Reactant Contains A Fluorine Atom Patents (Class 528/70)
  • Patent number: 7772353
    Abstract: This invention relates to polyurethane elastomers and to a process for their production. These elastomers comprise the reaction product of a (cyclo)aliphatic isocyanate component having an NCO group content of about 20 to about 45%, with an isocyanate-reactive component comprising one or more polyether polyols which is free of amine groups, and a low molecular weight organic compound containing two hydroxyl groups and which is free of amine groups, in the presence of one or more catalysts.
    Type: Grant
    Filed: December 15, 2005
    Date of Patent: August 10, 2010
    Assignee: Bayer MaterialScience LLC
    Inventors: Stephen J. Harasin, Richard R. Roesler, Rick V. Starcher, Carol L. Kinney, James T Garrett
  • Patent number: 7759447
    Abstract: The present invention is directed to polyisocyanate addition compounds which i) are substantially free from isocyanate groups and are prepared from one or more a) polyisocyanate adducts and/or b) NCO prepolymers, ii) contain urethane groups, iii) contain fluorine in an amount of 0.01 to 50% by weight, and iv) contain ethylenically unsaturated groups in an amount of 2 to 40% by weight, wherein the preceding percentages are based on the solids content of the polyisocyanate addition compounds. The fluorine is incorporated by reacting an isocyanate group with a compound containing two or more carbon atoms, one or more hydroxyl groups and one or more fluorine atoms to form urethane and optionally allophanate groups. More than 50 mole % of the groups that incorporate fluorine into the addition compounds are urethane groups. The polyisocyanate addition compounds are useful in coating compositions that are curable by free radical polymerization.
    Type: Grant
    Filed: November 17, 2005
    Date of Patent: July 20, 2010
    Assignee: Bayer MaterialScience LLC
    Inventors: Carol L. Kinney, Richard R. Roesler, James T. Garrett, Aaron Lockhart
  • Patent number: 7750093
    Abstract: The present invention relates to fluorochemical polyurethane compounds, a method for their preparation, a method of application, and compositions comprising that fluorochemical polyurethane compound. The compound and the composition comprising that compound are suitable to impart durable oil- and water-repellency to substrates.
    Type: Grant
    Filed: June 29, 2006
    Date of Patent: July 6, 2010
    Assignee: 3M Innovative Properties Company
    Inventors: Cheryl L. S. Elsbernd, Frans A. Audenaert, John C. Clark, Chetan P. Jariwala, George G. I. Moore, Zai-Ming Qiu
  • Publication number: 20100160595
    Abstract: Fluorocarbon- and urethane-(meth)acryl-containing additives and hardcoats. The hardcoats are particularly useful as a surface layer on an optical device.
    Type: Application
    Filed: March 5, 2010
    Publication date: June 24, 2010
    Inventors: Thomas P. Klun, Naiyong Jing, Richard J. Pokorny, Zai-Ming Qiu, Mark J. Pellerite, William D. Coggio, Christopher B. Walker, JR.
  • Patent number: 7728098
    Abstract: Fluorochemical oligomeric silanes, compositions comprising such silanes and/or the condensation products of such silanes, and coatings produced with such compositions.
    Type: Grant
    Filed: July 27, 2006
    Date of Patent: June 1, 2010
    Assignee: 3M Innovative Properties Company
    Inventors: Rudolf J. Dams, Zai-Ming Qiu
  • Publication number: 20100093925
    Abstract: A composition comprises a distribution of telomers of ethylene and at least one fluoroalkyl or perfluoroalkyl halide, the telomers comprising at least one polymethylene segment (—(CH2)n—) and at least one halomethyl group (—CXH2) and optionally comprising at least one non-fluorine heteroatom, and the halogen being selected from iodine and bromine; wherein the distribution has a number average ratio of methylene moieties of the polymethylene segment to the halomethyl groups of at least about 15.
    Type: Application
    Filed: December 27, 2007
    Publication date: April 15, 2010
    Inventors: George G.I. Moore, Yu Yang, Richard M. Flynn
  • Publication number: 20100055470
    Abstract: Presently described are optical substrates having a surface layer and optical displays comprising such optical substrates. The surface layer comprises the reaction product of a polymerizable mixture comprising at least one perfluoropolyether material comprising at least two free-radically polymerizable groups and at least one segment with greater than 6 ethylene oxide repeat units; and at least one non-fluorinated binder precursor comprising at least two free-radically polymerizable groups.
    Type: Application
    Filed: November 27, 2007
    Publication date: March 4, 2010
    Inventors: Thomas P. Klun, Richard J. Pokorny, Joan M. Noyola
  • Patent number: 7666964
    Abstract: A copolymer comprises repeating units derived from at least one co-reactant comprising two or more mercapto functional groups, and repeating units derived from a fluoroacrylate comprising the reaction product of: (a) at least one fluorochemical alcohol represented by the formula: C4F9—X—OH wherein: R=hydrogen or an alkyl group of 1 to 4 carbon atoms, m=2 to 8, Rf=CnF2n+1, n=1 to 5, y=0 to 6, and q=1 to 8; (b) at least one unbranched symmetric diisocyanate; and (c) at least one hydroxy-terminated alkyl (meth)acrylate or 2-fluoroacrylate monomer having 2 to about 30 carbon atoms in its alkylene portion.
    Type: Grant
    Filed: September 21, 2007
    Date of Patent: February 23, 2010
    Assignee: 3M Innovative Properties Company
    Inventors: Zai-Ming Qiu, John C. Clark, Ramesh C. Kumar
  • Patent number: 7659351
    Abstract: Fluoroacrylates comprise the reaction product of: (a) at least one fluorochemical alcohol represented by the formula: CnF2n+1—X—OH wherein: n=1 to 4, R=hydrogen or an alkyl group of 1 to 4 carbon atoms, m=2 to 8, Rf=CnF2n+1, y=0 to 6, and q=1 to 8; (b) at least one unbranched symmetric diusocyanate; and (c) at least one hydroxy-terminated alkyl (meth)acrylate or 2-fluoro acrylate monomer having 2 to about 30 carbon atoms in its alkylene portion.
    Type: Grant
    Filed: March 19, 2007
    Date of Patent: February 9, 2010
    Assignee: 3M Innovative Properties Company
    Inventors: Gregg A. Caldwell, John C. Clark, David J. Kinning, Alan R. Kirk, Thomas P. Klun, Ramesh C. Kumar, Roger A. Mader, George G I. Moore, Zai-Ming Qiu, Richard B. Ross
  • Patent number: 7655310
    Abstract: Polyurethanes-urea based on perfluoropolyethers comprising ionizable groups and pendant groups having the following structure: —RI—Si(ORII)n(OH)3?n??(I) wherein: RI is alkylene from 1 to 10 carbon atoms; RII is an alkyl group from 1 to 4 carbon atoms; n is an integer from 0 to 3.
    Type: Grant
    Filed: January 27, 2005
    Date of Patent: February 2, 2010
    Assignee: Solvay Solexis S.p.A.
    Inventor: Tania Trombetta
  • Publication number: 20090072183
    Abstract: A composition which provides surface effects to substrates comprising a polymer containing at least one urea linkage prepared by (i) reacting (1) at least one organic diioscyanate, polyisocyanate, or mixture thereof, and (2) at least one fluorochemical compound of Formula I Rf—O(CF2CF2)r(CH2CH2)q(R1)sXH??Formula (I) wherein Rf is a linear or branched C1 to C7 perfluoroalkyl optionally interrupted by one to three oxygen atoms, r is 1 to 3, q is 1 to 3, s is 0 or 1, X is O, S, or NR2 wherein R2 is H, or C1 to C6 alkyl, and R1 is a divalent radical selected from —S(CH2)n—, p is 1 to 50, and R3, R4 and R5 are each independently H or C1 to C6 alkyl; (ii) and then reacting with (3) water, a linking agent, or a mixture thereof.
    Type: Application
    Filed: November 20, 2008
    Publication date: March 19, 2009
    Inventors: Sheng Peng, Stephen James Getty, Timothy Edward Hopkins, Ying Wang
  • Patent number: 7501472
    Abstract: An aqueous fluoromodified polyurethane system for one- or two-component anti-graffiti and anti-soiling coatings is prepared by (a) preparing a binder component based on an aqueous solution or dispersion of optionally hydroxy- and/or amino-functional oligourethanes and/or polyurethanes having fluorinated side chains, and, optionally, (b) subsequently reacting the binder component with a crosslinker.
    Type: Grant
    Filed: February 26, 2003
    Date of Patent: March 10, 2009
    Assignee: Construction Research & Technology GmbH
    Inventors: Norbert Steidl, Alois Maier, Franz Wolfertstetter, Wolfgang Hiller, Rupert Stadler
  • Publication number: 20080314287
    Abstract: Fluorochemical urethane compounds and coating compositions derived therefrom are described. The compounds and composition may be used in treating substrates, in particular substrates having a hard surfaces such as ceramics or glass, to render them hydrophilic, oleophobic and easy to clean.
    Type: Application
    Filed: June 20, 2007
    Publication date: December 25, 2008
    Inventors: Gregory D. Clark, Patrick J. Hager, Jay S. Schlechte, John C. Clark
  • Publication number: 20080293910
    Abstract: The disclosure relates to biocompatible components useful for forming compositions for use as medical/surgical synthetic adhesives and sealants. Biocompatible components of the present disclosure may include a multifunctional amine or multifunctional polyol core, with isocyanate and/or polyalkylene oxide arms, which may optionally be capped with electrophilic or nucleophilic groups. These biocompatible components may, in embodiments, be combined with optional cross linkers to form adhesive and/or sealant compositions.
    Type: Application
    Filed: May 21, 2008
    Publication date: November 27, 2008
    Inventors: Mbiya Kapiamba, Ahmad R. Hadba
  • Patent number: 7405259
    Abstract: A silylated polymer contains repeating units derived from butadiene. The polymer when partially silylated is especially useful for pressure sensitive adhesives where it imparts superior solvent resistance performance thereto.
    Type: Grant
    Filed: December 8, 2005
    Date of Patent: July 29, 2008
    Assignee: Momentive Performance Materials Inc.
    Inventors: Robert L. Frye, Richard P. Eckberg, Roy M. Griswold
  • Publication number: 20080124555
    Abstract: Presently described are optical substrates having a surface layer and optical displays comprising such optical substrates. The surface layer comprises the reaction product of a polymerizable mixture comprising at least one perfluoropolyether urethane polymeric material comprising at least two free-radically polymerizable groups and greater than 6 ethylene oxide repeat units and at least one non-fluorinated crosslinker comprising at least two free-radically polymerizable groups.
    Type: Application
    Filed: November 29, 2006
    Publication date: May 29, 2008
    Inventors: THOMAS P. KLUN, Richard J. Pokorny, Joan M. Noyola
  • Publication number: 20080114147
    Abstract: A polymer having at least one urea linkage prepared by: (i) reacting (a) at least one diisocyanate, polyisocyanate, or mixture thereof, having isocyanate groups, and (b) at least one fluorinated compound selected from the formula (I): Rf(CH2CF2)p(CH2CH2)q(R1)r—XH ??Formula (I) wherein p and q are each independently an integer of 1 to 3; r is 0 or 1; X is —O—, —NH— or —S—; R1 is a divalent radical selected from the group consisting of —S(CH2)n—, n is an integer of 2 to 4; s is an integer of 1 to 50; R2, R3, and R4 are each independently hydrogen or an alkyl group containing 1 to 6 carbon atoms; and Rf is a linear or branched chain perfluoroalkyl group having 1 to 6 carbon atoms; and (ii) reacting with (c) water, a linking agent, or a mixture thereof and methods for treating substrates to obtain surface effects is disclosed.
    Type: Application
    Filed: November 13, 2006
    Publication date: May 15, 2008
    Inventors: Sheng Peng, Stephen James Getty, Timothy Edward Hopkins, Ying Wang
  • Patent number: 7358306
    Abstract: Curable (per)fluoropolyether polyurethanes obtained by reaction in a first step of a) (per)fluoropolyether diols having a number average molecular weight from 2,000 to 5,000; with b) diisocyanates of formula OCN—R—NCO ??(VIA) wherein R is a hydrogenated and/or fluorinated radical; in a second step with the compound c) saturated or unsaturated aliphatic hydrogenated diols, (alkyl)cycloaliphatic, aromatic; oligomers or polymers of butadiene with a number average molecular weight from 500 to 4,000 having end hydroxyl groups; provided that: when the diisocyanate b) is used and the radical R in formula (VIA) is: —Ph—CH2—Ph—, the hydrogenated diols c) are optional; when the radical R has a meaning different from that above mentioned, at least one of the used hydrogenated diols c) is selected from those belonging to the c2)-c6) groups; the sum of the equivalents of the compounds a) and c) being equal to the equivalents of the compound b).
    Type: Grant
    Filed: June 20, 2002
    Date of Patent: April 15, 2008
    Assignee: Ausimont S.p.A.
    Inventors: Stefano Turri, Sergio Novelli, Anna Staccione
  • Patent number: 7358320
    Abstract: A golf ball is disclosued, comprising: a core, the core having a diameter of 1.5 inches to 1.65 inches and a first coefficient of restitution of 0.8 or greater at 125 ft/s; an intermediate layer disposed about the core, the intermediate layer having a first Shore D hardness of 20 to 80 and comprising a blend of two or more ionomers; and an outer cover layer disposed about the intermediate layer; the outer cover layer having a thickness of 0.005 inches to 0.05 inches and a second Shore D hardness of 30 to 70, the outer cover layer being composed of a castable material formed from reactants comprising at least one fluorinated polyfunctional compound, wherein the golf ball has a second coefficient of restitution of 0.8 or greater at 125 ft/s and a compression of 50 to 120.
    Type: Grant
    Filed: March 4, 2005
    Date of Patent: April 15, 2008
    Assignee: Acushnet Company
    Inventors: Murali Rajagopalan, Kevin M. Harris
  • Patent number: 7354985
    Abstract: This application is directed to novel fluorinated polymers and prepolymers derived from mono-substituted oxetane monomers having fluorinated alkoxymethylene side-chains and the method of making these compositions. The mono-substituted fluorinated oxetane monomers having fluorinated alkoxymethylene side-chains are prepared in high yield by the reaction of a fluorinated alkoxides with either 3-halomethyl-3-methyloxetane premonomers or aryl sulfonate derivative of 3-hydroxymethyl-3-methyloxetane premonomers. Preparation of a mono-substituted 3-bromomethyl-3-methyloxetane premonomer via a simple, high yield process amenable to commercial scaleup is also disclosed. The fluorinated oxetane monomers of this invention can be readily homo/co-polymerized in the presence of a Lewis acid and polyhydroxy compounds to obtain hydroxy-terminated polyether prepolymers having fluorinated alkoxymethylene side chains.
    Type: Grant
    Filed: October 3, 2003
    Date of Patent: April 8, 2008
    Inventors: Aslam A. Malik, Thomas G. Archibald
  • Patent number: 7345123
    Abstract: A composition comprises a copolymer comprising repeating units derived from at least one co-reactant comprising two or more acrylate groups and repeating units derived from a fluoroacrylate comprising the reaction product of: (a) at least one fluorochemical alcohol represented by the formula: C4F9—X—OH wherein: R=hydrogen or an alkyl group of 1 to 4 carbon atoms, m=2 to 8, Rf=CnF2n+1, n=1 to 5, y 32 0 to 6, and q=1 to 8; (b) at least one unbranched symmetric diisocyanate; and (c) at least one hydroxy-terminated alkyl (meth)acrylate or 2-fluoroacrylate monomer having 2 to about 30 carbon atoms in its alkylene portion; wherein the composition is coatable.
    Type: Grant
    Filed: December 28, 2004
    Date of Patent: March 18, 2008
    Assignee: 3M Innovative Properties Company
    Inventors: Zai-Ming Qiu, George G. I. Moore, John C. Clark, Ramesh C. Kumar
  • Patent number: 7312298
    Abstract: A golf ball is disclosed, comprising: a core, the core having a diameter of 1.5 inches to 1.65 inches and a first coefficient of restitution of 0.8 or greater at 125 ft/s; an intermediate layer disposed about the core, the intermediate layer having a first Shore D hardness of 20 to 80 and comprising a blend of two or more ionomers; and an outer cover layer disposed about the intermediate layer; the outer cover layer having a thickness of 0.005 inches to 0.05 inches and a second Shore D hardness of 30 to 70, the outer cover layer being composed of a castable material formed from reactants comprising at least one fluorinated polyfunctional compound, wherein the golf ball has a second coefficient of restitution of 0.8 or greater at 125 ft/s and a compression of 50 to 120.
    Type: Grant
    Filed: March 4, 2005
    Date of Patent: December 25, 2007
    Assignee: Acushnet Company
    Inventors: Murali Rajagopalan, Kevin M. Harris
  • Patent number: 7291688
    Abstract: A copolymer comprises repeating units derived from at least one co-reactant comprising two or more mercapto functional groups, and repeating units derived from a fluoroacrylate comprising the reaction product of: (a) at least one fluorochemical alcohol represented by the formula: C4F9—X—OH wherein: R=hydrogen or an alkyl group of 1 to 4 carbon atoms, m=2 to 8, Rf=CnF2n+1, n=1 to 5, y=0 to 6, and q=1 to 8; (b) at least one unbranched symmetric diisocyanate; and (c) at least one hydroxy-terminated alkyl (meth)acrylate or 2-fluoroacrylate monomer having 2 to about 30 carbon atoms in its alkylene portion.
    Type: Grant
    Filed: December 28, 2004
    Date of Patent: November 6, 2007
    Assignee: 3M Innovative Properties Company
    Inventors: Zai-Ming Qiu, John C. Clark, Ramesh C. Kumar
  • Patent number: 7268197
    Abstract: A fluorochemical compound comprises the reaction product of: (a) the reaction product of: (i) at least one fluorochemical alcohol represented by the formula: CnF2n+1—X—OH wherein: n=1 to 6, R=hydrogen or an alkyl group of 1 to 4 carbon atoms, m=2 to 8, Rf=CnF2n+1, y=0 to 6, q=1 to 8; and (ii) at least one unbranched symmetric diisocyanate, and (b) at least one co-reactant comprising two or more functional groups that are capable of reacting with an isocyanate group.
    Type: Grant
    Filed: December 12, 2005
    Date of Patent: September 11, 2007
    Assignee: 3M Innovative Properties Company
    Inventors: George G. I. Moore, Ramesh C. Kumar, Zai-Ming Qiu, John C. Clark, Chetan P. Jariwala, Thomas P. Klun
  • Patent number: 7214736
    Abstract: Fluorochemical composition for rendering fibrous substrates oil repellent, water repellent, and/or stain or soil repellent. The composition comprises a dispersion or a solution of a fluorinated compound which comprises the reaction product of the following combination of reactants: (i) a fluorinated polyether according to the formula: Rf—Q—Tk ??(I) ?wherein Rf represents a monovalent perfluorinated polyether group having a molecular weight of at least 750 g/mol, Q represents a chemical bond or a divalent or trivalent organic linking group, T represents a functional group capable of reacting with an isocyanate and k is 1 or 2; (ii) an isocyanate component selected from a polyisocyanate compound that has at least 3 isocyanate groups or a mixture of polyisocyanate compounds wherein the average number of isocyanate groups per molecule is more than 2; and (iii) optionally one or more co-reactants capable of reacting with an isocyanate group.
    Type: Grant
    Filed: May 23, 2003
    Date of Patent: May 8, 2007
    Assignee: 3M Innovative Properties Company
    Inventors: Frans A. Audenaert, Rudolf J. Dams, Richard S. Buckanin, Cheryl L. S. Elsbernd, Chetan P. Jariwala, E. Steven McAlister, Pierre J. Vander Elst
  • Patent number: 7199197
    Abstract: Fluoroacrylates comprise the reaction product of: (a) at least one fluorochemical alcohol represented by the formula: CnF2n+1—X—OH wherein: R=hydrogen or an alkyl group of 1 to 4 carbon atoms, m=2 to 8, Rf=CnF2n+1, y=0 to 6, and q=1 to 8; (b) at least one unbranched symmetric diisocyanate; and (c) at least one hydroxy-terminated alkyl (meth)acrylate or 2-fluoro acrylate monomer having 2 to about 30 carbon atoms in its alkylene portion.
    Type: Grant
    Filed: December 28, 2004
    Date of Patent: April 3, 2007
    Assignee: 3M Innovative Properties Company
    Inventors: Gregg A. Caldwell, John C. Clark, David J. Kinning, Alan R. Kirk, Thomas P. Klun, Ramesh C. Kumar, Roger A. Mader, George G. I. Moore, Zai-Ming Qiu, Richard B. Ross
  • Patent number: 7148309
    Abstract: This invention is directed to mono- and bis-substituted oxetane monomers having fluorinated alkoxymethylene side chains, hydroxy-terminated prepolymers derived from these mono- and bis-substituted oxetane monomers and tetrahydrofuran (THF), and polymers produced from these prepolymers, as well as the synthesis processes associated with each, and the use of the monomers, prepolymers and ultimate polymers, both directly and as components of numerous compositions.
    Type: Grant
    Filed: February 13, 2006
    Date of Patent: December 12, 2006
    Assignee: AMPAC Fine Chemicals LLC
    Inventors: Aslam A. Malik, Thomas G. Archibald, Roland P. Carlson, Kenneth J. Wynne, Edward N. Kresge
  • Patent number: 7112647
    Abstract: An object of the present invention is to provide a fluorinated polymer of adequate molecular weight with excellent transparency in a wavelength range from visible to near infrared, and to also provide a method of producing such a polymer. The present invention provides a fluorinated polymer comprising a structure represented by a formula (1) as a structural unit, as well as a method of producing this polymer using a corresponding tetrafluoroxylylenediamine or a tetrafluoroxylylene glycol as a raw material.
    Type: Grant
    Filed: December 25, 2002
    Date of Patent: September 26, 2006
    Assignee: Showa Denko K.K.
    Inventors: Isamu Taguchi, Ryuji Monden, Nobutoshi Sasaki, Hideo Miyata, Kohei Morikawa
  • Patent number: 7056846
    Abstract: This invention provides compositions and methods for treating fibrous substrates to render those substrates durably repellent to water and oil and durably resistant to dry soil comprising a fluorochemical urethane formed by reacting a tri- or higher order isocyanate with a fluorochemical monofunctional compound; and optionally a non-fluorinated aliphatic monofunctional compound.
    Type: Grant
    Filed: December 4, 2001
    Date of Patent: June 6, 2006
    Assignee: 3M Innovative Properties Company
    Inventors: John C. Clark, Malcolm B. Burleigh, Chetan P. Jariwala, Qiu Zai-Ming
  • Patent number: 7030209
    Abstract: The present invention provides an energy curable composition including a compound having an aromatic or heteroaromatic moiety; at least two fluorinated alkylene, arylene or polyether moieties, each fluorinated alkylene, arylene or polyether moiety being linked to the aromatic or heteroaromatic moiety through an ether or thioether; and at least one ethylenically unsaturated moiety, each ethylenically unsaturated moiety being linked to one of the fluorinated alkylene, arylene or polyether moieties. The present invention also provides an energy curable composition including a compound having an isocyanurate moiety, three fluorinated alkylene, arylene, or polyether moieties linked to the isocyanurate moiety at the nitrogens of the isocyanurate, and at least one ethylenically unsaturated moiety linked to one of the fluorinated alkylene, arylene, or polyether moieties. The present invention further provides polymeric materials and optical devices made using these compositions.
    Type: Grant
    Filed: February 4, 2002
    Date of Patent: April 18, 2006
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Robert Blomquist, Jian Ming S. Deng
  • Patent number: 6998460
    Abstract: This invention is directed to mono- and bis-substituted oxetane monomers having fluorinated alkoxymethylene side chains, hydroxy-terminated prepolymers derived from these mono- and bis-substituted oxetane monomers and tetrahydrofuran (THF), and polymers produced from these prepolymers, as well as the synthesis processes associated with each, and the use of the monomers, prepolymers and ultimate polymers, both directly and as components of numerous compositions.
    Type: Grant
    Filed: November 29, 2004
    Date of Patent: February 14, 2006
    Assignees: Aerojet-General Corporation, Omnova Solutions Inc.
    Inventors: Aslam A. Malik, Thomas G. Archibald, Roland P. Carlson, Kenneth J. Wynne, Edward N. Kresge
  • Patent number: 6962966
    Abstract: Monofunctional polyfluorooxetane oligomers, polymers, and co-polymers are prepared by the cationic polymerization of fluorooxetane monomers with a monoalcohol. In addition to serving as an initiator, the monoalcohol can also serve as a solvent for the fluorooxetane or other monomers to produce oligomers, polymers, or copolymers having low cyclic content. Suitable comonomers generally include various cyclic ethers. The polyfluorooxetane oligomer, polymer, or copolymer having a single hydroxyl end group can be functionalized with a variety of compounds so as to yield a functional end group such as an acrylate, a methacrylate, an allylic, an amine, etc., with the functionalized oligomer or polymer being suitable for use in radiation curable or thermal curable coating compositions. These functionalized polymers can be copolymerized and cured to provide improvements in wetting and surface properties.
    Type: Grant
    Filed: December 1, 2000
    Date of Patent: November 8, 2005
    Assignee: OMNOVA Solutions Inc.
    Inventors: Robert Medsker, Gary L. Jialanella, Raymond J. Weinert, Guillermina C. Garcia, Aslam Malik, Roland Carlson
  • Patent number: 6927276
    Abstract: Monofunctional polyfluorooxetane oligomers, polymers, and copolymers are prepared by the cationic polymerization of fluorooxetane monomers with a monoalcohol. In addition to serving as an initiator, the monoalcohol can also serve as a solvent for the fluorooxetane or other monomers to produce oligomers, polymers, or copolymers having low cyclic content. Suitable comonomers generally include various cyclic ethers. The polyfluorooxetane oligomer, polymer, or copolymer having a single hydroxyl end group can be functionalized with a variety of compounds so as to yield a functional end group such as an acrylate, a methacrylate, an allylic, an amine, etc., with the functionalized oligomer or polymer being suitable for use in radiation curable or thermal curable coating compositions. These functionalized polymers can be copolymerized and cured to provide improvements in wetting and surface properties.
    Type: Grant
    Filed: December 11, 2002
    Date of Patent: August 9, 2005
    Assignee: OMNOVA Solutions Inc.
    Inventors: Robert Medsker, Gary L. Jialanella, Raymond J. Weinert, Guillermina C. Garcia, Aslam Malik, Roland Carlson
  • Patent number: 6906115
    Abstract: A perfluoropolyether-containing composition, which can easily conform to a fluorine-free substrate and can form a film on a surface of the substrate to fix the composition to the substrate surface, wherein the composition is a carbon-carbon double bond-containing composition comprising (A) a triisocyanate prepared by trimerizing a diisocyanate, and (B) a combination of at least two active hydrogen-containing compounds, and the component (B) comprises (B-1) a perfluoropolyether having at least one active hydrogen, and (B-2) a monomer having active hydrogen and a carbon-carbon double bond.
    Type: Grant
    Filed: June 10, 2002
    Date of Patent: June 14, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Makoto Hanazawa, Yasuo Itami
  • Patent number: 6894140
    Abstract: Fast curing surgical adhesives and sealants contain an NCO-terminated hydrophilic urethane prepolymer derived from an aromatic diisocyanate and a polyol. Substantially all the aromatic diisocyanate used to prepare the NCO-terminated hydrophilic urethane prepolymer is in the para form. Optionally, the aromatic diisocyanate is substituted with at least one electron withdrawing group, such as, for example, a fluorine group.
    Type: Grant
    Filed: October 27, 2003
    Date of Patent: May 17, 2005
    Assignee: Tyco Healthecare Gropu LP
    Inventor: Mark Roby
  • Patent number: 6891013
    Abstract: The present invention provides, inter alia, novel fluorinated polyurethane elastomers (e.g., fluorinated thermoset polyurethane elastomers and fluorinated thermoplastic elastomers) prepared from polyether prepolymers formed from mono-substituted fluorinated oxetane monomers (FOX monomers) and tetrahydrofuran (THF). In addition, the present invention provides methods of making such fluorinated polyurethane elastomers.
    Type: Grant
    Filed: March 8, 2000
    Date of Patent: May 10, 2005
    Assignee: Aerojet-General Corporation
    Inventors: Aslam A. Malik, Thomas G. Archibald
  • Patent number: 6890360
    Abstract: Fluorochemical urethane compositions comprising one or more fluorochemical urethane compounds, and one or more auxiliary compounds for treatment of a fibrous substrate are described. The fluorochemical compositions are capable of improving one or more of the oil- and/or water repellency, stain- and/or soil repellency and stain and/or soil release properties, with improved durability, of the fibrous substrate treated with the fluorochemical composition.
    Type: Grant
    Filed: December 17, 2001
    Date of Patent: May 10, 2005
    Assignee: 3M Innovative Properties Company
    Inventors: Linda G. Coté , Mitchell T. Johnson, Larry A. Lien, Richard S. Buckanin
  • Patent number: 6809152
    Abstract: A golf ball comprising a cover and a core, and at least one intermediate layer interposed between the cover and the core, wherein the cover is formed from a blend comprising of a segmented polyurethane elastomer copolymers of polyether (or ester)-ester and polyether (or ester)-amide.
    Type: Grant
    Filed: October 21, 2002
    Date of Patent: October 26, 2004
    Assignee: Acushnet Company
    Inventors: Kevin M Harris, Murali Rajagopalan
  • Patent number: 6790924
    Abstract: This invention relates to the application of fluorinated urethane compositions to stone in order to protect the stone from the deleterious effects of water and pollution.
    Type: Grant
    Filed: June 13, 2002
    Date of Patent: September 14, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Douglas Robert Anton, Jack Robert Kirchner, William Howard Tuminello
  • Patent number: 6770725
    Abstract: This invention relates to macromolecule modifiers containing biologically active drugs/biomolecules, or precursors thereof, and fluoroligomers; compositions comprising the macromolecules containing the drugs and fluoroligomers in admixture with polymers, particularly biomedical polymers; articles made from the admixtures, particularly medical devices.
    Type: Grant
    Filed: June 5, 2002
    Date of Patent: August 3, 2004
    Inventor: Paul J. Santerre
  • Patent number: 6756468
    Abstract: Cmpositions for coatings having a dry content higher than 80%, preferably of about 85-90% by weight, based on polyisocyanates and PFPEs, completely crosslinkable also in a range of temperatures between 5° C. and 20° C., comprising the following components: Component 1): mixture comprising: 1.a) Partially fluorinated prepolymers, having free NCO groups, obtained by reaction of (per)fluoropolyethers (PFPEs) diols having number average molecular weight Mn in the range 800-1,300 with the cyclic trimer of the isophorondiisocyanate, 1.b) non cyclic isocyanic trimer of hexamethylendiisocyanate, Component 2): (per) fluoropolyether (PFPE) diol with Mn in the range 350-700, preferably 500-650, component 3): inert organic solvent in crosslinking conditions, complement to 100% by weight of the composition.
    Type: Grant
    Filed: January 12, 2001
    Date of Patent: June 29, 2004
    Assignee: Ausimont S.p.A.
    Inventors: Stefano Turri, Carlo Pogliani
  • Patent number: 6753386
    Abstract: The present invention relates to a film forming composition, a method of forming the composition, and application of the composition to coating formulations which provide a cured coating having acid rain resistance. A film-forming polyurethane polyol composition comprises a reaction product of an n-functional isocyanate (wherein n is a number ranging from about 2 to about 5) with at least one diol or triol or mixtures thereof and a compound containing isocyanate-reactive functional groups, preferably a monofunctional alcohol or thiol. The low viscosity polyurethane polyol of the present invention is typically crosslinked/cured using a melamine to produce a cured coating which is highly acid etch resistant as well as having other desirable physical-mechanical properties. The coating compositions have improved flow characteristics compared to compositions containing polyurethane polyols prepared without the monofunctional alcohols or thiols.
    Type: Grant
    Filed: December 16, 1997
    Date of Patent: June 22, 2004
    Assignee: Akzo Nobel N.V.
    Inventors: Alexander Leo Yahkind, Ian Wagstaff, Frederick Herbert Walker
  • Patent number: 6689839
    Abstract: Thermoset paint compositions with which paint films can be formed which have excellent acid resistance, abrasion resistance and adhesion, and with which the water repelling properties and staining resistance can be retained for a longer period of time than with the conventional fluorine resin based paint films, are obtained. Constitution: Thermoset paint film compositions which contain (a) from 20 to 80% by weight of fluorine containing copolymer, comprising fluoro-olefin and vinyl based monomer, of which the solubility parameter value is from 9.0 to 10.5 and the hydroxy group value is within the range from 60 to 150 mgKOH/g; (b) from 20-80% by weight of vinyl based (co)polymer, comprising vinyl based monomer which contains at least 10% by weight of monomer which can be repesented by formula (1), of which the solubility parameter is from 9.0 to 10.
    Type: Grant
    Filed: September 11, 1998
    Date of Patent: February 10, 2004
    Assignee: BASF Coatings AG
    Inventors: Takehi Hayakawa, Kishio Shibato, Yasuhiro Monma
  • Patent number: 6673889
    Abstract: Acrylate, or methacrylate, or allylic, functionalized polyfluorooxetanes are disclosed for use in radiation curable coating compositions. These acrylate, or methacrylate, or allylic, functionalized polymers provide improvements in wetting and surface properties that have previously been provided by migratory chemicals such as waxes and oils. The partially or fully fluorinated side groups of the fluorooxetanes are believed to be disproportionately present at the interfaces between the coating and the substrate and between the coating and the atmosphere.
    Type: Grant
    Filed: September 16, 1999
    Date of Patent: January 6, 2004
    Assignee: Omnova Solutions Inc.
    Inventors: Raymond J. Weinert, Guillermina C. Garcia, James E. Robbins, Aslam Malik
  • Patent number: 6646093
    Abstract: Water-soluble polyurethane according to the present invention is obtained from polyalkylene glycols, diisocyanates, and comb-shaped hydrophobic diols represented by the following general formula (3): wherein each of R1, R2 and R3 is a hydrocarbon group; each of Y and Y′ is hydrogen, a methyl group or a CH2Cl group; each of Z and Z′ is oxygen, sulfur or a CH2 group; n is an integer of 0 to 15 when Z is oxygen and is 0 when Z is sulfur or a CH2 group; n′ is an integer of 0 to 15 when Z′ is oxygen and is 0 when Z′ is sulfur or a CH2 group. The water-soluble polyurethane is used as, for example, an extruding auxiliary for cement materials, a mortar thickening agent, an underwater concrete thickening agent, a ceramics forming binder and a moisturizer for hair cosmetics, all of which are characterized by excellent water retention and high shape retention.
    Type: Grant
    Filed: December 12, 2000
    Date of Patent: November 11, 2003
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Manabu Tsuruta, Masahiko Mitsuzuka, Yunzhi Wu
  • Patent number: 6646088
    Abstract: This invention relates to chemical compositions comprising one or more urethane oligomers of at least two repeating units selected from the group consisting of fluorine-containing urethane oligomers and long-chain hydrocarbon-containing urethane oligomers. These urethane oligomers comprise the reaction product of (a) one or, more polyfunctional isocyanate compounds; (b) one or more polyols; (c) one or more monoalcohols selected from the group consisting of fluorochemical monoalcohols, optionally substituted long-chain hydrocarbon monoalcohols, and mixtures thereof; (d) one or more silanes; and optionally (e) one or more water-solubilizing compounds comprising one or more water-solubilizing groups and at least one isocyanate-reactive hydrogen containing group. The chemical compositions of the present invention can be applied as coatings and these coatings can impart stain-release characteristics and resist being worn-off due to wear and abrasion.
    Type: Grant
    Filed: March 26, 2002
    Date of Patent: November 11, 2003
    Assignee: 3M Innovative Properties Company
    Inventors: Wayne W. Fan, Steven J. Martin, Zai-Ming Qiu, Michael S. Terrazas, Linda G. Coté, Mitchell T. Johnson, Larry A. Lien
  • Publication number: 20030208015
    Abstract: Monofunctional polyfluorooxetane oligomers, polymers, and copolymers are prepared by the cationic polymerization of fluorooxetane monomers with a monoalcohol. In addition to serving as an initiator, the monoalcohol can also serve as a solvent for the fluorooxetane or other monomers to produce oligomers, polymers, or copolymers having low cyclic content. Suitable comonomers generally include various cyclic ethers. The polyfluorooxetane oligomer, polymer, or copolymer having a single hydroxyl end group can be functionalized with a variety of compounds so as to yield a functional end group such as an acrylate, a methacrylate, an allylic, an amine, etc., with the functionalized oligomer or polymer being suitable for use in radiation curable or thermal curable coating compositions. These functionalized polymers can be copolymerized and cured to provide improvements in wetting and surface properties.
    Type: Application
    Filed: December 1, 2000
    Publication date: November 6, 2003
    Inventors: Robert Medsker, Gary L. Jialanella, Raymond J. Weinert, Guillermina C. Garcia, Aslam Malik, Roland Carlson
  • Patent number: 6584263
    Abstract: One aspect of the present invention relates to an optical fiber coating compositions having, when cured, a Young's modulus of greater than about 950 MPa and a film to film coefficient of friction of less than about 0.44. Another aspect of the present invention relates to an coated optical fiber having a coating having a modulus of greater than about 950 MPa and a fiber to fiber coefficient of friction of less than about 0.74 measured at a speed of about 0.423 cm/sec and with a weight of about 100 grams. The coatings may include additives such as surfactants, surface agents, slip additives, waxes, and micronized polytetrafluoroethylene. The coated optical fibers of the present invention can be freely and smoothly wound on a spool without the formation of fiber loops, crossovers, or other defects.
    Type: Grant
    Filed: December 17, 2001
    Date of Patent: June 24, 2003
    Assignee: Corning Incorporated
    Inventors: Edward J. Fewkes, Inna I. Kouzmina, Huan-Hung Sheng
  • Patent number: 6555230
    Abstract: Artificial leather has a base sheet and a resin layer arranged on at least one side of the base sheet.
    Type: Grant
    Filed: March 21, 2001
    Date of Patent: April 29, 2003
    Assignees: Dainichiseika Color & Chemicals Mfg. Co., Ltd., Ukima Colour & Chemicals Mfg. Co., Ltd.
    Inventors: Kazuyuki Hanada, Akihiro Watanabe, Kazuya Kimura
  • Patent number: 6509433
    Abstract: The present invention relates to blocked fluorine-containing polyisocyanates which have a fluorine content, calculated as F=19, of 1.0 to 20.0 wt. %, preferably 4.0 to 10.0 wt. %, and are suitable for preparing stoving coatings having a water- and soil-repellent surface, wherein the fluorine-containing polyisocyanates are based on the reaction product of aliphatic polyisocyanates or polyisocyanate mixtures having an NCO content of 10 to 25 wt. % and a functionality of at least 2.5 with monofunctional isocyanate blocking agents and a fluorinated monoalcohols wherein i) 75 to 95 equivalent-% of the isocyanate groups are reacted with isocyanate blocking agents, ii) 5 to 25 equivalent-% of the isocyanate groups are reacted with fluorinated monoalcohols and iii) the equivalents of i) and ii) add up to 100%.
    Type: Grant
    Filed: September 14, 2001
    Date of Patent: January 21, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Eberhard Koenig, Beate Baumbach, Christian Füssel, Juan Gonzalez-Blanco