Nitrogen Atom Containing Organic Ingredient Patents (Class 430/179)
  • Patent number: 7220529
    Abstract: A photopolymerizable composition comprising at least a polymerizable compound having an ethylenically unsaturated bond, a photo-radical generator, and an amine compound represented by the following Formula (I): wherein R1 and R2 independently represent an optionally substituted aliphatic group, or may be bound to each other to form a ring, A represents an optionally substituted divalent aliphatic linking group, or may be bound to R1 or R2 to form a ring, B represents an optionally substituted divalent linking group selected from an amide linkage, a sulfonamide linkage and an ester linkage, or may be bound to R1 or R2 to form a ring, and Ar represents an optionally substituted aromatic group.
    Type: Grant
    Filed: February 18, 2005
    Date of Patent: May 22, 2007
    Assignee: Fujifilm Corporation
    Inventor: Hirotaka Matsumoto
  • Patent number: 6864032
    Abstract: The present invention provides a method for forming an azo colorant by reaction of a diazo compound and a coupler. The coupler has a leaving group at the coupling position thereof, such that a coupling reaction rate is faster than it would be if the coupler did not have the leaving group. The coupling reaction rate constant k is preferably 0.1 (s?1) or more.
    Type: Grant
    Filed: April 18, 2001
    Date of Patent: March 8, 2005
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hisao Yamada, Mitsuyuki Tsurumi, Kazunori Nigorikawa
  • Patent number: 6346359
    Abstract: Disclosed are a pyrrolopyrimidineone compound represented by the following general formula (1) and a heat-sensitive recording material using the pyrrolopyrimidineone compound as a coupler: General formula (1) wherein R1 and R2 each independently represents a hydrogen atom, a halogen atom, an aryl group, an alkyl group, a cyano group, an acyl group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, or an arylsulfonyl group; R3 represents an amino group, a substituted amino group, a hydroxyl group, an acyloxy group, an arylcarboxyl group, an alkoxy group, an aryloxy group, an alkylthio group, or an arylthio group; R4 represents a hydrogen atom, a halogen atom, or an electron attracting group whose Hammett substituent constant &sgr;p is 0.2 or more; and L represents a substituent group which can leave when the compound reacts with a diazonium salt.
    Type: Grant
    Filed: April 24, 2000
    Date of Patent: February 12, 2002
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hisao Yamada, Mitsuyuki Tsurumi, Kazunori Nigorikawa
  • 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: 6228553
    Abstract: A pyrrolo[1,2-a]pyrimidine compound providing an excellent color-forming property is provided. Further, a novel cyan color-forming type diazo heat-sensitive recording material having excellent shelf life, image light-resistance and image fixing property is provided. The pyrrolo[1,2-a]pyrimidine compound is represented by following general formula (1). The heat-sensitive recording material comprises a substrate, and on the substrate, a heat-sensitive recording layer containing a diazonium salt compound and a coupler. The coupler contains at least one of pyrrolo[1,2-a]pyrimidine compounds represented by following general formula (1). In the formula, R1 represents an aryl group or the like, R2 represents an alkoxycarbonyl group or the like, R3 and R4 represent an acyl group or the like, and R5 represents a hydrogen atom or the like.
    Type: Grant
    Filed: July 8, 1999
    Date of Patent: May 8, 2001
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Tetsunori Matsushita, Naoto Yanagihara, Masanobu Takashima, Mitsuyuki Tsurumi
  • Patent number: 6060206
    Abstract: Disclosed is a photo- and heat-sensitive recording material comprising a substrate and a photo- and heat-sensitive recording layer formed thereon containing a diazo compound and a coupler, wherein the coupler is a compound represented by the general formula (1) or the general formula (2): ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each independently a hydrogen atom or a substituent group; and R.sup.1 and R.sup.2 may join with each other to form a ring. The reaction between the coupler represented by the general formula (2) and a specific diazo compound produces a magenta colorant having very sharp absorption characteristics. In short, the present invention provides a photo- and heat-sensitive recording material which does not inhibit the fixing and which exhibits excellent color formation, color reproduction, and image durability. Further, the present invention provides a magenta colorant which exhibits excellent absorption characteristics.
    Type: Grant
    Filed: October 1, 1998
    Date of Patent: May 9, 2000
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Koichi Hanaki, Yasuhiro Mitamura, Atsuhiro Ohkawa
  • 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: 5744281
    Abstract: A resist composition for forming a pattern, which comprises (a) a compound represented by the following formula (1) and satisfying the following inequalities, ##STR1## wherein R.sup.1 is hydrogen atom or methyl group, R.sup.2 is a monovalent organic group, m is 0 or a positive integer, n is a positive integer, and m and n satisfying a condition of 0.03.ltoreq.n/(m+n).ltoreq.1, (b) a compound capable of generating an acid when irradiated with light, and (c) 4-phenylpyridine, wherein a weight-average molecular weight, Mw and a number-average molecular weight, Mn satisfy the following inequality, 4,000.ltoreq.Mw.ltoreq.50,000, 1.10.ltoreq.Mw/Mn.ltoreq.2.50 (Mw and Mn respectively represent value converted in styrene).
    Type: Grant
    Filed: May 1, 1997
    Date of Patent: April 28, 1998
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Hirokazu Niki, Hiromitsu Wakabayashi, Rumiko Hayase, Naohiko Oyasato, Yasunobu Onishi, Kazuo Sato, Kenji Chiba, Takao Hayashi
  • Patent number: 5693451
    Abstract: The present invention relates to a single or multi-layer recording material for recording images or data, which material has at least one layer sensitive to light or to heat of a plastic containing a pyrrole compound or a pyrrole oligomer.
    Type: Grant
    Filed: September 23, 1994
    Date of Patent: December 2, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Alexa Sommer, Udo Herrmann, Robert Bloodworth, Gunther Penners, Klaus Sommer
  • Patent number: 5679494
    Abstract: A heat-sensitive recording material comprising a support having thereon a heat-sensitive recording layer and a protective layer in this sequence, said heat-sensitive recording material containing a compound represented by formula (1), (2), (3), or (4): ##STR1##
    Type: Grant
    Filed: February 16, 1995
    Date of Patent: October 21, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazumori Minami, Ken Iwakura
  • Patent number: 5658706
    Abstract: A resist composition for forming a pattern, which comprises (a) a compound represented by the following formula (1) and satisfying the following inequalities, ##STR1## wherein R.sup.1 is hydrogen atom or methyl group, R.sup.2 is a monovalent organic group, m is 0 or a positive integer, n is a positive integer, and m and n satisfying a condition of 0.03.ltoreq.n/(m+n).ltoreq.1, (b) a compound capable of generating an acid when irradiated with light, and (c) a nitrogen-containing compound, wherein a weight-average molecular weight, Mw and a number-average molecular weight, Mn satisfy the following inequality, 4,000.ltoreq.Mw.ltoreq.50,000, 1.10.ltoreq.Mw/Mn.ltoreq.2.50 (Mw and Mn respectively represent value converted in styrene).
    Type: Grant
    Filed: September 8, 1994
    Date of Patent: August 19, 1997
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Hirokazu Niki, Hiromitsu Wakabayashi, Rumiko Hayase, Naohiko Oyasato, Yasunobu Onishi, Kazuo Sato, Kenji Chiba, Takao Hayashi
  • Patent number: 5543260
    Abstract: A diazo heat-sensitive recording material containing a support having provided thereon a recording layer containing a diazo compound, a coupler, and an organic base, wherein the diazo compound is a compound represented by formula (I): ##STR1## wherein R.sub.1 represents --C(Z.sub.1)(Z.sub.2)--CH.sub.2 --A, --CH.sub.2 --C(Z.sub.1)(Z.sub.2)--A or --{C(Z.sub.1)(Z.sub.2)}.sub.m --A,wherein Z.sub.1 represents an alkyl group, an aralkyl group or an aryl group; Z.sub.2 represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group; A represents a halogen atom, an acyl group, a cyano group, or a group containing at least one oxygen, nitrogen, phosphorus or sulfur atom through which A is bonded to --CH.sub.2 -- or Z.sub.2 ; and m represents an integer of 1 to 5;R.sub.2 and R.sub.3, which may be the same or different, each represent an alkyl group, an aralkyl group or an aryl group; R.sub.1 and R.sub.
    Type: Grant
    Filed: November 8, 1994
    Date of Patent: August 6, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Keiichi Tateishi, Sadao Ishige, Hiroshi Kamikawa
  • Patent number: 5527659
    Abstract: There is described a chemical amplification resist composition which comprises squarylium compounds represented by the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and represent substituted or unsubstituted aminophenyl, 9-julodidyl, Y.dbd.CH-- (wherein Y represents substituted or unsubstituted heterocyclic group containing nitrogen, or a group: ##STR2## (wherein Z.sup.1 and Z.sup.2 are the same or different and represent substituted or unsubstituted phenyl), photochemical acid generator and binders.
    Type: Grant
    Filed: October 28, 1994
    Date of Patent: June 18, 1996
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Tsuguo Yamaoka, Kenichi Koseki, Mitsuharu Obara, Ikuo Shimizu, Yukiyoshi Ito
  • 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: 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: 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: 5049477
    Abstract: A radiation responsive composition containing a compound represented by the following formula (I) and a photoreducing agent capable of forming a redox couple together with said compound for many uses, e.g., image formation, etching, plating, etc.: ##STR1## wherein N represents a nitrogen atom; X represents an oxygen atom (--O--), a sulfur atom (--S--), or a nitrogen-containing group of formula, ##STR2## R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each represents a mere bond, a substituted or unsubstituted alkyl, aryl, heterocyclic, acyl, aralkyl, alkenyl, alkynyl or carbamoyl group, or a sulfonyl group into which a substituted or unsubstituted alkyl or aryl group has been introduced, provided that at least one of the substituents R.sup.1 to R.sup.3 be a substituted or unsubstituted aryl or heterocyclic group and that two or more of R.sup.1, R.sup.2 and R.sup.3, or of R.sup.1, R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: April 14, 1989
    Date of Patent: September 17, 1991
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Koki Nakamura, Masayoshi Tsuboi, Keizo Koya
  • Patent number: 5047309
    Abstract: A photosensitive recording material comprising (a) a substrate having a hydrophilic surface, (b) an undercoating layer comprising at least one compound having at least one functional group selected from the group consisting of thiol, thioether and disulfide groups, and (c) a photosensitive layer comprising at least one diazonium compound and a high molecular weight binder compound which is insoluble in water and soluble in aqueous alkaline solution. The resulting developed plate yields no background contamination in printing process.
    Type: Grant
    Filed: June 6, 1989
    Date of Patent: September 10, 1991
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Akinobu Koike, Keiji Akiyama
  • Patent number: 4980263
    Abstract: A light-sensitive composition comprises a diazo resin, a polymeric binder, and at least one compound having at least one structural unit selected from the group consisting of ureido bond, thioureido bond, urethane bond and thiourethane bond. The light-sensitive composition can suitably be used for preparing a presensitized plate for use in making lithographic printing plates and is excellent in developability with an aqueous alkaline developer.
    Type: Grant
    Filed: March 2, 1989
    Date of Patent: December 25, 1990
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Toshiyuki Sekiya
  • Patent number: 4968586
    Abstract: A negative-working imaging composition suitable for use as a dry film resist, comprises, in admixture, (a) a polymeric binder, (b) a Co (III) compound capable of partial reduction to Co (II) upon exposure to activating radiation, and (c) a redox transfer ligand capable of reacting with Co (II) to form a Co (II) chelate which reduces adjacent remaining Co (III) compound and forms a Co (III) chelate effective to provide imagewise differential solubility to the composition. The composition can be imagewise exposed to activating radiation, such as a laser, heated, and developed with a developer to form a resist image in the exposed areas. An element comprising a support and a layer of the above-described composition is particularly useful in the manufacture of printed circuit boards by laser direct imaging.
    Type: Grant
    Filed: December 14, 1989
    Date of Patent: November 6, 1990
    Assignee: Eastman Kodak Company
    Inventor: Thap DoMinh
  • 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: 4954418
    Abstract: A photoresist film containing a phosphate of a formalin condensate of diazodiphenylamine, 2.5-bis(4'-azide-2'-sulphobenzilidene) cyclopentanone Na, polyvinylalcohol, and polyvinylpyrrolidone is formed on the inner surface of a faceplate. The photoresist film is hardened by light exposure using a point or linear light source, which is essentially a circular light source, via a shadow mask having a large number of apertures. A light absorbing film is formed on this photoresist film. Then the hardened photoresist film and the light absorbing film on top of it are removed using a peeling agent.
    Type: Grant
    Filed: May 31, 1989
    Date of Patent: September 4, 1990
    Assignee: Kabushiki Kaisha Toshiba
    Inventor: Norio Koike
  • Patent number: 4842979
    Abstract: A heat-sensitive recording material comprising a support having provided thereon a heat-sensitive layer containing microcapsules containing at least one diazonium salt capable of azo-coupling with 2-hydroxy-3-naphthoic acid anilide to develop a blue color, a 2-hydroxy-3-naphthoic acid amide derivative, a benzoylacetic amide derivative represented by the following formula and a basic substance: ##STR1## wherein X represents a hydrogen atom, a halogen atom, a lower alkyl group or an alkoxy, aralkyloxy, phenoxy or acylamino group having up to 18 carbon atoms; Y represents an alkyl or aralkyl group having from 7 to 18 carbon atoms, an alkoxy, aralkyloxy, phenoxy, naphthyloxy, alkylthio, aralkylthio or phenylthio group having from 6 to 18 carbon atoms, a naphthylthio group, a sulfonyloxy group, a sulfamoyl gorup, a ureido group, a thioureido group or an acylamino group; X' and Y' each represents a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group; and Y and Y' may combine to form a substit
    Type: Grant
    Filed: November 30, 1987
    Date of Patent: June 27, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Sadao Ishige, Toshimasa Usami, Hiroshi Kamikawa, Toshiharu Tanaka
  • 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: 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: 4772534
    Abstract: A light-sensitive composition containing a novel light-sensitive s-triazine compound represented by the formula (I) as a free radical-generating agent is disclosed. The s-triazine compound responds radiation in the range of the near ultraviolet to visible light, shows high sensitivity for photolysis and, therefore, the compositon has high light-sensitivity.
    Type: Grant
    Filed: September 5, 1986
    Date of Patent: September 20, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kouichi Kawamura, Hirokazu Kondo, Yoshimasa Aotani
  • 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: 4701399
    Abstract: A photosensitive composition containing a 2-halomethyl-5-substituted-1,3,4-oxadiazole compound represented by the following general formula (I): ##STR1## wherein A represents a substituted or unsubstituted aromatic residue; X represents a hydrogen atom, a cyano group, an alkyl group or an aryl group; Y represents a chlorine atom or a bromine atom; and n represents an integer of 1 to 3.The free radical generating agent represented by the general formula (I) has a photosensitive wavelength range from near ultraviolet range to visible range, high photo-decomposition sensitivity and good compatibility with other components present in the photosensitive composition.The photosensitive composition is suitable for use in light-sensitive printing plates or photo-resists.
    Type: Grant
    Filed: February 25, 1985
    Date of Patent: October 20, 1987
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Teruo Nagano, Tadao Toyama, Akira Nagashima
  • Patent number: 4659644
    Abstract: A diazo-type thermosensitive recording material is disclosed, which comprises a support material and a thermosensitive coloring layer formed on the support material, which thermosensitive coloring layer comprises a diazonium compound, a coupler and a thermo-fusible or thermo-softening material, the coupler being a combination of a hydrazone-type coupler of the formula of R.sup.1 --NH--N.dbd.CH--R.sup.2 (wherein R.sup.1 and R.sup.2 are defined in detail in the specification) and a two-valence metal compound capable of chelating with the coupled product produced by the coupling of the diazonium compound and the hydrazone-type coupler.
    Type: Grant
    Filed: December 19, 1984
    Date of Patent: April 21, 1987
    Assignee: Ricoh Company, Ltd.
    Inventors: Takayuki Hoshina, Michihisa Takahashi, Masanori Rimoto, Masanaka Nagamoto
  • 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: 4652512
    Abstract: This invention provides a heat-sensitive recording material comprising a substrate and a heat-sensitive recording layer which is formed over the substrate and which contains a diazonium salt, a coupler and at least one of specific heat-fusible basic amidine and diamidine compounds in which the nitrogen atom(s) of ##STR1## moiety(moieties) has(have) a substituent and the nitrogen atom(s) or ##STR2## moiety(moieties) has(have) at least one substituent, the substituent being independently selected from the group consisting of phenyl, naphthyl, phenyl-C.sub.1 -C.sub.4 alkyl and naphthyl-C.sub.1 -C.sub.4 alkyl, each optionally substituted with C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, phenyloxy, nitro or halogen, and in which amidine compounds are other than formamidines. The heat-sensitive recording material is especially excellent in storage stability.
    Type: Grant
    Filed: January 29, 1986
    Date of Patent: March 24, 1987
    Assignee: Kanzaki Paper Manufacturing Company, Limited
    Inventors: Katsuhiko Ishida, Masaharu Nojima, Tosaku Okamoto
  • 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: 4640891
    Abstract: A heat developable light-sensitive material having an excellent stability with time and capable of providing a high quality image is disclosed, which contains a base precursor represented by the following general formula (I): ##STR1## wherein A represents an organic residue represented by the following formula (II): ##STR2## X represents an electron attractive substituent having a Hammett's sigma value of more than 0;l represents an integer of 1 to 5 and, when l represents 2 or more, a plurality of Xs may be the same or different;Y represents a substituent having a Hammett's sigma value of 0 or less;k represents an integer of 0 to 5 and, when k represents 2 or more, a plurality of Ys may be the same or different;Z represents a divalent organic residue selected from the group consisting of --C.dbd.
    Type: Grant
    Filed: August 23, 1985
    Date of Patent: February 3, 1987
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yoshiharu Yabuki, Kozo Sato, Ken Kawata, Hiroyuki Hirai
  • Patent number: 4637902
    Abstract: A base precursor represented by the following general formula (A) or (B): ##STR1## wherein A.sub.1, A.sub.2, A.sub.5, A.sub.6, A.sub.7, and A.sub.8 each represents a hydrogen atom, an alkyl group, a substituted alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, a substituted aryl group, an acyl group, or a heterocyclic group, and A.sub.1 and A.sub.2 can combine to form a ring and two of A.sub.5, A.sub.6, A.sub.7, and A.sub.8 can combine to form a ring, A.sub.3 and A.sub.4 each represents a hydrogen atom, an alkyl group, a substituted alkyl group, a cycloalkyl group, or an aralkyl group, and A.sub.3 and A.sub.4 can combine to form a ring or A.sub.3 and A.sub.4 can be a double bond forming an imino group from ##STR2## and X represents a nucleophilic group.
    Type: Grant
    Filed: March 14, 1984
    Date of Patent: January 20, 1987
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hiroyuki Hirai, Ken Kawata
  • 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
  • Patent number: 4598035
    Abstract: A heat-sensitive recording material, comprising a support having thereon a layer containing microcapsules containing at least a first component capable of causing a coloring reaction as a core material, and, outside of the microcapsules, at least a second component causing said coloring reaction with said first component in the microcapsules, wherein the microcapsules contain an organic solvent in the cores thereof, the average particle size of the microcapsules is 8 microns or less, and the value of (number average wall thickness .delta. (in microns)/volume average particle size D (in microns)) of the microcapsules is 1.times.10.sup.-2 or more. The coloring components that may be used in the core include leuco dyes and diazo compounds. The organic solvents have a boiling of 180.degree. C. or more. The heat-sensitive recording material has excellent pressure are friction resistance, a high heat coloring property and an excellent production aptitude.
    Type: Grant
    Filed: March 26, 1985
    Date of Patent: July 1, 1986
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshimasa Usami, Toshiharu Tanaka
  • Patent number: 4596876
    Abstract: Novel adducts of phthalaldehyde are disclosed, as well as imaging compositions and imaging elements incorporating them. A method is also disclosed for minimizing dimensional changes in the element during processing.
    Type: Grant
    Filed: September 14, 1983
    Date of Patent: June 24, 1986
    Assignee: Eastman Kodak Company
    Inventors: Thap DoMinh, Max H. Stern
  • Patent number: 4584256
    Abstract: The invention relates to new diazotype materials of which the sensitive layer contains, as a base generator, a compound comprising a basic part and an acid part, the acid part being a 2-carboxycarboxamide group and the basic part consisting of an alkali metal cation or alkaline earth metal cation or a tetraalkylammonium cation.These diazotype materials develop rapidly and possess an excellent resistance to ageing.
    Type: Grant
    Filed: November 21, 1984
    Date of Patent: April 22, 1986
    Assignee: Rhone-Poulenc Systemes
    Inventors: Claude Ceintrey, Michel Crochemore
  • Patent number: 4568628
    Abstract: A water developable printing plate is provided with a photopolymerizable system as a latex comprising a water soluble diazopolymer reaction product of a diazoaryl amine and an aldehyde and an aqueous cationic or nonionic dispersion of a water insoluble polymer. The inclusion of a water miscible organic solvent improves the shelf-life of the photopolymerizable system and the printing plate especially under high humidity conditions.
    Type: Grant
    Filed: October 23, 1984
    Date of Patent: February 4, 1986
    Assignee: Polychrome Corporation
    Inventor: Nils Eklund
  • Patent number: 4554236
    Abstract: This invention relates to light sensitive water soluble diazonium compound condensation products stabilized against degradation caused by heat and/or prolonged storage employing selected amino acids as stabilizers. The invention also relates to presensitized reproduction materials comprising the amino acid stabilized water soluble diazonium compound condensation products.
    Type: Grant
    Filed: October 19, 1983
    Date of Patent: November 19, 1985
    Assignee: American Hoechst Corporation
    Inventors: Trisha Bentley, John E. Walls, Major S. Dhillon
  • Patent number: 4542085
    Abstract: A negative working light-sensitive composition and a lithographic printing plate using the composition are described. The printing plate is comprised of a hydrophilic support and a thin layer of a negative working light-sensitive composition on the support. The light-sensitive composition contains a light-sensitive diazo compound and a compound capable of increasing absorption over the light-sensitive wavelength region of the composition with increasing exposure time.
    Type: Grant
    Filed: June 2, 1983
    Date of Patent: September 17, 1985
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hiroshi Takahashi, Akira Nishioka, Fumihiro Tokunaga, Yoshimasa Aotani, Koichiro Aono
  • Patent number: 4540648
    Abstract: The present invention relates to a two-component diazotype material comprising a support and one or several light-sensitive layers, each of which contains at least one light-sensitive diazonium salt, a coupler component and an acid stabilizer, and at least one of the layers contains a compound which absorbs light in the ultraviolet spectral region. The light-absorbing compound is present in the form of a dye salt of at least one benzothiazole which is converted into its leuco base under the action of an alkaline medium. It thus partially or completely loses its absorptivity toward radiation in the long-wave ultraviolet and short-wave visible spectral regions. The light-absorbing compound comprises a benzothiazole, in particular according to the general formula: ##STR1## wherein R.sub.1 denotes hydrogen, alkyl or aralkyl,R.sub.2 denotes hydrogen or an optionally substituted alkyl, aralkyl, aryl, pyridylalkyl, carbalkyl, carboxyalkyl, carboxyaryl, carbamoyl, or sulfamoyl radical, orR.sub.1 and R.sub.
    Type: Grant
    Filed: February 28, 1984
    Date of Patent: September 10, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Siegfried Scheler
  • Patent number: 4533619
    Abstract: This invention relates to light sensitive diazonium compound condensation products stabilized against degradation caused by heat and/or prolonged storage employing, as stabilizers, an acid selected from the group consisting of benzoic acid, m-nitro benzoic acid, p(p-anilino phenylazo) benzene sulfonic acid, 4,4'-dinitro-2,2'-stilbene disulfonic acid, itaconic acid, and mixtures thereof. The invention also relates to presensitized reproduction materials comprising the acid stabilized diazonium compound condensation products.
    Type: Grant
    Filed: September 12, 1983
    Date of Patent: August 6, 1985
    Assignee: American Hoechst Corporation
    Inventors: John E. Walls, Major Dhillon, Trisha Bentley
  • Patent number: 4529681
    Abstract: A light- and heat-sensitive recording material is disclosed. The material include microcapsule in which are encapsulated a particular combination comprised of a vinyl compound, a photopolymerization initiator, and a color forming component being capable of undergoing a color reaction with another color forming component to cause color formation. These coloring components are provided on the same side of a support.
    Type: Grant
    Filed: November 17, 1983
    Date of Patent: July 16, 1985
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshimasa Usami, Toshiharu Tanaka, Masato Satomura
  • Patent number: 4526854
    Abstract: A method for forming a pattern of a non-light-emitting black material on the inner surface of a faceplate of a color cathode ray tube is provided, which comprises the steps of forming a photoresist layer of a photoresist containing a water-soluble bisazidocompound, a water-soluble diazocompound, and a water-soluble polymeric material, on an inner surface of a faceplate of a color cathode ray tube, selectively exposing parts of the photoresist layer using a shadow mask so as to photocure the exposed parts, developing the photoresist layer to remove unexposed parts of the photoresist layer, thereby forming dots of the photoresist, forming a film of a non-light-emitting black material on the inner surface of the faceplate including the dots, and removing the dots and the non-light-emitting black material on the dots so as to form holes in the film of the non-light-emitting black material.
    Type: Grant
    Filed: February 18, 1983
    Date of Patent: July 2, 1985
    Assignee: Tokyo Shibaura Denki Kabushiki Kaisha
    Inventors: Shingo Watanabe, Takeo Itou
  • Patent number: 4499170
    Abstract: Plates such as those used in lithographic printing and photoresists such as those used in preparing printed circuit boards and the like are provided with a photopolymerizable photosensitive diazo resin that is unusually stable. The diazo resin is laid down from a stabilized diazonium composition that is an emulsion including the selected diazo resin, a purine derivative, especially a theophylline derivative, preferably in combination with a salt of a low molecular weight alkyl sulfonic acid or other supplementary stabilizer component.
    Type: Grant
    Filed: June 17, 1983
    Date of Patent: February 12, 1985
    Assignee: Richardson Graphics Company
    Inventors: Luigi Amariti, Llandro C. Santos
  • Patent number: 4497887
    Abstract: A thermal development type diazo copying material comprising a support material and a photosensitive layer formed on the support material, which photosensitive layer comprises a diazo compound, a coupling component and a thermo-fusible auxiliary coloring agent, and which coupling component is capsulated by a hydrophobic polymeric material with a softening point ranging from 50.degree. C. to 150.degree. C. selected from the group consisting of hydrophobic polyester resins, hydrophobic cellulose resins, hydrophobic polyamide resins and hydrophobic polyurethane resins.
    Type: Grant
    Filed: June 2, 1982
    Date of Patent: February 5, 1985
    Assignee: Ricoh Compay, Ltd.
    Inventors: Nobuyoshi Watanabe, Tsutomu Matsuda