With Ethylenic Reactant Patents (Class 522/107)
  • 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: 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: 5472992
    Abstract: Compounds of the formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.18 alkyl, cyclopentyl or cyclohexyl, and R.sub.2 and R.sub.3, independently of one another, are phenyl which is unsubstituted or monosubstituted to tetrasubstituted by halogen, C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkoxy, with the proviso that R.sub.1 is not decyl if R.sub.2 and R.sub.3 are chlorine-substituted phenyl, are suitable for the photopolymerisation of compounds containing ethylenically unsaturated double bonds.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: December 5, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: David G. Leppard, Manfred Kohler, Ljubomir Misev
  • 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: 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: 5446073
    Abstract: Composition containing charge transfer complex from at least one unsaturated compound having an electron donor group and having an electron withdrawing group and being free of any photoinitiating compound is polymerized by being subjected to ultraviolet light.
    Type: Grant
    Filed: March 31, 1993
    Date of Patent: August 29, 1995
    Assignee: Fusion Systems Corporation
    Inventors: Sonny Jonsson, Per-Erik G. Sundell, William R. Schaeffer
  • Patent number: 5416126
    Abstract: A composition which is cured upon exposure to ultraviolet light in the absence of solvent is disclosed. The liquid composition is prepared by combining a liquid maleate polyester and at least one of a vinyl compound and an allyl functional compound. A photoinitiator is then added to the polymerizable liquid composition. A substrate is impregnated with the polymerizable liquid composition and exposed to actinic energy of a sufficient dosage for a sufficient amount of time to polymerize the composition to a sufficient degree to impart useful properties to the substrate. The composition can be used as a binder for fiberglass insulation, in the manufacture of transparent or semi-transparent paper and to manufacture paper for use in photocopy machines.
    Type: Grant
    Filed: February 17, 1993
    Date of Patent: May 16, 1995
    Assignee: DSM N.V.
    Inventors: Edward J. Murphy, Edward P. Zahora, Sami A. Shama
  • Patent number: 5409965
    Abstract: An active energy ray-curing abrasion resistant coating composition is provided by incorporating following components: (a) a carboxylate-containing polyfunctional acrylate obtained by reacting a tetracarboxylic dianhydride and a hydroxyl group-containing polyfunctional acrylate having hydroxyl group(s) and at least three acryloyl groups and then neutralizing the reaction product; (b) a polyfunctional acrylate having at least three acryloyl groups; (c) an organic solvent; and (d) a photopolymerization initiator. The composition may comprise in addition to the components (e) a silica sol in an organic solvent as a dispersion medium. The composition may further comprise in addition to the components (f) an acrylic resin. Such composition is an active energy ray-curing abrasion-resistant coating composition which forms a film having excellent adhesion to a plastic sustrate, transparency, abrasion resistance and antistatic properties.
    Type: Grant
    Filed: July 26, 1994
    Date of Patent: April 25, 1995
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Noritaka Hosokawa, Kazuhide Hayama
  • 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: 5405657
    Abstract: A process for the production of flexible impregnated protective, auxiliary and insulating materials on a fibre basis for electrical purposes by the application of an impregnating agent to the material to be impregnated, followed by curing, characterised in that a solvent-free impregnating mass containing one or more olefinically unsaturated, radically polymerisable polyesters, which contain one or more radically polymerisable monomers as reactive diluents, one or more plasticizing agents and optionally one or more peroxide-free radical initiators is applied to the material to be impregnated and curing is then carried out with high energy radiation and optionally by further heating.
    Type: Grant
    Filed: November 2, 1993
    Date of Patent: April 11, 1995
    Assignee: Herberts G.m.b.H.
    Inventors: Udo Bastian, Rainer Krause, Gerhard Kiessling
  • 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: 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: 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: 5342860
    Abstract: This invention relates to alk-1-enyl ether-polyester 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 and R.sub.6 are independently hydrogen or C.sub.1 to C.sub.4 alkyl.
    Type: Grant
    Filed: August 18, 1993
    Date of Patent: August 30, 1994
    Assignee: ISP Investments Inc.
    Inventors: Jeffrey S. Plotkin, Mark M. Miller
  • Patent number: 5334456
    Abstract: A free-radical radiation curable composition comprising:a) at least one compound containing from one to about six vinyl ether groups; andb) at least one compound containing a saturated backbone and at least one maleate or fumarate end group per molecule,wherein the ratio of vinyl ether groups to maleate or fumarate groups in the composition is in the range of about 5:1 to about 1:5.
    Type: Grant
    Filed: May 26, 1992
    Date of Patent: August 2, 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: 5326822
    Abstract: A heat-curable molding material consists of an unsaturated polyester, monomers, a propylene polymer, free radical initiators and conventional additives and assistants, the propylene polymer being dispersed in the form of solid, round particles having a smooth surface and a mean diameter of from 1 to 200 .mu.m in the polyester resin.
    Type: Grant
    Filed: June 26, 1992
    Date of Patent: July 5, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Anton Hesse, Walter Heckmann, Harald Kroeger, Bernd L. Marczinke, Volker Warzelhan
  • Patent number: 5304458
    Abstract: Flexographic photosensitive printing plates are made with formulations comprising block polymers having an architecture of BA, CBA or CBCA, where A is poly(vinylpyridine), B is poly(butadiene) or poly(isoprene) and C is styrene. The polymers may be quaternized or neutralized with an organic acid. When made with quaternized polymers, the plates after imaging with UV may be developed in aqueous solutions. The block polymers offer further advantages as to ease of synthesis, safety and improved resolution.
    Type: Grant
    Filed: September 8, 1992
    Date of Patent: April 19, 1994
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Arthur L. Berrier, Rustom S. Kanga
  • Patent number: 5281569
    Abstract: A desensitizing ink for printing by wet or dry offset, flexographic or typographic printing is disclosed and claimed. This ink contains at least one desensitizing agent, at least one ink binder which is polymerizable or crosslinkable by UV light or electron beam radiations and, if necessary, an initiator system. Thus, the drying time of the printings is greatly reduced. The ink is free from vaporizable ink solvents.
    Type: Grant
    Filed: February 25, 1992
    Date of Patent: January 25, 1994
    Assignee: SICPA International S.A.
    Inventors: Albert Amon, Laszlo K. Boksanyi
  • Patent number: 5268257
    Abstract: A photocurable composition P(Y)(Y.sub.1)(Y.sub.2) is prepared by reacting a solid carboxylated copolymer P(Y) having at least one pendent carboxyl group Y, and optionally one or more terminal carboxyl groups Y, with (i) a photosensitive vinyl-containing compound, e.g. glycidyl (meth)acrylate, which produces Y.sub.1 and optionally, with (ii) an anhydride, e.g. maleic anhydride, to produce Y.sub.2. Y.sub.1 has free vinyl groups and Y.sub.2 has free vinyl and acid groups. In addition, P(Y) can be a liquid carboxylated copolymer which is chain extended in order to prepare a solid. Either of the resulting photocurable compositions can be used "as is" or can be formulated with vinyl containing monomers and photoinitiators to prepare solid, flexible photosensitive articles, e.g. flexographic printing plates, which are water dispersible, and yet possess acceptable mechanical properties for flexographic printing.
    Type: Grant
    Filed: March 9, 1993
    Date of Patent: December 7, 1993
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Srinivas K. Mirle, Arthur L. Berrier
  • Patent number: 5268255
    Abstract: A printed circuit board has a resist layer made from a photo-setting resist composition containing:(A) a polyfunctional unsaturated compound which is solid at room temperature,(B) a polyfunctional unsaturated compound which is liquid at room temperature,(C) a photopolymerization initiator,(D) an epoxy resin,(E) at least one member selected from the group consisting of:(i) a curing agent for the epoxy resin and either melamine or the derivative thereof, and(ii) a compound having a 2,4-diamino-s-triazine ring and an imidazole ring in the molecule.
    Type: Grant
    Filed: September 30, 1991
    Date of Patent: December 7, 1993
    Assignee: Hitachi, Ltd.
    Inventors: Hiroshi Kikuchi, Makio Watanabe, Shinichiro Imabayashi, Reiko Yano, Isamu Tanaka, Hitoshi Oka, Yukihiro Taniguchi, Shigeru Fujita
  • Patent number: 5254602
    Abstract: A photocurable compound prepared as a starting material by incorporation therein of a composition comprising a fluorescein compound photoreducing dye, tribenzylamine, and at least one specific peroxide permits production of a shaped article which, on exposure to visible light, exhibits high curability and acquires hardness virtually indiscriminately on the obverse and reverse sides of the article. A mixture comprising both or either of an unsaturated polyester resin and an epoxy acrylate resin which are photocurable compounds, glass fibers, and a specific peroxide, is convenient for the production of specific cured shaped articles particularly by the filament winding technique or the drawing technique.
    Type: Grant
    Filed: February 21, 1992
    Date of Patent: October 19, 1993
    Assignee: Nippon Oil & Fats Co., Ltd.
    Inventors: Yoshihiro Tomura, Shigeki Banno
  • Patent number: 5254603
    Abstract: A radiation curable coating composition comprising reactive monomers, a photoinitiator, between about 4 wt.% to 35 wt.% of a cellulose derivative, preferably nitrocellulose and an unsaturated polyester resin which is the reaction product of glycols and unsaturated dibasic acids. Coatings prepared in accordance with the present invention can be used as overprint varnishes for magazines and other coated papers. These coatings may also be used to provide a protective finish for wood.
    Type: Grant
    Filed: December 24, 1990
    Date of Patent: October 19, 1993
    Assignee: Hercules Incorporated
    Inventor: Steven H. Nahm
  • Patent number: 5232958
    Abstract: Electron-beam cure by itself or in combination with multifunctional additives is used to improve the high-temperature shear properties of emulsion polymerized pressure-sensitive adhesives.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: August 3, 1993
    Assignee: Avery Dennison Corporation
    Inventors: Prakash Mallya, Sebastian S. Plamthottam, Yehuda Ozari
  • Patent number: 5212212
    Abstract: A zinc-stable ceramic ink composition which contains a metal oxide, a glass frit, a UV-curable vehicle, zinc powder, and a calcium-containing organic complex. The calcium-containing organic complex prevents premature polymerization of the UV-curable vehicle so that the zinc-containing ink composition may be stored for extended periods of time prior to use.
    Type: Grant
    Filed: November 14, 1992
    Date of Patent: May 18, 1993
    Assignee: Lord Corporation
    Inventor: James B. Fonda
  • Patent number: 5212213
    Abstract: This invention relates to novel radiation-curable, rosin-based resins and the process for preparing them. In particular, the invention relates to unsaturated polyester resins containing fully fumarated rosin and/or fully maleated rosin which have softening points of at least 80.degree. C. and are capable of being flaked into solid chips; a property that make the resins useful in formulating vehicles for lithographic printing inks and other coating applications.
    Type: Grant
    Filed: May 20, 1992
    Date of Patent: May 18, 1993
    Assignee: Westvaco Corporation
    Inventor: G. Frederick Hutter
  • Patent number: 5145885
    Abstract: The photopolymerizable composition described containsA) at least one ethylenically unsaturated photopolymerizable compound,B) a photoinitiator of the formula I ##STR1## and C) a photosensitizer from the group of aromatic carbonyl compounds having a triplet energy of 225-310 kJ/mol, for example xanthones, thioxanthones, coumarins, phthalimides, phenones and the like.Ar is phenyl substituted in the 4-position by a substituted amino group, R.sup.1 and R.sup.2 are alkyl, R.sup.3 and R.sup.4 are alkyl or alkoxyalkyl, or R.sup.3 and R.sup.4 together are 3-oxapentamethylene. Said sensitizers C) raise the activity of said photoinitiators (B) without shortening the shelf life of the mixtures. The photocurable mixtures are used especially as binders for printing inks or paints.
    Type: Grant
    Filed: November 13, 1990
    Date of Patent: September 8, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Godwin Berner, Kurt Meier, Kurt Dietliker, Rinaldo Husler
  • Patent number: 5096938
    Abstract: Radiation-curable catalysts are obtainable by reactingA) 1 equivalent of a dihydric to hexahydric oxyalkylated C.sub.2 -C.sub.10 -alcohol withB) from 0.05 to 1 equivalent of a dibasic to tetrabasic C.sub.3 -C.sub.36 -carboxylic acid or its anhydride andC) from 0.1 to 1.5 equivalents of acrylic acid and/or methacrylic acidand reacting the excess carboxyl groups with an equivalent amount of epoxide compound, and are used in radiation-curable coating materials.
    Type: Grant
    Filed: April 3, 1990
    Date of Patent: March 17, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Erich Beck, Wolfram Weiss, Horst Schmidt
  • Patent number: 5095044
    Abstract: Compounds of the formula I ##STR1## in which n is 1-30 and X, Y, R, Ar.sup.1 and Ar.sup.2 are as defined in claim 1 can be prepared by reaction of a benzil dialkyl ketal with a diol. Depending on the molar ratio of the two reaction components, products having a different polycondensation degree n are obtained. the compounds can be used as photoinitiators.
    Type: Grant
    Filed: April 27, 1990
    Date of Patent: March 10, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Rinaldo Husler, Rudolf Kirchmayr, Werner Rutsch, Manfred Rembold
  • Patent number: 5077402
    Abstract: Compounds of the formula I, II, III and IIIa ##STR1## in which Ar.sup.1 is an unsubstituted or substituted aromatic radical and at least one of the radicals R.sup.1 and R.sup.2 is an alkenyl, cycloalkenyl or arylmethyl group, are effective photoinitiators for photopolymerization of unsaturated compounds. They are particularly suitable for photocuring of pigmented systems.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: December 31, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Vincent Desobry, Kurt Dietliker, Rinaldo Husler, Werner Rutsch, Manfred Rembold, Franciszek Sitek
  • Patent number: 5073476
    Abstract: Iron (II)-aromatic compound complexes mixed with electron acceptors as an oxidizing agent are suitable initiators for the polymerization by irradiation of organic material which can be polymerized by cations and/or free radicals. The composition composed of the polymerizable material and of the initiator mixture is suitable for the production of protective coatings and can be used as a photographic recording material.
    Type: Grant
    Filed: May 10, 1984
    Date of Patent: December 17, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Kurt Meier, Giuliano Eugster, Franz Schwarzenbach, Hans Zweifel
  • Patent number: 5045432
    Abstract: Radiation-sensitive compositions which are especially useful in the production of negative-working lithographic printing plates comprise a photocrosslinkable polymer containing the photosensitive group ##STR1## as an integral part of the polymer backbone and, in an amount sufficient to improve the properties of the composition, both a poly(N-acyl-alkyleneimine) and an unsaturated polyester such as a polyester derived from fumaric acid and a 4,4'-isopropylidenediphenol. The combination of a poly(N-acylalkyleneimine) and an unsaturated polyester improves the properties of the radiation-sensitive composition in regard to such factors as shelf life, image contrast, developability, ink receptivity and reduction in mottle and thereby provides a superior lithographic printing plate.
    Type: Grant
    Filed: July 17, 1990
    Date of Patent: September 3, 1991
    Assignee: Eastman Kodak Company
    Inventors: Paul R. West, James E. Mitchell, Gary R. Miller, Paul R. Josephson, Jr., Raymond W. Ryan, Jr.
  • Patent number: 5017626
    Abstract: A visible light-curing polyester resin composition comprises an unsaturated polyester resin and a photocuring agent composed of an .alpha.-diketone, a benzyidimethyl ketal, and at least one member selected from the group consisting of (1) 2-(dimethylamino)-ethyl benzoate, (2) 2-(dimethylamino)-ethyl benzoate plus a peroxy ketal, and (3) a peroxy ketal plus a tertiaryamine.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: May 21, 1991
    Assignee: Nippon Oil & Fats Co., Ltd.
    Inventors: Yoshihiro Tomura, Shigeki Banno
  • Patent number: 5002976
    Abstract: Acrylate polyesters are made by the reaction of a diol, a dibasic acid anhydride and glycidyl acrylate. When formulated into radiation curable compositions, the compositions can be used as coating, inks, and adhesives which cure at high rates when exposed to actinic radiation.
    Type: Grant
    Filed: February 23, 1989
    Date of Patent: March 26, 1991
    Assignee: Radcure Specialties, Inc.
    Inventors: JoAnn A. McConnell, F. Kurtis Willard, Morris A. Johnson
  • Patent number: 5001168
    Abstract: An adhesive for surface mounting devices comprising a polymerizable prepolymer, a reactive diluent, and a polymerization initiator, the adhesive further comprising as a chelating agent an aminopolycarboxylic acid having at least one hydroxyethyl group bound to the nitrogen atom thereof or an alkali metal salt thereof, and as a curing accelerator cupferron or a metallic salt thereof.
    Type: Grant
    Filed: July 6, 1989
    Date of Patent: March 19, 1991
    Assignee: Somar Corporation
    Inventors: Ryuichi Fujii, Rihei Nagase
  • Patent number: 4996243
    Abstract: A composition of matter comprising an acrylamido-acyl or methacrylamido-acyl oligomer derived from at least one nucleophilic oligomer having at least one amino-, hydroxyl-, or thiol-substituted polyoxyalkylene, polyalkyleneimine, polyester, polyolefin, polyacrylate, or polysiloxane oligomer, said nucleophilic oliogmer having a molecular weight in the range of 200 to 20,000 is disclosed. Also disclosed are free radially polymerizable monomer-containing compositions containing said oligomers as well as acrylamido- and methacrylamido-acylated polymers which are the thermal or photocured products of said oligomers. In addition, a process is disclosed for providing said acrylamido- and methacrylamido-acylated oligomers which are useful, for example, in coatings, films, printing inks, adhesives, and saturants.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: February 26, 1991
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Jerald K. Rasmussen, Steven M. Heilmann, Frederick J. Palensky
  • Patent number: 4994344
    Abstract: A light-sensitive recording element useful for preparing photopolymer flexographic relief printing plates, comprising at least one photopolymerizable recording layer having a thickness of from 0.1 to 7 mm and made up of:from 20 to 99.499% by weight of at least one polymeric binder which may be random ethylene-propylene-alkadiene terpolymers having an ethylene content of from 40 to 80% by weight and a double bond content of from 2 to 20 olefinic double bonds per 1,000 carbon atoms;from 0.001 to 10% by weight of at least one photopolymerization initiator,from 0.5 to 50% by weight of at least one monomer which is compatible with the binder and has at least one photopolymerizable olefinic double bond, andfrom 0.001 to 2% by weight of at least one inhibitor of thermally initiated polymerization and from 0.0001 to 5% by weight of at least one antioxidant as assistants.
    Type: Grant
    Filed: February 3, 1989
    Date of Patent: February 19, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl-Rudolf Kurtz, Horst Koch, Thomas Telser, Manfred Zuerger
  • Patent number: 4987054
    Abstract: Photopolymerizable compositions for image recording, containing, among other components, addition-polymerizable, ethylenically unsaturated compounds and polymeric binders, wherein at least one of these binders is a copolymer of the formula (I) containing 5 to 50 percent by weight of one or more different structural units C1, C2, or combinations thereof containing carboxyl groups.
    Type: Grant
    Filed: March 1, 1989
    Date of Patent: January 22, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Manfred Sondergeld, Jonathan W. Goodin
  • Patent number: 4985474
    Abstract: A resin composition hardenable by irradiation of a high energy ray is disclosed, which includes:(a) a resin selected from the group consisting of rosins and modified rosins and having an acid value of at least 150 and a Gardner color scale of not greater than 15;(b) a compound of the general formula (I):Y--CO--O--A--O).sub. m CO--CR.dbd.CH.sub.2 (I)wherein Y represents ##STR1## A represents an alkylene having 1-4 carbon atoms, R represents hydrogen or methyl and m is an integer of 1-4;(c) a hydroxyl group-containing compound having only one acrylic or methacrylic group and at least one hydroxyl group; and(d) a polyol compound having at least two hydroxyl groups. The resin composition is useful for plugging through-holes of a metal plated board in manufacturing printed wiring boards.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: January 15, 1991
    Assignee: Somar Corporation
    Inventors: Osamu Ogitani, Ryuichi Fujii
  • Patent number: 4921883
    Abstract: Unsaturated polyester resins having an acid number of from 0 to 50 and a hydroxyl number of from 10 to 150 which are composed of 0.6 to 0.8 moles of groups derived from maleic and/or fumaric acid, 0.2 to 0.4 moles of groups derived from norbornene dicarboxylic acid, 0.6 to 0.8 moles of groups derived from ethylene and/or propylene glycol, 0.2 to 0.4 moles of groups derived from diethylene glycol, 0.1 to 0.2 moles of groups derived from benzylalcohol and/or benzoic acid and 0 to 0.2 moles of groups derived from other alcohols, a process for their manufacture by a solvent-free or azeotropic esterification of said monomers and compositions which can be cured under influence of UV radiation, containing from 40 to 80 parts by weight of said polyester resins, from 20 to 60 parts by weight of styrene from 0.5 to 5 parts by weight of at least one photoinitiator and optionally known auxiliary agents and additives.
    Type: Grant
    Filed: March 18, 1988
    Date of Patent: May 1, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Meixner, Wolfgang Kremer, Manfred Muller
  • Patent number: 4886842
    Abstract: The present invention comprises a radiation immobilizable epoxy formulation which displays improved initial and thermal cycle strengths when bonding different materials such as terephthalate polyesters and aluminum.The composition comprises:(1) a compound or mixture of compounds having a plurality of epoxy groups per molecule;(2) a polyoxyalkylene amine curative for the epoxy;(3) an imide compound selected from those having the formulas; and ##STR1## (4) a photocurable ethylenically unsaturated compound and photoinitiator, said ethylenically unsaturated compound and photoinitiator present in amounts which together are effective to cause the composition to become immobilized when irradiated with actinic radiation.
    Type: Grant
    Filed: January 6, 1989
    Date of Patent: December 12, 1989
    Assignee: Loctite Corporation
    Inventors: Kieran F. Drain, Kris Kadziela
  • Patent number: 4886840
    Abstract: Acryloylmorpholine and/or methacryloylmorpholine useful as a reactive diluent for UV and EB curable resin compositions, which has low skin irritation, a little odor, low volatility, low weight loss and high workability and which provides, without imparing work environment, UV and EB curable compositions having a high curing rate and capable of forming films of high hardness with small deformation.
    Type: Grant
    Filed: January 5, 1987
    Date of Patent: December 12, 1989
    Assignee: Kohjin Co., Ltd.
    Inventors: Hideaki Mukohyama, Hiroshi Oka, Kenji Shibusawa
  • Patent number: 4874842
    Abstract: The present invention relates to a method for hot curing thermosetting resins and vulcanizable elastomers, based on the use of perfluoropolyethers in the liquid state as heat transfer media.
    Type: Grant
    Filed: April 13, 1988
    Date of Patent: October 17, 1989
    Assignee: Ausimont S.p.A.
    Inventors: Ken Johns, Alberto Re, Gianangelo Bargigia
  • Patent number: 4857434
    Abstract: This invention is directed to a thermal or radiation curable prepolymer, formulations containing same and processes of using same, said prepolymer comprising a liquid meth(acrylate) terminated polymeric hydrocarbon maleate having pendant maleate groups. Said prepolymer either per se or formulated with mono- or multi-functional unsaturated monomers and either a thermal or photoinitiator on exposure to heat or UV or high energy ionizing radiation forms a cured material utilizable as a printing plate, coating, adhesive or sealant.
    Type: Grant
    Filed: September 2, 1987
    Date of Patent: August 15, 1989
    Assignee: W. R. Grace & Co.
    Inventor: Lori J. Klinger
  • Patent number: 4849320
    Abstract: The invention provides a process for the production of an image which comprises(i) applying to a substrate a layer of a liquid composition comprising(A) a cationically polymerizable residue(B) a radiation-activated polymerization initator for (A)(C) a radiation-curable residue that is different from (A) and optionally(D) a radiation activated initiator for the cure of (C),(ii) subjecting the composition to actinic radiation having a wavelength at which initiator (B) is activated but at which the residue (C) and/or initiator (D) is not substantially activated, followed by heating, if necessary, so that (A) is polymerized and the layer of liquid composition is solidified, but remains curable,(iii) subjecting the solidified layer in a predetermined pattern to actinic radiation having a wavelength that is different from that of the radiation used in stage (ii) and at which the radiation-curable residue (C) and/or the initiator (D) is activated, such that in the exposed areas (C) is substantially cured, and(iv) re
    Type: Grant
    Filed: April 30, 1987
    Date of Patent: July 18, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Edward Irving, Christopher P. Banks
  • Patent number: 4788108
    Abstract: Disclosed is a curable filler composition which resists absorption into a porous substrate, particularly one derived from wood, comprising: (1) a liquid, ungelled binder of an unsaturated polyester resin having number average molecular weight of from 500 to 3,000 derived from an ethylenically unsaturated carboxylic acid or anhydride thereof, the unsaturated polyester resin having been iminated with an alkylenimine, (2) one or more ethylenically unsaturated compounds different from and cocurable with the unsaturated polyester resin, (3) pigment, (4) a free radical initiator, and (5) optionally a carrier solvent for the filler composition.Disclosed is a method of minimizing absorption of a filler composition into a warm or hot porous substrate.Also disclosed is a porous substrate, particularly one derived from wood, having adhered to a substrate thereof the cured filler composition.
    Type: Grant
    Filed: June 15, 1987
    Date of Patent: November 29, 1988
    Assignee: PPG Industries, Inc.
    Inventors: John B. Saunders, Jr., Robert M. Piccirilli, William J. Schillinger, Ken W. Niederst
  • Patent number: 4778831
    Abstract: The invention relates to a sealing compound which contains unsaturated polyester resins, crosslinking agents, light initiators, and elasticity-modifying agents as well as, optionally, adjuvants, pigments, and/or dyes. The invention also relates to a method for the production of the sealing compound and to its use on or in building structures.
    Type: Grant
    Filed: April 22, 1985
    Date of Patent: October 18, 1988
    Assignee: Kunststoff- & Lackfabrik Kemper
    Inventor: Heinz B. Kemper
  • Patent number: 4775597
    Abstract: Disclosed is a curable filler composition which resists absorption into a porous substrate, particularly one derived from wood, comprising: (1) a liquid, ungelled binder of an unsaturated polyester resin having number average molecular weight of from 500 to 3,000 derived from an ethylenically unsaturated carboxylic acid or anhydride thereof, the unsaturated polyester resin having been reacted with a hydroxyl-containing amine selected from the group consisting of an alkanol amine having a secondary amino group, an alkanol amine having a primary amino group and a mixture thereof, (2) one or more ethylenically unsaturated compounds different from and cocurable with the unsaturated polyester resin, (3) pigment, (4) a free radical initiator, and (5) optionally a carrier solvent for the filler composition.Disclosed is a method of minimizing absorption of a filler composition into a warm or hot porous substrate.
    Type: Grant
    Filed: June 15, 1987
    Date of Patent: October 4, 1988
    Assignee: PPG Industries, Inc.
    Inventors: William J. Birkmeyer, John B. Saunders, Jr., William J. Schillinger
  • Patent number: 4743631
    Abstract: Adhesion promoters for metal substrates for paints cross-linkable with U.V. or E.B. radiations or with peroxides of general formula: ##STR1## (wherein R, m and n have the meaning which we will specify in the disclosure), obtained by means of the reaction of glycidyl acrylate and/or glycidyl methacrylate with dihydrophosphonoacetic acid.
    Type: Grant
    Filed: September 6, 1985
    Date of Patent: May 10, 1988
    Assignee: Enichem Sintesi S.p.A.
    Inventors: Alberto Greco, Renato Butturini, Sergio Arrighetti