EP0378831B1 - Photographische Silberhalogenidemulsion - Google Patents

Photographische Silberhalogenidemulsion Download PDF

Info

Publication number
EP0378831B1
EP0378831B1 EP89123433A EP89123433A EP0378831B1 EP 0378831 B1 EP0378831 B1 EP 0378831B1 EP 89123433 A EP89123433 A EP 89123433A EP 89123433 A EP89123433 A EP 89123433A EP 0378831 B1 EP0378831 B1 EP 0378831B1
Authority
EP
European Patent Office
Prior art keywords
group
silver halide
acid
emulsion
salt
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
EP89123433A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0378831A1 (de
Inventor
Erich Wolfgang Friedrich
Alfred Dr. Wörsching
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.)
Sterling Diagnostic Imaging Inc
Original Assignee
DuPont de Nemours Deutschland GmbH
EI Du Pont de Nemours and Co
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 DuPont de Nemours Deutschland GmbH, EI Du Pont de Nemours and Co filed Critical DuPont de Nemours Deutschland GmbH
Publication of EP0378831A1 publication Critical patent/EP0378831A1/de
Application granted granted Critical
Publication of EP0378831B1 publication Critical patent/EP0378831B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/28—Sensitivity-increasing substances together with supersensitising substances
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/16—X-ray, infrared, or ultraviolet ray processes
    • G03C5/164—Infrared processes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/145—Infrared

Definitions

  • the invention relates to a photographic silver halide emulsion for the production of recording materials for the infrared spectral region.
  • the object of the present invention is accordingly to provide photographic silver halide emulsions which give infrared recording materials with high sensitivity. Another object is to provide emulsion additives which are super-sensitive to the infrared sensitivity of silver halide materials.
  • an infrared-sensitive silver halide emulsion which contains an aromatic thiosulfonic acid or a salt of such an acid as an emulsion additive.
  • aromatic thiosulfonic acids are known as additives to emulsions for recording materials for the visible spectral range. However, after their action in such emulsions, they are only described as "clearing agents", ie antifoggants in gold sensitization or together with aromatic sulfinic acids (DD 7 376; US 2,394,198).
  • a more recent Japanese patent application JP 57 176 032; cited from Chem. Abstr. 100: 42996 also describes the use of sodium thiotosylate (compound I-2, see below) in the physical ripening of emulsions, which are then mixed with mono-, tri- or pentaamethine cyanines have been sensitized to visible light.
  • EP 2 93 917 also describes the use of thiosulfonic acids and their salts and esters as clearing agents in color film emulsions.
  • aromatic thiosulfonic acids have a super-sensitizing effect in infrared-sensitized emulsions. Since they were previously only described as antifoggants and stabilizers in emulsions sensitized to visible light, this effect is surprising for the person skilled in the art.
  • Preferred thiosulfonic acids and salts for the emulsions according to the invention are represented by the general formula (I) reproduced.
  • R is an optionally divalent alkyl, aryl or aralkyl radical with 0 to 10 carbon atoms and M is a cation, preferably an alkali metal or ammonium ion, and n is the number 1 or 2.
  • the thiosulfonic acids or their salts must be used in amounts which are considerably higher than those described for the clarifying effect in the prior art. Additions of 0.1 to 5 millimoles per mole of silver halide are generally sufficient. The range between 0.2 and 2 millimoles per mole of silver halide is particularly preferred.
  • the emulsions according to the invention contain a suitable sensitizing dye for sensitization in the infrared spectral range.
  • cyanine dyes are used that have more than five optionally substituted methine groups (so-called polymethine cyanines).
  • Heptamethine cyanines are preferred because they sensitize to the near infrared range, which is primarily used for recording because of the lower thermal interference radiation and the inexpensive semiconductor lasers.
  • Particularly preferred sensitizers can be represented by the general formula (II).
  • R5 and R6 are each a hydrogen atom or together, linked together, a divalent alkylene group
  • R7 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a phenyl group, a benzyl group or wherein W1 and W2, which may be the same or different, each represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, with the proviso that W1 and W2 may be linked together to form a 5-membered or 6-membered nitrogen-containing heterocycl
  • the compounds are examples of suitable infrared sensitizers
  • the silver halide of the emulsions according to the invention can be silver chlorobromide, silver bromoiodide, silver chloroiodide or silver chlorobromoiodide.
  • Silver chlorobromides with a chloride content of at least 70 mole percent, which may also contain small amounts of iodide, and silver bromoiodides with an iodide content of at most 10 mole percent are preferred.
  • the crystal form can be polyhedral, platelet-shaped, spherical or irregular; the particle size distribution polydisperse or monodisperse.
  • the grains can also have a core-shell structure. In a preferred embodiment, a monodisperse cubic emulsion with a grain size between 0.05 and 1.0 ⁇ m is used. Methods for the production of emulsions of certain grain shape, grain size and grain size distribution are known to the person skilled in the art.
  • Chemical ripening can be carried out using the known methods of sulfur, noble metal or reduction sensitization or else using suitable combinations of these methods.
  • the aromatic thiosulfonic acids according to the invention can be added before, during or after chemical ripening. If they are present in the emulsion during chemical ripening, they also act as clarifiers in the known manner.
  • the infrared sensitizers are preferably added to the emulsion after chemical ripening or shortly before application to the layer support. However, if they are sufficiently stable, they can also be used in earlier stages of emulsion production.
  • the emulsions and the recording materials produced therefrom can contain other known agents for adjusting certain properties, for example antifoggants, agents for improving the storage stability, polymer dispersions (for improving the dimensional stability of the recording materials), hardening agents, coating aids, matting agents.
  • agents for adjusting certain properties for example antifoggants, agents for improving the storage stability, polymer dispersions (for improving the dimensional stability of the recording materials), hardening agents, coating aids, matting agents.
  • the emulsions of the invention provide photographic materials with superior infrared sensitivity.
  • the gradation of the emulsion is not significantly changed by the addition of the thiosulfonic acid. Suitable thiosulfonic acids or their salts for carrying out the invention are readily available.
  • the invention can be used in the production of infrared-sensitive photographic recording materials, for example for recordings with a scanning laser beam in reproduction technology or medical diagnosis, and for imagewise photography.
  • the following exemplary embodiments are intended to explain the invention in more detail.
  • all amounts of emulsion additives are based on 1 mol of silver halide; unless otherwise noted, the addition was in dissolved form.
  • a monodisperse silver chlorobromide emulsion with a chloride content of 70 mole percent was produced by pAg-regulated two-jet enema. This emulsion had cubic grains with an edge length of 0.22 ⁇ m. After removing the soluble salts by flaking and washing, it was subjected to a combined sulfur-gold ripening. Before chemical ripening began, 133 mg of Compound I-1 was added. The ripening was ended by adding 270 mg of 4-hydroxy-6-methyl-1,3,3a, 7-tetraazaindene.
  • a comparison test was carried out according to the same procedure, but without the addition of compound I-1.
  • the material obtained in this way was exposed in a sensitometer with an exposure time of 1 ms through interference filters with transmission maxima of 407 and 798 or 830 nm and processed in a X-ray roll developing machine filled with commercially available solutions at a developer temperature of 34 ° C in a total time of 90 s.
  • the reciprocal of the exposure required for a density of 1.0 above the minimum density (veil + underlay) was determined and related to the value 100 for the comparison test.
  • the test result is shown in Table 1.
  • Example 2 The experiment according to Example 1 was repeated, but the experimental and the comparative emulsions each containing 200 mg of nonylphenol ethoxylate (10 moles of ethylene oxide per mole of phenol) were added. The result is shown in Table 2.
  • a monodisperse silver chlorobromide emulsion with 80 mole percent chloride with cubic grains with an edge length of 0.23 ⁇ m was produced by pAg-regulated two-jet inlet. 0.052 mg of rhodium (III) chloride had been added to the precipitation mixture. The emulsion was subjected to a flocculation washing process and a combined gold-sulfur sensitization.
  • Example 3 Before the digestion, 140 mg of sodium toluenesulfinate and optionally the compound I-2, then 400 mg of 4-hydroxy-6-methyl-1,3,3a, 7-tetraazaindene, 70 mg of benzotriazole, 750 mg of sodium octylphenyldi (oxyethyl) sulfonate, 25 mg of the sensitizer II-1 and, if appropriate, 65 g of the latex of Example 3 were added. The emulsion was applied together with a protective gelatin layer to a support as in Example 1. The recording material thus produced contained 4.3 g of silver and 3.5 g of gelatin per m2 on the recording side.
  • Example 2 The material was exposed as in Example 1 and processed in a roll developing machine for photoset material with a commercially available rapid developer of the hydroquinone-phenidone type at 34 ° C. in a total time of 120 s.
  • the reciprocal of the exposure required for a density of 3.0 above the minimum density was determined and, for each wavelength, related to the value 100 for the comparison test. The result is shown in Table 4.
  • Examples 3 and 4 show that the addition of the aromatic thiosulfonate according to the invention increases the sensitivity even in the presence of known supersensitizing additives.
  • Example 5 Experiments were carried out after the comparative experiment from Example 4, in which the emulsion was sensitized with various sensitizers for the green, red and infrared spectral range with and without the addition of 75 mg of the compound I-1. The sensitivity was determined for each sensitizer at 407 nm and at the sensitization maximum. Table 5 shows the sensitivities of the test films containing the compound I-1 based on the value 100 for the films without this compound with otherwise the same sensitization.

Landscapes

  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Indole Compounds (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
EP89123433A 1989-01-18 1989-12-19 Photographische Silberhalogenidemulsion Expired - Lifetime EP0378831B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3901268 1989-01-18
DE3901268A DE3901268A1 (de) 1989-01-18 1989-01-18 Photographische silberhalogenidemulsion

Publications (2)

Publication Number Publication Date
EP0378831A1 EP0378831A1 (de) 1990-07-25
EP0378831B1 true EP0378831B1 (de) 1994-09-07

Family

ID=6372264

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89123433A Expired - Lifetime EP0378831B1 (de) 1989-01-18 1989-12-19 Photographische Silberhalogenidemulsion

Country Status (6)

Country Link
US (1) US5009992A (enrdf_load_stackoverflow)
EP (1) EP0378831B1 (enrdf_load_stackoverflow)
JP (1) JPH0772786B2 (enrdf_load_stackoverflow)
CA (1) CA2007993A1 (enrdf_load_stackoverflow)
DE (2) DE3901268A1 (enrdf_load_stackoverflow)
ES (1) ES2061915T3 (enrdf_load_stackoverflow)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2640978B2 (ja) * 1989-04-06 1997-08-13 富士写真フイルム株式会社 ハロゲン化銀写真感光材料
EP0495253B1 (en) * 1991-01-15 1995-05-10 Agfa-Gevaert N.V. Method for the photographic production of silver images
US5443947A (en) * 1993-11-30 1995-08-22 Eastman Kodak Company Heat stabilized silver chloride photographic emulsions containing thiosulfonate/sulfinate compounds
US6740482B1 (en) 1994-12-22 2004-05-25 Eastman Kodak Company High chloride emulsion having high sensitivity and low fog
US5620841A (en) * 1995-07-31 1997-04-15 Eastman Kodak Company Photographic element containing new gold(I) compounds
US5700631A (en) * 1996-03-14 1997-12-23 Eastman Kodak Company Photographic element containing new gold(I) compounds
JP2004226434A (ja) * 2003-01-20 2004-08-12 Konica Minolta Holdings Inc ハロゲン化銀乳剤、ハロゲン化銀写真感光材料及び画像形成方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2394198A (en) * 1944-10-17 1946-02-05 Gen Anilline & Film Corp Stabilized silver halide emulsions
JPS4974018A (enrdf_load_stackoverflow) * 1972-10-02 1974-07-17
JPS6045413B2 (ja) * 1976-08-11 1985-10-09 富士写真フイルム株式会社 熱現像感光材料
JPS5827486B2 (ja) * 1977-06-03 1983-06-09 富士写真フイルム株式会社 ハロゲン化銀写真乳剤
JPS59191032A (ja) * 1983-04-13 1984-10-30 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料
US4603104A (en) * 1985-05-31 1986-07-29 Minnesota Mining And Manufacturing Company Supersensitization of silver halide emulsions
GB8610615D0 (en) * 1986-04-30 1986-06-04 Minnesota Mining & Mfg Sensitisers
JP2664153B2 (ja) * 1987-06-05 1997-10-15 富士写真フイルム株式会社 ハロゲン化銀カラー写真感光材料およびその現像処理方法
US4780404A (en) * 1987-06-09 1988-10-25 Minnesota Mining And Manufacturing Company Supersensitization of silver halide emulsion
JPH0687123B2 (ja) * 1987-09-21 1994-11-02 富士写真フイルム株式会社 ハロゲン化銀写真感光材料

Also Published As

Publication number Publication date
CA2007993A1 (en) 1990-07-18
EP0378831A1 (de) 1990-07-25
ES2061915T3 (es) 1994-12-16
DE3901268C2 (enrdf_load_stackoverflow) 1992-04-02
DE58908327D1 (de) 1994-10-13
JPH02234152A (ja) 1990-09-17
JPH0772786B2 (ja) 1995-08-02
US5009992A (en) 1991-04-23
DE3901268A1 (de) 1990-07-19

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