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
  • G03C1/10—Organic substances
  • G03C1/12—Methine and polymethine dyes
  • G03C1/14—Methine and polymethine dyes with an odd number of CH groups
  • G03C1/20—Methine and polymethine dyes with an odd number of CH groups with more than three CH groups
• • 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
  • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
  • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
  • G03C1/83—Organic dyestuffs therefor
  • G03C1/832—Methine or polymethine dyes

Definitions

• the present invention relates to the use of indolenine cyanine dyes as infrared absorbing agents in photographic recording materials and photographic recording materials containing indolenine cyanine dyes.
• Photographic recording materials generally have a multilayer structure.
• Infrared-sensitive materials based on silver halide contain one or more colloid layers with one or more infrared-absorbing dyes. the image sharpness of the recording material is to be increased.
• These dye-containing layers can be used in various positions within the multilayer material, but dye-containing layers can also be applied to the back of a photographic material to suppress blurring effects by reflecting scattered light (anti-halo layers). It is also already known to introduce the dye directly into the light-sensitive colloid layers containing silver halides.
• Suitable dyes must have suitable absorption characteristics, be completely decolorized during the wet photographic processing process, and must be easily washed out of the photographic material so that the developed material has no residual color after processing. In addition, there should be no coloring of the baths.
• infrared-absorbing dyes of the heptamethine cyanine type Indolenine end groups (US 4,876,181, EP-A 445,627) or bridged and substituted indolenine cyanines (US 4,933,269, EP-A 350 026) are used.
• these dyes do not meet the requirements or only partially. For example, they are only slowly and / or imperfectly decolorized during the photographic processing process and / or are difficult to access synthetically, ie only with considerable effort and the associated costs.
• benz [e] indolenine cyanines the carcinogenic 2-naphthylamine must also be assumed.
• the present invention thus relates to the use of dyes of the general formula I. wherein R1 and R2 independently of one another hydrogen, hydroxy, (C1-C4) alkoxy, amino, (C1-C4) alkylamino, di- (C1-C4) alkylamino or halogen and M ⁇ a cation mean as infrared absorbing agents in silver halide photographic materials.
• (C1-C4) alkyl groups can be straight-chain or branched and mean, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl and tert-butyl. Methyl, ethyl and n-propyl are preferred.
• Halogen means in particular fluorine, chlorine, bromine and iodine, chlorine being preferred, R1 and R2 are preferably hydrogen.
• Cations standing for M ⁇ are preferably monovalent cations, alkali metal cations and substituted ammonium ions and the ammonium ion itself being particularly preferred.
• M ⁇ is particularly preferably the sodium ion, the potassium ion, the ammonium ion and the triethylammonium ion.
• the dyes of the general formula I are preferably used in amounts of 5 to 500 mg / m2, particularly preferably 20 to 200 mg / m2.
• the dyes of the general formula I can be obtained in a simple manner known per se, for example by reacting an appropriately substituted 2,3,3-trimethylindolenine with 2-chloroethanesulfonyl chloride and glutacondialdehyde, which is generally used in the form of its dianil hydrochloride.
• the dye of the general formula I in which R1 and R2 are hydrogen and M ⁇ is the triethylammonium ion is obtained as follows:
• the present invention also relates to silver halide-based photographic materials which are characterized in that they contain a dye of the general formula I as an infrared absorbing agent.
• the recording materials according to the invention generally have a multilayer structure, the dye of the general formula I can be used in any position within the material, preferably in the light-sensitive colloid layer containing silver halides, or else in separate hydrophilic colloid layers, e.g. in an antihalo layer.
• the colloid layers mentioned consist, for example, of polyvinyl alcohol, carboxymethyl cellulose, sodium alginate, casein, polyvinyl pyrrolidone, but preferably of gelatin.
• the materials mentioned can also be used in any mixtures with one another.
• the colloid layers also contain other auxiliaries, for example casting additives, wetting agents or curing agents (see e.g. Research Disclosure, Vol. 308, 1989, Item 308119).
• the dye of the general formula I is preferably present in the colloid layers in amounts of 5 to 500 mg / m2, particularly preferably 20 to 200 mg / m2.
• the dyes of the general formula I can be incorporated into the recording material according to the invention or a colloid layer in a simple manner known per se.
• the dyes are in a suitable solvent, especially water or alcohols, e.g. Ethanol, dissolved and then optionally in the presence of a wetting agent and / or other casting additives in the above material, preferably gelatin, introduced.
• a suitable solvent especially water or alcohols, e.g. Ethanol
• a wetting agent and / or other casting additives in the above material preferably gelatin, introduced.
• the casting solutions obtained in this way can then be applied in layer form by methods known per se (see, for example, "Science and Technology of Photography", Karlheinz Keller (Ed.), VCH Verlagsges.mbH., Weinheim 1993).
• the dyes of the general formula I can be easily incorporated into the photographic material, give it a suitable absorption characteristic, are irreversibly discolored during the photographic development process and are easily accessible synthetically.
• N-sulfoethyl groups are decisive for the advantages compared to the dyes used according to the prior art. Longer sulfoalkyl groups surprisingly lead to significantly poorer bleachability and washout behavior, which could at best be compensated for by introducing additional sulfo groups.
• gelatin layers obtained were subjected to the following photographic processing process: Development in a customary metol hydroquinone developer at 20 ° C. for 2 minutes, then treatment in a customary fixing bath (containing sodium thiosulfate and sodium disulfite) for 5 minutes and subsequent rinsing with water and subsequent drying for 10 minutes.

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• Chemical & Material Sciences (AREA)
• Physics & Mathematics (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• General Physics & Mathematics (AREA)
• Spectroscopy & Molecular Physics (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Plural Heterocyclic Compounds (AREA)
• Indole Compounds (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)

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Citations (4)

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• 1994
  • 1994-04-21 DE DE19944413893 patent/DE4413893A1/de not_active Withdrawn
• 1995
  • 1995-04-01 EP EP95104870A patent/EP0678778A1/fr not_active Withdrawn
  • 1995-04-19 JP JP7093879A patent/JPH0862781A/ja not_active Withdrawn
  • 1995-04-20 CA CA 2147450 patent/CA2147450A1/fr not_active Abandoned

Patent Citations (4)

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