Specified Rate-affecting Material Contains Onium Group Patents (Class 522/25)
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Patent number: 5639802Abstract: The present invention relates to a novel class of compounds which absorb light at wavelengths greater than 350 nm and are useful as fluorescers or as photoinitiators. The present invention provides compounds of the formulas (I) and (II) and their equivalents (the nomenclature of the compounds used herein is based on the numbering of positions as shown in formula (I)): ##STR1## where: when W is .dbd.O, W.sup.1 is hydrogen or --OR.sup.9 and when W is .dbd.NR.sup.+.sub.2, W is hydrogen or --NR.sub.2, A is hydrogen, alkenyl, alkyl or an election withdrawing group, and the remaining groups are as defined in the disclosure.Type: GrantFiled: November 23, 1993Date of Patent: June 17, 1997Assignee: Spectra Group Limited, Inc.Inventors: Douglas C. Neckers, Yubai Bi
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Patent number: 5631307Abstract: A photopolymerization initiator composition almost free from deactivation and capable of giving a photopolymerizable composition which is almost free from a decrease in the photopolymerization rate in a medium having a high viscosity and shows a high curing rate, containing(A) a sulfonium organoboron complex or oxosulfonium organoboron complex of the formula (1), ##STR1## (B) a sensitizer having electron donating capability and electron acceptability in an excited state.Type: GrantFiled: June 27, 1995Date of Patent: May 20, 1997Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Yasuhiro Tanaka, Yasumasa Toba, Madoka Yasuike, Tadashi Tanoue, Kaoru Nakajima
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Patent number: 5629354Abstract: Improved photopolymerization initiator systems are comprised of a spectral sensitizer that sensitizes in the ultraviolet or visible regions of the spectrum and an N-aryl, O-aryl or S-aryl polycarboxylic acid co-initiator. The improved initiator systems are incorporated in photo-polymerizable compositions containing one or more addition-polymerizable ethylenically-unsaturated compounds to form compositions suitable for the preparation of radiation-sensitive layers in lithographic printing plates adapted to be imagewise-exposed with ultraviolet- or visible-light-emitting lasers such as argon-ion lasers and frequency doubled Nd:YAG lasers. Such plates are able to effectively meet the dual requirements of very high photospeed and very good shelf-life required in computer-to-plate systems.Type: GrantFiled: February 28, 1995Date of Patent: May 13, 1997Assignee: Eastman Kodak CompanyInventors: Paul R. West, Jeffery A. Gurney
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Patent number: 5607817Abstract: A photopolymerizable composition comprising an addition polymerizable compound having at least one ethylenically unsaturated double bond and a photopolymerization initiator system, wherein the photopolymerization initiator system comprises:(a) a sensitizer of the formula (I) ##STR1## wherein -A is ##STR2## wherein each of R.sup.1 and R.sup.2 is a hydrogen atom, an alkyl group, an aryl group or a halogen atom, each of R.sup.3 and R.sup.4 is an alkyl group which may have substituents, each of R.sup.5 to R.sup.8 is a hydrogen atom, an alkyl group or an alkoxy group, or R.sup.3 and R.sup.4, R.sup.3 and R.sup.5 and/or R.sup.4 and R.sup.6 bond to each other to form a ring structure, and n is 0, 1 or 2; and each of X.sup.1 and X.sup.Type: GrantFiled: August 18, 1994Date of Patent: March 4, 1997Assignee: Mitsubishi Chemical CorporationInventors: Hideki Nagasaka, Masaaki Tsuchiyama, Toshiyuki Urano
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Patent number: 5605781Abstract: A photosensitive composition containing a curable cyanate ester and a cationic photoinitiator; and use thereof to form a resist image.Type: GrantFiled: June 7, 1995Date of Patent: February 25, 1997Assignee: International Business Machines CorporationInventors: Jeffrey D. Gelorme, Eugene R. Skarvinko, David W. Wang
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Patent number: 5602191Abstract: Radiation-curable acrylates are prepared by a process in which the hydroxy compound is reacted with acrylic acid or methacrylic acid in a first stage and, in a second stage, the reaction product of the first stage is reacted with an epoxide compound in the presence of, as a catalyst, a quaternary ammonium or phosphonium compound of the general formula ##STR1## where X.sup.- is an opposite ion and R.sup.1 to R.sup.4 independently of one another are each C.sub.1 -C.sub.18 -alkyl which may be substituted by one or two phenyl groups or are each C.sub.6 -C.sub.12 -aryl which may be substituted by one or two C.sub.1 -C.sub.6 -alkyl groups.Type: GrantFiled: May 31, 1995Date of Patent: February 11, 1997Assignee: BASF AktiengesellschaftInventors: Wolfgang Reich, Erich Beck, Edmund Keil, Ulrich Erhardt, Adolf Nuber
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Patent number: 5593812Abstract: The sensitivity of a photoresist to actinic light is improved by the addition of certain dyes. The photoresist includes a polymer matrix, a photosensitive acid generator and at least one compound selected from the group consisting of dyes containing at least one heterosulphur atom such as 2,2.sup.1,5.sup.1,2"-terthiophene and its derivatives; thianthrene and its derivatives, and 4,6-diphenylthieno(3,4-d)-1,3-dioxol-2-one-5,5-dioxide; phenylsulfone and its derivatives; and 4,5-diphenyl-1,3-dioxol-2-one; 3,4-bis(acetoxymethyl)furan; chelidonic acid and its derivatives; and 5,7,12,14-pentacenetetrone. Resist images on a substrate are formed from the compositions.Type: GrantFiled: February 17, 1995Date of Patent: January 14, 1997Assignee: International Business Machines CorporationInventors: Edward D. Babich, Karen E. Petrillo, John P. Simons, David E. Seeger
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Patent number: 5585414Abstract: Resin compositions useful for filament winding applications comprising an epoxy component including at least one polyepoxide resin curable by heat, an olefinicially unsaturated monomer component including at least one polyolefinically unsaturated monomer curable by actinic radiation, at least one photoinitiator, at least one organic peroxide, and a heat activated curing agent for epoxides. The compositions have a viscosity less than about 2000 centipoise (cps) and are capable of retaining this viscosity for at least about 2 hours at a temperature of from about ambient temperature to about 60.degree. C. The resins are capable of being immobilized by actinic radiation exposure and further heat cured without substantial resin drip. One or more organic peroxides are employed, selected from the group of organic peroxides having 10 hour decomposition half lives at temperatures of from about 50.degree. C. to less than about 104.degree. C.Type: GrantFiled: June 7, 1995Date of Patent: December 17, 1996Assignee: Loctite CorporationInventors: Philip T. Klemarczyk, Yoshihisa Okamoto, James P. Moran, Jr.
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Patent number: 5578417Abstract: A process is disclosed for producing a liquid jet recording head comprising applying an active energy-curing resin composition onto at least a part of a surface of a first member for forming a wall of the liquid path; exposing the applied active energy-ray-curing resin to an active energy ray selected from the group consisting of an ultraviolet-ray having an intensity of 1 mW/cm.sup.2 to 100 mW/cm.sup.2 and an electron beam having an intensity of 0.5M Rad to 20M Rad; and providing a second member on the exposed active energy-ray-curing resin composition.Type: GrantFiled: March 20, 1995Date of Patent: November 26, 1996Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Saito
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Patent number: 5578418Abstract: A process is disclosed for producing a liquid jet recording head comprising applying an active energy-curing resin composition onto at least a part of a surface of a first member for forming a wall of the liquid path; exposing the applied active energy-ray-curing resin to an active energy ray selected from the group consisting of an ultraviolet-ray having an intensity of 1 mW/cm.sup.2 to 100 mW/cm.sup.2 and an electron beam having an intensity of 0.5M Rad to 20M Rad; and providing a second member on the exposed active energy-ray-curing resin composition.Type: GrantFiled: March 20, 1995Date of Patent: November 26, 1996Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Saito
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Patent number: 5576357Abstract: A one-component reactive resin system which is stable in storage but nevertheless can readily be cured completely comprises a mixture of commercially available epoxy resins and phosphorus-containing glycidyl esters, in particular phosphonic acid diglycidyl esters, as well as cationic photoinitiators. The low-viscosity reactive resin systems cannot be cured purely by means of heat and can be processed at high temperatures and in particular can have a high filler content. The reactive resin systems, which are stable to storage even after UV activation, can be cured to flame-resistant molded materials under moderate conditions.Type: GrantFiled: May 3, 1995Date of Patent: November 19, 1996Assignee: Siemens AktiengesellschaftInventors: Heiner Bayer, Winfried Plundrich, Ernst Wipfelder
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Patent number: 5565499Abstract: Resin compositions useful for filament winding applications comprising an epoxy component including at least one polyepoxide resin curable by heat, an olefinicially unsaturated monomer component including at least one polyolefinically unsaturated monomer curable by actinic radiation, at least one photoinitiator, at least one organic peroxide, and a heat activated curing agent for epoxides. The compositions have a viscosity less than about 2000 centipoise (cps) and are capable of retaining this viscosity for at least about 2 hours at a temperature of from about ambient temperature to about 60.degree. C. The resins are capable of being immobilized by actinic radiation exposure and further heat cured without substantial resin drip. One or more organic peroxides are employed, selected from the group of organic peroxides having 10 hour decomposition half lives at temperatures of from about 50.degree. C. to less than about 104.degree. C.Type: GrantFiled: June 6, 1995Date of Patent: October 15, 1996Assignee: Loctite CorporationInventors: Philip T. Klemarczyk, Yoshihisa Okamoto, James P. Moran, Jr.
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Patent number: 5554664Abstract: An energy-sensitive (e.g., thermal, radiation or photosensitive) initiator, curative, and/or catalytic salt that has an anion comprising a tris-(highly fluorinated alkylsulfonyl)methide, tris-(fluorinated arylsulfonyl)methide, bis-(highly fluorinated alkyl)sulfonyl imide, bis-(fluorinated aryl)sulfonyl imide, mixed aryl- and alkylsulfonyl imides and methides and any combinations thereof, has improved solubility in organic solvents, exhibit minimal corrosiveness when coatings and adhesives are prepared using the initiator, curative and/or catalytic salts, generates a highly reactive initiator, curative, and/or catalyst upon activation by energy.Type: GrantFiled: November 17, 1995Date of Patent: September 10, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: William M. Lamanna, Michael C. Palazzotto, Wayne S. Mahoney, Michael A. Kropp
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Patent number: 5547713Abstract: A photocopolymerizable composition for backsealing a ceramic carrier and process for using the composition is disclosed. The composition comprises: a liquid, multifunctional, bisphenol based epoxy; a liquid, multifunctional hydroxyl containing organic material; a complex onium salt photoinitiator; and, a complex cupric salt initiator. The composition utilizes a strong Bronstead acid for additional deep curing created by iodonium salt thermolysis.Type: GrantFiled: August 14, 1994Date of Patent: August 20, 1996Assignee: International Business Machines CorporationInventor: Julio M. Alvarado
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Patent number: 5545676Abstract: Photocurable addition-polymerizable compositions containing a free-radically-polymerizable monomer and a photoinitiator system containing i) an arylidonium salt, ii) a sensitizing compound, and iii) an electron donor having an oxidation potential that is greater than zero and less than or equal to that of p-dimethyoxybenzene (1.32 volts vs. S.C.E.). The compositions cure rapidly and deeply under ultraviolet or visible light.Type: GrantFiled: December 28, 1994Date of Patent: August 13, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: Michael C. Palazzotto, F. Andrew Ubel, III, Joel D. Oxman, M. Zaki Ali
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Patent number: 5543262Abstract: A light sensitive composition which is capable of photopolymerization which includes a photopolymerizable compound a free radical generating component and a benzanthrone or substituted benzanthrone which substantially prevents photopolymerization when the light sensitive composition is exposed to actinic radiation below a threshold amount but permits photopolymerization when the light sensitive composition is exposed to actinic radiation above a threshold amount. This achieves a gate effect which eliminates or decreases unwanted partial exposure in the nonimage areas and hence improves reproduction quality.Type: GrantFiled: February 24, 1995Date of Patent: August 6, 1996Assignee: International Paper CompanyInventors: Maria T. Sypek, John R. Delude, Paul A. Perron
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Patent number: 5541235Abstract: A cationic dye in a ketone solvent, wherein the cationic dye has a counterion which comprises a linear, branched or cyclic highly fluorinated alkylsulfonyl methide or highly fluorinated alkyl sulfonyl imide.Type: GrantFiled: March 6, 1995Date of Patent: July 30, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: Stanley C. Busman, William M. Lamanna
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Patent number: 5534557Abstract: The composition of the present invention is excellent in compatibility, transparency and curability and give a cured coat of excellent gloss and of less smell, and cured products of excellent properties can be obtained by curing the composition.The present invention relates to an onium salt represented by the following formula (1): ##STR1## wherein Ar is a mono- to tetra-valent aromatic group, X is a bisphenylsulfonio group which may have a substituent, a is 1-4, b is 0 or 1-3, a+b is 1-4, n is 1-4, and Z is a halide represented by the following formula (3): ##STR2## where M is a boron atom, a phosphorus atom, an arsenic atom or an antimony atom, Q is a halogen atom, m is 3-6, l is 0 or 1, and m+l is 4-6; a photopolymerization initiator containing the onium salt as an active ingredient; an energy ray-curable composition containing the initiator; and a cured product.Type: GrantFiled: June 2, 1995Date of Patent: July 9, 1996Assignee: Nippon Kayaku Kabushiki KaishaInventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
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Patent number: 5516813Abstract: A balancing compound comprising an epoxy resin, a photoinitiator in an effective amount to cure the resin at ambient temperatures upon the application of ultraviolet light (10 nm to 400 nm) of less than 40 watts per square centimeter in less than about 30 seconds, and a filler in an effective amount to give the compound a specific gravity above 1.1.Type: GrantFiled: October 18, 1994Date of Patent: May 14, 1996Inventor: Donn R. Starkey
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Patent number: 5514521Abstract: A photocurable composition comprises a radical-polymerizable unsaturated group including a mixed material which consists of polyethylene glycol di(meth)acrylate and dipentaerythritol hexa(meth)acrylate as a base material, an iron arene compound as a photopolymerization initiator, and an aniline system compound which is N,N-Dimethylaniline as a photochemical sensitizer for having a photocuring sensitivity to light having a wavelength in the range from the ultraviolet region to the infrared region.Type: GrantFiled: August 8, 1994Date of Patent: May 7, 1996Assignee: Brother Kogyo Kabushiki KaishaInventor: Naomichi Kobayashi
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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: 5514729Abstract: A dimensionally stable, UV hardenable polymeric composition is provided in which a conductive filler material is combined with a solventless resin formulation comprising a low viscosity epoxide compound, a photo initiator, and a thermal cure initiator. The properties of the polymeric composition may be adjusted through the addition of reactive diluents, poly alcohol flexiblizers, and acrylate based polymers, photo initiators, and thermal cure initiators. Conductive traces produced by extruding the polymeric composition through a syringe are subjected to a preliminary UV hardening step followed by deposition of an insulator layer and additional conductive traces, until all layers of conductive traces have been deposited. The structure is then subjected to heat until the conductive traces are fully cured. The formulation and the process described produce traces with bulk conductivity at least two times higher than any comparable conductive polymer, without using solvents.Type: GrantFiled: June 27, 1995Date of Patent: May 7, 1996Assignee: Sophia Systems Co., Ltd.Inventors: Joram Diamant, Henry L. Myers
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Patent number: 5502083Abstract: The composition of the present invention is excellent in compatibility, transparency and curability and give a cured coat of excellent gloss and of less smell, and cured products of excellent properties can be obtained by curing the composition.The present invention relates to an onium salt represented by the following formula (1): ##STR1## wherein Ar is a mono- to tetra-valent aromatic group, X is a bisphenylsulfonio group which may have a substituent, a is 1-4, b is 0 or 1-3, a+b is 1-4, n is 1-4, and Z is a halide represented by the following formula (3):MQ.sub.m (OH).sub.l (3)where M is a boron atom, a phosphorus atom, an arsenic atom or an antimony atom, Q is a halogen atom, m is 3-6, l is 0 or 1, and m+l is 4-6; a photopolymerization initiator containing the onium salt as an active ingredient; an energy ray-curable composition containing the initiator; and a cured product.Type: GrantFiled: June 8, 1994Date of Patent: March 26, 1996Assignee: Nippon Kayaku Kabushiki KaishaInventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
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Patent number: 5500453Abstract: A sulfonium complex or oxosulfonium complex of the formula (1), ##STR1## wherein R.sup.1 is a benzyl group, a substituted benzyl group, a phenacyl group, a substituted phenacyl group, an aryloxy group, a substituted aryloxy group, an alkenyl group or a substituted alkenyl group, each of R.sup.2 and R.sup.3 is independently any one of groups defined as R.sup.1, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an aralkyl group, a substituted aralkyl group, an alkynyl group, a substituted alkynyl group, an alicyclic group, a substituted alicyclic group, an alkoxyl group, a substituted alkoxyl group, an alkylthio group, a substituted alkylthio group, an amino group or a substituted amino group, or R.sup.2 and R.sup.3 may bond together forming a ring structure, R.sup.4 is an oxygen atom or lone pair, and each of R.sup.5, R.sup.6, R.sup.7 and R.sup.Type: GrantFiled: August 4, 1994Date of Patent: March 19, 1996Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Yasumasa Toba, Madoka Yasuike, Yamaguchi Takeo
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Patent number: 5492793Abstract: 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 acrylate, methacrylate or a mixture of acrylate and methacrylate.Type: GrantFiled: May 11, 1994Date of Patent: February 20, 1996Assignee: International Business Machines CorporationInventors: Gregory Breyta, Christopher J. Knors, Hiroshi Ito, Ratnam Sooriyakumaran
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Patent number: 5492942Abstract: A pyran derivative has a structure ofR.sup.2 R.sup.3 C.dbd.(C.sub.5 H.sub.2 R.sup.1 O)--(CH.dbd.CH).sub.n --C.sub.6 H.sub.2 R.sup.6 R.sup.7 --NR.sup.4 R.sup.5wherein n is 3 or 4; R.sup.1 is a proton, alkyl or phenyl group; each of R.sup.2 and R.sup.3 is independently a cyano, alkoxycarbonyl having an alkyl, acyl having an alkyl, aracyl having phenyl, sulfonyl, aryl, or aryloxy; each of R.sup.4 and R.sup.5 is an alkyl group; and each of R.sup.6 and R.sup.7 is a proton, provided that R.sup.4 and R.sup.5 are alkyl groups, and a pair of R.sup.4 and R.sup.6 as well as a pair of R.sup.5 and R.sup.7 can be bonded to each other to form a heterocycle.A photosensitive composition comprises a polymerizable compound, a polymerization initiator and a photosensitizer which is the pyran derivative. A photosensitive resin composition comprises a crosslinkable polymer, a crosslinking agent and the photosensitizer.Type: GrantFiled: May 24, 1994Date of Patent: February 20, 1996Assignee: Canon Kabushiki KaishaInventors: Shin Kobayashi, Susumu Matsumura, Naosato Taniguchi, Yoko Yoshinaga, Toshiyuki Sudo, Hideki Morishima, Tadashi Kaneko
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Patent number: 5474876Abstract: A radiation-crosslinkable mixture which contains a carboxyl-containing precursor of a heterocyclic polymer, a copolymerizable ethylenically unsaturated ternary sulfonium salt, a photoinitiator and a polar aprotic organic solvent.Type: GrantFiled: October 5, 1994Date of Patent: December 12, 1995Assignee: BASF Lacke + Farben AGInventors: Hans-Joachim Haehnle, Manfred Schwarz, Rainer Blum
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Patent number: 5468890Abstract: The invention concerns iodonium salts of the general formula A-I.sup.+ --B X.sup.-, in which A is a group of the general formula ##STR1## in which C is a monovalent aromatic hydrocarbon group with 6 to 14 carbon atoms or a monovalent aromatic hydrocarbon group containing at least one oxygen and/or sulphur atom and with 5 to 14 atoms in the aromatic ring, D, E and F are each substituents of C, D being a group of the formula --(O).sub.x --(R).sub.y --SiR1/3, E being a group of the formula --OR.sup.2, F being a group of the formula --R.sup.3, a being 1, 2, or 3, b being 0, 1 or 2, c being 0, 1 or 2, x being 0 or 1 and y being 0 or 1, and R, R.sup.1, R.sup.2 and R.sup.3 are as defined in claim 1; B is a group of the formula ##STR2## in which E and F, which are as defined above, may each be bound to the 2, 3, 4, 5 or 6 position in the benzene ring, d is 0, 1 or 2, e is 0, 1 or 2 and X.sup.- is a tosylate anion or a weakly nucleophilic or non-nucleophilic anion Y.sup.- selected from the group comprising CF.sub.Type: GrantFiled: June 8, 1994Date of Patent: November 21, 1995Assignee: Wacker-Chemie GmbHInventors: Christian Herzig, Silke Scheiding
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Patent number: 5447797Abstract: A reaction resin mixture, which is able to be hardened thermally and by means of UV radiation, contains the following constituents:a cationically polymerizable epoxide resin;a latent hardening initiator in the form of an aralkyl-thiolanium salt; anda sensitizer of the structure ##STR1## A being --CO--, --NR-- and --CO--CO--, and D being --O--, --S--, --CO-- and --CH.sub.2).sub.x (where x= 1 or 2) or rather a single bond or two hydrogen atoms.Type: GrantFiled: August 9, 1993Date of Patent: September 5, 1995Assignee: Siemens AktiengesellschaftInventors: Bernhard Stapp, Lothar Schoen, Volker Muhrer
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Patent number: 5445855Abstract: An active energy ray-curable composition comprising (A) an epoxy resin, (B) a compound selected from the group consisting of sulfonium salts and cyclopentadienyl iron compounds, (C) a compound selected from the group consisting of acrylates, methacrylates and oligomers thereof, and (D) an organic peroxide, and optionally (E) a rubber component. The composition is useful for an adhesive layer of an optical recording medium.Type: GrantFiled: August 5, 1993Date of Patent: August 29, 1995Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Suguru Tokita, Kenji Yamane, Hajime Inagaki, Masayoshi Kurisu
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Patent number: 5422204Abstract: A photo-crosslinkable resin composition comprises (a) a polymer having an electron-donating group in a monomer unit, (b) a halogen compound, (c) an onium salt and (d) at least one sensitizer selected from the group consisting of coumarin derivatives, rhodanine derivatives, thioxanthene derivatives and unsaturated cyclopentanone compounds. The composition can be used as a hologram recording medium.Type: GrantFiled: July 16, 1992Date of Patent: June 6, 1995Assignee: Canon Kabushiki KaishaInventors: Yoko Yoshinaga, Shin Kobayashi, Susumu Matsumura, Naosato Taniguchi, Toshiyuki Sudoh, Hideki Morishima
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Patent number: 5403869Abstract: An adhesive comprising (a) solid epoxy resin having a molecular weight of 5000 or more, (b) a polyfunctional epoxy resin having at least three epoxy groups, (c) an intramolecular epoxy-modified polybutadiene having at least three epoxy groups, (d) a cationic photoinitiator, and (e) a tin compound in special weight ratios, is effective for producing multiple-wire wiring boards having good heat resistance, solvent resistance and wherein the adhesive layer has no voids and prevents shift of insulated encapsulated wires.Type: GrantFiled: August 17, 1993Date of Patent: April 4, 1995Assignee: Hitachi Chemical Company, Ltd.Inventors: Shigeharu Arike, Yorio Iwasaki, Eiichi Shinada, Toshiro Okamura, Kanji Murakami, Yuichi Nakazato
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Patent number: 5395862Abstract: Disclosed is a photooxidizable initiator composition comprising a fluorone initiator and a coinitiator which is capable of accepting an electron from the fluorone upon excitation of the fluorone by actinic radiation, wherein the composition produces free radicals which initiate free radical reactions; and photohardenable compositions which comprise a free radical polymerizable compound, a fluorone initiator and a coinitiator capable of accepting an electron from the fluorone upon exposure of the composition to actinic radiation, and producing free radicals which initiate free radical polymerization.Type: GrantFiled: December 9, 1992Date of Patent: March 7, 1995Assignee: Spectra Group Limited, Inc.Inventors: Douglas C. Neckers, Jianmin Shi
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Patent number: 5385807Abstract: A photopolymerizable composition comprises: (i) a polymerizable compound carrying an addition-polymerizable unsaturated bond; (ii) a methine compound; (iii) at least one compound selected from the group consisting of: (a) compounds having carbon-halogen bonds, (b) aromatic onium salts, (c) organic peroxides, (d) thio compounds, (e) hexaaryl-biimidazoles, (f) ketooxime esters, and (g) compounds represented by the following general formula (III): ##STR1## wherein R.sup.6, R.sup.7, R.sup.8 and R.sup.9 may be the same or different and each represents a substituted or unsubstituted alkyl, aryl, alkenyl, alkynyl or heterocyclic group, provided that at least two of R.sup.6, R.sup.7, R.sup.8 and R.sup.9 may be bonded together to form a ring structure and that at least one of them represents an alkyl group; and Z.sup.+ represents an alkali metal cation or a quaternary ammonium cation. The composition has a high sensitivity to a wide range of actinic light rays extending from ultraviolet to visible light.Type: GrantFiled: June 22, 1992Date of Patent: January 31, 1995Assignee: Fuji Photo Film Co., Ltd.Inventors: Yasuo Okamoto, Syunichi Kondo, Toshinao Ukai
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Patent number: 5384339Abstract: A balancing compound comprising an epoxy resin, a photoinitiator in an effective amount to cure the resin at ambient temperatures upon the application of ultraviolet light (10 nm to 400 nm) of less than 40 watts per square centimeter in less than about 30 seconds, and a filler in an effective amount to give the compound a specific gravity above 1.1.Type: GrantFiled: March 9, 1993Date of Patent: January 24, 1995Inventor: Donn R. Starkey
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Patent number: 5378579Abstract: A photopolymerizable composition comprising(A) an addition-polymerizable compound having an ethylenically unsaturated double bond,(B) a compound of the formula: ##STR1## [wherein R.sup.1 is a substituted or nonsubstituted phenyl group, R.sup.2 and R.sup.3 are the same or different and indicate a hydrogen atom or a C.sub.1-4 alkyl group, R.sup.4 in an alkylene group which may have at least one substituent selected from alkyl, hydroxyl and oxo (.dbd.O) on a main chain, or which may contain at least one member selected from an oxygen atom and a cycloalkylene group in a main chain, R.sup.5 is a hydrogen atom or a methyl group, and a and b are independently 0 or 1],(C) a light absorbing compound, and(D) a film-forming polymer having alkaline solubility or alkaline swelling characteristic is disclosed. There is also disclosed a photosensitive lithographic printing plate comprising the photopolymerizable composition.Type: GrantFiled: July 8, 1992Date of Patent: January 3, 1995Assignee: Nippon Paint Co., Ltd.Inventors: Seiji Arimatsu, Takakazu Hase, Yoshifumi Ichinose
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Patent number: 5374500Abstract: A positive acting photoresist comprising a film forming reactive polymer; an iodonium initiator or a non-ionic compound that generates triflic acid upon exposure to radiation; and a multifunctional organic carboxylic acid is provided as well as use thereof.Type: GrantFiled: April 2, 1993Date of Patent: December 20, 1994Assignee: International Business Machines CorporationInventors: Burton J. Carpenter, Jr., Michael G. McMaster, Joseph LaTorre, Logan L. Simpson
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Patent number: 5368990Abstract: A photopolymerizable composition comprising an addition polymerizable compound having an ethylenically unsaturated double bond and a photopolymerization initiating composition, said photopolymerizable initiating composition comprising (a) a dye of the formula: ##STR1## [wherein R.sub.1 is H, an alkyl group having 1 to 3 carbon atoms, a phenyl group or a halogen atom; R.sub.2 is a methyl group, an ethyl group or (CH.sub.2).sub.p -Q (wherein Q is a carboxyl group, a sulfonyl group or salt thereof and p is an integer of 1 to 4); X.sub.1 and X.sub.2 are independently --O--, --S--, --CH.dbd.CH-- or >N--R.sub.2 ; Y.sub.1 and Y.sub.2 are independently H, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a phenyl group or a halogen atom; Z is --COO or --SO.sub.3 ; m is 0 or 1; and n is an integer of 1 to 4] and (b) diaryliodonium salt as a polymerization initiator.Type: GrantFiled: November 5, 1992Date of Patent: November 29, 1994Assignee: Nippon Paint Co., Ltd.Inventors: Masami Kawabata, Akihiko Sato, Iwao Sumiyoshi
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Patent number: 5364738Abstract: A positive-working light-sensitive composition whose solubility in a developer is increased by irradiation of light, which comprises:(a) a vinyl ether compound having at least one group represented by the following formula (A); ##STR1## wherein R.sup.3 represents a linear or branched alkylene group having 1 to 10 carbon atoms and n represents an integer of 0 or 1;(b) a compound capable of being decomposed by irradiation of an actinic light ray or a radiant ray and releasing an acid; and(c) an alkali-soluble polymer, the light-sensitive composition having high sensitivity to light and permitting the use of light of a wide wavelength range.Type: GrantFiled: October 6, 1992Date of Patent: November 15, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Shunichi Kondo, Akira Umehara, Yoshimasa Aotani, Tsuguo Yamaoka
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Patent number: 5358978Abstract: This invention relates to alkenyl ether polycarbonates having the formula ##STR1## wherein A is selected from the group consisting of lower alkyl and R'HC.dbd.CHOR--, R and R" are each independently a divalent radical having from 2 to 20 carbon atoms and are selected from the group of alkylene, mono- or poly- alkoxylated alkylene, alkenylene, alkynylene, arylene, alkarylene and aralkylene radicals, which radicals are optionally substituted with halo, alkyl, cyano, nitro or alkoxy; R' is hydrogen or lower alkyl; (n) has a value of from 1 to 10 and (m) has a value of from 0 to 10; with the proviso that R" contains at least 3 carbon atoms when m is zero. The invention also concerns the preparation and use of said alkenyl ether polycarbonates.Type: GrantFiled: February 3, 1993Date of Patent: October 25, 1994Assignee: ISP Investments Inc.Inventors: Jeffrey S. Plotkin, Fulvio J. Vara, James A. Dougherty, Paul D. Taylor, Kolazi S. Narayanan
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Patent number: 5346805Abstract: A photopolymerizable composition comprises a polymerizable compound having at least one ethylenically unsaturated double bond and a photopolymerization initiator, wherein the photopolymerization initiator comprises an onium compound and an acridine derivative represented by the following general formula (I): ##STR1## wherein R.sup.1 represents an unsubstituted or substituted phenyl, alkyl or alkoxy group. The composition has high sensitivity to actinic rays over a wide range of wavelength extending from ultraviolet to visible region and thus can be used for preparing a lithographic printing plate, a resin-letterpress plate, a resist or photomask for making a printed board, a monochromatic and colored sheet for transfer or color-development and a color-developing sheet.Type: GrantFiled: September 17, 1993Date of Patent: September 13, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Syunichi Kondo, Akira Umehara
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Patent number: 5340847Abstract: A composition useful as a liquid gasket, having high working efficiency and high initial pressure resistance, is provided. The composition, characterized by being curable by ultraviolet light and by moisture, includes (a) a polysiloxane containing, on at least one molecular end, at least one group selected from the group consisting of (meth)acryl, glycidyl, propenyloxysilyl and thiol; (b) a polyorganosiloxane having silanol groups at both molecular ends; (c) a polyorganosiloxane having, on at least one molecular end, a hydrolyzable group; (d) a photopolymerization catalyst; and (e) a condensation catalyst.Type: GrantFiled: July 23, 1993Date of Patent: August 23, 1994Assignee: Three Bond Co., Ltd.Inventors: Yasuo Hanazuka, Ikuzo Usami, Kazuyuki Chiba, Noriko Mizutani
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Patent number: 5326621Abstract: 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: August 19, 1992Date of Patent: July 5, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Michael C. Palazzotto, Katherine A. Brown-Wensley, Robert J. DeVoe
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Patent number: 5322762Abstract: A highly stable photopolymerizable composition which is highly photosensitive to visible light, which can be hardened using a visible light laser, such as an argon laser, which provides excellent contrast between non-irradiated portions and the substrate under red light, and, moreover, which provides excellent contrast between the portions irradiated by the laser and the portions not irradiated. The photopolymerizable composition consists of 100 parts by weight of a resin which is hardenable under visible light having an irradiation energy mainly consisting of light rays in the 400 nm to 700 nm visible light region; 0.02 to 0.5 parts by weight of at least one dye selected from the group consisting of Victoria Pure Blue, anthraquinone dyes, monoazo dyes, and merocyanine dyes, these dyes having maximum absorption wavelengths from 550 to 700 nm; 0.1 to 5 parts by weight of the leuco dye 4,4'-(phenylmethylene bis[N,N-diethylbenzene amine]; and 0.1 to 5 parts by weight of tribromomethylphenyl sulphone.Type: GrantFiled: April 13, 1993Date of Patent: June 21, 1994Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Kenji Kushi, Chiho Tokuhara
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Patent number: 5300402Abstract: An improved photoimagable cationically polymerizable epoxy based coating material is provided. The material includes an epoxy resin system consisting essentially of between about 10% and about 80% by weight of a polyol resin which is a condensation product of epichlorohydrin and bisphenol A having a molecular weight of between about 40,000 and 130,000; between about 20% and about 90% by weight of an epoxidized octafunctional bisphenol A formaldehyde novolak resin having a molecular weight of 4,000 to 10,000; and if flame retardancy is required between about 35% and 50% by weight of an epoxidized glycidyl ether of tetrabromo bisphenol A having a softening point of between about 60 C. and about 110 C. and a molecular weight of between about 600 and 2,500. To this resin system is added about 0.Type: GrantFiled: July 15, 1991Date of Patent: April 5, 1994Assignee: International Business Machines CorporationInventors: Norman A. Card, Jr., Richard A. Day, Donald H. Glatzel, David J. Russell
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Patent number: 5275917Abstract: A photocurable composition comprises a radical polymerizable unsaturated group-bearing compound, a metal allene compound, and a squalilium compound. The composition is cured by application of low energy visible light or near infrared light having a long wavelength. In the composition, the metal allene compound and the squalilium dye serve as photopolymerization initiators, which are able to produce radicals by application of the long wavelength light and to polymerize the radical polymerizable unsaturated group-bearing compound.Type: GrantFiled: June 18, 1992Date of Patent: January 4, 1994Assignee: Brother Kogyo Kabushiki KaishaInventor: Kouji Inaishi
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Patent number: 5264325Abstract: An improved photoimagable cationically polymerizable epoxy based coating material is provided, that is suitable for use on a variety of substrates. The material includes an epoxy resin system consisting essentially of between about 10% and about 80% by weight of a polyol resin which preferably is a condensation product of epichlorohydrin and bisphenol A having a molecular weight of between about 40,000 and 130,000; and between about 35% and 72% by weight of an epoxidized glycidyl ether of a brominated bisphenol A having a softening point of between about 60.degree. C. and about 110.degree. C. and a molecular weight of between about 600 and 2,500. A third resin, either an epoxy cresol novolak or a polyepoxy resin, is also added to the resin system. To this resin system is added about 0.Type: GrantFiled: July 21, 1992Date of Patent: November 23, 1993Assignee: International Business Machines CorporationInventors: Robert D. Allen, Richard A. Day, Donald H. Glatzel, William D. Hinsberg, John R. Mertz, David J. Russell, Gregory M. Wallraff
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Patent number: 5260455Abstract: Polyepoxy silane compositions resulting from the reaction of olefinepoxide and poly(H)silanes crosslink in the presence of a catalytic amount of an 'onium catalyst when exposed to UV light. In one embodiment, two moles of an olefin-containing epoxy monomer are reacted with a bis(H)-containing silane of general formula R.sub.2 SiH.sub.2. Important to the success of this process is that RhCl.sub.3.xH.sub.2 O is capable of catalyzing the hydrosilation addition of 2 moles of olefin to R.sub.2 SiH.sub.2. The resulting diepoxysilanes are reactive monomers which undergo photopolymerization when exposed to ultraviolet light in the presence of iodonium photocatalysts.Type: GrantFiled: July 8, 1992Date of Patent: November 9, 1993Assignee: General Electric CompanyInventor: Richard P. Eckberg
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Patent number: 5260348Abstract: An improved silicone composition is disclosed, which comprises:a) at least one silanol chain-stopped polydiorganosiloxane polymer;b) an acyloxy, alkoxy, or aryloxy-functional crosslinking agent; andc) a catalytic amount of an onium salt photocatalyst.These materials are characterized by enhanced cure properties, such as short tack free time; and they can also include various other components, such as fillers, plasticizers, condensation cure catalysts, and adhesion promoters.Type: GrantFiled: January 31, 1992Date of Patent: November 9, 1993Assignee: General Electric CompanyInventors: Brian D. Shepherd, David C. Gross
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Patent number: 5254638Abstract: This invention relates to sol-gel methods for forming non-shrinking, high-glass composite materials and the products. Also taught is an inorganic-organic composite material having a solid interwoven network of an inorganic polymer matrix with interpenetrating polymerized alcohols. The inorganic matrix can be based on either Si or Ti atoms.Type: GrantFiled: March 25, 1991Date of Patent: October 19, 1993Assignee: The Reagents of the University of CaliforniaInventors: Bruce M. Novak, Mark W. Ellsworth