Specified Rate-affecting Material Is A Peroxide Patents (Class 522/24)
  • Patent number: 5512608
    Abstract: A multi-part composition is provided which is suitable for use as an adhesive, a potting compound, a coating or a sealant. It consists of a polymerizable acrylate formulation and an activating formulation, the latter usually comprising an amine-aldehyde condensation product diluted with a liquid vinyl ether; liquid epoxides may also be included as diluents in the activating formulation.
    Type: Grant
    Filed: January 27, 1995
    Date of Patent: April 30, 1996
    Assignee: Dymax Corporation
    Inventors: Andrew G. Bachmann, Stephen E. Cantor
  • Patent number: 5494944
    Abstract: A hardenable composition containing:a) a material polymerizable by free radical or cationic polymerization,b) at least one iron compound of the formula I ##EQU1## wherein a is 1 or 2 and q is 1, 2 or 3,L is a divalent to heptavalent metal or non-metal,Q is a halogen atom,m is an integer corresponding to the sum of the values of L and q,R.sup.1 is an unsubstituted or substituted .eta..sup.6 -benzene andR.sup.2 is an unsubstituted or substituted cyclopentadienyl anion, andc) at least one sensitizer for the compound of the formula I,and, in the case of materials polymerizable by free radical polymerization, also d) an electron acceptor as an oxidizing agent, which is also advantageously used concomitantly for the material polymerizable by cationic polymerization. The composition is suitable for the production of protective layers and photographic images.
    Type: Grant
    Filed: August 18, 1994
    Date of Patent: February 27, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Kurt Meier, Hans Zweifel
  • Patent number: 5492942
    Abstract: A pyran derivative has a structure ofR.sup.2 R.sup.3 C.dbd.(C.sub.5 H.sub.2 R.sup.1 O)--(CH.dbd.CH).sub.n --C.sub.6 H.sub.2 R.sup.6 R.sup.7 --NR.sup.4 R.sup.5wherein n is 3 or 4; R.sup.1 is a proton, alkyl or phenyl group; each of R.sup.2 and R.sup.3 is independently a cyano, alkoxycarbonyl having an alkyl, acyl having an alkyl, aracyl having phenyl, sulfonyl, aryl, or aryloxy; each of R.sup.4 and R.sup.5 is an alkyl group; and each of R.sup.6 and R.sup.7 is a proton, provided that R.sup.4 and R.sup.5 are alkyl groups, and a pair of R.sup.4 and R.sup.6 as well as a pair of R.sup.5 and R.sup.7 can be bonded to each other to form a heterocycle.A photosensitive composition comprises a polymerizable compound, a polymerization initiator and a photosensitizer which is the pyran derivative. A photosensitive resin composition comprises a crosslinkable polymer, a crosslinking agent and the photosensitizer.
    Type: Grant
    Filed: May 24, 1994
    Date of Patent: February 20, 1996
    Assignee: Canon Kabushiki Kaisha
    Inventors: Shin Kobayashi, Susumu Matsumura, Naosato Taniguchi, Yoko Yoshinaga, Toshiyuki Sudo, Hideki Morishima, Tadashi Kaneko
  • Patent number: 5486326
    Abstract: A polyketone is contacted with an organic peroxyacid in a reactive, oxidization, slurry process to produce a polyester polymer.
    Type: Grant
    Filed: May 17, 1995
    Date of Patent: January 23, 1996
    Assignee: Exxon Chemical Patents Inc.
    Inventor: Palanisamy Arjunan
  • Patent number: 5466780
    Abstract: A polyketone is contacted with an organic peroxyacid in a reactive, oxidization, slurry process to produce a polyester polymer.
    Type: Grant
    Filed: March 30, 1994
    Date of Patent: November 14, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventor: Palanisamy Arjunan
  • Patent number: 5462797
    Abstract: The present invention provides a pressure-sensitive adhesive composition and a method for producing the same. The pressure-sensitive adhesive composition is produced by the combination of at least one free-radically photopolymerizable monomer and at least one set of polyurethane precursors, and a suitable photoinitiation system consisting of at least one salt of a cationic organometallic complex, an additional free-radical photo initiator and the application of sufficient energy to photopolymerize same by sequential exposure to visible electromagnetic radiation and then to ultraviolet electromagnetic radiation.
    Type: Grant
    Filed: February 8, 1994
    Date of Patent: October 31, 1995
    Assignee: Minneapolis Mining and Manufacturing Company
    Inventors: Jerry W. Williams, Robert J. DeVoe, Thomas P. Klun, George F. Vesley, Patrick G. Zimmerman
  • Patent number: 5445855
    Abstract: An active energy ray-curable composition comprising (A) an epoxy resin, (B) a compound selected from the group consisting of sulfonium salts and cyclopentadienyl iron compounds, (C) a compound selected from the group consisting of acrylates, methacrylates and oligomers thereof, and (D) an organic peroxide, and optionally (E) a rubber component. The composition is useful for an adhesive layer of an optical recording medium.
    Type: Grant
    Filed: August 5, 1993
    Date of Patent: August 29, 1995
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Suguru Tokita, Kenji Yamane, Hajime Inagaki, Masayoshi Kurisu
  • Patent number: 5444104
    Abstract: A polycarbonate dimethacrylate which is the condensation product of 2 parts of hydroxyalkylmethacrylate of the formula. ##STR1## in which A is C.sub.1 -C.sub.6 alkylene, and 1 part of a bis(chloroformate) of the formula ##STR2## in which R is C.sub.2 -C.sub.5 alkylene having at least two carbon atoms in its principal chain and n is an integer from 1 to 4, is usable, admixed with a secondary monomer suitable for dental applications, such as BIS-GMA; UDMA or the like, as an adhesive system for dental restorative materials. Particularly useful is the novel condensation product of 2-hydroxyethylmethacrylate and triethylene glycol bis(chloroformate).Dental adhesives containing these components are suitable for application to enamel, pretreated dentin, porcelain and metallic surfaces. The dentin surfaces are pretreated by application of an alcoholic solution of an alkali metal salt of benzene sulfinic acid.
    Type: Grant
    Filed: October 12, 1993
    Date of Patent: August 22, 1995
    Assignee: Jeneric/Pentron, Inc.
    Inventor: Samuel Waknine
  • Patent number: 5420173
    Abstract: A novel and safe ethylenically unsaturated peroxyester composition derived from an ethylenically unsaturated dicarboxylic acid is provided, as well as processes for making and using the composition. The peroxyester composition comprises about 0.04 to about 0.70 mole fraction of a first component compound having a formula I: ##STR1## about 0.32 to about 0.50 mole fraction of a second component compound having a formula II: ##STR2## about 0.04 to about 0.70 mole fraction of a third component compound having a formula III: ##STR3## wherein Q is an unsaturated ethylene divalent radical and R.sup.1 and R.sup.2 are organic substituents. Polymeric-peroxides are prepared via polymerizing the peroxyester compositions. The peroxyester compositions are also used for curing unsaturated polyester resins and for initiating polymerization of ethylenically unsaturated monomers.
    Type: Grant
    Filed: March 30, 1994
    Date of Patent: May 30, 1995
    Inventor: Jose Sanchez
  • Patent number: 5415976
    Abstract: Aminoketone-substituted coumarin sensitizers having tethered tertiary amino groups are described which have extremely good photosensitivity. The sensitizers of the instant invention have the formula: ##STR1## wherein R.sub.1 and R.sub.2 each represent an alkyl group having 1 to 6 carbon atoms, and R.sub.3 and R.sub.4 each represent hydrogen; or at least one of R.sub.1 and R.sub.3 or R.sub.2 and R.sub.4 together represent an alkylene group having 2 to 4 carbon atoms,R.sub.5 represents an alkyl group having 1 to 6 carbon atoms or H,R.sub.6 represents an alkylene group having 1 to 6 carbon atoms, andR.sub.7 and R.sub.8 each independently represent an alkyl group having 1 to 6 carbon atoms, both of R.sub.7 and R.sub.8 taken together represent an alkylene group having 4 to 6 carbon atoms, or R.sub.5 or R.sub.6 taken together with R.sub.7 or R.sub.8 represent a five, six, or seven membered heterocyclic ring group.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: May 16, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: M. Zaki Ali
  • Patent number: 5409764
    Abstract: A curable adhesive composition comprising an unsaturated polyester oligomer (A) of any of the following formulae (I) to (IV), obtained by reacting a compound (a) having a hydroxyl group and/or an amino group, a cyclic acid anhydride (b) and an epoxide (c) having an ethylenically unsaturated group, and an adhesive polymer (B), ##STR1## wherein: R.sub.1 is a divalent organic moiety having 1 to 40 carbon atoms,R.sub.2 is a divalent organic moiety having 1 to 10 carbon atoms,R.sub.3 is hydrogen or methyl,R.sub.4 is a monovalent organic moiety having 1 to 40 carbon atoms,R.sub.5 is a monovalent organic moiety having 1 to 40 carbon atoms,R.sub.6 is hydrogen or a monovalent organic moiety having 1 to 10 carbon atoms, andn is an integer of 2 or greater.
    Type: Grant
    Filed: September 23, 1994
    Date of Patent: April 25, 1995
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Tsukasa Otsuki, Masato Yanagi, Toshikazu Onikubo, Kouichi Iibuchi
  • 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: 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: 5393644
    Abstract: Crosslinked polymer layers having nonlinear optical properties are produced by a process in which (A) diallyl esters of aromatic dicarboxylic acids or mixtures thereof with monoallyl monoalkyl esters of aromatic dicarboxylic acids are copolymerized with compounds having nonlinear optical activities and containing groups capable of polymerization or (B) prepolymers of diallyl esters of aromatic dicarboxylic acids or prepolymers of mixtures of diallyl esters of aromatic dicarboxylic acids and monoallyl monoalkyl esters of aromatic dicarboxylic acids are mixed with compounds having nonlinear optical activity and with or without polymerizable groups (=guest/host system), applied to a substrate and, after orientation in an electric field above 50.degree. C., crosslinked in a reaction which is initiated thermally or by free radicals.
    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: 5385807
    Abstract: A photopolymerizable composition comprises: (i) a polymerizable compound carrying an addition-polymerizable unsaturated bond; (ii) a methine compound; (iii) at least one compound selected from the group consisting of: (a) compounds having carbon-halogen bonds, (b) aromatic onium salts, (c) organic peroxides, (d) thio compounds, (e) hexaaryl-biimidazoles, (f) ketooxime esters, and (g) compounds represented by the following general formula (III): ##STR1## wherein R.sup.6, R.sup.7, R.sup.8 and R.sup.9 may be the same or different and each represents a substituted or unsubstituted alkyl, aryl, alkenyl, alkynyl or heterocyclic group, provided that at least two of R.sup.6, R.sup.7, R.sup.8 and R.sup.9 may be bonded together to form a ring structure and that at least one of them represents an alkyl group; and Z.sup.+ represents an alkali metal cation or a quaternary ammonium cation. The composition has a high sensitivity to a wide range of actinic light rays extending from ultraviolet to visible light.
    Type: Grant
    Filed: June 22, 1992
    Date of Patent: January 31, 1995
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasuo Okamoto, Syunichi Kondo, Toshinao Ukai
  • Patent number: 5384339
    Abstract: A balancing compound comprising an epoxy resin, a photoinitiator in an effective amount to cure the resin at ambient temperatures upon the application of ultraviolet light (10 nm to 400 nm) of less than 40 watts per square centimeter in less than about 30 seconds, and a filler in an effective amount to give the compound a specific gravity above 1.1.
    Type: Grant
    Filed: March 9, 1993
    Date of Patent: January 24, 1995
    Inventor: Donn R. Starkey
  • Patent number: 5380772
    Abstract: A modelling liquid used for building up dental porcelain, comprising:(A) a photopolymerizable compound having at least one ethylenically unsaturated double bond,(B) a photopolymerization initiator,(C) a reducing agent, and(D) a polymerization inhibitor.
    Type: Grant
    Filed: May 27, 1993
    Date of Patent: January 10, 1995
    Assignee: G-C Toshi Kogyo Corporation
    Inventors: Akira Hasegawa, Tsugumichi Kawasaki
  • Patent number: 5371115
    Abstract: A hardenable composition containing:a) a material polymerizable by free radical or cationic polymerization,b) at least one iron compound of the formula I ##EQU1## wherein a is 1 or 2 and q is 1, 2 or 3,L is a divalent to heptavalent metal or non-metal,Q is a halogen atom,m is an integer corresponding to the sum of the values of L and q,R.sup.1 is an unsubstituted or substituted .eta..sup.6 -benzene andR.sup.2 is an unsubstituted or substituted cyclopentadienyl anion, andc) at least one sensitizer for the compound of the formula I,and, in the case of materials polymerizable by free radical polymerization, also d) an electron acceptor as an oxidizing agent, which is also advantageously used concomitantly for the material polymerizable by cationic polymerization. The composition is suitable for the production of protective layers and photographic images.
    Type: Grant
    Filed: April 15, 1992
    Date of Patent: December 6, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Kurt Meier, Hans Zweifel
  • 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: 5340847
    Abstract: A composition useful as a liquid gasket, having high working efficiency and high initial pressure resistance, is provided. The composition, characterized by being curable by ultraviolet light and by moisture, includes (a) a polysiloxane containing, on at least one molecular end, at least one group selected from the group consisting of (meth)acryl, glycidyl, propenyloxysilyl and thiol; (b) a polyorganosiloxane having silanol groups at both molecular ends; (c) a polyorganosiloxane having, on at least one molecular end, a hydrolyzable group; (d) a photopolymerization catalyst; and (e) a condensation catalyst.
    Type: Grant
    Filed: July 23, 1993
    Date of Patent: August 23, 1994
    Assignee: Three Bond Co., Ltd.
    Inventors: Yasuo Hanazuka, Ikuzo Usami, Kazuyuki Chiba, Noriko Mizutani
  • Patent number: 5318998
    Abstract: An adhesive composition comprising a first liquid containing (A) an acrylic compound selected from the group consisting of (meth)acrylic acids and esters thereof, and (B) a polymerization initiator selected from the group consisting of peroxy esters and hydroperoxides, and a second liquid containing (C) a condensation product of an amine and an aldehyde, and (D) a copper salt, wherein an acid phosphate compound of the following formula (I): ##STR1## wherein R is an alkyl group, an alkoxyalkyl group or a CH.sub.2 .dbd.CR.sub.1 --CO(OR.sub.2).sub.m -- group, wherein R.sub.1 is H or CH.sub.3, R.sub.2 is --C.sub.2 H.sub.4 --, --C.sub.3 H.sub.6 --, ##STR2## --C.sub.4 H.sub.8 --, --C.sub.6 H.sub.12 -- or ##STR3## and m is an integer of from 1 to 10; and n is 1 or 2, is contained in the first liquid or in both the first and second liquids.
    Type: Grant
    Filed: September 10, 1990
    Date of Patent: June 7, 1994
    Assignee: Denki Kagaku Kogyo Kabushiki Kaisha
    Inventors: Kohichi Taguchi, Hiroshi Suto
  • Patent number: 5286603
    Abstract: A radiation sensitive plate comprises a substrate coated with a photopolymerisable composition. The composition comprises a polymerisable compound containing ethylenic unsaturation, a perester photoinitiator and optionally an optical sensitiser. The substrate may be a sheet of grained and anodised aluminum and the plate is useful in the production of lithographic printing plates.
    Type: Grant
    Filed: June 3, 1992
    Date of Patent: February 15, 1994
    Assignee: Vickers PLC
    Inventors: John R. Wade, Rodney M. Potts, Michael J. Pratt
  • Patent number: 5283160
    Abstract: A photopolymerisable composition comprising a polymerisable olefinically unsaturated compound and a photoinitiator composition(a) a photoinitiator comprising an anthraquinone compound having in the 2-position a substituent of the formula:--X COR.sup.1wherein R.sup.1 represents an optionally substituted hydrocarbyl radical and X represents ##STR1## wherein R.sup.2 represents hydrogen or an optionally substituted hydrocarbyl radical, and(b) a hydrogen donor capable of reducing the photoinitiator when the latter is in an excited state.
    Type: Grant
    Filed: November 10, 1992
    Date of Patent: February 1, 1994
    Assignee: Zeneca Limited
    Inventors: N. S. Allen, R. T. Cook, C. H. McLean, I. A. Weddell
  • Patent number: 5275372
    Abstract: UV-transparent forming tools or molds are prepared for molding resins comprising a urethane acrylate, e.g. urethane dimethacrylate oligomer, and an alpha,beta-ethylenically unsaturated monomer, e.g., styrene, cured in the presence of a peroxide initiator. The resins are tough, durable and have a wide range of other desirable properties.
    Type: Grant
    Filed: July 21, 1992
    Date of Patent: January 4, 1994
    Assignee: Cook Composites & Polymers Co.
    Inventor: Rudolph H. Boeckeler
  • Patent number: 5276068
    Abstract: A polycarbonate dimethacrylate which is the condensation product of 2 parts of hydroxyalkylmethacrylate of the formula ##STR1## in which A is C.sub.1 -C.sub.6 alkylene, and 1 part of a bis(chloroformate) of the formula ##STR2## in which R is C.sub.2 -C.sub.5 alkylene having at least two carbon atoms in its principal chain and n is an integer from 1 to 4, is usable, admixed with a secondary monomer suitable for dental applications, such as BIS-GMA; PUDMA or the like, as an adhesive system for dental restorative materials. Particularly useful is the novel condensation product of 2-hydroxyethylmethacrylate and triethylene glycol bis(chloroformate).
    Type: Grant
    Filed: January 28, 1992
    Date of Patent: January 4, 1994
    Assignee: Jeneric/Pentron, Inc.
    Inventor: Samuel Waknine
  • Patent number: 5254602
    Abstract: A photocurable compound prepared as a starting material by incorporation therein of a composition comprising a fluorescein compound photoreducing dye, tribenzylamine, and at least one specific peroxide permits production of a shaped article which, on exposure to visible light, exhibits high curability and acquires hardness virtually indiscriminately on the obverse and reverse sides of the article. A mixture comprising both or either of an unsaturated polyester resin and an epoxy acrylate resin which are photocurable compounds, glass fibers, and a specific peroxide, is convenient for the production of specific cured shaped articles particularly by the filament winding technique or the drawing technique.
    Type: Grant
    Filed: February 21, 1992
    Date of Patent: October 19, 1993
    Assignee: Nippon Oil & Fats Co., Ltd.
    Inventors: Yoshihiro Tomura, Shigeki Banno
  • Patent number: 5238744
    Abstract: A tough polymeric mixture comprises the polymerized product of admixture I or II, whereinadmixture I comprises 5 to 45 weight percent of a first monomer and a photoinitiator therefor, said first monomer being at least one free-radically polymerizable monomer, and 95 to 55 weight percent of a second monomer and a photoinitiator therefor, said second monomer being at least one set of polyurethane precursors, andadmixture II comprises 5 to 45 weight percent of a first monomer and a photoinitiator therefor, said first monomer being at least one set of polyurethane precursors, and 95 to 55 weight percent of a second monomer and a photoinitiator therefor, said second monomer being at least one free-radically polymerizable monomer,said polymeric mixture having been prepared by a process involving two sequential actinic radiations of wavelength ranges centered around .lambda..sub.1 and .lambda..sub.2, respectively, wherein .lambda..sub.1 and .lambda..sub.
    Type: Grant
    Filed: January 10, 1992
    Date of Patent: August 24, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Jerry W. Williams, Robert J. DeVoe
  • Patent number: 5237041
    Abstract: This invention relates to new phosphorus-containing duromers of oligophosphites and epoxides or bisacrylates or unsaturated polyesters.
    Type: Grant
    Filed: November 30, 1992
    Date of Patent: August 17, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Burkhard Kohler, Wolfgang Ebert
  • Patent number: 5212210
    Abstract: A composition and method provide improved physical properties and cure speed of polyurethane precursors, with or without free radical polymerizable monomers or oligomers present, by use of a two component catalyst system. The resin blend can be activated with a latent organometallic catalyst combined with an organic peroxide which can be a hydroperoxide or an acyl peroxide to decrease the cure time while increasing the break energy and tangent modulus of the system.
    Type: Grant
    Filed: March 18, 1992
    Date of Patent: May 18, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Leo W. Halm
  • Patent number: 5167882
    Abstract: An improved stereolithography method for building a three-dimensional article including the steps of patternwise curing successive layers of a bath of curable liquid resin formulation until the article has been completely built up, removing the article from the liquid resin bath and then post-curing the article, wherein the liquid resin is a "thiol/nene" formulation including:(a) a first compound having a plurality of norbornene groups thereon;(b) a second compound having a plurality of thiol groups therein; and(c) a free radical photoinitiator,the total functionality of the formulation being greater than 4.
    Type: Grant
    Filed: February 5, 1991
    Date of Patent: December 1, 1992
    Assignee: Loctite Corporation
    Inventors: Anthony F. Jacobine, Margaret A. Rakas, David M. Glaser
  • Patent number: 5137448
    Abstract: Disclosed in the present application is a method of curing a dental impression material by passing actinic light through a tray while the tray is in contact with the impression making composition, a new dental impression composition that is polymerizable by having an initiator activated by actinic light within the visible light range of 360 to 600 nanometers, a new composition of matter that is a compound having at least two terminal acrylate unsaturations and an organosilicone containing backbone and a new method of forming dental prosthetics by directly forming against the soft tissue of the oral cavity and then setting with visible light curing.
    Type: Grant
    Filed: February 4, 1991
    Date of Patent: August 11, 1992
    Assignee: Dentsply Research & Development Corp.
    Inventors: Emery W. Dougherty, Wu-Lan Wang
  • Patent number: 5137800
    Abstract: A polymerizable composition and a method are disclosed. The composition includes a photopolymerizable monomer and a photoinitiator system for the monomer. The system, in one embodiment, is one wherein a ray of activating radiation which enters a body of the composition through a surface thereof activates the photoinitiator system and causes polymerization at each of a succession of points, the first such point being immediately adjacent the surface and subsequent points being successively farther from the surface in the direction of travel of the ray of activating radiation, the distance from the surface to the point of the succession farthest therefrom varying as a function of at least one of(a) the intensity of the activating radiation and(b) the time during which the activating radiation enters the body through the surface.
    Type: Grant
    Filed: June 14, 1990
    Date of Patent: August 11, 1992
    Assignee: StereoGraphics Limited Partnership
    Inventors: Douglas C. Neckers, Oscar Valdes-Aguilera, Krishan S. Raghuveer, Darrell G. Watson
  • Patent number: 5130227
    Abstract: A radiation sensitive plate comprises a substrate coated with a photopolymerizable composition. The composition comprises a polymerizable compound containing ethylenic unsaturation, a perester photoinitiator and optionally an optical sensitiser. The substrate may be a sheet of grained and anodized aluminum and the plate is useful in the production of lithographic printing plates.
    Type: Grant
    Filed: October 5, 1989
    Date of Patent: July 14, 1992
    Assignee: Vickers Plc
    Inventors: John R. Wade, Rodney M. Potts, Michael J. Pratt
  • Patent number: 5102775
    Abstract: A composition for visible light sensitive electrodeposition coating which comprises (A) a photocurable resin having light sensitive groups capable of being crosslinked or polymerized by light irradiation and ionic groups, (B) a sensitizer which is excited by absorption of visible light and has a property to interact with the resin (A), (C) a water-insoluble polymerization initiator, and optionally, (D) at least one specific nitrogen-containing compound; and an image-forming method which comprises (i) coating the surface of a conductor by electrodeposition with the aforesaid composition, (ii) exposing the resulting film by electrodeposition by partially irradiating the film with visible light, and then (iii) contacting the resulting film with a developing solution to remove the unexposed areas.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: April 7, 1992
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Motoko Okuhara, Ichiro Yoshihara, Yasuo Doi, Takao Yamamoto, Kenji Seko, Yutaka Yoshikawa, Naozumi Iwasawa
  • Patent number: 5073476
    Abstract: Iron (II)-aromatic compound complexes mixed with electron acceptors as an oxidizing agent are suitable initiators for the polymerization by irradiation of organic material which can be polymerized by cations and/or free radicals. The composition composed of the polymerizable material and of the initiator mixture is suitable for the production of protective coatings and can be used as a photographic recording material.
    Type: Grant
    Filed: May 10, 1984
    Date of Patent: December 17, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Kurt Meier, Giuliano Eugster, Franz Schwarzenbach, Hans Zweifel
  • Patent number: 5063257
    Abstract: A dental glass ionomer cement composition comprises:(a) 5 to 100 parts by weight of a polymer of an .alpha.-.beta. unsaturated carboxylic acid having a weight average molecular weight of 5,000 to 40,000,(b) 5 to 100 parts by weight of a fluoroaluminosilicate glass powder having an average particle size of 0.02 to 10 .mu.m and a specific gravity of 2.4 to 4.0 and capable of reacting with said "polymer of an .alpha.-.beta. unsaturated carboxylic acid having a weight average molecular weight of 5,000 to 40,000",(c) 5 to 100 parts by weight of a polymerizable unsaturated organic compound having at least one CH.sub.2 .dbd.C(R1)--COO--group wherein R1=H or CH.sub.3,(d) 0.01 to 5 parts by weight of a polymerization catalyst,(e) 2 to 50 parts by weight of water,(f) 0.01 to 20 parts by weight of a surface active agent, and(g) 0.01 to 5 parts by weight of a reducing agent, and optionally h. 0 to 50 parts by weight of an inorganic filler having an average particle size of 0.02 to 10 .mu.
    Type: Grant
    Filed: December 11, 1989
    Date of Patent: November 5, 1991
    Assignee: G-C Dental Industrial Corp.
    Inventors: Shoji Akahane, Satoshi Tosaki, Yukiharu Kusayanagi, Shigenobu Kusakai, Kazuo Hirota, Kentaro Tomioka
  • Patent number: 5039715
    Abstract: A reactive acrylic adhesive, activated by actinic radiation, includes, in addition to a photoinitiator, at least about 1.0 percent by weight of a perester compound or cumene hydroperoxide, and 0.5 percent of a tautomeric organic acid, for enhanced bond strength.
    Type: Grant
    Filed: September 19, 1990
    Date of Patent: August 13, 1991
    Assignee: Dymax Corporation
    Inventors: Andrew G. Bachmann, James M. Hillman
  • Patent number: 5017406
    Abstract: UV curable compositions suitable for use as potting and encapsulating compounds for electrical and electronic devices are provided. The compositions comprise: (a) a UV curable compound polymerizable by a free radical process and containing reactive unsaturated groups, (b) a polysilane photoinitiator, and (c) a peroxide photoinitiator. The use of the two photoinitiators enables one to get a more complete cure, both at the surface and deep into the coating.
    Type: Grant
    Filed: December 8, 1988
    Date of Patent: May 21, 1991
    Assignee: Dow Corning Corporation
    Inventor: Michael A. Lutz
  • Patent number: 5017626
    Abstract: A visible light-curing polyester resin composition comprises an unsaturated polyester resin and a photocuring agent composed of an .alpha.-diketone, a benzyidimethyl ketal, and at least one member selected from the group consisting of (1) 2-(dimethylamino)-ethyl benzoate, (2) 2-(dimethylamino)-ethyl benzoate plus a peroxy ketal, and (3) a peroxy ketal plus a tertiaryamine.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: May 21, 1991
    Assignee: Nippon Oil & Fats Co., Ltd.
    Inventors: Yoshihiro Tomura, Shigeki Banno
  • Patent number: 4992547
    Abstract: The photopolymerizable mixture described contains(A) at least one ethylenically unsaturated photopolymerisable compound,(B) a photoinitiator of the formula I ##STR1## and (C) a photosensitiser from the group of aromatic carbonyl compounds having a triplet energy of 225-310 kJ/mol, for example xanthones, thioxianthones, coumarins, phthalimides, phenones and the like.Ar is phenyl substituted in the 4-position by a substituted amino group, R.sup.1 and R.sup.2 are alkyl, R.sup.3 and R.sup.4 are alkyl or alkoxyalkyl, or R.sup.3 and R.sup.4 together are 3-oxapentamethylene. Said sensitisers (C) raise the activity of said photoinitiators (B) without shortening the shelf life of the mixtures. The photocurable mixtures are used especially as binders for printing inks or paints.
    Type: Grant
    Filed: June 14, 1988
    Date of Patent: February 12, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Godwin Berner, Kurt Meier, Kurt Dietliker, Rinaldo Husler
  • Patent number: 4975471
    Abstract: A photo-curable epoxy resin type composition which comprises (a) an epoxy resin, (b) at least one compound selected from the group consisting of (i) a compound having a group, other than an imido group, which is represented by the formula --CONH and (ii) an aromatic amine, (c) an organic metal compound, where said metal is selected from the group consisting of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, aluminum and zirconium; and (d) an organic silicon compound having at least one group selected from the group consisting of a peroxysilyl group and an o-nitrobenzyloxy group capable of forming a silanol group by irradiation with light. The photo-curable epoxy resin type composition according to this invention is capable of readily curing by light (ultraviolet ray in particular) and also capable of heat curing at a temperature of 150.degree. C.
    Type: Grant
    Filed: August 29, 1988
    Date of Patent: December 4, 1990
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Shuzi Hayase, Shuichi Suzuki, Moriyasu Wada
  • Patent number: 4972006
    Abstract: A method of curing a three-dimensional specimen of preformed cross-linked polymeric material containing polymerizable ethylenically-unsaturated material is provided in which the specimen is immersed in water having dissolved therein an amount of a water-soluble organic free-radical polymerization catalyst effective to transfer a polymerization-initiating amount of the catalyst into the preformed cross-linked polymeric material. This specimen containing the water-soluble organic free-radical polymerization catalyst is heated to a temperature causing polymerization, and is maintained at that temperature while the cure is completed. The aqueous bath preferably contains a catalyst mixture which includes a catalyst of oxidizing character in admixture with a reducing agent, such as an amine, and is maintained at a polymerization temperature of from 60.degree. C. to 100.degree. C. so that immersion of the specimen in a single bath completes the cure.
    Type: Grant
    Filed: September 8, 1988
    Date of Patent: November 20, 1990
    Assignee: DeSoto, Inc.
    Inventors: Edward J. Murphy, John J. Krajewski, Robert E. Ansel
  • Patent number: 4952711
    Abstract: A composition curable to a solid crosslinked polyorganosiloxane comprises:(a) an acrylic functional silicone prepolymer having a plurality of acrylic groups of the formula: ##STR1## bound to silicon atoms thereof, where R is H or methyl, and R.sup.1 is a divalent olefinically unsaturated hydrocarbon group,(b) a silicone prepolymer having a plurality of organothiol groups thereon, and(c) an effective amount of a thiol-ene cure catalyst.Particularly preferred formulations are photoinitiated formulations employing alkylthiol functional silicones in which the total number of thiol groups is between 0.5 and 1.5 times the total number of ene groups counting both the acrylic and the linking group R.sup.1 as ene groups.
    Type: Grant
    Filed: May 25, 1989
    Date of Patent: August 28, 1990
    Assignee: Loctite Corporation
    Inventors: Anthony F. Jacobine, Steven T. Nakos
  • Patent number: 4950581
    Abstract: A photopolymerizable composition is provided containing a polymerizable compound having an ethylenically unsaturated bond, a photopolymerization initiator, and if necessary, a linear organic high molecular weight polymer. The photopolymerization initiator comprises a combination of (a) an organic compound represented by formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4, which may be the same or different, each represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkenyl group a substituted or unsubstituted alkynyl group, or a substituted or unsubstituted heterocyclic group, and at least two of said R.sup.1, R.sup.2, R.sup.3, and R.sup.4 may combine to form a cyclic structure, with the proviso that at least one of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 is an alkyl group, and wherein Z.sym. represents an alkali metal cation or a quaternary ammonium cation, and (b) an organic dye having no counter anion.
    Type: Grant
    Filed: July 5, 1988
    Date of Patent: August 21, 1990
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Mitsuru Koike, Nobuyuki Kita
  • Patent number: 4940648
    Abstract: A photo polymerization initiator composition is disclosed. The composition is comprised of an organic peroxide or perester in admixture with 9-phenyl acridine, or phenazine initiator compound. The initiator composition is useful in preparing photopolymerizable compositions having increased effective photospeed.
    Type: Grant
    Filed: February 12, 1988
    Date of Patent: July 10, 1990
    Assignee: Hoechst Celanese Corporation
    Inventor: Margaret W. Geiger
  • Patent number: 4939069
    Abstract: Disclosed is a photopolymerizable composition which is very sensitive to light, especially visible light having a wave length of 600 to 700 nm. The photopolymerizable composition comprising a polymerizable compound having an ethylenically unsaturated double bond and a photopolymerization initiator wherein the photopolymerization initiator comprises (a) a specific sensitizer and (b) a radical forming agent.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: July 3, 1990
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Masami Kawabata, Masahiko Harada, Yasuyuki Takimoto
  • Patent number: 4935454
    Abstract: A dielectric composition capable of being polymerized for use in sealing electrical and electro-optical connectors and devices is disclosed. Said composition is comprised of a major proportion of vinyl ester resins, a minor proportion of polymerizable acrylic diluent monomers, and a polymerization activation system comprised of from about 0.25 percent to about 17 percent by weight of the resin. A process of the present invention includes applying a layer of said composition to desired areas or to desired locations such as apertures surrounding electrical terminals extending from a connector housing, and exposing said composition to actinic radiation which activates the polymerization activation system which causes the composition to polymerize to form a sealant material that exclused solder and solvents from the connector and its apertures.
    Type: Grant
    Filed: May 16, 1989
    Date of Patent: June 19, 1990
    Assignee: AMP Incorporated
    Inventors: Francis F. Koblitz, Thomas M. O'Shea, Lynn K. Snyder
  • Patent number: 4925660
    Abstract: A crude drug ingredient having bactericidal activity incorporated into a curable composition comprising a (meth)acrylate type monomer, a polymerization initiator and if necessary a filler to formulate the ingredient into the drug having sustained release property. The curable composition containing the crude drug ingredient is applied to a defective part of a tooth or an artificial gum for preventing dental diseases such as carious tooth, pyorrhea alveolaris, and the like.
    Type: Grant
    Filed: April 7, 1988
    Date of Patent: May 15, 1990
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Mitsuru Atsuta, Takeshi Sakashita, Ryoichi Miyamoto, Yukinori Tanimura, Saburo Fuji
  • 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: 4865949
    Abstract: An optical information recording medium is disclosed, which comprises a pair of disc-shaped substrates, at least one of the substrates having a recording layer comprising an organic dye compound on one side thereof, which are disposed so as to face each other, with the recording layer positioned therebetween, with or without a space between the two substrates, by sealing with an adhesive agent comprising an alicyclic epoxy resin component having general formula ##STR1## where R.sup.1 .about.R.sup.9 each represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or halogen; and R represents (CH.sub.2).sub.n, where n is an integer of 1 to 4, ##STR2## and a composite catalyst comprising a photo-decomposition organic silicon compound and a metal complex.
    Type: Grant
    Filed: April 20, 1988
    Date of Patent: September 12, 1989
    Assignee: Ricoh Company, Ltd.
    Inventors: Tetsu Yamamuro, Yutaka Ueda