Patents Assigned to Toyo Gosei Kogyo Co., Ltd.
  • Patent number: 7335787
    Abstract: The invention provides a high-yield method for producing onium salt derivatives useful as agents, such as acid-generators, employed in chemically amplified resists; and to provide novel onium salt derivatives. Reaction of an onium salt derivative containing a halide anion or a carboxylate anion with a sulfonic acid ester derivative or a phosphoric acid derivative provides an onium sulfate derivative or an onium phosphate derivative at high yield.
    Type: Grant
    Filed: September 11, 2003
    Date of Patent: February 26, 2008
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Kyoichi Tomita, Shinji Ishii
  • Patent number: 6861456
    Abstract: The present invention provides a novel photosensitive compound having an azido group suitable for exposure to light of a short wavelength; a photosensitive resin containing the photosensitive compound; and a photosensitive composition containing the photosensitive compound or photosensitive resin. The photosensitive compound containing a photosensitive unit represented by formula (1): wherein R is selected from among the following groups, R: X is selected from among the following groups, X: and each of Y and Z represents a hydrogen atom, an alkyl group, an acetal-group-containing alkyl group, an aryl group, an aralkyl group, or a substituent containing a base-forming nitrogen atom, wherein at least one of R and X contains an azido group.
    Type: Grant
    Filed: March 27, 2003
    Date of Patent: March 1, 2005
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Toru Shibuya, Masanori Kurihara, Mineko Takeda, Kazuo Yamada
  • Patent number: 6797452
    Abstract: A photosensitive resin composition which includes a photosensitive saponified PVA having a pendant group derived from a quaternary styrylpyridinium or styrylquinolinium, or a derivative thereof. The composition comprises a photosensitive saponified PVA which has structural units represented by formulas (1) to (4): which product is dissolved in at least one organic solvent selected from the group consisting of compounds represented by formulas (5), (6), and (7). The resin composition can be dissolved in a comparatively safe high-boiling-point solvent, such as propylene glycol, and can be developed with water.
    Type: Grant
    Filed: July 12, 2002
    Date of Patent: September 28, 2004
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Masahiro Takano, Shin Utsunomiya, Nobuji Sakai, Noriaki Tochizawa
  • Patent number: 6777477
    Abstract: The invention relates to a coating solution for forming transparent conductive tin oxide film, a method for producing transparent conductive tin oxide film, and transparent conductive tin oxide film. The coating solution is capable of forming, from an inexpensive starting material such as tin oxide or tin chloride, strong tin oxide film endowed with excellent conductivity and transparency. The coating solution, which is intended to be used for forming, by way of coating, transparent conductive film predominantly containing tin oxide, contains stannic acid as its major component, and a water-soluble polymer having a polar group which is dissolved in the presence of at least one compound selected from the group consisting of ammonia and water-soluble amines.
    Type: Grant
    Filed: July 17, 2001
    Date of Patent: August 17, 2004
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Kazuma Niume, Takashi Uchida, Masateru Kimura
  • Patent number: 6768027
    Abstract: The invention provides a novel azidocinnamaldehyde compound which, when used as an intermediate for providing a photosensitive moiety of a photoresist, introduces a photosensitive moiety having high sensitivity and attaining high contrast between the exposed portion and the unexposed portion, and which per se can serve as a photosensitive moiety. The azidocinnamaldehyde compound is represented by formula(I): wherein R represents a lower alkyl group and Y represents hydrogen or a sulfonate salt group.
    Type: Grant
    Filed: March 27, 2003
    Date of Patent: July 27, 2004
    Assignee: Toyo Gosei Kogyo Co. Ltd.
    Inventor: Mineko Takeda
  • Patent number: 6713225
    Abstract: The invention provides a 1,2-naphthoquinone-2-diazidesulfonate ester photosensitive agent which is useful as a photosensitive agent employed in a photoresist for producing semiconductor integrated circuits, liquid crystal displays, EL displays, etc., a method for producing the photosensitive agent, and a photoresist composition containing the photosensitive agent.
    Type: Grant
    Filed: March 11, 2003
    Date of Patent: March 30, 2004
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Hirotada Iida, Miharu Suwa, Yuichi Hagiwara, Katsumi Tada, Suehiro Katori, Tsuneaki Miyazaki
  • Patent number: 6620957
    Abstract: The invention provides a high-yield method for producing onium salt derivatives useful as agents, such as acid-generators, employed in chemically amplified resists; and to provide novel onium salt derivatives. Reaction of an onium salt derivative containing a halide anion or a carboxylate anion with a sulfonic acid ester derivative or a phosphoric acid derivative provides an onium sulfate derivative or an onium phosphate derivative at high yield.
    Type: Grant
    Filed: August 3, 2001
    Date of Patent: September 16, 2003
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Kyoichi Tomita, Shinji Ishii
  • Patent number: 6448383
    Abstract: A method for producing a high-purity 1,2-naphthoquinonediazide photosensitive agent containing a low level of impurities, by condensing, in an organic solvent other than amide, polyhydric phenolic compound and 1,2-naphthoquinonediazide-sulfonic acid halide in the presence of organic amine; subsequently adding amide solvent to the resultant reaction mixture; and separating the resulting organic amine acid salt through filtration.
    Type: Grant
    Filed: May 8, 2001
    Date of Patent: September 10, 2002
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Tomotaka Yamanaka, Masamichi Hayakawa
  • Patent number: 6444391
    Abstract: Photosensitive compositions prepared without use of a chromium compound. The compositions exhibit high resolution and satisfactory sensitivity, and do not cause environmental pollution. The photosensitive compositions contain a water-soluble azide compound which serves as a photocrosslinking agent and poly(N-vinylacetamide) that is photocrosslinkable in the presence of the water-soluble azide compound.
    Type: Grant
    Filed: January 2, 2001
    Date of Patent: September 3, 2002
    Assignees: Toyo Gosei Kogyo Co., Ltd., Showa Denko K.K.
    Inventors: Masaharu Watanabe, Noriaki Tochizawa
  • Patent number: 6342330
    Abstract: Photosensitive compositions prepared without use of a chromium compound. The compositions exhibit high resolution and satisfactory sensitivity, and do not cause environmental pollution. The photosensitive compositions contain a water-soluble azide compound which serves as a photocrosslinking agent and poly(N-vinylacetamide) that is photocrosslinkable in the presence of the water-soluble azide compound.
    Type: Grant
    Filed: January 2, 2001
    Date of Patent: January 29, 2002
    Assignees: Toyo Gosei Kogyo Co., Ltd., Showa Denko K.K.
    Inventors: Masaharu Watanabe, Noriaki Tochizawa, Hirotaka Tagoshi, Tetsuhiko Yamaguchi
  • Patent number: 6274714
    Abstract: An effective method for producing 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride at high yield, wherein formation of impurities is prevented. The method includes the following steps: 1,2-naphthoquinone-2-diazide is reacted with chlorosulfuric acid, to thereby produce a mixture of a sulfonated compound and a chlorosulfonated compound of the diazide; and to the mixture, at least one substance selected from among thionyl chloride and phosphorus pentachloride is added for further reaction, to thereby obtain 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride.
    Type: Grant
    Filed: April 11, 2000
    Date of Patent: August 14, 2001
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Hirotada Iida, Seiju Tobishima, Naoki Sato, Nobuhiro Yoneyama, Yuki Hotta, Toshio Itahana, Yuichi Hagiwara
  • Patent number: 6140018
    Abstract: The invention provides a photosensitive resin and a photosensitive resin composition having excellent water resistance after hardening, excellent developability, and excellent patterning characteristics, and a pattern formation method making use of the composition. The invention provides saponified PVA photosensitive resin which contains structural units represented by formulas (I) and (II): ##STR1## the content of the structural units represented by formulas (I) and (II) in the resin being 0.5-10 mol % with respect to entirety of the structural units of the saponified product of PVA.
    Type: Grant
    Filed: August 5, 1999
    Date of Patent: October 31, 2000
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Noriaki Tochizawa, Mitsuharu Miyazaki, Takaho Ito
  • Patent number: 6140007
    Abstract: Photosensitive compositions prepared without use of a chromium compound. The compositions exhibit high resolution and satisfactory sensitivity, and do not cause environmental pollution. The photosensitive compositions contain a water-soluble azide compound which serves as a photocrosslinking agent and poly(N-vinylformamide) that is photocrosslinkable in the presence of the water-soluble azide compound.
    Type: Grant
    Filed: May 12, 1999
    Date of Patent: October 31, 2000
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Masaharu Watanabe, Noriaki Tochizawa, Yukari Imamura, Hideo Kikuchi
  • Patent number: 6077941
    Abstract: An effective method for producing a 1,2-naphthoquinone-2-diazide or a sulfo-substituted compound thereof from a 2-diazo-1-naphthalenesulfonic acid or a sulfo-substituted compound thereof. A 1,2-naphthoquinone-2-diazide derivative or a sulfo-substituted compound thereof is derived from a 2-diazo-1-naphthalenesulfonic acid or a sulfo-substituted compound thereof by use of an aqueous alkaline solution containing iodine; an aqueous alkaline solution containing iodine which is dissolved in an organic solvent; or an aqueous alkaline solution containing an oxidizing agent and iodine or an iodine compound.
    Type: Grant
    Filed: June 15, 1999
    Date of Patent: June 20, 2000
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Hirotada Iida, Nobuhiro Yoneyama, Seiju Tobishima, Toshio Itahana, Kunihiko Kojima
  • Patent number: 5965320
    Abstract: A positive photoresist composition including an alkali-soluble resin and a photosensitive agent including 1,2-naphthoquinone-diazide group. A first composition wherein the photosensitive agent is an ester of 1,2-naphthoquinone-(2)-diazide-6-sulfonic acid and alcohols or phenols, or a sulfonamide of 1,2-naphthoquinone-(2)-diazide-6-sulfonic acid and organic amines.A second composition wherein the photosensitive agent comprises (a) an ester compound of 1,2-naphthoquinone-(2)-diazide-6-sulfonic acid and phenols and (b) an ester of 1,2-naphthoquinone-(2)-diazide-5-sulfonic acid and phenols and/or an ester of 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid and phenols.A third composition wherein the photosensitive agent is a product obtained by condensation of phenols with (a) 1,2-naphthoquinone-(2)-diazide-6-sulfonylhalide and (b) 1,2-naphthoquinone-(2)-diazide-5-sulfonylhalide and/or 1,2-naphthoquinone-(2)-diazide-4-sulfonylhalide.
    Type: Grant
    Filed: September 7, 1993
    Date of Patent: October 12, 1999
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Kazue Torimitsu, Yuko Urano, Hideo Kikuchi
  • Patent number: 5807657
    Abstract: A polyvinyl alcohol base photosensitive resin comprised of a polyvinyl alcohol base polymer compound with the structural units of formulae (I) and (II) ##STR1## as well as a photosensitive resin composition comprising this resin and, optionally, an anionic additive and a method of forming a pattern using this photosensitive composition. R.sup.1 is a residue of a heterocyclic ring with quaternarized aromatic species, R.sup.2 is hydrogen atom or lower alkoxyl group, M is 0 or 1, and n is 1 to 6. X.sup.1, X.sup.2 are hydrogen atom, sodium, potassium or ammonium ion. These resins aid in water solubility, compatibility and sensitivity and are used in forming screen printing plates, black matrix or phosphor pattern formation of color cathode ray tubes, color filters, color printing proofs and etching resists.
    Type: Grant
    Filed: December 11, 1996
    Date of Patent: September 15, 1998
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Hideo Kikuchi, Noriaki Tochizawa, Yasuo Kuniyoshi
  • Patent number: 5639579
    Abstract: A photosensitive colored resin composition for the formation of colored images includes (a) a resin-based material hardenable with an acid, (b) a photoreactive acid-releasing agent, and (c) a pigment.A colored image formation method of a color filter suitable for liquid crystal display panel applications includes the steps of:(1) coating a photosensitive colored resin composition including (a) a resin-based material hardenable with an acid, (b) a photoreactive acid-releasing agent, and (c) a pigment on a transparent substrate, and drying the coating to form a colored resin layer;(2) pattern exposing the colored resin layer;(3) heating the exposed colored resin layer; and(4) developing the exposed and heated colored resin layer with an alkaline developing solution to form a colored image on the transparent substrate,the steps being repeated to form a multi-colored image on the same substrate.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: June 17, 1997
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Keiichi Hayashi, Nobuyuki Kurata, Keiji Ishii, Hideo Kikuchi
  • Patent number: 5589315
    Abstract: A photosensitive composition containing a polyfunctional aromatic diazo compound having at least two groups of Formula (uD) in the molecule, and a photosensitive composition using the same. The diazo compound can be handled under visible light free from ultraviolet, is highly photosensitive, has good shelf life, and lithographic printing plates and screen printing plates formed with the same: ##STR1## wherein G.sup.1 is a substituent derived from alcoholic hydroxyl group; R.sup.1 and R.sup.2 are hydrogen, or alkyl or alkyloxy of 1 to 8 carbon atoms;R.sup.3 is alkyl or substituted alkyl of 1 to 8 carbon atoms, aralkyl or substituted aralkyl of 7 to 14 carbon atoms, or --CH.sub.2 CHG.sup.2 --CH.sub.2 --;X.sup.- is an anion based on protonic acid from which a proton is removed.
    Type: Grant
    Filed: January 6, 1995
    Date of Patent: December 31, 1996
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Hirotada Iida, Noriaki Tochizawa, Yasuo Kuniyoshi, Masaharu Watanabe, Katsuyo Tokuda, Ichiro Hozumi
  • Patent number: 5459011
    Abstract: A photosensitive composition including a water-soluble aromatic diazo compound having at least two diazo groups and lactic acid, hydroxyacetic acid or, a mixture thereof in an amount of at least one third by weight of the diazo compound. The photosensitive composition is in the form of a liquid or paste, is thus easy to handle, is suitable for use in the production of photosensitive printing plates, and has good storage stability.
    Type: Grant
    Filed: February 27, 1995
    Date of Patent: October 17, 1995
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Hirotada Iida, Kieko Harada, Katsuyo Tokuda
  • Patent number: 5430130
    Abstract: An photosensitive polyfunctional aromatic diazo compound having at least two groups of Formula (uD) in the molecule, and a photosensitive composition using the same. The diazo compound can be handled under visible light free from ultraviolet, is highly photosensitive, has good shelf life, and is adequate as a photosensitive agent for lithographic printing plates and screen printing plates: ##STR1## wherein G.sup.1 is a substituent derived from alcoholic hydroxyl group; R.sup.1 and R.sup.2 are hydrogen, or alkyl or alkyloxy of 1 to 8 carbon atoms;R.sup.3 is alkyl or substituted alkyl of 1 to 8 carbon atoms, aralkyl or substituted aralkyl of 7 to 14 carbon atoms, or --CH.sub.2 CHG.sup.2 --CH.sub.2 --;X.sup.- is an anion based on protonic acid from which a proton is removed.
    Type: Grant
    Filed: July 21, 1993
    Date of Patent: July 4, 1995
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Hirotada Iida, Noriaki Tochizawa, Yasuo Kuniyoshi, Masaharu Watanabe, Katsuyo Tokuda, Ichiro Hozumi