Carbonyl In Heterocyclic Compound Patents (Class 430/924)
  • Patent number: 9005871
    Abstract: 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: Grant
    Filed: October 8, 2009
    Date of Patent: April 14, 2015
    Assignee: BASF SE
    Inventors: Hitoshi Yamato, Toshikage Asakura, Yuichi Nishimae
  • Patent number: 8956799
    Abstract: 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: Grant
    Filed: December 12, 2012
    Date of Patent: February 17, 2015
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Emad Aqad, Cheng-Bai Xu, Mingqi Li, William Williams, III
  • Patent number: 8557500
    Abstract: 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: Grant
    Filed: February 28, 2012
    Date of Patent: October 15, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Hiromu Sakamoto, Takahiro Yasue
  • Patent number: 8435717
    Abstract: 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: Grant
    Filed: February 14, 2008
    Date of Patent: May 7, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Yuji Hagiwara, Jonathan Joachim Jodry, Satoru Narizuka, Kazuhiko Maeda
  • Patent number: 8278030
    Abstract: 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: Grant
    Filed: April 27, 2009
    Date of Patent: October 2, 2012
    Assignee: San-Apro Limited
    Inventors: Issei Suzuki, Hideki Kimura
  • Patent number: 8048613
    Abstract: 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: Grant
    Filed: October 13, 2008
    Date of Patent: November 1, 2011
    Assignee: Taiyo Ink Mfg. Co., Ltd.
    Inventors: Nobuhito Itoh, Yoko Shibasaki, Kenji Kato, Masao Arima
  • Patent number: 8021823
    Abstract: 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: Grant
    Filed: February 18, 2009
    Date of Patent: September 20, 2011
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroaki Shimizu, Tsuyoshi Nakamura, Takahiro Dazai, Daiju Shiono, Tomoyuki Hirano
  • Patent number: 7927780
    Abstract: 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: Grant
    Filed: September 10, 2008
    Date of Patent: April 19, 2011
    Assignee: 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
  • Patent number: 7560219
    Abstract: 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: Grant
    Filed: April 26, 2007
    Date of Patent: July 14, 2009
    Assignee: Henkel AG & Co. KGaA
    Inventors: Yuxia Liu, Donald E. Herr
  • Patent number: 7378223
    Abstract: 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: Grant
    Filed: May 6, 2005
    Date of Patent: May 27, 2008
    Assignee: Dongjin Semichem, Co., Ltd.
    Inventors: Bong-gi Kim, Sung-mun Ryu, Seong-mo Park, Chan-seok Park
  • Patent number: 7232647
    Abstract: 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: Grant
    Filed: March 21, 2005
    Date of Patent: June 19, 2007
    Assignee: Hitachi Chemical Co., Ltd.
    Inventors: Yasuhara Murakami, Takahiro Hidaka
  • Publication number: 20040241569
    Abstract: A chemically-amplified resist composition is disclosed, which comprises a polymer of formula (I) below: 1
    Type: Application
    Filed: May 28, 2003
    Publication date: December 2, 2004
    Applicant: Everlight USA, Inc.
    Inventors: Chi-Sheng Chen, Chan-Chan Tsai, Bin Jian, Hsin-Ming Liao
  • Patent number: 6818375
    Abstract: 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: Grant
    Filed: November 28, 2001
    Date of Patent: November 16, 2004
    Assignee: Eternal Technology Corporation
    Inventors: Thomas A. Koes, Todd Johnson
  • Patent number: 6800420
    Abstract: 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: Grant
    Filed: December 4, 2002
    Date of Patent: October 5, 2004
    Assignee: Industrial Technology Research Institute
    Inventors: Tsing-Tang Song, Weir-Torn Jiang, Shung-Jim Yang, Sheng-Min Wang, Kom-Bei Shiu
  • Publication number: 20040067431
    Abstract: 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: Application
    Filed: October 2, 2002
    Publication date: April 8, 2004
    Applicant: 3M Innovative Properties Company
    Inventors: David S. Arney, Catherine A. Leatherdale, Manoj Nirmal
  • Publication number: 20030013037
    Abstract: 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: Application
    Filed: February 21, 2002
    Publication date: January 16, 2003
    Inventors: Geun Su Lee, Jae Chang Jung, Min Ho Jung, Cha Won Koh, Ki Soo Shin
  • Publication number: 20020168584
    Abstract: 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: Application
    Filed: March 19, 2002
    Publication date: November 14, 2002
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Toshiaki Aoai, Kazuyoshi Mizutani, Shinichi Kanna
  • Patent number: 6280905
    Abstract: 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: Grant
    Filed: April 21, 2000
    Date of Patent: August 28, 2001
    Assignee: JSR Corporation
    Inventors: Katsuo Koshimura, Tsukasa Toyoshima, Takashi Nishioka, Tadaaki Tanaka
  • Patent number: 6110646
    Abstract: A positive photosensitive composition comprising an alkali-soluble organic high molecular substance having phenolic hydroxyl groups and an acid color forming dye.
    Type: Grant
    Filed: August 13, 1998
    Date of Patent: August 29, 2000
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Toshiyuki Urano, Etsuko Hino
  • Patent number: 5985511
    Abstract: 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: Grant
    Filed: December 12, 1996
    Date of Patent: November 16, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yuko Yako, Naoki Takeyama, Kenji Takahashi
  • Patent number: 5891603
    Abstract: 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: Grant
    Filed: April 25, 1997
    Date of Patent: April 6, 1999
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kunihiko Kodama, Toshiaki Aoai, Kazuya Uenishi
  • Patent number: 5811218
    Abstract: 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: Grant
    Filed: July 17, 1995
    Date of Patent: September 22, 1998
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Makoto Kaji, Yasunori Kojima, Shigeki Katogi, Masataka Nunomura, Hideo Hagiwara, Dai Kawasaki, Mitsumasa Kojima, Hiroshi Suzuki, Hidetaka Satou
  • Patent number: 5770345
    Abstract: 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: Grant
    Filed: July 16, 1996
    Date of Patent: June 23, 1998
    Assignee: International Business Machines Corporation
    Inventors: Edward Darko Babich, Karen Elizabeth Petrillo, John Patrick Simons, David Earle Seeger
  • Patent number: 5753412
    Abstract: 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: Grant
    Filed: June 5, 1996
    Date of Patent: May 19, 1998
    Assignee: International Business Machines Corporation
    Inventors: Edward Darko Babich, Karen Elizabeth Petrillo, John Patrick Simons, David Earle Seeger
  • Patent number: 5723260
    Abstract: 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: Grant
    Filed: September 17, 1996
    Date of Patent: March 3, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Shigeo Tsuji, Hiroshi Tomiyasu
  • Patent number: 5627006
    Abstract: 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: Grant
    Filed: April 18, 1995
    Date of Patent: May 6, 1997
    Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.
    Inventors: Fumiyoshi Urano, Keiji Oono, Hirotoshi Fujie
  • Patent number: 5593812
    Abstract: 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: Grant
    Filed: February 17, 1995
    Date of Patent: January 14, 1997
    Assignee: International Business Machines Corporation
    Inventors: Edward D. Babich, Karen E. Petrillo, John P. Simons, David E. Seeger
  • Patent number: 5585218
    Abstract: 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: Grant
    Filed: May 25, 1994
    Date of Patent: December 17, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yuko Nakano, Naoki Takeyama, Yuji Ueda, Takehiro Kusumoto, Hiromi Oka
  • Patent number: 5415976
    Abstract: 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: Grant
    Filed: April 28, 1994
    Date of Patent: May 16, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: M. Zaki Ali
  • Patent number: 5286603
    Abstract: 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: Grant
    Filed: June 3, 1992
    Date of Patent: February 15, 1994
    Assignee: Vickers PLC
    Inventors: John R. Wade, Rodney M. Potts, Michael J. Pratt
  • Patent number: 5256520
    Abstract: 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: Grant
    Filed: November 10, 1992
    Date of Patent: October 26, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William K. Smothers
  • Patent number: 5236808
    Abstract: 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: Grant
    Filed: April 13, 1992
    Date of Patent: August 17, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William K. Smothers
  • Patent number: 5141841
    Abstract: 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: Grant
    Filed: August 17, 1989
    Date of Patent: August 25, 1992
    Assignee: Vickers PLC
    Inventor: John R. Wade
  • Patent number: 5130227
    Abstract: 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: Grant
    Filed: October 5, 1989
    Date of Patent: July 14, 1992
    Assignee: Vickers Plc
    Inventors: John R. Wade, Rodney M. Potts, Michael J. Pratt
  • Patent number: 5091282
    Abstract: 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: Grant
    Filed: April 3, 1990
    Date of Patent: February 25, 1992
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Yasunobu Onishi, Hirokazu Niki, Yoshihito Kobayashi, Rumiko Hayase, Toru Ushirogouchi
  • Patent number: 5011755
    Abstract: 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: Grant
    Filed: January 30, 1990
    Date of Patent: April 30, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Ottmar Rohde, Armin Schaffner, Martin Riediker, Kurt Meier
  • Patent number: 4987057
    Abstract: 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: Grant
    Filed: May 22, 1989
    Date of Patent: January 22, 1991
    Assignee: Hitachi Chemical Co., Ltd.
    Inventors: Makoto Kaji, Nobuyuki Hayashi
  • Patent number: 4948694
    Abstract: 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: Grant
    Filed: September 11, 1989
    Date of Patent: August 14, 1990
    Assignee: Canon Kabushiki Kaisha
    Inventors: Norio Ohkuma, Masanori Takenouchi, Masashi Miyagawa, Hiroshi Hayashi, Tooru Minami, Hiroharu Oobayashi
  • Patent number: 4935330
    Abstract: 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: Grant
    Filed: November 14, 1989
    Date of Patent: June 19, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Hofmann, Reiner Hoffman, Harald Lauke, Wilhelm Weber, Reinhold J. Leyrer
  • Patent number: 4923781
    Abstract: 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: Grant
    Filed: October 23, 1989
    Date of Patent: May 8, 1990
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Sadao Fujikura, Masayuki Iwasaki, Minoru Maeda, Ken Iwakura
  • Patent number: 4910115
    Abstract: A light-sensitive photohardenable composition comprising a reducing agent, a light-sensitive silver halide, a polymerizable compound, and a coumarin or a ketocoumarin.
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: March 20, 1990
    Assignee: The Mead Corporation
    Inventors: William H. Simpson, Katherine A. Gyure
  • Patent number: 4840872
    Abstract: 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: Grant
    Filed: October 15, 1987
    Date of Patent: June 20, 1989
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Masayuki Endo, Masaru Sasago, Kazufumi Ogawa
  • Patent number: 4698286
    Abstract: 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: Grant
    Filed: June 3, 1985
    Date of Patent: October 6, 1987
    Assignee: Hercules Incorporated
    Inventor: Wayne R. Messer
  • Patent number: 4657842
    Abstract: 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: Grant
    Filed: November 4, 1985
    Date of Patent: April 14, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Jurgen Finter, Walter Fischer, Friedrich Lohse
  • Patent number: 4636459
    Abstract: 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: Grant
    Filed: March 6, 1986
    Date of Patent: January 13, 1987
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kouichi Kawamura, Yoshimasa Aotani, Akira Umehara, Seiji Horie
  • Patent number: 4618564
    Abstract: 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: Grant
    Filed: May 24, 1985
    Date of Patent: October 21, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Christopher G. Demmer, Edward Irving
  • Patent number: 4563413
    Abstract: 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: Grant
    Filed: April 23, 1984
    Date of Patent: January 7, 1986
    Assignee: Hercules Incorporated
    Inventor: Wayne R. Messer
  • Patent number: 4563438
    Abstract: 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: Grant
    Filed: April 26, 1984
    Date of Patent: January 7, 1986
    Assignee: Ciba Geigy Corporation
    Inventors: Godwin Berner, Aloysius H. Manser
  • Patent number: 4543318
    Abstract: 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: Grant
    Filed: July 2, 1984
    Date of Patent: September 24, 1985
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Minoru Maeda, Masayuki Iwasaki, Fumiaki Shinozaki
  • Patent number: 4498964
    Abstract: 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: Grant
    Filed: June 9, 1983
    Date of Patent: February 12, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Rinaldo Husler, Werner Rutsch, Kurt Dietliker