Benzene Ring Bonded Directly To The Isocyanate Group Patents (Class 560/358)
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Patent number: 6576788Abstract: In a process for preparing mixtures of diphenylmethane diisocyanates and polyphenylpolymethylene polyisocyanates having a reduced content of chlorinated by-products and a reduced iodine color number by two-stage reaction of the corresponding mixtures of diphenylmethanediamines and polyphenylpolymethylenepolyamines with phosgene in the presence of at least one inert organic solvent at elevated temperature, separation of the excess phosgene and solvent after the phosgenation is complete and thermal treatment of the reaction product, the mass ratios of phosgene to hydrogen chloride in the residence time apparatus of the second stage of the phosgenation are at the same time 10-30:1 in the liquid phase and 1-10:1 in the gas phase.Type: GrantFiled: October 13, 2000Date of Patent: June 10, 2003Assignee: BASF AktiengesellschaftInventors: Ulrich Penzel, Volker Scharr, Dieter Starosta, Hilmar Boesel, Eckhard Ströfer, Joachim Pfeffinger, Frank Poplow, Jürgen Dosch, Hans Volkmar Schwarz, Fritz Näumann, Peter van den Abeel, Jan Jacobs, Filip Nevejans, Willy van Pee
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Publication number: 20030100607Abstract: The present invention relates to new thiolalkyl benzoic acids, pharmaceutical compositions and diagnostic kits comprising such compounds, and methods of using such compounds for inhibiting NAALADase enzyme activity, detecting diseases where NAALADase levels are altered, effecting neuronal activity, effecting TGF-&bgr; activity, inhibiting angiogenesis, and treating glutamate abnormalities, neuropathy, pain, compulsive disorders, prostate diseases, cancers, glaucoma, retinal disorders, and cancer.Type: ApplicationFiled: May 30, 2002Publication date: May 29, 2003Inventors: Takashi Tsukamoto, Doris Stoermer, Dilrukshi Vitharana
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Patent number: 6569352Abstract: 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: GrantFiled: October 25, 1999Date of Patent: May 27, 2003Assignee: Stepan CompanyInventors: Douglas K. Hillshafer, George Magnus
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Publication number: 20030065124Abstract: 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: ApplicationFiled: August 2, 2001Publication date: April 3, 2003Inventors: Ronald O. Rosenberg, Rui Xie, Ajaib Singh
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Patent number: 6515164Abstract: 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: GrantFiled: July 2, 1999Date of Patent: February 4, 2003Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Gerd Bolte, Guenter Henke, Markus Kruedenscheidt, Astrid Omoruyi
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Patent number: 6433219Abstract: A process for preparing methylenedianiline by reacting aniline with formaldehyde in the presence of acid catalysts comprising, in a semicontinuous process, introducing aniline with or without acid catalyst, feeding formaldehyde with or without acid catalyst through a mixing element into a circuit in which aniline with or without acid catalyst and with or without previously added formaldehyde is circulated and, after feeding in at least 50% of the total amount of formaldehyde to be fed in, heating the reaction mixture to a temperature above 75° C. In addition, the invention relates to a process for preparing polyisocyanates by phosgenation of amines obtainable in this manner and to the polyisocyanates obtainable by this process.Type: GrantFiled: September 8, 2000Date of Patent: August 13, 2002Assignee: BASF AktiengesellschaftInventors: Eckhard Ströfer, Jan Jacobs, Wilfried Seyfert, Hans Volkmar Schwarz, Olaf Schweers, Volker Scharr, Ulrich Penzel
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Publication number: 20020087030Abstract: A process for preparing polymerizable biaryl derivatives comprises reacting an aromatic comprising a 6-membered ring which bears ester or benzylic OH groups in the 1,4 position with a second aromatic in a palladium-catalyzed cross-coupling reaction to give a biaryl and converting the ester or benzylic OH groups into polymerizable groups in one or more steps. The biaryls obtained are suitable for preparing polymers which are used as electroluminescence materials.Type: ApplicationFiled: October 16, 2001Publication date: July 4, 2002Inventors: Hubert Spreitzer, Willi Kreuder, Heinrich Becker, Jochen Krause
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Patent number: 6410095Abstract: 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: GrantFiled: September 6, 1996Date of Patent: June 25, 2002Assignee: Bayer AktiengesellschaftInventors: Martin Brahm, Gerhard Ruttmann, Lutz Schmalstieg
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Publication number: 20020035232Abstract: 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: ApplicationFiled: October 9, 2001Publication date: March 21, 2002Inventor: Jean-Marie Bernard
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Publication number: 20020007036Abstract: High-functionality polyisocyanates are prepared by a process which comprisesType: ApplicationFiled: March 19, 2001Publication date: January 17, 2002Inventors: Bernd Bruchmann, Hans Renz, Rainer Koniger, Ulrike Ehe, Ulrich Treuling, Rudolf Muller-Mall
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Publication number: 20010039325Abstract: 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: ApplicationFiled: October 29, 1997Publication date: November 8, 2001Inventors: PIERRE ARDAUD, JEAN-MARIE BERNARD
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Patent number: 6313060Abstract: A resilient polyurethane foam produced by using a polyether polyol produced by reacting alkylene oxides with a polyhydroxy compound having at least 2 hydroxyl groups as an initiator in the presence of the catalyst for alkylene oxide ring-opening polymerization of the present invention, which is excellent in foam physical properties, vibration characteristics and molding properties.Type: GrantFiled: March 8, 2000Date of Patent: November 6, 2001Assignee: Asahi Glass Company, LimitedInventors: Kayoko Sugiyama, Hiroki Fukuda, Akio Horie, Hiroshi Wada
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Patent number: 6057269Abstract: Benzylhydroxylamines I ##STR1## (X=--N(R.sup.7)--O--; Y=O, S; R.sup.1 =halogen, CN, NO.sub.2, CF.sub.3 ; R.sup.2 =H, halogen; R.sup.3 =H, NH.sub.2, CH.sub.3 ;R.sup.4 =H, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylsulfinyl or C.sub.1 -C.sub.6 -alkylsulfonyl;R.sup.5 =H, halogen, C.sub.1 -C.sub.6 -alkyl;R.sup.6 =H, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.6 -alkenyl;R.sup.7 =H, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.3 -C.sub.6 -alkenylcarbonyl, C.sub.3 -C.sub.6 -alkynylcarbonyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.2 -C.sub.8 -alkenyloxycarbonyl, C.sub.2 -C.sub.6 -alkynyloxycarbonyl, C.sub.1 -C.sub.6 -alkylthiocarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.Type: GrantFiled: January 5, 1998Date of Patent: May 2, 2000Assignee: BASF AktiengesellschaftInventors: Ralf Klintz, Gerhard Hamprecht, Elisabeth Heistracher, Peter Schafer, Cyrill Zagar, Karl-Otto Westphalen, Helmut Walter, Ulf Misslitz, Olaf Menke, Markus Menges
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Patent number: 6036879Abstract: 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: GrantFiled: February 9, 1999Date of Patent: March 14, 2000Assignee: Arco Chemical Technology, L.P.Inventors: Bruce D. Lawrey, Stephen D. Seneker, Nigel Barksby
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Patent number: 6013606Abstract: Substituted cinnamic oxime derivatives I and cinnamic hydroxamide derivatives II ##STR1## (R.sup.1= halogen, NO.sub.2, CN, CF.sub.3 ; R.sup.2 =H, halogen; R.sup.3= H, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, hydroxy-C.sub.1 -C.sub.6 -alkyl;R.sup.4= H, halogen, CN, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl orR.sup.3 +R.sup.4 =chemical bond;Y=--O--, --S--, --O--CO--, --O--SO.sub.2 -- or chemical bond;Y'=--O-- or --S--;R.sup.5= unsubst. or subst. C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -haloalkyl; C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, unsubst. or subst. phenyl or phenyl-C.sub.1 -C.sub.6 -alkyl, or, if Y is --O--, --S-- or a chemical bond, is (C.sub.1 -C.sub.6 -alkyl)carbonyl or (C.sub.1 -C.sub.6 -alkoxy)carbonyl; or, if Y is a chemical bond, is hydrogen or halogen;R.sup.5 '=R.sup.5, H or (C.sub.1 -C.sub.6 -haloalkyl)carbonyl;R.sup.6= H, C.sub.1 -C.Type: GrantFiled: June 30, 1997Date of Patent: January 11, 2000Assignee: BASF AkteingesellschaftInventors: Ralf Klintz, Gerhard Hamprecht, Elisabeth Heistracher, Peter Schafer, Christoph-Sweder von dem Bussche-Hunnefeld, Peter Munster, Reinhard Kirstgen, Albrecht Harreus, Karl-Otto Westphalen, Matthias Gerber, Helmut Walter
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Patent number: 5981789Abstract: Disclosed is a method of preparing an aromatic compound having the general formula ##STR1## where R is CF.sub.3, OCF.sub.3, OC.sub.2 F.sub.5, CN, NCO, or COCl, m is 0, 1, or 2, n is 0, 1, or 2, q is 1 or 2, and q+m+n is an integer from 1 to 5. A vapor is prepared of a substrate having the general formula ##STR2## and a chlorinating agent. The mixture is reacted at a temperature above the boiling point of the substrate but below its decomposition temperature. The amount of chlorinating agent is about 0.5 to about 2 times the amount stoichiometrically required to replace the nitro groups on the substrate with chlorine. Unreacted substrate and partially reacted substrate are condensed from the product mixture and are recycled. The substrate is preferably in contact with the chlorinating agent before it is vaporized.Type: GrantFiled: December 30, 1998Date of Patent: November 9, 1999Assignee: Occidental Chemical CorporationInventors: John Hickey, Robert L. Bell, George Piotrowski
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Patent number: 5919888Abstract: 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: GrantFiled: June 1, 1998Date of Patent: July 6, 1999Assignee: Arco Chemical Technology, L.P.Inventors: Bruce D. Lawrey, Stephen D. Seneker, Nigel Barksby
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Patent number: 5905151Abstract: 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: GrantFiled: February 18, 1993Date of Patent: May 18, 1999Assignee: Bayer CorporationInventors: William E. Slack, Hersel T. Kemp, II
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Patent number: 5902459Abstract: There is now provided a method of recycling toluenediisocyanate residue resulting from the production of toluenediisocyanate by the reaction of toluenediamine by phosgenation in the presence of a solvent. In accordance with the teachings of the present invention, the toluenediisocyanate residue is treated at reflux with an alkanolamine to obtain an intermediary product which is distilled thereby giving rise to various products including but not limited to at least one component selected from toluenediamine, oxazolidone and hydroxyethylimidiazolidone. Preferably the alkanolamine employed is a monoethanolamine.Type: GrantFiled: June 10, 1996Date of Patent: May 11, 1999Assignee: BASF CorporationInventors: Steven D. Gagnon, Sandy A. Bananto
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Patent number: 5874507Abstract: The specification discloses a method and additive for increasing the surface activity of non-polar polymeric materials, and a non-polar polymeric material exhibiting increased surface activity. The invention employs an additive of the formulaA-B-A.sup.1wherein each of the A and A.sup.1 blocks which may be the same or different has a number molecular weight in the range of from about 200 to about 1000 daltons and is selected from the group substituted and unsubstituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl and alkylaryl units derived from one or more esters, organic acids, organic halides or organic acid halides, and units derived from alkyl or aryl isocyanates or ester-amides. The B-block is a polyepichlorohydrin unit derived from a polyepichlorohydrin polyol having at least two terminal hydroxyl groups and having an average molecular weight in the range of from about 400 to about 4000 daltons.Type: GrantFiled: September 15, 1997Date of Patent: February 23, 1999Assignee: Arizona Chemical CompanyInventors: Xinya Lu, Eric S. Gardiner
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Patent number: 5849944Abstract: 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: GrantFiled: May 27, 1997Date of Patent: December 15, 1998Assignee: ARCO Chemical Technology, L.P.Inventors: Gary L. Allen, Nigel Barksby, Stephen D. Seneker, Usama E. Younes
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Patent number: 5821316Abstract: 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: GrantFiled: January 24, 1997Date of Patent: October 13, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Jeffrey Raymond Quay, Edwin Lee McInnis
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Patent number: 5798409Abstract: 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: GrantFiled: April 1, 1997Date of Patent: August 25, 1998Assignee: Minnesota Mining & Manufacturing CompanyInventor: Chia-Tie Ho
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Patent number: 5770763Abstract: Novel difunctionalized cyclobutabenzene monomers of the general formula: ##STR1## wherein Z can be hydrogens or a cyclobutane ring; and X and Y are carboxyl, amino, alcohol, isocyanate, acid halide, or bis-acyl halide groups. Exemplary difunctional bitricyclodecatriene monomers are ?2,2'-bidicyclo?2.4.0!octa-1,3,5-triene!-5,5'-dicarboxylic acid (BXTA) and ?2,2'-bitricyclo?6.2.0.0!deca-1,3,(6),7-triene!-7,7'-dicarboxylic acid (QXTA). The difunctionalized bitricyclodecatriene monomers can form part of a polymer backbone chain in which the multiple butane ring functionalities can be easily opened to produce strong, three-dimensional covalent bond crosslinking between polymer chains. The crosslinking can be induced simply by heating the polymer to a temperature in excess of 250.degree. C.Type: GrantFiled: August 30, 1996Date of Patent: June 23, 1998Assignee: The Board of Regents of the Univ. of MichiganInventors: David C. Martin, Jeffrey S. Moore, Larry J. Markoski, Kenneth A. Walker, Gary E. Spilman
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Patent number: 5747628Abstract: Polyisocyanates based on polyhydroxy polyethers and tolylene diisocyanate containing ether and urethane groups and having an isocyanate group content of from 11.8 to 14.4% by weight, an average isocyanate functionality of from 3.1 to 4.0 and a free tolylene diisocyanate content of less than 0.1% by weight are produced by reacting a polyhydroxy polyether having a molecular weight in the range of from about 350 to about 500 with excess quantities of tolylene diisocyanate and subsequently distilling the mixture to remove unreacted excess of the starting diisocyanate. These polyisocyanates are particularly useful in the production of polyurethane lacquers.Type: GrantFiled: December 2, 1992Date of Patent: May 5, 1998Assignee: Bayer AktiengesellschaftInventors: Lutz Schmalstieg, Hermann Gruber, Bernd Riberi, Klaus Nachtkamp
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Patent number: 5710191Abstract: A method for preparing a polyurethane foam which comprises reacting an organic polyisocyanate and a polyol in the presence of a blowing agent, a cell stabilizer and a catalyst composition comprising at least one compound of either of the following formulas IA and IB: ##STR1## where R is hydrogen, methyl or hydroxymethyl. The preferred catalysts comprise 3-hydroxymethyl quinuclidine, 3-methyl-3-hydroxymethyl quinuclidine and 4-hydroxymethyl quinuclidine.Type: GrantFiled: May 21, 1996Date of Patent: January 20, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Mark Leo Listemann, Kristen Elaine Minnich, Brian Eugene Farrell, Lisa Ann Mercando, Michael John Kimock, James Dudley Nichols
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Patent number: 5693686Abstract: 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: GrantFiled: February 10, 1994Date of Patent: December 2, 1997Assignee: Bayer CorporationInventors: John F. Szabat, Charles E. Mortimer, Joseph M. Sutej, Jeanne L. Beaumont, Steven L. Schilling, Harold R. Parsons, Robert P. Yeater
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Patent number: 5691441Abstract: 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: GrantFiled: October 11, 1996Date of Patent: November 25, 1997Assignee: Arco Chemical Technology, L.P.Inventors: Stephen D. Seneker, Bruce D. Lawrey
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Patent number: 5677412Abstract: 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: GrantFiled: March 19, 1996Date of Patent: October 14, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventor: Neville Everton Drysdale
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Patent number: 5654479Abstract: 4,4'-disubstituted bis(2,6-diisopropylphenyl)carbodiimides of the formula (I) ##STR1## where R is 1-methyl-1-phenylethyl, phenoxy or tert-butyl, a process for their preparation, their use as stabilizers against hydrolytic degradation of polyaddition and polycondensation products containing ester groups, and the novel 4-(1-methyl-1-phenylethyl)-2,6-diisopropyl-, 4-phenoxy-2,6-diisopropyl- and 4-tert-butyl-2,6-diisopropylphenyl isocyanates which can be used for their preparation.Type: GrantFiled: July 15, 1996Date of Patent: August 5, 1997Assignee: BASF AktiengesellschaftInventors: Friedhelm Lehrich, Siegmund Pohl, Bernd Bruchmann, Helmut Tesch, Roland Minges, Johann Swoboda, Manfred Genz, Guenter Scholz, Joachim Streu
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Patent number: 5621138Abstract: 4,4'-disubstituted bis-(2,6-diisopropylphenyl)carbodiimides of the formula (I) ##STR1## where R is 1-methyl-1-phenylethyl, phenoxy or tert-butyl, a process for their preparation, their use as stabilizers against hydrolytic degradation of polyaddition and polycondensation products containing ester groups, and the novel 4-(1-methyl-1-phenylethyl)-2,6-diisopropyl-, 4-phenoxy-2,6-diisopropyl- and 4-tert-butyl-2,6-diisopropylphenyl isocyanates which can be used for their preparation.Type: GrantFiled: January 30, 1996Date of Patent: April 15, 1997Assignee: BASF AktiengesellschaftInventors: Friedhelm Lehrich, Siegmund Pohl, Bernd Bruchmann, Helmut Tesch, Roland Minges, Johann Swoboda, Manfred Genz, Guenter Scholz, Joachim Streu
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Patent number: 5606004Abstract: 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: GrantFiled: July 31, 1995Date of Patent: February 25, 1997Assignee: Bayer AktiengesellschaftInventors: Martin Brahm, Josef Pedain, Lutz Schmalstieg
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Patent number: 5580645Abstract: A substrate having oil-, water- and soil-repellency and/or soil release properties is produced by treating the substrate with a polyfluoro organic compound having at least 1 urea linkage derived from: (A) at least 1 polyisocyanate which contains at least three isocyanate groups per molecule, (B) at least 1 fluorochemical compound which contains (i) a single functional group having 1 or more Zerewitinoff hydrogen atom S and (ii) at least 2 carbon atoms each of which contains at least 2 fluorine atoms, and (C) sufficient water to react with from about 5% to about 60% of the isocyanate groups.Type: GrantFiled: August 8, 1995Date of Patent: December 3, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: Jack R. Kirchner
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Patent number: 5574124Abstract: 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: GrantFiled: August 3, 1995Date of Patent: November 12, 1996Assignees: Bayer Aktiengesellschaft, Bayer CorporationInventors: Lutz Schmalstieg, Rainer Rettig, Ulrich Walter, Edwin R. Hortelano
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Patent number: 5556891Abstract: 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.gtoreq.Type: GrantFiled: November 1, 1995Date of Patent: September 17, 1996Assignee: BASF Schwarzheide GmbHInventors: Holger Seifert, Juergen Winkler, Regina Pretzsch, Robert O'Meara
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Patent number: 5530154Abstract: 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: GrantFiled: May 17, 1995Date of Patent: June 25, 1996Assignee: BASF Schwarzheide GmbHInventors: Holger Seifert, Juergen Winkler, Regina Pretzsch, Robert O'Meara
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Patent number: 5527925Abstract: 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: GrantFiled: June 24, 1994Date of Patent: June 18, 1996Assignee: Ciba-Geigy CorporationInventors: Peter Chabrecek, Dieter Lohmann
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Hydroxy and amino functional pyrrolizidine catalyst compositions for the production of polyurethanes
Patent number: 5512603Abstract: 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: GrantFiled: February 22, 1994Date of Patent: April 30, 1996Assignee: 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: 5510432Abstract: Isocyanate prepolymers based on an aromatic diisocyanate and a polyether polyol in which at least 95% of the isocyanate groups are blocked by blocking agents selected fromA) about 50 to about 97 equivalent % of a phenol or substituted phenol,B) about 30 to about 50 equivalent % of a pyrazole or a substituted pyrazole andC) 0 to about 10 equivalent % of a blocking agent different from A) and B).These blocked isocyanate prepolymers are particularly useful for the production of flexible epoxy resin systems.Type: GrantFiled: May 31, 1995Date of Patent: April 23, 1996Assignee: Bayer AktiengesellschaftInventors: Lutz Schmalstieg, Rainer Rettig, Eberhard Konig
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Patent number: 5481027Abstract: Urea linkage-containing alkoxypolyoxyalkylene fluorocarbamates prepared by reacting (a) at least one polyisocyanate which contains at least three isocyanate groups with (b) at least one fluorochemical reagent which contains one functional group which has at least one H and at least two C atoms each of which contains at least two F atoms, (c) at least one hydrophilic, water-solvatable reagent which contains a single functional group which has at least one reactive H, (d) at least one reagent which contains one reactive H and which on reaction with an isocyanate group yields functionality which has abeyant chemical reactivity with fibrous substrates and (e) then with water, reactants (b), (c) and (d) being reacted with 55% to 95% of said isocyanate groups, and water with the remainder.Type: GrantFiled: March 7, 1994Date of Patent: January 2, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: Jack R. Kirchner
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Patent number: 5453517Abstract: The invention relates to fluorescent and/or reactive derivatives of 1,2-bis-(2-aminophenoxyethane)-N,N,N',N'-tetraacetic acid (BAPTA) according to the formula: ##STR1## where at least one of W and X is a functional group, with or without a spacer, that terminates in an alcohol or phenol, a thiol, a haloacetamide, an alkyl halide, an amine or aniline, a carboxylic acid, an anhydride, an isocyanate, an isothiocyanate, a maleimide, or an activated ester. The BAPTA-like molecule may be further substituted, one or more times, by additional functional groups with or without spacers or by CH.sub.3, NO.sub.2, CF.sub.3, F, Cl, Br, I, or carboxylic acid derivatives or pharmaceutically acceptable salts thereof, or by indolyl or benzofuran fluorophores. The functional groups allow for subsequent covalent attachment of one or more oxygen heterocycle fluorophores (e.g. fluorescein, coumarin, rhodamine); or polymolecular assemblies (e.g.Type: GrantFiled: February 25, 1992Date of Patent: September 26, 1995Assignee: Molecular Probes, Inc.Inventors: Michael A. Kuhn, Richard P. Haugland
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Patent number: 5414111Abstract: Polyfluoro organic compound having at least one urea linkage derived from: (1) at least one polyisocyanate containing at least three isocyanate groups, (2) at least one fluorochemical compound which contains per molecule (a) a single functional group having one or more Zerewitinoff hydrogen atoms and (b) at least two carbon atoms each of which contains at least two fluorine atoms, and (3) water in an amount sufficient to to react with from about 5% to about 60% of the isocyanate groups.Type: GrantFiled: February 2, 1994Date of Patent: May 9, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Jack R. Kirchner
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Patent number: 5410073Abstract: Process comprising (I) reacting (a) at least one polyisocyanate or mixture of polyisocyanates which contains at least three isocyanate groups per molecule with (b) a stoichiometric deficiency of at least one fluorochemical compound which contains per molecule (i) a single functional group having one or more Zerewitinoff hydrogen atoms and (ii) at least two carbon atoms each of which contains at least two fluorine atoms, and (II) thereafter forming one or more urea linkages per mol of said polyisocyanate by reacting the remaining isocyanate groups with water in an amount sufficient to to react with from about 5% to about 60% of the isocyanate groups in said polyisocyanate.Type: GrantFiled: February 4, 1994Date of Patent: April 25, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Jack R. Kirchner
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Patent number: 5364958Abstract: The hue of a methylene-crosslinked polyphenylene polyisocyanate continuously produced by the reaction with phosgene in an inert solvent of a polyamine mixture obtained by condensation of aniline and formaldehyde in the presence of an acid catalyst is improved by first removing any residual phosgene followed by heat treatment in the presence of hydrogen chloride gas.Type: GrantFiled: June 22, 1993Date of Patent: November 15, 1994Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Noritoshi Ishida, Zunzi Tashima, Naoki Sato, Michiya Takasaki, Masaaki Iijima, Kazuyuki Kuroda, Kazunari Nitta
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Patent number: 5324854Abstract: Compounds having the formula: ##STR1## wherein X is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.8 alkoxy or halogen;Y is hydrogen, halogen, or C.sub.1 -C.sub.4 dialkylamino;R.sup.1 is C.sub.1 -C.sub.8 straight chain or branched alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 alkenyl or C.sub.3 -C.sub.8 alkoxy;R.sup.2 is C.sub.1 -C.sub.8 straight chain or branched alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, halo substituted C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.1 -C.sub.4 alkoxy, cyano C.sub.1 -C.sub.4 alkyl, alkoxyalkyl, phenyl, aralkyl, C.sub.1 -C.sub.4 acyl, C.sub.1 -C.sub.4 carbalkoxyalkyl, C.sub.1 -C.sub.4 carbalkoxyalkyl substituted by C.sub.1 -C.sub.4 alkyl, phenylmethyl or methylthioethyl, dialkylaminoethyl, or tetrahydrofuranylmethyl;R.sup.1 and R.sup.2 taken together form a C.sub.3 -C.sub.8 membered heterocyclic ring containing one or more heteroatoms.The compounds are useful as intermediates for making herbicides.Type: GrantFiled: December 7, 1992Date of Patent: June 28, 1994Assignee: Uniroyal Chemical Company, Inc.Inventors: Richard J. Strunk, Allyn R. Bell
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Patent number: 5286760Abstract: Disclosed herein is a process for preparing a reaction product containing methylene diphenylamine comprising reacting aniline with an aldehyde, in the presence of a low level of an acid wherein the acid level is reduced before digesting reaction mixture at a high temperature which is sufficient to effect a rearrangement of the intermediates to produce a reaction product containing methylene diphenylamines and low levels of impurities.Type: GrantFiled: October 9, 1992Date of Patent: February 15, 1994Assignee: Miles, Inc.Inventors: Jeffrey S. Bolton, Robert L. Mayen
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Patent number: 5258548Abstract: A method for preventing coloration of an aromatic isocyanate compound, which is characterized in that an organic phosphite ester of formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are, the same or different, each a C.sub.4-20 hydrocarbon group, 2,6-di-tert.-butyl-4-methylphenol and triphenyl phosphite are added to the aromatic isocyanate compound.Type: GrantFiled: September 3, 1992Date of Patent: November 2, 1993Assignee: Sumitomo Bayer Urethane Co., Ltd.Inventor: Toshiaki Imokawa
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Patent number: 5256784Abstract: Nonlinear-optic (NLO) compositions containing functionalized merocyanine dyes, such that the molecules, comprising the NLO-active compositions have a functional group at each end of the molecule and each functional group differing in reactivity, thus permitting stepwise reaction of each functional group, and NLO-active molecules prepared from hemioxonol dyes derviatived with (meth)acrylate or (meth)acrylamide groups, and their uses in devices such as second harmonic generators or polymer integrated optics.Type: GrantFiled: January 16, 1992Date of Patent: October 26, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: Cecil V. Francis, Elisa M. Cross, Roberta E. Harelstad, Paul F. Korkowski, Peter C. Leung, David W. Macomber, John E. Trend
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Patent number: 5220000Abstract: Novel bifunctional bis-quinolinols are provided as well as their chelates and processes for their production. The quinolinols can be attached to organic substrates before or after chelation and are useful for diagnostic and therapeutic purposes.Type: GrantFiled: January 23, 1992Date of Patent: June 15, 1993Inventor: Spyros Theodoropulos
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Patent number: 5215618Abstract: Disclosed herein is a process for bonding substrates comprising applying a hot-melt adhesive to the surface of at least one of the substrates and contacting the surface of said substrate with the surface of the other substrate, said adhesive containing an ester group-containing polyisocyanate which is a solid below 30.degree. C. and liquid above 100.degree. C., corresponding to formula (I)A(OCO-B-NCO).sub.n (I)in whichn stands for a whole number or a fraction (statistical average) of from 2 to 6,A stands for an n-valent organic group such as is obtained by removal of hydroxyl groups from an n-valent polyhydroxyl compound in the molecular weight (Mn) range of from 800 to 6000 containing ester and/or carbonate groups andB stands for an aliphatic, cycloaliphatic or aromatic hydrocarbon group having up to 18 carbon atoms.Type: GrantFiled: August 8, 1991Date of Patent: June 1, 1993Assignee: Bayer AktiengesellschaftInventors: Lutz Schmalstieg, Eduard Haensel, Klaus Nachtkamp, Heinrich Konigshofen, Otto Ganster