Ether Group Patents (Class 522/181)
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Patent number: 6028124Abstract: This invention relates to a radiation curable compositions. More particularly this invention relates to radiation curable compositions comprising a vinyl ether compound which is free of silicon atoms, a cationic photoinitiator, a free radical photoinitiator, and dodecylphenol. The radiation curable compositions of this invention are useful for coating a thin layer film that has potential for many applications in the coating industry.Type: GrantFiled: November 25, 1998Date of Patent: February 22, 2000Assignee: Dow Corning CorporationInventors: Shedric Oneal Glover, Chi-long Lee, Wen-hong Tong
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Patent number: 6025410Abstract: The liquid oligomeric compositions of this invention are made by the Michael addition reaction of acetoacetate functional donor compounds with multifunctional acrylate receptor compounds where the equivalent ratios of multifunctional acrylate to acetoacetate vary from .gtoreq.1:1 to .gtoreq.13.2:1 depending on the functionality of both multifunctional acrylate and acetoacetate. Unuseable gelled or solid oligomer products occur below the claimed ranges. The liquid oligomers of this invention are further crosslinked to make coatings, laminates and adhesives.Type: GrantFiled: September 19, 1997Date of Patent: February 15, 2000Assignee: Ashland Inc.Inventors: Thomas M. Moy, Laurence Dammann, Roman Loza
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Patent number: 6017603Abstract: An ultraviolet-curable adhesive composition which comprises (A) a bisphenol type epoxy (meth)acrylate having a molecular weight of 450 to 3,000, (B) a urethane (meth)acrylate having a molecular weight of 400 to 10,000, (E) a (meth)acrylate monomer other than (A) and (B), and (F) a photopolymerization initiator, and an article having a cured layer of the above adhesive composition.Type: GrantFiled: December 22, 1997Date of Patent: January 25, 2000Assignee: Nippon Kayaku Kabushiki KaishaInventors: Kiyohisa Tokuda, Kenji Yoshida, Kazuhiko Ishii, Minoru Yokoshima
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Patent number: 6008265Abstract: An ionic compound comprising at least one group A.sup.+ X.sup.-, comprising:a cationic group A.sup.+ selected from the group consisting of biaryliodonium, arylsulfonium, arylacylsulfonium, diazonium and organometallic cations comprising a transition metal complexed with at least one unsaturated cyclic compound comprising 4-12 carbon atoms, said cationic group being part of a polymer chain; whereinX.sup.- is an imide anion, [FSO.sub.2 NSO.sub.2 R'.sub.F ].sup.- or [R.sub.F CH.sub.2 OSO.sub.2 NSO.sub.2 R'.sub.F ].sup.- or [(R.sub.F).sub.2 CHOSO.sub.2 NSO.sub.2 R'.sub.F ].sup.-, or a methylide anion [FSO.sub.2 C(Q)SO.sub.2 R'.sub.F ].sup.-, or a [R.sub.F CH.sub.2 OSO.sub.2 C(Q)SO.sub.2 R'.sub.F ].sup.- or [(R.sub.F).sub.2 CHOSO.sub.2 C(Q)SO.sub.2 R'.sub.F ].sup.31 .Type: GrantFiled: October 3, 1997Date of Patent: December 28, 1999Assignees: Hydro-Quebec, Centre National de la Recherche ScientifiqueInventors: Alain Vallee, Michel Armand, Xavier Ollivrin, Christophe Michot
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Patent number: 6001892Abstract: A liquid, radiation curable composition is disclosed that includes a reactive diluent to lower initial application viscosity without substantial reduction of cure rate. The composition of the present invention comprises: (a) an unsaturated polyester polymer; (b) a non-polymerized, cocurable polyfunctional vinyl ether component; and (c) a reactive diluent which is an unsaturated dioic acid ester having the following structural formula: ##STR1## wherein at least one of R.sup.1 and R.sup.2 is a group that includes an oxygen with a carbon adlacent thereto and an abstractable hydrogen attached to the carbon.Type: GrantFiled: February 16, 1996Date of Patent: December 14, 1999Assignee: PPG Industries Oho, Inc.Inventors: Alan B. Weissberg, Edward E. McEntire, Charles B. Friedlander
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Patent number: 5962546Abstract: Compositions containing conductivity enhancers, which are capable of being coated onto a substrate by means of electrostatic assistance. The compositions comprise one or more cationically polymerizable monomer(s), one or more cationic initiator(s), and one or more non-volatile conductivity enhancer(s) having anionic and cationic portions which are soluble in the monomer(s) and which do not interfere with cationic polymerization wherein the anionic portion is a non-coordinating carbon-containing anion. The compositions may further comprise one or more dissociation enhancing agent(s), oligomer(s) or polymer(s), preferably co-reactive, free-radically curable monomer(s), free-radical generating initiator(s), leveling agents, and other additives or adjuvants to impart specific properties to the polymerized composition.Type: GrantFiled: May 1, 1997Date of Patent: October 5, 1999Assignee: 3M Innovative Properties CompanyInventors: Albert I. Everaerts, William M. Lamanna, Albert E. Seaver, George V. D. Tiers
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Patent number: 5958997Abstract: The present invention provides a composition for a polymeric ion conductive membrane. Said composition comprises an alkaline salt, an acrylate and/or methacrylate of poly(ethylene glycol) alkyl ether with an unsaturated reactive radical, a poly(alkylene glycol) dimethacrylate or a poly(alkylene glycol) trimethacrylate, a vinylic monomer and an UV radiation curing initiator.The present invention further provides a method for producing said polymeric ion conductive membrane with the composition.The polymeric ion conductive membrane so produced according to the present invention has an excellent mechanical feature, strong adhesive strength and high ionic conductivity at room temperature.Type: GrantFiled: August 18, 1997Date of Patent: September 28, 1999Assignee: Korea Research Institute of Chemical TechnologyInventors: Kim Eunkyoung, Lee Seobong, Kim Heejung
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Patent number: 5945464Abstract: The ultraviolet-curable, resin-forming composition which comprises a polycarbonic acid ester such as diethylene glycol bis(allyl carbonate), a polythiol such as pentaerythritol tetrakis(3-mercaptopropionate) and an ultraviolet curing agent. The resin-forming composition can be photopolymerized in an atmospheric condition, and the thus produced resin has an elongated durability as well as excellent properties with regard to a transparency, heat resistance, adhesion property, resistance to shock, dyeing property and others.Type: GrantFiled: August 13, 1997Date of Patent: August 31, 1999Assignee: Asahi Kogaku Kogyo Kabushiki KaishaInventors: Hidenori Takushima, Kouji Futaki
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Patent number: 5942556Abstract: Disclosed is a radiation curable composition which includes: (a) an unsaturated ester compound, and (b) a pulverizable vinyl ether compound. The unsaturated ester compound is characterized as having a plurality of unsaturated ester groups per molecule. The pulverizable vinyl ether compound is characterized as including at least one of the following: (a) a compound having an average of greater than 1.0 reactive vinyl ether groups per molecule, and (b) a vinyl ether-containing group bonded to the unsaturated ester compound such that there is an average of at least 1.0 reactive vinyl ether group per molecule. The unsaturated ester compound, the vinyl ether compound and/or a mixture thereof is treated with a reducing agent so as to decompose destabilizing agents present therein that would initiate premature polymerization of the vinyl ether compound.Type: GrantFiled: November 27, 1996Date of Patent: August 24, 1999Assignee: PPG Industries Ohio, Inc.Inventors: Charles B. Friedlander, Ronald R. Ambrose, David A. Diehl, Alan B. Weissberg, Carolyn A. Novak
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Patent number: 5942290Abstract: Molecular complex compounds comprising a mono-, bis- or trisacylphosphine oxide compound with an .alpha.-hydroxy ketone compound are suitable as photoinitiators for the photopolymerization of free-radically polymerizable compounds.Type: GrantFiled: August 21, 1997Date of Patent: August 24, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: David George Leppard, Thomas Lloyd James, Nils Hock, Manfred Kohler, Ronald Salathe
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Patent number: 5922507Abstract: The present invention provides a photosensitive imaging element comprising on a support a two-phase layer, said two-phase layer comprising a disperse hydrophobic photopolymerizable. phase and a hydrophilic continuous phase, characterized in that the hydrophobic photopolymerizable phase comprises a multifunctional monomer with a perfluoroalkyl or perfluoroalkenyl group.Type: GrantFiled: February 25, 1997Date of Patent: July 13, 1999Assignee: AGFA-Gevaert, N.V.Inventors: Marc Van Damme, Joan Vermeersch, Wolfgang Podszun, Norbert Lui
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Patent number: 5902837Abstract: A photocurable resin composition comprising a propenyl ether group-containing compound (A) having propenyl ether groups of the following formula (1) and having a number-average molecular weight of not less than 500, and a cationic photopolymerization initiator (B).CH.sub.3 --CH.dbd.CH--O-- (1)The object is to provide a photocurable resin composition which cures at a higher speed than a vinyl ether compound on exposure to light irradiation, and has improved flow characteristics, physical property of cured resin, and adhesion to metal.Type: GrantFiled: August 9, 1996Date of Patent: May 11, 1999Assignee: Sanyo Chemical Industries, Ltd.Inventors: Takao Saito, Kohei Maeda, Naoshi Ozasa
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Patent number: 5872157Abstract: A process for making oxidized olefins is disclosed. Specifically, the process comprises providing an olefin and oxygen in combination in a reaction medium comprising carbon dioxide, and then oxidizing the olefin in the reaction medium to make the oxidized olefin. Preferably, a perfluoropolyether is produced by the process.Type: GrantFiled: January 30, 1996Date of Patent: February 16, 1999Assignee: The University of North Carolina at Chapel HillInventors: Joseph M. DeSimone, Timothy J. Romack
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Patent number: 5855837Abstract: A novel method for producing thick composite parts based upon photopolymerizable compositions is disclosed. The constituents of the photopolymerizable mixture comprise a monomer or monomers capable of polymerizing by free radical or cationic mechanisms, and a photoinitiator system which possesses an absorbance characteristic which is effectively reduced, or self-eliminating, upon initiation of the polymerization reaction. Parts having thicknesses up to 2 cm and thicker for varying end use applications are made by photopolymerizing such compositions. In addition, using such compositions composite parts can be made using a reinforcement material such as a glass fiber mat present in an amount by weight of from about 5 to about 70%.Type: GrantFiled: June 6, 1995Date of Patent: January 5, 1999Assignee: Michigan State UniversityInventors: Alec B. Scranton, Bharath Rangarajan, Lindsay S. Coons
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Patent number: 5817376Abstract: Compositions containing conductivity enhancers, which are capable of being coated onto a substrate by means of electrostatic assistance. The compositions comprise one or more free-radically curable monomer(s), and one or more non-volatile conductivity enhancer(s), having cationic and anionic portions, which are soluble in the monomer(s) and which do not interfere with free-radical polymerization, wherein said anionic portion is a non-coordinating organophilic carbon-containing anion. The compositions may further comprise one or more initiator(s), one or more dissociation enhancing agent(s), cross-linking agent(s), cationically polymerizable monomer(s), cationic initiator(s), leveling agents, oligomer(s) or polymer(s), preferably co-reactive, and other additives or adjuvants to impart specific properties to the cured coating.Type: GrantFiled: March 26, 1996Date of Patent: October 6, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Albert I. Everaerts, William M. Lamanna, Albert E. Seaver, George V. Tiers
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Patent number: 5804301Abstract: A radiation-curable coating composition is described which comprises (A) from about 70% to about 99% by weight of at least one polyfunctional acrylate monomer containing at least one internal flexible unit; (B) from about 1% to about 30% by weight of at least one other reactive vinyl or unsaturated monomer provided the reactive vinyl or unsaturated monomer (B) is not the same as the monomer of (A); and (C) from about 0% to about 10% by weight of at least one photoinitiator, provided that the composition is free of methacrylic functionalized colloidal silica. A method of coating a substrate utilizing the radiation-curable compositions of the present invention, and a substrate coated in accordance with the method of the invention are also described.Type: GrantFiled: January 11, 1996Date of Patent: September 8, 1998Assignee: Avery Dennison CorporationInventor: Benedict S. Curatolo
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Patent number: 5801033Abstract: This invention provides novel methods for the formation of biocompatible membranes around biological materials using photopolymerization of water soluble molecules. The membranes can be used as a covering to encapsulate biological materials or biomedical devices, as a "glue" to cause more than one biological substance to adhere together, or as carriers for biologically active species. Several methods for forming these membranes are provided. Each of these methods utilizes a polymerization system containing water-soluble macromers, species which are at once polymers and macromolecules capable of further polymerization. The macromers are polymerized using a photoinitiator (such as a dye), optionally a cocatalyst, optionally an accelerator, and radiation in the form of visible or long wavelength UV light. The reaction occurs either by suspension polymerization or by interfacial polymerization.Type: GrantFiled: June 7, 1995Date of Patent: September 1, 1998Assignee: The Board of Regents, The University of Texas SystemInventors: Jeffrey A. Hubbell, Chandrashekhar P. Pathak, Amarpreet S. Sawhney, Neil P. Desai, Syed F. A. Hossainy
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Patent number: 5798396Abstract: The present invention is directed to sulfonium salt-containing compounds represented by a following general formula; ##STR1## wherein R.sub.1 is alkyl containing from 1 to 18 carbon atoms, hydroxy, alkoxy containing from 1 to 18 carbon atoms, alkylcarbonyloxy containing from 1 to 18 carbon atoms or halogen, n is any of 0, 1, 2 or 3, however, each of R.sub.1 may be different from the others when n is 2 or more, R.sub.2 is alkyl containing from 1 to 6 carbon atoms, R.sub.3 and R.sub.4 are each independently hydrogen or alkyl containing from 1 to 6 carbon atoms, R.sub.5 and R.sub.6 are each independently hydrogen, alkyl containing from 1 to 6 carbon atoms, hydroxy, alkoxy containing from 1 to 6 carbon atoms, alkylcarbonyloxy containing from 1 to 18 carbon atoms or aromatic carbonyloxy, and R.sub.7 is alkyl containing from 4 to 20 carbon atoms or a group represented by a following formula; ##STR2## wherein R.sub.Type: GrantFiled: September 4, 1996Date of Patent: August 25, 1998Assignee: Nippon Soda Co., Ltd.Inventors: Eiji Takahashi, Hiroo Muramoto
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Patent number: 5783615Abstract: The invention relates to compounds having at least one vinyl ether group which also contain in the molecule at least one further functional group selected from acrylate, methacrylate, epoxy, alkenyl, cycloalkenyl and vinylaryl groups, to compositions, especially for stereolithography, comprising those vinyl ether compounds, and to a method of producing three-dimensional objects using those compositions.Type: GrantFiled: April 16, 1997Date of Patent: July 21, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Bettina Steinmann, Adrian Schulthess, Max Hunziker
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Patent number: 5759721Abstract: A holographic recording medium comprises an acid generator capable of producing an acid upon exposure to actinic radiation; a binder; and at least one monomer or oligomer capable of undergoing cationic polymerization initiated by the acid produced from the acid generator. This recording medium is not subject to the disadvantages (for example, oxygen sensitivity) associated with radical-polymerized prior art holographic recording media.Type: GrantFiled: November 1, 1996Date of Patent: June 2, 1998Assignee: Polaroid CorporationInventors: Pradeep K. Dhal, Michael G. Horner, Richard T. Ingwall, Eric S. Kolb, Parag G. Mehta, Richard A. Minns, Howard G. Schild, David A. Waldman
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Patent number: 5719008Abstract: A photoresist composition is disclosed which includes:(1) a photopolymerizable monomer represented by the following formula (I) or its derivative: ##STR1## wherein n represents a number of from 0 to 20; R.sub.1 and R.sub.2 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group or a cycloalkyl group; each of Q represents --OH or --OROCH.dbd.CH.sub.2 in which R represents an alkylene group, provided that the molar ratio of (--OH)/(--OROCH.dbd.CH.sub.2) is from 10/90 to 90/10; and A represents a divalent hydrocarbon group or a divalent group having Q on it;(2) a triazine compound having a methyl group substituted with one, two or three halogen atoms; and(3) a solvent,which can be used in photolithography or for producing a color filter.Type: GrantFiled: September 8, 1995Date of Patent: February 17, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Shigeo Hozumi, Hiroya Nakagawa
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Patent number: 5705316Abstract: The invention relates to compounds having at least one vinyl ether group which also contain in the molecule at least one further functional group selected from acrylate, methacrylate, epoxy, alkenyl, cycloalkenyl and vinylaryl groups, to compositions, especially for stereolithography, comprising those vinyl ether compounds, and to a method of producing three-dimensional objects using those compositions.Type: GrantFiled: November 9, 1995Date of Patent: January 6, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Bettina Steinmann, Adrian Schulthess, Max Hunziker
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Patent number: 5703137Abstract: The present invention relates to initiators for the polymerization and/or crosslinking, cationically and under photochemical and/or thermal activation and/or activation by a beam of electrons, of monomers and/or polymers containing organofunctional groups.The said initiators are of the type comprising an onium salt of an element from groups 15 to 17 of the Periodic Table (Chem & Eng News, Vol 63, N5, 26, of 4 Feb. 1985) and they are characterized in that they contain at least one polymerization and/or crosslinking accelerator chosen from .alpha.-hydroxylated carboxylic acid esters such as, for example, lactic acid esters. Another subject of the invention is compositions based on at least one cationically crosslinkable polyorganosiloxane and on at least one initiator.Type: GrantFiled: March 14, 1996Date of Patent: December 30, 1997Assignee: Rhone-Poulenc ChimieInventors: Christian Priou, Stuart Kerr, III
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Patent number: 5702991Abstract: Structure, composition and method in which a fiber reinforcement is impregnated with an interpenetrating network of a light cure resin and a thermosetting resin which are independently curable, enabling autobody component repair, electronic assembly bonding, etc. by selective cure first of one or the other resin, and the support against fluid flow of the uncured resin by the first cured resin.Type: GrantFiled: June 12, 1996Date of Patent: December 30, 1997Inventor: Richard L. Jacobs
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Patent number: 5672463Abstract: A polyfunctional vinyl ether compound represented by formula (I): ##STR1## wherein n, which is an average repeating number, represents a number of from 0 to 20; R.sub.1 and R.sub.2 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, or a cycloalkyl group; Q each independently represents --OH or a group represented by the formula --OROCH.dbd.CH.sub.2, wherein R represents an alkylene group having from 1 to 12 carbon atoms, the molar ratio of (--OH)/(--OROCH.dbd.CH.sub.2) being from 10/90 to 90/10; and A each independently represents a divalent hydrocarbon group having from 1 to 30 carbon atoms.Type: GrantFiled: October 20, 1995Date of Patent: September 30, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Shigeo Hozumi, Shinichiro Kitayama, Hiroya Nakagawa
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Patent number: 5672675Abstract: Oligomers of particular usefulness in coatings are vinyl ether terminated polyester oligomers which include 4,8-bis(hydroxymethyl) tricyclo?5.2.1.0.sup.2,6 !decane (BHTD).Type: GrantFiled: April 10, 1996Date of Patent: September 30, 1997Assignee: AlliedSignal, Inc.Inventors: George David Green, James Ronald Snyder, Raymond John Swedo
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Patent number: 5658964Abstract: A printing ink for the printing of security documents by the method of engraved steel die printing, having a viscosity of at least 1 Pa.multidot.s at 40.degree. C. under a shear of about 1000 sec.sup.-1, containing a binder matrix, a polymerization initiator for polymerizable matrix components, fillers and pigments, and the usual additives. The binder matrix contains at least one cationically polymerizable compound, modified to bring about the desired rheology of the ink, and the photoinitiator, activable by UV, heat and EB, is an onium salt capable of releasing a Lewis or Bronsted acid.This ink has best and very rapid drying characteristics.Type: GrantFiled: June 6, 1995Date of Patent: August 19, 1997Assignee: SICPA Holding S.A.Inventors: Philippe Amon, Haim Bretler, Anton Bleikolm, Olivier Rozumek, Pierre Degott
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Patent number: 5639802Abstract: The present invention relates to a novel class of compounds which absorb light at wavelengths greater than 350 nm and are useful as fluorescers or as photoinitiators. The present invention provides compounds of the formulas (I) and (II) and their equivalents (the nomenclature of the compounds used herein is based on the numbering of positions as shown in formula (I)): ##STR1## where: when W is .dbd.O, W.sup.1 is hydrogen or --OR.sup.9 and when W is .dbd.NR.sup.+.sub.2, W is hydrogen or --NR.sub.2, A is hydrogen, alkenyl, alkyl or an election withdrawing group, and the remaining groups are as defined in the disclosure.Type: GrantFiled: November 23, 1993Date of Patent: June 17, 1997Assignee: Spectra Group Limited, Inc.Inventors: Douglas C. Neckers, Yubai Bi
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Patent number: 5612387Abstract: A new nonlinear organic optical material having a high Second Harmonic Generation capability and a method of manufacturing the same is disclosed. Energy-beam sensitive monomer molecules having large molecular dipole-moments are sandwiched between two facing orientation films formed on respective substrates, and the energy-beam sensitive parts in said molecules are polymerized by irradiation with an energy-beam such as an X-ray beam after the dipole-moments of the energy-beam sensitive monomer molecules are aligned by applying a magnetic or an electric field. As a result of this, no cancellation of dipole-moments takes place, and polymers having extremely high dipole-moments and high Second Harmonic Generation efficiency can be derived and manufactured.Type: GrantFiled: May 31, 1995Date of Patent: March 18, 1997Assignee: Matsushita Electric Industrial Co., Ltd.Inventor: Kazufumi Ogawa
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Patent number: 5605941Abstract: The invention relates to compounds having at least one vinyl ether group which also contain in the molecule at least one further functional group selected from acrylate, methacrylate, epoxy, alkenyl, cycloalkenyl and vinylaryl groups, to compositions, especially for stereolithography, comprising those vinyl ether compounds, and to a method of producing three-dimensional objects using those compositions.Type: GrantFiled: September 12, 1994Date of Patent: February 25, 1997Inventors: Bettina Steinmann, Adrian Schulthess, Max Hunziker
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Patent number: 5585414Abstract: Resin compositions useful for filament winding applications comprising an epoxy component including at least one polyepoxide resin curable by heat, an olefinicially unsaturated monomer component including at least one polyolefinically unsaturated monomer curable by actinic radiation, at least one photoinitiator, at least one organic peroxide, and a heat activated curing agent for epoxides. The compositions have a viscosity less than about 2000 centipoise (cps) and are capable of retaining this viscosity for at least about 2 hours at a temperature of from about ambient temperature to about 60.degree. C. The resins are capable of being immobilized by actinic radiation exposure and further heat cured without substantial resin drip. One or more organic peroxides are employed, selected from the group of organic peroxides having 10 hour decomposition half lives at temperatures of from about 50.degree. C. to less than about 104.degree. C.Type: GrantFiled: June 7, 1995Date of Patent: December 17, 1996Assignee: Loctite CorporationInventors: Philip T. Klemarczyk, Yoshihisa Okamoto, James P. Moran, Jr.
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Patent number: 5567858Abstract: Propenyl ether monomers of formula VA(OCH.dbd.CHCH.sub.3).sub.nwherein n is an integer from one to six and A is selected from cyclic ethers, polyether and alkanes are disclosed. The monomers are readily polymerized in the presence of cationic photoinitiators, when exposed to actinic radiation, to form poly(propenyl ethers) that are useful for coatings, sealants, varnishes and adhesives. Compositions for preparing polymeric coatings comprising the compounds of formula V together with particular cationic photoinitiators are also disclosed, as are processes for making the monomers from allyl halides and readily available alcohols. The process involves rearranging the resulting allyl ethers to propenyl ethers.Type: GrantFiled: December 12, 1995Date of Patent: October 22, 1996Assignee: Rensselaer Polytechnic InstituteInventor: James V. Crivello
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Patent number: 5565500Abstract: The invention relates to mixtures containing:a) a cationically polymerizable compound andb) a compound of the formula I[R.sup.1 (Fe.sup.II R.sup.2).sub.a ].sub.q.sup..sym.an anX.sup..crclbar.q (I)in which a is 1 or 2, n is 1 or 2, R.sup.1 is a substituted or unsubstituted .pi.-arene, R.sup.2 is a substituted or unsubstituted .pi.-arene or cyclopentadienyl anion or indenyl anion, q is an integer from 1 to 3 and X is FSO.sub.3.sup.- or a q-valent anion of an organic sulfonic acid or of a carboxylic acid; R.sup.1 can also be a polymeric, aromatic ligand. The invention also relates to the novel compounds of the formula I. The curable mixtures can be processed in particular for the production of coatings having a good resistance to heat.Type: GrantFiled: September 22, 1994Date of Patent: October 15, 1996Assignee: Ciba-Geigy CorporationInventors: Kurt Meier, Roger P. Salvin
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Patent number: 5565499Abstract: Resin compositions useful for filament winding applications comprising an epoxy component including at least one polyepoxide resin curable by heat, an olefinicially unsaturated monomer component including at least one polyolefinically unsaturated monomer curable by actinic radiation, at least one photoinitiator, at least one organic peroxide, and a heat activated curing agent for epoxides. The compositions have a viscosity less than about 2000 centipoise (cps) and are capable of retaining this viscosity for at least about 2 hours at a temperature of from about ambient temperature to about 60.degree. C. The resins are capable of being immobilized by actinic radiation exposure and further heat cured without substantial resin drip. One or more organic peroxides are employed, selected from the group of organic peroxides having 10 hour decomposition half lives at temperatures of from about 50.degree. C. to less than about 104.degree. C.Type: GrantFiled: June 6, 1995Date of Patent: October 15, 1996Assignee: Loctite CorporationInventors: Philip T. Klemarczyk, Yoshihisa Okamoto, James P. Moran, Jr.
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Patent number: 5558937Abstract: A curable thiol-ene composition specially adapted for use as a primary coating on optical fibers comprises a polythiol and a compound having a plurality of norbornene groups thereon, are characterized in that one of either the compound having the plurality of norbornene groups or the polythiol has a backbone of a poly(tetramethylene oxide), or is an oligomer thereof, and the poly(tetramethylene oxide) has a molecular weight of between 250 and 5,000. The formulations are relatively low viscosity liquids at practical application temperatures and cure substantially completely with very low irradiation fluence. The formulations cure in ambient air. There is no need to exclude oxygen or to control humidity. The formulations of the invention can be cured using low intensity UV lamps which do not generate significant amounts of heat. The cured products have excellent low temperature flexibility, good humidity and water absorbtion resistance and good thermal oxidative stability.Type: GrantFiled: May 3, 1995Date of Patent: September 24, 1996Assignee: Loctite CorporationInventors: John G. Woods, Margaret A. Rakas, Anthony F. Jacobine, Louis M. Alberino, Philip L. Kropp, Donna M. Sutkaitis, David M. Glaser, Steven T. Nakos
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Patent number: 5552451Abstract: The present invention relates to a permanently removable, low melt viscosity acrylic pressure-sensitive adhesive comprising a lower alkylacrylate, a higher alkylacrylate and a crosslinker.Type: GrantFiled: November 4, 1994Date of Patent: September 3, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: Albert I. Everaerts, Jeffrey D. Malmer
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Patent number: 5539014Abstract: This invention relates to vinyl ether-based coatings for which properties such as color stability, thermal stability, mechanical stability, hydrolytic stability, and resistance to embrittlement may be maintained and properties hydrogen generation and blocking are minimized.Type: GrantFiled: August 19, 1994Date of Patent: July 23, 1996Assignee: AlliedSignal Inc.Inventors: Raymond J. Swedo, George D. Green, James R. Snyder
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Patent number: 5536760Abstract: Disclosed is a liquid, radiation curable composition comprising: (A) an unsaturated polyester component containing an unsaturated polyester polymer, an unsaturated polyester oligomer or a mixture thereof; and (B) a non-polymerized, cocurable vinyl ether component which may be separate from or structurally incorporated in the unsaturated polyester component, provided that the vinyl ether component contains an average of at least two vinyl ether groups per molecule of the vinyl ether component.Also disclosed is a method of coating comprising: applying to a substrate a film of a liquid, radiation curable composition of the invention, and curing the composition through its thickness to a tack-free state by exposing the film to ionizing radiation and/or ultraviolet light.Type: GrantFiled: December 10, 1993Date of Patent: July 16, 1996Assignee: PPG Industries, Inc.Inventors: Charles B. Friedlander, David A. Diehl
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Patent number: 5529914Abstract: This invention provides novel methods for the formation of biocompatible membranes around biological materials using photopolymerization of water soluble molecules. The membranes can be used as a covering to encapsulate biological materials or biomedical devices, as a "glue" to cause more than one biological substance to adhere together, or as carriers for biologically active species. Several methods for forming these membranes are provided. Each of these methods utilizes a polymerization system containing water-soluble macromers, species which are at once polymers and macromolecules capable of further polymerization. The macromers are polymerized using a photoinitiator (such as a dye), optionally a cocatalyst, optionally an accelerator, and radiation in the form of visible or long wavelength UV light. The reaction occurs either by suspension polymerization or by interfacial polymerization.Type: GrantFiled: October 7, 1992Date of Patent: June 25, 1996Assignee: The Board of Regents the Univeristy of Texas SystemInventors: Jeffrey A. Hubbell, Chandrashekhar P. Pathak, Amarpreet S. Sawhney, Neil P. Desai, Syed F. A. Hossainy
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Patent number: 5514727Abstract: This invention relates to vinyl ether-based coatings for which properties such as color stability, thermal stability, mechanical stability, hydrolyric stability, and resistance to embrittlement may be maintained and properties hydrogen generation and blocking are minimized. The invention also relates to stabilizers which control these properties in the coatings.Type: GrantFiled: July 13, 1994Date of Patent: May 7, 1996Assignee: AlliedSignal Inc.Inventors: George D. Green, James R. Snyder, Raymond J. Swedo
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Patent number: 5512608Abstract: A multi-part composition is provided which is suitable for use as an adhesive, a potting compound, a coating or a sealant. It consists of a polymerizable acrylate formulation and an activating formulation, the latter usually comprising an amine-aldehyde condensation product diluted with a liquid vinyl ether; liquid epoxides may also be included as diluents in the activating formulation.Type: GrantFiled: January 27, 1995Date of Patent: April 30, 1996Assignee: Dymax CorporationInventors: Andrew G. Bachmann, Stephen E. Cantor
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Patent number: 5502083Abstract: The composition of the present invention is excellent in compatibility, transparency and curability and give a cured coat of excellent gloss and of less smell, and cured products of excellent properties can be obtained by curing the composition.The present invention relates to an onium salt represented by the following formula (1): ##STR1## wherein Ar is a mono- to tetra-valent aromatic group, X is a bisphenylsulfonio group which may have a substituent, a is 1-4, b is 0 or 1-3, a+b is 1-4, n is 1-4, and Z is a halide represented by the following formula (3):MQ.sub.m (OH).sub.l (3)where M is a boron atom, a phosphorus atom, an arsenic atom or an antimony atom, Q is a halogen atom, m is 3-6, l is 0 or 1, and m+l is 4-6; a photopolymerization initiator containing the onium salt as an active ingredient; an energy ray-curable composition containing the initiator; and a cured product.Type: GrantFiled: June 8, 1994Date of Patent: March 26, 1996Assignee: Nippon Kayaku Kabushiki KaishaInventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
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Patent number: 5491178Abstract: This invention relates to vinyl ether-based coatings for which properties such as color stability, thermal stability, mechanical stability, hydrolytic stability, and resistance to embrittlement may be maintained and properties hydrogen generation and blocking are minimized.Type: GrantFiled: August 19, 1994Date of Patent: February 13, 1996Assignee: AlliedSignal Inc.Inventors: Raymond J. Swedo, George D. Green, James R. Snyder
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Patent number: 5486545Abstract: Propenyl ether monomers of formula VA(OCH.dbd.CHCH.sub.3).sub.nwherein n is an integer from one to six and A is selected from cyclic ethers, polyether and alkanes are disclosed. The monomers are readily polymerized in the presence of cationic photoinitiators, when exposed to actinic radiation, to form poly(propenyl ethers) that are useful for coatings, sealants, varnishes and adhesives. Compositions for preparing polymeric coatings comprising the compounds of formula V together with particular cationic photoinitiators are also disclosed, as are processes for making the monomers from allyl halides and readily available alcohols. The process involves rearranging the resulting allyl ethers to propenyl ethers.Type: GrantFiled: April 25, 1994Date of Patent: January 23, 1996Assignee: Rensselaer Polytechnic InstituteInventor: James V. Crivello
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Patent number: 5480917Abstract: An anti-fogging coating comprises from 40 to 80% by weight of at least one acrylic or methacrylic acid monomer, from 20 to 60% by weight of at least one short chain acrylic or methacrylic acid ester monomer and, in relation to the total weight of the preceding monomers, from 1 to 15% of a crosslinking agent and from 0.1 to 5% of a polymerization initiator compound using the action of ultraviolet radiation. Transparent products formed from a glass or poly(methyl methacrylate) support and a layer of the preceding composition, polymerized and crosslinked by the action of ultraviolet radiation, exhibit good anti-fogging and mechanical resistance properties.Type: GrantFiled: December 29, 1994Date of Patent: January 2, 1996Assignee: Saint-Gobain VitrageInventors: Albert A. Kruger, Pascal Chartier
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Patent number: 5479555Abstract: A photocurable resin composition useful for producing plastic optical materials, comprises at least one compound of formula (I) represented by the formula: ##STR1## wherein R.sub.1 is H or --CH.sub.3 ; R.sub.2 is --CH.sub.2 --CH.sub.2 --; --CH.sub.2 --CH(CH.sub.3)--; --CH.sub.2 --CH(CH.sub.2 Cl)--; n.sub.1 is 1 to 6R.sub.3 is --CH.sub.2 --CH.sub.2 --; --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --; --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --; --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --;R.sub.4 is ##STR2## n.sub.2 is 1 to 2 n.sub.3 is 0 to 3and a photoinitiator. Also a polymeric material, an optical material, a lens, a protective coating for optical fibers and an adhesive for multilayer glass with the inventive photocurable resin composition are proposed.Type: GrantFiled: June 9, 1994Date of Patent: December 26, 1995Inventors: Alfred Rot, Irina Zaks-Rot
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Patent number: 5470689Abstract: Photopolymerisable compositions comprising(a) a tetraacrylate of formula I or II ##STR1## wherein R.sub.1 is a hydrogen atom or methyl,X.sub.1 and X.sub.2 are each independently of the other --O-- or --CO--O--,R.sub.2 is a divalent aliphatic, cycloaliphatic or aromatic radical of a diglycidyl compound that contains no more glycidyl ether or ester groups,A is a divalent aliphatic, cycloaliphatic or aromatic radical of a diisocyanate compound that contains no more isocyanate groups,n is an integer from 1 to 8, andR.sub.3 is a tetravalent cycloaliphatic radical of a diepoxide compound that contains no more 1,2-epoxide groups at the cycloaliphatischen ring,(b) at least one liquid radically polymerisable compound that differs from component a), and(c) a radical photoinitiator, are suitable preferably for the production of three-dimensional objects by the stereolithographic technique.Type: GrantFiled: February 24, 1994Date of Patent: November 28, 1995Assignee: Ciba-Geigy AGInventors: Jean-Pierre Wolf, Adrian Schulthess, Bettina Steinmann, Max Hunziker
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Patent number: 5466496Abstract: Liquid crystal films which are stable to light, moisture and heat, and which have an improved response time and viewing angle are provided by combining ferroelectric liquid crystals and a polymer matrix. The invention further provides for liquid crystal display elements utilizing the liquid crystal films of the invention. Still further, the invention provides methods of producing the liquid crystal films. According to the invention, liquid crystalline polymers having optical anisotropy as a polymer matrix and functional side chain radicals having an asymmetric carbon atom and dipole moment in the polymer matrix are matched with the dipole moment of the ferroelectric crystals.Type: GrantFiled: April 13, 1994Date of Patent: November 14, 1995Assignee: Samsung Electron Devices Co., Ltd.Inventor: Yong W. Jin
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Patent number: 5461086Abstract: A photocurable resin composition for glass lamination, consisting essentially of a radical polymerizable monomer having at least two repeating units of ethylene oxide in its molecule and a photopolymerization initiator, a cured product of which has a volume resistivity of less than 5.times.10.sup.9 .OMEGA..cm.Type: GrantFiled: September 6, 1994Date of Patent: October 24, 1995Assignee: Denki Kagaku Kogyo Kabushiki KaishaInventors: Toshiyuki Kato, Syunzi Ito, Tsunehiko Shimizui
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Patent number: 5461087Abstract: A UV curable adhesive composition contains a C4 to C14 alkyl alcohol-acrylic acid ester monomer and a monofunctional oligoester acrylate. The composition is cured with UV rays to produce an adhesive the glass transition temperature of which is to be lower than -20.degree. C. Preferably, the composition also contains glass powders and/or polyolefin powders. A double-face adhesive tape includes two porous base sheets in an adhesive layer produced on curing a UV curable adhesive composition.Type: GrantFiled: July 29, 1993Date of Patent: October 24, 1995Assignee: Sony CorporationInventors: Satoshi Takahashi, Ikuo Mitushima