Two Or More Hetero Atoms In Hetero Ring At Least One Of Which Is Oxygen Patents (Class 522/169)
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Patent number: 8980971Abstract: A photocurable resin composition for three-dimensional photofabrication operations, including stereolithography, comprising (A) a cationically polymerizable compound having two or more bisphenol structures and one or more hydroxyl groups, (B) a cationically polymerizable compound other than the component (A), (C) a cationic photoinitiator, (D) a radically polymerizable compound, (E) a radical photoinitiator, and (F) multilayer polymer particles having a core and a shell layer, the shell layer containing functional group-modified rubber polymer particles having at least one reactive functional group.Type: GrantFiled: May 21, 2013Date of Patent: March 17, 2015Assignee: DSM IP Assets B.V.Inventors: Masahiro Ueda, Katsuyuki Takase, Takahiko Kurosawa
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Publication number: 20140349086Abstract: The present invention provides a photo-curable composition that requires a small demolding force. The present invention also provides a UV imprint method that requires a small demolding force. The photo-curable composition contains a polymerizable monomer (A), a polymerization initiator (B), and a fluorine-containing surfactant (C). A photo-cured product of the photo-curable composition has a water contact angle of 74 degrees or less.Type: ApplicationFiled: October 24, 2012Publication date: November 27, 2014Applicant: CANON KABUSHIKI KAISHAInventors: Toshiki Ito, Chieko Mihara, Kanae Kawahata, Motoki Okinaka
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Patent number: 8841064Abstract: Disclosed are a positive photosensitive resin composition that includes (A) an alkali soluble resin; (B) a dissolution controlling agent including the compound represented by Chemical Formula 6; (C) a photosensitive diazoquinone compound; (D) a silane compound; and (E) a solvent, and a photosensitive resin film prepared by using the same.Type: GrantFiled: November 11, 2011Date of Patent: September 23, 2014Assignee: Cheil Industries Inc.Inventors: Myoung-Hwan Cha, Jong-Hwa Lee, Mi-Ra Im, Min-Kook Chung, Ji-Young Jeong, Hyun-Yong Cho, Hwan-Sung Cheon
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Patent number: 8815970Abstract: A method of preparing polyurethane prepolymer does not require using a toxic isocyanate monomer (manufactured by harmful phosgene) as a raw material. Epoxy resin and carbon dioxide are used as major raw materials to form cyclic carbonates to be reacted with a functional group oligomer, and then amino groups in a hydrophilic (ether group) or hydrophobic (siloxane group) diamine polymer are used for performing a ring-opening polymerization, and the microwave irradiation is used in the ring-opening polymerization to efficiently synthesize the amino-terminated PU prepolymer, and then an acrylic group at an end is added to manufacture an UV cross-linking PU (UV-PU) oligomer which can be coated onto a fabric surface, and the fabric is dried by UV radiation for a surface treatment to form a washing-resisted long lasting hydrophilic or hydrophobic PU fabric.Type: GrantFiled: September 22, 2011Date of Patent: August 26, 2014Assignee: Tamkang University (A University of Taiwan)Inventors: Jing-Zhong Hwang, Guei-Jia Chang, Jhong-Jheng Lin, Cheng-Wei Tsai, Shih-Chieh Wang, Po-Cheng Chen, Kan-Nan Chen, Kan-Nan Chen
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Patent number: 8785515Abstract: Polycyclic aromatic compounds of formula (I) having at least two conjugated aromatic rings at least one of which has a substituent comprising a cyclic carbonate group can be used as sensitizers for cationic photoinitiators, especially iodonium compounds, and may also function as monomers in cationically initiated radiation curable compositions, especially coating compositions, such as printing inks and varnishes.Type: GrantFiled: May 9, 2008Date of Patent: July 22, 2014Assignee: Sun Chemical CorporationInventors: Shaun Lawrence Herlihy, Robert Stephen Davidson
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Patent number: 8697134Abstract: Described is a direct method for the fabrication of resorcinarene nanocapsules by photopolymerization of compounds of formula (I), such as resorcinarene tetraalkene tetrathiol (RTATT), in the absence of any template or preorganization. Further, by varying the polymerization media, a variety of other polymeric architectures like lattices, fibrous networks, and nanoparticles were obtained. The morphology and structure were characterized by transmission electron microscopy, energy dispersive spectroscopy, scanning electron microscopy, dynamic light scattering, infrared and nuclear magnetic resonance spectroscopy. These morphologically distinct resorcinarene polymeric architectures contain residual thiol and ene functional groups offering potential functionalization opportunities.Type: GrantFiled: June 21, 2011Date of Patent: April 15, 2014Assignee: Old Dominion University Research FoundationInventors: Ramjee Balasubramanian, Zaharoula M. Kalaitzis, Srujana Prayakarao
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Patent number: 8436066Abstract: Compositions that can be polymerized and/or crosslinked into coatings by cationic and/or radical irradiation contain at least one photoinitiator and at least one compound having at least one isocyanate function.Type: GrantFiled: July 23, 2007Date of Patent: May 7, 2013Assignee: Vencorex FranceInventors: Jean-Marc Frances, Philippe Barbeau, Jean-Marie Bernard, Damien Bourgeois
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Publication number: 20130010039Abstract: The present invention provides a photocurable ink composition for ink jet recording with excellent curability. The photocurable ink composition for ink jet recording includes polymerizable compounds, a photopolymerization initiator, and a colorant, wherein the polymerizable compounds include a vinyl ether group-containing (meth)acrylate represented by general formula (I): CH2?CR1—COOR2—O—CH?CH—R3??(I) (wherein R1 is a hydrogen atom or a methyl group, R2 is a divalent organic residue having 2 to 20 carbon atoms, and R3 is a hydrogen atom or a monovalent organic residue having 1 to 11 carbon atoms) and phenoxyethyl (meth)acrylate.Type: ApplicationFiled: July 9, 2012Publication date: January 10, 2013Applicant: SEIKO EPSON CORPORATIONInventors: Hiroaki Kida, Hiroshi Fukumoto, Toru Saito, Keitaro Nakano, Hiroki Nakane
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Publication number: 20130004677Abstract: A method of preparing polyurethane prepolymer does not require using a toxic isocyanate monomer (manufactured by harmful phosgene) as a raw material. Epoxy resin and carbon dioxide are used as major raw materials to form cyclic carbonates to be reacted with a functional group oligomer, and then amino groups in a hydrophilic (ether group) or hydrophobic (siloxane group) diamine polymer are used for performing a ring-opening polymerization, and the microwave irradiation is used in the ring-opening polymerization to efficiently synthesize the amino-terminated PU prepolymer, and then an acrylic group at an end is added to manufacture an UV cross-linking PU (UV-PU) oligomer which can be coated onto a fabric surface, and the fabric is dried by UV radiation for a surface treatment to form a washing-resisted long lasting hydrophilic or hydrophobic PU fabric.Type: ApplicationFiled: September 22, 2011Publication date: January 3, 2013Inventors: Jing-Zhong HWANG, Guei-Jia CHANG, Jhong-Jheng LIN, Cheng-Wei TSAI, Shih-Chieh WANG, Po-Cheng CHEN, Kan-Nan CHEN, Jen-Taut YEH
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Publication number: 20120288686Abstract: A multi-layer stack for imprint lithography is formed by applying a first polymerizable composition to a substrate, polymerizing the first polymerizable composition to form a first polymerized layer, applying a second polymerizable composition to the first polymerized layer, and polymerizing the second polymerizable composition to form a second polymerized layer on the first polymerized layer. The first polymerizable composition includes a polymerizable component with a glass transition temperature less than about 25° C., and the first polymerized layer is substantially impermeable to the second polymerizable composition.Type: ApplicationFiled: July 11, 2012Publication date: November 15, 2012Applicant: MOLECULAR IMPRINTS, INC.Inventors: Frank Y. Xu, Weijun Liu, Cynthia B. Brooks, Dwayne L. LaBrake, David J. Lentz
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Patent number: 8303860Abstract: A colored curable composition including: (A) a pigment dispersion containing (a-1) a pigment, (a-2) a compound having a pigment mother nucleus structure and an amino group in a molecule, and (a-3) a resin having an acid group and a polymerizable group; (B) an oxime ester initiator; and (C) a polymerizable compound.Type: GrantFiled: March 5, 2009Date of Patent: November 6, 2012Assignee: FUJIFILM CorporationInventors: Kazuto Shimada, Atsushi Sugasaki
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Patent number: 8236872Abstract: A photocationically polymerizable adhesive composition and an optical member, the photocationically polymerizable adhesive composition including about 75 to about 99.8 parts by weight of a compound including one of aliphatic epoxy, alicyclic epoxy, oxetane, and vinyl ether compounds, about 0.1 to about 5 parts by weight of a titanate coupling agent, and about 0.1 to about 20 parts by weight of a photopolymerization initiator, wherein a sum of weights of the compound, the titanate coupling agent, and the photopolymerization initiator is 100 parts by weight.Type: GrantFiled: April 22, 2011Date of Patent: August 7, 2012Assignee: Cheil Industries, Inc.Inventors: Cheong Hun Song, Hiroshi Ogawa, Tatsuhiro Suwa
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Patent number: 8192821Abstract: Disclosed is an ultraviolet-curable resin composition for multilayer optical discs, which contains (A) dioxane glycol di(meth)acrylate and/or tricyclodecane dimethylol di(meth)acrylate, and (B) a photopolymerization initiator.Type: GrantFiled: July 9, 2007Date of Patent: June 5, 2012Assignee: Nippon Kayaku Kabushiki KaishaInventors: Daisuke Kobayashi, Kiyohisa Tokuda, Masahiro Naito, Go Mizutani
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Patent number: 8129447Abstract: The invention provides an ink composition including (i) a sensitizing dye having a polymerizable group as a substituent, (ii) a polymerization initiator and (iii) a polymerizable compound having an ethylenically unsaturated bond. The invention also provides an inkjet recording method and a polymerizable compound useful as a sensitizing dye. The sensitizing dye (i) is represented by Formula (I) or (II) below. In the formulae, X represents O, S, NRa, or NRb, n1 and n2 each represent 0 or 1, Ra, Rb, and R1 to R18 each represent a hydrogen atom or a monovalent substituent, and one polymerizable group is present in the molecule.Type: GrantFiled: September 9, 2008Date of Patent: March 6, 2012Assignee: Fujifilm CorporationInventors: Tokihiko Matsumura, Tsutomu Umebayashi
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Publication number: 20110311639Abstract: Described is a direct method for the fabrication of resorcinarene nanocapsules by photopolymerization of compounds of formula (I), such as resorcinarene tetraalkene tetrathiol (RTATT), in the absence of any template or preorganization. Further, by varying the polymerization media, a variety of other polymeric architectures like lattices, fibrous networks, and nanoparticles were obtained. The morphology and structure were characterized by transmission electron microscopy, energy dispersive spectroscopy, scanning electron microscopy, dynamic light scattering, infrared and nuclear magnetic resonance spectroscopy. These morphologically distinct resorcinarene polymeric architectures contain residual thiol and ene functional groups offering potential functionalization opportunities.Type: ApplicationFiled: June 21, 2011Publication date: December 22, 2011Applicant: Old Dominion University Research FoundationInventors: Ramjee Balasubramanian, Zaharoula M. Kalaitzis, Srujana Prayakarao
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Patent number: 8030368Abstract: Photoinitiated reactions especially in photopolymer technology, as well as photoinitiated color forming reactions are achievable by applying a reactive substrate selected from a polymerisable and/or crosslinkable composition and a color changing substance to a support, activating a latent photoinitiator applied with the reactive substance and subsequently exposing the reactive substrate with the resulting photoinitiator therein to photoreaction conditions wherein actinic radiation causes the substrate to undergo polymerization and/or crosslinking or color change respectively, the substrate being locally modified in its constitution as a result of its exposure to actinic radiation at least one stage of the method, so that the resulting polymerised and/or crosslinked composition or color changed substance corresponds in its distribution on the support to the locations of the modification of the substrate.Type: GrantFiled: December 22, 2006Date of Patent: October 4, 2011Assignee: Lintfield LimitedInventor: Grant Bradley
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Patent number: 7888401Abstract: An active energy ray-curable ink composition, which contains a compound having, in its molecule, an oxetane ring and at least one selected from a dioxolane ring, a dioxane ring, and a dioxepane ring; an ink composition, which contains a cationically-polymerizable compound having, in its molecule, both an oxetane ring and a bicycloorthoester ring; an inkjet ink, which contains the active energy ray-curable ink composition or the ink composition; and an image-forming method and a recorded material, using the inkjet ink; an oxetane compound of a specific structure.Type: GrantFiled: July 27, 2007Date of Patent: February 15, 2011Assignee: FUJIFILM CorporationInventors: Hisato Nagase, Takehiko Sato
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Publication number: 20100285282Abstract: The invention describes a radiation-curable ink jet ink, which comprises at least 50% by weight of cyclic trimethyllolpropane formal acrylate (CTFA), and further comprises a free-radical photoinitiator, and which is substantially free of volatile compounds.Type: ApplicationFiled: September 15, 2008Publication date: November 11, 2010Inventors: Hartley David Selman, Graeme Edward Charles Beats, Nigel Anthony Caiger, Andrew David Speirs, Stephen Paul Wilson
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Publication number: 20100144917Abstract: The invention is to provide an epoxy compound or an actinic energy radiation hardenable composition each having high safety and stability, and to provide an actinic energy radiation hardenable composition with excellent photo-hardenability under high humidity, which gives high solvent resistance, high water proof and a hardened layer with high strength. There is provided an actinic energy radiation hardenable composition containing an epoxy compound represented by the following formula (1).Type: ApplicationFiled: July 12, 2006Publication date: June 10, 2010Applicant: KONICA MINOLTA MEDICAL & GRAPHIC, INC.Inventor: Nobumasa Sasa
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Patent number: 7718111Abstract: 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 0groups per 100 grams of said composition.Type: GrantFiled: April 11, 2007Date of Patent: May 18, 2010Assignee: Huntsman Advanced Materials Americas Inc.Inventors: David L. Johnson, Frank Tran, John Fong, Richard Leyden, Ranjana Patel
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Patent number: 7544721Abstract: A photosensitive adhesive composition of the polymerizable resin type, the hardening of which occurs by polymerization and/or reticulation, includes:—initiators for at least one chain polymerization reaction to guarantee the hardening of the composition and a sufficient quantity of at least one bifunctional monomer, including a photolabile center with at least one photolabile entity and at least two polymerizable units, connected by covalent skeletons to the photolabile center and located away from the cleavage sites of the photolabile center, such that the composition loses the integrity and adhesivity thereof under the influence of a reticulating radiation causing the cleavage of the photolabile sites. The composition is particularly of application in dentistry.Type: GrantFiled: April 2, 2003Date of Patent: June 9, 2009Assignee: Produits Dentaires Pierre RollandInventors: Vincent Gaud, Yves Gnanou, Jean-Pierre Desvergne, Francis Dieras, Alexandrine Roubiere
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Publication number: 20090142606Abstract: A process for the polymerization and/or crosslinking of an organic coating composition is provided. The process involves employing an organic coating composition which can crosslink and/or polymerize under irradiation with short-wave ultraviolet (UV C) radiation with a wavelength of between 200 and 280 nm.Type: ApplicationFiled: September 13, 2006Publication date: June 4, 2009Applicant: Bluestar Silicones FranceInventor: Christian Mirou
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Publication number: 20090142507Abstract: An ink composition for inkjet recording is provided. The ink composition contains (a) a monomer containing a fluorinated alkylene group and two or more polymerizable groups, (b) a photo initiator, and (c) a polymerizable monomer.Type: ApplicationFiled: November 20, 2008Publication date: June 4, 2009Applicant: FUJIFILM CORPORATIONInventors: Kazuhiro Yokoi, Taiji Katsumata
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Patent number: 7541391Abstract: Disclosed is an optical device structure comprising a low shrinkage mixture wherein the shrinkage of the mixture is limited after the curing of the mixture during optical device formation. Disclosed also are methods for forming optical devices which comprise the low shrinkage mixture.Type: GrantFiled: September 2, 2005Date of Patent: June 2, 2009Assignee: General Electric CompanyInventors: Thomas Bert Gorczyca, Renato Guida, Kung-Li Justin Deng, Hua Xia
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Patent number: 7538145Abstract: The phase change, curable composition comprises curable monomer, photoinitiator that initiates polymerization of the curable monomer, and phase change agent that provides the composition with an increase in viscosity of at least four orders of magnitude, from a first temperature, the first temperature being from 50° C. to 130° C., to a second temperature, the second temperature being from 0° C. to 70° C., wherein the second temperature is at least 10° C. below the first temperature. A coating over an image may be applied by providing a composition comprising curable monomer at a first temperature; applying the composition over the image, the image being at a second temperature; and exposing the composition to radiation to initiate polymerization of the curable monomer. In this process, the composition has a viscosity at the second temperature that is at least four orders of magnitude greater than its viscosity at the first temperature.Type: GrantFiled: November 30, 2005Date of Patent: May 26, 2009Assignee: Xerox CorporationInventors: Jennifer L. Belelie, Peter G. Odell, Darly Vanbesien, Marcel P. Breton
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Publication number: 20090053535Abstract: A multi-layer stack for imprint lithography is formed by applying a first polymerizable composition to a substrate, polymerizing the first polymerizable composition to form a first polymerized layer, applying a second polymerizable composition to the first polymerized layer, and polymerizing the second polymerizable composition to form a second polymerized layer on the first polymerized layer. The first polymerizable composition includes a polymerizable component with a glass transition temperature less than about 25° C., and the first polymerized layer is substantially impermeable to the second polymerizable composition.Type: ApplicationFiled: August 22, 2008Publication date: February 26, 2009Applicant: Molecular Imprints, Inc.Inventors: Frank Y. Xu, Weijun Liu, Cynthia B. Brooks, Dwayne L. LaBrake, David J. Lentz
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Patent number: 7485672Abstract: The present invention relates to a process comprising polymerizing via irradiation from a light source, a reaction mixture comprising at least one monomer and at least one photoinitiator wherein at least about 90% of incident light emitted by the light source is filtered to produce a soluble, high molecular weight polymer.Type: GrantFiled: October 19, 2004Date of Patent: February 3, 2009Assignee: Johnson & Johnson Vision Care, Inc.Inventors: Frank Molock, David C. Turner, Shivkumar Mahadevan, Joseph Hepting
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Publication number: 20090009061Abstract: The object of the present invention is to provide a composition for conductive materials from which a conductive layer having a high carrier transport ability can be made, a conductive material formed of the composition and having a high carrier transport ability, a conductive layer formed using the conductive material as a main material, an electronic device provided with the conductive layer and having high reliability, and electronic equipment provided with the electronic device.Type: ApplicationFiled: July 27, 2005Publication date: January 8, 2009Inventors: Yuji Shinohara, Koichi Terao, Takashi Shinohara
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Patent number: 7417074Abstract: There is disclosed an ink jet recording apparatus comprising a color ink container having a capacity V1 accommodating therein a solvent polymerizable in the presence of an acid and a colorant, a reaction liquid container having a capacity V2 (V2<V1) accommodating therein a reaction liquid comprising a solvent, and a photo-acid generating agent capable of generating an acid when irradiated with light, an stirring container mixing the color ink and the reaction liquid at a mixing ratio of S1:S2 (the color ink:the reaction liquid) to prepare a recording ink, a color ink supply means feeding the color ink to the stirring container, a reaction liquid supply means feeding the reaction liquid to the stirring container, an ink jet recording head ejecting the recording ink to a recording medium, and a supply tube feeding the recording ink to the recording head.Type: GrantFiled: March 22, 2004Date of Patent: August 26, 2008Assignees: Toshiba Tec Kabushiki Kaisha, Kabushiki Kaisha ToshibaInventors: Masashi Hiroki, Kazuhiko Ohtsu, Yoshito Endo, Toru Ushirogouchi, Ryozo Akiyama
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Patent number: 7378457Abstract: The present invention provides radiation curable resin compositions having enhanced low temperature flexibility and to methods of using these compositions. The radiation curable resin compositions contain no or essentially no volatile organic components (VOCs), and find particular use as coating compositions. In particular, the radiation curable resin compositions of this invention comprise a vinyl dioxolane end-capped oligomer blended with a photoinitiator.Type: GrantFiled: March 9, 2005Date of Patent: May 27, 2008Assignee: Foster Miller, Inc.Inventors: Robert F. Kovar, Nese Orbey
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Patent number: 7232850Abstract: 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: GrantFiled: October 3, 2003Date of Patent: June 19, 2007Assignee: Huntsman Advanced Materials Americas Inc.Inventors: David Johnson, Frank Tran, John Fong, Richard Leyden, Ranjana Patel
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Patent number: 7232852Abstract: A visible light cationically photopolymerizable composition is provided. This composition includes an expanding monomer and a dioxirane. More specifically, the expanding monomer used in this composition is one or more dioxiranyl tetraoxaspiro[5.5]undecanes. The composition of the present invention may be used as a matrix resin for dental restorative materials. Another embodiment of the present invention is various novel dioxiranyl tetraoxaspiro[5.5]undecanes.Type: GrantFiled: February 20, 2004Date of Patent: June 19, 2007Assignee: Curators of the University of MissouriInventors: Cecil C. Chappelow, Charles S. Pinzino, J. David Eick, Andrew J. Holder, Shin-Shi Chen, Li Jeang
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Patent number: 7217743Abstract: A curable ink for jet-ink recording comprising a white pigment and a polymerizable compound, wherein the polymerizable compound is a compound selected from the group consisting of: (a) oxetane compounds; (b) pyrrole or substituted pyrroles; (c) aniline or substituted anilines; and (d) thiophene or an substituted thiophenes, provided that when the polymerizable compound is the oxetane compound, the curable ink further comprises an epoxy compound or a vinyl ether compound.Type: GrantFiled: July 21, 2003Date of Patent: May 15, 2007Assignee: Konica CorporationInventor: Ai Kondo
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Patent number: 7169829Abstract: The present invention provides (meth)acrylate compounds bearing a specific maleimide group and resin compositions containing said compounds that can be cured by irradiation of light in a practical dose even when a photoinitiator is not used or used in a smaller amount than that of the prior art, and cured articles of the resin compositions.Type: GrantFiled: December 26, 2002Date of Patent: January 30, 2007Assignee: Nippon Kayaku Kabushiki KaishaInventors: Toru Ozaki, Hiroo Koyanagi, Minoru Yokoshima
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Patent number: 7098258Abstract: The heat-curable resin composition of the present invention comprises an epoxy-containing resin and a curing agent, wherein the curing agent is cyclohexanetricarboxylic acid and/or an anhydride thereof. The heat-curable resin composition exhibits an excellent curability without using an curing accelerator and provides a colorless transparent cured product which is little discolored under high-temperature conditions and irradiation conditions of high-energy light. The heat-curable resin composition is suitable for producing coating compositions, adhesives, shaped articles, protective films for color filters and sealing materials for photosemiconductors such as blue LED and white LED.Type: GrantFiled: June 30, 2004Date of Patent: August 29, 2006Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Ryuji Ideno, Takeshi Koyama, Masami Okuo
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Patent number: 6916855Abstract: The invention relates to a radiation curable composition comprising radiation curable components wherein at least one component of the radiation curable composition contains a functional group which, when attached to an acrylate group has a calculated Boltzmann average dipole moment of higher than 3.5 Debye. The invention further relates to radiation curable optical fiber coating compositions having a high dielectric constant.Type: GrantFiled: November 21, 2001Date of Patent: July 12, 2005Assignee: DSM IP Assets B.V.Inventors: Johan F. G. A. Jansen, Aylvin J. A. A. Dias, Marko Dorschu, Betty B Coussens
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Patent number: 6894084Abstract: The present invention provides radiation curable resin compositions that contain no or essentially no volatile organic components (VOCs), and to methods of using these compositions. The radiation curable resin compositions find particular use as coating compositions. In particular, the radiation curable resin compositions of this invention comprise a vinyl dioxolane end-capped oligomer blended with a photoinitiator.Type: GrantFiled: February 12, 2001Date of Patent: May 17, 2005Assignee: Foster-Miller, Inc.Inventors: Robert F. Kovar, Nese Orbey, Stanley Wentworth
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Patent number: 6844375Abstract: The invention relates to: 4-methylene-1,3-dioxolanes of the general formula (I) wherein R1 denotes hydrogen, C5-C6-cycloalkyl or C1-C4-alkyl; m and n, which may be the same or different, denote 0 or 1, whereby m?n, o denotes 2, 3 or 4 depending on the valency of the group X; and X denotes a C—C single bond, straight-chain or branched C1-C18-alkylene, C5-C6-cycloalkylene, C8-C18-arylalkylene, —CH2(OCH2CH2)pOCH2—, —CH2(OCH(CH3)CH2)pOCH2—, wherein p is an integer from 0 to 100; a process for their production; and intermediate products used. Moreover, compositions capable of emission-free, photocationic cross-linking, which comprise 4-methylene-1,3-dioxolanes of the general formula (I) and their use for the production of solvent-resistant and transparent films.Type: GrantFiled: August 23, 2001Date of Patent: January 18, 2005Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Helmut Hartl, Rainer B. Frings, Gerwald F. Grahe
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Patent number: 6777458Abstract: A process for producing scratch-resistant coatings, encompassing the following steps: applying at least one UV-curable coating composition to at least one surface of an article to be coated, said coating composition comprising at least one polymer and/or oligomer P1 containing on average at least one ethylenically unsaturated double bond per molecule, and curing the coating composition by exposure to UV radiation, which comprises conducting the curing of the coating composition under an oxygen-containing protective gas which has an oxygen partial pressure in the range from 0.2 to 18 kPa.Type: GrantFiled: February 25, 2002Date of Patent: August 17, 2004Assignee: BASF AktiengesellschaftInventors: Thomas Jaworek, Reinhold Schwalm, Rainer Königer, Reiner Kranwetvogel
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Patent number: 6689463Abstract: The present invention relates to a composition for coating optical fibers that includes a UV curable coating composition. The composition includes at least one component having at least one heterocyclic moiety capable of undergoing ring opening polymerization. The composition may also include at least one acrylate functional end group. The acrylate functional group may be on the same component as the heterocyclic moiety or on a second component. The cured composition has a Young's Modulus of at least about 100 MPa.Type: GrantFiled: December 18, 2001Date of Patent: February 10, 2004Assignee: Corning IncorporatedInventors: Kevin Y Chou, Michelle D Fabian, Jun Hou, Gregory F Jacobs, David N Schissel, Huan-Hung Sheng
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Patent number: 6653486Abstract: 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: GrantFiled: September 4, 2002Date of Patent: November 25, 2003Assignee: Curators of the University of MissouriInventors: Cecil C. Chappelow, Charles S. Pinzino, J. David Eick
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Patent number: 6649668Abstract: 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: GrantFiled: June 15, 2000Date of Patent: November 18, 2003Inventors: Marie-Anne David, Jean-Marc Frances
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Patent number: 6610759Abstract: 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: GrantFiled: March 6, 2000Date of Patent: August 26, 2003Assignees: Curators of the University of Missouri, 3M Innovative Properties CompanyInventors: Cecil C. Chappelow, Charles S. Pinzino, J. David Eick, James Code, Joel D. Oxman, Sharon M. Rozzi
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Patent number: 6592801Abstract: A process for polymerizing episulfide monomers comprising the steps of: (c) mixing to an episulfide monomer or a mixture of episulfide monomers an effective amount of at least one photopolymerization catalyst selected from the group consisting of (cyclopentadienyl) ruthenium and osmium complexes and an effective amount of at least a co-catalyst selected from phosphonium salts, phosphines and amines; and (d) irradiating the mixture of (a) with an ultra-violet radiation to polymerize the mixture.Type: GrantFiled: April 30, 2001Date of Patent: July 15, 2003Assignee: Essilor International Compagnie Generale d'OptiqueInventors: Sirisoma Wanigatunga, Yassin Yusef Turshani, Peiqi Jiang
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Patent number: 6590011Abstract: An epoxy-amine composition includes an epoxy resin, an amine curative and a latent catalyst. The latent catalyst does not cause the instant acceleration of the reaction between epoxides and amines. In the presence of radiation, the latent catalyst generates an active catalyst that accelerates/initiates the cure process of the epoxy-amine composition.Type: GrantFiled: April 30, 2001Date of Patent: July 8, 2003Assignee: Polymeright, Inc.Inventors: Leonid Rappoport, Alex Vainer, Aleksander Yam
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Patent number: 6489375Abstract: An Offset Lithographic Printing Process employing low VOC lithographic printing ink formulations containing monomeric diluents, curable by cationic polymerization in the presence of fountain solution and resin rheology modifiers compatible with cationic catalysts.Type: GrantFiled: September 20, 2001Date of Patent: December 3, 2002Assignee: Sun Chemical CorporationInventors: Edward Stone, Gordon Kotora, Mikhail Laksin, Subhankar Chatterjee, Bhalendra J. Patel
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Patent number: 6482868Abstract: Accelerators that can be useful for an energy polymerizable composition comprising a cationically curable material; energy polymerizable -compositions comprising at least one cationically curable material and an initiation system therefor, the initiation system comprising at least one organometallic complex salt and at least one accelerator; and a method for curing the compositions. The cured compositions can provide useful articles. The invention also provides compositions of matter comprising an organometallic complex salt and at least one compound selected from the Class 1 and Class 2 compounds disclosed herein.Type: GrantFiled: June 26, 2000Date of Patent: November 19, 2002Assignee: 3M Innovative Properties CompanyInventors: Wayne Scott Mahoney, Peggy Sperl Willett
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Patent number: 6458865Abstract: 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: GrantFiled: January 15, 1999Date of Patent: October 1, 2002Assignees: Curators of the University of Missouri, 3M Innovative Properties CompanyInventors: Cecil C. Chappelow, Charles S. Pinzino, J. David Eick, Joel D. Oxman
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Patent number: 6235808Abstract: Disclosed are compounds of the formulas which are useful as monomers in photopolymerizable compositions. Also disclosed are methods of polymerizing these monomers, and polymers produced thereby.Type: GrantFiled: April 11, 2000Date of Patent: May 22, 2001Assignee: Rensselaer Polytechnic InstituteInventor: James V. Crivello
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Patent number: 6191181Abstract: The present invention relates to urethane acrylates, which may be cured with high-energy radiation, in which the urethane acrylates are the reaction product of a) a polyisocyanate component containing 20 to 100 mole %, based on the moles of the polyisocyanate component a), of iminooxadiazine dione group-containing polyisocyanate trimers corresponding to formula A wherein R1, R2and R3 are the same or different and represent linear or branched, C4-C20 (cyclo)alkyl groups and X is the same or different and represents isocyanate groups or isocyanate group-containing radicals that also contain iminooxadiazine dione, isocyanurate, uretdione, urethane, allophanate, biuret or oxadiazine trione groups, wherein R1, R2 and R3 are attached to a nitrogen atom, with b) an alcohol component containing at least one monobasic, hydroxy-functional, linear or branched C1-C12 alkyl ester of (meth)acrylic acid.Type: GrantFiled: November 4, 1999Date of Patent: February 20, 2001Assignee: Bayer AktiengesellschaftInventors: Jan Weikard, Wolfgang Fischer, Frank Richter, Christian Zwiener