US3359106A - Photographic material - Google Patents

Photographic material Download PDF

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Publication number
US3359106A
US3359106A US355912A US35591264A US3359106A US 3359106 A US3359106 A US 3359106A US 355912 A US355912 A US 355912A US 35591264 A US35591264 A US 35591264A US 3359106 A US3359106 A US 3359106A
Authority
US
United States
Prior art keywords
light
sensitive
dihydrobenzimidazo
thioxo
compounds
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
US355912A
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English (en)
Inventor
Willems Jozef Frans
Poot Albert Lucien
Paul Desire Van Pee
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.)
Gevaert Photo Producten NV
Original Assignee
Gevaert Photo Producten NV
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 Gevaert Photo Producten NV filed Critical Gevaert Photo Producten NV
Application granted granted Critical
Publication of US3359106A publication Critical patent/US3359106A/en
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
    • G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
    • 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
    • G03C1/35—Antiplumming agents, i.e. antibronzing agents; Toners
    • G03C1/355—Organic derivatives of bivalent sulfur, selenium or tellurium
    • 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
    • Y10S430/13—Antibronze agent or process

Definitions

  • the present invention relates to photographic printing material containing compounds which prevent the image obtained from being bronzed by hot glazing or mechanical drying at elevated temperature, and to photographic baths wherein such compounds are dissolved.
  • the images obtained in light-sensitive silver halide emulsion layers of a photographic printing material often undergo changes during hot glazing or during mechanical drying at elevated temperature, since during these treatments a loss of density arises which is also called plumming or bronzing of the sliver image.
  • benzimidazo[1,2-c]quinazolines may be substituted e.g. by an alkyl radical, an alkoxy radical, a halogen atom, an amino group or an acetylamino group. They may also be applied in the form of their tautomers or salts of these tautomers.
  • benzimidazo[l,2-c]quinazolines can be prepared as described by A. Foot, J. Willems and F. Huygebaert, Bull. Soc. Chim. Belg, 72 (1963) 365.
  • all these 5,6-dihydrobenzimidazo[l,2-c]quinazolines may also be applied to high-sensitive negative material, often in combination with other stabilizers.
  • the benzimidazo[l,2-c]quinazolines of use according to the invention are generally incorporated into the light-sensitive silver halide emulsion printing layer itself. They can be added to the printing silver halide emulsion at any moment during its preparation, but preferably after chemical ripening or just before coating. This addition occurs in general from a solution of the compound in an appropriate solvent such as water, alcohol, dimethylformamide and so on.
  • the total concentration of benzimidazo[1,2-c]quinazolines in the light-sensitive printing material may vary within wide limits, but is preferably chosen in such a way that per sq. m. of light-sensitive material from some mg. to approximately 500 mg. of this compound or compounds are present.
  • Light-sensitive material may comprise any printing halogen silver emulsion layer such as for instance a gelatino silver chloride emulsion layer, a gelatino silver chlorobromide emulsion layer, a gelatino silver chloroiodide emulsion layer, a gelatino silver bromide emulsion layer, a gelatino silver bromoiodide emulsion layer and a gelatino silver chlorobromoiodide emulsion layer.
  • the silver halide emulsion may contain all known additives, such as anti-fogging agents, stabilizers, hardening agents, plasticizers and dispersing agents. Further, it may be sensitized chemically as well as spectrally.
  • the lightsensitive printing emulsions can also be sensitized by means of reducing agents for instance the tin compounds described in the Belgian patent specifications 493,464 and 568,687, the iminoaminomethane sulphinic acid compounds described in the British patent specification 78 9,- 823 or by means of small amounts of noble metal compounds such as gold compounds, platinum compounds, palladium compounds, iridinum compounds, ruthenium compounds and rhodium compounds.
  • polyoxyalkylene derivatives for instance polyoxyethylene of a molecular weight ranging between 1000 and 20,000 or condensation products of alkylene oxides with aliphatic alcohols, glycols, cyclic dehydration products of heXitols, alkylsubstituted phenols, aliphatic carboxylic acids, aliphatic amines, aliphatic diamines and aliphatic amides.
  • the condensation products have a molecular weight of at least 700, preferably of more than 1000.
  • these sensitizers can be applied in combination as described in the Belgian patent specificacation 537,278 and in the British patent specification 727,982.
  • the compounds to be used according to the invention can be dissolved in one of the processing baths such as the developing bath, the fixing bath, an additional hardening bath, and a bath which contains surfaceactive compounds and which is used as a last treating bath before hot glazing or before drying, at elevated temperature of the image-containing material.
  • the 6 thioxo 5,6 dihydrobenzimidazo[1,2 c]quinazolines are dissolved in the bath in the form of their alkali salts in concentrations which can vary within very wide limits preferably, however, between approximately 50 mg. and approximately 1000 mg./ liter.
  • the photographic printing material When the the photographic printing material is led through such a bath, it absorbs a certain amount of the benzimidazo[l,2-c]quinazoline into its water-permeable layers, which assures as well the retaining of the density of the silver-containing image during hot glazing or drying at high temperature as does the presence of the anti-bronzing agent in the light-sensitive material from its preparation on.
  • Material 1 is prepared as follows:
  • a gelatino silver chloride emulsion prepared with a proportion of silver nitrate to gelatin of 1 to 4 (28.3 g./ 113.2 g. per kg. of emulsion) is applied to a baryta-coated paper support in such a way that after drying an amount of silver halide, equivalent to 1.5 g. of silver nitrate is present per sq. m. of light-sensitive material.
  • This lightsensitive layer is coated with a thin gelatin covering layer which is hardened afterwards.
  • Material 2a is prepared as Material 1 with the difference, however, that per kg. of light-sensitive emulsion, ready for coating, 0.3 g. of 6-thioxo-5,6-dihydrobenzirnidazo [l,2-c]quinazoline is added from a 1% solution in dimethyl formamide.
  • Material 2b is prepared as Material 1 with the difference, however, that per kg. of light-sensitive emulsion, ready for coating, 1 g. of 6-thioxo-5,6-dihydrobenzimidazo[.1,2-c]quinazoline is added from a 1% solution in dimethyl forma-mide.
  • Material 3a is prepared as Material 1 with the difference, however, that per kg. of light-sensitive emulsion, ready for coating, 0.3 g. of 6-thioxo-9-methyl-5,6-dihydrobenzimidazo[l,2-c]quinazoline is added from a 1% solution in dimethyl formamide.
  • Material 3b is prepared asMaterial 1 with the diiference, however, that per kg. of light-sensitive emulsion, ready for coating 1g. of 6-thioxo-9-methyl-5,6-dihydrobenzimidazo [1,2-c]quinazoline is added from a 1% solution in dimethyl formamide.
  • a strip of each of these five materials is exposed for some minutes and developed for five minutes at 20 C. in a bath of the following composition:
  • the strips are rinsed for 30 minutes and dipped for some seconds in the following preservation solution:
  • Material 1 is prepared as Material 1 with the difference, however, that per kg. of light-sensitive emulsion, ready for coating, 0.3 g. of 6 thioxo 9 methyl 5,6 dihydrobenzimidazo[1,2-c]quinazoline is added from a 1% solution in dimethyl formamide.
  • Material 3 is prepared as Material 1 with the difference, however, that per kg. of light-sensitive emulsion, ready for coating, 0.3 g. of 6-thioxo-9-methexy-5,6-dihydrobenzimidazo[1,2-c]quinazoline is added from a 1% solution in dimethyl formamide.
  • Density before Density alter hot glazing hot glazing Material 1 (comparison material). 1. 98 1. 50 Material 2 2. 04 l. 98 Material 3 1. 97 1. 94
  • M aferial 2 Material 2 is prepared as Material 1 with the difference, however, that per kg. of light-sensitive emulsion, ready for methyl-5,-dihydrobenzimidazo[1,2-c]quinazoline is incorporated from a 1% solution in dimethyl formamide in such a Way that 20 mg. are present per sq. m. of lightsensitive material.
  • Density before Density after hot glazing hot glazing Material 1 (comparison material) 1. 96 1. 50 Material 2 a 2. 03 1. 96 Material 3- 1. 96 1. 93
  • Material 1 Material 2
  • Material 2 is prepared as Material 1 With the difference, however, that per kg. of light-sensitive emulsion, ready for coating, 0.3 g. of 6-thioXo-5,6-dihydrobenzimidazo [1,2-c]quinazoline is added from a 1% solution in dimethyl formamide.
  • Material 3 is prepared as Material 1 with the difference, however, that per kg. of light-sensitive emulsion, ready for coating, 0.3 g. of 6-thioxo-9-methyl-5,6-dihydrobenzimidazo[l,2-c]quinazoline is added from a 1% solution in dimethyl formamide.
  • Material 4 is prepared as Material 1 with the ditference, however, that per kg. of light-sensitive emulsion, ready for coating, 0.3 g. of 6-thioxo-9-methoXy-5,6-dihydrobenzimidazo [1,2-c]quinazoline is added from a 1% solution in dimethyl formamide.
  • EXAMPLE 5 Four strips of a material, composed as the comparison material from Example 4, are treated as the material strips of Example 1, with the difference, however, that (1) for the processing of the second material strip 0.5 g. of 6- thioXo-5,6-dihydrobenzirnidazo[ 1,2-c1quinazoline is dis- 20 solved in the developing bath (per liter), (2) for the processing of the third material strip 0.5 g. of the above compound is dissolved in the fixing composition (per liter) and (3) for the processing of the fourth material a hardening bath (4t)% aqueous formaldehyde solution) containing 5 per liter 0.5 g. of the above compound wherein the ma terial is treated for 10 minutes, is included as last processing bath.
  • a hardening bath (4t)% aqueous formaldehyde solution
  • Density before Density after hot glazing hot glazing Material 1 (comparison material) 1. 78 1. 34 Material 2 2.02 2.05 Material 3.- 1.88 1. 94 35 Material 4 1. 74 1. 78
  • Photographic material comprising a support and at least one light-sensitive silver halide emulsion printing layer incorporating a 6 thioxo 5,6 dihydrobenzimidazo [1,2-c] quinazoline.
  • Photographic material comprising a support, at least one light-sensitive silver halide emulsion printing layer and at least one additional Water-permeable layer incorporating a 6 thioxo-S,6-dihydrobenzimidazo[1,2-c] quinazoline.
  • Photographic material comprising a support, at least one light-sensitive silver halide emulsion printing layer incorporating a 6 thioxo 5,6 dihydrobenzimidazo[1,2-c] quinazoline, and at least one additional water-permeable layer incorporating a 6-thioxo-5,6-dihydrobenzimidazo [1,2-c] quinazoline.
  • Photographic processing bath incorporating a 6- thioxod,6-dihydrobenzimidazo[ 1,2-c1quinazoline.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US355912A 1963-03-29 1964-03-30 Photographic material Expired - Lifetime US3359106A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
BE2042481 1963-03-29

Publications (1)

Publication Number Publication Date
US3359106A true US3359106A (en) 1967-12-19

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ID=3864798

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US355912A Expired - Lifetime US3359106A (en) 1963-03-29 1964-03-30 Photographic material

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US (1) US3359106A (en)van)
BE (1) BE630297A (en)van)
DE (1) DE1177929B (en)van)
GB (1) GB1055715A (en)van)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3438777A (en) * 1966-02-14 1969-04-15 Agfa Gevaert Nv Photographic material
WO1991012564A1 (en) * 1990-02-07 1991-08-22 Eastman Kodak Company Fixing bath for black and white photographic elements

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1203051A (en) * 1967-02-15 1970-08-26 Agfa Gevaert Nv Improvements in or relating to photographic light-sensitive silver halide materials

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3438777A (en) * 1966-02-14 1969-04-15 Agfa Gevaert Nv Photographic material
WO1991012564A1 (en) * 1990-02-07 1991-08-22 Eastman Kodak Company Fixing bath for black and white photographic elements

Also Published As

Publication number Publication date
BE630297A (en)van)
GB1055715A (en) 1967-01-18
DE1177929B (de) 1964-09-10

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