EP0515388B1 - Stabilisatorverbindung enthaltende photographische silberhalogenidmaterialien - Google Patents

Stabilisatorverbindung enthaltende photographische silberhalogenidmaterialien Download PDF

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Publication number
EP0515388B1
EP0515388B1 EP91902089A EP91902089A EP0515388B1 EP 0515388 B1 EP0515388 B1 EP 0515388B1 EP 91902089 A EP91902089 A EP 91902089A EP 91902089 A EP91902089 A EP 91902089A EP 0515388 B1 EP0515388 B1 EP 0515388B1
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EP
European Patent Office
Prior art keywords
silver halide
photographic
coupler
chromanol
alkyl
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
EP91902089A
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English (en)
French (fr)
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EP0515388A1 (de
Inventor
Llewellyn James c/o Kodak Ltd LEYSHON
Jasbir C/O Kodak Ltd Sidhu
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.)
Kodak Ltd
Eastman Kodak Co
Original Assignee
Kodak Ltd
Eastman Kodak Co
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Filing date
Publication date
Application filed by Kodak Ltd, Eastman Kodak Co filed Critical Kodak Ltd
Priority to AT91902089T priority Critical patent/ATE97505T1/de
Publication of EP0515388A1 publication Critical patent/EP0515388A1/de
Application granted granted Critical
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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
    • 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 4 155 765 describes O-substituted 6-chromanols used as photographic dye image stabilisers.
  • JP-A-61 158 331 describes the use of 8-chromanols to provide magenta dyes of improved light fastness with certain bicyclic magenta couplers.
  • US-A-4 863 842 and US-A-4 623 617 have similar scope except that they concern 7-chromanols.
  • the present invention employs 7-chromanols as stabilisers in photographic materials containing yellow couplers which can form azomethine image 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 yellow dye-forming colour coupler and a 7-chromanol having the general formula: wherein R1 is H, alkyl, substituted alkyl (including arylalkyl), or -R8-COOR, R is an alkyl, R2 - R6 are each, independently, H or an alkyl group, and R8 is an alkylene group.
  • the present photographic materials have incorporated therein a dye-forming colour coupler.
  • a dye-forming colour coupler is well known and are often incorporated in photographic materials as a dispersion in droplets of a coupler solvent.
  • the chromanols and O-substituted-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. As in the production of ordinary coupler dispersions, 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. Also, the dispersion process can be assisted by the presence of a surface active compound, as usual in the manufacture of coupler dispersions.
  • the yellow couplers which may employed in the present photographic materials are water-insoluble acylacetanilide compounds containing ballast groups.
  • Patents describing yellow 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 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 invention are described in Research Disclosure Section IX and the publications cited therein.
  • the photographic elements of this invention or individual layers thereof can contain brighteners (see Research Disclosure Section V), antifoggants and stabilizers (see Research Disclosure Section VI), antistain agents and image dye stabilizer (see Research Disclosure Section VII, paragraphs I and J), light absorbing and scattering materials (see Research Disclosure Section VIII), hardeners (see Research Disclosure Section XI), plasticizers and lubricants (see Research Disclosure Section XII), antistatic agents (see Research Disclosure Section XIII), matting agents (see Research Disclosure Section XVI) and development modifiers (see Research Disclosure Section XXI).
  • brighteners see Research Disclosure Section V
  • antifoggants and stabilizers see Research Disclosure Section VI
  • antistain agents and image dye stabilizer see Research Disclosure Section VII, paragraphs I and J
  • light absorbing and scattering materials see Research Disclosure Section VIII
  • hardeners see Research Disclosure Section XI
  • plasticizers and lubricants see Research Disclosure Section XII
  • antistatic agents see Research Disclosure Section XIII
  • matting agents see Research Disclosure
  • the photogaphic elements can be coated on a variety of supports as described in Research Disclosure Section XVII and the references described therein.
  • 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 to form a visible dye image as described in Research Disclosure Section XIX.
  • 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 silver bromoiodide emulsion at 0.398 Ag/m2, gelatin at 1.36g/m2 and dispersion of coupler (9) in coupler solvent (10) (1.5 moles/mole of coupler).
  • the coupler coverage was 0.83 millimoles/m2.
  • the photographic layer was overcoated with a layer containing gelatin at 3.0g/m2 and bis-vinylsulphonylmethylether hardener at 1.5 weight percent based on total gelatin. Similar coatings were prepared using coupler dispersions which also contained one of the stabilisers (I) and (III) at 0.5 mole per mole coupler.
  • Stabiliser compounds (I) and (V) 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)

Claims (3)

  1. Farbphotographisches Material mit einem Träger, auf den mindestens eine photographische Silberhalogenidemulsionsschicht aufgetragen ist, der ein einen gelben Bildfarbstoff bildender Farbkuppler und ein 7-Chromanol-Bildfarbstoffstabilisator zugeordnet ist, der der folgenden allgemeinen Formel entspricht:
    Figure imgb0016
     worin bedeuten: R¹ gleich H, eine Alkylgruppe, eine substituierte Alkylgruppe (einschließlich einer Arylalkylgruppe), oder -R⁸-COOR,
    R eine Alkylgruppe,
    R² - R⁶ jeweils unabhängig voneinander H oder eine Alkylgruppe und
    R⁸ eine Alkylengruppe.
  2. Photographisches Material nach Anspruch 1, in dem die Alkylgruppen 1 bis 4 Kohlenstoffatome ausweisen.
  3. Photographisches Material nach Anspruch 1 oder 2, in dem das Chromanol ausgewählt ist aus einem der folgenden Chromanole:
    Figure imgb0017
    Figure imgb0018
    Figure imgb0019
    Figure imgb0020
    Figure imgb0021
EP91902089A 1990-01-23 1991-01-12 Stabilisatorverbindung enthaltende photographische silberhalogenidmaterialien Expired - Lifetime EP0515388B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT91902089T ATE97505T1 (de) 1990-01-23 1991-01-12 Stabilisatorverbindung enthaltende photographische silberhalogenidmaterialien.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9001487 1990-01-23
GB909001487A GB9001487D0 (en) 1990-01-23 1990-01-23 Photographic silver halide materials containing a stabiliser compound

Publications (2)

Publication Number Publication Date
EP0515388A1 EP0515388A1 (de) 1992-12-02
EP0515388B1 true EP0515388B1 (de) 1993-11-18

Family

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EP91902089A Expired - Lifetime EP0515388B1 (de) 1990-01-23 1991-01-12 Stabilisatorverbindung enthaltende photographische silberhalogenidmaterialien

Country Status (4)

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EP (1) EP0515388B1 (de)
DE (1) DE69100655T2 (de)
GB (1) GB9001487D0 (de)
WO (1) WO1991011749A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6790965B1 (en) * 1994-05-06 2004-09-14 Pharmacopeia Drug Discovery, Inc. Combinatorial dihydrobenzopyran library
JP5244437B2 (ja) 2008-03-31 2013-07-24 富士フイルム株式会社 紫外線吸収剤組成物
JP2010059235A (ja) 2008-09-01 2010-03-18 Fujifilm Corp 紫外線吸収剤組成物
JP5261319B2 (ja) 2008-09-10 2013-08-14 富士フイルム株式会社 照明カバー

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61158331A (ja) * 1984-12-28 1986-07-18 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5952421B2 (ja) * 1976-07-31 1984-12-19 コニカ株式会社 色素画像褪色防止剤を含有するカラ−写真材料
JPS5448538A (en) * 1977-09-12 1979-04-17 Konishiroku Photo Ind Co Ltd Color photographic material
US4623617A (en) * 1984-10-09 1986-11-18 Konishiroku Photo Industry Co., Ltd. Silver halide color photographic material
JPS61194444A (ja) * 1985-02-22 1986-08-28 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料
DE3666984D1 (en) * 1985-09-12 1989-12-21 Konishiroku Photo Ind Silver halide photographic material

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61158331A (ja) * 1984-12-28 1986-07-18 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料

Also Published As

Publication number Publication date
WO1991011749A1 (en) 1991-08-08
GB9001487D0 (en) 1990-03-21
DE69100655T2 (de) 1994-06-16
EP0515388A1 (de) 1992-12-02
DE69100655D1 (de) 1993-12-23

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