Material Contains A Phosphorus Atom Patents (Class 528/51)
  • Patent number: 4258169
    Abstract: A process is disclosed for the preparation of liquid, storage-stable, polyisocyanate compositions containing a release agent formed in situ which compositions are useful, for example, as binder resins in the formation of particle boards which latter, because of the presence of the release agent, show no tendency to adhere to the face of metal platens used in their formation. The process comprises heating an organic polyisocyanate (polymethylene polyphenyl polyisocyanate preferred) with an acid phosphate (e.g. a mixture of mono- and di-alkyl acid phosphates) under conditions controlled as to time and temperature so as to yield a product which is storage stable and shows no tendency to deposit solid or to separate into two liquid phases.
    Type: Grant
    Filed: March 26, 1980
    Date of Patent: March 24, 1981
    Assignee: The Upjohn Company
    Inventors: Richard A. Prather, David L. Williams, Robert M. Partin, Warren J. Rabourn
  • Patent number: 4256795
    Abstract: A heat transfer comprising a temporary support and a label carried on the support. The label comprises a layer of a polyurethane resin system which includes a polyurethane obtained by reaction of a diphenyl isocyanate, a free glycol and a polyester either of the formula ##STR1## wherein R is an alkylene radical of 2 to 8 carbon atoms and R.sup.1 is an alkylene radical of 4 to 10 carbon atoms or of the formula ##STR2## wherein R.sup.11 is an alkylene radical of 4 to 8 carbon atoms. The polyurethane resin system further includes a cross-linking agent and a catalyst so that when the label is placed in contact with an article to be marked and subjected to heat and pressure, the resin system is converted to an inert insoluble and wear resistant form and a substantially permanent marking is produced on the article.
    Type: Grant
    Filed: May 27, 1977
    Date of Patent: March 17, 1981
    Assignee: Polymark Corporation
    Inventors: Ian H. Day, William A. Baldwin, Harold J. Stern
  • Patent number: 4237252
    Abstract: Storage-stable, one-part, curable resin compositions comprising I. a latent catalyst which comprises rupturable microcapsules having shell walls of a crosslinked interfacial polyurethane-polyether reaction product and liquid fills of a Lewis acid-glycerol complex, II. a cationically curable monomer composition and III. a Lewis base scavenger.
    Type: Grant
    Filed: June 28, 1979
    Date of Patent: December 2, 1980
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Richard G. Newell, Harold E. Rude
  • Patent number: 4235976
    Abstract: The instant invention is directed to phosphonates of the formulae: ##STR1## in which n represents an integer of from 0 to 3,R represents H or --(CH.sub.2).sub.m --COOM,m represents an integer of from 0 to 3,M represents an alkali metal, or NR'.sub.4 wherein R' represents H or a C.sub.1 -C.sub.4 alkyl group; ##STR2## in which A represents (CH.sub.2).sub.x or C.sub.6 -C.sub.10 arylene (preferably phenylene),x represents an integer of from 0 to 5,R' and R" which may be the same or different representM represents an alkali metal, or NR'.sub.4.The invention is also directed to the use of these phosphonates as trimerization catalysts.
    Type: Grant
    Filed: June 27, 1979
    Date of Patent: November 25, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Haas, Rolf Wiedermann
  • Patent number: 4229560
    Abstract: A thermostable heterocyclic polymer constituted by monomer units of the general formula ##STR1## where R.sup.1 and R.sup.2 denote an organic radical having from 2 to 1000 carbon atoms;a radical having 2 to 1000 carbon atoms, containing:1 to 1000 atoms of Si,and/or 1 to 1000 atoms of F,and/or 1 to 1000 atoms of Cl,and/or 1 to 1000 atoms of Br,and/or 1 to 1000 atoms of N,and/or 1 to 1000 atoms of S,and/or 1 to 1000 atoms of P,and/or 1 to 1000 atoms of B,and/or 1 to 1000 atoms of O,R.sup.1 and R.sup.2 being either the same or different;R.sup.3 .dbd.NH, CH.sub.2 ;R.sup.4 is a radical which, with R.sup.3 .dbd.NH, may be ##STR2## while with R.sup.3 .dbd.CH.sub.
    Type: Grant
    Filed: May 30, 1978
    Date of Patent: October 21, 1980
    Inventors: Alexei Y. Chernikhov, Mikhail N. Yakovlev, Valentina B. Lysova, Evgeny L. Gefter, Nina N. Shmagina
  • Patent number: 4224422
    Abstract: Curable expoy resin-polyisocyanate systems which incorporate a minor amount of a cationically polymerizable, ethylenically unsaturated monomer and which are catalyzed by a Lewis acid.
    Type: Grant
    Filed: June 28, 1979
    Date of Patent: September 23, 1980
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Harold E. Rude, Richard G. Newell
  • Patent number: 4221572
    Abstract: An abrasive material which comprises abrasive grains and a polycarbodiimide and polyurethane resin as the binder for the abrasive grains and a method of preparation thereof are disclosed. The polycarbodiimide and polyurethane resin is prepared by reacting a polyisocyanate and a polyol in the presence of a catalyst. The resin has a specified amount of carbodiimide bonding and urethane bonding.
    Type: Grant
    Filed: March 2, 1978
    Date of Patent: September 9, 1980
    Assignee: Kao Soap Company
    Inventors: Yasuhiro Torimae, Tamio Ishiai
  • Patent number: 4217436
    Abstract: Novel bis cyclic ureas are disclosed having the formula ##STR1## wherein C.sub.n H.sub.a n represents alkylene from 4 to 12 inclusive and provided there are at least 4 carbon atoms in succession in the chain and R is the residue obtained by the removal of both halogen atoms from a diacid halide.The bis cyclic ureas are easily converted to a novel class of aliphatic diisocyanates simply by heating. Alternatively, they are blended with polymeric polyols to form one-component storage stable compositions which are thermally converted to polyurethane resins without any significant volatile or side product formation.
    Type: Grant
    Filed: December 11, 1978
    Date of Patent: August 12, 1980
    Assignee: The Upjohn Company
    Inventors: Reinhard H. Richter, Benjamin W. Tucker, Henri Ulrich
  • Patent number: 4206104
    Abstract: Resin mixtures of N,N'-dihydroxyalkyl ester substituted imidazolidinediones are especially useful in coating compositions having a low organic solvent content. The substituted imidazolidinediones have the formula ##STR1## wherein R and R' are independently hydrogen or hydrocarbon groups having from 1 to 8 carbon atoms, X is ##STR2## where the R" groups are independently hydrocarbon groups having from 1 to 17 carbon atoms.
    Type: Grant
    Filed: October 10, 1978
    Date of Patent: June 3, 1980
    Assignee: PPG Industries, Inc.
    Inventors: Rostyslaw Dowbenko, Ronald J. Lewarchik, William J. Birkmeyer
  • Patent number: 4203883
    Abstract: There are disclosed aqueous colloidal dispersions of tertiary amine salts of urea-urethane polymers of triamine-containing polyamines and isocyanate-terminated, urethane prepolymers having carboxylic groups. The urea-urethanes have sufficient tertiary amine neutralized, carboxylic groups to provide stable, aqueous dispersions having infinite dilutability with water, and the solids of the amine-neutralized dispersions are essentially of colloidal size. Carboxylic groups are supplied by polyol reactants employed in making the prepolymers. The colloidal, urea-urethane polymers may be stably dispersed in the aqueous medium, even in the absence of substantial amounts of cosolvents, and are useful in, for instance, coating compositions to provide water-resistant coatings.
    Type: Grant
    Filed: September 5, 1978
    Date of Patent: May 20, 1980
    Assignee: Textron, Inc.
    Inventor: David G. Hangauer, Jr.
  • Patent number: 4195132
    Abstract: The present invention relates to novel, substantially insoluble and infusible plastics which are cross-linked by way of triazine rings and, optionally, by way of tri-substituted bis-oxymethylene urea groups or urethane groups.
    Type: Grant
    Filed: May 5, 1977
    Date of Patent: March 25, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rudolf Sundermann, Gunther Rottloff, Ernst Grigat
  • Patent number: 4194068
    Abstract: Liquid flame-retardants for polyurethane compositions are disclosed. The liquid flame-retardants contain a mixture of a bromohydrin of pentaerythritol, a polyhydric alcohol, and a sufficient amount of a flame-retardant organo-phosphorus compound to render the mixture a substantially solids-free liquid at 25.degree. C., one atmosphere pressure. Illustrative of these flame-retardants is a solution of 2,2-bis(bromomethyl)-1,3-propanediol, a cyclic phosphonate ester of the formula ##STR1## where x=0 or 1, and a poly(oxypropylene) adduct of glycerol having an average molecular weight of about 300.
    Type: Grant
    Filed: March 21, 1978
    Date of Patent: March 18, 1980
    Assignee: The Dow Chemical Company
    Inventors: Dennis P. Miller, Masahiko Tamaki
  • Patent number: 4187215
    Abstract: A composition and method are disclosed in which a homopolymeric isocyanate such as a toluene diisocyanate polymer is formed IN SITU within a polyurethane composition containing a hydroxy-terminated organic compound, preferably a polybutadiene, an amount of self-polymerizable polyisocyanate in excess of the stoichiometric requirement, and a polymerization catalyst therefor. The composition can be fully cured on a surface and yet provides an excess of stable material, i.e. dormant isocyanate containing groups which are reactive on demand to strengthen interfaces with adjacent layers containing available hydroxyl groups, such as a layer of solid polyurethane-based propellant, without the need for intermediate reactive coatings.
    Type: Grant
    Filed: September 25, 1972
    Date of Patent: February 5, 1980
    Assignee: Aerojet-General Corporation
    Inventor: John M. Wrightson
  • Patent number: 4182812
    Abstract: A process is described for preparing hydantoins by reacting an isocyanate or isothiocyanate having 2 or more isocyanate or isothiocyanate groups with an unsaturated diamide at 0.degree.-450.degree. C. said diamide being a compound of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.6 may be the same or different and each is from the group consisting of hydrogen, alkyl of 1-20 carbon atoms, alkenyl or 1-20 carbon atoms, aryl of 4-20 carbon atoms and aralkyl or 7-20 carbon atoms, and R.sub.4 and R.sub.6 together are additionally together a heterocyclic having 3-7 carbon atoms wherein the nitrogen heteroatom is bonded to both R.sub.3 and R.sub.6, andR.sub.1 and R.sub.2 are also additionally halogen, andx and y each are integers from 1 to 3, with the proviso that at least one of x and y is 1.
    Type: Grant
    Filed: November 23, 1977
    Date of Patent: January 8, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilfried Zecher, Rudolf Merten
  • Patent number: 4174307
    Abstract: Novel compounds which are the products of monomeric organic reactants containing one or more active hydrogen atoms as determined by the Zerewitinoff method, e.g., a polyol, and organic polyisocyanates, e.g., diisocyanates, in such amounts as to provide about two isocyanate groups for each active hydrogen-containing group thereby forming isocyanate terminated intermediates which are reacted with monomeric organic reactants having at least one active hydrogen-containing group and preferably also an unsaturated group, preferably in a terminal position. One of the monomeric organic active hydrogen-containing reactants must have only one active hydrogen.
    Type: Grant
    Filed: July 31, 1978
    Date of Patent: November 13, 1979
    Assignee: Polychrome Corporation
    Inventor: William Rowe
  • Patent number: 4169196
    Abstract: An improved process for the preparation of thermoplastic polyurethane elastomers by a one-shot reaction of an organic diisocyanate, a polymeric diol, and a diol extender is disclosed wherein the diol components, either singly or together, are treated with a trivalent phosphorus compound prior to their reaction with the diisocyanate in the presence of a stannous tin urethane catalyst. The process when carried out with pure urethane grade diol components results in very efficient catalysis which in turn requires lower levels of stannous tin catalyst than would otherwise be employed. Moreover, the process can be carried out with diol components that are not urethane grade materials but which are contaminated by high levels of peroxidic impurities and which materials would otherwise be useless for the preparation of high grade elastomer products.
    Type: Grant
    Filed: October 14, 1977
    Date of Patent: September 25, 1979
    Assignee: The Upjohn Company
    Inventors: Benjamin S. Ehrlich, Curtis P. Smith
  • Patent number: 4156065
    Abstract: An improved process is described for the reaction of an isocyanate (mono or poly) with a carboxylic acid or anhydride (mono or poly) to form the corresponding imide, amide or amide-imides. The improvement lies in using as the catalyst the 1-oxide, 1-sulfide or 1-hydrocarbylimino derivative of a phospholene, phospholane or phosphetane. The latter compounds are also substituted in the 1-position by a hydrocarbyl (C.sub.1-12) or halohydrocarbyl (C.sub.1-12) and may additionally carry one or more halo, lower-alkoxy, phenoxy, lower-hydrocarbyl or halo-substituted hydrocarbyl groups on the ring carbon atoms.
    Type: Grant
    Filed: January 21, 1977
    Date of Patent: May 22, 1979
    Assignee: The Upjohn Company
    Inventors: Kemal B. Onder, Curtis P. Smith
  • Patent number: 4152309
    Abstract: A pressure-sensitive adhesive composition comprising a liquid diene polymer containing therein an average of about 2.0 to about 2.5 functional groups capable of reacting with an isocyanate group, an isocyanate compound containing therein 2 or more isocyanate groups, and a tackifier, wherein an anionic surface active agent is compounded therewith in an amount of about 0.2 to about 10 parts by weight per 100 parts by weight of the total weight of the liquid diene polymer and the isocyanate compound. This pressure-sensitive adhesive composition is coated on a support and heated to produce a pressure-sensitive adhesive layer whereby a pressure-sensitive adhesive tape, for example, can be obtained.
    Type: Grant
    Filed: January 23, 1978
    Date of Patent: May 1, 1979
    Assignee: Nitto Electric Industrial Company, Ltd.
    Inventors: Ichiro Ijichi, Shigetoshi Kai, Hikaru Teranishi, Akira Morioka, Kazuyoshi Seki
  • Patent number: 4150211
    Abstract: The present invention relates to mixtures which are suitable for use as lacquer powders or as binders for lacquer powders and which are solid and capable of being pulverized at temperatures below about 40.degree. C. and liquid at temperatures above about 150.degree. C., which mixtures comprise(a) an isocyanate component having masked isocyanate groups;(b) a polyhydroxyl component; and, optionally(c) the conventional auxiliary agents and additives;Characterized in that the substance used as component (a) is a polyisocyanate having isocyanurate groups and isocyanate groups which are masked with lactams. The present invention also relates to the use of these mixtures as lacquer powders or as binders for lacquer powders for coating any heat-resistant substrate by the conventional coating methods employed for lacquer powders.
    Type: Grant
    Filed: February 16, 1978
    Date of Patent: April 17, 1979
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hanns P. Muller, Kuno Wagner, Hans J. Kreuder
  • Patent number: 4147710
    Abstract: A compound adapted to be used to advantage as a catalyst for making carbodiimide foams is prepared by a process wherein(a) a phosphetane oxide or phosphetane sulphide of the general Formulae I and II: ##STR1## wherein X represents a C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.6 -C.sub.14 aryl, C.sub.7 -C.sub.20 aralkyl, C.sub.1 -C.sub.18 alkoxy or C.sub.6 -C.sub.14 aroxy group andR.sup.1 to R.sup.6 represent hydrogen and/or C.sub.1 -C.sub.4 alkyl groups and is reacted with(b) a mono-, di- and/or polyhydric alcohol having a molecular weight of about 32 to about 250, a protonic acid which has a pH of between 1 and 8 in N/10 aqueous solution, a metal salt or an acid chloride.
    Type: Grant
    Filed: September 23, 1975
    Date of Patent: April 3, 1979
    Assignee: Bayer Aktiengesellschaft
    Inventors: Andrea La Spina, Werner Dietrich, Reinhard Schliebs
  • Patent number: 4129715
    Abstract: Substantially linear, segmented polyester amides are described which contain aromatic residues in the "hard" segments but which still possess sufficiently low melt properties to be injection moldable. The polyester amides are obtained by reacting a carboxylic acid-terminated prepolymer (derived by reacting an excess of a dicarboxylic acid with a polymeric diol of molecular weight 400 to 4000) with a stoichiometric amount of methylenebis(phenyl isocyanate) or toluene diisocyanate or mixtures of these isocyanates and, optionally, a dicarboxylic acid.
    Type: Grant
    Filed: January 16, 1978
    Date of Patent: December 12, 1978
    Assignee: The Upjohn Company
    Inventors: Augustin T. Chen, William J. Farrissey, Jr., Robert G. Nelb, II
  • Patent number: 4128531
    Abstract: A thermosetting resin composition comprising a polyfunctional epoxy compound such as diglycidyl ether of bisphenol A, a polyfunctional isocyanate such as diphenylmethane diisocyanate, a curing agent and polybutadiene type polymer having terminal hydroxyl groups can produce cured articles excellent in heat resistance and crack resistance.
    Type: Grant
    Filed: October 18, 1977
    Date of Patent: December 5, 1978
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Shinichi Toyoda, Masahiko Sakai, Kazuo Goto, Toshikazu Narahara, Yoshiharu Karasawa
  • Patent number: 4128537
    Abstract: Process for the preparation of ethylenically unsaturated isocyanurates comprising reacting polyisocyanate with a monohydric alcohol containing a vinylidene group in the presence of a copper salt to form an isocyanate-containing urethane and then trimerizing the isocyanate-containing urethane to form an ethylenically unsaturated isocyanurate. The ethylenically unsaturated isocyanurate may be homopolymerized or copolymerized with ethylenically unsaturated monomers to form high molecular weight polymers having excellent physical properties.
    Type: Grant
    Filed: July 27, 1977
    Date of Patent: December 5, 1978
    Assignee: ICI Americas Inc.
    Inventor: Kenneth H. Markiewitz
  • Patent number: 4118373
    Abstract: Elastomers are prepared from a mixture comprising a 1600 equivalent weight polyether polyol such as a glycerine initiated polyoxypropylene glycol end-capped with ethylene oxide, a diol such as diethylene glycol, a liquid polyepoxide such as the diglycidyl ether of bisphenol A and a catalyst mixture containing a quaternary ammonium or phosphonium salt and an organometal salt of the metal tin or lead such as tetrabutyl ammonium bromide and lead octoate.
    Type: Grant
    Filed: May 4, 1977
    Date of Patent: October 3, 1978
    Assignee: The Dow Chemical Company
    Inventor: Jon A. Orvik
  • Patent number: 4115372
    Abstract: Novel solvent soluble and injection moldable copolyamideimides are disclosed that are characterized in that from about 30 percent to about 70 percent of the recurring units are ##STR1## and in the remaining 30-70 percent of the recurring units are ##STR2## wherein C.sub.n H.sub.2n represents alkylene from 7 to 12 carbon atoms, inclusive, and Ar is ##STR3## where X = --SO.sub.2 --, --CO--, --O--, or alkylene (C.sub.1-4). The copolyamideimides are further characterized by ease of melt processing such as by extruding or injection molding while at the same time prossessing good high temperature stability and unexpectedly high impact and tensile yield strengths.
    Type: Grant
    Filed: January 21, 1977
    Date of Patent: September 19, 1978
    Assignee: The Upjohn Company
    Inventor: Kemal B. Onder
  • Patent number: 4105642
    Abstract: Modified polystyrenes are described which are catalysts for the conversion of organic isocyanates to the corresponding carbodiimides. The modified polystyrenes are characterized by the presence of recurring units of the formula: ##STR1## WHEREIN THE BROKEN LINES IN THE PHOSPHOLENE NUCLEUS INDICATE A DOUBLE BOND LOCATED BETWEEN THE CARBON ATOM AT POSITION 3 AND ONE OF THE CARBON ATOMS AT POSITIONS 2 AND 4, THE H atom is attached to whichever carbon atom at positions 2 and 4 is not part of said double bond, R is halogen, alkoxy (C.sub.1-6), phenoxy, hydrocarbyl (C.sub.1-18), halohydrocarbyl (C.sub.1-18), m = 0-3; n = 0, 1; R.sub.1 is hydrogen or methyl; and R.sub.2 is hydrocarbyl free from substituents reactive with isocyanate.
    Type: Grant
    Filed: October 31, 1977
    Date of Patent: August 8, 1978
    Assignee: The Upjohn Company
    Inventor: Curtis P. Smith
  • Patent number: RE30067
    Abstract: Novel iminoimidazolidinedione polymers containing imide groups (hereinafter PIPA-IM) are prepared from mixtures of dianhydrides, hydrogen cyanide and diisocyanates in an appropriate solvent and with an appropriate catalyst. The cyanide ion is an effective catalyst for all of the reactions involved. Hydrolysis of these polymers produces novel parabanic acid polymers containing imide groups (hereinafter PPA-IM).
    Type: Grant
    Filed: November 2, 1977
    Date of Patent: August 7, 1979
    Assignee: Exxon Research & Engineering Co.
    Inventor: Tad L. Patton