Polyurethane Has An Oxygen Other Than As Part Of A Urethane Or Carboxylic Acid Ester Group Patents (Class 522/97)
  • Patent number: 5952154
    Abstract: The invention provides a negative-acting photoimageable composition comprising A) between about 30 and about 80 wt % based on total weight of A) plus B) of a binder polymer having acid functionality sufficient to render said photoimageable composition developable in alkaline aqueous solution, B) between about 20 and about 70 wt % based on total weight of A) plus B) of an addition-polymerizeable, non-gaseous .alpha.,.beta.-ethylenically unsaturated compound(s) capable of forming a high polymer by free-radical initiated chain-propagating addition polymerization, at least about 50 mole percent of the .alpha.,.beta.-ethylenically unsaturated moieties of B) being methacrylic moieties, and C) between about 0.1 and about 20 wt % based on total weigh of A) plus B) of a photoinitiator chemical system. Photopolymerizable component B comprises, at between about 1 and about 70 wt. % relative to total of A) plus B), a urethane oligomer having, in addition to .alpha.,.beta.
    Type: Grant
    Filed: May 29, 1998
    Date of Patent: September 14, 1999
    Assignee: Morton International, Inc.
    Inventors: Robert Barr, Daniel Lundy, Stephen Wheeler
  • Patent number: 5945463
    Abstract: A composition for a gasket which comprises (A) 100 parts by weight of a urethane acrylate oligomer having a weight-average molecular weight of 7,000 to 40,000, (B) 40 to 260 parts by weight of a polyether monoacrylate substituted at the end and/or a polyether polyester monoacrylate substituted at the end, and (C) 0.5 to 5 parts by weight of a photopolymerization initiator and has a viscosity of 4,000 to 100,000 centipoises at 25.degree. C.; and a process for producing a gasket by discharging the above composition on a substrate by using an X-Y-Z-driving automatic coating robot and curing the discharged composition by irradiation of ultraviolet light.A gasket can be formed to an accurate shape. Operations of forming and attaching the gasket can easily be conducted, and loss of the used material can be reduced. The gasket has a large tearing strength and a small compression set and is excellent in the flexibility and the sealing property.
    Type: Grant
    Filed: March 28, 1997
    Date of Patent: August 31, 1999
    Assignees: Zeon Rize Co., Ltd., Sunarrow Limited
    Inventors: Ichiro Kawabuchi, Tetsuro Yamada, Yoshio Kenmochi, Atsuo Ishikawa
  • 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: 5925715
    Abstract: A dental cement system containing a photocurable ionomer, reactive powder and water undergoes both a conventional setting reaction and a photocuring reaction.The cement system can provide a long working time and can be cured on demand by exposure to an appropriate source of radiant energy. The surface of the cement cured in this manner is then hard enough to allow subsequent clinical procedures to be performed, while the ongoing chemical-cure "setting" reaction hardens the remainder of the cement.
    Type: Grant
    Filed: November 12, 1997
    Date of Patent: July 20, 1999
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Sumita B. Mitra
  • Patent number: 5919569
    Abstract: A photosensitive resin composition comprising the following components (A), (B), (C) and (D): (A) a photopolymerizable urethane (meth)acrylate compound containing at least two acryloyl or methacryloyl groups, (B) an alkali-soluble polymer compound having an acid value of from 50 to 250 mgKOH/g, and (C) a photopolymerization initiator, (D) a polymeric complex of an alkali thioxanate wherein the photosensitive resin composition has an electrical insulation resistance of 8.0.times.10.sup.9 to 1.0.times.10.sup.14 .OMEGA..multidot.cm after photocuring. A photosensitive resin laminated film comprising a flexible film, a photosensitive layer provided on the flexible film, and a releasable film layer provided on the photosensitive layer, wherein the photosensitive layer comprises the above photosensitive resin composition.
    Type: Grant
    Filed: November 17, 1997
    Date of Patent: July 6, 1999
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroyuki Obiya, Ryuma Mizusawa
  • Patent number: 5908873
    Abstract: A one-part, cured, radiation-curable liquid matrix composition for affixing coated and inked optical fibers in a ribbon configuration which is peelable from the coated and inked fibers without damage to the integrity of itself or the fibers is disclosed. The composition comprises an aliphatic urethane acrylate oligomer; a reactive monomer having one or more acrylate or methacrylate moieties; a release agent; and an optional photoinitiator. Also disclosed are an optical fiber ribbon array prepared therefrom; a process for removing such matrix composition from inked and coated fibers; a process for preparing such ribbon array; and a radiation-curable coating composition generally applicable for coating a substrate.
    Type: Grant
    Filed: December 20, 1995
    Date of Patent: June 1, 1999
    Assignee: Borden Chemicals, Inc.
    Inventor: Paul J. Shustack
  • Patent number: 5900473
    Abstract: The present invention discloses radiation curable pressure-sensitive adhesives comprising the reaction product of a blend of at least two hydroxy polyesters having different Tgs, and at least one prepolymer functionalized with (Meth) acrylates, isocyanates and mixtures thereof. The present invention further discloses a blend of at least two hydroxy polyesters wherein at least one of the hydroxy polyesters has a Tg of less than -35.degree. C., and at least one of the other hydroxy polyesters has a Tg of greater than about -35.degree. C.
    Type: Grant
    Filed: June 2, 1998
    Date of Patent: May 4, 1999
    Assignee: H.B. Fuller Licensing & Financing, Inc.
    Inventors: Margarita Acevedo, Hans F. Huber
  • Patent number: 5859087
    Abstract: Provided is a radiation-curable primer coating composition, which is adapted to provide a printable primer coating on a polyolefin surface that is functionally resistant to delamination from the polyolefin surface over the temperature range from heat pasteurization temperatures to freezer storage temperatures. The primer composition being formulated from the following components:at least one monomer or oligomer having at least one functional group that polymerizes when exposed to radiation; andan effective amount of at least one zirconate or titanate, or a mixuture of a titanate and zirconate, to increase adhesion of the radiation-cured primer coating to said polyolefin surface.
    Type: Grant
    Filed: October 16, 1996
    Date of Patent: January 12, 1999
    Assignee: DSM NV
    Inventor: Edward P. Zahora
  • Patent number: 5851700
    Abstract: A filter for a liquid crystal display device, having a light diffusing plate which is obtained by forming a composition in the form of a film which contains at least two photopolymerizable oligomers or monomers having refractive indexes which differ from each other by at least 0.01 and irradiating UV light on the composition. When the filter is fitted to a light emitting side of a liquid crystal display device, an angle of view of the liquid crystal display face plane is widened, shadows due to opaque parts of the device are reduced, and a Moire fringe is hardly formed.
    Type: Grant
    Filed: February 28, 1997
    Date of Patent: December 22, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masaru Honda, Shigeo Hozumi, Shinichiro Kitayama
  • Patent number: 5837750
    Abstract: Provided is a radiation-curable, glass optical fiber coating composition which when suitably cured exhibits resistance to attack from hydrocarbon gel cable filing material. The composition containsabout 10 to about 90% by weight of a first radiation-curable oligomer;from 0 to about 40% by weight of a reactive diluent;from 0 to about 40% by weight of a photoinitiator;from 0 to about 10% by weight of a pigment; andabout 10 to about 90% by weight of a second radiation-curable oligomer according to the following formula:R.sup.1 -L.sup.1 -C.sup.1 -L.sup.2 -R.sup.2 (1)where:R.sup.1 and R.sup.2, independently, each represent a radiation-curable functional group;L.sup.1 and L.sup.2, independently, each represent an alkyleneoxy chain having from about 2 to about 40 carbon atoms, wherein L.sup.1 and L.sup.2 are linked to C.sup.1 through an oxygen atomC.sup.1 comprises a hydrocarbon having from about 5 to about 40 carbon atoms and containing at least one cyclic group.
    Type: Grant
    Filed: March 12, 1996
    Date of Patent: November 17, 1998
    Assignee: DSM N.V.
    Inventors: David M. Szum, Timothy E. Bishop, Steven R. Schmid
  • 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: 5776995
    Abstract: A photosensitive resin composition comprising the following components (A), (B) and (C): (A) a photopolymerizable urethane (meth)acrylate compound containing at least two acryloyl or methacryloyl groups, (B) an alkali-soluble polymer compound having an acid value of from 50 to 250 mgKOH/g, and (C) a photopolymerization initiator, wherein the photosensitive resin composition has an electrical insulation resistance of 8.0.times.10.sup.9 to 1.0.times.1.0.sup.14 .OMEGA..multidot.cm after photocuring. A photosensitive resin laminated film comprising a flexible film, a photosensitive layer provided on the flexible film, and a releasable film layer provided on the photosensitive layer, wherein the photosensitive layer comprises the above photosensitive resin composition.
    Type: Grant
    Filed: October 25, 1996
    Date of Patent: July 7, 1998
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroyuki Obiya, Ryuma Mizusawa
  • Patent number: 5741829
    Abstract: Radiation-curable (meth)acrylates obtainable by reacting compounds of the formula ##STR1## in which R is C.sub.1 -C.sub.4 -alkyl, aryl or R.sup.1 and R.sup.1 is ##STR2## in which R.sup.2 to R.sup.6 independently of one another are H, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, OH, phenyl, SH, SCH.sub.3, SC.sub.2 H.sub.5, F, Cl, Br, CN, COOH, COO--(C.sub.1 -C.sub.17 -alkyl), COO--(C.sub.5 -C.sub.10 -aryl), CF.sub.3, N(alkyl).sub.2, N(alkyl)(aryl), N(aryl).sub.2, N.sup..sym. (alkyl).sub.3 A.sup..crclbar., N.sup..sym. H(alkyl).sub.2 A.sup..crclbar., A.sup..crclbar. is the anion of an acid, and alkyl or aryl, unless indicated otherwise, is C.sub.1 -C.sub.10 -alkyl or C.sub.5 -C.sub.10 -aryl, respectively, and at least one but not more than 3 of R.sup.2 to R.sup.6 are ##STR3## with hydroxy(meth)acrylates containing at least 1 free hydroxyl group and at least 2 (meth)acrylic groups in the molecule.
    Type: Grant
    Filed: July 3, 1996
    Date of Patent: April 21, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Reich, Erich Beck, Ulrich Jager, Reinhold Schwalm
  • Patent number: 5739251
    Abstract: The present invention relates to ethylenically unsaturated polyurethanes which are substantially free from isocyanate groups and havea) a content of .beta.,.gamma.-ethylenically unsaturated ether groups (calculated as C.dbd.C, MW 24) incorporated through allophanate groups of 0.5 to 10% by weight,b) an allophanate group content (calculated as N.sub.2 C.sub.2 HO.sub.3, MW 101) of 1 to 20% by weight andc) a total content of ethylenically unsaturated groups of (calculated as C.dbd.C, MW 24) of 1 to 15% by weight.The present invention also relates to ethylenically unsaturated polyisocyanates which contain allophanate groups and havei) an NCO content of 5 to 25% by weight,ii) a content of .beta.,.gamma.-ethylenically unsaturated ether groups (calculated as C.dbd.C, MW 24) incorporated through allophanate groups of 0.5 to 15% by weight andiii) an allophanate group content (calculated as N.sub.2 C.sub.2 HO.sub.3, MW 101) of 1 to 30%.
    Type: Grant
    Filed: March 27, 1997
    Date of Patent: April 14, 1998
    Assignee: Bayer Corporation
    Inventors: Lanny D. Venham, Arthur W. Mason, Michael K. Jeffries, Michael J. Dvorchak
  • Patent number: 5733707
    Abstract: The present invention provides a negative-working image recording material which can be used as a lithographic printing plate for so-called direct plate making process comprising directly making plate from digital signal such as computer signal. A novel negative-working image recording material is provided, comprising a high-molecular compound having a weight-average molecular weight of from 5,000 to 400,000 and a repeating unit represented by the following general formula (I), and a substance which absorbs light to generate heat: ##STR1## wherein R.sup.1 represents a hydrogen atom, a halogen atom, a cyano group (--CN) or an alkyl group; R.sup.2 represents an alkyl group, an aralkyl group or an aromatic ring group; L.sup.1 represents a single bond or a phenylene group; L.sup.2 represents an alkylene group, an alkenylene group or an aromatic ring group; X represents a single bond, --O--, --OCO--, --COO--, --CONR.sup.3 --, --CONR.sup.3 CO--, --CONR.sup.3 SO.sub.2 --, --NR.sup.3 --, --NR.sup.3 CO--, --NR.sup.
    Type: Grant
    Filed: July 22, 1996
    Date of Patent: March 31, 1998
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Fumikazu Kobayashi
  • Patent number: 5712035
    Abstract: Provided is an optical fiber having a primary coating thereon wherein the coating is formulated from an ultra-violet light curable resin composition containing:(A) a polyether polyol compound containing, as structural units, groups represented by the following formulas (1), (2, and (3),(1) --CH.sub.2 CH.sub.2 O--(2) --CH.sub.2 CH(R)O--, and(3) one or more groups selected from groups (a), (b), and (c) below, ##STR1## wherein R represents an alkyl group containing two or more carbon atoms, and R.sup.1 and R.sup.2 are independently selected from a hydrogen atom or a methyl group;(B) a polyisocyanate compound; and(C) a (meth)acrylate compound having a hydroxy group.
    Type: Grant
    Filed: February 20, 1996
    Date of Patent: January 27, 1998
    Assignee: DSM N.V.
    Inventors: Tohru Ohtaka, Shinichirou Iwanaga, Tsuyoshi Watanabe, Katutoshi Igarashi
  • Patent number: 5710193
    Abstract: Colorants, polymeric binder resins, photoinitiators, photosensitizers, color-change agents, anti-halation agents, stabilizers, and other active hydrogen-containing components of radiation sensitive compositions for lithographic printing plate production and the like are reacted with a polyethylenically unsaturated monoisocyanate compound of the formula ##STR1## wherein Y is the residue of a monohydroxyl compound of formula YOH and Y contains at least two ethylenically unsaturated double bonds. In this way the components are bonded to the image on exposure.
    Type: Grant
    Filed: May 21, 1996
    Date of Patent: January 20, 1998
    Assignee: DuPont (UK) Limited
    Inventors: John Robert Wade, Michael John Pratt, Jianrong Ren
  • 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: 5703141
    Abstract: The present invention relates to oligomers or prepolymers which are formed by reacting an isocyanate, a lactone adduct and a hydroxyalkyl acrylate or methacrylate. These oligomers can be used to make UV curable coatings by adding acrylate monomers, photoinitiators and wetting agents. Transparent, abrasion resistant surfaces result from the cure by ultraviolet light of these coatings on substrates such as PVC based substrates. By adjusting the ratio of hydroxyalkyl acrylate or methacrylate and the lactone adduct component in the oligomer, coatings with both high tensile strength and elongation can be obtained.
    Type: Grant
    Filed: September 25, 1995
    Date of Patent: December 30, 1997
    Assignee: Tarkett AG
    Inventor: Peiwen Jin
  • Patent number: 5698371
    Abstract: A photocurable composition useful in preparing water-developable, solid printing plates is prepared by blending a urethane (meth)acrylate prepolymer with a complexing polymer based on poly(vinyl pyrrolidone) composition. The resulting composition 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 aqueous media, to give a plate with a desirable relief image. The use of the aqueous washout solution as opposed to organic solvents minimizes pollution problems. The use of the complexing polymer significantly reduces the cold flow of the uncured plate and both increases toughness and reduces tack of the cured plate.
    Type: Grant
    Filed: May 16, 1994
    Date of Patent: December 16, 1997
    Assignee: PT Sub, Inc.
    Inventors: Srinivas K. Mirle, Truc-Chi T. Huynh-Tran
  • 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: 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: 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: 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: 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: 5571659
    Abstract: A process is disclosed for producing a liquid jet recording head comprising applying an active energy-curing resin composition onto at least a part of a surface of a first member for forming a wall of the liquid path; exposing the applied active energy-ray-curing resin to an active energy ray selected from the group consisting of an ultraviolet-ray having an intensity of 1 mW/cm.sup.2 to 100 mW/cm.sup.2 and an electron beam having an intensity of 0.5M Rad to 20M Rad; and providing a second member on the exposed active energy-ray-curing resin composition.
    Type: Grant
    Filed: March 20, 1995
    Date of Patent: November 5, 1996
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Saito
  • 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: 5538821
    Abstract: The present invention relates to a resist ink composition characterized by comprising a specific unsaturated polycarboxylic acid resin (A) or a specific unsaturated polycarboxylic acid/urethane resin (A'), a photopolymerization initiator (B), a diluent (C), and a curing component (D) and a cured article prepared therefrom.In the formation of a solder resist pattern via selective UV-exposure through a patterned film followed by development of the unexposed part, the composition of the present invention is excellent in developability even though at a small acid value (mg KOH/g) or over a prolonged drying time and shows a resistance of the exposed part against the developing solution. Further, a cured article prepared therefrom is excellent in electroless gold plating resistance and fully satisfactory in adhesion and soldering heat resistance.
    Type: Grant
    Filed: May 9, 1994
    Date of Patent: July 23, 1996
    Assignees: Nippon Kayaku Kabushiki Kaisha, Taiyo Ink Manufacturing Co., Ltd.
    Inventors: Masahisa Kakinuma, Shigeru Komori, Kazuhiro Yoshida, Minoru Yokoshima, Tetsuo Ohkubo, Kazunori Sasahara
  • 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: 5514522
    Abstract: A photoreactive binder that may be used to enhance photospeed in either conventional plates or on-press developable lithographic printing plates. Briefly, a polymer of m-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate is derivatized for vinyl group reactivity by reacting the isocyanate groups thereof with hydroxyalkyl acrylate. The resulting photopolymeric binder provides significantly higher photospeed than the non-reactive binder currently utilized in the production of conventional printing plates. The resulting lithographic printing plate also shows better durability (as manifested by longer run-length) and is more easily developed by the microencapsulated developers utilized in the present invention. As to the preparation of the photoreactive binders, the application discloses a method of copolymerizing m-isopropenyl-.alpha.,.alpha.
    Type: Grant
    Filed: April 27, 1995
    Date of Patent: May 7, 1996
    Assignee: Polaroid Corporation
    Inventors: Maurice J. Fitzgerald, Frederick R. Kearney, Rong-Chang Liang, William C. Schwarzel
  • Patent number: 5502145
    Abstract: This invention provides an improved coating composition for glass substrates that comprises a poly(siloxane). The introduction of a poly(siloxane) in a coating composition for a glass substrate, and in particular an optical fiber, acts to delay the rate of deterioration of the glass or optical fiber due to moisture, and improves adhesion between the glass substrate and the coating composition. The introduction of a poly(siloxane) into a polymeric coating composition also improves the interlayer adhesion when more than one coating is applied to a glass substrate. This invention also provides an improved coated glass substrate having a decreased rate of deterioration due to moisture, improved adhesion between the glass substrate and the coating composition and between the various coatings, wherein the coating composition comprises a poly(siloxane).
    Type: Grant
    Filed: March 2, 1994
    Date of Patent: March 26, 1996
    Assignee: DSM Desotech. Inc.
    Inventor: David M. Szum
  • Patent number: 5496870
    Abstract: A curable liquid resin composition comprising a urethane (meth)acrylate polymer obtained by reacting:(A) a polyol compound containing as structural units groups which are represented by formulae--CH.sub.2 CH.sub.2 O-- or--CH.sub.2 CH(CH.sub.2 CH.sub.3)O--;(B) a polyisocyanate compound; and(C) at least one (meth)acrylate compound containing a hydroxyl group and coated articles produced therefrom.
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: March 5, 1996
    Assignee: DSM
    Inventors: Chander P. Chawla, Tohru Ohtaka, Shinichirou Iwanaga, Tsuyoshi Watanabe, Katsutoshi Igarashi
  • Patent number: 5475038
    Abstract: A print laminating adhesive composition comprising a selected acrylate terminated photopolymerizable oligomer of the formula: ##STR1## where A is the residue of a diisocyanate selected from the group consisting of diphenylmethane 4,4.sup.1 diisocyanate and 4,4.sup.1 dicyclohexylmethane diisocyanate; X is the residue of polypropylene glycol having a molecular weight of from about 150 to 4000; R is alkyl or hydroxyalkyl of 2 to 10 carbons; R.sup.1 is alkylene of 2 to 3 carbons; and R.sup.2 is hydrogen or methyl.
    Type: Grant
    Filed: May 10, 1994
    Date of Patent: December 12, 1995
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventor: Martin M. Skoultchi
  • Patent number: 5466723
    Abstract: A radiation curable adhesive composition which comprises from 15 to 85 percent by weight of beta-carboxyethyl acrylate and from 85 to 15 percent by weight of 2-phenoxyethyl acrylate based on the total weight of the composition.
    Type: Grant
    Filed: October 17, 1994
    Date of Patent: November 14, 1995
    Assignee: Eastman Kodak Company
    Inventor: Billy R. Dotson
  • Patent number: 5459196
    Abstract: This invention relates to new water-emulsifiable polyester resins, a process for their production and their use as a lacquer row material. These lacquer binders are produced by the reaction of at least one prepolymer A which contains (meth)acryloyl groups and at least one unsaturated water-emulsifiable polyester B with at least one polyisocynate C.
    Type: Grant
    Filed: June 10, 1993
    Date of Patent: October 17, 1995
    Assignee: Wolff Walsrode Aktiengesellschaft
    Inventors: Burkhard Kressdorf, Wolfgang Dannhorn, Erhard Luhmann, Lutz Hoppe
  • Patent number: 5456984
    Abstract: A halogen-free radiation curable flame retardant composition that comprises an end-capped oligomer of a phosphonate polyol and a polyisocyanate and an organic monomer.
    Type: Grant
    Filed: February 6, 1995
    Date of Patent: October 10, 1995
    Assignee: DSM Desotech, Inc.
    Inventors: Timothy E. Bishop, Erwin S. Poklacki
  • Patent number: 5439956
    Abstract: An adhesive for use in bonding finely processed parts such as parts of ink jet recording head has a composition which essentially contains: (A) a vinylester compound of an urethanated epoxy resin; (B) a partial vinylester compound of a multi-functional epoxy resin; (C) an acrylic reactive diluent; (D) a photopolymerization initiator; and(E) an epoxy cure agent. This adhesive is curable by ultraviolet irradiation or by application of heat, and does not flow or spread into areas where bonding is not necessary, so that finely processed parts are bonded with a high degree of precision of the bonding pattern.
    Type: Grant
    Filed: February 9, 1994
    Date of Patent: August 8, 1995
    Assignee: Canon Kabushiki Kaisha
    Inventor: Hiromichi Noguchi
  • Patent number: 5438080
    Abstract: A ultraviolet-curable coating composition is disclosed, which comprises a specific ultraviolet-curable polyfunctional (meth)acrylate, a specific urethane-curing polymer, and a specific polyisocyanate compound in a specific compounding ratio and having incorporated therein a photo stabilizer and a photopolymerization initiator. The composition provides a coating film of large thickness in one operation and is sufficiently cured even with non-uniform ultraviolet radiation and the coating film obtained from such a composition fully satisfies various requirements, such as appearance, adhesion, and weathering resistance.
    Type: Grant
    Filed: September 18, 1992
    Date of Patent: August 1, 1995
    Assignee: Nippon Oil and Fats Co., Ltd.
    Inventors: Yoshifumi Ohama, Yoshihide Chihara, Yasufumi Honda, Yasuhiro Miyamoto
  • Patent number: 5436279
    Abstract: A coating material crosslinkable by radiation comprising a) an olefinic unsaturated ester of an epoxy novolac resin, b) a binder formed by reaction of an epoxy compound having more than one epoxide group per molecule with at least one carboxylic acid in a molar ratio of epoxy groups per carboxyl group of 1:0.5 to 0.9 and subsequent reaction of the resulting reaction product with at least one unsaturated isocyanate ester formed by reaction of a compound with at least two isocyanate groups with a member of the group consisting of hydroxyl containing acrylic acid, methacrylic acid and cyanacrylic acid esters, c) at least one latent hardener, d) at least one photoinitiator e) 80-120% by weight of fillers and (f) additives, adjuvants and solvents and protective films formed with them.
    Type: Grant
    Filed: February 1, 1994
    Date of Patent: July 25, 1995
    Assignees: Rutgerswerke Aktingesellschaft, Lackwere Peters GmbH & Co. KG
    Inventors: Ulrich Grundke, Klaus-Peter Liebetanz, Achim Hansen, Jurgen Zehrfeld, Rainer Scharre, Werner Peters
  • Patent number: 5426131
    Abstract: An ultraviolet radiation curable silica coating composition containing (a) acrylic monomers, (b) functionalized colloidal silica, (c) acrylated urethanes, (d) an ultraviolet radiation absorber, and (e) a photoinitiator. The coating composition once applied to and cured on a thermoplastic substrate provides a coating which exhibits improved flexibility and weathering. The coatings are useful for providing abrasion resistance and weatherability to thermoplastic, for example polycarbonate, substrates.
    Type: Grant
    Filed: October 13, 1993
    Date of Patent: June 20, 1995
    Assignee: General Electric Company
    Inventor: Dimitris Katsamberis
  • Patent number: 5415972
    Abstract: An aqueous-developable dry-film photopolymerizable composition is disclosed wherein the photopolymerizable composition contains a carboxyl-containing polyurethane having at least one ethylenically unsaturated end group as a plasticizer.
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: May 16, 1995
    Assignee: Hercules Incorporated
    Inventor: Richard T. Mayes
  • Patent number: 5409740
    Abstract: A method of forming a fiber bundle which is useful as an industrial thread. The fiber bundle is prepared by integrating individual fiber filaments into a fiber bundle, applying a dual-cure adhesive material to the fiber bundle and initiating polymerization of the dual-cure adhesive material. The dual-cure adhesive material is a combination of a radiation-curable material and a moisture-curable material. The radiation-curable material contains an acrylourethane oligomer and a reactive diluent system, while the moisture-curable material contains a polyisocyanate or an isocyanate-functional urethane prepolymer. The use of a dual-cure material results in a synergistic curing process so as to form a durable and flexible industrial thread or fiber.
    Type: Grant
    Filed: December 18, 1992
    Date of Patent: April 25, 1995
    Assignee: Lord Corporation
    Inventor: Bill L. Brann
  • Patent number: 5402516
    Abstract: Optical fiber and cable performance are assured by a category of UV-cured polyurethane acrylates. Low cost is the consequence of use of the polycarbonate oligomer. Good performance and long life are ascribed to other ingredients of the coatings. Dependence on the hindered phenols for antioxidant protection assures sufficient protection for these inherently stable materials without incurring fiber damage found to result from use of hindered amine antioxidants.
    Type: Grant
    Filed: September 30, 1993
    Date of Patent: March 28, 1995
    Assignee: AT&T Bell Laboratories
    Inventors: Lee L. Blyler, Jr., Darryl L. Brownlow, Daryl Inniss, James R. Petisce, Lloyd Shepherd, Carl R. Taylor
  • Patent number: 5373032
    Abstract: This invention relates to alk-1-enyl etherurethanyl block prepolymers which are curable by cationically initiated radiation and which are defined by the formula ##STR1## wherein m has a value of from 1 to 25;A is C.sub.2 to C.sub.12 alkylene, C.sub.6 to C.sub.14 aryl, both groups optionally substituted with lower alkyl, halo lower alkyl, alkyleneoxy, halogen or aryl;R.sub.1 is alkylene containing from 1 to 6 carbon atoms;R.sub.2 is a saturated or unsaturated divalent radical containing from 1 to 14 carbon atoms and is selected from the group of alkylene, alkenylene and arylene, each group optionally substituted with oxygen, halogen, lower alkyl and/or hydroxy;R.sub.3 is hydrogen or C.sub.1 to C.sub.6 alkyl;R.sub.4 is C.sub.1 to C.sub.6 alkylene, C.sub.6 to C.sub.14 arylene, lower alkyl substituted phenylene or xylylene andR.sub.5 is hydrogen or C.sub.1 to C.sub.4 alkyl.
    Type: Grant
    Filed: August 18, 1993
    Date of Patent: December 13, 1994
    Assignee: ISP Investments Inc.
    Inventors: Mark M. Miller, Jeffrey S. Plotkin
  • Patent number: 5364691
    Abstract: This invention relates to radiation curable alk-1-enyloxy carbonate reaction products of a hydroxylated compound having the formula A-ROH and a dialk-1-enyloxy carbonate having the formula ##STR1## wherein R is a polymeric radical selected from the group of polyester, polyacetal, polyurethane, polyether, and polycarbonate, said polymers containing from about 10 to 50 repeating monomer units;A' is a terminating moiety and is hydrogen, lower alkyl or hydroxy;R' is hydrogen or lower alkyl;B is a linear, branched or cyclic divalent radicalhaving from 2 to 12 carbon atoms and is selected from the group of alkylene, mono or poly alkoxylated alkylene, alkenylene, alkynylene, arylene, alkarylene and aralkylene radicals, which radicals are optionally substituted with halo, lower alkyl, cyano, nitro or alkoxy and m has a value of from 1 to 10.
    Type: Grant
    Filed: March 9, 1990
    Date of Patent: November 15, 1994
    Assignee: ISP Investments Inc.
    Inventors: Paul D. Taylor, Kolazi S. Narayanan, Jeffrey S. Plotkin
  • Patent number: 5360835
    Abstract: Radiation-curable polyurethane emulsion compositions that can be diluted with water are disclosed. An emulsion of a polyurethane having active amino groups is prepared, and the emulsion is reacted, in the presence of water, with an isocyanate compound having a polymerizable unsaturated group to introduce the polymerizable unsaturated group into the polyurethane. The introduction of a polymerizable unsaturated group into the polyurethane is accomplished in the presence of water, thereby overcoming prior art problems of polymerization and gelation during the preparation of the emulsion. The present invention provides radiation-curable polyurethane emulsion compositions that can be produced on an industrial scale.
    Type: Grant
    Filed: November 30, 1993
    Date of Patent: November 1, 1994
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Kazuo Sato, Tadayuki Sugimoto, Naofumi Saiuchi