Carbonyl In Heterocyclic Compound Patents (Class 430/924)
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Patent number: 9005871Abstract: Compounds of the formula (I), wherein Ar1 is for example phenylene or biphenylene both unsubstituted or substituted; Ar2 and Ar3 are for example independently of each other phenyl, naphthyl, biphenylylyl or heteroaryl, all optionally substituted; or Ar1 and Ar2 for example together with a direct bond, O, S or (CO), form a fused ring system; R is for example hydrogen, C3-C30cycloalkyl or C1-C18alkyl; and R1, R2 and R3 independently of each other are for example C1-C10haloalkyl; are effective photoacid generators (PAG).Type: GrantFiled: October 8, 2009Date of Patent: April 14, 2015Assignee: BASF SEInventors: Hitoshi Yamato, Toshikage Asakura, Yuichi Nishimae
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Patent number: 8956799Abstract: A photoacid generator includes those of formula (I): wherein each Ra in formula 1 is independently H, F, a C1-10 nonfluorinated organic group, C1-10 fluorinated organic group, or a combination comprising at least one of the foregoing, provided at least one Ra is F or a C1-10 fluorinated organic group, the C1-10 fluorinated and nonfluorinated organic groups each optionally comprising O, S, N, or a combination comprising at least one of the foregoing heteroatoms; L1 is a linking group comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing; G+ is an onium salt of the formula (II): wherein in formula (II), X is S or I, each R0 is independently C1-30 alkyl group; a polycyclic or monocyclic C3-30 cycloalkyl group; a polycyclic or monocyclic C4-30 aryl group; or a combination comprising at least one of the foregoing, provided at least one R0 is substituted where each R0 is a C6 monocyclic aryl group, and wherein when X is I, a is 2, and where X is S, a is 3,Type: GrantFiled: December 12, 2012Date of Patent: February 17, 2015Assignee: Rohm and Haas Electronic Materials LLCInventors: Emad Aqad, Cheng-Bai Xu, Mingqi Li, William Williams, III
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Patent number: 8557500Abstract: The present invention provides a salt represented by the formula (I): wherein Q1 and Q2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents a C1-C17 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, L2 represents a single bond or a C1-C6 alkanediyl group in which one or more —CH2— can be replaced by —O— or —CO—, Y represents a C3-C18 alicyclic hydrocarbon group which can have one or more substituents, and one or more —CH2— in the alicyclic hydrocarbon group can be replaced by —O—, —CO— or —SO2—, and Z+ represents an organic counter ion.Type: GrantFiled: February 28, 2012Date of Patent: October 15, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Hiromu Sakamoto, Takahiro Yasue
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Patent number: 8435717Abstract: A sulfonic acid onium salt represented by the following formula (1) can be used as a superior radiosensitive acid generator for resist compositions. It is possible to form a good pattern by using a resist composition containing this sulfonic acid onium salt. In formula (1), R1 represents a monovalent organic group, and Q+ represents a sulfonium cation or iodonium cation.Type: GrantFiled: February 14, 2008Date of Patent: May 7, 2013Assignee: Central Glass Company, LimitedInventors: Yuji Hagiwara, Jonathan Joachim Jodry, Satoru Narizuka, Kazuhiko Maeda
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Patent number: 8278030Abstract: An object of the present invention is to provide a sulfonium salt that has sufficient photosensitivity by active energy rays, such as visible light, ultraviolet rays, electron beams, and X-rays. The present invention is a sulfonium salt represented by formula (1). It is noted that R1 is a group represented by formula (2); R2 and R3 each represent an aryl group having 6 to 30 carbon atoms, a heterocyclic hydrocarbon group having 4 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, or an alkynyl group having 2 to 30 carbon atoms; X? represents a monovalent polyatomic anion; R4 to R6 each represent an alkyl group, or the like; k represents an integer of 0 to 4; m represents an integer of 0 to 3; n represents an integer of 0 to 4; and A represents a group represented by —S—, —O—, —SO—, —SO2—, or —CO—.Type: GrantFiled: April 27, 2009Date of Patent: October 2, 2012Assignee: San-Apro LimitedInventors: Issei Suzuki, Hideki Kimura
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Patent number: 8048613Abstract: An alkali development-type solder resist includes (A) a carboxyl group-containing photosensitive resin obtained by reacting (a) a compound having two or more cyclic ether or thioether groups in the molecule with (b) an unsaturated monocarboxylic acid, reacting the product with (c) a polybasic acid anhydride, reacting the resulting resin with (d) a compound having a cyclic ether group and an ethylenic unsaturated group in the molecule, and reacting the product additionally with (c) a polybasic acid anhydride, (B) an oxime ester-based photopolymerization initiator containing a specific oxime ester group, (C) a compound having two or more ethylenic unsaturated groups in the molecule, and (D) a thermosetting component, wherein the dry film obtained by applying the composition has an absorbance of 0.3 to 1.2 per 25 ?m of the film thickness at a wavelength of 350 to 375 nm.Type: GrantFiled: October 13, 2008Date of Patent: November 1, 2011Assignee: Taiyo Ink Mfg. Co., Ltd.Inventors: Nobuhito Itoh, Yoko Shibasaki, Kenji Kato, Masao Arima
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Patent number: 8021823Abstract: There is provided a positive resist composition, including a base component (A) which exhibits increased solubility in an alkali developing solution under action of an acid, and an acid generator component (B) which generates an acid upon exposure, wherein the base component (A) includes a polymeric compound (A1) containing a structural unit (a0) represented by the general formula (a0-1) shown below: (wherein, R1 represents a hydrogen atom, a lower alkyl group or a halogenated lower alkyl group; A represents a bivalent linking group; B represents a bivalent linking group; and R2 represents an acid dissociable, dissolution inhibiting group).Type: GrantFiled: February 18, 2009Date of Patent: September 20, 2011Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hiroaki Shimizu, Tsuyoshi Nakamura, Takahiro Dazai, Daiju Shiono, Tomoyuki Hirano
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Patent number: 7927780Abstract: A compound represented by formula (I); and a compound represented by formula (b1-1): wherein X represents —O—, —S—, —O—R3— or —S—R4—, wherein each of R3 and R4 independently represents an alkylene group of 1 to 5 carbon atoms; R2 represents an alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms, a halogenated alkyl group of 1 to 6 carbon atoms, a halogen atom, a hydroxyalkyl group of 1 to 6 carbon atoms, a hydroxyl group or a cyano group; a represents an integer of 0 to 2; Q1 represents an alkylene group of 1 to 12 carbon atoms or a single bond; Y1 represents an alkylene group of 1 to 4 carbon atoms or a fluorinated alkylene group; M+ represents an alkali metal ion; and A+ represents an organic cation.Type: GrantFiled: September 10, 2008Date of Patent: April 19, 2011Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Akiya Kawaue, Takeshi Iwai, Hideo Hada, Shinichi Hidesaka, Tsuyoshi Kurosawa, Natsuko Maruyama, Kensuke Matsuzawa, Takehiro Seshimo, Hiroaki Shimizu, Tsuyoshi Nakamura
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Patent number: 7560219Abstract: Sulfonium salt photoinitiator compositions, precursors useful in the preparation of such photoinitiators and the use of these photoinitiators in, e.g., UV curable adhesives, UV curable sealants, UV curable coating compositions, such as printing inks and varnishes, and UV curable encapsulants.Type: GrantFiled: April 26, 2007Date of Patent: July 14, 2009Assignee: Henkel AG & Co. KGaAInventors: Yuxia Liu, Donald E. Herr
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Patent number: 7378223Abstract: The invention provides photoresist resin compositions and in particular, a photoresist resin compositions comprising a) an acrylate monomer having two urethane bonds, b) a crosslinkable urethane monomer having at least two ethylene double bonds, c) an alkali-soluble compound, d) a photopolymerization initiator and e) a solvent, and a photoresist dry film resists using the photoresist resins. The photoresist resin compositions and the photoresist dry film resists using the same in accordance with the invention have excellent adhesion to a substrate and sandblast resistance and at the same time, they have high sensitivity as well as high resolution, thereby enabling fine pattern formation on substrates.Type: GrantFiled: May 6, 2005Date of Patent: May 27, 2008Assignee: Dongjin Semichem, Co., Ltd.Inventors: Bong-gi Kim, Sung-mun Ryu, Seong-mo Park, Chan-seok Park
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Patent number: 7232647Abstract: The present invention provides a photosensitive resin composition for laser scanning exposure, which satisfies the following formula (1): - 25 ? E 1 - E 0 E 0 × 100 ? 25 ( 1 ) wherein E0 represents an exposure amount in mJ/cm2 at which the photosensitive resin composition is cured at the 21st step of the density 1.00 of a 41-step step tablet having a density range from 0.00 to 2.00, a density step of 0.05, a tablet size of 20 mm×187 mm and a step size of 3 mm×12 mm, by irradiation with a full wavelength active light of a high pressure mercury lamp and E1 represents an exposure amount in mJ/cm2 at which the photosensitive resin composition after being left for 2 hours under 40 W non-ultraviolet white lamp is cured at the 21st step of the 41-step step tablet by irradiation with a full wavelength active light from a high pressure mercury lamp.Type: GrantFiled: March 21, 2005Date of Patent: June 19, 2007Assignee: Hitachi Chemical Co., Ltd.Inventors: Yasuhara Murakami, Takahiro Hidaka
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Publication number: 20040241569Abstract: A chemically-amplified resist composition is disclosed, which comprises a polymer of formula (I) below: 1Type: ApplicationFiled: May 28, 2003Publication date: December 2, 2004Applicant: Everlight USA, Inc.Inventors: Chi-Sheng Chen, Chan-Chan Tsai, Bin Jian, Hsin-Ming Liao
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Patent number: 6818375Abstract: Disclosed are photoimageable compositions having improved stripping properties including a photoresist strip enhancer. Also disclosed are methods of enhancing the strippability of photoimageable compositions and methods for manufacturing printed wiring boards using such photoimageable compositions.Type: GrantFiled: November 28, 2001Date of Patent: November 16, 2004Assignee: Eternal Technology CorporationInventors: Thomas A. Koes, Todd Johnson
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Patent number: 6800420Abstract: A photosensitive thick film composition. The photosensitive thick film composition can produce electrode material with high resolution and high contrast. The photosensitive thick film composition includes an acrylic copolymer, a photoinitiator, a reactive monomer, a conductive metal, glass powder, an additive, and an organic solvent.Type: GrantFiled: December 4, 2002Date of Patent: October 5, 2004Assignee: Industrial Technology Research InstituteInventors: Tsing-Tang Song, Weir-Torn Jiang, Shung-Jim Yang, Sheng-Min Wang, Kom-Bei Shiu
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Publication number: 20040067431Abstract: A photoreactive composition comprises (a) at least one reactive species that is capable of undergoing an acid- or radical-initiated chemical reaction; and (b) a photoinitiator system comprising photochemically-effective amounts of (1) at least one type of semiconductor nanoparticle quantum dot that has at least one electronic excited state that is accessible by absorption of two or more photons, and (2) a composition, different from said reactive species, that is capable of interacting with the excited state of the semiconductor nanoparticle quantum dot to form at least one reaction-initiating species.Type: ApplicationFiled: October 2, 2002Publication date: April 8, 2004Applicant: 3M Innovative Properties CompanyInventors: David S. Arney, Catherine A. Leatherdale, Manoj Nirmal
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Publication number: 20030013037Abstract: Photoresist monomers, photoresist polymers prepared thereof, and photoresist compositions using the polymer are disclosed. More specifically, photoresist polymers comprising maleimide monomer represented by Formula 1, and a composition comprising the polymer thereof are disclosed. The photoresist composition has excellent etching resistance, heat resistance and adhesiveness, and can be developed in an aqueous tetramethylammonium hydroxide (TMAH) solution. As the composition has low light absorbance at 193 nm and 157 nm wavelength, and it is suitable for a process using ultraviolet light source such as VUV (157 nm).Type: ApplicationFiled: February 21, 2002Publication date: January 16, 2003Inventors: Geun Su Lee, Jae Chang Jung, Min Ho Jung, Cha Won Koh, Ki Soo Shin
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Publication number: 20020168584Abstract: A positive resist composition comprises: (A) a resin capable of decomposing by the action of an acid to increase the solubility in an alkali developer; and (B) a compound capable of generating an acid upon irradiation with one of an actinic ray and a radiation, wherein the resin (A) contains a specified repeating unit.Type: ApplicationFiled: March 19, 2002Publication date: November 14, 2002Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Toshiaki Aoai, Kazuyoshi Mizutani, Shinichi Kanna
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Patent number: 6280905Abstract: A photosensitive resin composition which comprises (1) a particulate copolymer comprising 10-99.8% by mole of the unit of (i) an aliphatic conjugated diene monomer, 0.1-30% by mole of the unit of (ii) a monomer having one polymerizable unsaturated group and an amino group, 0.1-20% by mole of the unit of (iii) a monomer having at least two polymerizable unsaturated groups and 0-40% by mole of the unit of (iv) a copolymerizable other monomer having one polymerizable unsaturated group, (2) a photopolymerizable unsaturated monomer and (3) a photopolymerization initiator typically represented by 9-fluorenone or 2-i-propylthioxanthone. A photosensitive resin composition is provided which can be developed by using water, has a low hardness and high resilience, and is excellent in balance of properties.Type: GrantFiled: April 21, 2000Date of Patent: August 28, 2001Assignee: JSR CorporationInventors: Katsuo Koshimura, Tsukasa Toyoshima, Takashi Nishioka, Tadaaki Tanaka
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Patent number: 6110646Abstract: A positive photosensitive composition comprising an alkali-soluble organic high molecular substance having phenolic hydroxyl groups and an acid color forming dye.Type: GrantFiled: August 13, 1998Date of Patent: August 29, 2000Assignee: Mitsubishi Chemical CorporationInventors: Toshiyuki Urano, Etsuko Hino
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Patent number: 5985511Abstract: A positive photoresist composition having excellent various performances (e.g. resolution, resistance to time delay effect, profile), small PEB dependence as well as excellent sensitivity, film retention and coatability, which comprises a polyvinylphenol resin whose phenolic hydroxyl group is partially protected; a sulfonate of a N-hydroxyimide compound as an acid generator; an amine compound; and an electron donor having a redox potential of not more than 1.7 eV is provided.Type: GrantFiled: December 12, 1996Date of Patent: November 16, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Yuko Yako, Naoki Takeyama, Kenji Takahashi
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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: 5811218Abstract: An N-aryl-.alpha.-amino acid (I), which is a novel compound, is effective as a photoinitiator. The photoinitiator composition including this photoinitiator is effective for improving photosensitive properties of photosensitive materials containing poly(amic acid) and an addition polymerizable compound used for pattern formation. Further, a photoinitiator composition (A) comprising an N-aryl-.alpha.-amino acid (I) or (I'), a 3-substituted coumarin (II) and/or an azabenzalcyclohexanone (III), or a photoinitiator composition (B) comprising an N-aryl-.alpha.-amino acid (I) or (I'), a 3-substituted coumarin (II) and a titanocene (IV), or a photoinitiator composition (C) comprising a 3-substituted coumarin (II), a titanocene (IV) and an oxime ester (V), is effective for improving photosensitive properties of photosensitive materials containing poly(amic acid) and an addition polymerizable compound used for pattern formation.Type: GrantFiled: July 17, 1995Date of Patent: September 22, 1998Assignee: Hitachi Chemical Company, Ltd.Inventors: Makoto Kaji, Yasunori Kojima, Shigeki Katogi, Masataka Nunomura, Hideo Hagiwara, Dai Kawasaki, Mitsumasa Kojima, Hiroshi Suzuki, Hidetaka Satou
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Patent number: 5770345Abstract: 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: July 16, 1996Date of Patent: June 23, 1998Assignee: International Business Machines CorporationInventors: Edward Darko Babich, Karen Elizabeth Petrillo, John Patrick Simons, David Earle Seeger
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Patent number: 5753412Abstract: 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-l,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: June 5, 1996Date of Patent: May 19, 1998Assignee: International Business Machines CorporationInventors: Edward Darko Babich, Karen Elizabeth Petrillo, John Patrick Simons, David Earle Seeger
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Patent number: 5723260Abstract: An unsaturated group-containing urethane compound of the following formula (I): ##STR1## wherein X is a C.sub.1-20 alkylene group which may be branched, and R.sup.1 is a group of the following structural formula (A) or (B): ##STR2## wherein each of R.sup.2 and R.sup.3 which are independent of each other, is a hydrogen atom or a methyl group, and Y is a C.sub.1-6 alkylene group which may be branched.Type: GrantFiled: September 17, 1996Date of Patent: March 3, 1998Assignee: Mitsubishi Chemical CorporationInventors: Shigeo Tsuji, Hiroshi Tomiyasu
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Patent number: 5627006Abstract: A photoresist composition comprising (a) a difficultly alkali-soluble special resin, (b) a photo-sensitive compound capable of generating a carboxylic acid, and (c) a solvent, is effective for pattern formation using deep ultraviolet light, KrF excimer laser beams, etc.Type: GrantFiled: April 18, 1995Date of Patent: May 6, 1997Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.Inventors: Fumiyoshi Urano, Keiji Oono, Hirotoshi Fujie
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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: 5585218Abstract: A negative or positive photoresist composition which comprises an alkali soluble resin containing at least one resin selected from the group consisting of a partially alkyletherified polyvinylphenol and a partially alkyletherified hydrogenated polyvinylphenol, a photo-induced acid precursor containing at least a kind of sulfonic acid ester of N-hydroxyimide compounds and crosslinking agent or dissolution inhibitor, and this photoresist composition is excellent in various properties such as heat resistance, film thickness retention, coating property, profile and the like, and further exhibits high sensitivity and high resolution when far ultraviolet rays including excimer laser is used as the light source. It also hardly cause a scam during the developing process.Type: GrantFiled: May 25, 1994Date of Patent: December 17, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Yuko Nakano, Naoki Takeyama, Yuji Ueda, Takehiro Kusumoto, Hiromi Oka
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Patent number: 5415976Abstract: Aminoketone-substituted coumarin sensitizers having tethered tertiary amino groups are described which have extremely good photosensitivity. The sensitizers of the instant invention have the formula: ##STR1## wherein R.sub.1 and R.sub.2 each represent an alkyl group having 1 to 6 carbon atoms, and R.sub.3 and R.sub.4 each represent hydrogen; or at least one of R.sub.1 and R.sub.3 or R.sub.2 and R.sub.4 together represent an alkylene group having 2 to 4 carbon atoms,R.sub.5 represents an alkyl group having 1 to 6 carbon atoms or H,R.sub.6 represents an alkylene group having 1 to 6 carbon atoms, andR.sub.7 and R.sub.8 each independently represent an alkyl group having 1 to 6 carbon atoms, both of R.sub.7 and R.sub.8 taken together represent an alkylene group having 4 to 6 carbon atoms, or R.sub.5 or R.sub.6 taken together with R.sub.7 or R.sub.8 represent a five, six, or seven membered heterocyclic ring group.Type: GrantFiled: April 28, 1994Date of Patent: May 16, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventor: M. Zaki Ali
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Patent number: 5286603Abstract: A radiation sensitive plate comprises a substrate coated with a photopolymerisable composition. The composition comprises a polymerisable compound containing ethylenic unsaturation, a perester photoinitiator and optionally an optical sensitiser. The substrate may be a sheet of grained and anodised aluminum and the plate is useful in the production of lithographic printing plates.Type: GrantFiled: June 3, 1992Date of Patent: February 15, 1994Assignee: Vickers PLCInventors: John R. Wade, Rodney M. Potts, Michael J. Pratt
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Patent number: 5256520Abstract: Photopolymerizable compositions containing photoinitiator systems that absorb in the visible are disclosed. The photopolymerizable compositions contain at least one ethylenically unsaturated monomer capable of free radical initiated addition polymerization and a photoinitiator system capable of being activated by actinic radiation. The photoinitiator system comprises a hexaarylbisimidazole, a chain transfer agent, and a sensitizer given by the formulae A or B wherein X and R.sub.1 -R.sub.13 are as defined herein.Type: GrantFiled: November 10, 1992Date of Patent: October 26, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: William K. Smothers
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Patent number: 5236808Abstract: Photopolymerizable compositions containing photoinitiator systems that absorb in the visible are disclosed. The photoinitiator system comprises a sensitizer which is a compound of the structure I: ##STR1## wherein R.sub.2 and R.sub.Type: GrantFiled: April 13, 1992Date of Patent: August 17, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: William K. Smothers
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Patent number: 5141841Abstract: A radiation-sensitive compound has the general formula ##STR1## wherein A represents the ring members required to complete a 5- or 6-membered heterocyclic ring which may optionally be fused to an optionally substituted aromatic nucleus,B represents H, acyl, aroyl, heterocyclyl carbonyl or ##STR2## R represents an optionally substituted alkyl group, E and G, which may be the same or different, each represents H or CH.sub.p X.sub.3-p,J and K, which may be the same or different, each represents an aryl or heterocyclic group, which may optionally include a substituent additional to E or G,X represents Cl or Br, and m,n and p, which may be the same or different, each represents an integer equal to 0, 1 or 2.The compound can be used to form radiation sensitive compositions for the production of radiation sensitive plates in lithographic printing plate manufacture.Type: GrantFiled: August 17, 1989Date of Patent: August 25, 1992Assignee: Vickers PLCInventor: John R. Wade
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Patent number: 5130227Abstract: A radiation sensitive plate comprises a substrate coated with a photopolymerizable composition. The composition comprises a polymerizable compound containing ethylenic unsaturation, a perester photoinitiator and optionally an optical sensitiser. The substrate may be a sheet of grained and anodized aluminum and the plate is useful in the production of lithographic printing plates.Type: GrantFiled: October 5, 1989Date of Patent: July 14, 1992Assignee: Vickers PlcInventors: John R. Wade, Rodney M. Potts, Michael J. Pratt
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Patent number: 5091282Abstract: This invention includes a photosensitive composition containing an alkali-soluble resin and a compound represented by formula (I), (II) or (III) described in the claims and the specification, a photosensitive composition containing an alkali-soluble polymer, a compound represented by formula (IV) described in the claims and the specification and a basic compound, and a photosensitive composition containing an alkali-soluble polymer, a compound represented by formula (VI) described in the claims and the specification and a compound which produces an acid upon radiation of light.Type: GrantFiled: April 3, 1990Date of Patent: February 25, 1992Assignee: Kabushiki Kaisha ToshibaInventors: Yasunobu Onishi, Hirokazu Niki, Yoshihito Kobayashi, Rumiko Hayase, Toru Ushirogouchi
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Patent number: 5011755Abstract: The present invention relates to compositions comprising(a) a titanocene photoinitiator of the formula I ##STR1## (b) a 3-ketocoumarin of the formula II ##STR2## in which both R.sup.1, R.sup.2 and R.sup.3 are as defined in claim 1, R.sup.4 is a radical of the formula V ##STR3## R.sup.5 is C.sub.1 -C.sub.20 alkyl, cycloalkyl having 5-7 ring carbon atoms, phenyl or naphthyl which are unsubstituted or substituted by one to three C.sub.1 -C.sub.6 alkyl groups, C.sub.1 -C.sub.6 alkoxy groups or halogen atoms or by one diphenylamino or C.sub.1 -C.sub.6 dialkylamino group, or is C.sub.7 -C.sub.9 aralkyl, a radical --(CH.dbd.CH).sub.a --C.sub.6 H.sub.5 or a radical of the formula V, a is 1 or 2, preferably 1, and R.sup.10, R.sup.11, R.sup.12, R.sup.13 and R.sup.14 independently of one another are hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, phenyl, tolyl, xylyl or benzyl, and R.sup.11 can additionally also be a group --NR.sup.15 R.sup.16 or --OR.sup.15, wherein R.sup.15 and R.sup.Type: GrantFiled: January 30, 1990Date of Patent: April 30, 1991Assignee: Ciba-Geigy CorporationInventors: Ottmar Rohde, Armin Schaffner, Martin Riediker, Kurt Meier
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Patent number: 4987057Abstract: A photoinitiator composition comprising (1) an aminobenzylidene carbonyl compound and (2) an N-aryl-.alpha.-amino acid is suitable for use in a photo-polymerizable composition comprising (a) an addition-polymerizable compound having a boiling point of 100.degree. C. or higher at an atmospheric pressure and (b) said photoinitiator composition.Type: GrantFiled: May 22, 1989Date of Patent: January 22, 1991Assignee: Hitachi Chemical Co., Ltd.Inventors: Makoto Kaji, Nobuyuki Hayashi
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Patent number: 4948694Abstract: A recording medium comprising a substrate and a transfer recording layer containing a photo-initiator comprising camphorquinone and a coumarin derivative. Such photo-initiator aids in realizing high sensitivity without lowering storage stability of the recording medium. The transfer recording layer causes a change in transfer characteristic when provided with light energy and heat energy, at least one of which is applied imagewise, to provide a transferable portion therein. The transferable portion is then transferred to a transfer-receiving medium such as plain paper to form a transferred image thereon.Type: GrantFiled: September 11, 1989Date of Patent: August 14, 1990Assignee: Canon Kabushiki KaishaInventors: Norio Ohkuma, Masanori Takenouchi, Masashi Miyagawa, Hiroshi Hayashi, Tooru Minami, Hiroharu Oobayashi
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Patent number: 4935330Abstract: A photopolymerizable mixture containing one or more ethylenically unsaturated, photopolymerizable or photocrosslinkable compounds and a photopolymerization initiator which comprises a combination of an aromatic carbonyl compound of the type stated in claim 1 and an s-triazine compound containing one or more halogen-substituted methyl groups, photosensitive recording elements which possess a photopolymerizable recording layer consisting of these photopolymerizable mixtures, and a process for the production of lithographic printing plates using these recording elements.Type: GrantFiled: November 14, 1989Date of Patent: June 19, 1990Assignee: BASF AktiengesellschaftInventors: Gerhard Hofmann, Reiner Hoffman, Harald Lauke, Wilhelm Weber, Reinhold J. Leyrer
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Patent number: 4923781Abstract: A photopolymerizable composition comprises a polyfunctional monomer, a photopolymerization initiator, an organic halogen compound and a 3,6-diaminofluoran derivative. The 3,6-diaminofluoran has the formula (I): ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 is hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an aryl group or a heterocyclic group, R.sup.1 and R.sup.2 (also R.sup.3 and R.sup.4 may form a heterocyclic ring in conjunction with the adjoining nitrogen atom, provided that at least two of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are aryl groups, or at least one group of the group containing R.sup.1 and R.sup.2 and the group containing R.sup.3 and R.sup.4 forms in conjunction with the adjoining nitrogen atom a heterocyclic ring; each of R.sup.5, R.sup.6 and R.sup.Type: GrantFiled: October 23, 1989Date of Patent: May 8, 1990Assignee: Fuji Photo Film Co., Ltd.Inventors: Sadao Fujikura, Masayuki Iwasaki, Minoru Maeda, Ken Iwakura
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Patent number: 4910115Abstract: A light-sensitive photohardenable composition comprising a reducing agent, a light-sensitive silver halide, a polymerizable compound, and a coumarin or a ketocoumarin.Type: GrantFiled: November 21, 1988Date of Patent: March 20, 1990Assignee: The Mead CorporationInventors: William H. Simpson, Katherine A. Gyure
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Patent number: 4840872Abstract: A pattern forming method in which a water-soluble organic film absorbing secondary electrons or soft X-rays is formed on a resist layer and thereafter, pattern exposure, development are carried out. The water-soluble organic film containing halogen, sulfur, metal atom, etc. absorbs secondary electrons or soft X-rays which are generated from a mask in X-rays exposure so that only X-rays passed through openings of the mask are applied to a resist layer and a super fine pattern of high aspect ratio can be obtained.Type: GrantFiled: October 15, 1987Date of Patent: June 20, 1989Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Masayuki Endo, Masaru Sasago, Kazufumi Ogawa
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Patent number: 4698286Abstract: Disclosed are plasma developable photoresist compositions that possess photosensitivity to 436 n.m. light and maintain this photosensitivity for suitable periods of time after coating are obtainable. These compositions comprise perylene, certain perylene derivatives, or certain coumarin derivatives as photosensitizers in combination with N-vinyl monomers, haloalkene photoinitiators, and suitable polymeric binders in a suitable solvent.Type: GrantFiled: June 3, 1985Date of Patent: October 6, 1987Assignee: Hercules IncorporatedInventor: Wayne R. Messer
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Patent number: 4657842Abstract: Photosensitive compositions of matter which are capable of undergoing condensation or addition reactions and may or may not be crosslinkable, and which contain an anthraquinone of the formula I ##STR1## in which X, X', R' and R" are as defined in patent claim 1 and X or X' is, for example, --OH or --NH.sub.2, at least one monomeric, oligomeric or polymeric compound which can be reacted with this anthraquinone, for example, if X is --OH, a polymer with terminal glycidyl groups, and, where relevant, a crosslinking agent and/or a salt of a metal of group Ib or VIII of the periodic table, are suitable for image formation by means of electroless metal deposition.Type: GrantFiled: November 4, 1985Date of Patent: April 14, 1987Assignee: Ciba-Geigy CorporationInventors: Jurgen Finter, Walter Fischer, Friedrich Lohse
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Patent number: 4636459Abstract: A photopolymerizable composition containing an addition polymerizable compound having at least one ethylenically unsaturated double bond and a photopolymerization initiator is disclosed, wherein the photopolymerizable composition contains at least one compound represented by following general formula (I) or (II) as the photopolymerization initiator: ##STR1## wherein, R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 each represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an allyl group or a substituted allyl group, said R.sub.1 and R.sub.2 may combine with each other to form a ring together with the carbon atoms to which they are bonded; Y represents --O--, --S--, --Se--, --C(CH.sub.3).sub.2 -- or --CH.dbd.CH--; X.sub.1 represents an oxygen atom or a sulfur atom; R.sub.11, R.sub.12, R.sub.17, and R.sub.Type: GrantFiled: March 6, 1986Date of Patent: January 13, 1987Assignee: Fuji Photo Film Co., Ltd.Inventors: Kouichi Kawamura, Yoshimasa Aotani, Akira Umehara, Seiji Horie
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Patent number: 4618564Abstract: Positive images are produced by (i) exposing to actinic radiation in a predetermined pattern a composition supported on a substrate, which composition comprises a film-forming organic material and a substance which releases a sulphonic acid on exposure to actinic radiation, thereby rendering the composition more soluble in the developer in the exposed areas than the unexposed areas, and (ii) treating the composition with the aqueous base developer to remove the unexposed areas. The image-forming process may be used in the production of printing plates and electrical circuits.Type: GrantFiled: May 24, 1985Date of Patent: October 21, 1986Assignee: Ciba-Geigy CorporationInventors: Christopher G. Demmer, Edward Irving
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Patent number: 4563438Abstract: There are obtained by mixing together approximately equal parts of 1-benzoylcyclohexanol and benzophenone or a benzophenone derivative liquid mixtures which possess a high activity as photoinitiators for the polymerization of ethylenically unsaturated compounds. The level of activity is higher than that of the individual components taken separately.Type: GrantFiled: April 26, 1984Date of Patent: January 7, 1986Assignee: Ciba Geigy CorporationInventors: Godwin Berner, Aloysius H. Manser
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Patent number: 4563413Abstract: The photosensitive composition of this invention contains (1) an ethylenically unsaturated component capable of forming a high polymer by addition polymerization or crosslinking, (2) a cyclic cisoid conjugated diene as a photooxidizable component capable of reacting with singlet oxygen to form an endoperoxide, and (3) a photooxygenation sensitizer. A process for preparing a photosensitive element, such as a relief printing plate, embodying a layer of such a composition is described.Type: GrantFiled: April 23, 1984Date of Patent: January 7, 1986Assignee: Hercules IncorporatedInventor: Wayne R. Messer
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Patent number: 4543318Abstract: A photopolymerizable composition is described, comprising (1) a non-gaseous ethylenically unsaturated compound which has at least two ethylenically unsaturated terminal groups and is capable of forming a polymer, (2) a thermoplastic polymeric binder, (3) a photopolymerization initiator which is activated by actinic radiation, and (4) at least one of certain heterocyclic compounds. The composition is useful as a photoresist for producing printed circuit boards, printing plates, etc., by etching or plating, and the photoresist has superior adhesion with respect to the base.Type: GrantFiled: July 2, 1984Date of Patent: September 24, 1985Assignee: Fuji Photo Film Co., Ltd.Inventors: Minoru Maeda, Masayuki Iwasaki, Fumiaki Shinozaki
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Patent number: 4498964Abstract: Compounds of the formula I, II, III, IV or V ##STR1## in which Ar, X, Y, Y', R.sup.1 to R.sup.5 and R.sup.1' to R.sup.5' are as defined in claim 1, can be used as photoinitiators for the photopolymerization of unsaturated compounds. They can be prepared by a Diels-Alder reaction and/or a Grignard reaction.Type: GrantFiled: June 9, 1983Date of Patent: February 12, 1985Assignee: Ciba-Geigy CorporationInventors: Rinaldo Husler, Werner Rutsch, Kurt Dietliker