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
  • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
  • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
  • G03C7/392—Additives
  • G03C7/39208—Organic compounds
  • G03C7/3924—Heterocyclic
  • G03C7/39268—Heterocyclic the nucleus containing only oxygen as hetero atoms

Definitions

• This invention relates to photographic silver halide materials containing a stabiliser compound and particularly to colour photographic materials.
• US Patent 3 591 381 describes the use of 6-chromanols as stabilisers for azo dyes, reducing fade caused by light, moisture and heat.
• US patent A 155 765 describes O-substituted 6—chromanols used as photographic dye image stabilisers.
• US patent 3 574 627 describes photographic dye image stabilisers which are A-chromanols having 2,2— entamethylene and 2,2-tetramethylene rings.
• the present invention employs related compounds, the 5-, 7— and 8—chromanols as stabilisers in photographic materials in which the image dyes, as is well known, are azomethine dyes. It has been found that not all chromanol-coupler combinations have the same properties, for example 6—chromanols have a deleterious effect on image dye stability when used in combination with yellow couplers.
• a colour photographic material comprising a support carrying at least one photographic silver halide emulsion layer having associated therewith a 5-, 7— or 8—chromanol image dye stabiliser.
• the preferred chromanols have one of the general formulae:
• -_- (including arylalkyl, eg benzyl), preferably wherein the alkyl groups have 1—4 carbon g atoms, or -R -COOR,
• R is an alkyl, preferably having 1-4 carbon atoms
• R — R are each, independently, H or an alkyl group, preferably having 1—4 carbon atoms, and
• R is an alkylene group, preferably having
• the present photographic materials have incorporated therein a dye— orming colour coupler.
• a dye— orming colour coupler Such couplers are well known and are often incorporated in photographic materials as a dispersion in droplets of a coupler solvent.
• the chromanols employed in the present invention may be prepared by reaction of the appropriate dihydric phenol with the appropriate diene, eg 2,5—dimethyl—2,4—hexadiene to form the basic chromanol followed by other reactions, in themselves known, to introduce a further substituents. Such processes are illustrated in Examples below.
• the chromanols are used in an amount sufficient to stabilize the photographic image dyes and their precursors e.g. in an amount from 0.2 to 2.0 mole per mole coupler, more preferably at approximately equimolar amounts.
• the chromanol may be incorporated in the silver halide emulsion layer or a layer adjacent thereto. It can be incorporated as a separate dispersion, but is preferably incorporated in admixture with the coupler. Both coupler and stabilizer may be dissolved in a conventional coupler ⁇ * * solvent, such as dibutyl phthalate.
• a volatile and/or water—miscible auxiliary solvent such as ethyl acetate, may be used to aid the dispersion process and then removed by evaporation or by washing the set
• dispersion process can be assisted by the presence of a surface active compound, as usual in the manufacture of coupler dispersions.
• the couplers which may employed in the present photographic materials are water—insoluble compounds containing ballast groups, phenolic (including naphtholic) couplers being used for producing cyan dyes, acylacetanilides for yellow dyes 0 and pyrazolones for producing magenta dyes.
• Patents describing couplers for use in the present invention include the following United States Patents:
• the stabilizers are useful in any coupler—incorporated silver halide photographic ,. materials, including monochrome materials, false—colour materials and colour transparency, negative and print materials, to stabilize the image dye obtained on development with a solution including a p_-phenylenediamine colour developing agent.
• Such developing agents are well—known, being described in,for example Photographic Processing Chemistry, L.F.A. Mason, Focal Press, London, 2nd edition (1975) pp 229—235 and Modern Photographic Processing,, Grant Haist, Wiley, New York (1979), Volume 2 pp 463-8. They may also be used in colour materials not containing couplers but processed in developer solutions containing couplers.
• the silver halide emulsion employed in the elements of this invention can be either 5 negative—working or positive-working. Suitable emulsions and their preparation are described in Research Disclosure Sections 1 and II and the publications cited therein. Suitable vehicles for the emulsion layers and other layers of elements of this
• the photographic elements of this invention or individual layers thereof, can contain brighteners (see Research Disclosure Section V), antifoggants and
• the photogaphic elements can be coated on a variety of supports as described in Research Disclosure Section XVII and the references described therein. 0 Photographic elements can be exposed to actinic radiation, typically in the visible region of the spectrum, to form a latent image as described in Research Disclosure Section XVIII and then processed
• Processing to form a visible dye image includes the step of contacting the element with a colour developing agent to reduce developable silver halide and oxidize the colour developing agent. Oxidized colour developing agent in turn reacts with the coupler to yield a dye.
• this processing step leads to a negative image.
• this step can be preceded by development with a non—chromogenic developing agent to develop exposed silver halide, but not form dye, and then uniform fogging of the element to render unexposed silver halide developable.
• a direct positive emulsion can be employed to obtain a positive image.
• Single layer film strips were prepared by coating a gel-subbed polyethylene-terephthalate support with a photosensitive layer containing a
• the photographic layer was overcoated with a layer containing gelatin
• Samples were exposed through a graduated density test object and developed with 4—amino-3- methyl-N-ethyl—N- ⁇ -(methanesulphonamido)ethyl-aniline in an EP-2 process.
• Coupler (9) 1.05 0.97 -0.08 (7.6%)
• Typical single layer film strips were prepared by coating, as in Example 4, a gel—subbed polyethylene- terephthalate support with a photosensitive layer containing a silver bromoiodide emulsion at 0.538 Ag/m 2, gelatin at 3.23g/m2 and dispersion of coupler (11) in coupler solvent (10)
• the photographic layer was overcoated with a layer containing gelatin at
• Coupler (11) had the formula:
• Stabiliser compounds (II) and (VII) greatly improved the fade performance in all cases.

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• Physics & Mathematics (AREA)
• Spectroscopy & Molecular Physics (AREA)
• General Physics & Mathematics (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)

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Citations (5)

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• 1990
  • 1990-01-23 GB GB909001487A patent/GB9001487D0/en active Pending
• 1991
  • 1991-01-12 WO PCT/EP1991/000068 patent/WO1991011749A1/en active IP Right Grant
  • 1991-01-12 EP EP91902089A patent/EP0515388B1/de not_active Expired - Lifetime
  • 1991-01-12 DE DE69100655T patent/DE69100655T2/de not_active Expired - Fee Related

Patent Citations (5)

Non-Patent Citations (1)

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