Ether Group Patents (Class 522/181)
  • Patent number: 6028124
    Abstract: 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: Grant
    Filed: November 25, 1998
    Date of Patent: February 22, 2000
    Assignee: Dow Corning Corporation
    Inventors: Shedric Oneal Glover, Chi-long Lee, Wen-hong Tong
  • Patent number: 6025410
    Abstract: 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: Grant
    Filed: September 19, 1997
    Date of Patent: February 15, 2000
    Assignee: Ashland Inc.
    Inventors: Thomas M. Moy, Laurence Dammann, Roman Loza
  • Patent number: 6017603
    Abstract: 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: Grant
    Filed: December 22, 1997
    Date of Patent: January 25, 2000
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Kiyohisa Tokuda, Kenji Yoshida, Kazuhiko Ishii, Minoru Yokoshima
  • Patent number: 6008265
    Abstract: 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: Grant
    Filed: October 3, 1997
    Date of Patent: December 28, 1999
    Assignees: Hydro-Quebec, Centre National de la Recherche Scientifique
    Inventors: Alain Vallee, Michel Armand, Xavier Ollivrin, Christophe Michot
  • Patent number: 6001892
    Abstract: 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: Grant
    Filed: February 16, 1996
    Date of Patent: December 14, 1999
    Assignee: PPG Industries Oho, Inc.
    Inventors: Alan B. Weissberg, Edward E. McEntire, Charles B. Friedlander
  • Patent number: 5962546
    Abstract: 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: Grant
    Filed: May 1, 1997
    Date of Patent: October 5, 1999
    Assignee: 3M Innovative Properties Company
    Inventors: Albert I. Everaerts, William M. Lamanna, Albert E. Seaver, George V. D. Tiers
  • Patent number: 5958997
    Abstract: 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: Grant
    Filed: August 18, 1997
    Date of Patent: September 28, 1999
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Kim Eunkyoung, Lee Seobong, Kim Heejung
  • Patent number: 5945464
    Abstract: 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: Grant
    Filed: August 13, 1997
    Date of Patent: August 31, 1999
    Assignee: Asahi Kogaku Kogyo Kabushiki Kaisha
    Inventors: Hidenori Takushima, Kouji Futaki
  • Patent number: 5942556
    Abstract: 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: Grant
    Filed: November 27, 1996
    Date of Patent: August 24, 1999
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Charles B. Friedlander, Ronald R. Ambrose, David A. Diehl, Alan B. Weissberg, Carolyn A. Novak
  • Patent number: 5942290
    Abstract: 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: Grant
    Filed: August 21, 1997
    Date of Patent: August 24, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: David George Leppard, Thomas Lloyd James, Nils Hock, Manfred Kohler, Ronald Salathe
  • Patent number: 5922507
    Abstract: 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: Grant
    Filed: February 25, 1997
    Date of Patent: July 13, 1999
    Assignee: AGFA-Gevaert, N.V.
    Inventors: Marc Van Damme, Joan Vermeersch, Wolfgang Podszun, Norbert Lui
  • Patent number: 5902837
    Abstract: 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: Grant
    Filed: August 9, 1996
    Date of Patent: May 11, 1999
    Assignee: Sanyo Chemical Industries, Ltd.
    Inventors: Takao Saito, Kohei Maeda, Naoshi Ozasa
  • Patent number: 5872157
    Abstract: 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: Grant
    Filed: January 30, 1996
    Date of Patent: February 16, 1999
    Assignee: The University of North Carolina at Chapel Hill
    Inventors: Joseph M. DeSimone, Timothy J. Romack
  • Patent number: 5855837
    Abstract: 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: Grant
    Filed: June 6, 1995
    Date of Patent: January 5, 1999
    Assignee: Michigan State University
    Inventors: Alec B. Scranton, Bharath Rangarajan, Lindsay S. Coons
  • Patent number: 5817376
    Abstract: 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: Grant
    Filed: March 26, 1996
    Date of Patent: October 6, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Albert I. Everaerts, William M. Lamanna, Albert E. Seaver, George V. Tiers
  • Patent number: 5804301
    Abstract: 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: Grant
    Filed: January 11, 1996
    Date of Patent: September 8, 1998
    Assignee: Avery Dennison Corporation
    Inventor: Benedict S. Curatolo
  • Patent number: 5801033
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: September 1, 1998
    Assignee: The Board of Regents, The University of Texas System
    Inventors: Jeffrey A. Hubbell, Chandrashekhar P. Pathak, Amarpreet S. Sawhney, Neil P. Desai, Syed F. A. Hossainy
  • Patent number: 5798396
    Abstract: 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: Grant
    Filed: September 4, 1996
    Date of Patent: August 25, 1998
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Eiji Takahashi, Hiroo Muramoto
  • Patent number: 5783615
    Abstract: 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: Grant
    Filed: April 16, 1997
    Date of Patent: July 21, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Bettina Steinmann, Adrian Schulthess, Max Hunziker
  • Patent number: 5759721
    Abstract: 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: Grant
    Filed: November 1, 1996
    Date of Patent: June 2, 1998
    Assignee: Polaroid Corporation
    Inventors: Pradeep K. Dhal, Michael G. Horner, Richard T. Ingwall, Eric S. Kolb, Parag G. Mehta, Richard A. Minns, Howard G. Schild, David A. Waldman
  • Patent number: 5719008
    Abstract: 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: Grant
    Filed: September 8, 1995
    Date of Patent: February 17, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shigeo Hozumi, Hiroya Nakagawa
  • Patent number: 5705316
    Abstract: 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: Grant
    Filed: November 9, 1995
    Date of Patent: January 6, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Bettina Steinmann, Adrian Schulthess, Max Hunziker
  • Patent number: 5703137
    Abstract: 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: Grant
    Filed: March 14, 1996
    Date of Patent: December 30, 1997
    Assignee: Rhone-Poulenc Chimie
    Inventors: Christian Priou, Stuart Kerr, III
  • Patent number: 5702991
    Abstract: 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: Grant
    Filed: June 12, 1996
    Date of Patent: December 30, 1997
    Inventor: Richard L. Jacobs
  • Patent number: 5672463
    Abstract: 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: Grant
    Filed: October 20, 1995
    Date of Patent: September 30, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shigeo Hozumi, Shinichiro Kitayama, Hiroya Nakagawa
  • Patent number: 5672675
    Abstract: 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: Grant
    Filed: April 10, 1996
    Date of Patent: September 30, 1997
    Assignee: AlliedSignal, Inc.
    Inventors: George David Green, James Ronald Snyder, Raymond John Swedo
  • Patent number: 5658964
    Abstract: 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: Grant
    Filed: June 6, 1995
    Date of Patent: August 19, 1997
    Assignee: SICPA Holding S.A.
    Inventors: Philippe Amon, Haim Bretler, Anton Bleikolm, Olivier Rozumek, Pierre Degott
  • Patent number: 5639802
    Abstract: 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: Grant
    Filed: November 23, 1993
    Date of Patent: June 17, 1997
    Assignee: Spectra Group Limited, Inc.
    Inventors: Douglas C. Neckers, Yubai Bi
  • Patent number: 5612387
    Abstract: 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: Grant
    Filed: May 31, 1995
    Date of Patent: March 18, 1997
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventor: Kazufumi Ogawa
  • Patent number: 5605941
    Abstract: 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: Grant
    Filed: September 12, 1994
    Date of Patent: February 25, 1997
    Inventors: Bettina Steinmann, Adrian Schulthess, Max Hunziker
  • Patent number: 5585414
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: December 17, 1996
    Assignee: Loctite Corporation
    Inventors: Philip T. Klemarczyk, Yoshihisa Okamoto, James P. Moran, Jr.
  • Patent number: 5567858
    Abstract: 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: Grant
    Filed: December 12, 1995
    Date of Patent: October 22, 1996
    Assignee: Rensselaer Polytechnic Institute
    Inventor: James V. Crivello
  • Patent number: 5565500
    Abstract: 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: Grant
    Filed: September 22, 1994
    Date of Patent: October 15, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Kurt Meier, Roger P. Salvin
  • Patent number: 5565499
    Abstract: 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: Grant
    Filed: June 6, 1995
    Date of Patent: October 15, 1996
    Assignee: Loctite Corporation
    Inventors: Philip T. Klemarczyk, Yoshihisa Okamoto, James P. Moran, Jr.
  • Patent number: 5558937
    Abstract: 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: Grant
    Filed: May 3, 1995
    Date of Patent: September 24, 1996
    Assignee: Loctite Corporation
    Inventors: John G. Woods, Margaret A. Rakas, Anthony F. Jacobine, Louis M. Alberino, Philip L. Kropp, Donna M. Sutkaitis, David M. Glaser, Steven T. Nakos
  • Patent number: 5552451
    Abstract: 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: Grant
    Filed: November 4, 1994
    Date of Patent: September 3, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Albert I. Everaerts, Jeffrey D. Malmer
  • Patent number: 5539014
    Abstract: 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: Grant
    Filed: August 19, 1994
    Date of Patent: July 23, 1996
    Assignee: AlliedSignal Inc.
    Inventors: Raymond J. Swedo, George D. Green, James R. Snyder
  • Patent number: 5536760
    Abstract: 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: Grant
    Filed: December 10, 1993
    Date of Patent: July 16, 1996
    Assignee: PPG Industries, Inc.
    Inventors: Charles B. Friedlander, David A. Diehl
  • Patent number: 5529914
    Abstract: 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: Grant
    Filed: October 7, 1992
    Date of Patent: June 25, 1996
    Assignee: The Board of Regents the Univeristy of Texas System
    Inventors: Jeffrey A. Hubbell, Chandrashekhar P. Pathak, Amarpreet S. Sawhney, Neil P. Desai, Syed F. A. Hossainy
  • Patent number: 5514727
    Abstract: 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: Grant
    Filed: July 13, 1994
    Date of Patent: May 7, 1996
    Assignee: AlliedSignal Inc.
    Inventors: George D. Green, James R. Snyder, Raymond J. Swedo
  • Patent number: 5512608
    Abstract: A multi-part composition is provided which is suitable for use as an adhesive, a potting compound, a coating or a sealant. It consists of a polymerizable acrylate formulation and an activating formulation, the latter usually comprising an amine-aldehyde condensation product diluted with a liquid vinyl ether; liquid epoxides may also be included as diluents in the activating formulation.
    Type: Grant
    Filed: January 27, 1995
    Date of Patent: April 30, 1996
    Assignee: Dymax Corporation
    Inventors: Andrew G. Bachmann, Stephen E. Cantor
  • Patent number: 5502083
    Abstract: 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: Grant
    Filed: June 8, 1994
    Date of Patent: March 26, 1996
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
  • Patent number: 5491178
    Abstract: 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: Grant
    Filed: August 19, 1994
    Date of Patent: February 13, 1996
    Assignee: AlliedSignal Inc.
    Inventors: Raymond J. Swedo, George D. Green, James R. Snyder
  • Patent number: 5486545
    Abstract: 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: Grant
    Filed: April 25, 1994
    Date of Patent: January 23, 1996
    Assignee: Rensselaer Polytechnic Institute
    Inventor: James V. Crivello
  • Patent number: 5480917
    Abstract: 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: Grant
    Filed: December 29, 1994
    Date of Patent: January 2, 1996
    Assignee: Saint-Gobain Vitrage
    Inventors: Albert A. Kruger, Pascal Chartier
  • Patent number: 5479555
    Abstract: 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: Grant
    Filed: June 9, 1994
    Date of Patent: December 26, 1995
    Inventors: Alfred Rot, Irina Zaks-Rot
  • Patent number: 5470689
    Abstract: 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: Grant
    Filed: February 24, 1994
    Date of Patent: November 28, 1995
    Assignee: Ciba-Geigy AG
    Inventors: Jean-Pierre Wolf, Adrian Schulthess, Bettina Steinmann, Max Hunziker
  • Patent number: 5466496
    Abstract: 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: Grant
    Filed: April 13, 1994
    Date of Patent: November 14, 1995
    Assignee: Samsung Electron Devices Co., Ltd.
    Inventor: Yong W. Jin
  • Patent number: 5461086
    Abstract: 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: Grant
    Filed: September 6, 1994
    Date of Patent: October 24, 1995
    Assignee: Denki Kagaku Kogyo Kabushiki Kaisha
    Inventors: Toshiyuki Kato, Syunzi Ito, Tsunehiko Shimizui
  • Patent number: 5461087
    Abstract: 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: Grant
    Filed: July 29, 1993
    Date of Patent: October 24, 1995
    Assignee: Sony Corporation
    Inventors: Satoshi Takahashi, Ikuo Mitushima