With Ethylenic Reactant Patents (Class 522/103)
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Patent number: 5468784Abstract: Disclosed is a photopolymerizable resin composition suitable for forming a solder mask layer, for example, on a printed circuit board. The photopolymerizable resin composition of the invention can be prepared in the form of an aqueous solution and is developable with water as the developer liquid so that the problems and disadvantages inherent in the use of organic solvents can be completely solved. The composition comprises, in addition to a photopolymerization initiator and a polyenic compound as a reactive diluent, a unique prepolymer as a resinous ingredient which is a copolymer of, for example, an alkyl (meth)acrylate and glycidyl (meth)acrylate modified at the epoxy groups in the copolymer partly by the reaction with (meth)acrylic acid and partly by the reaction with an onium group-containing compound, e.g. a quaternary ammonium compound, to impart solubility in water.Type: GrantFiled: February 23, 1994Date of Patent: November 21, 1995Assignee: Tamura Kaken CorporationInventors: Makoto Yanagawa, Hiroshi Yamamoto
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Patent number: 5466721Abstract: Provided are compounds having the formula: ##STR1## wherein: R.sup.1 and R.sup.2 are independently selected from the group consisting of a hydrogen atom, an aliphatic group, a hetero-aliphatic group, an aromatic group, and a heterocyclic group, provided that R.sup.1 and R.sup.2 may together form a divalent radical selected from the group consisting of an aliphatic radical and hetero-aliphatic group;each R.sup.3 is independently selected from the group consisting of an aliphatic group, a hetero-aliphatic group, an aromatic group, and a heterocyclic group;R.sup.4 is selected from the group consisting of an aliphatic group, a hetero-aliphatic group, an aromatic group, and a heterocyclic group; andn is an integer from 0 to 5.Also provided are polymerizable compositions containing such compounds and a method of coating a substrate which uses such polymerizable compositions.Type: GrantFiled: June 13, 1994Date of Patent: November 14, 1995Assignee: Henkel CorporationInventor: Paul E. Share
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Patent number: 5466723Abstract: A radiation curable adhesive composition which comprises from 15 to 85 percent by weight of beta-carboxyethyl acrylate and from 85 to 15 percent by weight of 2-phenoxyethyl acrylate based on the total weight of the composition.Type: GrantFiled: October 17, 1994Date of Patent: November 14, 1995Assignee: Eastman Kodak CompanyInventor: Billy R. Dotson
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Patent number: 5461088Abstract: Liquid radiation-curable formulation, in particular for stereolithography, based on at least one compound that contains free radically polymerisable groups, and at least one photoinitiator suitable for the polymerisation, which formulation additionally contains a polyoxyalkylene-polysiloxane block copolymer that is selected from copolymers of the chemical formulaeR.sup.1 --(OC.sub.c H.sub.2c).sub.d --{[T]--(C.sub.c H.sub.2c O).sub.d-1 --(C.sub.c H.sub.2c)}.sub.g --OR.sup.1 (I) ##STR1## wherein: R.sup.1 is a hydrogen atom or a C.sub.1 -C.sub.8 alkyl group;R.sup.2 is a methyl or phenyl group;[T] is a polysiloxane group [PS] terminated as described in the specification in more detail;[PS] is the group of formula ##STR2## and [Alk] is an alkylene group of 3 to 10 carbon atoms, as well as novel block copolymers of formulae (I) and (II). The cured formulations have, inter alia, superior impact strength.Type: GrantFiled: August 18, 1994Date of Patent: October 24, 1995Assignee: Ciba-Geigy CorporationInventors: Jean-Pierre Wolf, Adrian Schulthess, Bettina Steinmann, Max Hunziker
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Patent number: 5453451Abstract: 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: March 29, 1993Date of Patent: September 26, 1995Inventor: Andrew A. Sokol
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Patent number: 5453452Abstract: 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: December 16, 1993Date of Patent: September 26, 1995Assignee: Nippon Kayaku Kabushiki KaishaInventors: Kenji Nakayama, Katsunori Shimura, Minoru Yokoshima, Nobuo Taniguchi
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Patent number: 5449704Abstract: A liquid composition which on exposure to actinic radiation polymerises to form a heat-curable solid film adhesive, said composition comprising (A) a heat-curable phenol-aldehyde resol resin, (B) a photopolymerisable resin having, on average, more than one polymerisable acrylic group per molecule, (C) a photopolymerisation initiator for (B) and (D) an aminotriazine-formaldehyde resin.Type: GrantFiled: December 14, 1993Date of Patent: September 12, 1995Assignee: Ciba-Geigy CorporationInventors: Stuart J. Thompson, Stuart Mansfield
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Patent number: 5444104Abstract: A polycarbonate dimethacrylate which is the condensation product of 2 parts of hydroxyalkylmethacrylate of the formula. ##STR1## in which A is C.sub.1 -C.sub.6 alkylene, and 1 part of a bis(chloroformate) of the formula ##STR2## in which R is C.sub.2 -C.sub.5 alkylene having at least two carbon atoms in its principal chain and n is an integer from 1 to 4, is usable, admixed with a secondary monomer suitable for dental applications, such as BIS-GMA; UDMA or the like, as an adhesive system for dental restorative materials. Particularly useful is the novel condensation product of 2-hydroxyethylmethacrylate and triethylene glycol bis(chloroformate).Dental adhesives containing these components are suitable for application to enamel, pretreated dentin, porcelain and metallic surfaces. The dentin surfaces are pretreated by application of an alcoholic solution of an alkali metal salt of benzene sulfinic acid.Type: GrantFiled: October 12, 1993Date of Patent: August 22, 1995Assignee: Jeneric/Pentron, Inc.Inventor: Samuel Waknine
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Patent number: 5439956Abstract: An adhesive for use in bonding finely processed parts such as parts of ink jet recording head has a composition which essentially contains: (A) a vinylester compound of an urethanated epoxy resin; (B) a partial vinylester compound of a multi-functional epoxy resin; (C) an acrylic reactive diluent; (D) a photopolymerization initiator; and(E) an epoxy cure agent. This adhesive is curable by ultraviolet irradiation or by application of heat, and does not flow or spread into areas where bonding is not necessary, so that finely processed parts are bonded with a high degree of precision of the bonding pattern.Type: GrantFiled: February 9, 1994Date of Patent: August 8, 1995Assignee: Canon Kabushiki KaishaInventor: Hiromichi Noguchi
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Patent number: 5436279Abstract: A coating material crosslinkable by radiation comprising a) an olefinic unsaturated ester of an epoxy novolac resin, b) a binder formed by reaction of an epoxy compound having more than one epoxide group per molecule with at least one carboxylic acid in a molar ratio of epoxy groups per carboxyl group of 1:0.5 to 0.9 and subsequent reaction of the resulting reaction product with at least one unsaturated isocyanate ester formed by reaction of a compound with at least two isocyanate groups with a member of the group consisting of hydroxyl containing acrylic acid, methacrylic acid and cyanacrylic acid esters, c) at least one latent hardener, d) at least one photoinitiator e) 80-120% by weight of fillers and (f) additives, adjuvants and solvents and protective films formed with them.Type: GrantFiled: February 1, 1994Date of Patent: July 25, 1995Assignees: Rutgerswerke Aktingesellschaft, Lackwere Peters GmbH & Co. KGInventors: Ulrich Grundke, Klaus-Peter Liebetanz, Achim Hansen, Jurgen Zehrfeld, Rainer Scharre, Werner Peters
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Photosensitive compositions useful in three-dimensional part-building and having improved photospeed
Patent number: 5418112Abstract: A method useful for stereolithography that yields enhanced photospeed, as well as a photocurable polymer composition well adapted for use with same, are disclosed.A preferred combination includes 1,2-dimethoxy-2-phenyl acetophenone, benzophenone, and triphenyl phosphine combined with a polyurethane (meth)acrylate oligomer.Type: GrantFiled: November 10, 1993Date of Patent: May 23, 1995Assignee: W. R. Grace & Co.-Conn.Inventors: Srinivas K. Mirle, Ronald J. Kumpfmiller -
Patent number: 5409740Abstract: A method of forming a fiber bundle which is useful as an industrial thread. The fiber bundle is prepared by integrating individual fiber filaments into a fiber bundle, applying a dual-cure adhesive material to the fiber bundle and initiating polymerization of the dual-cure adhesive material. The dual-cure adhesive material is a combination of a radiation-curable material and a moisture-curable material. The radiation-curable material contains an acrylourethane oligomer and a reactive diluent system, while the moisture-curable material contains a polyisocyanate or an isocyanate-functional urethane prepolymer. The use of a dual-cure material results in a synergistic curing process so as to form a durable and flexible industrial thread or fiber.Type: GrantFiled: December 18, 1992Date of Patent: April 25, 1995Assignee: Lord CorporationInventor: Bill L. Brann
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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: 5395863Abstract: Radiation-curable compositions including a free radically polymerizable monomer or prepolymer and a different monomer containing an N-vinyl group, said different monomer being a solid at ambient temperature. The different monomer is preferably N-vinyl caprolactam, N-vinyl carbazole, or N,N'-divinyl-2-imidazolidone, for example in an amount of from 1 to 50 percent by weight of the said different monomer. Such compositions have shown good adhesion to and have rendered plastics substrates wettable by the compositions before curing, without the presence of N-vinyl-2-pyrrolidone.Type: GrantFiled: February 8, 1993Date of Patent: March 7, 1995Assignee: Sericol LimitedInventors: Kevin G. Burns, Helen Jezequel, Nigel P. Gould
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Patent number: 5395269Abstract: An electrical connector of the type having a housing with terminals extending from apertures thereof, is sealed at the aperture entrances around the extending terminal portions. The sealant material is polymerized of a major proportion of at least one vinyl ester resin, a minor proportion of at least one polymerizable acrylic diluent monomer and a polymerization activation system comprising from about 0.025% to about 17% by weight of the resin, by being exposed to actinic radiation selected to activate the system. The polymerized material excludes solder and solvents from the aperture entrances.Type: GrantFiled: August 26, 1991Date of Patent: March 7, 1995Assignee: The Whitaker CorporationInventors: Francis F. Koblitz, Thomas M. O'Shea, Lynn K. Snyder
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Patent number: 5393645Abstract: Structured polymer layers having nonlinear optical properties are produced by a process wherein either organic compounds containing ethylenically unsaturated groups are subjected to free radical copolymerization (A) with stilbene, azo or azomethine compounds containing ethylenically unsaturated groups and donor and acceptor groups, or organic compounds containing ethylenically unsaturated groups are subjected to free radical polymerization and are mixed (B) with stilbene, azo or azomethine compounds containing ethylenically unsaturated groups and donor and acceptor groups, the copolymers (A) or mixtures (B) thus obtained are exposed imagewise to high-energy radiation, the unexposed parts are removed and the structured polymer layers thus obtained are polarized in an electric field for orientation of the chromophoric structural units in the region of the glass transition temperature of the polymer and crosslinked in an applied electric field.Type: GrantFiled: December 16, 1993Date of Patent: February 28, 1995Assignee: BASF AktiengesellschaftInventors: Karl-Heinz Etzbach, Heike Kilburg, Hans-Joachim Lorkowski, Karl Pfeiffer
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Patent number: 5381735Abstract: Release of a resin mold from a photopolymeric mold is enhanced by using an unsaturated fatty acid ester release agent in the photopolymeric composition. In addition to providing quick release of the resin mold, the incorporation of the unsaturated fatty acid ester improves the flexibility of the photopolymeric mold without sacrificing tensile strength or hardness. The resin mold is used to fabricate rubber plates for ink printing.Type: GrantFiled: October 26, 1992Date of Patent: January 17, 1995Assignee: Hercules IncorporatedInventor: Charles C. Fifield
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Patent number: 5368985Abstract: Bisacylphosphine sulfides of formula I ##STR1## wherein R.sub.1 is unsubstituted C.sub.1 -C.sub.18 or C.sub.1 -C.sub.8 alkyl which is substituted by phenyl, --CN, C.sub.1 -C.sub.12 alkoxy or halogen, C.sub.2 -C.sub.18 alkenyl, unsubstituted C.sub.5 -C.sub.8 cycloalkyl or C.sub.5 -C.sub.8 cycloalkyl which is substituted by C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy or halogen, unsubstituted C.sub.6 -C.sub.12 aryl or C.sub.6 -C.sub.12 aryl which is substituted by halogen, C.sub.1 -C.sub.12 alkyl or C.sub.1 -C.sub.12 alkoxy, or a 5- or 6-membered aromatic heterocyclic radical which contains oxygen, sulfur and/or nitrogen and is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, andR.sub.2 and R.sub.3 are each independently of the other unsubstituted C.sub.1 -C.sub.18 alkyl or C.sub.1 -C.sub.8 alkyl which is substituted by phenyl, halogen or C.sub.1 -C.sub.12 alkoxy, C.sub.2 -C.sub.6 alkenyl, unsubstituted C.sub.5 -C.sub.8 cycloalkyl or C.sub.5 -C.sub.Type: GrantFiled: February 28, 1994Date of Patent: November 29, 1994Assignee: Ciba-Geigy CorporationInventors: Werner Rutsch, Gebhard Hug, Manfred Kohler
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Patent number: 5364889Abstract: A method and composition for forming investment casting patterns wherein thermally-collapsible microspheres are incorporated into the pattern composition. The patterns can be made either by conventional pattern forming techniques or by solid imaging techniques. After investing the microsphere containing pattern in the ceramic shell, the pattern and shell are heated, causing a collapse of the microspheres and thereby preventing cracking of the shell. The shell is then heated to burn-out the remaining pattern material and fire the shell, thereby creating a mold.Type: GrantFiled: April 27, 1992Date of Patent: November 15, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: John A. Quinn, Roxy N. Fan
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Patent number: 5360836Abstract: The subject of the invention is a process for the production of coatings by radiation crosslinking of compositions containing a resin which can be cured by the polymerization of the double bonds >C.dbd.CH.sub.2 and a reactive diluent system containing at least one reactive diluent corresponding to the general formula (I) ##STR1## in which R.sub.1 =H, CH.sub.3,R.sub.2 and R.sub.3 =H, C.sub.1 -C.sub.4 -alkyl chain or form an alkylene ring containing 5 or 6 carbon atoms,R.sub.4 =H, C.sub.1 -C.sub.4 -alkyl chain, phenyl,R.sub.5 =C.sub.1 -C.sub.10 aliphatic chain, C.sub.5 -C.sub.6 alicyclic chain, or C.sub.1 -C.sub.4 alkyl chain substituted with an aryl or aromatic heterocyclic group,or R.sub.4 and R.sub.5 form a 5- or 6-membered ring.One preferred compound (I) is to the acrylate of isopropyl beta-hydroxyethylcarbamate.Type: GrantFiled: March 22, 1993Date of Patent: November 1, 1994Assignee: Societe Nationale des Poudres et ExplosifsInventors: Francois Chevallier, Sammy Chevalier
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Patent number: 5358977Abstract: The invention is a method of manufacturing a substrate and, particularly, of manufacturing a release paper. The method comprises coating a release paper base with a primer coat, and curing the primer coat. The cured primer coat is then overlayed with a heat-curable or an ultraviolet-curable silicone coating which is, in turn, cured with heat or ultraviolet light. A product manufactured in accordance with this method enables a facing adhered to this release paper to be removed relatively easily from that release paper.Type: GrantFiled: January 27, 1992Date of Patent: October 25, 1994Assignee: Daubert Coated Products, Inc.Inventors: George Krankkala, John Bachman
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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: 5356949Abstract: An adhesive tape comprising an energy beam transmittable base sheet having a surface tension of not more than 40 dyne/cm and an adhesive layer formed on one surface of the base sheet, the adhesive layer comprising a (meth)acrylate polymer, an epoxy resin, a photopolymerizable low molecular weight compound, a heat activatable latent curing agent for the epoxy resin and a photopolymerization initiator for the photopolymerizable low molecular weight compound. The adhesive in the adhesive layer is curable with an energy beam and the so cured adhesive develops tackiness again when heated. When the tape is used in processing a semiconductor wafer, it serves as a dicing tape for holding the wafer in position during the dicing step. Each piece of the diced and cured adhesive layer, that is attached to each chip and capable of being tackified by heating, provides an adhesive required for securely mounting the chip on the lead frame in the die-bonding step.Type: GrantFiled: February 21, 1992Date of Patent: October 18, 1994Assignee: Lintec CorporationInventors: Mikio Komiyama, Yasunao Miyazawa, Kazuyoshi Ebe, Takanori Saito
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Patent number: 5352713Abstract: A radiation curable coating composition comprising acrylate oligomers and monomers, vinyl ether monomers, and a free radical photoinitiator. The vinyl ether monomers replace N-vinyl-pyrrolidone or other undesirable reactive diluents while retaining or modifying the properties of coatings using such diluents.Type: GrantFiled: April 1, 1992Date of Patent: October 4, 1994Assignee: Allied-Signal Inc.Inventors: James R. Snyder, George D. Green, John J. Krajewski
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Patent number: 5334455Abstract: A free-radical radiation curable composition comprising:a) at least one compound containing from one to about six vinyl ether groups; andb) at least one product obtainable by the reaction of a half-ester of maleic and/or fumaric acid with an epoxy functionalized compound,wherein the ratio of vinyl ether groups to maleate and/or fumarate groups is in the range of about 5:1 to about 1:5.Type: GrantFiled: May 26, 1992Date of Patent: August 2, 1994Assignee: Stamicarbon B.V.Inventors: Gerry K. Noren, John J. Krajewski, Sami A. Shama, John M. Zimmerman, Danny C. Thompson, John T. Vandeberg
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Patent number: 5321053Abstract: A dental composition comprising a vinyl monomer containing at least one acidic group in the molecule thereof and an initiator capable of photopolymerizing said monomer by visible light, characterized in that said initiator consisting essentially of:(a) a photosensitizer selected from an .alpha.-diketone, a quinone and a derivative thereof, and,(b) an accelerator selected from a compound containing at least one mercapto group in the molecule thereof is provided by the present invention.Type: GrantFiled: February 6, 1990Date of Patent: June 14, 1994Assignee: Kuraray Co., Ltd.Inventors: Kenichi Hino, Junichi Yamauchi, Koji Nishida
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Patent number: 5306739Abstract: A highly, filled composition is described containing a polymeric material, at least one filler, and at least one surface active agent. The filler(s) and surface active agent(s) are selected based upon the relationship between their pH's allowing for enhanced filler loading of the compositions. The compositions of the present invention can be used to coat electrical and electronic components or as inasfar covering substrates.Type: GrantFiled: July 22, 1992Date of Patent: April 26, 1994Assignee: MLT/Micro-Lite Technology CorporationInventor: Michael F. Lucey
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Patent number: 5304586Abstract: One component, visible light-cured dental restorative compositions having fluoride release properties for the purpose of reducing the chances of secondary caries are provided. The compositions include inorganic particulate fluoride leachable glass.Type: GrantFiled: August 2, 1991Date of Patent: April 19, 1994Assignee: Dentsply Research & Development Corp.Inventors: Paul D. Hammesfahr, Paul S. Danielson, Robert C. Campbell
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Patent number: 5281569Abstract: A desensitizing ink for printing by wet or dry offset, flexographic or typographic printing is disclosed and claimed. This ink contains at least one desensitizing agent, at least one ink binder which is polymerizable or crosslinkable by UV light or electron beam radiations and, if necessary, an initiator system. Thus, the drying time of the printings is greatly reduced. The ink is free from vaporizable ink solvents.Type: GrantFiled: February 25, 1992Date of Patent: January 25, 1994Assignee: SICPA International S.A.Inventors: Albert Amon, Laszlo K. Boksanyi
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Patent number: 5276068Abstract: A polycarbonate dimethacrylate which is the condensation product of 2 parts of hydroxyalkylmethacrylate of the formula ##STR1## in which A is C.sub.1 -C.sub.6 alkylene, and 1 part of a bis(chloroformate) of the formula ##STR2## in which R is C.sub.2 -C.sub.5 alkylene having at least two carbon atoms in its principal chain and n is an integer from 1 to 4, is usable, admixed with a secondary monomer suitable for dental applications, such as BIS-GMA; PUDMA or the like, as an adhesive system for dental restorative materials. Particularly useful is the novel condensation product of 2-hydroxyethylmethacrylate and triethylene glycol bis(chloroformate).Type: GrantFiled: January 28, 1992Date of Patent: January 4, 1994Assignee: Jeneric/Pentron, Inc.Inventor: Samuel Waknine
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Patent number: 5268255Abstract: A printed circuit board has a resist layer made from a photo-setting resist composition containing:(A) a polyfunctional unsaturated compound which is solid at room temperature,(B) a polyfunctional unsaturated compound which is liquid at room temperature,(C) a photopolymerization initiator,(D) an epoxy resin,(E) at least one member selected from the group consisting of:(i) a curing agent for the epoxy resin and either melamine or the derivative thereof, and(ii) a compound having a 2,4-diamino-s-triazine ring and an imidazole ring in the molecule.Type: GrantFiled: September 30, 1991Date of Patent: December 7, 1993Assignee: Hitachi, Ltd.Inventors: Hiroshi Kikuchi, Makio Watanabe, Shinichiro Imabayashi, Reiko Yano, Isamu Tanaka, Hitoshi Oka, Yukihiro Taniguchi, Shigeru Fujita
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Patent number: 5262449Abstract: This invention relates to a coating composition which can be cured by exposure to radiation energy in the presence of a cationic photoinitiator. The composition comprises a mixture of between about 1 and about 75 wt. % of a reactive vinyl or alk-1-enyl ether cyclocarbonate having the formula ##STR1## wherein R is hydrogen or lower alkyl; R' is C.sub.2 to C.sub.4 alkylene; n has a value of from 0 to 4 and n' has a value of from 1 to 4 and between about 99 and about 25 wt. % of a polymerizable compound containing an onium salt initiator which is normally insoluble in said polymerizable compound or a mixture thereof. The invention also relates to the use of the composition as a protective coating on a substrate.Type: GrantFiled: August 28, 1992Date of Patent: November 16, 1993Assignee: ISP Investments Inc.Inventors: Kolazi S. Narayanan, Jeffrey S. Plotkin, Fulvio J. Vara, James A. Dougherty
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Patent number: 5248805Abstract: Radiation-sensitive, ethylenically unsaturated compounds and a process for their preparation. The ethylenically unsaturated organic compounds are of the general formula ##STR1## where R is alkyl, aryl or a radical R.sup.1 andR.sup.1 is a radical ##STR2## where R.sup.2 to R.sup.6 are each H, alkyl, OH, OAlkyl, SH, SAlkyl, halogen, N (Alkyl).sub.2 or N (Alkyl) (Aryl) and at least one but not more than three of the radicals R.sup.2 to R.sup.6 is or are a radical ##STR3## where X is alkylene, cycloalkylene, oxaalkylene or arylene, Y is H or CH.sub.3 -- and Z is O or NY.The novel radiation-sensitive ethylenically unsaturated compounds are suitable for the preparation of polymeric radiation-sensitive compounds.Type: GrantFiled: March 2, 1992Date of Patent: September 28, 1993Assignee: BASF AktiengesellschaftInventors: Andreas Boettcher, Gerd Rehmer
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Patent number: 5213875Abstract: Resin compositions comprising 20 to 50% by weight, based on total composition weight, of a first resin which comprises an acrylate-epoxy oligomer having a molecular weight of from 2000 to 5000; from 2 to 10% of a second resin which comprises an acrylate-urethane oligomer; up to 50% of a third resin which comprises a second acrylate-epoxy oligomer, where from 1 to 5% of the epoxy is an epoxy novolac; from 10 to 40% of a liquid acrylate; from 2 to 20% of a liquid diacrylate having an ether linkage; from 5 to 25% of a liquid alkylene diacrylate; and from 1 to 5% of a UV photoinitiator. The compositions also preferably includes from 0.05 to 1% of a flow control agent. The compositions are applied to substrates such as printed wiring boards and cured with ultraviolet light to form a conformal coating on the substrate.Type: GrantFiled: September 7, 1988Date of Patent: May 25, 1993Assignee: Westinghouse Electric Corp.Inventors: Wei-Fang A. Su, Anthony P. Barrett
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Patent number: 5212271Abstract: A process for texturing a coating via exposing a photocurable composition comprising a multifunctional urea compound, an ethylenically unsaturated compound, and an aromatic ketone photosensitizer that functions through a hydrogen abstraction mechanism when exposed to ultraviolet light.Type: GrantFiled: December 22, 1989Date of Patent: May 18, 1993Assignee: Texaco Chemical CompanyInventors: Alison D. Beckett, Joseph V. Koleske, Richard M. Gerkin
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Patent number: 5202360Abstract: An adhesive composition comprising a photopolymerization initiator or curing agent and the compound represented by the formula (I) ##STR1## wherein M is a divalent organic group comprising at least one substituted or unsubstituted alicyclic hydrocarbon group or a divalent organic group comprising at least two substituted or unsubstituted aromatic hydrocarbon groups, the alicyclic hydrocarbon group or aromatic hydrocarbon group may be linked by O, S or CH.sub.2 or may form a condensed ring, n is zero or a positive number.Type: GrantFiled: July 29, 1991Date of Patent: April 13, 1993Assignees: Daiken Industries, Ltd., Nippon Telegraph & Telephone Corp.Inventors: Akira Ohmori, Yoshiki Shimizu, Motonobu Kubo, Kouzaburou Nakamura, Tohru Maruno, Norio Murata, Hideo Kobayashi
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Patent number: 5198509Abstract: A composition comprising a lactone-modified alicyclic compound (I), or an epoxidized lactone-modified alicyclic compound (II) of the following formulae: ##STR1## wherein R is an alkyl group, an aromatic group or an alkenyl group having carbon number of from 1 to 30, Y.sup.1 is at least one of the structural groups; ##STR2## Y.sup.2 is at least one of the structural group; ##STR3## X is the structural group; ##STR4## R.sup.a and R.sup.b each independently is hydrogen or a methyl group, c and c' represent a number of from 4 to 8, from n1 to nL represents 0 or a number of more than 0, respectively, and n1+n2+n3+. . . +nL corresponds to the total mole numbers of a lactone introduced into one molecule.These compositions can be made into a heat-curable composition, a photo-curable composition, a polymerizable composition and another photo-curable composition.Type: GrantFiled: June 8, 1992Date of Patent: March 30, 1993Assignee: Daicel Chemical Industries, Ltd.Inventors: Takaaki Fujiwa, Shin Takemoto, Tomohisa Isobe, Yoshiyuki Harano
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Patent number: 5196457Abstract: Resin composition, that can be used for manufacturing a prepreg, comprising a liquid epoxy resin, a monomer reactive with the epoxy resin and a hardening catalyst for the epoxy resin, an unsaturated polyester, a monomer reactive with the unsaturated polyester and a hardening catalyst for the unsaturated polyester, whereby the catalyst for the unsaturated polyester is a first catalyst that has a working range below 40.degree. C. and the catalyst for the epoxy resin is a second catalyst that has a working range above 40.degree. C.Type: GrantFiled: June 28, 1990Date of Patent: March 23, 1993Assignee: DSM N.V.Inventors: Paul Wilkinson, Arno Montorfano
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Patent number: 5196296Abstract: Epoxy acrylate resins of this invention having a structure of the general formula (I) ##STR1## in which R is hydrogen or a lower alkyl group, R' is hydrogen or methyl group, and n is an integer from 0 to 20 are heat-resistant, solvent-soluble, and photosensitive and photosensitive resin compositions containing said epoxy acrylate resins as main component exhibit high photosensitivity in addition to strong adhesion to substrates, good resistance to heat and chemicals, and good mechanical and electrical properties and are useful as materials for forming insulation films for multilayer devices and protective films for image sensors and as protective films for solder resists, plating resists, and color filters.Type: GrantFiled: July 26, 1990Date of Patent: March 23, 1993Assignees: Nippon Steel Corporation, Nippon Steel Chemical Co., Ltd.Inventors: Kazuhiro Watanabe, Takero Teramoto
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Patent number: 5183832Abstract: Coating agent for collagen-containing materials, comprising an aldehyde, unsaturated monomers with and without active hydrogen, solubilizers and/or dispersants, activators and conventional additives.Type: GrantFiled: October 15, 1991Date of Patent: February 2, 1993Assignee: Bayer AktiengesellschaftInventors: Erik Asmussen, Erik C. Munksgaard, Michael Muller, Wolfgang Podszun, Jens Winkel
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Patent number: 5182316Abstract: A curable composition, the cure of which can be monitored optically, comprises at least one of a hydride curable silicone, an ethylenically unsaturated compound, and a cationically polymerizable monomer, and as cure monitor dibenzofulvene or derivative thereof. The cure monitor is a latent fluorophore which reacts under the cure conditions to form a UV-detectable fluorophore.The invention also provides a method for measuring degree of cure of a polymeric material which can be a coating or an article.Type: GrantFiled: November 26, 1991Date of Patent: January 26, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: Robert J. DeVoe, Katherine A. Brown-Wensley, George V. D. Tiers
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Patent number: 5180757Abstract: Actinic radiation curable composition suitable for use in coating electronic components and as a printing ink comprising as the essential components:(a) a monomer selected from the group consisting of monofunctional vinyl monomers and multifunctional vinyl monomers; or(b) a prepolymer selected from the group consisting of monofunctional vinyl polymers and multifunctional vinyl polymers;(c) a photoinitiator;(d) at least one filler; and(e) at least one surface active agent having a molecular weight greater than or equal to about 227;wherein one of the surface active agent or the filler has a pH greater than or equal to 7 and the other of the surface active agent or the filler has a pH less than or equal to 7 such that dispersion of the filler in the composition is enhanced and relative high loading of filler in the composition is obtainable;(f) or at least two surface active agents having a molecular weight greater than or equal to about 227 wherein one of the surface active agents has a pH greater than or equaType: GrantFiled: May 16, 1991Date of Patent: January 19, 1993Inventor: Michael Lucey
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Patent number: 5147900Abstract: An energy polymerizable composition comprises at least one ethylenically-unsaturated monomer, one of polyurethane precursors, and at least one epoxy monomer, and a curing agent comprising an organometallic compound, and an onium salt.Type: GrantFiled: April 24, 1990Date of Patent: September 15, 1992Assignee: Minnesosta Mining and Manufacturing CompanyInventors: Michael C. Palazzotto, Katherine A. Brown-Wensley, Robert J. DeVoe
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Patent number: 5147901Abstract: Propiophenones of the formula I ##STR1## in which R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl, --Si(CH.sub.3).sub.3, allyl or benzyl, R.sup.2 is hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.4 -alkyl which is substituted by C.sub.1 -C.sub.4 -alkoxy or --OH, --(CH.sub.2 --CH.sub.2 --O).sub.n --R.sup.5 where n is 2 to 20 and R.sup.5 is H or C.sub.1 -C.sub.4 -alkyl, --Si(CH.sub.3).sub.3, benzyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.4 -alkynyl or 2-tetrahydrofuranyl, or R.sup.1 and R.sup.2 together are a C.sub.1 -C.sub.6 -alkylidene radical or a C.sub.2 -C.sub.6 -alkylidene radical which is substituted by hydroxyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, a linear or branched C.sub.2 -C.sub.6 -alkanediyl radical, a benzylidene, cyclopentylidene or cyclohexylidene radical or a 2,2,2-trichloroethylidene, 2-furylmethylidene or dimethylsilylidene radical, R.sup.3 is phenyl which is unsubstituted or substituted by one or more --Cl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.Type: GrantFiled: September 22, 1989Date of Patent: September 15, 1992Assignee: Ciba-Geigy CorporationInventors: Werner Rutsch, Rudolf Kirchmayr, Rinaldo Husler, Kurt Dietliker
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Patent number: 5137936Abstract: An adhesive composition comprising 10 to 60 parts by weight per 100 parts of the total weight of components (1) to (4) of a monofunctional (meth)acrylic monomer, 0.01 to 10 parts by weight per 100 parts of the total weight of components (1) to (4) of a compound having at least two (meth)acryloyl groups in a molecule, 30 to 80 parts by weight per 100 parts by weight of the total weight of components (1) to (4) of a heat resistant epoxy resin, 0.1 to 20 parts by weight per 100 parts by weight of the total weight of components (1) to (4) of an imidazole compound, 0.001 to 10 parts by weight per 100 parts by weight of the total weight of components (1) to (4) of a photopolymerization initiator, and 0.01 to 20 parts by weight per 100 parts by weight of the total weight of components (1) to (4) of a thixotropic agent, with which an electronic part can be effectively packaged to a printed board.Type: GrantFiled: July 26, 1990Date of Patent: August 11, 1992Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Takashi Akiguchi, Yukio Maeda, Daisuke Irii
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Patent number: 5134175Abstract: Actinic radiation curable composition suitable for use in coating electronic components and as a printing ink comprising as the essential components:(a) a prepolymer selected from the group consisting of monofunctional vinyl resins and multifunctional vinyl resins;(b) a monomer selected from the group consisting of monofunctional vinyl monomers and multifunctional vinyl monomers;(c) a photoinitiator;(d) a filler; and(e) at least one surface active agent having a molecular weight greater than about 227;wherein one of the surface active agent or the filler has a pH greater than or equal to 7 and the other of the surface active agent or the filler has a pH less than or equal to 7 such that dispersion of the filler in the composition is enhanced and relatively high loading of filler in the composition is obtainable.Type: GrantFiled: November 29, 1990Date of Patent: July 28, 1992Inventor: Michael Lucey
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Patent number: 5100767Abstract: The present invention provides a photopolymerizable composition useful as a liquid photoimageable solder mask comprising (a) a reaction product obtained by reacting epoxy resin A containing at least two terminated epoxy groups with 0.8 to 1.2 mol, per 1 epoxy equivalent of epoxy resin A, of an .alpha.,.beta.-unsaturated carboxylic acid and then reacting same with 0.2 to 1.0 mol, per 1 epoxy equivalent of epoxy resin A, of polybasic acid anhydride, (b) diluent, (c) sensitizer, (d) epoxy resin B consisting of tris (2,3-epoxypropyl) isocyanurate whose melting point is 130.degree. C. or less, and (e) an epoxy resin curing agent represented by the general formula [I:] ##STR1## wherein R is --H, halogen, --NH.sub.2, --SH, aromatic hydrocarbon, a C.sub.1 -C.sub.4 alkyl group or NHR' (R' is a C.sub.1 -C.sub.4 alkyl group having --CN or NH.sub.2 C.dbd.NH).Type: GrantFiled: December 19, 1989Date of Patent: March 31, 1992Assignee: Tamura Kaken Co., Ltd.Inventors: Makoto Yanagawa, Shinji Santo
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Patent number: 5096938Abstract: Radiation-curable catalysts are obtainable by reactingA) 1 equivalent of a dihydric to hexahydric oxyalkylated C.sub.2 -C.sub.10 -alcohol withB) from 0.05 to 1 equivalent of a dibasic to tetrabasic C.sub.3 -C.sub.36 -carboxylic acid or its anhydride andC) from 0.1 to 1.5 equivalents of acrylic acid and/or methacrylic acidand reacting the excess carboxyl groups with an equivalent amount of epoxide compound, and are used in radiation-curable coating materials.Type: GrantFiled: April 3, 1990Date of Patent: March 17, 1992Assignee: BASF AktiengesellschaftInventors: Erich Beck, Wolfram Weiss, Horst Schmidt
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Patent number: 5095044Abstract: Compounds of the formula I ##STR1## in which n is 1-30 and X, Y, R, Ar.sup.1 and Ar.sup.2 are as defined in claim 1 can be prepared by reaction of a benzil dialkyl ketal with a diol. Depending on the molar ratio of the two reaction components, products having a different polycondensation degree n are obtained. the compounds can be used as photoinitiators.Type: GrantFiled: April 27, 1990Date of Patent: March 10, 1992Assignee: Ciba-Geigy CorporationInventors: Rinaldo Husler, Rudolf Kirchmayr, Werner Rutsch, Manfred Rembold
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Patent number: 5093386Abstract: A liquid photocurable plastic composition is disclosed which comprises:(a) from 14% to 70% by weight of a polyurethane (meth)acrylate having a polyoxyalkylene structure in the backbone of the polyurethane, said polyurethane (meth)acrylate containing 0.8 to 8 weight percent of ethylenic unsaturation, from 50% to 98% by weight of the polyoxyalkylene structure, and having a number average molecular weight of 1,000 to 7,000;(b) from 5% to 40% by weight of a polyurethane (meth)acrylate having at least 15% by weight of a tricyclodecane structure in the backbone of the polyurethane and a number average molecular weight of from 500 to 1,000;(c) a reactive diluent; and(d) a polymerization initiator.Type: GrantFiled: March 5, 1991Date of Patent: March 3, 1992Assignee: Stamicarbon B.V.Inventors: Timothy E. Bishop, Tohru Ohtaka, Osamu Ishikawa, Masanobu Takahashi, Katsutoshi Igarashi