EP0504154B1 - Photographisches silberhalogenidmaterial - Google Patents

Photographisches silberhalogenidmaterial Download PDF

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Publication number
EP0504154B1
EP0504154B1 EP90916275A EP90916275A EP0504154B1 EP 0504154 B1 EP0504154 B1 EP 0504154B1 EP 90916275 A EP90916275 A EP 90916275A EP 90916275 A EP90916275 A EP 90916275A EP 0504154 B1 EP0504154 B1 EP 0504154B1
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EP
European Patent Office
Prior art keywords
group
substituted
coupler
silver halide
aryl
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.)
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Application number
EP90916275A
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English (en)
French (fr)
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EP0504154A1 (de
Inventor
Llewellyn James Leyshon
John Demita Goddard
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
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Kodak Ltd
Eastman Kodak Co
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Priority to AT90916275T priority Critical patent/ATE98787T1/de
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Publication of EP0504154B1 publication Critical patent/EP0504154B1/de
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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
    • G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
    • G03C7/30511—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the releasing group
    • G03C7/30517—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution
    • G03C7/30535—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution having the coupling site not in rings of cyclic compounds
    • 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
    • G03C7/39212—Carbocyclic
    • G03C7/39216—Carbocyclic with OH groups

Definitions

  • the coupling-off group X may be chlorine a heterocyclic group or an aryloxy or arylthio group optionally substituted with alkyl or arylsulphonyl, alkylsulphonamido, or alkoxycarbonyl groups which themselves are optionally substituted.
  • Preferred coupling-off groups are phenoxy groups containing electron-withdrawing substituents at the ortho- and/or para positions, especially at the para- and one ortho-position. In addition, ionisable substituents are also beneficial. Examples of coupling-off groups that may be used are the following:
  • a preferred group of bisphenol compounds are known dye image stabilisers represented by the following general formula wherein A is a blocking group such as alkyl e.g. methyl, ethyl, propyl or butyl; cycloalkyl e.g. cyclohexyl; alkenyl; aryl e.g. phenyl; acyl e.g. acetyl or benzoyl; alkylsulphonyl or arylsulphonyl; L is a single bond or a linking group such as alkylene e.g. methylene; alkylidene e.g. butylidene or 3,5,5,-trimethylhexylidene; a heteroatom e.g.
  • A is a blocking group such as alkyl e.g. methyl, ethyl, propyl or butyl; cycloalkyl e.g. cyclohexyl; alkenyl; aryl
  • each R independently represents one or more substituents each independently selected from alkyl, alkoxy, alkenyl, cycloalkyl, or aryl; or each R independently represents the atoms necessary to complete with the benzene ring to which it is attached a fused polycyclic aromatic ring structure; all the above mentioned alkyl, cycloalkyl, alkylene, alkenyl, acyl and aryl groups being optionally substituted.
  • Particularly preferred bisphenols are represented by the general formula wherein A and L are as defined above; and, R3, R4, R5 and R6 each independently represent substituted or unsubstituted alkyl, alkenyl, cycloalkyl or aryl.
  • R3 and R4 are identical and R5 and R6 are identical.
  • Alkylidene bisphenols represent a preferred group of stabilizers in which the linking group L may be -(CR7R8) n - wherein each of R7 and R8 independently is hydrogen or optionally substituted alkyl, cycloalkyl, alkenyl or aryl and n is an integer from 1 to 10, preferably 1 to 3, most preferably 1.
  • both the coupler and the bisphenol derivative are dissolved in a coupler solvent and this solution is dispersed in an aqueous gelatin solution.
  • coupler solvents that may be used are dibutyl phthalate, tricresyl phosphate, diethyl lauramide and 2,4-di-tertiary-amylphenol.
  • an auxiliary coupler solvent may also be used, for example ethyl acetate, cyclohexanone, and 2-(2-butoxy-ethoxy)ethyl acetate, which are removed from the dispersion before incorporation into the photographic material.
  • the photographic elements can be single colour elements or multicolour elements.
  • the yellow dye-forming couplers of this invention would usually be associated with a blue-sensitive emulsion, although they could be associated with an emulsion sensitised to a different region of the spectrum, or with a panchromatically sensitised, orthochromatically sensitised or unsensitised emulsion.
  • Multicolour elements contain dye image-forming units sensitive to each of the three primary regions of the spectrum. Each unit can be comprised of a single emulsion layer or of multiple emulsion layers sensitive to a given region of the spectrum.
  • the layers of the elements, including the layers of the image-forming units can be arranged in various orders as known in the art.
  • a typical multicolour photographic element comprises a support bearing a yellow dye image-forming unit comprised of at least one blue-sensitive silver halide emulsion layer having associated therewith at least one yellow dye-forming coupler and magenta and cyan dye image-forming units comprising at least one green- or red-sensitive silver halide emulsion layer having associated therewith at least one magenta or cyan dye-forming coupler respectively.
  • the element can contain additional layers, such as filter layers.
  • the silver halide emulsion employed in the elements improved by this invention can be either negative-working or positive-working.
  • Suitable emulsions and their preparation are described in Research Disclosure Sections I 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 or individual layers thereof can contain brighteners (see Research Disclosure Section V), antifoggants and stabilisers (see Research Disclosure Section VI), antistain agents and image dye stabiliser (see Research Disclosure Section VII, paragraphs I and J), light absorbing and scattering materials (see Research Disclosure Section VIII), hardeners (see Research Disclosure Section XII, plasticisers and lubricants (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 stabilisers see Research Disclosure Section VI
  • antistain agents and image dye stabiliser see Research Disclosure Section VII, paragraphs I and J
  • light absorbing and scattering materials see Research Disclosure Section VIII
  • hardeners see Research Disclosure Section XII, plasticisers and lubricants (see Research Disclosure Section XIII), matting agents (see Research Disclosure Section XVI) and development modifiers (see Research Disclosure Section XXI).
  • the photographic 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 elements with a colour developing agent to reduce developable silver halide and oxidise the colour developing agent. Oxidised colour developing agent in turn reacts with the coupler to yield a dye.
  • Preferred colour developing agents are p-phenylene diamines.
  • Preferred colour developing agents are 4-amino-3-methyl-N,N-diethylaniline hydrochloride, 4-amino-3-methyl-N-ethyl-N- ⁇ -(methylanesulphonamido)ethylaniline sulphate hydrate, 4-amino-3-methyl-N-ethyl-N- ⁇ -(methanesulphonamide)ethyl-N,N-diethylaniline hydrochloride and 4-amino-N-ethyl-N-(2-methoxyethyl)-m-toluidine di-p-toluene sulphonate.
  • this processing step leads to a negative image.
  • this step can be preceded by development with a non-chromagenic developing agent to develop exposed silver halide, but not form dye, and then uniform fogging of the elements to render unexposed silver halide developable.
  • a direct positive emulsion can be employed to obtain a positive image.
  • Coupler (1) Two dispersions of Coupler (1) in gelatin, with and without added Compound (1), were prepared by ultrasonic agitation (Dawe Instruments "Soniprobe"). Details of the method are given below:
  • Coupler (1) dispersions were coated with a blue-sensitive AgCl emulsion to give coatings of the following structure:
  • Coupler (A) dispersion was coated similarly except that the coupler coverage was increased to 0.753g per square metre.
  • Coupler (A) has the formula:
  • Example 1 Further Coupler (1) dispersions were prepared and coated as in Example 1, containing, respectively, no stabiliser, and various stabilisers including some outside the present invention. Compared with Example 1, the coating coverages were reduced to 0.382g per square metre coupler and 0.17g per square metre Ag.

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

Claims (9)

  1. Verfahren zur Erhöhung von Dmax und Gamma sowie zur Verminderung von Dmin des gelben Farbstoffbildes, das in einem photosensitiven photographischen Farbmaterial erzeugt worden ist, das aufweist einen Träger, auf dem sich eine Silberhalogenidemulsionsschicht befindet, wobei der Halogenidgehalt derselben bei mindestens 85 % Chlorid liegt und das in oder benachbart zur Silberhalogenidschicht einen eine Ballastgruppe aufweisenden gelben Kuppler der allgemeinen Formel aufweist:
    Figure imgb0045
     worin bedeuten: L¹ eine Gruppe der Formeln -NHSO₂-, -SO₂NH-, -OCO-, -COO-, -OSO₂- oder -SO₂O-,
    R¹ ein Halogenatom oder eine Alkoxygruppe mit 1 bis 4 Kohlenstoffatomen,
    R² eine substituierte oder unsubstituierte Alkyl- oder eine substituierte oder unsubstituierte Arylgruppe einer solchen Größe und Konfiguration um den Kuppler in dem photographischen Material nicht-diffundierend zu machen, und
    X eine ab-kuppelnde Halogen-, Aryloxy-, Arylthio- oder heterocyclische Gruppe,
    das die bildweise Exponierung und Farbentwicklung umfaßt einschließlich der Stufe der Farbentwicklung in Abwesenheit von Benzylalkohol, durch Einverleiben eines Bisphenolderivates mit zwei miteinander verbundenen Phenolringen, wobei eine der phenolischen Hydroxygruppen substituiert ist durch eine blokkierende Gruppe und wobei mindestens einer der Phenolringe substituiert ist, in die Schicht, die den Kuppler enthält.
  2. Verfahren nach Anspruch 1, bei dem die Gruppe R² eine Gruppe der folgenden Formeln umfaßt:
    Figure imgb0046
  3. Verfahren nach Anspruch 1 oder 2, bei dem die Gruppe R¹ eine Chlor- oder Methoxygruppe ist.
  4. Verfahren nach einem der Ansprüche 1 bis 3, in dem die abkuppelnde Gruppe X eine Gruppe der folgenden Formeln ist:
    (a)
    Figure imgb0047
    (b)
    Figure imgb0048
    (c)
    Figure imgb0049
    (d)
    Figure imgb0050
    (e)
    Figure imgb0051
    (f)
    Figure imgb0052
    (g)
    Figure imgb0053
    (h)
    Figure imgb0054
    (i)
    Figure imgb0055
    (j)

            -Cl

    (k)
    Figure imgb0056
  5. Verfahren nach einem der Ansprüche 1 bis 4, bei dem das Bisphenolderivat der folgenden allgemeinen Formel entspricht:
    Figure imgb0057
     worin bedeuten:
    A eine blockierende Gruppe, wie z. B. eine Alkylgruppe, z. B. Methyl, Ethyl, Propyl oder Butyl; eine Cycloalkylgruppe, z. B. Cyclohexyl; eine Alkenylgruppe; eine Arylgruppe, z. B. Phenyl; eine Acylgruppe, z. B. Acetyl oder Benzoyl; Alkylsulphonyl oder Arylsulphonyl;
    L eine einzelne Bindung oder eine verbindende Gruppe, z. B. eine Alkylengruppe, z. B. Methylen; eine Alkylidengruppe, z. B. Butyliden oder 3,5,5-Trimethylhexyliden; ein Heteroatom, z. B. Sauerstoff oder Schwefel; oder eine Sulphonylgruppe; und
    R jeweils unabhängig voneinander einen oder mehrere Substituenten, jeweils unabhängig voneinander ausgewählt aus Alkyl, Alkoxy, Alkenyl, Cycloalkyl oder Aryl; oder R unabhängig voneinander die Atome, die gemeinsam mit dem Benzolring, an den R gebunden ist, eine ankondensierte polycyclische aromatische Ringstruktur bilden;
    wobei gilt, daß sämtliche der angegebenen Alkyl-, Cycloalkyl-, Alkylen-, Alkenyl-, Acyl- und Arylgruppen gegebenenfalls substituiert sein können.
  6. Verfahren nach einem der Ansprüche 1 bis 5, bei dem das Bisphenolderivat der allgemeinen Formel:
    Figure imgb0058
     entspricht, worin bedeuten:
    A und L Reste der in Anspruch 5 angegebenen Bedeutung; und
    R³, R⁴, R⁵ und R⁶ jeweils unabhängig voneinander substituierte oder unsubstituierte Alkyl-, Alkenyl-, Cycloalkyl- oder Aryl-gruppen, wobei R³ und R⁴ vorzugsweise identisch sind und R⁵ und R⁶ identisch sind, wobei
    Alkylidenbisphenole eine bevorzugte Gruppe von Stabilisatoren darstellen, in denen die verbindende Gruppe L der Formel (CR⁷R⁸)n- entsprechen kann, worin R⁷ und R⁸ jeweils unabhängig voneinander stehen für Wasserstoff oder gegebenenfalls substituierte Alkyl-, Cycloalkyl-, Alkenyl- oder Arylgruppen und worin n eine Zahl von 1 bis 10, vorzugsweise 1 bis 3 und insbesondere 1 ist.
  7. Verfahren nach einem der Ansprüche 1 bis 6, in dem die Bisphenol-Verbindung einer der folgenden Formeln entspricht:
    Figure imgb0059
    Figure imgb0060
     und
    Figure imgb0061
  8. Verfahren nach einem der Ansprüche 1 bis 7, in dem der Kuppler ein Kuppler der in der folgenden Tabelle angegebenen Struktur ist:
    Figure imgb0062
    Figure imgb0063
    worin die Gruppen (f), (c), (g) und (k) die in Anspruch 4 angegebene Bedeutung besitzen.
  9. Verfahren nach einem der Ansprüche 1 bis 8, bei dem das photographische Material ein mehrfarbiges photographisches Element ist mit einem Träger, auf dem sich eine ein gelbes Farbstoffbild bildende Einheit befindet, mit mindestens einer blau-empfindlichen Silberhalogenidemulsionsschicht, der mindestens ein Kuppler und ein blockiertes Bis-Phenol wie in einem der Ansprüche 1 bis 8 definiert zugeordnet ist, sowie purpurrote und blaugrüne Farbstoffbilder bildende Einheiten mit mindestens einer grün- oder rot-empfindlichen Silberhalogenidemulsionsschicht, der mindestens ein ein purpurrotes Farbstoffbild bildender Kuppler beziehungsweise ein ein blaugrünes Farbstoffbild bildender Kuppler zugeordnet ist, aufweist.
EP90916275A 1989-12-06 1990-11-14 Photographisches silberhalogenidmaterial Expired - Lifetime EP0504154B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT90916275T ATE98787T1 (de) 1989-12-06 1990-11-14 Photographisches silberhalogenidmaterial.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8927563 1989-12-06
GB898927563A GB8927563D0 (en) 1989-12-06 1989-12-06 Photographic silver halide materials

Publications (2)

Publication Number Publication Date
EP0504154A1 EP0504154A1 (de) 1992-09-23
EP0504154B1 true EP0504154B1 (de) 1993-12-15

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EP90916275A Expired - Lifetime EP0504154B1 (de) 1989-12-06 1990-11-14 Photographisches silberhalogenidmaterial

Country Status (5)

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EP (1) EP0504154B1 (de)
DE (1) DE69005313T2 (de)
ES (1) ES2062565T3 (de)
GB (1) GB8927563D0 (de)
WO (1) WO1991008515A1 (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9001078D0 (en) * 1990-01-17 1990-03-14 Kodak Ltd Photographic silver chloride emulsions
GB9201235D0 (en) * 1992-01-21 1992-03-11 Kodak Ltd Improvements in dye stability
US5534390A (en) * 1993-11-12 1996-07-09 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US5451492A (en) * 1994-03-17 1995-09-19 Eastman Kodak Company Photographic elements containing certain acylacetanilide couplers in combination with development inhibitor releasing couplers
US5498515A (en) * 1994-03-17 1996-03-12 Eastman Kodak Company Photographic element containing a certain sulfonated acylacetanilide coupler in combination with low- or non-chloride emulsions
US5451493A (en) * 1994-03-17 1995-09-19 Eastman Kodak Company Photographic element containing a certain sulfonated acylacetanilide coupler in combination with a development inhibitor releasing coupler
US5891613A (en) * 1997-08-22 1999-04-06 Eastman Kodak Company Silver halide light-sensitive element
US6162598A (en) * 1998-12-22 2000-12-19 Eastman Kodak Company Silver halide photographic element containing improved yellow dye-forming coupler
US6312881B1 (en) * 2000-01-14 2001-11-06 Eastman Kodak Company Photographic element with yellow dye-forming coupler and stabilizing compounds
US6555306B1 (en) 2001-12-21 2003-04-29 Eastman Kodak Company Photographic element with dye-forming coupler and image dye stabilizing compound
US6846620B1 (en) 2003-06-27 2005-01-25 Albert J. Mura, Jr. Photographic element with dye-forming coupler and image dye stabilizing coupler solvent

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3933501A (en) * 1973-11-28 1976-01-20 Eastman Kodak Company Photographic elements containing color-forming couplers having and inhibiting effect upon the reactivity of competing couplers
JPS62153953A (ja) * 1985-12-27 1987-07-08 Fuji Photo Film Co Ltd カラ−写真感光材料
JPS62153954A (ja) * 1985-12-27 1987-07-08 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真感光材料
JPH0621949B2 (ja) * 1986-01-23 1994-03-23 富士写真フイルム株式会社 カラ−画像形成法
GB8610610D0 (en) * 1986-04-30 1986-06-04 Kodak Ltd Stabilization of dye images
JPS6344658A (ja) * 1986-08-13 1988-02-25 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真感光材料

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
British Journal of Photography annual 1986,pages 37 and 38 *
Kubo:Toward the New Age of Colour Print,Shashin Koggo,vol.44,No.8,08.86,pages 95-98 and English translation *
Research Disclosure No.17 643(12.78) *

Also Published As

Publication number Publication date
ES2062565T3 (es) 1994-12-16
DE69005313T2 (de) 1994-07-21
DE69005313D1 (de) 1994-01-27
EP0504154A1 (de) 1992-09-23
GB8927563D0 (en) 1990-02-07
WO1991008515A1 (en) 1991-06-13

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