With Ethylenic Reactant Patents (Class 522/103)
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Patent number: 6087417Abstract: The invention provides aqueous, solvent based, and solvent-free curable coating compositions which include (A) the reaction product of epoxy resin, acid, and tertiary amine; (B) reactive diluent, and, optionally, (C) curing agent. The compositions are useful for forming cured coated substrates, that are especially suitable for food and beverage packaging.Type: GrantFiled: January 16, 1998Date of Patent: July 11, 2000Assignee: The Valspar CorporationInventors: Thomas A. Stevenson, Larry Brandenburger, William McCarty, John Mazza, Jeffrey Niederst
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Patent number: 6054250Abstract: The present invention relates to polymer precursors used in sterolithography. Specifically, the invention provides a novel resin having a glass transition temperature (Tg) that is substantially higher than any existing resins. The polymer precursors comprise an admixture of at least one vinyl ether, functionalized compound and at least one epoxy functionalized compound, at least one acrylate functionalized compound, and a photoinitiator, wherein the polymer precursor composition cures by a dual cure mechanism utilizing a free radical pathway as well as a cationic pathway thus yielding improved green strength.Type: GrantFiled: January 26, 1998Date of Patent: April 25, 2000Assignee: AlliedSignal Inc.Inventors: Eugene V. Sitzmann, Russell F. Anderson, Mathias P. Koljack, Julietta G. Cruz, Chandra M. Srivastava
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Patent number: 6039798Abstract: 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: GrantFiled: February 12, 1999Date of Patent: March 21, 2000Assignee: Crosfield LimitedInventors: Derek Aldcroft, Sharron Bates, Graham James Earl
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Patent number: 6013339Abstract: This invention relates to a liquid crystal display apparatus formed by sealing a liquid crystal between two substrates having electrodes and an alignment film with a seal material, the production process comprising the steps of attaching two substrates in a vacuum, compressing under atmospheric pressure to provide a uniform cell gap, a temporary hardening process of the seal material by ultraviolet ray irradiation and a main hardening process of the seal material by heating, wherein a radically polymerizable curing resin is used in the liquid crystal seal material. The method provides a liquid crystal display panel having a uniform cell gap, without dislocation of the alighnment between substrates, or discharge of uncured component of a seal material to the liquid crystal, capable of having a seal material firmly attached to the substrates even at panel corner portions, and having an excellent straightness and moisture resistance of the seal material.Type: GrantFiled: December 10, 1997Date of Patent: January 11, 2000Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Satoshi Yamada, Hideki Matsukawa
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Patent number: 6011078Abstract: Described are aqueous, radiation-curable coating compositions comprising:a) from 5.0 to 90.0% by weight of at least one water-dispersible polymer P comprising at least one .alpha.,.beta.-ethylenically unsaturated, radiation-polymerizable double bond,b) from 0.1 to 90% by weight of at least one radiation-curable compound S which is different from P and which is soluble in water or is dilutable with at least 10% by weight of water, based on the overall weight of the coating composition, and which comprises at least one .alpha.,.beta.-ethylenically unsaturated, radiation-polymerizable double bond,c) from 0 to 20% by weight of a photoinitiator,d) from 0 to 60% by weight of a filler,e) from 0 to 20% by weight of further additives,f) water to 100% by weight and their use.Type: GrantFiled: May 4, 1998Date of Patent: January 4, 2000Assignee: BASF AktiengesellschaftInventors: Wolfgang Reich, Peter Enenkel, Edmund Keil, Matthias Lokai, Erich Beck, Klaus Menzel
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Patent number: 6008266Abstract: An uncured thermosetting composition which is capable of curing upon exposure to actinic radiation is disclosed. The composition includes an acetal diepoxide of the formula: ##STR1## wherein R and R' are individually an aliphatic epoxy, or a cycloaliphatic epoxy; R.sub.1 and R.sub.4 are individually an alkyl, substituted alkyl, aryl, aryl alkyl; and R.sub.2 and R.sub.3 are individually hydrogen, alkyl, alkoxy, substituted alkyl aryl, alkyl aryl, and cyclic alkyl; as well as a photoinitiator, and an inorganic filler. The composition of the invention may also include a second epoxy functional resin, a flexibilizer, and other adjuvants. Other aspects of the invention include the cured resin encapsulant and a method of recovering the resin from a circuit assembly.Type: GrantFiled: August 14, 1996Date of Patent: December 28, 1999Assignee: International Business Machines CorporationInventors: Joseph Paul Kuczynski, Laura Marie Mulholland
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Patent number: 6002511Abstract: 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: GrantFiled: January 14, 1998Date of Patent: December 14, 1999Assignee: Donnelly CorporationInventors: Desaraju V. Varaprasad, Mingtang Zhao, Craig Allen Dornan, Anoop Agrawal, Pierre-Marc Allemand, Niall R. Lynam
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Patent number: 6001203Abstract: This invention relates to a liquid crystal display apparatus formed by sealing a liquid crystal between two substrates having electrodes and an alignment film with a seal material, the production process comprising the steps of attaching two substrates in a vacuum, compressing under atmospheric pressure to provide a uniform cell gap, a temporary hardening process of the seal material by ultraviolet ray irradiation and a main hardening process of the seal material by heating, wherein a radically polymerizable curing resin is used in the liquid crystal seal material. The method provides a liquid crystal display panel having a uniform cell gap, without dislocation of the alighnment between substrates, or discharge of uncured component of a seal material to the liquid crystal, capable of having a seal material firmly attached to the substrates even at panel corner portions, and having an excellent straightness and moisture resistance of the seal material.Type: GrantFiled: December 10, 1997Date of Patent: December 14, 1999Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Satoshi Yamada, Hideki Matsukawa
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Patent number: 5998495Abstract: Photocurable, addition polymerizable compositions contain an epoxy resin and a photoinitiator system containing (a) an epoxy resin, (b) a hydroxyl containing material and (c) a photoinitiator system comprising: (i) an iodonium salt; (ii) a visible light sensitizer; and (iii) an electron donor compound, wherein the photoinitiator system has a photoinduced potential of at least about 100 mV relative to a standard solution of 2.9.times.10.sup.-5 moles/g diphenyl iodonium hexafluoroantimonate and 1.5.times.10.sup.-5 moles/g camphorquinone in 2-butanone. The compositions cure on exposure to light in the visible spectrum and are useful in a variety of applications, including dental adhesives and composites.Type: GrantFiled: April 11, 1997Date of Patent: December 7, 1999Assignee: 3M Innovative Properties CompanyInventors: Joel D. Oxman, Dwight W. Jacobs
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Patent number: 5990189Abstract: A photopolymerizable material is provided that is suitable for use in the production of coatings or resists on printed circuit boards, for example The material is an ethylenically unsaturated polymerizable reaction product of a polyepoxide and a mixture of (i) a major proportion of an ethylenically unsaturated carboxylic acid and (ii) a minor. proportion of a saturated aliphatic or aromatic carboxylic acid, the reaction product being further modified by reaction with a dicarboxylic acid or anhydride thereof.Type: GrantFiled: January 14, 1998Date of Patent: November 23, 1999Assignee: Coates Brothers PLCInventors: Stephen Anthony Hall, Nicholas Eric Ivory
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Patent number: 5948514Abstract: A photocurable and thermosetting resin composition developable with an aqueous alkali solution is disclosed. The composition comprises in combination: (A) a photosensitive prepolymer soluble in a dilute aqueous alkali solution obtained by esterifying an epoxy resin represented by the following general formula (1) with (meth)acrylic acid and further adding an acid anhydride thereto until an acid value reaches a level in the range of 60 to 120 mg KOH/g, (B) a diglycidyl ether type epoxy compound containing two epoxy groups in the molecular unit thereof, (C) a photopolymerization initiator, and (D) a diluent at such ratios of combination that said epoxy compound (B) accounts for a proportion in the range of 5 to 120 parts by weight and said photopolymerization initiator (C) for a proportion in the range of 0.1 to 30 parts by weight, based on 100 parts by weight of said photosensitive prepolymer (A): ##STR1## wherein X represents CH.sub.2, C(CH.sub.3).sub.2, or SO.sub.Type: GrantFiled: June 5, 1996Date of Patent: September 7, 1999Assignee: Taiyo Ink Manufacturing Co., Ltd.Inventors: Shigeru Komori, Kazuo Suda, Masao Arima, Miyako Juni
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Patent number: 5945463Abstract: 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: GrantFiled: March 28, 1997Date of Patent: August 31, 1999Assignees: Zeon Rize Co., Ltd., Sunarrow LimitedInventors: Ichiro Kawabuchi, Tetsuro Yamada, Yoshio Kenmochi, Atsuo Ishikawa
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Patent number: 5942371Abstract: Photopolymerisable compositions are described which comprisea) 20 to 80% by weight of a specific film-forming, acid group-containing acrylate of higher molecular weight which is neutralised with ammonia or an amine or an inorganic base, at least 10% by weight of component a) consisting of a acrylate of higher molecular weight which is derived from a reaction product of a polymolecular epoxy resin that is advanced with a bisphenol and an ethylenically unsaturated monocarboxylic acid and after subsequent reaction with a cyclic anhydride of an organic polycarboxylic acid,b) 0.1 to 15% by weight of a photoinitiator,c) 1 to 25% by weight of optional components, andd) water, as well ase) at least one additional optional (meth)acrylate monomer or (meth)acrylate oligomer or a vinyl compound that can be crosslinked with light.The compositions contain no additional polymolecular polymer binders and which can be used as aqueous applicable photoresist compositions, preferably for coating printed circuit boards.Type: GrantFiled: September 13, 1996Date of Patent: August 24, 1999Assignee: Ciba Specialty Chemicals Corp.Inventors: Roger Pierre-Elie Salvin, Martin Roth
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Patent number: 5919834Abstract: 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: GrantFiled: September 29, 1997Date of Patent: July 6, 1999Assignee: Illinois Tool Works Inc.Inventors: Myron H. Downs, James D. Singelyn, Bruce W. Downs
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Patent number: 5898041Abstract: This invention relates to a liquid crystal display apparatus formed by sealing a liquid crystal between two substrates having electrodes and an alignment film with a seal material, the production process comprising the steps of attaching two substrates in a vacuum, compressing under atmospheric pressure to provide a uniform cell gap, a temporary hardening process of the seal material by ultraviolet ray irradiation and a main hardening process of the seal material by heating, wherein a radically polymerizable curing resin is used in the liquid crystal seal material. The method provides a liquid crystal display panel having a uniform cell gap, without dislocation of the alighnment between substrates, or discharge of uncured component of a seal material to the liquid crystal, capable of having a seal material firmly attached to the substrates even at panel corner portions, and having an excellent straightness and moisture resistance of the seal material.Type: GrantFiled: February 28, 1996Date of Patent: April 27, 1999Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Satoshi Yamada, Hideki Matsukawa
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Patent number: 5858618Abstract: A photopolymerizable resinous composition includes a photocurable prepolymer which is prepared by a three-step reaction. The first step of the reaction includes reacting epoxide compounds containing at least two epoxy groups with an unsaturated carboxylic acid containing at least three vinyl linkages and an unsaturated carboxylic acid containing one vinyl group. The second step includes reacting the reaction product formed from the first step in a reaction with polybasic acid anhydride, and a third step of reacting the reaction product formed from the second step with a monoepoxide containing one vinyl group. The composition further includes a photocurable monomer containing one carboxylic acid having at least three vinyl linkages, a photocurable monomer containing at least one vinyl group, a photopolymerization initiator, a curing agent, and organic solvents. The composition exhibits photo- and thermal-curability, and the ability to develop with a weak alkaline aqueous solution.Type: GrantFiled: December 2, 1996Date of Patent: January 12, 1999Assignee: Nan Ya Plastics CorporationInventor: Ming-Jen Tzou
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Patent number: 5855837Abstract: A novel method for producing thick composite parts based upon photopolymerizable compositions is disclosed. The constituents of the photopolymerizable mixture comprise a monomer or monomers capable of polymerizing by free radical or cationic mechanisms, and a photoinitiator system which possesses an absorbance characteristic which is effectively reduced, or self-eliminating, upon initiation of the polymerization reaction. Parts having thicknesses up to 2 cm and thicker for varying end use applications are made by photopolymerizing such compositions. In addition, using such compositions composite parts can be made using a reinforcement material such as a glass fiber mat present in an amount by weight of from about 5 to about 70%.Type: GrantFiled: June 6, 1995Date of Patent: January 5, 1999Assignee: Michigan State UniversityInventors: Alec B. Scranton, Bharath Rangarajan, Lindsay S. Coons
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Patent number: 5853957Abstract: For instance, when a washing-free yet low-residue type of flux is coated on a solder resist film, soldering can be carried out while no solder balls remain on a circuit substrate.A photosensitive resin composition comprises a photopolymerizable and photosensitive resin having at least one of a carboxyl group and an onium group, a photopolymerizable reactive diluent, a photopolymerization initiator, a thermosetting component, and an inorganic powder having an average particle size of 2 .mu.m to 20 .mu.m. A cured film thereof is used as a solder resist film for circuit substrate fabrication.A washing-free yet low-residue type of flux is so uniformly coated on the solder resist film that soldering can be carried out in the absence of any solder ball.Type: GrantFiled: May 8, 1996Date of Patent: December 29, 1998Assignee: Tamura Kaken Co., LtdInventors: Makoto Yanagawa, Rinzo Tachibana, Hiroshi Yamamoto, Tetsuji Ishikawa, Tetsuo Kurokawa, Kohichi Ishida
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Patent number: 5852067Abstract: A near infrared rays-curing putty composition containing (A) a polymerizable ethylenically unsaturated group-containing resin, (B) a polymerizable ethylenically unsaturated compound and (C) a near infrared rays polymerization initiator, said near infrared rays polymerization initiator (C) being a near infrared rays-absorbing cationic dye and a resin powder consisting of gelation polymer fine particles.Type: GrantFiled: November 15, 1996Date of Patent: December 22, 1998Assignees: Showa Denko K. K., Kansai Paint Co., Ltd.Inventors: Hajime Sukejima, Shinji Tomita, Shuichi Sugita, Kazuhiko Ooga
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Patent number: 5837746Abstract: Compounds of the formulaRG--A--INwherein IN is a photoinitiator basic structure A is a spacer group and RG is a functional reactive group can be employed as coreactive photoinitiators for photo-polymerization of systems containing ethylenically unsaturated compounds.Type: GrantFiled: June 23, 1997Date of Patent: November 17, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Manfred Kohler, Jorg Ohngemach, Eike Poetsch, Rudolf Eidenschink, Gerhard Greber, Dieter Dorsch, Jurgen Gehlhaus, Konrad Dorfner, Hans Ludwig Hirsch
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Patent number: 5824715Abstract: A marking composition comprising an energy ray curing resin, a leuco dye and a color developer both of which are low in solubility in toluene, which composition is capable of forming a vivid black color on irradiation with laser beams, and a laser marking method for forming a clear-cut black-colored mark by using the above composition.Type: GrantFiled: February 6, 1996Date of Patent: October 20, 1998Assignee: Nippon Kayaku Kabushiki KaishaInventors: Shoiti Hayashihara, Masaru Kudo, Masaki Shinmoto
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Patent number: 5821276Abstract: 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: GrantFiled: July 23, 1996Date of Patent: October 13, 1998Assignee: Tioxide Specialties LimitedInventor: Robert Hume Duncan
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Patent number: 5821031Abstract: Disclosed herein is a photosensitive solder resist ink capable of development with a dilute alkaline solution. It has a wide pre-curing latitude. It permits the pre-cured board to be stored for a long period of time. It is superior in resolution, sensitivity, and solder resistance. Disclosed also herein is a printed circuit board having good adhesion, chemical resistance, electrical properties, gold plating resistance, solder heat resistance, and electrocorrosion resistance. Disclosed also herein is a process for producing said printed circuit board by using said solder resist ink.The photosensitive solder resist ink comprises (A) an ultraviolet-curable resin containing 0-20 wt % of aromatic ring moiety which is obtained by reacting a polymer composed of (a) 40-100 mol % of ethylenically unsaturated monomer having an epoxy group and (b) 0-60 mol % of ethylenically unsaturated monomer capable of copolymerization therewith, with (meth)acrylic acid in an amount of 0.7-1.Type: GrantFiled: May 22, 1996Date of Patent: October 13, 1998Assignee: Goo Chemical Co., Ltd.Inventors: Soichi Hashimoto, Fumito Suzuki, Toshikazu Oda
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Patent number: 5821277Abstract: 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: GrantFiled: November 1, 1996Date of Patent: October 13, 1998Assignees: Nippon Oil Co., Ltd., Dai Nippon Printing Co., Ltd.Inventors: Takayuki Hirayama, Haruyoshi Sato, Yutaka Otsuki, Masayuki Ando
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Patent number: 5804680Abstract: A flame-resistant, UV-curable single-component reactive resin system comprises a phosphorus-containing acrylate, another unsaturated compound which can undergo free radical copolymerization with acrylates and a free radical initiator system.Type: GrantFiled: March 5, 1997Date of Patent: September 8, 1998Assignee: Siemens AktiengesellschaftInventors: Winfried Plundrich, Ernst Wipfelder
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Patent number: 5801213Abstract: Radiation-curable compositions of reduced oxygen sensitivity comprisea) radiation-curable, free-radically polymerizable compounds, andb) capped amino compounds which are surface-active in compounds a) and on irradiation with high-energy light liberate amino compounds having primary, secondary or primary and secondary amino groups, the overall number of hydrogen atoms bonded in the amino groups (amine hydrogens) being at least 2.Type: GrantFiled: September 16, 1996Date of Patent: September 1, 1998Assignee: BASF AktiengesellschaftInventors: Reinhold Schwalm, Wolfgang Reich, Lukas Haussling, Erich Beck
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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: 5780526Abstract: 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: GrantFiled: November 14, 1996Date of Patent: July 14, 1998Assignee: Nippon Paint Co., Ltd.Inventors: Sakae Matsui, Hiroyuki Nakamura, Shizuo Kudo, Hiroaki Konse
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Patent number: 5773487Abstract: A sprayable coating composition is formulated using one or more acrylates and one or more photoinitiators which act to polymerize the composition when exposed to ultraviolet light. Because of the use of low molecular weight monomers or oligomers, the composition is essentially free of volatile organic solvents, and therefore evaporative emissions in curing are substantially eliminated.Type: GrantFiled: September 26, 1995Date of Patent: June 30, 1998Assignee: UV Coatings, Inc.Inventor: Andrew A. Sokol
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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: 5744512Abstract: Compounds of the formulaRG--A--INwhereinIN is a photoinitiator basic structureA is a spacer group andRG is a functional reactive group can be employed as coreactive photoinitiators for photopolymerization of systems containing ethylenically unsaturated compounds.Type: GrantFiled: March 20, 1996Date of Patent: April 28, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Manfred Kohler, Jorg Ohngemach, Eike Poetsch, Rudolf Eidenschink, Gerhard Greber, Dieter Dorsch, Jurgen Gehlhaus, Konrad Dorfner, Hans Ludwig Hirsch
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Patent number: 5726219Abstract: The present invention provides a rein composition comprising the following components (a), (b), (c), (d) and (e) as essential components; and an excellent multilayer printed circuit board obtained by using the resin composition:(a) a polyfunctional epoxy resin having an epoxy equivalent of 120-500,(b) a modified phenol novolac obtained by reacting 20-60 mole % of the phenolic hydroxyl groups of a phenol novolac obtained by condensing a phenol compound with formaldehyde in the presence of an acidic catalyst, with a glycidyl group-containing acrylate or methacrylate,(c) an epoxy acrylate or epoxy methacrylate compound,(d) a diluent consisting of a polyfunctional monomer having a plurality of photosensitive functional groups or a polyfunctional monomer having a photosensitive functional group and a heat-sensitive functional group, or a diluent consisting of a combination of the two monomers, and(e) a photopolymerization initiator.Type: GrantFiled: March 4, 1997Date of Patent: March 10, 1998Assignee: Sumitomo Bakelite Company LimitedInventors: Takeshi Hosomi, Hiroshi Hayai, Takayuki Baba
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Patent number: 5723512Abstract: n and m are independently of one another 0 or 1,R.sub.1, R.sub.2, R.sub.3, R.sub.4 and X are as defined in claim 1,are suitable as photoinitiators for the polymerization of ethylenically unsaturated compounds.Type: GrantFiled: June 27, 1996Date of Patent: March 3, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: David G. Leppard, Manfred Kohler
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Patent number: 5705316Abstract: 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: November 9, 1995Date of Patent: January 6, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Bettina Steinmann, Adrian Schulthess, Max Hunziker
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Patent number: 5681684Abstract: To provide a water-developable photosensitive resin composition capable of forming a resist film that excels in hardness, heat resistance and water resistance.The photosensitive resin composition of this invention is characterized by containing an unsaturated epoxy ester compound which is obtained by reacting the remaining epoxy side group of a partially carboxylic acid-esterified unsaturated epoxy ester compound with an aliphatic tertiary amine in the presence of an alcoholic solvent to convert it into a quaternary ammonium salt.Type: GrantFiled: September 20, 1995Date of Patent: October 28, 1997Assignee: National Starch and Chemical Investment Holding CorporationInventors: Keiichi Kinashi, Reiko Chiba
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Patent number: 5679722Abstract: A resin composition for production of a three-dimensional object by curing, which comprises a) a liquid photocurable resin, and b) a reinforcing agent selected from an inorganic solid particle having an average particle diameter of 3 to 70 .mu.m, whisker having an average particle diameter of 0.3 to 1.0 .mu.m, a length of 10 to 70 .mu.m and an aspect ratio of 10 to 100, and a combination of these.Type: GrantFiled: January 24, 1996Date of Patent: October 21, 1997Assignee: Teijin Seiki Co., Ltd.Inventor: Yorikazu Tamura
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Patent number: 5629445Abstract: This invention relates to (meth)acrylates represented by formula (1): ##STR1## wherein, R.sub.1 and R.sub.2 are each independently H or CH.sub.3 and average value of n is 1-5; resin composite comprising (A) an urethane (meth)-acrylate and/or epoxy (meth)acrylate, (B) a (meth)-acrylate represented by formula (1) above, (C) an ethylenically unsaturated compound other than component (A) or (B), and (D) a photopolymerization initiator; and cured products of said resin composites. The cured products of said resin composites of this invention have high refractive index and are superior in mold release property, shape reproducibility, restorability, and scratch resistance and suited in particular for transmission type screens.Type: GrantFiled: June 6, 1995Date of Patent: May 13, 1997Assignee: Nippon Kayaku Kabushiki KaishaInventors: Kenji Nakayama, Katsunori Shimura, Minoru Yokoshima, Nobuo Taniguchi
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Patent number: 5596024Abstract: A sealing compound for use in production of a liquid crystal display unit, comprises isobornyl(meth)acrylate, epoxy acrylate, a photopolymerizable initiator, epoxy resin having one or more polymerizable groups in one molecule, a latent thermosetting agent obtained by pretreating imidazole compounds, adducts of imidazole compounds and carboxylate of imidazole compounds, and/or adducts of imidazole compounds and epoxy resin with isocyanate compounds. The sealing compound is applicable particularly for sealing liquid crystal in between substrates of the liquid crystal display unit, and can secure the electrode substrates without misregistration of the substrates and uneven separation of the substrates.Type: GrantFiled: April 18, 1995Date of Patent: January 21, 1997Assignee: Three Bond Co., Ltd.Inventors: Ken'ichi Horie, Hidefumi Miura, Eiichi Tomioka
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Patent number: 5591562Abstract: A photopolymerizable composition suitable as a solder resist and capable of forming a resist film having characteristics in no way inferior to those of the conventional heat-curable type or organic solvent developed type solder resist, with the use of water or a dilute aqueous solution which is completely innocuous and higher in safety than the aqueous alkaline solution, and a method for producing a cured coated film pattern using the photopolymerizable composition.Type: GrantFiled: October 13, 1994Date of Patent: January 7, 1997Assignee: Sony CorporationInventors: Nobuo Komatsu, Ikuyo Kai, Nami Konishi, Naozumi Iwasawa, Satoru Furusawa
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Patent number: 5589230Abstract: A polymerizable curable molding composition comprising (A) 100 parts by weight of an unsaturated epoxyester resin with an acid value below 3.0, (B) 10 to 40 parts by weight of a polymerizable monomer selected from the group consisting of phenoxyethyl acrylate, 2-acroyloxyethyl-2-hydroxypropyl phthalate and mixtures thereof and (C) 1 to 5 parts by weight of a mixture of hydroxyketone oligomer and 2-hydroxy-2-methyl-1-phenylpropan-1-one. The molding composition also preferably comprises 0.5 to 5 parts by weight of polystyrene microbeads. Also provided are a molding process using the polymerizable curable molding composition and a coating process using the polymerizable curing molding composition, each process being characterized by combined exposure of the composition to UV radiation and heating.Type: GrantFiled: April 7, 1995Date of Patent: December 31, 1996Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Yoshitami Yamamura, Nobuhiko Morimoto, Nobuyuki Tanaka
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Patent number: 5585417Abstract: Process for the hardening, curing or setting of a bis-maleimide resin and a composite material using said resin.The setting process according to the invention of a basic resin A having at least one bis-maleimide monomer consists of adding to the basic resin A, prior to the use thereof, at least one reactive diluent B consisting of a monomer having a copolymerizable vinyl termination with the basic resin A when subjecting the mixture of the basic resin A and the diluent B to the action of ionizing radiation (34), the total quantity of the diluent B being such that the maleimide functions of the basic resin A are consumed following the ionizing radiation action and being chosen in the range 10 to 50 parts by weight for 100 parts by weight of the basic resin A. This resin is more particularly intended for the production of a composite material (16, 18) having a fibrous reinforcement (26, 28, 30, 32) by filamentary winding.Type: GrantFiled: April 4, 1996Date of Patent: December 17, 1996Assignee: Aerospatiale Societe Nationale IndustrielleInventors: Daniele Beziers, Yves Camberlin, Evelyne Chataignier, Patrice Dourthe
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Patent number: 5548005Abstract: 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: GrantFiled: December 16, 1994Date of Patent: August 20, 1996Assignee: Hoechst AktiengesellschaftInventors: Inge Kurth, Gerhard Brindoepke, Manfred Marten
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Patent number: 5539014Abstract: This invention relates to vinyl ether-based coatings for which properties such as color stability, thermal stability, mechanical stability, hydrolytic stability, and resistance to embrittlement may be maintained and properties hydrogen generation and blocking are minimized.Type: GrantFiled: August 19, 1994Date of Patent: July 23, 1996Assignee: AlliedSignal Inc.Inventors: Raymond J. Swedo, George D. Green, James R. Snyder
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Patent number: 5539064Abstract: A resist ink composition developable with a diluted, alkaline solution, which exhibits high dispersion stability itself, can form a pattern with excellent resolution, even in the case of a low exposure amount, and can produce a cured resist film excellent in solvent resistance for high-performance printed circuits and which comprises an ultraviolet-curable resin obtained by copolymerizing (a) from 5 to 50% by weight of an ethylenically unsaturated monomer of a general formula: ##STR1## wherein R.sub.1 represents a hydrogen atom or a methyl group; R.sub.2 represents a hydrogen atom or an alkyl group; n represent an integer of from 1 to 4, and/or glycerol mono(meth)acrylate, (b) from 10 to 90% by weight or glycidyl (meth)acrylate and (c) from 0 to 80% by weight of other ethylenically unsaturated monomers capable of copolymerizing with these (a) and (b), followed by reacting the resulting copolymer with from 0.7 to 1.Type: GrantFiled: September 12, 1995Date of Patent: July 23, 1996Assignee: Goo Chemical Industries Co., Ltd.Inventors: Soichi Hashimoto, Satoshi Miyayama, Toshiaki Nishimura, Toshikazu Oda
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Patent number: 5521228Abstract: A method for forming simulated hair strands on the scalp by utilizing a composition containing an ethylenically unsaturated monomer and a photoinitiator. The composition is applied to the scalp, strands are formed and the strands are cured by light.Type: GrantFiled: January 17, 1995Date of Patent: May 28, 1996Inventors: Michael R. Weber, Paul J. Weber
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Patent number: 5514727Abstract: This invention relates to vinyl ether-based coatings for which properties such as color stability, thermal stability, mechanical stability, hydrolyric stability, and resistance to embrittlement may be maintained and properties hydrogen generation and blocking are minimized. The invention also relates to stabilizers which control these properties in the coatings.Type: GrantFiled: July 13, 1994Date of Patent: May 7, 1996Assignee: AlliedSignal Inc.Inventors: George D. Green, James R. Snyder, Raymond J. Swedo
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Patent number: 5498782Abstract: Distortion control additives are disclosed which comprise a polyisocyanate, a polyol or polyol blend having a hydroxyl functionality of 2 to 3 hydroxyl groups per molecule and an average molecular weight of at least about 500 grams per gram mole, a diol chain extender having from about 2 to 35 carbon atoms per molecule and an acrylate or methacrylate having an acrylate functionality of from 1 to 5 acrylate groups per molecule. Ultraviolet-curable liquid compositions comprising an unsaturated polymeric resin, a monomer and the distortion control additives of the present invention are also disclosed. The distortion control additives can provide substantial reductions in distortion, e.g., shrinkage, of objects produced by ultraviolet curing, e.g., stereolithography.Type: GrantFiled: September 8, 1993Date of Patent: March 12, 1996Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Gary C. Rex
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Patent number: 5492733Abstract: A gloss coating composition comprising radiation curable oligomers and monomers, and photosensitizers in a homogeneous mixture having a viscosity in the range of 4500 to 8000 cps; wherein the presence of the photosensitizers causes polymerization of the radiation curable oligomers and monomers when exposed to an ultraviolet light source. The coating composition is applied to at least one surface of a substrate and exposed to an ultraviolet light source resulting in curing of the composition onto the substrate surface without substantial penetration into the substrate surface forming a gloss coated substrate.Type: GrantFiled: September 20, 1993Date of Patent: February 20, 1996Assignee: International Paper CompanyInventors: Guy D'Anna, Stephen H. Monroe, Peter J. Angelini, James A. Goettmann, John R. Boylan
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Patent number: 5484823Abstract: A photopolymerizable adhesive comprises (A) an acrylic resin having groups represented by the formulae: --COOH, --OH and --NHCH.sub.2 OR (wherein R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), a number average molecular weight of from 3,000 to 200,000 and a glass transition temperature of at least 70.degree. C., (B) a photopolymerizable oligomer containing at least one member selected from the group consisting of (a) an acrylate or a methacrylate of a novolak epoxy resin, (b) an acrylate or a methacrylate of a bisphenol epoxy resin and (c) an urethane acrylate of aromatic alcohol or cycloaliphatic alcohol, and (C) a photoinitiator capable of discharging radicals with the action of activation energy.Type: GrantFiled: August 29, 1994Date of Patent: January 16, 1996Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Naohito Asai, Yuko Suga
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Patent number: RE35135Abstract: Disclosed is a photocurable composition comprising (a) a radical-polymerizable monomer, (b) an .alpha.-ketocarbonyl compound and (c) a derivative of mercaptobenzimidazole, mercaptobenzothiazole or mercaptobenzoxazole or an aromatic amine nucleus-substituted with an electron-attractive group. This composition has a high photocuring speed at a temperature close to normal temperature and gives a cured product excellent in various physical properties. This composition is valuable as a dental adhesive or resin.Type: GrantFiled: March 15, 1994Date of Patent: December 26, 1995Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Takeshi Sakashita, Takayuki Nakano