Processing Ingredient Other Than Coupler Or Carboxylic Acid Compound Patents (Class 430/177)
  • Patent number: 7935776
    Abstract: The present invention relates to a radiation curable and developable polyurethane which is characterized by having a carboxy group in its main chain and a acryloyl group in its side chain and comprising the following repeat units (I), (II), and (II) in a random arrangement: wherein R1, R2, R3, R4, and T are defined in the specification. The polyurethane has a weight molecular weight measured by GPC in a range of from 3,000 to 400,000; an acid value in a range of from 5 to 120 mgKOH/g. The present invention also relates to a radiation curable and developable composition containing the polyurethane.
    Type: Grant
    Filed: March 20, 2008
    Date of Patent: May 3, 2011
    Assignee: AGI Corporation
    Inventors: Wei Hsiang Huang, Ying Jen Chen, Jui Ming Chang, Chun Hung Kuo, Hong Ye Lin, Li Chung Chang
  • Patent number: 6835522
    Abstract: Disclosed is a heat-sensitive recording material containing an ultraviolet light absorber precursor which forms an ultraviolet light absorber by being irradiated with light, and a hydrogen donor.
    Type: Grant
    Filed: March 13, 2002
    Date of Patent: December 28, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazumori Minami, Masanobu Takashima
  • Publication number: 20040161693
    Abstract: The present invention provides a thermal recording material comprising a support and at least a thermal recording layer disposed on the support, wherein at least one of the thermal recording layer includes, together with an electron donating colorless dye, at least an electron accepting compound represented by the following general formula (1). R1 and R2 each independently represents a hydrogen atom, an alkyl group or an aryl group; and Ar is represented by the following general formula (2). In the general formula(2), R11 to R14 each independently represents a hydrogen atom, an alkyl group with 1 to 4 carbon atoms or an aryl group.
    Type: Application
    Filed: February 19, 2003
    Publication date: August 19, 2004
    Applicant: FUJI PHOTO FILM CO., LTD
    Inventors: Kazumori Minami, Hisao Yamada, Hiroshi Sato
  • Patent number: 6720124
    Abstract: A recording material includes a support having disposed thereon a recording layer including at least: a diazo compound having no diazonio group; a coupler compound that colors by reacting with the diazo compound; and a polymerizable compound.
    Type: Grant
    Filed: May 31, 2002
    Date of Patent: April 13, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Masanobu Takashima, Hiroshi Sato, Yoshimitsu Arai, Kyoko Hanasaki
  • Patent number: 6716566
    Abstract: There is provided a negative planographic printing plate which can be directly recorded based on digital data from computers and the like, excellent in storage stability, shows no reduction in sensitivity with the lapse of time, and has excellent face flatness. It comprises a substrate having disposed thereon a photosensitive layer which is obtained by applying a photosensitive layer application solution containing an infrared absorber, a compound which generates a radical or acid due to heat, a polymerizable compound or a crosslinking compound, and a silicon-based surfactant such as a siloxane/oxyethylene copolymer and the like, onto the substrate and drying the solution, and which is hardened by exposure to an infrared laser ray.
    Type: Grant
    Filed: July 2, 2001
    Date of Patent: April 6, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Keitaro Aoshima
  • Publication number: 20010008739
    Abstract: A positive photoresist composition for exposure to a far ultraviolet ray which comprises (A) a compound which generates an acid upon irradiation with an actinic ray or radiation, (B) a resin which contains a repeating unit corresponding to hydroxystyrene and solubility of which increases in an alkaline developing solution by the action of an acid, and (C) (1) at least one solvent selected from the group consisting of propylene glycol monomethyl ether acetate and propylene glycol monomethyl ether propionate, and (2) at least one solvent selected from the group consisting of propylene glycol monomethyl ether and ethoxyethyl propionate. The positive photoresist composition of the present invention is suitable for exposure to a far ultraviolet ray, particularly a KrF excimer laser beam, is improved in line edge roughness and micro grain, is excellent in uniformity of carting on a substrate and has less particles in its resist solution.
    Type: Application
    Filed: December 22, 2000
    Publication date: July 19, 2001
    Inventors: Fumiyuki Nishiyama, Toru Fujimori
  • Patent number: 6248497
    Abstract: A light-sensitive and heat-sensitive recording material containing a diazo compound and a coupling component or a coupler, in which a density of a recorded image and a whiteness of a base portion are both improved. The recording material includes a recording layer disposed on a substrate. The recording layer preferably contains the diazo compound in the form of a diazonium salt and enclosed in micro-capsules together with an acylphosphine oxide compound, wherein the diazonium salt is reactive with the coupler.
    Type: Grant
    Filed: March 29, 2000
    Date of Patent: June 19, 2001
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shojiro Sano, Masanobu Takashima
  • Patent number: 6127085
    Abstract: A novel photo-curable resin composition. The resin composition capable of providing a cured product having excellent mechanical strength, high dimensional accuracy, and excellent toughness. The resin composition is capable of providing a cured product which experiences little change in mechanical strength over time. The resin composition is capable of forming, by photo-fabricating, a three-dimensional object which can be used for a long period of time in a humid atmosphere. The composition comprises, (A) an epoxy compound having a cyclohexene oxide, (B) a cationic photo-initiator, (C) an ethylenically unsaturated monomer, (D) a radical photo-initiator, and (E) a polyol.
    Type: Grant
    Filed: October 17, 1997
    Date of Patent: October 3, 2000
    Assignees: DSM N.V., JSR Corporation, Japan Fine Coatings Co., LTD
    Inventors: Tetsuya Yamamura, Tsuyoshi Watanabe, Akira Takeuchi, Takashi Ukachi
  • 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: 5633112
    Abstract: A photosensitive resin composition comprising (a) a polymer having carboxyl groups (b) a photoacid generator which generates an acid when irradiated with light, and (c) an aliphatic amine is capable of development with ease by use of a wide variety of aqueous solvents.
    Type: Grant
    Filed: October 7, 1994
    Date of Patent: May 27, 1997
    Assignees: Hitachi, Ltd., Hitachi Chemical Company, Ltd.
    Inventors: Takao Miwa, Yoshiaki Okabe, Mina Ishida, Akio Takahashi, Shunichi Numata
  • Patent number: 5629135
    Abstract: Positive-tone and negative-tone chemically amplified resist compositions comprising: (a-1) a blocked resin, (a-2) a combination of an alkali-soluble resin and a dissolution controlling agents, or (a-3) a combination of an alkali-soluble resin and a crosslinking agent, (b) a photoacid generator, and (c) specific kinds of solvents. The both positive-tone and negative-tone resist compositions exhibits superior sensitivity, high resolution capability, and excellent storage stability, and can be excellently applied especially to large sized substrates by spincoating for producing excellently shaped patterns by irradiation. The compositions can be used with advantage as a chemically amplified resist for the manufacture of semiconductor devices or integrated circuits (ICs).
    Type: Grant
    Filed: January 29, 1996
    Date of Patent: May 13, 1997
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Eiichi Kobayashi, Makoto Murata, Toshiyuki Ota, Akira Tsuji
  • Patent number: 5556733
    Abstract: A thermal development diazo copying material is composed of a support, a diazo layer which contains a diazo compound, and a coupler layer which contains a coupling component, an alkali-soluble resin and a thermofusible material, which are overlaid on the support.
    Type: Grant
    Filed: March 4, 1994
    Date of Patent: September 17, 1996
    Assignee: Ricoh Company, Ltd.
    Inventors: Shigeru Kusakata, Masanori Rimoto
  • Patent number: 5536616
    Abstract: A photoresist is provided. The photoresist comprises a polymer, a photoactive agent, and a crosslinking agent. The crosslinking agent comprises a water soluble sugar. The present invention also provides a method of making microelectronic structures.
    Type: Grant
    Filed: September 21, 1994
    Date of Patent: July 16, 1996
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Jean M. J. Frechet, Sze-Ming Lee
  • 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: 5424164
    Abstract: A recording material which comprises a support having provided thereon capsules containing a photosensitive diazonium salt, and a polymerizable coupler. The recording material can give a predetermined hue when light, pressure, heat and the like are applied alone or in combination. The main advantages of the recording material are that a specific hue can be selected safely, mixing of colors can be avoided, desensitization problem does not occur and a fixed image can be obtained.
    Type: Grant
    Filed: November 10, 1994
    Date of Patent: June 13, 1995
    Assignee: Fuji Photo Film Co., Ltd
    Inventors: Masato Satomura, Ken Iwakura, Akira Igarashi
  • Patent number: 5407777
    Abstract: A diazo-type recording material comprising a support having thereon a recording layer comprising a photosensitive diazo compound enclosed in microcapsules, a coupling component which reacts with said diazo compound by heating at a basic pH to develop a color, and a 1-phenyl-3-pyrazolidone compound represented by the formula: ##STR1## wherein the substituents X, and R.sub.1 -R.sub.4 are defined in the specification.
    Type: Grant
    Filed: November 17, 1992
    Date of Patent: April 18, 1995
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hirokazu Shimada, Akihiro Shimomura
  • Patent number: 5389491
    Abstract: A negative working resist composition comprising (a) an alkali-soluble resin, (b) an aromatic compound having at least two groups of the formula: --OCH.sub.2 OR.sup.1 wherein R.sup.1 is alkyl or aralkyl, (c) a photoacid generator, and (d) a solvent, can form fine patterns with high resolution when exposed to deep UV, KrF excimer laser light, etc. due to high light transmittance and high sensitivity.
    Type: Grant
    Filed: June 28, 1993
    Date of Patent: February 14, 1995
    Assignees: Matsushita Electric Industrial Co., Ltd., Wako Pure Chemical Industries, Ltd.
    Inventors: Yoshiyuki Tani, Masayuki Endo, Fumiyoshi Urano, Takanori Yasuda
  • Patent number: 5328797
    Abstract: The present invention relates to a process for producing a negative-working photosensitive lithographic printing form, in which a negative-working photosensitive mixture which is dissolved in a solvent mixture and which contains a negative-working photosensitive compound and a polymeric binder which is insoluble in water but soluble in aqueous alkaline solution is applied to a base and the layer obtained is subsequently dried, which process comprises using a mixture of more than 2% by weight of at least one monoether of diethylene glycol with one or more organic solvent(s) having a boiling point below 200.degree. C. as the solvent mixture.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: July 12, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudolf Neubauer, Roman Keiper, Siegfried Nuernberger, Sabine Pilger
  • 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: 5272035
    Abstract: A light-sensitive composition comprising (a) a diazonium compound, (b) a polyurethane resin having a substituent group with an acidic hydrogen atom, and (c) a compound of the following general formula: ##STR1## wherein X is a single bond, --O--, --CH.sub.2 --, or --CH.sub.2 O--; Y is an alkyl group, a hydroxy group, an alkoxy group, a nitro group or a halogen atom; n is an interger of from 0 to 5; R is a hydrogen atom, an alkyl group, a phenyl group or a substituted phenyl group; and wherein, when n.gtoreq.2, Y may be the same or different.Also disclosed is a photosensitive lithographic printing plate having a support and a light-sensitive layer deposited thereon. The light-sensitive layer comprises the above novel light-sensitive composition.
    Type: Grant
    Filed: May 15, 1991
    Date of Patent: December 21, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Toshiyuki Sekiya
  • Patent number: 5143813
    Abstract: A light-sensitive mixture is described which contains a diazonium salt polycondensation product, a free-radical polymerizable compound having at least one terminal ethylenically unsaturated group and a boiling point at atmospheric pressure above 100.degree. C., a polymerization initiator which forms free radicals under the action of actinic radiation, and, as a first binder, a water-insoluble reaction product which is soluble in organic solvents and in aqueous alkaline solutions, which is a reaction product of an intramolecular anhydride of an organic polycarboxylic acid with a hydroxyl-containing synthetic polymer, and which has no further functional groups capable of reacting with acid anhydrides, and, as a further binder, an acid organic polymer having an acid number above 70, preferably a (meth)acrylic acid copolymer. The mixture is useful for producing planographic printing plates which give long print runs, and is notable for a long shelf life at elevated temperature.
    Type: Grant
    Filed: February 1, 1990
    Date of Patent: September 1, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Klaus Joerg
  • Patent number: 5080999
    Abstract: A light-sensitive composition which comprises, (a) an ethylenically unsaturated addition polymerizable compound, (b) an alkaline water-soluble or swellable, and film-forming polymer, (c) a photopolymerization initiator, (d) a negative working diazo resin, and (e) at least one compound selected from the group consisting of a higher fatty acid and a higher fatty acid amide which are solid at ordinary temperatures.The light-sensitive composition is hardly influenced by oxygen and is suitable for a presensitized plate from which a printing plate is to be prepared.
    Type: Grant
    Filed: May 28, 1991
    Date of Patent: January 14, 1992
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Masanori Imai, Mitsuru Koike, Noriaki Watanabe, Nobuyuki Kita, Tatsuji Higashi
  • Patent number: 5037721
    Abstract: A positive radiation-sensitive mixture is disclosed containing a compound which forms an acid under the influence of actinic radiation, and an acid-cleavable compound, wherein the acid-cleavable compound is monomeric and contains an acetal group whose aldehyde or ketone component has a developer solubility of about 0.1 to 100 g/l and a boiling point above about 150.degree. C. The mixture does not exhibit different development properties, even at different "holding times", and therefore exhibits a wide processing latitude and makes possible a high structural resolution.
    Type: Grant
    Filed: September 13, 1988
    Date of Patent: August 6, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Karl-Friedrich Doessel
  • Patent number: 5009981
    Abstract: A photosensitive composition, comprising a photosensitive diazo compound and a polymeric binder, wherein the diazo compound has a polymerizable unsaturated bond in the molecule.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: April 23, 1991
    Assignees: Konica Corporation, Mitsubishi Kasei Corporation
    Inventors: Shinichi Matsubara, Masafumi Uehara, Shinichi Bunya, Eriko Katahashi
  • 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: 4970133
    Abstract: Presensitized imaging element comprising a support and a light-sensitive hyrophilic layer thereon, said light-sensitive hydrophilic layer containing in homogeneously distributed state throughout the entire layer a hydrophilic (co)polymer or (co)polymer mixture, a tetraalkyl orthosilicate crosslinking agent in an amount of at least 0.2 parts by weight per part by weight of hydrophilic (co)polymer or (co)polymer mixture and a low-molecular weight diazonium salt and preferably also (a) substance(s) that increase(s) the mechanical strength and the porosity of the layer, by means of which a lithographic printing plate can be produced by imagewise exposing said imaging element to an ultraviolet radiation source, subsequently bringing it in the presence of an aqueous liquid in contact with a receptor element comprising a receiving layer containing a polyionic mordant for the diazonium salt and separating it from the receiving layer to leave the residual non-exposed diazonium salt on the receiving layer.
    Type: Grant
    Filed: October 13, 1988
    Date of Patent: November 13, 1990
    Assignee: Agfa-Gevaert, N.V.
    Inventors: Joan T. Vermeersch, Paul J. Coppens
  • Patent number: 4968582
    Abstract: The invention is a modified organic photoresist which is resistant to etching in oxygen-containing plasmas and therefore particularly useful for masking and etching organic polymer materials in VLSI and advanced packaging applications. The invention comprises adding a phosphorous-containing compound to a conventional photoresist. The phosphorous-containing compound is of a type and in an amount effective to substantially prevent etching of the modified photoresist in an oxygen-containing plasma without substantially adversely affecting the photosensitivity of the photoresist or the elasticity or the adhesion of the etch resistant film formed during oxygen-containing plasma exposure to an underlying material to be patterned and etched.
    Type: Grant
    Filed: June 28, 1988
    Date of Patent: November 6, 1990
    Assignee: MCNC and University of NC at Charlotte
    Inventors: Farid M. Tranjan, Thomas D. DuBois, Rudolf G. Frieser, Stephen M. Bobbio, Susan K. S. Jones
  • Patent number: 4957847
    Abstract: A heat-sensitive recording material comprising a base and, on top of the said base, a heat-sensitive layer containing a cyclic diazo component and a coupling component, the cyclic diazo component being a benzotriazine compound of the formula ##STR1## wherein Q is --CH.sub.2 --, --CO-- or --SO.sub.2 --, R is hydrogen, hydroxyl, or aryl or alkenyl, each unsubstituted or substituted by halogen, hydroxyl, cyano, lower alkoxy, lower alkylthio, acyloxy, lower alkoxycarbonyl or lower alkylsulfonyl, or is acyl, acyloxy or acylamino, cycloalkyl, or is aryl or aralkyl such as phenyl, phenylalkyl or naphthyl each unsubstituted or substituted on the ring by cyano, halogen, nitro, trifluoromethyl, lower alkyl, lower alkylthio, lower alkoxy, lower alkylcarbonyl or lower alkoxycarbonyl, or is a heterocyclic radical, and the benzene ring A is unsubstituted or substituted by halogen, cyano, nitro, lower alkyl, lower alkoxy, lower alkylthio, lower alkylcarbonyl or lower alkoxycarbonyl.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: September 18, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Jean-Marie Adam, Hans Baumann
  • Patent number: 4946759
    Abstract: A positive radiation-sensitive mixture is disclosed comprising a compound which forms an acid under the action of actinic radiation, and an acid-cleavable compound, the acid-cleavable compound producing, as cleavage product, an aromatically-substituted alcohol of the general formula I. The radiation-sensitive mixture according to the inventionexhibits a wide processing latitude since different holding times do not cause any changes with respect to the development times.
    Type: Grant
    Filed: September 13, 1988
    Date of Patent: August 7, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl-Friedrich Doessel, Ralph Dammel, Juergen Lingnau
  • Patent number: 4929533
    Abstract: A process is described for producing a presensitized lithographic printing plate by coating onto a surface-roughened aluminum plate a solution having dissolved in a solvent containing at least 10 wt % 1-methoxy-2-propanol a negative-working, light-sensitive composition which contains a light-sensitive diazo resin and a high-molecular weight compound and which is developable with an aqueous alkali developer, and drying the coated solution.
    Type: Grant
    Filed: July 1, 1988
    Date of Patent: May 29, 1990
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Nobuo Nishikawa, Hiroshi Misu
  • Patent number: 4917988
    Abstract: A process for producing a photosensitive lithographic plate comprises coating onto a substrate having a hydrophilic surface a solution of a negative working photosensitive composition containing a photosensitive diazo resin and a linear organic polymer dissolved in a solvent mixture comprising:(a) at least 10 wt. % of 1-methoxy-2-propanol,(b) an amino group-free polar solvent having a boiling point under 1 atm of 50.degree. to 100.degree. C. and a dielectric constant at 20.degree. C. of at least 5.5, and(c) 2 to 50 wt. % of methyl lactate,and drying the coated solution.
    Type: Grant
    Filed: February 17, 1988
    Date of Patent: April 17, 1990
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shigeo Koizumi, Nobuo Nishikawa, Nobuyuki Kita
  • Patent number: 4912013
    Abstract: A photosensitive composition principally comprised of a photosensitive diazo resin and a lipophilic high molecular compound, wherein said photosensitive composition further contains a metal complex dye soluble in an organic solvent. Also disclosed is a photosensitive lithographic printing plate employing such a photosensitive composition.
    Type: Grant
    Filed: November 8, 1988
    Date of Patent: March 27, 1990
    Assignees: Konishiroku Photo Industry Co., Ltd., Mitsubishi Chemical Industries Limited
    Inventors: Norihito Suzuki, Kiyoshi Goto, Yoshihiro Maeda, Shigeki Shimizu
  • Patent number: 4891297
    Abstract: A heat-sensitive recording material is disclosed. The material comprises a support having provided thereon a recording layer containing one or more diazo compound, a coupling component, and at least one thiohydroquinone derivative as a sensitizing agent.
    Type: Grant
    Filed: March 25, 1988
    Date of Patent: January 2, 1990
    Assignee: Fuji Photo Film Co.,Ltd.
    Inventors: Masanobu Takashima, Ken Iwakura, Masato Satomura, Kimio Ichikawa
  • Patent number: 4877711
    Abstract: A light-sensitive composition which contains a polyurethane resin having a carbon-carbon unsaturated bond and a carboxyl group. A presensitized plate using the above light-sensitive composition can be developed with an aqueous alkaline developing solution and provides a lithographic printing plate having excellent printing durability.
    Type: Grant
    Filed: May 12, 1987
    Date of Patent: October 31, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Kazuo Maemoto, Akihiko Kamiya, Hiroshi Misu
  • Patent number: 4851319
    Abstract: This invention relates to a radiation polymerizable composition for use in a photographic element such as a lithographic printing plate comprising in admixturea) a polymeric binder;b) a photoinitiator;c) a diazonium salt; andd) a photopolymerizable mixture ofi) a polyfunctional acrylic monomer having from 3 to 6 unsaturated groups; andii) a monofunctional acrylic monomer having 1 unsaturated group.
    Type: Grant
    Filed: April 19, 1988
    Date of Patent: July 25, 1989
    Assignee: Hoechst Celanese Corporation
    Inventors: John E. Walls, Carlos Tellechea
  • Patent number: 4840869
    Abstract: Light sensitive compositions are disclosed which comprise 2-halomethyl-1,3,4,-oxadiazole compounds having a heterocyclic radical in the fifth position containing at least one element selected from the group consisting of oxygen, nitrogen, sulphur, and selenium directly or through a vinyl radical.
    Type: Grant
    Filed: August 10, 1987
    Date of Patent: June 20, 1989
    Assignee: Konishiroku Photo Industry Co., Ltd.
    Inventors: Noriyasu Kita, Kiyoshi Goto
  • Patent number: 4828959
    Abstract: A light-sensitive mixture that contains a diazonium salt polycondensation product, a polymeric binder and an organic peroxide which has a scorch temperature of at least 100.degree. C. and, above this temperaure, is capable of forming free radicals is especially useful for the preparation of planographic printing plates, the print run of which can be extended by burning-in the exposed and developed plate. The light-sensitive mixture has a long storage life in the dark.
    Type: Grant
    Filed: May 22, 1987
    Date of Patent: May 9, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Dieter Mohr, Guenter Jung
  • Patent number: 4828957
    Abstract: Disclosed is a two-color heat-sensitive recording material which comprises a base sheet and a recording layer of single-layer or multi-layer structure formed on the base sheet, the recording layer comrising:(a) a diazonium salt,(b) a basic leuco dye,(c) a 2-hydroxy-3-naphthoic acid derivative which acts as a coupler compound for causing the diazonium salt to develop color when heated and which also acts as a color developing material for causing the basic leuco dye to develop color when heated, and(d) a basic substance, wherein the diazonium salt and the basic leuco dye each form a color upon application of heat, thereby giving the first image of a mixed color, and, then, after irradiation of an active ray to decompose the diazonium salt, the basic leuco dye alone forms its own color upon application of heat, thereby giving the second image whose color is different from the mixed color of the first image.
    Type: Grant
    Filed: May 26, 1987
    Date of Patent: May 9, 1989
    Assignee: Kanzaki Paper Manufacturing Company, Ltd.
    Inventors: Naoki Yonese, Tosaku Okamoto, Mitsuru Kondo
  • Patent number: 4777111
    Abstract: This invention relates to a composition and method for enhancing the contrast of images of an underlying photolithographic layer. A photographic element, including a photoresist layer, is applied to a substrate. The photoresist layer contains a contrast-enhancing layer including at least one light-sensitive compound capable of producing acidic photoproducts upon exposure to actinic radiation, at least one indicator dye that changes color on exposure to acidic conditions and at least one polymeric binder soluble in water or weakly alkaline aqueous solutions. The photographic element is exposed to active radiation sufficient to cause photobleaching of the contrast enhancement layer and exposure of the photoresist layer. The photographic element is exposed to actinic radiation sufficient to cause photobleaching of the contrast enhancement layer and exposure of the photoresist layer.
    Type: Grant
    Filed: March 23, 1987
    Date of Patent: October 11, 1988
    Assignee: Fairmount Chemical Company, Inc.
    Inventors: David B. Blumel, Albert S. Deutsch
  • Patent number: 4752552
    Abstract: A photosolubilizable composition contains both a compound capable of producing an acid by irradiation with actinic rays and a compound which has at least one silyl ether or silyl ester group capable of being decomposed by an acid; optionally, a compound having at least one silyl ether group has at least one hydrophilic group, providing for increased solubility in a developing solution under the action of an acid, thus enhancing the photosensitivity and the development latitude of the composition.
    Type: Grant
    Filed: August 12, 1987
    Date of Patent: June 21, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Toshiaki Aoai
  • Patent number: 4737436
    Abstract: A method of forming an image on a substrate is described which comprises blending a desired coloring pigment, adding the coloring pigment to a water soluble photoresist, coating the substrate with the pigmented photoresist, exposing the photoresist to actinic radiation to harden the parts of the photoresist occupying the desired image area, and removing with a water based solvent the unexposed photoresist.
    Type: Grant
    Filed: November 18, 1985
    Date of Patent: April 12, 1988
    Assignee: Grafmark International Limited
    Inventor: Colin G. Thompson
  • Patent number: 4737426
    Abstract: Compounds of formula I ##STR1## in conjunction with compounds that donate acid when exposed to actinic radiation, are suitable for use as positive photoresists. In formula I, R.sup.1 and R.sup.2 are hydrogen, alkyl, aryl, cycloalkyl, aralkyl or alkaryl, R.sup.3 to R.sup.8 are hydrogen or lower alkyl, X is --O-- or --NR.sup.9 --, where R.sup.9 is hydrogen or C.sub.1 -C.sub.4 alkyl, n is 0 or 1, m is 2, 3 or 4 and Q is an organic radical of valency m.The photoresists are suitable for making printing forms, printed circuits, integrated circuits or silver-free photographic films.
    Type: Grant
    Filed: May 5, 1986
    Date of Patent: April 12, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Martin Roth
  • Patent number: 4737484
    Abstract: A heat-sensitive recording material is described, comprising a support having provided thereon a recording layer comprising a diazo compound and a coupling component, wherein the improvement comprises including said diazo compound and at least one compound selected from a polymerizable compound containing an ethylenically unsaturated bond therein or at least one compound capable of releasing a free radical upon exposure to light together in microcapsules.
    Type: Grant
    Filed: April 19, 1985
    Date of Patent: April 12, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Masayuki Iwasaki, Hiroshi Kamikawa, Toshimasa Usami
  • Patent number: 4705736
    Abstract: A diazotype sheet is developable solely by heat, the sheet comprising in at least one layer a heat-softenable, organic solvent-soluble resin, an acid-stabilized diazonium salt, at least one azo-coupler compound capable of reacting to form a dye, and an acid neutralizing component immobilized either by encapsulation or by coating as a separate layer with or without a binder. The sheet has incorporated therein at least one plasticizer which is either liquid at room temperature (i.e., 20.degree. to 25.degree. C.) or fusible at a temperature between room temperature and the development temperature.
    Type: Grant
    Filed: December 5, 1985
    Date of Patent: November 10, 1987
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Norman T. Notley
  • 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: 4659643
    Abstract: A heat-sensitive recording material comprising a substrate and a heat-sensitive recording layer thereon, the heat-sensitive recording layer containing a diazonium salt, coupler compound, heat-fusible basic compound and at least one of the compounds represented by the formula [I] below ##STR1## wherein X is --O-- or --CONH--, R.sub.1 and R.sub.2 are each hydrogen, halogen, alkyl having 1 to 8 carbon atoms, cycloalkyl, aryl, aralkyl or alkoxyl and n is an integer of 1 to 10.
    Type: Grant
    Filed: October 21, 1985
    Date of Patent: April 21, 1987
    Assignee: Kanzaki Paper Manufacturing Co. Ltd.
    Inventors: Katsuhiko Ishida, Masaharu Nojima, Tosaku Okamoto
  • Patent number: 4659645
    Abstract: A photosensitive mixture comprised of(a) a diazonium salt polycondensation product comprising recurring units of the formulas A--N.sub.2 X and B, which units are linked by bivalent intermediate members derived from a carbonyl compound which is capable of condensation, wherein the A--N.sub.2 X units are derived from aromatic diazonium compounds that are capable of condensation with formaldehyde, and the B units are derived from compounds which are free from diazonium groups and are also capable of condensation with formaldehyde in a strongly acidic medium;(b) a compound which can be polymerized by a free-radical process;(c) a photopolymerization initiator; and(d) a polymeric binder that is insoluble in water, but soluble in organic solventscan be used in the production of photosensitive printing plates and photoresists.
    Type: Grant
    Filed: July 9, 1985
    Date of Patent: April 21, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans-Dieter Frommeld, Walter Lutz, Hartmut Steppan
  • Patent number: 4650740
    Abstract: A heat-sensitive recording material is described, comprising a support having provided thereon a recording layer comprising a binder containing a diazonium compound and a coupling component, said diazonium compound being a diazonium salt represented by formula (I)ArN.sub.2.sup.+ X.sup.- (I)wherein Ar represents a substituted or unsubstituted aromatic moiety; and X.sup.- represents an acid anion containing an alkyl group having three or more fluorine atoms.
    Type: Grant
    Filed: September 13, 1984
    Date of Patent: March 17, 1987
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshimasa Usami, Toshiharu Tanaka, Fumiaki Shinozaki
  • Patent number: 4645730
    Abstract: The lithographic printing plate of the invention comprises a substrate having a hydrophilic surface, a coating on said surface of a light sensitive material (e.g., a water soluble diazo) and a top coating of discrete, oleophilic resin particles (e.g., an emulsion polymer), the resin particle coating being:(a) transparent to actinic light;(b) sufficiently permeable to allow a developer for the light sensitive material to penetrate through to the underlying light sensitive coating;(c) insoluble in said developer;(d) capable of being coalesced in situ after the plate is imaged and developed.
    Type: Grant
    Filed: September 17, 1984
    Date of Patent: February 24, 1987
    Assignee: Howard A. Fromson
    Inventors: Howard A. Fromson, Robert F. Cracia
  • Patent number: 4617250
    Abstract: A light-sensitive composition for use with lithographic printing plates is described which comprises (1) a light-sensitive, organic solvent soluble and substantially water-insoluble diazo resin which is the reaction product of a water-soluble, light-sensitive condensate of an aromatic diazonium compound and an organic condensing agent with a halogenated Lewis acid or a salt thereof, (2) a substantially water-insoluble, film forming organic high-molecular weight compound having an acid value of from 10 to 200, (3) a polynuclear aromatic sulfonic acid or a salt thereof, and (4) a salt-forming organic dye compound.
    Type: Grant
    Filed: June 1, 1984
    Date of Patent: October 14, 1986
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Eiji Nakakita, Akinobu Koike, Toshiyuki Sekiya, Hiroshi Misu, Nobuyuki Kita