Specified Rate-affecting Material Contains Onium Group Patents (Class 522/15)
  • Patent number: 7365106
    Abstract: A cationically curable composition for dental use containing a cationic polymerization initiator (I) and cationically polymerizable monomers (II), the cationically polymerizable monomers (II) containing an oxetane compound and an epoxy compound or an alkenyl ether compound at a ratio of amounts that satisfy the conditions expressed by the following formula, (a×A):(b×B)=91:9 to 45:55 wherein A is a mol number of the oxetane compound, “a” is an average number of the oxetane functional group contained in one molecule of the oxetane compound, B is a mol number of the epoxy compound or the alkenyl ether compound, and “b” is an average number of the epoxy functional group contained in one molecule of the epoxy compound or an average number of the alkenyl ether functional group contained in one molecule of the alkenyl ether compound.
    Type: Grant
    Filed: April 26, 2005
    Date of Patent: April 29, 2008
    Assignees: Tokuyama Corporation, Tokuyama Dental Corporation
    Inventors: Takeshi Suzuki, Hideki Kazama
  • Patent number: 7232850
    Abstract: A photocurable composition comprising cationically curable compound, an acrylate-containing compound; a hydroxyl-containing compound; a cationic photoinitiator; and a free radical photoinitiator; wherein said composition has less than 0.54 equivalents of cationically curable groups, less than 0.10 equivalents of acrylate groups and less than 0.10 equivalents of hydroxyl groups per 100 grams of said composition.
    Type: Grant
    Filed: October 3, 2003
    Date of Patent: June 19, 2007
    Assignee: Huntsman Advanced Materials Americas Inc.
    Inventors: David Johnson, Frank Tran, John Fong, Richard Leyden, Ranjana Patel
  • Patent number: 7160669
    Abstract: The present invention provides a sulfonium salt of the formula (Ia) a polymeric compound comprising a structural unit of the formula (Ib) and a chemical amplification type positive resist composition comprising (A) an acid generator comprising at least one compound selected from the group consisting of a sulfonium salt of the formula (Ia), a polymeric compound comprising a structural unit of the formula (Ib), and a sulfonium salt of the formula (Ic); and (B) resin which contains a structural unit having an acid labile group and which itself is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid.
    Type: Grant
    Filed: October 10, 2003
    Date of Patent: January 9, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Airi Yamada, Yasunori Uetani, Akira Kamabuchi
  • Patent number: 7122294
    Abstract: Photoacid generators (PAGs) comprising photoactive moieties and perfluorinated, multifunctional anionic moieties (or incipient anionic moieties) are disclosed which provide photoacids with high acid strength, low volatility and low diffusivity. The present invention further relates to photoacid generators as they are used in photoinitiated or acid-catalyzed processes for uses such as photoresists for microlithography and photopolymerization.
    Type: Grant
    Filed: May 22, 2003
    Date of Patent: October 17, 2006
    Assignee: 3M Innovative Properties Company
    Inventor: William M. Lamanna
  • Patent number: 7078444
    Abstract: Photoacid generator salts comprising photoactive cationic moieties and segmented, highly fluorinated-hydrocarbon anionic moieties are disclosed which provide high photoacid strength and can be tailored for solubility and polarity. The present invention further relates to photoacid generators as they are used in photoinitiated acid-catalyzed processes for uses such as photoresists for microlithography and photopolymerization.
    Type: Grant
    Filed: January 5, 2005
    Date of Patent: July 18, 2006
    Assignee: 3M Innovative Properties Company
    Inventors: William M. Lamanna, Gregory D. Clark, Richard M. Flynn, Zai-Ming Qiu
  • Patent number: 7064152
    Abstract: Compositions are provided that include an electron donor and a sensitizing compound. More specifically, the electron donor is an arylsulfinate salt. Methods of polymerization are also provided that can be used to prepare polymeric material from a photopolymerizable composition that includes ethylenically unsaturated monomers and a photoinitiator system. The photoinitiator system includes an electron donor and a sensitizing compound.
    Type: Grant
    Filed: May 17, 2004
    Date of Patent: June 20, 2006
    Assignee: 3M Innovative Properties Company
    Inventors: Rajdeep S. Kalgutkar, Michael C. Palazzotto
  • Patent number: 7026367
    Abstract: Compositions are provided that include a photoinitiator system for free radical polymerization reactions. More specifically, the photoinitiator includes an arylsulfinate ion and a triarylsulfonium ion. Polymerization methods are also provided those include the photoinitiator in a photopolymerizable composition. Additionally, triarylsulfonium arylsulfinate salts are disclosed.
    Type: Grant
    Filed: September 26, 2003
    Date of Patent: April 11, 2006
    Assignee: 3M Innovative Properties Company
    Inventor: Rajdeep S. Kalgutkar
  • Patent number: 6998425
    Abstract: The present invention is directed to curable acrylate coating compositions and coated articles resulting therefrom. The curable acrylate coating composition comprises at least two polyfunctional acrylate derivatives, at least one photoinitiator and at least one nanoscale filler.
    Type: Grant
    Filed: December 23, 2003
    Date of Patent: February 14, 2006
    Assignee: General Electric Company
    Inventors: Bret Ja Chisholm, James Norman Cawse, Chris Anthony Molaison, Michael Jorlath Brennan, Jr.
  • Patent number: 6949297
    Abstract: Described are curable adhesives containing a polyacrylate component and an epoxy component, and that are preferably optically clear, as well as methods of using such adhesives and optical components and optical elements prepared from the adhesives.
    Type: Grant
    Filed: November 2, 2001
    Date of Patent: September 27, 2005
    Assignee: 3M Innovative Properties Company
    Inventors: Jie Yang, Dmitriy Salnikov, Jason W. Balich
  • Patent number: 6905735
    Abstract: The present invention discloses an ultraviolet light curable paint composition and method for applying and making such a composition to a substrate. Suitable substrates include glass, metals, and various plastics such as polycarbonates. The disclosed composition does not contain any significant amount of volatile organic solvents that do not become incorporated in the coating or are released to ambient after curing.
    Type: Grant
    Filed: November 15, 2002
    Date of Patent: June 14, 2005
    Assignee: Allied PhotoChemical, Inc.
    Inventor: Roy C. Krohn
  • Patent number: 6900250
    Abstract: A polymerizable composition comprising a polymerization initiator (A) represented by the formula (1) and a radical-polymerizable compound (B): (wherein R5, R6, R7, R8 and R9 are each independently a hydrogen atom, an alkyl, alkoxyl, hydroxyl or acyloxy group, a halogen atom, or —NR10R11, but at least one of them is —NR10R11; wherein R1, R2, R3, R4, R10 and R11 are each independently a hydrogen atom, or an alkyl or aryl group; and Z? is an arbitrary anion).
    Type: Grant
    Filed: March 12, 2002
    Date of Patent: May 31, 2005
    Assignee: Toyo Ink Mfg. Co., Ltd.
    Inventors: Takahiko Uesugi, Masashi Arishima, Tadao Yagi
  • Patent number: 6833231
    Abstract: A liquid radiation-curable composition that comprises (A) at least one polymerizing organic substance; (B) at least one free-radical polymerizing organic substance; (C) at least one cationic polymerization initiator; (D) at least one free-radical polymerization initiator; (E) at least one hydroxyl-functional compound; and (F) at least one epoxy interpenetrating polymer compound;
    Type: Grant
    Filed: July 31, 2002
    Date of Patent: December 21, 2004
    Assignee: 3D Systems, Inc.
    Inventors: Khalil M. Moussa, Jiaching Liu
  • Patent number: 6783840
    Abstract: The present invention provides a resist ink composition comprising a compound (a) having at least one oxetanyl group and at least one epoxy group within the same molecule and a compound (b) capable of initiating cationic polymerization under irradiation by an active energy ray and/or under heat. This resist ink composition has high photosensitivity and enables the final curing by a brief heating and the cured film exhibits good physical properties.
    Type: Grant
    Filed: October 29, 2001
    Date of Patent: August 31, 2004
    Assignee: Showa Denko K.K.
    Inventors: Takeo Watanabe, Takashi Sato, Hirotaka Tagoshi
  • Publication number: 20040152009
    Abstract: The present invention provides a sulfonate of the formula (I): 1
    Type: Application
    Filed: August 25, 2003
    Publication date: August 5, 2004
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Satoshi Yamaguchi, Yasunori Uetani, Hiroshi Moriuma
  • Patent number: 6765036
    Abstract: Photopolymerizable compositions comprise a cationically polymerizable resin and a photoinitiator system comprising: (i) an iodonium salt; (ii) a visible light sensitizer; and (iii) an electron donor compound having an oxidation potential less than that of 1,4-dimethoxybenzene when measured versus a saturated calomel electrode, wherein the photoinitiator system has a photoinduced potential of less than that of 3-dimethylaminobenzoic acid in a standard solution of 2.9×10−5 moles/g diphenyl iodonium hexafluoroantimonate and 1.5×10−5 moles/g camphorquinone in 2-butanone. The compositions polymerize on exposure to light in the visible spectrum and are useful in a variety of applications, including dental adhesives and dental composites.
    Type: Grant
    Filed: January 15, 2002
    Date of Patent: July 20, 2004
    Assignee: 3M Innovative Properties Company
    Inventors: Karsten Dede, Thomas Klettke, Thomas Luchterhandt, Joel D. Oxman
  • Patent number: 6706779
    Abstract: This invention relates to radiation curable compositions comprising an alkenyl ether functional polyisobutylene, a cationic photoinitiator, and a miscible reactive diluent selected from specified organic vinyl ether compounds, epoxy functional compounds, or compounds having the formula R8Xb, wherein R8 is a non-silicon containing organic group, X is an organic group containing at-least one acrylate functional group, and b has a value of 1-3. The radiation curable compositions exhibit a low cure energy, have a high moisture vapor barrier, high damping characteristics, and a high refractive index, and provide a barrier to corrosive vapors and have maintained or enhanced modulus, tensile strength, and toughness.
    Type: Grant
    Filed: August 27, 2001
    Date of Patent: March 16, 2004
    Assignee: Dow Corning Corporation
    Inventors: Maneesh Bahadur, Susan Victoria Perz, Toshio Suzuki
  • Patent number: 6703433
    Abstract: This invention relates to radiation curable compositions comprising an alkenyl ether functional polyisobutylene, a cationic photoinitiator, and a miscible reactive diluent selected from specified organic vinyl ether compounds or compounds having the formula R8Xb, wherein R8 is a non-silicon containing organic group, X is an organic group containing at-least one acrylate functional group, and b has a value of 1-3. The radiation curable compositions exhibit a low cure energy, have a high moisture vapor barrier, high damping characteristics, and a high refractive index, and provide a barrier to corrosive vapors and have maintained or enhanced modulus, tensile strength, and toughness.
    Type: Grant
    Filed: May 12, 2000
    Date of Patent: March 9, 2004
    Assignee: Dow Corning Corporation
    Inventors: Maneesh Bahadur, Susan Victoria Perz, Toshio Suzuki
  • Patent number: 6703181
    Abstract: There is provided a photosensitive composition suitable for a resist material. This photosensitive composition has a high sensitivity and a high resolution with respect to a light source having a short wavelength, does not cause a phase separation in a film state, and makes it possible to stably form fine resist patterns. The photosensitive composition contains a polymer obtained by protecting an alkali-soluble group of an alkali-soluble polymer by a group which is unstable with respect to an acid, a compound which generates an acid upon being irradiated with light, at least one compound which is selected from the group consisting of an imidazole compound, an alanine compound, an adenine compound, an adenosine compound, and a quaternary ammonium salt compound, and which increases miscibility in a resist film, and a phenol compound.
    Type: Grant
    Filed: September 9, 1996
    Date of Patent: March 9, 2004
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Takao Hayashi, Yasunobu Onishi, Kazuo Sato, Kenji Chiba, Masataka Miyamura
  • Publication number: 20040023145
    Abstract: A liquid radiation-curable composition that comprises
    Type: Application
    Filed: July 31, 2002
    Publication date: February 5, 2004
    Applicant: 3D Systems, Inc.
    Inventors: Khalil M. Moussa, Jiaching Liu
  • Patent number: 6677390
    Abstract: An iodonium salt compound which is colored little, can be easily synthesized in high yield, is highly sensitive to irradiation with actinic energy rays such as light, electronic beams, or X-rays, is highly soluble in monomers, and is lowly toxic; and a photocurable composition which can cure in a short time even when the counter anion is a hexafluorophosphonate, tetrafluoroborate, etc., regardless of whether it is clear or pigmented, and which gives a cured object having excellent properties. The photocurable composition is prepared by compounding an iodonium salt compound represented by the general formula (I) with a cationically polymerizable compound, a sensitizer, etc.
    Type: Grant
    Filed: January 31, 2002
    Date of Patent: January 13, 2004
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Eiji Takahashi, Akihiro Shirai, Hiroshi Takahashi, Shinichi Kimizuka
  • Patent number: 6670017
    Abstract: Photocurable compositions and process for providing form-in-place gaskets using automated placement followed by photocuring of a pattern of a non-silicone composition comprising a liquid polyolefin oligomer, a reactive diluent, and a curative. The form-in-place gasket, after curing, has a level of total outgassing components of about 10 &mgr;g/g to about 45 &mgr;g/g. The curative responds to actinic radiation and heat, and may contain a photoinitiator. Optionally a photocurable, form-in-place gasket according to the present invention further comprises a thixotropic filler in an amount from about 8.0 wt. % to about 12.0 wt. %, and preferably comprises a fumed silica.
    Type: Grant
    Filed: September 4, 2001
    Date of Patent: December 30, 2003
    Assignee: 3M Innovative Properties Company
    Inventors: Mitchell Huang, Michael A. Kropp
  • Patent number: 6649668
    Abstract: The invention concerns the field of polymerization and/or cross-linking reaction catalysis by cationic process of monomers, oligomers and/or polymers. In particular, novel polymerization and/or cross-linking initiator systems comprising at least one onium borate and at least one benzophenone are described to satisfy the ever greater exigencies of productivity and manufacture. The initiators are used in particular for preparing resins and/or composite materials based on an organic and/or silicon matrix or optionally a matrix of acrylic monomers, oligomers, or polymers.
    Type: Grant
    Filed: June 15, 2000
    Date of Patent: November 18, 2003
    Inventors: Marie-Anne David, Jean-Marc Frances
  • Patent number: 6610759
    Abstract: An adhesive composition that includes a mixture of a cationically polymerizable component, an acidic component, and an initiator is provided. Preferably, the initiator comprises an iodonium salt, a visible light sensitizer, and an electron donor compound, wherein the initiator has a photoinduced potential greater than or equal to that of N,N-dimethylaniline in a standard solution of 2.9×10−5 moles/g diphenyl iodonium hexafluoroantimonate and 1.5×10−5 moles/g camphorquinone in 2-butanone. This adhesive composition is cationically polymerizable and is able to bond to hard tissue and cationic restorative materials upon curing.
    Type: Grant
    Filed: March 6, 2000
    Date of Patent: August 26, 2003
    Assignees: Curators of the University of Missouri, 3M Innovative Properties Company
    Inventors: Cecil C. Chappelow, Charles S. Pinzino, J. David Eick, James Code, Joel D. Oxman, Sharon M. Rozzi
  • Publication number: 20030118939
    Abstract: The present invention provides an IR-sensitive composition, which includes: a polymeric binder; and a free radical polymerizable system consisting of: at least one component selected from unsaturated free radical polymerizable monomers, oligomers which are free radical polymerizable and polymers containing C═C bonds in the backbone and/or in the side chain groups; and an initiator system, which includes: (a) at least one compound capable of absorbing IR radiation; (b) at least one compound capable of producing radicals; and (c) at least one carboxylic co-initiator, provided that the total acid number of the polymeric binder is 70 mg KOH/g or less. The present invention further provides a printing plate precursor, a process for preparing the printing plate and a method of producing an image.
    Type: Application
    Filed: November 9, 2001
    Publication date: June 26, 2003
    Applicant: KODAK POLYCHROME GRAPHICS, L.L.C.
    Inventors: Heidi Munnelly, Paul West
  • Patent number: 6545064
    Abstract: This invention relates to a curable coating composition which comprises: (A) a compound represented by the formula wherein in formula (A-I) each R independently is hydrogen or a hydrocarbyl group of 1 to about 8 carbon atoms, and n is a number that is about 4 or higher; and (B) a reactive vinyl or unsaturated monomer or oligomer, provided said reactive vinyl or unsaturated monomer or oligomer is not the same as (A). In one embodiment the inventive composition further comprises (C) a photoinitiator. In one embodiment, the inventive composition further comprises (D) a thermal initiator. In one embodiment, the inventive composition further comprises (E) a latent acid catalyst. The invention also relates to a method of coating a substrate utilizing the foregoing coating composition, as well as to a substrate coated in accordance with foregoing method.
    Type: Grant
    Filed: November 24, 1999
    Date of Patent: April 8, 2003
    Assignee: Avery Dennison Corporation
    Inventor: Wayne Louis Bilodeau
  • Publication number: 20030004221
    Abstract: A curable composition that is curable by polymerizing both a group capable of ring-opening polymerization and an ethylenically unsaturated group includes a cross-linkable polymer containing a repeating unit represented by the formula below, the group capable of ring-opening polymerization being present in a side chain of the polymer. A hardcoated article is formed by curing the curable composition. Its hardcoat layer has a pencil hardness of 4H to 9H. A hardcoated film is formed by coating on a plastic film the curable composition and curing it. The hardcoated film is used, for example, to laminate the front face of an image display device.
    Type: Application
    Filed: February 22, 2002
    Publication date: January 2, 2003
    Inventors: Seiya Sakurai, Yuuzou Muramatsu, Akihiro Matsufuji, Kenichirou Hatayama
  • Patent number: 6500877
    Abstract: The present invention discloses an ultraviolet light curable paint composition and method for applying and making such a composition to a substrate. Suitable substrates include glass, metals, and various plastics such as polycarbonates. The disclosed composition does not contain any significant amount of volatile organic solvents that do not become incorporated in the coating or are released to ambient after curing.
    Type: Grant
    Filed: September 25, 2000
    Date of Patent: December 31, 2002
    Assignee: Krohn Industries, Inc.
    Inventor: Roy C. Krohn
  • Patent number: 6498200
    Abstract: A cationically polymerizable resin composition which comprises (A) a compound containing at least one ring selected from the group consisting of an oxirane ring and an oxetane ring; (B) an onium salt; (C) an organic peroxide; and (D) an alkaline filler except for a hydroxide.
    Type: Grant
    Filed: January 11, 2000
    Date of Patent: December 24, 2002
    Assignee: Namics Corporation
    Inventors: Osamu Suzuki, Haruyuki Yoshii, Hisao Kondo, Kenichi Suzuki
  • Patent number: 6486225
    Abstract: A photocurable composition comprising (A) 100 parts by weight of a compound having an ethylenically unsaturated group, (B) from 0.001 to 5 parts by weight of a cationic dye having an absorption maximum wavelength in the wavelength region of from 400 to 1,200 nm represented by formula (1: D+·A1−  (1) wherein D+ represents a cation having an absorption maximum wavelength in the wavelength region of from 400 to 1,200 nm, and A1 31 represents an anion, and (C) from 0.
    Type: Grant
    Filed: November 17, 1999
    Date of Patent: November 26, 2002
    Assignee: Showa Denko Kabushiki Kaisha
    Inventors: Hirotoshi Kamata, Takeo Watanabe, Kazuhiko Ooga, Toshio Koshikawa
  • Publication number: 20020156142
    Abstract: A thermally-stable cationic photoinitiator capable of flash vaporization under vacuum and temperature conditions of an available flash-evaporation chamber is selected. The photoinitiator is mixed with a cation-polymerizable monomer and/or oligomer of interest and the mixture is flash evaporated and condensed in conventional manner as a film on a cold substrate. The resulting vacuum-deposited, homogeneous layer is cured with a high-energy radiation source that causes the cationic photoinitiator to liberate acidic species that catalyze the crosslinking of the monomer/oligomer compounds in its deposited film form. As a result of the homogeneous, pinhole-free nature of the vacuum deposition process, the thin-film polymer product does not suffer from the disadvantages attendant to prior-art atmospheric processes for cationically-cured polymers.
    Type: Application
    Filed: February 13, 2001
    Publication date: October 24, 2002
    Inventors: Michael G. Mikhael, Angelo Yializis
  • Patent number: 6468595
    Abstract: A thermally-stable cationic photoinitiator capable of flash vaporization under vacuum and temperature conditions of an available flash-evaporation chamber is selected. The photoinitiator is mixed with a cation-polymerizable monomer and/or oligomer of interest and the mixture is flash evaporated and condensed in conventional manner as a film on a cold substrate. The resulting vacuum-deposited, homogeneous layer is cured with a high-energy radiation source that causes the cationic photoinitiator to liberate acidic species that catalyze the crosslinking of the monomer/oligomer compounds in its deposited film form. As a result of the homogeneous, pinhole-free nature of the vacuum deposition process, the thin-film polymer product does not suffer from the disadvantages attendant to prior-art atmospheric processes for cationically-cured polymers.
    Type: Grant
    Filed: February 13, 2001
    Date of Patent: October 22, 2002
    Assignee: Sigma Technologies International, Inc.
    Inventors: Michael G. Mikhael, Angelo Yializis
  • Patent number: 6465541
    Abstract: Polymerizable composition that include: (a) a cationically active functional group; (b) an initiation system capable of initiating cationic polymerization of the cationically active functional group; and (c) a filler composition that includes various radiopacifying fillers in an amount sufficient to render the polymerizable composition radiopaque. Components (a), (b), and (c) are selected such that the polymerizable composition polymerizes to form a polymerized composition having a Barcol hardness, measured using a GYZJ-935 meter, of at least 10 within 30 minutes following initiation of the cationically active functional group are a reaction temperature of 25° C.
    Type: Grant
    Filed: July 3, 2001
    Date of Patent: October 15, 2002
    Assignee: 3M Innovative Properties Company
    Inventors: Kathyrn R. Bretscher, Richard P. Rusin, Sumita B. Mitra, Janis R. Gust, Cheryl A. Hayne, Dwight W. Jacobs, David A. Kaisaki
  • Patent number: 6465537
    Abstract: A photocurable composition is provided which can be produced and cured by both free-radical and cationic polymerization modes, which provides a sufficient length of open time to be bonded to an adherend, and which exhibts a good adhesive property. A photocurable composition containing a compound (A) having at least one free-radically polymerizable unsaturated bond in a molecule, a compound (B) having at least one epoxy group in a molecule, a free-radical polymerization catalyst (C), a cationic polymerization catalyst (D) and a compound (E) represented by the following formula (1).
    Type: Grant
    Filed: December 22, 2000
    Date of Patent: October 15, 2002
    Assignee: Sekisui Chemical Co., Ltd.
    Inventor: Hiroji Fukui
  • Patent number: 6458865
    Abstract: Photopolymerizable compositions are provided which are the reaction products of a vinyl ether, a photoinitiator system comprising an iodonium salt, a visible light sensitizer, and an electron donor compound. These monomeric/oligomeric compositions may also include epoxides, polyols, spiroorthocarbonates. One embodiment of the present invention is a polymerizable composition comprised of a vinyl ether, a spiroorthocarbonate, and a photoinitiator system. Another embodiment of the present invention is a polymerizable composition comprised of a vinyl ether, an epoxide, a polyol, and a photoinitiator system. Still another embodiment of the present invention is a polymerizable composition comprised of a vinyl ether, an epoxide, a polyol, a spiroorthocarbonate, and a photoinitiator system. Still further, another embodiment of the present invention is certain novel spiroorthocarbonate compounds. Each of these novel spiroorthocarbonate compounds include at least one epoxy group as a substituent.
    Type: Grant
    Filed: January 15, 1999
    Date of Patent: October 1, 2002
    Assignees: Curators of the University of Missouri, 3M Innovative Properties Company
    Inventors: Cecil C. Chappelow, Charles S. Pinzino, J. David Eick, Joel D. Oxman
  • Publication number: 20020132872
    Abstract: Photocurable resin composition for photofabrication of three-dimensional objects comprising
    Type: Application
    Filed: October 18, 2001
    Publication date: September 19, 2002
    Inventors: Tetsuya Yamamura, Yukitoshi Kato, Takayoshi Tanabe, Takashi Ukachi
  • Patent number: 6433035
    Abstract: Selectively colorable compositions and a method for forming selectively colored polymeric bodies using such compositions are disclosed. In accordance with the invention, a selectively colorable polymerizable composition comprising a leucobase color former is irradiated with light of a particular wavelength and specific intensity for a specified duration. Exposure to actinic radiation cures the composition and activates the color former. Exposure to higher dosages of actinic radiation can bleach the composition. The irradiation dosage can be varied to selectively color the polymeric body whereby the resultant color of any particular area depends on the exposure dose received at that location. By varying the dose, a polymeric body can be prepared having distinctly colored elements at specific locations.
    Type: Grant
    Filed: August 14, 2000
    Date of Patent: August 13, 2002
    Assignee: Spectra Group Limited, Inc.
    Inventors: Oleg V. Grinevich, Douglas C. Neckers
  • Patent number: 6420450
    Abstract: Cationically hardening masses are described, which can be stored and handled as single-component masses and comprise at least one difunctional cationically polymerizable compound; a photo-initiator for the cationic hardening based upon diaryliodonium salts; at least one compound containing an hydroxyl group; a compound releasing radicals when heated and having a half-life of one hour at a temperature of less than 100° C.; a photo-initiator forming radicals or of a photo-sensitizing agent for diaryliodonium salts; and from 0 to 60 parts by mass of modifier. The compounds are used for bonding, casting, sealing and coating of substrates.
    Type: Grant
    Filed: June 14, 2000
    Date of Patent: July 16, 2002
    Assignee: Delo Industrieklebstoffe GmbH & Co. KG
    Inventors: Dietmar Dengler, Michael Stumbeck
  • Patent number: 6368769
    Abstract: Novel aromatic sulfonium compounds of general formula (I), photoacid generators comprising the same, and photopolymerizable compositions containing the same, capable of providing stereolithographic resin compositions which do not suffer from the hindrance to curing by oxygen, can easily give shaped articles having desired sizes by virtue of the high accuracy thereof in curing, and can attain a satisfactory curing depth owing to the high sensitivity thereof for radiant energy; and a stereolithographic process.
    Type: Grant
    Filed: July 6, 2000
    Date of Patent: April 9, 2002
    Assignee: Asahi Denki Kogyo Kabushiki Kaisha
    Inventors: Kazuo Ohkawa, Hiroyuki Tachikawa, Satoyuki Chikaoka
  • Patent number: 6350792
    Abstract: A radiation-curable composition in a liquid or solid form comprises at least one solid, non-crystalline radiation-transmissible material, dispersed in at least one cationic-curable or free-radical curable composition or mixture thereof. The solid, non-crystalline radiation-transmissible materials comprise glasses and other suitable materials that transmit (i.e., are transparent to) at least about 40% of radiation having a wavelength from about 180 to about 600 nanometers. The solid forms of the radiation-curable compositions of the invention are useful as powder coatings for coating decorative and functional objects and that would be cured by a thermal heating flow process followed by radiation exposure. The cured compositions of the invention are useful as coatings and inks for metal, paper, plastics, glass, ceramics, and wood, as adhesives, as sealants, and as composite materials and other articles and in biomedical and dental applications.
    Type: Grant
    Filed: July 13, 2000
    Date of Patent: February 26, 2002
    Assignee: Suncolor Corporation
    Inventors: David A. Smetana, Joseph V. Koleske
  • Publication number: 20020013380
    Abstract: Photopolymerizable compositions are provided which are the reaction products of a vinyl ether, a photoinitiator system comprising an iodonium salt, a visible light sensitizer, and an electron donor compound. These monomeric/oligomeric compositions may also include epoxides, polyols, spiroorthocarbonates. One embodiment of the present invention is a polymerizable composition comprised of a vinyl ether, a spiroorthocarbonate, and a photoinitiator system. Another embodiment of the present invention is a polymerizable composition comprised of a vinyl ether, an epoxide, a polyol, and a photoinitiator system. Still another embodiment of the present invention is a polymerizable composition comprised of a vinyl ether, an epoxide, a polyol, a spiroorthocarbonate, and a photoinitiator system.
    Type: Application
    Filed: January 15, 1999
    Publication date: January 31, 2002
    Inventors: CECIL C. CHAPPELOW, CHARLES S. PINZINO, J. DAVID EICK, JOEL D. OXMAN
  • Patent number: 6342333
    Abstract: A photosensitive resin composition comprising an aromatic polyimide precursor, wherein a 10 &mgr;m thick layer of precursor has light transmittance at a wavelength of 365 nm of at least 1% and a 10 &mgr;m thick polyimide film made from the resin composition by imidation ring closure and deposited on a silicon substrate results in a residual stress of at most 25 MPa. The composition can be patterned through i-line exposure followed by development with alkaline solutions, and can be imidized into low-stress polyimide patterns. Electronic components having the polyimide patterns have high reliability.
    Type: Grant
    Filed: September 23, 1999
    Date of Patent: January 29, 2002
    Assignees: Hitachi Chemical DuPont Microsystems, L.L.C., Hitachi Chemical DuPont Microsystems, Ltd.
    Inventors: Akihiro Sasaki, Noriyoshi Arai, Makoto Kaji, Toshiki Hagiwara, Brian C. Auman
  • Patent number: 6319603
    Abstract: A liquid curable resin composition comprising (1) a (meth)acrylate polymer having a weight average molecular weight relative to polystyrene standard of at least about 5,000, (2) a ring-opening polymerizable monomer containing at least one epoxy group, and (3) a cationic photopolymerization initiator is disclosed. The composition produces cured products which exhibit superior heat resistance, excellent mechanical strength, and superb adhesive characteristics, and is suitable for use as a photo-curable adhesive, a photo-curable sealing material, a resin for optical three-dimensional molding, and a coating material for optical fibers, and optical fiber ribbon matrix.
    Type: Grant
    Filed: March 2, 1999
    Date of Patent: November 20, 2001
    Assignees: DSM N.V., JSR Corporation, Japan Fine Coatings Co., Ltd.
    Inventors: Zen Komiya, Yoshikazu Yamaguchi, Tsuyoshi Watanabe, Takashi Ukachi
  • Patent number: 6306926
    Abstract: Polymerizable compositions that include: (a) a cationically active functional group; (b) an initiation system capable of initiating cationic polymerization of the cationically active functional group; and (c) a filler composition that includes various radiopacifying fillers in an amount sufficient to render the polymerizable composition radiopaque. Components (a), (b), and (c) are selected such that the polymerizable composition polymerizes to form a polymerized composition having a Barcol hardness, measured using a GYZJ-935 meter, of at least 10 within 30 minutes following initiation of the cationically active functional group at a reaction temperature of 25° C.
    Type: Grant
    Filed: October 7, 1998
    Date of Patent: October 23, 2001
    Assignee: 3M Innovative Properties Company
    Inventors: Kathyrn R. Bretscher, Richard P. Rusin, Bradley D. Craig, Sumita B. Mitra, Joel D. Oxman, Janis R. Gust, Cheryl A. Hayne, James W. Westberg, Matthew C. Trom, Brant U. Kolb, Dwight W. Jacobs, David A. Kaisaki, James A. Baker
  • Patent number: 6262147
    Abstract: The present invention provides a thermosetting organic solvent type coating capable of forming a cured coating film having a TUKON hardness at 20° C. of 15 or more and the minimum value of dynamic modulus E′ at a frequency of 110 Hz in the temperature range of 150-200° C., of 1×109 dyn/cm2 or more. The cured film formed from the coating, as compared with the cured films formed from conventional organic solvent type coatings used as a top coat for automobile (e.g. an organic solvent type coating containing, as main components, a hydroxyl group-containing acrylic resin and a melamine resin, or a carboxylic-epoxy type coating), is at least equivalent in weatherability, finish appearance, acid resistance, etc. and superior in stain resistance.
    Type: Grant
    Filed: August 26, 1999
    Date of Patent: July 17, 2001
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Satoshi Ikushima, Seiji Wada, Yasumasa Okumura, Haruhiko Aida, Motoshi Yabuta, Yoshiyuki Yukawa, Ken-ichi Hasada
  • Patent number: 6248804
    Abstract: Radiation curing of inks on game balls, golf balls and the like is disclosed. The radiation used is ultraviolet and/or visible light. Production inks, logo inks and methods for forming production prints and logos on golf balls, game balls and the like are disclosed. To ensure that the ink is sufficiently through-cured, visible light photoinitiators are added to the ink. In addition, co-initiators and ultraviolet light photoinitiators can also be included in the ink. To form a radiation curable water-insoluble production ink, at least an adhesion promoting component is added to an ink base. The adhesion promoting component is sufficient to maintain adhesion of the production ink of at least about 75% of the inked surface to the topcoat and to the surface of the game ball or the golf ball after radiation curing and after coating the production ink with the topcoat. To form radiation curable water-insoluble logo ink, at least a toughening agent is added to an ink base.
    Type: Grant
    Filed: January 20, 1998
    Date of Patent: June 19, 2001
    Assignee: Acushnet Company
    Inventor: Mitchell E. Lutz
  • Patent number: 6245827
    Abstract: This invention is of a resin composition including an additive of one or more organic peroxide thermal imitators to cationic photoinitiators, that are sensitized with alpha-hydroxy-ketones, which composition provides a self-propagating thermal curing reaction first activated by a short duration of surface ultraviolet radiation. The thermal reaction is non-directional, thus eliminating the line of sight limitation of current radiation curing processes. Complete curing can be achieved of the composition in a very short time; often after only a few minutes or less. The activation period can be provided by only a few seconds of ultraviolet light using a wide variety of commercial ultraviolet light sources.
    Type: Grant
    Filed: October 12, 1999
    Date of Patent: June 12, 2001
    Assignee: Elementis Specialties, Inc.
    Inventor: Scott Gregory
  • Patent number: 6235807
    Abstract: A curing process for cationically polymerisable monomers, which comprises applying a composition comprising: (a) at least one cationically polymerisable monomer, (b) as photoinitiator at least one iodonium salt containing an SbF6, PF6 or BF4 anion, (c) one pigment, and (d) at least one sensitiser, to a substrate, irradiating it with light having a wavelength of 200-600 nm and then heat-postcuring it, is distinguished by little yellowing of the cured formulation.
    Type: Grant
    Filed: December 14, 1998
    Date of Patent: May 22, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventor: Ljubomir Misev
  • Patent number: 6217984
    Abstract: An energy sensitive composition comprising a monomeric organometallic complex essentially free of nucleophilic groups and which, upon exposure to energy, bonds to basic reactive sites on a substrate via the metal center, leaving the polymerizable group of the complex unreacted and unrestricted; an energy sensitive composition at least one energy sensitive organometallic group is incorporated in or appended to the backbone of a polymer, such that the resulting coordinatively unsaturated organometallic group or groups bond to basic reactive sites on a substrate, thus forming permanent bonds, and further, the adherent compositions are useful in applications such as adhesion of polymers to substrates, protective coatings, printing plates, durable release coatings, primers, binders, and paints.
    Type: Grant
    Filed: May 21, 1992
    Date of Patent: April 17, 2001
    Assignee: 3M Innovative Properties Company
    Inventors: Wesley J. Bruxvoort, Steven J. Keipert, Fred B. McCormick, Jerry W. Williams, Bradford B. Wright
  • Patent number: 6211260
    Abstract: A photocurable paint composition for road markings is disclosed, comprising (A) a compound having an ethylenically unsaturated group, (B) a filler, (C) a cationic dye represented by formula (1): D+&Circlesolid;A1−  (1) (wherein D+ represents a cation having an absorption maximum wavelength in the wavelength region of from 400 to 1,200 nm, and A1− represents an optional anion), (D) a quaternary organic borate-type sensitizer represented by formula (2): (wherein R1, R2, R3 and R4 each independently represents an alkyl group, an aryl group, an aralkyl group, an alkenyl group, an alkynyl group, a silyl group, a heterocyclic group or a halogen atom, and Z+ represents an optional cation) and (E) an ultraviolet radical polymerization initiator capable of generating a radical upon absorption of light at a wavelength of 400 nm or less, or additionally comprising (F) glass beads.
    Type: Grant
    Filed: November 4, 1998
    Date of Patent: April 3, 2001
    Assignee: Showa Denko K.K.
    Inventors: Kenichi Nakamura, Hirotoshi Kamata, Toshio Koshikawa, Shuichi Sugita
  • Patent number: 6200728
    Abstract: The invention provides new photoresist compositions that contain a resin binder and a blend of photoacid generators. Photoacid generator blends of the invention produce photoacids that differ in acid strength and/or size.
    Type: Grant
    Filed: February 20, 1999
    Date of Patent: March 13, 2001
    Assignee: Shipley Company, L.L.C.
    Inventors: James F. Cameron, James Michael Mori, George W. Orsula, James W. Thackeray