With Solid Polymer Derived Solely From Ethylencally Unsaturated Monomers Patents (Class 522/102)
  • 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: 5393645
    Abstract: Structured polymer layers having nonlinear optical properties are produced by a process wherein either organic compounds containing ethylenically unsaturated groups are subjected to free radical copolymerization (A) with stilbene, azo or azomethine compounds containing ethylenically unsaturated groups and donor and acceptor groups, or organic compounds containing ethylenically unsaturated groups are subjected to free radical polymerization and are mixed (B) with stilbene, azo or azomethine compounds containing ethylenically unsaturated groups and donor and acceptor groups, the copolymers (A) or mixtures (B) thus obtained are exposed imagewise to high-energy radiation, the unexposed parts are removed and the structured polymer layers thus obtained are polarized in an electric field for orientation of the chromophoric structural units in the region of the glass transition temperature of the polymer and crosslinked in an applied electric field.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: February 28, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl-Heinz Etzbach, Heike Kilburg, Hans-Joachim Lorkowski, Karl Pfeiffer
  • Patent number: 5364889
    Abstract: A method and composition for forming investment casting patterns wherein thermally-collapsible microspheres are incorporated into the pattern composition. The patterns can be made either by conventional pattern forming techniques or by solid imaging techniques. After investing the microsphere containing pattern in the ceramic shell, the pattern and shell are heated, causing a collapse of the microspheres and thereby preventing cracking of the shell. The shell is then heated to burn-out the remaining pattern material and fire the shell, thereby creating a mold.
    Type: Grant
    Filed: April 27, 1992
    Date of Patent: November 15, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: John A. Quinn, Roxy N. Fan
  • Patent number: 5356949
    Abstract: An adhesive tape comprising an energy beam transmittable base sheet having a surface tension of not more than 40 dyne/cm and an adhesive layer formed on one surface of the base sheet, the adhesive layer comprising a (meth)acrylate polymer, an epoxy resin, a photopolymerizable low molecular weight compound, a heat activatable latent curing agent for the epoxy resin and a photopolymerization initiator for the photopolymerizable low molecular weight compound. The adhesive in the adhesive layer is curable with an energy beam and the so cured adhesive develops tackiness again when heated. When the tape is used in processing a semiconductor wafer, it serves as a dicing tape for holding the wafer in position during the dicing step. Each piece of the diced and cured adhesive layer, that is attached to each chip and capable of being tackified by heating, provides an adhesive required for securely mounting the chip on the lead frame in the die-bonding step.
    Type: Grant
    Filed: February 21, 1992
    Date of Patent: October 18, 1994
    Assignee: Lintec Corporation
    Inventors: Mikio Komiyama, Yasunao Miyazawa, Kazuyoshi Ebe, Takanori Saito
  • Patent number: 5352556
    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: March 23, 1993
    Date of Patent: October 4, 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: 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: 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: 5227279
    Abstract: Disclosed is a polymer having a group represented by the following formula (I) or (II) in a side chain on a main chain consisting of carbon-carbon bonds: ##STR1## [wherein X is an oxygen atom, a sulfur atom or N--R.sup.1, R.sup.1 is a hydrogen atom, an alkyl group containing 1 to 3 carbon atoms or CH.sub.2 CO.sub.2 H], said group being decarboxylated by photo-reaction of its own or by photo-reaction with a photo-sensitizer which absorbs light to generate a free radical.
    Type: Grant
    Filed: March 24, 1992
    Date of Patent: July 13, 1993
    Assignee: Nippon Paint Co., Ltd.
    Inventor: Masami Kawabata
  • Patent number: 5215863
    Abstract: Disclosed herein is a resin composition or a solder resist resin composition comprising an epoxy resin (A) and/or an epoxy acrylate (B) obtained by reacting one chemical equivalent of epoxy groups in an epoxy resin with 0.1 to 1.0 chemical equivalent of acrylic acid, a styrene-maleic anhydride copolymer (C), an unsaturated group-containing compound (D) other than (B), and a photopolymerization initiator (E).
    Type: Grant
    Filed: October 11, 1991
    Date of Patent: June 1, 1993
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Kazuyoshi Nawata, Tetsuo Ohkubo, Minoru Yokoshima
  • Patent number: 5194516
    Abstract: The viscosity of copolymers of a) ethylene and C.sub.1 -C.sub.8 acrylate or methacrylates or b) ethylene, vinyl esters of C.sub.1 -C.sub.4 carboxylic acids, and another comonomer selected from the group consisting of carbon monoxide, acrylic acid, methacrylic acid, or a glycidyl ester of acrylic or methacrylic acid is increased, while maintaining gel content at a level of less than 3%, by treatment with a free radical generating agent.
    Type: Grant
    Filed: October 1, 1991
    Date of Patent: March 16, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: John R. Fisher, Jerald R. Harrell, Wolfgang Honsberg, John W. Paul
  • Patent number: 5149776
    Abstract: A photopolymerizing cross-linking hardenable resin composition is disclosed which is comprised of a binder resin, cross-linking monomer and photopolymerization initiator. The composition of each of the above mentioned components is such that dry film resist incorporating the resin composition of the present invention and used in processes for selective etching and plating of printed circuit boards can be developed in weak aqueous alkaline solution after selective exposure to light. In this way, the efficient and economical manufacture of high definition printed circuit boards is made possible. Additionally, dry film resist incorporating the photopolymerizing cross-linking hardenable resin composition of the present invention lends to easy handling and storage characteristics.
    Type: Grant
    Filed: November 16, 1990
    Date of Patent: September 22, 1992
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Kenji Kushi, Ken-ichi Inukai, Takayuki Iseki, Seiya Koyanagi, Yasuyuki Fujimoto
  • Patent number: 5128388
    Abstract: A hot melt adhesive crosslinkable by UV irradiation comprising a hot melt adhesive base, a saturated hydrocarbon oligomer containing at least one acryloyl group in a molecule for affording crosslinkability by UV irradiation, and a photopolymerization initiator, an optical disc comprising a pair of substrate, at least one of which is provided with an information recording layer, adhered to each other by means of a hot melt adhesive crosslinkable by UV irradiation and the process for preparing the same are disclosed. The adhesive of the present invention has a high heat resistance and heat stability, is applicable at a low temperature and at a low viscosity, has high softening point and high viscosity by UV irradiation. The optical disc of the present invention has high productivity, no corrosion and high heat resistance.
    Type: Grant
    Filed: November 29, 1988
    Date of Patent: July 7, 1992
    Assignee: Sunstar Giken Kabushiki Kaisha
    Inventors: Isamu Komori, Satoshi Nishikawa, Masao Shizuki
  • Patent number: 5096800
    Abstract: A resin composition for forming a durable protection coating contains (A) an alkali-soluble resin which is a polymer of a conjugated diene and has a monoamidated succinic acid group represented by the following formula (I) of: ##STR1## wherein R.sup.1 and R.sup.2 each stand for a hydrogen atom, a halogen atom or an organic residue having 1 to 3 carbon atoms; and R.sup.3 stands for an organic residue having 1 to 16 carbon atoms; (B) a pre-polymer having a photosensitive ethylenic double bond; and (C) a photopolymerization initiator. The mixing ratio by weight of the alkali-soluble resin (A) to the pre-polymer (B) ranges from 1:4 to 4:1. A process for preparing the durable protection coating contains applying the resin composition on a substrate, and exposing the resin composition to ultraviolet ray through a circuit pattern mask to cure the resin composition followed by development and after-curing to form the protection coating.
    Type: Grant
    Filed: November 27, 1990
    Date of Patent: March 17, 1992
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Hitoshi Yuasa, Eiji Yoda, Haruyoshi Sato, Yutaka Otsuki
  • Patent number: 5087552
    Abstract: The invention provides a photosensitive resin composition useful as a solder resist, etching resist or plating resist in the manufacture of printed circuit boards to exhibit excellent resistance against heat and chemicals and good adhesion to the substrate surface. The composition essentially comprises (a) a copolymeric resin of an .alpha.,.beta.-unsaturated dicarboxylic acid anhydride and an ethylenically unsaturated polymerizable compound, of which the acid anhydride units are partially esterified with an unsaturated alcohol and a saturated alcohol, and (b) a photopolymerization initiator. The composition may further comprise optional ingredients such as (c) a photopolymerizable monomeric compound, (d) an epoxy-based resin and (e) an aromatic diamine compound.
    Type: Grant
    Filed: October 13, 1989
    Date of Patent: February 11, 1992
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tomoki Horigome, Kenji Tazawa, Toshimi Aoyama
  • Patent number: 5086307
    Abstract: A liquid jet recording head comprising a cured product of an active energy-ray-curing resin composition as at least a part of its constitution, said composition comprises:(A) a graft copolymerized polymer having a number average molecular weight of 5,000 or more and a weight average molecular weight of 50,000 or less which comprises a trunk chain composed mainly of structural units derived from at least one monomer (hereinafter referred to as "monomer (a)") selected from the group consisting of alkyl methacrylates, acrylonitrile and stylene and has graft chains having structural units derived from at least one monomer (hereinafter referred to as "Monomer (b)") selected from the group consisting of the monomers represented by the following formula x and other monomers presented by the formula y: ##STR1## (B) a linear polymer having a number average molecular weight of 50,000 or more and a weight average molecular weight of 350,000 or less and having a glass transition temperature of 60.degree. C.
    Type: Grant
    Filed: February 13, 1991
    Date of Patent: February 4, 1992
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Saito
  • Patent number: 5069929
    Abstract: An actinic radiation-curable, rust-preventive coating composition suitable for use in temporary protection of steel products from rusting and having improved rust preventing property even in the presence of oil on the steel surface is disclosed. The coating composition comprises: (A) from 10 to 50 parts by weight of a vinyl polymer having a glass transition temperature of not lower than 5.degree. C. and a solubility parameter in the range of 9 to 11.5; (B) from 50 to 90 parts by weight of one or more polymerizable compounds having at least one unsaturated group capable of initiating reaction by actinic radiation; and (C) from 0.1 to 20 parts by weight of an organic phosphate of the formula: ##STR1## wherein R.sub.1 is hydrogen or methyl; Y is a straight or branched chain alkylene having 2 to 20 carbon atoms which may be interrupted by one or more ester or oxy linkages and/or aromatic rings; and n is an integer of 1 to 3.
    Type: Grant
    Filed: November 27, 1989
    Date of Patent: December 3, 1991
    Assignees: Sumitomo Metal Industries, Ltd., Nippon Paint Co., Ltd.
    Inventors: Tetsuzo Arai, Yasushi Yamamoto, Mitsuyuki Raijo, Isao Fujita
  • Patent number: 5068260
    Abstract: An improved active energy ray-curing resin composition comprising (i) a graft copolymerized polymer having a number average molecular weight of 5,000 or more and a weight average molecular weight of 50,000 or less; (ii) a linear polymer having a number average molecular weight of 5,000 or more and a weight average molecular weight of 350,000 or less and having a glass transition temperature of 60.degree. C. or more: (iii) an epoxy resin containing at least one compound having one or more epoxy groups in one molecule: and (iv) a polymerization initiator capable of generating a Lewis acid by irradiation of an active energy ray. The resin composition can be desirably cured with an active energy ray such as ultraviolet ray or electron beam and it is capable of being laminated in a desired pattern on a copper-coated laminate for use as a printed board or on a plate of metal, glass, ceramics or plastic.
    Type: Grant
    Filed: September 15, 1988
    Date of Patent: November 26, 1991
    Assignee: Canon Kabushiki Kaisha
    Inventor: Hiromichi Noguchi
  • Patent number: 5068258
    Abstract: An improved active energy ray-curing resin composition comprising (i) a graft copolymerized polymer having a number average molecular weight of 5,000 or more and a weight average molecular weight of 50,000 or less: (ii) a linear polymer having a number average molecular weight of 5,000 or more and a weight average molecular weight of 350,000 or less and having a glass transition temperature of 60.degree. C. or more: (iii) a half-esterificated epoxy resin: and (iv) a polymerization initiator capable of generating a Lewis acid by irradiation of an active energy ray. The resin composition can be desirably cured with an active energy ray such as ultraviolet ray or electron beam and it is capable of being laminated in a desired pattern on a copper-coated laminate for use as a printed board or on a plate of metal, glass, ceramics or plastic.
    Type: Grant
    Filed: September 15, 1988
    Date of Patent: November 26, 1991
    Assignee: Canon Kabushiki Kaisha
    Inventor: Hiromichi Noguchi
  • Patent number: 5068259
    Abstract: An improved active energy ray-curing resin composition comprising (i) a graft copolymerized polymer having a number average molecular weight of 5,000 or more and a weight average molecular weight of 50,000 or less: (ii) a linear polymer having a number average molecular weight of 5,000 or more and a weight average molecular weight of 350,000 or less and having a glass transition temperature of 60.degree. C. or more: (iii) an epoxy resin containing at least one compound having one or more epoxy groups in one molecule, (iv) a monomer having an ethylenically unsaturated bond and (v) a polymerization initiator capable of generating a Lewis acid by irradiation of an active energy ray. The resin composition can be desirably cured with an active energy ray such as ultraviolet ray or electron beam and it is capable of being laminated in a desired pattern on a copper-coated laminate for use as a printed board or on a plate of metal, glass, ceramics or plastic.
    Type: Grant
    Filed: September 15, 1988
    Date of Patent: November 26, 1991
    Assignee: Canon Kabushiki Kaisha
    Inventor: Hiromichi Noguchi
  • Patent number: 5068257
    Abstract: An improved active energy ray-curing resin composition comprising (i) a graft copolymerized polymer having a number average molecular weight of 5,000 or more and a weight average molecular weight of 50,000 or less: (ii) a linear polymer having a number average molecular weight of 5,000 or more and a weight average molecular weight of 350,000 or less and having a glass transition temperature of 60.degree. C. or more: (iii) a half-esterificated epoxy resin: (iv) a monomer having an ethylenically unsaturated bond: and (v) a polymerization initiator capable of generating a Lewis acid by irradiation of an active energy ray.The resin composition can be desirably cured with an active energy ray such as ultraviolet ray or electron beam and it is capable of being laminated in a desired pattern on a copper-coated laminate for use as a printed board or on a plate of metal, glass, ceramics or plastic.
    Type: Grant
    Filed: September 15, 1988
    Date of Patent: November 26, 1991
    Assignee: Canon Kabushiki Kaisha
    Inventor: Hiromichi Noguchi
  • Patent number: 5043362
    Abstract: Water-processable screenprinting stencils and resists are based upon photopolymerizable systems in which the hydrogen donor compound is a modified polyvinylalcohol having pendant dialkylamino groups.
    Type: Grant
    Filed: June 28, 1988
    Date of Patent: August 27, 1991
    Assignee: Autotype International Limited
    Inventors: Ross A. Balfour, John A. Sperry
  • Patent number: 5043363
    Abstract: An active energy ray-curing resin composition comprises (i) a heat-crosslinkable linear copolymer comprising 5 to 30 mol % of a monomer represented by the general formula I shown below and 5 to 50 mol % of a monomer represented by the general formula II shown below as the copolymer constituents: ##STR1## (wherein R.sup.1 is hydrogen or alkyl or hydroxyalkyl group having 1 to 3 carbon atoms; R.sup.2 is hydrogen or alkyl or acyl group having 1 to 4 carbon atoms which may have a hydroxyl group; R.sup.3 is hydrogen or alkyl group having 1 to 3 carbon atoms; R.sup.4 is a divalent hydrocarbon group which may have internally an ether bond and may also be substituted with halogen atoms; and R.sup.5 is alkyl having 3 to 12 carbon atoms or phenylalkyl group or phenyl group), and (ii) a monomer having an ethylenically unsaturated bond.
    Type: Grant
    Filed: September 12, 1990
    Date of Patent: August 27, 1991
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Munakata
  • Patent number: 4996132
    Abstract: The photosensitive resin composition comprises (a) a ternary copolymer of an ethylenically unsaturated amide, carboxyl-containing monomer and third monomer, (b) an esterified resin by the reaction of an unsaturated carboxylic acid and a novolactype epoxy resin, (c) a photopolymerizable monomer, (d) a photopolymerization initiator and (e) a powder such as a finely divided silica filler. The resist layer formed from the composition is capable of being developed with an alkaline aqueous solution and has excellent heat resistance in addition to other desirable properties when the patterned resist layer by the pattern-wise exposure to ultraviolet light and development is subjected to a heat treatment to effect thermal curing.
    Type: Grant
    Filed: February 23, 1988
    Date of Patent: February 26, 1991
    Assignee: Toyko Ohka Kogyo Co. Ltd.
    Inventors: Kenji Tazawa, Akira Iwata, Tomoki Horigome, Hiroyuki Tohda
  • 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: 4987053
    Abstract: Compounds of the general formula I ##STR1## are described in which Q denotes ##STR2## R denotes alkyl, hydroxyalkyl or aryl, R.sup.1 and R.sup.2 denote H, alkyl or alkoxyalkyl,R.sup.3 denotes H, methyl or ethyl,D.sup.1 and D.sup.2 denote saturated hydrocarbon groups,E denotes alkylene, cycloalkylene, arylene, saturated or unsaturated heteroyls or a group of the formula II ##STR3## a and b denote integers from 1 to 4. c denotes an integer from 1 to 3,m denotes 2, 3 or 4, depending on the valency of Q, andn denotes an integer from 1 to m, where all radicals of the same definition may be identical to or different from one another.The compounds are suitable as polymerizable compounds for photopolymerizable mixtures and are distinguished by ready polymerizability in combination with photoinitiators and long shelf lives in the layer.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: January 22, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Joachim Gersdorf, Klaus Rose
  • Patent number: 4970532
    Abstract: An ink jet recording head having an ink pathway in communication with a jetting exit formed on a substance on which an active element generating energy utilized for jetting out an ink is disposed, at least a portion of the ink pathway being constituted with a cured film of photosensitive resin, wherein the photosensitive resin composition includes (a) a specific high molecular compound, (b) a photopolymerizable compound having two or more acryloyl groups or methacryloyl groups in one molecule, and (c) a photopolymerization initiator. The ink jet recording head has various advantages, for example, (i) having satisfactory durability against a change in temperature during working conditions, (ii) causing no defoliation between the ink pathway walls and other constituent members even under continuous long-term use, (iii) developing no crack in the ink pathway walls even for continuous long-term use, and (iv) having satisfactory jetting durability.
    Type: Grant
    Filed: March 16, 1989
    Date of Patent: November 13, 1990
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hirokazu Komuro, Hiromichi Noguchi, Takahiro Mori
  • Patent number: 4956265
    Abstract: Aqueous solvent dispersible, radiation crosslinkable compounds and oligomers containing poly(ethylenically unsaturated) group-containing components and carboxyl groups are disclosed. Each compound is a monoester of a cyclic dicarboxylic acid anhydride and a 2-hydroxyalkylpolyester, said 2-hydroxyalkylpolyester being the ester of a polyepoxide with a monoester which is the monoester of a poly(ethylenically-unsaturated)alkanol and a dicarboxylic acid. These compounds and oligomers are useful in the field of graphic arts and protective coatings.
    Type: Grant
    Filed: January 22, 1990
    Date of Patent: September 11, 1990
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Thomas P. Klun, Aida F. Robbins, M. Zaki Ali
  • Patent number: 4952481
    Abstract: There is hereby provided a photosensitive resin composition suitable for a relief printing plate having an excellent resistance to a water based ink, whereby water or a water like solvent can be employed as a developing solution, which comprises;(i) a polymer (A) having a molecular weight of 5,000 to 500,000 which contains an amino group and a polymerizable double bond moiety,(ii) a monomer (B) having an .alpha.,.beta.-ethylenically unsaturated bond and a free acid group which can quaternize the nitrogen atom of the polymer (A),(iii) a photopolymerizable unsaturated compound (C), and(iv) a photopolymerization initiator (D).
    Type: Grant
    Filed: December 27, 1988
    Date of Patent: August 28, 1990
    Assignee: Napp Systems (USA), Inc.
    Inventors: Mamoru Seio, Hidefumi Kusuda, Masami Kawabata
  • Patent number: 4942112
    Abstract: Solid photopolymerizable compositions and photosensitive elements are provided that are useful in preparing optical elements, and especially holograms. The composition contains a polymeric binder, a liquid ethylenically unsaturated monomer, and a photoinitiator system. Typical compositions have a refractive index modulation of at least 0.005 when measured per the specified test.
    Type: Grant
    Filed: January 15, 1988
    Date of Patent: July 17, 1990
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Bruce M. Monroe, William K. Smothers
  • 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: 4937172
    Abstract: A photopolymerizable composition comprising(a) a monomeric component which is a half acryloyl ester of bisphenol A epoxy monomer;(b) an initiating system activated by actinic radiation; and(c) a preformed macromolecular elastomeric polymer binder.
    Type: Grant
    Filed: October 20, 1988
    Date of Patent: June 26, 1990
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Joseph E. Gervay
  • 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: 4929403
    Abstract: A process for rapidly forming a flexible mold for finely detailed objects from a radiatively curable molding composition includes coating at least a portion of the surface of a three-dimensional object with a fluid molding composition. The coating is cured by exposing the fluid coating to radiative energy to form an elastic, flexible layer of cured molding composition on the object. The coating and curing steps can be repeated to build up the flexible mold until a predetermined minimum has been attained. The cured molding composition is removed from the object, and is suitable for immediate use as a mold to cast duplicate reproductions of the object.
    Type: Grant
    Filed: July 25, 1989
    Date of Patent: May 29, 1990
    Inventor: Edwin F. Audsley
  • Patent number: 4923905
    Abstract: A light curable dental composition is provided. The composition comprises an ethylenic unsaturated compound and a light polymerization initiator. The light polymerization initiator is a combination of an .alpha.-diketone and a polyperoxy ester containing a benzophenone group and represented by the general formula (I) of: ##STR1## wherein R.sub.1 and R.sub.1 ' represent a tertiary alkyl group or a tertiary aralkyl group and R.sub.2 and R.sub.2 ' represent a hydrogen atom, a tertiary alkoxy group or a tertiary aralkyloxy group.
    Type: Grant
    Filed: February 26, 1988
    Date of Patent: May 8, 1990
    Assignee: Nippon Oil and Fats Co., Ltd.
    Inventors: Eiichi Masuhara, Yoshinori Kadoma, Takeo Matsumoto, Takeshi Komai, Eiichi Yamada, Osamu Nakachi, Godo Irukayama
  • Patent number: 4914165
    Abstract: Aqueous solvent dispersible, radiation crosslinkable compounds and oligomers containing poly(ethylenically unsaturated) group-containing components and carboxyl groups are disclosed. Each compound is a monester of a cyclic dicarboxylic acid anhydride and a 2-hydroxyalkylpolyester, said 2-hydroxyalkylpolyester being the ester of a polyepoxide with a monoester which is the monoester of a poly(ethylenically-unsaturated)alkanol and a dicarboxylic acid. These compounds and oligomers are useful in the field of graphic arts and protective coatings.
    Type: Grant
    Filed: February 3, 1988
    Date of Patent: April 3, 1990
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Thomas P. Klun, Aida F. Robbins, M. Zaki Ali
  • Patent number: 4855215
    Abstract: A photosetting polymer composition comprises:a base polymer comprising a denatured copolymer which is produced by reacting a copolymer of maleic anhydride and an unsaturated hydrocarbon compound with a specific aminocarboxylic acid, an alcohol or a cellosolve derivative, and a glycidyl (meth)acrylate compound under specific conditions;5-500 weight parts of a photopolymerizable monomer per 100 weight parts of the base polymer; and1-50 weight parts of a photopolymerization initiator per 100 weight parts of the base polymer.
    Type: Grant
    Filed: October 15, 1987
    Date of Patent: August 8, 1989
    Assignee: Ube Industries, Ltd.
    Inventors: Tsunetomo Nakano, Toshikazu Hayashi, Toshinori Tsukada
  • Patent number: 4849322
    Abstract: Photopolymer positive surprint color proofing film based on epoxy acrylate monomer exhibits low dot gain, low time dependence of toning and good tonal range. Binder can be methylmethacrylate/ethyl acrylate/acrylic acid copolymer, preferably cross-linked with zinc ions and plasticized with a second acrylate monomer and a mixture of triacetin and trimethylol propane.
    Type: Grant
    Filed: January 6, 1988
    Date of Patent: July 18, 1989
    Assignee: E. I. Du Pont De Nemours and Company
    Inventors: Richard D. Bauer, John G. Buzzell, Rusty E. Koenigkramer
  • Patent number: 4839400
    Abstract: An active energy ray-curable resin composition comprises (A) a graft copolymerized polymer comprising graft chains composed mainly of structural units derived from at least one monomer selected from the group consisting of (a) hydroxyl containing (meth)acrylic monomers, (b) amino or alkylamino containing (meth)acrylic monomers, (c) carboxyl containing (meth)acrylic or vinyl monomers, (d) N-vinylpyrrolidone, (e) vinylpyridine or its derivatives and (f) (meth)acrylic amide derivatives represented by the general formula (II) shown below: ##STR1## (wherein R.sub.1 is hydrogen or methyl group and R.sub.2 is hydrogen or an alkyl or acyl group having 1 to 4 carbon atoms which may have hydroxyl group added to trunk chains composed mainly of structural units compsiting at least one monomer selected from the group consisting of the monomer represented by the general formula (I) shown below: ##STR2## (wherein R.sub.1 to R.sub.
    Type: Grant
    Filed: March 6, 1987
    Date of Patent: June 13, 1989
    Assignee: Canon Kabushiki Kaisha
    Inventors: Yasufumi Sato, Megumi Munakata, Hiromichi Noguchi
  • Patent number: 4839399
    Abstract: An active energy beam-curable type resin composition, which comprises (A) a graft copolymer comprising a main chain composed mainly of structural units of monomers containing one (meth)acryloyl group and a dicyclopentenyl derivative group represented by the following general formula (I): ##STR1## wherein Z represents a five-membered ring given by ##STR2## and R.sub.1 and R.sub.
    Type: Grant
    Filed: March 5, 1987
    Date of Patent: June 13, 1989
    Assignee: Canon Kabushiki Kaisha
    Inventors: Yasufumi Sato, Megumi Munakata, Hiromichi Noguchi
  • Patent number: 4824876
    Abstract: A light curable dental liquid or paste comprises an ethylenic unsaturated monomer, a light polymerization initiator and an organic filler. The light polymerization initiator is a combination of an organic peroxide and a pyrylium salt compound of: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 each represents a hydrogen atom, an alkyl group and the like, X stands for an oxygen or sulfur atom and Y for an anionic functional group.
    Type: Grant
    Filed: March 23, 1987
    Date of Patent: April 25, 1989
    Assignee: Nippon Oil and Fats Co., Ltd.
    Inventors: Takeo Matsumoto, Eiichi Yamada, Osamu Nakachi, Godo Irukayama, Yoshihiro Minoshima
  • 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: 4756994
    Abstract: A photocurable composition comprising (a) 100 parts by weight of a resin having structural units derived from at least one alpha, beta-unsaturated ethylenically unsaturated monomer, (b) 10 to 300 parts by weight of a photopolymerizable monomer, (c) 0.1 to 20 parts by weight of a photopolymerization initiator, and (d) 0.01 to 1 part by weight of a compound represented by the following general formula (I) or general formula (II) ##STR1## wherein R.sup.1 represents a divalent aromatic hydrocarbon group having bonds at the ortho-position to each other; R.sup.2 represents hydrogen, an alkyl group having 1 to 4 carbon atoms, a phenyl group or an aryl group having a C.sub.1 -C.sub.4 alkyl; R.sup.3 and R.sup.4 each represent an alkyl group having 1 to 10 carbon atoms, an aryl group or an aralkyl group; X.sup.1 represents oxygen, sulfur or N--R.sup.5 ; X.sup.2 represents oxygen, sulfur or NH; X.sup.3 represents nitrogen or CR.sup.6 ; X.sup.4 represents oxygen, sulfur or NR.sup.6 ; X.sup.5 represents nitrogen or CR.
    Type: Grant
    Filed: June 6, 1986
    Date of Patent: July 12, 1988
    Assignee: Sekisui Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yasuhiko Araki, Shigeru Danjo, Hajime Shohi
  • 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: 4698373
    Abstract: Compositions hardenable by exposure to heat or electromagnetic radiation are provided by dissolving together to form a blend from about 0% to about 50% by weight of an uncrosslinked polymer, from about 2% to about 30% of a polymerizable monomer, from about 10% to about 70% of a crosslinked polymer in the form of discrete particles having average diameters of from 0.001 micron to about 500 microns and being swollen in said solution and from about 20% to about 70% of a crosslinking agent for said monomer. Such compositions exhibit superior chemical and physical characteristics when hardened and are suitable in a wide variety of applications as construction media. Such compositions are especially suitable in the production of prosthetic dental appliances, such as, for example, prosthetic teeth. It is believed that the hardening of such compositions as, for example, during the preparation of dental appliances forms a polymer system known as an interpenetrating polymer network.
    Type: Grant
    Filed: April 30, 1984
    Date of Patent: October 6, 1987
    Assignee: Dentsply Research & Development Corp.
    Inventors: Louis Tateosian, Frederick D. Roemer
  • Patent number: 4688055
    Abstract: A liquid jet recording head has a liquid passage communicated to the discharging outlet of the liquid which is formed with a resin composition cured with an active energy ray. The resin composition to be cured comprises (i) a heat-crosslinkable linear copolymer containing 5-30 mol % of a monomer of formula I and 5-50 mol % of a monomer of formula II ##STR1## and (ii) a monomer having an ethylenically unsaturated bond.
    Type: Grant
    Filed: July 3, 1986
    Date of Patent: August 18, 1987
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Munakata
  • Patent number: 4688052
    Abstract: A light jet recording head has a liquid passage communicated to the discharging outlet of the liquid provided on a substrate surface, said passage being formed by subjecting a layer of a resin composition curable with an active energy ray to a predetermined pattern exposure with the use of said active energy ray to thereby form a cured region of said resin composition and removing the uncured region from said layer, said resin composition comprising:(i) a linear polymer having a glass transition temperature of 50.degree. C. or higher and a weight-average molecular weight of about 3.0.times.10.sup.4 or more; and(ii) an epoxy resin comprising at least one compound having two or more epoxy groups in the molecule, the epoxy groups existing in said epoxy resin being partially esterified with an unsaturated carboxylic acid.
    Type: Grant
    Filed: July 8, 1986
    Date of Patent: August 18, 1987
    Assignee: Canon Kabushiki Kaisha
    Inventors: Tadayoshi Inamoto, Hiromichi Noguchi, Megumi Munakata
  • Patent number: 4688054
    Abstract: A liquid jet recording head has a liquid passage communicated to the discharging outlet of the liquid provided on a substrate surface, said passage being formed by subjecting a layer of a resin composition curable with an active energy ray to a predetermined pattern exposure with the use of said active energy ray to thereby form a cured region of said resin composition and removing the uncured region from said layer, said resin composition comprising the component (i) shown below and at least one of the components (ii) and (iii) shown below:(i) a graft copolymerized polymer comprising a trunk chain composed mainly of structural units derived from at least one monomer selected from the group consisting of alkyl methacrylate, acrylonitrile and styrene, having graft chains composed mainly of structural units derived from at least one monomer selected from the group consisting of (A) hydroxyl containing acrylic monomers, (B) amino or alkylamino containing acrylic monomers, (C) carboxylic containing acrylic or vin
    Type: Grant
    Filed: June 30, 1986
    Date of Patent: August 18, 1987
    Assignee: Canon Kabushiki Kaisha
    Inventors: Tadayoshi Inamoto, Hiromichi Noguchi, Megumi Munakata
  • Patent number: 4688053
    Abstract: A liquid jet recording head having a liquid passage communicated to a liquid discharging outlet provided on a substrate surface is obtained, said passage being formed by subjecting a layer of a resin composition curable with an active energy ray to a predetermined pattern exposure with the use of said active energy ray to thereby form a cured region of said resin composition and removing the uncured region from said layer, said resin composition comprising:(i) a linear polymer having a glass transition temperature of 50.degree. C. or higher and a weight average molecular weight of about 3.0.times.10.sup.4 or higher;(ii) a monomer having an ethylenically unsaturated bond;(iii) an epoxy resin comprising at least one compound having one or more epoxy groups in the molecule; and(iv) a polymerization initiator capable of generating a Lewis acid by irradiation with an active energy ray.
    Type: Grant
    Filed: July 8, 1986
    Date of Patent: August 18, 1987
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Munakata
  • Patent number: 4688056
    Abstract: A liquid jet recording head, having a liquid passage communicated to the discharging outlet of the liquid provided on a substrate surface, said passage being formed by subjecting a layer of a resin composition curable with an active energy ray to a predetermined pattern exposure with the use of said active energy ray to thereby form a cured region of said resin composition and removing the uncured region from said layer, said resin composition comprising (i) a graft copolymerized polymer, (iii) an epoxy resin comprising at least one compound having one or more epoxy groups in the molecule and (iv) a polymerization initiator capable of generating a Lewis acid by irradiation of an active energy ray.
    Type: Grant
    Filed: July 3, 1986
    Date of Patent: August 18, 1987
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Munakata