With N-containing Reactant Patents (Class 524/874)
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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: 4721751Abstract: A polymerizable ethylenically unsaturated urea urethane polymer dispersed in a polymerizable ethylenically unsaturated compound is prepared by a process which comprises reacting a polyisocyanate, at least a portion of which is a diisocyanate, with a polyfunctional amine containing primary and/or secondary amino groups in the presence of:(a) a polyol, at least a portion of which is a polymeric polyol containing ethylenic unsaturation and having a carbon to oxygen ratio of at least 4/1;(b) a diluent which is an ethylenically unsaturated compound free of active hydrogens; and(c) an active hydrogen containing polymerizable ethylenically unsaturated compound; under conditions sufficient to form a polymerizable ethylenically unsaturated urea urethane polymer dispersed in a polymerizable ethylenically unsaturated compound.The aforedescribed urea urethane polymer dispersions are particularly useful in formulating curable compositions suitable for use as adhesives and sealants.Type: GrantFiled: March 26, 1987Date of Patent: January 26, 1988Assignee: PPG Industries, Inc.Inventors: Raymond F. Schappert, Joseph M. Makhlouf, Michael M. Chau
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Patent number: 4673705Abstract: Liquid coating compositions adapted to be cured by exposure to ionizing radiation are disclosed in which a liquid vehicle of coating viscosity having an ethylenically unsaturated portion comprising one or more polyethylenically unsaturated materials adapted to cure on radiation exposure, pigment dispersed in the vehicle, and an acrylate-functional radiation-curable dispersant having free carboxyl group for wetting the pigment and assisting in the stable dispersion of the pigment in the vehicle. This dispersant is an acrylate-functional carboxylic acid amide carrying free carboxyl groups, especially an adduct of a polyacrylate and a stoichiometric deficiency of a primary amine to provide a secondary amine having acrylate functionality, the secondary amine functionality being reacted with a polycarboxylic acid anhydride to form amide groups therewith.Type: GrantFiled: April 5, 1985Date of Patent: June 16, 1987Assignee: DeSoto, Inc.Inventors: Robert E. Ansel, Kevin P. Murray
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Patent number: 4661099Abstract: The present disclosure is concerned with self-adhesive sheet-like structures made by adhering an adhesive polyurethane gel material to a supporting substrate and the utilization of such structures in the medical field to adhere materials such as plasters, wound dressings and appliances to the human body, and in other fields to connect articles, such as the parts of a fractured or cracked object, to one another by means of an adhesive bond. The gel is formed by immobilizing a high molecular weight polymeric polyol in the matrix of a covalently crosslinked polyurethane which is prepared by reacting polyisocyanates having an isocyanate functionality of at least 2 with higher molecular weight polyhydroxyl compounds having a hydroxyl functionality of at least 3. These reactants are selected in accordance with the following formula which relates the isocyanate number, K, (isocyanate to hydroxyl equivalents ratio times 100) to the average functionalities of the polyisocyanates (F.sub.Type: GrantFiled: November 8, 1984Date of Patent: April 28, 1987Assignee: Bayer AktiengesellschaftInventors: Miklos von Bittera, Dietmar Schapel, Ulrich von Gizycki, Roland Rupp
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Patent number: 4622360Abstract: Removable water-borne urethane resin coating composition comprising polyurethane resin containing carboxyl groups and/or carboxylate groups and polyvalent metal complex as a cross-linking agent and method for removing the coating formed by using the removable water-borne urethane resin coating composition which comprises treating said coating with a ligand containing alkaline solution and removing the coating.The coating formed by using the composition is superior in water resistance, recoatability, detergent resistance, black heel mark resistance, abrasion resistance and service life.Type: GrantFiled: November 6, 1985Date of Patent: November 11, 1986Assignees: Yuho Chemicals Inc., Mitsui Toatsu Chemical Inc.Inventors: Tadashi Gomi, Kenji Sakata, Ichiro Aoyama, Nobuo Sono
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Patent number: 4619966Abstract: The present invention is directed to a process for the production of water- and solvent-resistant coated substrates by coating heat-resistant substrates with a solution or dispersion of an anionic group-containing polyisocyanate addition product in an aqueous solvent or dispersant and subsequently thermally treating the coating at a temperature of about 60.degree. to 200.degree. C., with evaporation or vaporization of the solvent or dispersant and simultaneous crosslinking of the polyisocyanate addition product which has been applied to the substrate, characterized in that incorporated anionic structural units corresponding to the formula ##STR1## are used in a quantity of about 5 to 1000 milliequivalents per 100 g of solids and the solids are based on reaction products of organic polyisocyanates with salts of cyanamide and bases selected from ammonia, primary and secondary amines having a minimum pKb value of 3.1, tertiary amines and mixtures thereof.Type: GrantFiled: November 7, 1985Date of Patent: October 28, 1986Assignee: Bayer AktiengesellschaftInventors: Walter Schafer, Manfred Hajek, Hanns P. Muller, Rolf Dhein, Rolf Kuchenmeister, Armin Sickert
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Patent number: 4617341Abstract: A sizing agent for the paper industry comprising a cationic oligourethane latex; said urethane having the formula: ##STR1## in which R.sub.2 is an alkylene radical containing a C.sub.2 -C.sub.6 radical or a polyoxyalkylenic radical of a degree of polycondensation of 1 to 4,R.sub.3 is an alkyl radical containing at least 7 carbon atoms, andR.sub.4 and X represent the remainder of the quaternizing agent R.sub.4 Xwith(a) R.sub.1 representing ##STR2## R.sub.5 being an aliphatic radical containing C.sub.4 as a maximum and n varying from 1 to 3; or(b) R.sub.1 representing ##STR3## R.sub.5 being ##STR4## in which R.sub.2, R.sub.3, R.sub.4 and X having the preceding definitions and n varying from 2 to 6; and the method of making the oligourethane latex.Type: GrantFiled: May 20, 1985Date of Patent: October 14, 1986Assignee: AtochemInventors: Antoine Laine, Claude Senez
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Patent number: 4598121Abstract: A method for preparing an aqueous polyurethane dispersion, comprising (a) preparing a prepolymer with free NCO groups by reacting an aliphatic or cycloaliphatic polyisocyanate with a polyol, and an anionic compound; (b) dispersing said prepolymer in water; (c) reacting said water-dispersed prepolymer with a diamino hydrazide of the formula: ##STR1## wherein R is an alkylene group of 2 to 15 carbon atoms or a cycloalkylene or arylene group of 6 to 15 carbon atoms as a chain lengthening agent; (d) reacting the prepolymer of step (c) in said dispersion with formaldehyde to effect crosslinking.Type: GrantFiled: June 5, 1985Date of Patent: July 1, 1986Assignee: Chemische Werke Huls AGInventors: Josef Disteldorf, Hans-Jurgen Haage, Horst Schnurbusch
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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: 4576989Abstract: The present invention is directed to aqueous solutions or dispersions which may contain blocked polyisocyanates of cationic oligourethanes which are crosslinkable at elevated temperature and contain(a) about 0.1 to 3% by weight of ternary or quaternary ammonium ions introduced through Michael adducts of secondary amines having at least one hydroxyl group and specific acrylic acid derivatives,(b) up to about 2.8% by weight of tert. amino nitrogen atoms incorporated through Michael adducts of secondary amines having at least one hydroxyl group and specific acrylic acid derivatives and(c) about 0 to 15% by weight of blocked isocyanate groups, provided that the ternary ammonium groups of (a), the tert. nitrogen atoms of (b) and the blocked isocyanate groups are present in an equivalent ratio of (a+b):blocked isocyanate groups of about 1:1 to 1:1.5.Type: GrantFiled: February 14, 1985Date of Patent: March 18, 1986Assignee: Bayer AktiengesellschaftInventors: Klaus Noll, Terry Potter, Josef Pedain, Jurgen Schwindt
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Patent number: 4554300Abstract: A method for preparing a polyurethane suitable for lining fuel tanks, said polyurethane having good, fuel resistance and improved hydrolysis resistance by using a ketimine of an aliphatic diamine as a curing agent in a three-component system composed of a prepolymer solution, a cement solution and a curing agent solution.Type: GrantFiled: April 12, 1985Date of Patent: November 19, 1985Assignee: Goodyear Aerospace CorporationInventors: Paul E. Liggett, Daniel A. Chung
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Patent number: 4554299Abstract: A method for preparing a polyurethane which has good long term flexibility, solvent resistance and resistance to hydrolysis, said method comprising mixing three components just prior to curing said components comprising a prepolymer solution, a cement solution and a crosslinking solution, said crosslinking solution comprising a solvent, an aromatic diamine and the ketimine of an aliphatic diamine.Type: GrantFiled: April 12, 1985Date of Patent: November 19, 1985Assignee: Goodyear Aerospace CorporationInventor: Paul E. Liggett
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Patent number: 4543366Abstract: Sprayable urethane resin compositions and a process for preparing the sprayable resin compositions particularly with reinforcing materials such as chopped fiberglass, which process comprises reacting generally equal volumes of A and B side mixtures in a sprayable reaction to form a fast reacting, fast curing urethane resin, the A side mixture comprising an MDI or an MDI prepolymer prepared by reacting an MDI with a triol and a B side mixture comprising an auto catalytic, aromatic amine polyol having a hydroxyl number ranging from about 300 to 600, a viscosity reducing amount of a tetraethylene glycol and a catalyst to affect the rapid reaction and cure of the A and B side mixtures on spraying, the process may optionally include the incorporation of reinforcing materials, such as glass fibers and optionally may include the use of blowing agents to provide a lower density reinforced cured product.Type: GrantFiled: October 15, 1984Date of Patent: September 24, 1985Assignee: Thermocell Development, Ltd.Inventor: Stuart B. Smith
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Patent number: 4522969Abstract: A novel, heat curable, liquid polymer composition is disclosed which comprises a modified polyurethane oligomer containing terminal ethylenic unsaturation, a free radical generating catalyst, and at least one additional component selected from a reinforcing agent and a filler. The cured composition demonstrates desirable impact properties and is particularly useful in automotive body constructions.Type: GrantFiled: March 20, 1984Date of Patent: June 11, 1985Assignee: Olin CorporationInventors: James M. O'Connor, Donald L. Lickei, Michael L. Rosin
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Patent number: 4521490Abstract: A solventless, fluid epoxy resin composition is storage-stable against separation of phases for at least one year, and when cured provides adhesive bonds of improved peel strength at room and low temperatures without loss of lap shear strength at room and elevated temperatures. The composition comprises an epoxide group-containing compound having in situ polymerized, elastomeric particles colloidally dispersed therein, and as curing agent a poly(oxyhydrocarbolene)diamine compound and optionally, and preferably, a cure accelerator.Type: GrantFiled: August 11, 1983Date of Patent: June 4, 1985Assignee: Minnesota Mining and Manufacturing Co.Inventors: Alphonsus V. Pocius, William J. Schultz
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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: 4513112Abstract: The use of isocyanate-functional prepolymers containing from recurring poly(ethylene oxide) units and colloidal silica in two-pack polyurethane compositions not only increases the flexibility of high build coatings prepared from such compositions but is also effective in controlling the mixed viscosity.Type: GrantFiled: March 7, 1984Date of Patent: April 23, 1985Assignee: Lord CorporationInventors: Bruce H. Ernst, Dennis D. Howard, Thomas E. Gismondi
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Patent number: 4507410Abstract: A solid catalyst composition comprising a silica or silica-treated compound and a tin catalyst compound bonded to the surface of the silica compound which is not deactivated in the presence of silica or silica-treated compounds. A process for preparing the solid catalyst by contacting a silica compound containing reactive hydroxyl groups with a tin catalyst compound at a temperature range from about 130.degree. to 165.degree. C. under dynamic conditions whereby the tin catalyst compound bonds to the silica compound. Generally, after the reaction, at least a portion of the hydroxyl groups present on the silica compound are absent and, more preferably, substantially all the isolated hydroxyl groups are absent. A urethane composition containing the solid catalyst is also provided wherein the solid catalyst is not deactivated by the addition of silica or silica-treated compounds.Type: GrantFiled: February 6, 1984Date of Patent: March 26, 1985Assignee: The Dow Chemical CompanyInventors: Edward R. Falardeau, Kurt C. Frisch, Jr., Michele R. Lock
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Patent number: 4458041Abstract: A heat-resistant composition containing an organic or elemento-organic binder and a filler. As a binder the composition contains at least one compound of the formula: ##STR1## wherein R is an organic radical with a number of carbon atoms of from 2 to 1,000; a radical with a number of carbon atoms of from 2 to 1,000 containing 1 to 1,000 atoms of silicon and/or1 to 1,000 atoms of fluorine, and/or1 to 1,000 atoms of chlorine, and/or1 to 1,000 atoms of bromine, and/or1 to 1,000 atoms of nitrogen, and/or1 to 1,000 atoms of sulphur, and/or1 to 1,000 atoms of phosphorus, and/or1 to 1,000 atoms of boron, and/or1 to 1,000 atoms of oxygen,X and Y are each --NH.sub.2, --OH, --SH, --NCO, --NSO, --NCS, said X and Y may be the same or different; Z is --C.tbd.N, --C.tbd.CH and is located in the same or different positions selected from alpha-, beta-, ortho- and peri- positions relative to X and Y; n.gtoreq.1, m.gtoreq.1, p.gtoreq.Type: GrantFiled: October 17, 1980Date of Patent: July 3, 1984Inventors: Alexei Y. Chernikhov, Mikhail N. Yakovlev, Nikolai S. Rogov, Aleftina P. Petrova, Eduard B. Martirosov, Valentin E. Gul
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Patent number: 4456707Abstract: Polyurethane moldings having an inhomogeneously colored surface with color contrasts in fiber-like distribution are made by incorporating colored fibers of a specified type in a polyurethane forming reactionmixture. The colored fibers must have a staple length of from 0.1 to 6 mm, a denier of from 0.1 to 25 dtex, and a coloring agent that does not migrate or dissolve in the polyurethane-forming materials. These fibers are generally used in a quantity such that they represent from 0.1 to 10 wt. % of the polyurethane-forming reaction mixture. Shoe soles, shoe heels, multiple layer soles and padded components are examples of moldings which may be produced in accordance with the present invention.Type: GrantFiled: April 11, 1983Date of Patent: June 26, 1984Assignee: Bayer AktiengesellschaftInventors: Lothar Hille, Heimo Ludke, Nikolaus Hansjosten
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Patent number: 4439576Abstract: A novel, heat curable, liquid polymer composition is disclosed which comprises a modified polyurethane oligomer containing terminal ethylenic unsaturation, a free radical generating catalyst, and at least one additional component selected from a reinforcing agent and a filler. The cured composition demonstrates desirable impact properties and is particularly useful in automotive body constructions.Type: GrantFiled: September 29, 1981Date of Patent: March 27, 1984Assignee: Olin CorporationInventors: James M. O'Connor, Donald L. Lickei, Michael L. Rosin
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Patent number: 4439577Abstract: A novel, heat curable, liquid polymer composition is disclosed which comprises a modified polyurethane oligomer containing terminal ethylenic unsaturation and a free radical generating catalyst. In a preferred embodiment, the polymer composition further includes at least one additional component selected from a reinforcing agent and a filler.Type: GrantFiled: April 1, 1982Date of Patent: March 27, 1984Assignee: Olin CorporationInventors: James M. O'Connor, Donald L. Lickei, Michael L. Rosin
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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: 4409340Abstract: The invention relates to a heat-curable coating composition, comprising:(A) a prepolymer with ketoxime-blocked NCO groups, which are linked to the prepolymer via cycloaliphatic and/or aliphatic groups,(B) a diamine cross linker,(C) organic solvents in an amount of 0 to 50 weight percent, based on the total weight of the coating composition,(D) optionally pigments, fillers, blowing agents and other known additives.The equivalence ratio of blocked NCO groups of component (A) to NH.sub.2 groups of component (B) lies between 1.3:1 and 0.75:1. The invention also relates to processes for its application and its use. The composition has a long shelf life and is advantageously used as an impact resistive coating on metal substrates such as automobile parts.Type: GrantFiled: March 1, 1982Date of Patent: October 11, 1983Assignee: Herberts GmbHInventors: Heinrich Stolzenbach, Rudolf Heitzmann, Siegfried Heinrich
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Patent number: 4397983Abstract: The invention is concerned with the preparation of polyurethane compositions in which the deleterious effect of gaseous by-products formed in the reaction is minimized. This is achieved by the use of coupling reagents which incorporate a steric hindrance function. The latter does not interfere with the normal coupling reactions between the coupling agent and polymer matrix and filler material but it does prevent such reaction between the coupling agent and filler material as would cause release of low molecular weight compounds occluded by the filler. Since the release of low molecular weight compounds is avoided, the formation or evolution of gases which give rise to unwanted cellularity of the cured composition is at least minimized.Type: GrantFiled: December 28, 1981Date of Patent: August 9, 1983Assignees: Aerofoam Industries Proprietary Limited, Polyeth Marketing Proprietary LimitedInventors: Edward T. Hill, Bernard L. Kaplan, Paul V. Farkas
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Patent number: 4383070Abstract: The present invention is directed to an organic polyurethane composition having a solids content of about 10 to 100 weight percent which comprises(1) isocyanate-terminated prepolymers which are prepared by reacting reaction products of the phosgenation of aniline-formaldehyde condensates containing specific ratios of isomers and homologues with polyether polyols containing at least two hydroxyl groups and at least one tertiary nitrogen atom and, optionally, an additional polyol which does not contain a tertiary nitrogen atom and optionally,(2) a monoisocyanate comprising a member selected from para-toluenesulfonyl isocyanate and the reaction product of 2,4- or 2,6-toluene diisocyanate or mixtures thereof with specific monoalcohols.The present invention is also directed to the coatings produced from the polyurethane compositions, optionally containing pigments.Type: GrantFiled: May 27, 1982Date of Patent: May 10, 1983Assignee: Mobay Chemical CorporationInventors: Peter H. Markusch, Terry A. Potter, Kenneth P. Yonek, James W. Rosthauser
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Patent number: 4370445Abstract: The invention concerns a material having good resistance to mechanical stresses and heat and in particular having substantial resistance to the penetration of a directed flame such as the pointed flame of a blowpipe.The material comprises a substance which can be polymerized such as a polyurethane, sulfur, and possibly halogenated compounds, phosphorus-bearing compounds, phosphohalogenated compounds, trivalent antimony oxide, solid or liquid fillers and pigments.The material may be used for the production of strong walls, in particular by filling internal cavities of armoured doors, walls of strong rooms or safes.Type: GrantFiled: November 13, 1980Date of Patent: January 25, 1983Assignee: Chloe-ChimieInventors: Norbert Depetris, Claude Bovis
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Patent number: 4337184Abstract: Rheology modifiers useful in water-based and organic solvent-based compositions are derived from the reaction of polyalkylene oxide, polyfunctional material, diisocyanate and little or no water. The modifiers are characterized by having a branched structure and containing substantially no terminal hydrophobic groups.Type: GrantFiled: December 29, 1980Date of Patent: June 29, 1982Assignee: PPG Industries, Inc.Inventors: Karl F. Schimmel, Jerome A. Seiner, Rostyslaw Dowbenko, Roger M. Christenson
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Patent number: 4336180Abstract: The instant invention is directed to a substantially solvent-free molding material, comprising(A) from 92 to 30% by weight, of an active-hydrogen containing prepolymer containing: from 0.3 to 4% by weight, based on the prepolymer, of free primary and/or secondary amino groups, from 1.5 to 10% by weight, based on the prepolymer, of urethane groups, and from 1.5 to 10% by weight, based on the prepolymer, of urea groups;(B) from 24 to 1% by weight of a polyisocyanate having a melting point above 120.degree. C.; and(C) from 5 to 69% by weight of an organic or inorganic fibrous material with a fiber length of from 0.1 to 100 mm, the equivalent ratio between NCO groups, including masked NCO groups, and active H-atoms of components (A) and (B) is between 1:1 and 1:1.75. The instant invention is also directed to a process for the production of the substantially solvent-free molding material.Type: GrantFiled: March 23, 1981Date of Patent: June 22, 1982Assignee: Bayer AktiengesellschaftInventors: Klaus Recker, Gerhard Grogler
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Patent number: 4336298Abstract: An adhesive system that can be used for bonding together fiberglass reinforced polyester (FRP) panels is provided. The adhesive system is comprised of a "hardener component" containing a polyester or polyether triol, paraphenylene diamine or ortho-phenylene diamine, and desirably a tin compound catalyst, and a "base component" containing an aromatic diisocyanate. The two components are mixed together just prior to bonding and the mixture is spread on the FRP panel surfaces desired to be bonded together. The panels are assembled and held clamped together until the adhesive sets.Type: GrantFiled: June 12, 1981Date of Patent: June 22, 1982Assignee: The B. F. Goodrich CompanyInventor: David S. Schwarz
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Patent number: 4329277Abstract: Polyurethane formulations that are resistant to fouling by marine organisms when exposed to sea water are prepared by mixing tetrachloroisophthalonitrile with a polyurethane. Any of the known polyurethanes may be used and liquid castable compositions are particularly useful.Type: GrantFiled: October 3, 1980Date of Patent: May 11, 1982Assignee: The B. F. Goodrich CompanyInventor: Walter T. Murphy
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Patent number: 4324716Abstract: This invention relates to solutions of polyisocyanate polyaddition products with a solids content of from 5 to 70% by weight ofA. Reaction products of(a) polyisocyanates,(b) hydrazines and/or polyamines and/or dihydrazides and/or ammonia and/or urea and/or low molecular weight polyols,(c) optionally higher molecular weight polyols and(d) optionally formaldehyde inB. polyhydric alcohols having a molecular weight of between 62 and 450.Type: GrantFiled: November 24, 1980Date of Patent: April 13, 1982Assignee: Bayer AktiengesellschaftInventors: Artur Reischl, Gert Jabs