Material Contains A Phosphorus Atom Patents (Class 528/51)
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Patent number: 4258169Abstract: 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: GrantFiled: March 26, 1980Date of Patent: March 24, 1981Assignee: The Upjohn CompanyInventors: Richard A. Prather, David L. Williams, Robert M. Partin, Warren J. Rabourn
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Patent number: 4256795Abstract: 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: GrantFiled: May 27, 1977Date of Patent: March 17, 1981Assignee: Polymark CorporationInventors: Ian H. Day, William A. Baldwin, Harold J. Stern
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Patent number: 4237252Abstract: 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: GrantFiled: June 28, 1979Date of Patent: December 2, 1980Assignee: Minnesota Mining and Manufacturing CompanyInventors: Richard G. Newell, Harold E. Rude
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Patent number: 4235976Abstract: 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: GrantFiled: June 27, 1979Date of Patent: November 25, 1980Assignee: Bayer AktiengesellschaftInventors: Peter Haas, Rolf Wiedermann
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Patent number: 4229560Abstract: 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: GrantFiled: May 30, 1978Date of Patent: October 21, 1980Inventors: Alexei Y. Chernikhov, Mikhail N. Yakovlev, Valentina B. Lysova, Evgeny L. Gefter, Nina N. Shmagina
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Patent number: 4224422Abstract: 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: GrantFiled: June 28, 1979Date of Patent: September 23, 1980Assignee: Minnesota Mining and Manufacturing CompanyInventors: Harold E. Rude, Richard G. Newell
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Patent number: 4221572Abstract: 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: GrantFiled: March 2, 1978Date of Patent: September 9, 1980Assignee: Kao Soap CompanyInventors: Yasuhiro Torimae, Tamio Ishiai
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Patent number: 4217436Abstract: 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: GrantFiled: December 11, 1978Date of Patent: August 12, 1980Assignee: The Upjohn CompanyInventors: Reinhard H. Richter, Benjamin W. Tucker, Henri Ulrich
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Patent number: 4206104Abstract: 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: GrantFiled: October 10, 1978Date of Patent: June 3, 1980Assignee: PPG Industries, Inc.Inventors: Rostyslaw Dowbenko, Ronald J. Lewarchik, William J. Birkmeyer
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Patent number: 4203883Abstract: 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: GrantFiled: September 5, 1978Date of Patent: May 20, 1980Assignee: Textron, Inc.Inventor: David G. Hangauer, Jr.
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Patent number: 4195132Abstract: 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: GrantFiled: May 5, 1977Date of Patent: March 25, 1980Assignee: Bayer AktiengesellschaftInventors: Rudolf Sundermann, Gunther Rottloff, Ernst Grigat
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Patent number: 4194068Abstract: 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: GrantFiled: March 21, 1978Date of Patent: March 18, 1980Assignee: The Dow Chemical CompanyInventors: Dennis P. Miller, Masahiko Tamaki
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Patent number: 4187215Abstract: 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: GrantFiled: September 25, 1972Date of Patent: February 5, 1980Assignee: Aerojet-General CorporationInventor: John M. Wrightson
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Patent number: 4182812Abstract: 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: GrantFiled: November 23, 1977Date of Patent: January 8, 1980Assignee: Bayer AktiengesellschaftInventors: Wilfried Zecher, Rudolf Merten
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Patent number: 4174307Abstract: 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: GrantFiled: July 31, 1978Date of Patent: November 13, 1979Assignee: Polychrome CorporationInventor: William Rowe
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Patent number: 4169196Abstract: 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: GrantFiled: October 14, 1977Date of Patent: September 25, 1979Assignee: The Upjohn CompanyInventors: Benjamin S. Ehrlich, Curtis P. Smith
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Patent number: 4156065Abstract: 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: GrantFiled: January 21, 1977Date of Patent: May 22, 1979Assignee: The Upjohn CompanyInventors: Kemal B. Onder, Curtis P. Smith
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Patent number: 4152309Abstract: 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: GrantFiled: January 23, 1978Date of Patent: May 1, 1979Assignee: Nitto Electric Industrial Company, Ltd.Inventors: Ichiro Ijichi, Shigetoshi Kai, Hikaru Teranishi, Akira Morioka, Kazuyoshi Seki
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Patent number: 4150211Abstract: 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: GrantFiled: February 16, 1978Date of Patent: April 17, 1979Assignee: Bayer AktiengesellschaftInventors: Hanns P. Muller, Kuno Wagner, Hans J. Kreuder
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Patent number: 4147710Abstract: 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: GrantFiled: September 23, 1975Date of Patent: April 3, 1979Assignee: Bayer AktiengesellschaftInventors: Andrea La Spina, Werner Dietrich, Reinhard Schliebs
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Patent number: 4129715Abstract: 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: GrantFiled: January 16, 1978Date of Patent: December 12, 1978Assignee: The Upjohn CompanyInventors: Augustin T. Chen, William J. Farrissey, Jr., Robert G. Nelb, II
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Patent number: 4128531Abstract: 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: GrantFiled: October 18, 1977Date of Patent: December 5, 1978Assignee: Hitachi Chemical Company, Ltd.Inventors: Shinichi Toyoda, Masahiko Sakai, Kazuo Goto, Toshikazu Narahara, Yoshiharu Karasawa
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Patent number: 4128537Abstract: 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: GrantFiled: July 27, 1977Date of Patent: December 5, 1978Assignee: ICI Americas Inc.Inventor: Kenneth H. Markiewitz
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Patent number: 4118373Abstract: 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: GrantFiled: May 4, 1977Date of Patent: October 3, 1978Assignee: The Dow Chemical CompanyInventor: Jon A. Orvik
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Patent number: 4115372Abstract: 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: GrantFiled: January 21, 1977Date of Patent: September 19, 1978Assignee: The Upjohn CompanyInventor: Kemal B. Onder
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Patent number: 4105642Abstract: 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: GrantFiled: October 31, 1977Date of Patent: August 8, 1978Assignee: The Upjohn CompanyInventor: Curtis P. Smith
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Patent number: RE30067Abstract: 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: GrantFiled: November 2, 1977Date of Patent: August 7, 1979Assignee: Exxon Research & Engineering Co.Inventor: Tad L. Patton