Specified Rate-affecting Material Contains Onium Group Patents (Class 522/31)
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Patent number: 6150430Abstract: Described is a process for producing an adherent organic polymeric layer on organic polymeric substrates following the steps of (a) treating the surface of the polymeric substrate to provide reactive groups; (b) applying to the treated surface a polymerizable composition of a surface modifying amount of an organofunctional silane, a catalyzing amount of material which generates acid upon exposure to actinic radiation, and a solvating amount of solvent; (c) exposing the coated surface to an adhesion improving amount of actinic radiation; and (d) applying and curing a photochromic or non-photochromic polymer-forming composition on the coated surface. Also described are articles produced by the process.Type: GrantFiled: July 6, 1999Date of Patent: November 21, 2000Assignee: Transitions Optical, Inc.Inventors: Robert W. Walters, Kevin J. Stewart
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Patent number: 6133336Abstract: Process for forming a selectively colored polymeric layer, or a three-dimensional article made of polymeric layers, wherein a photocurable, photocolorable composition is irradiated with a low dose of light to cure and a different, preferably higher, dose of light to color. The process is particularly useful for preparing selectively colored ornamental and industrial articles and models of plant and animal parts, especially medical models.Type: GrantFiled: August 30, 1996Date of Patent: October 17, 2000Assignee: Zeneca LimitedInventors: Ajay Haridas Popat, Martin Russell Edwards
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Patent number: 6129955Abstract: An electronic package assembly where a low profile integrated circuit chip package is soldered to an organic (e.g., epoxy resin) substrate, e.g., a printed circuit board or card, the projecting conductive leads of the integrated circuit chip package and the solder which substantially covers these leads (and respective conductors on the substrate) having been substantially covered with ultraviolet photocured encapsulant material (e.g., an epoxy resin or a cyanate with a photoinitiator and silica) to provide reinforcement for the solder-lead connections. The encapsulant material is dispensed about the solder and lead joints following solder reflow and solidification so as to substantially surround the solder and any portions of the leads not covered with solder.Type: GrantFiled: June 13, 1997Date of Patent: October 10, 2000Assignee: International Business Machines CorporationInventors: Konstantinos I. Papathomas, Stephen Joseph Fuerniss, Deborah Lynn Dittrich, David Wei Wang
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Patent number: 6130025Abstract: The stereolithographic resin composition comprising,(1)a catinically polymerizing organic compound, (2)an energy beam sensitive cationic polymerization initiator, and (3)a thermoplastic polymer compound which uniformly dissolves in said resin composition was provided. Therefore, the process for optical solid molding, which enabled the production of highly precise solid shape, was provided using said resin composition.Type: GrantFiled: November 12, 1997Date of Patent: October 10, 2000Assignee: Asahi Denka Kogyo Kabushiki KaishaInventors: Satoyuki Chikaoka, Kazuo Ohkawa
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Patent number: 6127092Abstract: Curable reaction resin mixtures which are suitable for stereolithography have the following composition:a cationically curable monomer and/or oligomer,an initiator with the following structure: ##STR1## where the following applies: R.sup.1 and R.sup.2 are alkyl or cycloalkyl, or together with the S atom they form a heterocyclic ring,R.sup.3 is H or alkyl,R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are H, alkyl or alkoxy,X.sup.- is a non-nucleophilic anion,and optionally a filler, pigment and/or additive.Type: GrantFiled: June 26, 1998Date of Patent: October 3, 2000Assignee: Siemens AGInventors: Lothar Schon, Wolfgang Rogler, Volker Muhrer, Manfred Fedtke, Andreas Palinsky
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Patent number: 6121340Abstract: The present invention relates to a photodefinable dielectric composition comprising a photoinitiator and a polycyclic addition polymer comprising polycyclic repeating units that contain pendant silyl functionalities containing hydrolyzable substituents. Upon exposure to a radiation source the photoinitiator catalyzes the hydrolysis of the hydrolyzable groups to effect the cure of the polymer and adhesion of the polymer to desired substrates.Type: GrantFiled: November 4, 1997Date of Patent: September 19, 2000Assignee: The B. F. Goodrich CompanyInventors: Robert A. Shick, Saikumar Jayaraman, Edmund Elce, Brian L. Goodall
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Patent number: 6121339Abstract: An epoxy resin composition according to the present invention is one initiating cationic polymerization upon irradiation with energy rays. The epoxy resin composition is formed of at least bisphenol epoxy resin (A) as an active ingredient, epoxy resin (B) shown in the following formula and cationic polymerization catalyst (C).Type: GrantFiled: February 12, 1998Date of Patent: September 19, 2000Assignee: Sony Chemicals CorporationInventors: Hiraku Kominami, Kozaburo Hayashi, Kazuki Shibata
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Patent number: 6103450Abstract: A photosensitive polymer, a dissolution inhibitor, and a chemically amplified photoresist composition containing the photosensitive polymer and the dissolution inhibitor are provided. The photosensitive polymer is a copolymer polymerized with 5-norbornene-2-methanol derivative monomer having a C.sub.1 to C.sub.20 aliphatic hydrocarbon as a side chain, and a maleic anhydride monomer. The dissolution inhibitor is a tricyclodecane derivative or a sarsasapogenin derivative, each having an acid-labile group as a functional group. The chemically amplified photoresist composition containing the photosensitive polymer and/or dissolution inhibitor has a strong resistance to etching and excellent adherence to underlying layer.Type: GrantFiled: March 26, 1999Date of Patent: August 15, 2000Assignee: Samsung Electronics Co., Ltd.Inventor: Sang-jun Choi
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Patent number: 6096796Abstract: A photo-curable resin composition capable of providing a three-dimensional object having excellent mechanical strength and high dimensional accuracy when used in a photo-fabrication process. The resin composition is also capable of providing a three-dimensional object with excellent stability in shape and properties in a photo-fabrication process. The photo-curable composition includes:(A) a compound represented by the formula (1) ##STR1## wherein R.sup.1 and R.sup.2 independently represent a hydrogen atom or a methyl group;(B) a compound having a cyclohexene oxide structure;(C) a cationic photo-initiator;(D) an ethylenically unsaturated monomer;(E) a radical photo-initiator; and(F) a polyol having three or more hydroxyl groups.Type: GrantFiled: December 10, 1997Date of Patent: August 1, 2000Assignees: DSM N.V., JSR Corporation, Japan Fine Coatings Co., Ltd.Inventors: Tsuyoshi Watanabe, Tetsuya Yamamura, Akira Takeuchi, Takashi Ukachi
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Patent number: 6093753Abstract: The present invention is to provide curable compositions usable appropriately in coatings, adhesives, photoresists, etc. and directed to sulfonium salt compounds represented by general formula [I]; ##STR1## wherein R.sub.1 and R.sub.2 represent alkyl, hydroxy, alkoxy, alkylcarbonyl, aromatic carbonyl, aromatic thio or halogeno; R.sub.3 represents alkyl; R.sub.4 represents optionally substituted alkyl, alkenyl or cycloalkyl; m and n are each 0, 1, 2 or 3; and X represents a non-nucleophilic anionic residue; a cationic polymerization initiator containing the compound; and a curable composition which contains the compound and a cationically polymerizable compound optionally together with a sensitizer.Type: GrantFiled: February 19, 1998Date of Patent: July 25, 2000Assignee: Nippon Soda Co., Ltd.Inventor: Eiji Takahashi
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Patent number: 6090487Abstract: The present invention relates to a sizing composition for glass threads which comprises a solution of a viscosity of less than or equal to 400 cP containing less than 5% by weight of solvent and containing at least one base system which can be polymerised under the action of ultraviolet radiation or an electron beam, the said base system comprising at least one component that has a molecular mass of less than 750 and that has at least one reactive epoxy group and comprising at least 60% by weight of one or more components that have a molecular mass of less than 750 and that have at least one reactive group selected from the following groups: epoxy, hydroxy, vinyl ether, acrylic and methacrylic.The invention relates also to a process using this composition and to the threads coated with the said composition.Type: GrantFiled: December 15, 1998Date of Patent: July 18, 2000Assignee: Vetrotex FranceInventor: Patrick Moireau
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Patent number: 6084004Abstract: The invention relates to compositions which undergo cationic curing with visible light, comprising:(a) 0.01 to 8 wt. % of at least one diaryliodonium compound,(b) 0.01 to 8 wt. % of at least one .alpha.-dicarbonyl compound,(c) 10.0 to 99.9 wt. % of at least one compound containing epoxide groups and/or oxetane groups,(d) 0 to 85 wt. % of modifiers, such as fillers, dyestuffs, pigments, flow improvers, thixotropic agents, polymeric thickeners, additives having an oxidizing action, stabilizers and retardants, characterized in that they additionally comprise(e) 0.001 to 5 wt. % of at least one aromatic amine.The compositions have a low intrinsic color, cure with little smell and, after curing, give compositions with very good mechanical properties.Type: GrantFiled: August 21, 1998Date of Patent: July 4, 2000Assignee: Espe Dental AGInventors: Wolfgang Weinmann, Gunther Eckhardt
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Patent number: 6084035Abstract: A resin composition for powder coating, comprising(A) a carboxyl group-containing resin having a number average molecular weight of 1000 to 20000, an acid value of 5 to 200 and a glass transition temperature of 30 to 120.degree. C.,(B) bis(.beta.-methylglycidyl)terephthalate of the formula (1): ##STR1## as a curing agent, and (D) at least one compound selected from the group consisting of amines having the linkage of the formula (2): ##STR2## in the molecule, a triarylphosphines and onium salts as a ring-opening polymerization inhibitor, the equivalent ratio of (.beta.-methylglycidyl group of the component (B))/(carboxyl group of the component (A)) being 0.5 to 3.0. The composition can give a product of curing excellent in impact resistance, weathering resistance and so on.Type: GrantFiled: November 4, 1998Date of Patent: July 4, 2000Assignee: Nissan Chemical Industries, Ltd.Inventors: Satoru Miyake, Hisao Ikeda, Toshinari Koda, Motohiko Hidaka
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Patent number: 6063896Abstract: A copolymer of maleimide derivative and acrylic acid, represented by Formula I, is of high etch resistance and thermal resistance and can be used for photoresist in submicrolithography.Type: GrantFiled: June 24, 1997Date of Patent: May 16, 2000Assignee: Hyundai Electronics Industries Co., Ltd.Inventors: Jae Chang Jung, Cheol Kyu Bok
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Patent number: 6060207Abstract: A photosensitive material which is very low in absorption of a light source of short wavelength and excellent in dry etch resistance. This photosensitive material comprises a compound having a terpenoid skeleton. Preferably, the compound having a terpenoid skeleton is a compound having a monovalent menthyl group or menthyl derivative group which can be represented by the general formula (1). ##STR1## wherein R is a hydrogen atom or a monovalent hydrocarbon group, R.sup.1 may be the same with or different from each other and individually represents a hydrogen atom, a halogen atom, a hydrocarbon group, a hydroxyl group, an alkoxyl group, an amino group, an alkoxy group, an amino group, an imide group, an amide group, or a sulfonyl group, a carboxyl group, a carbonyl group, or a sulfonamide group, and a pair of neighboring R.sup.1 may be connected together to form a closed ring.Type: GrantFiled: July 10, 1995Date of Patent: May 9, 2000Assignee: Kabushiki Kaisha ToshibaInventors: Naomi Shida, Toru Ushirogouchi, Takuya Naito, Makoto Nakase
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Patent number: 6054501Abstract: This invention provides an energy ray curable composition which has excellent curability. The composition contains a cationic polymerizable substance, a photopolymerization initiator comprised of a specified onium salt and a pigment as occasion demands. The curable composition is excellent in curability, and cured paint films obtained therefrom shows excellent glossiness. This composition can be blended in white inks, printing inks, paints, resist inks, wood fillers and the like.Type: GrantFiled: March 9, 1998Date of Patent: April 25, 2000Assignee: Nippon Kayaku Kabushiki KaishaInventors: Nobuo Taniguchi, Minoru Yokoshima
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Patent number: 6051370Abstract: A radiation-sensitive mixture suitable for producing relief structures consists essentially of(a) a water-insoluble but alkali-soluble binder or binder mixture and(b) a compound which forms a strong acid on irradiation, wherein component (a) is a phenolic resin whose phenolic hydroxyl groups have been replaced to a certain extent by groups (I) ##STR1## where R.sup.1 is alkyl, andR.sup.2 and R.sup.3 are each hydrogen or alkyl, or R.sup.1 forms a ring with R.sup.2.Type: GrantFiled: January 9, 1995Date of Patent: April 18, 2000Assignee: BASF AktiengesellschaftInventor: Son Nguyen Kim
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Patent number: 6031014Abstract: Cationic polymerization initiators of formula ##STR1## are disclosed. The acyl sulfonium salts of the present invention differ from known acyl sulfonium initiators in that the substituents R.sup.2 and R.sup.3 on the sulfur are larger and more complex than the lower alkyl and lower alkylene of known photoinitiators. Processes for the synthesis of the novel acyl sulfonium salts and prepolymer compositions containing them are also disclosed.Type: GrantFiled: December 8, 1998Date of Patent: February 29, 2000Inventor: James V. Crivello
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Patent number: 6028124Abstract: This invention relates to a radiation curable compositions. More particularly this invention relates to radiation curable compositions comprising a vinyl ether compound which is free of silicon atoms, a cationic photoinitiator, a free radical photoinitiator, and dodecylphenol. The radiation curable compositions of this invention are useful for coating a thin layer film that has potential for many applications in the coating industry.Type: GrantFiled: November 25, 1998Date of Patent: February 22, 2000Assignee: Dow Corning CorporationInventors: Shedric Oneal Glover, Chi-long Lee, Wen-hong Tong
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Patent number: 6017976Abstract: Process for producing coatings or moldings by radiation curing, which involves using high-energy light to irradiate radiation-curable compositions containing 1-100% by weight, based on the total amount of free-radically or cationically polymerizable compounds, of compounds A) containing at least one cationically polymerizable 2,3-dihydrofuran structure.Type: GrantFiled: October 22, 1996Date of Patent: January 25, 2000Assignee: BASF AktiengesellschaftInventors: Wolfgang Reich, Reinhold Schwalm, Erich Beck, Lukas Haussling, Oskar Nuyken, Roman-Benedikt Raether
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Patent number: 6013411Abstract: A positive working photosensitive composition comprising a resin having repeating units represented by the following formulae (I), (II) and (III), respectively and a compound which generates an acid with irradiation of an active ray or radiation: ##STR1## wherein R.sub.1 represents a hydrogen atom or a methyl group; R.sub.2 represents --C(.dbd.O)--O--C(R.sub.6) (R.sub.7) (R.sub.8) or --O--R.sub.5 --C(.dbd.O)--O--(R.sub.6) (R.sub.7) (R.sub.8); R.sub.3 represents --O--C(R.sub.6)(R.sub.7) (R.sub.8), --O--Si(R.sub.6)(R.sub.7)(Rs) or --O--C(R.sub.9)(R.sub.10)--OR.sub.11 ; R.sub.4 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an acyl group or an acyloxy group; R.sub.5 represents an alkylene group; R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an alkenyl group, provided that at least two among R.sub.6, R.sub.7 and R.sub.8 are groups other than a hydrogen atom; R.sub.Type: GrantFiled: February 5, 1997Date of Patent: January 11, 2000Assignee: Fuji Photo Film Co., Ltd.Inventors: Toshiaki Aoai, Toru Fujimori, Tsukasa Yamanaka, Kazuya Uenishi
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Patent number: 6011079Abstract: A radiation curable release coating composition comprising, by weight,(a) 10-90% of an acrylate-functional silicone resin,(b) 10-90% of a vinylether monomer as reactive diluent therein, and(c) a photoinitiator.Type: GrantFiled: October 9, 1997Date of Patent: January 4, 2000Assignee: ISP Investments Inc.Inventors: James A. Dougherty, John Mc Kittrick
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Patent number: 6010820Abstract: Provided is a positive photosensitive composition which has high photosensitivity, is capable of giving an excellent resist pattern, and changes little with time after exposure. The positive photosensitive composition comprises (1) a resin having group(s) capable of decomposing by the action of an acid to enhance solubility of the resin in an alkaline developing solution and (2) a compound represented by formula (I), (II) or (III) which is capable of generating a sulfonic acid upon irradiation with actinic rays or a radiation: ##STR1## wherein R.sub.1 to R.sub.5 and R.sub.7 to R.sub.10 each represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a hydroxy group, a halogen atom, or a group represented by --S--R.sub.6, where R.sub.6 represents an alkyl group or an aryl group; X.sup.- represents the anion of a benzenesulfonic, naphthalenesulfonic, or anthracenesulfonic acid as defined in the specification; and m, n, p and q each represents an integer of 1 to 3.Type: GrantFiled: March 11, 1997Date of Patent: January 4, 2000Assignee: Fuji Photo Film Co., Ltd.Inventors: Toshiaki Aoai, Kunihiko Kodama, Kazuya Uenishi, Tsukasa Yamanaka
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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: 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: 6008267Abstract: Polymer or oligomer ionic compound made of a polycationic part (A.sup.+).sub.p comprising a plurality of onium units and a sufficient number of anions X.sup.- to provide electrical neutrality to the compound, characterized in thatthe onium units are selected from the group consisting of biaryliodonium, arylsulfonium, arylacylsulfonium, diazonium, organometallic cations comprising a transition metal which is complexed by at least one unsaturated cycle comprising 4 to 12 carbon atoms;X.sup.- is an imide anion [R.sub.F SO.sub.2 NSO.sub.2 R'.sub.F ].sup.- or a methylide anion [R.sub.F SO.sub.2 C(Q)SO.sub.2 R'.sub.F ].sup.- in which:1) Q represents:H--, Cl--, F--, Br--or CN--;an alkyl radical having 1 to 30 carbon atoms;an aryl, alkylaryl or arylakyl radical having 6 to 30 carbon atoms;a group R".sub.F or a group R".sub.F SO.sub.2 ;2) R.sub.F and R'.sub.F, as well as R".sub.F possibly when X.sup.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: 6008268Abstract: A method of generating reactive species which includes exposing a photoreactor composition to radiation, in which the photoreactor composition comprises a wavelength-specific sensitizer associated with one or more reactive species-generating photoinitiators. Also described are methods of polymerizing unsaturated monomers and curing an unsaturated oligomer/monomer mixture.Type: GrantFiled: January 22, 1998Date of Patent: December 28, 1999Assignee: Kimberly-Clark Worldwide, Inc.Inventors: Ronald Sinclair Nohr, John Gavin MacDonald
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Patent number: 6004721Abstract: A positive photoresist composition is disclosed which comprises (a) a resin obtained from an alkali-soluble resin containing phenolic hydroxyl groups by replacing from 10 to 80% of the phenolic hydroxyl groups each with a group having a specific structure, (b) a compound which generates an acid upon irradiation with actinic rays or a radiation, and (c) a solvent. This composition is an excellent, chemically amplified photoresist composition which has high resolution and gives a resist pattern having no depressions in an upper part thereof and having satisfactory adhesion to the substrate.Type: GrantFiled: February 5, 1998Date of Patent: December 21, 1999Assignee: Fuji Photo Film Co., Ltd.Inventors: Shiro Tan, Toshiaki Aoai, Toru Fujimori
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Patent number: 6001428Abstract: 1. A solid composition comprising(a) a solid oligomeric, cationically polymerisable polyglycidyl ether or polyglycidyl ester, a mixture of a solid oligomeric, cationically polymerisable polyglycidyl ether or polyglycidyl ester and a liquid or crystalline monomeric mono-, di- or polyepoxy resin, or a mixture of a solid oligomeric, cationically polymerisable polyglycidyl ether or polyglycidyl ester and a cyclic acetal, said oligomeric polyglycidyl ether or polyglycidyl ester and the mixtures containing the oligomeric polyglycidyl ether or polyglycidyl ester having a glass transition temperature (T.sub.G) higher than 35.degree. C.,(b) a multifunctional nucleophilic chain transfer agent,(c) 0.Type: GrantFiled: April 10, 1996Date of Patent: December 14, 1999Assignee: Ciba Specialty Chemicals Corp.Inventors: Jurgen Finter, Philippe-Guilhaume Gottis, Alfred Mockli
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Patent number: 5998099Abstract: A process for device fabrication and resist materials that are used in the process are disclosed. The resist material contains a substituted amine-containing component and a polymer. The substituted-amine containing component is either a photoacid generator, or an amine additive to the resist material that also contains a photoacid generator. The resist material contains acid labile groups either pendant to the polymer or to a dissolution inhibitor that is combined with the polymer. The acid labile groups significantly decrease the solubility of the polymer in a solution of aqueous base. A film of the resist material is formed on a substrate and exposed to delineating radiation. The radiation induces a chemical change in the resist material rendering the exposed resist material substantially more soluble in aqueous base solution than the unexposed portion of the resist material.Type: GrantFiled: May 22, 1998Date of Patent: December 7, 1999Assignee: Lucent Technologies Inc.Inventors: Francis Michael Houlihan, Omkaram Nalamasu, Thomas Ingolf Wallow
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Patent number: 5998496Abstract: A compound of the general formula:A-L.sup.+ D.sup.-where A is a moiety which absorbs radiation and enters an excited state in which it accepts an electron; D.sup.- is a moiety which donates an electron to the excited state A and releases a free radical; and L.sup.+ is a cationic linking group which tethers electron acceptor moiety A to electron donor moiety D.sup.-. Cationic linking moiety L.sup.+ has the formula:-L'-G-where L' is a moiety which forms a stable radical with acceptor moiety A upon transfer of an electron from donor moiety D.sup.- to electron acceptor moiety A, and G is a moiety which forms a leaving group upon transfer of the electron from donor moiety D.sup.- to acceptor moiety A.Type: GrantFiled: August 19, 1996Date of Patent: December 7, 1999Assignee: Spectra Group Limited, Inc.Inventors: Salah A. Hassoon, Ananda M. Sarker, Douglas C. Neckers
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Patent number: 5985447Abstract: A method of producing glass strands, the method comprising coating glass strands with a heat-polymerizable composition constituted by a solution with a solvent content of less than 5% by weight and a viscosity of less than 400 cP, the solution comprising a basic structure which can be polymerized or cross-linked thermally, the structure comprising at least 60% by weight of one or more components with molecular weights of less than 750, having at least one acrylic and/or methacrylic and/or vinyl ether and/or N-vinylamide and/or N-vinyllactam function, the proportion of polyfunctional components within these components being at least 45% by weight of these components, so as to produce glass strands coated with a non-polymerized, heat-polymerizable composition; the glass strands produced, as well as to composites produced from the strands.Type: GrantFiled: January 15, 1997Date of Patent: November 16, 1999Assignee: Vetrotex FranceInventor: Patrick Moireau
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Patent number: 5980253Abstract: In a first aspect, a method for treating hard tissue that includes: (a) applying to hard tissue a composition that includes a cationically active functional group, a free radically active functional group, and a polymerization initiator capable of initiating free radical polymerization, where the number of moles of cationically active functional groups per gram of composition is no greater than about 0.0075; and (b) exposing the composition to polymerization conditions to form an adhesive bonded to the hard tissue.Type: GrantFiled: January 12, 1998Date of Patent: November 9, 1999Assignee: 3M Innovative Properties CompanyInventors: Joel D. Oxman, Hoa T. Bui, Dwight W. Jacobs
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Patent number: 5973020Abstract: The present invention relates to a photoinitiator composition that can be used to initiate polymerization upon exposure to radiation. The said composition includes both a composition which yields cations upon exposure to actinic radiation, such as an iodonium borate initiator and a stabilizing amino agent. The amino agent is a secondary or tertiary amine having the general formula (VIII), a sterically arranged cyclic amine having the general formula (IX), or an amine consisting of groups that have the general formulas (VIII) and (IX) and that are interconnected. ##STR1## The compositions are particularly useful when used in conjunction with polyorganosiloxane monomers and when exposed to ultraviolet radiation.Type: GrantFiled: January 6, 1998Date of Patent: October 26, 1999Assignee: Rhodia Inc.Inventors: Stuart R. Kerr, III, Reeshemah L. Beaty
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Patent number: 5962184Abstract: The present invention relates to an improved chemically amplified photoresist composition comprising (i) a photosensitive acid generator and (ii) a polymer comprising the reaction product of hydroxystyrene with a monomer selected from acrylate or methacrylate having an alicyclic ester substituent.Type: GrantFiled: December 13, 1996Date of Patent: October 5, 1999Assignee: International Business Machines CorporationInventors: Robert David Allen, Ratnam Sooriyakumaran
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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: 5945250Abstract: A photosensitive composition containing a sulfonium or iodonium salt resin having a specific repeating structural units has good solubility in solvents and high photosensitivity, are capable of giving an excellent resist pattern, and change little with time after exposure.Type: GrantFiled: June 4, 1997Date of Patent: August 31, 1999Assignee: Fuji Photo Film Co., Ltd.Inventors: Toshiaki Aoai, Kenichiro Sato, Kunihiko Kodama
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Patent number: 5942554Abstract: A method for the formation of a colored polymeric body which comprises subjecting a curable composition containing a color precursor and an onium salt to heat or actinic radiation to cure the composition, wherein the color precursor is converted to its colored form, and a curable composition capable of forming a colored polymeric body, are disclosed.Type: GrantFiled: February 20, 1996Date of Patent: August 24, 1999Assignee: Spectra Group Limited, Inc.Inventors: Yuijin Ren, Wolter Jager, Douglas C. Neckers
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Patent number: 5939465Abstract: A photopolymerizable composition comprises (i) a compound represented by formula (I): ##STR1## wherein R.sup.1 and R.sup.2 each independently represents a hydrogen atom, a cyano group, a substituted carbonyl group, a substituted or unsubstituted, alkyl group, aryl group, alkenyl group, or alkynyl group; R.sup.3, R.sup.4 and R.sup.5 each independently represents a substituted or unsubstituted, alkyl group, aryl group, alkenyl group, or alkynyl group; Z represents a nonmetallic atom group necessary for forming a heterocyclic nucleus containing an N atom; n represents an integer of 0, 1 or 2; and G.sup.1 and G.sup.2 each independently represents a hydrogen atom, a cyano group, a substituted, carbonyl group, oxy group, amino group, thio group, sulfonyl group, sulfinyl group or an atomic group represented by formula (II) described in the specification, provided that G.sup.1 and G.sup.Type: GrantFiled: July 30, 1997Date of Patent: August 17, 1999Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuto Kunita, Yasuo Okamoto
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Patent number: 5928818Abstract: Polymers having an average molecular weight M.sub.w (weight average) of 5,000 to 1,000,000 (measured by gel permeation chromatography), comprising structural repeating units of the formulae I-IV: ##STR1## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another are hydrogen, methyl or halogen, R.sub.5 and R.sub.6 independently of one another are C.sub.1 -C.sub.6 alkyl, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 independently of one another are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, and w, x, y and z are numbers equal to or greater than 1, with the provision that the quotient ##EQU1## which is obtainable from the sum of the structural units having protecting groups divided by the sum of all of the structural units present, obeys the condition 0.10.ltoreq.Q.ltoreq.0.50, are suitable as binders for DUV photoresists of high processing stability and flow resistance.Type: GrantFiled: February 26, 1997Date of Patent: July 27, 1999Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Carl-Lorenz Mertesdorf, Hans-Thomas Schacht, Norbert Muenzel, Pasquale Alfred Falcigno
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Patent number: 5919596Abstract: Disclosed is an admixture which is curable to form a crack resistant, photosensitive polycyanurate resist. Also disclosed is a structure for its use and process of making. The resist can be tailored to be either positively or negatively sensitive to actinic radiation. Because of its improved thermal and mechanical properties, the cured resist is suitable for use at high temperature, such as in electronic packaging applications.Type: GrantFiled: February 11, 1997Date of Patent: July 6, 1999Assignee: International Business Machines CorporationInventors: Jeffrey C. Hedrick, Konstantinos Papathomas, Stephen L. Tisdale, Alfred Viehbeck, Jeffrey D. Gelorme, Voya Rista Markovich, Thomas H. Lewis, Stephen Joseph Fuerniss
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Patent number: 5914219Abstract: Positive-working radiation-sensitive mixtures, essentially consisting of(a1) a water-insoluble organic binder which contains acid-labile groups and is rendered soluble in aqueous alkaline solutions by the action of an acid, or(a2.1) a polymeric binder which is insoluble in water but soluble in aqueous alkaline solutions and(a2.2) an organic compound whose solubility in an aqueous alkaline developer is increased by the action of an acid, and(b) an organic compound which produces an acid under the action of actinic radiation, which additionally contain(c) a strongly basic organic compound having hydroxide, alkoxide or phenoxide anions, are suitable for the production of relief structures having improved contrast.Type: GrantFiled: October 22, 1996Date of Patent: June 22, 1999Assignee: BASF AktiengesellschaftInventors: Dirk Funhoff, Reinhold Schwalm, Horst Binder
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Patent number: 5902838Abstract: Cationically curable adhesives and sealants with increased viscosities and improved rheological control and good storage stability are prepared using a cationically curable monomer and a thickening polymer which is the alkylation reaction product of poly(4-hydroxystyrene) or poly(2-hydroxystyrene) with a compound RX where R is allyl, methallyl, crotyl or prenyl and X is Cl, Br or I. The cationically curable monomer suitably includes at least one alkenyloxystyrene monomer. Such thickened adhesives are useful as edge sealants for flat panel display devices. A-stage curing of the adhesive with UV irradiation allows for near ambient temperature fixturing of the device assemblies and B-stage thermal curing of the adhesive can be conducted at much lower temperatures than are needed for glass frit sealants. The B-stage cured products have thermal resistance, outgassing and substrate adhesion properties adequate for flat panel display devices.Type: GrantFiled: October 1, 1996Date of Patent: May 11, 1999Assignee: Loctite CorporationInventors: John G. Woods, Maria L. Masterson, Matthew P. Burdzy, Bernard M. Malofsky
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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: 5891603Abstract: Provided is a positive working photosensitive composition comprising (a) a compound represented by the following formula (I) which generates a sulfonic acid by irradiation with active rays or radiation, and (b) a resin comprising constitutional repeating units of the following formulae (II) and (III) and having groups which enable an increase of the solubility in an alkali developer through their decomposition due to the action of an acid: ##STR1## wherein Y represents an alkyl group, an aralkyl group, or a specific phenyl, naphthyl or anthracenyl group and Y may be bonded to the other imidesulfonate compound residue; and X represents an alkylene group, an alkenylene group, an arylene group, or an aralkylene group, and X may be bonded to the other imidesulfonate compound residue: ##STR2## wherein R.sub.22 represents a hydrogen atom, an alkyl group, or an aralkyl group; and A represents an alkyl group or an aralkyl group, and A may combine with R.sub.22 to complete a 5- or 6-membered ring.Type: GrantFiled: April 25, 1997Date of Patent: April 6, 1999Assignee: Fuji Photo Film Co., Ltd.Inventors: Kunihiko Kodama, Toshiaki Aoai, Kazuya Uenishi
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Patent number: 5891930Abstract: Provided is a radiation-curable optical glass fiber coating composition adapted to provide the combination of properties of:(i) enhanced resistance to thermal degradation when suitably cured; and(ii) a viscosity sufficient to provide a surface substantially free-of pitting.The composition is formulated from components including:(A) at least one epoxy silicone monomer or oligomer which is crosslinkable via actinic radiation, or mixture thereof;(B) at least one thermoplastic resin which is substantially unreactive to actinic radiation and which is soluble or dispersible in component (A), said thermoplastic resin being present in an amount to provide said composition with a viscosity suitable for application to an optical glass fiber; and(C) a catalytically effective amount of a photoinitiator for catalyzing the crosslinking reaction of component (A) and which is soluble or dispersible in component (A) or a mixture of said component (A) and said thermoplastic resin.Type: GrantFiled: August 9, 1996Date of Patent: April 6, 1999Assignee: DSM N.V.Inventors: Stephen C. Lapin, Edward J. Murphy
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Patent number: 5882844Abstract: A chemically amplified positive resist composition contains (A) an organic solvent, (B) a base resin in the form of a polysiloxane having phenolic hydroxyl groups some of which are protected with alkoxyalkyl groups and having a weight average molecular weight of 2,000-50,000, (C) a photoacid generator, and (D) a vinyl ether group-containing compound. The composition has high sensitivity to actinic radiation, is developable with aqueous base to form a resist pattern, and lends itself to fine patterning.Type: GrantFiled: April 1, 1997Date of Patent: March 16, 1999Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Junji Tsuchiya, Toshinobu Ishihara, Shigehiro Nagura, Katsuya Takemura, Tsuguo Yamaoka
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Patent number: 5882842Abstract: An active energy ray-curable resin composition, particularly an active energy ray-curable coating composition, both comprising:(A) a resin having oxetane functional groups and epoxy groups in the molecule, and(B) a photo-induced cationic polymerization initiator.Type: GrantFiled: February 12, 1997Date of Patent: March 16, 1999Assignee: Kansai Paint Co., Ltd.Inventors: Yu Akaki, Fumio Yamashita, Yasuo Takaya, Osamu Isozaki
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Patent number: 5882835Abstract: A chemical amplified positive photoresist composition including a resin having the repeating unit of Formula I and a photoacid generator. The resin ranges, in polystyrene-reduced molecular weight, from about 2,000 to 1,000,000. In Formula I, k and l each represent a mole ratio satisfying the condition of k+l=l. R.sub.1 is a hydrogen atom or a methyl group. R.sub.2 and R.sub.3 are independently either a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group. R.sub.4 is an acetate group, a t-butoxycarbonyl group, a benzyl group, a trialkylsilyl group or an alkyl group. The photoacid generator which generates an acid by radiation.Type: GrantFiled: September 17, 1997Date of Patent: March 16, 1999Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Joo-Hyeon Park, Seong-Ju Kim, Ki-Dae Kim, Sun-Yi Park
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Patent number: 5882792Abstract: The present invention relates to a sizing composition for glass threads which comprises a solution of a viscosity of less than or equal to 400 cP containing less than 5% by weight of solvent and containing at least one base system which can be polymerized under the action of ultraviolet radiation or an electron beam, the said base system comprising at least one component that has a molecular mass of less than 750 and that has at least one reactive epoxy group and comprising at least 60% by weight of one or more components that have a molecular mass of less than 750 and that have at least one reactive group selected from the following groups: epoxy, hydroxy, vinyl ether, acrylic and methacrylic. The invention relates also to a process using this composition and to the threads coated with the said composition.Type: GrantFiled: October 10, 1996Date of Patent: March 16, 1999Assignee: Vetrotex FranceInventor: Patrick Moireau