With Ethylenic Reactant Patents (Class 522/96)
  • Patent number: 5514522
    Abstract: A photoreactive binder that may be used to enhance photospeed in either conventional plates or on-press developable lithographic printing plates. Briefly, a polymer of m-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate is derivatized for vinyl group reactivity by reacting the isocyanate groups thereof with hydroxyalkyl acrylate. The resulting photopolymeric binder provides significantly higher photospeed than the non-reactive binder currently utilized in the production of conventional printing plates. The resulting lithographic printing plate also shows better durability (as manifested by longer run-length) and is more easily developed by the microencapsulated developers utilized in the present invention. As to the preparation of the photoreactive binders, the application discloses a method of copolymerizing m-isopropenyl-.alpha.,.alpha.
    Type: Grant
    Filed: April 27, 1995
    Date of Patent: May 7, 1996
    Assignee: Polaroid Corporation
    Inventors: Maurice J. Fitzgerald, Frederick R. Kearney, Rong-Chang Liang, William C. Schwarzel
  • Patent number: 5514727
    Abstract: This invention relates to vinyl ether-based coatings for which properties such as color stability, thermal stability, mechanical stability, hydrolyric stability, and resistance to embrittlement may be maintained and properties hydrogen generation and blocking are minimized. The invention also relates to stabilizers which control these properties in the coatings.
    Type: Grant
    Filed: July 13, 1994
    Date of Patent: May 7, 1996
    Assignee: AlliedSignal Inc.
    Inventors: George D. Green, James R. Snyder, Raymond J. Swedo
  • Patent number: 5512608
    Abstract: A multi-part composition is provided which is suitable for use as an adhesive, a potting compound, a coating or a sealant. It consists of a polymerizable acrylate formulation and an activating formulation, the latter usually comprising an amine-aldehyde condensation product diluted with a liquid vinyl ether; liquid epoxides may also be included as diluents in the activating formulation.
    Type: Grant
    Filed: January 27, 1995
    Date of Patent: April 30, 1996
    Assignee: Dymax Corporation
    Inventors: Andrew G. Bachmann, Stephen E. Cantor
  • Patent number: 5498782
    Abstract: Distortion control additives are disclosed which comprise a polyisocyanate, a polyol or polyol blend having a hydroxyl functionality of 2 to 3 hydroxyl groups per molecule and an average molecular weight of at least about 500 grams per gram mole, a diol chain extender having from about 2 to 35 carbon atoms per molecule and an acrylate or methacrylate having an acrylate functionality of from 1 to 5 acrylate groups per molecule. Ultraviolet-curable liquid compositions comprising an unsaturated polymeric resin, a monomer and the distortion control additives of the present invention are also disclosed. The distortion control additives can provide substantial reductions in distortion, e.g., shrinkage, of objects produced by ultraviolet curing, e.g., stereolithography.
    Type: Grant
    Filed: September 8, 1993
    Date of Patent: March 12, 1996
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Gary C. Rex
  • Patent number: 5496870
    Abstract: A curable liquid resin composition comprising a urethane (meth)acrylate polymer obtained by reacting:(A) a polyol compound containing as structural units groups which are represented by formulae--CH.sub.2 CH.sub.2 O-- or--CH.sub.2 CH(CH.sub.2 CH.sub.3)O--;(B) a polyisocyanate compound; and(C) at least one (meth)acrylate compound containing a hydroxyl group and coated articles produced therefrom.
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: March 5, 1996
    Assignee: DSM
    Inventors: Chander P. Chawla, Tohru Ohtaka, Shinichirou Iwanaga, Tsuyoshi Watanabe, Katsutoshi Igarashi
  • Patent number: 5491178
    Abstract: This invention relates to vinyl ether-based coatings for which properties such as color stability, thermal stability, mechanical stability, hydrolytic stability, and resistance to embrittlement may be maintained and properties hydrogen generation and blocking are minimized.
    Type: Grant
    Filed: August 19, 1994
    Date of Patent: February 13, 1996
    Assignee: AlliedSignal Inc.
    Inventors: Raymond J. Swedo, George D. Green, James R. Snyder
  • Patent number: 5475038
    Abstract: A print laminating adhesive composition comprising a selected acrylate terminated photopolymerizable oligomer of the formula: ##STR1## where A is the residue of a diisocyanate selected from the group consisting of diphenylmethane 4,4.sup.1 diisocyanate and 4,4.sup.1 dicyclohexylmethane diisocyanate; X is the residue of polypropylene glycol having a molecular weight of from about 150 to 4000; R is alkyl or hydroxyalkyl of 2 to 10 carbons; R.sup.1 is alkylene of 2 to 3 carbons; and R.sup.2 is hydrogen or methyl.
    Type: Grant
    Filed: May 10, 1994
    Date of Patent: December 12, 1995
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventor: Martin M. Skoultchi
  • Patent number: 5466723
    Abstract: A radiation curable adhesive composition which comprises from 15 to 85 percent by weight of beta-carboxyethyl acrylate and from 85 to 15 percent by weight of 2-phenoxyethyl acrylate based on the total weight of the composition.
    Type: Grant
    Filed: October 17, 1994
    Date of Patent: November 14, 1995
    Assignee: Eastman Kodak Company
    Inventor: Billy R. Dotson
  • Patent number: 5462797
    Abstract: The present invention provides a pressure-sensitive adhesive composition and a method for producing the same. The pressure-sensitive adhesive composition is produced by the combination of at least one free-radically photopolymerizable monomer and at least one set of polyurethane precursors, and a suitable photoinitiation system consisting of at least one salt of a cationic organometallic complex, an additional free-radical photo initiator and the application of sufficient energy to photopolymerize same by sequential exposure to visible electromagnetic radiation and then to ultraviolet electromagnetic radiation.
    Type: Grant
    Filed: February 8, 1994
    Date of Patent: October 31, 1995
    Assignee: Minneapolis Mining and Manufacturing Company
    Inventors: Jerry W. Williams, Robert J. DeVoe, Thomas P. Klun, George F. Vesley, Patrick G. Zimmerman
  • Patent number: 5461691
    Abstract: The present invention is directed to a beam-curable coating composition for coating glass surfaces, particularly, optical glass fibers. The resultant coatings show slight or no loss of adhesion after exposure to moisture. The coating composition includes ethylenically unsaturated polyurethane, ethylenically unsaturated monomer, photoinitiator and a silane compound. The silane compound is an azidosilane and is added to improve adhesion of the coating agents exposed to moisture. Optionally, aminoalkoxysilanes may also be included.
    Type: Grant
    Filed: May 26, 1994
    Date of Patent: October 24, 1995
    Assignee: BASF Lacke + Farben AG
    Inventors: Stephan Schunck, Horst Hintze-Bruning, Rainer Blum
  • Patent number: 5456984
    Abstract: A halogen-free radiation curable flame retardant composition that comprises an end-capped oligomer of a phosphonate polyol and a polyisocyanate and an organic monomer.
    Type: Grant
    Filed: February 6, 1995
    Date of Patent: October 10, 1995
    Assignee: DSM Desotech, Inc.
    Inventors: Timothy E. Bishop, Erwin S. Poklacki
  • Patent number: 5453452
    Abstract: This invention relates to (meth)acrylates represented by formula (1): ##STR1## wherein, R.sub.1 and R.sub.2 are each independently H or CH.sub.3 and average value of n is 1-5; resin composite comprising (A) an urethane (meth)acrylate and/or epoxy (meth)acrylate, (B) a (meth)acrylate represented by formula (1) above, (C) an ethylenically unsaturated compound other than component (A) or (B), and (D) a photopolymerization initiator; and cured products of said resin composites. The cured products of said resin composites of this invention have high refractive index and are superior in mold release property, shape reproducibility, restorability, and scratch resistance and suited in particular for transmission type screens.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: September 26, 1995
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Kenji Nakayama, Katsunori Shimura, Minoru Yokoshima, Nobuo Taniguchi
  • Patent number: 5449704
    Abstract: A liquid composition which on exposure to actinic radiation polymerises to form a heat-curable solid film adhesive, said composition comprising (A) a heat-curable phenol-aldehyde resol resin, (B) a photopolymerisable resin having, on average, more than one polymerisable acrylic group per molecule, (C) a photopolymerisation initiator for (B) and (D) an aminotriazine-formaldehyde resin.
    Type: Grant
    Filed: December 14, 1993
    Date of Patent: September 12, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Stuart J. Thompson, Stuart Mansfield
  • Patent number: 5444104
    Abstract: A polycarbonate dimethacrylate which is the condensation product of 2 parts of hydroxyalkylmethacrylate of the formula. ##STR1## in which A is C.sub.1 -C.sub.6 alkylene, and 1 part of a bis(chloroformate) of the formula ##STR2## in which R is C.sub.2 -C.sub.5 alkylene having at least two carbon atoms in its principal chain and n is an integer from 1 to 4, is usable, admixed with a secondary monomer suitable for dental applications, such as BIS-GMA; UDMA or the like, as an adhesive system for dental restorative materials. Particularly useful is the novel condensation product of 2-hydroxyethylmethacrylate and triethylene glycol bis(chloroformate).Dental adhesives containing these components are suitable for application to enamel, pretreated dentin, porcelain and metallic surfaces. The dentin surfaces are pretreated by application of an alcoholic solution of an alkali metal salt of benzene sulfinic acid.
    Type: Grant
    Filed: October 12, 1993
    Date of Patent: August 22, 1995
    Assignee: Jeneric/Pentron, Inc.
    Inventor: Samuel Waknine
  • Patent number: 5439956
    Abstract: An adhesive for use in bonding finely processed parts such as parts of ink jet recording head has a composition which essentially contains: (A) a vinylester compound of an urethanated epoxy resin; (B) a partial vinylester compound of a multi-functional epoxy resin; (C) an acrylic reactive diluent; (D) a photopolymerization initiator; and(E) an epoxy cure agent. This adhesive is curable by ultraviolet irradiation or by application of heat, and does not flow or spread into areas where bonding is not necessary, so that finely processed parts are bonded with a high degree of precision of the bonding pattern.
    Type: Grant
    Filed: February 9, 1994
    Date of Patent: August 8, 1995
    Assignee: Canon Kabushiki Kaisha
    Inventor: Hiromichi Noguchi
  • Patent number: 5426131
    Abstract: An ultraviolet radiation curable silica coating composition containing (a) acrylic monomers, (b) functionalized colloidal silica, (c) acrylated urethanes, (d) an ultraviolet radiation absorber, and (e) a photoinitiator. The coating composition once applied to and cured on a thermoplastic substrate provides a coating which exhibits improved flexibility and weathering. The coatings are useful for providing abrasion resistance and weatherability to thermoplastic, for example polycarbonate, substrates.
    Type: Grant
    Filed: October 13, 1993
    Date of Patent: June 20, 1995
    Assignee: General Electric Company
    Inventor: Dimitris Katsamberis
  • Patent number: 5416880
    Abstract: The use of an ethylenically-terminated urethane oligomer for the provision of a radiation-cured coating material of an optical fiber, the urethane oligomer being derived from reactants which include a hydroxyl-terminated polyester polyol having dimer acid residues in its structure.
    Type: Grant
    Filed: March 28, 1994
    Date of Patent: May 16, 1995
    Assignee: Zeneca Limited
    Inventors: Martin R. Edwards, Julie A. Waller, Stephen Byrne
  • Patent number: 5409740
    Abstract: A method of forming a fiber bundle which is useful as an industrial thread. The fiber bundle is prepared by integrating individual fiber filaments into a fiber bundle, applying a dual-cure adhesive material to the fiber bundle and initiating polymerization of the dual-cure adhesive material. The dual-cure adhesive material is a combination of a radiation-curable material and a moisture-curable material. The radiation-curable material contains an acrylourethane oligomer and a reactive diluent system, while the moisture-curable material contains a polyisocyanate or an isocyanate-functional urethane prepolymer. The use of a dual-cure material results in a synergistic curing process so as to form a durable and flexible industrial thread or fiber.
    Type: Grant
    Filed: December 18, 1992
    Date of Patent: April 25, 1995
    Assignee: Lord Corporation
    Inventor: Bill L. Brann
  • Patent number: 5407972
    Abstract: A photocurable composition comprising the reaction products of hydroxy terminated liquid sulfide or polysulfide oligomers with photocurable ethylenically unsaturated compounds. The products provide improved sealants for air and marine vehicles.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: April 18, 1995
    Assignee: Sunrez Corp.
    Inventors: W. Novis Smith, Mark Livesay
  • Patent number: 5402516
    Abstract: Optical fiber and cable performance are assured by a category of UV-cured polyurethane acrylates. Low cost is the consequence of use of the polycarbonate oligomer. Good performance and long life are ascribed to other ingredients of the coatings. Dependence on the hindered phenols for antioxidant protection assures sufficient protection for these inherently stable materials without incurring fiber damage found to result from use of hindered amine antioxidants.
    Type: Grant
    Filed: September 30, 1993
    Date of Patent: March 28, 1995
    Assignee: AT&T Bell Laboratories
    Inventors: Lee L. Blyler, Jr., Darryl L. Brownlow, Daryl Inniss, James R. Petisce, Lloyd Shepherd, Carl R. Taylor
  • Patent number: 5395909
    Abstract: The present invention provides a composition comprising, as the essential components, an aromatic compound represented by the following general formula ##STR1## (m is an integer of 2-3, n is an integer of 1-3 and R is a hydrocarbon group of 3-6 carbon atoms or a hydrocarbon group of 3-6 carbon atoms containing a bivalent sulfur atom), an isocyanate compound and a radical polymerization initiator.Said composition is useful for producing a plastic lens having a high refractive index, a small specific gravity, excellent heat resistance and excellent processability.
    Type: Grant
    Filed: October 13, 1993
    Date of Patent: March 7, 1995
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Masanori Shimuta, Toru Takahashi, Hisato Abe, Kenichi Takahashi, Akira Kurata, Osamu Aoki
  • Patent number: 5395863
    Abstract: Radiation-curable compositions including a free radically polymerizable monomer or prepolymer and a different monomer containing an N-vinyl group, said different monomer being a solid at ambient temperature. The different monomer is preferably N-vinyl caprolactam, N-vinyl carbazole, or N,N'-divinyl-2-imidazolidone, for example in an amount of from 1 to 50 percent by weight of the said different monomer. Such compositions have shown good adhesion to and have rendered plastics substrates wettable by the compositions before curing, without the presence of N-vinyl-2-pyrrolidone.
    Type: Grant
    Filed: February 8, 1993
    Date of Patent: March 7, 1995
    Assignee: Sericol Limited
    Inventors: Kevin G. Burns, Helen Jezequel, Nigel P. Gould
  • Patent number: 5395269
    Abstract: An electrical connector of the type having a housing with terminals extending from apertures thereof, is sealed at the aperture entrances around the extending terminal portions. The sealant material is polymerized of a major proportion of at least one vinyl ester resin, a minor proportion of at least one polymerizable acrylic diluent monomer and a polymerization activation system comprising from about 0.025% to about 17% by weight of the resin, by being exposed to actinic radiation selected to activate the system. The polymerized material excludes solder and solvents from the aperture entrances.
    Type: Grant
    Filed: August 26, 1991
    Date of Patent: March 7, 1995
    Assignee: The Whitaker Corporation
    Inventors: Francis F. Koblitz, Thomas M. O'Shea, Lynn K. Snyder
  • Patent number: 5384342
    Abstract: The present invention is directed to a compound of the Formula:R.sub.1 --R.sub.2 --R.sub.3 --R.sub.4 --A--(R.sub.5).sub.n (R.sub.6).sub.3-nwherein: A is Si or Ti; R.sub.1 is an alkenoxy, acryloxy or ethylenically unsaturated dicarboxylate group; R.sub.2 is a 2 to 18 carbon linear, branched or cyclo alkyl, alkenyl, alkynyl, acyl, aryl or poly(alkoxy) group; R.sub.3 contains a urethane, urea, or thiourethane linkage; R.sub.4 is a 2 to 18 carbon linear, branched, or cyclic alkyl, alkenyl, alkynyl, aryl or acyl non-hydrolyzable silyl linking group; R.sub.5 is a 2 to 18 carbon linear, branched, or cyclic alkyl, alkenyl, alkynyl, aryl or acyl group; R.sub.6 is any hydrolyzable silyl linking group (alkoxy, alkenoxy, or halogen); and n is 0 to 2.The present invention is further directed to an improved method of using of a compound of the above Formula as an adhesion promoter in a UV-curable composition for a surface with a free nucleophilic group. Preferably, that surface is glass.
    Type: Grant
    Filed: August 30, 1993
    Date of Patent: January 24, 1995
    Assignee: DSM Desotech, Inc.
    Inventor: David M. Szum
  • Patent number: 5381735
    Abstract: Release of a resin mold from a photopolymeric mold is enhanced by using an unsaturated fatty acid ester release agent in the photopolymeric composition. In addition to providing quick release of the resin mold, the incorporation of the unsaturated fatty acid ester improves the flexibility of the photopolymeric mold without sacrificing tensile strength or hardness. The resin mold is used to fabricate rubber plates for ink printing.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: January 17, 1995
    Assignee: Hercules Incorporated
    Inventor: Charles C. Fifield
  • Patent number: 5378735
    Abstract: An ultraviolet-curing covering composition comprising Component A which is obtained by reacting a hydroxyl group-containing polyfunctional acrylate with a silane coupling agent containing an isocyanate group(s), Component B of a polyfunctional acrylate having 3 or more acryloyl groups in the molecule, Component C of a silica sol in an organic solvent, and Component D of a photopolymerization initiator. This composition forms a coating film shows excellent hardwearing properties and adhesion to plastic substrates after ultraviolet-curing. Blending Component E of an acrylic resin and Component F of a solvent to the composition forms a coating film which can be processed before curing.
    Type: Grant
    Filed: April 6, 1993
    Date of Patent: January 3, 1995
    Assignee: Mitsubishi Petrochemical Company, Ltd.
    Inventors: Noritaka Hosokawa, Kazuhide Hayama
  • Patent number: 5373033
    Abstract: A cross-linkable polymeric casting composition includingA) a polyoxy alkylene glycol diacrylate or dimethacrylate;B) a monomer having a recurring unit derived from at least one radical-polymerisable bisphenol monomer capable of forming a homopolymer having a refractive index of more than 1.55; andC) a urethane monomer having 2 to 6 terminal groups selected from a group comprising acrylic and methacrylic groups.
    Type: Grant
    Filed: February 1, 1994
    Date of Patent: December 13, 1994
    Assignee: Sola International Holdings Limited
    Inventors: Huan K. Toh, Chong M. Kok, Michael Pittolo
  • Patent number: 5373032
    Abstract: This invention relates to alk-1-enyl etherurethanyl block prepolymers which are curable by cationically initiated radiation and which are defined by the formula ##STR1## wherein m has a value of from 1 to 25;A is C.sub.2 to C.sub.12 alkylene, C.sub.6 to C.sub.14 aryl, both groups optionally substituted with lower alkyl, halo lower alkyl, alkyleneoxy, halogen or aryl;R.sub.1 is alkylene containing from 1 to 6 carbon atoms;R.sub.2 is a saturated or unsaturated divalent radical containing from 1 to 14 carbon atoms and is selected from the group of alkylene, alkenylene and arylene, each group optionally substituted with oxygen, halogen, lower alkyl and/or hydroxy;R.sub.3 is hydrogen or C.sub.1 to C.sub.6 alkyl;R.sub.4 is C.sub.1 to C.sub.6 alkylene, C.sub.6 to C.sub.14 arylene, lower alkyl substituted phenylene or xylylene andR.sub.5 is hydrogen or C.sub.1 to C.sub.4 alkyl.
    Type: Grant
    Filed: August 18, 1993
    Date of Patent: December 13, 1994
    Assignee: ISP Investments Inc.
    Inventors: Mark M. Miller, Jeffrey S. Plotkin
  • Patent number: 5369140
    Abstract: A radiation curable composition contains as light stabiliser a UV absorber of formula I ##STR1## wherein R is hydrogen or C.sub.1 -C.sub.18 alkyl, R.sub.1 and R.sub.2 are each independently of the other H, OH, C.sub.1 -C.sub.12 alkyl, halogen or halomethyl,R.sub.3 and R.sub.4 are each independently of the other H, OH, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.18 alkoxy or halogen, andR.sub.5 and R.sub.6 are each independently of the other H, C.sub.1 -C.sub.12 alkyl or halogen. These UV absorbers are substantially non-yellowing.
    Type: Grant
    Filed: May 3, 1991
    Date of Patent: November 29, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas Valet, Manfred Kohler
  • Patent number: 5364691
    Abstract: This invention relates to radiation curable alk-1-enyloxy carbonate reaction products of a hydroxylated compound having the formula A-ROH and a dialk-1-enyloxy carbonate having the formula ##STR1## wherein R is a polymeric radical selected from the group of polyester, polyacetal, polyurethane, polyether, and polycarbonate, said polymers containing from about 10 to 50 repeating monomer units;A' is a terminating moiety and is hydrogen, lower alkyl or hydroxy;R' is hydrogen or lower alkyl;B is a linear, branched or cyclic divalent radicalhaving from 2 to 12 carbon atoms and is selected from the group of alkylene, mono or poly alkoxylated alkylene, alkenylene, alkynylene, arylene, alkarylene and aralkylene radicals, which radicals are optionally substituted with halo, lower alkyl, cyano, nitro or alkoxy and m has a value of from 1 to 10.
    Type: Grant
    Filed: March 9, 1990
    Date of Patent: November 15, 1994
    Assignee: ISP Investments Inc.
    Inventors: Paul D. Taylor, Kolazi S. Narayanan, Jeffrey S. Plotkin
  • Patent number: 5362603
    Abstract: The present invention relates to a photopolymerizable composition containing a photopolymerizable compound having at least one ethylenically unsaturated double bond, a photopolymerization initiator, a pigment and optionally another resin, wherein said photopolymerizable compound contained therein comprises not less than 60%.
    Type: Grant
    Filed: February 24, 1993
    Date of Patent: November 8, 1994
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Yoshinori Katoh, Naoko Ichinose, Teruhito Sotogoshi
  • Patent number: 5361616
    Abstract: A coating composition having photopolymerizability and heat curability, which comprises, as main components,(A) a vinyl copolymer having polymerizable double bonds and crosslinkable hydroxyl groups,(B) a condensation polymerizable compound of the following formula (i) or a condensation polymer thereof, and(C) a photopolymerization initiator: ##STR1## wherein each of the plurality of R which may be the same or different, is --H, --CH.sub.2 OH, --CH.sub.2 OCH.sub.3, --CH.sub.2 OC.sub.4 H.sub.
    Type: Grant
    Filed: June 9, 1992
    Date of Patent: November 8, 1994
    Assignee: Dai Nippon Toryo Co., Ltd.
    Inventors: Toshiya Takahashi, Norio Uriya, Yoshihisa Nagashima
  • Patent number: 5360836
    Abstract: The subject of the invention is a process for the production of coatings by radiation crosslinking of compositions containing a resin which can be cured by the polymerization of the double bonds >C.dbd.CH.sub.2 and a reactive diluent system containing at least one reactive diluent corresponding to the general formula (I) ##STR1## in which R.sub.1 =H, CH.sub.3,R.sub.2 and R.sub.3 =H, C.sub.1 -C.sub.4 -alkyl chain or form an alkylene ring containing 5 or 6 carbon atoms,R.sub.4 =H, C.sub.1 -C.sub.4 -alkyl chain, phenyl,R.sub.5 =C.sub.1 -C.sub.10 aliphatic chain, C.sub.5 -C.sub.6 alicyclic chain, or C.sub.1 -C.sub.4 alkyl chain substituted with an aryl or aromatic heterocyclic group,or R.sub.4 and R.sub.5 form a 5- or 6-membered ring.One preferred compound (I) is to the acrylate of isopropyl beta-hydroxyethylcarbamate.
    Type: Grant
    Filed: March 22, 1993
    Date of Patent: November 1, 1994
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Francois Chevallier, Sammy Chevalier
  • Patent number: 5360835
    Abstract: Radiation-curable polyurethane emulsion compositions that can be diluted with water are disclosed. An emulsion of a polyurethane having active amino groups is prepared, and the emulsion is reacted, in the presence of water, with an isocyanate compound having a polymerizable unsaturated group to introduce the polymerizable unsaturated group into the polyurethane. The introduction of a polymerizable unsaturated group into the polyurethane is accomplished in the presence of water, thereby overcoming prior art problems of polymerization and gelation during the preparation of the emulsion. The present invention provides radiation-curable polyurethane emulsion compositions that can be produced on an industrial scale.
    Type: Grant
    Filed: November 30, 1993
    Date of Patent: November 1, 1994
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Kazuo Sato, Tadayuki Sugimoto, Naofumi Saiuchi
  • Patent number: 5358978
    Abstract: This invention relates to alkenyl ether polycarbonates having the formula ##STR1## wherein A is selected from the group consisting of lower alkyl and R'HC.dbd.CHOR--, R and R" are each independently a divalent radical having from 2 to 20 carbon atoms and are selected from the group of alkylene, mono- or poly- alkoxylated alkylene, alkenylene, alkynylene, arylene, alkarylene and aralkylene radicals, which radicals are optionally substituted with halo, alkyl, cyano, nitro or alkoxy; R' is hydrogen or lower alkyl; (n) has a value of from 1 to 10 and (m) has a value of from 0 to 10; with the proviso that R" contains at least 3 carbon atoms when m is zero. The invention also concerns the preparation and use of said alkenyl ether polycarbonates.
    Type: Grant
    Filed: February 3, 1993
    Date of Patent: October 25, 1994
    Assignee: ISP Investments Inc.
    Inventors: Jeffrey S. Plotkin, Fulvio J. Vara, James A. Dougherty, Paul D. Taylor, Kolazi S. Narayanan
  • Patent number: 5356947
    Abstract: The present invention provides controllably curable photoiniferter containing adhesive compositions which are suitable for the mounting of microelectronic devices such as flip chips onto transparent wiring boards, a method of making the adhesive compositions, and a method of using the adhesive compositions in order to bond microelectronic devices to transparent wiring boards by intermittent exposure of the adhesive composition to a radiant energy source. The adhesive compositions can be cured in a stepwise fashion by intermittent controlled exposure to a source of radiation thus providing exactly the amount of cure and hardening desired.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: October 18, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Mahfuza B. Ali, Jean M. Pujol
  • Patent number: 5352713
    Abstract: A radiation curable coating composition comprising acrylate oligomers and monomers, vinyl ether monomers, and a free radical photoinitiator. The vinyl ether monomers replace N-vinyl-pyrrolidone or other undesirable reactive diluents while retaining or modifying the properties of coatings using such diluents.
    Type: Grant
    Filed: April 1, 1992
    Date of Patent: October 4, 1994
    Assignee: Allied-Signal Inc.
    Inventors: James R. Snyder, George D. Green, John J. Krajewski
  • Patent number: 5352712
    Abstract: Ultraviolet radiation-curable primary and secondary coating compositions for optical fibers are disclosed. The primary coatings comprise a hydrocarbon polyol-based reactively terminated aliphatic urethane oligomer; a hydrocarbon monomer terminated with at least one end group capable of reacting with the terminus of the oligomer; and an optional photoinitiator. The secondary coatings comprise a polyester and/or polyether-based aliphatic urethane reactively terminated oligomer; a hydrocarbonaceous viscosity-adjusting component capable of reacting with the reactive terminus of (I); and an optional photoinitiator. Also disclosed are optical fibers coated with the secondary coating alone or with the primary and secondary coatings of the invention.
    Type: Grant
    Filed: April 16, 1992
    Date of Patent: October 4, 1994
    Assignee: Borden, Inc.
    Inventor: Paul J. Shustack
  • Patent number: 5344353
    Abstract: A method for manufacturing a cathode ray tube is provided which comprises (a) spraying on the inner surface of a phosphor layer of a phosphor coated panel, an organic composition for forming a heat labile film, the organic composition being free of flammable or explosive organic solvents and including an initiator capable of forming a radical or cation when exposed to ultraviolet or electron rays and at least one resin containing at least one group consisting of acrylate, vinyl and diazo functional groups to form a heat labile film thereon; (b) exposing the heat labile film to ultraviolet or electron rays to from a hardened film layer; (c) forming an aluminum layer on a surface of the hardened film layer to form a screen; (d) sealing with heat the panel and a funnel to form a bulb with a mount including an electron gun and a stem, wherein the step of sealing to form a bulb decomposes the hardened film layer.
    Type: Grant
    Filed: November 1, 1991
    Date of Patent: September 6, 1994
    Assignee: Samsung Electron Devices Co., Ltd.
    Inventors: Dong-sik Jang, Byeong-yong Lee
  • Patent number: 5340653
    Abstract: A free-radical radiation curable composition comprising:a) at least one compound containing one to six vinyl ether groups; andb) at least one compound containing a urethane backbone with one to six maleate and/or fumarate end groups,wherein the ratio of vinyl ether groups to maleate and/or fumarate groups is in the range of about 1 to about 1:5.
    Type: Grant
    Filed: May 26, 1992
    Date of Patent: August 23, 1994
    Assignee: Stamicarbon B.V.
    Inventors: Gerry K. Noren, John J. Krajewski, Sami A. Shama, John M. Zimmerman, Danny C. Thompson, John T. Vandeberg
  • Patent number: 5338613
    Abstract: A photocurable resin composition comprising (a) 10 to 90 parts by weight of a urethane acrylate resin which is obtainable by reacting a polyester in which an alicyclic dicarboxylic acid component accounts for 100 mole percent of the total acid component and an aliphatic diol having a side chain and/or alicyclic diol accounts for 60 to 100 mole percent of the total alcohol component while an aliphatic tri- or polyol accounts for 40 to 0 mole percent with (i) an aliphatic or alicyclic polyisocyanate and an active hydrogen compound containing a polymerizable unsaturated group or (ii) a monofunctional isocyanate compound containing a polymerizable unsaturated group within the molecule, (b) 90 to 10 parts by weight of a non-aromatic crosslinking agent having at least one (meth)acryloyl group within the molecule, and (c) an effective amount of a photosensitizer to initiate a photopolymerization reaction between (a) and (b).
    Type: Grant
    Filed: April 9, 1992
    Date of Patent: August 16, 1994
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Akio Tomotsugu, Keiji Hida
  • Patent number: 5336585
    Abstract: A photosensitive resin composition for use in forming a relief structure, which comprises, in specific proportions, a liquid photosensitive resin component comprising a urethane prepolymer and an addition-polymerizable ethylenically unsaturated monomer; a photopolymerization initiator; a thermal polymerization inhibitor; and a specific unsaturated amine compound. The photosensitive resin composition exhibits excellent performances such that it does not suffer from tunnel phenomenon which is frequently observed in relief formation with respect to conventional photosensitive resin compositions, so that a photoresin relief structure made therefrom not only is characterized with a tunnel-free structure and excellent mechanical properties, but also exhibits excellent performances.
    Type: Grant
    Filed: December 30, 1992
    Date of Patent: August 9, 1994
    Assignee: Asahi Kasei Kogyo Kabushiki
    Inventors: Gensho Takahashi, Reijiro Sato
  • Patent number: 5336563
    Abstract: 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: Grant
    Filed: January 26, 1993
    Date of Patent: August 9, 1994
    Assignee: DSM Desotech, Inc.
    Inventors: Clive J. Coady, Erwin S. Poklacki, John M. Zimmerman, Timothy E. Bishop, John L. Derer
  • Patent number: 5318998
    Abstract: An adhesive composition comprising a first liquid containing (A) an acrylic compound selected from the group consisting of (meth)acrylic acids and esters thereof, and (B) a polymerization initiator selected from the group consisting of peroxy esters and hydroperoxides, and a second liquid containing (C) a condensation product of an amine and an aldehyde, and (D) a copper salt, wherein an acid phosphate compound of the following formula (I): ##STR1## wherein R is an alkyl group, an alkoxyalkyl group or a CH.sub.2 .dbd.CR.sub.1 --CO(OR.sub.2).sub.m -- group, wherein R.sub.1 is H or CH.sub.3, R.sub.2 is --C.sub.2 H.sub.4 --, --C.sub.3 H.sub.6 --, ##STR2## --C.sub.4 H.sub.8 --, --C.sub.6 H.sub.12 -- or ##STR3## and m is an integer of from 1 to 10; and n is 1 or 2, is contained in the first liquid or in both the first and second liquids.
    Type: Grant
    Filed: September 10, 1990
    Date of Patent: June 7, 1994
    Assignee: Denki Kagaku Kogyo Kabushiki Kaisha
    Inventors: Kohichi Taguchi, Hiroshi Suto
  • Patent number: 5304586
    Abstract: One component, visible light-cured dental restorative compositions having fluoride release properties for the purpose of reducing the chances of secondary caries are provided. The compositions include inorganic particulate fluoride leachable glass.
    Type: Grant
    Filed: August 2, 1991
    Date of Patent: April 19, 1994
    Assignee: Dentsply Research & Development Corp.
    Inventors: Paul D. Hammesfahr, Paul S. Danielson, Robert C. Campbell
  • Patent number: 5302627
    Abstract: Adding a dye with a visible color to an ultraviolet radiation curable composition which contains a photoinitiator which generates free radicals upon exposure to ultraviolet radiation produces a composition which changes visible color upon exposure to ultraviolet radiation. This visible color change indicates that the composition has cured. This cure indication is useful for compositions curable by ultraviolet radiation in the electronics and electrical industry.
    Type: Grant
    Filed: March 9, 1992
    Date of Patent: April 12, 1994
    Assignee: Dow Corning Corporation
    Inventors: Arthur J. Field, Michael R. Strong
  • Patent number: 5290663
    Abstract: A photopolymer useful in preparing water-developable, solid printing plates is prepared by (A) preparing a urethane prepolymer by reacting a polyoxyalkylene diol (optionally carboxylic acid grafted) with an excess of diisocyanate, followed by chain extending the resulting prepolymer mixture with a dialkylolpropionic acid and preferably with additional diols(s) such as alkane diol(s) and (meth)acrylate-containing diol(s). Use of a new (meth)acrylate-containing diol in such chain extension completes the formation of photopolymer. However, in a third operation (B) hydroxyalkylmethacrylate may be reacted with the result of (A) whether or not (meth)acrylate-containing diol is used in (A). The carboxylic acid groups of the photopolymer may also be partially neutralized with a base. The photopolymer is suitably formulated with additional photoactive (meth)acrylate monomers or oligomers and photoinitiator for casting on a substrate or extruding to form a flexographic printing plate.
    Type: Grant
    Filed: March 1, 1991
    Date of Patent: March 1, 1994
    Assignee: W. R. Grace & Co.-Conn.
    Inventor: Truc-Chi T. Huynh-Tran
  • Patent number: 5288571
    Abstract: A photoresin printing plate having a Shore A hardness at 20.degree. C. of 25 to 60, an impact resilience at 20.degree. C. of 35% or more as measured by a falling ball method and a surface tack at 20.degree. C. of 40 g/cm or less has been found not only to be capable of providing prints having an image of high precision but also to be capable of releasing the paper dust or the like, which has adhered to the printing plate, in a short period of time during the printing operation, so that it did not become necessary to interrupt the printing operation in order to clean the printing plate, which leads to an efficient production of the prints.
    Type: Grant
    Filed: February 27, 1992
    Date of Patent: February 22, 1994
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Shohei Nakamura, Kuniaki Minonishi
  • Patent number: 5283265
    Abstract: A photopolymerizable rubber being obtained by copolymerizing four compounds consisting of a dienic liquid rubber having hydroxyl groups, an ethylenically unsaturated monomer having hydroxyl groups, a dihydric alcohol having a molecular weight of less than 2,000 and a diisocyanate compound. The photocured product of this composition has higher tensile strength and elongation than that of the prior photopolymerizable rubbers.
    Type: Grant
    Filed: April 18, 1988
    Date of Patent: February 1, 1994
    Assignee: Hayakawa Rubber Company Limited
    Inventors: Tetsuya Kimura, Syuno Suto, Fujii Toshihiro, Toshihiro Fujii, Kimio Mori, Tsuguo Yamaoka
  • Patent number: 5281473
    Abstract: There is provided a radiation-curable adhesive tape comprising a radiation-curable adhesive layer which is formed on a radiation transmitting-substrate. The radiation-curable adhesive layer is composed of an acrylic adhesive and radiation-curable compound having carbon-carbon double bonds. The radiation-curable tape can be used preferably in processing steps for the production of semiconductor wafer, ceramics and glass employing a direct picking-up system.
    Type: Grant
    Filed: February 25, 1992
    Date of Patent: January 25, 1994
    Assignee: Furakawa Electric Co., Ltd.
    Inventors: Shinichi Ishiwata, Michio Ueyama, Hiroyuki Nakae, Yoshiyuki Funayama, Kazushige Iwamoto, Isamu Noguchi