Diazonium Compound Containing Patents (Class 430/171)
  • Patent number: 5952477
    Abstract: The present invention is concerned with a novel azo compound represented by formula (1), (2) or (3), a water-soluble dye comprising this azo compound, and a polarizing film containing this azo compound. The obtained polarizing film has high hydrothermoresistance and a high polarization degree and is excellent in optical characteristics: ##STR1## wherein each of the groups is defined.
    Type: Grant
    Filed: October 15, 1997
    Date of Patent: September 14, 1999
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Tsutami Misawa, Akira Ogiso, Rihoko Imai, Hisato Itoh
  • Patent number: 5945247
    Abstract: A heat development type duplicating material having a recording layer which is formed on a support. The recording layer comprises a photosensitive diazo compound and a coupler that reacts with the diazo compound to develop color. Furthermore, the duplicating material contains an ascorbic acid derivative. The heat development type duplicating material generates little stain in background areas, exhibits satisfactory storage stability, and provides a high image density.
    Type: Grant
    Filed: April 17, 1997
    Date of Patent: August 31, 1999
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Hirokazu Shimada
  • Patent number: 5935756
    Abstract: A diazonium salt for a color-forming layer of a thermosensitive recording medium, having formula (1): ##STR1## wherein R is an alkyl group having four carbon atoms which is selected from the group consisting of n-butyl, t-butyl, and sec-butyl, and X.sup.- is selected from the group consisting of hexafluorophosphate ion PF.sub.6.sup.-, tetrafluoroborate ion BF.sub.4.sup.- and tetraphenylborate ion (C.sub.6 H.sub.5).sub.4 B.sup.-. In a first embodiment, a thermosensitive recording medium has a color-forming layer which includes a diazonium salt as described above, a basic compound and a coupler. In a second embodiment, a thermosensitive recording medium has a color-forming layer which includes: a diazonium salt, a basic compound, and a coupler, wherein the diazonium salt has a formula (2): ##STR2## where R.sup.1 and R.sup.2 are alkyl groups each having one or more carbon atoms, and X.sup.- is selected from the group consisting of hexafluorophosphate ion PF.sub.6.sup.-, tetrafluoroborate ion BF.sub.4.sup.
    Type: Grant
    Filed: June 16, 1997
    Date of Patent: August 10, 1999
    Assignee: Oki Electric Industry Co., Ltd.
    Inventors: Katsuaki Kaifu, Akihiko Nishiki, Takeshi Koyano
  • Patent number: 5935757
    Abstract: A heat-sensitive recording material having a support and a heat-sensitive recording layer provided thereon. The heat-sensitive recording layer contains a diazonium salt compound and a coupler which reacts with the diazonium salt compound upon heating to form a color. The heat-sensitive recording layer contains a compound of the following formula (I): ##STR1## wherein R represents a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, and an aryl group; X represents a member selected from the group consisting of --COOR.sup.1, --OCOR.sup.--1, --CONR.sup.1 R.sup.2, and --NR.sup.2 COR.sup.1 ; R.sup.1 represents an alkyl group or an aryl group, R.sup.2 represents a member selected from the group consisting of a hydrogen atom, an alkyl group, and an aryl group; n represents an integer from 1 to 5.
    Type: Grant
    Filed: November 20, 1997
    Date of Patent: August 10, 1999
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hisao Yamada, Yoshihiro Jinbo, Naoto Yanagihara
  • Patent number: 5925489
    Abstract: Disclosed is a heat-sensitive recording material comprising a substrate having thereon a heat-sensitive recording layer containing a diazonium salt compound and a coupler, pyrrolo?1,2-a! pyrimidine compound, as the coupler, being represented by the following general formula (1): ##STR1## wherein R.sup.1 to R.sup.4 each represents a hydrogen atom, a halogen atom, an aryl group, an alkyl group, a cyano group, an acyl group, a substituted carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an alkoxy group, an aryloxy group, an alkylthio group, or an arylthio group.The diazo-type heat-sensitive recording material, which develops a violet to cyan color, has excellent image stability and image fixing characteristics.
    Type: Grant
    Filed: February 13, 1998
    Date of Patent: July 20, 1999
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Tatsuo Kawabuchi, Hiroshi Sato, Kimiatsu Nomura, Masanobu Takashima
  • Patent number: 5891604
    Abstract: The present invention aims to solve problems involved in the formation of a conductive or insulating layer in a pattern form by photolithography, i.e., an environmental problem associated with handling a solvent and a problem associated with wastewater treatment in the development with an aqueous alkaline solution. A method for forming a conductive layer (an anode bus 3) or an insulating layer (a barrier 1) on a glass substrate by photolithography using a photosensitive slurry solution prepared by mixing a low-melting glass powder as a binder and a conductive or insulating powder into a PVA-based, water-soluble photosensitive solution, wherein the content of B.sub.2 O.sub.3 component in the whole low-melting glass powder is closely regulated to not more than 6% by weight. This enables coating without gelation of PVA.
    Type: Grant
    Filed: May 16, 1997
    Date of Patent: April 6, 1999
    Assignees: Nippon Hoso Kyokai, Dai Nippon Printing Co.,Ltd.
    Inventors: Toshihiro Katoh, Takao Kuriyama, Tatsuya Takei, Takashi Kawai, Hiroshi Murakami, Eiji Munemoto, Norio Ohta, Koji Shimada
  • Patent number: 5879856
    Abstract: Photoresist compositions are provided comprising 1) a resin binder having photoacid-labile groups, 2) an acid generator and 3) a photospeed control agent. Photoresists of the invention exhibit good photospeed and can provide highly resolved relief images of small dimensions, including lines of sub-micron and sub-half micron dimensions with at least essentially vertical side walls. Methods are also provided that include control of photospeed of a photoresist composition of the invention.
    Type: Grant
    Filed: December 5, 1995
    Date of Patent: March 9, 1999
    Assignee: Shipley Company, L.L.C.
    Inventors: James W. Thackeray, Peter R. Hagerty
  • Patent number: 5866293
    Abstract: A heat-sensitive recording material having excellent light-fastness and raw stock storability is disclosed. The material includes a support and a heat-sensitive recording layer provided on the support, and the heat-sensitive recording layer contains a diazo compound and a coupler. The coupler contains at least one species of pyrazolone compounds represented by the following formula (1): ##STR1## wherein Ar represents a phenyl group, a naphthyl group, or an aromatic heterocyclic group, any one of which may have a substituent bonded to the nucleus, said substituent may be a halogen atom, a cyano group, a trifluoromethyl group, an alkyl group, an aryl group, an alkoxycarbonyl group, a carbamoyl group, or a sulfamoyl group; R.sup.1 and R.sup.2 independently represent an alkyl group, an alkenyl group, or an aryl group, or R.sup.1 and R.sup.2 may be linked to each other so as to form a heterocycle.
    Type: Grant
    Filed: May 21, 1997
    Date of Patent: February 2, 1999
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kimiatsu Nomura, Hiroshi Sato, Naoto Yanagihara, Tetsunori Matsushita, Shojiro Sano
  • Patent number: 5773186
    Abstract: A heat-sensitive recording material comprises a substrate and a heat-sensitive recording layer provided on the substrate, and the heat-sensitive layer contains a diazo compound and a coupler compound which produces color, reacting with the diazo compound. The heat-sensitive recording material contains a diazo compound represented by the following general formula (I) or (II) ##STR1## wherein R.sup.1 to R.sup.4 each independently represents a hydrogen atom, an alkyl group, --OR.sup.5, --SR.sup.6, --NR.sup.7 R.sup.8, --COR.sup.10, a halogen atom, --SO.sub.2 R.sup.10, --CN, --NO.sub.2, or the like, in which R.sup.7 and R.sup.8 are coupled together to form an alkylene group which may contain --O--, --S--, --SO.sub.2 -- or --NR.sup.9 ; A represents --CO-- or --S0.sub.2 --; B represents --SO.sub.2 R.sup.11 or --POR.sup.12 R.sup.13, in which R.sup.11 represents an alkyl group, --NR.sup.7 R.sup.8 or the like and R.sup.12 and R.sup.13 each independently represents an alkyl group, an aryl group or the like, R.sup.
    Type: Grant
    Filed: February 18, 1997
    Date of Patent: June 30, 1998
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Masanobu Takashima
  • Patent number: 5763134
    Abstract: Photochemical acid progenitors in combination with dihydroperimidine squarylium dyes have been found to be particularly effective at generating acid upon irradiation with near-infrared radiation. It has been found that dihydroperimidine squarylium dyes that are particularly useful in this invention have an oxidation potential greater than about 0.5 V relative to SCE as measured in dichloromethane.
    Type: Grant
    Filed: May 13, 1996
    Date of Patent: June 9, 1998
    Assignee: Imation Corp
    Inventors: Stanley C. Busman, Richard J. Ellis, Jeanne E. Haubrich, William D. Ramsden, Tran Van Thien, Gregory D. Cuny
  • Patent number: 5707776
    Abstract: Disclosed is a positive radiation-sensitive resist composition comprising polymer(s) of the following general formula (1) and a radiation-sensitive agent. ##STR1## Ra, Rb, Rc and Rd each are independently a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, an aralkyl group, an alkoxycarbonyl group, an arylcarbonyl group, an acyloxy group, an acyl group, or a cycloalkyl group; k is an integer of from 1 to 30; (1+n) is an integer of from 1 to 100; m is an integer of from 1 to 50; p1, p2 and p3 each are an integer of from 1 to 3; q1 is an integer of from 1 to 4. The resist composition has high resolution to give resist patterns with good profiles and has high heat resistance and good storage stability.
    Type: Grant
    Filed: May 10, 1995
    Date of Patent: January 13, 1998
    Assignee: Fuji Photo Film Co., LTD.
    Inventors: Yasumasa Kawabe, Tsukasa Yamanaka, Toshiaki Aoai
  • Patent number: 5700624
    Abstract: The invention comprises an acid hardened resist system consisting of a resin binder having acid labile blocking groups and inert blocking groups and a photoacid generator. The inclusion of inert blocking groups on the resin improves shelf life without deleteriously affecting photolithographic properties of the resist.
    Type: Grant
    Filed: May 9, 1995
    Date of Patent: December 23, 1997
    Assignee: Shipley Company, L.L.C.
    Inventors: James W. Thackeray, Roger F. Sinta, Mark D. Denison, Sheri L. Ablaza
  • Patent number: 5683850
    Abstract: A diazo heat-sensitive recording material having excellent raw stock storability and image storage characteristics, which comprises a support having thereon a recording layer comprising a diazo compound, a coupling component and an organic base. The diazo compound is a 4-disubstituted amino-2-alkoxybenzenediazonium salt and the coupling component is a compound represented by the following general formula: ##STR1## wherein R.sub.4, R.sub.5, R.sub.6 and R.sub.7 each represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an alkyloxy group, an aryloxy group, an alkylthio group, an arylthio group, an acyl group, an alkoxycarbonyl group, an acyloxy group, a carbamoyl group, a sulfamoyl group, a halogen atom, a cyano group or a nitro group.
    Type: Grant
    Filed: December 2, 1996
    Date of Patent: November 4, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Tetunori Matushita, Hiroshi Sato, Sadao Ishige, Kimiatsu Nomura, Mitsuyuki Tsurumi
  • Patent number: 5672463
    Abstract: A polyfunctional vinyl ether compound represented by formula (I): ##STR1## wherein n, which is an average repeating number, represents a number of from 0 to 20; R.sub.1 and R.sub.2 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, or a cycloalkyl group; Q each independently represents --OH or a group represented by the formula --OROCH.dbd.CH.sub.2, wherein R represents an alkylene group having from 1 to 12 carbon atoms, the molar ratio of (--OH)/(--OROCH.dbd.CH.sub.2) being from 10/90 to 90/10; and A each independently represents a divalent hydrocarbon group having from 1 to 30 carbon atoms.
    Type: Grant
    Filed: October 20, 1995
    Date of Patent: September 30, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shigeo Hozumi, Shinichiro Kitayama, Hiroya Nakagawa
  • Patent number: 5667930
    Abstract: A photopolymerization photoresist composition having a binder resin, a multifunctional compound, a photopolymerization initiator, a sensitizer and other additives. The photopolymerization initiator has one or more 4,6-bis(chloromethyl)-s-triazine compound containing a diazophenyl group. The initiator acts as a chromophore and is represented by the following general formula I: ##STR1## wherein the position at which the diazo group bonds to phenyl group may be changed. R is an aliphatic radical or an unsubstituted- or substituted aromatic radical and n is an integer of 0 to 2.
    Type: Grant
    Filed: May 20, 1996
    Date of Patent: September 16, 1997
    Assignee: Cheil Synthetics Incorporation
    Inventors: Bo Sung Kim, Soon Sik Kim, Dae Woo Ihm
  • Patent number: 5552260
    Abstract: Acid-sensitive polymers and imageable articles employing them are disclosed. In particular, photosensitive compositions are disclosed comprising: (a) a photoinitiator which generates an acid upon exposure to radiation; and (b) a polymer having acid labile groups pendant from the polymer backbone, said acid labile pendant groups comprising at least one each of A and B wherein A has the formula --T-(C.dbd.O)OCR.sup.1 R.sup.2 OR.sup.3, and B has the formula --T-(C.dbd.O)OR.sup.4 Si(R.sup.5).sub.3, wherein R.sup.1 and R.sup.2 each represent H or an alkyl group with the proviso that at least one of R.sup.1 and R.sup.2 must be hydrogen; R.sup.3 represents an alkyl group; or any two of R.sup.1, R.sup.2, and R.sup.3 may together form a ring group having from 3 to 36 carbon atoms; R.sup.5 represents an alkyl group, aryl group, an alkoxy group, an aryloxy group, an acyloxy group, or a trialkylsiloxy group; and R.sup.4 and T represents a divalent linking group wherein T is bonded to the polymer backbone and R.sup.
    Type: Grant
    Filed: November 16, 1994
    Date of Patent: September 3, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Dennis E. Vogel, Leonard J. Stulc
  • Patent number: 5543262
    Abstract: A light sensitive composition which is capable of photopolymerization which includes a photopolymerizable compound a free radical generating component and a benzanthrone or substituted benzanthrone which substantially prevents photopolymerization when the light sensitive composition is exposed to actinic radiation below a threshold amount but permits photopolymerization when the light sensitive composition is exposed to actinic radiation above a threshold amount. This achieves a gate effect which eliminates or decreases unwanted partial exposure in the nonimage areas and hence improves reproduction quality.
    Type: Grant
    Filed: February 24, 1995
    Date of Patent: August 6, 1996
    Assignee: International Paper Company
    Inventors: Maria T. Sypek, John R. Delude, Paul A. Perron
  • Patent number: 5494772
    Abstract: A heat-sensitive recording material comprising on a support a heat-sensitive layer comprising color-forming component A, color-forming component B which forms a color by reacting with the color-forming component A, and a tricarbocyanine dye having at least two acidic groups, wherein the tricarbocyanine dye has an absorption maximum wavelength of 650 to 1300 nm in the heat-sensitive layer and has an absorption maximum wavelength 50 nm or more longer than that of an aqueous solution of the tricarbocyanine dye.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: February 27, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Noriyuki Hosoi, Koh Takeuchi, Yoshio Inagaki
  • Patent number: 5482816
    Abstract: A radiation-sensitive composition comprising (A) a polymer having a recurring unit represented by formula (1): ##STR1## wherein R.sup.1 represents a substituted methyl group, a substituted ethyl group, a silyl group, a germyl group or an alkoxycarbonyl group, and R.sup.2 represents --OR.sup.3 or --NR.sup.4 R.sup.5 in which R.sup.3 is a hydrogen atom, a straight-chain alkyl group, a cyclic alkyl group, an aryl group, an aralkyl group, a substituted methyl group, a substituted ethyl group, a silyl group, a germyl group or an alkoxycarbonyl group, and R.sup.4 and R.sup.5, which may be the same or different, are hydrogen atoms, straight-chain alkyl groups, cyclic alkyl groups, aralkyl groups or aryl groups, and (B) a radiation-sensitive acid forming agent.
    Type: Grant
    Filed: June 21, 1994
    Date of Patent: January 9, 1996
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Makoto Murata, Mikio Yamachika, Yoshiji Yumoto, Takao Miura
  • Patent number: 5478689
    Abstract: A thermal development diazo copying material is composed of a support, and a photosensitive layer formed thereon, which includes a diazo compound, a coupler, an alkali-soluble resin, and a sensitizer, with only the coupler being contained in microcapsules made of the alkali-soluble resin.
    Type: Grant
    Filed: February 18, 1994
    Date of Patent: December 26, 1995
    Assignee: Ricoh Company, Ltd.
    Inventors: Masanori Rimoto, Shigeru Kusakata
  • 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
  • Patent number: 5409797
    Abstract: A heat-sensitive recording material for laser recording is provided including a support having thereon a heat-sensitive layer including at least a first substantially colorless coloring component, a second substantially colorless coloring component which reacts with the first substantially colorless coloring component to develop a color, and an infrared-absorbing dye.
    Type: Grant
    Filed: September 7, 1993
    Date of Patent: April 25, 1995
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Noriyuki Hosoi, Masao Yabe, Naoto Yanagihara
  • Patent number: 5340699
    Abstract: A radiation-sensitive composition especially adapted to prepare a lithographic printing plate that is sensitive to both ultraviolet and infrared radiation and capable of functioning in either a positive-working or negative-working manner is comprised of (1) a resole resin, (2) a novolac resin, (3) a latent Bronsted acid and (4) an infrared absorber. The solubility of the composition in aqueous alkaline developing solution is both reduced in exposed areas and increased in unexposed areas by the steps of imagewise exposure to activating radiation and heating.
    Type: Grant
    Filed: August 4, 1993
    Date of Patent: August 23, 1994
    Assignee: Eastman Kodak Company
    Inventors: Neil F. Haley, Steven L. Corbiere
  • Patent number: 5328796
    Abstract: A diazo type recording material, which has a substantially unstained background, a superior preservability, and is capable of producing images of high density, wherein the diazo recording material comprises a support having thereon a recording layer comprising a photosensitive diazo compound, a hydroxyphenylsulfone derivative and a coupling component which forms a color by reacting with the diazo compound, with the diazo compound being enclosed in microcapsules.
    Type: Grant
    Filed: April 28, 1993
    Date of Patent: July 12, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Akihiro Shimomura, Taketatsu Sugiyama, Makoto Ohno, Toshiharu Tanaka
  • Patent number: 5310618
    Abstract: A light-sensitive composition comprising either an alkali-soluble resin or radical-polymerizable, unsaturated compound, and a diazonium compound represented by general formula (I) or (II):(S).sub.1 --(L.sup.1).sub.m --(D).sub.n (I)--(L.sup.2 (S)).sub.o --(L.sup.3 (D)).sub.P -- (II)wherein D is a diazonium salt group, S is a light absorbing group, L.sup.1, L.sup.2 and L.sup.3 are connecting groups connecting S and D, provided that S and D are not conjugated by L.sup.1, L.sup.2 and L.sup.3 ; l, m, n, o and p are integers.
    Type: Grant
    Filed: May 24, 1991
    Date of Patent: May 10, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Kouichi Kawamura
  • Patent number: 5264318
    Abstract: A positive type photosensitive composition developable with water or warm water alone of water-soluble photocrosslinking agent, water-soluble resin and synthetic resin emulsion and further a coloring agent, if necessary.
    Type: Grant
    Filed: January 7, 1992
    Date of Patent: November 23, 1993
    Assignee: Sanyo-Kokusaku Pulp Co., Ltd.
    Inventors: Norio Yabe, Kuniaki Monden, Hisashi Mino
  • Patent number: 5254431
    Abstract: A radiation sensitive material suitable for the production of radiation sensitive plates for lithographic printing plate manufacture comprises a polymer having appendent azide-substituted aromatic ester groups and sulphonyl urethane groups. The radiation sensitive compound is produced by a process in which some hydroxyl and/or epoxide groups of a polymer are reacted with an azide substituted carboxylic acid or ester forming derivative thereof, and some hydroxyl groups are reacted with a sulphonyl isocyanate.
    Type: Grant
    Filed: November 23, 1992
    Date of Patent: October 19, 1993
    Assignee: Vickers plc
    Inventors: Terence Etherington, Victor Kolodziejczyk
  • Patent number: 5236800
    Abstract: A heat-developable copying material comprising a support having thereon a heat-developable light-sensitive layer comprising microcapsules containing a diazo compound and substantially no solvent, a coupling component and a color basic substance.
    Type: Grant
    Filed: April 12, 1989
    Date of Patent: August 17, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kotaro Nakamura, Hirokazu Shimada
  • Patent number: 5225309
    Abstract: Disclosed is a light-sensitive litho printing plate comprising:a support, a light-sensitive layer and a silicone rubber layer provided thereon,wherein said light-sensitive layer contains a substance,whereby said substance forms a color during developing or after developing.
    Type: Grant
    Filed: March 19, 1992
    Date of Patent: July 6, 1993
    Assignees: Konica Corporation, Mitsubishi Kasei Corporation
    Inventors: Norihito Suzuki, Kiyoshi Goto, Hiroshi Tomiyasu, Kazuo Noguchi, Akeo Kasakura
  • Patent number: 5213939
    Abstract: A light- and heat-sensitive recording material is disclosed which includes a support having thereon a recording layer containing a diazo compound, a coupling component, and an organic base compound, wherein the diazo compound is a 1-substituted amino-3-alkoxybenzene-4-diazonium salt and the coupling component is a compound prepared from any of cyclohexane-1,3-dione, 3-cyclohexenone, or 2-cyclohexenone. The light- and heat-sensitive recording material according to the present invention can develop an excellent magenta color hue and has excellent storage properties before recording use (shelf life).
    Type: Grant
    Filed: September 23, 1991
    Date of Patent: May 25, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Takekatsu Sugiyama, Sadao Ishige, Naoto Yanagihara, Hiroshi Kamikawa, Keiichi Tateishi
  • Patent number: 5206349
    Abstract: An aromatic diazo compound having at least two groups of Formula (I) in the molecule.This aromatic diazo compound can be handled under visible light free from ultraviolet, is high in photosensitivity, and can be produced by a simple synthesis method.The diazo compound has a high solubility in organic solvents, appropriate for use as a photosensitive material for a lithographic printing plate, can be easily developed by an alkaline developing solution mainly based on an alkaline aqueous solution, and has a water solubility appropriate for use in a screen printing plate. ##STR1## wherein Z.sup.1 indicates ##STR2## wherein .phi..sup.1 is arylene or substituted arylene; and -.phi..sup.2 is >C.dbd.O, lower alkyl, lower alkylene, or aryl or substituted aryl.R.sup.1 and R.sup.2 are H, alkyl of C.sub.1 to C.sub.8, or alkyloxy of C.sub.1 to C.sub.8 ; X.sup.- is anion; and R.sup.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: April 27, 1993
    Assignee: Toyo Gosei Kogy Co., Ltd.
    Inventors: Hirotada Iida, Hajime Arai, Hitoshi Sugiura, Katsuhiko Sugou, Kieko Harada
  • Patent number: 5053288
    Abstract: An optical recording medium, particularly a magneto-optical recording medium, resistant to oxidation deterioration even in a hot and humid atmosphere, is provided by forming an organic protecting adhesive layer of a UV-curved resin having (1) an acid value of not more than 1.5; and (2) a softening point of not less than 50.degree. C. The UV-curved resin layer comprises 15 to 85% by weight of acrylate and/or methacrylate having at least three functionalities; 15 to 70% by weight of a compound having a linear structure and having a molecular weight of at least 300, the compound preferably having at least one ethylenically unsaturated bond and a molecular weight of at least 150 per ethylenically unsaturated bond; and (3) a photopolymerization initiator.
    Type: Grant
    Filed: November 18, 1988
    Date of Patent: October 1, 1991
    Assignee: Teijin Limited
    Inventors: Eiichi Hashimoto, Tetsuo Sato, Kiyoshi Chiba
  • Patent number: 5002856
    Abstract: This invention relates to carbazole diazonium salts which are used in pre-polymer or polymer compositions as sources of photoinitiated strong acids in such developments as imaging films where strong acids are needed to effect polymerization of the film or to remove protective groups.
    Type: Grant
    Filed: August 2, 1989
    Date of Patent: March 26, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Albert G. Anderson
  • Patent number: 4983501
    Abstract: A positive-working radiation-sensitive composition is described, which comprises a binder which is insoluble in water and soluble or swellable in organic solvents and in aqueous-alkaline solutions, a compound which forms a strong acid upon irradiation, and a compound of the general formula ##STR1## wherein R denotes an alkyl group which may be substituted andR.sub.1 and R.sub.2 are identical or different and denote alkyl groups containing 1 to 6 carbon atoms.The composition is suitable for use in the production of radiation-sensitive recording materials such as printing plates or photoresists and is characterized by increased flexibility and good overdevelopment resistance.
    Type: Grant
    Filed: August 3, 1989
    Date of Patent: January 8, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hans Ruckert
  • Patent number: 4983491
    Abstract: A photosensitive composition is described, comprising a diazonium compound and a polyurethane resin having a carboxyl group in its main chain. The composition can be developed with an aqueous alkali developer to provide a lithographic printing plate having a long press life.
    Type: Grant
    Filed: September 22, 1989
    Date of Patent: January 8, 1991
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Kazuo Maemoto, Akihiko Kamiya
  • Patent number: 4980260
    Abstract: A multicolor image-forming method which comprises image-exposing a light-sensitive heat-sensitive recording material having a diazo compound and a coupling component on a support using a positive image followed by developing to form a color image, image-exposing a light-solubilizing color image-forming material having a coloring material on a substantially transparent support using a positive image followed by developing to form a color image, and superposing the light-solubilizing color image-forming material having the color image on the light-sensitive heat-sensitive recording material having the color image or, further, heat-pressing the light-solubilizing color image-forming material having the color image superposed on the light-sensitive heat-sensitive recording material having the color image.
    Type: Grant
    Filed: April 25, 1988
    Date of Patent: December 25, 1990
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Fumiaki Shinozaki, Mikio Totsuka, Tomizo Namiki
  • Patent number: 4957845
    Abstract: The present invention is concerned with a printing plate of which image formation is done by photoirradiation, having a front side covered waith a peelable or removable protective layer which contains a photofading material. The printing plate is safe against fogging to light and can be used under ordinary illumination.
    Type: Grant
    Filed: May 17, 1989
    Date of Patent: September 18, 1990
    Assignee: Toray Industries, Incorporated
    Inventors: Masanao Isono, Ken Kawamura, Masaya Asano, Tetuo Suzuki, Shigeo Abiko
  • Patent number: 4937175
    Abstract: Compositions comprising a free radical sensitive compound and a thermally stable substituted diazene which upon exposure to electromagnetic radiation is convertible to a thermally unstable substituted diazene may be formed and processed utilizing thermally intense techniques and thereafter the free radically initiated changes initiated by exposing the substituted diazene to light and heat.
    Type: Grant
    Filed: January 23, 1989
    Date of Patent: June 26, 1990
    Assignee: The Dow Chemical Company
    Inventors: Jerry E. White, Richard A. Wolf
  • Patent number: 4914000
    Abstract: A light-sensitive compound having the formula: ##STR1## wherein R.sub.3 is selected from the group consisting of phenyl and C.sub.1 to C.sub.4 alklyl substituted phenyl.--K-- is selected from the group consisting of ##STR2## --S--, --O--, and --CH.sub.2 --, or is absent; R.sub.1 and R.sub.2 are independently selected from the group consisting of C.sub.1 to C.sub.4 alkyl, methoxy, ethoxy, butoxy, and H;X-- is an anion; andR denotes a hydrogen atom or a C.sub.1 to C.sub.4 alkyl group.
    Type: Grant
    Filed: February 3, 1988
    Date of Patent: April 3, 1990
    Assignee: Hoechst Celanese Corporation
    Inventor: Major S. Dhillon
  • Patent number: 4895826
    Abstract: A heat-sensitive recording material is disclosed, which comprises a support having thereon a heat-sensitive recording layer comprising a diazo compound and a coupler precursor compound, said coupler precursor compound being capable of forming a compound having an ability of coupling with said diazo compound upon heating.
    Type: Grant
    Filed: April 25, 1988
    Date of Patent: January 23, 1990
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Katsuhiko Watanabe, Takayuki Hayashi, Hiroshi Kamikawa, Masato Satomura, Takekatsu Sugiyama
  • Patent number: 4789619
    Abstract: A positive-working radiation-sensitive mixture is described that contains (a) a radiation-sensitive compound which forms a strong acid under the action of actinic radiation, (b) a compound with at least one C--O--C bond cleavable by acid, (c) a binder which is insoluble in water but soluble in aqueous-alkaline solutions, and (d) a polymethine dye. The polymethine dyes used are hemioxonol dyes or symmetrical cyanine dyes. In the light-sensitive mixture, these dyes effect high sensitization and high image sharpness contrast which, in addition, is substantially irreversible.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: December 6, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans Ruckert, Joachim Knaul
  • Patent number: 4770973
    Abstract: In a heat-sensitive recording material which comprises a substrate and a heat-sensitive recording layer thereon containing a diazonium salt and coupler compound, the heat-sensitive recording material characterized in that the coupler compound comprises at least one compound represented by the formula [I] below ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are each hydrogen atom, halogen atom, alkyl or alkoxyl; R.sub.9 is hydrogen atom or alkyl; X and Y are each hydrogen atom, --OR.sub.10 or --N(R.sub.11)(R.sub.12), R.sub.10, R.sub.11 and R.sub.12 being each hydrogen atom, alkyl, alicyclic group, aryl or aralkyl, these R.sub.10, R.sub.11 and R.sub.12 may have a substituent selected from among halogen atom, alkyl and alkoxy, R.sub.11 and R.sub.12 may link together to form a heteroring, or, one or both of R.sub.11 and R.sub.12 may form a heteroring together with an adjacent benzene ring; n is 0 or 1.
    Type: Grant
    Filed: November 7, 1986
    Date of Patent: September 13, 1988
    Assignee: Kanzaki Paper Manufacturing Limited
    Inventors: Nobuo Kanda, Katsuhiko Ishida, Tosaku Okamoto, Mitsuru Kondo
  • Patent number: 4760048
    Abstract: A multicolor heat-sensitive recording material is disclosed, comprising a support having carried thereon at least two colorless or light-colored color formers capable of developing different colors and color developers capable of reacting with said color formers upon heating to develop colors, wherein at least one of the color formers and color developers is encapsulized, at least one of the color formers is a diazo compound which is substantially decomposed by light, and at least one of the other color formers is a compound which is not substantially decomposed by light. The material provide a multicolor image having excellent hues and sharpness without color smearing and is free from undesired color formation before or after recording.
    Type: Grant
    Filed: February 28, 1986
    Date of Patent: July 26, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Nobuhiro Kurihara, Sumitaka Tatsuta, Jun Yamaguchi, Toshimasa Usami
  • Patent number: 4731316
    Abstract: A photosensitive composition of this invention comprises:(a) a photosensitive diazo resin represented by the following general formula (I): ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 each represents a hydrogen atom, an alkyl or alkoxy group, R represents a hydrogen atom, an alkyl or phenyl group, X represents PF.sub.6 or BF.sub.4 and n represents a number of 1 to 200, in which a resin with the number n in the above formula being 5 or more is contained by more than 20 mol %,(b) an oleophilic high molecular weight compound with hydroxyl group and(c) a high molecular weight organic acid without hydroxyl group, and in which the content of the ingredient (c) is from 1.5 to 30% by weight based on the solid matter in said composition.The photosensitive composition of this invention can provide a photosensitive layer having high sensitivity and being excellent in storage stability and developability as well as excellent in the film strength.
    Type: Grant
    Filed: October 1, 1985
    Date of Patent: March 15, 1988
    Assignees: Mitsubishi Chemical Industries Limited, Konishiroku Photo Industry Co., Ltd.
    Inventors: Hiroshi Tomiyasu, Yoshihiro Maeda, Kiyoshi Goto, Norihito Suzuki
  • Patent number: 4687728
    Abstract: Radiation sensitive compositions are image-wise exposed and developed to form an image which is then heated to improve its strength as a lithographic printing image or etch resist. The heating is carried out in the presence of a heat sensitive dye which undergoes a color change at a temperature of at least 180.degree. C. so as to obtain an indication of whether or not the heating has been adequate. The dye may be an integral component of the composition or it may be applied to the image, after development, in combination with a substance capable of forming a shield against contaminating residues produced during the heating step.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: August 18, 1987
    Assignee: Vickers PLC
    Inventors: Christopher W. Folkard, Christopher R. Millross
  • Patent number: 4668615
    Abstract: A heat developable light-sensitive material containing a compound represented by the general formula (I):[Ar.sub.n (R).sub.3-n CCO.sub.2 H].sub.l .multidot.B.sub.m (I)wherein ar represents an aryl group or a heterocyclic group; R represents a substituent other than an aryl group and a heterocyclic group; Ar and R may be bonded in a part thereof to form a ring; B represents a mono- or diacidic base which has a pKa of 7 or more and contains 12 or less carbon atoms; n represents an integer from 1 to 3; l and m each represents an integer of 1 or 2 and maintain a relationship in that a number of positive charge and a number of negative charge are equal; when n represents 1 or 2, two R's or Ar's may be the same or different, when n represents 3, three Ar's may be the same or different; and the substituent represented by Ar or R may be further substituted with a substituent.
    Type: Grant
    Filed: August 21, 1985
    Date of Patent: May 26, 1987
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Ken Kawata, Yoshiharu Yabuki, Kozo Sato, Hiroyuki Hirai
  • Patent number: 4661432
    Abstract: A light-sensitive, diazonium group-containing polycondensation product is described which comprises(a) an optionally substituted diphenylamine-dianzonium salt I.(b) a compound corresponding to the formula IIR.sup.4 --O--CH.sub.2 --R.sup.5 (II)whereinR.sup.4 is H, alkyl or acyl, andR.sup.5 is an optionally substituted aromatic radical, and(c) a compound corresponding to the formula IIIR.sup.6 --O--CH.sub.2 --R.sup.8 --CH.sub.2 --O--R.sup.7 (III)whereinR.sup.6 and R.sup.7 are H, alkyl, or acyl andR.sup.8 is the radical of a compound selected from the group consisting of aromatic hydrocarbons, phenols, phenolethers, aromatic thioethers, aromatic heterocyclic compounds, and organic acid amides,with the radicals resulting from compound II being directing linked to the units of the diazonium salt I.In the production of the polycondensation product, I is first condensed with II and then with III.
    Type: Grant
    Filed: January 23, 1986
    Date of Patent: April 28, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Walter Lutz, Hartmut Steppan
  • Patent number: 4659653
    Abstract: A heat developable light-sensitive material comprising a support having thereon at least a layer containing a novel compound having a group accelerating a reaction of decarboxylation, which releases a base by decarboxylation on heating. The heat developable light-sensitive material provides an image having a high density in a short time and has an improved storage stability.
    Type: Grant
    Filed: August 26, 1985
    Date of Patent: April 21, 1987
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazo Sato, Yoshiharu Yabuki, Hiroyuki Hirai, Ken Kawata
  • Patent number: 4657848
    Abstract: A heat-developable light-sensitive material is described, containing a compound represented by formula (I) ##STR1## wherein R.sub.1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted alkynylene group, a substituted or unsubstituted aralkylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group; R.sub.2 represents a hydrogen atom, a substituted or unsubstituted alkyl group; R.sub.
    Type: Grant
    Filed: October 2, 1985
    Date of Patent: April 14, 1987
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kozo Sato, Yoshiharu Yabuki, Hiroyuki Hirai, Ken Kawata