With Organic Compound Reactant Containing At Least Two Nh, Hnh Or =nh Groups And Wherein The Reactant Composition Is Devoid Of -c-xh, -c(=x)xh Or Anhydride Patents (Class 528/68)
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Patent number: 4738989Abstract: An aliphatic, isocyanate-base, polyurethane polymer and a process for preparing the polymer. The process comprises reacting, such as by spraying onto a substrate or an open mold, a caprolactone polyol with an aliphatic polyisocyanate in the presence of a catalytic amount of a metallo catalyst, and also in the presence of a fast-curing amount of a curing agent comprising an amine, particularly an aromatic diamine, such as diethyl toluene diamine, to provide a fast-reaction aliphatic polyurethane polymer.Type: GrantFiled: March 24, 1986Date of Patent: April 19, 1988Assignee: Urylon Development, Inc.Inventor: Stuart B. Smith
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Patent number: 4735984Abstract: A composition containing dispersed pigment comprises, as a dispersing agent, a reaction product of at least one polyamine having two or more primary amino groups and/or secondary amino groups and at least one polyisocyanate having two or more isocyanate groups.Type: GrantFiled: December 20, 1985Date of Patent: April 5, 1988Assignee: Nippon Paint Co., Ltd.Inventors: Harunori Gouji, Hisao Kato, Hiroyoshi Kataoka
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Patent number: 4736009Abstract: Partially alkylated polyamines which may be viewed as low molecular weight polymers of x-amino-y-methylenephenyl are effective curing agents in combination with other polyamines and polyols in reaction injection molding for diverse class of polyisocyanates. Alkylation may range from 5 up to 100 percent to afford polyamines with a board spectrum of cure times, as well as to give elastomers with an interesting and useful diversity of properties. Such polyamines may be used as a constituent in a blend of polyamines as the isocyanate-reactive component, in which case the elastomer may be viewed as predominantly a polyurea, or as a constituent in a blend with polyols, in which case the elastomer may be viewed as an elastomer with both urethane and urea segments.Type: GrantFiled: December 29, 1986Date of Patent: April 5, 1988Assignee: UOP Inc.Inventors: David W. House, Ray V. Scott, Jr., William M. Baumann
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Patent number: 4732919Abstract: This invention relates to a reaction injection molded elastomer made by reacting ingredients comprising a high molecular weight polyol or polyoxyalkylene polyamine, a chain extender and a quasi-prepolymer of a polyoxyalkylene polyamine and an aromatic isocyanate.Type: GrantFiled: November 6, 1986Date of Patent: March 22, 1988Assignee: Texaco Inc.Inventors: Robert A. Grigsby, Jr., Richard J. G. Dominguez, Wheeler C. Crawford
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Patent number: 4732959Abstract: A polymer comprising a poly(urethane)ureamide is prepared by a reaction of a polyisocyanate and a polyesterpolyol derivative of the formula [I] ##STR1## wherein A is an n-valaent radical obtained by removal of terminal hydrogen atoms from an n-valaent polyester-polyol having a molecular weight of 400 to 10,000 and containing ##STR2## group in the main chain, n is an integer of 2.ltoreq.n.ltoreq.4,x is an average value and a number of 0.ltoreq.x.ltoreq.(n-1),--NH-- group of ##STR3## in the main chain forms an amido group connected with a carbonyl group of an aminobenzoic acid and/or a carbonyl group of a polybasic acid component of the polyesterpolyol and,--CO-- group of ##STR4## in the main chain forms an ester group or amido group. The polymer has higher heat resistance and greater mechanical strength as compared to corresponding polyester-urethanes.Type: GrantFiled: November 13, 1985Date of Patent: March 22, 1988Assignee: Toyo Tire & Rubber Company LimitedInventors: Kozo Otani, Yoshio Yamada
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Patent number: 4719281Abstract: This invention provides novel polymers which are characterized by a recurring structural unit that contains a pendant quinoid structure and that exhibits nonlinear optical response.The following structure is illustrative of an invention polymer: ##STR1## where m is an integer of at least 3.Type: GrantFiled: April 21, 1986Date of Patent: January 12, 1988Assignee: Hoechst Celanese CorporationInventor: Eui W. Choe
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Patent number: 4714778Abstract: This invention relates to a class of alkenylated toluenediamines having at least one alkenyl group ortho to an amine group. More particularly the toluenediamines are represented by the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen, C.sub.1-3 aliphatic, phenyl, halogen or alkoxy radicals, or R.sub.2 and R.sub.4 or R.sub.5 are bridged via an alkylene radical --(CH.sub.2).sub.y -- wherein y=2 to 5, and x is one or two provided that in said formula at least one of R.sub.1, R.sub.2, R.sub.3, R.sub.4 or R.sub.5 is C.sub.1 or greater.The above described alkenylated toluenediamines have been found to be well suited as antioxidants and as tri- and tetra functional chain extenders in forming polyurethane/urea elastomers systems and for providing pendant unsaturation for post curing and polymerization.Type: GrantFiled: March 7, 1986Date of Patent: December 22, 1987Assignee: Air Products and Chemicals, Inc.Inventors: William F. Burgoyne, Jr., Dale D. Dixon
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Patent number: 4705814Abstract: This invention relates to a reaction product of polyoxyalkylene polyamine and an isocyanate wherein the polyoxyalkylene polyamine is present in less than the stoichiometric amount.Type: GrantFiled: November 6, 1986Date of Patent: November 10, 1987Assignee: Texaco Inc.Inventors: Robert A. Grigsby, Jr., Richard J. G. Dominguez, George P. Speranza
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Patent number: 4686242Abstract: This invention comprises a process whereby an amine functional compound having an equivalent weight of at least about 400 is reacted with an excess of a polyisocyanate to form an isocyanate-terminated prepolymer or quasi prepolymer, which polymer or quasi prepolymer is reacted with an isocyanate-reactive material which is preferably a relatively low equivalent weight polyol or mixture thereof with an additional amount of said amine functional compound or a relatively high equivalent weight polyol to form a polyurea containing polymer which is preferably non-cellular or microcellular.Type: GrantFiled: January 31, 1986Date of Patent: August 11, 1987Assignee: The Dow Chemical CompanyInventors: Robert B. Turner, Richard D. Peffley, Raymond A. Plepys, Ralph D. Priester, Manuel Gonzales, Jr., Kimbley A. Bushman
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Patent number: 4673722Abstract: A method of forming a high impact strength article of nylon/polyurea copolymer by reaction injection molding precursors of a polyurea prepolymer and a caprolactam together including the steps of prereacting a diisocyanate, a diamine and caprolactam to form a polyurea prepolymer having carbamyl caprolactam terminated end groups and then rapidly mixing the prepolymer with suitable amounts of caprolactam and a caprolactam alkali metal salt initiator and adding the mixture to a heated mold to polymerize the mixture and form the article.Type: GrantFiled: December 23, 1985Date of Patent: June 16, 1987Assignee: General Motors CorporationInventors: Zachariah G. Gardlund, MaryAnn Bator
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Patent number: 4670346Abstract: A process for preparing a slow-burning, low-smoking, high heat-distortion-temperature polyisocyanurate polymer and the polymer produced thereby, which process comprises reacting an MDI prepolymer with a caprolactone polyol in the presence of a trimerization catalyst, wherein the MDI prepolymer is prepared from an MDI having a functionality of about 2.4 or less, and particularly a 2.4 isomer, and with an ethylene-oxide-capped polypropylene oxide polyol, the process providing for the formation of a rigid, high heat-distortion RIM or an open-spray molded part.Type: GrantFiled: June 2, 1986Date of Patent: June 2, 1987Assignee: Thermocell Development, Ltd.Inventor: Stuart B. Smith
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Patent number: 4668734Abstract: The present invention is directed to a stable dispersion of a polyurea and/or a polyhydrazodicarbonamide in a relatively high molecular weight hydroxyl-group containing material, which dispersion has a solids content of from 5 to 50 percent by weight and which is obtained by reacting(a) an organic di- and/or polyisocyanate with(b) an amine-functional material comprising an addition product of(1) acrylonitrile and(2) a member selected from the group consisting of(i) hydrazine,(ii) aliphatic di- or polyamines containing at least two primary amino groups,(iii) cycloaliphatic di- or polyamines containing at least two primary amino groups,(iv) araliphatic di- or polyamines containing at least two primary amino groups, and(v) mixtures thereof,the ratio of (1) to (2) being at least one mol of (1) per mol of (2) and at most one mol of (1) for each nitrogen atom contained in (2) per mol of (2),the reaction of component (a) and component (b) being conducted at a temperature of from 30.degree. to 170.degree. C.Type: GrantFiled: December 20, 1985Date of Patent: May 26, 1987Assignee: Bayer AktiengesellschaftInventors: Manfred Dietrich, Klaus K/o/ nig, Hans Hettel, Peter Seifert, Peter Vehlewald
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Patent number: 4667009Abstract: Reaction injection molded polyurea elastomers are disclosed that are derived from the reaction of (1) an aromatic polyisocyanate; (2) primary or secondary amine terminated polyethers; and (3) an aromatic amine extender combination comprising (a) an aromatic diamine having at least one of the positions ortho to each amine group substituted by a lower alkyl group and (b) a polymethylene polyphenylamine.The use of the polymethylene polyphenylamine component allows for the retention of the good physical properties of the prior art polyureas while at the same time effecting a cost reduction in the preparation of this useful class of polymers.Type: GrantFiled: September 25, 1985Date of Patent: May 19, 1987Assignee: The Dow Chemical CompanyInventors: James H. Ewen, John O. Guerrero
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Patent number: 4667008Abstract: This invention relates to the production of polymer-coated, finely divided polyisocyanates by mixing(A) solid, finely divided polyisocyanates (preferably dimeric diisocyanates or urea diisocyanates) with(B) polyisocyanates differing in composition from those mentioned under (A) (preferably (cyclo) aliphatic polyisocyanates, such as biuretized diisocyanates or trimers or NCO-prepolymers),in quantities of from 0.05 to 50 parts by weight, and preferably in quantities of from 0.2 to 25 parts by weight, of (B) per 100 parts by weight of (A). The solid polyisocyanate particles surface-modified by covering with polyisocyanates (B) and then reacted with(D) isocyanate-reactive compounds containing reactive hydrogen atoms or with compounds free from active hydrogen atoms which form polymers with isocyanates in sub-equivalent to substantially equivalent quantities (preferably 0.5 to 1.Type: GrantFiled: May 8, 1985Date of Patent: May 19, 1987Assignee: Bayer AktiengesellschaftInventors: Gerhard Grogler, Richard Kopp, Heinrich Hess
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Patent number: 4624995Abstract: A poly(triazolinethione) is prepared by a process comprising the steps:(a) providing a poly(acylthiosemicarbazide),(b) cyclodehydrating the poly(acylthiosemicarbazide) by subjecting it to an elevated temperature in the presence of an aqueous alkaline solution to form a polyanion of a poly(triazolinethione),(c) treating the polyanion of the poly(triazolinethione) with aqueous acid solution to provide the poly(triazolinethione), and(d) isolating the resulting poly(triazolinethione).Type: GrantFiled: April 9, 1985Date of Patent: November 25, 1986Assignee: Minnesota Mining and Manufacturing CompanyInventors: Alan R. Katritzky, Stephen J. Cato, Jerald K. Rasmussen, Larry R. Krepski, Steven M. Heilmann
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Patent number: 4603189Abstract: Triisocyanates and isomeric mixtures of triisocyanates corresponding to the formula ##STR1## in which R represents hydrogen or an alkyl group having from 1 to 4 carbon atoms are made by phosgenating the corresponding triamine. These triisocyanates are particularly useful in the production of polyurethanes, especially polyurethane lacquer coats.Type: GrantFiled: April 29, 1985Date of Patent: July 29, 1986Assignee: Bayer AktiengesellschaftInventors: Hartmut Knofel, Stefan Penninger, Michael Brockelt, Gunter Hammen, Herbert Stutz
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Patent number: 4581432Abstract: The invention relates to compositions which are storage-stable at room temperature and which can be heat-cured to form molded parts having polyurethane, polyurea, and polyisocyanurate groups, said composition containing(a) one or more polyols having a molecular weight of from 400 to 10,000 and a functionality of from 2 to 8,(b) at least one polyfunctional compound having a molecular weight of 62 to 400 and being selected from the group consisting of aliphatic hydroxyl compound, cycloaliphatic hydroxyl compounds, aromatic amino compounds, or mixtures thereof, and(c) an organic polyisocyanate which is present in the form of discrete particles, which are deactivated on their surfaces and are dispersed in the liquid component, and depending on the product needs,(d) catalysts,(e) blowing agents,(f) reinforcing materials, and(g) auxiliaries and additives,The single-component systems are used for the preparation of cellular or noncellular, optionally reinforced polyurethane, polyurea, and/or polyisocyanurate group-cType: GrantFiled: November 23, 1984Date of Patent: April 8, 1986Assignee: BASF AktiengesellschaftInventors: Rainer Blum, Frank Werner, Peter Horn, Rolf Osterloh, Martin Welz
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Patent number: 4581435Abstract: Alkyl-substituted thiapolycyclic polyahls such as dimethyl-9-thiabicyclononane diamines form polymers that have improved physical properties.Type: GrantFiled: April 27, 1984Date of Patent: April 8, 1986Assignee: The Dow Chemical CompanyInventor: David W. Hughes
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Patent number: 4576747Abstract: Novel isocyanato-azetidinedione compounds are provided which have the formula ##STR1## wherein R and R.sub.1 can be independently selected from hydrogen and hydrocarbyl or can be joined together and along with the carbon to which they are attached represent a cycloalkane residue having 4 to 6 ring carbon atoms, y is an integer from 1 to 7 and X is a hydrocarbon radical having a valency of y plus one.The monoisocyanate compounds are used as intermediates to provide further novel azetidinedione containing derivatives in the form of azetidinedione-isocyanurates (II) and azetidinedione-urethanes (III).All three classes of compounds can be employed as acid scavenging agents for stabilizing various kinds of halogenated polymer systems. Notably, (I) and (III) form highly useful polyamide-polyureas and polyamide-polyurethanes respectively by reaction with organic polyamines.Type: GrantFiled: May 7, 1984Date of Patent: March 18, 1986Assignee: The Upjohn CompanyInventor: Shenghong A. Dai
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Patent number: 4569982Abstract: According to the present invention, relatively high molecular weight aliphatic and/or aromatic polyamines having molecular weights of from 400 to 8,000 (preferably from 600 to 4,000) are mixed with substantially equivalent quantities of low molecular weight, solid, finely-divided diisocyanates having a melting point of >40.degree. C., (preferably >80.degree. C.), such as phenylene diisocyanate, naphth lene-1,5-diisocyanate, dimeric toluylene-2,4-diisocyanate or the urea diisocyanate of toluylene-2,4-diisocyanate. This mixture, having a pot life of at least several minutes, is subsequently heated to a relatively high temperature, such as from 80.degree. to 200.degree. C.The products obtained have excellent elastic properties over a broad temperature range. They have an exceptionally flat modulus of elasticity curve (G') in the torsional vibration test. The hard and soft segments are markedly segregated and are thus not substantially disturbed by reciprocal interaction causing "softening".Type: GrantFiled: January 24, 1985Date of Patent: February 11, 1986Assignee: Bayer AktiengesellschaftInventors: Gerhard Grogler, Heinrich Hess, Richard Kopp, Werner Rasshofer
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Patent number: 4569981Abstract: The present invention relates to water-dispersible plastics precursors which are solid at temperatures below about 40.degree. C. The plastics precursors are based on isocyanate-terminated prepolymers which have been hydrophilically modified with ionic groups and/or ethylene oxide units and which contain specified amounts of isocyanate groups and --NH-- groups.The present invention also relates to processes for preparing aqueous dispersions from the solid plastics precursors and to using the plastics precursors for cross-linking dispersed plastics containing isocyanate-reactive groups.Type: GrantFiled: July 6, 1981Date of Patent: February 11, 1986Assignee: Bayer AktiengesellschaftInventors: Wolfgang Wenzel, Dieter Dieterich
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Patent number: 4547548Abstract: Polycondensation compounds containing piperidine and triazine groups, having a mean molecular weight from 1000 to 20,000 and constituted by structural units a and b of the formula ##STR1## are suitable as anti-actinic stabilizers for incorporation in polymeric materials.Type: GrantFiled: July 19, 1984Date of Patent: October 15, 1985Assignee: Ciba-Geigy S.p.A.Inventor: Giuseppe Cantatore
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Patent number: 4544624Abstract: The invention provides a photosensitive resin composition containing a soluble synthetic linear high-molecular compound in an amount of 25 to 95 weight percent based on the whole composition, a monomer having at least one photopolymerizable unsaturated bond and a photopolymerization initiator and characterized in that part or all of the soluble synthetic linear high-molecular compound is an addition polymer of an organic diisocyanate compound with an amide compound, both terminals of the amide compound being either primary or secondary amide groups and the equivalent ratio of amino groups to isocyanate groups in the addition polymer is not less than 1.0. The high-molecular weight compound makes up at least 50% by weight base on the total amount of the polymer material present in the composition.Type: GrantFiled: January 2, 1985Date of Patent: October 1, 1985Assignee: Toyo Boseki Kabnushiki KaishaInventors: Masaru Nanpei, Akira Tomita, Toshiaki Fujimura, Kuniomi Etoh
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Patent number: 4537945Abstract: A poly(urethane)ureamide which comprises a polymer obtained by a reaction of (a) a polyether derivative of the general formula [I] and (b) a polyisocyanate exhibits an excellent wear resistance and heat resistance due to the presence of the aromatic amido groups ##STR1## wherein A is an n-valent radical obtained by removal of hydroxyl groups from an n-valent polyoxyalkylenepolyol having a molecular weight of 400 to 10,000,n is an integer of 2 to 8,x is an average value and a number of 0.ltoreq.x<(n-1) andy is an average value and a number of 0.05.ltoreq.y<1.Type: GrantFiled: September 17, 1984Date of Patent: August 27, 1985Assignee: Toyo Tire & Rubber Company LimitedInventors: Kozo Otani, Yoshio Yamada
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Patent number: 4532266Abstract: Polyether-based urethane-group-containing polyamines containing polymers and/or copolymers of unsaturated monomers and, optionally, urea and/or biuret and/or allophanate groups are produced by (a) reacting an NCO-prepolymer in aqueous alkaline solution at 0.degree. to 40.degree. C. to form a carbamate; (b) converting this carbamate to an amine by adding an ion exchanger to the reaction mixture; and (c) separating the polyamine from the reaction mixture. The NCO-prepolymers used as starting materials are prepolymers of (i) polyalkylene ether polyols having a molecular weight of from 1,000 to 10,000 containing from 1 to 60 wt. % of graft (co)polymers of unsaturated monomers; and (ii) excess molar quantities of organic polyisocyanate; and optionally, (iii) a low molecular weight chain-extending agent. The product polyamines have a molecular weight of from 1,000 to 10,000 and contain from 0.65 to 59.3 wt. % graft (co)polymer and from 0.11 to 2.9 wt. % terminal NH.sub.Type: GrantFiled: March 19, 1982Date of Patent: July 30, 1985Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Gerhard Balle, Dieter Dieterich, Holger Meyborg
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Patent number: 4525534Abstract: Polyamines containing aromatic and/or aliphatic primary amino groups are produced by hydrolyzing an isocyanate compound in the presence of water, an insoluble basic compound as a catalyst and a water-miscible solvent in a single reaction step. The isocyanate compound has an NCO-content of from 0.5 to 40 wt % and is preferably a prepolymer. The (pH-) basic compound is substantially insoluble in both water and the organic solvents generally used in such processes. An isocyanate-reactive compound may also be included in the reaction mixture in an amount which is from 0.1 to 15 wt % (based on isocyanate compound). The hydrolysis reaction is generally carried out at a temperature from 50.degree. to 165.degree. C. in a manner such that the reaction mixture remains substantially homogeneous. The product polyamines contain from 0.19 to 20.3 wt % primary amino groups. These polyamines are particularly useful in the production of polyurethanes.Type: GrantFiled: July 6, 1983Date of Patent: June 25, 1985Assignee: Bayer AktiengesellschaftInventor: Werner Rasshofer
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Patent number: 4520186Abstract: Aromatic uret dione diurea diamines corresponding to the formula ##STR1## in which X, Y, m and n are as defined herein are produced by reacting an aromatic diamine with a diisocyanate corresponding to a specified formula in a molar ratio of diamine to diisocyanate of at least 1.8 to 1. These diamines are particularly useful in the production of elastomers.Type: GrantFiled: August 25, 1983Date of Patent: May 28, 1985Assignee: Bayer AktiengesellschaftInventors: Heinrich Hess, Gerhard Grogler, Richard Kopp
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Patent number: 4518760Abstract: A novel process is provided for producing a poly(dithiocarbamate) resin chelating agent which comprises dissolving a polyimine in an alcohol solvent to form a polyimine solution. A polyisocyanate is admixed in the polyimine solution to produce a cross-linked polyamine-polyurea precursor resin. The cross-linked polyamine-polyurea precursor resin is then reacted with a mixture of NH.sub.4 OH and CS.sub.2 to produce a poly(dithiocarbamate) resin chelating agent.The novel process can employ a polyimine in anhydrous or aqueous suspension form and uses non-hazardous solvents for the polyisocyanate reactant.Type: GrantFiled: July 13, 1984Date of Patent: May 21, 1985Assignee: Olin CorporationInventors: Maurice R. Smith, Harvey B. Cochran
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Patent number: 4515923Abstract: Polyamines containing aromatically bound primary amino groups having an NH.sub.2 -content of from 0.19 to 20.3 wt % are produced by a single stage process. A compound containing aromatically bound NCO-groups and having an isocyanate content of from 0.5 to 40 wt % is hydrolyzed with an excess of water in the presence of a water-miscible polar solvent and optionally a catalyst. The hydrolysis is carried out at a temperature of from -10.degree. to 150.degree. C. in a manner such that the reaction mixture is substantially homogeneous. The water-miscible polar solvent generally has a boiling point of from 56.degree. to 250.degree. C. and a dielectric constant of at least 10. This polar solvent is used in a quantity of at least 5 parts solvent for every 100 parts of isocyanate. Tertiary amines are the preferred catalysts. These polyamines are particularly useful in the production of polyurethanes.Type: GrantFiled: June 21, 1983Date of Patent: May 7, 1985Assignee: Bayer AktiengesellschaftInventors: Rudolf Fauss, Hans J. Meiners, Werner Rasshofer, Holger Meyborg
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Patent number: 4506039Abstract: Polymer-containing polyether polyamines containing terminal aromatically-bound amino groups are produced by in situ polymerization of a polyether polyamine with an olefinically unsaturated monomer. The polyether polyamine starting material must have terminal aromatic amino groups, a molecular weight of from 800 to 10,000 and an aromatic amino group content of from 0.3 to 16 wt. %. Suitable olefinically unsaturated monomers include .alpha.,.beta.-unsaturated nitriles, aromatic vinyl compounds, .alpha.,.beta.-unsaturated carboxylic acids and esters thereof, vinyl esters, vinyl halides, vinylidene halides, .alpha.,.beta.-unsaturated carboxylic acid amides and aminoalkyl esters of unsaturated carboxylic acids. Acrylonitrile/styrene mixtures are preferred monomers. The starting materials are employed in quantities such that the product modified polyether polyamine contains from 1 to 60 wt. % polymer or graft-polymer. The product polyamines are particularly useful in the production of polyurethanes.Type: GrantFiled: December 20, 1982Date of Patent: March 19, 1985Assignee: Bayer AktiengesellschaftInventors: Gerhard Balle, Werner Rasshofer, Winfried Schoberth
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Patent number: 4504647Abstract: New compounds having one, two or three aldimine groups and one, two or three oxazolidine groups in their molecule are curing agents for organic polyisocyanates. Mixtures of said new compounds with polyisocyanates are stable for long periods if humidity is absent, if they however come into contact with water or the humidity of the environment they rapidly cure resulting in elastic or hard polymers. The new compounds are prepared by reacting a diamine or polyamine with up to 6 amino groups with an epoxy compound, yielding a polyamino alcohol, which is thereafter reacted with an aldehyde, e.g. formaldehyde, an aliphatic, cyclic or heterocyclic or aromatic aldehyde.Type: GrantFiled: May 20, 1981Date of Patent: March 12, 1985Inventors: Lutz D. Zabel, Jurg Widmer, Ueli Sulser
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Patent number: 4495081Abstract: A composition consisting essentially of (I) at least one polyol having an average of more than 2 hydroxyl groups per molecule and an average hydroxyl equivalent weight of at least about 500 and (II) as a chain extender composition (A) an aliphatic amine-containing material having at least one primary aliphatic amine group per molecule and (B) at least one material selected from (1) hydroxyl-containing materials, or (2) aromatic amine-containing materials.These compounds are useful in preparing polyurethane articles employing reaction injection molding technology.Type: GrantFiled: November 7, 1983Date of Patent: January 22, 1985Assignee: The Dow Chemical CompanyInventors: James A. Vanderhider, Gerald M. Lancaster
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Patent number: 4483974Abstract: A process for the production of solid polyisocyanates stabilized by a polymer coating and showing retarded reactivity comprising reacting(1) one or more solid polyisocyanates in particulate form, said polyisocyanates having melting points above 30.degree. C., and(2) from 0.1 to 25 equivalent percent of amine per isocyanate equivalent of an organic compound having a molecular weight of from 32 to 6000, said organic compound being selected from the group consisting of(a) di- or higher functional compounds containing 2 or more aliphatically-bound primary and/or secondary amino groups,(b) compounds containing one or more terminal --CO--, --NH--, --NH.sub.Type: GrantFiled: July 18, 1983Date of Patent: November 20, 1984Assignee: Bayer AktiengesellschaftInventors: Gerhard Grogler, Heinrich Hess, Richard Kopp
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Patent number: 4478938Abstract: Polyalkylenepolyamines are crosslinked in a non-anhydrous environment to yield water-swellable, essentially water-insoluble gels. The polyalkylenepolyamine is contacted with a polyisocyanate at a pH between about 5 and about 8 and subjected to a high rate of agitation. The process of this invention can be employed to immobilize proteins, enzymes, antibodies, etc.Type: GrantFiled: March 2, 1984Date of Patent: October 23, 1984Assignee: The Dow Chemical CompanyInventor: Harold H. Freedman
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Patent number: 4472568Abstract: This invention relates to an improved process for the preparation of aromatic polyamines containing urethane and/or biuret and/or urea and/or isocyanurate groups and preferably also ether groups by the hydrolysis of poly-N-monoaryl-N',N'-dialkyl urea compounds (1-aryl-3,3-dialkyl ureas). The ureas are obtained by the reaction of secondary aliphatic, cycloaliphatic or saturated heterocyclic amines with divalent to tetravalent isocyanate compounds containing isocyanate end groups attached to aromatic residues. The ureas correspond to the general formula: ##STR1## wherein R.sup.1, R.sup.2 denote alkyl or cycloalkyl groups, or together form a ring andA denotes a divalent to tetravalent residue attached to the ureas by aromatic groups.Hydrolysis is carried out in the presence of water and up to two equivalents of a base containing hydroxide ions and/or up to two equivalents of a compound containing tertiary amino groups, optionally in the presence of solvents.Type: GrantFiled: October 28, 1982Date of Patent: September 18, 1984Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Gerhard Grogler
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Patent number: 4469856Abstract: This invention relates to new liquid or fluid polyamine/carbonic acid salt compositions free from crystalline content and their preparation from mixtures containing at least one aliphatic or cycloaliphatic polyamine, an aliphatic or cycloaliphatic hydroxyamine having at least one hydroxyl group and at least one amino group, and water and optionally diluents and/or conventional auxiliary agents and additives, by the addition of carbon dioxide. The proportion of polyamine to hydroxyamine is in the range of from about 95:5 to 10:90 % by weight, the quantity of water added is from about 0.01 to 5 mol of H.sub.2 O per amine equivalent (but at least 1 mol of water per mol of CO.sub.2) and the quantity of CO.sub.2 added is from about 0.01 to 0.99 mol of CO.sub.2 per amine equivalent.Type: GrantFiled: October 18, 1982Date of Patent: September 4, 1984Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Wilhelm Thoma, Anton Schmitz
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Patent number: 4465825Abstract: This invention is directed to processes for forming either solid, linear polymers or thermoset polymers from novel N-cyanourea compounds of the formula: ##STR1## wherein n is at least 2 and R is the organic moiety of a polyisocyanate remaining after reacting the NCO groups of the polyisocyanate with cyanamide, preferably under atmospheric conditions. These N-cyanourea compounds are polymerized to solid, linear polymers useful as an epoxy curing agent, by agitation for about 50 hours under atmospheric conditions or to a thermoset polymer useful per se as an adhesive or sealant by heating at a temperature above 90.degree. C.Type: GrantFiled: December 18, 1981Date of Patent: August 14, 1984Assignee: W. R. Grace & Co.Inventor: Shiow-Ching Lin
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Patent number: 4463157Abstract: Self-curing cationic amide-group-containing aminourea resins are disclosed, if necessary with urethane groupings, which are the reaction product of at least(A) a polyaminoamide which has been produced from(1) one or more predominantly higher fatty acids and one or more alkylene or polyalkylene-polyamines and/or(2) dimer fatty acids, if necessary in mixture with predominantly higher, substantially unsaturated fatty acids, and one or more alkylene- or polyalkylene-polyamines, and additionally partially contains cyclic amidine-groupings produced under splitting off of water and, if necessary, amino-groups blocked by ketimine,(B) a diisocyanate and, if necessary, of(C)(1) a primary and/or secondary allyl- or methallylamine and/or(2) one or more saturated primary and/or secondary aliphatic, cycloaliphatic, heterocyclic or aromatic amines and/or(3) an allyl- or methallyl-alcohol and/or(4) one or more cyclic or polycyclic alcohols, which are olefinically unsaturated in their cyclic or polyclicic ring systems, and/orType: GrantFiled: January 20, 1983Date of Patent: July 31, 1984Assignee: Akzo NVInventors: Hilde Kersten, Helmut Magerlein
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Patent number: 4448904Abstract: The invention is a method of making a molded reaction injection molded elastomer. The reaction injection molded (RIM) elastomer is made by injecting via a RIM machine into a mold cavity of the desired configuration, a formulation comprising in the first stream amine terminated polyethers of greater than 1,500 molecular weight, a chain extender, and in the second stream methylene bis(phenylisocyanate) with a 2,4' isomer of greater than about 10%. RIM elastomers are useful, for example, for automobile body parts.Type: GrantFiled: June 8, 1983Date of Patent: May 15, 1984Assignee: Texaco Inc.Inventor: Richard J. G. Dominguez
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Patent number: 4426485Abstract: A water-soluble, thermoplastic, organic polymer is disclosed having segments of bunched monovalent hydrophobic groups. These polymers provide superior thickening and leveling in aqueous systems, through micelle-like associations, and aid suspension of particulate materials in non-aqueous systems.Type: GrantFiled: June 14, 1982Date of Patent: January 17, 1984Assignee: Union Carbide CorporationInventors: Kenneth L. Hoy, Richard C. Hoy
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Patent number: 4418160Abstract: A compound having a terminal isocyanate group is hydrolyzed to produce a polyamine having a urethane and/or a urea and/or a biuret group. More particularly, a carbamate is made by mixing an isocyanate prepolymer having urethane and/or urea and/or biuret groups present with aqueous base solutions at a temperature of from 0.degree. to 0.degree. C. and in quantities such that the equivalent ratio of hydroxyl to isocyanate groups is between from 0,3:1 to .gtoreq.1,01 to 1. The carbamate is then treated with an acid ion exchanger to form an amine. The amine is then removed from any other material which may be present. A preferred polyamine thus-produced corresponds to the general formula: ##STR1## in which each R radical may represent a divalent straight or branched- chain aliphatic radical; a divalent cycloaliphatic radical; a 4,4'- and/or a 2,4'-dicyclohexylmethane radical; or a 2,4- and/or 2,6-methyl cyclohexane radical.Type: GrantFiled: August 30, 1982Date of Patent: November 29, 1983Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Dieter Dieterich, Holger Meyborg
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Patent number: 4408008Abstract: The present invention relates to a process for the preparation of stable, colloidal, aqueous dispersions of cross-linked urea-urethanes which comprises reacting(a) an aqueously dispersed, substantially linear, isocyanate-terminated prepolymer having a molecular weight of up to about 25,000 and containing(i) about 0 to 120 milliequivalents of ionic groups per 100 grams of prepolymer, and(ii) about 0.35 to 10% by weight, based on the weight of the prepolymer, of lateral and/or terminal, hydrophilic ethylene oxide units wherein components (i) and (ii) are present in an amount sufficient to provide a stable dispersion of the prepolymer in the aqueous medium, with(b) polyfunctional amine chain extenders having an average functionality between about 2.2 and 6.0.The present invention additionally relates to the aqueous dispersions produced by the above process and to the films, coatings or adhesives produced from these dispersions.Type: GrantFiled: July 24, 1981Date of Patent: October 4, 1983Assignee: Mobay Chemical CorporationInventor: Peter Markusch
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Patent number: 4386218Abstract: A compound having a terminal isocyanate group is hydrolyzed to produce a polyamine having a urethane and/or a urea and/or a biuret group. More particularly, a carbamate is made by mixing an isocyanate prepolymer having urethane and/or urea and/or biuret groups present with aqueous base solutions at a temperature of from 0.degree. to 0.degree. C. and in quantities such that the equivalent ratio of hydroxyl to isocyanate groups is between from 0.3:1 to .gtoreq.1.01 to 1. The carbamate is then treated with an acid ion exchanger to form an amine. The amine is then removed from any other material which may be present. A preferred polyamine thus-produced corresponds to the general formula: ##STR1## in which each R radical may represent a divalent straight or branched-chain aliphatic radical; a divalent cycloaliphatic radical; a 4,4'- and/or a 2,4'-dicyclohexylmethane radical; or a 2,4- and/or 2,6-methyl cyclohexane radical.Type: GrantFiled: October 5, 1981Date of Patent: May 31, 1983Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Dieter Dieterich, Holger Meyborg
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Patent number: 4384052Abstract: Reaction products of an organic polyisocyanate with a reactive diamine such as bis(4-aminocyclohexyl)methane and isophorone diamine, prepared at a temperature of between 135.degree. C. and 200.degree. C., are used to prepare polyurethanes useful for comfort cushioning applications such as automotive seating, furniture, mattresses, and large automotive body panels.Type: GrantFiled: June 8, 1981Date of Patent: May 17, 1983Assignee: BASF Wyandotte CorporationInventors: Robert L. McBrayer, John G. Demou, Peter T. Kan, William E. Volz
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Patent number: 4369256Abstract: A novel polyaminic resin obtained by crosslinking a polyalkyleneamine (in particular polyethyleneamine) with diisocyanates in solution, is useful as a selective separation or extraction agent of a component having a "complementary" chemical structure (particularly heparin), by means of mere contact or "ionic exchange" with aqueous solutions containing it. Heparin is thus even quantitatively extracted from solutions containing it alone or in mixture with other glucosaminoglycanes. The polyamine can then release the "adsorbed" heparin and be recovered by a treatment with saline solutions. The novel resin is used in pharmaco-biological fields.Type: GrantFiled: April 6, 1981Date of Patent: January 18, 1983Assignee: Crinos Industria Farmacobiologica S.p.A.Inventors: Benito Casu, Giangiacomo Torri, Giorgio Zoppetti
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Patent number: 4369301Abstract: The present invention relates to lacquer polyisocyanates which contain about 0 to 8% free isocyanate groups, about 10 to 28% blocked isocyanate groups and about 2 to 10% of the structural units, --NH--NH--CO--O, all percentages based on the weight of the polyisocyanates, but excluding the weight of the blocking agent. Also provided is a process for preparing these polyisocyanates which comprises reacting about 10 to 30 mol % of the isocyanate groups of an organic polyisocyanate with reaction products which have (i) alcoholic hydroxyl groups and (ii) structural units of the formula, --O--CO--NH--NH--CO--O--, and/or of the formula H.sub.2 N--NH--CO--O--, with the formation of urethane groups and optionally groups corresponding to the formula, --NH--NH--CO--O--, and reacting about 50 to 90 mol % of the isocyanate groups of the organic polyisocyanate with a blocking agent.Type: GrantFiled: October 16, 1981Date of Patent: January 18, 1983Assignee: Bayer AktiengesellschaftInventors: Eberhard Konig, Josef Pedain, Hans J. Kreuder
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Patent number: 4365051Abstract: A polyurethane prepared by reacting specifically identified substituted aromatic diamines with isocyanate-terminated prepolymer. Prepolymer is prepared by reacting polyisocyanate with polymeric polyol. Diamines are required to be selected from specified substituted butylbenzoates, benzonitriles or benzoates. The diamine curative is taught to enhance the processing of the prepolymer/diamine mixture for commercial application.Type: GrantFiled: April 3, 1981Date of Patent: December 21, 1982Assignee: The Goodyear Tire & Rubber CompanyInventors: Daniel A. Chung, John P. Lawrence
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Patent number: 4362827Abstract: The invention concerns the production of particle board with a very substantially lowered formaldehyde emission as well as suitable binding agents. According to the invention the binding agent used in the production of the board is a combination of a polyisocyanate with a aminoplast resin containing 0.25 to 0.625 moles of formaldehyde per mole equivalent of aminogroups. The particle boards thus obtained possess satisfactory mechanical properties and a strongly reduced formaldehyde emission.Type: GrantFiled: September 3, 1980Date of Patent: December 7, 1982Assignees: Methanol Chemic Nederland V.O.F., Stamicarbon B.V.Inventors: Arie Tinkelenberg, Henricus W. L. M. Vaessen, Kwai W. Suen
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Patent number: 4347348Abstract: A heat-resistant heterocyclic polymer consisting of units of the general formula ##STR1## wherein R, R.sup.1 and X are as defined hereinbelow anda method for producing heat-resistant heterocyclic polymers, consisting in that, at a temperature of 90.degree. to 400.degree. C., there is conducted a reaction of polyfunctional nitrile-containing compounds with polyfunctional isocyanates.The proposed polymers are stable at temperatures from 300.degree. to 350.degree. C. Materials based thereon are capable of retaining their properties at a temperature of up to 400.degree. C. for long periods of time. The method is simple and can be effected without isolation, purification or drying the polymer, which allows combining the process of producing the polymer with that of producing a finished article.Type: GrantFiled: June 20, 1980Date of Patent: August 31, 1982Inventors: Alexei Y. Chernikhov, Mikhail N. Yakovlev, Valentina B. Lysova, Evgeny L. Gefter, Nina N. Shmagina
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Patent number: 4342861Abstract: A coating or molding composition including a polyisocyanate and an unsaturated imide, and having a ratio of total isocyanate functions to total polymerizable double bonds in the imide in the range of from 0.3 to 15, is addition polymerized to hard, imide group containing polymers characterized by the recurring unit: ##STR1## Coatings and shaped articles formed from such polymers are hard, tough, thermally stable, solvent resistant and are good insulators.Type: GrantFiled: January 15, 1981Date of Patent: August 3, 1982Assignee: Rhone-Poulenc IndustriesInventors: Jean-Louis Locatelli, Jean Robin