With Ethylenic Reactant Patents (Class 522/96)
  • Patent number: 6063888
    Abstract: A liquid radiation curable resin composition comprising a polydimethylsiloxane compound which has (i) at least two urethane bonds in one molecule, (ii) an unreactive organic group at at least one of the ends of the molecule, and (iii) a radical curable ethylenically unsaturated group at the other end of the molecule. The resin composition exhibits superior shelf life in a liquid state and produces cured products having slippery surface. It is suitable as a coating material for optical fibers.
    Type: Grant
    Filed: October 9, 1998
    Date of Patent: May 16, 2000
    Assignees: DSM N.V., JSR Corporation
    Inventors: Yoshikazu Yamaguchi, Junji Yoshizawa, Zen Komiya, Takashi Ukachi
  • Patent number: 6057381
    Abstract: A method is disclosed for preparing an electronic assembly using a reworkable underfill encapsulant in which the encapsulant is cured in situ from a curable composition comprising one or more mono-functional maleimide compounds, or one or more mono-functional vinyl compounds other than maleimide compounds, or a combination of maleimide and vinyl compounds, a curing initiator and optionally, one or more fillers or adhesion promoters.
    Type: Grant
    Filed: July 2, 1998
    Date of Patent: May 2, 2000
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventors: Bodan Ma, Quinn K. Tong, Chaodong Xiao
  • Patent number: 6054502
    Abstract: A radiation curable coating composition comprising: (A) an unsaturated polyester component; and (B) a non-polymerized, cocurable vinyl ether component. Component (B) may be separate from or structurally incorporated in the unsaturated polyester component. The vinyl ether component contains an average of at least two vinyl ether groups per molecule of the vinyl ether component.
    Type: Grant
    Filed: March 23, 1998
    Date of Patent: April 25, 2000
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Charles B. Friedlander, David A. Diehl
  • Patent number: 6054503
    Abstract: Disclosed herein are a plastic lens material having both excellent optical and mechanical properties and having a low specific gravity, and a production process for producing the plastic lens material having excellent various properties and a low specific gravity. The plastic lens material comprises a copolymer obtained by radical-polymerizing a reaction product of a component [A] containing a polyhydric alcohol obtained by subjecting a dimer and/or a trimer of a higher unsaturated fatty acid having 11 to 22 carbon atoms with a component [B] containing an isocyanate compound having a radical-polymerizable unsaturated bond in its molecule together with a copolymerizable monomer [C].
    Type: Grant
    Filed: December 8, 1998
    Date of Patent: April 25, 2000
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yukio Ichikawa, Teruo Sakagami
  • Patent number: 6048911
    Abstract: Coated optical fibers comprise a glass optical fiber and a radiation-cured coating formed from a radiation-curable liquid coating composition. The liquid coating composition comprises at least one aliphatic urethane acrylate oligomer, at least one acrylated or methacrylated compound selected from the group consisting of isobornyl acrylate, isobornyl methacrylate, alkanediol diacrylate, alkanediol dimethacrylates, alkoxylated derivatives thereof, and mixtures thereof, and a photoinitiator. In one embodiment, the compositions further include a silicone compatibility agent which reduces the coefficient of friction of the radiation-cured coating without disadvantageously effecting other physical properties of the liquid coating compositions or the cured coating, and particularly without disadvantageously effecting the optical clarity of the liquid coating compositions.
    Type: Grant
    Filed: December 12, 1997
    Date of Patent: April 11, 2000
    Assignee: Borden Chemical, Inc.
    Inventors: Paul J. Shustack, Daniel A. Wilson
  • Patent number: 6039798
    Abstract: Wax coated silica matting agent wherein the silica is an amorphous silica having a pore volume of at least 1.5 cm.sup.3 /g, preferably at least 1.8 cm.sup.3 /g. The wax coating is present in the range from 6% to 15% by weight of the matting agent and comprises a synthetic polyethylene wax.
    Type: Grant
    Filed: February 12, 1999
    Date of Patent: March 21, 2000
    Assignee: Crosfield Limited
    Inventors: Derek Aldcroft, Sharron Bates, Graham James Earl
  • Patent number: 6036910
    Abstract: A resin composition for three-dimensional object by optical stereolithography containing a colorant, such as carbon black, in an amount of 0.05 to 0.5% by weight can provide a colored three-dimensional object which has excellent physical and mechanical properties such as dimensional accuracy, shape stability, hardness and tensile strength and elastic modulus in tension, as well as light-shielding properties, gives a massive impression and is colorful at a high optical shaping speed and in a good productivity.
    Type: Grant
    Filed: September 23, 1997
    Date of Patent: March 14, 2000
    Assignee: Teijin Seiki Co., Ltd.
    Inventors: Yorikazu Tamura, Tsuneo Hagiwara
  • Patent number: 6031015
    Abstract: A dental material based on polymerizable monomers is described which contains at least one polymerizable monomer which has liquid crystalline properties. Compared with traditional materials, the dental material displays a lower decrease in volume upon polymerization and, because of its low viscosity, higher filler contents can be achieved.
    Type: Grant
    Filed: July 17, 1996
    Date of Patent: February 29, 2000
    Assignee: Ivoclar AG
    Inventors: Helmut Ritter, Georg Draheim, Norbert Moszner, Ulrich Salz, Volker Rheinberger
  • Patent number: 6031044
    Abstract: A polyurethane which is substantially self-dispersible in water and is obtainable by reactinga) at least one polyisocyanate withb) at least one polyol andc) at least one photoinitiator of the general formula I ##STR1## where R is a radical of the formula II ##STR2## or is --CR.sup.7 R.sup.8 R.sup.9, P(.dbd.O)(R.sup.10).sub.2 or SO.sub.2 R.sup.11,the number-average molecular weight M.sub.n of the polyurethane being greater than 2700, and its use. The invention also relates to aqueous polyurethane resin dispersions and coating compositions comprising the novel polyurethanes, and to their use.
    Type: Grant
    Filed: December 18, 1997
    Date of Patent: February 29, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Nicolas Kokel, Harald Larbig, Klaus Menzel, Erich Beck, Wolfgang Reich, Guido Voit
  • Patent number: 6025114
    Abstract: 1. This invention relates to a liquid composition comprising:a) 2 to 20 parts of a monomeric poly(meth)acrylate having a functionality of at least 3 and a MW of at least 650;b) 20 to 60 parts of a urethane(meth)acrylate having a functionality of 2 to 4 and a MW of 400 to 10,000;c) 20 to 80 parts of a monomeric or oligomeric di(meth)acrylate based on bisphenol A or bisphenol F; andd) 0.1 to 10 parts of a photoinitiator;wherein all parts are by weight and the total number of parts of a)+b)+c)+d) add up to 100.The compositions are suitable for the stereolithographic production of three-dimensional articles such as models of mechanical and body parts and are particularly notable for their low curl & shrinkage coupled with fast rate of cure.
    Type: Grant
    Filed: September 11, 1997
    Date of Patent: February 15, 2000
    Assignee: Zeneca Limited
    Inventors: Ajay Haridas Popat, John Robert Lawson
  • Patent number: 6017603
    Abstract: An ultraviolet-curable adhesive composition which comprises (A) a bisphenol type epoxy (meth)acrylate having a molecular weight of 450 to 3,000, (B) a urethane (meth)acrylate having a molecular weight of 400 to 10,000, (E) a (meth)acrylate monomer other than (A) and (B), and (F) a photopolymerization initiator, and an article having a cured layer of the above adhesive composition.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: January 25, 2000
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Kiyohisa Tokuda, Kenji Yoshida, Kazuhiko Ishii, Minoru Yokoshima
  • Patent number: 6017973
    Abstract: A photocurable resin composition comprising (A) at least one urethane di- or triacrylate, which is a novel compound, (B) a radical polymeriable compound, and (C) a photopolymerization initiator, the weight ratio of the urethane acrylate (A) to the radical polymerizable compound (B) being 65/35 to 25/75; a method of producing a photo-cured object by photo-curing the above composition; a vacuum casting mold obtained by the above method; and a vacuum casting method using the above mold.
    Type: Grant
    Filed: May 16, 1997
    Date of Patent: January 25, 2000
    Assignee: Teijin Seiki Company, Ltd.
    Inventors: Yorikazu Tamura, Tsuneo Hagiwara, Yasushi Ishihama, Minoru Kayanoki, Takakuni Ueno
  • Patent number: 6008296
    Abstract: A monomer composition characterized by being curable to form a resin suitable for optical products having a balanced refractive index and Abbe's number range and good tintability comprising a polyene monomer; a polyisocyanate, polyisothiocyanate, or an isocyanate monomer containing at least one isothiocyanate group; and a monomer having two or more active hydrogen groups such as polythiols, polyamines, and polyols. The invention also provides a special process for making the composition and for curing the composition to form a resin product.
    Type: Grant
    Filed: April 19, 1995
    Date of Patent: December 28, 1999
    Assignee: Optima, Inc.
    Inventors: Zhou Yang, Yin-Nian Lin, Zhenya Zhu, Brian George Risch
  • Patent number: 6002511
    Abstract: The present invention relates to electrochromic polymeric solid films, manufacturing electrochromic devices using such solid films and processes for making such solid films and devices. The electrochromic polymeric solid films of the present invention exhibit beneficial properties and characteristics, especially when compared to known electrochromic media. The electrochromic polymeric solid films are transformed in situ from a low viscosity electrochromic monomer composition by exposure to electromagnetic radiation, and in so doing minimum shrinkage occurs. The electrochromic polymeric solid films of the present invention also perform well under prolonged coloration, outdoor weathering and all-climate exposure, and provide an inherent safety aspect not known to electrochromic media heretofore.
    Type: Grant
    Filed: January 14, 1998
    Date of Patent: December 14, 1999
    Assignee: Donnelly Corporation
    Inventors: Desaraju V. Varaprasad, Mingtang Zhao, Craig Allen Dornan, Anoop Agrawal, Pierre-Marc Allemand, Niall R. Lynam
  • Patent number: 5998497
    Abstract: A liquid photocurable resin composition having excellent applicability in a high speed drawing condition and high curability, providing a stable coating film which generates little hydrogen gas when used as a coating material for optical fiber. The liquid photocurable resin composition comprises 10-80 wt % of a polymer having an ether bond or an ester bond, and an ethylenically unsaturated group; 5-50 wt % of at least one monomer according to the formula ##STR1## wherein R.sup.9 is a hydrogen atom or a methyl group, R.sup.10 is an alkylene group having 2-4 carbon atoms, and n denotes an integer from 1-10; 0.1-10% by weight of a photopolymerization initiator; and optionally other compounds comprising one or more ethylenically unsaturated groups.
    Type: Grant
    Filed: May 28, 1998
    Date of Patent: December 7, 1999
    Assignees: DSM N.V., JSR Corporation
    Inventors: Miyuki Ishikawa, Takashi Ukachi
  • Patent number: 5990188
    Abstract: The present invention provides the discovery of an improved radiation curable coating composition comprising at least one acrylic monomer, a photoinitiator, and an ultraviolet light absorber selected from triazine or a dibenzoyl resorcinol derivative or a mixture thereof, the dibenzoyl resorcinol derivative having the formula ##STR1## where Ar and Ar' are independently substituted or unsubstituted monocyclic or polycyclic aryl groups and R' is H or a linear or branched alkyl chain having less than about 10 carbons bearing a --Si(OR.sup.2).sub.3, where R.sup.2 is a C.sub.1 to C.sub.6 alkyl group.
    Type: Grant
    Filed: August 15, 1996
    Date of Patent: November 23, 1999
    Assignee: General Electric Company
    Inventors: Gautam Ambalal Patel, James Edward Pickett, Gregory Ronald Gillette, George Frederic Medford
  • Patent number: 5990190
    Abstract: A photosensitive resin composition for cast molding, which has an ultraviolet transmittance of 0.05-5% as measured at a 1-mm thickness.
    Type: Grant
    Filed: July 15, 1997
    Date of Patent: November 23, 1999
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Shohei Nakamura, Kousi Anai
  • Patent number: 5977200
    Abstract: An ultraviolet curable clearcoat composition comprising (exclusive of any solvent present): (a) about 30% to about 90% by weight of an acrylated aliphatic urethane having a molecular weight of about 1200 to 2600 and formed by the reaction of a multifunctional acrylate with a molecular weight of between about 110 and about 500 with an aliphatic urethane based on a polyether and having a molecular weight of about 800 to about 2200; (b) about 15% to about 70% by weight of a multifunctional acrylate having a molecular weight of about 170 to about 1000 and containing at least two polymerizable unsaturated groups per molecule; and (c) a photopolymerization initiator and/or sensitizer. Also described are preferred processes and clearcoated articles involving preferred clearcoat compositions.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: November 2, 1999
    Assignee: Red Spot Paint & Varnish Co., Inc.
    Inventor: Randall T. Lake
  • Patent number: 5972563
    Abstract: A liquid, radiation-curable composition which in addition to a liquid, free-radically polymerizable component comprises at least the following additional components: (A) from 40 to 80 percent by weight of a liquid difunctional or more highly functional epoxy resin or of a liquid mixture consisting of difunctional or more highly functional epoxy resins; (B) from 0.1 to 10 percent by weight of a cationic photoinitiator or of a mixture of cationic photoinitiators; and (C) from 0.
    Type: Grant
    Filed: July 28, 1997
    Date of Patent: October 26, 1999
    Assignee: Ciba Specialty Chemicals Corp.
    Inventors: Bettina Steinmann, Adrian Schulthess
  • Patent number: 5965460
    Abstract: Particular polyurethane photopolymers are disclosed as materials of construction in producing improved polishing pads. The polyurethane photopolymers are formed from a polyurethane prepolymer prepared from the reaction products of a first reactant selected from the group consisting of polyesters, polyethers, polybutadienes and mixtures of the foregoing with diisocyanates, further reacted with acrylates and/or methacrylates.
    Type: Grant
    Filed: January 29, 1997
    Date of Patent: October 12, 1999
    Assignee: Mac Dermid, Incorporated
    Inventors: Joseph Rach, Douglas Leach
  • Patent number: 5955512
    Abstract: A pressure sensitive adhesive composition is disclosed which comprises an acrylic copolymer (A), an energy beam polymerizable urethane acrylate oligomer (B) and an energy beam polymerizable compound having one acryloyl group or methacryloyl group in each molecule thereof (C). This composition is preferred to further contain a plasticizer (D), a crosslinking agent (E) and/or a photopolymerization initiator (F) according to necessity. The pressure sensitive adhesive composition has satisfactory pressure sensitive adherence and initial adhesion before the irradiation with energy beam and the adhesive strength thereof is sharply reduced with maintaining the rubber elasticity after the irradiation with energy beam. Further, the pressure sensitive adhesive composition ensures excellent chip alignability in the expanding step subsequent to dicing.
    Type: Grant
    Filed: April 24, 1997
    Date of Patent: September 21, 1999
    Assignee: Lintec Corporation
    Inventors: Hideki Numazawa, Yoshihisa Mineura
  • 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: 5929130
    Abstract: Photocurable resin compositions capable of producing plastic molds with improved durability by stereolithography in the presence of a photoinitiator includes unsaturated urethane of a specified kind, vinyl monomer of a specified kind, a filler and salt of phosphoric acid ester of specified kinds at a specified ratio.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: July 27, 1999
    Assignee: Takemoto Yushi Kabushiki Kaisha & Teijin Seiki Co., Ltd.
    Inventors: Toshiharu Suzuki, Tatsuhiko Ozaki, Hirokazu Matsueda, Yorikazu Tamura, Tsuneo Hagiwara
  • Patent number: 5919834
    Abstract: Disclosed are UV-cured heat transfer labels prepared from a mixture containing at least one thermoplastic resin, at least one material for solvating the thermoplastic resin, the solvating material being either a solvent or liquid monomer, and at least one photo-initiable material which initiates curing of the composition.
    Type: Grant
    Filed: September 29, 1997
    Date of Patent: July 6, 1999
    Assignee: Illinois Tool Works Inc.
    Inventors: Myron H. Downs, James D. Singelyn, Bruce W. Downs
  • 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: 5908874
    Abstract: A polymerizable composition has added thereto a fluorochemical in sufficient quantities to reduce the melting temperature of the composition compared with that of the composition absent the fluorochemical.
    Type: Grant
    Filed: June 18, 1996
    Date of Patent: June 1, 1999
    Assignee: 3M Innovative Properties Company
    Inventors: Bettie C. Fong, Myles L. Brostrom
  • Patent number: 5907023
    Abstract: The invention provides a radiation-curable coating composition comprising:(A) 30-90% by weight of a urethane oligomer having three types of moieties: (I) a polyether/polyolefin block copolymeric backbone, (II) an aromatic group having one or more alkyl substituents, and (III) reactive termini, the three types of moieties being connected via urethane and/or urea linkages, the aromatic group being connected to a urethane and/or urea linkage via the one or more alkyl substituents;(B) 5-65% by weight of one or more reactive diluents, each diluent being terminated with at least one end group capable of reacting with the reactive terminus of (A);(C) optionally, 0-10% by weight of at least one photoinitiator;(D) optionally, 0-5% by weight antioxidant; and(E) 0-30% by weight adhesion promoter.The compositions have an excellent combination of properties including good optical clarity, good resistance to moisture and hexane, and high refractive index.
    Type: Grant
    Filed: June 16, 1997
    Date of Patent: May 25, 1999
    Assignee: DSM NV
    Inventor: Chander P. Chawla
  • Patent number: 5907000
    Abstract: A curable composition for coating eyeglass lenses and other transparent substrates and capable of producing a hard coating, the index of refraction of which can be easily matched, through proper formulating, to the index refraction of the substrate to be coated to thereby avoid visible interference fringes. The composition comprises, in an organic solvent, a plurality of acrylate or methacrylate-functional monomers or oligomers and specifically including a (meth)acrylate-functional monomer having an (meth)acrylate-functionality of at least three and, when cured by itself, having a predetermined index of refraction. Optionally and preferably, the coating composition includes as well a different (meth)acrylate monomer having a functionality of one or more and, when cured by itself, exhibiting a different predetermined index of refraction.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: May 25, 1999
    Assignee: The Walman Optical Company
    Inventor: Gerald D. Treadway
  • Patent number: 5902837
    Abstract: A photocurable resin composition comprising a propenyl ether group-containing compound (A) having propenyl ether groups of the following formula (1) and having a number-average molecular weight of not less than 500, and a cationic photopolymerization initiator (B).CH.sub.3 --CH.dbd.CH--O-- (1)The object is to provide a photocurable resin composition which cures at a higher speed than a vinyl ether compound on exposure to light irradiation, and has improved flow characteristics, physical property of cured resin, and adhesion to metal.
    Type: Grant
    Filed: August 9, 1996
    Date of Patent: May 11, 1999
    Assignee: Sanyo Chemical Industries, Ltd.
    Inventors: Takao Saito, Kohei Maeda, Naoshi Ozasa
  • Patent number: 5903399
    Abstract: UV-curable Fresnel lens resin compositions ?a! comprising a (meth)acrylate containing hydroxyl group and aromatic ring (A1), a urethane group-contining (meth) acrylate (A2) comprising an aromatic diol, an aromatic ringcontaining 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: February 4, 1998
    Date of Patent: May 11, 1999
    Assignees: Sanyo Chemical Industries, Ltd., Dainippon Printing Co., Ltd.
    Inventors: Tsutomu Yamashita, Michiharu Okubo, Makoto Honda, Futoshi Osawa
  • Patent number: 5900444
    Abstract: Disclosed is a radiation-crosslinkable thermoplastic polyurethane composition comprising (a) the reaction product of: (i) an aliphatic polyisocyanate, and (ii) a polyahl, and (b) a reactive monomer cross-linker. The reactive monomer cross-linker facilitates cross-linking of the reaction product upon contact of the cross-linker-containing composition with photons from a radiation source. Also disclosed is a process for converting this thermoplastic polyurethane into a thermoset polyurethane by irradiating the thermoplastic polyurethane with a beam of photons.
    Type: Grant
    Filed: October 8, 1996
    Date of Patent: May 4, 1999
    Inventor: Alan Zamore
  • Patent number: 5883148
    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 1,2-vinyl polybutadiene component, and zero to about 50% by weight of a tackifier agent.
    Type: Grant
    Filed: August 19, 1997
    Date of Patent: March 16, 1999
    Assignee: Acheson Industries, Inc.
    Inventors: Mark A. Lewandowski, Anthony M. Chasser
  • Patent number: 5881194
    Abstract: A radiation-curable matrix material for affixing coated and inked optical fibers in a ribbon configuration is disclosed. The material comprises an aliphatic polyether-based urethane acrylate; a monomer having a plurality of acrylate or methacrylate moieties; an alkyl acrylate or methacrylate; and an optional photoinitiator. Also disclosed are an optical fiber ribbon prepared therefrom; a process for preparing such ribbon; and a radiation-curable coating composition generally applicable for coating a substrate.
    Type: Grant
    Filed: March 17, 1994
    Date of Patent: March 9, 1999
    Inventor: David Clarke Duecker
  • Patent number: 5866628
    Abstract: The present invention provides ultraviolet curable or electron beam curable fluorescent inks and ink concentrates, which cure upon exposure to ultraviolet or electron beam radiation. The synthesis of the fluorescent ink and ink concentrates does not involve the use of volatile organic solvents, so removal of solvents is not necessary during the manufacturing process. The fluorescent inks and ink concentrates display minimal, consistent color shift when cured. The cured fluorescent inks and ink concentrates are solvent resistant, particularly to methyl ethyl ketone, methanol, nonane, and sec butyl alcohol. The fluorescent ink and ink concentrate is comprised of: from about 20 to 90%, preferably from about 30 to 70%, more preferably from about 30 to 60% by weight of an oligomer, which is either a formaldehyde oligomer or a cyclic-aliphatic oligomer; from about 0.
    Type: Grant
    Filed: August 30, 1996
    Date of Patent: February 2, 1999
    Assignee: Day-Glo Color Corp.
    Inventors: Wayne R. Likavec, Curtis Ray Bradley
  • 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: 5854300
    Abstract: A water-based, UV-curable ink for plastic substrates, comprising:a) a water-dispersible or water-soluble urethane acrylate oligomer;b) a monomer that is capable of softening the substrate in part or in full; the monomer being resistant to hydrolysis; andc) a passive resin that is soluble in the monomer.
    Type: Grant
    Filed: March 26, 1997
    Date of Patent: December 29, 1998
    Assignee: Sericol Limited
    Inventors: Nigel Paul Gould, Fereidoun Abbasi
  • 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: 5847021
    Abstract: The invention relates to a solvent-free radiation curable, optical glass fiber coating composition containing:a) a urethane oligomer having a functional group capable of polymerization in the presence of actinic radiation, with an average functionality of at least about 1.2, having a vinyl addition polymer as backbone.b) a urethane compound having a functional group capable of polymerization in the presence of actinic radiation, with an average functionality of at least about 1, containing an organic moiety having about 5 or more carbon atoms as backbone.c) a reactive diluent.Furthermore, the invention relates to a solvent-free method for producing a solvent-free, radiation curable urethane oligomer composition.
    Type: Grant
    Filed: November 1, 1996
    Date of Patent: December 8, 1998
    Assignee: DSM N.V.
    Inventors: Anthony J. Tortorello, Edward J. Murphy
  • Patent number: 5843576
    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: November 3, 1997
    Date of Patent: December 1, 1998
    Assignee: Armstrong World Industries, Inc.
    Inventors: Angela S. Rosenberry, Claude R.. Rupp, Songvit Setthachayanon
  • Patent number: 5843622
    Abstract: Disclosed is a liquid photosensitive resin composition for use in forming a relief structure, comprising (A) an unsaturated polyurethane prepolymer comprising a plurality of diol segments comprising at least one polyester diol segment and at least one polyether diol segment, wherein the weight ratio of the at least one polyester diol segment to the at least one polyether diol segment is from 1:3 to 4:1, and wherein each of the at least one polyester diol segment is independently a polyester diol segment comprising recurring units of a unit represented by the following formula (1): ##STR1## wherein R.sup.1 represents a divalent aliphatic group or a divalent aromatic group,or a polyester diol segment comprising recurring units of a unit represented by the following formula (2): ##STR2## (B) an addition-polymerizable ethylenically unsaturated monomer, and (C) a photopolymerization initiator.
    Type: Grant
    Filed: September 4, 1996
    Date of Patent: December 1, 1998
    Assignee: Ashai Kasei Kogyo Kabushiki Kaisha
    Inventors: Hiroaki Tomita, Takashi Kobayashi, Norihiko Sakata
  • Patent number: 5837422
    Abstract: A photopolymerizable composition comprising addition-polymerizable ethylenically unsaturated double bond-containing compounds and a photopolymerization initiator system, wherein, as the addition-polymerizable ethylenically unsaturated double bond-containing compounds, a compound (A) having at least 2 urethane bonds and at least 6 ethylenically unsaturated double bonds, and a compound (B) having no urethane bond and at least 3 ethylenically unsaturated double bonds, are contained in a weight ratio of from 4:1 to 1:4.
    Type: Grant
    Filed: July 11, 1996
    Date of Patent: November 17, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Mitsuru Sasaki, Fumiyuki Matsuo, Toshiaki Yokoo
  • 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: 5837746
    Abstract: 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: Grant
    Filed: June 23, 1997
    Date of Patent: November 17, 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: 5821276
    Abstract: A printing ink for radiation curing, e.g. by UV radiation or an electron beam, comprises a mixture of a polymerizable composition, a pigment or a dye and a titanium or zirconium compound which is an alkoxide of an unsaturated alcohol, said polymerizable composition comprising at least one unsaturated monomer and, optionally, at least one prepolymer and being polymerizable by exposure to radiation. The titanium or zirconium compound acts as an adhesion promoter for the ink.
    Type: Grant
    Filed: July 23, 1996
    Date of Patent: October 13, 1998
    Assignee: Tioxide Specialties Limited
    Inventor: Robert Hume Duncan
  • Patent number: 5821277
    Abstract: A thermosetting composition containing a carbonaceous material (1-1) and a thermosetting resin (1-2), the carbonaceous material (1-1) being obtained by reacting by contacting a carbon material (a) with a polymer (b) having in the molecule thereof at least one particular reactive group such as aziridine group, oxazoline group, N-hydroxyalkylamido group, epoxy group, or hydroxyl group, and an alkoxycarbonyl group represented by the formulaR.sup.1 R.sup.2 R.sup.3 C--O--CO-- (1)wherein each of R.sup.1, R.sup.2, and R.sup.3 stands for a hydrogen atom or an organic residue selected from an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 16 carbon atoms, or an aryl group having 6 to 16 carbon atoms, wherein at least two of R.sup.1, R.sup.2, and R.sup.
    Type: Grant
    Filed: November 1, 1996
    Date of Patent: October 13, 1998
    Assignees: Nippon Oil Co., Ltd., Dai Nippon Printing Co., Ltd.
    Inventors: Takayuki Hirayama, Haruyoshi Sato, Yutaka Otsuki, Masayuki Ando
  • Patent number: 5817376
    Abstract: Compositions containing conductivity enhancers, which are capable of being coated onto a substrate by means of electrostatic assistance. The compositions comprise one or more free-radically curable monomer(s), and one or more non-volatile conductivity enhancer(s), having cationic and anionic portions, which are soluble in the monomer(s) and which do not interfere with free-radical polymerization, wherein said anionic portion is a non-coordinating organophilic carbon-containing anion. The compositions may further comprise one or more initiator(s), one or more dissociation enhancing agent(s), cross-linking agent(s), cationically polymerizable monomer(s), cationic initiator(s), leveling agents, oligomer(s) or polymer(s), preferably co-reactive, and other additives or adjuvants to impart specific properties to the cured coating.
    Type: Grant
    Filed: March 26, 1996
    Date of Patent: October 6, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Albert I. Everaerts, William M. Lamanna, Albert E. Seaver, George V. Tiers
  • Patent number: 5807905
    Abstract: Compounds of the formula I ##STR1## in which n and o are a number from 0 to 50, m is a number from 1 to 50, u and v are 0 or 1, and at least one of the indices u and v is 1, R.sub.1, R.sub.2, R.sub.2a, R.sub.3 and R.sub.4 independently of one another are, for example, aromatic hydrocarbons, R.sub.5, if n and o are 0, is for example C.sub.1 -C.sub.12 alkyl and, if n and/or o are greater than 0, or if n and o are 0 and at the same time only one index u or v is 1, R.sub.5 may additionally, for example, be an aromatic hydrocarbon, at least one of the radicals R.sub.1, R.sub.2, R.sub.2a, R.sub.3, R.sub.4 and R.sub.5 being an aromatic hydrocarbon radical which is sterically hindered ortho to the boron atom, X is, for example, C.sub.1 -C.sub.20 alkylene, phenylene, biphenylene, etc., and Z is a radical which is able to form positive ions, are suitable as photoinitiators, both the compounds per se and their combination with dyes or other electron acceptors.
    Type: Grant
    Filed: November 21, 1996
    Date of Patent: September 15, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Allan Francis Cunningham, Martin Kunz, Hisatoshi Kura
  • Patent number: 5807519
    Abstract: A plastic mold is produced by first repeating the process of forming a layer of a photocurable resin composition of a specified kind and exposing it to actinic radiation to at least partially photocure it to produce a photocured layered structure having a glass transition temperature of 70.degree.-120.degree. C. This structure is then subjected to a post-cure process at a temperature high than the glass transition temperature by 30.degree.-100.degree. C. Plastic molds made by this method have superior heat distortion temperature and tensile elastic modulus.
    Type: Grant
    Filed: June 19, 1997
    Date of Patent: September 15, 1998
    Assignees: Takemoto Yushi Kbushiki Kaisha, Teijin Seiki Co., Ltd.
    Inventors: Toshiharu Suzuki, Tatsuhiko Ozaki, Hirokazu Matsueda, Yorikazu Tamura, Tsuneo Hagiwara