Reactant Contains At Least One Bridged- Or Fused-ring System Patents (Class 528/74)
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Patent number: 4395530Abstract: A process for the manufacture of a polyurethane prepolymer adhesive by a catalyst initiated reaction of polyol and isocyanate copolymers is performed under room temperature conditions, and in convenient quantities for application, storage, and transportation purposes. Compounding includes alternatives of catalyst and co-catalyst combinations, and additives, including a reaction inhibitor, plasticizer, delayed reaction catalyst and surfactant.Type: GrantFiled: November 27, 1981Date of Patent: July 26, 1983Assignee: Colamco, Inc.Inventor: James A. Hammond
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Patent number: 4385165Abstract: The present invention relates to oligomeric and/or polymeric radiation-reactive precursor stages of polyimides, polyisoindoloquinazoline diones, polyoxazine diones and polyquinazoline diones as well as to a method for the preparation of these radiation-reactive precursor stages. The invention provides addition products of olefinically unsaturated monoepoxides on carboxyl group-containing polyaddition products of aromatic and/or heterocyclic tetracarboxylic-acid dianhydrides and diamino compounds or diamino compounds with at least one ortho-position amido group, or on carboxyl group-containing polyaddition products of aromatic and/or heterocyclic dihdyroxy dicarboxylic acids or corresponding diaminodicarboxylic acids and diisocyanates. The radiation-reactive precursor stages according to the invention are suitable, for example, for the manufacture of highly heat-resistant relief structures.Type: GrantFiled: August 19, 1980Date of Patent: May 24, 1983Assignee: Siemens AktiengesellschaftInventors: Hellmut Ahne, Eberhard Kuhn, Roland Rubner
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Patent number: 4354965Abstract: Novel high molecular weight resins, useful for electrically insulating conductors, are prepared by polycondensing a mixture of anhydrides, and a diisocyanate and/or a diamine in an inert organic solvent, preferably in the presence of a catalytic amount of 2-methylimidazole.Type: GrantFiled: March 20, 1981Date of Patent: October 19, 1982Assignee: General Electric CompanyInventors: Yue-Guey L. Lee, Otto S. Zamek
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Patent number: 4348511Abstract: Novel crosslinked unsaturated polymers, which have better properties than conventional crosslinked unsaturated polymers are obtained by reacting a .beta.-aminocrotonic acid ester, .beta.-aminocrotononitrile or .beta.-aminocrotonamide with a diisocyanate or polyisocyanate and a polyol, for example at temperatures of between 50.degree. and 180.degree. C.Type: GrantFiled: April 30, 1981Date of Patent: September 7, 1982Assignee: Ciba-Geigy CorporationInventor: Theobald Haug
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Patent number: 4339566Abstract: A water-dispersible urethane acrylate binding agent which comprises a reaction product of: (A) 1 gram equivalent NCO of a di- or tri-isocyanate; (B) from 0 to 0.7 gram equivalent OH of a polyol, free of organically bound sulphur; (C) from 0.1 to 0.7 gram equivalent OH of a hydroxy-(C.sub.2 -C.sub.6 alkyl)-acrylate; and (D) from 0.01 to 0.5 gram equivalent NH of an amino sulphonic acid or an alkali metal or an alkaline earth metal salt thereof having from 1 to 4 amino groups per sulphonic acid group; the ratio of NCO group: NCO-reactive groups being from 1:1 to 1:1.2 which are prepared by reacting components (A), (B), (C), and (D) in a ratio of NCO groups:NCO-reactive groups of from 1:1 to 1:1.2 at a temperature of from 20.degree. to 100.degree. C.Type: GrantFiled: September 2, 1980Date of Patent: July 13, 1982Assignee: Bayer AktiengesellschaftInventors: Hans J. Rosenkranz, Hellmut Striegler, Otto Bendszus
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Activated isocyanate prepolymers and a process for the production of elastomeric polyurethane resins
Patent number: 4330656Abstract: This invention relates to isocyanate prepolymers activated with alkyl ureas and to a two-stage process for the production of polyurethane elastomers based on 1,5-naphthylene diisocyanate, using alkyl ureas as activators.Type: GrantFiled: October 4, 1979Date of Patent: May 18, 1982Assignee: Bayer AktiengesellschaftInventors: Gerhard Grogler, Wilhelm Kallert -
Patent number: 4298515Abstract: A process for the production of modified polyhydantions by reacting polyglycine acid derivatives with optionally masked polyisocyanates with the addition of cyclic anhydride compounds containing at least one further functional group capable of condensation in lactones as solvents.Type: GrantFiled: December 6, 1979Date of Patent: November 3, 1981Assignee: Bayer AktiengesellschaftInventors: Jurgen Lewalter, Ludwig Rottmaier, Rudolf Merten, Wilfried Zecher, Willi Dunwald, Bernhard Schulte
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Patent number: 4288562Abstract: The reaction of isocyanates with substances containing isocyanate groups or active hydrogen groups, such as hydroxyl groups, amino groups and the like, are initiated by sulfonium zwitterions such as the ar-cyclic sulfonium areneoxides. Accordingly, partially trimerized isocyanates, polyurethanes and other useful materials can be made.Type: GrantFiled: April 28, 1980Date of Patent: September 8, 1981Assignee: The Dow Chemical Co.Inventors: Jiri Kresta, Chen S. Shen
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Patent number: 4284729Abstract: A process is provided for coloring thermosetting resins, made by polyaddition reaction of a nucleophile with an electrophile, with a polymeric liquid reactive coloring agent suitable for incorporation in the resin with the formation of covalent bonds, said coloring agent having the formula:R-(polymeric constituent-X).sub.nwherein R is an organic dyestuff radical; the polymeric constituent is selected from polyalkylene oxides and copolymers of polyalkylene oxides in which the alkylene moiety of the polymeric constituent contains 2 or more carbon atoms and such polyeric constituent has a molecular weight of from about 44 to about 1500; and n is an integer of from 1 to about 6; and X is selected from --OH, --NH.sub.2 and --SH, said coloring agent being added in an amount sufficient to provide coloration of said thermosetting resin.Type: GrantFiled: March 31, 1980Date of Patent: August 18, 1981Assignee: Milliken Research CorporationInventors: John P. Cross, George H. Britton, Jr.
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Patent number: 4281106Abstract: High molecular weight processible polymers derived from 2,6- and 2,7-diacids, diols and diamines of 9,10-dihydro-9,10-ethanoanthracenes and various complementary comonomers are prepared. These are converted into rigid, thermally-stable anthraceno polyesters and polyamides by thermal removal of the 9,10-ethano bridge.Type: GrantFiled: July 12, 1979Date of Patent: July 28, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventors: Burton C. Anderson, August H. Frazer
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Patent number: 4280007Abstract: The instant invention is directed to a process for the production of a cellular polyurethane elastomer having a density of 0.45 to 0.8 g/cm.sup.3, comprising:(a) preparing a prepolymer having an isocyanate content of 10 to 25% by weight from aromatic polyisocyanates and a portion of one or more polyhydroxyl compounds having a molecular weight of from 400 to 6,000; and(b) reacting said prepolymer with the remainder of said polyhydroxyl compound and water;wherein the quantity of said water is 0.3 to 1% by weight and the equivalent ratio of isocyanate groups to isocyanate reactive compounds is in the range of 0.95:1 to 1.1:1, characterized in that from 0.1 to 0.8% by weight, based on the whole reaction mixture, of aromatic diprimary diamines having a molecular weight from 108 to 500 are also used in (a) or (b).Type: GrantFiled: May 8, 1980Date of Patent: July 21, 1981Assignee: Bayer AktiengesellschaftInventors: Ernst Meisert, Franz-Josef Bohne, Klaus Brecht, Werner Mormann, Wolfgang Krohn, Gerhard Henes
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Patent number: 4269750Abstract: A process for the production of compounds containing hydantoin groups by reacting .alpha.-amino-carboxylic acid derivatives and organic isocyanates in the presence of acid groups and either in absence of any solvent or in the presence of a non-phenolic solvent.Type: GrantFiled: December 5, 1979Date of Patent: May 26, 1981Assignee: Bayer AktiengesellschaftInventors: Jurgen Lewalter, Ludwig Rottmaier, Rudolf Merten, Wilfried Zecher, Willi Dunwald, Bernhard Schulte
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Patent number: 4245067Abstract: A thermosetting resin composition comprising (I) a polybutadiene derivative obtained by conducting reaction of (A) a compound having active hydrogen obtained by reacting dicyclopentadiene or hydroxylated dicyclopentadiene with maleic anhydride or acid to yield partially esterified dicyclopentadienecarboxylic acid, which is further reacted with monoglycidyl ether or ester, (B) a butadiene homopolymer or copolymer having one or more hydroxyl groups and number average molecular weight of 1000 to 5000, and (C) a diisocyanate in ratios in terms of functional group equivalent ratio of (A)/(B)/(C) being 0.6-1.0/1.0/1.2-2.0, and (II) a polymerizable monomer having at least one polymerizable double bond in the molecule can be handled easily and cured at normal temperatures to give cured articles having good properties without losing excellent properties of polybutadiene as elastomer.Type: GrantFiled: November 21, 1979Date of Patent: January 13, 1981Assignee: Hitachi Chemical Company, Ltd.Inventors: Iwao Maekawa, Akira Kageyama, Uchigasaki, Isao
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Patent number: 4226967Abstract: An electron acceptor polycondensation polymer of the formula (I) ##STR1## wherein R.sub.1 is a hydrogen atom or an alkyl group, an aryl group or an aralkyl group having not more than 15 carbon atoms; C.sub.m is a divalent connecting group; FLac is an electron acceptor group having a fluorene nucleus as its basic structure; X and Y are a carbonyl group or an acid amide group forming a urethane linkage with the oxygen atom of the diol; R.sub.2 is a bifunctional organic residue having not more than 20 carbon atoms, n is a number greater than 10 which represents the degree of polycondensation of the resultant polycondensation polymer.Type: GrantFiled: April 30, 1979Date of Patent: October 7, 1980Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Shigeo Tazuke, Hajime Nagahara
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Patent number: 4224418Abstract: The instant invention is directed to compounds having an average molecular weight of from 300 to 12,000, containing: at least one hydroxyl group and at least one urethano-aryl-sulfonic acid group and a method for their preparation. The process is characterized as a process for the preparation of compounds having a number average molecular weight of from 300 to 12,000 having at least one hydroxyl group and at least one urethano-aryl-sulfonic acid group, comprising: reacting at from 0.degree. to 190.degree. C.(A) compounds having a molecular weight of from 62 to 10,000 having at least two hydroxyl groups; with(B) aromatic isocyanato sulfonic acids, wherein the equivalent ratio of the total quantity of isocyanate groups (including any isocyanate groups present in dimerized form) to sulfonic acid groups is from 0.5:1 to 50:1 and the equivalent ratio of the sum of hydroxyl groups in (A) to NCO groups is from 1.5:1 to 30:1. The invention is also directed to the product by the process.Type: GrantFiled: June 15, 1979Date of Patent: September 23, 1980Assignee: Bayer AktiengesellschaftInventors: Dieter Dieterich, Gerhard Balle, Hans G. Schmelzer
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Patent number: 4224430Abstract: A resinous composition comprising(1) 40-90 parts by weight of one or more oligomers obtained by reacting a polyhydric alcohol or its derivative with a monobasic acid of the formula, ##STR1## wherein X is an .alpha.,.beta.-unsaturated hydrocarbon group having 2 or 3 carbon atoms, and(2) 10-60 parts by weight of one or more polymerizable monomers having at least one polymerizable double bond in the molecule, has high solid content and gives molded articles excellent in water resistance, chemical resistance and hardness rise in addition to excellent properties of conventional unsaturated polyester resins.Type: GrantFiled: April 28, 1977Date of Patent: September 23, 1980Assignee: Hitachi Chemical Company, Ltd.Inventors: Iwao Maekawa, Isao Uchigasaki, Shouzi Takamizawa, Akira Kageyama
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Patent number: 4220728Abstract: The reaction of isocyanates with substances containing isocyanate groups or active hydrogen groups, such as hydroxyl groups, amino groups and the like, are initiated by sulfonium zwitterions such as the ar-cyclic sulfonium areneoxides. Accordingly, partially trimerized isocyanates, polyurethanes and other useful materials can be made.Type: GrantFiled: March 27, 1978Date of Patent: September 2, 1980Assignee: The Dow Chemical CompanyInventors: Jiri Kresta, Chen S. Shen
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Patent number: 4196277Abstract: This invention relates to a novel aromatic dianhydride and more particularly to the use of said dianhydride for the preparation of thermally stable high-molecular weight polymers including, for example, polybenzimidazoles, polypyrrones, polyimides, and the like. This dianhydride is obtained by reacting a stoichiometric amount of a disodium salt of 2,2-bis(4-hydroxyphenyl) hexafluoropropane with 4-chloro-N-phenylphthalimide to obtain an intermediate, 2,2-bis[4-(3,4-phenylphthalimidephenoxy)phenyl] hexafluoropropane, which is oxidized to the corresponding bis[4-(3,4-dicarboxyphenoxy)phenyl]perfluoroisopropylidene dianhydride.Type: GrantFiled: June 12, 1978Date of Patent: April 1, 1980Assignee: TRW Inc.Inventors: Robert J. Jones, Michael K. O'Rell
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Patent number: 4195132Abstract: The present invention relates to novel, substantially insoluble and infusible plastics which are cross-linked by way of triazine rings and, optionally, by way of tri-substituted bis-oxymethylene urea groups or urethane groups.Type: GrantFiled: May 5, 1977Date of Patent: March 25, 1980Assignee: Bayer AktiengesellschaftInventors: Rudolf Sundermann, Gunther Rottloff, Ernst Grigat
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Patent number: 4191818Abstract: Polyurethane elastomers of improved heat stability are made by a process in which a polyisocyanate is reacted with a polyol of high molecular weight with an OH:NCO ratio of 1:0.66 to 1:0.85, and the resulting adduct is later reacted with an excess of symmetrical diisocyanate and a diol as chain extender.Type: GrantFiled: July 10, 1978Date of Patent: March 4, 1980Assignee: BASF Wyandotte CorporationInventors: Karl H. Illers, Herbert Stutz
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Patent number: 4180645Abstract: This invention is concerned with autoxidizable coating compositions which contain(a) a member selected from the group consisting of an organic polyisocyanate, a urethane oil, and a uralkyd;(b) at least one non-volatile reactive liquid monomer selected from the group consisting of dicyclopentenyl acrylate and dicyclopentenyl methacrylate; and(c) an effective amount of a polyvalent metal-containing complex or salt that catalyzes the curing of (a) and (b).Use of the non-volatile reactive liquid component enables the production of coating compositions having high application solids content and yet having suitable viscosity for efficient handling. The coatings obtained from the compositions of the present invention combine the typical desirable properties including durability, weather-resistance, etc.Type: GrantFiled: May 22, 1978Date of Patent: December 25, 1979Assignee: Rohm and Haas CompanyInventors: William D. Emmons, Kayson Nyi, Peter R. Sperry
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Polyurethane coating compositions containing unsaturated esters of glycol monodicyclopentenyl ethers
Patent number: 4178425Abstract: This invention is concerned with autoxidizable coating compositions which contain(1) a member of the group consisting of an organic polyisocyanate, an isocyanate-modified drying oil, and a uralkyd;(2) at least one non-volatile reactive liquid monomer selected from the group consisting of dicyclopentenyloxyalkyl acrylate and dicyclopentenyloxyalkyl methacrylate; and(3) an effective amount of a polyvalent metal-containing complex or salt that catalyzes the curing of (1) and (2).Use of the non-volatile reactive liquid component enables the production of coating compositions having high application solids content and yet having suitable viscosity for efficient handling. The reduced volatile component improves the environmental aspects of preparing and using the coating compositions while the combining of these materials in the film results in enhancement of the film properties without detriment to the qualities normally desired and attained with the polyurethane type of coating composition.Type: GrantFiled: May 22, 1978Date of Patent: December 11, 1979Assignee: Rohm and Haas CompanyInventors: William D. Emmons, Kayson Nyi -
Patent number: 4174434Abstract: The instant invention is directed to compounds having an average molecular weight of from 300 to 12,000, containing: at least one hydroxyl group and at least one urethano-aryl-sulfonic acid group and a method for their preparation. The process is characterized as a process for the preparation of compounds having a number average molecular weight of from 300 to 12,000 having at least one hydroxyl group and at least one urethano-aryl-sulfonic acid group, comprising: reacting at from 0.degree. to 190.degree. C.(A) compounds having a molecular weight of from 62 to 10,000 having at least two hydroxyl groups; with(B) aromatic isocyanato sulfonic acids, wherein the equivalent ratio of the total quantity of isocyanate groups (including any isocyanate groups present in dimerized form) to sulfonic acid groups is from 0.5:1 to 50:1 and the equivalent ratio of the sum of hydroxyl groups in (A) to NCO groups is from 1.5:1 to 30:1. The invention is also directed to the product by the process.Type: GrantFiled: July 31, 1978Date of Patent: November 13, 1979Assignee: Bayer AktiengesellschaftInventors: Dieter Dieterich, Gerhard Balle, Hans G. Schmelzer
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Patent number: 4170697Abstract: Silicon halides will react chemically with polyols to produce polyol silicate resinous products which will react chemically with polyisocyanates to produce polyisocyanate silicate solid or cellular solid products.Type: GrantFiled: June 23, 1978Date of Patent: October 9, 1979Inventor: David H. Blount
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Patent number: 4151153Abstract: Improved elastomers are made by cross-linking a polyurethane through double bonds derived from a diisocyanato bicyclo octene used together with a linear prepolymer to make the polyurethane.Type: GrantFiled: June 2, 1977Date of Patent: April 24, 1979Assignee: Imperial Chemical Industries LimitedInventors: Peter L. Ashcroft, John Crosby
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Patent number: 4151194Abstract: A mixture of 3,8- and 4,8-dicyanotricyclo[5.2.1.0]decane is prepared by the hydrocyanation of 8-cyanotricyclo[5.2.1.0]dec-3-ene in the presence of a catalyst system comprising a zero valent nickel complex, free of carbon monoxide, a promoting amount of a metal compound such as zinc chloride and a hydroxy-containing aryl compound such as p-cresol as a solvent.Type: GrantFiled: December 12, 1977Date of Patent: April 24, 1979Assignee: Gulf Research & Development CompanyInventors: Ching-Yong Wu, Harold E. Swift
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Patent number: 4145516Abstract: Condensation polymers such as polyamides, polyesters, polyurethanes, polyepoxides, polyamide esters, polyureas and polyamino-acids which are photodegradable on exposure to U.V. light, due to the presence in the copolymer backbone of units of structure ##STR1## in small amounts.Type: GrantFiled: May 11, 1977Date of Patent: March 20, 1979Assignee: The Governing Council of the University of TorontoInventors: James E. Guillet, Ervin Dan
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Patent number: 4112152Abstract: Method for manufacturing polyurethane films and surface coatings from tall oil pitch. Tall oil pitch with an acid number of about 30-60 and a hydroxyl number of about 60-90 is esterified by adding about 5-15 weight fractions of an aliphatic alcohol comprising at least three OH-groups and about 0.1-0.5 weight fractions preferably p-toluenesulphonic acid per 100 weight fractions tall oil pitch, and by heat treatment at a lowered pressure until the acid number of the mixture is about 5-35 and the hydroxyl number is about 200-350. Aliphatic triisocyanate preferably dissolved in an inert organic solvent is added to the tall oil pitch ester thus attained in an amount such that the amount of isocyanate groups is 10-35 weight fractions per 100 weight fractions tall oil pitch ester. To the mixture thus attained is added known dilution agents and additives; the mixture is spread on a base material in a known way and the film or surface coating is finally polymerized at room temperature or at higher temperatures.Type: GrantFiled: April 2, 1976Date of Patent: September 5, 1978Inventors: Matti Dolk, Vaino Era, Jarl Johan Lindberg
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Patent number: 4111863Abstract: A non-swellable three-dimensional polymer having a component which is a residue of an optically active compound, which residue is chemically removable from said polymer to leave behind in the physical structure of said polymer a void corresponding to the size and shape of said residue of optically active compound, and a particular steric arrangement of functional groups within the void of said polymer corresponding to the chemical structure of said residue of optically active compound, the original polymer having recurring units of the formulas ##STR1## wherein A, C and D are residues bonded to B of compounds which residues are polymerizable or polycondensable and B is a residue of an optically active compound; a process for preparing such polymer and the form of such polymer containing such void and free of the residue of optically active compounds.Type: GrantFiled: April 16, 1975Date of Patent: September 5, 1978Assignee: Dynamit Nobel AktiengesellschaftInventors: Gunter Wulff, Ali Sarhan
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Patent number: 4108843Abstract: Random copolymers of polyparabanic acids and polyamide-imides are described. The copolymers are highly useful engineering thermoplastics which, unlike the corresponding polyparabanic acid homopolymers, are readily moldable by compression molding and like techniques. The copolymers are readily prepared by the one-shot reaction of bis(alkoxyoxalyl)amides of aliphatic, araliphatic or aromatic diamines, with organic diisocyanates and trimellitic anhydride.Type: GrantFiled: July 5, 1977Date of Patent: August 22, 1978Assignee: The Upjohn CompanyInventors: Augustin T. Chen, Kemal B. Onder