Specified Rate-affecting Material Contains Onium Group Patents (Class 522/31)
  • Patent number: 5880169
    Abstract: The invention provides a novel sulfonium salt having at least one acid labile group attached to a phenyl group in a molecule and a normal, branched or cyclic C.sub.1 -C.sub.20 alkylsulfonate anion. The novel sulfonium salt is effective for increasing the dissolution contrast between exposed and unexposed areas. Upon exposure, it generates an alkylsulfonic acid which is a weak acid, minimizing the influence of side reaction and deactivation during PEB step. The sulfonium salt is useful in a chemically amplified positive resist composition which lends itself to fine patterning and features high resolution.
    Type: Grant
    Filed: November 1, 1996
    Date of Patent: March 9, 1999
    Assignees: Shin-Etsu Chemical Co., Ltd., Nippon Telegraph and Telephone Corp.
    Inventors: Yoichi Osawa, Satoshi Watanabe, Katsuya Takemura, Shigehiro Nagura, Akinobu Tanaka, Yoshio Kawai
  • Patent number: 5879852
    Abstract: The invention relates to a positive-working radiation-sensitive mixture containing a) a polymeric binder having acid-labile groups and b) a compound which forms a strong acid on irradiation, in which the binder simultaneously contains units of the formulae I, II and IIIR.sup.1 --OH (I),R.sup.1 --O--CO.sub.2 R.sup.2 (II)R.sup.1 --O--CH.sub.2 --CHR.sup.3 --OH (III).The mixture is used to coat radiation-sensitive recording material which can be used to produce printing plates and photoresists.
    Type: Grant
    Filed: April 30, 1997
    Date of Patent: March 9, 1999
    Assignee: AGFA-Gevaert AG
    Inventors: Mathias Eichhorn, Gerhard Buhr
  • Patent number: 5877229
    Abstract: A mixture of epoxy resins such as a semi-solid triglycidyl ether of tris (hydroxyphenyl) methane and a low viscosity bisphenol A glycidyl ether and a cationic photoinitiator such as a diaryliodonium salt is cured by irradiating with a dosage of electron beams from about 50 to about 150 kGy, forming a cross-linked epoxy resin polymer.
    Type: Grant
    Filed: July 26, 1995
    Date of Patent: March 2, 1999
    Assignee: Lockheed Martin Energy Systems, Inc.
    Inventors: Christopher J. Janke, Vincent J. Lopata, Stephen J. Havens, George F. Dorsey, Richard J. Moulton
  • Patent number: 5866261
    Abstract: A composition of matter comprising:(a) about 60 to about 99 parts by weight of a curable epoxypolyorganosiloxane;(b) about 1 to about 40 parts by weight of a crosslinkable silicone hydride resin having no epoxy functionality; and(c) about 0.1 to about 5 parts by weight of an curing agent, which, upon exposure to actinic radiation is capable of curing components (a) and (b);wherein the total amount of components (a) and (b) is 100 parts by weight and wherein said composition demonstrates surface release properties when coated and cured onto a substrate is provided. The composition is particularly useful in articles of manufacture where release properties are desired.
    Type: Grant
    Filed: December 20, 1996
    Date of Patent: February 2, 1999
    Assignee: Rhodia Inc.
    Inventors: Stuart R. Kerr, III, Reeshemah Beaty
  • Patent number: 5863699
    Abstract: A photosensitive composition for forming a pattern through a light-exposure with either one of ArF excimer laser and F.sub.2 excimer laser, which comprises a compound having either an acid-decomposable or acid-crosslinkable group, and a compound represented by the following general formula (1): ##STR1## wherein Ar.sup.1 and Ar.sup.2 are individually an aromatic ring or condensed aromatic ring, R.sup.1 and R.sup.2 are individually halogen atoms or monovalent organic group, X is a group selected from the group consisting of CF.sub.3 SO.sub.3, CH.sub.3 SO.sub.3, CF.sub.3 COOH, ClO.sub.4, SbF.sub.6 and AsF.sub.6, Z is a group selected from the group consisting of Cl, Br, I, S--R and Se--R (R is an alkyl group having 1 to 10 carbon atoms or perfluoroalkyl group having 1 to 10 carbon atoms), and m and n are 0 or a positive integer.
    Type: Grant
    Filed: October 9, 1996
    Date of Patent: January 26, 1999
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Koji Asakawa, Toru Ushirogochi, Naomi Shida, Makoto Nakase
  • Patent number: 5858545
    Abstract: Free-radically polymerizable release coating compositions containing conductivity enhancers, which are capable of being electrosprayed onto a substrate. The compositions comprise (a) about 100 parts by weight of one or more free-radically polymerizable vinyl monomer(s), (b) from about 0.05 to about 250 parts by weight of one or more polydiorganosiloxane polymer(s) copolymerizable with the vinyl monomer(s), and (c) from about 0.10 to about 10 parts by weight, based on 100 parts by weight of (a) and (b), of one or more non-volatile conductivity enhancer(s), which are soluble in the monomer(s) and which do not interfere with polymerization, wherein the composition may be electrosprayed.The composition may further comprise from about 0.1 to about 5 parts by weight of one or more initiator(s) based on 100 parts by weight of monomer(s) and polydiorganosiloxane polymer(s).Another embodiment of the present invention further comprises at least 0.
    Type: Grant
    Filed: March 26, 1996
    Date of Patent: January 12, 1999
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Albert I. Everaerts, Mieczyslaw H. Mazurek, Albert E. Seaver
  • Patent number: 5851728
    Abstract: A three-component chemical amplified photoresist composition, comprising: an alkali soluble resin; a dissolution inhibitor of aromatic polyhydroxy compound substituted by at least two acid-decomposable radicals; and a photo acid generating agent of an onium salt, which is capable of forming good profiles when exposed to light with a short wavelength and is superior in heat resistance and storage stability.
    Type: Grant
    Filed: October 9, 1996
    Date of Patent: December 22, 1998
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Seong-Ju Kim, Joo-Hyeon Park, Ki-Dae Kim, Dong-Chui Seo
  • Patent number: 5849808
    Abstract: A polymer which is insoluble in aqueous-alkaline developer solutions, and comprises structural units of the formula (I): ##STR1## in which R.sub.2 is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.10 cycloalkyl, C.sub.5 -C.sub.14 aryl, C.sub.6 -C.sub.30 aralkyl, R.sub.3 is C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.10 cycloalkyl, C.sub.5 -C.sub.14 aryl, or C.sub.6 -C.sub.30 aralkyl, it being possible for the alkyl, cycloalkyl, aryl, or aralkyl groups to be substituted if desired by one or more hydroxyl groups or nitro groups or by one or more halogen atoms, and X is a k+1 valent organic radical, k being a number from 1 to 5, and 1 is a number from 0 to 4, in a quantity such that the cleavage products obtained by reaction with an acid are soluble in aqueous-alkaline developer solutions, is suitable as a binder for DUV photoresists of high processing stability, high contrast, and good resolution.
    Type: Grant
    Filed: April 19, 1996
    Date of Patent: December 15, 1998
    Assignee: Olin Microelectronic Chemicals, Inc.
    Inventors: Hans-Thomas Schacht, Norbert Muenzel
  • Patent number: 5837420
    Abstract: A positive working photosensitive composition is disclosed, which comprises (a) a resin having groups capable of increasing solubility of the resin in an alkali developer through their decomposition due to the action of an acid and (b) a compound represented by formula (I) or (II) generating sulfonic acid by irradiation with active rays or radiant rays: ##STR1##
    Type: Grant
    Filed: March 6, 1997
    Date of Patent: November 17, 1998
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Kunihiko Kodama, Kazuya Uenishi, Tsukasa Yamanaka
  • Patent number: 5837749
    Abstract: The invention herein is curable adhesive and sealant compositions and a non-aqueous solvent free process for producing such compositions which comprise a mono-ol, tackifying resin, and a monohydroxylated epoxidized polydiene polymer which is comprised of at least two polymerizable ethylenically unsaturated hydrocarbon monomers wherein at least one is a diene monomer which yields unsaturation suitable for epoxidation and wherein the polymer contains from 0.1 to 7.0 milliequivalents of epoxy per gram of polymer. The process involves mixing the components together with a photoinitiator which is selected from the group consisting of diaryl, especially diaryliodonium, salts characterized by the general formula: ##STR1## where Y is ##STR2## where R is hydrogen, aryl, alkyl, or an alkylhalide; n is an integer of at least 1, Z is I, Cl, or Br, preferably I, and X is a complex metal halide anion or a complex halide anion of a strong protonic acid.
    Type: Grant
    Filed: April 15, 1997
    Date of Patent: November 17, 1998
    Assignee: Shell Oil Company
    Inventors: James Robert Erickson, James Crivello
  • Patent number: 5824716
    Abstract: This invention relates to dicyclopentyl-oxyethyl methacrylate acrylic copolymer latices forming photocurable coalesced films and prepared by adding a photoinitiator to the latex, and which are useful for preparing lacquers and paints, particularly for building facades.
    Type: Grant
    Filed: July 19, 1996
    Date of Patent: October 20, 1998
    Assignee: Elf Atochem S.A.
    Inventors: Xavier Coqueret, Pierre Rousseau, Christophe Verge
  • Patent number: 5824761
    Abstract: The present invention relates to radiation curable silicone vinyl ethers and methods for preparing silicone vinyl ethers. More particularly, the present invention relates compositions containing vinyl ether functional silicones and to the preparation and use of silicone vinyl ethers which are curable by addition of photocleavable acids and exposure to ultraviolet or electron beam radiation.
    Type: Grant
    Filed: January 16, 1997
    Date of Patent: October 20, 1998
    Assignee: Dow Corning Corporation
    Inventors: Valerie Joy Bujanowski, Shedric Oneal Glover, Susan Victoria Perz, Maris Jazeps Ziemelis, Gary Rex Homan, Michael Ward Skinner
  • Patent number: 5814679
    Abstract: Carbinol functionalized silicones provide improved release properties to epoxy silicone photo-curable release compositions, by co-photo-curing with the epoxy functionalized silicone.
    Type: Grant
    Filed: October 18, 1996
    Date of Patent: September 29, 1998
    Assignee: General Electric Company
    Inventors: Richard P. Eckberg, Robert F. Agars
  • Patent number: 5798396
    Abstract: The present invention is directed to sulfonium salt-containing compounds represented by a following general formula; ##STR1## wherein R.sub.1 is alkyl containing from 1 to 18 carbon atoms, hydroxy, alkoxy containing from 1 to 18 carbon atoms, alkylcarbonyloxy containing from 1 to 18 carbon atoms or halogen, n is any of 0, 1, 2 or 3, however, each of R.sub.1 may be different from the others when n is 2 or more, R.sub.2 is alkyl containing from 1 to 6 carbon atoms, R.sub.3 and R.sub.4 are each independently hydrogen or alkyl containing from 1 to 6 carbon atoms, R.sub.5 and R.sub.6 are each independently hydrogen, alkyl containing from 1 to 6 carbon atoms, hydroxy, alkoxy containing from 1 to 6 carbon atoms, alkylcarbonyloxy containing from 1 to 18 carbon atoms or aromatic carbonyloxy, and R.sub.7 is alkyl containing from 4 to 20 carbon atoms or a group represented by a following formula; ##STR2## wherein R.sub.
    Type: Grant
    Filed: September 4, 1996
    Date of Patent: August 25, 1998
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Eiji Takahashi, Hiroo Muramoto
  • Patent number: 5789136
    Abstract: Proposed is an alkali-developable negative-working photoresist composition in the form of a solution capable of exhibiting high sensitivity and greatly improved stability of the resist layer of the composition on a substrate surface after pattern-wise exposure to actinic rays and kept for a substantial length of time before further processing. The photoresist composition comprises, as the essential ingredients, (a) an alkali-soluble resin such as a copolymer of hydroxystyrene and styrene; (b) a compound capable of releasing an acid when irradiated with actinic rays such as tris(2,3-dibromopropyl) isocyanurate; (c) a crosslinking agent selected from the group consisting of melamine resins and urea resins substituted at the N-positions by methylol groups, alkoxy methyl groups or a combination thereof; and (d) a sensitivity improver which is hexa(methoxymethyl) melamine or di(methoxymethyl) urea, each in a specified proportion.
    Type: Grant
    Filed: April 5, 1996
    Date of Patent: August 4, 1998
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Mitsuru Sato, Katsumi Oomori, Kiyoshi Ishikawa, Etsuko Iguchi, Fumitake Kaneko
  • Patent number: 5783358
    Abstract: The invention relates to a process for stabilizing a liquid radiation-curable composition comprising a cationically polymerizable compound and a photoinitiator for cationic polymerization against premature commencement of the polymerization, in which a basic ion exchanger is brought into contact with the composition, at least for a certain time. The ion exchanger is preferably removed before commencement of the radiation curing, at least from the part of the radiation-sensitive composition which comes into contact with the radiation. The process is particularly suitable for stabilizing stereolithography baths in extended use against an undesired increase in viscosity.
    Type: Grant
    Filed: March 6, 1996
    Date of Patent: July 21, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Adrian Schulthess, Bettina Steinmann, Manfred Hofmann
  • Patent number: 5783354
    Abstract: A positive-working radiation-sensitive mixture essentially consists of(a.sub.1) at least one water-insoluble, organic polymeric binder which contains acid-labile groups and becomes soluble in aqueous alkaline solutions as a result of the action of acid, or(a.sub.2.1) a polymeric binder which is insoluble in water and soluble in aqueous alkaline solutions and(a.sub.2.2) a low molecular weight organic compound whose solubility and aqueous alkaline developer is increased as a result of the action of acid, and(b) at least one organic compound which produces an acid under the action of actinic radiation, and, if required,(c) one or more further organic compounds which differ from (b),at least one of the components (a.sub.1), (a.sub.2.1), (a.sub.2.2), (b) and (c) containing a bonded group of the general formula (I) --O.sup..crclbar. N.sup..sym. R.sub.4, or component (c) being of the formula (II) ##STR1## The radiation-sensitive mixture is suitable for the production of relief structures.
    Type: Grant
    Filed: September 9, 1996
    Date of Patent: July 21, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhold Schwalm, Dirk Funhoff, Horst Binder
  • Patent number: 5776995
    Abstract: A photosensitive resin composition comprising the following components (A), (B) and (C): (A) a photopolymerizable urethane (meth)acrylate compound containing at least two acryloyl or methacryloyl groups, (B) an alkali-soluble polymer compound having an acid value of from 50 to 250 mgKOH/g, and (C) a photopolymerization initiator, wherein the photosensitive resin composition has an electrical insulation resistance of 8.0.times.10.sup.9 to 1.0.times.1.0.sup.14 .OMEGA..multidot.cm after photocuring. A photosensitive resin laminated film comprising a flexible film, a photosensitive layer provided on the flexible film, and a releasable film layer provided on the photosensitive layer, wherein the photosensitive layer comprises the above photosensitive resin composition.
    Type: Grant
    Filed: October 25, 1996
    Date of Patent: July 7, 1998
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroyuki Obiya, Ryuma Mizusawa
  • Patent number: 5776998
    Abstract: The invention herein is a non-aqueous solvent free process for producing UV curable adhesive and sealant compositions comprising a tackifying resin and a monohydroxylated epoxidized polydiene polymer which is comprised of at least two polymerizable ethnically unsaturated hydrocarbon monomers wherein at least one is a diene monomer which yields unsaturation suitable for epoxidation and wherein the polymer contains from 0.1 to 7.0 milliequivalents of epoxy per gram of polymer. The process involves mixing the components with an insoluble photoinitiator under conditions of high shear and/or cavitation. The invention also relates to a film of 5 mils to one inch thick which is formed from the composition made according to the process above.
    Type: Grant
    Filed: April 26, 1996
    Date of Patent: July 7, 1998
    Assignee: Shell Oil Company
    Inventors: Jeffrey George Southwick, Kathleen Suzanne Kiibler, James Robert Erickson
  • Patent number: 5773194
    Abstract: A light sensitive composition comprising (a) a vinyl type polymer having a unit represented by the following Formula (1) and a carboxyl group, (b) a monomer, oligomer or polymer containing at least one polymerizable double bond in its molecule, (c) a photopolymerization initiator and (d) a polymerization inhibitor capable of trapping a radical, ##STR1##
    Type: Grant
    Filed: August 29, 1996
    Date of Patent: June 30, 1998
    Assignee: Konica Corporation
    Inventors: Ryoji Hattori, Tatsuichi Maehashi, Takaaki Kuroki, Sota Kawakami
  • Patent number: 5773192
    Abstract: Disclosed are an organic silicon compound having a repeating unit represented by general formula (I) shown below, a resist, a thermal polymerization composition and a photopolymerization composition containing the organic silicon compound, ##STR1## wherein R.sup.1 is a t-butyl group or a pyranyl group, R.sup.2 is an hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 1 to 24 carbon atoms, or a substituted or unsubstituted aralkyl having 7 to 24 carbon atoms, R.sup.3 is a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 24 carbon atoms or an alkoxyl group, and k represents an integer from 0 to 4.
    Type: Grant
    Filed: February 3, 1997
    Date of Patent: June 30, 1998
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Shinji Murai, Yoshihiko Nakano, Ken Uchida, Shuji Hayase
  • Patent number: 5759721
    Abstract: A holographic recording medium comprises an acid generator capable of producing an acid upon exposure to actinic radiation; a binder; and at least one monomer or oligomer capable of undergoing cationic polymerization initiated by the acid produced from the acid generator. This recording medium is not subject to the disadvantages (for example, oxygen sensitivity) associated with radical-polymerized prior art holographic recording media.
    Type: Grant
    Filed: November 1, 1996
    Date of Patent: June 2, 1998
    Assignee: Polaroid Corporation
    Inventors: Pradeep K. Dhal, Michael G. Horner, Richard T. Ingwall, Eric S. Kolb, Parag G. Mehta, Richard A. Minns, Howard G. Schild, David A. Waldman
  • Patent number: 5759750
    Abstract: A radiation-sensitive mixture essentially consisting of(a) a water-insoluble binder or binder mixture and(b) a compound which forms a strong acid on exposure to radiation,component (a) being a phenolic resin in which some or all of the phenolic hydroxyl groups have been replaced with groups (IA) or (IB) ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each alkyl or R.sup.1 together with R.sup.2 forms a ring and X is CH.sub.2, O, S, SO.sub.2 or NR.sup.4, is suitable for the production of relief structures.
    Type: Grant
    Filed: April 18, 1997
    Date of Patent: June 2, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Binder, Reinhold Schwalm, Dirk Funhoff
  • Patent number: 5750587
    Abstract: The present invention relates to a radiation curable silicone release coating composition comprising (A) an alicyclic epoxy-functional silicone graft copolymer, (B) an organic compound having at least 2 alicyclic epoxy groups, and (C) a photocuring catalyst. The compositions of this invention are highly adhesive to a variety of substrates, have excellent coatability, and the release resistance values of films having the composition of this invention cured thereon can be adjusted over a wide range of values.
    Type: Grant
    Filed: April 24, 1996
    Date of Patent: May 12, 1998
    Assignee: Dow Corning Toray Silicone Co., Ltd.
    Inventors: Ryuko Manzouji, Tadashi Okawa
  • Patent number: 5750590
    Abstract: Polymerizable materials that contain "oxetanes" (trimethylene oxides) shrink only slightly when polymerized in the presence of a cationic polymerization catalyst. The materials are particular appropriate for coatings and for medical and dental purposes.
    Type: Grant
    Filed: July 3, 1996
    Date of Patent: May 12, 1998
    Assignee: Heraeus Kulzer GmbH
    Inventors: Roland Schaefer, Detlef Heindl, Dieter Schodel, Oskar Nuyken, Ralf Bohner, Christoph Erdmann
  • Patent number: 5747172
    Abstract: Silicone release agents comprising propenyl-ether functionalized silicones exhibit a rapid cationic induce photo-cure. Such propenyl-ether functionalized silicones are synthesized by the hydrosilation of various .alpha.-allyloxy-.omega.-(1-propenoxy) alkanes with various linear and cyclic hydrogen functional siloxanes.
    Type: Grant
    Filed: August 30, 1995
    Date of Patent: May 5, 1998
    Assignee: General Electric Company
    Inventor: James V. Crivello
  • Patent number: 5731364
    Abstract: The invention provides positive- and negative-acting a photoresist compositions that contain a photoacid generator component that includes multiple aryl sulfonium compounds. Specifically, the photoactive component contains at least one multiple cation aryl sulfonium compound, preferably a di-cation compound. The photoactive component of the resists of the invention can be conveniently prepared and provide a deep UV sensitive resist with excellent microlithographic properties.
    Type: Grant
    Filed: January 24, 1996
    Date of Patent: March 24, 1998
    Assignee: Shipley Company, L.L.C.
    Inventors: Roger F. Sinta, James F. Cameron, Timothy G. Adams, Martha M. Rajaratnam, Michael F. Cronin
  • Patent number: 5730764
    Abstract: Coated abrasive products are disclosed in which an ionizing irradiation curable epoxy resin formulation is employed as an abrasive binder. The ionizing irradiation curable epoxy resin formulation contains an onium salt initiator and is employed as at least one of the coatings of the coated abrasive product.
    Type: Grant
    Filed: January 24, 1997
    Date of Patent: March 24, 1998
    Inventors: Sue Ellen Williamson, Richard R. Kemmerer
  • Patent number: 5726216
    Abstract: Mixtures of epoxy resins with cationic initiators are curable under high energy ionizing radiation such as electron beam radiation, X-ray radiation, and gamma radiation. The composition of this process consists of an epoxy resin, a cationic initiator such as a diaryliodonium or triarylsulfonium salt of specific anions, and a toughening agent such as a thermoplastic, hydroxy-containing thermoplastic oligomer, epoxy-containing thermoplastic oligomer, reactive flexibilizer, rubber, elastomer, or mixture thereof. Cured compositions have high glass transition temperatures, good mechanical properties, and good toughness. These properties are comparable to those of similar thermally cured epoxies.
    Type: Grant
    Filed: July 8, 1996
    Date of Patent: March 10, 1998
    Assignee: Lockheed Martin Energy Systems, Inc.
    Inventors: Christopher J. Janke, George F. Dorsey, Stephen J. Havens, Vincent J. Lopata
  • Patent number: 5721290
    Abstract: Oxo acids having the formula:HOOC(((CH2).sub.s O).sub.t ((CH2).sub.u O).sub.v R"where R" is a monovalent radical selected from the group consisting of hydrogen, one to forty carbon alkyl, alkylene, alkynylene, aromatic, alkylaromatic or carboxyl groups and the subscripts s, t, u and v are zero or positive subject to the limitation that at least s and t or u and v must be positive reacted with epoxy functional silicones according to scheme: ##STR1## at a molar level that is less than stoichiometric with respect to the epoxy functionality present improve the miscibility of certain photo-catalysts in the epoxy functional silicone.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: February 24, 1998
    Assignee: General Electric Company
    Inventors: Richard P. Eckberg, Robert F. Agars
  • Patent number: 5721289
    Abstract: A curable pressure sensitive adhesive having long shelf stability comprising (a) at least one free radically polymerized polymer; (2) at least one cationically-polymerizable monomer; (3) a photo-activatable catalyst system for the cationically-polymerizable monomer comprising either at least one organometallic complex salt or at least one onium salt; and (4) optionally, a monohydric or polyhydric alcohol, wherein there is essentially no conversion of the cationically-polymerizable monomer of the curable pressure sensitive adhesive when stored in a manner to exclude actinic radiation, and methods of making the same.
    Type: Grant
    Filed: October 5, 1995
    Date of Patent: February 24, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Naimul Karim, Kevin E. Kinzer, Albert I. Everaerts, Leo W. Halm, Steven J. Keipert, Jerry W. Williams
  • Patent number: 5721291
    Abstract: The invention relates to a composition based on crosslinkable epoxy-functional organopolysiloxanes. This composition comprises:A. at least 10% by weight of a linear polyorganosiloxane A (POS) of average general formula (II): ##STR1## in which: R.sub.1 is CH.sub.3, R' is an alkylene containing 2 to 50 C, R is an alkyl having from 6 to 26 C, X is R.sub.1, H, --R'-epoxy or hydroxyl, x=40-150, t=3-9, z=0-5 and y=0,B. at least one second crosslinkable epoxy-functional POS (B), B being present in the proportion of at most 90% by weight and corresponding to: B(a) with x=160-1000, t=1-15, z=0-5 and y=0, B(b) with x=0-120, t=10-30, z=0-5 and y=0, or B(c) with x=0-200, t=0-5, z=0-5 and y=10-90,C. and at least one photoinitiator.This composition can be used in the manufacture of protectors for adhesive bodies ("release liners"), papers or plastics or of liner-free self-adhesive labels.
    Type: Grant
    Filed: February 20, 1996
    Date of Patent: February 24, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Eric Gaulle, Christian Priou, Andre Soldat
  • Patent number: 5708047
    Abstract: A method for decorating a substrate with hot stamping foil comprising the steps of:a) applying an ink composition comprised of a cationically radiation cured cycloaliphatic epoxide to the substrate in a predetermined design, said ink being operable when cured to bond to the substrate,b) curing the ink on the substrate by exposing to the radiation by which it is curable, thereby bonding the ink composition to the substrate,c) pressing a sheet of hot stamping foil against the substrate with a die heated to a temperature sufficient to cause a portion of the hot stamping foil to adhere to the heated, cured ink design but not to the ink-free areas of the substrate, andd) removing the die, thereby leaving behind a portion of the foil adhered to the ink design.
    Type: Grant
    Filed: December 30, 1994
    Date of Patent: January 13, 1998
    Assignee: Revlon Consumer Products Corporation
    Inventors: Melvin Edwin Kamen, Bhupendra Patel
  • Patent number: 5703137
    Abstract: The present invention relates to initiators for the polymerization and/or crosslinking, cationically and under photochemical and/or thermal activation and/or activation by a beam of electrons, of monomers and/or polymers containing organofunctional groups.The said initiators are of the type comprising an onium salt of an element from groups 15 to 17 of the Periodic Table (Chem & Eng News, Vol 63, N5, 26, of 4 Feb. 1985) and they are characterized in that they contain at least one polymerization and/or crosslinking accelerator chosen from .alpha.-hydroxylated carboxylic acid esters such as, for example, lactic acid esters. Another subject of the invention is compositions based on at least one cationically crosslinkable polyorganosiloxane and on at least one initiator.
    Type: Grant
    Filed: March 14, 1996
    Date of Patent: December 30, 1997
    Assignee: Rhone-Poulenc Chimie
    Inventors: Christian Priou, Stuart Kerr, III
  • Patent number: 5696177
    Abstract: An active energy ray-curable resin composition comprises:(i) a linear polymer having a glass transition temperature at least equal to 50.degree. C. and a weight-average molecular weight of at least about 3.0.times.10.sup.4 ; and(ii) a resin obtained by esterifying, with an unsaturated carboxylic acid, a part of epoxy groups present in an epoxy resin comprising at least one compound having at least two epoxy groups in a molecule.
    Type: Grant
    Filed: May 10, 1994
    Date of Patent: December 9, 1997
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Munakata
  • Patent number: 5691395
    Abstract: Radiation sensitive compositions, processes for using the compositions, and articles of manufacture comprising the compositions. The photoimageable compositions of the invention comprises a radiation sensitive component, a resin binder and a polybutadiene that comprises one or more internal epoxide groups. In preferred aspects, the compositions of the invention further comprise a crosslinking agent such as a melamine or an epoxidized material, or mixtures thereof.
    Type: Grant
    Filed: July 12, 1994
    Date of Patent: November 25, 1997
    Assignee: Shipley Company Inc.
    Inventors: Philip D. Knudsen, Charles R. Shipley, Daniel Y. Pai
  • Patent number: 5684065
    Abstract: To provide a fluorine-containing resin molded article surface-modified by irradiating, onto a surface thereof, a laser beam having a wavelength of 150 to 370 nm through a basic solution, preferably an aqueous basic solution. The surface-modified fluorine-containing resin molded article is excellent in adhesion to not only organic materials but also metals.
    Type: Grant
    Filed: December 19, 1996
    Date of Patent: November 4, 1997
    Assignee: Daikin Industries, Ltd.
    Inventors: Hiroyuki Hiraoka, Shinji Tamaru, Osamu Tanaka
  • Patent number: 5679496
    Abstract: A chemically amplified positive resist composition contains a novel trifluoromethanesulfonic or p-toluenesulfonic acid sulfonium salt having at least one tert-butoxycarbonylmethoxy group as an acid labile group. The composition is highly sensitive to high energy radiation, especially KrF excimer laser and has high sensitivity, resolution and plasma etching resistance while the resulting resist pattern is heat resistant.
    Type: Grant
    Filed: December 4, 1995
    Date of Patent: October 21, 1997
    Assignees: Shin-Etsu Chemical Co., Ltd., Nippon Telegraph and Telephone Corp.
    Inventors: Youichi Ohsawa, Satoshi Watanabe, Katsuyuki Oikawa, Akinobu Tanaka, Yoshio Kawai, Jiro Nakamura
  • Patent number: 5674922
    Abstract: Active energy beam-curable compositions which comprise (1) at least one compound having one oxetane ring and one hydroxyl group in the molecule, (2) at least one compound having one or more oxirane rings in the molecule and (3) at least one compound which initiates cathionic polymerization by irradiation of active energy beams, are provided. The compositions can be rapidly cured by irradiation of active energy beams, such as ultraviolet rays and electron beams, to give excellent adhesion to basic materials.
    Type: Grant
    Filed: July 16, 1996
    Date of Patent: October 7, 1997
    Assignee: Toagosei Co., Ltd.
    Inventors: Ichiro Igarashi, Hiroshi Sasaki
  • Patent number: 5667937
    Abstract: A combination of a photoacid precursor and sensitizer for use with multiple wavelengths of an argon ion laser.
    Type: Grant
    Filed: July 2, 1996
    Date of Patent: September 16, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: John Alan Lawton, Jonathan V. Caspar
  • Patent number: 5667934
    Abstract: A thermally stable photoimaging composition and a method of using the same, especially on circuit boards as a solder mask is provided. The composition includes a polymerizable resin or resin system, a cationic photoinitiator, a solvent, and an optically transparent ceramic filler. Preferably, the composition has a coefficient of thermal expansion of about 28-40 ppm/.degree.C., which closely matches the coefficient of thermal expansion of the solder used on the circuit board components.
    Type: Grant
    Filed: October 9, 1990
    Date of Patent: September 16, 1997
    Assignee: International Business Machines Corporation
    Inventors: Voya Rista Markovich, Ashit Arvind Mehta, Eugene Roman Skarvinko, David Wei Wang
  • Patent number: 5665792
    Abstract: The present invention discloses stabilizers for formulations containing photoacid precursors and cationically polymerizable materials. The stabilizers have a limited solubility in the formulations and are in solubility equilibrium in the formulation. The stabilizers being present as a solid phase in the formulation in excess of their solubility limit, the concentration of the stabilizers is continuously replenished as the stabilizer reacts with undesired free acid.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: September 9, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: John Alan Lawton, William John Nebe, Glen Anthony Thommes
  • Patent number: 5665526
    Abstract: A thermally stable photoimaging composition and a method of using the same, especially on circuit boards as a solder mask is provided. The composition includes a polymerizable resin or resin system, a cationic photoinitiator, a solvent, and an optically transparent ceramic filler. Preferably, the composition has a coefficient of thermal expansion of about 28-40 ppm/.degree. C., which closely matches the coefficient of thermal expansion of the solder used on the circuit board components.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: September 9, 1997
    Assignee: International Business Machines Corporation
    Inventors: Voya Rista Markovich, Ashit Arvind Mehta, Eugene Roman Skarvinko, David Wei Wang
  • Patent number: 5665791
    Abstract: Novel photosensitive polymer films are provided that include (1) a polymer carrier having .dbd.N--C(.dbd.O)-- groups; (2) an initiation system for photo polymerization; (3) polymerizable compounds; and (4) other chemicals as appropriate. The photosensitive polymer films demonstrate short pump times, short DRAW times, short fix times, and reduced noise levels equal to one-third to one-fifth the noise level of prior photosensitive polymer films.
    Type: Grant
    Filed: September 21, 1995
    Date of Patent: September 9, 1997
    Assignee: Tamarack Storage Devices, Inc.
    Inventors: Chung J. Lee, Jahja I. Trisnadi
  • Patent number: 5658964
    Abstract: A printing ink for the printing of security documents by the method of engraved steel die printing, having a viscosity of at least 1 Pa.multidot.s at 40.degree. C. under a shear of about 1000 sec.sup.-1, containing a binder matrix, a polymerization initiator for polymerizable matrix components, fillers and pigments, and the usual additives. The binder matrix contains at least one cationically polymerizable compound, modified to bring about the desired rheology of the ink, and the photoinitiator, activable by UV, heat and EB, is an onium salt capable of releasing a Lewis or Bronsted acid.This ink has best and very rapid drying characteristics.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: August 19, 1997
    Assignee: SICPA Holding S.A.
    Inventors: Philippe Amon, Haim Bretler, Anton Bleikolm, Olivier Rozumek, Pierre Degott
  • Patent number: 5658965
    Abstract: The present invention relates to a radiation curable silicone release coating composition comprising an alicyclic epoxy-functional silicone graft copolymer and a photocuring catalyst. The release coatings of this invention upon curing by exposure to UV light form release films that are highly adhesive for a variety of substrates, have an excellent coatability, and its release resistance can be adjusted over a wide range of values.
    Type: Grant
    Filed: March 27, 1996
    Date of Patent: August 19, 1997
    Assignee: Dow Corning Toray Silicone Co., Ltd.
    Inventors: Ryuko Manzouji, Tadashi Okawa
  • Patent number: 5656336
    Abstract: A method for applying a decoration to a glass substrate comprising applying an ink composition comprising a bis phenol-A epoxy resin to the glass in a predetermined design that leaves some areas of the glass ink free, said ink being operable when cured to bond to the glass substrate, and curing the ink on the substrate by exposing it to the radiation by which it is curable thereby bonding the ink to the glass substrate.
    Type: Grant
    Filed: March 8, 1996
    Date of Patent: August 12, 1997
    Assignee: Revlon Consumer Products Corporation
    Inventors: Melvin Edwin Kamen, Ming Hu
  • Patent number: 5654121
    Abstract: The invention relates to a positive-working radiation-sensitive mixture containing a) a polymeric binder having acid-labile groups and b) a compound which forms a strong acid on irradiation, in which the binder simultaneously contains units of the formulae I, II and IIIR.sup.1 --OH (I) ,R.sup.1 --O--CO.sub.2 R.sup.2 (II)R.sup.1 --O--CH.sub.2 --CHR.sup.3 --OH (III).The mixture is used to coat radiation-sensitive recording material which can be used to produce printing plates and photoresists.
    Type: Grant
    Filed: April 27, 1995
    Date of Patent: August 5, 1997
    Assignee: Agfa-Gevaert AG
    Inventors: Mathias Eichhorn, Gerhard Buhr
  • Patent number: 5650453
    Abstract: Blends of epoxysilicone polymers and vinyl ether monomers or oligomers and an effective amount of a suitable iodonium photocatalyst provide an ultraviolet curable low viscosity silicone coating composition.
    Type: Grant
    Filed: April 28, 1995
    Date of Patent: July 22, 1997
    Assignee: General Electric Company
    Inventors: Richard P. Eckberg, Michael J. O'Brien
  • Patent number: 5648196
    Abstract: The present invention provides positive-tone and negative-tone photoresists including a photoinitiator comprising a compound of Formula (I): ##STR1## wherein R.sub.1 and R.sub.2 are independently selected from C.sub.1 -C.sub.6 alkyl; n is a number from 2 to 5, and An.sup.- is an anion. The photoinitiator comprising the compound of Formula (I) being soluble in water. Methods of preparing positive-tone and negative-tone photoresists are also provided.
    Type: Grant
    Filed: July 14, 1995
    Date of Patent: July 15, 1997
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Jean M. J. Frechet, Sang-Yeon Shim