Processes Of Preparing A Solid Polymer From At Least One Nitrogen Containing Monomer; Or Compositions Therefore Patents (Class 522/173)
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Patent number: 6110988Abstract: Described is a preferred UV curable coating composition comprising (exclusive of any solvent present): (a) about 5% to 90% by weight of an acrylated aliphatic urethane having a molecular weight of about 500 to 2000 and formed by the reaction of a multifunctional acrylate with a molecular weight of about 190 to 500 and containing at least three polymerizable unsaturated groups per molecule, with an aliphatic urethane based on a polymer of alkyl carbomonocycle diisocyanate with alkanepolyol polyacrylates; (b) about 5% to 30% by weight of a multifunctional acrylate having a molecular weight of about 170 to 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 coated articles involving the preferred coating compositions.Type: GrantFiled: June 7, 1995Date of Patent: August 29, 2000Assignee: Red Spot Paint & Varnish Co, Inc.Inventor: Randall Todd Lake
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Patent number: 6080450Abstract: The use of a phosphine oxide photoinitiator enables the effective curing of a polymerizable acrylate formulation despite the incorporation of a high concentration of a fluorescing agent, thereby facilitating, and enhancing the efficiency of, evaluation of the cured deposit utilizing its fluorescent response.Type: GrantFiled: February 10, 1997Date of Patent: June 27, 2000Assignee: Dymax CorporationInventor: Stephen E. Cantor
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Patent number: 6069219Abstract: A composition of matter includes a polymerizable mixture comprising 1 to 99 weight percent of a first monomer and an initiator therefor, the first monomer being one of 1) at least one free-radically polymerizable monomer or 2) at least one cyanate ester monomer, and 99 to 1 weight percent of a second monomer and an initiator therefor, the second monomer being the member of 1) or 2) that is not selected as the first monomer, wherein the curative for the cyanate ester is a transition metal-containing organometallic compound curing agent and the curative for the free-radically polymerizable monomer is a free-radical generating curing agent or a transition metal-containing organometallic compound.Type: GrantFiled: April 27, 1998Date of Patent: May 30, 2000Assignee: 3M Innovative Properties CompanyInventors: Fred B. McCormick, David J. Drath, Ilya Gorodisher, Michael A. Kropp, Michael C. Palazzotto, Melville R. V. Sahyun
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Patent number: 6017974Abstract: An activation energy beam curable coating composition containing (A) a polymer having an organopolysiloxane unit and a quaternary ammonium salt unit and (B) a polyfunctional acrylate having 3 or more acryloyl groups in the molecule is disclosed. A film excellent in abrasion resistance, antistatic properties and transparency can be formed by applying the activation energy beam curable coating composition of the present invention to the surface of a material, and irradiating the coated surface with an activation energy beam.Type: GrantFiled: April 2, 1998Date of Patent: January 25, 2000Assignee: Mitsubishi Chemical CorporationInventors: Noritaka Hosokawa, Kazuhide Hayama
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Patent number: 6008296Abstract: 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: GrantFiled: April 19, 1995Date of Patent: December 28, 1999Assignee: Optima, Inc.Inventors: Zhou Yang, Yin-Nian Lin, Zhenya Zhu, Brian George Risch
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Patent number: 6008265Abstract: An ionic compound comprising at least one group A.sup.+ X.sup.-, comprising:a cationic group A.sup.+ selected from the group consisting of biaryliodonium, arylsulfonium, arylacylsulfonium, diazonium and organometallic cations comprising a transition metal complexed with at least one unsaturated cyclic compound comprising 4-12 carbon atoms, said cationic group being part of a polymer chain; whereinX.sup.- is an imide anion, [FSO.sub.2 NSO.sub.2 R'.sub.F ].sup.- or [R.sub.F CH.sub.2 OSO.sub.2 NSO.sub.2 R'.sub.F ].sup.- or [(R.sub.F).sub.2 CHOSO.sub.2 NSO.sub.2 R'.sub.F ].sup.-, or a methylide anion [FSO.sub.2 C(Q)SO.sub.2 R'.sub.F ].sup.-, or a [R.sub.F CH.sub.2 OSO.sub.2 C(Q)SO.sub.2 R'.sub.F ].sup.- or [(R.sub.F).sub.2 CHOSO.sub.2 C(Q)SO.sub.2 R'.sub.F ].sup.31 .Type: GrantFiled: October 3, 1997Date of Patent: December 28, 1999Assignees: Hydro-Quebec, Centre National de la Recherche ScientifiqueInventors: Alain Vallee, Michel Armand, Xavier Ollivrin, Christophe Michot
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Patent number: 5962546Abstract: Compositions containing conductivity enhancers, which are capable of being coated onto a substrate by means of electrostatic assistance. The compositions comprise one or more cationically polymerizable monomer(s), one or more cationic initiator(s), and one or more non-volatile conductivity enhancer(s) having anionic and cationic portions which are soluble in the monomer(s) and which do not interfere with cationic polymerization wherein the anionic portion is a non-coordinating carbon-containing anion. The compositions may further comprise one or more dissociation enhancing agent(s), oligomer(s) or polymer(s), preferably co-reactive, free-radically curable monomer(s), free-radical generating initiator(s), leveling agents, and other additives or adjuvants to impart specific properties to the polymerized composition.Type: GrantFiled: May 1, 1997Date of Patent: October 5, 1999Assignee: 3M Innovative Properties CompanyInventors: Albert I. Everaerts, William M. Lamanna, Albert E. Seaver, George V. D. Tiers
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Patent number: 5942372Abstract: Improved photopolymerization initiator systems are comprised of a spectral sensitizer that sensitizes in the ultraviolet or visible regions of the spectrum and an N-aryl, O-aryl or S-aryl polycarboxylic acid co-initiator. The improved initiator systems are incorporated in photo-polymerizable compositions containing one or more addition-polymerizable ethylenically-unsaturated compounds to form compositions suitable for the preparation of radiation-sensitive layers in lithographic printing plates adapted to be imagewise-exposed with ultraviolet- or visible-light-emitting lasers such as argon-ion lasers and frequency doubled Nd:YAG lasers. Such plates are able to effectively meet the dual requirements of very high photospeed and very good shelf-life required in computer-to-plate systems.Type: GrantFiled: November 19, 1996Date of Patent: August 24, 1999Assignee: Kodak Polychrome Graphics, LLCInventors: Paul Richard West, Jeffery Allen Gurney
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Patent number: 5922783Abstract: A radiation-curable composition which includes a cyanoacrylate component or a cyanoacrylate-containing formulation; a metallocene component; and a polymerizingly effective amount of a photoinitiator to accelerate the rate of cure is provided.Type: GrantFiled: February 27, 1997Date of Patent: July 13, 1999Assignee: Loctite CorporationInventor: Stan Wojciak
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Patent number: 5919603Abstract: In an additive process for producing printed wiring boards, by using a developer comprising a chlorine-free organic solvent and an alkaline aqueous solution and as a resist material a copolymer of methacrylic acid and methyl methacrylate or the like, the production steps are simplified even if a substrate having a large area is used, and abolishment of chlorine-containing organic solvent as a developer becomes possible.Type: GrantFiled: October 29, 1997Date of Patent: July 6, 1999Assignee: Hitachi, Ltd.Inventors: Masashi Miyazaki, Haruo Akahoshi, Shozo Nohara, Kenzi Kikuta, Toshiaki Ishimaru
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Patent number: 5908876Abstract: Disclosed are: (1) an optical resin composition comprising Component A: a thiourethane prepolymer compound prepared by reacting a polythiol compound having at least 3 functional groups and an intramolecular sulfide bond, with a polyisocyanate compound in a molar ratio of --SH to --NCO ranging from 3.0 to 7.0 Component B: at least one (meth)acrylate compound having at least 2 functional groups; and Component C: a compound radically polymerizable with Components A and B, in 10 to 50% by weight, 35 to 70% by weight, and 5 to 30% by weight, respectively; (2) a preparation process for an optical resin by photopolymerization; (3) an optical resin; and (4) a prepolymer suitable for Component A. The composition is a novel, rapidly polymerizable composition for an optical resin. Furthermore, a resin prepared by curing the composition not only has a high refractive index and a high Abbe number, but also is excellent in transparency and optical homogeneity.Type: GrantFiled: April 7, 1997Date of Patent: June 1, 1999Assignee: Mitsui Chemicals, Inc.Inventors: Kenichi Fujii, Nobuya Kawauchi, Toshiyuki Suzuki, Seiichi Kobayashi, Masao Imai
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Patent number: 5905099Abstract: A heat-activatable adhesive comprising an acrylic copolymer, which copolymer comprises a monomer consisting of an acrylate or methacrylate ester of a non-tertiary alkyl alcohol having a Tg of about 0.degree. C. or lower; a monomer consisting of an acrylate or methacrylate ester of an alcohol having a Tg of at least about 5.degree. C.; and a functional monomer. Selected embodiments include a retroreflective article comprising a film having a substantially flat surface and a structured surface, the structured surface comprising a plurality of precisely shaped projections, a colored layer disposed on the structured surface and adhered thereto in a plurality of discrete locations, and a heat-activatable adhesive layer disposed on the colored layer.Type: GrantFiled: November 6, 1995Date of Patent: May 18, 1999Assignee: Minnesota Mining and Manufacturing CompanyInventors: Albert I. Everaerts, Yoshinori Araki, Michiru Hata
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Patent number: 5902837Abstract: 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: GrantFiled: August 9, 1996Date of Patent: May 11, 1999Assignee: Sanyo Chemical Industries, Ltd.Inventors: Takao Saito, Kohei Maeda, Naoshi Ozasa
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Patent number: 5900444Abstract: 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: GrantFiled: October 8, 1996Date of Patent: May 4, 1999Inventor: Alan Zamore
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Patent number: 5877230Abstract: A method for the anionic photoinitiation of polymerization or crosslinking of a substrate by irradiating a mixture of a substrate and a photoinitiator, where the photoinitiator is an inorganic transition metal complex which releases on irradiation a polymerization initiating substance consisting essentially of an anionically charged nucleophile that initiates the polymerization or crosslinking reaction, under conditions that allow the anion to initiate polymerization. FIG. 3 is plot of percentage polymerization of ethyl .alpha.-cyanoacrylate containing different concentration of Reineckate's anion.Type: GrantFiled: July 25, 1997Date of Patent: March 2, 1999Assignees: University of Georgia Research Foundation, Inc., The University of GeorgiaInventor: Charles R. Kutal
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Patent number: 5859087Abstract: 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: GrantFiled: October 16, 1996Date of Patent: January 12, 1999Assignee: DSM NVInventor: Edward P. Zahora
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Patent number: 5821278Abstract: Process for the photocatalytic polymerization of a cyclic olefin or at least two different cyclic olefins in the presence of a metal compound as catalyst, which comprises carrying out a photochemical ring-opening metathesis polymerization in the presence of a catalytic amount of at least one heat-stable niobium(V) or tantalum(V) compound which contains at least two methyl groups or two monosubstituted methyl groups bound to the metal, the substituent containing no hydrogen atom in the .alpha.-position.The process can also be carried out by first performing the irradiation and completing the polymerization by heating. The process is suitable, for example, for the preparation of thermoplastic molding materials, coatings and relief images.Type: GrantFiled: May 22, 1997Date of Patent: October 13, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Paul Adriaan Van Der Schaaf, Andreas Hafner, Andreas Muhlebach
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Patent number: 5798397Abstract: Provided is a composition curable by active energy rays, comprising a cationic polyacryloyl compound having two or more acryloyl groups and one or more cation groups in a molecule, represented by any of General Formulae (1) to (6) ##STR1## wherein Z.sub.1 to Z.sub.6 represent independently a residue derived from a polyhydric alcohol or a polyepoxide,K.sub.1 represents independently a radical of the formula ##STR2## K.sub.2 represents a radical of the formula ##STR3## R.sub.1 represents independently a radical of the formula ##STR4## wherein R.sub.3 is independently H-- or CH.sub.3 --, and R.sub.2 represents independently a radical of the formulaCH.sub.2 .dbd.CHCOO--, or CH.sub.2 .dbd.C(CH.sub.3)COO--.Type: GrantFiled: December 24, 1996Date of Patent: August 25, 1998Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Makiko Kimura, Masato Katayama, Akio Kashiwazaki, Yoshie Nakata, Yuko Nishioka
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Patent number: 5783615Abstract: 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: GrantFiled: April 16, 1997Date of Patent: July 21, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Bettina Steinmann, Adrian Schulthess, Max Hunziker
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Patent number: 5767170Abstract: A single package adhesive for tooth bonding applications which comprises a bulk-water-free solvent-based homogeneous liquid containing:1) An ethylenically unsaturated monomer that possesses a hygroscopic functional group that (a) is capable of chemically reacting with and through the ethylenic bond of the ethylenically unsaturated-functional monomer of 2) below, and (b) provides the capacity for chemical bonding to the surface to which the adhesive is applied.Type: GrantFiled: April 30, 1996Date of Patent: June 16, 1998Assignee: Den-Mat CorporationInventors: Robert L. Ibsen, Alan B. Matthews, William R. Glace
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Patent number: 5763503Abstract: 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: GrantFiled: May 3, 1996Date of Patent: June 9, 1998Assignee: Esschem, Inc.Inventors: George F. Cowperthwaite, Gary R. Shaw, Susan C. Sheariss
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Patent number: 5728750Abstract: Radiation-curable compositions comprisinga) compounds having at least two carbon-carbon double bonds with which it is possible for primary or secondary amino groups to form adducts in the form of a Michael-analogous addition reaction (referred to in short below as activated double bonds)b) capped amino compounds which 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 hydrogen atoms) being at least 2.Type: GrantFiled: May 29, 1996Date of Patent: March 17, 1998Assignee: BASF AktiengesellschaftInventors: Reinhold Schwalm, Wolfgang Reich, Lukas Haussling, Erich Beck
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Patent number: 5721286Abstract: A method for curing polymers (11) incorporating a variable frequency microwave furnace system (10) designed to allow modulation of the frequency of the microwaves introduced into a furnace cavity (34). By varying the frequency of the microwave signal, non-uniformities within the cavity (34) are minimized, thereby achieving a more uniform cure throughout the workpiece (36). A directional coupler (24) is provided for detecting the direction of a signal and further directing the signal depending on the detected direction. A first power meter (30) is provided for measuring the power delivered to the microwave furnace (32). A second power meter (26) detects the magnitude of reflected power. The furnace cavity (34) may be adapted to be used to cure materials defining a continuous sheet or which require compressive forces during curing.Type: GrantFiled: September 6, 1995Date of Patent: February 24, 1998Assignee: Lockheed Martin Energy Systems, Inc.Inventors: Robert J. Lauf, Don W. Bible, Felix L. Paulauskas
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Patent number: 5710233Abstract: Polyurethane elastomers with reduced gas permeability are prepared by reaction of:a) diisocyanates,b) compounds with a molecular weight of 500 to 10,000 having at least two hydrogen atoms that are reactive towards isocyanates,c) compounds with a molecular weight of 61 to 499 having at least two hydrogen atoms that are reactive towards isocyanates, and optionallyd) further auxiliaries and additives,characterized in thati) the ratio of the isocyanate groups in a) to the sum of the isocyanate-reactive groups in b) and c) is between 1:0.80 and 1:1.05 (isocyanate:isocyanate-reactive), andii) the compound b) contains 3 to 15% by wt.Type: GrantFiled: January 6, 1997Date of Patent: January 20, 1998Assignee: Rhein Chemie Rheinau GmbHInventors: Walter Meckel, Klaus Konig, Hans-Dieter Thomas
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Patent number: 5703140Abstract: A photopolymerizable composition is disclosed, comprising at least (i) a compound having an addition-polymerizable ethylenically unsaturated bond, and (ii) an oxime ether compound. The photopolymerizable composition of the present invention shows high sensitivity to active light rays over a wide range of from ultraviolet ray to visible light and at the same time, the photosensitive material using the photopolymerizable composition of the present invention is improved in the storage stability. Further, the development precipitate generated from the developer waste after development of the photosensitive material is restrained.Type: GrantFiled: January 23, 1996Date of Patent: December 30, 1997Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuto Kunita, Syunichi Kondo
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Patent number: 5652280Abstract: A method for the anionic photoinitiation of polymerization or crosslinking of a substrate by irradiating a mixture of a substrate and a photoinitiator, where the photoinitiator is an inorganic transition metal complex which releases on irradiation a polymerization initiating substance consisting essentially of an anionically charged nucleophile that initiates the polymerization or crosslinking reaction, under conditions that allow the anion to initiate polymerization.Type: GrantFiled: May 17, 1994Date of Patent: July 29, 1997Assignee: University of Georgia Research Foundation, Inc.Inventor: Charles R. Kutal
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Patent number: 5635544Abstract: Disclosed is a process for preparing a UV-curable coating material comprising the steps of effecting a hydrolysis reaction of (a-1) 40 to 90 parts by weight of colloidal silica, and (a-2) 60 to 10 parts by weight of a hydrolyzate of an alkoxy silane compound containing not less than 50% by weight of a compound of the formula (I) ##STR1## replacing the dispersion medium of the colloidal silica with a nonpolar solvent when the amount of dehydration is in the range of 50 to 90% of theoretical value; and effecting a further condensation reaction while maintaining in the state of 30 to 90% by weight of solid components in the presence of the nonpolar solvent.A coating composition containing the UV-curable coating material can form an anti-abrasion-coating film having excellent abrasion resistance, surface smoothness, thermal resistance, chemical resistance, durability, weather resistance and adhesion to the substrate.Type: GrantFiled: June 7, 1995Date of Patent: June 3, 1997Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Misao Tamura, Hiroshi Fukushima
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Patent number: 5629354Abstract: Improved photopolymerization initiator systems are comprised of a spectral sensitizer that sensitizes in the ultraviolet or visible regions of the spectrum and an N-aryl, O-aryl or S-aryl polycarboxylic acid co-initiator. The improved initiator systems are incorporated in photo-polymerizable compositions containing one or more addition-polymerizable ethylenically-unsaturated compounds to form compositions suitable for the preparation of radiation-sensitive layers in lithographic printing plates adapted to be imagewise-exposed with ultraviolet- or visible-light-emitting lasers such as argon-ion lasers and frequency doubled Nd:YAG lasers. Such plates are able to effectively meet the dual requirements of very high photospeed and very good shelf-life required in computer-to-plate systems.Type: GrantFiled: February 28, 1995Date of Patent: May 13, 1997Assignee: Eastman Kodak CompanyInventors: Paul R. West, Jeffery A. Gurney
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Patent number: 5612390Abstract: A thiol methacrylate or acrylate compound represented by the formula (1) or (2), ##STR1## wherein R.sup.1 is H or CH.sub.3 and X is selected from: ##STR2## wherein R.sup.1 is H or CH.sub.3 and m is an integer of 1 to 4. The thiol methacrylate or acrylate compound gives a resin having a high refractive index, a large Abbe number, and a good hardness and heat resistance, and giving little or no smell at processing.Type: GrantFiled: June 7, 1995Date of Patent: March 18, 1997Assignee: Toray Industries, Inc.Inventors: Yuichiro Iguchi, Michio Kimura, Koichiro Oka
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Patent number: 5612387Abstract: A new nonlinear organic optical material having a high Second Harmonic Generation capability and a method of manufacturing the same is disclosed. Energy-beam sensitive monomer molecules having large molecular dipole-moments are sandwiched between two facing orientation films formed on respective substrates, and the energy-beam sensitive parts in said molecules are polymerized by irradiation with an energy-beam such as an X-ray beam after the dipole-moments of the energy-beam sensitive monomer molecules are aligned by applying a magnetic or an electric field. As a result of this, no cancellation of dipole-moments takes place, and polymers having extremely high dipole-moments and high Second Harmonic Generation efficiency can be derived and manufactured.Type: GrantFiled: May 31, 1995Date of Patent: March 18, 1997Assignee: Matsushita Electric Industrial Co., Ltd.Inventor: Kazufumi Ogawa
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Patent number: 5608013Abstract: A polyimide obtained by reacting an acid dianhydride such as catechol bistrimellitate dianhydride, bisphenol A bistrimellitate dianhydride, etc. with a diamine such as 4,4'-diamino-3,3',5,5'-tetraisopropyl-diphenylmethane, etc. has high solubility in organic solvents and good moldability at low temperatures, and can provide a thermosetting resin composition together with a polymaleimide.Type: GrantFiled: March 7, 1995Date of Patent: March 4, 1997Assignee: Hitachi Chemical Company, Ltd.Inventors: Hidekazu Matsuura, Yasuo Miyadera
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Patent number: 5605781Abstract: A photosensitive composition containing a curable cyanate ester and a cationic photoinitiator; and use thereof to form a resist image.Type: GrantFiled: June 7, 1995Date of Patent: February 25, 1997Assignee: International Business Machines CorporationInventors: Jeffrey D. Gelorme, Eugene R. Skarvinko, David W. Wang
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Patent number: 5539012Abstract: Resin compositions useful for filament winding applications comprising an epoxy component including at least one polyepoxide resin curable by heat, an olefinicially unsaturated monomer component including at least one polyolefinically unsaturated monomer curable by actinic radiation, a cyanate ester component including at least one cyanate ester compound having at least two cyanate functional groups per molecule, at least one organic peroxide, at least one photoinitiator, and a heat activated curing agent for epoxides. The compositions have a viscosity less than about 2000 centipoise (cps) and are capable of retaining this viscosity for at least about 6 months at about ambient temperature. The resins are capable of being immobilized by actinic radiation exposure and further heat cured without substantial resin drip. One or more organic peroxides are employed, selected from the group of organic peroxides having 10 hour decomposition half-lives at temperatures of from about 50.degree. C. to less than about 104.Type: GrantFiled: August 18, 1993Date of Patent: July 23, 1996Assignee: Loctite CorporationInventors: Philip T. Klemarczyk, Yoshihisa Okamoto
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Patent number: 5530037Abstract: A curable cyanoacrylate adhesive composition intended for medical and/or veterinary uses is sterilized in liquid form by gamma irradiation. The composition comprisesa) a cyanoacrylate monomerb) a combination of an anionic stabilizer and a free-radical stabilizer in amounts effective to stabilize the composition during irradiation and to stabilize the sterilized composition during storage prior to cure, wherein the free radical stabilizer is a selected phenolic antioxidant (but not including hydroquinone).The preferred free radical stabilizer is butylated hydroxyanisole. After irradiation the cyanoacrylate monomer is substantially ungelled.Type: GrantFiled: December 21, 1994Date of Patent: June 25, 1996Assignee: Loctite (Ireland) LimitedInventors: Patrick F. McDonnell, Robert J. Lambert
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Patent number: 5502083Abstract: The composition of the present invention is excellent in compatibility, transparency and curability and give a cured coat of excellent gloss and of less smell, and cured products of excellent properties can be obtained by curing the composition.The present invention relates to an onium salt represented by the following formula (1): ##STR1## wherein Ar is a mono- to tetra-valent aromatic group, X is a bisphenylsulfonio group which may have a substituent, a is 1-4, b is 0 or 1-3, a+b is 1-4, n is 1-4, and Z is a halide represented by the following formula (3):MQ.sub.m (OH).sub.l (3)where M is a boron atom, a phosphorus atom, an arsenic atom or an antimony atom, Q is a halogen atom, m is 3-6, l is 0 or 1, and m+l is 4-6; a photopolymerization initiator containing the onium salt as an active ingredient; an energy ray-curable composition containing the initiator; and a cured product.Type: GrantFiled: June 8, 1994Date of Patent: March 26, 1996Assignee: Nippon Kayaku Kabushiki KaishaInventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
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Patent number: 5489664Abstract: Crosslinkable liquid composition based on organic isocyanates and epoxy compounds, comprising the following components:(A) an organic polyisocyanate;(B) a polyepoxide or mixture of a polyepoxide and a monoepoxide; and(C) a catalyst constituted by at least one cyanoderivative containing a quaternary nitrogen atom,which composition can be polymerized at temperatures of 40.degree. C. or higher, by a process comprising exposure thereof to a non-ionizing electromagnetic radiation having a frequency comprised in the microwave range of frequencies, to obtain a solid material endowed with an excellent combination of physical, chemical and mechanical properties.Type: GrantFiled: November 4, 1994Date of Patent: February 6, 1996Assignees: Enichem S.p.A., Eniricerche S.p.A.Inventors: Fabrizio Parodi, Renata Gerbelli, Mark De Meuse
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Patent number: 5484821Abstract: A novel photocrosslinkable polymeric system has been developed for processing into films having stable second-order nonlinear optical properties. In the present system, polymers bearing photo-crosslinkable chromophores, such as polyvinylcinnamate and are reacted with appropriately designed nonlinear optical molecules with the cinnamate or other photocrosslinkable functionalities for photocrosslinking at one, two or more points. The system can be poled and photocrosslinked in the poled state to yield a material with stable optical nonlinearity and large electro-optic coefficients.Type: GrantFiled: February 7, 1994Date of Patent: January 16, 1996Assignee: University of LowellInventors: Braja K. Mandal, Sukant K. Tripathy, Jan-Chan Huang, Jayant Kumar
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Patent number: 5484864Abstract: UV curable adhesive compositions which provide improved bonding to substrates such as carbonates and metals is provided. The compositions are formed as the reaction product of a urethane methacrylate and reactive diluents such as N-vinyl caprolactam and isobornyl acrylate, a photoinitiator compound, and adhesion promoting additives. Urethane methacrylates which may be employed include ester-based urethane methacrylates as well as ether based urethane methacrylates. Also, methods of bonding substrates using their compositions and the articles produced by the methods.Type: GrantFiled: January 31, 1995Date of Patent: January 16, 1996Assignee: CasChem, Inc.Inventors: Douglas A. Usifer, Ifeanyi C. Broderick
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Patent number: 5466496Abstract: Liquid crystal films which are stable to light, moisture and heat, and which have an improved response time and viewing angle are provided by combining ferroelectric liquid crystals and a polymer matrix. The invention further provides for liquid crystal display elements utilizing the liquid crystal films of the invention. Still further, the invention provides methods of producing the liquid crystal films. According to the invention, liquid crystalline polymers having optical anisotropy as a polymer matrix and functional side chain radicals having an asymmetric carbon atom and dipole moment in the polymer matrix are matched with the dipole moment of the ferroelectric crystals.Type: GrantFiled: April 13, 1994Date of Patent: November 14, 1995Assignee: Samsung Electron Devices Co., Ltd.Inventor: Yong W. Jin
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Patent number: 5453429Abstract: New bile acid sequestrant polymer compositions and a process for preparing the polymers in particulate form, preferably in spherical form, are described. The polymer particles are prepared by crosslinking an amine-containing polymer with an amount of a polyfunctional amine-reactive compound sufficient to crosslink the polymer so that it is essentially water insoluble and has bile acid sequestering efficacy greater than that of cholestyramine, preferably greater than about three times the efficacy of cholestyramine. A preferred polymerization process involves suspension polymerization of water-soluble amine-containing monomers, such as dialkylaminoalkyl (meth)acrylate esters and dialkylaminoalkyl (meth)acrylamides, in the presence of polyfunctional amine-reactive compounds, such as substituted dihaloalkanes. Pharmaceutical compositions containing the bile acid sequestrant polymer particles and a method for lowering blood cholesterol levels using the pharmaceutical compositions are also described.Type: GrantFiled: February 6, 1995Date of Patent: September 26, 1995Assignee: Rohm and Haas CompanyInventors: Paul E. Bliem, Larry W. Steffier
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Patent number: 5449702Abstract: Disclosed is a coating composition comprising(A) 5 to 60 parts by weight, on a solid basis, of colloidal silica,(B) 5 to 70 parts by weight of a hydrolyzate and/or hydrolyzed and partially condensed product of a compound of the general formula ##STR1## (C) 10 to 80 parts by weight of a polyfunctional monomer containing a monomer of the general formula ##STR2## and (D) 0.01 to 5 parts by weight of a photopolymerization initiator containing a compound of the general formula ##STR3## provided that the combined amount of components (A), (B), (C) and (D) is 100 parts by weight.This coating composition can be cured in air by exposure to ultraviolet light, and the resulting cured film is excellent in various properties (such as abrasion resistance) and adhesion to the substrate.Type: GrantFiled: November 27, 1992Date of Patent: September 12, 1995Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Suehiro Tayama, Misao Tamura, Tsukasa Mizobuchi
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Patent number: 5446073Abstract: Composition containing charge transfer complex from at least one unsaturated compound having an electron donor group and having an electron withdrawing group and being free of any photoinitiating compound is polymerized by being subjected to ultraviolet light.Type: GrantFiled: March 31, 1993Date of Patent: August 29, 1995Assignee: Fusion Systems CorporationInventors: Sonny Jonsson, Per-Erik G. Sundell, William R. Schaeffer
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Patent number: 5405366Abstract: This invention relates to a non-stringy adhesive hydrophilic gel comprising an aqueous mixture of a radiation crosslinkable water-soluble polymer, at least one humectant effective to extend the moisture retaining characteristics of the gel and which inhibits the ability of radiant energy to crosslink the water-soluble polymer, a pharmacologically active agent, and a crosslinking promoter effective to counteract the crosslinking inhibitory effect of humectant. The aqueous mixture is exposed to radiant energy effective to provide a non-stringy adhesive cohesive homogeneous hydrophilic gel that has an extended in-use lifetime. The gels can be formed into PATCHES for long term application of the pharmacologically active agent to a patient.Type: GrantFiled: November 12, 1992Date of Patent: April 11, 1995Assignee: Nepera, Inc.Inventors: Adrian S. Fox, Christine A. Czap, Robin R. Wiser
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Patent number: 5397812Abstract: An adhesive composition for being applied to at least one of thread contact faces of screw members so as to stick said thread contact faces to each other in engaging the screw members with each other for the purpose of locking and sealing the engaged screw members, in which micro-capsules enclosing at least a reactive monomer of a reactive adhesive composition comprising said monomer, a polymerization initiator of the aforesaid monomer and/or an activator of the aforesaid polymerization initiator is dispersed in a binder comprising a photo-hardening resin composition.Type: GrantFiled: March 9, 1993Date of Patent: March 14, 1995Assignee: Three Bond Co., Ltd.Inventors: Ikuzo Usami, Makoto Kurihara, Minami Hanada, Kunihiko Nakajima
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Patent number: 5384342Abstract: The present invention is directed to a compound of the Formula:R.sub.1 --R.sub.2 --R.sub.3 --R.sub.4 --A--(R.sub.5).sub.n (R.sub.6).sub.3-nwherein: A is Si or Ti; R.sub.1 is an alkenoxy, acryloxy or ethylenically unsaturated dicarboxylate group; R.sub.2 is a 2 to 18 carbon linear, branched or cyclo alkyl, alkenyl, alkynyl, acyl, aryl or poly(alkoxy) group; R.sub.3 contains a urethane, urea, or thiourethane linkage; R.sub.4 is a 2 to 18 carbon linear, branched, or cyclic alkyl, alkenyl, alkynyl, aryl or acyl non-hydrolyzable silyl linking group; R.sub.5 is a 2 to 18 carbon linear, branched, or cyclic alkyl, alkenyl, alkynyl, aryl or acyl group; R.sub.6 is any hydrolyzable silyl linking group (alkoxy, alkenoxy, or halogen); and n is 0 to 2.The present invention is further directed to an improved method of using of a compound of the above Formula as an adhesion promoter in a UV-curable composition for a surface with a free nucleophilic group. Preferably, that surface is glass.Type: GrantFiled: August 30, 1993Date of Patent: January 24, 1995Assignee: DSM Desotech, Inc.Inventor: David M. Szum
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Patent number: 5356947Abstract: The present invention provides controllably curable photoiniferter containing adhesive compositions which are suitable for the mounting of microelectronic devices such as flip chips onto transparent wiring boards, a method of making the adhesive compositions, and a method of using the adhesive compositions in order to bond microelectronic devices to transparent wiring boards by intermittent exposure of the adhesive composition to a radiant energy source. The adhesive compositions can be cured in a stepwise fashion by intermittent controlled exposure to a source of radiation thus providing exactly the amount of cure and hardening desired.Type: GrantFiled: October 29, 1992Date of Patent: October 18, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Mahfuza B. Ali, Jean M. Pujol
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Patent number: 5344701Abstract: Supports having azlactone-functional surfaces, adduct supports prepared from such azlactone-functional supports, and methods of preparing both are disclosed. Azlactone functionality is introduced to surfaces of a pre-existing support in a manner which retains useful physical and chemical characteristics of the pre-existing support. One method involves exposing surfaces with high energy radiation to generate free radical reaction sites on the surfaces and causing azlactone-functional moieties to react with the free radical reaction sites. Another method involves coating surfaces with azlactone monomers, crosslinking monomers, and optionally co-monomers and polymerizing the monomers to form a polymerized coating of azlactone-functionality on the surfaces. Another method involves dispersion polymerization of azlactone-functional moieties to produce azlactone-functional particles within pores and interstices of a pre-existing support.Type: GrantFiled: June 9, 1992Date of Patent: September 6, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: David R. Gagnon, Patrick L. Coleman, Gary J. Ortina, Christopher S. Lyons, Dean S. Milbrath, Jerald K. Rasmussen, Julie B. Stahl
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Patent number: 5344353Abstract: A method for manufacturing a cathode ray tube is provided which comprises (a) spraying on the inner surface of a phosphor layer of a phosphor coated panel, an organic composition for forming a heat labile film, the organic composition being free of flammable or explosive organic solvents and including an initiator capable of forming a radical or cation when exposed to ultraviolet or electron rays and at least one resin containing at least one group consisting of acrylate, vinyl and diazo functional groups to form a heat labile film thereon; (b) exposing the heat labile film to ultraviolet or electron rays to from a hardened film layer; (c) forming an aluminum layer on a surface of the hardened film layer to form a screen; (d) sealing with heat the panel and a funnel to form a bulb with a mount including an electron gun and a stem, wherein the step of sealing to form a bulb decomposes the hardened film layer.Type: GrantFiled: November 1, 1991Date of Patent: September 6, 1994Assignee: Samsung Electron Devices Co., Ltd.Inventors: Dong-sik Jang, Byeong-yong Lee
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Patent number: 5334486Abstract: A photopolymerizable composition comprising: (a) a compound obtained by reacting one mole of a polyamine represented by the following general formula (I) with at least 2 moles of a compound having a group capable of reacting with the polyamine and a polymerizable ethylenically unsaturated group: ##STR1## wherein n is an integer of not less than 1 and (b) a photopolymerization initiator.A dry PS plate comprises a substrate provided thereon with, in order, a light-sensitive resin layer and a silicone rubber layer wherein the light-sensitive resin layer comprises the photopolymerizable composition and a polymeric compound having film-forming ability.The photopolymerizable composition and the dry PS plate have very high sensitivity.Type: GrantFiled: December 23, 1991Date of Patent: August 2, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Yukio Abe, Tatsuji Higashi, Tsumoru Hirano, Syunichi Kondo
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Patent number: 5317081Abstract: A method and apparatus are disclosed for conducting a physical process and a chemical reaction by exposing a material containing a volatile substance to microwave radiation where the morphology of said material will change when exposed to such radiation. The power of said radiation is adjusted over time as the morphology of the material changes to maximize the effect of the radiation in order to produce a product in a minimum amount of time that is substantially free of said volatile substance.The method and apparatus can also be used to conduct such a process or reaction with materials that do not contain a volatile material.In one embodiment a method and apparatus are disclosed for manufacturing a polyimide from a precursor in a solvent by exposing the precursor to microwave radiation in a tuneable microwave resonant cavity that is tuned during imidization to achieve critical coupling of the system. Microwave power is controlled to remove the solvent and obtain the desired level of reaction.Type: GrantFiled: November 27, 1991Date of Patent: May 31, 1994Assignee: International Business Machines CorporationInventors: Jeffrey D. Gelorme, David A. Lewis, Jane M. Shaw