EP0987593A1 - Produit photographique couleur - Google Patents

Produit photographique couleur Download PDF

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Publication number
EP0987593A1
EP0987593A1 EP99116900A EP99116900A EP0987593A1 EP 0987593 A1 EP0987593 A1 EP 0987593A1 EP 99116900 A EP99116900 A EP 99116900A EP 99116900 A EP99116900 A EP 99116900A EP 0987593 A1 EP0987593 A1 EP 0987593A1
Authority
EP
European Patent Office
Prior art keywords
formula
compounds
alkyl
photographic material
color photographic
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.)
Withdrawn
Application number
EP99116900A
Other languages
German (de)
English (en)
Inventor
Jörg Dr. Hagemann
Günter Dr. Helling
Heinz Wiesen
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.)
Agfa Gevaert AG
Original Assignee
Agfa Gevaert AG
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 Agfa Gevaert AG filed Critical Agfa Gevaert AG
Publication of EP0987593A1 publication Critical patent/EP0987593A1/fr
Withdrawn legal-status Critical Current

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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
    • G03C7/3003—Materials characterised by the use of combinations of photographic compounds known as such, or by a particular location in the photographic element
    • G03C7/3005—Combinations of couplers and photographic additives
    • G03C7/3008—Combinations of couplers having the coupling site in rings of cyclic compounds and photographic additives
    • G03C7/301—Combinations of couplers having the coupling site in pyrazoloazole rings and photographic additives
    • 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
    • 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
    • G03C7/32—Colour coupling substances
    • G03C7/34—Couplers containing phenols
    • 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
    • G03C7/32—Colour coupling substances
    • G03C7/36—Couplers containing compounds with active methylene groups
    • G03C7/38—Couplers containing compounds with active methylene groups in rings
    • G03C7/381—Heterocyclic compounds
    • G03C7/382—Heterocyclic compounds with two heterocyclic rings
    • G03C7/3825—Heterocyclic compounds with two heterocyclic rings the nuclei containing only nitrogen as hetero atoms
    • G03C7/3835—Heterocyclic compounds with two heterocyclic rings the nuclei containing only nitrogen as hetero atoms four nitrogen atoms
    • 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
    • G03C7/39236—Organic compounds with a function having at least two elements among nitrogen, sulfur or oxygen

Definitions

  • the invention relates to a color photographic material with an emulsified heterocyclic Teal couplers from the group of pyrazolo-azoles and certain Coupler solvents.
  • naphtholic ones are usually used or phenolic cyan couplers.
  • color photographic supervisory materials So far, the latter has been given preference because of the more favorable absorption (at approx. 660 nm) and greater dark storage stability from them in the chromogenic Development generated image dyes.
  • the object of the present invention was to use color photographic materials To provide pyrazolo-azole-cyan couplers that improved through Characterize light stability and at the same time have stability against heat.
  • a Another task was to provide cyan couplers, their color rendering compared to the materials known from the prior art is improved.
  • Alkyl or linear in the sense of the present application are linear or branched straight-chain or cyclic, substituted or unsubstituted hydrocarbon groups to understand, preferably it is alkyl groups with 1 to 32 carbon atoms.
  • Open-chain alkyl groups include, in particular, methyl, ethyl, n-propyl, n-butyl, n-octyl, n-dodecyl, n-hexadecyl and n-octadecyl and as branched Alkyl radicals, in particular 2-hexyl-decyl, 2-octyldodecyl and 2-ethylhexyl radicals in question.
  • cycloalkyl groups are cyclohexyl, in particular 4-t-butylcyclohexyl, 2,6-di-t-butyl-4-methyl-cyclohexyl preferred.
  • alkenyl in For the purposes of the present application, linear or branched cyclic or straight chain substituted or unsubstituted unsaturated hydrocarbon radicals to understand such as ethenyl, 2-propenyl, isopropenyl and oleyl.
  • Aryl in the sense of the present application are aromatic hydrocarbons understand, it is preferably phenyl or naphthyl. This can be both substituted and unsubstituted.
  • aromatic systems are to be understood, which at least contain a heteroatom. It is also preferably 5- or 6-membered Ring systems, which are monocyclic but also as condensed ring systems can be present. It can be both substituted and act unsubstituted ring systems. In particular come as heteroatoms N, S and O in question.
  • a ring system can preferably be between 1 and 3 Have heteroatoms, which are the same or different heteroatoms can act. With the condensed ring systems, several of the same can be used or various heterocyclic systems can be condensed, as well as hetaryls Arylene.
  • Typical examples are: pyridine, pyridazine, pyrimidine, pyrazine, oxazole, Isoxazole, thiazole, 3,4-oxdiazole, 1,2,4-oxdiazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, especially furan, pyrrole, thiophene and indole.
  • Alkoxy in the sense of the present application includes residues of the formula OR ' understand, wherein R 'for an alkyl radical according to the above. Definition stands.
  • Aryloxy in the sense of the present application includes residues of the type OR '' understand, in which R '' for an aryl radical as defined above stands.
  • Acyl in the sense of the present application can be an aliphatic, olefinic or aromatic carbon, carbon, carbamine, sulfone, amidosulfone, Act sulfinic, phosphoric, phosphonic or phosphonic acid residue.
  • an electron-withdrawing group in the sense of the present application is an optionally substituted carboxy, carbamoyl, acyloxy, oxycarbonyl, halogenated alkoxy, halogenated aryloxy, aryloxy, acyl, sulfonyl, sulfinyl, Sulfonyloxy, sulfonylmethyl, sulfamoyl, tetrazolyl, pyrrolyl, phosphonyl, halogenated alkyl, halogenated aryl, cyano, alkylsulfonylmethyl, arylsulfonylmethyl or a nitro group, and a halogen atom.
  • Splitting groups X 11 can be halogen, for example chlorine, N-linked, optionally substituted N-heteroaromatics, for example pyrrazoles, imidazole, triazoles or non-aromatic heterocycles, for example hydantoins, oxazolidinediones, S-linked aliphatic or aromatic mercaptans, for example mercaptopropionic acid, 2-acylaminophenyl mercaptane act over 0 linked aliphatic or aromatic hydroxy compounds, for example ethylene glycol, p-salicylic acid ethyl ester.
  • halogen for example chlorine, N-linked, optionally substituted N-heteroaromatics, for example pyrrazoles, imidazole, triazoles or non-aromatic heterocycles, for example hydantoins, oxazolidinediones, S-linked aliphatic or aromatic mercaptans, for example mercapto
  • the compounds of the formula (I) and (II) according to the invention can be used in the usual amounts in the photographic material.
  • the compounds of formula (I) are preferably used with 20 to 2,000 mg / m 2 of the photographic material, in particular 50 to 500 mg / m 2 of the photographic material.
  • the compounds of the formula (II) are preferably used in a weight ratio of 20: 1 to 1:10 to compounds of the formula (I), in particular in a weight ratio of 10: 1 to 1: 5 and particularly preferably in a weight ratio of 5: 1 to 1: 2.
  • the compounds of the formulas (I) and (II) according to the invention are preferably in a red-sensitized silver halide emulsion layer or directly adjacent used for a red-sensitized silver halide emulsion layer.
  • the compounds of the formulas (I) and (II) are used in the same layer.
  • color photographic materials are color negative films, color reversal films, Color positive films, color photographic paper, color reversal photographic paper, color sensitive Materials for the color diffusion transfer process or the silver color bleaching process.
  • the photographic materials consist of a support on which at least one photosensitive silver halide emulsion layer is applied. Suitable as a carrier especially thin films and foils.
  • An overview of carrier materials and auxiliary layers applied on the front and back are in Research Disclosure 37254, Part 1 (1995), p. 285 and in Research Disclosure 38957, Part XV (1996), p. 627.
  • the color photographic materials usually contain at least one red-sensitive, green sensitive and blue sensitive silver halide emulsion layer and optionally intermediate layers and protective layers.
  • these layers can vary be arranged. This is shown for the most important products:
  • Color photographic films such as color negative films and color reversal films show in the the following sequence on the carrier 2 or 3 red-sensitive, cyan-coupling silver halide emulsion layers, 2 or 3 green-sensitive, purple-coupling silver halide emulsion layers and 2 or 3 blue-sensitive, yellow-coupling silver halide emulsion layers.
  • the layers are the same spectral sensitivity differ in their photographic sensitivity, the less sensitive sub-layers usually closer to Carriers are arranged than the more sensitive sub-layers.
  • a yellow filter layer is applied, which prevents blue light from penetrating into the one below Layers.
  • Color photographic paper which is usually much less sensitive to light as a color photographic film, points in the order given below usually a blue-sensitive, yellow-coupling silver halide emulsion layer on the support, a green sensitive, purple coupling silver halide emulsion layer and a red sensitive, cyan-coupling silver halide emulsion layer on; the yellow filter layer can be omitted.
  • Deviations in the number and arrangement of the photosensitive layers can occur to achieve certain results. For example, you can all highly sensitive layers in one layer package and all low-sensitive layers Layers combined into another layer package in a photographic film be to increase the sensitivity (DE-25 30 645).
  • Essential components of the photographic emulsion layers are binders, Silver halide grains and color couplers.
  • Photographic materials with camera sensitivity usually contain silver bromoiodide emulsions, which may also contain small amounts of silver chloride can contain.
  • Photographic copying materials contain either silver chloride bromide emulsions with up to 80 mol% of AgBr or silver chloride bromide emulsions over 95 mol% AgCl.
  • the maximum absorption of the dyes formed from the couplers and the color developer oxidation product is preferably in the following ranges: yellow coupler 430 to 460 nm, purple coupler 540 to 560 nm, cyan couplers 630 to 700 nm.
  • Color photographic films are used to improve sensitivity, royalty, Sharpness and color separation are often used in the compounds in the reaction with the developer oxidation product release compounds that are photographic are effective, e.g. DIR couplers that release a development inhibitor.
  • the mostly hydrophobic color coupler, but also other hydrophobic components of the Layers are usually found in high-boiling organic solvents dissolved or dispersed. These solutions or dispersions are then in one emulsified aqueous binder solution (usually gelatin solution) and lie after drying the layers as fine droplets (0.05 to 0.8 ⁇ m diameter) in the layers before.
  • emulsified aqueous binder solution usually gelatin solution
  • the usually arranged between layers of different spectral sensitivity non-photosensitive intermediate layers can contain agents which an undesirable diffusion of developer oxidation products from a photosensitive in another light-sensitive layer with different spectral Prevent awareness.
  • Suitable connections can be found in Research Disclosure 37254, Part 7 (1995), p. 292, in Research Disclosure 37038, Part III (1995), p. 84 and in Research Disclosure 38957, part X.D (1996), p. 621 ff.
  • the photographic material can also UV-absorbing compounds, whiteners, spacers, filter dyes, formalin scavengers, light stabilizers, antioxidants, D Min dyes, plasticizers (latices), biocides and additives to improve the coupler and dye stability, to reduce the color fog and for Reducing yellowing and other included.
  • Suitable compounds can be found in Research Disclosure 37254, Part 8 (1995), p. 292, in Research Disclosure 37038, Parts IV, V, VI, VII, X, XI and XIII (1995), p. 84 ff and in Research Disclosure 38957, parts VI, VIII, IX and X (1996), pp. 607 and 610 ff.
  • the layers of color photographic materials are usually hardened, i.e. that Binder used, preferably gelatin, is replaced by suitable chemical Process networked.
  • Suitable hardener substances can be found in Research Disclosure 37254, Part 9 (1995), P. 294, in Research Disclosure 37038, Part XII (1995), p. 86 and in Research Disclosure 38957, Part II.B (1996), p. 599.
  • the compounds of the formula (III) are preferably used together with the Compounds of formulas (I) and (II) used in the same layer.
  • the layer structures 2 to 10 correspond in layer structure and composition to layer structure 1 and differ only in that the cyan coupler C-1 and TKP in layer 6 were replaced by the substances specified in Table 1. In addition, for samples 4, 9 and 10, the silver application was reduced to 0.30 g / m 2 .

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
EP99116900A 1998-09-19 1999-09-07 Produit photographique couleur Withdrawn EP0987593A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19843057A DE19843057A1 (de) 1998-09-19 1998-09-19 Farbfotografisches Material
DE19843057 1998-09-19

Publications (1)

Publication Number Publication Date
EP0987593A1 true EP0987593A1 (fr) 2000-03-22

Family

ID=7881586

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99116900A Withdrawn EP0987593A1 (fr) 1998-09-19 1999-09-07 Produit photographique couleur

Country Status (4)

Country Link
US (1) US6242169B1 (fr)
EP (1) EP0987593A1 (fr)
JP (1) JP2000112093A (fr)
DE (1) DE19843057A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6537712B1 (en) 2000-06-13 2003-03-25 Eastman Kodak Company Color photothermographic elements comprising blocked developing agents
US6759187B1 (en) 1999-12-30 2004-07-06 Eastman Kodak Company Imaging element containing a blocked photographically useful compound

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0130416D0 (en) * 2001-12-20 2002-02-06 Eastman Kodak Co Photographic elements containing a de-aggregating compound dye-forming coupler and stabilizer
GB0130418D0 (en) 2001-12-20 2002-02-06 Eastman Kodak Co Photographic elements containing a deaggregating compound and dye forming coupler
US6680165B1 (en) 2002-10-24 2004-01-20 Eastman Kodak Company Cyan coupler dispersion with increased activity
AU2003275678A1 (en) * 2002-10-30 2004-05-25 Nippon Soda Co., Ltd. Recording material comprising diphenyl sulfone derivative and novel diphenyl sulfone derivative compound
DE102009004739A1 (de) 2008-06-14 2009-12-17 Helling, Günter, Dr. Mehrschichtiges abbaubares Polymersystem als Sicherheitselement

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0145342A2 (fr) * 1983-11-18 1985-06-19 Konica Corporation Matériau photographique couleur à l'halogénure d'argent
JPH01172956A (ja) * 1987-12-28 1989-07-07 Konica Corp 色再現性に優れたハロゲン化銀写真感光材料
EP0545305A1 (fr) * 1991-11-27 1993-06-09 Fuji Photo Film Co., Ltd. Matériau photographique couleur à l'halogénure d'argent
EP0610029A1 (fr) * 1993-02-05 1994-08-10 Konica Corporation Matériau photographique couleur à l'halogénure d'argent sensible à la lumière
US5756274A (en) * 1995-07-27 1998-05-26 Fuji Photo Film Co., Ltd. Silver halide color photographic material and method for forming images

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05232651A (ja) * 1992-02-21 1993-09-10 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料
JP3236461B2 (ja) 1994-12-15 2001-12-10 コニカ株式会社 写真用シアンカプラー
US5679506A (en) * 1995-05-23 1997-10-21 Konica Corporation Cyan coupler for silver halide color photographic light-sensitive material

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0145342A2 (fr) * 1983-11-18 1985-06-19 Konica Corporation Matériau photographique couleur à l'halogénure d'argent
JPH01172956A (ja) * 1987-12-28 1989-07-07 Konica Corp 色再現性に優れたハロゲン化銀写真感光材料
EP0545305A1 (fr) * 1991-11-27 1993-06-09 Fuji Photo Film Co., Ltd. Matériau photographique couleur à l'halogénure d'argent
EP0610029A1 (fr) * 1993-02-05 1994-08-10 Konica Corporation Matériau photographique couleur à l'halogénure d'argent sensible à la lumière
US5756274A (en) * 1995-07-27 1998-05-26 Fuji Photo Film Co., Ltd. Silver halide color photographic material and method for forming images

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section PQ Week 8933, Derwent World Patents Index; Class P83, AN 1989-238000 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6759187B1 (en) 1999-12-30 2004-07-06 Eastman Kodak Company Imaging element containing a blocked photographically useful compound
US6537712B1 (en) 2000-06-13 2003-03-25 Eastman Kodak Company Color photothermographic elements comprising blocked developing agents

Also Published As

Publication number Publication date
JP2000112093A (ja) 2000-04-21
US6242169B1 (en) 2001-06-05
DE19843057A1 (de) 2000-03-23

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