EP0871066B1 - Matériau photographique couleur à l'halogénure d'argent - Google Patents

Matériau photographique couleur à l'halogénure d'argent Download PDF

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Publication number
EP0871066B1
EP0871066B1 EP98105593A EP98105593A EP0871066B1 EP 0871066 B1 EP0871066 B1 EP 0871066B1 EP 98105593 A EP98105593 A EP 98105593A EP 98105593 A EP98105593 A EP 98105593A EP 0871066 B1 EP0871066 B1 EP 0871066B1
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EP
European Patent Office
Prior art keywords
silver halide
layer
colour photographic
photographic silver
sensitive
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
EP98105593A
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German (de)
English (en)
Other versions
EP0871066A1 (fr
Inventor
Heinrich Dr. Odenwälder
Hans Dr. Langen
Jörg Dr. Hagemann
Klaus Henseler
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 NV
Original Assignee
Agfa Gevaert NV
Agfa Gevaert AG
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Publication of EP0871066A1 publication Critical patent/EP0871066A1/fr
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Anticipated expiration legal-status 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
    • G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor
    • G03C7/3882—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor characterised by the use of a specific polymer or latex
    • 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
    • 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
    • G03C7/396—Macromolecular additives

Definitions

  • the invention relates to a color photographic silver halide material with improved Characteristics.
  • So-called white couplers or redox-active are used to solve these tasks Connections used. These are usually pyrazolone couplers with a methyl group in the coupling site or around diffusion-resistant Hydroquinones, disulfonamidophenols and N-aryl-N'-acylhydrazine. These connections but can meet the requirements of practice as described above are not sufficiently fulfilled.
  • Acyl residues R 1 can be residues of an aromatic or aliphatic carboxylic, carbamic, carbonic, sulfonic, sulfinic or phosphoric acid.
  • the incorporation into a polymer chain can take place via an unsaturated group, for example a styrene, acrylic acid or methacrylic acid group.
  • unsaturated group for example a styrene, acrylic acid or methacrylic acid group.
  • a suitable monomer is, for example
  • the compound of formula I can be made to a polymer via a polymer-analogous reaction.
  • a polymer-analogous reaction For example, the following connection be bound to a polymer:
  • R 2 is R 3 and n is m.
  • R 1 is preferably hydrogen or acyl
  • R 2 and R 3 are alkyl, the sum of the C atoms in the alkyl radicals R 2 and R 3 being 8 8.
  • Preferred acyl residues are the residues of aromatic and aliphatic carboxylic acids.
  • the position of the substituents relates to the oxygen.
  • the position is 3 para-constant to the 2nd ring link.
  • the other compounds mentioned are obtained in a corresponding manner. If the reactivity of the phenolic component is reduced, it can be aggravated Reaction conditions become necessary e.g. by increasing the temperature, Increasing the concentration of sulfuric acid in the melt etc. Furthermore, all or part of the sulfuric acid can be replaced by other acids e.g. by p-toluenesulfonic acid, methanesulfonic acid, phosphoric acid, polyphosphoric acid, Phthalic acid, trifluoroacetic acid, boric acid and the like. like.
  • the compounds of formula (I) are preferably used in an amount of 5 to 1000 mg / m 2 , in particular 10 to 500 mg / m 2 .
  • the compounds of formula (I) can also be present as a salt (phenolate); as Cations are particularly suitable for metal cations and ammonium ions Alkali metal ions and trialkyl or tetraalkylammonium ions.
  • 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.
  • 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 in the following order 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 same spectral sensitivity differ in their photographic sensitivity, with the less sensitive sub-layers usually closer arranged to the carrier than the higher sensitive sub-layers.
  • a yellow filter layer is applied, which prevents blue light from entering the to get layers below.
  • 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 to another layer package in a photographic film be summarized to increase 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 bromide iodide or silver bromide iodide chloride emulsions.
  • Photographic copy materials contain either silver chloride bromide emulsions with up to 80 mol% AgBr or silver chloride bromide emulsions with over 95 mol% AgCl.
  • the maximum absorption of that from the couplers and the color developer oxidation product Dyes formed are preferably in the following areas: Yellow coupler 430 to 460 nm, purple coupler 540 to 560 nm, cyan coupler 630 up to 700 nm.
  • hydrophobic color couplers but also other hydrophobic components of the layers, are usually 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.
  • aqueous binder solution usually gelatin solution
  • the usually between layers of different spectral sensitivity arranged non-light-sensitive intermediate layers can contain agents which an undesirable diffusion of developer oxidation products from a photosensitive to another photosensitive layer with different prevent spectral sensitization.
  • Suitable connections can be found in Research Disclosure 37254, Part 7 (1995), p. 292 and in Research Disclosure 37038, Part III (1995), p. 84.
  • the photographic material can also contain UV light-absorbing compounds, white toners, spacers, filter dyes, formalin scavengers, light stabilizers, antioxidants, D min dyes, additives to improve the stability of dyes, couplers and whites and to reduce the color fog, plasticizers (latices), Contain biocides and others.
  • Suitable compounds can be found in Research Disclosure 37254, Part 8 (1995), P. 292 and in Research Disclosure 37038, parts IV, V, VI, VII, X, XI and XIII (1995), p. 84 ff.
  • the layers of color photographic materials are usually hardened, i.e. the binder used, preferably gelatin, is by suitable cross-linked chemical processes.
  • Suitable hardener substances can be found in Research Disclosure 37254, Part 9 (1995), p. 294 and in Research Disclosure 37038, Part XII (1995), page 86.
  • the compounds of formula (I) are in particular in at least one neighboring layer to a green sensitive, containing at least one purple coupler Silver halide emulsion layer used, the silver halide emulsion is a silver bromide chloride emulsion with at least 95 mol% AgCl.
  • a color photographic recording material was produced by applying the following layers in the order given to a support made of paper coated on both sides with polyethylene. The quantities given relate to 1 m 2 . The corresponding amounts of AgNO 3 are given for the silver halide application.
  • Samples 2 to 14 are prepared like sample 1 with the difference that in layers 2, 3, 4 and 5 the compounds Y-1, SC-1, SC-2 and M-1 are replaced by those given in table 1 , In addition, the silver coating in layer 4 was reduced to 0.28 g for samples 4 to 9 and to 0.22 g for samples 10 to 14. (V: comparison, E: according to the invention) [amount in mg / m 2 ] Sample No.
  • a color photographic recording material for color negative development was produced (sample 15 - comparison) by applying the following layers in the order given to a transparent layer support made of cellulose triacetate with a thickness of 120 ⁇ m and having an adhesive layer. The amounts are given in g / m 2 . The corresponding amounts of AgNO 3 are given for the silver halide application. All silver halide emulsions per 100 g of AgNO 3 were stabilized with 0.1 g of 4-hydroxy-6-methyl-1,3,3a, 7-tetraazaindene. The silver halide emulsions are characterized by the halide composition and in terms of grain size by the center of gravity (VSP).
  • VSP center of gravity
  • red-sensitized silver bromoiodide emulsion (10.0 mol% iodide; VSP 0.56) 1.2 gelatin 0.9 Teal Coupler C-2 0.2 colored coupler CR-1 7.0 x 10 -2 colored coupler CY-1 3.0 x 10 -2 DIR coupler DIR-1 4.0 x 10 -2
  • red-sensitized silver bromoiodide emulsion (6.8 mol% iodide; VSP 1.2) 1.6 gelatin 1.2 Teal coupler C-3 0.15 DIR coupler DIR-3 3.0 x 10 -2
  • the colorless and colored couplers were used together with the same Amount of tricresyl phosphate (CPM) according to the emulsification methods known in the art brought in.
  • CPM tricresyl phosphate
  • Samples 16 to 18 differ from sample 15 in that they additionally contain compounds of the formula (I) (g / m 2 ) in layer 1.
  • the samples were then exposed to daylight behind a graduated gray wedge.
  • the materials were then processed according to the process described in E. Ch. Gehret, The British J. of Photography 1974, p. 597.
  • the relative red sensitivity and the bluish-green haze were measured from the samples obtained.
  • the results are shown in Table 3.
  • Samples 19 to 24 differ from sample 15 in that an additional 0.125 mmol of the compounds listed in table 4 / m 2 were used in layer 5. Samples 23 and 24 instead contained white couplers W-1 and W-2 in an amount of 0.125 mmol / m 2 .
  • White coupler W 2 has the formula:

Landscapes

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

Claims (7)

  1. Matériau à l'halogénure d'argent pour la photographie en couleur comprenant un support et au moins une couche d'émulsion à l'halogénure d'argent, caractérisé en ce que, dans au moins une couche, est contenu un composé répondant à la formule générale (I)
    Figure 00380001
    dans laquelle
    R1
    représente un atome d'hydrogène, un groupe alkyle ou un groupe acyle,
    R2, R3
    représentent indépendamment l'un de l'autre, un groupe alkyle, un groupe cycloalkyle, un groupe alcényle, un groupe aryle, un atome d'halogène, un groupe OR4, un groupe SR5, un groupe NR6R7, un groupe nitro, un groupe cyano, un groupe SO2R8, un groupe COOR9, un groupe COR10 ou un groupe hétaryle,
    R4, R5, R9
    représentent, indépendamment l'un de l'autre, un groupe alkyle, un groupe cycloalkyle, un groupe alcényle, un groupe aryle ou un groupe hétaryle,
    R6, R7
    représentent, indépendamment l'un de l'autre, un atome d'hydrogène, un groupe R4, un groupe COR10, un groupe COOR9, un groupe SO2R8,
    R8, R10
    représentent, indépendamment l'un de l'autre, un groupe alkyle, un groupe cycloalkyle, un groupe alcényle, un groupe aryle, un groupe hétaryle ou un groupe NR6R7,
    n, m
    représentent 0, 1, 2, 3 ou 4 ou bien deux radicaux R2, respectivement R3, peuvent représenter un noyau carbocyclique ou hétérocyclique condensé, ou bien les composés répondant à la formule I sont liés via un des radicaux R1, R2 ou R3 à une chaíne polymère.
  2. Matériau à l'halogénure d'argent pour la photographie en couleur selon la revendication 1, caractérisé en ce que R1 représente un atome d'hydrogène ou un groupe acyle, R2 est égal à R3 et m et n sont égaux.
  3. Matériau à l'halogénure d'argent pour la photographie en couleur selon la revendication 1, caractérisé en ce que R1 représente un atome d'hydrogène et, R2 et R3 représentent un groupe alkyle, la somme des atomes de carbone dans les radicaux alkyle R2 et R3 étant ≥ 8.
  4. Matériau à l'halogénure d'argent pour la photographie en couleur selon la revendication 1, caractérisé en ce que les composés répondant à la formule (I) sont mis en oeuvre en une quantité de 5 à 1000 mg/m2 de matériau.
  5. Matériau à l'halogénure d'argent pour la photographie en couleur selon la revendication 1, caractérisé en ce qu'il contient des émulsions au chlorobromure d'argent dont la teneur en AgCl est supérieure à 95 moles %.
  6. Matériau à l'halogénure d'argent pour la photographie en couleur selon la revendication 5, caractérisé en ce que le matériau contient au moins une couche d'émulsion à l'halogénure d'argent sensible au vert contenant un copulant pour le magenta et les composés répondant à la formule I sont mis en oeuvre dans au moins une couche voisine de la couche d'émulsion à l'halogénure d'argent sensible au vert.
  7. Matériau à l'halogénure d'argent pour la photographie en couleur selon la revendication 6, caractérisé en ce que le copulant pour le magenta est un copulant pour le magenta à base de pyrazolotriazole.
EP98105593A 1997-04-09 1998-03-27 Matériau photographique couleur à l'halogénure d'argent Expired - Lifetime EP0871066B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19714614 1997-04-09
DE19714614A DE19714614A1 (de) 1997-04-09 1997-04-09 Farbfotografisches Silberhalogenidmaterial

Publications (2)

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EP0871066A1 EP0871066A1 (fr) 1998-10-14
EP0871066B1 true EP0871066B1 (fr) 2002-06-19

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US (1) US5981160A (fr)
EP (1) EP0871066B1 (fr)
JP (1) JP3190617B2 (fr)
DE (2) DE19714614A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2343007B (en) 1998-10-19 2001-11-07 Ciba Sc Holding Ag Colour photographic material
DE19916650A1 (de) 1999-04-14 2000-10-19 Agfa Gevaert Ag Farbfotografisches Silberhalogenidmaterial
DE19938508A1 (de) 1999-08-13 2001-02-15 Agfa Gevaert Ag Farbfotografisches Silberhalogenidmaterial
EP1109062A1 (fr) 1999-12-17 2001-06-20 Agfa-Gevaert N.V. Matériau photographique couleur à l' halogénure d' argent
TW593303B (en) * 2001-09-11 2004-06-21 Ciba Sc Holding Ag Stabilization of synthetic polymers
US8623946B2 (en) * 2008-06-27 2014-01-07 Basf Se Stabilization of body-care and household products
TWI403507B (zh) * 2011-03-17 2013-08-01 Chitec Technology Co Ltd 苯并呋喃衍生物及其應用
ES2765411T3 (es) 2016-01-21 2020-06-09 Basf Se Mezcla de aditivos para la estabilización de poliol y poliuretano
US20240360295A1 (en) 2021-09-02 2024-10-31 Basf Se Stabilizer combination for preventing degradation of synthetic polymers

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3006268A1 (de) * 1980-02-20 1981-08-27 Agfa-Gevaert Ag, 5090 Leverkusen Farbphotografisches aufzeichnungsmaterial mit nicht diffundierenden elektronendonor-vorlaeuferverbindungen
US4369243A (en) * 1981-03-06 1983-01-18 Agfa-Gevaert Aktiengesellschaft Photographic recording material for diffusion processes and useful non-diffusing sulfilimine compounds
DE3215834A1 (de) * 1982-04-28 1983-11-03 Agfa-Gevaert Ag, 5090 Leverkusen Fotografisches aufzeichnungsmaterial fuer diffusionsverfahren und hierfuer geeignete neue nichtdiffundierende sulfiliminverbindungen
TW260686B (fr) * 1992-05-22 1995-10-21 Ciba Geigy
DE19749083A1 (de) * 1997-11-06 1998-07-23 Agfa Gevaert Ag Farbfotografisches Aufzeichnungsmaterial

Also Published As

Publication number Publication date
US5981160A (en) 1999-11-09
JP3190617B2 (ja) 2001-07-23
JPH10282615A (ja) 1998-10-23
DE59804481D1 (de) 2002-07-25
DE19714614A1 (de) 1998-10-15
EP0871066A1 (fr) 1998-10-14

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