120699
    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: September 21, 1998
    Date of Patent: September 19, 2000
    Assignee: BASF Corporation
    Inventors: Thirumurti Narayan, Anthony Lunato, Jon S. Speier, David D. Peters, Cynthia Loop, Filip Nevejans
  • 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: 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: 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: 5756636
    Abstract: A substantially solid free isocyanate prepolymer is made by reacting an isocyanate mixture which is made up of a toluene diisocyanate residue containing monomeric toluene diisocyanate and optionally, additional monomeric toluene diisocyanate in an amount such that the total NCO content is at least 37% with a polyether polyol having an ethylene oxide content of at least 30%. The polyether polyol has a molecular weight of from about 200 to about 6,000 and a functionality of from 2 to 6. The product prepolymers are particularly useful in the production of polyurethanes.
    Type: Grant
    Filed: December 27, 1996
    Date of Patent: May 26, 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: 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: 5750629
    Abstract: The present invention relates to a process for preparing pure bis(isocyanatoalkyl)monouretdiones corresponding to formula (I) ##STR1## wherein R represents identical or different, linear or branched alkyl groups having 4 to 9 carbon atoms,by oligomerizing at least a portion of the isocyanate groups of aliphatic diisocyanates in the presence of catalysts which accelerate the dimerization of isocyanate groups, terminating the reaction at the desired degree of oligomerization, removing unreacted excess diisocyanate by extraction or thin film distillation to obtain a distillation residue, subjecting the distillation residue to thin film distillation at a temperature of 160.degree. to 220.degree. C. and a pressure of 0.01 to 1.0 mbar and obtaining bis(isocyanato-alkyl)monouretdiones corresponding to formula (I) as the distillate.
    Type: Grant
    Filed: January 23, 1997
    Date of Patent: May 12, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Laas, Reinhard Halpaap, Josef Pedain, Klaus Konig
  • 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: 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: 5606001
    Abstract: The present invention relates to a polyisocyanates containing allophanate groups and optionally isocyanurate groups that are prepared by reacting compounds whichi) are substantially free of hydroxyl groups and isocyanate groups,ii) have an average of at least two urethane groups per molecule andiii) are the reaction products of linear or branched, aliphatic isocyanates with organic hydroxyl compounds,with an excess quantity, based on the urethane groups, of 4,4'-bis-(isocyanatocyclohexyl)-methane to form polyisocyanates containing allophanate groups and optionally isocyanurate groups and optionally removing at least a portion of the unreacted excess 4,4'-bis-(isocyanatocyclohexyl)-methane. The present invention also relates to a process for the production of these polyisocyanates and to their use as binders or binder components in coating compositions.
    Type: Grant
    Filed: September 14, 1995
    Date of Patent: February 25, 1997
    Assignee: Bayer Corporation
    Inventor: Myron W. Shaffer
  • Patent number: 5606004
    Abstract: A process for preparing liquid lacquer polyisocyanates with aliphatically and aromatically bound isocyanate groups and an NCO content of 5 to 25 wt. % by trimerizing an isocyanate component A), containing A1) 70 to 100 wt. % of diisocyanatotoluene and A2) 0 to 30 wt. % of other aromatic isocyanates and B) aliphatic lacquer polyisocyanates, optionally with prior, simultaneous and/or subsequent reaction of a portion of the isocyanate groups with an alcohol component C) having a molecular weight of 32 to 900, and optionally in the presence of D) inert solvents; the resulting lacquer polyisocyanates; and their use in coating compositions, in particular as a cross-linking agent for polyhydroxyl compounds in two-component polyurethane coating compositions.
    Type: Grant
    Filed: July 31, 1995
    Date of Patent: February 25, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Martin Brahm, Josef Pedain, Lutz Schmalstieg
  • 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: 5534185
    Abstract: Method for preparation of fluorochlorohydrocarbon-free (FCHC-free) low-density polyurethane soft-foam materials and soft-elastic polyurethane soft-foam materials as well as polyisocyanate mixtures modified with urethane groups, and based on diphenylmethane-diisocyanate, which are applicable thereto.
    Type: Grant
    Filed: September 21, 1994
    Date of Patent: July 9, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Hinz, Ruth Zschiesche, Heinz-Dieter Lutter, Bernd Bruchmann
  • Patent number: 5386057
    Abstract: The invention concerns a process for the preparation of acyl isocyanates which consists of reacting oxalyl chloride with a salt selected from the group consisting of hydrohalides and sulphates of carboxamides and/or carbamates, unsubstituted on nitrogen, then heating the reaction mixture at a temperature between 30.degree. and 150.degree. C. The process is suitable for preparation of acyl isocyanates with excellent yields in easy to control operational conditions.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: January 31, 1995
    Assignees: Societe Nationale des Poudres et Explosifs, Nippon Paint Co. Ltd.
    Inventors: Philippe Le Goff, Daniele Dewilde, Noriyuki Tsuboniwa, Satoshi Urano
  • Patent number: 5300616
    Abstract: Polyisocyanate mixtures are isolated in pure or more concentrated form from isomeric mixtures by liquid-liquid extraction using a two-phase system. The two phases are 1) a non-polar solvent phase and 2) a polar solution in which a hydrogen halide is present. In a preferred embodiment, the extraction is carried out in a countercurrent extractor.
    Type: Grant
    Filed: December 30, 1992
    Date of Patent: April 5, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventor: Wolfgang Friederichs
  • Patent number: 5298651
    Abstract: A process for preparing isocyanates comprising (a) contacting carbon dioxide and a primary amine in the presence of an aprotic organic solvent and a phosphazene compound or a mixture of a phosphazene compound and an organic, nitrogenous base selected from the group consisting of guanidine compounds, amidine compounds, tertiary amines, pyridine and mixtures thereof to produce the corresponding ammonium carbamate salt, and (b) reacting the ammonium carbamate salt with an electrophilic or oxophilic dehydrating agent to produce the corresponding isocyanate. A second embodiment comprises recovering the ammonium carbamate salt of step (a) prior to reacting the ammonium carbamate salt with an electrophilic or oxophilic dehydrating agent in the presence of an aprotic organic solvent and a phosphazene compound or a mixture of a phosphazene compound and an organic, nitrogenous base selected from the group consisting of guanidine compounds, amidine compounds, tertiary amines, pyridine and mixtures thereof.
    Type: Grant
    Filed: October 15, 1992
    Date of Patent: March 29, 1994
    Assignee: Monsanto Company
    Inventors: William D. McGhee, Thomas E. Waldman
  • Patent number: 5288742
    Abstract: The invention concerns .alpha.,.alpha.-dialkylbenzyl derivatives of the formula I ##STR1## wherein Ar.sup.1 is phenyl or naphthyl, or a 10-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from nitrogen, oxygen and sulphur;A.sup.1 is a direct link to X.sup.1 or is (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;the phenylene group may optionally bear one or two substituents R.sup.3 ;each of R.sup.1 and R.sup.2, which may be the same or different, is (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, fluoro-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl, provided that both of R.sup.1 and R.sup.2 are not methyl or fluoromethyl; andQ is cyano, amino, nitro, formyl, (1-4C)alkoxy, thiazolyl or (2-4C)alkanoyl;or a pharmaceutically-acceptable salt thereof;processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.
    Type: Grant
    Filed: March 18, 1992
    Date of Patent: February 22, 1994
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Philip N. Edwards, David Waterson
  • Patent number: 5233010
    Abstract: A process for preparing an isocyanate having at least two --N.dbd.C.dbd.O groups is provided which comprises preparing a substituted aromatic amine having at least two --NH.sub.2 groups, recovering the substituted aromatic amine having at least two --NH.sub.2 groups, and preparing an isocyanate from the substituted aromatic amine having at least two --NH.sub.2 groups by (1) contacting the substituted aromatic amine with CO.sub.2 under conditions sufficient to produce the corresponding ammonium carbamate salt, and reacting the ammonium carbamate salt with an electrophilic or oxophilic dehydrating agent under conditions sufficient to produce the corresponding isocyanate, or (2) contacting the substituted aromatic amine with CO.sub.
    Type: Grant
    Filed: October 15, 1992
    Date of Patent: August 3, 1993
    Assignee: Monsanto Company
    Inventors: William D. McGhee, Michael K. Stern, Thomas E. Waldman
  • Patent number: 5233079
    Abstract: Disclosed herein is a free-flowing solid of 4,4'-diisocyanato dicyclohexylmethane consisting essentially of at least 90 percent of the trans,trans isomer.
    Type: Grant
    Filed: October 8, 1991
    Date of Patent: August 3, 1993
    Assignee: Miles Inc.
    Inventors: Stephen D. Seneker, Peter H. Markusch
  • Patent number: 5223635
    Abstract: Process for the removal of isocyanic acid from a gaseous mixture of isocyanic acid and ammonia by introducing a tertiary amine or ether at 250.degree. to 600.degree. C. The gaseous reaction mixture is passed into an inert diluent and cooled, to condense an adduct of isocyanic acid and tertiary amine or ether, and the ammonia being removed as a gas.
    Type: Grant
    Filed: September 25, 1991
    Date of Patent: June 29, 1993
    Assignee: Chemie Linz Gesellschaft m.b.H.
    Inventors: Martin Mullner, Gerhard Stern, Erich Schulz
  • Patent number: 5149805
    Abstract: Monoblocked diisocyanates which contain little free and diblocked diisocyanate are obtained by a process which involves adding 1 mole of a blocking agent to a diisocyanate which is present in excess and subsequently removing the excess diisocyanate by thin film evaporation. The compounds produced are useful for the production of cataphoresis resins.
    Type: Grant
    Filed: September 13, 1988
    Date of Patent: September 22, 1992
    Assignee: Huels Aktiengesellschaft
    Inventors: Rainer Gras, Elmar Wolf, Josef Disteldorf, Werner Huebel, Horst Schnurbusch
  • Patent number: 5096994
    Abstract: The present invention relates to polyisocyanates which contain ester groups and havea) a content of aliphatically bound isocyanate groups of 18 to 33% by weight,b) an average NCO functionality of 4.1 to 10, preferably from 4.5 to 10, andc) a viscosity of 200 to 2,5000 mPa.s at 22.degree. C.The present invention also relates to preferred polyisocyanates which contain ester groups and havea) a content of aliphatically bound isocyanate groups of 20 to 33% by weight,b) an average NCO functionality of 5 to 8 andc) a viscosity of 500 to 1,000 mPa.s at 22.degree. C.The present invention further relates to a process for the preparation of these preferred polyisocyanates by reacting isocyanatocarboxylic acid chlorides with O-silylated, polyhydric alcohols at a temperature of about 50.degree. to 150.degree. C. Finally, the present invention relates to the use of the polyisocyanates as the isocyanate component for two-component polyurethane coating compositions.
    Type: Grant
    Filed: August 2, 1990
    Date of Patent: March 17, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Lutz Schmalstieg, Josef Pedain, Klaus Nachtkamp, Lothar Kahl, Manfred Schonfelder
  • Patent number: 4983763
    Abstract: The present invention is directed to a simple process for preparing a 4,4'-diisocyanato dicyclohexylmethane containing at least 90% by weight of the trans, trans-isomer. More particularly, the process comprises:(a) melting a mixture of 4,4'-diisocyanato dicyclohexylmethane isomers containing at least 30% by weight, and preferably from 45 to 55% by weight, of the trans,trans-isomer,(b) cooling the melted mixture to a temperature of from about 20.degree. to about 25.degree. C.
    Type: Grant
    Filed: April 19, 1990
    Date of Patent: January 8, 1991
    Assignee: Mobay Corporation
    Inventors: Stephen D. Seneker, Terry A. Potter, Kenneth L. Dunlap
  • Patent number: 4968830
    Abstract: Halogen substituted aromatic compounds of the formula ##STR1## wherein Y is selected from the group CO.sub.2 H, COF, COCl, COBr, CF.sub.3, CN, NCO, or F, and X and X' are independently hydrogen or a halogen selected from the group F-, Cl- and Br-, at least one of X and X' being halogen; may be prepared by the liquid phase reaction of a brominating agent, at temperatures below about 190.degree. Celsius, with a correspondingly substituted cyclohexene or cyclohexadiene.
    Type: Grant
    Filed: September 11, 1989
    Date of Patent: November 6, 1990
    Assignee: Occidental Chemical Corporation
    Inventor: David Y. Tang
  • Patent number: 4925974
    Abstract: A process for the production of a blocked urea group-containing polyisocyanate from a partially blocked polyisocyanate and polyamine, comprising the steps of:(i) reacting a partially blocked polyisocyanate, said polyisocyanate being made substantially free of monomeric polyisocyanate, by vacuum thin layer evaporation with a primary polyamine, secondary polyamine, or mixtures thereof, in relative proportions such that the ratio of isocyanate groups to amino groups is in the range from about 1:1 to 1.3:1, and(ii) isolating said urea group-containing polyisocyanate by wherein the vacuum boiling point of said polyisocyanate is lower than the deblocking temperature of said urea group-containing polyisocyanate.
    Type: Grant
    Filed: September 16, 1988
    Date of Patent: May 15, 1990
    Assignee: Huels Aktiengesellschaft
    Inventor: Rainer Gras
  • Patent number: 4769485
    Abstract: A process for preparing alkenoyl isocyanates of the formula: ##STR1## wherein R is a hydrogen atom or a lower alkyl group which comprises subjecting an oxazolinedione hydrohalide of the formula: ##STR2## wherein X is a halogen atom and R is as defined above to decomposition under an ordinary pressure, in the presence of a hydrogen halide-eliminating agent and/or in a liquid medium having a dielectric constant of not more than 4.
    Type: Grant
    Filed: May 13, 1986
    Date of Patent: September 6, 1988
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Satoshi Urano, Noriyuki Tsuboniwa, Kei Aoki, Akira Matsumura, Yuji Suzuki, Ryuzo Mizuguchi
  • Patent number: 4745212
    Abstract: Isocyanates containing ester and/or amide groups are produced by reacting (a) an isocyanatocarboxylic acid chloride with (b) an organic compound containing a silylated alcoholic group and/or silylated phenolic hydroxyl group and/or silylated amino group which compound contains no other group which is reactive with isocyanate and chlorocarbonyl groups under the reaction conditions. The reaction of (a) with (b) is carried out at a temperature of from -20.degree. to 150.degree. C. This process makes it possible to produce the desired isocyanates with a high degree of selectivity.
    Type: Grant
    Filed: October 8, 1987
    Date of Patent: May 17, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Mormann, Edith Hissmann
  • Patent number: 4734516
    Abstract: The reaction of a zinc compound compound of formula IIICF.sub.3 CCl.sub.2 ZnCl.yL (III)wherein y is 1 or 2 and L is a solvent ligand selected from the group consisting of the N-disubstituted acid amides, N-substituted lactams and organic sulfoxides, with an aldehyde of formula IIR--CHO (II)wherein R is an aliphatic or aromatic hydrocarbon radical or an aliphatic or aromatic heterocyclic radical, gives 1-propanols of formula I ##STR1## in high yields.
    Type: Grant
    Filed: March 19, 1986
    Date of Patent: March 29, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Robert W. Lang
  • Patent number: 4663473
    Abstract: An isocyanate compound of the general formula R(NCO).sub.n, wherein R is her an aliphatic or an aromatic radical or a combination of both, and n is 1 or a larger integer is prepared by the process comprising dissolving in a high temperature boiling point solvent contained in an agitated, jacketed reactor vessel, an amine of the formula R(NH.sub.2).sub.n, completing a hydrochlorination and precipitation step to form a colloidal suspension of microcrystalline salt particles of amine hydrochloride salt R(NH.sub.2).sub.n.nHCl, introducing oxalyl chloride with agitation and by subsurface injection into the amine hydrochloride salt solution to form an intermediate of amine oxamyl chloride in situ which is thermally decomposed to yield an isocyanate of the general formula R(NCO).sub.n, and separating and purifying the isocyanate by distillation. The unreacted oxalyl chloride and high temperature reaction solvent are recovered by distillation and by absorption from the HCl by-product and are recycled.
    Type: Grant
    Filed: August 25, 1986
    Date of Patent: May 5, 1987
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: Maria A. Geigel, Chester W. Marynowski
  • Patent number: 4576771
    Abstract: The present invention relates to aqueous isocyanate emulsions and their use as binders in the production of shaped articles. These emulsions contain(A) from 80 to 20% by weight, based on the total emulsion, of water;(B) from 18 to 79% by weight, based on the total emulsion, of an organic polyisocyanate;(C) from 0.5 to 15% by weight, based on the total emulsion of a sulfonic acid corresponding to the formula:R.sub.1 --SO.sub.3 H).sub.nwhereinn represents the integers 1 or 2, andR.sub.1 represents an aromatic hydrocarbon radical containing from 6 to 14 carbon atoms, an aliphatic hydrocarbon radical containing from 10 to 18 carbon atoms, a cyclo-aliphatic hydrocarbon radical containing from 6 to 15 carbon atoms, an araliphatic hydrocarbon radical containing from 7 to 15 carbon atoms or an alkaromatic hydrocarbon radical containing from 7 to 24 carbon atoms; and(D) from 0 to 10% by weight, based on the polyisocyanate, of a nonionic, surface-active agent as an emulsifier.
    Type: Grant
    Filed: August 17, 1984
    Date of Patent: March 18, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Scholl, Helmut Reiff, Hanns I. Sachs