Patents Examined by Michael L Leonard
  • Patent number: 11414578
    Abstract: Solvent-based adhesive compositions are disclosed herein. In some embodiments, the solvent-based adhesive compositions include (A) an isocyanate component comprising an isocyanate curing agent and (B) a hydroxyl component comprising a polyester polyol, a polyether polyol, and a phosphate ester compound. The isocyanate curing agent of the isocyanate component (A) crosslinks the components of the hydroxyl component. In some embodiments, the phosphate ester compound has the structure (I): (I) wherein R1 is any organic group. Methods for preparing solvent-based adhesive compositions are also disclosed.
    Type: Grant
    Filed: June 28, 2018
    Date of Patent: August 16, 2022
    Assignees: DOW GLOBAL TECHNOLOGIES LLC, ROHM AND HAAS COMPANY
    Inventors: Wenwen Li, Joseph J. Zupancic, Ludwik S. Cygan
  • Patent number: 11401375
    Abstract: A flame-retardant polyether polyol is provided, including a Mannich base and an epoxide. The epoxide is selected from ethylene oxide, propylene oxide and butylene oxide. The Mannich base has a structure represented by a formula (I). In the Mannich base, flame-retardant groups, i.e., halogens are introduced at the second, fourth and sixth positions of a phenyl group, and flame-retardant elements, i.e., halogens and nitrogen are introduced into synthesized polyether polyol. The amount of active hydrogen in the Mannich base is small so that side reactions during synthesis of the polyether polyol are reduced, and the viscosity of the polyether polyol is lowered. A flame-retardant polyurethane material is also provided, synthesized from raw materials comprising the above-mentioned flame-retardant polyether polyol and an isocyanate. Due to autocatalytic performance of tertiary amido in the flame-retardant polyether polyol, use of a catalyst can be reduced and even avoided during the synthesis.
    Type: Grant
    Filed: November 15, 2019
    Date of Patent: August 2, 2022
    Assignees: Jiahua Science & Technology Development (Shanghai) Ltd., Jiahua Chemicals Inc.
    Inventors: Yongjian Guan, Ping Li, Zhijun Li, Feng Wang, Yubo Li
  • Patent number: 11401238
    Abstract: Carbon dioxide-reversibly-protected chain extension-crosslinking agents and a preparation method and use thereof are disclosed, The carbon dioxide-reversibly-protected chain extension-crosslinking agents have chemical structures represented by Formula I, Formula II, Formula III or Formula IV, wherein, n, m and p are integers, R is either OCH2CH(CH3) or OCH2CH2, 1?n?20, 1?m?10, and 1?p?10.
    Type: Grant
    Filed: February 2, 2019
    Date of Patent: August 2, 2022
    Assignee: CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY, CHINESE ACADEMY OF SCIENCES
    Inventors: Xiaoniu Yang, Bo Zhang, Xiaoli Zhao, Xiaoxiao Li, Yumeng Tian
  • Patent number: 11396575
    Abstract: The present invention provides a thermoplastic polyurethane (TPU) having a glass transition temperature between an ambient temperature and normal body temperature, wherein the TPU contains dicarboxyphenyl polyester structure represented by Formula 1 or 10-(2,3-dicarboxypropyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide n(DOPO-ITA) polyester structure represented by Formula 2. The present invention also provides a polyester polyol containing DOPO-ITA polyester structure represented by Formula 2, a molar percentage of the 10-(2,3-dicarboxypropyl)-9,10-dihydro-9-oxa-10-oxide polyester structure in the whole polyester polyol ranges from 30% to 70%. The present invention further provides an article thereof. in Formula 1, R is C2 to C8 alkylene group or CH2CH2OCH2CH2; in Formula 2, R is C2 to C8 alkylene group or CH2CH2OCH2CH2.
    Type: Grant
    Filed: September 19, 2019
    Date of Patent: July 26, 2022
    Assignee: SUNKO INK CO., LTD.
    Inventors: Chiu-Peng Tsou, Zhen-Wei Chen, Wen-Wei Cheng, Ting-Ti Huang, Sheng-Mao Tseng
  • Patent number: 11396607
    Abstract: This invention provides durable, low-ice-adhesion coatings with excellent performance in terms of ice-adhesion reduction. Some variations provide a low-ice-adhesion coating comprising a microstructure with a first-material phase and a second-material phase that are microphase-separated on an average length scale of phase inhomogeneity from 1 micron to 100 microns. Some variations provide a low-ice-adhesion material comprising a continuous matrix containing a first component; and a plurality of discrete inclusions containing a second component, wherein the inclusions are dispersed within the matrix to form a phase-separated microstructure that is inhomogeneous on an average length scale from 1 micron to 100 microns, wherein one of the first component or the second component is a low-surface-energy polymer, and the other is a hygroscopic material. The coatings are characterized by an AMIL Centrifuge Ice Adhesion Reduction Factor up to 100 or more.
    Type: Grant
    Filed: February 19, 2020
    Date of Patent: July 26, 2022
    Assignee: HRL Laboratories, LLC
    Inventors: Andrew P. Nowak, April R. Rodriguez, Elena Sherman, Adam F. Gross
  • Patent number: 11396574
    Abstract: The disclosure relates to a self-healing omniphobic composition including a self-healing omniphobic polymer with a crosslinked backbone. The crosslinked backbone includes a reaction product between a polyisocyanate, a functionalized omniphobic polymer reactive therewith, a reversible polyfunctional linker including a hindered secondary amino group and/or an aromatic hydroxy group, and one or more polymeric backbone components. The crosslinked backbone includes reversible urea or reversible urethane bonds between the reversible polyfunctional linker and the polyisocyanate, which in turn provide self-healing properties to the omni-phobic composition. The self-healing omniphobic composition has favorable omniphobic properties, for example as characterized by water and/or oil contact and/or sliding angles. The omniphobic composition can be used as a coating on any of a variety of substrates to provide self-healing omniphobic properties to a surface of the substrate.
    Type: Grant
    Filed: January 2, 2020
    Date of Patent: July 26, 2022
    Assignee: BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY
    Inventors: Muhammad Rabnawaz, Ajmir Khan, Kun Huang
  • Patent number: 11390707
    Abstract: The present invention relates to novel polyisocyanurate plastics which are obtainable by catalytic trimerization of a polyisocyanate composition A) which contains oligomeric polyisocyanates and is low in monomeric diisocyanates. “Low in monomeric diisocyanates” means that the polyisocyanate composition A) has a content of monomeric diisocyanates of at most 20% by weight. The invention further relates to the use of these polyisocyanurate plastics for production of coatings, films, semi-finished products and mouldings, and to a process for producing polyisocyanurate plastics comprising the following steps: (a) providing a polyisocyanate composition A) which contains oligomeric polyisocyanates and is low in monomeric diisocyanates, “low in monomeric diisocyanates” meaning that the polyisocyanate composition A) has a content of monomeric diisocyanates of at most 20% by weight; (b) catalytically trimerizing the polyisocyanate composition A).
    Type: Grant
    Filed: June 18, 2018
    Date of Patent: July 19, 2022
    Assignee: Covestro Deutschland AG
    Inventors: Hans-Josef Laas, Dieter Mager, Mathias Matner, Dirk Achten, Heiko Hocke
  • Patent number: 11390712
    Abstract: Methods are provided for producing bio-oil polyols, alkoxylating bio-oil polyols to provide polyols, and for employing the alkoxylated bio-oil polyols for making polymers or copolymers of polyesters or polyurethanes.
    Type: Grant
    Filed: August 20, 2020
    Date of Patent: July 19, 2022
    Assignee: BATTELLE MEMORIAL INSTITUTE
    Inventors: Daniel Garbark, Herman Benecke, Megan Moore, Mark J. Perry, Jeffrey T. Cafmeyer
  • Patent number: 11384194
    Abstract: The present invention relates to a composition comprising the reaction product of a block copolymer based on OH-functional polyolefin which is unhydrogenated, preferably polybutadiene, and cyclic esters in the form of a polyol having at least 1.8, preferably at least two, OH groups and at least one isocyanate compound having at least two isocyanate groups, which is notable in that the composition includes at least 0.0001% to 40% by weight of titanium and has a content of free isocyanate groups of at least 0.1% by weight based on the overall composition, to a process for preparation thereof and to the use of the composition for bonding of substrates.
    Type: Grant
    Filed: October 31, 2018
    Date of Patent: July 12, 2022
    Assignee: Evonik Operations GmbH
    Inventors: Nicolai Kolb, Gabriele Brenner, Bernhard Schleimer
  • Patent number: 11370912
    Abstract: The invention relates to polymer comprising structural units according to formula (I), R1—X—(C?O)—NH—R2—NH—(C?O)—O—POA-R3—(O—POA-R4)n wherein R1 represents an organic group terminated by a hydrocarbyl group having 6 to 50 carbon atoms, X represents O or N—R5, wherein R5 represents a hydrogen atom or a hydrocarbyl group having 1 to 30 carbon atoms, R2 represents a hydrocarbyl group comprising an aromatic group and having 6 to 40 carbon atoms, POA represents a polyoxyalkylene group, R3 represents an organic group having 2 to 40 carbon atoms, n is an integer from 1 to 6, R4 is independently selected from —(C?O)—NH—R2—NH—(C?O)—NH—R1, —R6, wherein R6 represents a hydrogen atom or an aliphatic or aromatic group having 1 to 24 carbon atoms, and wherein the polymer has an average of at least 1.8 end groups R1 per molecule, a number average molecular weight in the range of 2000 to 100000 Daltons, and a polydispersity in the range of 1.0 to 5.
    Type: Grant
    Filed: April 12, 2018
    Date of Patent: June 28, 2022
    Assignee: BYK-CHEMIE GMBH
    Inventors: Dominika Bernert, René Nagelsdiek, Alan L. Steinmetz, Justin Adams, George M. Zody, Wesley A. Huff, Daniela Leutfeld
  • Patent number: 11365281
    Abstract: A coating composition includes a blocked urethane elastomer (A) containing a terminal isocyanate group blocked with an oxime compound and having a number average molecular weight of 800 to 5,000, an aromatic diamine compound (B) containing an electron-donating group, and an amide compound (C). An equivalent ratio (amino group/isocyanate group) of the amino group of the aromatic diamine compound (B) to the isocyanate group of the blocked urethane elastomer (A) is within a range of 1.0 to 2.0. A solid content of the amide compound (C) is within a range of 0.5 mass % to 5 mass % based on a total solid content of the blocked urethane elastomer (A) and the aromatic diamine compound (B).
    Type: Grant
    Filed: October 11, 2019
    Date of Patent: June 21, 2022
    Assignee: KANSAI PAINT CO.. LTD.
    Inventors: Mayu Kawagishi, Katsuto Komura
  • Patent number: 11359084
    Abstract: The disclosure provides a cross-linkable polymer composition, a core layer for an information carrying card comprising such cross-linked composition, resulting information carrying card, and methods of making the same. A crosslinkable polymer composition comprises a curable base polymer resin in a liquid or paste form, and a particulate thermoplastic filler. The base polymer resin is selected from the group consisting of urethane acrylate, silicone acrylate, epoxy acrylate, urethane, acrylate, silicone and epoxy. The particulate thermoplastic filler may be polyolefin, polyvinyl chloride (PVC), a copolymer of vinyl chloride and at least another monomer, or a polyester such as polyethylene terephthalate (PET), a compound or blend thereof.
    Type: Grant
    Filed: January 14, 2020
    Date of Patent: June 14, 2022
    Assignee: X-Card Holdings, LLC
    Inventor: Mark A. Cox
  • Patent number: 11359045
    Abstract: The invention relates to a continuous method for producing an isocyanurate-containing isocyanate mixture, in which in a step a) a mixture of a first and a second isocyanate component and an isocyanate group trimerization catalyst is provided; in a step b) the mixture obtained in step a) is reacted in a first residence time zone at an elevated temperature; in a step c), the reaction mixture obtained in step b) is further heated in a second residence time zone, optionally after adding a stopper; and in a step d), the reaction mixture obtained in step c) is cooled down in a third residence time zone by way of lowering the temperature, thus obtaining the desired isocyanurate-containing isocyanate mixture.
    Type: Grant
    Filed: December 14, 2018
    Date of Patent: June 14, 2022
    Assignee: Covestro Deutschland AG
    Inventors: Christian Hahn, Hans-Detlef Arntz, Stephan Schubert, Ernst Felske, Claudia Houben, Frank Behrendt
  • Patent number: 11345776
    Abstract: Disclosed is a carboxy group-containing aqueous resin composition containing a carboxy group-containing aqueous resin and a polycarbodiimide compound (X) represented by the following general formula (1): wherein R1 represents a residue obtained by removing a functional group capable of reacting with an isocyanate from a hydrophilic compound having the functional group capable of reacting with an isocyanate; R2 represents a divalent residue obtained by removing isocyanate groups from a diisocyanate compound; R3 represents a divalent residue obtained by removing hydroxy groups from a glycol compound; X represents a group to be formed through a reaction between the hydrophilic compound and the diisocyanate compound; n1 represents a number of 1 to 10; n2 represents a number of 1 to 10; m represents a number of 1 to 5; and plural R1's may be the same or different and plural R2's may be the same or different.
    Type: Grant
    Filed: November 22, 2017
    Date of Patent: May 31, 2022
    Assignee: NISSHINBO CHEMICAL INC.
    Inventors: Kimiyo Banno, Kenichi Yanagisawa
  • Patent number: 11339288
    Abstract: A photocurable composition is provided. The photocurable composition includes: a urethane acrylamide oligomer derived from a first urethane prepolymer having an isocyanate end group and a polar group-containing acrylamide; a urethane acrylate oligomer derived from a second urethane prepolymer having an isocyanate end group and a polar group-containing (meth)acrylate; and an amide group-containing acrylic polymer derived from acrylamide and a polar group-containing (meth)acrylate.
    Type: Grant
    Filed: November 6, 2018
    Date of Patent: May 24, 2022
    Inventors: Sang Hwan Kim, Sle Lee, Jang Soon Kim, Kwang Su Seo
  • Patent number: 11326018
    Abstract: A method for the production of polyoxazolidinone compounds, comprising the step of reacting an isocyanate compound (A) with an epoxide compound (B) in the presence of a catalyst (C), wherein the isocyanate compound (A) comprises a isocyanate compound (A1) wherein the a isocyanate compound (A1) comprising at least two isocyanate groups (I1?2), preferred two isocyanate groups (I1=2), wherein the epoxide compound (B) comprises a epoxide compound (B1) and an epoxide compound (B2), wherein the epoxide compound (B2) is different from the epoxide compound (B1) wherein the epoxide compound (B1) comprising at least two terminal epoxide groups (F1?2), preferred two terminal epoxide groups (F1=2), linked together by a linking group (L1) and the epoxide compound (B2) comprising at least two terminal epoxide groups (F2?2)), preferred two terminal epoxide groups (F2=2), linked together by a linking group (L2), wherein the linking group (L2) comprises acyclic and covalent bonds to each other free of conjugated multiple bond
    Type: Grant
    Filed: August 16, 2017
    Date of Patent: May 10, 2022
    Assignee: Covestro Deutschland AG
    Inventors: Anna Weber, Claudine Rangheard, Michael Kessler, Walter Leitner, Christoph Gürtler, Carsten Koopmans, Thomas Ernst Müller
  • Patent number: 11312817
    Abstract: An alternative polyurethane composition is provided which comprises a reaction product of an azidated polyol and a poly(alkynyl carbamate) prepolymer reacted at a temperature of from 20° C. to 120° C., wherein the poly(alkynyl carbamate) prepolymer comprises a reaction product of a polyisocyanate and a stoichiometric equivalent of an alkynol of the formula (I), HC?C—R1R2—OH??(I), and wherein R1 is an electron-withdrawing group selected from the group consisting of carbonyl, ester, amide, and urethane and R2 is a linear or branched alkyl chain having from 1 to 15 carbon atoms. The inventive alternative polyurethane composition position may be used to provide adhesives, sealants, films, elastomers, castings, foams, and composites.
    Type: Grant
    Filed: November 25, 2019
    Date of Patent: April 26, 2022
    Assignees: Covestro LLC, The University Of Southern Mississippi
    Inventors: Robson F. Storey, Alan Ekin, R. Hunter Cooke, III, Jie Wu
  • Patent number: 11312810
    Abstract: The invention relates to a thermoplastic polyurethane matrix resin composition, comprising at least one C3-8 alkane diol, at least one alkoxylated aromatic diol and at least one polyisocyanate. Furthermore, the present invention relates to a fiber-reinforced composite comprising a cured thermoplastic polyurethane polymer matrix according to the present invention and a fiber material. Moreover, a method for the manufacture of the fiber-reinforced composite according to the present invention and use of the composition or the fiber-reinforced composite in railway vehicles, automotive vehicles, aircraft vehicles, boats, space vehicles, motorbikes, bicycles, sporting goods, helmets, functional clothing, shoes, construction parts in bridges and buildings or wind turbine blades are described.
    Type: Grant
    Filed: June 3, 2019
    Date of Patent: April 26, 2022
    Assignee: Henkel AG & Co. KGaA
    Inventors: Andreas Niegemeier, Andreas Ferencz, Tamara Schmidt, Wolfgang Lupp
  • Patent number: 11312813
    Abstract: In various embodiments, coated infill includes a plurality of infill granules and a preformed coating on the infill granules including a cured polyurethane product of at least one polyurethane prepolymer component and a curative component. The polyurethane prepolymer component includes a reaction product of an isocyanate component including diphenylmethane diisocyanate (MDI) and a polyol component, and has a free isocyanate content (% NCO) from 2 wt % to 12 wt %. The curative component includes water. Methods for making an artificial turf surface using the coated infill are also provided.
    Type: Grant
    Filed: February 22, 2018
    Date of Patent: April 26, 2022
    Assignee: Dow Global Technologies LLC
    Inventors: Virginie Assemat, Andrea Benvenuti, Amber Marie Stephenson
  • Patent number: 11306175
    Abstract: The present invention relates to a polymer composition comprising a polymeric matrix and particles of an impact modifier within the polymeric matrix, wherein the impact modifier comprises at least one urethane group and the impact modifier is obtainable by reacting in situ within the polymeric matrix a) a polyol comprising a dimer fatty residue; and b) a polyisocyanate. The invention also relates to a method of making the polymer composition.
    Type: Grant
    Filed: November 3, 2016
    Date of Patent: April 19, 2022
    Assignee: Croda International PLC
    Inventors: Angela Leonarda Maria Smits, Johannes Rutger Idsard Knoop