With Three-membered Heterocyclic Reactant Containing Two Carbon Atoms And A Hetero Atom (i.e., Nitrogen Or A Chalcogen Atom) Patents (Class 521/156)
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Patent number: 5302626Abstract: The invention relates to the use of reaction mixtures containing polyester polyols which have been obtained by ring opening of epoxidized esters with carboxylic acids, as polyol component, optionally in admixture with polybutadiene diol, in the production of solid polyurethane materials by casting.Type: GrantFiled: June 23, 1992Date of Patent: April 12, 1994Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Rainer Hoefer, Gerhard Stoll, Peter Daute, Roland Gruetzmacher
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Patent number: 5288833Abstract: The present invention relates to quaternary .beta.-hydroxy-alkyl-ammonium halides and quaternary .beta.-hydroxy-cycloalkylammonium halides, which are liquid at temperatures lower than 60.degree. C., are easily and rapidly miscible in liquid epoxides, as well as in liquid poly-isocianates, generating liquid compositions which spontaneously polymerize, with fast polymerization rate, already at temperatures comprised within the range of from 0.degree. C. to 60.degree. C., yielding a solid, insoluble polymeric material endowed with very high values of softening temperature.Type: GrantFiled: May 20, 1992Date of Patent: February 22, 1994Assignee: Istituto Guido Donegani S.p.A.Inventors: Fabrizio Parodi, Carlo Belgiovine, Carla Zannoni
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Patent number: 5256726Abstract: Reactive systems comprising of a specific polyisocyanate component and a reactive component for this polyisocyanate component, as well as non-reactive plasticizers and if appropriate other auxiliaries and additives, and a process for the preparation of polyurethane plastics containing isocyanurate groups using this reactive system.Type: GrantFiled: September 13, 1991Date of Patent: October 26, 1993Assignee: Bayer AktiengesellschaftInventors: Hanns-Peter Muller, Joachim Franke, Renate Bulan
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Patent number: 5216042Abstract: A method of preparing viscosity-stabilized toluene diisocyanate distillation residues comprising contacting toluene diisocyanate distillation residue with a material suitable for purging chloride-containing vapors under reaction conditions suitable to remove chloride-containing vapors from the toluene diisocyanate distillation residues. The material may be, for example, an aromatic solvent and/or a gas which associates, physically, chemically, or a combination thereof, with the vapors but not with significant amount of other components that may be present in the toluene diisocyanate distillation residue. The viscosity-stabilized and reactive residue can then be used alone or blended with one or more other isocyanate products, such as polymeric methylene diphenylisocyanate, to prepare materials such as polyurethane, polyisocyanurate, polyurethane-polyurea or polyurea compositions including, for example, foams.Type: GrantFiled: July 10, 1991Date of Patent: June 1, 1993Assignee: The Dow Chemical CompanyInventors: Rory D. Daussin, Steven B. Lowenkron, John L. Nafziger
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Patent number: 5162387Abstract: A process for the preparation of a polyurethane elastomer by reactinga) an organic and/or modified organic polyisocyanate withb) at least one relatively high-molecular-weight polyoxybutylene-polyoxyalkylene glycol from the group comprising polyoxybutylene-polyoxyethylene glycols, polyoxybutylene-polyoxypropylene glycols and/or polyoxybutylene-polyoxpropylene-polyoxyethylene glycols,c) at least one chain extender and/or crosslinking agent andd) at least one glycidyl compound containing units having the structure ##STR1## in which n is a number from 1 to 6,X is an alkylene, arylene, --O-- or --N-- bridge, andR.sup.1 and R.sub.2 are identical or different and are hydrogen, methyl or ethyl,in the presence or absence ofe) blowing agents,f) catalysts andg) assistants and/or additives,and mixtures of polyoxybutylene-polyoxyalkylene glycols (b) and glycidyl compounds (d).Type: GrantFiled: February 11, 1992Date of Patent: November 10, 1992Assignee: BASF AktiengesellschaftInventors: Ulrich Abel, Friedhelm Lehrich, Wolfgang Straehle, Peter Groll
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Patent number: 5096934Abstract: Packaging materials containing inherently antistatic foams and a method of using the foams are disclosed. The foam used is a polyether polyurethane foam prepared from an isocyanate containing prepolymer which is the reaction product of a oxyethylene containing polyol and a polyisocyanate. The foams show surface resistivity of less than 1.times.10.sup.12 ohms/square and static decay times of about two seconds or less. A preferred foam shows static decay times of 0.1 seconds or less. The packaging includes articles used around static sensitive devices or used to store or transport static sensitive devices.Type: GrantFiled: September 21, 1989Date of Patent: March 17, 1992Assignee: W. R. Grace & Co.-Conn.Inventors: William P. Roberts, Cynthia L. Ebner, Timothy G. Grasel
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Patent number: 5021536Abstract: This invention relates to storage stable resin reaction mixtures obtained by mixing at least one organic polyisocyanate, at least one organic compound containing at least two epoxide groups, at least one alkylating agent that inhibits the reaction of the polyisocyanate and epoxide components, and optional auxiliary agents and additives. The present invention further relates to a process for the preparation of such reaction mixtures and to their use.Type: GrantFiled: February 28, 1989Date of Patent: June 4, 1991Assignee: Bayer AktiengesellschaftInventors: Hanns P. Muller, Heinrich Heine
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Patent number: 5019602Abstract: Polyurethane foams, varying in nature from soft to hard, tough skin and a process for their preparation comprising reacting approximately equal volumes of substantially liquid mixtures from a two part dispensing system, Part A comprising a substantially liquid, stable mixture of an isocyanate and an epoxide and Part B comprising a substantially liquid mixture of a polyether polyol, a catalyst and an accelerator.Type: GrantFiled: December 12, 1989Date of Patent: May 28, 1991Assignee: Premier Industrial CorporationInventor: Frank J. Lowe
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Patent number: 4990543Abstract: Described is a lightweight open-cell flexible foam having a density no greater than about 6 pounds per cubic foot, preferably less than 1.0 pound per cubic foot (pcf) comprising the reaction product of an organic polyisocyanate and a mixture of difunctional acids, acid anhydrides, and difunctional anhydrides in the presence of a tertiary amine triazine catalyst, which reactants during the manufacturing process generate carbon dioxide, wherein the ratio of imide groups in the final product is greater than 1.Type: GrantFiled: July 13, 1989Date of Patent: February 5, 1991Assignee: Manville CorporationInventors: David G. Wernsing, Royce M. Feagans, Daniel E. Near, John Sznopek
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Patent number: 4980387Abstract: Described is a lightweight open-cell flexible foam having a density no greater than about 6 pounds per cubic foot, preferably less than 1.0 pound per cubic foot (pcf) comprising the reaction product of an organic polyisocyanate and a mixture of difunctional acids, acid anhydrides, and difunctional anhydrides in the presence of a tertiary amine triazine catalyst, which reactants during the manufacturing process generate carbon dioxide, wherein the ratio of imide to amide groups in the final product is greater than 1.Type: GrantFiled: August 9, 1990Date of Patent: December 25, 1990Assignee: Manville CorporationInventors: David G. Wernsing, Royce M. Feagans, Daniel E. Near, John Sznopek
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Patent number: 4925881Abstract: A foamable thermosetting resin system is disclosed comprising:(a) about 50 to about 85 weight percent, based on the weight of the composition, of a trimerisable polyisocyanate;(b) about 5 to about 20 weight percent of a liquid epoxy resin having an epoxy group content in the range from about 3500 to about 7500 mmol/kg;(c) about 5 to about 20 weight percent of a vinyl ester of a saturated aliphatic monocarboxylic acid in which the carboxyl group is attached to a tertiary or quarternary carbon atom;(d) about 1 to about 20 weight percent of a foaming agent, and(e) about 0.005 to about 5 weight percent of an isocyanate trimerization catalyst.Type: GrantFiled: October 12, 1988Date of Patent: May 15, 1990Assignee: Shell Oil CompanyInventor: Anne C. Udding
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Patent number: 4904704Abstract: A method of treating toluene diisocyanate distillation residues comprising reacting the residues with at least about 0.5 equivalents, based on hydrolyzable chloride concentration of the residues, of an epoxy compound at a temperature of from about 155 to about 220.degree. C. to produce a treated distillation residue having a hydrolyzable chloride level of less than about 800 parts per million (ppm) is taught. The product of the method is useful, for instance, in producing rigid foams with low K Factors.Type: GrantFiled: December 22, 1988Date of Patent: February 27, 1990Assignee: The Dow Chemical CompanyInventors: John L. Nafziger, Steven B. Lowenkron, Charles E. Koehler, Debkumar Bhattacharjee
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Patent number: 4859713Abstract: Flame-retardant polyols are produced by chemically reacting an epoxy compound, a phosphorus-containing compound and a compound containing 1 or more active hydrogens to produce a phosphorus-containing polyol with acid radicals which are reacted with an alkali compound. The flame-retardant polyol will react with polyisocyanates to produce solid or foamed products which may be used as coating agents, adhesive or for insulation.Type: GrantFiled: December 4, 1987Date of Patent: August 22, 1989Inventor: David H. Blount
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Patent number: 4831076Abstract: A modified polyol, suitable for use as a non-aqueous dispersant in the preparation of polymer/polyols containing high levels of polymer, is provided. The modified polyol comprises the product obtained by reaction of a polyol with a coupling agent having at least two functional groups which are reactable with hydroxyl groups on the polyol. Suitable coupling agents include silicon compounds having two such functional groups, organic compounds having two or more alkoxy groups, saturated dicarboxylic acid derivatives, alkyl or aryl esters of carbonic acid, alkyl or aryl sulphonates, boric acid or its esters and titanates.Type: GrantFiled: April 24, 1985Date of Patent: May 16, 1989Assignee: BP Chemicals LimitedInventors: Werner A. Lidy, Huy P. Thanh
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Patent number: 4789690Abstract: A polyurethane foam is the reaction product of at least one polyol and at least one polyisocyanate in the presence of at least one blowing agent. The polyol contains a polymer polyol dispersion prepared by reacting an epoxy resin with an epoxy hardener in the presence of a liquid polyol.Type: GrantFiled: March 30, 1987Date of Patent: December 6, 1988Assignee: The Dow Chemical CompanyInventors: Olga Milovanovic-Lerik, Hanno R. van der Wal, Ulrich Tribelhorn
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Patent number: 4788224Abstract: Molded articles are produced in a two-stage process. In the first stage, an organic polyisocyanate is reacted with an organic compound containing at least two epoxide groups (NCO: epoxide equivalent ratio of 1.2:1 to 500:1) in the presence of a tertiary amine catalyst. This reaction is stopped when no more than 65% of the isocyanate groups have reacted by adding an alkylating sulfonic acid alkyl ester of methyl iodide and/or of dimethyl sulfate in an amount equivalent to the amount of tertiary amine catalyst present. A latent catalyst capable of being activated by heat is subsequently added to the intermediate product and the resultant mixture is heated in a mold to complete the crosslinking of the intermediate product and to form the molded article.Type: GrantFiled: December 11, 1987Date of Patent: November 29, 1988Assignee: Bayer AktiengesellschaftInventors: Hanns P. Muller, Walter Uerdingen, Heinrich Heine
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Patent number: 4766158Abstract: Urethane and oxazolidone-containing isocyanurate foams characterized by cracking resistance and scorching resistance and thermal stability at a temperature of about 160.degree. C. or higher. These foams are produced by reacting at least one polyisocyanate with at least one polyepoxide and at least one polyol in the presence of catalyst, surfactant, and blowing agent.Type: GrantFiled: August 3, 1987Date of Patent: August 23, 1988Assignee: Olin CorporationInventors: Stephen Fuzesi, Robert W. Brown
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Patent number: 4704409Abstract: A process for preparing a poly(alkylene amido-ether) polyols by reaction of a bicyclic amide acetal with a polyol at a temperature in the range of from 140.degree.-240.degree. C. and the use of these poly(alkylene amidoether) polyols in the formation of polyurethanes are described.Type: GrantFiled: January 20, 1987Date of Patent: November 3, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4699931Abstract: Oxazolidone-containing isocyanurate foams characterized by thermal stability at a temperature of about 140.degree. C. or higher. These foams are produced by reacting at least one polyisocyanate with at least one polyepoxide in the presence of catalyst, surfactant, and blowing agent.Type: GrantFiled: April 25, 1986Date of Patent: October 13, 1987Assignee: Olin CorporationInventors: Stephen Fuzesi, Robert W. Brown
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Patent number: 4690953Abstract: A method of mechanically frothing and casting an aqueous ionic polyurethane dispersion to yield a mechanically frothed polyurethane foam. The method comprises admixing an aqueous ionic polyurethane dispersion with a stearate stabilizer and an optional aziridine crosslinking agent, and frothing the low viscosity admixture. The polyurethane dispersion contains particles having an average size of less than one micron, and contains between 35 and 70 percent by weight dispersed polyurethane solids. Preferably, each polyurethane particle in the aqueous dispersion is crosslinked. Before frothing, the low viscosity admixture contains between 33 and 87 percent by weight of the polyurethane dispersion, up to 33 percent by weight of an azirdine composition and between 13 and 50 percent by weight of a 33 percent aqueous dispersion of a stearate salt and has, as a result, a viscosity in the range of 100 to 200 centipoise. After frothing, the frothed admixture is knife-coated and cured into a flexible foam sheet.Type: GrantFiled: March 11, 1986Date of Patent: September 1, 1987Assignee: Seton CompanyInventors: Robert B. Orr, Leon Chicosky, Jr.
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Patent number: 4524157Abstract: Adducts and improved polymer-polyols, both useful in the production of polyurethane foams and other synthetic materials are provided, as well as synthetic end products. The adducts are produced by combining polyols and compounds having carboxylic carbon atoms and/or epoxy groups.Type: GrantFiled: June 6, 1983Date of Patent: June 18, 1985Assignee: Union Carbide CorporationInventor: Paul Stamberger
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Patent number: 4518720Abstract: Flexible polyurethane foams having improved properties and made from modified polyether polyols are described. The polyether polyols are modified with adducts of epoxy resins, such as the diglycidyl ether of Bisphenol A, and diamines, such a polyoxypropylenediamine. The resulting modified polyether polyols have a molecular weight of from about 2,000 to 7,000. The mole ratio of epoxy equivalents to amine equivalents in the adduct ranges from about 2/1 to 10/1.Type: GrantFiled: June 11, 1984Date of Patent: May 21, 1985Assignee: Texaco Inc.Inventors: Michael Cuscurida, Harold G. Waddill, Bruce W. Peterson
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Patent number: 4508853Abstract: Polyurethane prepolymers containing terminal isocyanate groups in which oleochemical polyols are present as the polyol component. The oleochemical polyols are ring opened products or partial ring-opened products of epoxidized fatty acid triglycerides with alcohols. The use of oleochemical polyols having a residual epoxide number of from 1.0 to 4.0% by weight of epoxide oxygen is preferred. The polyurethane prepolymers are particularly suitable for use in one-component or two-component polyurethane foam formulations.Type: GrantFiled: May 8, 1984Date of Patent: April 2, 1985Assignee: Henkel KommanditgesellschaftInventors: Hermann Kluth, Alfred Meffert
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Patent number: 4474900Abstract: The invention relates to reaction injection molded elastomers derived from high molecular weight amine terminated polyethers and/or high molecular weight polyols, a chain extender, a polyisocyanate and an epoxy modified filler material. The reaction injection molded (RIM) elastomers of this invention are useful, for example, as automobile body parts.Type: GrantFiled: June 8, 1983Date of Patent: October 2, 1984Assignee: Texaco Inc.Inventor: Richard J. G. Dominguez
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Patent number: 4430454Abstract: Polymeric foam compositions, useful as insulating material are obtained from the reaction of polymaleic anhydride with a hydroxyl-containing compound like ethylene glycol or its derivatives, in the presence of an organic isocyanate. Hydroxyl-containing compounds suitable for reaction with polymaleic anhydride include C.sub.2 -C.sub.10 diols, C.sub.3 -C.sub.6 trilos, C.sub.4 -C.sub.5 tetraols and their derivatives.Type: GrantFiled: May 9, 1983Date of Patent: February 7, 1984Assignee: FMC CorporationInventors: Harry M. Castrantas, Sidney Berkowitz
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Patent number: 4377646Abstract: Poly(epoxy-polyisocyanate) silicate foamed products are produced by mixing and reactng an epoxide compound, an oxidated silicon compound and a polyisocyanate in the presence of a Lewis acid. The foam produced by this process may be utilized for thermal and sound insulation.Type: GrantFiled: August 5, 1982Date of Patent: March 22, 1983Inventor: David H. Blount
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Patent number: 4357463Abstract: Polyester silicate resinous products are produced by mixing an organic epoxide compound, hydrated silica, Lewis acid and a polycarboxylic acid and/or polycarboxylic acid anhydride, then heating the mixture to from 150.degree. C. to 250.degree. C. for 30 minutes to 4 hours. The polyester is silicate resinous products may be used as a coating agent, as a molding powder and as an adhesive.Type: GrantFiled: December 3, 1981Date of Patent: November 2, 1982Inventor: David H. Blount
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Patent number: 4302272Abstract: The instant invention is directed to a process for heat sealing flexible polyurethane foam, comprising:A. reacting and foaming a polyurethane foam produced by the steps comprising reacting:(I) an organic polyisocyanate;(II) a polyol having a molecular weight of 2,000 to 8,000 comprising the adduct obtained by sequentially reacting:(a) a polyhydroxyl initiator, with a functionality of 2 to 5 and a weight average molecular weight as determined by gel permeation chromatography of from 62 to 200; with(b) 10 to 90%, most preferably 10 to 50%, by weight, based on the total oxide present in (b)+(c)+(d), a first alkylene oxide; and subsequently reacting the product with(c) 10 to 80%, preferably 20 to 50% by weight, based on the total oxide present in (b)+(c)+(d), 4,4,4-trichloro-1,2-epoxybutane and/or epihalohydrin; and subsequently reacting the product with(d) 10 to 60%, most preferably 10 to 40%, by weight, based on the total oxide present in (b)+(c)+(d), a second alkylene oxide.Type: GrantFiled: January 14, 1980Date of Patent: November 24, 1981Assignee: Mobay Chemical CorporationInventors: Barry A. Phillips, Keith G. Spitler, Richard E. Keegan
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Patent number: 4267078Abstract: A method for easily degrading wastes consisting of the reaction products of organic materials containing isocyanate groups and specifically foamed polyurethane wastes by comminuting the waste and reacting it with alkylene oxide at 120.degree. C. to 200.degree. C. and removing the unreacted alkylene oxide. The products obtained are homogeneous liquids which can be added to polyols for reaction with isocyanates to form foamed polyurethanes.Type: GrantFiled: July 5, 1979Date of Patent: May 12, 1981Assignee: Th. Goldschmidt AGInventors: Werner Lidy, Gerd Rossmy, Hans-Joachim Kollmeier
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Patent number: 4258137Abstract: This invention relates to the preparation of a flexible, open cell polyurethane foam which can be rigidized by incorporating an epoxy resin into the mixture prior to foaming and, after forming a flexible foam, adding an epoxy curing agent thereto to cause the epoxy resin to cure thereby rigidizing the previously flexible foam. The flexible foam can be reshaped prior to rigidizing if desired.Type: GrantFiled: October 11, 1979Date of Patent: March 24, 1981Assignee: W. R. Grace & Co.Inventor: Joseph A. Cogliano
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Patent number: 4220731Abstract: The invention relates to a process for the preparation of crosslinked polymers by reacting liquid epoxide compounds and polyisocyanates and, if desired, polyhydroxy compounds. The curing catalysts used are complex compounds of BF.sub.3 with ethers or phosphonium compounds or H.sub.2 O. If desired, a compound of one of the metals Sn, Zn or Fe which is soluble in the reaction mixture is also added.In most cases it is possible to dispense completely with the external supply of heat when carrying out the process according to the invention, since the reaction is sufficiently exothermic. The technical advance lies in the fact that it is largely possible to dispense with heating and insulating equipment when carrying out the reaction industrially. Despite this, astonishingly high glass transition temperatures are obtained.Type: GrantFiled: June 7, 1978Date of Patent: September 2, 1980Assignee: Ciba-Geigy CorporationInventor: Paul Zuppinger
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Patent number: 4220729Abstract: A method of producing foams by utilizing the reactivity of isocyanate groups comprising the steps of reacting an organic polyisocyanate in the presence of a foaming agent and, optionally, at least one member selected from the group consisting of polyols, polyepoxides, polycarboxylic acids, acid anhydrides and other compounds capable of reacting with the isocyanate groups and, if necessary, a catalyst, a foam stabilizer and other additives, the improvement wherein at least one organic amine-metal complex soluble in the liquid raw material and containing a metal selected from the group consisting of copper, nickel, lead, cobalt, manganese, zinc, and chromium is added to the reaction system in an amount of 0.5 to 30 weight % based on the total weight of the raw materials used for the preparation of foams. The foams containing flame-retardant organic amine-metal complexes prepared by the aforementioned method.Type: GrantFiled: July 14, 1977Date of Patent: September 2, 1980Assignee: Mitsubishi Chemical Industries, LimitedInventors: Shinzi Uchida, Takashi Yokoyama, Shoichi Ohkubo
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Patent number: 4129695Abstract: Polymers comprising polyoxazolidone and carbodiimide recurring units of the formula: ##STR1## are prepared from polyisocyanates and polyepoxides. Non-friable, low density fire resistant foams are prepared directly from the polymers of the invention without the equisite addition of pore-forming agents.Type: GrantFiled: March 16, 1977Date of Patent: December 12, 1978Assignee: Rhone-Poulenc IndustriesInventor: Yves Bonin
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Patent number: 4108810Abstract: Storage-stable solid intermediate products, capable of being foamed and polymerized to cellular highly crosslinked three dimensional ethylenic polymer resin products having amic acid groups and/or cyclic imide linkages, are obtained by inter-reacting, at temperature above the melting point but below about 100.degree. C, a polyisocyanate illustrated by tolylene diisocyanate, a dicarboxylic acid illustrated by maleic or malonic acid, and an unsaturated dicarboxylic acid anhydride illustrated by maleic anhydride, subsequently adding catalyst, surfactant and water while allowing CO.sub.2 to evolve, finally allowing the reaction mixture to solidify. The stable solid, e.g. in the form of granules or powder, can subsequently be shaped, foamed and polymerized by heating to 150.degree.-300.degree. C to provide infusible, insoluble, flame-resistant, rigid cellular resin products having low apparent density.Type: GrantFiled: October 17, 1977Date of Patent: August 22, 1978Assignee: The Dow Chemical CompanyInventor: Ann Marie Baker
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Patent number: 4101465Abstract: A novel cocatalyst combination for the trimerization of polyisocyanates to polyisocyanurates is disclosed. The catalyst combination comprises: (a) alkali metal glycine salts, (b) hydroxyalkyltrialkylammonium carboxylate salts, and (c) alkali metal salts selected from the group consisting of (i) alkali metal salts of N-phenyl aliphatic amides, and (ii) alkali metal salts of aliphatic carboxylic acids. The use of the cocatalyst combination provides for the facile formation of polyisocyanurate foam laminate boardstock which is characterized by good fire resistance and good physical properties.Type: GrantFiled: October 6, 1976Date of Patent: July 18, 1978Assignee: The Upjohn CompanyInventors: Robert J. Lockwood, Alexander McLaughlin, Harold E. Reymore, Jr.