[go: up one dir, main page]

WO1991011749A1 - Materiaux photographiques a l'halogenure d'argent contenant un compose de stabilisation - Google Patents

Materiaux photographiques a l'halogenure d'argent contenant un compose de stabilisation Download PDF

Info

Publication number
WO1991011749A1
WO1991011749A1 PCT/EP1991/000068 EP9100068W WO9111749A1 WO 1991011749 A1 WO1991011749 A1 WO 1991011749A1 EP 9100068 W EP9100068 W EP 9100068W WO 9111749 A1 WO9111749 A1 WO 9111749A1
Authority
WO
WIPO (PCT)
Prior art keywords
chromanol
photographic
coupler
silver halide
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.)
Ceased
Application number
PCT/EP1991/000068
Other languages
English (en)
Inventor
Llewellyn James Leyshon
Jasbir 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
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 Kodak Ltd, Eastman Kodak Co filed Critical Kodak Ltd
Priority to AT91902089T priority Critical patent/ATE97505T1/de
Priority to DE69100655T priority patent/DE69100655T2/de
Publication of WO1991011749A1 publication Critical patent/WO1991011749A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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.

Landscapes

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

Abstract

Matériau photographique couleur constitué d'un support contenant au moins une couche d'émulsion photographique à l'halogénure d'argent à laquelle est associé un stabilisant de colorant d'image à base de chromanol en positions 5, 7 ou 8.
PCT/EP1991/000068 1990-01-23 1991-01-12 Materiaux photographiques a l'halogenure d'argent contenant un compose de stabilisation Ceased WO1991011749A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AT91902089T ATE97505T1 (de) 1990-01-23 1991-01-12 Stabilisatorverbindung enthaltende photographische silberhalogenidmaterialien.
DE69100655T DE69100655T2 (de) 1990-01-23 1991-01-12 Stabilisatorverbindung enthaltende photographische silberhalogenidmaterialien.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9001487.9 1990-01-23
GB909001487A GB9001487D0 (en) 1990-01-23 1990-01-23 Photographic silver halide materials containing a stabiliser compound

Publications (1)

Publication Number Publication Date
WO1991011749A1 true WO1991011749A1 (fr) 1991-08-08

Family

ID=10669735

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1991/000068 Ceased WO1991011749A1 (fr) 1990-01-23 1991-01-12 Materiaux photographiques a l'halogenure d'argent contenant un compose de stabilisation

Country Status (4)

Country Link
EP (1) EP0515388B1 (fr)
DE (1) DE69100655T2 (fr)
GB (1) GB9001487D0 (fr)
WO (1) WO1991011749A1 (fr)

Cited By (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
WO2009123141A1 (fr) 2008-03-31 2009-10-08 富士フイルム株式会社 Compositions absorbant les rayons ultraviolets
WO2010024441A1 (fr) 2008-09-01 2010-03-04 富士フイルム株式会社 Composition d'agent absorbant l'uv
WO2010029926A1 (fr) 2008-09-10 2010-03-18 富士フイルム株式会社 Protège-lampe

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4155765A (en) * 1976-07-31 1979-05-22 Konishiroku Photo Industry Co., Ltd. Color photographic materials containing agents for preventing dye images from fading
US4254216A (en) * 1977-09-12 1981-03-03 Konishiroku Photo Industry Co., Ltd. Color photographic material
US4623617A (en) * 1984-10-09 1986-11-18 Konishiroku Photo Industry Co., Ltd. Silver halide color photographic material
US4863842A (en) * 1985-09-12 1989-09-05 Konica Technosearch Corporation Silver halide photographic light sensitive material
US4906559A (en) * 1985-02-22 1990-03-06 Konishiroku Photo Industry Co., Ltd. Light-sensitive silver halide photographic material

Family Cites Families (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

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4155765A (en) * 1976-07-31 1979-05-22 Konishiroku Photo Industry Co., Ltd. Color photographic materials containing agents for preventing dye images from fading
US4254216A (en) * 1977-09-12 1981-03-03 Konishiroku Photo Industry Co., Ltd. Color photographic material
US4623617A (en) * 1984-10-09 1986-11-18 Konishiroku Photo Industry Co., Ltd. Silver halide color photographic material
US4906559A (en) * 1985-02-22 1990-03-06 Konishiroku Photo Industry Co., Ltd. Light-sensitive silver halide photographic material
US4863842A (en) * 1985-09-12 1989-09-05 Konica Technosearch Corporation Silver halide photographic light sensitive material

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JP, A, 61-158331 (KONISHIROKU PHOTO KK) 18 July 1986, see page 307 & Orbit Search Service, File WPAT, Accession number 86-228719/35, (KONISHIROKU PHOTO KK), J61158331-A, 860718, 8635, abstract *

Cited By (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
WO2009123141A1 (fr) 2008-03-31 2009-10-08 富士フイルム株式会社 Compositions absorbant les rayons ultraviolets
WO2010024441A1 (fr) 2008-09-01 2010-03-04 富士フイルム株式会社 Composition d'agent absorbant l'uv
WO2010029926A1 (fr) 2008-09-10 2010-03-18 富士フイルム株式会社 Protège-lampe

Also Published As

Publication number Publication date
EP0515388B1 (fr) 1993-11-18
GB9001487D0 (en) 1990-03-21
DE69100655T2 (de) 1994-06-16
DE69100655D1 (de) 1993-12-23
EP0515388A1 (fr) 1992-12-02

Similar Documents

Publication Publication Date Title
EP0337784B1 (fr) Stabilisation d'images de colorant produites dans des matériaux photographiques
US4782011A (en) Bisphenol derivative stabilizers
US4749645A (en) Heterocyclic phosphorus compound stabilizers
EP0164961B1 (fr) Eléments photographiques utilisant de nouveaux solvants pour coupleurs
EP0080355B1 (fr) Eléments photographiques contenant des coupleurs photographiques substitués par aryloxy
US4923787A (en) Photographic element containing scavenger for oxidized developing agent
EP0249473A2 (fr) Coupleurs photographiques acétanilides et éléments photographiques les contenant
EP0296794B1 (fr) Elément formateur d'image contenant un composé couplant libérateur de colorant fluorescent
US4207393A (en) Photographic contrast enhancers
EP0286253B1 (fr) Stabilisation d'images de colorants produites dans des matériaux photographiques
EP0504154B1 (fr) Materiaux photographiques a base d'halogenure d'argent
EP0486029B1 (fr) Eléments photographiques comprenant des composés libérés II
EP0515388B1 (fr) Materiaux photographiques a l'halogenure d'argent contenant un compose de stabilisation
EP0229720B1 (fr) Organosilanes pour l'augmentation du développement photographique en couleur
US5283162A (en) Photographic elements containing sulfite releasable release compounds
US4359523A (en) Photographic element containing a UV-filter layer
EP0572054A1 (fr) Matériaux photographiques couleur à l'halogénure d'argent
EP0679942B1 (fr) Matériau photographique couleur à l'halogénure d'argent
EP0272041B1 (fr) Coupleurs photographiques acétanilide avec un nouveau groupe ballast et éléments photographiques les contenant
US4973545A (en) Photographic couplers with aryloxysilyl groups
US5262291A (en) Photographic elements containing release compounds
EP0600563B1 (fr) Copulants jaune ayant un groupe libéré aryloxy comprenant un groupe fonctionnel orthopolarisable
US5262284A (en) Arylidene pyrazolone coupler
EP0463136B1 (fr) Emulsions photographiques de chlorure d'argent
JPS6286361A (ja) ハロゲン化銀写真感光材料

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): JP US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IT LU NL SE

WWE Wipo information: entry into national phase

Ref document number: 1991902089

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1991902089

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: 1991902089

Country of ref document: EP