Polyurethane Having Terminal Ethylenic Unsaturation Patents (Class 525/920)
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Patent number: 11708428Abstract: The present disclosure provides a photopolymerizable composition. The photopolymerizable composition includes a) 40-60 parts by weight of a monofunctional (meth)acrylate monomer, per 100 parts of the total photopolymerizable composition; b) a photoinitiator; and c) a polymerization reaction product of components. A cured homopolymer of the monofunctional (meth)acrylate monomer has a glass transition temperature of 125 degrees Celsius or greater. The polymerization reaction product of components includes i) a diisocyanate; ii) a hydroxy functional methacrylate; iii) a polycarbonate diol; and iv) a catalyst. The polymerization reaction product includes a polyurethane methacrylate polymer. Often, the polyurethane methacrylate polymer has a weight average molecular weight of 8,000 g/mol or greater. The present disclosure further provides an article and methods thereof.Type: GrantFiled: June 10, 2021Date of Patent: July 25, 2023Assignee: 3M Innovative Properties CompanyInventors: Thomas P. Klun, Zeba Parkar, John M. Riedesel, Richard J. Pokorny, Chad M. Amb, Benjamin R. Coonce, Robert S. Clough, Tianyu Wu, Saswata Chakraborty, Yongshang Lu, Benjamin C. MacMurray
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Patent number: 10941523Abstract: A paperboard carrier suitable for use with textiles may include one or more strips of paperboard secured together to form a hollow tubular body, the body having an outer surface, and a coating covering some or all of the outer surface. The coating comprises a coating agent such as a silicon resin dispersed in a solvent such as isopropyl alcohol and little or no water. The coating may be applied to the outer surface by using a plurality spray nozzles arranged axially or circumferentially about the carrier.Type: GrantFiled: May 21, 2019Date of Patent: March 9, 2021Assignee: Sonoco Development, Inc.Inventors: Ismael Antonio Hernandez Rosario, Aaron Edward Lintz, Kevin Manly Kelley
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Patent number: 9023933Abstract: An autoxidisable coating composition comprising i) 10 to 60 wt % of an autoxidisable material with: a) a number average molecular weight <4500 g/mol; b) optionally 1 to 20 carbohydrate units; c) a fatty acid content of ?60 wt %; d) a viscosity at 100% solids in the range of from 0.05 to 5 Pa·s at 20+/?5° C. at a shear rate of 5000 s?1; ii) 90 to 40 wt % of an autoxidisable urethanised resin with: e) a number average molecular weight ?4000 g/mol; f) a fatty acid content of ?50 wt %; g) an acid value in the range of from 0 to 20 mgKOH/g resin; h) an isocyanate content in the range of from 1 to 35 wt % by weight of autoxidisable urethanised resin; where i)+ii)=100 wt %, based on the total solids content of the autoxidisable coating composition.Type: GrantFiled: April 27, 2010Date of Patent: May 5, 2015Assignee: DSM IP Assets B.V.Inventors: Willem Grisnich, Fokeltje Akke Koldijk, Adrianus Jozephus Hendricus Lansbergen, Albertus Johannes Reuvers, Stefan Hendrikus Maria Willems
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Patent number: 8853318Abstract: The invention relates to radiation-curable aqueous composition comprising a high molecular weight ethylenically unsaturated polyurethane obtained from the reaction of a polyisocyanate, at least one hydrophilic compound which is capable to render the polyurethane prepolymer dispersible in aqueous medium, an ethylenically unsaturated compound containing at least two reactive groups capable to react with isocyanate groups and an active hydrogen containing chain extender and a low molecular weight ethylenically unsaturated polyurethane end-capped with an ethylenically unsaturated compound containing essentially one reactive group capable to react with isocyanate groups.Type: GrantFiled: May 29, 2009Date of Patent: October 7, 2014Assignee: Allnex Belgium S.A.Inventor: Michel Tielemans
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Patent number: 8742022Abstract: Presently described are coating compositions comprising a polymerizable resin composition and a non-ionic unpolymerizable surfactant. In some embodiments, the coating comprises greater than 10 wt-% of non-ionic unpolymerizable surfactant. In other embodiments, the coating composition comprises an an additive comprising a silicone group or a fluorinated group and a hydrophobic group. Also described are articles comprising the cured coating compositions. In one embodiment, an article is described comprising a cured coating wherein the cured coating exhibits a property of an initially visible simulated fingerprint reducing in visibility in 1-20 minutes. Also described is a method of determining the fingerprint visibility of a coating composition and a polyacylate composition useful as an additive. In another embodiment a coated surface is described comprising a polymeric organic material comprising a plurality of pores wherein a portion of the pores are interconnected and comprise a lipophilic liquid.Type: GrantFiled: November 30, 2011Date of Patent: June 3, 2014Assignee: 3M Innovative Properties CompanyInventors: Richard J. Pokorny, Thomas P. Klun, Christopher B. Walker, Jr., David B. Olson, Joan M. Noyola, Michelle L. Toy, Evan L. Schwartz
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Patent number: 8507585Abstract: A non-aqueous pigment ink comprising a pigment, a non-aqueous solvent, and non-aqueous resin dispersion microparticles having a pigment dispersion capability, wherein the non-aqueous resin dispersion microparticles are an acrylic polymer comprising an alkyl (meth)acrylate unit having an alkyl group of 12 or more carbon atoms and a (meth)acrylate unit having a urethane group. The acrylic polymer is a copolymer of a monomer mixture comprising an alkyl (meth)acrylate (A) having an alkyl group of 12 or more carbon atoms and a reactive (meth)acrylate (B) having a functional group capable of reacting with an amino group, wherein the urethane group is introduced by a reaction between the functional group capable of reacting with an amino group, an amino alcohol and a polyvalent isocyanate compound, and the mass ratio within the acrylic polymer between the copolymer portion and the introduced urethane group portions is within a range from 60:40 to 99:1.Type: GrantFiled: April 8, 2009Date of Patent: August 13, 2013Assignee: Riso Kagaku CorporationInventors: Tetsuo Hosoya, Hiroshi Hayashi, Yoshifumi Watanabe, Kazuyuki Ando, Marie Morinaga
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Patent number: 7687411Abstract: The speaker member includes: a base material; and a resin film layer laminated on the base material through an adhesive layer. The adhesive layer has a heat shrinkage ratio of 0.5 to 1.0%; the resin film layer has a heat shrinkage ratio of 0.8 to 1.3%; and the heat shrinkage ratio of the adhesive layer is smaller than the heat shrinkage ratio of the resin film layer. The method of manufacturing a speaker comprises the steps of: applying a predetermined resin composition on a release material; drying the resin composition, so as to form a resin film layer on the release material; applying a predetermined adhesive on the resin film layer, so as to form an adhesive layer; attaching together the resin film layer formed on the release material and a base material through the adhesive layer, so as to form a laminate; subjecting the laminate to aging; and molding the laminate subjected to aging by using a metal mold having a predetermined shape.Type: GrantFiled: February 16, 2006Date of Patent: March 30, 2010Assignee: Onkyo CorporationInventors: Takeshi Fujitani, Masahiro Yoshida
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Patent number: 7064154Abstract: Compositions for use in optical fiber coatings and optical fibers and optical fiber arrays using these coatings are disclosed, as are methods for making the same. The compositions comprise a combination of two different radiation curable urethane oligomers, and can further comprise one or more reactive monomers. One of the oligomers has at least three functional groups that can undergo radiation cure, and comprises a lactone modified polyol.Type: GrantFiled: January 9, 2004Date of Patent: June 20, 2006Assignee: PPG Industries Ohio, Inc.Inventors: Shengkui Hu, Alan B. Weissberg
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Patent number: 6884843Abstract: A method of preparing a cured laminate employing electron beam radiation is provided. The cured laminate is prepared from an uncured laminate including a prepolymer composition containing oligomer, tackifying resin, and optionally, monomer. Also provided are a prepolymer composition and an article including the cured laminate prepared by the method of this invention. The method is useful for preparing cured laminates such as flexible laminates for food packaging.Type: GrantFiled: April 30, 2002Date of Patent: April 26, 2005Assignee: Rohm and Haas CompanyInventors: Thomas Frederick Kauffman, David William Whitman
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Patent number: 6872760Abstract: Compositions for use in optical fiber coatings and optical fibers and optical fiber arrays using these coatings are disclosed, as are methods for making the same. The compositions comprise a combination of two different radiation curable urethane oligomers, and can further comprise one or more reactive monomers. One of the oligomers has at least three functional groups that can undergo radiation cure.Type: GrantFiled: February 6, 2003Date of Patent: March 29, 2005Assignee: PPG Industries Ohio, Inc.Inventors: Shengkui Hu, Alan B. Weissberg
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Patent number: 6734263Abstract: The present invention provides a polymeric material and a process for making the polymeric material. The polymeric material has adhesive and noise abatement properties over a broad temperature range. Further, the material is chip and corrosion resistant and provides metal panel reinforcement.Type: GrantFiled: April 19, 2002Date of Patent: May 11, 2004Assignee: Diversified Chemical Technologies, Inc.Inventors: Rajan Eadara, Roy P. Jacob, Yushin Ahn, Biju Philip, Jori Joseff
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Patent number: 6719872Abstract: A hot melt composition containing, as essential ingredients, a specific high-molecular weight styrene block copolymer, a specific polyphenylene ether resin and a viscosity adjuster. The hot melt composition permits an easy assembling and sealing between a plurality of members. More particularly, it is possible for the hot melt composition to be melted and applied to one member in advance of the assembling work, such that the one member with the hot melt composition already applied thereto can be carried into a work site or a work line and simply joined to another member at those places. Further advantageously, the members joined or assembled via the hot melt composition can be disassembled without difficulty, which enables recycling of the used members.Type: GrantFiled: June 22, 2001Date of Patent: April 13, 2004Assignee: Aica Kogyo Co., Ltd.Inventors: Atsushi Tomita, Yuji Iwatsuka
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Patent number: 6696593Abstract: A method of preparing UV-curable urethane compositions is disclosed. The method comprises two steps. First, isophorone diisocyanate (IPDI) reacts with a hydroxy-functional resin to form an NCO prepolymer. Second, the NCO prepolymer reacts with a hydroxy-functional ethylenic monomer to form the UV-curable urethane composition. The hydroxy-functional resin comprises at least about 2 wt % of recurring units of a propoxylated allylic alcohol. The method of the invention allows the preparation of UV-curable urethane compositions from acrylic polyols without gel.Type: GrantFiled: July 10, 2002Date of Patent: February 24, 2004Assignee: Arco Chemical Technology, L.P.Inventors: Wei Wang, Daniel B. Pourreau
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Patent number: 6635706Abstract: A precrosslinked, urethane-acrylic dispersion formed from an isocyanate terminated urethane prepolymer reacted with mono-functional active hydrogen containing vinyl monomer and vinyl monomers inert to isocyanate functionality. To this polyurethane prepolymer having 0 to 100 percent vinyl termination—vinyl monomer blend is added a polyisocyanate having an average isocyanate functionality of less than 4 such that 0.5 to 20 percent of the urethane solids of the blend are polyisocyanate. The mixture containing less than 3 percent NCO groups, on solids, is dispersed into water and any residual isocyanate groups chain extended with one or more active hydrogen containing compounds. Optionally, the polyisocyanate can be added directly into the dispersion once the polyurethane prepolymer and the vinyl monomer blend is dispersed. The vinyl monomers are then reacted by free radical polymerization.Type: GrantFiled: June 23, 1999Date of Patent: October 21, 2003Assignee: Reichhold, Inc.Inventors: Glenn Petschke, Shi Yang
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Patent number: 6610876Abstract: A yellow colorant comprising a chromophore having at least one poly(oxy-C2-C4-alkylene) chain attached to an aromatic methine backbone having at least one cyanoester moiety attached thereto is provided. The ester portion must include a C1-C8 (such as ethyl, butyl, hexyl, or ethyl-hexyl) pendant group and the poly(oxyalkylene) chain must be at most 10 monomers and at least 3 monomers, with ethylene oxide as the capping group. Such a specific group of coloring agents provides the best overall yellow colorations or effects (either alone or in blends with other coloring agents, particularly at low color loadings) as well as the best overall low extraction levels when present within clear polyester (such as polyethylene terephthalate, for example), when compared to all other known polymeric yellow colorants for the same end-use. Compositions and articles comprising such colorants are provided as well as methods for producing such inventive colorants.Type: GrantFiled: February 6, 2003Date of Patent: August 26, 2003Assignee: Milliken & Co.Inventor: Eric B. Stephens
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Patent number: 6521718Abstract: A pavement marking composition comprises (a) a polyfunctional ethylenically unsaturated polymer selected from the group consisting of polyfunctional ethylenically unsaturated polyurethanes, polyureas, polythiocarbamates, polythiocarbamateurethanes, polythiocarbamateureas, and polyurethaneureas comprising at least one chain extender-derived segment and at least one polycarbonate, polyether, or polyester segment; and (b) at least one ethylenically unsaturated monomer. The composition can be easily applied, cures in a reasonable amount of time at any of a wide range of commonly-encountered temperatures, and provides pavement markings that exhibit both improved cold impact resistance and improved wear resistance.Type: GrantFiled: June 13, 2001Date of Patent: February 18, 2003Assignee: 3M Innovative Properties CompanyInventors: Siegfried Rainer Goeb, Anja Christina Rohmann
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Publication number: 20030008967Abstract: The invention relates to urethane prepolymers, obtainable by reaction of:Type: ApplicationFiled: June 14, 2002Publication date: January 9, 2003Inventors: Reinhold Hecht, Gunther Lechner, Thomas Lehmann, Gunther Eckhardt, Bernd Gangnus
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Patent number: 6500513Abstract: The invention provides a two-part adhesive composition making it possible to mutually bond disk substrates within a relatively short time and to produce an optical disk, and an optical disk having a metal film, corrosion of which is restricted under a high-temperature high-humidity condition, and which is produced by using the two-part adhesive composition. A two-part adhesive composition of the invention comprises first and second parts each containing urethane acrylate having a polytetramethylene glycol skeleton and an acrylate having a hydroxyl group in its molecule, wherein the first part further contains a diacyl peroxide and the second part further contains a tertiary amine. Organic peroxide is preferably diacyl peroxide and a setting promoter is preferably a tertiary amine. Either one, or both, of the first and second parts may further contain a photo-polymerization initiator.Type: GrantFiled: November 29, 2000Date of Patent: December 31, 2002Assignee: 3M Innovative Properties CompanyInventors: Sana Fujii, Sumita B. Mitra, Katsuya Takamori, Kazuta Saito
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Patent number: 6399718Abstract: The present invention provides a polyurethane resin obtainable by (A) in a first reaction stage (A) reacting (a) one or more di- and/or polyisocyanates, (b) one or more compounds (b) which have at least one group which ensures dispersibility in water and more than one group which is reactive toward isocyanate groups, and (c) if desired, one or more compounds having at least 2 and not more than 3 OH groups to give an intermediate (A) having free isocyanate groups and having urethane groups, (B) in a second reaction stage (B) adding (d) one or more monoisocyanates to the intermediate (A) obtained in stage (A), and (C) subsequently reacting the resulting mixture (B) with one or more hydroxyl-containing polymers (D) to give the polyurethane resin (P), using less than 20% by weight, based on the weight of the polyurethane resin (solids content), of polyalkylene oxide diols and/or polyalkylene oxide polyols to prepare the polyurethane resin.Type: GrantFiled: February 21, 2000Date of Patent: June 4, 2002Assignee: BASF Coatings AGInventors: Heinz-Peter Rink, Horst Hintze-Brüning, Peter Weinert
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Patent number: 6355351Abstract: The present invention provides a cationically electrodepositable coating composition capable of forming a coating film which is excellent in both of coating film physical properties such as a chipping resistance and an impact resistance and a corrosion resistance. The composition comprises an amine-modified epoxy resin (A) and a blocked polyisocyanate (B), further comprising 5 to 50 parts by weight of a cationic urethane-modified polymer emulsion (C) per 100 parts by weight of the total of the amine-modified epoxy resin (A) and the blocked polyisocyanate (B) in terms of a solid matter.Type: GrantFiled: February 16, 2001Date of Patent: March 12, 2002Assignee: Kansai Paint Co., Ltd.Inventors: Hidenori Sawada, Shigeo Nishiguchi, Koji Kamikado
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Patent number: 6350823Abstract: A pavement marking composition comprises (a) a polyfunctional ethylenically unsaturated polymer selected from the group consisting of polyfunctional ethylenically unsaturated polyurethanes, polyureas, polythiocarbamates, polythiocarbamateurethanes, polythiocarbamateureas, and polyurethaneureas comprising at least one chain extender-derived segment and at least one polycarbonate, polyether, or polyester segment; and (b) at least one ethylenically unsaturated monomer. The composition can be easily applied, cures in a reasonable amount of time at any of a wide range of commonly-encountered temperatures, and provides pavement markings that exhibit both improved cold impact resistance and improved wear resistance.Type: GrantFiled: October 5, 1998Date of Patent: February 26, 2002Assignee: 3M Innovative Properties CompanyInventors: Siegfried Rainer Goeb, Anja Christina Rohmann
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Patent number: 6306947Abstract: An aqueous emulsion which comprises as a resin component a self-emulsifiable copolymer in which at least one ethylenically unsaturated monomer and at least one urethane prepolymer having at least one mercapto group and at least one hydrophilic, polar group are bonded by radical polymerization or in which at least one ethylenically unsaturated monomer, at least one organic polyisocyanate, at least one compound having at least one mercapto group and at least one active hydrogen-containing group and at least one compound having at least one hydrophilic, polar group and at least one active hydrogen-containing group are bonded by urethanization reaction and radical polymerization. The aqueous emulsion is better in storage stability than conventional ones.Type: GrantFiled: May 27, 1999Date of Patent: October 23, 2001Assignees: Nippon Polyurethane Industry Co., Ltd., Asia Industry Co., Ltd.Inventors: Takeshi Morishima, Shunsuke Murakami, Toshiaki Sasahara, Shin Konishi, Kazuya Sugimoto
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Patent number: 6284321Abstract: Binders for powder coatings are disclosed that contain, solid, unsaturated polyesterurethane (meth)acrylates having a melting temperature of from 35 to 180° C.Type: GrantFiled: November 3, 1999Date of Patent: September 4, 2001Assignee: Solutia Germany GmbH & Co. KGInventors: Gerhard Brindoepke, Dietmar Fink
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Patent number: 6258441Abstract: The present invention relates to a composition for soft coat films having a soft tactile impression, which is characterized by containing as essential components (a) an urethane acrylate having a molecular weight of 500-50,000 and (b) a tactile improver, and to a method for producing soft coat films using such a composition. The soft coat film obtained by the present invention has a soft surface tactile impression just like buckskin and excels in such surface properties as wear resistance, impact resistance and scuffing resistance.Type: GrantFiled: August 4, 1998Date of Patent: July 10, 2001Assignee: Dai Nippon Insatsu Kabushiki KaishaInventors: Kiyoshi Oguchi, Yozo Kosaka
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Patent number: 6239209Abstract: The polyurethane-acrylic hybrid interpenetrating polymer network is formed by blending a polyurethane prepolymer having acid or amine salt forming groups, air curable ethylenic unsaturation and terminal isocyanate groups or both terminal isocyanate groups and terminal vinyl groups, with one or more vinyl monomers, inert to isocyanate functionality, dispersing the prepolymer/vinyl monomer blend into water, chain extending the terminal isocyanate groups of the prepolymer with one or more active hydrogen containing compound, and reacting the vinyl monomers by free radical polymerization.Type: GrantFiled: February 23, 1999Date of Patent: May 29, 2001Assignee: Reichhold, Inc.Inventors: Shi Yang, Glenn Petschke
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Patent number: 6177507Abstract: The disclosed polymerizable compositions comprise a monomer or a mixture of hydrophilic monomers, as well as a crosslinking agent comprised of an oligomer or a mixture of urethane oligomers having a mole weight of between 500 and 5,000 and two to six (meth)acrylate functions. The invention can be used in the manufacture of contact lenses.Type: GrantFiled: October 13, 1998Date of Patent: January 23, 2001Assignees: Essilor International Compagnie Generale d'Optique, Sunsoft CorporationInventor: Isabelle Calderada
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Patent number: 5770739Abstract: An apparatus and process for hydrogen peroxide vapor sterilization of medical instruments and similar devices make use of hydrogen peroxide vapor released from a substantially non-aqueous organic hydrogen peroxide complex, such as a urea-peroxide complex. Optionally, a plasma can be used in conjunction with the vapor. A method for preparing substantially non-aqueous hydrogen peroxide complexes is also provided. These complexes are useful as a source of peroxide vapor in hydrogen peroxide vapor sterilizers and as a component of self-sterilizing packaging materials.Type: GrantFiled: August 26, 1996Date of Patent: June 23, 1998Assignee: Johnson & Johnson Medical, Inc.Inventors: Szu-Min Lin, James Archie Swanzy, Paul Taylor Jacobs
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Patent number: 5688590Abstract: The invention is directed to a process for preparing SRIM molded article. The process broadly requires the use of a fiber reinforcement mat which is placed inside the mold cavity, and then a polyurethane reaction system is injected into the mold. The system comprising a polyisocyanate and a blend of active hydrogen containing compounds requires aldimines as part of the blend of active hydrogen containing compounds.Type: GrantFiled: August 21, 1995Date of Patent: November 18, 1997Assignee: Bayer CorporationInventors: E. Haakan Jonsson, Kristen L. Parks, Harald Pielartzik, Philip E. Yeske, Douglas A. Wicks
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Patent number: 5554712Abstract: A photopolymer useful in preparing water-developable, solid printing plates is prepared by preparing a urethane prepolymer by reacting polyoxyalkylene diols or polyester diols, or a mixture thereof, with an excess of diisocyanate, followed by chain extending the resulting prepolymer mixture with an alkyldialkanolamine, then reacting the chain-extended product with a hydroxyalkyl(meth)acrylate. The resulting photopolymer is suitably formulated with additional photoactive (meth)acrylate monomers or oligomers and photoinitiator for casting or extrusion on a substrate to form a flexographic printing plate. Following UV exposure of the plate through a negative, unexposed areas can be removed by washing with a slightly acidic aqueous medium, to give a plate with a desirable relief image. The use of the aqueous washout solution as opposed to organic solvents minimizes pollution problems.Type: GrantFiled: May 19, 1994Date of Patent: September 10, 1996Assignee: W.R. Grace & Co.-Conn.Inventors: Truc-Chi T. Huynh-Tran, Ronald J. Kumpfmiller, Cynthia L. Ebner
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Patent number: 5531546Abstract: For fastening anchoring means, such as anchor rods, in solid accommodating materials without expansion pressure, mortar compositions are used, which consist of a hardener and a resin. To improve the strength properties, vinyl ester urethane resin is employed, which optionally can be accelerated.Type: GrantFiled: April 19, 1995Date of Patent: July 2, 1996Assignee: Hilti AktiengesellschaftInventors: Alwin Herdlicka, Ludwig Gebauer, Gabriele Grundmann
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Patent number: 5426157Abstract: This invention relates to improved polyepoxide resins having enhanced physical and elastic properties. The polyepoxide resins comprise a polyepoxide resin based on a polyglycidyl ether of a phenolic-type compound and an acrylate-terminated urethane prepolymer. The improvement in the polyepoxide resin formulation comprises incorporating a polymethylated amine curative having two secondary amine hydrogens represented by the formula: ##STR1## wherein R is alkylene or polyalkylene polyamine having from 2 to 20 carbon atoms. The presence of the aliphatic amine reactive component along with the acrylate-terminated urethane prepolymer results in an epoxy resin having enhanced properties.Type: GrantFiled: March 16, 1994Date of Patent: June 20, 1995Assignee: Air Products and Chemicals, Inc.Inventors: William E. Starner, John A. Marsella, Richard S. Myers
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Patent number: 5385966Abstract: Adhesives and sealants, based on polyurethane reactants, are provided. The one-component frozen premix material of the invention comprises: (a) up to about 60 vol % of at least one filler; (b) about 0.5 to 5 wt % of a thixotrope comprising hydrophobic fumed silica; and (c) the balance a urethane matrix. The urethane matrix comprises at least one polyol that includes at least one carbon-carbon double bond in its backbone and has less than 20 wt % of ether and ester moieties, at least one aliphatic polyisocyanate in stoichiometric amount relative to the polyol, and about 0.01 to 0.1 wt % of an organo-metallic catalyst. The urethanes of the invention can be stored as one-component, frozen, premix materials for a minimum of three months, and, when thawed, can be applied with a spatula or trowel to form non-sag fillets. The cured elastomers are free of voids, tears, or bubbles.Type: GrantFiled: January 28, 1994Date of Patent: January 31, 1995Assignee: Hughes Aircraft CompanyInventors: Ralph D. Hermansen, Steven E. Lau
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Patent number: 5359014Abstract: Disclosed are novel nitrogen containing heterocyclic compounds and novel vinyl terminated polyurethane/polyamide polymers together with the use of both of these compounds in a novel adhesive and coating composition. The nitrogen containing heterocyclic compounds of the invention contain two vinyl-terminated substituents and at least one carbamylmethyl substituent and have a nucleus selected from melamine, oligomers of melamine, benzoguanamine, and oligomers of benzoguanamine, glycoluril and oligomers of glycoluril. The vinyl terminated polyurethane compounds of the invention have a molecular weight of from about 3000 to about 80000, and contain at least two vinyl end groups.Type: GrantFiled: September 11, 1992Date of Patent: October 25, 1994Assignee: Cytec Technology Corp.Inventors: Peter S. Forgione, Yuhshi Luh, Balwant Singh, William A. Henderson, Jr.
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Patent number: 5336716Abstract: The invention relates to paints comprising(i) a resin (A) which contains hydroxyl groups and .alpha.,.beta.-unsaturated carbonyl groups or a mixture of such resins, and/or(ii) a mixture consisting ofa) a hydroxyl-containing resin (B) or a mixture of such resins andb) a crosslinking agent (C) which contains .alpha.,.beta.-unsaturated carbonyl groups or a mixture of such crosslinking agents and(iii) a catalyst (D) which catalyzes the reaction of hydroxyl groups with .alpha.,.beta.-unsaturated carbonyl groups or a mixture of such catalysts.The invention is characterized in that the catalyst (D) is a Bronsted acid.Type: GrantFiled: February 25, 1993Date of Patent: August 9, 1994Assignee: BASF Lacke + Farben AktiengesellschaftInventors: Elisabeth Kappes, Ulrich Poth
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Patent number: 5336563Abstract: Photocurable liquid coating compositions adapted to provide primary coatings for optical glass fibers are disclosed. These compositions comprise an acrylate-terminated polyurethane, an acrylate of an unsubstituted or C.sub.1 -C.sub.10 alkyl substituted phenol that is alkoxylated with a C.sub.2 -C.sub.4 alkylene oxide and at least one alkylacrylate having a T.sub.g below about -45.degree. C. Films produced from these ultraviolet light curable compositions are flexible and possess good water resistance and good wet adhesion.Type: GrantFiled: January 26, 1993Date of Patent: August 9, 1994Assignee: DSM Desotech, Inc.Inventors: Clive J. Coady, Erwin S. Poklacki, John M. Zimmerman, Timothy E. Bishop, John L. Derer
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Patent number: 5331041Abstract: A polymerizable composition contains unsaturated urethane shown by Formula (1) given below, vinyl monomer which is copolymerizable with this unsaturated urethane, and an inorganic powder filler at weight ratio of (unsaturated urethane)/(vinyl monomer)=10/90-90/10, the inorganic powder filler being 30-300 weight parts with respect to 100 weight parts of the sum of the unsaturated urethane and vinyl monomer: ##STR1## where R.sup.1 is hydrogen atom or methyl group; X is a residual group obtained by removing isocyanate groups from diisocyanate; Y is a residual group obtained by removing hydroxyl groups from non-radical polymerizable di-ol or tri-ol of a specified kind; Z is an organic group in the form of (R.sup.2 O).sub.m or R.sup.3 O, R.sup.2 being an alkylene group with 2-4 carbon atoms, R.sup.3 being an alkylene group with 2-12 carbon atoms, and m being an integer 2-10; and n is 2 or 3.Type: GrantFiled: April 22, 1993Date of Patent: July 19, 1994Assignee: Takemoto Yushi Kabushiki KaishaInventors: Yuji Takayama, Hirokazu Matsueda, Masato Sugiura, Tatsuhiko Ozaki, Hirotaka Wada, Toshiharu Suzuki
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Patent number: 5306764Abstract: Amine-containing, water dispersible polyurethanes made by the following process: (1) in a reactive diluent such as acrylate, methacrylate, acrylonitrile monomer, low viscosity epoxy compound or epoxy resin, or mixture thereof, using an excess amount of polyisocyanate to react with polyol to form NCO-terminated urethane prepolymer; (2) adding hydroxy alkyl acrylate or hydroxy alkyl methacrylate monomer to react with the prepolymer in step (1) to convert its -NCO end group into alkyl acrylate or alkyl methacrylate end group; and (3) using an excess amount of polyamine to react with the alkyl (meth)acrylate-terminated prepolymer in step (2) and the reactive diluent and the residual hydroxy-containing monomer in step (2), if any. The polyurethane can be mixed with a crosslinking agent having multi-epoxy or blocked polyisocyanate functionalities, to prepare a stable aqueous coating composition.Type: GrantFiled: September 3, 1992Date of Patent: April 26, 1994Assignee: China Technical Consultants Inc.Inventor: Der-Shyang Chen
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Patent number: 5286832Abstract: The present invention relates to a process for the manufacture of a cast, injection moulded or compression moulded articles by curing a resin composition in a desired shape using catalysts, and allowing the shaped piece to post-cure under such conditions that an HDT of at least 150.degree. C. is obtained. The resin composition comprises a polyisocyanate, an ethylenically unsaturated monomer and a vinyl ester compound, and the vinyl ester compound contains on average about two to about 6 (meth)acrylate groups and on average about two to about 6 hydroxyl groups, and has a molecular weight higher than 300. The invention also relates to a resin composition suitable for use in the process.Type: GrantFiled: March 20, 1991Date of Patent: February 15, 1994Assignee: Stamicarbon B.V.Inventors: Ronald L. Verleg, Adrianus J. De Koning
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Patent number: 5284883Abstract: A radiation crosslinked molding of a urethane resin composition comprising a thermoplastic urethane resing having incorporated therein a polyfunctional monomer selected from the group consisting of trimethylolpropane triacrylate, trimethylolpropane trimethacrylate and triacrylformal., is disclosed. The molding according to the present invention has excellent resistance to hot water and heat.Type: GrantFiled: December 8, 1992Date of Patent: February 8, 1994Assignee: Sumitomo Electric Industries, Inc.Inventors: Keiji Ueno, Ikujiro Uda
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Patent number: 5281682Abstract: Improved radiation curable compositions are provided which comprises N-vinylformamide and an oligomer selected from the group consisting of epoxy-acrylate resins, polyester acrylate resins, polyurethane acrylate resins and mixtures thereof. A photoinitiator is also added to the composition. A process is also provided whereby the composition is applied to the surface of a substrate and subsequently exposed to a radiation source until an adherent dry polymerized film is formed on the substrate. These compositions are useful as pigmented and unpigmented coatings, printing inks, adhesives and the like.Type: GrantFiled: March 3, 1992Date of Patent: January 25, 1994Assignee: Air Products and Chemicals, Inc.Inventors: David A. Cornforth, Dawn Fowler, Walter L. Renz
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Patent number: 5232996Abstract: A two-part adhesive composition useful for bonding various materials including plastic or thermoplastic substrates. The first part of the adhesive contains an epoxy compound and an acrylate-terminated polyurethane while the second part of the adhesive contains an amine hardener. The presence of the acrylate-terminated polyurethane allows the adhesive composition to be applied to unprepared substrates to form a bond having high strength.Type: GrantFiled: May 7, 1992Date of Patent: August 3, 1993Assignee: Lord CorporationInventors: Dilip N. Shah, Terrance H. Dawdy
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Patent number: 5223565Abstract: Molded products with improved dimensional stability and surface property can be obtained by in-mold curing of a polymerizable composition containing unsaturated urethane of a specified structure, alkyl (meth)acrylate, and a thermoplastic macromolecular compound capable of dissolving in or swelling by impregnating alkyl (meth)acrylate. These components are contained at specified weight ratio. The mold is initially at temperature 30.degree..about.120.degree. C. and the curing is effected in the presence of a radical initiator.Type: GrantFiled: May 23, 1991Date of Patent: June 29, 1993Assignee: Takemoto Yushi Kabushiki KaishaInventors: Yuuji Takayama, Hirokazu Matsueda, Maseto Sugiura, Tatsuhiko Ozaki, Hirotaka Wada, Iwao Komiya
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Patent number: 5219896Abstract: Photocurable liquid coating compositions adapted to provide primary coatings for optical glass fibers are disclosed. These compositions comprise polycarbonate-based acrylate-terminated polyurethane, an acrylate of an unsubstituted or C.sub.1 -C.sub.10 alkyl substituted phenol that is alkoxylated with a C.sub.2 -C.sub.4 alkylene oxide and at least one alkylacrylate having a T.sub.g below about -45.degree. C. Films produced from these ultraviolet light curable compositions are flexible and possess good water resistance and good wet adhesion.Type: GrantFiled: March 27, 1992Date of Patent: June 15, 1993Assignee: Stamicarbon, B.V.Inventors: Clive J. Coady, Erwin S. Poklacki, John M. Zimmerman, Timothy E. Bishop, John L. Derer
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Patent number: 5200483Abstract: Describes organic resin compositions of from about 30 to 90 weight percent of a polyol(allyl carbonate), e.g., diethylene glycol bis(allyl carbonate), and from about 10 to 70, e.g., 10 to 30, weight percent of a mixture of aliphatic urethanes, the terminal portions of which contain allyl or acrylyl functional groups. Polymerizable compositions prepared from such compositions produce castings which have low yellowness (b*) values and which do not pre-release from the molds in which they are formed. Polymerizates prepared from such compositions may be used to prepare photochromic articles, e.g., lenses, by incorporating a photochromic substance, e.g., by thermal transfer, into the polymerizate.Type: GrantFiled: November 7, 1991Date of Patent: April 6, 1993Assignee: PPG Industries, Inc.Inventor: Christopher D. Selvig
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Patent number: 5177120Abstract: Disclosed is a new urethane polyacrylate having at least one terminal isocyanato acrylic pendent radical. Preferably the molecular chain within the acrylate caps has been extended with a polyhydroxy compound just before final end capping with isocyanato acrylic. The isocyanato acrylic is preferably isocyanato ethyl methacrylate and the urethane is diisocyanate capped polyether and the polyether radical is oxyalkylene. The method for producing the urethane polyacrylate involves end capping a polyol with diisocyanate yielding a reaction product with two reactive equivalents of isocyanate and then capping less than all of the isocyanate with a hydroxyacrylate, after which the remaining isocyanate is reacted with polyol to provide chain extension. The chain extending polyol is then capped with a isocyanato acrylic.Type: GrantFiled: November 13, 1987Date of Patent: January 5, 1993Assignee: Dentsply Research & Development Corp.Inventors: Pamela H. Hare, Paul D. Hammesfahr
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Patent number: 5169719Abstract: Water-dilutable polyurethane/acrylic copolymers which may be either completely nonionically stabilized or partically nonionically and partically anionically stabilized comprise the reaction product of an ethylenically terminated polyurethane macromonomer containing poly(oxyalklyene) segments and one or more ethylencially unsaturated monomers selected from acrylic acid, methacruylic acid, fumaric acid, styrene, vintyltoluene, and alkyl and hydroxyalkyl esters of acrylic, methacrylic, and furamic acids. The copolymers are useful as principal resins and as pigment grind resins in water-borne automotive base coat paint formulations.Type: GrantFiled: October 6, 1989Date of Patent: December 8, 1992Assignee: BASF CorporationInventor: Sergio E. Balatan
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Patent number: 5144056Abstract: The invention relates to fluorinated acrylic monomers of the formula: ##STR1## in which A and W denote divalent linkages, R is a hydrogen atom or a methyl radical, R.sub.F is a perfluoroalkyl radical and Q denotes an oxygen or sulphur atom or the group--NR'--, where R' denotes a hydrogen atom or an alkyl radical. Homo- or copolymers derived from these monomers are useful for the water or oil-repellent treatment of various substrates, particularly leather.Type: GrantFiled: March 14, 1989Date of Patent: September 1, 1992Assignee: AtochemInventors: Marie-Jose Lina, Andre Dessaint
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Patent number: 5126396Abstract: A polymerisable composition which comprises an unsaturated urethane, a C.sub.1 or C.sub.2 alkyl methacrylate and at least one other ethylenically unsaturated addition polymerisable substance copolymerisable therewith, such polymerisable compositions, where they contain an inorganic filler, overcome some of the problems associated with the polymerisable compositions described in European 0.064,809. Where the polymerisable substance comprises an unsaturated polyester, the shelf-life of the polymerisable composition can be extended by adding thereto a reagent which reacts with a portion of the free carboxyl group in the unsaturated polyester. The compositions may be used, for example, in the production of fibre-reinforced composites.Type: GrantFiled: November 20, 1990Date of Patent: June 30, 1992Assignee: Imperial Chemical Industries PLCInventors: Michael L. Orton, William I. Spurr
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Patent number: 5118779Abstract: A non-toxic hydrophilic polyurethane elastomer having less than about 0.5% by weight extractables and which is curable in the absence of heat is disclosed. The elastomers are prepared from suitable hydrophilic polyurethane oligomers in combination with suitable ultraviolet light absorbers which become chemically bound into the elastomer during the polymerization (curing) thereof and thus become essentially non-extractable therefrom.Type: GrantFiled: October 10, 1989Date of Patent: June 2, 1992Assignee: PolyMedica Industries, Inc.Inventor: Michael Szycher
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Patent number: 5110881Abstract: A photochromic article having improved pohotochromic equilibrium response is described. In particular, a phtochromic compound is incorporation into or applied to an article, e.g., matrix, of a synthetic organic resin prepared from a composition comprising from about 55 to about 90 weight percent of a polyol(allyl carbonate), e.g., diethylene glycol bis(allyl carbonate), from about 10 to about 40 weight percent of an aliphatic polyurethane having terminal ethylenic unsaturation, e.g., an aliphatic polyesterurethane diacrylate, and from about 0 to about 5 weight percent of a difunctional monomer selected from the group consisting of allyl methacrylate and allyl acrylate. Such photochromic articles have an improved photochromic equilibrium response at ambient temperatures compared to the response of a comparable photochromic article prepared from a polyol(allyl carbonate) homopolymer, e.g., homopolymers of diethylene glycol bis(allyl carbonate), at the same ambient temperatures.Type: GrantFiled: January 10, 1991Date of Patent: May 5, 1992Assignee: PPG Industries, Inc.Inventors: Douglas S. McBain, John C. Crano