Containing C-co-c(h)(or) Wherein R Is Organic, E.g., Benzoin Methyl Ether, Etc. Patents (Class 522/43)
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Patent number: 6232360Abstract: UV-curable coating compositions containing urethane acrylates prepared from hydroxyalkyl acrylates and low-viscosity polyisocyanates having isocyanurate groups, low-viscosity acrylic ester components as reactive diluents, initiators, and optionally solvents and/or other known additives, and their use for coating molded articles of thermoplastic polycarbonates.Type: GrantFiled: February 3, 1995Date of Patent: May 15, 2001Assignee: Bayer AktiengesellschaftInventors: Jürgen Meixner, Wolfgang Fischer, Josef Pedain
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Patent number: 6156816Abstract: A substantially water-free, water-washable, energy-curable composition includes an epoxy oligomer and/or urethane oligomer having at least two ethylenically unsaturated moieties, at least one alkoxylated polyol monomer having at least two ethylenically unsaturated moieties and capable of being copolymerized with the oligomer, and a surface active agent capable of being integrated into the molecular structure of the cured polymer and further capable of rendering the uncured composition dispersible in water. Optionally, the composition can contain a photoinitiator. The composition is self-dispersible in water and is especially suitable for use as a coating material for a printing screen.Type: GrantFiled: August 20, 1998Date of Patent: December 5, 2000Assignee: Henkel CorporationInventor: Marie-Esther Saint Victor
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Patent number: 6130269Abstract: A thermosetting pressure-sensitive adhesive comprising a photopolymerization product of a composition containing a) 100 parts by weight of a (meth) acrylic acid alkyl ester wherein the average carbon atom number of the alkyl group is from 2 to 14 and from 30 to 1% by weight of a monoethylenically unsaturated acid copolymerizable with the ester, b) from 0.02 to 5 parts by weight of a polyfunctional (meth)acrylate as a crosslinking agent, c) from 0.01 to 4 parts by weight of a photopolymerization initiator, and d) from 5 to 30 parts by weight of an epoxy resin, and not substantially containing a curing agent for the epoxy resin, and an adhesive sheet using the thermosetting type pressure-sensitive adhesive.Type: GrantFiled: November 24, 1998Date of Patent: October 10, 2000Assignee: Nitto Denko CorporationInventors: Kazuhito Hosokawa, Shigeki Muta, Hitoshi Takahira, Takao Yoshikawa
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Patent number: 6099783Abstract: A novel method for producing thick composite parts based upon photopolymerizable compositions is disclosed. Also disclosed are novel methods for encapsulation of microelectronic devices based upon novel photopolymerizable compositions. 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: August 7, 1998Date of Patent: August 8, 2000Assignee: Board of Trustees Operating Michigan State UniversityInventors: Alec B. Scranton, Bharath Rangarajan, Kiran K. Baikerikar
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Patent number: 6090236Abstract: A method of generating reactive species which includes exposing a polymolecular photoreactor to radiation, in which the polymolecular photoreactor comprises a wavelength-specific sensitizer associated with a reactive species-generating photoinitiator. The sensitizer absorbs energy and transfers the absorbed energy to the photoinitiator which in turn, generates reactive species. The wavelength-specific sensitizer is adapted to have an absorption wavelength band generally corresponding to an emission peak of the radiation. The radiation to which the polymolecular photoreactor is exposed generally will have a wavelength of from about 4 to about 1,000 nanometers. Thus, the radiation may be ultraviolet radiation, including near ultraviolet and far or vacuum ultraviolet radiation: visible radiation: and near infrared radiation. Desirably, the radiation will have a wavelength of from about 100 to about 900 nanometers.Type: GrantFiled: December 31, 1997Date of Patent: July 18, 2000Assignee: Kimberly-Clark Worldwide, Inc.Inventors: Ronald Sinclair Nohr, John Gavin MacDonald
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Patent number: 6030703Abstract: Composition suitable for free radical, radiation curable coating comprising at least one polyester having unsaturated backbone and at least one compound having two to six propenyl ether groups, and optionally, a free radical photoinitiator. The equivalent ratio of propenyl ether groups to maleimide, maleate and/or fumarate groups in the polyester is preferably about 5:1 to about 1:5.The process for curing the composition includes exposing it to ionizing radiation and/or ultraviolet light. The resultant cured coatings and coated articles are similar in performance to their vinyl ether analogues, but the propenyl ethers are easier to prepare than the vinyl ether analogues.Type: GrantFiled: August 13, 1997Date of Patent: February 29, 2000Assignee: Sartomer Company, Inc.Inventors: Mingxin Fan, Gary W. Ceska, James Horgan, Nicholas Trainer
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Patent number: 5998496Abstract: A compound of the general formula:A-L.sup.+ D.sup.-where A is a moiety which absorbs radiation and enters an excited state in which it accepts an electron; D.sup.- is a moiety which donates an electron to the excited state A and releases a free radical; and L.sup.+ is a cationic linking group which tethers electron acceptor moiety A to electron donor moiety D.sup.-. Cationic linking moiety L.sup.+ has the formula:-L'-G-where L' is a moiety which forms a stable radical with acceptor moiety A upon transfer of an electron from donor moiety D.sup.- to electron acceptor moiety A, and G is a moiety which forms a leaving group upon transfer of the electron from donor moiety D.sup.- to acceptor moiety A.Type: GrantFiled: August 19, 1996Date of Patent: December 7, 1999Assignee: Spectra Group Limited, Inc.Inventors: Salah A. Hassoon, Ananda M. Sarker, Douglas C. Neckers
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Patent number: 5948514Abstract: A photocurable and thermosetting resin composition developable with an aqueous alkali solution is disclosed. The composition comprises in combination: (A) a photosensitive prepolymer soluble in a dilute aqueous alkali solution obtained by esterifying an epoxy resin represented by the following general formula (1) with (meth)acrylic acid and further adding an acid anhydride thereto until an acid value reaches a level in the range of 60 to 120 mg KOH/g, (B) a diglycidyl ether type epoxy compound containing two epoxy groups in the molecular unit thereof, (C) a photopolymerization initiator, and (D) a diluent at such ratios of combination that said epoxy compound (B) accounts for a proportion in the range of 5 to 120 parts by weight and said photopolymerization initiator (C) for a proportion in the range of 0.1 to 30 parts by weight, based on 100 parts by weight of said photosensitive prepolymer (A): ##STR1## wherein X represents CH.sub.2, C(CH.sub.3).sub.2, or SO.sub.Type: GrantFiled: June 5, 1996Date of Patent: September 7, 1999Assignee: Taiyo Ink Manufacturing Co., Ltd.Inventors: Shigeru Komori, Kazuo Suda, Masao Arima, Miyako Juni
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Patent number: 5945462Abstract: The present invention relates to an aqueous-based coating composition for forming strippable, protective coating for protecting surfaces, such as glass, metal, ceramic, plastic or other materials of construction. More specifically, the compositions and coatings formed therefrom of this invention are particularly useful in connection with protecting precision surfaces, such as optical lenses, including but not limited to ophthalmic lenses, telescopic lenses, microscopic lenses, and the like, which protection is desirably only of a temporary nature.Type: GrantFiled: October 2, 1997Date of Patent: August 31, 1999Assignee: Loctite CorporationInventor: Peter A. Salamon
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Patent number: 5942555Abstract: A photoactivatable reagent useful as a chain transfer reagent for providing a semitelechelic polymer having one or more terminal photoactivatable groups. The reagent provides one or more photoactivatable groups and one or more sulfhydryl (or other chain transfer) groups, the photoactivatable and chain transfer groups optionally being joined together by a spacer group. The reagent can be used to prepare a polymer by serving to initiate the polymerization of ethylenically unsaturated monomers. The reagent itself becomes an integral part of the resultant polymer, thereby providing the polymer with a terminal photoactivatable nature. The method provides a number of benefits, including the ability to provide homogeneous photoactivatable polymer compositions, e.g., in terms of the uniform location of the photogroup(s) on the terminal portion of each polymer molecule and the ability to build a desired nonpolar quality, and in turn improved surfactancy, into otherwise polar polymers.Type: GrantFiled: March 21, 1996Date of Patent: August 24, 1999Assignee: SurModics, Inc.Inventors: Melvin J. Swanson, Richard A. Amos, Dale G. Swan, Gary W. Opperman
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Patent number: 5932625Abstract: A photo-curable resin composition suitable as a material for photo-fabricating and capable of producing cured products with excellent mechanical strength and high heat resistance. Further disclosed is a process for molding a resin-based mold which provides superior molding dimensional precision and superb repetition durability. The resin composition contains a monomer component containing (A) 30-70 wt % of a polyfunctional unsaturated monomer having a cyclic structure and (B) 70-30 wt % of a monofunctional unsaturated monomer having a cyclic structure of which the homopolymer has a glass transition temperature (Tg) of 70.degree. C. or higher; (C) a photo-initiator; and (D) an inorganic filler having an average particle diameter or an average fiber length of 1-50 .mu.Type: GrantFiled: May 30, 1997Date of Patent: August 3, 1999Assignees: DSM N.V., JSR Corporation, Japan Fine Coatings Co., Ltd.Inventors: Tsuyoshi Watanabe, Ayao Matsumura, Yuichi Haruta, Takashi Ukachi
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Patent number: 5902599Abstract: Biodegradable polymer networks are provided which are useful in a variety of dental and orthopedic applications. The biodegradable polymer networks can be formed in one embodiment by polymerizing anhydride prepolymers including crosslinkable groups, such as unsaturated moieties. The anhydride prepolymers can be crosslinked, for example in a photopolymerization reaction by irradiation of the prepolymer with light in the presence of a free radical initiator. Suitable anhydride prepolymers include dianhydrides of a dicarboxylic acid and a carboxylic acid molecule comprising a crosslinkable group. For example, methacrylic acid dianhydrides of monomers or oligomers of a diacid such as sebacic acid or 1,3-bis(p-carboxyphenoxy)-hexane can be used. The anhydride prepolymers can be applied in vivo to a site where an orthopedic implant is needed, and then may be crosslinked, for example, by irradiation with U.V. light, to form a biodegradable implant such as a rods, pin or plate.Type: GrantFiled: February 20, 1996Date of Patent: May 11, 1999Assignee: Massachusetts Institute of TechnologyInventors: Kristi S. Anseth, Robert Langer, Venkatram R. Shastri
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Patent number: 5858545Abstract: Free-radically polymerizable release coating compositions containing conductivity enhancers, which are capable of being electrosprayed onto a substrate. The compositions comprise (a) about 100 parts by weight of one or more free-radically polymerizable vinyl monomer(s), (b) from about 0.05 to about 250 parts by weight of one or more polydiorganosiloxane polymer(s) copolymerizable with the vinyl monomer(s), and (c) from about 0.10 to about 10 parts by weight, based on 100 parts by weight of (a) and (b), of one or more non-volatile conductivity enhancer(s), which are soluble in the monomer(s) and which do not interfere with polymerization, wherein the composition may be electrosprayed.The composition may further comprise from about 0.1 to about 5 parts by weight of one or more initiator(s) based on 100 parts by weight of monomer(s) and polydiorganosiloxane polymer(s).Another embodiment of the present invention further comprises at least 0.Type: GrantFiled: March 26, 1996Date of Patent: January 12, 1999Assignee: Minnesota Mining and Manufacturing CompanyInventors: Albert I. Everaerts, Mieczyslaw H. Mazurek, Albert E. Seaver
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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: 5837746Abstract: Compounds of the formulaRG--A--INwherein IN is a photoinitiator basic structure A is a spacer group and RG is a functional reactive group can be employed as coreactive photoinitiators for photo-polymerization of systems containing ethylenically unsaturated compounds.Type: GrantFiled: June 23, 1997Date of Patent: November 17, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Manfred Kohler, Jorg Ohngemach, Eike Poetsch, Rudolf Eidenschink, Gerhard Greber, Dieter Dorsch, Jurgen Gehlhaus, Konrad Dorfner, Hans Ludwig Hirsch
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Patent number: 5811199Abstract: A method of generating reactive species which includes exposing a photoreactor composition to radiation, in which the photoreactor composition comprises a wavelength-specific sensitizer associated with a reactive species-generating photoinitiator. Also described are methods of polymerizing unsaturated monomers and curing an unsaturated oligomer/monomer mixture.Type: GrantFiled: June 5, 1995Date of Patent: September 22, 1998Assignee: Kimberly-Clark Worldwide, Inc.Inventors: John Gavin MacDonald, Ronald Sinclair Nohr
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Patent number: 5744248Abstract: The present invention relates to coating compositions, which are curable by radiation and containI) 0 to 95 parts by weight of at least one binder curable by radiation and containing maleate, fumarate and/or acryloyl groups other than those of component II),II) 5 to 100 parts by weight of a mixture ofA) 20 to 80 parts by weight of at least one polyester resin prepared from fatty acids, provided that at least 20 wt. % of component A) is a fatty acid having a number average molecular weight of 112 to 400 andB) 20 to 80 parts by weight of compounds containing (meth)acryloyl groups, having a viscosity at 23.degree. C. of 10 to 1,000 mPa.s and having a number average molecular weight of 170 to 1,000,wherein the sum of the parts by weight of components I) and II) adds up to 100, based on the weight of components I) and II), and the sum of the parts by weight of components A) and B) adds up to 100, based on the weight of components A) and B).Type: GrantFiled: January 28, 1997Date of Patent: April 28, 1998Assignee: Bayer AktiengesellschaftInventors: Jurgen Meixner, Wolfgang Fischer, Manfred Muller, Gunter Ruf
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Patent number: 5744512Abstract: Compounds of the formulaRG--A--INwhereinIN is a photoinitiator basic structureA is a spacer group andRG is a functional reactive group can be employed as coreactive photoinitiators for photopolymerization of systems containing ethylenically unsaturated compounds.Type: GrantFiled: March 20, 1996Date of Patent: April 28, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Manfred Kohler, Jorg Ohngemach, Eike Poetsch, Rudolf Eidenschink, Gerhard Greber, Dieter Dorsch, Jurgen Gehlhaus, Konrad Dorfner, Hans Ludwig Hirsch
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Patent number: 5736589Abstract: Absorbable polymers and blends of acrylated poly(alkylene diglycolate)s and aliphatic polyesters based on lactone monomers such as lactide, glycolide, e-caprolactone, p-dioxanone, and trimethylene carbonate are described. The polymers and blends exhibit a broad range of properties, useful in a variety of medical devices.Type: GrantFiled: July 30, 1996Date of Patent: April 7, 1998Assignee: Ethicon, Inc.Inventors: Kevin Cooper, Angelo Scopelianos
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Patent number: 5696178Abstract: Absorbable polymers and blends of acrylated poly(alkylene diglycolate)s and aliphatic polyesters based on lactone monomers such as lactide, glycolide, e-caprolactone, p-dioxanone, and trimethylene carbonate are described. The polymers and blends exhibit a broad range of properties, useful in a variety of medical devices.Type: GrantFiled: July 22, 1996Date of Patent: December 9, 1997Assignee: Ethicon, Inc.Inventors: Kevin Cooper, Angelo Scopelianos
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Patent number: 5616629Abstract: A radiation-curable release composition is disclosed which comprises:(A) an organopolysiloxane represented by the formulaRSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n (Si(CH.sub.3)(R)O).sub.m Si(CH.sub.3).sub.2 R (I)wherein in Formula (I), each R is --R.sup.1 --O(O)C--C(R.sup.2).dbd.CH.sub.2, --R.sup.1 --O--C(R.sup.2).dbd.CH.sub.2 or is derived from an organic molecule containing both ethylenic unsaturation and epoxide functionality; R.sup.1 is a hydrocarbylene group; each R.sup.2 is independently hydrogen or a methyl or ethyl group; m is a number from about 1 to about 15; and n is a number from about 50 to about 300; and(B) an organosiloxane copolymer represented by the formula(R.sub.3 SiO).sub.x (SiO.sub.4/2).sub.y (II)wherein in Formula (II), each R is independently a hydrocarbon group or a group represented by the formula--O(O)C--C(R*).dbd.CH.sub.2wherein R* is hydrogen or a methyl or ethyl group; x is a number from about 0.Type: GrantFiled: February 27, 1995Date of Patent: April 1, 1997Assignee: Avery Dennison CorporationInventors: Thanh V. Nguyen, John Allen, Qun Yu
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Patent number: 5559163Abstract: UV curable coatings comprising at least one photoinitiator and at least one photopolymerizable UV absorber, wherein the photoinitiator has the ability to absorb a significant portion of the total energy needed to cure the coating from wavelengths in which the UV absorber does not appreciably absorb.Type: GrantFiled: August 31, 1994Date of Patent: September 24, 1996Assignee: The Sherwin-Williams CompanyInventors: William R. Dawson, Goutam Gupta
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Patent number: 5539012Abstract: 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, a cyanate ester component including at least one cyanate ester compound having at least two cyanate functional groups per molecule, at least one organic peroxide, at least one photoinitiator, 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 6 months at about ambient temperature. 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.Type: GrantFiled: August 18, 1993Date of Patent: July 23, 1996Assignee: Loctite CorporationInventors: Philip T. Klemarczyk, Yoshihisa Okamoto
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Patent number: 5532286Abstract: A photopolymerizable composition comprising a crosslinking agent, a UV sensitive photopolymerization initiator and a thioether compound having a vinyl ester or vinyl amide component; wherein the crosslinking agent and the thioether may be the same compound.Type: GrantFiled: March 16, 1995Date of Patent: July 2, 1996Assignee: Eastman Kodak CompanyInventors: Elizabeth G. Burns, Susan A. Visser, Jeffrey F. Taylor
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Patent number: 5532112Abstract: Compounds of the formulaRG--A--INwhereinIN is a photoinitiator basic structureA is a spacer group andRG is a functional reactive groupcan be employed as coreactive photoinitiators for photopolymerization of systems containing ethylenically unsaturated compounds.Type: GrantFiled: June 2, 1994Date of Patent: July 2, 1996Assignee: Ciba-Geigy CorporationInventors: Manfred Kohler, Jorg Ohngemach, Eike Poetsch, Rudolf Eidenschink, Gerhard Greber, Dieter Dorsch, Jurgen Gehlhaus, Konrad Dorfner, Hans L. Hirsch
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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: 5436281Abstract: Proposed is an improved radiation-curable organopolysiloxane composition capable of giving a cured surface film on a substrate surface which exhibits excellent releasability against sticky substances. The composition is obtained by combining two kinds of (meth)acryloxyalkyl-containing organopolysiloxanes in a specified weight proportion, of which one has a relatively large degree of polymerization but contains only a relatively small amount of the silicon-bonded (meth)acryloxyalkyl groups while the other has a relatively small degree of polymerization but contains a relatively large amount of the silicon-bonded (meth)acryloxyalkyl groups.Type: GrantFiled: May 13, 1994Date of Patent: July 25, 1995Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Shinji Irifune, Toshio Ohba
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Patent number: 5412002Abstract: An epoxy resin composition contains an epoxy resin represented by the formula (I) and a curing accelerator: ##STR1## wherein R.sup.1 stands for ##STR2## where G stands for a glycidyl group, R.sup.2 stands for an alkyl group having 1 to 4 carbon atoms, R.sup.3 and R.sup.4 stand for the same or different groups and each denote a hydrogen atom or a glycidyl group, m and x each denote an integer of 0 to 10, n denotes an integer of 0 to 2, provided that m.gtoreq.x and, if m=0, then x=0, in which case at least one of R.sup.3 and R.sup.4 denotes a glycidyl group on the condition that when m.gtoreq.1 and m>x, R.sup.1 may each stand for different groups.Type: GrantFiled: December 9, 1992Date of Patent: May 2, 1995Assignee: Nippon Oil Co., Ltd.Inventors: Masami Enomoto, Susumu Kubota, Hitoshi Yuasa, Fumiaki Oshimi, Yutaka Otsuki
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Patent number: 5391587Abstract: Photoinitiators having a terminal fluoroalkyl moiety are useful for photopolymerizing and photocuring fluorinated as well as non-fluorinated monomers, especially fluorinated acrylic monomers.Type: GrantFiled: April 30, 1993Date of Patent: February 21, 1995Assignee: AlliedSignal Inc.Inventor: Chengjiu Wu
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Patent number: 5378734Abstract: A UV and moisture-curable organopolysiloxane composition comprising (i) an organopolysiloxane terminated with a radical of formula (1): ##STR1## wherein R.sup.1 is a hydrogen atom or monovalent hydrocarbon radical, each of R.sup.2 and R.sup.3 is a divalent hydrocarbon radical which may contain a NH bond or ether bond, each of R.sup.4 and R.sup.5 is a monovalent hydrocarbon radical which may contain an ether bond, and a is equal to 0 or 1, (ii) a photo-polymerization initiator, and (iii) a curing catalyst. The composition readily cures either upon exposure to UV radiation or upon contact with moisture and from the surface to the deep interior within a short time, yielding cured products having satisfactory physical properties.Type: GrantFiled: August 27, 1993Date of Patent: January 3, 1995Assignee: Shin-Etsu Chemical Company, Ltd.Inventor: Yoshio Inoue
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Patent number: 5371116Abstract: Vulcanizable organopolysiloxane compositions comprise a hydroxy-terminated organopolysiloxane, an acrylic or methacryllc functional alkoxy silane, a divalent tin compound, an alkoxy-.alpha.-silyl ester, a photopolymerization initiator, and a curing catalyst whereby the composition is cured by UV irradiation and/or by the action of moisture in air. The composition has good shelf stability and can yield rubber elastomers having good physical properties.Type: GrantFiled: July 13, 1993Date of Patent: December 6, 1994Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takafumi Sakamoto, Masatoshi Arai, Kei Miyoshi
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Patent number: 5360834Abstract: A process is described for photoinitiated control of inorganic network fotion in the sol-gel process, which comprises eitherA) subjecting one or more hydrolytically polycondensable compounds of constituent elements of glass or ceramic, excluding silicon compounds containing polymerizable organic groups, to hydrolytic polycondensation in a liquid reaction medium to form a sol andirradiating the resulting sol in a structured or unstructured manner in the presence of a photoinitiator which can change the pH of the reaction medium on irradiation, using radiation of a wavelength range in which the photoinitiator absorbs;orB) liberating water in an anhydrous reaction medium which contains an alcohol, one or more hydrolytically polycondensable compounds of constituent elements of glass or ceramic and a photoinitiator which can liberate water by a photochemical reaction or a secondary reaction when irradiated, by structured or non-structured irradiation using radiation of a wavelength range in which the photoinitiatoType: GrantFiled: January 31, 1994Date of Patent: November 1, 1994Assignee: Fraunhofer-Gesellschaft Zur Forderung der Angewandten Forschung e.V.Inventors: Michael Popall, Jochen Schulz, Helmut Schmidt
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Patent number: 5352713Abstract: A radiation curable coating composition comprising acrylate oligomers and monomers, vinyl ether monomers, and a free radical photoinitiator. The vinyl ether monomers replace N-vinyl-pyrrolidone or other undesirable reactive diluents while retaining or modifying the properties of coatings using such diluents.Type: GrantFiled: April 1, 1992Date of Patent: October 4, 1994Assignee: Allied-Signal Inc.Inventors: James R. Snyder, George D. Green, John J. Krajewski
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Patent number: 5334456Abstract: A free-radical radiation curable composition comprising:a) at least one compound containing from one to about six vinyl ether groups; andb) at least one compound containing a saturated backbone and at least one maleate or fumarate end group per molecule,wherein the ratio of vinyl ether groups to maleate or fumarate groups in the composition is in the range of about 5:1 to about 1:5.Type: GrantFiled: May 26, 1992Date of Patent: August 2, 1994Assignee: Stamicarbon B.V.Inventors: Gerry K. Noren, John J. Krajewski, Sami A. Shama, John M. Zimmerman, Danny C. Thompson, John T. Vandeberg
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Patent number: 5334455Abstract: A free-radical radiation curable composition comprising:a) at least one compound containing from one to about six vinyl ether groups; andb) at least one product obtainable by the reaction of a half-ester of maleic and/or fumaric acid with an epoxy functionalized compound,wherein the ratio of vinyl ether groups to maleate and/or fumarate groups is in the range of about 5:1 to about 1:5.Type: GrantFiled: May 26, 1992Date of Patent: August 2, 1994Assignee: Stamicarbon B.V.Inventors: Gerry K. Noren, John J. Krajewski, Sami A. Shama, John M. Zimmerman, Danny C. Thompson, John T. Vandeberg
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Patent number: 5331018Abstract: The present invention is directed to a non-emissive, bimodal cured polymeric network which has an onset degradation temperature that is about 100.degree. C. above the onset degradation temperature of a base polymer. The novel cured polymeric network comprises the cured reaction product of the following ingredients: (a) combination of one or more liquid carrier monomers or prepolymers which combination is reactive to form a base polymer by exposure to ultraviolet (UV) radiation in the presence of a UV photosensitizer at a temperature, T.sub.uv ; and (b) between about 10 and 100 wt-% based on ingredient (a) of a combination of one or more monomers or prepolymers which combination is reactive to form a cured high temperature stable polymer by heating at a temperature, T.sub..DELTA.. Ingredient (b) is soluble or dispersible in ingredient (a) at a temperature, T.sub.s, wherein T.sub.s is equal to or lower than T.sub.uv, and T.sub.uv is at least about 50.degree. C. lower than T.sub..DELTA..Type: GrantFiled: August 26, 1992Date of Patent: July 19, 1994Assignee: Three Bond Co., Ltd.Inventors: Vincent D. McGinniss, James L. White, Hiroyuki Mikuni
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Patent number: 5283265Abstract: A photopolymerizable rubber being obtained by copolymerizing four compounds consisting of a dienic liquid rubber having hydroxyl groups, an ethylenically unsaturated monomer having hydroxyl groups, a dihydric alcohol having a molecular weight of less than 2,000 and a diisocyanate compound. The photocured product of this composition has higher tensile strength and elongation than that of the prior photopolymerizable rubbers.Type: GrantFiled: April 18, 1988Date of Patent: February 1, 1994Assignee: Hayakawa Rubber Company LimitedInventors: Tetsuya Kimura, Syuno Suto, Fujii Toshihiro, Toshihiro Fujii, Kimio Mori, Tsuguo Yamaoka
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Patent number: 5260361Abstract: Disclosed is a coating composition comprising (A) 10 to 70 parts by weight of a poly(meth)acrylate of mono- or polypentaerythritol, (B) 5 to 50 parts by weight of a urethane poly(meth)acrylate having at least two unsaturated double bonds in the molecule, (C) 5 to 50 parts by weight of a poly[(meth)acryloyloxyalkyl] (iso)cyanurate, (D) 2 to 30 parts by weight of an ultraviolet absorber, (E) 0.1 to 10 parts by weight of a photopolymerization initiator, and (F) 0.1 to 5 parts by weight of a hindered amine type light stabilizer, provided that the combined amount of components (A) to (F) is 100 parts by weight. This coating composition can form a crosslinked and cured film having excellent abrasion resistance, surface smoothness, thermal resistance, chemical resistance, durability, weather resistance and adhesion to the substrate.Type: GrantFiled: November 18, 1992Date of Patent: November 9, 1993Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Hiroshi Fukushima, Misao Tamura, Osamu Takemoto, Takaji Kawaguchi
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Patent number: 5246979Abstract: The heat stability of acrylamide functional polydiorganosiloxanes which cure by exposure to ultraviolet radiation can be improved by the addition of nickel carboxylate, stannous naphthenate, cerium carboxylate, manganese carboxylate, aluminum carboxylate, silver carboxylate, copper undecylenate, cobalt carboxylate, mono(methacrylate) tripropoxyzirconate, mono(ethylacetoacetonate) aluminum di-(sec-butoxide), di-(ethylacetoacetonate) aluminum sec-butoxide, zinc acetylacetonate, molybdenum acetylacetonate, and dibutyltin dicarboxylate.Type: GrantFiled: May 31, 1991Date of Patent: September 21, 1993Assignee: Dow Corning CorporationInventors: Michael A. Lutz, Kristen A. Scheibert
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Patent number: 5236967Abstract: An optical molding composition is used for casting and does not cause irritation to the skin or possess a bad smell. This composition comprises1. an actinic radiation-curable, radical-polymerizable organic compound comprising(1) one or more polythiol compounds and(2) one or more polyene compounds each having at least two actinic radiation-reactive carbon-to-carbon double bonds in the molecule, and2. an actinic radiation-sensitive radical polymerization initiator.Type: GrantFiled: February 18, 1992Date of Patent: August 17, 1993Assignee: Asahi Denka Kogyo K.K.Inventors: Kazuo Ohkawa, Seiichi Saito
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Patent number: 5213875Abstract: Resin compositions comprising 20 to 50% by weight, based on total composition weight, of a first resin which comprises an acrylate-epoxy oligomer having a molecular weight of from 2000 to 5000; from 2 to 10% of a second resin which comprises an acrylate-urethane oligomer; up to 50% of a third resin which comprises a second acrylate-epoxy oligomer, where from 1 to 5% of the epoxy is an epoxy novolac; from 10 to 40% of a liquid acrylate; from 2 to 20% of a liquid diacrylate having an ether linkage; from 5 to 25% of a liquid alkylene diacrylate; and from 1 to 5% of a UV photoinitiator. The compositions also preferably includes from 0.05 to 1% of a flow control agent. The compositions are applied to substrates such as printed wiring boards and cured with ultraviolet light to form a conformal coating on the substrate.Type: GrantFiled: September 7, 1988Date of Patent: May 25, 1993Assignee: Westinghouse Electric Corp.Inventors: Wei-Fang A. Su, Anthony P. Barrett
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Patent number: 5207577Abstract: A dental adhesive comprising a (meth)acryloylaminoalkyl carboxylate of the formula ##STR1## in which R.sup.1 represents hydrogen or methyl;R.sup.2 represents methylene or ethylene; andR.sup.3 represents hydrogen, methyl, or ethyl;and at least one of an initiator, a non-toxic solvent, and a filler. The dental adhesive is useful to effect a strong adhesive bonding of dental materials to collagen-containing materials.Type: GrantFiled: January 25, 1991Date of Patent: May 4, 1993Assignee: Bayer AktiengesellschaftInventors: Michael Muller, Wolfgang Podszun
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Patent number: 5204378Abstract: The fluorine-containing epoxy(meth)acrylate resin of the invention is represented by the following general formula (I). ##STR1## wherein R.sub.f is selected from the group consisting of --.phi.--C(CF.sub.3).sub.2 --.phi.--(where .phi. stands for ##STR2## --C(CF.sub.3).sub.2 --.phi.'--C(CF.sub.3).sub.2 --(where .phi.' stands for and --CH.sub.2 (CF.sub.2).sub.6 CH.sub.2 --; n is zero or a positive interger; and X is hydrogen or methyl group. The resin of the invention may be prepared by reacting a diglycidyl ether of a fluorine-containing hydrocarbon (R.sub.f) with acrylic acid or methacrylic acid. Further provided is an adhesive composition comprising the aforementioned fluorine-containing epoxy(meth)acrylate resin and a photo-polymerization initiator, which can be cured at room temperature within a short time by irradiation with UV rays to form a cured product having a refractive index N.sub.D.sup.20 ranging from 1.434 to 1.532.Type: GrantFiled: March 18, 1991Date of Patent: April 20, 1993Assignee: Nippon Telegraph and Telephone CorporationInventors: Tohru Maruno, Shigeki Ishibashi, Kouzaburou Nakamura
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Patent number: 5191039Abstract: The fluorine-containing epoxy(meth)acrylate resin of the invention is represented by the following general formula (I). ##STR1## wherein R.sub.f is selected from the group consisting of --.phi.--C(CF.sub.3).sub.2 --.phi.-- (where .phi. stands for ##STR2## --C(CF.sub.3).sub.2 --.phi.'--C(CF.sub.3).sub.2 -- (where .phi.' stands for ##STR3## and --CH.sub.2 (CF.sub.2).sub.6 CH.sub.2 --; n is zero or a positive integer; and X is hydrogen or methyl group. The resin of the invention may be prepared by reacting a diglycidyl ether of a fluorine-containing hydrocarbon (R.sub.f) with acrylic acid or methacrylic acid. Further provided is an adhesive composition comprising the aforementioned fluorine-containing epoxy(meth)acrylate resin and a photo polymerization initiator, which can be cured at room temperature within a short time by irradiation with an UV ray to form a cured product having a refractive index n.sub.D.sup.20 ranging from 1.434 to 1.532.Type: GrantFiled: May 2, 1991Date of Patent: March 2, 1993Assignee: Nippon Telegraph and Telephone CorporationInventors: Tohru Maruno, Shigeki Ishibashi, Kouzaburou Nakamura
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Patent number: 5166186Abstract: A resin composition, particularly for an ink printing composition, comprising a polyurethane (meth-) acrylate resin, N-vinylpyrrolidone, and acryloylmorphline, with a photoinitiator when used as an ultraviolet raycurable ink printing composition, and without a photoinitiator when used as an electron beam-curable ink printing composition.Type: GrantFiled: July 28, 1989Date of Patent: November 24, 1992Assignees: Nippondenso Co., Ltd., Nippon Kayaku Kabushiki Kaisha, Jujo Chemical Co., Ltd.Inventors: Hisano Kojime, Yoshinori Asano, Yoshiharu Ohi, Shigeo Date
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Patent number: 5087550Abstract: Radiation-reactive mixtures suitable for producing insulating layers and printed circuits are composed of certain precursors for preparing polyimides, polyisoindoloquinazolinediones, polyoxiazinediones, polyquinazolinediones or polyquinazolones and aryl-containing carbonyl compounds which when excited by UV radiation are capable of hydrogen abstraction, these mixtures undergoing solubility differentiation on irradiation with actinic light.Type: GrantFiled: September 26, 1989Date of Patent: February 11, 1992Assignee: BASF AktiengesellschaftInventors: Rainer Blum, Gerd Rehmer, Hans Schupp
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Patent number: 5073477Abstract: Disclosed is a photosensitive resin composition for flexographic printing which has high water developability and good mechanical strength. The resin composition comprises (A) a partially crosslinked copolymer prepared by a radical emulsion polymerization of a specific monomer mixture (B) a linear polymer having a molecular weight of at least 5,000, which has at least 30 mol % of a conjugated diene unit, (C) a basic nitrogen atom-containing compound, (D) a photopolymerizable ethylenically unsaturated monomer, and (E) a photopolymerization inhitiator. The present invention also provides a resin plate for flexographic printing obtained from the above mentioned resin composition and a process for preparing it. The present invention further provides a printing plate obtained from the resin plate and a process for preparing it.Type: GrantFiled: December 4, 1990Date of Patent: December 17, 1991Assignee: Nippon Paint Co., Ltd.Inventors: Hidefumi Kusuda, Katsuji Konishi, Koichi Ueda
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Patent number: 5068261Abstract: The fluorine-containing epoxy(meth)acrylate resin of the invention is represented by the following general formula (I). ##STR1## wherein R.sub.f is selected from the group consisting of --.phi.--C(CF.sub.3).sub.2 --.phi.-- ##STR2## --C(CF.sub.3).sub.2 --.phi.'--C(CF.sub.3).sub.2 -- ##STR3## and --CH.sub.2 (CF.sub.2).sub.6 CH.sub.2 --; n is zero or a positive integer; and X is hydrogen or methyl group.The resin of the invention may be prepared by reacting a diglycidyl ether of a fluorine-containing hydrocarbon (R.sub.f) with acrylic acid or methacrylic acid. Further provided is an adhesive composition comprising the aforementioned fluorine-containing epoxy(meth)acrylate resin and a photo polymerization initiator, which can be cured at room temperature within a short time by irradiation with an UV ray to form a cured product having a refractive index n.sub.d.sup.20 ranging from 1.434 to 1.532.Type: GrantFiled: April 3, 1989Date of Patent: November 26, 1991Assignee: Nippon Telegraph and Telephone CorporationInventors: Tohru Maruno, Shigeki Ishibashi, Kouzaburou Nakamura
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Patent number: 5063254Abstract: A polysiloxane comprising a linear polydiorganosiloxane chain joined at one terminus to an acrylic-functional end group, and joined at its other end to a cross-linked MTQ moiety comprising a multiplicity of monofunctional siloxane units (M), trifunctional siloxane units (T), and tetrafunctional siloxane units (Q), wherein the concentration ratio of M units to the sum of T units and Q units, M/(T+Q), in the MTQ moiety is from about 0.55 to about 0.75, and wherein the number of siloxy repeating units in the linear polydiorganosiloxane chain is from 25 to 1,000. The M and or /T units may also contain (meth)acrylate groups. The MTQ/silicone hybrid resins of the invention are curable by UV radiation, to provide high tensile strength silicone compositions having utility in potting and conformal coating apllications.Type: GrantFiled: November 27, 1989Date of Patent: November 5, 1991Assignee: Loctite CorporationInventor: Steven T. Nakos
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Patent number: 5045573Abstract: Compounds of the general formula I ##STR1## wherein Z is CR.sup.1 R.sup.2 (OR.sup.3) or phenyl,R.sup.1 being H, C.sub.1-6 -alkyl or phenyl,R.sup.2 being H, C.sub.1-6 -alkyl or C.sub.1-6 -alkoxy andR.sup.3 being H, C.sub.1-6 -alkyl or C.sub.1-6 -alkanoyl andZ' is Y-[(CH.sub.2).sub.m -X].sub.n -,X being CH.sub.2 or 0,Y being OH; COOH or SO.sub.3 H including the alkali metal, alkaline earth metal or ammonium salts thereof and also the salts thereof with organic nitrogen bases; or NRR' in which R and R' are in each case H, C.sub.1-20 -alkyl or C.sub.1-4 -hydroxyalkyl, if appropriate quaternized or in the form of the acid addition salts, andn and m each being the numbers 1-4, are excellently suitable as photoinitiators for the photopolymerization of ethylenically unsaturated compounds, in particular in aqueous systems.Type: GrantFiled: April 13, 1989Date of Patent: September 3, 1991Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Manfred Kohler, Jorg Ohngemach, Gregor Wehner, Jurgen Gehlhaus