Specified Rate-affecting Material Contains Onium Group Patents (Class 522/31)
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Patent number: 5635332Abstract: A photoresist composition containing an alkylsulfonium salt compound represented by the following general formula (I): ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different, each being a linear, branched or cyclic C.sub.1 to C.sub.8 alkyl radical, R.sup.3 is a linear, branched or cyclic C.sub.1 to C.sub.8 alkyl radical, a C.sub.5 to C.sub.7 2-oxocycloalkyl radical, or a linear or branched C.sub.3 to C.sub.8 2-oxoalkyl radical, and Y.sup.- represents a counter ion. The photoresist composition has high transparency to deep U.V. light having wavelengths of 220 nm or less and is capable of forming good fine patterns with high sensitivity, thus being useful as chemically amplified type resist which is exposed to the deep U.V. light from an ArF excimer laser.Type: GrantFiled: July 13, 1994Date of Patent: June 3, 1997Assignee: NEC CorporationInventors: Kaichiro Nakano, Katsumi Maeda, Shigeyuki Iwasa, Etsuo Hasegawa
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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: 5629095Abstract: The present invention relates to radiation curable silicone vinyl ethers and methods for preparing silicone vinyl ethers. More particularly, the present invention relates compositions containing vinyl ether functional silicones and to the preparation and use of silicone vinyl ethers which are curable by addition of photocleavable acids and exposure to ultraviolet or electron beam radiation.Type: GrantFiled: May 18, 1995Date of Patent: May 13, 1997Assignee: Dow Corning CorporationInventors: Valerie J. Bujanowski, Shedric O. Glover, Susan V. Perz, Maris J. Ziemelis, Gary R. Homan, Michael W. Skinner
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Patent number: 5629355Abstract: The invention is a polymeric photoinitiator having the formula: ##STR1## wherein n=10 to 50; each of a and b may be 0-4 while c is 0-5; A is an alkyl or aryl group; X is an anion; and each of R, R', and R" is independently H or one or more groups substituted onto the respective phenyl moieties. The substituted groups are independently selected from various kinds of groups excluding basic groups such as amino groups. Preferably, they are a hydrogen atom, halogen atom (e.g., F, Cl, Br, and I) , nitro group, alkoxy group (e.g. , CH.sub.3 O-- and C.sub.2 H.sub.5 O--) , C.sup.1 -C.sub.18 aliphatic group (e.g., hydrocarbon group such as CH.sub.3 --, C.sub.2 H.sub.5 --, and (CH.sub.3).sub.2 CH--; cyclic hydrocarbon group such as cyclohexyl group; and those which contain a heteroatom in the main chain or substituent group. The substituted groups may also be a C.sub.1 -C.sub.18 aliphatic group having at least one hydroxyl group or a C.sub.3 -C.sub.19 aliphatic group having a group of --OCH.sub.2 CH.sub.2 O--.Type: GrantFiled: May 29, 1996Date of Patent: May 13, 1997Assignee: International Business Machines CorporationInventor: Joseph P. Kuczynski
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Patent number: 5624787Abstract: A chemically amplified, positive resist composition contains a trifluoromethanesulfonic or p-toluenesulfonic acid bis- or tris(p-tert-butoxyphenyl)sulfonium salt and a nitrogenous compound. The composition is highly sensitive to high energy radiation, especially KrF excimer laser and has high sensitivity, resolution and plasma etching resistance while the resulting resist pattern is heat resistant.Type: GrantFiled: June 6, 1995Date of Patent: April 29, 1997Assignees: Shin-Etsu Chemical Co., Ltd., Nippon Telegraph and Telephone Corp.Inventors: Satoshi Watanabe, Katsuyuki Oikawa, Toshinobu Ishihara, Akinobu Tanaka, Tadahito Matsuda, Yoshio Kawai
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Patent number: 5624788Abstract: Disclosed are an organic silicon compound having a repeating unit represented by general formula (I) shown below, a resist, a thermal polymerization composition and a photopolymerization composition containing the organic silicon compound, ##STR1## wherein R.sup.1 is a t-butyl group or a tetrahydropyranyl group, R.sup.2 is an hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 1 to 24 carbon atoms, or a substituted or unsubstituted aralkyl having 7 to 24 carbon atoms, R.sup.3 is a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 24 carbon atoms or an alkoxyl group, and k represents an integer from 0 to 4.Type: GrantFiled: June 15, 1995Date of Patent: April 29, 1997Assignee: Kabushiki Kaisha ToshibaInventors: Shinji Murai, Yoshihiko Nakano, Ken Uchida, Shuji Hayase
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Patent number: 5624762Abstract: The present invention relates to compositions comprising vinyl ether functional siloxanes and aromatic iodonium salt or aromatic sulfonium salt photoinitiators which cure upon exposure to ultraviolet or electron beam radiation. The present invention further relates to use of these compositions in pressure sensitive release applications.Type: GrantFiled: May 18, 1995Date of Patent: April 29, 1997Assignee: Dow Corning CorporationInventors: Shedric O. Glover, Valeris J. Bujanowski, Maris J. Ziemelis, Michael W. Skinner, Gary R. Homan, Susan V. Perz, John P. Cannady
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Patent number: 5609992Abstract: A photopolymerizable composition is disclosed, comprising (i) a compound having at least one addition-polymerizable, ethylenically unsaturated bond; (ii) a compound represented by formula (IA) or (IB): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 each independently represents a hydrogen atom, a halogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, a hydroxyl group, a substituted oxy group, a mercapto group, a substituted thio group, an amino group, a substituted amino group, a substituted carbonyl group, a sulfo group, a sulfonato group, a substituted sulfinyl group, a substituted sulfonyl group, a phosphono group, a substituted phosphono group, a phosphonato group, a substituted phosphonato group, a cyano group or a nitro group or R.sup.1 and R.sup.2, R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.9 and R.sup.10, R.sup.10 and R.sup.11 or R.sup.11 and R.sup.Type: GrantFiled: October 27, 1995Date of Patent: March 11, 1997Assignee: Fuji Photo Film Co., Ltd.Inventors: Tadahiro Sorori, Yasuo Okamoto, Syunichi Kondo, Hiromichi Kurita
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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: 5594042Abstract: The present invention relates to compositions comprising vinyl ether functional siloxanes and aromatic iodonium salt or aromatic sulfonium salt photoinitiators which cure upon exposure to ultraviolet or electron beam radiation. The present invention further relates to use of these compositions in pressure sensitive release applications.Type: GrantFiled: August 17, 1994Date of Patent: January 14, 1997Assignee: Dow Corning CorporationInventors: Shedric O. Glover, Valeris J. Bujanowski, Maris J. Ziemelis, Michael W. Skinner, Gary R. Homan, Susan V. Perz, John P. Cannady
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Patent number: 5591562Abstract: A photopolymerizable composition suitable as a solder resist and capable of forming a resist film having characteristics in no way inferior to those of the conventional heat-curable type or organic solvent developed type solder resist, with the use of water or a dilute aqueous solution which is completely innocuous and higher in safety than the aqueous alkaline solution, and a method for producing a cured coated film pattern using the photopolymerizable composition.Type: GrantFiled: October 13, 1994Date of Patent: January 7, 1997Assignee: Sony CorporationInventors: Nobuo Komatsu, Ikuyo Kai, Nami Konishi, Naozumi Iwasawa, Satoru Furusawa
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Patent number: 5591783Abstract: An ultraviolet-curable silicone composition involving:(A) 100 parts by weight of a polyorganosiloxane comprising structural units represented by the general formula R.sup.1.sub.m R.sup.2.sub.n SiO.sub.(4-m-n)/2 ;(B) from 0.1 to 10 parts by weight of a polyorganosiloxane which is blocked by (OH)R.sup.3.sub.2 Si.sub. 1/2 at both ends or (b) an alcohol-modified polyorganosiloxane containing two or more alcoholic OH groups per molecule; and(C) a catalytically effective amount of an onium salt as a photoinitiator.Type: GrantFiled: February 9, 1995Date of Patent: January 7, 1997Assignee: Toshiba Silicone Co., Ltd.Inventors: Keiji Kobayashi, Roy M. Griswold
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Patent number: 5585219Abstract: A resist composition and a process for forming a resist pattern using a resist composition are disclosed. The present composition includes 100 parts by weight of a copolymer of a 2-norbornene-2-substituent unit and an acrylic acid ester unit of the formula I; ##STR1## wherein, X is a cyano or chloro group, R is tert-butyl, dimethylbenzyl, or tetrahydropyranyl, m is an integer of 9 to 2390, and n is an integer of 21 to 5180, and 1 to 20 parts by weight of a photo acid generator. A finely-resolved resist pattern with high sensitivity and good dry etch resistance is obtained by the present composition and present process for forming the resist pattern.Type: GrantFiled: May 10, 1995Date of Patent: December 17, 1996Assignee: Fujitsu LimitedInventors: Yuko Kaimoto, Koji Nozaki
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Patent number: 5583195Abstract: Epoxysilicone polymers partially or completely functionalized by a fluorescent, photo-sensitizing, or simultaneously fluorescing and photo-sensitizing substituent bonded to the silicone polymer by means of a carbon oxygen carbon bond provide fluorescent dye marking compounds for silicone compositions that are particularly useful in determining the quality of release coatings made therewith.Type: GrantFiled: September 29, 1995Date of Patent: December 10, 1996Assignee: General Electric CompanyInventor: Richard P. Eckberg
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Patent number: 5582672Abstract: A coated abrasive article comprises a backing, a first binder on the backing, and a plurality of abrasive particles in the first binder. The first binder is a hot melt pressure sensitive adhesive that is energy cured to provide a crosslinked coating. The invention also relates to a method of producing such articles.Type: GrantFiled: June 1, 1995Date of Patent: December 10, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: Gary J. Follett, Clayton A. George
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Patent number: 5580695Abstract: A chemically amplified resist comprising an alkali-soluble resin or a resin having at least one acid-dissociable group which is alkali-insoluble or -sprairingly soluble but becomes alkali-soluble upon dissociation of said acid dissociable group due to an acid; a radiation-sensitive, acid-generating agent; and an optional component in which resist, the radiation-sensitive, acid-generating agent generates an acid upon irradiation with a radiation in the irradiated portion and the solubility of the resin component and optional component in a developing solution is varied in the irradiated portion by a chemical reaction caused by the catalytic action of the acid, whereby a pattern is formed, characterized in that a compound having a nitrogen-containing basic group is contained in the resist.Type: GrantFiled: November 10, 1994Date of Patent: December 3, 1996Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Makoto Murata, Takao Miura, Yoshiji Yumoto, Toshiyuki Ota, Eiichi Kobayashi
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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: 5576461Abstract: The present invention provides a process for preparing a sulphoxonium salt from the corresponding sulphonium salt which comprises oxidising the sulphonium salt using a peracid, under basic conditions, in a solvent other than a ketone.Some of the sulphoxonium salts are new compounds.Type: GrantFiled: December 6, 1990Date of Patent: November 19, 1996Assignee: Ciba-Geigy CorporationInventors: Edward Irving, Robert J. Lunn, David A. Taylor, Alan H. Haines, John P. Innocenzi
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Patent number: 5576356Abstract: The invention provides a radiation curable release coating composition comprising:(a) about 1 to about 50 percent by weight of a cationically reactive polydiorganosiloxane liquid rubber having the following formula: ##STR1## wherein R are monovalent moieties which can be the same or different selected from the group consisting of alkyl, substituted alkyl, aryl, and substituted aryl wherein at least about 50% of the total number of silicon atoms have two methyl groups bonded thereto;E is an organic monovalent functional group comprising from about 1 to about 20 carbon atoms having at least one cationically co-reactive functional group;a and b both represent integers, wherein the sum of a plus b is an integer of about 10 to about 1200;b has a value ranging from about 0 to about 0.Type: GrantFiled: November 2, 1994Date of Patent: November 19, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: Charles M. Leir, William R. Berggren, William R. Bronn, David J. Kinning, Olester Benson, Jr.
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Patent number: 5569784Abstract: A novel sulfonium salt having at least one substituted aromatic group having acid labile groups and at least one nitrogenous aromatic group is provided. A chemically amplified, positive resist composition comprising the sulfonium salt as well as an alkali soluble resin and a dissolution inhibitor in an organic solvent has solved the PED problem.Type: GrantFiled: January 27, 1995Date of Patent: October 29, 1996Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Satoshi Watanabe, Junji Shimada, Youichi Ohsawa, Katsuya Takemura, Toshinobu Ishihara, Kazumasa Maruyama
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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: 5552260Abstract: Acid-sensitive polymers and imageable articles employing them are disclosed. In particular, photosensitive compositions are disclosed comprising: (a) a photoinitiator which generates an acid upon exposure to radiation; and (b) a polymer having acid labile groups pendant from the polymer backbone, said acid labile pendant groups comprising at least one each of A and B wherein A has the formula --T-(C.dbd.O)OCR.sup.1 R.sup.2 OR.sup.3, and B has the formula --T-(C.dbd.O)OR.sup.4 Si(R.sup.5).sub.3, wherein R.sup.1 and R.sup.2 each represent H or an alkyl group with the proviso that at least one of R.sup.1 and R.sup.2 must be hydrogen; R.sup.3 represents an alkyl group; or any two of R.sup.1, R.sup.2, and R.sup.3 may together form a ring group having from 3 to 36 carbon atoms; R.sup.5 represents an alkyl group, aryl group, an alkoxy group, an aryloxy group, an acyloxy group, or a trialkylsiloxy group; and R.sup.4 and T represents a divalent linking group wherein T is bonded to the polymer backbone and R.sup.Type: GrantFiled: November 16, 1994Date of Patent: September 3, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: Dennis E. Vogel, Leonard J. Stulc
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Patent number: 5550171Abstract: The invention is a polymeric photoinitiator having the formula: ##STR1## wherein n=10 to 50; each of a and b may be 0-4 while c is 0-5; A is an alkyl or aryl group; X is an anion; and each of R, R', and R" is independently H or one or more groups substituted onto the respective phenyl moieties. The substituted groups are independently selected from various kinds of groups excluding basic groups such as amino groups. Preferably, they are a hydrogen atom, halogen atom (e.g., F, Cl, Br, and I), nitro group, alkoxy group (e.g., CH.sub.3 O-- and C.sub.2 H.sub.5 O--), C.sup.1 -C.sub.18 aliphatic group (e.g., hydrocarbon group such as CH.sub.3 --, C.sub.2 H.sub.5 --, and (CH.sub.3).sub.2 CH--; cyclic hydrocarbon group such as cyclohexyl group; and those which contain a heteroatom in the main chain or substituent group. The substituted groups may also be a C.sub.1 -C.sub.18 aliphatic group having at least one hydroxyl group or a C.sub.3 -C.sub.19 aliphatic group having a group of --OCH.sub.2 CH.sub.2 O--.Type: GrantFiled: May 31, 1995Date of Patent: August 27, 1996Assignee: International Business Machines CorporationInventor: Joseph P. Kuczynski
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Patent number: 5543266Abstract: An active energy ray-curing resin composition comprises (i) a graft copolymerized polymer, (iii) an epoxy resin comprising at least one compound having one or more epoxy groups in the molecule and (iv) a polymerization initiator capable of generating a Lewis acid by irradiation of an active energy ray.Type: GrantFiled: March 13, 1995Date of Patent: August 6, 1996Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Munakata
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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: 5529886Abstract: The invention relates to monomers of the formulae R.sup.1 -SO.sub.2 -N(CO-OR.sup.2)-R3-O-CO-CR.sup.4 =CH.sub.2 and R.sup.1 -N(CO-OR.sup.2) -SO.sub.2 -R.sup.3 -O-CO-CR.sup.4 =CH.sub.2, in which R.sup.1 is a (C.sub.1 -C.sub.20)alkyl, (C.sub.3 -C.sub.10)cycloalkyl, (C.sub.6 -C.sub.14)aryl or (C.sub.7 -C.sub.20)aralkyl radical, individual methylene groups in the radicals containing alkyl being optionally replaced by heteroatoms, R.sup.2 is a (C.sub.3 -C.sub.11)alkyl, C.sub.3 -C.sub.11) alkenyl or (C.sub.7 -C.sub.11)aralkyl radical, R.sup.3 is an unsubstituted or substituted (C.sub.1 -C.sub.6)alkyl, (C.sub.3 -C.sub.6)cycloalkyl, (C.sub.6 -C.sub.14)aryl or (C.sub.7 -C.sub.20)aralkyl radical and R.sup.4 is a hydrogen atom or a methyl group. It further relates to polymers having at least 5 mol % of units with pendent groups of the formula(e) -R.sup.3 -N(CO-OR.sup.2)-SO.sub.2 -R.sup.1 (I) and/or -R.sup.3 -SO.sub.2 -N(CO-OR.sup.2)-R.sup.Type: GrantFiled: May 1, 1995Date of Patent: June 25, 1996Assignee: Hoechst AktiengesellschaftInventors: Mathias Eichhorn, Gerhard Buhr
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Patent number: 5525645Abstract: The present invention relates to a resin composition for optical molding which comprises (a) an actinic radical-curable and cationically polymerizable organic substance and (b) an actinic radiation-sensitive initiator for cationic polymerization. This composition can be cured without being affected by atmospheric oxygen.Type: GrantFiled: April 6, 1995Date of Patent: June 11, 1996Assignee: Asahi Denka Kogyo K.K.Inventors: Kazuo Ohkawa, Seiichi Saito
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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: 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: 5514728Abstract: Salts having a cationic portion of either a mono-, polyvent metal center, onium salts or organometallic salts and a nonnucleophilic anion are useful as catalysts and initiators that may be photochemically or thermally-activated, and polymerizable compositions containing such catalysts and initiator salts and at least one of a cationic or free-radical addition polymerizable monomers, or catalyzed step-growth polymerizable monomers.Type: GrantFiled: July 23, 1993Date of Patent: May 7, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: William M. Lamanna, Michael C. Palazzotto, Robert J. DeVoe, Fred B. McCormick, Jeffrey M. Olofson, Allen R. Siedle, Peggy S. Willett
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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: 5512605Abstract: Epoxysilicone polyether block copolymers, when combined with certain sulfonium photocatalysts, provide one-component shelf-stable UV curable compositions. Non-polyether containing epoxy silicones form one part UV curable compositions with sulfonium salt solubilized in the presence of fluoroalcohols.Type: GrantFiled: December 28, 1994Date of Patent: April 30, 1996Assignee: General Electric CompanyInventors: Richard P. Eckberg, Michael J. O'Brien
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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: 5496678Abstract: A photosensitive composition which comprises, as essential components:(A) a polymer having carboxyl group(s) and hydroxyphenyl group(s), or (A') a polymer having carboxyl group(s) and (A") a polymer having hydroxyphenyl group(s),(B) a compound having at least two vinyl ether groups in the molecule, and(C) a compound which generates an acid when irradiated with an actinic ray, and which is useful as a positive type photoresist having high resolution and excellent formability of fine image pattern, a material for printing, etc.; and a process for pattern formation using said composition.Type: GrantFiled: April 14, 1994Date of Patent: March 5, 1996Assignee: Kansai Paint Co., Ltd.Inventors: Genji Imai, Naozumi Iwasawa, Tsuguo Yamaoka
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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: 5486422Abstract: The invention is concerned with silicone copolymer containing terminal and/or pendant oxyalkylene styrene groups which are crosslinkable in the presence of a photoinitiator when exposed to UV radiation and their use in a compositions for coating substrates to provide substrates with anti-adhesive properties.Type: GrantFiled: April 17, 1995Date of Patent: January 23, 1996Assignee: Dow Corning CorporationInventors: Bernard J. L. Boutevin, Latifa Abdellah, Gerardo Caporiccio
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Patent number: 5486545Abstract: Propenyl ether monomers of formula VA(OCH.dbd.CHCH.sub.3).sub.nwherein n is an integer from one to six and A is selected from cyclic ethers, polyether and alkanes are disclosed. The monomers are readily polymerized in the presence of cationic photoinitiators, when exposed to actinic radiation, to form poly(propenyl ethers) that are useful for coatings, sealants, varnishes and adhesives. Compositions for preparing polymeric coatings comprising the compounds of formula V together with particular cationic photoinitiators are also disclosed, as are processes for making the monomers from allyl halides and readily available alcohols. The process involves rearranging the resulting allyl ethers to propenyl ethers.Type: GrantFiled: April 25, 1994Date of Patent: January 23, 1996Assignee: Rensselaer Polytechnic InstituteInventor: James V. Crivello
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Patent number: 5482816Abstract: A radiation-sensitive composition comprising (A) a polymer having a recurring unit represented by formula (1): ##STR1## wherein R.sup.1 represents a substituted methyl group, a substituted ethyl group, a silyl group, a germyl group or an alkoxycarbonyl group, and R.sup.2 represents --OR.sup.3 or --NR.sup.4 R.sup.5 in which R.sup.3 is a hydrogen atom, a straight-chain alkyl group, a cyclic alkyl group, an aryl group, an aralkyl group, a substituted methyl group, a substituted ethyl group, a silyl group, a germyl group or an alkoxycarbonyl group, and R.sup.4 and R.sup.5, which may be the same or different, are hydrogen atoms, straight-chain alkyl groups, cyclic alkyl groups, aralkyl groups or aryl groups, and (B) a radiation-sensitive acid forming agent.Type: GrantFiled: June 21, 1994Date of Patent: January 9, 1996Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Makoto Murata, Mikio Yamachika, Yoshiji Yumoto, Takao Miura
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Patent number: 5476752Abstract: An active energy ray-curing resin composition comprises:(i) a linear polymer having a glass transition temperature of 50.degree. C. or higher and a weight average molecular weight of about 3.0.times.10.sup.4 or higher;(ii) a monomer having an ethylenically unsaturated bond;(iii) an epoxy resin comprising at least one compound having one or more epoxy groups in the molecule; and(iv) a polymerization initiator capable of generating a Lewis acid by irradiation with an active energy ray.Type: GrantFiled: April 3, 1995Date of Patent: December 19, 1995Assignee: Canon Kabushiki KaishaInventors: Hiromichi Noguchi, Tadayoshi Inamoto, Megumi Munakata
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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: 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: 5449588Abstract: A photosensitive resin composition containing 0.5 to 15 parts by weight of a compound generating an acid by light irradiation in 100 parts by weight of a polyamic acid amide having an alkoxysilane having a specified structure at its terminals are provided,which composition has superior resolution properties, a small shrinkage of volume, a superior adhesion onto a substrate, and can prepare a polyimide by baking.Type: GrantFiled: May 27, 1994Date of Patent: September 12, 1995Assignee: Chisso CorporationInventors: Hirotoshi Maeda, Eiji Watanabe, Kouichi Katou, Kouichi Kunimune
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Patent number: 5439766Abstract: According to the present invention, good image resolution of a cationically polymerized epoxy based coating, such as a solder mask or dielectric or etch resist, is provided by combining a cationically polymerized epoxy based coating with conventional epoxy glass substrates cured with a curing agent that does not produce basic reaction products. Preferably, the coating is photoimagable. The method for making the same is also provided. The coating material includes an epoxy resin system comprising between from about 10% to about 90%, preferably about 28% to about 57% by weight of a polyol epoxy resin, and from about 10% to about 90%, preferably about 43% to 72% by weight, of a brominated epoxy resin. Optionally, a polyepoxy resin or an epoxy creosol novolak resin is added to the resin system. The polyepoxy resin may be added from an effective amount up to less than 90% of the resin system; the epoxy creosol novolak may be added from an effective amount up to about 80 pph.Type: GrantFiled: November 13, 1992Date of Patent: August 8, 1995Assignee: International Business Machines CorporationInventors: Richard A. Day, Donald H. Glatzel, John R. Mertz, Joel L. Roth, David J. Russell, Logan L. Simpson
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Patent number: 5439779Abstract: The present invention provides a photoimageable soldermask that may be applied using aqueous solvents, thereby reducing the emission of organic solvents. The soldermask contains an epoxy based resin system comprised of at least one epoxy resin, a coating agent, and preferably a cationic photoinitiator and a dye.Type: GrantFiled: June 13, 1994Date of Patent: August 8, 1995Assignee: International Business Machines CorporationInventors: Richard A. Day, Donald H. Glatzel, David J. Russell, Jeffrey D. Gelorme, John R. Mertz
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Patent number: 5436309Abstract: The invention is concerned with silicone copolymer containing terminal and/or pendant oxyalkylene styrene groups which are crosslinkable in the presence of a photoinitiator when exposed to UV radiation and their use in a compositions for coating substrates to provide substrates with anti-adhesive properties.Type: GrantFiled: April 19, 1994Date of Patent: July 25, 1995Assignee: Dow Corning CorporationInventors: Bernard J. L. Boutevin, Latifa Abdellah, Gerardo Caporiccio
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Patent number: 5411996Abstract: Epoxysilicone polyether block copolymers, when combined with certain sulfonium photocatalysts, provide one-component shelf-stable UV curable compositions. Non-polyether containing epoxy silicones form one part UV curable compositions with sulfonium salt solubilized in the presence of fluoroalcohols.Type: GrantFiled: June 25, 1992Date of Patent: May 2, 1995Assignee: General Electric CompanyInventors: Richard P. Eckberg, Michael J. O'Brien
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Patent number: 5409963Abstract: A silicone composition capable of being cured by both a moisture-curing mechanism and an ultraviolet (UV) curing mechanism is provided. The silicone composition comprises:1 a reactive organosiloxane prepared by a condensation reaction of a silicone (1) represented by the general formula ##STR1## where R.sup.1 and R.sup.2 are each an organo group, and a is a number corresponding to a kinematic viscosity of 25-50,000 cSt, measured at 25.degree. C., with a vinyl ether silane compound represented by the general formula: ##STR2## where m and n are each an integer of 1 to 5, R.sup.3 and R.sup.4 are each an alkyl group having 1 to 3 carbon atoms or allyl, and b is 0 or 1;2 0-70 parts by weight of a silicone oil having trimethylsilyl group as an end group;3 a catalytic amount of a photopolymerization catalyst; and4 a catalytic amount of a silicone moisture-curing catalyst.Type: GrantFiled: December 28, 1993Date of Patent: April 25, 1995Assignee: Three Bond Co., Ltd.Inventor: Toru Takfoka