With Polycarboxylic Acid Or Derivative And A Polyol, Condensate Or Solid Polymer Thereof Patents (Class 522/101)
  • Patent number: 6555595
    Abstract: Disclosed are radiation-curable or photopolymerizable compositions, processes for applying and curing the compositions and articles bearing a cured coating of the compositions utilizing radiation-curable compositions which contain, in addition to the typical components of radiation-curable compositions, a polymer derived from 3,4-epoxy-1-butene.
    Type: Grant
    Filed: October 10, 2001
    Date of Patent: April 29, 2003
    Assignee: Rensselaer Polytechnic Institute
    Inventors: James Vincent Crivello, Marco Sangermano, Stephen Neal Falling
  • Patent number: 6531521
    Abstract: A practically excellent method for preserving a photosensitive composition Containing a photopolymerization initiator and a photopolymerizable monomer and/or oligomer, which comprises placing and preserving the photosensitive composition in a light shielding vessel, wherein the product of the void ratio (%) in the vessel and the oxygen partial pressure (hPa) in the void part is 1500 (%·hPa) or more is provided; and the method imparts remarkably improved preservation stability.
    Type: Grant
    Filed: April 17, 2001
    Date of Patent: March 11, 2003
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Baba, Toshiya Inoue, Shigeo Hozumi
  • Publication number: 20020177072
    Abstract: According to the present invention, an improved photoimagable cationically polymerizable epoxy based solder mask is provided that contains a non-brominated epoxy resin system and from about 0.1 to about 15 parts, by weight per 100 parts of resin system, of a cationic photoinitiator. The non-brominated epoxy-resin system has solids that are comprised of from about 10% to about 80% by weight, of a polyol resin having epoxy functionality; from about 0% to about 90% by weight of a polyepoxy resin; and from about 25% to about 85% by weight of an difunctional epoxy resin. Since the photosensitive cationically polymerizable epoxy based solder mask does not contain bromine, it is particularly advantageous halogens in waste processing chemicals or in incinerated scrap circuit boards are regulated by environmental concerns. The photosensitive cationically polymerizable non-brominated epoxy based solder mask has a glass transition temperature greater than about 100° C., preferably greater than about 110° C.
    Type: Application
    Filed: May 9, 2002
    Publication date: November 28, 2002
    Applicant: International Business Machines Corporation
    Inventors: Richard Allen Day, David John Russell, Donald Herman Glatzel
  • Patent number: 6465540
    Abstract: An ultraviolet curable resin composition includes (A) an ultraviolet curable resin, (B) an epoxy compound having at least two epoxy groups in one molecule, (C) a photopolymerization initiator and (D) a diluent. The ultraviolet curable resin (A) is obtained by the steps of polymerizing an ethylenically unsaturated monomer component containing (a) an ethylenically unsaturated monomer having epoxy group and (b) a compound having at least two ethylenically unsaturated groups in one molecule to prepare a copolymer, reacting the copolymer with (c) an ethylenically unsaturated monomer having carboxyl group to prepare a chemical intermediate, and reacting the chemical intermediate with (d) one of saturated and unsaturated polybasic acid anhydrides. This resin composition will be preferably used to prepare a photo solder resist ink developable with diluted alkaline aqueous solution.
    Type: Grant
    Filed: March 14, 2000
    Date of Patent: October 15, 2002
    Assignee: Goo Chemical Co., Ltd.
    Inventors: Tatsuya Kubo, Masatoshi Fujimoto, Soichi Hashimoto
  • Patent number: 6432613
    Abstract: The present invention discloses a photo-sensitive composition, used as a solder resist or a photosensitive material for insulation layers in the production of printed circuit boards. The photo-sensitive composition comprises a prepolymer containing carboxylic groups and unsaturated vinyl groups; photoinitiator; unsaturated photo-monomer; and the reaction adduct of bismaleimide derivative, barbituric acid derivative and epoxy compounds. The obtained photosensitive composition exhibits high adhesion towards PI substrates, in addition, it can be developed with alkaline water. The photosensitive composition obtained in the invention is very useful in packaging substrates, such as P-BGA, T-BGA and F-CSP due to its high heat resistance and solder resistance.
    Type: Grant
    Filed: May 30, 2001
    Date of Patent: August 13, 2002
    Assignee: Industrial Technology Research Institute
    Inventors: Man-Lin Chen, Jing-Pin Pan, Hsien-Kuang Lin, Shur-Fen Liu
  • Patent number: 6350791
    Abstract: The invention relates to a thermosettable adhesive comprising a thermosettable polymer component, a thermoformable polymer component, an effective amount of a heat-activatable and/or photoactivatable curing system for curing the thermosettable polymer component, and from 0.5-20 wt. % with respect to the mass of the thermosettable adhesive of one or more hydroxides and/or hydroxyoxides of Al, Mg and/or Zr.
    Type: Grant
    Filed: June 27, 2000
    Date of Patent: February 26, 2002
    Assignee: 3M Innovative Properties Company
    Inventors: Georg Feichtmeier, Peggy S. Willett
  • Patent number: 6350792
    Abstract: A radiation-curable composition in a liquid or solid form comprises at least one solid, non-crystalline radiation-transmissible material, dispersed in at least one cationic-curable or free-radical curable composition or mixture thereof. The solid, non-crystalline radiation-transmissible materials comprise glasses and other suitable materials that transmit (i.e., are transparent to) at least about 40% of radiation having a wavelength from about 180 to about 600 nanometers. The solid forms of the radiation-curable compositions of the invention are useful as powder coatings for coating decorative and functional objects and that would be cured by a thermal heating flow process followed by radiation exposure. The cured compositions of the invention are useful as coatings and inks for metal, paper, plastics, glass, ceramics, and wood, as adhesives, as sealants, and as composite materials and other articles and in biomedical and dental applications.
    Type: Grant
    Filed: July 13, 2000
    Date of Patent: February 26, 2002
    Assignee: Suncolor Corporation
    Inventors: David A. Smetana, Joseph V. Koleske
  • Patent number: 6332291
    Abstract: This invention relates to radiation-curable coating compositions which contain A) compounds having one or more free-radically polymerisable double bonds which additionally contain at least one further functional group reactive for the purposes of an addition and/or condensation reaction, B) compounds having one or more free-radically polymerisable double bonds, which additionally contain at least one further functional group reactive for the purposes of an addition and/or condensation reaction, wherein the additional reactive functional group is complementary to or reactive towards the additional reactive functional groups of component A), C) optionally at least one monomeric, oligomeric and/or polymeric compound having at least one functional group reactive towards the functional groups from component A) or component B) D) one or more photoinitiators as well as E) optionally solvents, water, pigments and/or extenders as well as conventional lacquer additives, wherein component A) and component B) diffe
    Type: Grant
    Filed: December 17, 1999
    Date of Patent: December 25, 2001
    Assignee: Herberts GmbH & Co. KG
    Inventors: Carmen Flosbach, Helmut Löffler, Karin Maag
  • Patent number: 6326415
    Abstract: Provided is a support for an ink jet recording material. The support comprises a substrate and a UV cured resinous coating layer on the substrate, with said resinous coating layer being comprised of a tetrafunctional polyester acrylate, a difunctional acrylic ester, a UV photoinitiator and a polyether.
    Type: Grant
    Filed: August 5, 1999
    Date of Patent: December 4, 2001
    Assignee: Rexam Graphics Inc.
    Inventors: Alexander J. Miklasiewicz, Son T. Vo, Everett Wyman Bennett
  • Patent number: 6303670
    Abstract: Disclosed is an ultraviolet-curable cellulosic coating composition comprising cellulose acetate, diepoxy compound and photo cationic polymerization catalyst. The objective is to provide a novel ultraviolet-curable cellulosic coating composition capable of forming a film excellent in the adherence to polar substrate, solvent resistance, gloss and impact resistance.
    Type: Grant
    Filed: February 25, 2000
    Date of Patent: October 16, 2001
    Assignee: Nippon Paper Industries Co., Ltd.
    Inventors: Kenichi Fujino, Shelby F. Thames
  • Patent number: 6300428
    Abstract: The invention provides aqueous, solvent based, and solvent-free curable coating compositions which include (A) the reaction product of an epoxy resin, acid, and tertiary amine; (B) a reactive diluent, and, optionally, (C) a curing agent. The compositions are useful for forming cured coated substrates, that are especially suitable for food and beverage packaging.
    Type: Grant
    Filed: January 27, 2000
    Date of Patent: October 9, 2001
    Assignee: The Valspar Corporation
    Inventors: Thomas A. Stevenson, Larry Brandenburger, William McCarty, John Mazza, Jeffrey Niederst
  • Patent number: 6239189
    Abstract: A radiation-polymerizable composition contains at least one radiation curable acrylate resin oligomer prepared by reacting an alkoxylated polyol with a first acid component which includes an ethylenically unsaturated carboxylic acid; and a rheology modifier prepared by reacting a diepoxide with a second acid component which includes an ethylenically unsaturated carboxylic acid or reactive derivative thereof in the presence of a polyamide based on a polymerized fatty acid. The ethylenically unsaturated carboxylic acids of the first and second acid components are preferably acrylic acid or methacrylic acids. The diepoxide is preferably a diglycidyl ether such as bisphenol A. Colorants such as pigments or dyes optionally may be incorporated into the composition to form a printing ink which is curable by ultraviolet (UV) or electron beam radiation.
    Type: Grant
    Filed: March 27, 1998
    Date of Patent: May 29, 2001
    Assignee: Henkel Corporation
    Inventors: Ramesh Narayan, Miguel Dones, Theresa Miller
  • Patent number: 6207726
    Abstract: A photocurable prepreg composition which is characterized by easy control of a B stage state of a thermosetting resin such as an unsaturated polyester resin or an epoxy acrylate resin, excellent storage stability, and remarkable curability after being shaped; as well as a production method therefor. A photocurable prepreg composition which contains an unsaturated polyester resin and/or an epoxy acrylate resin; at least two photopolymerization initiators with photosensitivity in different wavelength ranges; and an inorganic or an organic fiber-reinforcing material and/or filler, and which composition is treated with light of a specific wavelength such that at least one photopolymerization initiator and radical-polymerizable unsaturated groups remain partially in said resin; a production method therefor; and formed articles produced therefrom.
    Type: Grant
    Filed: February 11, 1999
    Date of Patent: March 27, 2001
    Assignees: Showa Denko Kabushiki Kaisha, Showa Highpolymer Co., Ltd.
    Inventors: Kazuo Ohtani, Tomio Yamamoto, Hidetake Sendai, Shuichi Sugita, Hirotoshi Kamata, Takeo Watanabe
  • Patent number: 6180317
    Abstract: An improved photoimagable cationically polymerizable epoxy based coating material is provided, that is suitable for use on a variety of substrates including epoxy-glass laminate boards cured with dicyandiamide. 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; 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° C. and about 110° C. and a molecular weight of between about 600 and 2,500. Optionally, a third resin may be added to the resin system. To this resin system is added about 0.
    Type: Grant
    Filed: November 18, 1991
    Date of Patent: January 30, 2001
    Assignee: International Business Machines Corporation
    Inventors: Robert David Allen, Richard Allen Day, Donald Herman Glatzel, William Dinan Hinsberg, John Richard Mertz, David John Russell, Gregory Michael Wallraff
  • Patent number: 6087417
    Abstract: The invention provides aqueous, solvent based, and solvent-free curable coating compositions which include (A) the reaction product of epoxy resin, acid, and tertiary amine; (B) reactive diluent, and, optionally, (C) curing agent. The compositions are useful for forming cured coated substrates, that are especially suitable for food and beverage packaging.
    Type: Grant
    Filed: January 16, 1998
    Date of Patent: July 11, 2000
    Assignee: The Valspar Corporation
    Inventors: Thomas A. Stevenson, Larry Brandenburger, William McCarty, John Mazza, Jeffrey Niederst
  • Patent number: 6077879
    Abstract: The present invention provides a radically polymerizable curable resin obtained by modifying an epoxy resin by reacting a phenol compound having an alcoholic hydroxyl group; and an unsaturated monobasic acid, to the epoxy resin having two or more epoxy groups in a molecule. The epoxy resin is reacted with the phenol compound and the unsaturated monobasic acid. The curable resin is subjected to polymerization curing with heat or light to form a cured product having excellent heat resistance, moisture resistance, and adhesion to substrates. The present invention also provides a curable resin composition containing the curable resin, as well as an alkaline-developable curable resin capable of forming a coating layer having excellent tack-free property, quick developability and excellent properties of cured layer.
    Type: Grant
    Filed: November 10, 1998
    Date of Patent: June 20, 2000
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Nobuaki Ohtsuki, Toshio Awaji
  • Patent number: 5993960
    Abstract: A printing sheet having a high gloss and an enhanced ink-setting property has an outermost surface coating layer formed on a substrate sheet from an electron beam-cured resin produced from at least one electron beam-curable unsaturated organic compound having a dimer acid structure derived from unsaturated higher fatty acid.
    Type: Grant
    Filed: October 31, 1997
    Date of Patent: November 30, 1999
    Assignee: New Oji Paper Co., Ltd.
    Inventors: Yasufumi Nakayama, Masahiro Kamiya, Shinichi Nagasaki, Yoshihide Kawano, Toshifumi Fujii
  • Patent number: 5858618
    Abstract: A photopolymerizable resinous composition includes a photocurable prepolymer which is prepared by a three-step reaction. The first step of the reaction includes reacting epoxide compounds containing at least two epoxy groups with an unsaturated carboxylic acid containing at least three vinyl linkages and an unsaturated carboxylic acid containing one vinyl group. The second step includes reacting the reaction product formed from the first step in a reaction with polybasic acid anhydride, and a third step of reacting the reaction product formed from the second step with a monoepoxide containing one vinyl group. The composition further includes a photocurable monomer containing one carboxylic acid having at least three vinyl linkages, a photocurable monomer containing at least one vinyl group, a photopolymerization initiator, a curing agent, and organic solvents. The composition exhibits photo- and thermal-curability, and the ability to develop with a weak alkaline aqueous solution.
    Type: Grant
    Filed: December 2, 1996
    Date of Patent: January 12, 1999
    Assignee: Nan Ya Plastics Corporation
    Inventor: Ming-Jen Tzou
  • Patent number: 5849460
    Abstract: A photosensitive resin composition for use in manufacture of multi-layer circuit boards with connecting holes between layers is disclosed. The resin composition has excellent adhesion with a plating metal, resolution, photo-curing, thermosetting, thermal resistance, and is capable of being developed using an alkaline solution or an aqueous solution containing a non-halogen based organic solvent as the developing solution. The resin composition comprises a photosensitive epoxy resin, a thermosetting epoxy resin, a reactant of a carboxylic acid added to an acrylonitrile-butadiene rubber and an epoxy resin, a photo-polymerization initiator and a thermosetting agent. This reactant facilitates a high density pattern of connecting holes for circuit boards of the layered type.
    Type: Grant
    Filed: July 16, 1997
    Date of Patent: December 15, 1998
    Assignee: Hitachi, Ltd.
    Inventors: Yoshinori Kawai, Mineo Kawamoto, Junichi Katagiri, Masanori Nemoto, Akio Takahashi
  • Patent number: 5821031
    Abstract: Disclosed herein is a photosensitive solder resist ink capable of development with a dilute alkaline solution. It has a wide pre-curing latitude. It permits the pre-cured board to be stored for a long period of time. It is superior in resolution, sensitivity, and solder resistance. Disclosed also herein is a printed circuit board having good adhesion, chemical resistance, electrical properties, gold plating resistance, solder heat resistance, and electrocorrosion resistance. Disclosed also herein is a process for producing said printed circuit board by using said solder resist ink.The photosensitive solder resist ink comprises (A) an ultraviolet-curable resin containing 0-20 wt % of aromatic ring moiety which is obtained by reacting a polymer composed of (a) 40-100 mol % of ethylenically unsaturated monomer having an epoxy group and (b) 0-60 mol % of ethylenically unsaturated monomer capable of copolymerization therewith, with (meth)acrylic acid in an amount of 0.7-1.
    Type: Grant
    Filed: May 22, 1996
    Date of Patent: October 13, 1998
    Assignee: Goo Chemical Co., Ltd.
    Inventors: Soichi Hashimoto, Fumito Suzuki, Toshikazu Oda
  • Patent number: 5780526
    Abstract: An ultraviolet-curing liquid undercoating composition for use in metallizing FRP, which is a one-component type, has an unlimited pot life, and is excellent in adhesion and heat resistance. The composition comprises 20 to 80 parts by weight of a compound(s) containing at least two (meth)acryloyl groups in its molecule, 80 to 20 parts by weight of oil-modified alkyd resin(s), and 2 to 15 parts by weight of a sensitizer, optionally further 5 to 20 parts by weight of an amino resin based on 100 parts by weight in total of the above compound and the above alkyd resin(s). It is suited for the undercoating of an automotive reflector.
    Type: Grant
    Filed: November 14, 1996
    Date of Patent: July 14, 1998
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Sakae Matsui, Hiroyuki Nakamura, Shizuo Kudo, Hiroaki Konse
  • Patent number: 5750313
    Abstract: Disclosed are a photosensitive resin composition essentially comprising 100 parts by weight of modified polyvinyl alcohol comprising a structural units of formulae (I), (II) and (III): ##STR1## wherein R represents a hydrocarbon group having 1 to 20 carbon atoms; X represents an aliphatic, alicyclic or aromatic divalent hydrocarbon group having 1 to 20 carbon atoms or a divalent group having at least one carboxyl group in the molecule thereof, the proportion of the structural unit of formula (I) being from 1 to 40 mol %, the total proportion of the structural units of formulae (II) and (III) being from 60 to 99 mol %, and the carboxyl equivalent attributed to the structural unit of formula (III) being from 0.3 to 5 mol/kg, (B) from 0.1 to 10 parts by weight of an unsaturated epoxy compound, (C) from 20 to 200 parts by weight of a polymerizable unsaturated compound having an ethylenical double bond in the molecule thereof, and (D) from 0.1 to 10 parts by weight of a photopolymerization initiator.
    Type: Grant
    Filed: January 13, 1997
    Date of Patent: May 12, 1998
    Assignee: Toray Industries, Inc.
    Inventors: Hiroshi Tamada, Shigetora Kashio, Tamio Adachi
  • Patent number: 5726219
    Abstract: The present invention provides a rein composition comprising the following components (a), (b), (c), (d) and (e) as essential components; and an excellent multilayer printed circuit board obtained by using the resin composition:(a) a polyfunctional epoxy resin having an epoxy equivalent of 120-500,(b) a modified phenol novolac obtained by reacting 20-60 mole % of the phenolic hydroxyl groups of a phenol novolac obtained by condensing a phenol compound with formaldehyde in the presence of an acidic catalyst, with a glycidyl group-containing acrylate or methacrylate,(c) an epoxy acrylate or epoxy methacrylate compound,(d) a diluent consisting of a polyfunctional monomer having a plurality of photosensitive functional groups or a polyfunctional monomer having a photosensitive functional group and a heat-sensitive functional group, or a diluent consisting of a combination of the two monomers, and(e) a photopolymerization initiator.
    Type: Grant
    Filed: March 4, 1997
    Date of Patent: March 10, 1998
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Takeshi Hosomi, Hiroshi Hayai, Takayuki Baba
  • Patent number: 5677398
    Abstract: Disclosed are an epoxy acrylate resin of the general formula (1) ##STR1## and an acid-modified epoxy acrylate resin obtained by reacting the epoxy acrylate resin with a carboxylic acid or an anhydride thereof, as well as curable resin compositions containing such a resin and the cured products thereof.
    Type: Grant
    Filed: April 3, 1996
    Date of Patent: October 14, 1997
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Toshihiro Motoshima, Akio Karasawa, Keisuke Takuma, Akihiro Yamaguchi
  • Patent number: 5674623
    Abstract: A solid photocurable film adhesive comprising (I) a photocurable material having, on average, more than one acrylic group per molecule, at least 20% by weight of said material being a urethane acrylate, a polyester acrylate or a mixture of a urethane acrylate and a polyester acrylate, (II) as sole or major solid film-forming component, a solid polyvinylacetal and (III) a photoinitiator for photopolymerisation of acrylic compounds.The film adhesive is useful in the production of data-carrying laminates such as identity cards.
    Type: Grant
    Filed: November 14, 1994
    Date of Patent: October 7, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Margaret Ruth Haddon, Terence James Smith
  • Patent number: 5401602
    Abstract: Low fix temperature toner resins are fabricated by a reactive melt mixing process wherein polymer resins are cross-linked at high temperature and high shear. The resins are particularly suitable for high speed fusing, show excellent offset resistance and wide fusing latitude and superior vinyl offset properties.
    Type: Grant
    Filed: March 23, 1993
    Date of Patent: March 28, 1995
    Assignee: Xerox Corporation
    Inventors: Hadi K. Mahabadi, Enno E. Agur, Gerald R. Allison, Michael S. Hawkins, Stephan Drappel, Maria N. V. McDougall, Bernard Grushkin, Thomas R. Hoffend, Angelo J. Barbetta
  • Patent number: 5397671
    Abstract: A reactive melt mixing process for preparing toner resin, comprising: melting a reactive base resin, thereby forming a polymer melt; adding to said polymer melt a free radical initiator compound and optionally a vinyl monomer compound to form a second melt; and heating and mixing under high shear said second melt with optional addition of a vinyl monomer compound to form a partially crosslinked and partially gelled toner resin.
    Type: Grant
    Filed: February 10, 1994
    Date of Patent: March 14, 1995
    Assignee: Xerox Corporation
    Inventors: Robert D. Bayley, Carol A. Fox, Thomas R. Hoffend
  • Patent number: 5376494
    Abstract: Low fix temperature toner resins are fabricated by a reactive melt mixing process wherein polymer resins are cross-linked at high temperature and high shear. The resins are particularly suitable for high speed fusing, show excellent offset resistance and wide fusing latitude and superior vinyl offset properties.
    Type: Grant
    Filed: December 30, 1991
    Date of Patent: December 27, 1994
    Assignee: Xerox Corporation
    Inventors: Hadi K. Mahabadi, Enno E. Agur, Gerald R. Allison, Michael S. Hawkins, Stephan Drappel, Maria N. V. McDougall, Bernard Grushkin, Thomas R. Hoffend, Angelo J. Barbetta
  • Patent number: 5304628
    Abstract: A radiation-curing resin composition comprising (A) a resin having a carboxylic acid group and an unsaturated double bond and (B) a compound containing a cyclocarbonate group. The composition is excellent in stability and curing properties and provides a cured film excellent in water resistance, solvent resistance, chemical resistance, and heat resistance.
    Type: Grant
    Filed: August 4, 1992
    Date of Patent: April 19, 1994
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Masashi Kinoshita, Hidenobu Ishikawa
  • 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: 5278199
    Abstract: An actinic radiation-reactive pressure-sensitive adhesive composition can be cured in air at a high speed, without irritation and bad smell, and comprises1 a pressure-sensitive adhesive organic compound, and2 an actinic radiation-curable resin comprising (1) one or more polythiol compounds and (2) one or more polyene compounds each having at least two actinic radiation-reactive carbon-to-carbon double bonds in the molecule.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: January 11, 1994
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Kazuo Ohkawa, Seiichi Saito
  • 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: 5229252
    Abstract: A photoimageable composition for forming a solder mask has a photopolymerizable acrylate chemical system which renders exposed portions insolvable to alkaline aqueous developers and an epoxy chemical system which hardens the composition after exposure and development. The acrylate chemical system comprises acrylate monomers, epoxy-acrylate oligomers and a photoinitiator. The epoxy chemical system comprises an epoxy resin and a curative therefore. The composition further comprises a cross-linking agent which is reactive with hydroxyl groups of the acrylate and epoxy chemical systems.
    Type: Grant
    Filed: October 21, 1991
    Date of Patent: July 20, 1993
    Assignee: Morton International, Inc.
    Inventors: Kathy M. Flynn, Vinai M. Tara, Kathleen L. Nelson
  • Patent number: 5227460
    Abstract: A low melt toner resin with low minimum fix temperature and wide fusing latitude contains a linear portion and a cross-linked portion containing high density cross-linked microgel particles, but substantially no low density cross-linked polymer. The resin may be formed by reactive melt mixing.
    Type: Grant
    Filed: December 30, 1991
    Date of Patent: July 13, 1993
    Assignee: Xerox Corporation
    Inventors: Hadi K. Mahabadi, Enno E. Agur, Gerald R. Allison, Michael S. Hawkins, Stephan Drappel, Maria N. V. McDougall, Bernard Grushkin, Thomas R. Hoffend, Angelo J. Barbetta
  • Patent number: 5110857
    Abstract: Ultravioletsetting resin composition contains fragmentary quartz glass powder in the ratio of 50 to 200 parts to 100 parts of the ultravioletsetting resin. The surface hardness of the ultravioletsetting resin of the present invention is increased in a short time by the application of ultraviolet rays.
    Type: Grant
    Filed: March 23, 1990
    Date of Patent: May 5, 1992
    Assignee: Aisin Seiki Kabushiki Kaisha
    Inventors: Akio Inagaki, Kiyotaka Nakai, Hitoshi Tauchi
  • Patent number: 5053316
    Abstract: (I) A photosensitive resin composition comprising(i) a thermoplastic elastomer selected from(A) a poly(amide-imide) ester produced by reacting a polyamide-forming monomer with either an aromatic carboxylic acid or its anhydride and either a polyalkylene glycol or an .alpha.,.omega.-dihydroxy hydrocarbon,(B) a poly(amide-imide) urethane produced by reacting the above poly(amide-imide) ester with a diisocyanate compound, and(C) a poly(amide-imide) urethane produced by reacting the above diisocyanate compound with a mixture of polymer diol and a poly(amide-imide) ester obtained from a Chthd 2-C.sub.4 alkylene glycol and a polyamide-forming monomer, and(ii) an ethylenic unsaturated compound, and(iii) a photopolymerization initiator,(II) a photosensitive sheet for printing plate formation which comprises a resin layer formed of the above composition, and(III) the above defined thermoplastic elastomer.
    Type: Grant
    Filed: June 8, 1989
    Date of Patent: October 1, 1991
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Yoshio Suzuki, Yutaka Usubuchi, Yakeshi Oguri
  • Patent number: 5026624
    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.degree. C. and about 110.degree. C. and a molecular weight of between about 600 and 2,500. To this resin system is added about 0.
    Type: Grant
    Filed: March 3, 1989
    Date of Patent: June 25, 1991
    Assignee: International Business Machines Corporation
    Inventors: Richard A. Day, Jeffrey D. Gelorme, David J. Russell, Steven J. Wih
  • Patent number: 5011560
    Abstract: A method of adhesion which comprises applying a two-step reactive type tacky adhesive agent comprising (1) a non-photopolymerizable epoxy resin or isocyanate compound, (2) a curing agent therefor and (3) a compound having at least one photopolymerizable vinyl group in one molecule onto a substrate, irradiating the whole applied surface with light to develop the tackiness, and sticking the substrate together to a material to be bonded, while the tackiness is retained, followed by curing.The method provides excellent green bonding strength and can permit the satisfactory adhesion without clamping, and can be particularly suitably utilized in the adhesion of materials to be bonded which have a curved surface difficult to be clumped.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: April 30, 1991
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yoshikazu Nakai, Tsutomu Kubota
  • Patent number: 5009982
    Abstract: A photosetting liquid ink composition developable with a dilute alkaline aqueous solution and comprising (A) a resin curable with an activated energy ray, obtained by the reaction of a saturated or unsaturated polybasic acid anhydride with a product of the reaction of a novolak type epoxy compound and an unsaturated monocarboxylic acid, (B) a photopolymerization initiator, and (C) a diluent can be used for the production of an etching resist or a solder resist in the manufacture of a printed circuit. This composition, when combined with a thermosetting component, produces a photosetting and thermosetting liquid ink composition.
    Type: Grant
    Filed: June 6, 1988
    Date of Patent: April 23, 1991
    Assignee: Taiyo Ink Manufacturing Co., Ltd.
    Inventors: Yuichi Kamayachi, Syoji Inagaki
  • Patent number: 4994348
    Abstract: A light-sensitive recording material for the production of intaglio printing plates comprises a photopolymerizable and/or photocrosslinkable material which is soluble or dispersible in a developer liquid and on exposure to actinic light is rendered insoluble or no longer dispersible in this developer liquid and which, at least in a surface zone of the surface of the layer which forms the later surface of the printing plate, contains finely divided abrasive particles whose average particle size is within the range from 0.1 to 6 .mu.m, which have a hardness of >4.0 on the Mohs hardness scale, the surface of the layer which forms the later surface of the printing plate has a peak-to-valley height of <2 .mu.m, and the photocrosslinkable and/or photopolymerizable material contains a reaction product of a cycloaliphatic epoxy with acrylic acid or methacrylic acid.
    Type: Grant
    Filed: February 24, 1989
    Date of Patent: February 19, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Eleonore Raabe, Erich Beck
  • Patent number: 4992547
    Abstract: The photopolymerizable mixture described contains(A) at least one ethylenically unsaturated photopolymerisable compound,(B) a photoinitiator of the formula I ##STR1## and (C) a photosensitiser from the group of aromatic carbonyl compounds having a triplet energy of 225-310 kJ/mol, for example xanthones, thioxianthones, 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 sensitisers (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: June 14, 1988
    Date of Patent: February 12, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Godwin Berner, Kurt Meier, Kurt Dietliker, Rinaldo Husler
  • Patent number: 4948700
    Abstract: A liquid heat- and light-sensitive resinous composition which contains as main components (A) a photopolymerizable compound prepared by reacting a novolak type epoxy compound with successively, an unsaturated monocarboxylic acid represented by at least one of formula (I) and (II) and a saturated or unsaturated polybasic acid anhydride, (B) a photopolymerizable compound having at least one ethylenic unsaturated double bond, (C) an epoxy compound having at least one epoxy group, (D) a photopolymerization initiator, (E) a thermosetting catalysts capable of making an epoxy group undergo a thermal reaction, and (F) an organic solvent; ##STR1## wherein R represents -H or -CH.sub.3 ; R.sup.1, R.sup.2 and R.sup.3 each represents an unsubstituted or substituted alkylene group, an unsubstituted or substituted arylene group, or an unsubstituted or substituted aralkylene group; and X represents -COO-, -OCO- or -O-.
    Type: Grant
    Filed: August 3, 1989
    Date of Patent: August 14, 1990
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Minoru Maeda, Yuichi Wakata, Sadao Fujikura, Masayuki Iwasaki
  • Patent number: 4937173
    Abstract: A radiation curable liquid resin composition comprising a radiation curable liquid base resin and polymer microparticles having an average particle size from 0.01 to 0.6 microns. The incorporation of polymer microparticles to the base resin may improve the rheological property of the liquid composition and also the physical properties of cured film therefrom.
    Type: Grant
    Filed: December 13, 1988
    Date of Patent: June 26, 1990
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Kazunori Kanda, Ryuzo Mizuguchi
  • Patent number: 4933259
    Abstract: A composition useful as an alkaline developable liquid photoimageable solder resist ink comprising a photocurable resin, a photopolymerization initiator, a reactive diluent, a solvent and optionally, a thermosetting material as main components wherein the photocurable resin comprises a reaction product of: (A) an epoxy vinyl ester resin obtained by reacting a cresol novolak epoxy resin and an unsaturated monobasic acid, (B) a polybasic acid anhydride and (C) an alkyl ketene dimer, wherein the hydroxyl value of the photocurable resin is not more than 10 carbons. Coating films formed from the subject composition have excellent adhesion, heat resistance, moisture insulation resistance and alkaline developable properties.
    Type: Grant
    Filed: August 24, 1988
    Date of Patent: June 12, 1990
    Assignee: Arakawa Chemical Industries, Ltd.
    Inventors: Machio Chihara, Mitsukazu Funahashi
  • Patent number: 4876173
    Abstract: A photopolymerizable composition is described, comprising an addition polymerizable unsaturated compound having at least two ethylenically unsaturated double bonds per molecule, a photopolymerization initiator, and a binder, wherein said binder is a copolymer represented by formula (I) ##STR1## wherein Ar.sup.1 and Ar.sup.2 each represent a substituted or unsubstituted phenyl group; and n.sub.1, n.sub.2, n.sub.3, and n.sub.4 each represents mol % of the respective repeating unit, wherein n.sub.1 is from 0 to about 70; n.sub.2 is from 0 to about 70; n.sub.3 is from about 5 to 50; and n.sub.4 is from about 5 to 50; provided that n.sub.1 and n.sub.2 are not 0 at the same time, the sum of n.sub.3 and n.sub.4 is from about 30 to 80. The composition is useful as an alkali-developable light-sensitive layer which provides a photosensitive dry film resist having excellent performance characteristics.
    Type: Grant
    Filed: September 2, 1988
    Date of Patent: October 24, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuo Maemoto, Masayuki Iwasaki, Minoru Maeda, Yoshimasa Aotani
  • Patent number: 4789620
    Abstract: Disclosed is a liquid photosensitive resin composition comprising(a) an at least partially carboxyl-modified multifunctional epoxy acrylate and/or multifunctional epoxy methacrylate having an average acid value of 4 to 150 and a number average molecular weight of not greater than 5,000,(b) an acrylic and/or methacrylic cross-linking monomer and/or oligomer other than the epoxy acrylate and/or epoxy methacrylate,(c) an acrylic and/or methacrylic monoethylenically vinyl monomer,(d) an inorganic filler, and(e) a photo-initiator and/or photosensitizer.This liquid photosensitive resin composition has excellent alkali developability, yields a cured coating film having good adhesion and good electrical insulating properties under high-humidity conditions, and is suitable for use as a solder resist in the fabrication of printed circuit boards.
    Type: Grant
    Filed: July 1, 1986
    Date of Patent: December 6, 1988
    Assignee: Mitsubishi Rayon Co. Ltd.
    Inventors: Isao Sasaki, Kenji Kushi, Ken-ichi Inukai
  • Patent number: 4786579
    Abstract: The inventive photosensitive resin composition has excellent heat resistance, adhesiveness to substrate surface and photosensitivity and suitable as a material for solder resist or plating resist on printed circuit boards. The resin composition comprises, in addition to a photopolymerization initiator and curing agent for epoxy resins, a resinous ingredient composed of a diallyl phthalate resin, a first esterified resin as a reaction product of a cresol novolac type epoxy resin and 0.2-0.8 mole per mole of epoxy groups of an ethylenically unsaturated carboxylic acid and a second esterified resin as a reaction product of a phenol and/or cresol novolac type epoxy resins and 0.9-1.1 moles per mole of epoxy resins of an ethylenically unsaturated carboxylic acid in a limited proportion.
    Type: Grant
    Filed: April 14, 1987
    Date of Patent: November 22, 1988
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kenji Tazawa, Akihiko Saito
  • Patent number: 4785062
    Abstract: This invention is directed to the reaction product of an O-epoxyalkylated tetrakis (hydroxyphenyl) alkane resin with a phenol, which is used either as an upper layer over a lower layer of a diazo resin in a bi-layer system or as a homogeneous mixture with a diazo resin in a mono-layer system to provide a water-developable, negative-working, lithographic printing plate.
    Type: Grant
    Filed: July 31, 1984
    Date of Patent: November 15, 1988
    Assignee: W. R. Grace & Co.-Conn.
    Inventor: Alan R. Browne
  • Patent number: 4725524
    Abstract: In dry film resists possessing a solid photopolymerizable resist layer, which is applied on a temporary base and can be developed with aqueous, in particular aqueous alkaline, media, and, if required, a cover sheet on the resist layer, the said resist layer is built from a homogeneous mixture of (a) not less than 40% by weight of one or more oligomers which contain free carboxyl groups and more than two acryloyl and/or methacryloyl groups and are soluble or dispersible in aqueous alkaline solutions, (b) from 1 to 35% by weight of one or more film-forming compatible polymers which are soluble in aqueous media, (c) from 1 to 30% by weight of one or more compatible photopolymerizable monomers, (d) from 0.001 to 10% by weight of one or more photoinitiators and (e) from 0 to 30% by weight of further additives and/or assistants. Resist images are produced on a substrate by a process employing photopolymerizable resist layers of the type stated above.
    Type: Grant
    Filed: December 18, 1985
    Date of Patent: February 16, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Albert Elzer, Gunnar Schornick, Axel Sanner
  • Patent number: 4649062
    Abstract: Vehicles for ultraviolet radiation-curable ceramic enamels comprise (a) acrylate- or methacrylate-modified oligomers; (b) acrylate or methacrylate monomers, the functionality of (a) and (b) being selected to provide desired film and firing characteristics; (c) a combination of photoinitiators to provide a balance of surface and through cure; and an inhibitor to enhance shelf life. Printing media comprising pigmented frits and the vehicles are described, as are methods for their application to heat-resistant substrates, especially glass.
    Type: Grant
    Filed: April 25, 1985
    Date of Patent: March 10, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Raymond S. Kosiorek, Leslie R. Gatechair