Reactant Contains A Fluorine Atom Patents (Class 528/70)
  • Patent number: 5672651
    Abstract: This invention provides compositions for treating fibrous substrates to render those substrates durably repellent to water and oil and durably resistant to dry soil comprising a fluorochemical polymer formed by: (a) reacting a tri- or higher order isocyanate with a fluorochemical alcohol; (b) reacting the resulting product with an amount of water sufficient to react with between 5 and 50% of the isocyanate groups present in the product compound; and (c) thereafter reacting the product with a difunctional poly(oxyalkylene)-containing material.
    Type: Grant
    Filed: October 20, 1995
    Date of Patent: September 30, 1997
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Richard S. Smith
  • Patent number: 5663273
    Abstract: Di-, tri- and poly-perfluoroalkyl-substituted alcohols and acids and derivatives thereof are described which are prepared from perfluoroalkyl iodides and di-, tri- or polyallyl alcohols or acids. These compounds contain two or more perfluoroalkyl-iodoalkyl or perfluoroalkyl-alkenyl groups and one or two alcohol or acid groups or derivatized alcohol or acid functions. They can be reacted with isocyanates, epoxy compounds, anhydrides, acids or acid derivatives to prepare a great variety of oil- and water-repellent compositions which are useful for oil- and water-repellent treatment of textiles, glass, paper, leather and other substrates.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: September 2, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Marlon Haniff, Robert Falk, Ted Deisenroth, Karl F. Mueller
  • Patent number: 5632958
    Abstract: A ratiometric method for using optical sensors is provided to measure dissolved oxygen in a fluid sample. The sensor is formulated so as to contain an oxygen permeable membrane of a cured perfluorinated urethane polymer and, incorporated therein, an oxygen-sensitive indicator component and a reference dye component. The emission spectrum from the indicator component is calibrated by comparison with that of the reference dye, which is substantially less sensitive to oxygen-quenching and which has a photodecomposition rate similar to the indicator component. Methods for making and using the membrane and sensor are provided as well.
    Type: Grant
    Filed: May 24, 1995
    Date of Patent: May 27, 1997
    Assignee: Optical Sensors Incorporated
    Inventors: James Kane, Roy Martin, Anne Schilling
  • Patent number: 5631340
    Abstract: An optical sensor is provided for measuring dissolved gases such as O.sub.2 or CO.sub.2 in a fluid sample. The sensor is formulated so as to contain a gas permeable membrane of a cured perfluorinated urethane polymer and, incorporated therein, a gas-sensitive indicator component. Methods for making and using the membrane and sensor are provided as well.
    Type: Grant
    Filed: March 1, 1995
    Date of Patent: May 20, 1997
    Assignee: Optical Sensors Incorporated
    Inventor: Alan Olstein
  • Patent number: 5627238
    Abstract: A coating composition containing about 45-80% by weight of a binder and 20-55% by weight of an organic liquid; wherein the binder contains(A) about 40-90% by weight, based on the weight of the binder, of an acrylic polymer containing polymerized hydroxyl containing monomers of the following group of hydroxy alkyl acrylate or methacrylates having 1-4 carbon atoms in the alkyl group, and polymerized alkyl acrylates and methacrylates having 1-18 carbon atoms in the alkyl groups, or styrene or any mixtures of the above and(B) about 10-60% by weight, based on the weight of the binder, of a fluorinated organic polyisocyanate crosslinking agent.
    Type: Grant
    Filed: October 16, 1995
    Date of Patent: May 6, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Douglas R. Anton, Michael J. Darmon, William F. Graham, Richard R. Thomas
  • Patent number: 5607644
    Abstract: An optical sensor is provided for measuring the pH of a fluid sample. The sensor is formulated using a fluorescent polymer composition comprising a copolymer of a water-dispersable, polyether-containing urethane olefin precursor and a fluorescent monomer species, wherein the ratio of precursor and fluorescent monomer species is such that a predetermined apparent pKa is provided. The sensor is prepared by coating the distal end of an optical waveguide with the fluorescent polymer composition, and curing the copolymer contained in the composition, e.g., by exposure to radiation of a suitable wavelength.
    Type: Grant
    Filed: June 10, 1993
    Date of Patent: March 4, 1997
    Assignee: Optical Sensors Incorporated
    Inventors: Alan Olstein, William Fowler, Jo Pritchard
  • Patent number: 5608013
    Abstract: A polyimide obtained by reacting an acid dianhydride such as catechol bistrimellitate dianhydride, bisphenol A bistrimellitate dianhydride, etc. with a diamine such as 4,4'-diamino-3,3',5,5'-tetraisopropyl-diphenylmethane, etc. has high solubility in organic solvents and good moldability at low temperatures, and can provide a thermosetting resin composition together with a polymaleimide.
    Type: Grant
    Filed: March 7, 1995
    Date of Patent: March 4, 1997
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Hidekazu Matsuura, Yasuo Miyadera
  • Patent number: 5605956
    Abstract: A fluorinated polyisocyanate which comprises an organic polyisocyanate reacted with a fluorinated monofunctional alcohol represented by the formula ##STR1## where R.sub.f is a fluoroalkyl containing group having at least 4 carbon atoms, X is a divalent radical, R.sup.3 is H or an alkyl group having 1-4 carbon atoms, n is 0-1 and m is 0-30, provided that when n is 0 then m must be equal to or greater than 1 and when m is 0, n is 1, wherein about 0.1-33 mole percent of active isocyanate groups are reacted with the fluorinated monofunctional alcohol; the fluorinated polyisocynate can be used with acrylic polymers, polyesters, alkyd resins, polyols and the like to form coating compositions, sealants, adhesives and the like.
    Type: Grant
    Filed: October 16, 1995
    Date of Patent: February 25, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Douglas R. Anton, Michael J. Darmon, William F. Graham, Richard R. Thomas
  • Patent number: 5580645
    Abstract: 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: Grant
    Filed: August 8, 1995
    Date of Patent: December 3, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Jack R. Kirchner
  • Patent number: 5576411
    Abstract: The present invention is directed to a polyisocyanate mixturei) having an NCO content of 5 to 35% by weight and prepared from an organic diisocyanate,ii) containing at least 1% by weight of isocyanurate groups (calculated as N.sub.3, C.sub.3, O.sub.3, MW 126),iii) containing allophanate groups in an amount such that there are more equivalents of allophanate groups than urethane groups andiv) containing fluorine (calculated as F, AW 19) in an amount of 0.
    Type: Grant
    Filed: September 14, 1994
    Date of Patent: November 19, 1996
    Assignee: Bayer Corporation
    Inventors: Philip E. Yeske, Edward P. Squiller, William E. Slack
  • Patent number: 5567794
    Abstract: A polymer material of the fluorine-containing polyurethane acrylate type for coating an optical fiber or for an optical fiber tape, the material being based on at least a diol, a diisocyanate, and an acrylate, and being characterized by the fact that at least one of the above compounds contains fluorine and that at least one of the above compounds contains sulfur.
    Type: Grant
    Filed: April 7, 1993
    Date of Patent: October 22, 1996
    Assignee: Alcatel Cable
    Inventors: Jean-Yves Barraud, Sophie Gervat, Victorin Ratovelomanana, Bernard Boutevin, Jean-Pierre Parisi, Aline Cahuzac, Robert Jocteur
  • Patent number: 5548019
    Abstract: An aqueous coating composition comprising a polyisocyanate compound and a fluorine-containing copolymer having hydroxyl groups, wherein the fluorine-containing copolymer having hydroxyl groups is a copolymer comprising 20-80 mol % of polymer units derived from a fluoroolefin and 0.1-25 mol % of polymer units derived from a monomer having a hydrophilic site, said polyisocyante compound and said fluorine-containing copolymer both being dispersed in water.
    Type: Grant
    Filed: January 4, 1995
    Date of Patent: August 20, 1996
    Assignees: Asahi Glass Company Ltd, Asahi Glass Coat & Resin Co., Ltd., Asia Industry Co., Ltd.
    Inventors: Shoichi Kawakami, Toru Okamoto, Nobuyuki Miyazaki, Bunji Uchino, Kazuyoshi Nomura, Hiroyuki Kato
  • Patent number: 5543200
    Abstract: A urethane coating composition is disclosed which uses fluorinated monohydric alcohols to increase abrasion resistance. One specific use of the coating is on vehicle sealing systems which use elastomeric substrates. The coating composition was found to have dramatically improved abrasion resistance in glass run channel applications over similar coatings without the fluorinated component.
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: August 6, 1996
    Assignee: GenCorp Inc.
    Inventors: I. Glen Hargis, Russell A. Livigni, Earl G. Melby, Francis J. Vitus
  • Patent number: 5541281
    Abstract: The present invention is directed to a polyisocyanate mixturei) having an NCO content of 5 to 35% by weight and prepared from an organic diisocyanate,ii) containing less than 5% by weight of isocyanurate groups (calculated as N.sub.3, C.sub.3, O.sub.3, MW 126),iii) containing allophanate groups in an amount such that there are more equivalents of allophanate groups than urethane groups andiv) containing fluorine (calculated as F, AW 19) in an amount of 0.001 to 50% by weight, based on solids.,wherein fluorine is incorporated with compounds containing two or more carbon atoms, one or more hydroxyl groups and one or more fluorine atoms. The present invention is also directed to a process for the production of this polyisocyanate mixture and to its use, optionally in blocked form, as an isocyanate component in one- or two-component coating compositions.
    Type: Grant
    Filed: December 20, 1994
    Date of Patent: July 30, 1996
    Assignee: Bayer Corporation
    Inventors: Philip E. Yeske, Edward P. Squiller, William E. Slack
  • Patent number: 5536783
    Abstract: An optical sensor is provided for measuring the pH of a fluid sample. The sensor is formulated using a fluorescent polymer composition comprising a copolymer of a water-dispersable, polyether-containing urethane olefin precursor and a fluorescent monomer species, wherein the ratio of precursor and fluorescent monomer species is such that a predetermined apparent pKa is provided. The sensor is prepared by coating the distal end of an optical waveguide with the fluorescent polymer composition, and curing the copolymer contained in the composition, e.g., by exposure to radiation of a suitable wavelength.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: July 16, 1996
    Assignee: Optical Sensors Incorporated
    Inventors: Alan Olstein, William Fowler, Jo Pritchard
  • Patent number: 5508370
    Abstract: The invention relates to a blocked polyisocyanate having an NCO functionality of from 2.2 to 4.5 and an average molecular weight of 800 to 25,000 and containing (1) blocked isocyanate groups corresponding to an NCO content of 5 to 20 wt. % calculated as free NCO, relative to unblocked polyisocyanate, (2) 1 to 75 meq of ionic groups per 100 g of blocked polyisocyanate, and (3) 3 to 40 wt.
    Type: Grant
    Filed: October 12, 1993
    Date of Patent: April 16, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut Reiff, Karl-Heinz Passon, Hans-Albert Ehlert, Peter Nussbaum
  • Patent number: 5488092
    Abstract: A primerless, one-part, heat curable, low volatile organic compound, polyurethane composition comprises a blocked polyurethane prepolymer made from a liquid hydroxyl terminated intermediate and an excess of a polyisocyanate, a curing agent, silicone and/or low friction polymer and optional fillers. Upon cure of the polyurethane composition, the silicone oil and/or low friction polymer generally imparts low friction and high abrasive resistant properties. A desired use is as a glass run channel coating.
    Type: Grant
    Filed: April 26, 1994
    Date of Patent: January 30, 1996
    Assignee: GenCorp Inc.
    Inventors: Charles M. Kausch, Earl G. Melby, Satish C. Sharma
  • Patent number: 5466770
    Abstract: The invention provides new fluorine-efficient oil- and water-repellent compositions comprising a fluorochemical oil- and water-repellent agent and a polymer extender comprising at least one percent by weight based on the weight of the extender of interpolymerized units derived from monomers containing at least one blocked or masked isocyanate function.
    Type: Grant
    Filed: May 26, 1994
    Date of Patent: November 14, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Frans A. Audenaert, Rudolf J. Dams, Robert F. Kamrath
  • Patent number: 5462880
    Abstract: A ratiometric method for using optical sensors is provided to measure dissolved oxygen in a fluid sample. The sensor is formulated so as to contain an oxygen permeable membrane of a cured perfluorinated urethane polymer and, incorporated therein, an oxygen-sensitive indicator component and a reference dye component. The emission spectrum from the indicator component is calibrated by comparison with that of the reference dye, which is substantially less sensitive to oxygen-quenching and which has a photodecomposition rate similar to the indicator component. Methods for making and using the membrane and sensor are provided as well.
    Type: Grant
    Filed: September 13, 1993
    Date of Patent: October 31, 1995
    Assignee: Optical Sensors Incorporated
    Inventors: James Kane, Roy Martin, Anne Schilling
  • Patent number: 5453248
    Abstract: An optical sensor is provided for measuring dissolved gases such as O.sub.2 or CO.sub.2 in a fluid sample. The sensor is formulated so as to contain a gas permeable membrane of a cured perfluorinated urethane polymer and, incorporated therein, a gas-sensitive indicator component. Methods for making and using the membrane and sensor are provided as well.
    Type: Grant
    Filed: August 12, 1992
    Date of Patent: September 26, 1995
    Assignee: Optical Sensors Incorporated
    Inventor: Alan Olstein
  • Patent number: 5441771
    Abstract: Moisture-hardening one-component polyurethane paints for coating elastomeric parts, consisting of polyfunctional isocyanate compounds, solvents and, optionally, auxiliaries and/or coupling agents, which contain reactive polysiloxanes and reactive surfactants for improving surface slip, may be applied by a simple painting process to elastomers, particularly apolar elastomers, for example based on styrene-butadiene rubber or polyethylene-propylene-diene and, after drying, have an optically smooth surface with good surface-slip properties with respect to glass and no abrasive effect.
    Type: Grant
    Filed: November 10, 1994
    Date of Patent: August 15, 1995
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Hans-Guenter Seltmann, Hartmut Lippert
  • Patent number: 5439948
    Abstract: The invention provides a process for the preparation of a cellular polymeric product which comprises reaction of a polyisocyanate composition with an isocyanate-reactive composition having a functionality of at least 2, in the presence of a blowing agent and in the presence of an inert, organic liquid which is substantially insoluble in the reaction mixture and which is present as the disperse phase of an emulsion or a microemulsion, characterized in that the polyisocyanate composition comprises polymethylene polyphenylene polyisocyanate having a functionality of at least 2.5 and a urethane-modified, isocyanate-ended prepolymer, wherein the isocyanate functionality of the polyisocyanate composition is at least 2.3 and wherein the concentration of urethane linkages in the polyisocyanate composition is in the range from 1 millimole to 150 millimoles per 100 grams thereof.
    Type: Grant
    Filed: November 22, 1993
    Date of Patent: August 8, 1995
    Assignee: Imperial Chemical Industries PLC
    Inventors: Rik De Vos, David Randall
  • Patent number: 5410009
    Abstract: A polyurethaneurea elastomer obtained by reacting a polyisocyanate component obtained by reacting 1,5-naphthalene diisocyanate with a polyol, with an amine component consisting essentially of an amine compound of the formula (1): ##STR1## wherein R is a bivalent polyalkylene polyether or polyalkylene polyester having an average molecular weight of at least 200, which may contain unsaturated bonds in the polyalkylene.
    Type: Grant
    Filed: June 28, 1993
    Date of Patent: April 25, 1995
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Kaneyoshi Kato, Yoshijiro Oyaizu
  • Patent number: 5410010
    Abstract: A class of cross-linked fluorinated polyurethanes, which can be used for protecting and reinforcing coatings on films, sheets, laminates and similar thin structures made of cellulose, graphite, mica, kaolin, leather etc. as well as for adhesive and reinforcing material in multi-layer structures made of films, sheets, laminates and similar thin structures made of graphite, mica, kaolin, etc. These polyurethanes can be obtained starting from the following components:(A) a polyisocyanate consisting of a perfluoropolyether chain bound to the --NCO terminal groups through an aromatic or cycloaliphatic radical; and(B) a polyol consisting of a perfluoropolyether chain bound to the --OH terminal groups through an aromatic or cycloaliphatic radical.
    Type: Grant
    Filed: July 29, 1992
    Date of Patent: April 25, 1995
    Assignee: Ausimont S.p.A.
    Inventors: Claudio Tonelli, Giovanni Simeone
  • Patent number: 5350795
    Abstract: Fluorochemical compositions for treating textile fibers and fabrics to impart oil and water repellency without thermal treatment are provided. The compositions comprise an aqueous, substantially organic solvent free, solution or dispersion of (a) a fluorochemical acrylate copolymer comprised of a fluorinated acrylate monomer, polyalkylene glycol acrylate or methacrylate, and polyalkylene glycol diacrylate or dimethacrylate; and (b) a polyalkoxylated polyurethane having pendant perfluoroalkyl groups comprised of an aliphatic or aromatic tri- or higher order isocyanate, a fluorinated alcohol, amine, or mercaptan, and a poly(oxyalkylene) diol or dithiol.
    Type: Grant
    Filed: July 9, 1993
    Date of Patent: September 27, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Richard S. Smith, Frans Audenaert
  • Patent number: 5332798
    Abstract: Fluorinated polyurethanes and polyurethane-ureas, of heat-processable, elastomeric type, constituted by rubber-like blocks and hard blocks, comprising segments derived from:(a) a macroglycol or polybutadiene-diol;(b) a perfluoropolyether-diol of formulaHO(CH.sub.2 CH.sub.2 O).sub.n --CH.sub.2 --Q--CH.sub.2 --(OCH.sub.2 CH.sub.2).sub.n OHwherein Q is a perfluoropolyether chain and "n" is comprised within the range of from 1 to 5;(c) an aromatic, aliphatic, or cycloaliphatic diisocyanate; and(d) an aliphatic, cycloaliphatic or aromatic diol or diamine, containing from 2 to 14 carbon atoms.They contain from 4 to 30% by weight of fluorine, from 10 to 60% by weight of hard components, with the molar ratio of rubber-like components (a): (b) comprised within the range of from 2 to 20. At least 80% of rubber-like segments deriving from (b) component are connected, at least at one of their sides, through a segment deriving from (c) component, with a rubber-like segment deriving from (a) component.
    Type: Grant
    Filed: December 22, 1992
    Date of Patent: July 26, 1994
    Assignee: Ausimont S.p.A.
    Inventors: Enrico Ferreri, Francesco Giavarini, Claudio Tonelli, Tania Trombetta, Ronald E. Zielinski
  • Patent number: 5319244
    Abstract: Disclosed are thin film triazine adhesives on organic carriers, method for making them and microelectronic circuit packages incorporating them. The circuit package has a substrate made up of organic, dielectric, polymeric sheets. At least one pair of the polymeric sheets face each other and are adhesively joined together by a triazine polymer.
    Type: Grant
    Filed: December 13, 1991
    Date of Patent: June 7, 1994
    Assignee: International Business Machines Corporation
    Inventors: Konstantinos I. Papathomas, David W. Wang, William J. Summa, Ashit A. Mehta
  • Patent number: 5283311
    Abstract: Fatty prepolymers and fatty modidified organic polyisocyantes are provided as internal mold release agents useful in Reaction Injection Molded (RIM) parts. A terminal fatty chain-containing molecule having a primary or secondary hydroxyl group, a primary or secondary amine group, an epoxide group, or an isocyanate group is reacted with an organic aromatic polyisocyanate to yield a fatty prepolymer having a urethane linkage, a urea linkage, or an oxazolidinone linkage; or to yield a fatty modified polyisocyanate having an allophanate linkage, a biuret linkage, or a carbodiimide-uretonimine linkage. The terminal chain on the molecule contains at least 8 branched or unbranched, saturated or unsaturated, hydrogen substituted aliphatic carbon atoms in succession or at least 5 branched or unbranched, aliphatic or cycloaliphatic perfluorinated atoms in succession.
    Type: Grant
    Filed: December 30, 1992
    Date of Patent: February 1, 1994
    Assignee: BASF Corporation
    Inventors: Thirumurti Narayan, Anthony Tantillo, William G. Conger
  • Patent number: 5254660
    Abstract: Solutions of a) a fluorine-containing polyisocyanate in b) an isocyanate-inert solvent are used to impart water, oil and dirt resistance to porous inorganic substrates impregnated therewith. The fluorine-containing polyisocyanate is preferably selected from fluorine-containing polyisocyanates having a fluorine content in the form of perfluorinated alkyl groups of from about 15 to about 60% by weight and an isocyanate content of from about 0.5 to about 15% by weight. These isocyanates are obtained by reaction of (cyclo)aliphatic isocyanates with fluorine-containing mono- and polyhydric alcohols, and selected fluorine-containing alcohols suitable for the production of these polyisocyanates.
    Type: Grant
    Filed: November 2, 1992
    Date of Patent: October 19, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Stephan Kirchmeyer, Hanns-Peter Muller, Hermann Kober, Stefan Bohm, Josef Pedain
  • Patent number: 5214121
    Abstract: Diols containing perfluoroalkyl radicals are produced by reacting compounds of the formulaR.sub.f --(E).sub.m --X'--H(R.sub.f =perfluoroalkyl radical, E is an alkylene group optionally interrupted by certain groups and/or substituted at the end, m=0 or 1, X'--H=--CONRH, --SO.sub.2 NRH or --SH) in a first step with diols containing at least 2 halogen atoms. Preferably the obtained products are reacted in a second reaction step with polyvalent isocyanates to prepolymers with free --NCO-- or free --OH--groups and these prepolymers are reacted in a third step with compounds containing isocyanate groups and/or hydroxyl groups. The first reaction step is carried out in an aprotic solvent which is insoluble in water, in the presence of an aqueous solution of an alkali metal carbonate. Intermediate products have not to be isolated.The obtained polyurethanes can be used in form of aqueous dispersions for the oil- and water repellent finishing of textiles.
    Type: Grant
    Filed: May 17, 1991
    Date of Patent: May 25, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Franz Mosch, LuSimpert, Michael Bernheim
  • Patent number: 5206074
    Abstract: Disclosed is a polymeric product of diglycidyl bis phenol p-dialkyl benzene, and dicyanate diphenyl hexafluoro isopropane. Also disclosed is an organic polymeric dielectric composite of organic polymeric films, as polyimide films, dispersed in and reinforcing the organic polymeric adhesive reaction product of diglycidyl bis phenol p-dialkyl benzene, and dicyanate diphenyl hexafluoro isopropane. Further disclosed is an electronic circuit package that is adapted to receive at least one microelectronic circuit chip, with at least one layer having a substrate of an organic polymeric dielectric composite of organic polymeric films and the organic polymeric adhesive reaction product of diglycidyl bis phenol p-dialkyl benzene, and dicyanate diphenyl hexafluoro isopropane.
    Type: Grant
    Filed: February 20, 1991
    Date of Patent: April 27, 1993
    Assignee: International Business Machines Corporation
    Inventors: Charles R. Davis, Ashit A. Mehta, Konstantinos Papathomas, Lee P. Springer, William J. Summa, David W. Wang
  • Patent number: 5204441
    Abstract: Branched-chain diols and a method of forming them by reacting 1,4-diiodoperfluorobutane and perfluoropropylene to obtain branched-chain diiodide adducts thereof, reacting the diiodide adducts with ethylene to obtain I--CH.sub.2 CH.sub.2 --R--CH.sub.2 CH.sub.2 --I, wherein R is a branched-chain perfluoroalkyl radical, and hydrolysing the iodo groups to alcohols to obtain HO--CH.sub.2 CH.sub.2 --R--CH.sub.2 CH.sub.2 --OH. These diols can be reacted with branched-chain diisocyanates to form polyurethanes of better processability and lower glass transition temperatures than polyurethanes prepared from linear fluorinated monomers.
    Type: Grant
    Filed: March 12, 1990
    Date of Patent: April 20, 1993
    Assignee: Fluorochem Inc.
    Inventors: Kurt Baum, Thomas G. Archibald, Aslam A. Malik
  • Patent number: 5200493
    Abstract: Heteroatom containing perfluoroalkyl terminated neopentyl mercapto-alcohols of the formulas I and IIHS--[CH.sub.2 C(CH.sub.2 X--E--R.sub.f).sub.2 CH.sub.2 ]--OH (I)HS--[CH.sub.2 C(CH.sub.2 X.sub.1 --R.sub.f).sub.2 CH.sub.2 ]--OH (II)are prepared from the corresponding perfluorinated neopentyl oxetanes where R.sub.f is a straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms, E is a linking group, and X and X.sub.1 are heteroatom moieties.The reaction products of these fluorinated mercapto-alcohols with electrophiles are disclosed as are certain functional derivatives. Compositions containing such materials provide improved thermal stability and useful low surface energy oil and water repellent coatings for textiles, glass, paper, leather, and other materials.
    Type: Grant
    Filed: June 19, 1992
    Date of Patent: April 6, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Michael Jacobson, Kirtland P. Clark
  • Patent number: 5194463
    Abstract: Provided are novel light-absorbing polyurethane compositions and blends of said polyurethane compositions with other thermoplastic polymers. Also provided are shaped or formed articles comprised of the light-absorbing polyurethane compositions and light-absorbing thermoplastic polymer blends.
    Type: Grant
    Filed: September 27, 1991
    Date of Patent: March 16, 1993
    Assignee: Eastman Kodak Company
    Inventors: James J. Krutak, Max A. Weaver, William W. Parham, Wayne P. Pruett
  • Patent number: 5189135
    Abstract: Low molecular weight non-film forming fluorinated polyurethanes having a hydroxy functionality obtained from the reaction of at least one diisocyanate with at least one hydroxy-capped perfluoropolyether having a molecular weight within the range of from greater than 1,000 to 5,000 and with at least one polyol with a functionality of at least 2.
    Type: Grant
    Filed: May 5, 1992
    Date of Patent: February 23, 1993
    Assignee: Syremont S.p.A.
    Inventors: Ennio Cozzi, Franco Federici, Paolo Parrini
  • Patent number: 5185421
    Abstract: Disclosed are fluorinated macromonomers containing one or more hydroxy groups, which are useful as monomers in other polymerization. Also disclosed are processes and an intermediate for making such macromonomers, and condensation and free radically made polymers which contain the macromonomers. The macromonomers are useful for modifying the properties of the polymers into which they are incorporated.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: February 9, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Gordon M. Cohen, William B. Farnham, Andrew E. Feiring
  • Patent number: 5173301
    Abstract: Surgical adhesives, comprising an NCO-terminated hydrophilic urethane prepolymer derived from an organic polyisocyanate and a polyol component comprising a polyester polyol derived from an electron-attracting group-containing dicarboxylic acid, such as 2-ketoglutaric acid, are capable of being easily hydrolyzed within a living body after a certain period of time.
    Type: Grant
    Filed: November 27, 1991
    Date of Patent: December 22, 1992
    Assignee: Sanyo Chemical Industries, Ltd.
    Inventors: Tetsuo Itoh, Takehisa Matsuda
  • Patent number: 5153297
    Abstract: The present invention relates to water-dispersible polyetherester-modified polyurethane ionomers containing 10 to 100 milliequivalents of ionic, preferably cationic, groups per 100 g of ionomer; 2 to 40% by weight of polyetherester groups; and 1 to 35% by weight of ethylene oxide units, in which the percentages are based on the weight of the polyetherester-modified polyurethane ionomer.The present invention also relates to a process for the preparation of these polyetherester-modified polyurethane ionomers and to aqueous compositions containing these polyetherester-modified polyurethane ionomers and polymers containing perfluoralkyl groups.
    Type: Grant
    Filed: December 5, 1991
    Date of Patent: October 6, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Thomas Munzmay, Manfred Schmidt, Peter Nussbaum, Hans-Albert Ehlert
  • Patent number: 5128435
    Abstract: A resin composition comprising an epoxy resin and an isocyanate group-containing fluorine compound is particularly suitable for covering a magnetic recording medium comprising a non-magnetic substrate and formed thereon a thin magnetic film so as to give excellent sliding durability.
    Type: Grant
    Filed: July 16, 1990
    Date of Patent: July 7, 1992
    Assignee: Hitachi, Ltd.
    Inventors: Mitsuyoshi Shoji, Takayuki Nakakawaji, Yutaka Ito, Shigeki Komatsuzaki, Toshikazu Narahara
  • Patent number: 5080976
    Abstract: A blade comprising a polymeric elastomer containing a low surface energy compound, wherein the low surface energy compound exists in the polymeric elastomer as primary particles with an average particle size of 1 .mu.m or less or the low surface energy compound is in a mutually dissolved state in the polymeric elastomer, and a method for preparation thereof.A blade comprising a molded product obtained by curing a silicone-modified prepolymer formed by the reaction of a polyurethane prepolymer and silicone oil in a solvent, and a method for preparation thereof.
    Type: Grant
    Filed: February 14, 1989
    Date of Patent: January 14, 1992
    Assignee: Canon Kabushiki Kaisha
    Inventors: Noriyuki Yanai, Masahiro Watabe
  • Patent number: 5077372
    Abstract: A thermoplastic polyurethaneurea having free amino groups is the reaction product of a diisocyanate, a fluorinated polyol, a non-fluorinated polyol and a polyamine. The invention includes a shaped polymeric support structure having the thermoplastic polyurethaneurea coated thereon and a medical article comprising the coated support and heparin covalently bonded to the free amino groups of the coated support. In another aspect of the invention, a method for preparing the heparinized medical article is provided.
    Type: Grant
    Filed: March 20, 1991
    Date of Patent: December 31, 1991
    Assignee: Becton, Dickinson and Company
    Inventors: Can B. Hu, Donald D. Solomon
  • Patent number: 5075409
    Abstract: Marterials which are active in nonlinear optics, having a repeating unit of the following formula I: ##STR1## in which R.sub.1 and R.sub.2, are either identical or different, and denote a linear or branched methylenic chain, preferably containing from 2 to 6 carbon atoms; R.sub.3 is an aliphatic, aromatic or arylaliphatic hydrocarbon radical; R.sub.4 and R.sub.5, which are identical or different, denote a nitrogen atom or a CH radical, or alternatively R.sub.4 and R.sub.5 are both carbon with the R.sub.4 -R.sub.5 bond being a double or a triple bond; and Z.sub.1 and Z.sub.2, which are identical or different, denote an aromatic group wherein Z.sub.1 optionally contains one or more substituents R.sub.7 and wherein Z.sub.2 optionally contains one or more substituents R.sub.7 in addition to group A, each substituent R.sub.7 may be lower alkyl, halogen, amido, amino, sulfoxide, hydroxyl radical, alkoxy and trifluoromethyl; and A denotes an electron-acceptor group, with Z.sub.2 having one or more groups A.
    Type: Grant
    Filed: May 3, 1990
    Date of Patent: December 24, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventors: Pascal Barthelemy, Remi Meyrueix, Gerard Mignani
  • Patent number: 5045624
    Abstract: Heteroatom containing perfluoroalkyl terminated neopentyl glycols of the formulas HO[--CH.sub.2 C(CH.sub.2 X--E--R.sub.f).sub.2 CH.sub.2 O].sub.1-3 --H or HO[--CH.sub.2 C(CH.sub.2 X--R.sub.f).sub.2 CH.sub.2 O].sub.1-3 --H are prepared from halogenated neopentyl glycols or oxetanes and thiols of the formula R.sub.f --E--SH, amines of the formula R.sub.f --E--NH--R, alcohols of the formula R.sub.f --E--OH or perfluoro-amides, wherein R.sub.f is a straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms.The polymeric reaction products of said fluorinated diols, and optionally other diols with isocyanates to prepare polyurethanes; with amines and isocyanates to prepare polyureas/polyuretanes; with acids or derivatives to prepare polyesters or polycarbonates are disclosed. These include polymeric, random or block urethane, and/or urea, and/or ester compositions containing the residue of at least one R.sub.
    Type: Grant
    Filed: June 5, 1990
    Date of Patent: September 3, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert A. Falk, Kirtland P. Clark, Athanasios Karydas, Michael Jacobson
  • Patent number: 5043410
    Abstract: Fluorinated polyurethanes containing blocks having a perfluoropolyethereal structure, with rubber-like properties, alternated with stiff structural units are taught. The stiff units are at least partially provided with a double bond of the olefinic type, which is suitable for causing the cross-linking of the polymeric chains with a cross-linking system of the radicalic type.
    Type: Grant
    Filed: September 15, 1989
    Date of Patent: August 27, 1991
    Assignee: Ausimont S.r.l.
    Inventors: Alberto Re, Francesco Giavarini, Cesare Cova
  • Patent number: 5041516
    Abstract: Dendritic macromolecules and a novel convergent process for producing the same are disclosed. The convergent process enables the accurate control and design of the surface functionality of the macromolecule.
    Type: Grant
    Filed: June 21, 1989
    Date of Patent: August 20, 1991
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Jean M. J. Frechet, Craig J. Hawker, Athena E. Philippides
  • Patent number: 5032666
    Abstract: A thermoplastic polyurethaneurea having free amino groups is the reaction product of a diisocyanate, a fluorinated polyol, a non-fluorinated polyol and a polyamine. The invention includes a shaped polymeric support structure having the thermoplastic polyurethaneurea coated thereon and a medical article comprising the coated support and heparin covalently bonded to the free amino groups of the coated support. In another aspect of the invention, a method for preparing the heparinized medical article is provided.
    Type: Grant
    Filed: June 19, 1989
    Date of Patent: July 16, 1991
    Assignee: Becton, Dickinson and Company
    Inventors: Can B. Hu, Donald D. Solomon
  • Patent number: 5026814
    Abstract: The invention relates to polyurethanes comprising polyoxyperfluoroalkylene blocks of rubber-like nature and rigid segments derived from short-chain aliphatic diols, optionally from aliphatic diamines, and from aliphatic or cycloaliphatic or aromatic diisocyanate. The number of the rigid-type segments is equal to or greater than the number of the polyoxyperfluoroalkylene blocks. The polyurethane are characterized by a glass transition temperature lower than -80.degree. C., a tensile strength greater than 30 kg/cm.sup.2, a hardness between 50 Shore A and 75 Shore D, and good thermoforming characteristics.
    Type: Grant
    Filed: September 15, 1989
    Date of Patent: June 25, 1991
    Assignee: Ausimont S.r.l.
    Inventors: Alberto Re, Francesco Giavarini
  • Patent number: 5015719
    Abstract: Dicyanato diphenyl fluorinated alkane resin precursor compositions are modified by the addition of minor predetermined amounts of aromatic diepoxides having high epoxide equivalent weights in order to reduce the curing temperature of prepregs and laminates, such as circuit boards, while retaining low dielectric constants, heat stability and high flame retardance.
    Type: Grant
    Filed: July 14, 1989
    Date of Patent: May 14, 1991
    Assignee: International Business Machines Corporation
    Inventors: Kostas I. Papathomas, William J. Summa, David W. Wang
  • Patent number: 5001209
    Abstract: Polyurethanes having high hyperpolarizability densities and other favorable properties can be easily prepared from nonlinear optical active diols (NLO-diols) of a certain general formula, which have a delocalized .pi. electron system to which both an electron donor group and an electron acceptor group are coupled directly (D.pi.A system). The polyurethanes may be used in optical waveguides.
    Type: Grant
    Filed: June 29, 1989
    Date of Patent: March 19, 1991
    Assignee: Akzo N.V.
    Inventors: Carel T. J. Wreesmann, Doetze J. Sikkema, Erwin W. P. Erdhuisen
  • Patent number: 4994542
    Abstract: Elastomeric or flexible surgical adhesives, comprising (i) a NCO-terminated hydrophilic urethane prepolymer derived from a fluorine-containing polyisocyanate and a hydrophilic polyether polyol of higher oxyethylene content, or a combinatioin of (i) with (ii) an unsaturated cyano compound containing a cyano group directly bonded to a polymerizable double bond, exhibit low toxicity, may be safely used for bonding of tissues and possess a rapid cure rate and sufficient bonding power.
    Type: Grant
    Filed: March 7, 1989
    Date of Patent: February 19, 1991
    Assignees: Asahi Glass Co., Ltd., Sanyo Chemical Industries, Ltd.
    Inventors: Takehisa Matsuda, Teruo Takakura, Tetsuo Itoh