US3782945A - Mercaptotetrazaindene in photographic printing plate development - Google Patents

Mercaptotetrazaindene in photographic printing plate development Download PDF

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Publication number
US3782945A
US3782945A US00152397A US3782945DA US3782945A US 3782945 A US3782945 A US 3782945A US 00152397 A US00152397 A US 00152397A US 3782945D A US3782945D A US 3782945DA US 3782945 A US3782945 A US 3782945A
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US
United States
Prior art keywords
compound
developer
developing
tetraazaindene
silver halide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US00152397A
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English (en)
Inventor
T Shishido
R Ohi
E Okutsu
H Iwano
I Shimamura
Y Iijima
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fujifilm Holdings Corp
Original Assignee
Fuji Photo Film Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Fuji Photo Film Co Ltd filed Critical Fuji Photo Film Co Ltd
Application granted granted Critical
Publication of US3782945A publication Critical patent/US3782945A/en
Anticipated expiration legal-status Critical
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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/005Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/34Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
    • G03C1/346Organic derivatives of bivalent sulfur, selenium or tellurium

Definitions

  • R and R which may be the same or different, represent a hydrogen atom, a hydroxyl group, a hydrocarbon group or -SR,-,; at least one of said R and R being -SR R represents a hydrogen atom or an alkyl radical; and R and R, which may be the same or different, represent a hydrogen atom, a hydroxyl group, a halogen atom, or a hydrocarbon group; said R and R may be ring-closed to form a 5- or 6-membered ring.
  • the present invention relates to a process for developing a silver halide photographic element for printing plate and more particularly the invention relates to a developing process having a wide developing latitude and giving images having good quality.
  • lith-type light-sensitive materials include a lith plate (lithographic plate) or lith film (lithographic film).
  • the original picture consisting of a continuous tone image is recorded on these materials with a continuous regularly distributed crowd of dots, namely, the continuous tone image is converted to a divided discontinuous dot image. In this process the density variation of the original is changed to a dot size variation.
  • the other group of lithographic materials include lith line plate (lithographic line dry plate) or lith line film (lithographic line film) for recording line image.
  • photographic plates for prinitng Furthermore, at the development of such photographic silver halide element for printing plates (hereinafter referred to as photographic plates for prinitng), the control of the developing period of time is an important problem.
  • a photographic plate for printing has a feature that the latitude of the developing time thereof for obtaining the optimum dot qualities is quite narrow. Particularly, if a developing period of time is prolonged, the qualities of dots are degraded. It is an important theme in the development of the photographic plate for printing to overcome such difiiculties and widen the latitude of the optimum developing time.
  • An object of this invention is to provide a developing process for lithographic materials, which can reduce fringe and can improve latitude of development.
  • R and R which may be the same or different, represent a hydrogen atom, a hydroxyl group, a hydrocarbon group or -SR at least one of said R and R being SR R represents a hydrogen atom or an alkyl group, and R and R.,, which may be the same or different,
  • Compound 2 fi-methyl-l,3,3a,7-tetraazaindene-4-thiol.
  • Compound 6 G-undecyl-l,3,3a,7-tetraazatndeno-4'thiol.
  • Compound 7 6-heptadecyl-l,3,3a,7-tetraazindene-4-thiol.
  • Compound 10 2, fi-dlmethyl-l, 3, 3a, 7-tctraazulndoneA-thlol.
  • Compound 12 fi-iso-butyl-G-mothyl-l, 3, 3a, 7-tetraazaindene-4thiol1 I SH Compound 13: 2-benzyl-6-methyl-l, 3, 3a, 7-tetraazaindenet-thiol.
  • Compound 14 2-mcthyltl1io-4-hydroxy-61nothyl-1,3,3a,7-totraazaindeno.
  • the Compounds 1-8 may be prepared by reacting 3-amino-1,2,4-triazole with corresponding acylacetic acid esters, followed by chlorination of the products by phosphorus oxychloride then reacting the products with thiourea.
  • the Compound 9 may be obtained by bromination of the Compound 2 in acetic acid.
  • the Compounds 14-17 may be obtained by the coudensation reaction of 3-amino-5-methylthio-1,2,4-triazole and corresponding ketoesters or diethyl malonate (Compound 15).
  • the amount of the compound used in this invention is varied according to the composition of the developing solution and the nature of the emulsion to be employed, but in case of incorporating the compound in the developing solution, it is preferable that the amount of the compound b from 1 10- mol to 1 10- mol per liter of the developing solution, and in case of incorporating it in the silver halide emulsion, it is preferable that the amount of it be in a range of from 1 10 mol to 1 10 mol per mol of the silver halide.
  • the developing solution for lithographic materials ordinarily contains hydroquinone as a developing agent
  • the developing solution may sometimes contain a softener for hard water, an organic solvent, a polyalkylene oxide compound, ascorbic acid, etc.
  • the emulsion used for the photographic plate for printing is an ordinary silver halide photographic emulsion and a silver chloride emulsion, a silver bromide emulsion, a silver chlorobromide emulsion, a silver iodobromide emulsion, and a silver chloroiodobromide emulsion are employed, although the silver chlorobromide is particularly preferable.
  • a silver halide emulsion is prepared by dispersing the silver halide in a medium, such as gelatin or a mixture of gelatin and a synthetic polymer.
  • the silver halide emulsion may be sensitized chemically by ammonium thiosulfate, sodium thiosulfate, or allylthiourea; a gold compound, such as a complex salt of a monovalent gold and thiocyanic acid; or a combination of them.
  • the silver halide emulsion may be optically sensitized by adding thereto a spectral sensitizer such as a cyanine dye, merocyanine dye and the like.
  • the silver halide emulsion may contain a heterocyclic compound, such as benzotriazole or a polyalkylene oxide compound, an amine compound, and further may contain' a hardening agent such as formaldehyde or mucochloric acid. Furthermore, the silver halide emulsion may contain a surface active agent such as saponine for facilitating the coating operation.
  • a heterocyclic compound such as benzotriazole or a polyalkylene oxide compound, an amine compound
  • a hardening agent such as formaldehyde or mucochloric acid.
  • the silver halide emulsion may contain a surface active agent such as saponine for facilitating the coating operation.
  • the compound may be incorporated in the silver halide emulsion at any stage during the preparation of the photographic emulsion, but the most preferable results are obtained by adding the compound at a stage after the postripening and before coating.
  • the compound may be added as a solution thereof in an organic solvent, such as methanol, ethanol, acetone, etc.
  • the compound may of course be incorporated directly in the silver halide emulsion but may be incorporated in an adjacent layer of the silver halide emulsion layer such as a protective layer to diifuse the compound into the silver halide emulsion layer from the protective layer.
  • EXAMPLE 1 A commercially available lithographic film was exposed by a sensitometer using an optical wedge attached with a magenta contact screen of 150 lines and then developed for 2-5 minutes at 20 C. in the developing solution prepared from the two kinds of the concentrated liquids having the following formulas:
  • Distilled water (50 C.) cc 100 Sodium sulfite g 2 Sodium carbonate (monohydrate) g 30 Sodium hydroxide g 5 Boric acid g 5 Sodium bromide g 2 Distilled water to make 125 cc.
  • the liquid A was first added to 750 cc. of water and then the liquid B was added to the mixture so that the whole volume of the final solution became 1,000 cc.
  • the widths of the fringes around the dots were measured by tracing the dots of 20% in dot area ratio by means of a microdensitometer.
  • EXAMPLE 2 A commercial lithographic film was exposed with a sensitometer through an optical wedge for sensitometry attached with a magenta contact screen of 150 lines and then developed for 2-5 minutes at 20 C. in the developer prepared by mixing the two kinds of the concentrated liquids having the following composition:
  • Distilled water (50 C.) cc 50 Diethylene glycol cc 15 'Methyl Cellosolve cc 15 Formaldehyde-potassium bisulfite addition product g 45 Hydroquinone g 16 L-ascorbic acid g 1 Distilled water to make 125 cc.
  • the liquid A was added to 750 cc. of water and then the liquid B was added to the mixture so that the whole volume of the resultant developer became 1,000 cc.
  • the widths of the fringes around the dots of each of the two samples thus developed were measured by tracing the dots of 20% in dot area ratio by means of a microdensitometer.
  • EXAMPLE 3 A commercially available lithographic film was used to take a photograph of an optical wedge for sensitometry through contact screen of 150 lines magenta and then developed for 2-5 minutes at 20 C. in the developer having the following composition:
  • the widths of the fringes around the dots of the samples thus developed were measured by tracing the dots of 20% in dot area ratio by means of microdensitometer.
  • the widths of the fringes around the dots of each sample were measured by tracing the dots of 20% in dot area ratio by means of a microdensitometer.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US00152397A 1970-06-11 1971-06-11 Mercaptotetrazaindene in photographic printing plate development Expired - Lifetime US3782945A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP45050564A JPS503170B1 (xx) 1970-06-11 1970-06-11

Publications (1)

Publication Number Publication Date
US3782945A true US3782945A (en) 1974-01-01

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US00152397A Expired - Lifetime US3782945A (en) 1970-06-11 1971-06-11 Mercaptotetrazaindene in photographic printing plate development

Country Status (5)

Country Link
US (1) US3782945A (xx)
JP (1) JPS503170B1 (xx)
DE (1) DE2128498A1 (xx)
FR (1) FR2096049A5 (xx)
GB (1) GB1312864A (xx)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4043817A (en) * 1974-11-07 1977-08-23 Fuji Photo Film Co., Ltd. Method of forming photographic images for lithographic use
US4108662A (en) * 1976-01-28 1978-08-22 Fuji Photo Film Co., Ltd. Process for developing photographic light-sensitive materials for the graphic arts
US4292391A (en) * 1980-02-06 1981-09-29 E. I. Du Pont De Nemours And Company Silver halide development accelerators
US5175289A (en) * 1989-01-11 1992-12-29 Ciba-Geigy Corporation 1,2,4-triazolo-[1,5a]pyrimidin-2-yl derivatives
EP0601503A2 (en) * 1992-12-09 1994-06-15 Konica Corporation Composition for developing a black-and-white silver halide photographic light-sensitive material
EP0631179B1 (en) * 1993-06-10 2000-04-05 Konica Corporation Method for processing a black-and-white silver halide photographic light-sensitive material
US20030005945A1 (en) * 2000-03-13 2003-01-09 Hiroyuki Onishi Method for surface-treatment, surface-treated article and device for surface treatment

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2327133A1 (de) * 1972-06-07 1974-01-03 Icn Pharmaceuticals 2-subst.-thio-s-triazolo eckige klammer auf 1,5a eckige klammer zu -pyrimidine
JPS60142987A (ja) * 1983-12-29 1985-07-29 Mochida Pharmaceut Co Ltd セフアロスポリン誘導体
DE3485860T2 (de) * 1983-12-29 1993-01-14 Mochida Pharm Co Ltd Cephalosporinverbindungen, verfahren zu ihrer herstellung und pharmazeutishe praeparate.
US4840945A (en) * 1985-04-01 1989-06-20 Mochida Pharmaceutical Co., Ltd. Cephalosporin derivatives
US4880798A (en) * 1986-11-25 1989-11-14 Mochida Pharmaceutical Co., Ltd. Cephalosporin derivatives
JPS63132893A (ja) * 1986-11-25 1988-06-04 Mochida Pharmaceut Co Ltd 新規セフアロスポリン誘導体、その製法およびそれらを有効成分とする抗菌剤
EP0378508B1 (de) * 1989-01-11 1995-03-01 Ciba-Geigy Ag Antidots zur Verbesserung der Kulturpflanzenvertäglichkeit agrochemischer Wirkstoffe

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4043817A (en) * 1974-11-07 1977-08-23 Fuji Photo Film Co., Ltd. Method of forming photographic images for lithographic use
US4108662A (en) * 1976-01-28 1978-08-22 Fuji Photo Film Co., Ltd. Process for developing photographic light-sensitive materials for the graphic arts
US4292391A (en) * 1980-02-06 1981-09-29 E. I. Du Pont De Nemours And Company Silver halide development accelerators
US5175289A (en) * 1989-01-11 1992-12-29 Ciba-Geigy Corporation 1,2,4-triazolo-[1,5a]pyrimidin-2-yl derivatives
EP0601503A2 (en) * 1992-12-09 1994-06-15 Konica Corporation Composition for developing a black-and-white silver halide photographic light-sensitive material
EP0601503A3 (en) * 1992-12-09 1994-07-06 Konica Corporation Composition for developing a black-and-white silver halide photographic light-sensitive material
US5508153A (en) * 1992-12-09 1996-04-16 Konica Corporation Composition for developing a black-and-white silver halide photographic light-sensitive material
EP0631179B1 (en) * 1993-06-10 2000-04-05 Konica Corporation Method for processing a black-and-white silver halide photographic light-sensitive material
US20030005945A1 (en) * 2000-03-13 2003-01-09 Hiroyuki Onishi Method for surface-treatment, surface-treated article and device for surface treatment
US7169444B2 (en) * 2000-03-13 2007-01-30 Seiko Epson Corporation Method for treating surface of ink jet recording medium having recorded image

Also Published As

Publication number Publication date
FR2096049A5 (xx) 1972-02-11
DE2128498A1 (de) 1971-12-16
JPS503170B1 (xx) 1975-01-31
GB1312864A (en) 1973-04-11

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