Specified Rate-affecting Material Contains Onium Group Patents (Class 522/25)
  • Patent number: 5639802
    Abstract: The present invention relates to a novel class of compounds which absorb light at wavelengths greater than 350 nm and are useful as fluorescers or as photoinitiators. The present invention provides compounds of the formulas (I) and (II) and their equivalents (the nomenclature of the compounds used herein is based on the numbering of positions as shown in formula (I)): ##STR1## where: when W is .dbd.O, W.sup.1 is hydrogen or --OR.sup.9 and when W is .dbd.NR.sup.+.sub.2, W is hydrogen or --NR.sub.2, A is hydrogen, alkenyl, alkyl or an election withdrawing group, and the remaining groups are as defined in the disclosure.
    Type: Grant
    Filed: November 23, 1993
    Date of Patent: June 17, 1997
    Assignee: Spectra Group Limited, Inc.
    Inventors: Douglas C. Neckers, Yubai Bi
  • Patent number: 5631307
    Abstract: A photopolymerization initiator composition almost free from deactivation and capable of giving a photopolymerizable composition which is almost free from a decrease in the photopolymerization rate in a medium having a high viscosity and shows a high curing rate, containing(A) a sulfonium organoboron complex or oxosulfonium organoboron complex of the formula (1), ##STR1## (B) a sensitizer having electron donating capability and electron acceptability in an excited state.
    Type: Grant
    Filed: June 27, 1995
    Date of Patent: May 20, 1997
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Yasuhiro Tanaka, Yasumasa Toba, Madoka Yasuike, Tadashi Tanoue, Kaoru Nakajima
  • Patent number: 5629354
    Abstract: Improved photopolymerization initiator systems are comprised of a spectral sensitizer that sensitizes in the ultraviolet or visible regions of the spectrum and an N-aryl, O-aryl or S-aryl polycarboxylic acid co-initiator. The improved initiator systems are incorporated in photo-polymerizable compositions containing one or more addition-polymerizable ethylenically-unsaturated compounds to form compositions suitable for the preparation of radiation-sensitive layers in lithographic printing plates adapted to be imagewise-exposed with ultraviolet- or visible-light-emitting lasers such as argon-ion lasers and frequency doubled Nd:YAG lasers. Such plates are able to effectively meet the dual requirements of very high photospeed and very good shelf-life required in computer-to-plate systems.
    Type: Grant
    Filed: February 28, 1995
    Date of Patent: May 13, 1997
    Assignee: Eastman Kodak Company
    Inventors: Paul R. West, Jeffery A. Gurney
  • Patent number: 5607817
    Abstract: A photopolymerizable composition comprising an addition polymerizable compound having at least one ethylenically unsaturated double bond and a photopolymerization initiator system, wherein the photopolymerization initiator system comprises:(a) a sensitizer of the formula (I) ##STR1## wherein -A is ##STR2## wherein each of R.sup.1 and R.sup.2 is a hydrogen atom, an alkyl group, an aryl group or a halogen atom, each of R.sup.3 and R.sup.4 is an alkyl group which may have substituents, each of R.sup.5 to R.sup.8 is a hydrogen atom, an alkyl group or an alkoxy group, or R.sup.3 and R.sup.4, R.sup.3 and R.sup.5 and/or R.sup.4 and R.sup.6 bond to each other to form a ring structure, and n is 0, 1 or 2; and each of X.sup.1 and X.sup.
    Type: Grant
    Filed: August 18, 1994
    Date of Patent: March 4, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hideki Nagasaka, Masaaki Tsuchiyama, Toshiyuki Urano
  • Patent number: 5605781
    Abstract: A photosensitive composition containing a curable cyanate ester and a cationic photoinitiator; and use thereof to form a resist image.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: February 25, 1997
    Assignee: International Business Machines Corporation
    Inventors: Jeffrey D. Gelorme, Eugene R. Skarvinko, David W. Wang
  • Patent number: 5602191
    Abstract: Radiation-curable acrylates are prepared by a process in which the hydroxy compound is reacted with acrylic acid or methacrylic acid in a first stage and, in a second stage, the reaction product of the first stage is reacted with an epoxide compound in the presence of, as a catalyst, a quaternary ammonium or phosphonium compound of the general formula ##STR1## where X.sup.- is an opposite ion and R.sup.1 to R.sup.4 independently of one another are each C.sub.1 -C.sub.18 -alkyl which may be substituted by one or two phenyl groups or are each C.sub.6 -C.sub.12 -aryl which may be substituted by one or two C.sub.1 -C.sub.6 -alkyl groups.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: February 11, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Reich, Erich Beck, Edmund Keil, Ulrich Erhardt, Adolf Nuber
  • Patent number: 5593812
    Abstract: The sensitivity of a photoresist to actinic light is improved by the addition of certain dyes. The photoresist includes a polymer matrix, a photosensitive acid generator and at least one compound selected from the group consisting of dyes containing at least one heterosulphur atom such as 2,2.sup.1,5.sup.1,2"-terthiophene and its derivatives; thianthrene and its derivatives, and 4,6-diphenylthieno(3,4-d)-1,3-dioxol-2-one-5,5-dioxide; phenylsulfone and its derivatives; and 4,5-diphenyl-1,3-dioxol-2-one; 3,4-bis(acetoxymethyl)furan; chelidonic acid and its derivatives; and 5,7,12,14-pentacenetetrone. Resist images on a substrate are formed from the compositions.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: January 14, 1997
    Assignee: International Business Machines Corporation
    Inventors: Edward D. Babich, Karen E. Petrillo, John P. Simons, David E. Seeger
  • Patent number: 5585414
    Abstract: Resin compositions useful for filament winding applications comprising an epoxy component including at least one polyepoxide resin curable by heat, an olefinicially unsaturated monomer component including at least one polyolefinically unsaturated monomer curable by actinic radiation, at least one photoinitiator, at least one organic peroxide, and a heat activated curing agent for epoxides. The compositions have a viscosity less than about 2000 centipoise (cps) and are capable of retaining this viscosity for at least about 2 hours at a temperature of from about ambient temperature to about 60.degree. C. The resins are capable of being immobilized by actinic radiation exposure and further heat cured without substantial resin drip. One or more organic peroxides are employed, selected from the group of organic peroxides having 10 hour decomposition half lives at temperatures of from about 50.degree. C. to less than about 104.degree. C.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: December 17, 1996
    Assignee: Loctite Corporation
    Inventors: Philip T. Klemarczyk, Yoshihisa Okamoto, James P. Moran, Jr.
  • Patent number: 5578417
    Abstract: A process is disclosed for producing a liquid jet recording head comprising applying an active energy-curing resin composition onto at least a part of a surface of a first member for forming a wall of the liquid path; exposing the applied active energy-ray-curing resin to an active energy ray selected from the group consisting of an ultraviolet-ray having an intensity of 1 mW/cm.sup.2 to 100 mW/cm.sup.2 and an electron beam having an intensity of 0.5M Rad to 20M Rad; and providing a second member on the exposed active energy-ray-curing resin composition.
    Type: Grant
    Filed: March 20, 1995
    Date of Patent: November 26, 1996
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Saito
  • Patent number: 5578418
    Abstract: A process is disclosed for producing a liquid jet recording head comprising applying an active energy-curing resin composition onto at least a part of a surface of a first member for forming a wall of the liquid path; exposing the applied active energy-ray-curing resin to an active energy ray selected from the group consisting of an ultraviolet-ray having an intensity of 1 mW/cm.sup.2 to 100 mW/cm.sup.2 and an electron beam having an intensity of 0.5M Rad to 20M Rad; and providing a second member on the exposed active energy-ray-curing resin composition.
    Type: Grant
    Filed: March 20, 1995
    Date of Patent: November 26, 1996
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Saito
  • Patent number: 5576357
    Abstract: A one-component reactive resin system which is stable in storage but nevertheless can readily be cured completely comprises a mixture of commercially available epoxy resins and phosphorus-containing glycidyl esters, in particular phosphonic acid diglycidyl esters, as well as cationic photoinitiators. The low-viscosity reactive resin systems cannot be cured purely by means of heat and can be processed at high temperatures and in particular can have a high filler content. The reactive resin systems, which are stable to storage even after UV activation, can be cured to flame-resistant molded materials under moderate conditions.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: November 19, 1996
    Assignee: Siemens Aktiengesellschaft
    Inventors: Heiner Bayer, Winfried Plundrich, Ernst Wipfelder
  • Patent number: 5565499
    Abstract: Resin compositions useful for filament winding applications comprising an epoxy component including at least one polyepoxide resin curable by heat, an olefinicially unsaturated monomer component including at least one polyolefinically unsaturated monomer curable by actinic radiation, at least one photoinitiator, at least one organic peroxide, and a heat activated curing agent for epoxides. The compositions have a viscosity less than about 2000 centipoise (cps) and are capable of retaining this viscosity for at least about 2 hours at a temperature of from about ambient temperature to about 60.degree. C. The resins are capable of being immobilized by actinic radiation exposure and further heat cured without substantial resin drip. One or more organic peroxides are employed, selected from the group of organic peroxides having 10 hour decomposition half lives at temperatures of from about 50.degree. C. to less than about 104.degree. C.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: October 15, 1996
    Assignee: Loctite Corporation
    Inventors: Philip T. Klemarczyk, Yoshihisa Okamoto, James P. Moran, Jr.
  • Patent number: 5554664
    Abstract: An energy-sensitive (e.g., thermal, radiation or photosensitive) initiator, curative, and/or catalytic salt that has an anion comprising a tris-(highly fluorinated alkylsulfonyl)methide, tris-(fluorinated arylsulfonyl)methide, bis-(highly fluorinated alkyl)sulfonyl imide, bis-(fluorinated aryl)sulfonyl imide, mixed aryl- and alkylsulfonyl imides and methides and any combinations thereof, has improved solubility in organic solvents, exhibit minimal corrosiveness when coatings and adhesives are prepared using the initiator, curative and/or catalytic salts, generates a highly reactive initiator, curative, and/or catalyst upon activation by energy.
    Type: Grant
    Filed: November 17, 1995
    Date of Patent: September 10, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: William M. Lamanna, Michael C. Palazzotto, Wayne S. Mahoney, Michael A. Kropp
  • Patent number: 5547713
    Abstract: A photocopolymerizable composition for backsealing a ceramic carrier and process for using the composition is disclosed. The composition comprises: a liquid, multifunctional, bisphenol based epoxy; a liquid, multifunctional hydroxyl containing organic material; a complex onium salt photoinitiator; and, a complex cupric salt initiator. The composition utilizes a strong Bronstead acid for additional deep curing created by iodonium salt thermolysis.
    Type: Grant
    Filed: August 14, 1994
    Date of Patent: August 20, 1996
    Assignee: International Business Machines Corporation
    Inventor: Julio M. Alvarado
  • Patent number: 5545676
    Abstract: Photocurable addition-polymerizable compositions containing a free-radically-polymerizable monomer and a photoinitiator system containing i) an arylidonium salt, ii) a sensitizing compound, and iii) an electron donor having an oxidation potential that is greater than zero and less than or equal to that of p-dimethyoxybenzene (1.32 volts vs. S.C.E.). The compositions cure rapidly and deeply under ultraviolet or visible light.
    Type: Grant
    Filed: December 28, 1994
    Date of Patent: August 13, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Michael C. Palazzotto, F. Andrew Ubel, III, Joel D. Oxman, M. Zaki Ali
  • Patent number: 5543262
    Abstract: A light sensitive composition which is capable of photopolymerization which includes a photopolymerizable compound a free radical generating component and a benzanthrone or substituted benzanthrone which substantially prevents photopolymerization when the light sensitive composition is exposed to actinic radiation below a threshold amount but permits photopolymerization when the light sensitive composition is exposed to actinic radiation above a threshold amount. This achieves a gate effect which eliminates or decreases unwanted partial exposure in the nonimage areas and hence improves reproduction quality.
    Type: Grant
    Filed: February 24, 1995
    Date of Patent: August 6, 1996
    Assignee: International Paper Company
    Inventors: Maria T. Sypek, John R. Delude, Paul A. Perron
  • Patent number: 5541235
    Abstract: A cationic dye in a ketone solvent, wherein the cationic dye has a counterion which comprises a linear, branched or cyclic highly fluorinated alkylsulfonyl methide or highly fluorinated alkyl sulfonyl imide.
    Type: Grant
    Filed: March 6, 1995
    Date of Patent: July 30, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Stanley C. Busman, William M. Lamanna
  • Patent number: 5534557
    Abstract: The composition of the present invention is excellent in compatibility, transparency and curability and give a cured coat of excellent gloss and of less smell, and cured products of excellent properties can be obtained by curing the composition.The present invention relates to an onium salt represented by the following formula (1): ##STR1## wherein Ar is a mono- to tetra-valent aromatic group, X is a bisphenylsulfonio group which may have a substituent, a is 1-4, b is 0 or 1-3, a+b is 1-4, n is 1-4, and Z is a halide represented by the following formula (3): ##STR2## where M is a boron atom, a phosphorus atom, an arsenic atom or an antimony atom, Q is a halogen atom, m is 3-6, l is 0 or 1, and m+l is 4-6; a photopolymerization initiator containing the onium salt as an active ingredient; an energy ray-curable composition containing the initiator; and a cured product.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: July 9, 1996
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
  • Patent number: 5516813
    Abstract: A balancing compound comprising an epoxy resin, a photoinitiator in an effective amount to cure the resin at ambient temperatures upon the application of ultraviolet light (10 nm to 400 nm) of less than 40 watts per square centimeter in less than about 30 seconds, and a filler in an effective amount to give the compound a specific gravity above 1.1.
    Type: Grant
    Filed: October 18, 1994
    Date of Patent: May 14, 1996
    Inventor: Donn R. Starkey
  • Patent number: 5514521
    Abstract: A photocurable composition comprises a radical-polymerizable unsaturated group including a mixed material which consists of polyethylene glycol di(meth)acrylate and dipentaerythritol hexa(meth)acrylate as a base material, an iron arene compound as a photopolymerization initiator, and an aniline system compound which is N,N-Dimethylaniline as a photochemical sensitizer for having a photocuring sensitivity to light having a wavelength in the range from the ultraviolet region to the infrared region.
    Type: Grant
    Filed: August 8, 1994
    Date of Patent: May 7, 1996
    Assignee: Brother Kogyo Kabushiki Kaisha
    Inventor: Naomichi Kobayashi
  • 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: 5514729
    Abstract: A dimensionally stable, UV hardenable polymeric composition is provided in which a conductive filler material is combined with a solventless resin formulation comprising a low viscosity epoxide compound, a photo initiator, and a thermal cure initiator. The properties of the polymeric composition may be adjusted through the addition of reactive diluents, poly alcohol flexiblizers, and acrylate based polymers, photo initiators, and thermal cure initiators. Conductive traces produced by extruding the polymeric composition through a syringe are subjected to a preliminary UV hardening step followed by deposition of an insulator layer and additional conductive traces, until all layers of conductive traces have been deposited. The structure is then subjected to heat until the conductive traces are fully cured. The formulation and the process described produce traces with bulk conductivity at least two times higher than any comparable conductive polymer, without using solvents.
    Type: Grant
    Filed: June 27, 1995
    Date of Patent: May 7, 1996
    Assignee: Sophia Systems Co., Ltd.
    Inventors: Joram Diamant, Henry L. Myers
  • Patent number: 5502083
    Abstract: The composition of the present invention is excellent in compatibility, transparency and curability and give a cured coat of excellent gloss and of less smell, and cured products of excellent properties can be obtained by curing the composition.The present invention relates to an onium salt represented by the following formula (1): ##STR1## wherein Ar is a mono- to tetra-valent aromatic group, X is a bisphenylsulfonio group which may have a substituent, a is 1-4, b is 0 or 1-3, a+b is 1-4, n is 1-4, and Z is a halide represented by the following formula (3):MQ.sub.m (OH).sub.l (3)where M is a boron atom, a phosphorus atom, an arsenic atom or an antimony atom, Q is a halogen atom, m is 3-6, l is 0 or 1, and m+l is 4-6; a photopolymerization initiator containing the onium salt as an active ingredient; an energy ray-curable composition containing the initiator; and a cured product.
    Type: Grant
    Filed: June 8, 1994
    Date of Patent: March 26, 1996
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
  • Patent number: 5500453
    Abstract: A sulfonium complex or oxosulfonium complex of the formula (1), ##STR1## wherein R.sup.1 is a benzyl group, a substituted benzyl group, a phenacyl group, a substituted phenacyl group, an aryloxy group, a substituted aryloxy group, an alkenyl group or a substituted alkenyl group, each of R.sup.2 and R.sup.3 is independently any one of groups defined as R.sup.1, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an aralkyl group, a substituted aralkyl group, an alkynyl group, a substituted alkynyl group, an alicyclic group, a substituted alicyclic group, an alkoxyl group, a substituted alkoxyl group, an alkylthio group, a substituted alkylthio group, an amino group or a substituted amino group, or R.sup.2 and R.sup.3 may bond together forming a ring structure, R.sup.4 is an oxygen atom or lone pair, and each of R.sup.5, R.sup.6, R.sup.7 and R.sup.
    Type: Grant
    Filed: August 4, 1994
    Date of Patent: March 19, 1996
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Yasumasa Toba, Madoka Yasuike, Yamaguchi Takeo
  • Patent number: 5492793
    Abstract: The present invention relates to an improved chemically amplified photoresist composition comprising (i) a photosensitive acid generator and (ii) a polymer comprising the reaction product of hydroxystyrene with acrylate, methacrylate or a mixture of acrylate and methacrylate.
    Type: Grant
    Filed: May 11, 1994
    Date of Patent: February 20, 1996
    Assignee: International Business Machines Corporation
    Inventors: Gregory Breyta, Christopher J. Knors, Hiroshi Ito, Ratnam Sooriyakumaran
  • Patent number: 5492942
    Abstract: A pyran derivative has a structure ofR.sup.2 R.sup.3 C.dbd.(C.sub.5 H.sub.2 R.sup.1 O)--(CH.dbd.CH).sub.n --C.sub.6 H.sub.2 R.sup.6 R.sup.7 --NR.sup.4 R.sup.5wherein n is 3 or 4; R.sup.1 is a proton, alkyl or phenyl group; each of R.sup.2 and R.sup.3 is independently a cyano, alkoxycarbonyl having an alkyl, acyl having an alkyl, aracyl having phenyl, sulfonyl, aryl, or aryloxy; each of R.sup.4 and R.sup.5 is an alkyl group; and each of R.sup.6 and R.sup.7 is a proton, provided that R.sup.4 and R.sup.5 are alkyl groups, and a pair of R.sup.4 and R.sup.6 as well as a pair of R.sup.5 and R.sup.7 can be bonded to each other to form a heterocycle.A photosensitive composition comprises a polymerizable compound, a polymerization initiator and a photosensitizer which is the pyran derivative. A photosensitive resin composition comprises a crosslinkable polymer, a crosslinking agent and the photosensitizer.
    Type: Grant
    Filed: May 24, 1994
    Date of Patent: February 20, 1996
    Assignee: Canon Kabushiki Kaisha
    Inventors: Shin Kobayashi, Susumu Matsumura, Naosato Taniguchi, Yoko Yoshinaga, Toshiyuki Sudo, Hideki Morishima, Tadashi Kaneko
  • Patent number: 5474876
    Abstract: A radiation-crosslinkable mixture which contains a carboxyl-containing precursor of a heterocyclic polymer, a copolymerizable ethylenically unsaturated ternary sulfonium salt, a photoinitiator and a polar aprotic organic solvent.
    Type: Grant
    Filed: October 5, 1994
    Date of Patent: December 12, 1995
    Assignee: BASF Lacke + Farben AG
    Inventors: Hans-Joachim Haehnle, Manfred Schwarz, Rainer Blum
  • Patent number: 5468890
    Abstract: The invention concerns iodonium salts of the general formula A-I.sup.+ --B X.sup.-, in which A is a group of the general formula ##STR1## in which C is a monovalent aromatic hydrocarbon group with 6 to 14 carbon atoms or a monovalent aromatic hydrocarbon group containing at least one oxygen and/or sulphur atom and with 5 to 14 atoms in the aromatic ring, D, E and F are each substituents of C, D being a group of the formula --(O).sub.x --(R).sub.y --SiR1/3, E being a group of the formula --OR.sup.2, F being a group of the formula --R.sup.3, a being 1, 2, or 3, b being 0, 1 or 2, c being 0, 1 or 2, x being 0 or 1 and y being 0 or 1, and R, R.sup.1, R.sup.2 and R.sup.3 are as defined in claim 1; B is a group of the formula ##STR2## in which E and F, which are as defined above, may each be bound to the 2, 3, 4, 5 or 6 position in the benzene ring, d is 0, 1 or 2, e is 0, 1 or 2 and X.sup.- is a tosylate anion or a weakly nucleophilic or non-nucleophilic anion Y.sup.- selected from the group comprising CF.sub.
    Type: Grant
    Filed: June 8, 1994
    Date of Patent: November 21, 1995
    Assignee: Wacker-Chemie GmbH
    Inventors: Christian Herzig, Silke Scheiding
  • Patent number: 5447797
    Abstract: A reaction resin mixture, which is able to be hardened thermally and by means of UV radiation, contains the following constituents:a cationically polymerizable epoxide resin;a latent hardening initiator in the form of an aralkyl-thiolanium salt; anda sensitizer of the structure ##STR1## A being --CO--, --NR-- and --CO--CO--, and D being --O--, --S--, --CO-- and --CH.sub.2).sub.x (where x= 1 or 2) or rather a single bond or two hydrogen atoms.
    Type: Grant
    Filed: August 9, 1993
    Date of Patent: September 5, 1995
    Assignee: Siemens Aktiengesellschaft
    Inventors: Bernhard Stapp, Lothar Schoen, Volker Muhrer
  • Patent number: 5445855
    Abstract: An active energy ray-curable composition comprising (A) an epoxy resin, (B) a compound selected from the group consisting of sulfonium salts and cyclopentadienyl iron compounds, (C) a compound selected from the group consisting of acrylates, methacrylates and oligomers thereof, and (D) an organic peroxide, and optionally (E) a rubber component. The composition is useful for an adhesive layer of an optical recording medium.
    Type: Grant
    Filed: August 5, 1993
    Date of Patent: August 29, 1995
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Suguru Tokita, Kenji Yamane, Hajime Inagaki, Masayoshi Kurisu
  • Patent number: 5422204
    Abstract: A photo-crosslinkable resin composition comprises (a) a polymer having an electron-donating group in a monomer unit, (b) a halogen compound, (c) an onium salt and (d) at least one sensitizer selected from the group consisting of coumarin derivatives, rhodanine derivatives, thioxanthene derivatives and unsaturated cyclopentanone compounds. The composition can be used as a hologram recording medium.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: June 6, 1995
    Assignee: Canon Kabushiki Kaisha
    Inventors: Yoko Yoshinaga, Shin Kobayashi, Susumu Matsumura, Naosato Taniguchi, Toshiyuki Sudoh, Hideki Morishima
  • Patent number: 5403869
    Abstract: An adhesive comprising (a) solid epoxy resin having a molecular weight of 5000 or more, (b) a polyfunctional epoxy resin having at least three epoxy groups, (c) an intramolecular epoxy-modified polybutadiene having at least three epoxy groups, (d) a cationic photoinitiator, and (e) a tin compound in special weight ratios, is effective for producing multiple-wire wiring boards having good heat resistance, solvent resistance and wherein the adhesive layer has no voids and prevents shift of insulated encapsulated wires.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: April 4, 1995
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Shigeharu Arike, Yorio Iwasaki, Eiichi Shinada, Toshiro Okamura, Kanji Murakami, Yuichi Nakazato
  • Patent number: 5395862
    Abstract: Disclosed is a photooxidizable initiator composition comprising a fluorone initiator and a coinitiator which is capable of accepting an electron from the fluorone upon excitation of the fluorone by actinic radiation, wherein the composition produces free radicals which initiate free radical reactions; and photohardenable compositions which comprise a free radical polymerizable compound, a fluorone initiator and a coinitiator capable of accepting an electron from the fluorone upon exposure of the composition to actinic radiation, and producing free radicals which initiate free radical polymerization.
    Type: Grant
    Filed: December 9, 1992
    Date of Patent: March 7, 1995
    Assignee: Spectra Group Limited, Inc.
    Inventors: Douglas C. Neckers, Jianmin Shi
  • Patent number: 5385807
    Abstract: A photopolymerizable composition comprises: (i) a polymerizable compound carrying an addition-polymerizable unsaturated bond; (ii) a methine compound; (iii) at least one compound selected from the group consisting of: (a) compounds having carbon-halogen bonds, (b) aromatic onium salts, (c) organic peroxides, (d) thio compounds, (e) hexaaryl-biimidazoles, (f) ketooxime esters, and (g) compounds represented by the following general formula (III): ##STR1## wherein R.sup.6, R.sup.7, R.sup.8 and R.sup.9 may be the same or different and each represents a substituted or unsubstituted alkyl, aryl, alkenyl, alkynyl or heterocyclic group, provided that at least two of R.sup.6, R.sup.7, R.sup.8 and R.sup.9 may be bonded together to form a ring structure and that at least one of them represents an alkyl group; and Z.sup.+ represents an alkali metal cation or a quaternary ammonium cation. The composition has a high sensitivity to a wide range of actinic light rays extending from ultraviolet to visible light.
    Type: Grant
    Filed: June 22, 1992
    Date of Patent: January 31, 1995
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasuo Okamoto, Syunichi Kondo, Toshinao Ukai
  • Patent number: 5384339
    Abstract: A balancing compound comprising an epoxy resin, a photoinitiator in an effective amount to cure the resin at ambient temperatures upon the application of ultraviolet light (10 nm to 400 nm) of less than 40 watts per square centimeter in less than about 30 seconds, and a filler in an effective amount to give the compound a specific gravity above 1.1.
    Type: Grant
    Filed: March 9, 1993
    Date of Patent: January 24, 1995
    Inventor: Donn R. Starkey
  • Patent number: 5378579
    Abstract: A photopolymerizable composition comprising(A) an addition-polymerizable compound having an ethylenically unsaturated double bond,(B) a compound of the formula: ##STR1## [wherein R.sup.1 is a substituted or nonsubstituted phenyl group, R.sup.2 and R.sup.3 are the same or different and indicate a hydrogen atom or a C.sub.1-4 alkyl group, R.sup.4 in an alkylene group which may have at least one substituent selected from alkyl, hydroxyl and oxo (.dbd.O) on a main chain, or which may contain at least one member selected from an oxygen atom and a cycloalkylene group in a main chain, R.sup.5 is a hydrogen atom or a methyl group, and a and b are independently 0 or 1],(C) a light absorbing compound, and(D) a film-forming polymer having alkaline solubility or alkaline swelling characteristic is disclosed. There is also disclosed a photosensitive lithographic printing plate comprising the photopolymerizable composition.
    Type: Grant
    Filed: July 8, 1992
    Date of Patent: January 3, 1995
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Seiji Arimatsu, Takakazu Hase, Yoshifumi Ichinose
  • Patent number: 5374500
    Abstract: A positive acting photoresist comprising a film forming reactive polymer; an iodonium initiator or a non-ionic compound that generates triflic acid upon exposure to radiation; and a multifunctional organic carboxylic acid is provided as well as use thereof.
    Type: Grant
    Filed: April 2, 1993
    Date of Patent: December 20, 1994
    Assignee: International Business Machines Corporation
    Inventors: Burton J. Carpenter, Jr., Michael G. McMaster, Joseph LaTorre, Logan L. Simpson
  • Patent number: 5368990
    Abstract: A photopolymerizable composition comprising an addition polymerizable compound having an ethylenically unsaturated double bond and a photopolymerization initiating composition, said photopolymerizable initiating composition comprising (a) a dye of the formula: ##STR1## [wherein R.sub.1 is H, an alkyl group having 1 to 3 carbon atoms, a phenyl group or a halogen atom; R.sub.2 is a methyl group, an ethyl group or (CH.sub.2).sub.p -Q (wherein Q is a carboxyl group, a sulfonyl group or salt thereof and p is an integer of 1 to 4); X.sub.1 and X.sub.2 are independently --O--, --S--, --CH.dbd.CH-- or >N--R.sub.2 ; Y.sub.1 and Y.sub.2 are independently H, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a phenyl group or a halogen atom; Z is --COO or --SO.sub.3 ; m is 0 or 1; and n is an integer of 1 to 4] and (b) diaryliodonium salt as a polymerization initiator.
    Type: Grant
    Filed: November 5, 1992
    Date of Patent: November 29, 1994
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Masami Kawabata, Akihiko Sato, Iwao Sumiyoshi
  • Patent number: 5364738
    Abstract: A positive-working light-sensitive composition whose solubility in a developer is increased by irradiation of light, which comprises:(a) a vinyl ether compound having at least one group represented by the following formula (A); ##STR1## wherein R.sup.3 represents a linear or branched alkylene group having 1 to 10 carbon atoms and n represents an integer of 0 or 1;(b) a compound capable of being decomposed by irradiation of an actinic light ray or a radiant ray and releasing an acid; and(c) an alkali-soluble polymer, the light-sensitive composition having high sensitivity to light and permitting the use of light of a wide wavelength range.
    Type: Grant
    Filed: October 6, 1992
    Date of Patent: November 15, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shunichi Kondo, Akira Umehara, Yoshimasa Aotani, Tsuguo Yamaoka
  • 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: 5346805
    Abstract: A photopolymerizable composition comprises a polymerizable compound having at least one ethylenically unsaturated double bond and a photopolymerization initiator, wherein the photopolymerization initiator comprises an onium compound and an acridine derivative represented by the following general formula (I): ##STR1## wherein R.sup.1 represents an unsubstituted or substituted phenyl, alkyl or alkoxy group. The composition has high sensitivity to actinic rays over a wide range of wavelength extending from ultraviolet to visible region and thus can be used for preparing a lithographic printing plate, a resin-letterpress plate, a resist or photomask for making a printed board, a monochromatic and colored sheet for transfer or color-development and a color-developing sheet.
    Type: Grant
    Filed: September 17, 1993
    Date of Patent: September 13, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Syunichi Kondo, Akira Umehara
  • Patent number: 5340847
    Abstract: A composition useful as a liquid gasket, having high working efficiency and high initial pressure resistance, is provided. The composition, characterized by being curable by ultraviolet light and by moisture, includes (a) a polysiloxane containing, on at least one molecular end, at least one group selected from the group consisting of (meth)acryl, glycidyl, propenyloxysilyl and thiol; (b) a polyorganosiloxane having silanol groups at both molecular ends; (c) a polyorganosiloxane having, on at least one molecular end, a hydrolyzable group; (d) a photopolymerization catalyst; and (e) a condensation catalyst.
    Type: Grant
    Filed: July 23, 1993
    Date of Patent: August 23, 1994
    Assignee: Three Bond Co., Ltd.
    Inventors: Yasuo Hanazuka, Ikuzo Usami, Kazuyuki Chiba, Noriko Mizutani
  • Patent number: 5326621
    Abstract: An energy polymerizable composition comprises at least one ethylenically-unsaturated monomer, one of polyurethane precursors, and at least one epoxy monomer, and a curing agent comprising an organometallic compound, and an onium salt.
    Type: Grant
    Filed: August 19, 1992
    Date of Patent: July 5, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Michael C. Palazzotto, Katherine A. Brown-Wensley, Robert J. DeVoe
  • Patent number: 5322762
    Abstract: A highly stable photopolymerizable composition which is highly photosensitive to visible light, which can be hardened using a visible light laser, such as an argon laser, which provides excellent contrast between non-irradiated portions and the substrate under red light, and, moreover, which provides excellent contrast between the portions irradiated by the laser and the portions not irradiated. The photopolymerizable composition consists of 100 parts by weight of a resin which is hardenable under visible light having an irradiation energy mainly consisting of light rays in the 400 nm to 700 nm visible light region; 0.02 to 0.5 parts by weight of at least one dye selected from the group consisting of Victoria Pure Blue, anthraquinone dyes, monoazo dyes, and merocyanine dyes, these dyes having maximum absorption wavelengths from 550 to 700 nm; 0.1 to 5 parts by weight of the leuco dye 4,4'-(phenylmethylene bis[N,N-diethylbenzene amine]; and 0.1 to 5 parts by weight of tribromomethylphenyl sulphone.
    Type: Grant
    Filed: April 13, 1993
    Date of Patent: June 21, 1994
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Kenji Kushi, Chiho Tokuhara
  • Patent number: 5300402
    Abstract: An improved photoimagable cationically polymerizable epoxy based coating material is provided. The material includes an epoxy resin system consisting essentially of between about 10% and about 80% by weight of a polyol resin which is a condensation product of epichlorohydrin and bisphenol A having a molecular weight of between about 40,000 and 130,000; between about 20% and about 90% by weight of an epoxidized octafunctional bisphenol A formaldehyde novolak resin having a molecular weight of 4,000 to 10,000; and if flame retardancy is required between about 35% and 50% by weight of an epoxidized glycidyl ether of tetrabromo bisphenol A having a softening point of between about 60 C. and about 110 C. and a molecular weight of between about 600 and 2,500. To this resin system is added about 0.
    Type: Grant
    Filed: July 15, 1991
    Date of Patent: April 5, 1994
    Assignee: International Business Machines Corporation
    Inventors: Norman A. Card, Jr., Richard A. Day, Donald H. Glatzel, David J. Russell
  • Patent number: 5275917
    Abstract: A photocurable composition comprises a radical polymerizable unsaturated group-bearing compound, a metal allene compound, and a squalilium compound. The composition is cured by application of low energy visible light or near infrared light having a long wavelength. In the composition, the metal allene compound and the squalilium dye serve as photopolymerization initiators, which are able to produce radicals by application of the long wavelength light and to polymerize the radical polymerizable unsaturated group-bearing compound.
    Type: Grant
    Filed: June 18, 1992
    Date of Patent: January 4, 1994
    Assignee: Brother Kogyo Kabushiki Kaisha
    Inventor: Kouji Inaishi
  • Patent number: 5264325
    Abstract: An improved photoimagable cationically polymerizable epoxy based coating material is provided, that is suitable for use on a variety of substrates. The material includes an epoxy resin system consisting essentially of between about 10% and about 80% by weight of a polyol resin which preferably is a condensation product of epichlorohydrin and bisphenol A having a molecular weight of between about 40,000 and 130,000; and between about 35% and 72% by weight of an epoxidized glycidyl ether of a brominated bisphenol A having a softening point of between about 60.degree. C. and about 110.degree. C. and a molecular weight of between about 600 and 2,500. A third resin, either an epoxy cresol novolak or a polyepoxy resin, is also added to the resin system. To this resin system is added about 0.
    Type: Grant
    Filed: July 21, 1992
    Date of Patent: November 23, 1993
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Richard A. Day, Donald H. Glatzel, William D. Hinsberg, John R. Mertz, David J. Russell, Gregory M. Wallraff
  • Patent number: 5260455
    Abstract: Polyepoxy silane compositions resulting from the reaction of olefinepoxide and poly(H)silanes crosslink in the presence of a catalytic amount of an 'onium catalyst when exposed to UV light. In one embodiment, two moles of an olefin-containing epoxy monomer are reacted with a bis(H)-containing silane of general formula R.sub.2 SiH.sub.2. Important to the success of this process is that RhCl.sub.3.xH.sub.2 O is capable of catalyzing the hydrosilation addition of 2 moles of olefin to R.sub.2 SiH.sub.2. The resulting diepoxysilanes are reactive monomers which undergo photopolymerization when exposed to ultraviolet light in the presence of iodonium photocatalysts.
    Type: Grant
    Filed: July 8, 1992
    Date of Patent: November 9, 1993
    Assignee: General Electric Company
    Inventor: Richard P. Eckberg
  • Patent number: 5260348
    Abstract: An improved silicone composition is disclosed, which comprises:a) at least one silanol chain-stopped polydiorganosiloxane polymer;b) an acyloxy, alkoxy, or aryloxy-functional crosslinking agent; andc) a catalytic amount of an onium salt photocatalyst.These materials are characterized by enhanced cure properties, such as short tack free time; and they can also include various other components, such as fillers, plasticizers, condensation cure catalysts, and adhesion promoters.
    Type: Grant
    Filed: January 31, 1992
    Date of Patent: November 9, 1993
    Assignee: General Electric Company
    Inventors: Brian D. Shepherd, David C. Gross
  • Patent number: 5254638
    Abstract: This invention relates to sol-gel methods for forming non-shrinking, high-glass composite materials and the products. Also taught is an inorganic-organic composite material having a solid interwoven network of an inorganic polymer matrix with interpenetrating polymerized alcohols. The inorganic matrix can be based on either Si or Ti atoms.
    Type: Grant
    Filed: March 25, 1991
    Date of Patent: October 19, 1993
    Assignee: The Reagents of the University of California
    Inventors: Bruce M. Novak, Mark W. Ellsworth