With A Tertiary Amine Specified Rate-affecting Material Patents (Class 522/10)
  • Patent number: 11622916
    Abstract: [Problem] To provide a photocurable composition having a high curing depth. [Solution] To provide a photocurable composition of the present disclosure comprises (A) polymerizable monomer, (B) photosensitizer, (C) photoacid generator, and (D) photopolymerization accelerator, wherein, the photocurable composition comprises (D-1) amine compound represented by formula (1) as the (D) photopolymerization accelerator. (In the formula (1), R1 is a substituent represented by formula (2), and R2 and R3 are substituents represented by formula (2) or substituents selected from —OH group, —O— group, —S— group, —NH—C(O)—NH— group, —C(O)—O— group, —OC(O)— group, —OC(O)—NH— group, —NH—C(O)—O— group, halogen, an organic group which may have an alkoxysilyl group, an aromatic ring which may have a substituent and an alicyclic heterocycle which may have a substituent.
    Type: Grant
    Filed: March 15, 2021
    Date of Patent: April 11, 2023
    Assignee: SHOFU INC.
    Inventors: Kenzo Yamamoto, Hiroyuki Kobayashi, Daisuke Hara, Shunsuke Miyata
  • Patent number: 10501402
    Abstract: The invention relates to a multifunctional acrylic product having a number-average functionality f of acrylate groups greater than 2.1, which is the product of reaction by esterification and by etherification, via Michael addition reaction, between a) a polyol or a mixture of polyols R(OH)m having a functionality m of at least 3 for a polyol alone or having an average functionality greater than 2.1 for a mixture of polyols, and b) the acrylic acid (R1OH) in the presence of c) at least one cyclic polycarboxylic anhydride or of its polyacid form having a carboxy functionality z of at least 2 and up to 4, the ratio r1 of number of carboxy groups of said anhydride or polyacid c) with respect to those of the acrylic acid b) r1=CO2Hc/CO2Hb being from 0.01 to 0.
    Type: Grant
    Filed: October 13, 2015
    Date of Patent: December 10, 2019
    Assignee: Arkema France
    Inventors: Guillaume P. Monnier, Philippe Ciceron, Catherine M. Leroy, Charles Bourrousse
  • Patent number: 9844494
    Abstract: Provided is a polymerizable composition hardly having oxygen inhibition layer by polymerization under an oxygen environment, including a first paste including (a) a (meth)acrylate compound, (b) at least one of an aromatic sulfinic acid and a salt thereof, and (c) an acidic compound; and a second paste including (a) a (meth)acrylate compound, (d) an organic metal compound, and (e) an organic halogen compound, wherein at least either one of the first paste and the second paste includes (f) a filler.
    Type: Grant
    Filed: March 6, 2015
    Date of Patent: December 19, 2017
    Assignee: GC CORPORATION
    Inventors: So Ishizuka, Naofumi Matsumoto
  • Patent number: 9388281
    Abstract: Polythioethers and methods for forming polythioethers are described. These polythioethers can be crosslinked materials. The polythioethers are prepared from thiols and hexahydrotriazines. The thiols may be, for example, dithiols, trithiols, monothiols, or mixtures thereof. The polythioethers are prepared from an efficient and simple synthetic method, and the properties of the prepared polythioethers can be readily tuned. The prepared polythioethers may additionally have improved thermal properties, improved mechanical properties, and enhanced functionality.
    Type: Grant
    Filed: June 30, 2015
    Date of Patent: July 12, 2016
    Assignee: INTERNATIONAL BUSINESS MACHINES CORPORATION
    Inventors: Dylan J. Boday, Jeannette M. Garcia, James L. Hedrick, Rudy J. Wojtecki
  • Patent number: 9228059
    Abstract: Polythioethers and methods for forming polythioethers are disclosed herein. The polythioethers are prepared from thiols and hexahydrotriazines. The thiols may be, for example, dithiols, trithiols, monothiols, or mixtures thereof. The polythioethers are prepared from an efficient and simple synthetic method, and the properties of the prepared polythioethers can be readily tuned. The prepared polythioethers may additionally have improved thermal properties, improved mechanical properties, and enhanced functionality.
    Type: Grant
    Filed: December 16, 2014
    Date of Patent: January 5, 2016
    Assignee: International Business Machines Corporation
    Inventors: Dylan J. Boday, Jeannette M. Garcia, James L. Hedrick, Rudy J. Wojtecki
  • Patent number: 9206289
    Abstract: Polysulfones and methods for forming polysulfones are disclosed herein. The polysulfones are prepared from thiols and hexahydrotriazines. The thiols may be, for example, dithiols, trithiols, monothiols, or mixtures thereof. The thiols and hexahydrotriazines may be polymerized to form a polythioether. The polythioether may thereafter be oxidized to form a polysulfone. The polysulfones are prepared from an efficient and simple synthetic method, and the properties of the prepared polysulfones can be readily tuned. The prepared polysulfones may have improved thermal properties, improved mechanical properties, and enhanced functionality.
    Type: Grant
    Filed: February 10, 2015
    Date of Patent: December 8, 2015
    Assignee: International Business Machines Corporation
    Inventors: Dylan J. Boday, Jeannette M. Garcia, James L. Hedrick, Rudy J. Wojtecki
  • Patent number: 9139698
    Abstract: Polysulfones and methods for forming polysulfones are disclosed herein. The polysulfones are prepared from thiols and hexahydrotriazines. The thiols may be, for example, dithiols, trithiols, monothiols, or mixtures thereof. The thiols and hexahydrotriazines may be polymerized to form a polythioether. The polythioether may thereafter be oxidized to form a polysulfone. The polysulfones are prepared from an efficient and simple synthetic method, and the properties of the prepared polysulfones can be readily tuned. The prepared polysulfones may have improved thermal properties, improved mechanical properties, and enhanced functionality.
    Type: Grant
    Filed: December 15, 2014
    Date of Patent: September 22, 2015
    Assignee: International Business Machines Corporation
    Inventors: Dylan J. Boday, Jeannette M. Garcia, James L. Hedrick, Rudy J. Wojtecki
  • Patent number: 9120899
    Abstract: Polysulfones and methods for forming polysulfones are disclosed herein. The polysulfones are prepared from thiols and hexahydrotriazines. The thiols may be, for example, dithiols, trithiols, monothiols, or mixtures thereof. The thiols and hexahydrotriazines may be polymerized to form a polythioether. The polythioether may thereafter be oxidized to form a polysulfone. The polysulfones are prepared from an efficient and simple synthetic method, and the properties of the prepared polysulfones can be readily tuned. The prepared polysulfones may have improved thermal properties, improved mechanical properties, and enhanced functionality.
    Type: Grant
    Filed: June 2, 2014
    Date of Patent: September 1, 2015
    Assignee: International Business Machines Corporation
    Inventors: Dylan J. Boday, Jeannette M. Garcia, James L. Hedrick, Rudy J. Wojtecki
  • Patent number: 9120897
    Abstract: Polythioethers and methods for forming polythioethers are disclosed herein. The polythioethers are prepared from thiols and hexahydrotriazines. The thiols may be, for example, dithiols, trithiols, monothiols, or mixtures thereof. The polythioethers are prepared from an efficient and simple synthetic method, and the properties of the prepared polythioethers can be readily tuned. The prepared polythioethers may additionally have improved thermal properties, improved mechanical properties, and enhanced functionality.
    Type: Grant
    Filed: May 27, 2014
    Date of Patent: September 1, 2015
    Assignee: International Business Machines Corporation
    Inventors: Dylan J. Boday, Jeanette M. Garcia, James L. Hedrick, Rudy J. Wojtecki
  • Patent number: 8367745
    Abstract: To provide a dual curing type composite resin for core build-up having improved curing property by chemical polymerization with improved mechanical strength of a cured body under the condition of no light irradiation and with a shortened setting time, the composite resin is composed of a first component including a (meth)acrylate polymerizable resin and an organic peroxide, and a second component including (meth)acrylate polymerizable resin and a reducing agent, a photopolymerizaton initiator and a filler are included in the first component and/or the second component, and oxide powder of a Group II element in the periodic table having an average particle diameter of 1 ?m or less is blended in the first component and/or the second component.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: February 5, 2013
    Assignee: GC Corporation
    Inventors: Yugo Kosaka, Yutaka Shinozaki, Tomohiro Kumagai
  • Patent number: 8338499
    Abstract: A radiation curable composition comprising a curable compound, a photo-initiator and a co-initiator characterized in that said co-initiator is represented by Formula I, wherein MA is the residue of a mono- or oligofunctional Michael acceptor; L is a divalent linking group positioning the two tertiary amines in a 1-3 to 1-10 position, with the proviso that both amines are aliphatic; R1, R2 and R3 independently represent an optionally substituted alkyl group, an optionally substituted alkenyl group , an optionally substituted alkynyl group or an optionally substituted (hetero) alkaryl group; any two of R1, R2 and R3 may represent the necessary atoms to form a ring; any two of R1, R2 and R3 may represent the necessary atoms to form a ring with any of the atoms of the linking group L; n is an integer ranging from 1 to 6.
    Type: Grant
    Filed: December 17, 2007
    Date of Patent: December 25, 2012
    Assignee: Agfa Graphics NV
    Inventors: Johan Loccufier, Roland Claes, Jaymes Van Luppen
  • Patent number: 8227047
    Abstract: A radiation curable inkjet fluid includes a radiation curable composition including at least 25 wt % of a vinylether acrylate and at least 15 wt % of a polymerizable compound including at least three acrylate groups, each wt % being based upon the total weight of the radiation curable composition; and a photoinitiator including a tertiary amine group and 0 to 3 wt % of isopropylthioxanthone based upon the total weight of the radiation curable inkjet fluid. Also, an inkjet printing method using the radiation curable inkjet fluid.
    Type: Grant
    Filed: October 22, 2008
    Date of Patent: July 24, 2012
    Assignee: Agfa Graphics NV
    Inventors: Johan Loccufier, Ivan Hoogmartens
  • Patent number: 8217095
    Abstract: The object of the present invention is to provide an active energy ray-curable ink-jet printing ink, including: a coloring agent; a compound having an ethylenic double bond; and a photo-polymerization initiator, wherein the photo-polymerization initiator includes a compound represented by general formula (1): (wherein A represents any one of —O—, —CH2—, —CH(CH3)—, and —C(CH3)2—; and each of R1 and R2 independently represents a hydrogen atom, a methyl group, or a trimethylsilyl group), and an ?-aminoketone-based compound and/or an acyl phosphine oxide-based compound, and 40% by mass or more of the compound represented by general formula (1) is included with respect to the total photo-polymerization initiator.
    Type: Grant
    Filed: October 28, 2005
    Date of Patent: July 10, 2012
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Hisao Yamaguchi, Yutaka Yamada, Naohito Saito, Osamu Oshima
  • Patent number: 8158212
    Abstract: An ink composition is provided that includes (A) an N-vinyllactam, (B) another polymerizable compound, (C) a polymerization initiator, and (D) a basic compound, the content of the N-vinyllactam (A) being less than 15 wt % of the total weight of the ink composition. There is also provided an inkjet recording method that includes (a1) a step of discharging the ink composition onto a recording medium and (b1) a step of curing the ink composition by irradiating the discharged ink composition with actinic radiation. There is also provided a printed material recorded by the inkjet recording method.
    Type: Grant
    Filed: February 15, 2008
    Date of Patent: April 17, 2012
    Assignee: FUJIFILM Corporation
    Inventors: Kaoru Tojo, Hironori Ohnishi
  • Patent number: 8137890
    Abstract: The invention provides a colored photosensitive composition including: a coloring agent with a content of from 50% by weight to 80% by weight with respect to the total solid content of the composition; an oxime-based initiator with a content of from 5% by weight to 20% by weight with respect to the total solid content of the composition; and a resin containing at least one first structural unit represented by any one of the following formulae (1) to (3) containing an unsaturated double bond, and at least one second structural unit represented by the following formula (4) containing an acid group, wherein a ratio of the first structural unit to the second structural unit is 1.5 or more (molar ratio).
    Type: Grant
    Filed: August 15, 2008
    Date of Patent: March 20, 2012
    Assignee: Fujifilm Corporation
    Inventors: Hideki Takakuwa, Kazuto Shimada
  • Patent number: 8110610
    Abstract: A radiation curable composition comprising a curable compound, a photo-initiator and a co-initiator, characterized in that said co-initiator is a oligomer or polymer having a repeating unit, said repeating unit comprising at least two tertiary amines, and said polymer being prepared by the polycondensation of di- or oligofunctional Michael acceptors with mono- or oligofunctional aliphatic primary amines or with di- or oligofunctional aliphatic secondary amines or with a mixture thereof.
    Type: Grant
    Filed: December 17, 2007
    Date of Patent: February 7, 2012
    Assignee: Agfa Graphics N.V.
    Inventors: Johan Loccufier, Roland Claes
  • Patent number: 7985785
    Abstract: An ink composition of the present invention is disclosed, which contains (i) a sensitizing dye represented by the following Formula (I); (ii) at least one polymerization initiator selected from the group consisting of ?-aminoketones and acyl phosphine oxides; and (iii) an ethylenically unsaturated bond-containing polymerizable compound. In Formula (I), X represents O, S or NR; n represents an integer of 0 or 1; R represents a hydrogen atom, an alkyl group or an acyl group; R1 to R8 each independently represent a hydrogen atom or a monovalent substituent; R1 and R2, R2 and R3, and R3 and R4 may be connected to each other to form a ring; and R5 or R6 may be connected to R7 or R8 to form an aliphatic ring but not to form an aromatic ring.
    Type: Grant
    Filed: January 14, 2008
    Date of Patent: July 26, 2011
    Assignee: FUJIFILM Corporation
    Inventors: Tokihiko Matsumura, Ippei Nakamura
  • Publication number: 20110170209
    Abstract: Compounds of the formula I or (I?), wherein R1 and R?1 for example are hydrogen, C3-C8cycloalkyl or C1-C12alkyl, R2 and R2? for example are hydrogen; unsubstituted C1-C20alkyl or substituted C1-C20alkyl; and R8 and R9 for example are hydrogen, C1-C12alkyl which optionally is substituted, or phenyl which optionally is substituted; exhibit an unexpectedly good performance in photopolymerization reactions.
    Type: Application
    Filed: May 27, 2009
    Publication date: July 14, 2011
    Applicant: BASF SE
    Inventors: Akira Matsumoto, Hisatoshi Kura
  • Patent number: 7863473
    Abstract: A method of producing an organosilylamine containing a radiation-polymerizable functional group that is useful as a surface treatment agent is provided. The method includes reacting an organosilylamine containing a haloalkyl group, and at least one salt having a radiation-polymerizable functional group selected from the group consisting of alkali metal salts of organic acids having a radiation-polymerizable functional group and alkaline earth metal salts of organic acids having a radiation-polymerizable functional group, at a temperature within a range from 50 to 150° C. An organosilylamine containing a radiation-polymerizable functional group composed of a specific silazane unit is also provided.
    Type: Grant
    Filed: August 20, 2008
    Date of Patent: January 4, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Kazuhiro Tsuchida, Masaaki Yamaya
  • Patent number: 7754779
    Abstract: An ink for an ink jet printer includes an ink vehicle of at least one radically curable, multifunctional acrylate monomer or oligomer, at least one colorant, and at least one photoinitiator. The ink has a low viscosity at low jetting temperatures of 30 to 50° C. and is curable upon exposure to ultraviolet radiation.
    Type: Grant
    Filed: January 13, 2005
    Date of Patent: July 13, 2010
    Assignee: Xerox Corporation
    Inventors: Peter G. Odell, Adela Goredema
  • Publication number: 20100048756
    Abstract: A radiation curable composition comprising a curable compound, a photo-initiator and a co-initiator, characterized in that said co-initiator is a oligomer or polymer having a repeating unit, said repeating unit comprising at least two tertiary amines, and said polymer being prepared by the polycondensation of di- or oligofunctional Michael acceptors with mono- or oligofunctional aliphatic primary amines or with di- or oligofunctional aliphatic secondary amines or with a mixture thereof.
    Type: Application
    Filed: December 17, 2007
    Publication date: February 25, 2010
    Applicant: Agfa Graphics NV
    Inventors: Johan Loccufier, Roland Claes
  • Patent number: 7569618
    Abstract: A method of surface cross-linking superabsorbent polymer particles using UV irradiation is provided. The method is carried out in a so-called drum reactor, which comprises a hollow drum and an irradiation source. The drum has a longitudinal axis and a cross-section. Radical former molecules are applied on the surface of superabsorbent polymer particles. These superabsorbent polymer particles are fed into the drum and are irradiated while they move within the drum, which is rotated around its longitudinal axis. The irradiation source is provided such that the radiation emitted by the irradiation source is able to reach superabsorbent polymer particles within said drum. The irradiation source for use in the method is able to emit UV radiation of a wavelength between about 201 nm and about 400 nm.
    Type: Grant
    Filed: August 23, 2006
    Date of Patent: August 4, 2009
    Assignee: The Procter & Gamble Company
    Inventors: Andreas Flohr, Torsten Lindner, Esther Oliveros, Yoshiro Mitsukami
  • Publication number: 20090048363
    Abstract: A description is given of radiation-sensitive compositions composed of a binder component and low-odor polymeric reaction products composed of the reaction product of aldehydes and ketones.
    Type: Application
    Filed: July 28, 2005
    Publication date: February 19, 2009
    Applicant: Degussa GmbH
    Inventors: Patrick Glockner, Michael Ewald, Peter Denkinger
  • Patent number: 7368484
    Abstract: The present invention relates to novel polymeric compositions that exhibit Reverse Thermal Gelation (RTG) properties for use as Support Materials (SM) in the manufacture of three-dimensional objects. These polymers are Temperature Sensitive Polymers that respond with a significant change of properties to a small change in temperature. Temperature Sensitive Polymers exhibit cloud point (CP) or lower critical solution temperature (LCST) in aqueous solutions. Water-soluble Temperature Sensitive Polymers are chosen to give low viscosity liquid at low temperature when dissolved in water and by that to permit easy dispensing at low temperature. Raising the temperature above their gelation temperature (Tgel) will result in solidification of the composition. At its gel position the material has favorable characteristics as a support and building material. The gel layers have the appropriate toughness and dimensional stability to support the model layers during the building process.
    Type: Grant
    Filed: October 10, 2006
    Date of Patent: May 6, 2008
    Assignee: Objet Geometries Ltd.
    Inventor: Avraham Levy
  • Patent number: 7276543
    Abstract: The present invention relates to a coated optical fiber comprising a glass optical fiber with a single protective coating or a combination of an inner and an outer primary coating applied thereon and optionally with a colored coating subsequently applied thereon wherein the inner primary coating or at least a portion of the single coating is prepared from a radiation curable composition which when cured as a capillary film with a 100W medium pressure mercury lamp has a percentage reacted acrylate unsaturation of at least about 54% after exposure to a dose of about 4.4 mJ/cm2 or wherein the outer primary coating is prepared from a radiation curable composition which when cured as a capillary film with a 100 W medium pressure mercury lamp has a percentage reacted acrylate unsaturation of at least about 56% after exposure to a dose of about 4.4 mJ/cm2. The invention further relates to a radiation curable composition having a high cure speed.
    Type: Grant
    Filed: October 9, 2001
    Date of Patent: October 2, 2007
    Assignee: DSM IP Assets B.V.
    Inventors: Timothy E. Bishop, Paul E. Snowwhite, Tyson Norlin, James J. Schouten, John Southwell, Anthony Toussaint
  • Patent number: 6896937
    Abstract: Radiation-curable ink compositions and methods of printing including the compositions are disclosed. In some embodiments, a radiation-curable hot melt ink composition includes a colorant, a polymerizable monomer, and a photoinitiating system. The photoinitiating system can include 0.5-1.5% by weight of an aromatic ketone photoinitiator, 2-10% by weight of an amine synergist, 3-8% by weight of an alpha-cleavage type photoinitiator, and 0.5-1.5% by weight of a photosensitizer.
    Type: Grant
    Filed: November 14, 2003
    Date of Patent: May 24, 2005
    Assignee: Markem Corporation
    Inventor: Richard C. Woudenberg
  • Patent number: 6756166
    Abstract: Disclosed is a photosensitive resin composition which can be developed using a dilute aqueous alkaline solution after ultraviolet ray exposure, is excellent in pot life, capable of preventing deposits from being generated in a cured coated film, capable of widening heat control tolerance, and is excellent in sensitivity, in heat resistance, in chemical resistance and in electric insulating properties, thereby rendering the composition suitable for use as a solder resist for producing a printed wiring board. This photosensitive resin composition comprises (A) an active energy ray-curable resin having at least two ethylenic unsaturated linkages per molecule thereof, (B) at least one kind material selected from acid salts of N-substituted melamine compound and acid salts of guanamine compound, (C) a photopolymerization initiator, (D) a diluent, and (E) a thermosetting compound. There is also disclosed a printed wiring board where this photosensitive resin composition is employed.
    Type: Grant
    Filed: September 23, 2002
    Date of Patent: June 29, 2004
    Assignee: Tamurakaken Corporation
    Inventors: Takao Ono, Ichiro Miura
  • Patent number: 6645696
    Abstract: The use of selected buffering amines in a photoimageable composition prevents process bias which with conventional photoresists causes designed features to be distorted, especially in corners and high resolution features. It is believed that the amines react with the catalysts, e.g., photoacids, generated to create an inert salt. The presence of the amines also increases resolution. Suitable photoimageable compositions includes: (a) a multifunctional polymeric epoxy resin that is dissolved in an organic solvent wherein the epoxy resin comprises oligomers of bisphenol A that is quantitatively protected by glycidyl ether and wherein the oligomers have an average functionality that ranges from about 3 to 12; (b) a photoactive compound; and (c) an amine that is selected from the group consisting of triisobutylamine, 1,8-bis(dimethylamino)naphthalene (also known as PROTON SPONGET™), 2,2′-diazabicyclo[2.2.2] octane and mixtures thereof.
    Type: Grant
    Filed: November 30, 2001
    Date of Patent: November 11, 2003
    Assignee: Euv LLC.
    Inventors: Kelby Liv Simison, Paul Dentinger
  • Patent number: 6448302
    Abstract: A radiation curable coating comprising: (i) at least one radiation polymerizable reactant; (ii) at least one initiator for initiating cure; (iii) at least one wax; wherein the wax is present in an amount sufficient to reduce the 60° gloss of the cured coating to a gloss level less than 40 when the coating is cured by exposure to radiation in the presence of oxygen to provide a dry film thickness of 1.0±0.1 mil.
    Type: Grant
    Filed: November 28, 2000
    Date of Patent: September 10, 2002
    Assignee: The Sherwin-Williams Company
    Inventors: William R. Dawson, Tai M. Liang, Joseph E. Miller
  • Publication number: 20020042022
    Abstract: Compounds of the formula I 1
    Type: Application
    Filed: May 18, 2001
    Publication date: April 11, 2002
    Inventors: David George Leppard, Manfred Kohler, Andreas Valet
  • Patent number: 6361925
    Abstract: Compounds of the formula I in which R1 is C1-C4alkyl, R2 is hydrogen, C1-C4alkyl or C1-C4alkoxy and R3, R4, R5, R6 and R7 independently of one another are hydrogen, halogen, C1-C20alkyl, cyclopentyl, cyclohexyl, C2-C12alkenyl, C2-C18alkyl which is interrupted by one or more oxygen atoms, or are phenyl-substituted C1-C4alkyl, or are phenyl which is unsubstituted or is mono- or disubstituted by C1-C4alkyl and/or C1-C4alkoxy, with the provisos that at least one of the radicals R3, R4, R5, R6 and R7 is other than hydrogen and that, if R1 and R2 are methyl, R3 and R6 are not methyl, and mixtures of such compounds with &agr;-hydroxy ketones, benzophenones and &agr;-amino ketones, are suitable as photoinitiators.
    Type: Grant
    Filed: May 18, 2001
    Date of Patent: March 26, 2002
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: David George Leppard, Manfred Köhler, Andreas Valet
  • Publication number: 20010012596
    Abstract: Compounds of the formulae I, II, III, IV and V 1
    Type: Application
    Filed: December 12, 2000
    Publication date: August 9, 2001
    Inventors: Kazuhiko Kunimoto, Hidetaka Oka, Masaki Ohwa, Junichi Tanabe, Hisatoshi Kura, Jean-Luc Birbaum
  • Patent number: 6204302
    Abstract: A photoinitiator composition that includes (a) 1-aryl-2-alkyl-1,2-ethanedione and (b) a rigid 1,2-dione in a weight ratio of (a):(b) in a range of about 1:20 to about 20:1 is disclosed. The photoinitiator composition can be used in a photocurable dental composition in an amount sufficient to achieve a degree of double-bond conversion of at least 50%. Methods for making the photocurable dental composition are also disclosed.
    Type: Grant
    Filed: November 19, 1999
    Date of Patent: March 20, 2001
    Assignee: Bisco, Inc.
    Inventors: H. Ralph Rawls, Yeong-Joon Park, Kyu-Ho Chae
  • Patent number: 6054251
    Abstract: The present invention provides a visible laser-curable resist composition which contains at least one radical-protecting compound selected from a phosphorous acid ester compound and an aromatic compound having N,N-dimethylamino group bonded to the carbon atom forming the aromatic ring and which is free from the hindrance of curing caused by deactivation of radical by oxygen and has excellent curability, and a process for formation of a resist pattern using the above composition.
    Type: Grant
    Filed: September 25, 1997
    Date of Patent: April 25, 2000
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Genji Imai, Hideo Kogure
  • Patent number: 6025112
    Abstract: A photocurable composition comprises an unsaturated group-containing compound as a base material, a metal arene compound as a photopolymerization initiator and an aniline compound as a photosensitizer. As the photosensitizer aniline compound, any one or both of 2,6-diisopropyl-N,N-dimethylaniline and 2,4,6,N,N-pentamethylaniline is/are used.
    Type: Grant
    Filed: February 4, 1997
    Date of Patent: February 15, 2000
    Assignee: Brother Kogyo Kabushiki Kaisha
    Inventor: Masashi Tsuda
  • Patent number: 5994424
    Abstract: A free-radical curable polish composition is described. The composition can be applied and cured as an ultra thin film on finished surfaces to provide enhanced chemical and mar resistance. The composition comprises an aqueous emulsion including an olefin-functional polymer or an olefin-functional prepolymer, and a silicone or silicone copolymer preferably with photoinitiators for UV and EB cure. The polish/emulsion can be applied, for example, to wet the surface of nitrocellulose lacquer wood finishes. The polish wet surface is first wiped to remove excess polish and thereafter exposed to UV radiation to provide a thin, polymerized protective film.
    Type: Grant
    Filed: February 12, 1998
    Date of Patent: November 30, 1999
    Assignee: Lilly Industries, Inc.
    Inventors: Eugen Safta, Frank Chen, Greg Muselman, James V. Mirante, Danny R. Linthicum
  • Patent number: 5962547
    Abstract: Radiation- or thermally-initiated cationically-curable styrene oxides of the structure ##STR1## are suitable for use in cationically curable adhesive and coating compositions.
    Type: Grant
    Filed: May 14, 1998
    Date of Patent: October 5, 1999
    Inventors: Nikola A. Nikolic, Rose Ann Schultz
  • Patent number: 5837745
    Abstract: A free-radical polish composition is described. The composition can be applied and cured as an ultra thin film on finished surfaces to provide enhanced chemical and mar resistance. The composition comprises an aqueous emulsion including an olefin-functional polymer having low glass transition temperature or an olefin-functional prepolymer, and a silicone or silicone copolymer preferably with photoinitiators for UV and EB cure. The polish/emulsion can be applied, for example, to wet the surface of nitrocellulose lacquer wood finishes. The polish wet surface is first wiped to remove excess polish and thereafter exposed to UV radiation to provide a thin, polymerized permanent protective film on the polished surface.
    Type: Grant
    Filed: April 10, 1997
    Date of Patent: November 17, 1998
    Assignee: Lilly Industries, Inc.
    Inventors: Eugen Safta, James V. Mirante, Danny R. Linthicum, Greg Muselman
  • Patent number: 5719202
    Abstract: Polymerizable compounds based on N-acylamido-piperazines are provided. Such compounds have the formula: ##STR1## wherein: R.sup.1, R.sup.2, and R.sup.3 are each independently selected from the group consisting of hydrogen and lower alkyl,B is a linking group selected from the group consisting of carbonyl, sulfonyl, amide, and carboxyl;n is one or zero;R.sup.4 is a radical selected from the group consisting of a higher aliphatic group (i.e. at least four carbon atoms, preferably from about 6 to about 50 carbon atoms), a substituted higher aliphatic group, an alicyclic group, a heterocyclic group a non-benzenoid aromatic group, and a substituted aromatic group. These compounds can be incorporated into a polymerizable composition. The compounds is preferably present in said composition in a major amount on a mole percent basis of th polymerizable monomers. These polymerizable compositions are useful as coatings, particularly in formulations containing a photoinitiator susceptible to ultra-violet radiation.
    Type: Grant
    Filed: February 27, 1996
    Date of Patent: February 17, 1998
    Assignee: Henkel Corporation
    Inventor: Paul E. Share
  • Patent number: 5712322
    Abstract: A composition of matter useful in the production of photoinitiator compositions, said compositions of matter comprising 100 parts by weight of camphorquinone and from 1 to 50 parts by weight of an anthraquinone compound having in the 2-position a substituent of the formula:--X--COR.sup.1 (1)wherein 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.
    Type: Grant
    Filed: October 6, 1995
    Date of Patent: January 27, 1998
    Assignee: Zeneca Limited
    Inventors: Pushpito Kumar Ghosh, Iain Andrew Weddell, John Edward Yates
  • Patent number: 5418112
    Abstract: A method useful for stereolithography that yields enhanced photospeed, as well as a photocurable polymer composition well adapted for use with same, are disclosed.A preferred combination includes 1,2-dimethoxy-2-phenyl acetophenone, benzophenone, and triphenyl phosphine combined with a polyurethane (meth)acrylate oligomer.
    Type: Grant
    Filed: November 10, 1993
    Date of Patent: May 23, 1995
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Srinivas K. Mirle, Ronald J. Kumpfmiller
  • Patent number: 5344353
    Abstract: A method for manufacturing a cathode ray tube is provided which comprises (a) spraying on the inner surface of a phosphor layer of a phosphor coated panel, an organic composition for forming a heat labile film, the organic composition being free of flammable or explosive organic solvents and including an initiator capable of forming a radical or cation when exposed to ultraviolet or electron rays and at least one resin containing at least one group consisting of acrylate, vinyl and diazo functional groups to form a heat labile film thereon; (b) exposing the heat labile film to ultraviolet or electron rays to from a hardened film layer; (c) forming an aluminum layer on a surface of the hardened film layer to form a screen; (d) sealing with heat the panel and a funnel to form a bulb with a mount including an electron gun and a stem, wherein the step of sealing to form a bulb decomposes the hardened film layer.
    Type: Grant
    Filed: November 1, 1991
    Date of Patent: September 6, 1994
    Assignee: Samsung Electron Devices Co., Ltd.
    Inventors: Dong-sik Jang, Byeong-yong Lee
  • Patent number: 5246979
    Abstract: The heat stability of acrylamide functional polydiorganosiloxanes which cure by exposure to ultraviolet radiation can be improved by the addition of nickel carboxylate, stannous naphthenate, cerium carboxylate, manganese carboxylate, aluminum carboxylate, silver carboxylate, copper undecylenate, cobalt carboxylate, mono(methacrylate) tripropoxyzirconate, mono(ethylacetoacetonate) aluminum di-(sec-butoxide), di-(ethylacetoacetonate) aluminum sec-butoxide, zinc acetylacetonate, molybdenum acetylacetonate, and dibutyltin dicarboxylate.
    Type: Grant
    Filed: May 31, 1991
    Date of Patent: September 21, 1993
    Assignee: Dow Corning Corporation
    Inventors: Michael A. Lutz, Kristen A. Scheibert
  • Patent number: 5212271
    Abstract: A process for texturing a coating via exposing a photocurable composition comprising a multifunctional urea compound, an ethylenically unsaturated compound, and an aromatic ketone photosensitizer that functions through a hydrogen abstraction mechanism when exposed to ultraviolet light.
    Type: Grant
    Filed: December 22, 1989
    Date of Patent: May 18, 1993
    Assignee: Texaco Chemical Company
    Inventors: Alison D. Beckett, Joseph V. Koleske, Richard M. Gerkin
  • Patent number: 5096938
    Abstract: Radiation-curable catalysts are obtainable by reactingA) 1 equivalent of a dihydric to hexahydric oxyalkylated C.sub.2 -C.sub.10 -alcohol withB) from 0.05 to 1 equivalent of a dibasic to tetrabasic C.sub.3 -C.sub.36 -carboxylic acid or its anhydride andC) from 0.1 to 1.5 equivalents of acrylic acid and/or methacrylic acidand reacting the excess carboxyl groups with an equivalent amount of epoxide compound, and are used in radiation-curable coating materials.
    Type: Grant
    Filed: April 3, 1990
    Date of Patent: March 17, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Erich Beck, Wolfram Weiss, Horst Schmidt
  • Patent number: 5071888
    Abstract: Photopolymerizable prepolymer compositions are provided comprising an unsaturated compound having at least one ethylenic double bond that is photopolymerizable to form a polymer, and a photoinitiator having one of the formulae: ##STR1##
    Type: Grant
    Filed: July 8, 1985
    Date of Patent: December 10, 1991
    Assignee: Asahi Denka Kogyo K.K.
    Inventor: Naohiro Kubota
  • Patent number: 5043361
    Abstract: A combined chemical-/light-polymerization type composition for dental restoration consists of a formulation A composed main of a. an ethylenically polymerizable unsaturated compound, b. a photo-polymerization initiator and c. a reducing agent, and a formulation B composed mainly of d. a filler and e. an organic peroxide. The formulations A and B are separately packaged and designed to be mixed for use.
    Type: Grant
    Filed: June 7, 1990
    Date of Patent: August 27, 1991
    Assignee: G-C Dental Industrial Corporation
    Inventors: Takao Kubota, Tetsuro Sakuma, Ryoji Nakazato
  • 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: 5008300
    Abstract: A visible light ray-curable monomeric composition for fastening loose teeth, comprising: a filler component consisting of fine, solid particles having an average size of 0.01 to 100 .mu.m and in an amount of 40% to 85% based on the weight of the total weight of the composition; a polyfunctional monomer component consisting of a radical-polymerizable, polyfunctional monomer; a monofunctional monomer consisting of a radical-polymerizable, monofunctional monomer; and a photopolymerization initiator; having a viscosity of 1,000 to 500,000 cps at a temperature of 25.degree. C., and contained in a light-shielded container.
    Type: Grant
    Filed: September 11, 1989
    Date of Patent: April 16, 1991
    Assignee: Mitsubishi Rayon Company Ltd.
    Inventors: Takayuki Makino, Nobuhiro Mukai, Hitoshi Ige
  • Patent number: 4961960
    Abstract: There is provided a photo-curable coating composition comprising (a) a photo-curable monomer of polymer and (b) a compound having a blocked isocyanate group and at least one ethylenically unsaturated group.
    Type: Grant
    Filed: April 13, 1984
    Date of Patent: October 9, 1990
    Assignee: Nippon Paint Co., Ltd.
    Inventor: Tamio Iimure