With Preservative Or Stabilizer Patents (Class 560/331)
  • Patent number: 11673992
    Abstract: An embodiment relates to an isocyanate composition with improved stability and reactivity and a plastic optical lens using the same. The isocyanate composition has improved stability since the content of chlorine in the composition is adjusted to 22-500 ppm, and thus the isocyanate composition can prevent the deterioration in reactivity even in the long-term storage. Therefore, the isocyanate composition according to an example, even when used after long-term storage after preparation, can be prepared, through polymerization with a thiol-based compound, as a polythiourethane-based optical material with excellent physical properties, such as refractive index, Abbe number, transparency, glass transition temperature, and yellowness, and thus the isocyanate composition is useful in fields of glass lenses, a camera lens, and the like.
    Type: Grant
    Filed: December 26, 2018
    Date of Patent: June 13, 2023
    Assignee: SKC CO., LTD.
    Inventors: Junghwan Shin, Jung Hwan Myung, Hyuk Hee Han
  • Patent number: 11661474
    Abstract: A composition is provided including a compound (A) represented by Formula (1) and a compound (B) represented by Formula (2), wherein the compound (B) is contained in an amount of 0.00002 to 0.2 parts by mass with respect to 100 parts by mass of the compound (A): (R1—COO)n—R2—(NCO)m . . . (1) (in Formula (1), R1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R2 is an (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms; and n and m are each an integer of 1 or 2) (in Formula (2), R is (—R2—(OCO—R1), and R1 and R2 are the same as those in Formula (1)).
    Type: Grant
    Filed: August 16, 2019
    Date of Patent: May 30, 2023
    Assignee: SHOWA DENKO K.K.
    Inventors: Norihito Nishimura, Katsutoshi Ohno
  • Patent number: 11401237
    Abstract: The invention relates to a composition excellent in stability during storage and stability during utilization, and relates to a method of producing the composition. The composition includes a compound (A) represented by general formula (1) and a compound (B) represented by general formula (2), and includes 0.00002 to 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A), (R1—COO)n—R2—(NCO)m??(1) (R1—COO)n—R2—(R3—R1)m??(2) wherein in general formulae (1) and (2), R1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R2 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and optionally contains an ether group; R1 and R2 in the general formula (1) are the same as R1 and R2 in the general formula (2); in general formula (2), R3 is —NHC(?O)—; and n and m each represent an integer of one or two.
    Type: Grant
    Filed: August 16, 2019
    Date of Patent: August 2, 2022
    Assignee: SHOWA DENKO K.K.
    Inventors: Norihito Nishimura, Katsutoshi Ohno
  • Patent number: 9926447
    Abstract: Curable composition obtained by combining and mixing an epoxy resin composition, comprising an epoxy resin and a carboxamide, and a polyisocyanate composition, comprising a polyisocyanate, a lithium halide and a urea compound, wherein the number of moles of lithium halide per isocyanate equivalent ranges of from 0.0001-0.04 and the number of urea+biuret equivalents per isocyanate equivalent of from 0.0001-0.4.
    Type: Grant
    Filed: November 7, 2012
    Date of Patent: March 27, 2018
    Assignee: HUNTSMAN INTERNATIONAL LLC
    Inventors: Christian Esbelin, Hans Godelieve Guido Verbeke, Hugo Verbeke
  • Patent number: 9631045
    Abstract: Disclosed are polycarbodiimides having onium salt groups, as well as methods for their production.
    Type: Grant
    Filed: February 12, 2009
    Date of Patent: April 25, 2017
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Anthony M. Chasser, Lawrence J. Fitzgerald, Venkateshwarlu Kalsani
  • Publication number: 20130317252
    Abstract: An object of the present invention is to improve the stability of an ethylenically unsaturated compound having an isocyanate group in the molecule by preventing a polymerization, a multimerization reaction and a discoloration reaction of the ethylenically unsaturated compound. The present invention relates to a stabilizing composition for an isocyanate group-containing ethylenically unsaturated compound, comprising: an isocyanate group-containing ethylenically unsaturated compound (A) which comprises one or more isocyanate groups and one or more ethylenically unsaturated groups in the molecule; and a stabilizing agent (B) which is a compound in which at least one of the ethylenically unsaturated groups in the compound (A) is replaced with an alkyl halide group or an amino alkyl group which may have a substituent.
    Type: Application
    Filed: February 2, 2012
    Publication date: November 28, 2013
    Applicant: SHOWA DENKO K.K.
    Inventors: Norihito Nishimura, Shinichi Yorozuya, Katsutoshi Ohno
  • Publication number: 20100168329
    Abstract: The invention relates to aliphatic, cycloaliphatic or (cyclo)aliphatic diisocyanates, in addition to a method for their production.
    Type: Application
    Filed: October 14, 2005
    Publication date: July 1, 2010
    Applicant: DEGUSSA GmbH
    Inventors: Dirk Hoppe, Rainer Lomoelder, Stephan Kohlstruk, Hans-Werner Michalczak
  • 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: 7297746
    Abstract: A hardener composition for use as a component of a two component polyurethane coating composition, comprising a polyisocyanate, a catalyst for promoting reaction of the polyisocyanate with a reactive hydrogen compound, and one or more antioxidants selected from: a first antioxidant comprising one or more of sterically hindered phenol antioxidants and secondary aryl amine antioxidants, and a second antioxidant comprising one or more organophosphite antioxidant, exhibits improved color stability.
    Type: Grant
    Filed: July 14, 2004
    Date of Patent: November 20, 2007
    Assignee: Rhodia Inc.
    Inventors: Richard Rosen, Jean-Marie Bernard, Shiming Wo, Corinne Simone Duffy
  • 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: 6800667
    Abstract: The present invention relates to a mixture that contains (i) at least one isocyanate and (ii) at least one organic and/or inorganic acid anhydride.
    Type: Grant
    Filed: February 20, 2001
    Date of Patent: October 5, 2004
    Assignee: BASF Corporation
    Inventors: Martin Kreyenschmidt, Andreas Arlt, Reinhard Lorenz, Ulrich Treuling
  • Patent number: 6576788
    Abstract: 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: Grant
    Filed: October 13, 2000
    Date of Patent: June 10, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: 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
  • 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
  • Patent number: 6166128
    Abstract: This invention relates to a process for the reduction of color of polymethylene poly(phenylisocyanates). This process comprises mixing a polymethylene poly(phenylisocyanate) with an epoxide having an epoxide equivalent weight of about 44 to about 700, and heating this mixture to a temperature of from about 35 to about 150.degree. C. for at least about 15 minutes, with stirring. Suitable epoxides include epoxidized fatty acid monoglycerides, epoxidized fatty acid diglycerides, epoxidized fatty acid triglycerides, epoxidized dimer fatty acids and epoxidized trimer fatty acids.
    Type: Grant
    Filed: December 8, 1998
    Date of Patent: December 26, 2000
    Assignee: Bayer Corporation
    Inventors: Rick L. Adkins, Clarence D. Blue, Jeffrey S. Bolton, Kirk J. Bourgeois, Mark R. Kratz, Brian H. Peterson, Roger C. Suter, Kenneth P. Yonek
  • 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: 6060573
    Abstract: The present invention relates to a stabilized, aliphatic and/or cycloaliphatic, blocked polyisocyanates which havei) isocyanate groups blocked with CH-acidic esters,ii) a content of blocked isocyanate groups (calculated as NCO, MW 42) of 5 to 20, preferably 7 to 15 wt. %, based on the solids content of the blocked polyisocyanate andiii) a content of formaldehyde of 0.1 to 5 wt. %, based on the solids content of the blocked polyisocyanate.The present invention also related to a process for the preparation of these stabilized, blocked polyisocyanates and to their use in one-component polyurethane stoving compositions, which may be cured at relatively low stoving temperature of about 100.degree. C., as crosslinking agents for organic polyhydroxy compounds.
    Type: Grant
    Filed: March 17, 1999
    Date of Patent: May 9, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Eberhard Konig, Claus Kobusch, Wolfram Kuttner
  • Patent number: 5961878
    Abstract: The invention relates to non-crystallising, amine-blocked polyisocyanates, to the preparation thereof and to their in one-component polyurethane stoving compositions, in particular for coil-coating applications.
    Type: Grant
    Filed: September 2, 1998
    Date of Patent: October 5, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Eberhard Konig, Karl-Ludwig Noble, Christian Fussel
  • Patent number: 5849855
    Abstract: Disclosed is a blocked polyisocyanate composition comprising: a blocked polyisocyanate obtained by blocking the terminal isocyanate groups of a two or more terminal isocyanate groups-containing polyisocyanate derived from at least one diisocyanate selected from an aliphatic diisocyanate and an alicyclic diisocyanate with a blocking agent comprising at least one active methylene compound selected from a malonic diester and an acetoacetic ester; and a salt of a basic compound with an acidic compound, or a mixture of the salt with the basic compound or the acidic compound, the composition having a pH value of from 1 to 8.5. The blocked polyisocyanate composition of the present invention not only exhibits high stability even under high temperature conditions, but also is capable of maintaining such high stability for a prolonged period of time.
    Type: Grant
    Filed: August 19, 1996
    Date of Patent: December 15, 1998
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Taketoshi Usui, Yoshiyuki Asahina
  • Patent number: 5808138
    Abstract: Stable (cyclo)aliphatic polyisocyanate compositions obtainable by phosgene-free methods, preferably by thermal cleavage of (cyclo)aliphatic polycarbamates, are stabilized with carbon dioxide, advantageously in an amount of up to 0.3% by weight.
    Type: Grant
    Filed: November 21, 1995
    Date of Patent: September 15, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Laqua, Bernd Bruchmann, Stefan Wolff
  • Patent number: 5728317
    Abstract: (Cyclo)aliphatic polyisocyanate compositions which have a long shelf life, are obtainable by phosgene-free methods, preferably by thermal cleavage of (cyclo)aliphatic polycarbamates, and, for stabilization, contain at least one primary stabilizer (2a), preferably a sterically hindered phenol and/or an aromatic amine, or at least one secondary stabilizer (2b), preferably an organic phosphite and/or a thioether, or at least one acidic stabilizer (2c), preferably a carboxylic acid, an acyl chloride, an inorganic acid, an inorganic acid chloride and/or a diester of phosphoric acid, or a stabilizer system comprising at least 2 of the stabilizers (2a) to (2c), a process for the preparation of the (cyclo)aliphatic polyisocyanate compositions and their preferred use for the preparation of isocyanurate-containing polyisocyanates.
    Type: Grant
    Filed: May 13, 1996
    Date of Patent: March 17, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Laqua, Franz Merger, Tom Witzel, Ursula Siebenhaar, David Agar
  • Patent number: 5726240
    Abstract: This invention relates to mixtures of polymethylene poly(phenylisocyanate) blends with epoxides. The addition of the epoxide stabilizes the reactivity of the polyisocyanate blends such that it is no longer dependent on the acidity. It is now possible to form polyurethanes from these mixtures based on polymethylene poly(phenylisocyanate) blends wherein less catalyst is necessary.
    Type: Grant
    Filed: November 25, 1996
    Date of Patent: March 10, 1998
    Assignee: Bayer Corporation
    Inventors: James W. Rosthauser, Robert L. Cline, Richard S. Pantone
  • Patent number: 5693686
    Abstract: A polyisocyanate having an acid value of at least 0.01% HCl is used to produce polyisocyanate, polyisocyanurate and polyurethane urea foams with an HCFC blowing agent. The use of such a polyisocyanate is advantageous because the polyisocyanate does not cause significant decomposition of the HCFC blowing agent.
    Type: Grant
    Filed: February 10, 1994
    Date of Patent: December 2, 1997
    Assignee: Bayer Corporation
    Inventors: John F. Szabat, Charles E. Mortimer, Joseph M. Sutej, Jeanne L. Beaumont, Steven L. Schilling, Harold R. Parsons, Robert P. Yeater
  • Patent number: 5561172
    Abstract: A primary object of the invention is to provide a method of producing rigid polyurethane foams using 1,1-dichloro-1-fluoroethane (HCFC-141b) as the blowing agent while substantially avoiding the formation of decomposition products from HCFC-141b. The above object can be achieved by a method of producing rigid polyurethane foams which comprises reacting a polyol with an organic polyisocyanate for foaming in the presence of HCFC-141b and a stabilizer therefor and in the presence of an organic metal catalyst and/or an imidazole compound catalyst and by the thus-produced rigid polyurethane foams.
    Type: Grant
    Filed: November 12, 1994
    Date of Patent: October 1, 1996
    Assignee: Daikin Industries, Ltd.
    Inventors: Yukio Omure, Tatsumi Tsuchiya, Kiyohiro Yuge, Hitoshi Muramatsu
  • Patent number: 5455374
    Abstract: The present invention relates to a liquid, storage-stable isocyanate having a viscosity of less than 100,000 mPa.s at 23.degree. C. and an isocyanate content of from about 9 to 20% by weight, and is prepared by reacting a solid 4,4'-methylene bis(cyclohexyl isocyanate) with a blocking agent. The 4,4'-methylene bis(cyclohexyl isocyanate) must contain at least 35 to 100% by weight of the trans,trans isomer. More generally, this liquid isocyanate is prepared by reacting the solid or semi-solid 4,4'-methylene bis (cyclohexyl isocyanate) with the blocking agent in quantities such that at least 22% but less than 60% of the isocyanate groups are blocked. Preferred blocking agents are the ketoximes, and mixtures thereof.
    Type: Grant
    Filed: June 30, 1993
    Date of Patent: October 3, 1995
    Assignee: Bayer Corporation
    Inventors: Stephen D. Seneker, Scott A. Kane
  • Patent number: 5359129
    Abstract: A method for preventing the coloration of a diphenylmethane diisocyanate compound, which comprises adding, to the diphenylmethane diisocyanate compound, a hindered amine compound of the formula: ##STR1## wherein R.sup.1 and R.sup.3 are, the same or different, each a hydrogen atom or a C.sub.1 -C.sub.8 hydrocarbon group,R.sup.2 and R.sup.4 are, the same or different, each a C.sub.1 -C.sub.8 hydrocarbon group,R.sup.5 is a hydrogen atom, a methyl group, an ethyl group, a phenoxymethyl group or a phenyl group, andm is 0, 1 or 2,in an amount of 0.001 to 1.0 parts by weight per 100 parts by weight of the diphenylmethane diisocyanate compound.An excellent effect of preventing the coloration can be achieved only by the addition of a small amount of the hindered amine compound of the formula (I).
    Type: Grant
    Filed: December 15, 1993
    Date of Patent: October 25, 1994
    Assignee: Sumitomo Bayer Urethane Co. Ltd.
    Inventors: Masato Shimizu, Toshiaki Nakano
  • Patent number: 5312971
    Abstract: The present invention is directed to a process for the production of polymethylene polyphenyl polyisocyanates by phosgenating the corresponding polyamines in solution in an inert organic solvent, removing excess phosgene, and stripping the solvent. The improvement resides in adding at least 0.02 parts by weight of reducing agent per 150 parts by weight of polyamine to the polyamines at any time prior to the stripping step.
    Type: Grant
    Filed: July 23, 1992
    Date of Patent: May 17, 1994
    Assignee: Miles Inc.
    Inventors: Rick L. Adkins, Clarence D. Blue
  • Patent number: 5288899
    Abstract: The present invention relates to a liquid, storage-stable isocyanate having a viscosity of less than 100,000 mPa.s at 25.degree. C. and an isocyanate content of from about 10 to 29% by weight, and is prepared by reacting a solid or semi-solid diphenylmethane diisocyanate with a blocking agent. More generally, the liquid isocyanate is prepared by reacting the solid or semi-solid diphenylmethane diisocyanate with the blocking agent in quantities such that from 7 to 55% of the isocyanate groups are blocked. Preferred blocking agents are the ketoximes, and mixtures thereof.
    Type: Grant
    Filed: June 30, 1993
    Date of Patent: February 22, 1994
    Assignee: Miles Inc.
    Inventors: Stephen D. Seneker, Scott A. Kane, James W. Rosthauser
  • Patent number: 5258548
    Abstract: 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: Grant
    Filed: September 3, 1992
    Date of Patent: November 2, 1993
    Assignee: Sumitomo Bayer Urethane Co., Ltd.
    Inventor: Toshiaki Imokawa
  • Patent number: 5240991
    Abstract: This invention relates to a polyisocyanate composition which contains a specific amount of denatured silicon oil being inactive to polyisocyanate compound comprising a specific diphenylmethane diisocyanate oligomer and/or its derivatives. The polyisocyanate composition of this invention has excellent storage stability at low temperature.
    Type: Grant
    Filed: November 12, 1992
    Date of Patent: August 31, 1993
    Assignee: Dow Mitsubishi Kasei Limited
    Inventors: Shigeru Yamaguchi, Hiroaki Katano
  • Patent number: 5068402
    Abstract: The present invention is directed to polyisocyanates containing a stabilizing amount of a carboxylic acid corresponding to the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 represent hydrogen or C.sub.1 -C.sub.5 -alkyl andX and Y represent hydrogen, chlorine or methyl, with the proviso that when X=Cl, Y=H or CH.sub.3 and when Y=Cl, X=H or CH.sub.3.The present invention is also directed to the use of the stabilized polyisocyanates as binders for coating compositions, sealing compounds and adhesives.
    Type: Grant
    Filed: July 20, 1990
    Date of Patent: November 26, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Josef Pedain, Lothar Kahl, Karl-Arnold Weber
  • Patent number: 4904704
    Abstract: A method of treating toluene diisocyanate distillation residues comprising reacting the residues with at least about 0.5 equivalents, based on hydrolyzable chloride concentration of the residues, of an epoxy compound at a temperature of from about 155 to about 220.degree. C. to produce a treated distillation residue having a hydrolyzable chloride level of less than about 800 parts per million (ppm) is taught. The product of the method is useful, for instance, in producing rigid foams with low K Factors.
    Type: Grant
    Filed: December 22, 1988
    Date of Patent: February 27, 1990
    Assignee: The Dow Chemical Company
    Inventors: John L. Nafziger, Steven B. Lowenkron, Charles E. Koehler, Debkumar Bhattacharjee
  • Patent number: 4677154
    Abstract: The invention relates to elimination of discoloration in polyurethanes, particularly thermoplastic polyurethanes, by the addition to the reaction mixture from 0.
    Type: Grant
    Filed: December 18, 1985
    Date of Patent: June 30, 1987
    Assignee: BASF Corporation
    Inventors: Thirumurti Narayan, Peter T. Kan