Material Contains A Transition Metal Atom Patents (Class 528/56)
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Patent number: 4740577Abstract: A polymerizable composition of polyurethane precursors is rapidly cured using energy-activated catalysts to provide polyurethanes. The polymerizable composition is comprised of polyisocyanates with polyols, fillers, coating aids, adjuvants, and a latent catalyst. Latent catalysts are ionic salts of organometallic complex cations. The cured polyurethanes are useful as abrasion resistant coatings, protective finishes such as furniture finishes and floor tiles, binders for magnetic media, adhesives, and have various applications in industries which use photoresist technologies such as graphic arts and electronics, and in the paint and ink industries.Type: GrantFiled: August 28, 1987Date of Patent: April 26, 1988Assignee: Minnesota Mining and Manufacturing CompanyInventors: Robert J. DeVoe, Doreen C. Lynch
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Patent number: 4738991Abstract: Organic polyisocyanates characterized by allophanate linkages are prepared by reacting an organic polyisocyanate with a mono- or polyhydric compound in the presence of an organo metal catalyst. The catalyst is then deactivated using a compound such as an inorganic acid, organic acid, organic chloroformate or an organic acid chloride. The isocyanates are useful in preparing polyurethane foams.Type: GrantFiled: January 23, 1987Date of Patent: April 19, 1988Assignee: BASF CorporationInventor: Thirumurti Narayan
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Patent number: 4721767Abstract: An improved process for the copolymerization of a mixture of a bicyclic amide acetal and a polyisocyanate comprising carrying out the copolymerization reaction at a temperature in the range of from about ambient temperature up to about 200.degree. C. in the presence of a catalytic amount of a salt of a metal selected from the group consisting of bismuth, lead, mercury, copper, vanadium, cobalt, nickel, potassium, zinc and antimony is described.Type: GrantFiled: January 20, 1987Date of Patent: January 26, 1988Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4695618Abstract: A method for preparing polyurethane by spraying solventless, equal volume mixtures of:(a) a liquid polyisocyanate; polyisocyanurate or isocyanate terminated quasi-prepolymer; and(b) a curing agent comprised of a blend of from about 0 to 15% of a polyamine having an equivalent weight from about 30 to about 200, about 10 to 20% of a low molecular weight glycol having an equivalent weight of from about 30 to 200, about 40 to 80% of a relatively high molecular weight polyol or polyamine having an equivalent weight of about 350 to 2000, and about 1 to 20% of a synthetic zeolite molecular sieve, wherein the average equivalent weight of (b) is from about 150 to 500.Type: GrantFiled: May 23, 1986Date of Patent: September 22, 1987Assignee: Ameron, Inc.Inventor: Norman R. Mowrer
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Patent number: 4681926Abstract: The process for preparing a polyurethane which sets rapidly and can be demolded within minutes by the reaction of a bicyclic amide acetal, a polyol and a polyisocyanate in the presence of a plasticizer such as dioctyl phathalate and a polyurethane catalyst such as stannous octoate is described.Type: GrantFiled: April 11, 1986Date of Patent: July 21, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4657988Abstract: Polymeric materials are repolymerized by intensely admixing the polymer with an additive having the formula: ##STR1## wherein M is titanium or zirconium, R, R.sup.1 and R.sup.2 are each a monovalent alkyl, alkenyl, alkynyl, aralkyl, aryl or alkaryl group having up to 20 carbon atoms or a halogen or ether substituted derivative thereof, and, in addition, R.sup.2 may also be an oxy derivative or an ether substituted oxy derivative of said groups; A, B, and C are each a monovalent aroxy, thioaroxy, diester phosphate, diester pyrophosphate, oxyalkylamino, sulfonyl or carboxyl containing up to 30 carbon atoms; and a+b+c=3. The repolymerized polymers have improved physical properties and higher heat distortion temperatures, experience less thermal degradation and show greater solvolysis resistance than the polymers prior to the repolymerization.Type: GrantFiled: February 28, 1986Date of Patent: April 14, 1987Assignee: Kenrich Petrochemicals, Inc.Inventors: Gerald Sugerman, Salvatore J. Monte
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Patent number: 4626475Abstract: A process for the production of a pressure sensitive adhesive comprising the interaction of a high molecular weight polyol, a polyisocyanate and a small amount of a bicyclic amide acetal wherein the process results in significant improvement in physical properties, e.g., a high degree of adhesive and cohesive strength, is described.Type: GrantFiled: September 18, 1985Date of Patent: December 2, 1986Assignee: Ashland Oil, Inc.Inventors: Anil Goel, Joseph Holehouse, Kenneth Barnett
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Patent number: 4613660Abstract: Fast curing adhesives which are free of solvent and have high heat resistant bonding strength composed of mixtures of polyols, polyepoxides and polyisocyanates are described.Type: GrantFiled: February 19, 1985Date of Patent: September 23, 1986Assignee: Ashland Oil, Inc.Inventors: Anil B. Goel, Harvey J. Richards, Robert A. Grimm
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Patent number: 4611044Abstract: This invention is an improvement in a process for preparing a polyurethane backed substrate whereby a reacting polyurethane forming mixture comprising at least one polyahl and at least one polyisocyanate as applied to a substrate and subsequently curing thereon to form an attached polyurethane backing. The improvement which is this invention comprises employing an organoiron or organobismuth catalyst for said polyurethane forming mixture. The organoiron or organobismuth catalyst is employed in an amount such that the polymer forming mixture exhibits the viscosity of not greater than about 20,000 cps 2 minutes after the polyahl and polyisocyanates are contacted in the presence of said catalyst at 20.degree.-50.degree. C. and the polyurethane forming mixture cures to a tack free state at an elevated temperature in the presence of said catalyst in less than about 8 minutes.Type: GrantFiled: May 28, 1985Date of Patent: September 9, 1986Assignee: The Dow Chemical CompanyInventors: Louis W. Meyer, Linda M. McKinney, Don H. Kelley
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Patent number: 4598136Abstract: Aliphatic embedding masses are disclosed, prepared by initially reacting one or more aliphatic diisocyanates with castor oil or a mixture of castor oil and further hydroxyl compounds, such as e.g., trimethylol propane into a NCO-group-displaying pre-adduct, and the pre-adduct is then hardened in a catalyzed reaction with a mixture containing castor oil, trimethylol propane and N-methyldiethanol amine. Preferably iron acetyl acetonate, dibutyl tin diacetate or titanium tetrabutylate are employed as catalysts. Isophoron diisocyanate is particularly suitable as diisocyanate.The embedding masses are useful for the embedding of membranes, preferably membranes to be employed in medical fields. The embedding masses are bio-compatible, especially with regard to blood, and are non-toxic. They allow for the embedding of membranes with the aid of automatic machinery. The embedding masses display no or only negligible swelling when used in contact with blood, blood-like and aqueous systems.Type: GrantFiled: March 26, 1985Date of Patent: July 1, 1986Assignee: Akzo NVInventor: Gerhard Wick
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Patent number: 4556703Abstract: A prepolymer curable with a hydroxyl or amine functional curative to form a polyurethane elastomer composition having low heat buildup characteristics is disclosed. Specifically, the polyurethane prepolymer has terminally reactive isocyanate groups and is prepared by reaction of polymeric diol with a stoichiometric excess of a mixture of the 2,6- and 2,4-isomers of tolylene diisocyanate, said mixture containing from about 50 to about 90 wt % of the 2,6-isomer.The invention also relates to a polyurethane elastomer composition comprising the aforementioned prepolymer and a curingly effective amount of a curative selected from the group consisting of aromatic diamines, hydroxy functional compounds, and mixtures thereof, and optionally, from about 0.01 to 1 part of catalyst per hundred parts of prepolymer.Also disclosed are articles of manufacture produced from the above composition, as well as compositions wherein the mixture contains 40 to 100 wt % of the 2,6-isomer.Type: GrantFiled: May 14, 1984Date of Patent: December 3, 1985Assignee: American Cyanamid CompanyInventors: Ignazio S. Megna, Curtis A. Franz
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Patent number: 4552944Abstract: A super-soft polyurethane elastomer is prepared by reacting an organic polyisocyanate in the presence of a specified organometallic catalyst, with a molar ratio specified mixture of (a) low molecular weight triol and high molecular weight polyol, or (b) low molecular weight triol, aromatic ring containing low molecular weight diol and high molecular weight polyol.Type: GrantFiled: September 20, 1984Date of Patent: November 12, 1985Assignee: Mitsui-Nisso CorporationInventors: Masayuki Kamiyama, Takashi Saito, Kiyotsugu Asai
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Patent number: 4546167Abstract: Polyurethane elastomer compositions, having a compression set less than or equal to about 40% are disclosed. These polyurethane elastomer compositions comprise the reaction product of:(a) A polyurethane prepolymer having terminally reactive isocyanate groups and formed as a reaction product of polymeric diol with a stoichiometric excess of p-tetramethylxylene diisocyanate (p-TMXDI); with(b) A curatively effective amount of a curative selected from the group consisting of: diethyltoluenediamine (DETDA), 2,4-bis (p-aminobenzyl)aniline (BABA), and mixtures thereof; and(c) Optionally, from about 0.01% to about 2% by weight of catalyst, based on the weight of curative.These polyurethane elastomers are used in molded articles which are to be used under load as in machine rolls and wheels.Type: GrantFiled: July 30, 1984Date of Patent: October 8, 1985Assignee: American Cyanamid CompanyInventor: Eugene Y. C. Chang
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Patent number: 4515933Abstract: A heat-curable polyurethane composition, comprising:(a) a secondary or tertiary aliphatic diisocyanate prepolymer;(b) a polyol compound;(c) a chain extender selected from the group consisting of sucrose and sorbitol; and(d) a curingly effective amount of a catalyst selected from the group consisting of magnesium acetylacetonate, nickel acetylacetonate, magnesium stearate, cadmium stearate, and organic acid salts of 1,8-diazabicyclo [5.4.0]undec-7-ene.Type: GrantFiled: April 11, 1983Date of Patent: May 7, 1985Assignee: American Cyanamid CompanyInventor: Eugene Y. C. Chang
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Patent number: 4506086Abstract: Liquid dianhydrohexitol mixtures are prepared from diacylation products of hexitols and compounds such as organic carboxylic acids, carboxylic acid anhydrides, carboxylic acid halides, ketene and carbonic acid ester derivatives. More specifically, such diacylation products are simultaneously dehydrated and isomerized by subjecting them to a temperature of at least 130.degree. C. in the presence of a strong acid to yield diacylated dianhydrohexitol isomer mixtures. These isomer mixtures are then converted to dianhydrohexitol isomer mixtures by hydrolysis or transesterification. Suitable strong acids include proton acids, Lewis acids and heterogeneous acid catalysts (e.g., ion exchange resins). The mixtures of the present invention are characterized by a minimal tendency towards crystallization. These mixtures are particularly useful as chain extending agents in the production of polyurethanes.Type: GrantFiled: July 20, 1983Date of Patent: March 19, 1985Assignee: Bayer AktiengesellschaftInventors: Herbert Salzburg, Manfred Hajek, Holger Meyborg
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Patent number: 4496706Abstract: A heat-curable polyurethane composition, comprising:(a) a secondary or tertiary aliphatic diisocyanate;(b) a hydroxyl compound; and(c) a curingly effective amount of a catalyst selected from the group consisting of magnesium acetylacetonate, nickel acetylacetonate, magnesium stearate, cadmium stearate, and organic acid salts of 1,8-diazabicyclo [5.4.0]undec-7-ene.Type: GrantFiled: April 11, 1983Date of Patent: January 29, 1985Inventor: Eugene Y. C. Chang
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Patent number: 4438235Abstract: Filled liquid, polyhydroxyl-containing polymers such as polyether and polyester polyols can be increased in viscosity by incorporating therein a tertiary alkanol monoamine.Type: GrantFiled: September 30, 1982Date of Patent: March 20, 1984Assignee: BASF Wyandotte CorporationInventor: Bernardas Brizgys
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Patent number: 4421905Abstract: The process described herein comprises the preparation of polyimides by the reaction of aromatic dianhydrides and aromatic diisocyanates in the presence of a metal acetylacetonate, such as Al, Co, Fe, Ni, Zr, etc. By using appropriate proportions, the polyimides may be end-capped with either anhydride or isocyanate groups. The use of the acetylacetonate permits the use of lower temperatures for imide ring closure thereby avoiding undesirable coreaction between anhydride groups and certain solvents. "Polyimide dianhydride" is an anhydride-terminated polyimide; and "polyimide diisocyanate" is an isocyanate-terminated polyimide as represented by the respective formulas: ##STR1## wherein Ar', Ar and n are as defined hereinafter. By this process, the polyimide dianhydride product has an anhydride activity of at least 0.17 as defined herein regardless of the type of solvent used.Type: GrantFiled: September 20, 1982Date of Patent: December 20, 1983Assignee: Plastics Engineering CompanyInventor: Chung J. Lee
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Patent number: 4412033Abstract: The disclosed one-part curable polyurethane prepolymer compositions comprise a continuous phase and, distributed uniformly through this phase, a discontinuous phase containing a polyol curing agent of the pentaerythritol type. At moderately elevated temperatures, the polyol phase begins to enter into a curing reaction which has a single exotherm peak. The prepolymers are made from aliphatic or cycloaliphatic polyisocyanates and polymeric polyols. The one-part curable system is stable for long periods at room temperature. The curable polyurethane systems can be used in adhesives, coatings, sealants, and similar applications.Type: GrantFiled: September 13, 1982Date of Patent: October 25, 1983Assignee: H. B. Fuller CompanyInventors: Stanley B. LaBelle, James A. E. Hagquist
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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: 4359359Abstract: Production of a polyurethane embedding material from an aromatic diisocyanate in stoichiometric excess with a polyol mixture consisting essentially of castor oil and trimethylolpropane to first form a prepolymer containing unreacted isocyanate groups and being sufficiently flowable to permit coating onto membrane surfaces in all types of coating methods, and subsequently hardening the prepolymer by addition of a cross-linking agent consisting essentially of castor oil alone or another mixture of castor oil with trimethylolpropane in an amount sufficient to cross-link the prepolymer through at least a majority of its unreacted isocyanate groups. The products obtained in the invention are the embedding materials or the resulting hardened or cured embedded products or more simply "bedded" final products which have excellent properties particularly adapted to the mounting of semipermeable membranes in dialysis equipment to give an improved and more useful construction.Type: GrantFiled: January 5, 1981Date of Patent: November 16, 1982Assignee: Akzo N.V.Inventors: Klaus Gerlach, Gerhard Wick
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Patent number: 4328138Abstract: Curable N-acylurea polymers and coating compositions are provided which cure by reaction of ethylenic unsaturation of the acyl group. The subject polymers are prepared by reaction of a polymeric carbodiimide with an ethylenically unsaturated monocarboxylic acid. Coating compositions so provided may have N-acylurea polymer solids contents of about 30% to about 95% by weight, exclusive of pigment.Type: GrantFiled: December 4, 1980Date of Patent: May 4, 1982Assignee: DeSoto, Inc.Inventors: Shiow-Ching Lin, Gerry K. Noren
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Patent number: 4312971Abstract: The subject matter of this invention relates to the preparation of polyurethanes. It is particularly concerned with the use of certain organo-zirconium and organo-mercury compounds as co-catalysts in the preparation of polyurethanes.Type: GrantFiled: December 8, 1980Date of Patent: January 26, 1982Assignee: BASF Wyandotte CorporationInventors: James A. Gallagher, Bernardas Brizgys
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Patent number: 4307000Abstract: A coating composition of an aliphatic polyurethane resin in an organic solvent; wherein the resin has terminal hydroxyl groups, a weight average molecular weight of about 3,000 to 30,000, and is the reaction product of a fatty acid ester of drying oil fatty acids, polyol, having at least three reactive hydroxyl groups, aromatic monobasic and an alkyl amino aromatic acid that provides ultraviolet light absorbing groups, and an aliphatic diisocyanate; the composition can contain conventional pigments, organo metallic driers, and light stabilizers and cures at ambient temperatures and is useful as primary finish for metals, plastics and reinforced plastics, and can be used as a refinish composition for automobiles and trucks.Type: GrantFiled: December 1, 1980Date of Patent: December 22, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Joseph A. Vasta
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Patent number: 4306052Abstract: Novel thermoplastic polyester polyurethanes are disclosed which are obtained by reacting a polyester diol, a difunctional extender, a methylenebis(phenyl isocyanate), and from about 0.0025 mole to about 0.03 mole per equivalent of isocyanate of a monocarbodiimide product derived from a methylenebis(phenyl isocyanate) or the corresponding uretidinedioneimine adduct thereof with said latter methylenebis(phenyl isocyanate).The polyester polyurethanes are characterized by a combination of thermoplasticity, extremely good hydrolytic stability which cannot be diminished by solvent action, good physical properties, particularly tensile strength and elongation, and enhanced clarity of molded articles.Type: GrantFiled: September 25, 1980Date of Patent: December 15, 1981Assignee: The Upjohn CompanyInventors: Henry W. Bonk, Richard W. Oertel
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Patent number: 4294951Abstract: Rapidly cured polyurethane elastomers are prepared by mixing a diphenylmethanediisocyanate based liquid prepolymer obtained from polytetramethylene ether glycol and an aliphatic diol at specified proportions, and a curing agent essentially containing said polytetramethylene ether glycol, diol and organometallic catalyst.Type: GrantFiled: July 14, 1980Date of Patent: October 13, 1981Assignee: Mitsui-Nisso CorporationInventors: Toshio Sugita, Hiroaki Sakaguchi, Hisanobu Tsuda, Tsuyoshi Suzuki
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Patent number: 4293669Abstract: Heat resistant polymers connected by ester and/or urethane groups and optionally amide- and/or imide groups and/or hydantoin and/or isocyanurate rings are obtained by crosslinking the polymers with trishydroxy alkyl triazolidine -3,5-diones.Type: GrantFiled: March 3, 1980Date of Patent: October 6, 1981Assignee: Bayer AktiengesellschaftInventors: Ludwig Rottmaier, Rudolf Merten, Jurgen Lewalter, Wilfried Zecher, Willi Dunwald
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Patent number: 4289868Abstract: Poly(thio)hydantoins are prepared by reacting an iso(thio)cyanate having at least two iso(thio)cyanate moieties with a compound of the formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each represents hydrogen, halogen, a C.sub.1 -C.sub.20 aliphatic group, a C.sub.7 -C.sub.20 aliphatic-aromatic group, a C.sub.6 -C.sub.20 aromatic group or a heterocyclic group having from 4 to 16 ring members and at least one N, O or S atom;A represents CN, COR, substituted or unsubstituted C.sub.1 -C.sub.20 aliphatic group, C.sub.7 -C.sub.20 aliphatic-aromatic group, C.sub.6 -C.sub.20 aromatic group or a heterocyclic group having from 4 to 16 ring members and at least one N, O or S atom wherein the substituents are NO.sub.2, COOR.sub.4, CN, CO or OH; R and R.sup.4 are selected from the definition of R.sup.1 and R.sup.2 with the exclusion of halogen;M represents OH or ##STR2## and R.sup.6 represents hydrogen, unsubstituted or substituted C.sub.2 -C.sub.20 aliphatic, C.sub.5 -C.sub.12 cycloaliphatic, C.Type: GrantFiled: December 6, 1979Date of Patent: September 15, 1981Assignee: Bayer AktiengesellschaftInventors: Jurgen Lewalter, Rudolf Merten, Wilfried Zecher, Willi Dunwald
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Patent number: 4288586Abstract: The present invention relates to a new process for the preparation of polyisocyanates containing isocyanurate groups by the partial trimerization of the isocyanate groups of 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane (also known as isophorone diisocyanate and abbreviated IPDI), using catalysts which accelerate the trimerization of isocyanate groups, characterized in that the catalysts used are quaternary hydroxyalkyl ammonium hydroxides containing at least one hydroxyalkyl group. The present invention also relates to the polyisocyanates containing isocyanurate groups produced according to this process and to their use, optionally in the form of products which are blocked with blocking agents for isocyanate groups, as isocyanate components for polyurethane lacquers.Type: GrantFiled: February 12, 1979Date of Patent: September 8, 1981Assignee: Bayer AktiengesellschaftInventors: Manfred Bock, Josef Pedain, Wilhelm Slawyk
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Patent number: 4271289Abstract: Compositions which are stable in the absence of oxygen are formed by mixing the following substantially in the absence of oxygen(A) 100 parts by weight of at least one mercapto-functional organic compound which contains at least two mercapto groups per molecule;(B) 0 to 200 parts by weight of at least one filler; and(C) a catalytic amount of a metal carbonyl compound selected from the group consisting of Fe(CO).sub.5, Fe.sub.2 (CO).sub.9, Fe.sub.3 (CO).sub.12, dicyclopentadienyldiiron tetracarbonyl, butadieneiron tricarbonyl, cyclohexadieneiron tricarbonyl, Ni(CO).sub.4, dicyclopentadienyldinickel dicarbonyl, Mn.sub.2 (CO).sub.10, methylcyclopentadienylmanganese tricarbonyl and cyclopentadienylcobalt dicarbonyl, preferably from 0.1 to 6 parts by weight of an iron carbonyl compound per 100 parts by weight of (A).Such compositions polymerize or cure upon exposure to oxygen.Type: GrantFiled: December 3, 1979Date of Patent: June 2, 1981Assignee: Dow Corning CorporationInventors: Gary R. Homan, Chi-long Lee
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Patent number: 4268649Abstract: A binder for cellulose fiber reinforced board material comprising a mixture of:(a) a weakly alkaline phenol-formaldehyde condensate resin with a phenolic compound to formaldehyde mol ratio of 1:1.5 to 1:3.0, preferably of 1:1.8 to 1:2.7, and with an alkali content of .ltoreq.15% by weight NaOH or KOH, related to the solids content of the resin;(b) a di- and/or poly-functional isocyanate in a quantity of from 5% to 25% by weight, related to (a); and(c) a tertiary alkyl and/or aralkyl amine and/or alkylene polyamine in a quantity of from 0.1% to 5% by weight, related to (a),a boiling water and weather resistant board material containing said binder and a process for the production of said board material.Type: GrantFiled: May 29, 1979Date of Patent: May 19, 1981Assignee: Rutgerswerke AktiengesellschaftInventors: Karl Jellinek, Rolf Muller
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Patent number: 4263411Abstract: A process of forming polyurethane compositions which emit reduced amounts of toxic smoke on burning is described. The process comprises reacting a mixture of an organic compound having two or more active hydrogen atoms, an organic polyfunctional isocyanate, a catalyst and at least one metal salt of an aliphatic or alicyclic monocarboxylic acid wherein the metal is cobalt, copper, nickel or manganese. The metal salt is added to the mixture in an amount which is sufficient to reduce the formation of toxic substances when the polyurethane is ignited.Type: GrantFiled: September 28, 1979Date of Patent: April 21, 1981Assignee: Mooney Chemicals, Inc.Inventor: Eugene Bak
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Patent number: 4263423Abstract: The instant invention is directed to a process for the production of a light fast, transparent polyurethane elastomer comprising reacting:(A) from 90 to 50% by weight, based on the polyurethane solids content, of a compound having a molecular weight of from 400 to 10,000 which has at least two Zerewitinoff active hydrogen atoms;(B) from 50 to 10% by weight, based on the polyurethane solids content, of an aliphatic and/or alicyclic polyisocyanate; and(C) from 0 to 20% by weight, based on the polyurethane solids content, of a chain-lengthening agent having a molecular weight of from 60 to 400; in the presence of:(D) catalysts for the isocyanate polyaddition reaction, the improvement wherein said catalysts, component (D), is a catalyst combination of:(a) an alkali metal hydroxide and/or alkaline earth metal hydroxide; and(b) an organometallic compound selected from the group consisting of the acetyl acetonate of iron, C.sub.1 -C.sub.Type: GrantFiled: July 16, 1979Date of Patent: April 21, 1981Assignee: Bayer AktiengesellschaftInventors: Jurgen Schwindt, Holger Meyborg, Gerhard Grogler, Klaus Recker
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Patent number: 4263408Abstract: The instant invention is directed to a process for the production of molded foams having a compact surface and cellular core and an integral density distribution over the cross-section of the body, comprising reacting(A) polyisocyanates, and(B) relatively high molecular and/or low molecular compounds having an average of at least two isocyanate-reactive hydrogen atoms in the presence of:(C) catalysts for the isocyanate polyaddition reaction and(D) blowing agents and optionally other known additives, in a closed mold under the conditions of foaming inside molds, the improvement wherein said polyisocyanates are aliphatic and/or alicyclic polyisocyanates and said catalysts are catalyst combinations of:(i) an alkali metal and/or alkaline earth metal hydroxide and(ii) a metal compound, the metal compound being the acetylacetonate of iron, C.sub.1 -C.sub.Type: GrantFiled: July 16, 1979Date of Patent: April 21, 1981Assignee: Bayer AktiengesellschaftInventors: Holger Meyborg, Werner Mormann, Gerhard Grogler, Jurgen Schwindt
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Patent number: 4237235Abstract: Urethane polymers are produced by reacting isocyanate with hydroxyl compounds in the presence of a catalytic amount of a chelating catalyst or cocatalyst which is a complex of a chelating agent with metallic ions and which does not react with the reagents.Type: GrantFiled: August 21, 1978Date of Patent: December 2, 1980Inventor: Rosalba Mazzucco
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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: 4211848Abstract: A polyisocyanate is reacted with an unsaturated polyester containing a vinyl monomer and a water-binding agent, then cured with water containing an oxidated silicon compound and an initiator such as a peroxide to produce solid or cellular solid inorganic-organic plastic.Type: GrantFiled: January 26, 1979Date of Patent: July 8, 1980Inventor: David H. Blount
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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: 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: 4180645Abstract: This invention is concerned with autoxidizable coating compositions which contain(a) a member selected from the group consisting of an organic polyisocyanate, a urethane oil, and a uralkyd;(b) at least one non-volatile reactive liquid monomer selected from the group consisting of dicyclopentenyl acrylate and dicyclopentenyl methacrylate; and(c) an effective amount of a polyvalent metal-containing complex or salt that catalyzes the curing of (a) and (b).Use of the non-volatile reactive liquid component enables the production of coating compositions having high application solids content and yet having suitable viscosity for efficient handling. The coatings obtained from the compositions of the present invention combine the typical desirable properties including durability, weather-resistance, etc.Type: GrantFiled: May 22, 1978Date of Patent: December 25, 1979Assignee: Rohm and Haas CompanyInventors: William D. Emmons, Kayson Nyi, Peter R. Sperry
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Polyurethane coating compositions containing unsaturated esters of glycol monodicyclopentenyl ethers
Patent number: 4178425Abstract: This invention is concerned with autoxidizable coating compositions which contain(1) a member of the group consisting of an organic polyisocyanate, an isocyanate-modified drying oil, and a uralkyd;(2) at least one non-volatile reactive liquid monomer selected from the group consisting of dicyclopentenyloxyalkyl acrylate and dicyclopentenyloxyalkyl methacrylate; and(3) an effective amount of a polyvalent metal-containing complex or salt that catalyzes the curing of (1) and (2).Use of the non-volatile reactive liquid component enables the production of coating compositions having high application solids content and yet having suitable viscosity for efficient handling. The reduced volatile component improves the environmental aspects of preparing and using the coating compositions while the combining of these materials in the film results in enhancement of the film properties without detriment to the qualities normally desired and attained with the polyurethane type of coating composition.Type: GrantFiled: May 22, 1978Date of Patent: December 11, 1979Assignee: Rohm and Haas CompanyInventors: William D. Emmons, Kayson Nyi -
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: 4160853Abstract: Energy-absorbing laminates for use in automobile windshields or other safety glass applications comprising a polycarbonate urethane and a sheet of glass are disclosed. The polyurethane is formed from a cycloaliphatic diisocyanate, a compound containing at least two active hydrogens per molecule and having a molecular weight below 250, and a polycarbonate diol prepared by the reaction of an aliphatic diol and a dialkyl carbonate using a titanium catalyst.CROSS-REFERENCE TO RELATED APPLICATIONSThis application is a continuation-in-part of application Ser. No. 681,012 entitled "Catalyst for Making Polycarbonate Diols for Use in Polycarbonate Urethanes" filed Apr. 28, 1976, now abandoned which in turn is a continuation-in-part of application Ser. No. 385,019 entitled "Transparent, Impact-Resistant Poly(alkylenecarbonate Urethane) Laminates" filed Aug. 2, 1973, now abandoned.Type: GrantFiled: November 29, 1977Date of Patent: July 10, 1979Assignee: PPG Industries, Inc.Inventor: Vernon G. Ammons
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Patent number: 4151345Abstract: A process for preparing polyurethanes comprising reacting a polyol with an organic polyisocyanate in the presence of a catalytic amount of nickel acetylacetonate, wherein the polyol and nickel acetylacetonates are held at elevated temperatures prior to being mixed with the polyisocyanate.Type: GrantFiled: October 17, 1977Date of Patent: April 24, 1979Assignee: The Goodyear Tire & Rubber CompanyInventor: Donald V. Hillegass
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Patent number: 4150212Abstract: This invention relates to new catalyst combinations having improved catalytic activity for isocyanate polyaddition reactions. The catalysts are combinations of known metal catalysts with aromatic compounds which contain at least one nitrogen atom as a hetero atom and have at least one primary amino group in the ortho- or para-position to the hetero atom. Preferred aromatic compounds include ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different, each represent a hydrogen atom, an aliphatic hydrocarbon group having from 1 to 6 carbon atoms or an aromatic hydrocarbon group having from 6 to 12 carbon atoms or two of the groups R.sub.1 to R.sub.4 represent a condensed aromatic ring.Type: GrantFiled: June 23, 1978Date of Patent: April 17, 1979Assignee: Bayer AktiengesellschaftInventor: Holger Meyborg
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Patent number: 4125487Abstract: Polyurethane/vinyl polymer composites are prepared without the requirement of the application of an external source of heat by the admixture of a composition comprising(A) a polyether polyol having an equivalent weight of 30-2500, such as an adduct of glycerine with propylene oxide;(B) an organic polyisocyanate, such as toluene diisocyanate;(C) an ethylenically unsaturated monomer, such as styrene;(D) a catalyst for polymerizing ethylenically unsaturated monomers such as tertiary butyl perbenzoate; and(E) a catalyst for urethane formation such as cobalt naphthenate.Foams may also be prepared by adding an appropriate foaming agent.Type: GrantFiled: May 23, 1977Date of Patent: November 14, 1978Assignee: The Dow Chemical CompanyInventor: Franciszek Olstowski
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Patent number: 4122046Abstract: Elastomeric, chemically stable, flame resistant polymers are obtained by polymerizing acrylamide or mixtures of acrylamide and at least one ethylenically unsaturated monomer copolymerizable therewith in the presence of a catalyst having the structure: ##STR1## wherein: Q = Na, K, NH.sub.4, Ca or Ban = 2 to 5 ##STR2## Me = Ti, Mn, Mo, Zr or W x = 0 to 1a, b, c each = 0 to 1a+b+c+d = valence of Me.The catalyst may be used alone as well as with UV, electron beam, ionizing radiation and combinations of these and with general redox systems known in the literature.Type: GrantFiled: June 17, 1975Date of Patent: October 24, 1978Inventor: John Joseph Waldmann