From N=c=x Reactant Having At Least Two -c-nh-c(=x)- Groups Patents (Class 528/59)
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Patent number: 4672100Abstract: A chemically-hardening two-component material based on polyurethane is provided, having a first component being a prepolymer with isocyanate end groups and a second component being a product which has been obtained from that prepolymer with isocyanate end groups by reacting it with a reactive compound which has at least two active groups, containing active hydrogen and which do not react identically with isocyanate. The prepolymer is a reaction product of an aliphatic or aromatic di-isocyanate with a polyol.Such a material can be produced by reacting a prepolymer which contains isocyanate end groups, with a second component, which, in turn, has resulted from a prepolymer with isocyanate end groups by reacting with a reactive compound which has at least two molecule groups, containing hydrogen and reacting differently with isocyanate. The material is especially suitable as a self-hardening gluing, coating, sealing and molding material.Type: GrantFiled: December 13, 1984Date of Patent: June 9, 1987Assignee: Gurit-Essex AGInventors: Max Schonbachler, Wolfgang Saur
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Patent number: 4661542Abstract: Pressure-sensitive adhesives which are mixed immediately prior to application, or need drying equipment tend to be expensive in use while those applied as hot melts tend to have poor heat resistance. According to the invention an adhesive composition curable by atmospheric moisture is provided, the composition comprising a prepolymer component with isocyanate functionality between 2.0 and 3.0 together with one or more polyetherurethane prepolymers having NCO groups available for reaction with water for chain extension, the cured adhesive composition having a glass transition temperature below 20.degree. C.Type: GrantFiled: January 29, 1986Date of Patent: April 28, 1987Assignee: USM CorporationInventors: Heinz Gilch, Hubertus von Voithenberg, Reinhard Rengel
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Patent number: 4652494Abstract: Preformed, energy-absorbing, scratch resistant, optical, flexible, and self-healing polyurethane sheets, which are adhesive under the influence of heat and pressure; bilayer glazing laminates and bilayer safety windshields including said sheets; wherein said polyurethane sheet is prepared preferably by reactive-casting on a horizontal support and formed preferably from a polyisocyanate monomer including about 2 to about 10 wt. % of urea groups.Type: GrantFiled: July 10, 1984Date of Patent: March 24, 1987Assignee: Saint-Gobain VitrageInventors: Jean L. Bravet, Daniel Colmon, Gerard Daude, Michel J. Moncheaux
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Patent number: 4649162Abstract: The invention relates to a process for the preparation of cellular or noncellular plastics, preferably polyurethane coatings, by reacting at least two components with one another, preferably organic polyisocyanates and polyhydroxyl compounds, by feeding the components into a mixing zone separately, and mixing them together and then discharging the reaction mixture from the mixing zone, while adding air heated to a temperature of 100.degree. to 1200.degree. C. to the reaction mixture as it emerges from the mixing zone.Type: GrantFiled: January 23, 1986Date of Patent: March 10, 1987Assignee: BASF AktiengesellschaftInventors: Peter Roche, Mathaeus Rank
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Patent number: 4647647Abstract: Addition compounds suitable as dispersing agents, obtainable by the reaction of polyisocyanates having an average functionality of from 2.5 to 6 with monohydroxyl compounds, reaction of the resulting reaction product with compounds of the formula IIG--(E).sub.n IIwherein E stands for --OH, --NH.sub.2 and/or --NHR (wherein R represents an alkyl group with 1 to 4 carbon atoms) and n stands for 2 or 3, and G represents an aliphatic, cycloaliphatic and/or aromatic group, and further reaction of the reaction product thus obtained with compounds of the formula IIIZ--Q IIIwherein Q stands for --OH, --NH.sub.2, --NHR (wherein R stands for an alkyl group having 1 to 4 carbon atoms) or --SH, and Z denotes a group having at least one basic group containing nitrogen. The invention also relates to processes for the preparation of these addition compounds, their use, and pulverulent or fibrous solids which are coated with these dispersing agents and are to be incorporated in liquid systems.Type: GrantFiled: December 24, 1984Date of Patent: March 3, 1987Assignee: BYK-Chemie GmbHInventors: Karlheinz Haubennestel, Peter Kramp
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Patent number: 4639502Abstract: The present invention relates to substantially colorless organic polyisocyanates, optionally in solution in an inert solvent, having a Hazen color index according to DIN 53 409 of at most 60 and a yellow value according to DIN 6167 of at most 3.0, characterized by a content of about 0.01 to 1 ppm (by weight), based on polyisocyanate, of an organic dye soluble in the polyisocyanate and having an absorption maximum of about 560 to 590 nm or a mixture of such dyes.The present invention also relates to two processes for preparing the substantially colorless organic polyisocyanates. In the first process, the organic dye is added to the prepared polyisocyanate while in the second process the organic dye is added to the starting materials used to prepare the polyisocyanate. Finally, the present invention is directed to the production of polyisocyanate polyaddition products from the substantially colorless organic polyisocyanates and isocyanate-reactive compounds.Type: GrantFiled: May 3, 1985Date of Patent: January 27, 1987Assignee: Bayer AktiengesellschaftInventors: Hanns P. Muller, Werner Clarenz, Ulrich von Gizycki, Kuno Wagner
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Patent number: 4623709Abstract: Polyurethane prepolymers in which polyhydric alcohols are initially reacted with the faster reacting isocyanate group of an asymmetrical diisocyanate with the slowly reacting group remaining intact, after which the reaction products are combined with a symmetrical diisocyanate of which the equally reactive isocyanate groups again react more quickly than the slowly reacting groups of the first polyfunctional isocyanate compound. The products obtained by this process are distinguished by a low residual monomer content.Type: GrantFiled: January 11, 1985Date of Patent: November 18, 1986Assignee: Henkel Kommanditgesellschaft auf AktienInventor: Hans Bauriedel
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Patent number: 4619955Abstract: A flexibilizing additive compatible with a wide variety of polymeric vehicles is provided wherein the additive comprises the reaction product of (a) an aliphatic polyisocyanate; (b) at least one monofunctional alcohol containing an ether or carboxyl oxygen; and (c) at least one diol. The flexibilizing additive can be combined with a thermoplastic or thermosetting film-forming vehicle to provide improved coating compositions.Type: GrantFiled: September 9, 1985Date of Patent: October 28, 1986Assignee: The Sherwin-Williams CompanyInventor: Thomas W. Druetzler
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Patent number: 4618667Abstract: Urethane compositions generally free of phase separation patterns and flow lines are produced. One method includes the utilization of a nucleating compound which is generally added to a urethane prepolymer before any chain extension thereof. Examples of nucleating agents include urethanes, ureas and allophanates such as carboxylic acids, organic acid and anhydrides, amides, imides and the like. Another method includes adding a very small initial incremental amount of a curing agent to the prepolymer with an insoluble product being produced thereby and subsequently adding the remainder of the curing agent.Type: GrantFiled: April 18, 1985Date of Patent: October 21, 1986Assignee: The Firestone Tire & Rubber CompanyInventors: Edward L. Kay, Kenneth B. Roskos
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Patent number: 4616043Abstract: A light stable, fast reacting, aliphatic polyurethane sprayable coating composition and injectable open molding material is prepared by reacting an A side composition comprising a trimerized or biuret polymethylene polyisocyanate prepolymer with a B side composition comprising an admixture of an alkoxy polyalkylene glycol, such as methoxypolyethylene glycol and an aromatic polyamine such as a diethyl toluene diamine to provide a polyurethane reaction product which rapidly gels, may be quickly removed from the mold, has good green strength and high temperature resistance and is characterized by good ultraviolet or light stability properties. Optionally, the B side composition may contain a catalytic amount of a metal carboxylate like lead napthenate. The A and B side compositions may be sprayed onto a mat in an open mold and also may be sprayed in conjunction with chopped glass fibers, to form a glass-fiber spray coating.Type: GrantFiled: April 26, 1985Date of Patent: October 7, 1986Assignee: Thermocell Development, Ltd.Inventor: Stuart B. Smith
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Patent number: 4609683Abstract: Quasi-prepolymers are made from aromatic isocyanates and aromatic-amine amides which comprise the reaction product of a polyoxyalkylene polyamine selected from the group consisting of diamines, triamines and mixtures thereof, and an isatoic anhydride of the formula: ##STR1## where B is selected from the group consisting of hydrogen, alkyl, nitro, halo, hydroxy, amino and cyano and n is a number from 1 to 4. Such materials are useful for the production of reaction injection molded elastomers having improved properties.Type: GrantFiled: June 21, 1985Date of Patent: September 2, 1986Assignee: Texaco Inc.Inventors: Robert A. Grigsby, Jr., Richard J. G. Dominguez
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Patent number: 4605756Abstract: The invention relates to a process for the in situ production of dispersions or solutions of urea group-containing aromatic isocyanates by the low temperature reaction of aromatic diisocyanates and/or polyisocyanates (the NCO groups of which preferably exhibit different reactivities) with from 0.15 to 0.4 mols of water per NCO equivalent in relatively high molecular weight polyols and in the presence of catalysts accelerating the NCO/water reaction. Such catalysts are preferably selected from peralkylaminoalkyl ethers, peralkylamino-polyalkylene ethers and/or peralkyl-polyalkylene-polyamines. The present invention also relates to the resulting metastable solutions or dispersions and to the use thereof, optionally with the further addition of relatively high and low molecular weight compounds having hydroxyl, amino or hydrazide groups and with the optional addition of other polyisocyanates in polyurethane-forming ratios for the production of polyurethanes.Type: GrantFiled: December 17, 1984Date of Patent: August 12, 1986Assignee: Bayer AktiengesellschaftInventors: Gerhard Grogler, Richard Kopp, Heinrich Hess
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Patent number: 4598138Abstract: Stable phenolic-modified hydrocarbon resins with an OH number which is 4.5 or greater are resonably priced and toxicologically generally regarded as safe resins for the development of leucopigments, especially for the development of colors in pressure sensitive recording materials. The softening point may be varied by copolymerization with multivalent phenolic compounds and vinyl phenol within the range of 70.degree.-90.degree. C.Type: GrantFiled: November 15, 1983Date of Patent: July 1, 1986Assignee: Rutgerswerke AktiengesellschaftInventors: Wolfgang Lucke, Herbert Beneke, Peter Staglich
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Patent number: 4590225Abstract: The subject invention relates to alkylene oxide adducts of aniline prepared by reacting an alkylene oxide with an aniline in the presence of preferably at least 0.1 part of alkali metal hydroxide per 100 parts by weight of aniline.The resulting compositions may be used in the preparation of polyurethane products, such as rigid polyurethane foams, and may also be used as nonionic surfactants.Type: GrantFiled: January 22, 1985Date of Patent: May 20, 1986Assignee: BASF CorporationInventors: Alexander Korczak, William W. Levis, Jr.
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Patent number: 4587281Abstract: Bisimide resins having improved fracture toughness and resistance to microcracking comprise a mixture of,(a) a bisimide of the general formula (I) ##STR1## in which B represents a divalent radical containing a carbon-carbon double bond and A is a divalent radical containing at least two carbon atoms and(b) a polyisocyanate of the general formula (II)D(NCO).sub.x (II)in which x has a value of between 2 and 4 and D stands for an x-valent radical.Type: GrantFiled: February 28, 1985Date of Patent: May 6, 1986Assignee: The Boots Company PLCInventor: Horst Stenzenberger
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Patent number: 4582889Abstract: There is disclosed a corrosion preventive resin composition comprising an epoxy resin and at least one curing agent therefor. The epoxy resin comprises at least 40 wt % of a specific type of urethane-modified epoxy resin which is obtained by reaction between a compound having at least one epoxy group and at least one hydroxyl group and a urethane bond-bearing compound having isocyanate end groups and obtained by reaction between a polyhydroxyl compound and a polyisocyanate compound. The curing agent for the epoxy resin is at least one member selected from the group consisting of polyamines, polyamides and polymercaptans, all of which are sparingly soluble in water.Type: GrantFiled: May 31, 1985Date of Patent: April 15, 1986Assignee: The Yokohama Rubber Co., Ltd.Inventors: Kiyonaga Yamaguchi, Toshinobu Takahashi, Shigeo Omote, Mimuo Kawaguchi
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Patent number: 4579928Abstract: Urethane elastomers are produced by initially adding at least one incremental amount of a curing agent to a urethane prepolymer, having free polyisocyanate therein. Generally, free polyisocyanate-curing agent adducts are precipitated. Subsequently, the remaining amount of curing agent is added. Chain extension, accordingly, is favored which produces hard segment domains more evenly distributed in the polymer chain and imparts improved physical properties such as hardness, tear strength and high-low strain modulus.Type: GrantFiled: April 18, 1985Date of Patent: April 1, 1986Assignee: The Firestone Tire & Rubber CompanyInventors: Edward L. Kay, Kenneth B. Roskos
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Patent number: 4574793Abstract: Stabilized, catalyzed polyurethane systems are disclosed which are comprised of a polyurethane prepolymer, a tertiary amine catalyst and a stabilizing agent. To extend shelf life, and lend stability to the composition, the stabilizing agent is comprised of methane sulfonic acid. The stabilizer is suitable for use with most polyurethane systems catalyzed by tertiary amines, and produces longer shelf life or stability with lesser amounts than conventional stabilizers.In a particular embodiment requiring extended shelf life but quick curing times, a catalyst yielding these qualities is bis(2,6-dimethylmorpholino)diethylether. The catalyst, when incorporated in a polyurethane prepolymer coated on a flexible substrate, can be immersed in water, the material thereafter being wrapped about the portion of the patient's body to be immobilized, and cures rapidly, within about 15 minutes. The catalyst can optionally be combined with a stabilizer, such as methane sulfonic acid.Type: GrantFiled: August 21, 1984Date of Patent: March 11, 1986Assignee: Hexcel CorporationInventors: Kyu-Wang Lee, Winston L. Hedges, Kenneth S. Baron
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Patent number: 4562227Abstract: The invention relates to heat-hardenable reaction resin mixtures which contain polyfunctional epoxides, polyfunctional isocyanates and a reaction accelerator as well as, optionally containing customary additives and/or fillers. The invention has the object of achieving reaction resin mixtures which are stable in storage, consist of individual components that are easy to mix, exhibit a prolonged prehardening period and permit at the same time the manufacture of materials which combine the good mechanical properties and the high temperature-cycle resistance of polyurethane structures with the good thermal properties of oxazolidinone and isocyanurate structures. According to the invention, the reaction resin mixtures contain as polyfunctional isocyanates, isocyanate prepolymerisates in the form of reaction products of diphenyl methanediisocyanate and a diol, or of an isocyanate mixture of diphenyl-methanediisocyanate and a polymethylenepolyphenylisocyanate (with a functionality greater than 2) and a diol.Type: GrantFiled: June 27, 1984Date of Patent: December 31, 1985Assignee: Siemens AktiengesellschaftInventors: Wolfgang Rogler, Helmut Markert, Klaus Kretzschmar, Gerhard Piecha
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Patent number: 4560494Abstract: A flexibilizing additive compatible with a wide variety of polymeric vehicles is provided wherein the additive comprises the reaction product of (a) an aliphatic polyisocyanate; (b) at least one monofunctional alcohol containing an ether or carboxyl oxygen; and (c) at least one diol. The flexibilizing additive can be combined with a thermoplastic or thermosetting film-forming vehicle to provide improved coating compositions.Type: GrantFiled: December 27, 1984Date of Patent: December 24, 1985Assignee: The Sherwin-Williams CompanyInventor: Thomas W. Druetzler
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Patent number: 4558113Abstract: A process for preparing novel polymers having excellent physical properties by the polymerization of (A) a bicyclic amide acetal component and (B) a polyisocyanate component optionally with a small amount of water wherein the bicyclic amide acetal component is composed of two designated different types of bicyclic amide acetal is disclosed.Type: GrantFiled: March 11, 1985Date of Patent: December 10, 1985Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4552934Abstract: Improved two component adhesives allowing the components to be mixed at essentially a 1:1 ratio, giving excellent sag resistance, low viscosity, excellent handling ability and satisfactory gel time, said adhesives being composed of a prepolymer composition and a curative composition that can be mixed preferably at 1:2 to 2:1 ratio and a curative composition composed of a mixture of a reaction product of a multiple hydroxyl polyol of relatively low equivalent weight with a small amount of an organic polyiisocyanate and a polyamine.Type: GrantFiled: April 6, 1981Date of Patent: November 12, 1985Assignee: Ashland Oil, Inc.Inventors: Thomas G. Rabito, Richard L. Cline, Stephen M. Oswalt, Marvin T. Randleman, Michael E. Kimball
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Patent number: 4544763Abstract: Urethane-modified polyisocyanates prepared from toluene diisocyanate are desirable for economic, processing, and product property reasons. Such products should be low in viscosity to allow spray application and low in free TDI content to avoid undue physiological hazard.By use of prescribed reaction condition and reactant ratios, a suitable product can be prepared from hydroxyl-terminated polyoxyalkylene compounds, toluene diisocyanate, and diphenylmethane diisocyanate.Type: GrantFiled: October 19, 1984Date of Patent: October 1, 1985Assignee: Basf Wyandotte CorporationInventor: Thirumurti Narayan
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Patent number: 4532316Abstract: Reactive, 100 percent solids, segmented, phase-separating polyurethane prepolymers are provided, being the reaction products of:(i) a polyol (A) having a number average molecular weight of from about 600 to about 3500 and having a functionality of at least 2;(ii) an isocyanate (B) having a functionality of at least 2; and(iii) a low molecular weight chain extender (C) having a molecular weight in a range lower than about 500 and having a functionality of at least 2,characterized in that the above reactants are employed in such proportions as to satisfy the following equations: ##EQU1##Eq.sub.OH .gtoreq.Eq.sub.CE (b)Eq.sub.CE >O, (c)wherein Eq.sub.NCO is the equivalents of the isocyanate species employed, and Eq.sub.OH and Eq.sub.CE denote the equivalents, respectively, of the polyol and chain extender.Type: GrantFiled: May 29, 1984Date of Patent: July 30, 1985Assignee: W. L. Gore & Assoc., Inc.Inventor: Robert L. Henn
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Patent number: 4528153Abstract: The present invention relates to a substantially anhydrous binder having a self-releasing effect for the production of pressed articles comprising:(A) a polyisocyanate; and(B) a sulfonic acid corresponding to the general formula:R--SO.sub.3 H).sub.nwhereinn represents an integer of 1 or 2;R represents an aromatic hydrocarbon radical having from 6 to 14 carbon atoms, an aliphatic hydrocarbon radical having from 10 to 18 carbon atoms, a cycloaliphatic hydrocarbon radical having from 6 to 15 carbon atoms, an araliphatic hydrocarbon radical having from 7 to 15 carbon atoms or an alkaromatic hydrocarbon radical having from 7 to 24 carbon atoms; andthe equivalent ratio of the components (A) and (B) is 100:0.5 to 100:20.The invention is also directed to the use of such binders in the production of shaped articles by the hot pressing of a wide variety of organic and/or inorganic materials.Type: GrantFiled: September 20, 1982Date of Patent: July 9, 1985Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Scholl, Hanns I. Sachs, Gert Jabs, Gunther Loew
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Patent number: 4522986Abstract: Urethane-urea flow control agents are synthesized by a two-step process. First, an isocyanate-terminated urethane prepolymer is prepared by reacting a polyether polyol with a stoichiometric excess of a saturated cyclic aliphatic polyisocyanate. These isocyanate-terminated prepolymers are then modified by reaction with an ethanolamine to form urea endcapped flow control agents having number average molecular weight of between 1000 and 4000. These urea endcapped flow control agents can be blended with any urethane paint system and be compatible in structure. They have shown specifically superior compatibility with melamine cured high solids urethane paint systems. When blended with pigmented urethane paint at relatively small amounts, these flow control agents greatly reduce sagging while maintaining excellent leveling and viscosity properties of the paint.Type: GrantFiled: July 20, 1984Date of Patent: June 11, 1985Assignee: General Motors CorporationInventors: William T. Short, Robert A. Ottaviani
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Patent number: 4520145Abstract: Bisimide resins having improved fracture toughness and resistance to microcracking comprise a mixture of,(a) a bisimide of the general formula (I) ##STR1## in which B represents a divalent radical containing a carbon-carbon double bond and A is a divalent radical containing at least two carbon atoms and(b) a polyisocyanate of the general formula (II)D(NCO).sub.x (II)in which x has a value of between 2 and 4 and D stands for an x-valent radical .Type: GrantFiled: October 29, 1982Date of Patent: May 28, 1985Assignee: The Boots Company PLCInventor: Horst Stenzenberger
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Patent number: 4504648Abstract: A polyurethaneurea which comprises a polymer obtained by a polyaddition reaction of (a) a polyetherpolyol derivative and (b) an at least 2-valent polyisocyanate, the polyetherpolyol derivative having at least, on average, one terminal amino group in which at least, on average, one hydroxyl group is substituted by a residue of para-aminobenzoic acid ester, and having the general formula ##STR1## wherein n is an integer of 2 to 8, x is an average value and a positive number of 0.05 n to (n-1), 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.Type: GrantFiled: November 7, 1983Date of Patent: March 12, 1985Assignee: Toyo Tire & Rubber Company, LimitedInventors: Kozo Otani, Yoshio Yamada, Hiroyuki Okumura
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Patent number: 4485222Abstract: Thermosetting polyurethane compositions comprising a polymer having a molecular weight of from 500 to 10,000 and containing from about 0.3 to about 15 percent by weight of one or more functional groups selected from the group consisting of --OH, --COOH, --CONH.sub.2 and ##STR1## and a mixture of monomeric and oligomeric polyfunctional substituted urethane compounds, which may be derived by reaction of a polyol and isocyanic acid, followed by methylolation and alkylation. Such compositions may be cured at elevated temperature to produce solvent-resistant coatings.Type: GrantFiled: March 28, 1983Date of Patent: November 27, 1984Assignee: American Cyanamid CompanyInventor: Girish G. Parekh
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Patent number: 4483798Abstract: A method for producing a polyaddition product of isophorone diisocyanate and diols which comprises, reacting a uretidione group-containing dimer of isophoronediisocyanate, which is decomposable by heat into 98% isophorone diisocyanate, with a diol, wherein the ratio of NCO to OH groups is such that the final polyaddition product has free terminal NCO groups, or free terminal OH groups.Type: GrantFiled: August 13, 1981Date of Patent: November 20, 1984Assignee: Chemische Werke Huls AktiengesellschaftInventors: Josef Disteldorf, Rainer Gras, Werner Hubel, Elmar Wolf, Horst Schnurbusch
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Patent number: 4481345Abstract: Process for the production of water-hardenable compositions of organic polyisocyanates and polyamines containing at least partly blocked amino groups present as ketimines, the combinations essentially representing mixtures and optionally reaction products containing urea groups by mixing the organic polyisocyanates with the polyamines in such quantities that the equivalent ratio of isocyanate groups to blocked and free amino groups is between about 0.9:1 and 4:1 and reacting any free amino groups present with some of the isocyanate groups in the polyisocyanate to form ureas, characterized in that the polyamines containing at least partly blocked amino groups used are mixtures comprising(a) from about 50 to 95 amine equivalent percent of organic compounds which are free from primary and secondary amino groups and which contain at least two ketimine groups corresponding to the following formula ##STR1## in which R.sup.1 represents an alkyl or cycloalkyl radical and R.sup.Type: GrantFiled: February 27, 1984Date of Patent: November 6, 1984Assignee: Bayer AktiengesellschaftInventors: Klaus Nachtkamp, Manfred Bock, Reinhard Halpaap, Josef Pedain
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Patent number: 4478975Abstract: The invention concerns the oilproofing and waterproofing treatment of construction materials by applying to them a composition which comprises by weight:(A) from 0.1 to 25% of a fluorinated copolymer formed from(1) 5 to 70% of a fluorinated ester of the formula: ##STR1## in which Rf represents a perfluoro-alkyl radical, Q represents an oxygen or sulfur atom, W represent a bivalent linkage, one of the symbols R represents a hydrogen atom and the other a hydrogen atom or an alkyl radical,(2) 4 to 50% of a monomer of the formula: ##STR2## in which R' represent a hydrogen atom or an alkyl radical and R' represents an alkylene radical and(3) 0 to 91% of any other monomers'(B) from 2 to 25% of a polyisocyanate or isocyanate prepolymer;(C) from 0.1 to 10% of a catalyst; and(D) one or more diluting solvents to make up to 100%.Type: GrantFiled: January 19, 1984Date of Patent: October 23, 1984Assignee: AtochemInventors: Andre L. Dessaint, Marie-Jose Lina
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Patent number: 4471102Abstract: A storage stable one-component air curable urethane coating composition having improved color and abrasion resistance comprising at least twenty percent by weight or resin solids of a compound comprising at least one oxazolidine ring chemically combined from the nitrogen atom of the ring through an alkylene-urethane linking group to an isophorone diisocyanate prepolymer radical.The invention also comprises the method for preparing the compound and composition and a method for coating a surface by applying the composition of the invention to the surface and exposing the applied composition to air having a relative humidity of at least 10% and includes an article coated with the cured composition.Type: GrantFiled: November 4, 1983Date of Patent: September 11, 1984Assignee: Textron, Inc.Inventor: Glenn H. Petschke
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Patent number: 4471106Abstract: Phenolic-modified hydrocarbon polymers with a high OH-number yet with excellent compatibility with non-polar solvents are suitable for preparing adhesives and coating materials. The polymers are obtained by isothermal, catalytic copolymerization of:30-40% by weight phenolic compounds,65-30% by weight aromatic, unsaturated hydrocarbons, and5-30% by weight isobutene.Type: GrantFiled: November 4, 1983Date of Patent: September 11, 1984Assignee: Rutgerswerke AktiengesellschaftInventors: Wolfgang Luecke, Herbert Beneke, Peter Staeglich, Manfred Muehlenkamp
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Patent number: 4469857Abstract: A two-component system for producing a flowable to plastic synthetic resin composition comprising, as the first component, a combination of a polyisocyanate and an enamine, and the second component comprising a carrier compound having water aggregated thereto.Type: GrantFiled: June 17, 1983Date of Patent: September 4, 1984Assignee: Minnesota Mining and Manufacturing CompanyInventor: Gunther John
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Patent number: 4469831Abstract: The object of this invention is a moisture-curing, storage stable, single-component polyurethane system comprising:A. a polyurethane prepolymer with a free isocyanate content of 1 to 5 percent by weight;B. a dialdimine having the formulaR[--N.dbd.CH--C(CH.sub.3).sub.2 --CH.sub.2 --O--CO--CH--(CH.sub.3).sub.2 ].sub.2in whichR is a divalent aliphatic radical with 2 to 10 carbon atoms, aliphatic radical having 4 to 10 carbon atoms and containing ether oxygen and/or lower alkylamino nitrogen atoms, cycloaliphatic radical with 6 to 15 carbon atoms oraromatic radical with 6 to 21 carbon atoms;andC. an acid catalyst selected from the group consisting of aliphatic carboxylic acids, aromatic carboxylic acids, toluenesulfonic acid, and mixtures thereof.The polyurethane systems are used as coating, sealing, casting, spackling and bonding materials.Type: GrantFiled: April 28, 1983Date of Patent: September 4, 1984Assignee: BASF AktiengesellschaftInventors: Uwe Bueltjer, Heinrich Horacek, Wolfgang Druschke, Gernot Franzmann, Erhard Klahr, Hans-Juergen Foerster
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Polyurethane elastomer and an improved hypoallergenic polyurethane flexible glove prepared therefrom
Patent number: 4463156Abstract: A soft, low modulus, non-crystalline segmented polyurethane characterized by a 100% modulus less than about 250 psi, initial tensile set less than about 30% and tensile strength of about 3500 to 6500 psi obtained by balancing the percent hard segment and the degree of cross-linking within the ranges 14 to 25% hard segment and 5,000 to 30,000 molecular weight per cross-link in a segmented polyurethane; and a flexible glove for use by surgeons and others which is easily donned and comfortable on the hand, wherein the glove forming material consists essentially of the aforesaid polyurethane.Type: GrantFiled: March 15, 1982Date of Patent: July 31, 1984Assignee: Warner-Lambert Co., Inc.Inventors: Charles W. McGary, Jr., Vincent J. Pascarella, Delmer R. Rhodes, Robert A. Taller -
Patent number: 4456730Abstract: Polymer modified polyamines having a polymer content of from 1 to 30 wt. % and an aromatic amino group content of from 1 to 12.5 wt. % are produced by hydrolyzing a polyisocyanate prepolymer in an aqueous alkaline medium. The polyisocyanate prepolymer is polymer modified by in situ polymerization of either the prepolymer or the isocyanate used in making the prepolymer with an unsaturated monomer in the presence of a radical forming polymerization catalyst in a manner such that a solution and/or dispersion is formed. The prepolymer is formed from a relatively high molecular weight polyhydroxyl compound, aromatic polyisocyanate, and optionally a chain extender or crosslinking agent. The aromatic polyisocyanate used is from 60-100 wt. % polyisocyanate of the diphenyl alkane series and from 0 to 60 wt. % tolylene diisocyanate. The preferred unsaturated monomer is acrylonitrile containing up to 20 wt. % comonomer.Type: GrantFiled: June 21, 1983Date of Patent: June 26, 1984Assignee: Bayer AktiengesellschaftInventors: Gerhard Balle, Werner Rasshofer
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Patent number: 4456658Abstract: The present invention relates to a process for coating polyvinyl chloride sheet products, optionally containing plasticizers, with clear coatings which can be hardened under the influence of atmospheric moisture and have a viscosity at 23.degree. C. of from about 60 to 2500 mPa.s, and which contain (a) at least one polyisocyanate which is liquid at room temperature, (b) up to about 15% by weight, based on the coating of solvents, and optionally (c) conventional auxiliary agents and additives, and to the coated products produced therefrom.Type: GrantFiled: January 10, 1983Date of Patent: June 26, 1984Assignee: Bayer AktiengesellschaftInventors: Werner Kubitza, Gerhard Mennicken
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Patent number: 4451635Abstract: Polyurethane quaternary ammonium salts are obtained by heating a solution of a polyurethane resin characterized by having present in the polymer backbone hydroxyl groups and at least one substituent selected from the group consisting of carboxylate radicals and carboxyl radicals dissolved in a water-miscible organic solvent for the resin at a temperature above 64.degree. C. and below the decomposition temperature of said polyurethane resin with an organic chloride for a period of time; adding a strong base to the reaction mixture and continuing to heat said mixture to form a polyurethane quaternary ammonium hydroxide in solution; and precipitating the polyurethane quaternary ammonium hydroxide by pouring the reaction mixture into an excess of water.Type: GrantFiled: March 8, 1982Date of Patent: May 29, 1984Assignee: Tyndale Plains-Hunter, Ltd.Inventors: Francis E. Gould, Christian W. Johnston
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Patent number: 4440901Abstract: The present invention is directed to a process for the production of plastics based on an isocyanate-polyaddition product by(1) forming an isocyanate group-containing prepolymer from(a) a compound which has a molecular weight of from 146 to about 10,000, is substantially free from hydroxyl groups, contains at least two terminal carboxyl groups and optionally contains ether and/or ester groups,(b) excess quantities of an organic nonaromatic polyisocyanate which has at least one cyclohexane ring and exclusively contains aliphatically- and/or cycloaliphatically-bound isocyanate groups and(c) up to 10 equivalent percent, based on the isocyanate-reactive groups in component (a), of a compound which is monofunctional for the purposes of the isocyanate-addition reaction and,(2) reacting the product of step (1) with(d) a chain-lengthening agent such as water, a polyamine containing at least two primary and/or secondary amino groups or hydrazine or a derivative thereof containing at least two primary and/or secondaryType: GrantFiled: July 1, 1983Date of Patent: April 3, 1984Assignee: Bayer AktiengesellschaftInventors: Helmut Reiff, Dieter Dieterich
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Patent number: 4439553Abstract: This invention relates to hydrophilic, urethane-forming compositions and a method of forming polyurethanes having low residual, potentially carcinogenic, aromatic amines by adding scavengers comprising polyols end-capped with aliphatic polyisocyanates.Type: GrantFiled: January 17, 1983Date of Patent: March 27, 1984Assignee: W. R. Grace & Co.Inventors: James L. Guthrie, Clifton L. Kehr
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Patent number: 4438250Abstract: The invention is directed to suspensions of isocyanato ureas in isocyanate prepolymers; to a process for their production by reacting mixtures of aromatic diisocyanates containing isocyanate groups of different reactivities and prepolymers containing terminal isocyanate groups, with water; and to the use of the suspensions as synthesis components in the production of polyurethane plastics.Type: GrantFiled: January 16, 1980Date of Patent: March 20, 1984Assignee: Bayer AktiengesellschaftInventors: Gerhard Grogler, Otto Ganster, Klaus Recker
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Patent number: 4429098Abstract: Modified crude toluene diisocyanate characterized by the fact that it is obtained by reaction first of a crude toluene diisocyanate with a polyol in such a quantity that the lowering of the isocyanate concentration of the crude toluene diisocyanate at the most amounts to about 2.0--NCO groups per kilogram of crude toluene diisocyanate and by the fact that in a second step the above reaction product is aged under heat application for such a temperature and period of time that the lowering of the isocyanate concentration of this reaction product at the most amounts to 0.4--NCO groups per kilogram of product. This modified crude toluene diisocyanate can be used for making high resiliency polyurethane foam with improved properties.Type: GrantFiled: August 30, 1982Date of Patent: January 31, 1984Assignee: Produits Chimiques Ugine KuhlmannInventors: Jean Bertrand, Michel Gaillard
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Patent number: 4426487Abstract: This invention relates to a mixture which is stable in storage in the absence of moisture and comprises the following:(a) polyurethane prepolymers containing incorporated tertiary nitrogen atoms, structural units corresponding to the following formula:--O--CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --O--and terminal isocyanate groups,(b) aromatic or aliphatic orthophosphoric acid esters;(c) one or more inert solvents, and(d) optionally other auxiliaries and additives, and to the use of these mixtures as adhesives or coatings for flexible or rigid substrates.Type: GrantFiled: September 27, 1982Date of Patent: January 17, 1984Assignee: Bayer AktiengesellschaftInventors: Eberhard Konig, Rudolf Hombach, Manfred Dollhausen, Josef Pedain
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Patent number: 4424316Abstract: Reaction of a diepoxide with a mono-, or, preferably, dicarboxylic acid yields a prepolymer having both hydroxy and epoxy groups. This prepolymer, when reacted with a polyisocyanate, yields a poly(oxazolidone/urethane) thermoset composition which is substantially free of isocyanurate linkages. The thermoset contains oxazolidone linkages in its backbone which are separated from one another by ester linkages. Urethane linkages are present in side chains attached to the polymer backbone of the thermoset.Type: GrantFiled: October 8, 1981Date of Patent: January 3, 1984Assignee: Stauffer Chemical CompanyInventors: Anthony L. DiSalvo, Arthur J. Yu
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Patent number: 4419293Abstract: The present invention relates to a modified polyisocyanate having improved compatibility with aliphatic hydrocarbon solvents comprising the reaction product of(a) an aliphatic biuret isocyanate having the formula ##STR1## and (b) about 0.05 to 0.5 mols per equivalent of isocyanate of an aliphatic monohydroxy alcohol having at least 8 carbon atoms.Type: GrantFiled: July 10, 1981Date of Patent: December 6, 1983Assignee: Mobay Chemical CorporationInventors: George A. Hudson, deceased, Helmut F. Reiff
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Patent number: 4417043Abstract: A polymer capable of forming an anisotropic melt characterized in that the polymer chain includes residues of cross-linking reactants at a concentration sufficient to give a polymer with a melt viscosity of not greater than 10.sup.7 Nsec/m.sup.2 measured by capillary rheometry at a shear rate of 10.sup.4 N/m.sup.2. The polymers exhibit favorable shear dependent viscosity characteristics in that the viscosity is high under low shear conditions and is low under high shear conditions, as judged by the viscosity characteristics of polymers of the same composition but not containing the residues of cross-linking reactants.Type: GrantFiled: January 5, 1981Date of Patent: November 22, 1983Assignee: Imperial Chemical Industries PLCInventors: Frederic N. Cogswell, Brian P. Griffin, Clive P. Smith
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Patent number: 4413079Abstract: A polyurethene powder enamel comprising a mixture of(a) an adduct of a uretidinedione dimer of isophorone diisocyanate and a diol having the following formula: ##STR1## n.gtoreq.1, and R'=a divalent aliphatic, cycloaliphatic, araliphatic, or aromatic hydrocarbon radical, which is the residue of the diol,wherein the ratio of NCO to OH groups in the formation of said condensation product is from 1:0.5 to 1;0.9, the mole ratio of uretidinedione to diol is from 2:1 to 6:5, the content of free isocyanate groups in said adduct is not greater than 8% by weight, and said adduct has a molecular weight between 500 and 4000 and a melting point between 70.degree. C. and 130.degree. C., and(b) a polyol having an OH-functionality of 2.2 to 3.5, an average molecular weight of 2000 to 4500, a hydroxyl number of 30 to 100 mg KOH/g, a viscosity of <80,000 mPa.s at 160.degree. C. and a melting point between 65.degree. C. and 120.degree. C.Type: GrantFiled: August 13, 1981Date of Patent: November 1, 1983Assignee: Chemische Werke Huls AGInventors: Josef Disteldorf, Rainer Gras, Horst Schnurbusch
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Patent number: 4413112Abstract: This invention relates to new emulsifiers for aqueous isocyanate emulsions and to their use as binders in the production of molded articles, in particular plates, e.g., from materials containing lignocellulose.Type: GrantFiled: May 16, 1980Date of Patent: November 1, 1983Assignee: Bayer AktiengesellschaftInventors: Helmut Reiff, Hanns I. Sachs