Chemical Reactant Has Two Or More Ethylenic Groups Patents (Class 522/121)
  • Patent number: 5565501
    Abstract: The present invention provides a composition comprising (a) a carboxyl-group containing multifunctional acrylate; (b) a multifunctional acrylate having three or more acryloyl groups in the molecule; (c) an organic solvent; and optionally, (d) a photopolymerization initiator, (e) a colloidal metal oxide and (f) an acrylic resin is provided. This composition is applied to a plastic substrate and then irradiated with active energy rays, thereby forming a hard-coating layer having good adhesiveness to the substrate, transparency and hardwearing properties.
    Type: Grant
    Filed: April 17, 1995
    Date of Patent: October 15, 1996
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Noritaka Hosokawa, Kazuhide Hayama
  • Patent number: 5558975
    Abstract: A process is disclosed for producing a liquid jet recording head comprising applying an active energy-curing resin composition onto at least a part of a surface of a first member for forming a wall of the liquid path; exposing the applied active energy-ray-curing resin to an active energy ray selected from the group consisting of an ultraviolet-ray having an intensity of 1 mW/cm.sup.2 to 100 mW/cm.sup.2 and an electron beam having an intensity of 0.5M Rad to 20M Rad; and providing a second member on the exposed active energy-ray-curing resin composition.
    Type: Grant
    Filed: March 13, 1995
    Date of Patent: September 24, 1996
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Saito
  • Patent number: 5536621
    Abstract: An active energy ray-curing resin composition of (a) butadiene polymer having a number-average molecular weight of not less than about 10,000, and (b) a liquid polybutadiene having in the molecule 1.5 or more, on the average, of at least one of acryloyl group and methacryloyl group.
    Type: Grant
    Filed: February 6, 1995
    Date of Patent: July 16, 1996
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takahiro Mori, Hiromichi Noguchi, Tadayoshi Inamoto
  • Patent number: 5532111
    Abstract: Reactive polymeric dyes are provided comprising a chromophoric moiety derived from at least one free radically polymerizable dye and an azlactone moiety derived from 2-alkenylazlactone such that the free radically polymerizable dye is incorporated into the backbone of the polymer. Alternatively, 2-alkenylazlactone is polymerized and then derivatized with a nucleophilic dye or dyes, such that the chromophoric portion of the dye is pendent to the polymer backbone. Both types of reactive polymeric dyes may also contain additional polymerized monomeric units. The reactive polymeric dyes of the present invention can be used in a photoresist system and in particular in a color proofing construction.
    Type: Grant
    Filed: November 4, 1994
    Date of Patent: July 2, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Gary L. Holmes, Terrance P. Smith, Mahfuza B. Ali, David W. Macomber
  • Patent number: 5530036
    Abstract: An epoxy group-containing thermosetting resin composition comprising (A) a copolymer obtained From (a) at least one member selected from an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride, (b) an epoxy group-containing unsaturated compound, (c) a monoolefin unsaturated compound, and optionally (d) a conjugated diolefin unsaturated compound, and (B) an organic solvent for dissolving the above copolymer. There is also provided another epoxy-group containing thermosetting resin composition which contains the above component (A), (C) a polymerizable compound having at least one ethylenically unsaturated double bond, and (D) a photopolymerization initiator. These epoxy-group containing thermosetting resin compositions are excellent in storage stability.
    Type: Grant
    Filed: December 15, 1994
    Date of Patent: June 25, 1996
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Kimiyasu Sano, Masayuki Endo, Atsufumi Shimada, Yasuaki Yokoyama, Nobuo Bessho
  • Patent number: 5514727
    Abstract: This invention relates to vinyl ether-based coatings for which properties such as color stability, thermal stability, mechanical stability, hydrolyric stability, and resistance to embrittlement may be maintained and properties hydrogen generation and blocking are minimized. The invention also relates to stabilizers which control these properties in the coatings.
    Type: Grant
    Filed: July 13, 1994
    Date of Patent: May 7, 1996
    Assignee: AlliedSignal Inc.
    Inventors: George D. Green, James R. Snyder, Raymond J. Swedo
  • Patent number: 5500453
    Abstract: A sulfonium complex or oxosulfonium complex of the formula (1), ##STR1## wherein R.sup.1 is a benzyl group, a substituted benzyl group, a phenacyl group, a substituted phenacyl group, an aryloxy group, a substituted aryloxy group, an alkenyl group or a substituted alkenyl group, each of R.sup.2 and R.sup.3 is independently any one of groups defined as R.sup.1, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an aralkyl group, a substituted aralkyl group, an alkynyl group, a substituted alkynyl group, an alicyclic group, a substituted alicyclic group, an alkoxyl group, a substituted alkoxyl group, an alkylthio group, a substituted alkylthio group, an amino group or a substituted amino group, or R.sup.2 and R.sup.3 may bond together forming a ring structure, R.sup.4 is an oxygen atom or lone pair, and each of R.sup.5, R.sup.6, R.sup.7 and R.sup.
    Type: Grant
    Filed: August 4, 1994
    Date of Patent: March 19, 1996
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Yasumasa Toba, Madoka Yasuike, Yamaguchi Takeo
  • Patent number: 5498641
    Abstract: A photopolymerizable composition comprising at least an addition polymerizable compound having at least one ethylenically unsaturated double bond and a photopolymerization initiator system, which system comprises (a) a sensitizer of the formula (I): ##STR1## wherein each of R.sup.1 to R.sup.6 is hydrogen, halogen, alkyl, aryl, aralkyl, acyl, alkoxycarbonyl, optionally substituted hydrocarbon ring, optionally substituted heterocyclic residue or --SO.sub.3 --R.sup.8, wherein R.sup.8 is hydrogen, alkyl, aryl, aralkyl, alkali metal, or quaternary ammonium, R.sup.7 is hydrogen, alkyl, aryl, aralkyl, optionally substituted hydrocarbon ring, or optionally substituted heterocyclic group, each of X.sup.1 and X.sup.2 is halogen, alkyl, aryl, aralkyl, optionally substituted hydrocarbon ring, or optionally substituted heterocyclic group, and (b) a titanocene compound.
    Type: Grant
    Filed: April 8, 1994
    Date of Patent: March 12, 1996
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Toshiyuki Urano, Hideki Nagasaka, Masaaki Tsuchiyama, Hiroshi Ide
  • Patent number: 5484823
    Abstract: A photopolymerizable adhesive comprises (A) an acrylic resin having groups represented by the formulae: --COOH, --OH and --NHCH.sub.2 OR (wherein R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), a number average molecular weight of from 3,000 to 200,000 and a glass transition temperature of at least 70.degree. C., (B) a photopolymerizable oligomer containing at least one member selected from the group consisting of (a) an acrylate or a methacrylate of a novolak epoxy resin, (b) an acrylate or a methacrylate of a bisphenol epoxy resin and (c) an urethane acrylate of aromatic alcohol or cycloaliphatic alcohol, and (C) a photoinitiator capable of discharging radicals with the action of activation energy.
    Type: Grant
    Filed: August 29, 1994
    Date of Patent: January 16, 1996
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiromichi Noguchi, Naohito Asai, Yuko Suga
  • Patent number: 5459174
    Abstract: A radiation curable functionalized polymer is disclosed. The functionalized polymer is a copolymer of an isoolefin of 4 to 7 carbon atoms and para-alkylstyrene, wherein the para-alkylstyrene is functionalized with an acrylate or a mixture of acrylates and/or a photosensitizer and/or other functional groups at the para-alkyl groups of the para-alkylstyrene.
    Type: Grant
    Filed: June 24, 1994
    Date of Patent: October 17, 1995
    Inventors: Natalie A. Merrill, Hsian-Chang Wang, Anthony J. Dias
  • Patent number: 5445919
    Abstract: A photopolymerizable composition for forming protective layers of color filters, which comprises:(1) a photopolymerization initiator or a photopolymerization initiator system,(2) an addition-polymerizable monomer having an ethylenically unsaturated double bond, and(3) a resin produced by reaction of an anhydride-containing copolymer having a number average molecular weight of 500 to 30,000 which contains repeating units represented by at least formulas (I), (II) and (III), respectively, with a primary amine represented by formula (IV) with the ratio of the primary amine to the copolymer being 0.1 to 1.0 equivalent per equivalent of the anhydride in the copolymer: ##STR1## wherein the variables in formulas (I), (II), (III) and (IV) are defined in the specification.
    Type: Grant
    Filed: June 10, 1994
    Date of Patent: August 29, 1995
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yuichi Wakata, Masayuki Iwasaki, Koji Inoue
  • Patent number: 5439982
    Abstract: This invention relates to reactive polymers, e.g., aqueous emulsion polymers, having pendant flexible or dangling side chains prepared from ethylenically unsaturated carbodiimides, e.g., carbodiimide (meth)acrylates. The reactive polymers contain ethylenic unsaturation near the surface or in the surface area of the particles that form the polymers, the ethylenic unsaturation being connected to the polymer through the pendant flexible or dangling side chains. This invention also relates to the process for preparing the reactive polymers, to crosslinkable formulations based on the reactive polymers, and to thermoplastic and crosslinked films prepared from the reactive polymers. The reactive polymers are useful as decorative and functional coatings, inks, adhesives, textile coatings and sealants.
    Type: Grant
    Filed: August 25, 1994
    Date of Patent: August 8, 1995
    Assignee: Union Carbide Chemical & Plastic Technology Corporation
    Inventors: James W. Taylor, Martha J. Collins, David R. Bassett
  • Patent number: 5437932
    Abstract: Novel photosensitive compositions based on azlactone derived polymers are described. The polymers have a hydroearbyl backbone and pendant peptide groups with free-radically polymerizable functionality attached thereto, said polymer further comprising at least one oxyacid group or salt thereof, and optionally quaternary ammonium salt groups. A high speed durable printing plate having a mild pH aqueous developability is disclosed which incorporates these polymers in combination with a photoinitiator. The polymers are also useful as proofing films in graphic arts applications.
    Type: Grant
    Filed: May 13, 1994
    Date of Patent: August 1, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: M. Zaki Ali, Mahfuza B. Ali, Dean M. Moren
  • Patent number: 5426008
    Abstract: A photocurable gel suitable for articles such as printing plates, photoresists and the like is disclosed. The photocurable eel comprises (a) a polymer composition having isotactic polymethyl methacrylate moiety; and syndiotactic polymethyl methacrylate moiety; (b) a photopolymerizable ethylenically unsaturated compound; and (c) a photopolymerization initiator. The gel is solid at ambient temperature and is capable of undergoing reversible gel/sol transition by heating or cooling. Methods of preparing articles, as well as methods of fixing articles, which use the gel are also disclosed. Such methods include sealing or affixing component parts on an electronic circuit board.
    Type: Grant
    Filed: November 15, 1993
    Date of Patent: June 20, 1995
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Yoshichi Hagiwara, Yuichi Mori, Hiroshi Samukawa, Kazuhide Saigo
  • Patent number: 5420171
    Abstract: A UV curable organic solvent soluble, aqueous nonalkaline soluble and peelable temporary solder mask composition to be applied to a surface to be protected, having a reactive diluent monomer capable of polymerization upon exposure to ultraviolet light and a photoinitiator serving as a free radical source to initiate polymerization.
    Type: Grant
    Filed: December 31, 1991
    Date of Patent: May 30, 1995
    Assignee: Tech Spray, Inc.
    Inventor: Greg R. Unruh
  • Patent number: 5413863
    Abstract: Holographic films are disclosed that contain a binder having the following formula:(M).sub.w (VAc).sub.x (VOH).sub.y (VOS).sub.zwherein M is a fluoromonomer; VAc is vinyl acetate; VOH is vinyl alcohol; and VOS is vinyl trimethylsilyl ether; and wherein w, x, y, and z are percentages by weight; w is 5 to 30, x is 40 to 80, y is 0 to 20, and z is 2 to 30; said copolymers containing 3 to 23% by weight fluorine. These imaged films are particularly suited for lamination to glass in head-up display applications.
    Type: Grant
    Filed: November 4, 1993
    Date of Patent: May 9, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Andrew M. Weber, Aleksander Beresniewicz
  • Patent number: 5411994
    Abstract: Disclosed are graft copolymers of polyolefins and a method of preparing said graft copolymers. The method comprises irradiating a mass of olefin polymer particles and thereafter treating the mass of particles with a vinyl monomer in liquid form. A nonoxidizing environment is maintained throughout the process while free radicals produced in the olefin polymer by the irradiation are present, thereby preventing degradation of the polymer. In a final step, residual free radicals are deactivated, and any unreacted monomer is removed.
    Type: Grant
    Filed: November 6, 1992
    Date of Patent: May 2, 1995
    Assignee: Himont Incorporated
    Inventors: Paolo Galli, Anthony J. DeNicola, Jr., Jeanine A. Smith
  • Patent number: 5409965
    Abstract: An active energy ray-curing abrasion resistant coating composition is provided by incorporating following components: (a) a carboxylate-containing polyfunctional acrylate obtained by reacting a tetracarboxylic dianhydride and a hydroxyl group-containing polyfunctional acrylate having hydroxyl group(s) and at least three acryloyl groups and then neutralizing the reaction product; (b) a polyfunctional acrylate having at least three acryloyl groups; (c) an organic solvent; and (d) a photopolymerization initiator. The composition may comprise in addition to the components (e) a silica sol in an organic solvent as a dispersion medium. The composition may further comprise in addition to the components (f) an acrylic resin. Such composition is an active energy ray-curing abrasion-resistant coating composition which forms a film having excellent adhesion to a plastic sustrate, transparency, abrasion resistance and antistatic properties.
    Type: Grant
    Filed: July 26, 1994
    Date of Patent: April 25, 1995
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Noritaka Hosokawa, Kazuhide Hayama
  • Patent number: 5407784
    Abstract: An aqueous-developable article is made from a photoprepolymer made by reacting a maleated polyalkadienyl homo- or copolymer (e.g., polybutadiene) with an olefinically unsaturated compound capable of opening anhydride rings (e.g., hydroxyethyl methacrylate) with simultaneous chain extension using a polyalkadienyl polyol, followed by hydrolysis and neutralization with Li--, Na--, or K-containing base. When formulated with unsaturated monomers and photoinitiators, the photoprepolymer is particularly useful in making photopolymer-based flexographic printing plates.
    Type: Grant
    Filed: March 22, 1991
    Date of Patent: April 18, 1995
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Arthur L. Berrier, Ronald J. Kumpfmiller
  • Patent number: 5399655
    Abstract: This invention concerns positive-working photodefinable polyimide precursors which make use of chemical amplification based on photoacid catalyzed cleavage of acid labile-poly(amic acetal esters).
    Type: Grant
    Filed: October 29, 1993
    Date of Patent: March 21, 1995
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Howard E. Simmons, III
  • Patent number: 5393801
    Abstract: An electron beam-crosslinkable plastisol is provided comprising, as requisite components, (A) a particulate epoxy group-containing paste resin for plastisol processing having an epoxy group concentration on the particle surface of 1.times.10.sup.-5 to 1.times.10.sup.-3 g equivalent/g and an average particle size of 0.05 to 5 .mu.m, (B.sub.1) an unsaturated acid having a pKa less than 4, (B.sub.2) an amino group-containing unsaturated compound, and (C) a plasticizer. This plastisol can effectively be crosslinked by application of an electron beam of low-speed energy to give moldings having suitable properties.
    Type: Grant
    Filed: February 28, 1992
    Date of Patent: February 28, 1995
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Eitaro Nakamura, Kazunori Ueki
  • Patent number: 5385956
    Abstract: The method concerns preparing a polymer composition containing an electrically conductive polymer which is formed, in the presence of a catalyst, from polymerizable monomer units that are converted from non-polymerizable precursor monomers with the aid of a sufficiently energy-intense light source. In this method according to the invention is that the precursor monomers have a structure according to formula (I). The method according to the invention makes it possible to very easily and rapidly, and thus economically, prepare a polymer composition containing an electrically conductive polymer. Furthermore, the method according to the invention permits a polymer composition to be produced that contains an electrically conductive polymer in specifically pre-selected areas.
    Type: Grant
    Filed: July 15, 1993
    Date of Patent: January 31, 1995
    Assignee: DSM N.V.
    Inventors: Ronald M. A. M. Schellekens, Hans K. Van Dijk
  • Patent number: 5373031
    Abstract: A styrene-based polymer molding is obtained molding a styrene-based polymer having mainly syndiotactic configuration and then irradiating the molding thus obtained with electron rays. This molding is excellent in heat resistance and further inexpensive. Thus the molding is useful as a material required to have high heat resistance, such as a structural material, a food container material, a food wrapping material or an electric or electronic part material, particularly as an electric or electronic part material, because it is excellent in soldering resistance.
    Type: Grant
    Filed: September 20, 1993
    Date of Patent: December 13, 1994
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Keisuke Funaki, Komei Yamasaki
  • Patent number: 5362603
    Abstract: The present invention relates to a photopolymerizable composition containing a photopolymerizable compound having at least one ethylenically unsaturated double bond, a photopolymerization initiator, a pigment and optionally another resin, wherein said photopolymerizable compound contained therein comprises not less than 60%.
    Type: Grant
    Filed: February 24, 1993
    Date of Patent: November 8, 1994
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Yoshinori Katoh, Naoko Ichinose, Teruhito Sotogoshi
  • Patent number: 5360873
    Abstract: An actinic radiation-reactive pressure-sensitive adhesive composition which can be cured in air at a high speed, without irritation and bad smell, comprises1 a pressure-sensitive adhesive compound comprising an acrylate copolymer and2 an actinic radiation-curable resin comprising (1) one or more polythiol compounds and (2) one or more polyene compounds each having an least two actinic radiation-reactive acrylate carbon-to-carbon double bonds in the molecule.
    Type: Grant
    Filed: August 20, 1993
    Date of Patent: November 1, 1994
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Kazuo Ohkawa, Seiichi Saito
  • Patent number: 5356754
    Abstract: A photopolymerizable or radiation polymerizable alkaline developing crosslinking curable resin composition possessing superior antiplating properties and a short stripping period, in which the stripped plate is not easily dissolved in the stripping fluid, and which is comprising:(a) 5-30 parts by weight of at least one compound possessing in one molecule on the average 1.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: October 18, 1994
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Kenji Kushi, Ken-ichi Inukai, Takayuki Iseki, Seiya Koyanagi
  • 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: 5322762
    Abstract: A highly stable photopolymerizable composition which is highly photosensitive to visible light, which can be hardened using a visible light laser, such as an argon laser, which provides excellent contrast between non-irradiated portions and the substrate under red light, and, moreover, which provides excellent contrast between the portions irradiated by the laser and the portions not irradiated. The photopolymerizable composition consists of 100 parts by weight of a resin which is hardenable under visible light having an irradiation energy mainly consisting of light rays in the 400 nm to 700 nm visible light region; 0.02 to 0.5 parts by weight of at least one dye selected from the group consisting of Victoria Pure Blue, anthraquinone dyes, monoazo dyes, and merocyanine dyes, these dyes having maximum absorption wavelengths from 550 to 700 nm; 0.1 to 5 parts by weight of the leuco dye 4,4'-(phenylmethylene bis[N,N-diethylbenzene amine]; and 0.1 to 5 parts by weight of tribromomethylphenyl sulphone.
    Type: Grant
    Filed: April 13, 1993
    Date of Patent: June 21, 1994
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Kenji Kushi, Chiho Tokuhara
  • Patent number: 5304458
    Abstract: Flexographic photosensitive printing plates are made with formulations comprising block polymers having an architecture of BA, CBA or CBCA, where A is poly(vinylpyridine), B is poly(butadiene) or poly(isoprene) and C is styrene. The polymers may be quaternized or neutralized with an organic acid. When made with quaternized polymers, the plates after imaging with UV may be developed in aqueous solutions. The block polymers offer further advantages as to ease of synthesis, safety and improved resolution.
    Type: Grant
    Filed: September 8, 1992
    Date of Patent: April 19, 1994
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Arthur L. Berrier, Rustom S. Kanga
  • Patent number: 5298291
    Abstract: An infinite network polymer containing fluorine as a coating or cladding material for optical fibers. Fluoropolymers, such as silicone amine C.sub.0 -C.sub.16 fluoroepoxy resin and cis-trans fluoropolyol polyacrylate, reduce water permeability because of the bonding between the fluoropolymer and the substrate. The fluoropolymers exhibit substantially increased moisture resistance when compared to conventional fiber coating materials. Variations in chemical structure effect physical properties of the polymer and different compounds can be chosen for their desired physical properties, such as moisture resistance or abrasion resistance. Incorporation of fluorine into the polymer structure lowers the index of refraction such that the polymer can be used as a cladding for silica glass in an optical fiber. One fluoropolymer formulation allows in-line coating of the optical fiber in a oxygen environment.
    Type: Grant
    Filed: March 19, 1993
    Date of Patent: March 29, 1994
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Liliana Klinger, James R. Griffith
  • Patent number: 5292618
    Abstract: A photocurable gel suitable for articles such as printing plates, photoresists and the like is disclosed. The photocurable gel comprises (a) a polymer composition having isotactic polymethyl methacrylate moiety; and syndiotactic polymethyl methacrylate moiety; (b) a photopolymerizable ethylenically unsaturated compound; and (c) a photopolymerization initiator. The gel is solid at ambient temperature and is capable of undergoing reversible gel/sol transition by heating or cooling. Methods of preparing articles, as well as methods of fixing articles, which use the gel are also disclosed. Such methods include sealing or affixing component parts on an electronic circuit board.
    Type: Grant
    Filed: April 18, 1991
    Date of Patent: March 8, 1994
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Yoshichi Hagiwara, Yuichi Mori, Hiroshi Samukuaa, Kazuhide Saigo
  • Patent number: 5284736
    Abstract: A flame-resistant, photo-curing resin composition of the present invention consists of:(a) 35 to 65 parts by weight of an acrylic thermoplastic polymer, the acrylic thermoplastic polymer being 15 to 30% by weight copolymerized with at least one of monomer containing an alpha, beta-unsaturated carboxyl group,(b) 5 to 30 parts by weight of a bromine-substituted monomer represented by a general formula [I]: ##STR1## wherein R.sub.1 is H or CH.sub.3,A is ##STR2## wherein R.sub.2 is an alkylene group containing two or three carbon atoms,n is an integer between 1 and 4, andX.sub.1, X.sub.2, and X.sub.3 are Br or H, under a condition that at least two of the X.sub.1, X.sub.2, and X.sub.3 are Br,(c) 0 to 10 parts by weight of antimony trioxide particles with an average diameter of 0.1 .mu.m or smaller,(d) 20 to 50 parts by weight of a vinyl monomer, excluding component (b), and(e) 0.
    Type: Grant
    Filed: December 2, 1991
    Date of Patent: February 8, 1994
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Kenji Kushi, Ken-ichi Inukai
  • Patent number: 5281510
    Abstract: A photosensitive elastomeric composition comprising (1) at least one elastomer, (2) an addition-polymerizable compound having at least one CH.sub.2 .dbd.C< group and (3) a polymerization initiator activatable by actinic light, wherein the elastomer (1) is an elastomer selected from (a) an elastomeric polymer composed of a polyene monomer containing at least two non-conjugated double bonds and a conjugated diene-type monomer or both a conjugated diene-type monomer and a copolymerizable vinyl monomer and (b) an elastomeric linear A-B type (wherein A represents a polymer block of a monovinyl aromatic compound and B represents a polymer block of a conjugated diene-type monomer) block copolymer in which a terminal group having a polymerizable ethylenic double bond is present in at least one end of the molecular chain.
    Type: Grant
    Filed: December 30, 1992
    Date of Patent: January 25, 1994
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Fusayoshi Sakurai, Hiroto Kidokoro, Mitsuhiro Tamura
  • Patent number: 5256446
    Abstract: A process for the manufacture of reflectors, in particular reflectors for automotive vehicle headlamps, wherein a metallic film is applied to a metallization primer cured by UV or electron radiation. The radiation-curable metallization primer comprisesA) 10 to 50% by weight of an acrylate copolymer containing ethylenically unsaturated side chains and having a number average molecular weight of 6,000 to 14,000,B) 4 to 50% by weight of a mixture ofb1) 2 to 20% by weight of a monomer or oligomer containing three acryloyl groups,b2) 2 to 20% by weight of a polyethylenically unsaturated aliphatic oligomer of the formula (I) ##STR1## b3) 5 to 20% by weight of a difunctional acrylic carbonate monomer, C) 1 to 8% by weight of a photoinitiator,D) 0 to 5% by weight of customary auxiliaries and additives, andE) 0 to 60% by weight of one or more solvents inert toward components A-D the components A to E in each case totalling 100% by weight.
    Type: Grant
    Filed: September 12, 1991
    Date of Patent: October 26, 1993
    Assignee: BASF Lacke + Farben Aktiengesellschaft[DE/DE]
    Inventor: Hans-Werner Bogen
  • Patent number: 5250390
    Abstract: A light-curable elastomeric mixture is described, containinga) an elastomeric binder or binder mixture,b) a low molecular-weight compound which is polymerizable by a free-radical mechanism, is compatible with said binder or binder mixture, has at least one ethylenically unsaturated end group and has a boiling point above 100.degree. C. at normal pressure, andc) a compound or combination of compounds which is capable of initiating the polymerization of compound (b) under the action of actinic light,wherein said elastomeric binder is a block copolymer, soluble or dispersible in water or in an aqueous solution, having a structure selected from the group consisting of A--B, B--A--B, C--A--B, C--A--C--B, B--C--A--C--B, A.sub.n XB.sub.n, (A--B).sub.x X, C.sub.n X(A--B).sub.n, (C--A).sub.n XB.sub.n, (C--A--B).sub.n X, C.sub.n X(A--C--B).sub.n, (C--A).sub.n X(C--B).sub.n, (C--A--C).sub.n XB.sub.n, (C--A--C--B).sub.n X, B.sub.n XA.sub.n XB.sub.n, X(B--A--B).sub.n X, (B--C).sub.n XA.sub.n X(C--B).sub.n, B.sub.
    Type: Grant
    Filed: October 8, 1991
    Date of Patent: October 5, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Willi-Kurt Gries
  • Patent number: 5250389
    Abstract: Disclosed is a photosensitive elastomer composition comprising (1) a thermoplastic block copolymer comprising at least one monovinyl substituted aromatic hydrocarbon polymer block and at least one conjugated diene polymer block, wherein a monovinyl substituted aromatic hydrocarbon content (A) is 10 to 35% by weight, and the vinyl content (V) of a conjugated diene is 20 to 50%, and the (A) and the (V) satisfy the formula: 40.ltoreq.(A)+(V).ltoreq.70; (2) an ethylenically unsaturated compound component; and (3) a photopolymerization initiator.
    Type: Grant
    Filed: May 12, 1992
    Date of Patent: October 5, 1993
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Shohei Nakamura, Kousi Anai
  • Patent number: 5244935
    Abstract: An ultraviolet curing antifogging agent is disclosed. The composition includes block copolymer (a) having a hydrophilic polymer segment (a1) and a hydrophobic polymer segment (a2). A polar solvent (c) is provided in which the hydrophilic polymer segment (a1) can easily be dissolved while the hydrophobic polymer segment (a2) can not. It further includes a photopolymerizable compound (b), and a photopolymerization initiator (d). The block copolymer (a) contains at least one hydrophilic monomer selected from the group of: a (meth) acrylamide compound represented by the general formula: CH.sub.2 .dbd.CR.sub.1 CONR.sub.2 R.sub.3 ; a cyclic (meth)acrylamide compound represented by the general formula ##STR1## and a hydroxyalkyl (meth)acrylate. Further, the hydrophilic polymer segment (a1) is formed by a radically polymerizable monomer having a functional group such as glycidyl group.
    Type: Grant
    Filed: July 31, 1992
    Date of Patent: September 14, 1993
    Assignee: Nippon Oil and Fats Co., Ltd.
    Inventors: Yoshihiro Oshibe, Yasuhiro Yamamoto, Hiroshi Ohmura, Keiji Kumazawa
  • Patent number: 5244962
    Abstract: There are provided pressure-sensitive adhesives which comprise free radical cured mixtures of at least one crosslinkable olefin polymer and at least one tackifying organic additive, preferably a hydrogenated additive, which is substantially nonresponsive to action of free radicals and present in an amount sufficient to tackify the cured mixture of polymer and additive.
    Type: Grant
    Filed: August 14, 1991
    Date of Patent: September 14, 1993
    Assignee: Avery Dennison Corporation
    Inventors: Sebastian S. Plamthottam, Roger H. Mann, John O. Landers
  • Patent number: 5235015
    Abstract: Novel photosensitive compositions based on azlactone derived polymers are described. The polymers have a hydrocarbyl backbone and pendant peptide groups with free-radically polymerizable functionality attached thereto, said polymer further comprising at least one oxyacid group or salt thereof, and optionally quaternary ammonium salt groups. A high speed durable printing plate having a mild pH aqueous developability is disclosed which incorporates these polymers in combination with a photoinitiator. The polymers are also useful as proofing films in graphic arts applications.
    Type: Grant
    Filed: February 21, 1991
    Date of Patent: August 10, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: M. Zaki Ali, Mahfuza B. Ali, Dean M. Moren
  • Patent number: 5232767
    Abstract: A biaxially stretched heat-shrinkable laminated film is disclosed which possesses good heat-shrinkability, excellent melt hole resistance and heat-resistant sealing property (the heat resistance of a seal portion), and highly satisfactory cold resistance, retains transparency even after shrinkage, and serves advantageously as a wrap for packaging foodstuffs. The laminated film is provided as an oxygen barrier layer with a layer of a mixture of vinylidene chloride resin and a low melting point polyamide resin having a crystalline melting point of not higher than 210.degree. C. This mixed resin has been cross-linked by applying the electron beam to the laminate in a dosage in the range of 1 to 12 megarads. The laminated film exhibits a heat shrinkage percentage of not less than 15% at 90.degree. C. and excels in gas barrier property.
    Type: Grant
    Filed: January 6, 1992
    Date of Patent: August 3, 1993
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Nobuyuki Hisazumi, Tsutomu Uehara, Hiroyuki Ohba, Kazuhiko Hirose, Yoshihiro Matsukura, Kunio Shibuya
  • Patent number: 5232958
    Abstract: Electron-beam cure by itself or in combination with multifunctional additives is used to improve the high-temperature shear properties of emulsion polymerized pressure-sensitive adhesives.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: August 3, 1993
    Assignee: Avery Dennison Corporation
    Inventors: Prakash Mallya, Sebastian S. Plamthottam, Yehuda Ozari
  • Patent number: 5221595
    Abstract: A photopolymerizable mixture is disclosed that contains a polymer binder, a polymerizable compound having at least one terminal ethylene double bond and a boiling point above 100.degree. C. at normal pressure, a hexaarylbisimidazole and a 1,3-diarylpyrazoline or a 1-aryl-3-aralkenyl-pyrazoline. The mixture is suitable for the preparation of printing plates and photoresists and is distinguished by high photosensitivity and low sensitivity towards acid solutions.
    Type: Grant
    Filed: March 27, 1991
    Date of Patent: June 22, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Juergen Lingnau, Hans-Dieter Frommeld
  • Patent number: 5218009
    Abstract: Compounds of the formula I ##STR1## in which at least one of the radicals R.sub.1, R.sub.2 and R.sub.3 is a substituted alkyl radical or cycloalkyl radical, or R.sub.1 and R.sub.2 together with the phosphorus atom form a monocyclic or tricyclic ring, are effective photoinitiators for the photopolymerization of ethylenically unsaturated compounds.
    Type: Grant
    Filed: August 28, 1991
    Date of Patent: June 8, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Werner Rutsch, Kurt Dietliker, Roger G. Hall
  • Patent number: 5213723
    Abstract: A process for producing a rubber product by vulcanizing a molded article composed of a rubber composition containing a peroxide as a crosslinking agent in the presence of oxygen, wherein said molded article is irradiated with electron beams, is disclosed. The rubber article produced by the invention is not sticky on the surface and exhibits excellent tensile properties.
    Type: Grant
    Filed: July 19, 1991
    Date of Patent: May 25, 1993
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Masashi Aoshima, Tadashi Jinno
  • Patent number: 5212047
    Abstract: Excellent resolution and sensitivity in the patterning of resists utilized in device and mask manufacture is obtained with a specific composition. In particular this composition involves polymers having recurring pendant acid labile .alpha.-alkoxyalkyl carboxylic acid ester moieties in the presence of an acid generator activated by actinic radiation such as UV-visible, deep ultraviolet, e-beam and x-ray radiation.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: May 18, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Walter R. Hertler, Dotsevi Y. Sogah, Gary N. Taylor
  • Patent number: 5202361
    Abstract: Radiation-curable, tackifier-free compositions are provided which contain: (i) a blend of certain acrylate esters and monoethylenically-unsaturated copolymerizable monomers; (ii) certain .alpha.-olefin polymers; and (iii) a photoinitiator and optionally, a crosslinker. Pressure-sensitive adhesives having good adhesion to both low and high energy surfaces as well as possessing excellent low and high temperature performance properties are prepared by exposing the radiation-curable compositions to light having a wavelength in the range of from about 280 to 400 nm.
    Type: Grant
    Filed: December 23, 1991
    Date of Patent: April 13, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Patrick G. Zimmerman, Gaddam N. Babu, Lang N. Nguyen, Ingrid E. Blair, George F. Vesley
  • Patent number: 5187235
    Abstract: There is provided a radiation-curable, pressure-sensitive-adhesive layer formed of at least one monomer having a glass-transition temperature greater than about -25.degree. C. and an entanglement molecular-weight less than about 20,000; at least one monomer having a glass-transistion temperature less than about -25.degree. C. and an entanglement molecular-weight greater than about 20,000; and at least one tackifier monomer having a glass-transistion temperature greater than -25.degree. C. and an entanglement molecular-weight of at least about 20,000 and present in an interpolymerized amount sufficient to form an interpolymer having a glass-transition temperature less than about -25.degree. C. and an entanglement molecular-weight greater than about 20,000. Cure is preferably by electron beam, and a multifunctional monomer is preferably provided to improve shear.
    Type: Grant
    Filed: December 27, 1991
    Date of Patent: February 16, 1993
    Assignee: Avery Dennison Corporation
    Inventors: Binoy K. Bordoloi, Sebastian S. Plamthottan, Yehuda Ozari, Robert V. Ham
  • Patent number: 5183833
    Abstract: A pressure sensitive adhesive is prepared by the polymerization of an appropriate acrylic ester formulation of the type that includes an ethylenically unsaturated monomer having a polar group, and at least part of such polymerization is accomplished by photopolymerization using a source of ultraviolet radiation that provides a substantial portion of its ultraviolet radiation in the wavelength band of from about 280 to about 350 nm and a light intensity at the surface of the formulation being polymerized of no more than about 4.0 milliwatts/cm.sup.2.
    Type: Grant
    Filed: August 17, 1990
    Date of Patent: February 2, 1993
    Assignee: Adco Products Inc.
    Inventors: Dennis K. Fisher, Brian J. Briddell
  • Patent number: 5182332
    Abstract: Disclosed is a dental composition comprising a (meth)acrylic ester compound as the principal component and containing a polymerization initiator, which is characterized by having incorporated therein a grafted rubber obtained by polymerizing at least one ethylenically unsaturated monomer in the presence of a rubber. This dental composition can be cured to yield a cured product having excellent strength properties and, therefore, is particularly useful in applications such as a molar restoration material and a denture base resin.
    Type: Grant
    Filed: August 1, 1990
    Date of Patent: January 26, 1993
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Naoki Yamamoto, Nobuhiro Mukai, Hitoshi Ige, Junko Atarashi
  • Patent number: 5180756
    Abstract: Agents which are curable by ultraviolet radiation are based on a binder formulation of (1) from 99.0 to 20% by weight of a copolymer, (2) from 1.0 to 80% by weight of monoolefinically unsaturated compounds and (3) from 0.0 to 20% by weight of polyolefinically unsaturated compounds. The agents contain copolymers (1) which are obtainable by subjecting a mixture of (A) from 80 to 99.9% by weight of olefinically unsaturated monomers, (B) from 0 to 10% by weight of a copolymerizable olefinically unsaturated photoinitiator and (C) from 0 to 10% by weight of a polymerization-regulating photoinitiator to free radical polymerization, the sum of (B) and (C) being not less than 0.1% by weight and the stated percentages by weight being based on the sum of the weights of (A)+(B)+(C).
    Type: Grant
    Filed: April 6, 1990
    Date of Patent: January 19, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Rehmer, Andreas Boettcher