With Ethylenic Reactant Patents (Class 522/96)
  • Patent number: 5805358
    Abstract: UV-curable Fresnel lens resin compositions ?1a! comprising a (meth)acrylate containing hydroxyl group and aromatic ring (A1), a urethane group-containing (meth)acrylate (A2) comprising an aromatic diol, an aromatic ring-containing monofunctional (meth)acrylate (A3), and a photopolymerization initiator (B) and ?1b! comprising (A1), a mono- or di(meth)acrylate monomer (A4), and (B), further supplemented with a polyester (C1) comprising an aromatic diol and a phosphate (C2) for the formation of a Fresnel lens on a sheet or plate made of a methyl methacrylate (co)polymer; a Fresnel lens formed by UV cure of composition ?1a! or ?1b!; and a rear projection screen including a sheet or plate carrying said Fresnel lens. The Fresnel lens has high refractive index, antistatic properties and is satisfactory in adhesion to a sheet or plate.
    Type: Grant
    Filed: July 29, 1996
    Date of Patent: September 8, 1998
    Assignees: Sanyo Chemical Industries, Ltd., Dainippon Printing Co., Ltd.
    Inventors: Tsutomu Yamashita, Michiharu Okubo, Makoto Honda, Futoshi Osawa
  • Patent number: 5804311
    Abstract: A liquid curable resin composition for optical fibers comprising a polymer (a) having a number average molecular weight of 5,000 or more and derived from at least two types of recurring ethylenic units, of which one type has a substituent group containing an ethylenically unsaturated group and the second type is substituted by a group --COOR.sup.3 (wherein R.sup.3 is a hydrogen atom or a hydrocarbon group having 1-30 carbon atoms), an aryl group, a cyano group, an alkyl group having 1-10 carbon atoms or by one or more halogen atoms.
    Type: Grant
    Filed: August 22, 1996
    Date of Patent: September 8, 1998
    Assignee: DSM N.V.
    Inventors: Mitsuhito Suwa, Zen Komiya, Yuji Takasugi, Takashi Ukachi
  • Patent number: 5801213
    Abstract: Radiation-curable compositions of reduced oxygen sensitivity comprisea) radiation-curable, free-radically polymerizable compounds, andb) capped amino compounds which are surface-active in compounds a) and on irradiation with high-energy light liberate amino compounds having primary, secondary or primary and secondary amino groups, the overall number of hydrogen atoms bonded in the amino groups (amine hydrogens) being at least 2.
    Type: Grant
    Filed: September 16, 1996
    Date of Patent: September 1, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhold Schwalm, Wolfgang Reich, Lukas Haussling, Erich Beck
  • Patent number: 5787218
    Abstract: A liquid curable resin composition containing urethane bond at a concentration of 2.0.times.10.sup.-3 mole/gm or more and comprising:(a) a urethane (meth)acrylate having at least three cyclic structures in the molecule;(b) a polymerizable mono-functional vinyl monomer of which the homopolymer has a glass transition point of 50.degree. C. or more; and(c) a polymerization initiator.The liquid curable resin composition possesses a high Young's modulus, exhibits very little contraction stress, has high tenacity and good curing characteristics. Along with these superior characteristics, the high reliability of the composition makes it a suitable coating material for optical fiber. Furthermore, since the resin composition possesses a high Young's modulus and high tenacity, it is also useful as a protective coating material for metals, plastics, wood, ceramics, glass, and the like.
    Type: Grant
    Filed: August 10, 1995
    Date of Patent: July 28, 1998
    Assignee: DSM NV
    Inventors: Tohru Ohtaka, Yuichi Hashiguchi, Mitsuhito Suwa, Katsutoshi Igarashi
  • Patent number: 5780526
    Abstract: An ultraviolet-curing liquid undercoating composition for use in metallizing FRP, which is a one-component type, has an unlimited pot life, and is excellent in adhesion and heat resistance. The composition comprises 20 to 80 parts by weight of a compound(s) containing at least two (meth)acryloyl groups in its molecule, 80 to 20 parts by weight of oil-modified alkyd resin(s), and 2 to 15 parts by weight of a sensitizer, optionally further 5 to 20 parts by weight of an amino resin based on 100 parts by weight in total of the above compound and the above alkyd resin(s). It is suited for the undercoating of an automotive reflector.
    Type: Grant
    Filed: November 14, 1996
    Date of Patent: July 14, 1998
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Sakae Matsui, Hiroyuki Nakamura, Shizuo Kudo, Hiroaki Konse
  • Patent number: 5763503
    Abstract: The disclosed method for making hollow shells (e.g. housing for in-ear hearing aids) employs a radiation-curable polymer comprising (a) a major amount of urethane methacrylate monomer (molecular weight 360-950) having a viscosity less than about 15,000 cps at 25.degree. C., (b) a viscosity-adjusting minor amount of unreacted hydroxyalkyl-methacrylate monomer, (c) a photoinitiating amount of a photoinitiator of the formula Ar.sup.1 --CO--C(OR).sub.2 --R', where Ar.sup.1 is aryl (e.g. phenyl), R is C.sub.1 -C.sub.4 -alkyl (e.g. methyl), and R' is hydrogen or alkyl or, preferably, aryl, and, optionally, (d) a coloring agent, e.g. a pigment concentrate. Viscosity control is of major importance; so the curable composition is generally solvent-free and free of viscosity-modifying solids (other than coloring agents). Acrylates (as distinct from methacrylates) are also omitted. The fully-formulated, curable composition is easily pourable and has a viscosity of less than about 2,000 cps.
    Type: Grant
    Filed: May 3, 1996
    Date of Patent: June 9, 1998
    Assignee: Esschem, Inc.
    Inventors: George F. Cowperthwaite, Gary R. Shaw, Susan C. Sheariss
  • Patent number: 5747552
    Abstract: An acrylic urethane prepolymer composition and an unsaturated polyester resin composition to which the prepolymer has been added. The prepolymer composition includes an acrylic urethane prepolymer prepared by the reaction of diisocyanate, like MDI, with an hydroxyl-containing acrylate monomer, such as a pentaerythritol triacrylate. The prepolymer composition contains a styrene monomer and an inhibitor, such as benzoquinone, to retard the reaction of the prepolymer and styrene monomer prior to the addition of the prepolymer composition into the polyester resin composition and a photoinitiator to promote the polymerization of the resin by exposure to radiant energy. The employment of the urethane prepolymer composition provides for the reduction in the amount of styrene monomer used in the unsaturated resin composition and also provides for improved chemical and physical properties of the photocured, unsaturated resin composition.
    Type: Grant
    Filed: September 12, 1996
    Date of Patent: May 5, 1998
    Assignee: Hehr International Inc.
    Inventor: Stuart B. Smith
  • Patent number: 5747551
    Abstract: A new UV curable pressure sensitive adhesive composition, which comprises in weight percent: about 0.1% to about 15% of a photoinitiator agent, about 10% to about 80% of a polyurethane resin with a pendent acrylate functionality, zero to about 70% by of an acrylate monomer, about 0.1% to about 25% by weight of a an acrylated polybutadiene component, and zero to about 50% by weight of a tackifier agent.
    Type: Grant
    Filed: August 22, 1996
    Date of Patent: May 5, 1998
    Assignee: Acheson Industries, Inc.
    Inventors: Mark A. Lewandowski, Anthony M. Chasser
  • Patent number: 5747550
    Abstract: 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: Grant
    Filed: June 5, 1995
    Date of Patent: May 5, 1998
    Assignee: Kimberly-Clark Worldwide, Inc.
    Inventors: Ronald Sinclair Nohr, John Gavin MacDonald
  • Patent number: 5744514
    Abstract: Coated optical fibers with radiation-curable coatings which include mercaptofunctional oligomers are disclosed. Specifically, the coatings may comprise the cured reaction products of mercapto-terminated urethane oligomers of number average molecular weight as determined by gel permeation chromatography (GPC) of at least about 3,000 daltons, particularly in combination with one or more (meth)acrylate-terminated urethane oligomers; monomer diluents; and optional silane adhesion promoter, photoinitiator and stabilizers. The coatings, when cured, exhibit a percent extractables content, as obtained by Soxhlet extraction, of no more than about 15%, and preferably of no more than about 8%, and a volatiles content, as obtained by thermogravimetric analysis, of less than about 7%, and preferably less than about 3%. Processes for preparing such coated optical fibers and the coatings per se are also disclosed.
    Type: Grant
    Filed: October 31, 1996
    Date of Patent: April 28, 1998
    Assignee: Borden Chemical, Inc.
    Inventor: Paul J. Shustack
  • Patent number: 5744512
    Abstract: 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: Grant
    Filed: March 20, 1996
    Date of Patent: April 28, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Manfred Kohler, Jorg Ohngemach, Eike Poetsch, Rudolf Eidenschink, Gerhard Greber, Dieter Dorsch, Jurgen Gehlhaus, Konrad Dorfner, Hans Ludwig Hirsch
  • Patent number: 5736298
    Abstract: A photo-sensitive resin composition is provided which contains (1) a particulate polymer of a carboxy-group-containing-diene having a cross-linked structure; (2) a polymer having two or more photo-polymerizable unsaturated groups at its molecular chain terminals, and, optionally, a photo-polymerizable unsaturated group, carboxyl group, hydroxy group, amino group, or epoxy group in side chains, or (2') a non-diene-type polymer having a photo-polymerizable unsaturated group, carboxyl group, hydroxy group, amino group, or epoxy group in side chains, or a low molecular weight linear diene-type polymer; (3) a photo-polymerizable unsaturated monomer; (4) a polymer containing an amino group; and (5) a photo-polymerization initiator. The photo-sensitive resin composition has excellent water-developing capability and shows almost no swelling in water, causing minimal reduction in strength and only minimal dimensional changes during development.
    Type: Grant
    Filed: October 2, 1995
    Date of Patent: April 7, 1998
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Katsuo Koshimura, Takayoshi Tanabe, Hozumi Sato, Noboru Ohshima, Takashi Nishioka
  • Patent number: 5733948
    Abstract: A photopolymer resin composition useful in producing printing plates with low levels of surface tack is disclosed. Acetal compounds are incorporated into the photopolymer resin composition to achieve the low tack results.
    Type: Grant
    Filed: July 15, 1996
    Date of Patent: March 31, 1998
    Assignee: MAC Dermid, Imaging Technology, Inc.
    Inventor: Lawrence Nelson
  • Patent number: 5731388
    Abstract: Photocurable resins containing unsaturated urethane of a specified form and vinyl monomer which is N-(meth)acryloylmorpholine or its mixture with di-ol di(meth)acrylate at a rate within a specified range and compositions containing such a resin and a filler such as solid particles and/or inorganic whiskers of specified kinds at a specified rate are capable of yielding stereo lithographed objects with improved mechanical and thermal properties and form precision.
    Type: Grant
    Filed: November 7, 1995
    Date of Patent: March 24, 1998
    Assignee: Takemoto Yushi Kabushiki Kaisha
    Inventors: Toshiharu Suzuki, Tatsuhiko Ozaki, Hirokazu Matsueda
  • Patent number: 5723513
    Abstract: Radiation-sensitive organo-halogen compounds that have a photo-labile halomethyl-1,3,5-triazine moiety and a polymeric moiety within the same molecule. The compounds of this invention are comprised of a polymeric moiety having attached or incorporated within its structure at least one 1,3,5-triazine nucleus, said triazine nucleus having at least one halomethyl substituent attached to a carbon atom of the triazine nucleus. These compounds are capable of being stimulated by actinic radiation at wavelengths of from about 250 to about 900 nanometers to generate free radicals and/or acids. The compounds of this invention are useful as photoinitiators in free radical polymerization reactions, oxidation-reduction reactions, or reactions sensitive to acid, and they also exhibit the capability to crosslink upon exposure to light.
    Type: Grant
    Filed: March 8, 1996
    Date of Patent: March 3, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: James A. Bonham, Mitchell A. Rossman, Richard J. Grant
  • Patent number: 5719227
    Abstract: Floor coverings include a wear layer made from a coat composition including a multifunctional polyurethane (meth)acrylate oligomer. The multifunctional polyurethane is made by reacting a polyisocyanate with a functionality equal or higher than 3, a polyester polyol, and a hydroxyalkyl-(meth)acrylate with a number average molecular weight of about 344 to about 472. The coating composition preferably includes a reactive (meth)acrylate diluent and a photoinitiator.
    Type: Grant
    Filed: May 9, 1997
    Date of Patent: February 17, 1998
    Assignee: Armstrong World Industries, Inc.
    Inventors: Angela S. Rosenberry, Claude R. Rupp, Songvit Setthachayanon
  • Patent number: 5716757
    Abstract: The present invention provides a liquid photosensitive resin composition used for forming a printing plate to print on a corrugated board comprising:(A) 100 parts by weight of an unsaturated polyurethane prepolymer having a polyether polyol as a polyol segment,(B) 17 to 200 parts by weight of an ethylenically unsaturated compound and(C) 0.01 to 10 parts by weight of a photopolymerization initiator, characterized by comprising 17 to 65 parts by weight of an acrylate monomer represented by the following formula (I) per 100 parts by weight of the prepolymer of component (A) as the ethylenically unsaturated compound of component (B):CH.sub.2 .dbd.CH--CO--O--(C.sub.2 H.sub.4 O).sub.n --R (I)wherein n represents a number of 1 to 20, R represents a linear or branched alkyl group having 2 to 22 carbon atoms.A printing plate for use in printing a corrugated board obtained by curing the present composition has an increased impact resilience.
    Type: Grant
    Filed: May 17, 1995
    Date of Patent: February 10, 1998
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Norihiko Sakata, Shusaku Tabata, Yoko Ueno
  • Patent number: 5712324
    Abstract: A radiation curable, organic coating for improving the weatherability of a thermoplastic resin substrate employs as a polymerizable, cross-linking monomer component, a 2-hydroxy-5-acrylyloxyphenyl-2H-benzotriazole.
    Type: Grant
    Filed: November 21, 1996
    Date of Patent: January 27, 1998
    Assignee: General Electric Company
    Inventor: Kenneth L. Lilly
  • Patent number: 5709955
    Abstract: An adhesive composition, a laminated structure, and a method of laminating a structure. The adhesive composition comprises an admixture of unsaturated polymerizable material and a photoreactor, the photoreactor comprising a wavelength-specific sensitizer covalently bonded to a reactive species-generating photoinitiator. Suitable wavelength-specific sensitizers have a molar extinction coefficient greater than about 5000 liters per mole per cm at an absorption maximum and resulting photoreactors have a quantum yield of greater than about 0.5 at an absorption maximum. Suitable photoreactors include 2-?p-(2-methyllactoyl)phenoxy!ethyl-1,3-dioxo-2-isoindolineacetate, 2-hydroxy-2-methyl-4'-?2-?p-(3-oxobutyl)phenoxy!ethoxy!propiophenone, 4-?p-?(4-benzoylcyclohexyl)oxy!phenyl!-2-butanone, and 1,3-dioxo-2-isoindolineacetic acid diester with 2-hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone.
    Type: Grant
    Filed: October 16, 1996
    Date of Patent: January 20, 1998
    Assignee: Kimberly-Clark Corporation
    Inventors: Ronald Sinclair Nohr, John Gavin MacDonald
  • 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: 5696179
    Abstract: The invention provides a silane-oligomer (A) of the following formula:(R.sup.3)--X--(R.sup.1.sub.x)--Y--Si(R.sup.2).sub.3 ( 1)wherein R.sup.3 is a group having a functionality that can be polymerized through actinic radiation, R.sup.1.sub.x is a backbone-oligomer having a molecular weight of more than about 200, R.sup.2 is a hydrolyzable group, and X and Y are coupling groups. The invention also provides a glass coating composition containing the silane-oligomer.
    Type: Grant
    Filed: December 8, 1994
    Date of Patent: December 9, 1997
    Assignee: DSM, N.V.
    Inventor: Chander P. Chawla
  • Patent number: 5688633
    Abstract: A photosensitive resin composition includes a urethane oligomer prepared from a hydroxy-functionalized acrylate and/or methacrylate, at least one diol, and 2,4-toluene diisocyanate and 2,6-toluene diisocyanate in a 65:35 weight ratio. The resin composition additionally contains a monomer having at least one acrylate or methacrylate group, and a photoreactive initiator. The photosensitive resin composition may be cured to provide a soft photopolymer printing plate, particularly well suited for printing on corrugated bard.
    Type: Grant
    Filed: September 6, 1996
    Date of Patent: November 18, 1997
    Assignee: MacDermid Imaging Technology, Inc.
    Inventor: Douglas R. Leach
  • Patent number: 5685754
    Abstract: A polymer coated fiber, a polymer-coated web, and a method of coating a fiber or a web. The fiber or web is coated with a composition comprising an admixture of unsaturated polymerizable material and a photoreactor, and the composition on the fiber or web is irradiated with an amount of radiation sufficient to cure the composition and form a coating on the fiber or web. The photoreactor comprises a wavelength-specific sensitizer covalently bonded to a reactive species-generating photoinitiator. Suitable wavelength-specific sensitizers have a molar extinction coefficient greater than about 5000 liters per mole per cm at an absorption maximum and resulting photoreactors have a quantum yield of greater than about 0.5 at an absorption maximum.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: November 11, 1997
    Assignee: Kimberly-Clark Corporation
    Inventors: Ronald Sinclair Nohr, John Gavin MacDonald
  • Patent number: 5686503
    Abstract: 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: Grant
    Filed: January 22, 1996
    Date of Patent: November 11, 1997
    Assignee: Kimberly-Clark Corporation
    Inventors: Ronald Sinclair Nohr, John Gavin MacDonald
  • Patent number: 5679722
    Abstract: A resin composition for production of a three-dimensional object by curing, which comprises a) a liquid photocurable resin, and b) a reinforcing agent selected from an inorganic solid particle having an average particle diameter of 3 to 70 .mu.m, whisker having an average particle diameter of 0.3 to 1.0 .mu.m, a length of 10 to 70 .mu.m and an aspect ratio of 10 to 100, and a combination of these.
    Type: Grant
    Filed: January 24, 1996
    Date of Patent: October 21, 1997
    Assignee: Teijin Seiki Co., Ltd.
    Inventor: Yorikazu Tamura
  • Patent number: 5679721
    Abstract: A radiation-curable coating composition comprising a PVC resin, an acrylic or methacrylic compound and a radiation-reactive urethane oligomer. Also described is a process for coating a material, comprising the steps of applying to the material a coating composition according to the invention, heating to heart-cure the coating composition and irradiating the composition to radiation-cure the coating composition. There is also provided an article comprising a material coated with the composition according to the invention. The invention is particularly useful for coating resilient vinyl flooring materials.
    Type: Grant
    Filed: February 27, 1995
    Date of Patent: October 21, 1997
    Assignee: Domco Industries Ltd.
    Inventors: Jean-Fran.cedilla.ois Courtoy, Claude Charest
  • Patent number: 5674921
    Abstract: A radiation-curable prepolymer of a polyurethane endtipped with an hydroxy (acrylate or methacrylate) is disclosed. The polyurethane is derived from the reaction of a polyfunctional isocyanate with a hydrolyzable oligomer of an anhydrous cyclic ester of an hydroxy acid. Crosslinked polymers prepared by irradiating the prepolymers are also disclosed. The crosslinked polymers are bioabsorbable and biocompatible with bodily tissue, yet still maintain the outstanding mechanical properties one would expect from a polyurethane. The prepolymers and crosslinked polymers are especially well-suited for the fabrication of surgical devices, particularly wound closure devices such as surgical staples and clips, in a stereolithography apparatus.
    Type: Grant
    Filed: February 1, 1995
    Date of Patent: October 7, 1997
    Assignee: Ethicon, Inc.
    Inventors: Donald W. Regula, Michael F. Bregen, Stuart L. Cooper, Dennis D. Jamiolkowski, Rao S. Bezwada
  • 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: 5667856
    Abstract: A pigmented ink composition comprising a radiation curable component and a pyrrolopyrrol or isoindolinone pigment; a method for decorating a substrate with the pigmented ink compositions; and a method for decorating a substrate with hot stamping foil and the pigmented ink compositions.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: September 16, 1997
    Assignee: Revlon Consumer Products Corporation
    Inventors: Melvin Edwin Kamen, Bhupendra Patel
  • Patent number: 5629358
    Abstract: A photocurable resin composition comprising the components (a), (b), (c) and (d) or the components (a), (b) and (e) of the following components:(a) a polymerisable compound having at least one ethylenically unsaturated group per molecule;(b) a photopolymerisation initiator;(c) the hydrolysis product of at least one compound of the general Formula: ##STR1## wherein R.sup.1 represents a hydrogen atom or lower alkyl group, A represents --O--or --NH--, R.sup.2 represents a C.sub.1-6 -alkylene group, R.sup.3 represents a lower alkyl group, X represents a lower alkoxy group or halogen atom and m represents 0, 1 or 2;(d) at least one compound of the general formula: ##STR2## wherein R.sup.4 represents a glycidoxy or C.sub.5-6 -epoxycycloalkyl group, R.sup.5 represents a C.sub.1-6 -alkylene group, R.sup.
    Type: Grant
    Filed: December 22, 1992
    Date of Patent: May 13, 1997
    Assignee: Imperial Chemical Industries PLC
    Inventors: Masaji Nagahata, Hiroshi Masaoka
  • Patent number: 5629804
    Abstract: A diffraction grating is constituted by a substrate and a resin layer having a repetitive pattern formed on the substrate. The resin layer is characterized by showing a Young's modulus at 100.degree. C. which is at least 2% of that at 20.degree. C. The resin layer may be obtained by curing a photocurable resin composition, including: (A) a polyfunctional urethane-modified polyester (meth)acrylate comprising a polyester oligomer and a plurality of (meth)cryloyl groups bonded to the polyester oligomer via a urethane group, and having a number-average molecular weight of at least 700, (B) a polyfunctional (meth)acrylate having a number-average molecular weight of less than 700, (C) a monofunctional (meth)acrylate, and (D) a photopolymerization initiator.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: May 13, 1997
    Assignee: Canon Kabushiki Kaisha
    Inventor: Haruo Tomono
  • Patent number: 5629359
    Abstract: Radiation curable compositions, comprising, per 100 parts by weight,(a) at least 20 parts by weight of at least one radiation polymerizable compound containing at least two groups selected from CH.sub.2 .dbd.CH--COO-- and CH.sub.2 .dbd.C(CH.sub.3)--COO-- and(b) at least 5 parts by weight of at least one (2-oxo-1-pyrrolidinyl)alkyl acrylate or methacrylate of the formula: ##STR1## wherein R represents an alkylene radical containing 2 to 4 carbon atoms and R.sub.1 represents a hydrogen atom or a methyl radical.These radiation curable compositions exhibit a high speed of curing by ultraviolet irradiation or by an accelerated electron beam, and are suitable for the production of coatings with excellent qualities such as good adhesion to the most diverse substrates, a high surface hardness, an improved abrasion resistance and chemical resistance, and good mechanical properties.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: May 13, 1997
    Assignee: U C B S.A.
    Inventors: Stephan Peeters, Ivan Vanden Eynde, August Van Gysel, Jean-Marie Loutz
  • Patent number: 5629445
    Abstract: This invention relates to (meth)acrylates represented by formula (1): ##STR1## wherein, R.sub.1 and R.sub.2 are each independently H or CH.sub.3 and average value of n is 1-5; resin composite comprising (A) an urethane (meth)-acrylate and/or epoxy (meth)acrylate, (B) a (meth)-acrylate represented by formula (1) above, (C) an ethylenically unsaturated compound other than component (A) or (B), and (D) a photopolymerization initiator; and cured products of said resin composites. The cured products of said resin composites of this invention have high refractive index and are superior in mold release property, shape reproducibility, restorability, and scratch resistance and suited in particular for transmission type screens.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: May 13, 1997
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Kenji Nakayama, Katsunori Shimura, Minoru Yokoshima, Nobuo Taniguchi
  • Patent number: 5624974
    Abstract: A photopolymerizable resin material composition for forming a polymer used for a liquid crystal display apparatus includes at least one acrylate compound selected from the group consisting of a bifunctional acrylate compound having a fluorine substitution ratio .alpha. in the range of 0.1<.alpha.<0.8, a bifunctional acrylate compound having a fluorine substitution ratio .alpha. in the range of 0.ltoreq..alpha.<0.8, a bifunctional acrylate compound having a fluorine substitution ratio .alpha. in the range of 0.1<.alpha.<0.8, a bifunctional acrylate compound having a fluorine substitution ratio .alpha. in the range of 0.1<.alpha.<0.8 and a bifunctional acrylate compound having a fluorine substitution ratio .alpha. in the range of 0.1<.alpha.<0.8 and a bifunctional acrylate compound having a fluorine substitution ratio .alpha. in the range of 0.1<.alpha.<0.8, and a photopolymerization delaying resin material.
    Type: Grant
    Filed: December 27, 1995
    Date of Patent: April 29, 1997
    Assignees: Sharp Kabushiki Kaisha, Nippon Kayaku Co., Ltd.
    Inventors: Noriaki Onishi, Nobuaki Yamada, Shuichi Kohzaki, Daisaku Matsunaga, Takao Aizawa, Toru Ozaki
  • Patent number: 5616630
    Abstract: An ester/urethane acrylate hybrid oligomer which is the reaction product of an acrylate/hydroxy-functional polyester, an isocyanate compound, and a hydroxy-functional acrylate compound. The acrylate/hydroxy-functional polyester is prepared by reacting a polyester polyol and an acrylate compound. The polyester backbone of the oligomer has both ester and urethane linkages to the terminal acrylate functionality. This hybrid nature of the polyester backbone provides an oligomer which can be utilized at low viscosity to facilitate processing while maintaining effective stain resistance and flexibility.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: April 1, 1997
    Assignee: Lord Corporation
    Inventor: Richard E. Heinze
  • Patent number: 5607813
    Abstract: The present invention provides an imaging element comprising on a support a photosensitive layer containing a photopolymerizable composition containing a urethane type monomer mixture according to the formula (I) as defined in the claims and description. There is further provided a method for obtaining images and/or a lithographic printing plate therewith.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: March 4, 1997
    Assignee: Agfa-Gevaert, N.V.
    Inventors: Herman J. Uytterhoeven, Michael M uller, Wolfgang Podszun, Marc I. Van Damme, Hans-Josef Laas
  • Patent number: 5591563
    Abstract: Photocurable resins containing unsaturated urethane of a specified form and vinyl monomer which is N-(meth)acryloylmorpholine or its mixture with di-ol di(meth)acrylate at a rate within a specified range and compositions containing such a resin and a filler such as solid particles and/or inorganic whiskers of specified kinds at a specified rate are capable of yielding stereolithographed objects with improved mechanical and thermal properties and form precision.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: January 7, 1997
    Assignee: Takemoto Yushi Kabushiki Kaisha
    Inventors: Toshiharu Suzuki, Tatsuhiko Ozaki, Hirokazu Matsueda
  • Patent number: 5587405
    Abstract: A radiation-curable ink composition contains a vehicle mixture comprising: (A) at least one linear polyester oligomer and/or polymer substantially free of an acid group and free of a polymerizable double bond in a molecule, wherein 1 to 10 double bonds are pendent from the linear polyester chain, and/or mixture thereof, (B) at least one single double bond-containing carboxylic acid wherein the acid has at least one acid group, and/or carboxylic ester of the said acid, and/or carboxylic amide of the said acid, and/or mixture thereof, (C) a double bond-containing polycarboxylic ester, wherein 2 to 10 acid groups are present and at least 2 double bonds are pendent from the ester having 2 to 10 acid groups, (D) at least one double bond-containing fluorinated carboxylic ester, and/or block copolymer comprising a fluorinated alkyl group-containing polymer segment and a (meth)acrylic polymer segment, and/or block copolymer comprising a siloxane group-containing polymer segment and a (meth)acrylic polymer segment, an
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: December 24, 1996
    Assignees: Yoshino Kogyosho Co., Ltd., Hayakawa Rubber Co., Ltd.
    Inventors: Ban Tanaka, Hiroki Nii, Kosaku Yamada, Hideo Kushida, Takashi Miya, Shuichi Koshio, Tadashi Hayakawa
  • Patent number: 5587403
    Abstract: Ultraviolet radiation-curable primary coating compositions for optical fibers are disclosed. The primary coatings comprise a polyether polyol-based reactively terminated aliphatic urethane oligomer; one or more diluent monomers terminated with at least one end group capable of reacting with the reactive terminus of the oligomer; an organofunctional silane adhesion promoter; and an optional photoinitiator. Also disclosed are optical fibers coated with the coatings of the invention, and processes for preparing same.
    Type: Grant
    Filed: January 17, 1996
    Date of Patent: December 24, 1996
    Assignee: Borden, Inc.
    Inventor: Paul J. Shustack
  • Patent number: 5569725
    Abstract: A class of unsaturated resins which are suitable for use in radiation curable coatings has been developed. The resins comprise N-vinyl-N-acyl oligomers made by reacting a secondary N-vinylamide with a polyisocyanate monomer which is reacted with at least one mono- or polyhydric alcohol to form a urethane linkage.
    Type: Grant
    Filed: October 14, 1994
    Date of Patent: October 29, 1996
    Assignee: Air Products and Chemicals, Inc.
    Inventors: W. Eamon Carroll, Walter L. Renz, Andrew F. Nordquist, Robert K. Pinschmidt, Jr.
  • Patent number: 5569705
    Abstract: There are described aqueous dispersions of polyurethane resins, the production thereof and their use in aqueous coating agents, said dispersions being obtainable in aqueous or non-aqueous phase froma) polyurethane resins with at least one CH acidic group, an ionic or non-ionic hydrophilic group and, optionally, OH and/or NH groups, byb) introduction of olefinic double bonds by reaction withb.sub.1) compounds with a CH acidic group and an olefinic double bond, and/orb.sub.2) compounds with an olefinic double bond and also a group that is capable of reacting with CH acidic groups, and/orb.sub.3) compounds with an olefinic double bond and also a group that is capable of reacting with OH or NH groups, orb.sub.4) formaldehyde,whereupon, optionally, conversion into the aqueous phase and radical polymerization are effected.
    Type: Grant
    Filed: February 27, 1995
    Date of Patent: October 29, 1996
    Assignee: Herberts Gesellschaft Mit Beschrankter Haftung
    Inventors: Bettina Vogt-Birnbrich, Hans-Peter Patzschke, Werner Lenhard, Jurgen Dobert, Marcus Brunner, Walter Schubert
  • Patent number: 5566027
    Abstract: A resin layer having an improved durability may be obtained by curing a photocurable resin composition, including: (A) a polyfunctional urethane-modified polyester (meth)acrylate comprising a polyester oligomer and a plurality of (meth)acryloyl groups bonded to the polyester oligomer via a urethane group, and having a number-average molecular weight of at least 700, (B) a polyfunctional (meth)acrylate having a number-average molecular weight of less than 700, (C) a monofunctional (meth)acrylate, and (D) a photopolymerization initiator. The cured resin layer shows a Young's modulus which shows a small temperature-dependence, and reduces the possibility of peeling of an optional overcoating layer formed thereon.
    Type: Grant
    Filed: December 11, 1995
    Date of Patent: October 15, 1996
    Assignee: Canon Kabushiki Kaisha
    Inventors: Osamu Saitoh, Haruo Tomono
  • Patent number: 5554712
    Abstract: A photopolymer useful in preparing water-developable, solid printing plates is prepared by preparing a urethane prepolymer by reacting polyoxyalkylene diols or polyester diols, or a mixture thereof, with an excess of diisocyanate, followed by chain extending the resulting prepolymer mixture with an alkyldialkanolamine, then reacting the chain-extended product with a hydroxyalkyl(meth)acrylate. The resulting photopolymer is suitably formulated with additional photoactive (meth)acrylate monomers or oligomers and photoinitiator for casting or extrusion on a substrate to form a flexographic printing plate. Following UV exposure of the plate through a negative, unexposed areas can be removed by washing with a slightly acidic aqueous medium, to give a plate with a desirable relief image. The use of the aqueous washout solution as opposed to organic solvents minimizes pollution problems.
    Type: Grant
    Filed: May 19, 1994
    Date of Patent: September 10, 1996
    Assignee: W.R. Grace & Co.-Conn.
    Inventors: Truc-Chi T. Huynh-Tran, Ronald J. Kumpfmiller, Cynthia L. Ebner
  • Patent number: 5548005
    Abstract: Aqueous, radiation-curable binders and binder dispersions are disclosed that contain (A) a radiation-curable binder, and (B) a radiation-curable, hydrophilic polyepoxy-acrylate.
    Type: Grant
    Filed: December 16, 1994
    Date of Patent: August 20, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Inge Kurth, Gerhard Brindoepke, Manfred Marten
  • Patent number: 5538791
    Abstract: Ultraviolet radiation-curable primary coating compositions for optical fibers are disclosed. The primary coatings comprise a polyether polyol-based reactively terminated aliphatic urethane oligomer; one or more diluent monomers terminated with at least one end group capable of reacting with the reactive terminus of the oligomer; an organofunctional silane adhesion promoter; and an optional photoinitiator. Also disclosed are optical fibers coated with the coatings of the invention, and processes for preparing same.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: July 23, 1996
    Assignee: Borden, Inc.
    Inventor: Paul J. Shustack
  • 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: 5536758
    Abstract: A formulation for a resilient gasket coating which is curable by ultraviolet radiation without emitting fumes into the surrounding environment. Different portions of the coating are cured by successive exposure to two different wavelengths of ultraviolet radiation during a continuous in-line process. The first wavelength cures an inner portion of the coating and bonds the coating to the substrate. The second wavelength cures a coating surface. The formulation permits ultraviolet curing of thicker pigmented coatings than have been previously known.
    Type: Grant
    Filed: July 27, 1993
    Date of Patent: July 16, 1996
    Assignee: Dana Corporation
    Inventor: Brent R. Boldt
  • Patent number: 5527835
    Abstract: Ultraviolet radiation-curable primary coating compositions for optical fibers are disclosed. The primary coatings comprise a polyether polyol-based reactively terminated aliphatic urethane oligomer; one or more diluent monomers terminated with at least one end group capable of reacting with the reactive terminus of the oligomer; an organofunctional silane adhesion promoter; and an optional photoinitiator. Also disclosed are optical fibers coated with the coatings of the invention, and processes for preparing same.
    Type: Grant
    Filed: November 16, 1994
    Date of Patent: June 18, 1996
    Assignee: Borden, Inc.
    Inventor: Paul J. Shustack
  • Patent number: 5521228
    Abstract: A method for forming simulated hair strands on the scalp by utilizing a composition containing an ethylenically unsaturated monomer and a photoinitiator. The composition is applied to the scalp, strands are formed and the strands are cured by light.
    Type: Grant
    Filed: January 17, 1995
    Date of Patent: May 28, 1996
    Inventors: Michael R. Weber, Paul J. Weber