Processes Involving An Ethylenically Unsaturated Material Derived From Poly 1,2-epoxide As Reactant Or A Solid Polymer; Or Compositions Thereof Patents (Class 522/100)
  • Patent number: 5945463
    Abstract: A composition for a gasket which comprises (A) 100 parts by weight of a urethane acrylate oligomer having a weight-average molecular weight of 7,000 to 40,000, (B) 40 to 260 parts by weight of a polyether monoacrylate substituted at the end and/or a polyether polyester monoacrylate substituted at the end, and (C) 0.5 to 5 parts by weight of a photopolymerization initiator and has a viscosity of 4,000 to 100,000 centipoises at 25.degree. C.; and a process for producing a gasket by discharging the above composition on a substrate by using an X-Y-Z-driving automatic coating robot and curing the discharged composition by irradiation of ultraviolet light.A gasket can be formed to an accurate shape. Operations of forming and attaching the gasket can easily be conducted, and loss of the used material can be reduced. The gasket has a large tearing strength and a small compression set and is excellent in the flexibility and the sealing property.
    Type: Grant
    Filed: March 28, 1997
    Date of Patent: August 31, 1999
    Assignees: Zeon Rize Co., Ltd., Sunarrow Limited
    Inventors: Ichiro Kawabuchi, Tetsuro Yamada, Yoshio Kenmochi, Atsuo Ishikawa
  • Patent number: 5882842
    Abstract: An active energy ray-curable resin composition, particularly an active energy ray-curable coating composition, both comprising:(A) a resin having oxetane functional groups and epoxy groups in the molecule, and(B) a photo-induced cationic polymerization initiator.
    Type: Grant
    Filed: February 12, 1997
    Date of Patent: March 16, 1999
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Yu Akaki, Fumio Yamashita, Yasuo Takaya, Osamu Isozaki
  • Patent number: 5861444
    Abstract: A refractive-index imaging material which includes a binder made of either of a copolymer having acrylic epoxy, chain epoxy, organic denatured silicone, and ethylene unsaturated compound having a hydroxyl group in its end in the building block of the copolymer and a copolymer having any one of ethylene unsaturated compounds containing silicone in the building block of the copolymer, a photosensitive monomer made of a mixture including multifunctional acrylate or multifunctional methacrylate and an ethylene unsaturated monomer containing an aromatic ring or halogen and a photopolymerization initiator.
    Type: Grant
    Filed: May 7, 1997
    Date of Patent: January 19, 1999
    Assignee: Fujitsu Limited
    Inventors: Koji Tsukamoto, Takeshi Ishitsuka, Tetsuzo Yoshimura, Katsusada Motoyoshi, Yasuhiro Yoneda
  • Patent number: 5859084
    Abstract: A process for the preparation of a radiation-curable acrylate composition, wherein to compounds A containing at least 2 acrylic groups there are added benzophenone derivatives which are not copolymerizable by free-radical copolymerization and which contain at least one primary or secondary amino group or a hydroxyl group or a mercapto group.
    Type: Grant
    Filed: July 15, 1996
    Date of Patent: January 12, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Jochen Schroder, Wolfgang Reich, Erich Beck, Martin Fischer, Wolfram Weiss
  • 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: 5855837
    Abstract: A novel method for producing thick composite parts based upon photopolymerizable compositions is disclosed. The constituents of the photopolymerizable mixture comprise a monomer or monomers capable of polymerizing by free radical or cationic mechanisms, and a photoinitiator system which possesses an absorbance characteristic which is effectively reduced, or self-eliminating, upon initiation of the polymerization reaction. Parts having thicknesses up to 2 cm and thicker for varying end use applications are made by photopolymerizing such compositions. In addition, using such compositions composite parts can be made using a reinforcement material such as a glass fiber mat present in an amount by weight of from about 5 to about 70%.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: January 5, 1999
    Assignee: Michigan State University
    Inventors: Alec B. Scranton, Bharath Rangarajan, Lindsay S. Coons
  • Patent number: 5854313
    Abstract: Fine particles of high heat resistant polymer obtained by emulsion polymerization or seeded polymerization of at least one epoxy ester (C) having two or more unsaturated bonds in one molecule and at least one reactive monomer (D) having at least one unsaturated double bond in one molecule, in the absence of a water-insoluble inorganic material as a dispersion stabilizer, the epoxy ester (C) being obtained by adding at least one unsaturated monobasic acid (B) to at least one epoxide (A-1) having at least one glycidyl group and one monocyclic hydrocarbon group in one molecule, and/or at least one epoxide (A-2) having at least one cycloaliphatic epoxy group in one molecule. The fine polymer particles have excellent heat resistance and solvent resistance, and an aqueous or alcoholic dispersion of such fine polymer particles is produced therefrom.
    Type: Grant
    Filed: April 21, 1997
    Date of Patent: December 29, 1998
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yoshimasa Omori, Hiroya Okumura, Takashi Shibata
  • Patent number: 5849857
    Abstract: The present invention provides a production method for a photo-sensitive resin, characterized in reacting a difunctional epoxy resin (B) having two epoxy groups in a molecule with carboxyl groups contained in a resin (A) having two or more (meth)acryloyl groups and at least one carboxyl group in a molecule. Since the photo-sensitive resin prepared by extending the resin (A) to a high molecular weight linearly via the difunctional epoxy resin (B) is obtained, a resist layer having an excellent tack-free property can be formed. Further, a resist layer irradiated with rays through a patterning film can be developed rapidly and correctly in an alkaline aqueous solution. Accordingly, it has been possible to provide the high-performance liquid photo-sensitive resin compositions useful for a solder resist used for producing printed circuit boards and for an electroless plating resist or useful for producing black matrices and color filters for liquid crystal displays.
    Type: Grant
    Filed: May 14, 1996
    Date of Patent: December 15, 1998
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Toshio Awaji, Nobuaki Ohtsuki, Motohiro Arakawa
  • Patent number: 5849459
    Abstract: A resin composition for stereolithography and a process for producing a three-dimensional object using the same. The resin composition comprises (1) a liquid photohardenable resin composition containing at least one of photo-polymerizable compounds and a photosensitive polymerization initiator, and (2) at least one of radiation energy absorbers in an amount of from 0.001 to 1.0% by weight based on the total amount of the liquid photohardenable resin composition (1).
    Type: Grant
    Filed: November 28, 1995
    Date of Patent: December 15, 1998
    Assignee: Teijin Seiki Co., Ltd.
    Inventors: Tsuneo Hagiwara, Yorikazu Tamura
  • Patent number: 5827604
    Abstract: This invention is to provide a multilayer printed circuit board having excellent appearance and reliability and a method of producing the same, and proposes a build-up multilayer printed circuit board comprising an interlaminar insulating layer 4 comprised of an adhesive for additive process between an inner layer copper pattern 3 provided at its surface with a fine uneven layer 9 and an outer layer copper pattern 6 in which the surface of uneven layer 9 in the inner layer copper pattern 3 is covered with a metal layer containing one or more of metals having an ionization tendency not lower than that of copper but not higher than that of titanium, or a noble metal layer 10, and a production technique therefor.
    Type: Grant
    Filed: July 31, 1996
    Date of Patent: October 27, 1998
    Assignee: Ibiden Co., Ltd.
    Inventors: Hiroaki Uno, Masato Kawade
  • Patent number: 5804671
    Abstract: A composition that is useful in the preparation of radiation curable coatings is provided. The composition comprises the reaction product of an epoxy component comprised of a diepoxide and an acid component comprised of an ethylenically unsaturated carboxylic acid or reactive derivative thereof, reacted in the presence of a polyamide based on a polymerized fatty acid. The polyamide preferably has a number average molecular weight of less than about 10,000 g/mole. Also provided is a polymerizable composition comprised of the reaction product and a reactive diluent. A method of coating a substrate is also provided which comprises applying to a substrate a composition comprised of the reaction product and exposing said composition to radiation to cure said composition.
    Type: Grant
    Filed: April 8, 1996
    Date of Patent: September 8, 1998
    Assignee: Henkel Corporation
    Inventors: Miguel A. Dones, Theresa M. Miller
  • Patent number: 5798397
    Abstract: Provided is a composition curable by active energy rays, comprising a cationic polyacryloyl compound having two or more acryloyl groups and one or more cation groups in a molecule, represented by any of General Formulae (1) to (6) ##STR1## wherein Z.sub.1 to Z.sub.6 represent independently a residue derived from a polyhydric alcohol or a polyepoxide,K.sub.1 represents independently a radical of the formula ##STR2## K.sub.2 represents a radical of the formula ##STR3## R.sub.1 represents independently a radical of the formula ##STR4## wherein R.sub.3 is independently H-- or CH.sub.3 --, and R.sub.2 represents independently a radical of the formulaCH.sub.2 .dbd.CHCOO--, or CH.sub.2 .dbd.C(CH.sub.3)COO--.
    Type: Grant
    Filed: December 24, 1996
    Date of Patent: August 25, 1998
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiromichi Noguchi, Makiko Kimura, Masato Katayama, Akio Kashiwazaki, Yoshie Nakata, Yuko Nishioka
  • Patent number: 5789039
    Abstract: The present invention relates to powder coatings curable by exposure to radiation, typically ultraviolet radiation. Powder coatings based upon cationically catalyzed resins (typically epoxy resins) are described including bisphenols, bisphenols modified by novolac, as well as aliphatic type epoxides including hydrogenated bisphenol-A, glycidyl methacrylic, glycidyl acrylics or related compounds, and vinyl ethers including mixtures of the foregoing compounds. Photoinitiators of sulfonium type, ferrocinium type, iodonium type, triphenolic types and related compounds are also included. Opacifiers, flow agents and plasticizers are also included. Charge additives for improved electrostatic deposition of the power coating are also described. Degassing agents are also typically included in the formulation, both for degassing the powder coating during cure, and to assist in degassing those substrates (such as wood) which tend to form bubbles during cure. Flow agents are also typically included in the formulation.
    Type: Grant
    Filed: January 26, 1996
    Date of Patent: August 4, 1998
    Assignee: Herberts Powder Coatings, Inc.
    Inventors: Kevin M. Biller, Ben A. MacFadden
  • 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: 5741829
    Abstract: Radiation-curable (meth)acrylates obtainable by reacting compounds of the formula ##STR1## in which R is C.sub.1 -C.sub.4 -alkyl, aryl or R.sup.1 and R.sup.1 is ##STR2## in which R.sup.2 to R.sup.6 independently of one another are H, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, OH, phenyl, SH, SCH.sub.3, SC.sub.2 H.sub.5, F, Cl, Br, CN, COOH, COO--(C.sub.1 -C.sub.17 -alkyl), COO--(C.sub.5 -C.sub.10 -aryl), CF.sub.3, N(alkyl).sub.2, N(alkyl)(aryl), N(aryl).sub.2, N.sup..sym. (alkyl).sub.3 A.sup..crclbar., N.sup..sym. H(alkyl).sub.2 A.sup..crclbar., A.sup..crclbar. is the anion of an acid, and alkyl or aryl, unless indicated otherwise, is C.sub.1 -C.sub.10 -alkyl or C.sub.5 -C.sub.10 -aryl, respectively, and at least one but not more than 3 of R.sup.2 to R.sup.6 are ##STR3## with hydroxy(meth)acrylates containing at least 1 free hydroxyl group and at least 2 (meth)acrylic groups in the molecule.
    Type: Grant
    Filed: July 3, 1996
    Date of Patent: April 21, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Reich, Erich Beck, Ulrich Jager, Reinhold Schwalm
  • 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: 5721076
    Abstract: This invention relates to alkali-developable photosensitive or thermosetting resin compositions obtained by mixing (A) polymerizable unsaturated compounds having main structural units represented by the following general formulas (1) and (2) ##STR1## ?wherein R.sub.1, and R.sub.2 designate hydrogen, alkyl group with 1 to 5 carbon atoms or halogen, R.sub.3 designates hydrogen or methyl group, X designates --CO--, --SO.sub.2 --, --C(CF.sub.3).sub.2 --, --Si(CH.sub.3).sub.2 --, --CH.sub.2 --, --C(CH.sub.3).sub.2 --, --O--, ##STR2## or direct linkage, Y designate acid anhydride residue, Z designates acid dianhydride residue and the mole ratio of the structural units (m/n) is from 1/99 to 90/10 and showing an inherent viscosity (.eta..sub.inh) of 0.1 dl/g or more as determined on a solution of 0.5 g of said compounds in 100 ml of N-methylpyrrolidone at 30.degree. C.
    Type: Grant
    Filed: February 27, 1995
    Date of Patent: February 24, 1998
    Assignees: Nippon Steel Corporation, Nippon Steel Chemical Co., Ltd.
    Inventors: Kazuhiro Watanabe, Takero Teramoto, Kohki Inada
  • Patent number: 5705316
    Abstract: The invention relates to compounds having at least one vinyl ether group which also contain in the molecule at least one further functional group selected from acrylate, methacrylate, epoxy, alkenyl, cycloalkenyl and vinylaryl groups, to compositions, especially for stereolithography, comprising those vinyl ether compounds, and to a method of producing three-dimensional objects using those compositions.
    Type: Grant
    Filed: November 9, 1995
    Date of Patent: January 6, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Bettina Steinmann, Adrian Schulthess, Max Hunziker
  • Patent number: 5694852
    Abstract: A printing medium or image carrier for application to a printing apparatus or substrate which comprises a plastic composition which is applied to a printing substrate to form a plastic coating covering the substrate, which plastic coating is engraved to provide a printing medium. Preferred plastic compositions are those including epoxide resins such as cycloaliphatic epoxide resins, reaction products of epichlorohydrin and bisphenol A, bisphenol A epoxy resins modified with cresol novolac(s), epoxy-novolac resins, and epoxy-novolac based vinyl esters. The present invention provides for an effective rotogravure printing medium without the use and/or disposal of hazardous chemicals.
    Type: Grant
    Filed: July 16, 1996
    Date of Patent: December 9, 1997
    Assignee: W.R. Chesnut Engineering, Inc.
    Inventors: David E. Bressler, W. Richard Chesnut, Daniel Calligaro
  • 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: 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: 5623023
    Abstract: Disclosed is a curable composition comprising (A) an imidazole derivative represented by the following general formula (1), which is capable of generating free imidazole by exposure to light, and (B) a polyfunctional epoxy compound: ##STR1## wherein R represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an aralkyl group, a nitro group, a cyano group, an alkoxyl group, a phenoxy group, or an aromatic ring residue capable of forming a condensed ring in combination with a benzene ring. The composition may further incorporate therein at least one compound selected from the group consisting of polyfunctional phenol compounds, polyfunctional carboxylic acids, acid anhydrides, and amine compounds.
    Type: Grant
    Filed: May 21, 1996
    Date of Patent: April 22, 1997
    Assignee: Taiyo Ink Manufacuturing Co., Ltd.
    Inventor: Tadatomi Nishikubo
  • Patent number: 5596023
    Abstract: A liquid crystal display panel in which a liquid crystal composition is held between a pair of transparent substrates and the peripheral edges of both the substrates are sealed with a sealing material comprising (a) a partially esterified epoxy (meth)acrylate resin where 10-90% of an equivalent of the epoxy group of a bisphenol A type epoxy resin is (meth)acrylated, (b) a photopolymerization initiator, and (c) a thermosetting agent; and a sealing material for the liquid crystal display panel comprising the above-mentioned components (a), (b) and (c).
    Type: Grant
    Filed: February 22, 1995
    Date of Patent: January 21, 1997
    Assignee: Sharp Kabushiki Kaisha
    Inventors: Kojiro Tsubota, Kazuyoshi Fujioka, Yutaka Takafuji, Tsuyoshi Kurokawa, Fumio Tanaka
  • Patent number: 5565246
    Abstract: A method of forming heat-resistant raised print on a substrate using a thermographic radiation-curable powder by a thermographic process that includes radiation curing. The powders include free radical photoinitiated compositions of acrylated polymers and acrylate-modified aminoamides, and cationic photoinitiated compositions of resins using sulfonium salts.
    Type: Grant
    Filed: June 28, 1995
    Date of Patent: October 15, 1996
    Inventor: Timothy S. Hyde
  • Patent number: 5548005
    Abstract: Aqueous, radiation-curable binders and binder dispersions are disclosed that contain (A) a radiation-curable binder, and (B) a radiation-curable, hydrophilic polyepoxy-acrylate.
    Type: Grant
    Filed: December 16, 1994
    Date of Patent: August 20, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Inge Kurth, Gerhard Brindoepke, Manfred Marten
  • Patent number: 5539064
    Abstract: A resist ink composition developable with a diluted, alkaline solution, which exhibits high dispersion stability itself, can form a pattern with excellent resolution, even in the case of a low exposure amount, and can produce a cured resist film excellent in solvent resistance for high-performance printed circuits and which comprises an ultraviolet-curable resin obtained by copolymerizing (a) from 5 to 50% by weight of an ethylenically unsaturated monomer of a general formula: ##STR1## wherein R.sub.1 represents a hydrogen atom or a methyl group; R.sub.2 represents a hydrogen atom or an alkyl group; n represent an integer of from 1 to 4, and/or glycerol mono(meth)acrylate, (b) from 10 to 90% by weight or glycidyl (meth)acrylate and (c) from 0 to 80% by weight of other ethylenically unsaturated monomers capable of copolymerizing with these (a) and (b), followed by reacting the resulting copolymer with from 0.7 to 1.
    Type: Grant
    Filed: September 12, 1995
    Date of Patent: July 23, 1996
    Assignee: Goo Chemical Industries Co., Ltd.
    Inventors: Soichi Hashimoto, Satoshi Miyayama, Toshiaki Nishimura, Toshikazu Oda
  • Patent number: 5538821
    Abstract: The present invention relates to a resist ink composition characterized by comprising a specific unsaturated polycarboxylic acid resin (A) or a specific unsaturated polycarboxylic acid/urethane resin (A'), a photopolymerization initiator (B), a diluent (C), and a curing component (D) and a cured article prepared therefrom.In the formation of a solder resist pattern via selective UV-exposure through a patterned film followed by development of the unexposed part, the composition of the present invention is excellent in developability even though at a small acid value (mg KOH/g) or over a prolonged drying time and shows a resistance of the exposed part against the developing solution. Further, a cured article prepared therefrom is excellent in electroless gold plating resistance and fully satisfactory in adhesion and soldering heat resistance.
    Type: Grant
    Filed: May 9, 1994
    Date of Patent: July 23, 1996
    Assignees: Nippon Kayaku Kabushiki Kaisha, Taiyo Ink Manufacturing Co., Ltd.
    Inventors: Masahisa Kakinuma, Shigeru Komori, Kazuhiro Yoshida, Minoru Yokoshima, Tetsuo Ohkubo, Kazunori Sasahara
  • Patent number: 5525645
    Abstract: The present invention relates to a resin composition for optical molding which comprises (a) an actinic radical-curable and cationically polymerizable organic substance and (b) an actinic radiation-sensitive initiator for cationic polymerization. This composition can be cured without being affected by atmospheric oxygen.
    Type: Grant
    Filed: April 6, 1995
    Date of Patent: June 11, 1996
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Kazuo Ohkawa, Seiichi Saito
  • Patent number: 5512607
    Abstract: This invention provides a photosensitive resin composition which can be developed using water and can form a resist layer having superior hardness, adhesion and water resistance.The photosensitive resin composition of the present invention is characterized by containing an unsaturated epoxyester compound prepared by esterifying some of the epoxy side groups of an unsaturated epoxyester compound, and then reacting the remained epoxy groups of the epoxyester compound with a tertiary amine and acid component, such as phosphoric acid, a monoester of phosphoric acid or a diester of phosphoric acid or combination thereof, to convert the epoxy groups into quaternary ammonium salt groups having phosphate anions.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: April 30, 1996
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Keiichi Kinashi, Hiroshi Samukawa, Reiko Chiba
  • Patent number: 5468784
    Abstract: Disclosed is a photopolymerizable resin composition suitable for forming a solder mask layer, for example, on a printed circuit board. The photopolymerizable resin composition of the invention can be prepared in the form of an aqueous solution and is developable with water as the developer liquid so that the problems and disadvantages inherent in the use of organic solvents can be completely solved. The composition comprises, in addition to a photopolymerization initiator and a polyenic compound as a reactive diluent, a unique prepolymer as a resinous ingredient which is a copolymer of, for example, an alkyl (meth)acrylate and glycidyl (meth)acrylate modified at the epoxy groups in the copolymer partly by the reaction with (meth)acrylic acid and partly by the reaction with an onium group-containing compound, e.g. a quaternary ammonium compound, to impart solubility in water.
    Type: Grant
    Filed: February 23, 1994
    Date of Patent: November 21, 1995
    Assignee: Tamura Kaken Corporation
    Inventors: Makoto Yanagawa, Hiroshi Yamamoto
  • Patent number: 5449704
    Abstract: A liquid composition which on exposure to actinic radiation polymerises to form a heat-curable solid film adhesive, said composition comprising (A) a heat-curable phenol-aldehyde resol resin, (B) a photopolymerisable resin having, on average, more than one polymerisable acrylic group per molecule, (C) a photopolymerisation initiator for (B) and (D) an aminotriazine-formaldehyde resin.
    Type: Grant
    Filed: December 14, 1993
    Date of Patent: September 12, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Stuart J. Thompson, Stuart Mansfield
  • Patent number: 5447996
    Abstract: There are disclosed an adhesive obtained by dispersing a cured amino resin fine powder soluble in acid or oxidizing agent into an uncured heat-resistant resin matrix hardly soluble in acid or oxidizing agent when being subjected to a curing treatment as well as a printed circuit board using this adhesive and a method of producing the same. The adhesive has excellent properties such as resistance to chemicals, heat resistance, electric properties, hardness and adhesion property owing to the use of the amino resin fine powder. Therefore, the printed circuit board using such an adhesive is not influenced by service circumstance and is high in the connection reliability without forming short circuit between patterns. Furthermore, in the method of producing the printed circuit board, the adhesive is provided in form of a sheet-or a prepreg, whereby the printed circuit board can be produced easily and cheaply.
    Type: Grant
    Filed: May 24, 1994
    Date of Patent: September 5, 1995
    Assignee: Ibiden Co., Ltd.
    Inventors: Motoo Asai, Chie Onishi
  • Patent number: 5436279
    Abstract: A coating material crosslinkable by radiation comprising a) an olefinic unsaturated ester of an epoxy novolac resin, b) a binder formed by reaction of an epoxy compound having more than one epoxide group per molecule with at least one carboxylic acid in a molar ratio of epoxy groups per carboxyl group of 1:0.5 to 0.9 and subsequent reaction of the resulting reaction product with at least one unsaturated isocyanate ester formed by reaction of a compound with at least two isocyanate groups with a member of the group consisting of hydroxyl containing acrylic acid, methacrylic acid and cyanacrylic acid esters, c) at least one latent hardener, d) at least one photoinitiator e) 80-120% by weight of fillers and (f) additives, adjuvants and solvents and protective films formed with them.
    Type: Grant
    Filed: February 1, 1994
    Date of Patent: July 25, 1995
    Assignees: Rutgerswerke Aktingesellschaft, Lackwere Peters GmbH & Co. KG
    Inventors: Ulrich Grundke, Klaus-Peter Liebetanz, Achim Hansen, Jurgen Zehrfeld, Rainer Scharre, Werner Peters
  • Patent number: 5434196
    Abstract: The present invention relates to a resin composition for optical molding which comprises (a) an actinic radical-curable and cationically polymerizable organic substance and (b) an actinic radiation-sensitive initiator for cationic polymerization. This composition can be cured without being affected by atomospheric oxygen.
    Type: Grant
    Filed: July 1, 1994
    Date of Patent: July 18, 1995
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Kazuo Ohkawa, Seiichi Saito
  • Patent number: 5420172
    Abstract: Cross-linked epoxy resins having nonlinear optical properties may be used in nonlinear optical media. These cross-linked epoxy resins may have the following structure: ##STR1## Z.sup.1 and Z.sup.2 being NLO-chromophores.
    Type: Grant
    Filed: August 23, 1993
    Date of Patent: May 30, 1995
    Assignee: Siemens Aktiengesellschaft
    Inventors: Jens Nordmann, Rainer Puehl
  • Patent number: 5418112
    Abstract: A method useful for stereolithography that yields enhanced photospeed, as well as a photocurable polymer composition well adapted for use with same, are disclosed.A preferred combination includes 1,2-dimethoxy-2-phenyl acetophenone, benzophenone, and triphenyl phosphine combined with a polyurethane (meth)acrylate oligomer.
    Type: Grant
    Filed: November 10, 1993
    Date of Patent: May 23, 1995
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Srinivas K. Mirle, Ronald J. Kumpfmiller
  • Patent number: 5409740
    Abstract: A method of forming a fiber bundle which is useful as an industrial thread. The fiber bundle is prepared by integrating individual fiber filaments into a fiber bundle, applying a dual-cure adhesive material to the fiber bundle and initiating polymerization of the dual-cure adhesive material. The dual-cure adhesive material is a combination of a radiation-curable material and a moisture-curable material. The radiation-curable material contains an acrylourethane oligomer and a reactive diluent system, while the moisture-curable material contains a polyisocyanate or an isocyanate-functional urethane prepolymer. The use of a dual-cure material results in a synergistic curing process so as to form a durable and flexible industrial thread or fiber.
    Type: Grant
    Filed: December 18, 1992
    Date of Patent: April 25, 1995
    Assignee: Lord Corporation
    Inventor: Bill L. Brann
  • Patent number: 5397812
    Abstract: An adhesive composition for being applied to at least one of thread contact faces of screw members so as to stick said thread contact faces to each other in engaging the screw members with each other for the purpose of locking and sealing the engaged screw members, in which micro-capsules enclosing at least a reactive monomer of a reactive adhesive composition comprising said monomer, a polymerization initiator of the aforesaid monomer and/or an activator of the aforesaid polymerization initiator is dispersed in a binder comprising a photo-hardening resin composition.
    Type: Grant
    Filed: March 9, 1993
    Date of Patent: March 14, 1995
    Assignee: Three Bond Co., Ltd.
    Inventors: Ikuzo Usami, Makoto Kurihara, Minami Hanada, Kunihiko Nakajima
  • Patent number: 5370971
    Abstract: A photopolymerizable composition comprising:(a) an aromatic epoxy resin derivative containing, per kilogram of the resin, 0.3 to 10 mole equivalents of a polymerizable unsaturated group and 0.1 to 3 mole equivalents of a specific aprotic onium salt-containing group,(b) a polysiloxane having a specific polysiloxane chain in a molecule, and containing 0.01 to 5 mole equivalents, per kilogram of the polysiloxane, of the aprotic onium salt-containing group, and(c) a photopolymerization initiator.Said photopolymerizable composition can form a resist film excellent in adhesion to a substrate, heat resistance, chemical resistance, impact resistance and solder plating property, and is suitable as a solder resist in particular.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: December 6, 1994
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Tetsuo Ogawa, Kenji Seko, Tetsu Maki, Naozumi Iwasawa
  • Patent number: 5369139
    Abstract: Radiation and peroxide-curable oligomeric emulsions are prepared by mixing water, an .alpha.,.beta.-ethylenically unsaturated oligomer (e.g. an unsaturated polyester), a reactive, nonionic surfactant containing allyl unsaturation, and a metallic salt drier under high shear agitation until a stable emulsion is formed. Coatings prepared from these emulsions are tack and mar free and demonstrate good resistance to organic solvents and water.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: November 29, 1994
    Assignee: Cook Composites and Polymers Company
    Inventors: Rudolph H. Boeckeler, Delano R. Eslinger
  • Patent number: 5358977
    Abstract: The invention is a method of manufacturing a substrate and, particularly, of manufacturing a release paper. The method comprises coating a release paper base with a primer coat, and curing the primer coat. The cured primer coat is then overlayed with a heat-curable or an ultraviolet-curable silicone coating which is, in turn, cured with heat or ultraviolet light. A product manufactured in accordance with this method enables a facing adhered to this release paper to be removed relatively easily from that release paper.
    Type: Grant
    Filed: January 27, 1992
    Date of Patent: October 25, 1994
    Assignee: Daubert Coated Products, Inc.
    Inventors: George Krankkala, John Bachman
  • Patent number: 5356947
    Abstract: The present invention provides controllably curable photoiniferter containing adhesive compositions which are suitable for the mounting of microelectronic devices such as flip chips onto transparent wiring boards, a method of making the adhesive compositions, and a method of using the adhesive compositions in order to bond microelectronic devices to transparent wiring boards by intermittent exposure of the adhesive composition to a radiant energy source. The adhesive compositions can be cured in a stepwise fashion by intermittent controlled exposure to a source of radiation thus providing exactly the amount of cure and hardening desired.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: October 18, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Mahfuza B. Ali, Jean M. Pujol
  • Patent number: 5344893
    Abstract: There are disclosed an adhesive obtained by dispersing a cured amino resin fine powder soluble in acid or oxidizing agent into an uncured heat-resistant resin matrix hardly soluble in acid or oxidizing agent when being subjected to a curing treatment as well as a printed circuit board using this adhesive and a method of producing the same. The adhesive has excellent properties such as resistance to chemicals, heat resistance, electric properties, hardness and adhesion property owing to the use of the amino resin fine powder. Therefore, the printed circuit board using such an adhesive is not influenced by service circumstance and is high in the connection reliability without forming short circuit between patterns. Furthermore, in the method of producing the printed circuit board, the adhesive is provided in form of a sheet or a prepreg, whereby the printed circuit board can be produced easily and cheaply.
    Type: Grant
    Filed: July 17, 1992
    Date of Patent: September 6, 1994
    Assignee: Ibiden Co., Ltd.
    Inventors: Motoo Asai, Chie Onishi
  • Patent number: 5338769
    Abstract: A photo-curable resin composition containing a polycarbonate having a number average molecular weight of between 200 and 10,000 and containing at least two (meth)acrylate groups in the molecule, or a diglycidyl phthalate (meth)acrylate, an organic polymer fine powder having an average particle diameter of between 1 .mu.m and 50 .mu.m and a photo-radical polymerization initiator; and a coating liquid to be applied to a resin pattern. This resin composition is useful for preparing a clasp pattern exhibiting a theoretical form for retention, durability, etc., i.e., a cast clasp basic pattern, for producing, by a lost wax method, a cast clasp which is a metal component for holding a partial denture, retaining it and supporting it.
    Type: Grant
    Filed: February 11, 1992
    Date of Patent: August 16, 1994
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventor: Ryoichi Miyamoto
  • 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: 5284884
    Abstract: An antistatic resin composition comprised of (A) a radiation-curable acrylic, methacrylic or epoxy compound having an --(OR)m-- chain and (B) a minor amount of a quaternary ammonium salt of the formula (1): ##STR1## wherein R and R.sub.4 are an alkylene group of 1 to 3 carbon atoms, R.sub.1, R.sub.2 and R.sub.3 independently represent an alkyl or alkenyl group having up to 20 carbon atoms, or an acryloyl or methacryloyl group, n is an integer of at least 4, and A.sup.- is a counter ion. The antistatic resin-forming composition is useful, for example, for a protective layer of an optical recording medium, which is formed on the light incident side of a substrate of the optical recording medium.
    Type: Grant
    Filed: June 11, 1992
    Date of Patent: February 8, 1994
    Assignee: Kao Corporation
    Inventor: Kenichi Ueyama
  • Patent number: 5281569
    Abstract: A desensitizing ink for printing by wet or dry offset, flexographic or typographic printing is disclosed and claimed. This ink contains at least one desensitizing agent, at least one ink binder which is polymerizable or crosslinkable by UV light or electron beam radiations and, if necessary, an initiator system. Thus, the drying time of the printings is greatly reduced. The ink is free from vaporizable ink solvents.
    Type: Grant
    Filed: February 25, 1992
    Date of Patent: January 25, 1994
    Assignee: SICPA International S.A.
    Inventors: Albert Amon, Laszlo K. Boksanyi
  • Patent number: 5236967
    Abstract: An optical molding composition is used for casting and does not cause irritation to the skin or possess a bad smell. This composition comprises1. an actinic radiation-curable, radical-polymerizable organic compound 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, and2. an actinic radiation-sensitive radical polymerization initiator.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: August 17, 1993
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Kazuo Ohkawa, Seiichi Saito
  • Patent number: 5223553
    Abstract: An antistatic resin composition which is the electron radiation cured reaction product of an electron radiation curable prepolymer and an electron radiation reactive antistatic agent soluble in the prepolymer. An antistatic laminate is made by applying a mixture of the prepolymer and antistatic agent to a substrate and then contacting the mixture with electron radiation.
    Type: Grant
    Filed: November 27, 1991
    Date of Patent: June 29, 1993
    Assignee: Metallized Products, Inc.
    Inventor: Allen H. Keough
  • Patent number: H1786
    Abstract: In a process of curing epoxidized polymers of conjugated dienes which contain aromatic moieties by exposing the polymers to ultraviolet radiation in the presence of a photoinitiator, the improvement which comprises reducing the amount of irradiation necessary to achieve an effective cure by adding a small but effective amount of a photosensitizer which absorbs UV radiation in a wavelength range which is not obscured by the polymer to the polymer prior to or during irradiation.
    Type: Grant
    Filed: July 12, 1993
    Date of Patent: February 2, 1999
    Assignee: Shell Oil Company
    Inventors: Michael Alan Masse, James Robert Erickson