EP0543921B1 - Photographisches material - Google Patents

Photographisches material Download PDF

Info

Publication number
EP0543921B1
EP0543921B1 EP91915799A EP91915799A EP0543921B1 EP 0543921 B1 EP0543921 B1 EP 0543921B1 EP 91915799 A EP91915799 A EP 91915799A EP 91915799 A EP91915799 A EP 91915799A EP 0543921 B1 EP0543921 B1 EP 0543921B1
Authority
EP
European Patent Office
Prior art keywords
group
layer
coupler
compound
competitor
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
EP91915799A
Other languages
English (en)
French (fr)
Other versions
EP0543921A1 (de
Inventor
John Victor Nelson
Arlyce Tolman Bowne
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.)
Eastman Kodak Co
Original Assignee
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 Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of EP0543921A1 publication Critical patent/EP0543921A1/de
Application granted granted Critical
Publication of EP0543921B1 publication Critical patent/EP0543921B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/3003Materials characterised by the use of combinations of photographic compounds known as such, or by a particular location in the photographic element

Definitions

  • This invention relates to photography and to radiation-sensitive silver halide photographic materials.
  • Color silver halide photographic materials rely on coupler compounds to form dyes that make up the image recorded in such materials.
  • a yellow dye-forming coupler will be associated with a blue-sensitive silver halide emulsion layer
  • a magenta dye-forming coupler will be associated with a green-sensitive silver halide emulsion layer
  • a cyan dye-forming coupler will be associated with a red-sensitive silver halide emulsion layer.
  • These couplers will be referred to below simply as yellow couplers, magenta couplers, and cyan couplers.
  • With color negative materials the material is exposed to light and processed with a color developer that imagewise forms a silver image and a dye image.
  • the silver image is formed by the color developer reducing the exposed silver halide to form silver and oxidized color developer.
  • the dye image is formed by the reaction of oxidized color developer with dye-forming coupler.
  • the silver image is bleached and solubilized for removal, leaving only a negative color dye image. This image is then used to expose another color negative material to form a positive color dye image.
  • the material With reversal materials, the material is generally exposed and processed with a black-and-white developer to form a negative silver image in each layer.
  • the remaining undeveloped silver halide thus forms a positive imagewise pattern.
  • the remaining silver halide is then fogged and processed in a color developer to form a dye image along with the silver. All the silver is then bleached and solubilized for removal, leaving only the positive color dye image.
  • 5-Pyrazolone compounds and pyrazoloazole (e.g., pyrazolotriazole) compounds are well-known as magenta couplers.
  • magenta couplers Such couplers are described in, for example, James, The Theory of the Photographic Process , MacMillan, 1977.
  • Couplers may be of the 2-equivalent or the 4-equivalent type.
  • 4-equivalent couplers a hydrogen atom is cleaved from the coupler compound at the coupling position when the compound couples with the oxidized color developer.
  • This type of coupler requires the reduction of four moles of silver halide to silver in order to form one mole of dye.
  • 2-equivalent couplers a coupling-off group, such as halogen, is cleaved from the coupler compound at the coupling position during coupling with oxidized color developer. This type of coupler requires the reduction of two moles of silver halide to silver to form one mole of dye.
  • Exemplary photographic elements containing dye forming couplers are shown in EP A 0 362 406, EP A 0 327 274, EP A 0 338 785 and EP A 0 368 356.
  • magenta couplers contained in known photographic elements are those that can wander out of the layer in which they are coated. It has now been discovered that when such magenta couplers are used in a photographic material containing a yellow coupler having a low enough relative reactivity with oxidized developer compared to the reactivity of the magenta coupler with oxidized developer, unwanted dye can be formed as a result of reaction between magenta coupler that has wandered out of its layer and developer that has been oxidized by reaction with silver halide from the yellow coupler layer. This results in undesirable magenta contamination of the yellow record of the photographic material.
  • a color reversal photographic material comprising a support having thereon: a magenta coupler layer that includes a silver halide emulsion and a magenta coupler compound, a yellow coupler layer that includes a silver halide emulsion and a yellow coupler compound, characterized in that: the magenta coupler compound is one that is susceptible to wandering out of the layer in which it is coated, the yellow coupler compound has a relative reactivity, as defined herein, of not greater than 0.9, and the yellow coupler layer, or a layer between it and the magenta coupler layer, includes an oxidized developer competitor compound having a relative reaction rate, as defined herein, of at least 1.6.
  • Scavengers for oxidized developing agent have been placed in an interlayer between coupler containing silver halide emulsion layers (see, e.g., EP A 0 327 274 and EP A 0 338 785) to prevent oxidized developing agent generated in one layer from wandering to an adjacent layer.
  • Such scavengers have also been coated in a coupler containing silver halide emulsion layer (see, e.g., EP A 0 326 406) to compete for oxidized developing agent with the coupler in that layer.
  • neither of these situations is the same as the present invention.
  • magenta couplers useful in the practice of the invention can be a member of any of the known classes of couplers that are well-known in the art, as described, for example in the above-referenced James. These include both 5-pyrazolone couplers and pyrazoloazole couplers such as pyrazolotriazole couplers. In order to achieve the benefit of the invention, the magenta coupler should be one that is susceptible to wandering out of the layer in which it is coated.
  • the degree of susceptibility to wandering that it should have, however, will vary with factors such as the reactivity of the magenta coupler with oxidized developer, the choice of yellow coupler and its reactivity with oxidized developer, the processing conditions, the concentration of the magenta coupler, and the concentration of the yellow coupler.
  • High concentrations of the magenta coupler, low concentrations of the yellow coupler, high reactivity and/or extinction of the magenta coupler, low reactivity and/or extinction of the yellow coupler, and combinations thereof are all factors that would allow the invention to be practiced with a magenta coupler having a relatively low susceptibility to wandering compared to the situation where those factors are reversed (e.g., low concentrations of the magenta coupler, etc.).
  • magenta coupler used in the practice of the invention can be from any class.
  • One such class of couplers is the 5-pyrazolone class, which can be represented by the formula: wherein R1 represents a carbonamido group, an arylamino (preferably anilino) group, a ureido group, a sulfonamido group, an alkylamino group, or a heterocyclic amino group, R2 represent a substituted or unsubstituted aryl group, and X represents hydrogen, or a group capable of being released by a coupling reaction with an oxidized aromatic primary amine developing agent. This group is hereinafter referred to as a coupling-off group.
  • Coupling-off groups are known in the art and may include a group containing an aliphatic group, an aromatic group, a heterocyclic group, an aliphatic, aromatic, or heterocyclic sulfonyl group, or an aliphatic, aromatic, or heterocyclic carbonyl group that is bonded to the coupling active carbon via an oxygen atom, a nitrogen atom, a sulfur atom, or a carbon atom, a halogen atom, an aromatic azo group, and the like.
  • the aliphatic, aromatic, or heterocyclic group contained in such coupling-off groups may have one or more substituents, as described below.
  • Examples of coupling-off groups include a halogen atom (e.g., fluorine, chlorine, bromine), an alkoxy group (e.g., ethoxy, dodecyloxy, carboxypropyloxy), an aryloxy group (e.g., 4-chlorophenoxy group, a 4-methoxyphenoxy group), an acyloxy group (e.g., an acetoxy group, a tetradecanoyloxy group), an aliphatic or aromatic sulfonyloxy group (e.g., a methanesulfonyloxy group, a toluenesulfonyloxy group), an acylamino group (e.g., a dichloroacetylamino group, a trifluoroacetylamino group), an aliphatic or aromatic sulfonamido group (e.g., a methanesulfonamido group, a p
  • the aliphatic, aromatic, or heterocyclic groups included in X and the groups shown by R1 and R2 may be substituted by a substituent such as, for example, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, etc.), an alkyl group (e.g., a methyl group, a t-octyl group, a dodecyl group, a trifluoromethyl group, etc.), an alkenyl group (e.g., an allyl group, an octadecenyl group, etc.), an aryl group (e.g., a phenyl group, a p-tolyl group, a naphthyl group, etc.), an alkoxy group (e.g., a methoxy group, a benzyloxy group, a methoxyethoxy group, etc.), an aryloxy group (e.g
  • Pyrazoloazole couplers useful in the practice of the invention include those according to the formula: wherein R3 represents hydrogen or a substituent, X is as defined above for formula (I), and Z represents the non-metallic atoms necessary to complete a heterocyclic ring.
  • magenta coupler used in the practice of the invention is preferably susceptible to wandering, it will include non-polymeric couplers according to formulas (I) or (II); however, it may also be a polymer, oligomer, or dimer coupler. Such couplers are included in the description of formula (II) above.
  • any of R1, R2, or X may also be a divalent or a more polyvalent group to form an oligomer such as a dimer, etc., or may connect a polymeric main chain and a coupler skeleton to form a polymeric coupler.
  • magenta coupler is a polymeric coupler
  • low molecular weight polymer chains or polymer compositions containing unreacted coupler monomer that would exhibit a tendency to wander are preferred.
  • a typical amount of polymeric coupler that would be used in a photographic material will generally represent a number of polymer molecule chains having a distribution of varying molecular weights.
  • the molecular weight of the polymer is usually described as having a single molecular weight, which is actually a mean or average molecular weight around which the actual molecular weights of the molecules are distributed.
  • some so-called high molecular weight polymeric couplers may contain a sufficient number of low molecular weight molecules so as to make wandering a problem.
  • Such polymeric couplers are intended to be included within the scope of the present invention.
  • magenta couplers useful in the practice of the invention are presented below.
  • the yellow coupler useful in the practice of the invention can be essentially any type of yellow coupler, as is well-known in the art.
  • the reactivity of the yellow coupler with oxidized color developer must be low enough so that, in the absence of the oxidized developer competitor, magenta dye would be formed as a result of reaction between magenta coupler that has wandered out of its layer and developer that has been oxidized by reaction with silver halide from the yellow coupler layer.
  • a yellow coupler that will benefit from practice of the present invention depends on a number of factors, including the specific magenta coupler involved and its reactivity with oxidized color developer, the choice of oxidized color developer, the concentrations of the yellow and magenta couplers, and other factors affecting the reaction kinetics of oxidized developer and couplers (e.g., pH).
  • the present invention is applicable to color reversal systems, which, unlike color negative systems, do not offer the option of compensating for unwanted magenta dye stain during the printing process.
  • the photographic material is a reversal material, such as Kodak Ektachrome® or Fuji Fujichrome®.
  • the yellow coupler preferably has a relative reactivity, as defined below, of not greater than 0.9.
  • the relative reactivity of the yellow coupler is determined as follows.
  • a photographic element is prepared by coating a cellulose acetate-butyrate film support with a photosensitive layer containing 3.77 gm/m2 gelatin, 0.76 gm/m2 silver bromoiodide emulsion, and 2.7 mmole/m2 or the yellow coupler which had been dispersed in half its weight of dibutylphthalate.
  • the photosensitive layer is overcoated with a layer containing gelatin at 1.08 gm/m2 and bis-vinyl sulfonyl methyl ether at 1.75 weight percent based upon total gelatin.
  • the sample is imagewise exposed and processed using Kodak E-6® processing (E-6® processing is described in British Journal of Photography Annual , 1977, pp. 194-197).
  • E-6® processing is described in British Journal of Photography Annual , 1977, pp. 194-197.
  • the relative reactivities represent the status A blue D-max obtained for the sample compared to that obtained for an identical coating, but containing a coupler having the structure:
  • the oxidized developer competitor compound useful in the practice of the invention has a relative reaction rate of at least 1.6.
  • Such competitor compounds are described as "quencher” compounds in European patent application publication no. 326,406.
  • the relative reaction rate herein considered is what can be determined as a relative value obtainable by measuring the dye density of the color image that coupler N forms after the competitor has been mixed with said coupler, incorporated with a silver halide emulsion, and subjected to color development.
  • reaction rate of a competitor with the oxidation product of a color developing agent can be determined as a relative value by finding R for the competitor against coupler N in the above formula.
  • the oxidized developer competitor compound may be incorporated in any layer between the magenta coupler layer and the yellow coupler layer, or within the yellow coupler layer.
  • This layer can be a yellow filter layer, such as a Carey Lea silver layer or a yellow filter dye-containing layer, or it can be a separate interlayer.
  • the effectiveness of the oxidized developer competitor will be felt to a greater extent when the yellow coupler layer and the magenta coupler layer are closer in physical proximity.
  • preferred embodiments are contemplated when there are no additional silver halide layers between the magenta coupler layer and the competitor layer, between the yellow coupler layer and the competitor layer, or both.
  • the competitor is preferably incorporated in the material at levels of from about 0.03 g/m2 to about 0.22 g/m2, although other levels may be useful.
  • oxidized developer compounds are described in U.S. Patent 4,923,787.
  • Such compounds have the formula: wherein R1 represents an electron donating group, R2 represents hydrogen, alkyl, alkoxy, aryl, aryloxy, aralkyl or amino of the formula -NHR3, where R3 is phenyl or benzyl, with the proviso that at least one of the substituents R1 and R2 (a) represents (1) a ballast group of sufficient size as to render the hydrazide compound non-diffusible in the photographic element prior to development in alkaline processing solution and (b) comprises a polar group, and n is 0, 1 or 2.
  • R1 substituents which are electron donating groups, include alkyl, which can be substituted or unsubstituted, straight or branched chain, having from 1 to about 20 carbon atoms, preferably from about 8 to about 16 carbon atoms; alkoxy, which can be substituted or an unsubstituted, straight or branched chain, having from 1 to about 20 carbon atoms, preferably from about 8 to about 16 carbon atoms; carboxy; carbonamido having the formula -NR4COR5; sulfonamido having the -NR4SO2R5; or amino having the formula -NR4R5 where R4 is hydrogen or alkyl having from 1 to about 8 carbon atoms and R5 is as defined for R4 or is a benzyl or a phenyl group which may be substituted.
  • R2 substituents that are alkyl or alkoxy can be as defined for these same substituents in R1, or R2 can be substituted or unsubstituted aryl or substituted or unsubstituted aryloxy having from 6 to about 30 carbon atoms, such as phenyl, phenoxy, naphthyl or naphthoxy.
  • R2 represents phenyl or phenoxy it is preferred that the aryl ring have a hydrogen bonding substituent in a position ortho to the point of attachment of the carbonyl group to a hydrazide nitrogen atom.
  • Preferred hydrogen bonding groups include hydroxy, primary or secondary amino groups of the formula -NR4R5, sulfonamido of the formula -NHSO2R4, carbonamido of the formula -NR4COR5, and ureido of the formula -NHCONHR4 where R4 and R5 can be hydrogen or alkyl of from 1 to about 8 carbon atoms and R5 is as defined for R4 or a benzyl or phenyl group.
  • R2 alkyl groups can also be present as substituents on R2 alkyl groups or on other positions of R2 aryl groups.
  • a polar group which can represent R1 or R2 can be a single group or a combination of groups which have a ⁇ constant which is more negative than -1.0.
  • the ⁇ constant is defined by C. Hansch, A.
  • the R1 or R2 polar group or groups include, but are not limited to, -NHSO2CH3, -NHSO2aryl, -CH2OH, -NH2, -COOH, -CONH2, -NHCONH2, -NHCSNH2, -N+(R5)3, -SO3 ⁇ , -SO2 ⁇ and These groups tend to increase the surfactant nature of the hydrazine during alkaline processing.
  • alkyl, alkoxy, aryl, aryloxy, aralkyl and benzyl groups which are represented by one or more of R1, R2, R3, R4 and R5 can be substituted with halogen atoms, for example chlorine, or with haloalkyl groups, for example trifluoromethyl, or with -NO2 , -CN,
  • oxidized developer competitor compounds useful in the practice of the invention are disclosed in the above-referenced EP 326,406 and U.S. 4,923,787, and include:
  • the support of the element of the invention can be any of a number of well-known supports for photographic elements. These include polymeric films such as cellulose esters (e.g., cellulose triacetate and diacetate) and polyesters of dibasic aromatic carboxylic acids with divalent alcohols (e.g., poly(ethylene terephthalate)), paper, and polymer-coated paper. Such supports are described in further detail in Research Disclosure , December, 1989, Item 308119 [hereinafter referred to as Research Disclosure I] , Section XVII.
  • the silver halide emulsion used in the practice of the invention can contain, for example, silver bromide, silver chloride, silver iodide, silver chlorobromide, silver chloroiodide, silver bromoiodide, or mixtures thereof.
  • the emulsions can include coarse, medium, or fine silver halide grains bounded by 100, 111, or 110 crystal planes.
  • Silver halide emulsions and their preparation are further described in Research Disclosure I , Section I. Also useful are tabular grain silver halide emulsions, as described in Research Disclosure , January, 1983, Item 22534 and U.S. Patent 4,425,426.
  • couplers and competitor compound described above used in the practice of the invention can be incorporated in hydrophilic layers of photographic materials by techniques well-known in the art.
  • One common technique involves the use of high-boiling water-immiscible organic solvents and/or surfactants.
  • Useful organic solvents include tricresyl phosphates, di-n-butyl phthalate, and others described in Research Disclosure I , Section XIV.
  • Surfactants are well-known to one skilled in the art, and are described in Research Disclosure I , Section XI. Mixtures of solvents and surfactants may also be used.
  • the silver halide described above can be sensitized to a particular wavelength range of radiation, such as the red, blue, or green portions of the visible spectrum, or to other wavelength ranges, such as ultraviolet, infrared, and the like.
  • the silver halide emulsion associated with the magenta coupler is spectrally sensitized to green light so as to complement the magenta color of the dye formed by the coupler during processing.
  • the silver halide emulsion associated with the yellow coupler is preferably spectrally sensitized to blue light so as to complement the yellow color of the dye formed by the coupler.
  • Chemical sensitization of silver halide can be accomplished with chemical sensitizers such as gold compounds, iridium compounds, or other group VIII metal compounds.
  • Spectral sensitization is accomplished with spectral sensitizing dyes such as cyanine dyes, merocyanine dyes, styryls, or other known spectral sensitizers. Additional information on sensitization of silver halide is described in Research Disclosure I , Sections I-IV.
  • multicolor photographic elements generally comprise a blue-sensitive silver halide layer having a yellow color-forming coupler associated therewith, a green-sensitive layer having a magenta color-forming coupler associated therewith, and a red-sensitive silver halide layer having a cyan color-forming coupler associated therewith.
  • the oxidized developer competitor compound can be incorporated in the yellow coupler layer or, more preferably, in an interlayer between the yellow coupler layer and the magenta coupler layer. This interlayer can be the yellow filter layer typically used in color photographic materials between the yellow and magenta layers, or it can be a separate layer.
  • Color photographic elements and color-forming couplers are well-known in the art and are further described in Research Disclosure I , Section VII.
  • the element of the invention can also include any of a number of other well-known additives and layers, as described in Research Disclosure I .
  • additives and layers include, for example, optical brighteners, antifoggants, oxidized developer scavengers (which can be the same as or different than the competitor according to formula (I)), development accelerators, image stabilizers, light-absorbing materials such as filter layers or intergrain absorbers, light-scattering materials, gelatin hardeners, coating aids and various surfactants, overcoat layers, interlayers and barrier layers, antistatic layers, plasticizers and lubricants, matting agents, development inhibitor-releasing couplers, bleach accelerator-releasing couplers, and other additives and layers known in the art.
  • the photographic elements of the invention when exposed, are processed to yield an image. Processing can be by any type of known photographic processing, as described in Research Disclosure I , Sections XIX-XXIV.
  • a negative image can be developed by color development with a chromogenic developing agent followed by bleaching and fixing.
  • a positive image can be developed by first developing with a non-chromogenic developer, then uniformly fogging the element, and then developing with a chromogenic developer.
  • Bleaching and fixing can be performed with any of the materials known to be used for that purpose.
  • Bleach baths generally comprise an aqueous solution of an oxidizing agent such as water soluble salts and complexes of iron (III) (e.g., potassium ferricyanide, ferric chloride, ammonium or potassium salts of ferric ethylenediaminetetraacetic acid), water-soluble persulfates (e.g., potassium, sodium, or ammonium persulfate), water-soluble dichromates (e.g., potassium, sodium, and lithium dichromate), and the like.
  • an oxidizing agent such as water soluble salts and complexes of iron (III) (e.g., potassium ferricyanide, ferric chloride, ammonium or potassium salts of ferric ethylenediaminetetraacetic acid), water-soluble persulfates (e.g., potassium, sodium, or ammonium persulfate), water-soluble dichromates (e.g., potassium
  • Fixing baths generally comprise an aqueous solution of compounds that form soluble salts with silver ions, such as sodium thiosulfate, ammonium thiosulfate, potassium thiocyanate, sodium thiocyanate, thiourea, and the like.
  • the invention is further illustrated by the following Example.
  • sample 101 On a cellulose triacetate film support provided with a subbing layer was coated each layer having the composition set forth below to prepare a multilayer color photographic light-sensitive material which was designated sample 101.
  • the coating amounts are shown as g/m2 except for sensitizing dyes, which are shown as the molar amount per mole of silver halide present in the same layer.
  • Samples 102 to 106 were prepared in the same manner as described above for Sample 101 except for the addition of the competitors listed in Table I to the Eighth Layer. The added competitors were coated at the levels (in g/m2) shown in Table I.
  • Each of the samples thus prepared was cut into a 35mm width strip.
  • the samples were exposed to a step exposure using green and red light followed by a series of blue flash exposures and processed using standard Kodak E-6® processing solutions and methods.
  • the Status A green density was measured (or interpolated) for an area in the reversal D-min region of the step exposure of each sample with a Status A blue density of 3.0.
  • Table I higher values indicate an increased amount of magenta dye formed by magenta coupler which has migrated out of its layer.
  • the degree of coupler wandering was confirmed by photomicrography.

Landscapes

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

Claims (10)

  1. Photographisches Farbumkehrmaterial mit einem Träger, auf dem sich befinden:
    eine Purpurrot-Kuppler-Schicht, die eine Silberhalogenidemulsion und eine Purpurrot-Kupplerverbindung enthält,
    eine Gelb-Kuppler-Schicht, die eine Silberhalogenidemulsion und eine Gelb-Kupplerverbindung enthält,
    dadurch gekennzeichnet, daß:
    die Purpurrot-Kupplerverbindung eine solche ist, die für eine Auswanderung aus der Schicht, in der sie aufgetragen ist, zugänglich ist,
    die Gelb-Kupplerverbindung eine relative Reaktivität von nicht größer als 0,9 aufweist, und
    die Gelb-Kuppler-Schicht oder eine Schicht zwischen dieser und der Purpurrot-Kuppler-Schicht eine Mitbewerberverbindung für oxidierten Entwickler enthält, die eine relative Reaktionsgeschwindigkeit von mindestens 1,6 aufweist, wobei
    die relative Reaktivität des Gelb-Kupplers bestimmt werden kann durch Herstellung eines photographischen Elementes, das bildweise exponiert und entwickelt wird, wobei die relative Reaktivität der D-max-Wert für Status-A-Blau ist, erhalten für das photographische Element im Vergleich zu dem Wert, der im Falle einer identischen Beschichtung, jedoch mit einem Kuppler der folgenden Struktur:
    Figure imgb0053
    erhalten wird,
    und wobei die relative Reaktionsgeschwindigkeit der Mitbewerberverbindung für oxidierten Entwickler bestimmt werden kann durch Messung der Farbstoffdichte des Farbbildes, das der Kuppler N bildet, nachdem die Mitbewerberverbindung mit dem Kuppler vermischt worden ist, in eine Silberhalogenidemulsion eingearbeitet und einer Farbentwicklung unterworfen wurde, wobei die relative Reaktionsgeschwindigkeit der Mitbewerberverbindung definiert ist als das Verhältnis der Dichte eines Farbbildes des Kupplers N, wenn eine Mitbewerberverbindung nicht verwendet wird, zur Dichte des Farbbildes des Kupplers N, wenn eine Mitbewerberverbindung zugesetzt wird, wobei der Kuppler N der folgenden Formel entspricht:
    Figure imgb0054
  2. Photographisches Farbumkehrmaterial nach Anspruch 1, weiter dadurch gekennzeichnet, daß die Purpurrot-Kupplerverbindung ein 5-Pyrazolon ist, das der Formel entspricht:
    Figure imgb0055
    worin bedeuten:
    R₁ eine Carbonamidogruppe, eine Arylaminogruppe, eine Ureidogruppe, eine Sulfonamidogruppe, eine Alkylaminogruppe oder eine heterocyclische Aminogruppe,
    R₂ eine substituierte oder unsubstituierte Arylgruppe, und
    X ein Wasserstoffatom oder eine Gruppe, die durch eine Kupplungsreaktion mit einer oxidierten, aus einem primären aromatischen Amin bestehenden Entwicklerverbindung freigesetzt wird.
  3. Photographisches Farbumkehrmaterial nach Anspruch 2, weiter dadurch gekennzeichnet, daß die Mitbewerberverbindung für oxidierten Entwickler die folgende Struktur hat:
    Figure imgb0056
    worin bedeuten:
    R¹ eine Elektronen spendende Gruppe,
    R² gleich Wasserstoff, Alkyl, Alkoxy, Aryl, Aryloxy, Aralkyl oder Amino der Formel -NHR³, worin R³ für Phenyl oder Benzyl steht, wobei gilt, daß mindestens einer der Substituenten R¹ und R² (a) eine Ballastgruppe einer ausreichenden Größe ist, um die Hydrazidverbindung in dem photographischen Element vor der Entwicklung in alkalischer Entwicklungslösung nicht-diffundierend zu machen und (b) eine polare Gruppe aufweist, und
    n gleich 0, 1 oder 2.
  4. Photographisches Farbumkehrmaterial nach Anspruch 3, weiter dadurch gekennzeichnet, daß, falls n gleich 1 oder 2 ist, dann R¹ eine Carbonamidogruppe der Formel -NR⁴COR⁵ ist, worin R⁴ steht für Wasserstoff oder Alkyl mit 1 bis 8 Kohlenstoffatomen, und worin R⁵ wie R⁴ definiert ist oder eine Benzyl- oder Phenylgruppe ist.
  5. Photographisches Farbumkehrmaterial nach einem der Ansprüche 1 bis 4, weiter dadurch gekennzeichnet, daß der Gelb-Kuppler eine relative Reaktionsgeschwindigkeit von nicht größer als 0,8 hat, und daß die Mitbewerberverbindung für oxidierten Entwickler eine relative Reaktionsgeschwindigkeit von mindestens 1,7 hat.
  6. Photographisches Farbumkehrmaterial nach einem der Ansprüche 1 bis 5, weiter dadurch gekennzeichnet, daß die Gelb-Kuppler-Schicht näher der Purpurrot-Kuppler-Schicht liegt als jede andere Gelb-Kuppler-Schicht in dem Material.
  7. Photographisches Farbumkehrmaterial nach einem der Ansprüche 1 bis 6, weiter dadurch gekennzeichnet, daß die Purpurrot-Kuppler-Schicht näher der Gelb-Kuppler-Schicht liegt als irgendeine andere Purpurrot-Kuppler-Schicht in dem Material.
  8. Photographisches Farbumkehrmaterial nach einem der Ansprüche 1 bis 7, weiter dadurch gekennzeichnet, daß die Schicht, die die Mitbewerberverbindung für oxidierten Entwickler enthält, ferner eine Gelbfilterschicht ist.
  9. Photographisches Farbumkehrmaterial nach einem der Ansprüche 1 bis 7, weiter dadurch gekennzeichnet, daß die Schicht, die die Mitbewerberverbindung für oxidierten Entwickler enthält, eine andere Schicht als eine Gelbfilterschicht ist.
  10. Photographisches Farbumkehrmaterial nach einem der Ansprüche 1 bis 7, weiter dadurch gekennzeichnet, daß der Mitbewerber für oxidierten Entwickler in der Gelb-Kuppler-Schicht vorhanden ist.
EP91915799A 1990-08-16 1991-08-09 Photographisches material Expired - Lifetime EP0543921B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US56839890A 1990-08-16 1990-08-16
US568398 1990-08-16
PCT/US1991/005673 WO1992003762A1 (en) 1990-08-16 1991-08-09 Photographic material

Publications (2)

Publication Number Publication Date
EP0543921A1 EP0543921A1 (de) 1993-06-02
EP0543921B1 true EP0543921B1 (de) 1995-03-08

Family

ID=24271122

Family Applications (1)

Application Number Title Priority Date Filing Date
EP91915799A Expired - Lifetime EP0543921B1 (de) 1990-08-16 1991-08-09 Photographisches material

Country Status (4)

Country Link
EP (1) EP0543921B1 (de)
JP (1) JPH05509420A (de)
DE (1) DE69108037T2 (de)
WO (1) WO1992003762A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5695917A (en) * 1995-11-22 1997-12-09 Eastman Kodak Company Combination of yellow filter dye and 4-equivalent pyrazolone magenta coupler

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0326406A2 (de) * 1988-01-28 1989-08-02 Konica Corporation Photographisches lichtempfindliches Silberhalogenidmaterial

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2767422B2 (ja) * 1988-01-30 1998-06-18 コニカ株式会社 ハロゲン化銀写真感光材料
EP0338785B1 (de) * 1988-04-21 1999-07-07 EASTMAN KODAK COMPANY (a New Jersey corporation) Photographisches Element, das einen Fänger für das Entwickleroxidationsprodukt enthält
JPH02131233A (ja) * 1988-11-11 1990-05-21 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0326406A2 (de) * 1988-01-28 1989-08-02 Konica Corporation Photographisches lichtempfindliches Silberhalogenidmaterial

Also Published As

Publication number Publication date
WO1992003762A1 (en) 1992-03-05
JPH05509420A (ja) 1993-12-22
EP0543921A1 (de) 1993-06-02
DE69108037D1 (en) 1995-04-13
DE69108037T2 (de) 1995-10-19

Similar Documents

Publication Publication Date Title
EP0218266B1 (de) Farbphotographisches lichtempfindliches Silberhalogenidmaterial
EP0081768A2 (de) Farbphotographisches lichtempfindliches Material
US4774166A (en) Method for the formation of color images using a color developer not substantially containing benzyl alcohol
US3935016A (en) Silver halide color photographic materials containing 3-anilino-5-pyrazolone couplers
JPS59229557A (ja) カラ−写真感光材料
JP3283917B2 (ja) マゼンタカプラー、抑制剤放出カプラー及びカルボンアミド化合物を含有するカラー写真材料
US4187110A (en) Silver halide photographic light-sensitive material
US4203768A (en) Silver halide color photographic material and method for formation of color photographic images
US5147764A (en) Photographic element with 2-equivalent 5-pyrazolone and competitor for oxidized developing agent
US4874689A (en) Silver halide color photographic material
EP0529737B1 (de) Photographisches Element mit 2-Äquivalenten-Magentafarbkuppler und Filterfarbstoff
US3984245A (en) Photographic sensitive materials
US5164288A (en) Photographic element containing pyrazoloazole coupler and oxidized developer competitor
JPS62278552A (ja) ハロゲン化銀カラ−感光材料
JPS6224250A (ja) ハロゲン化銀カラ−写真感光材料
EP0543921B1 (de) Photographisches material
JPH01101549A (ja) 色素像形成性カプラー化合物を含む写真記録材料
US3352673A (en) Multilayer color photographic element
US5100772A (en) Magenta dye forming coupler for photographic material
EP0545248B1 (de) Verwendung von heterocyclischen Stickstoff-Zusätzen zur Verminderung einer fortgesetzten Kupplung von purpurrote Farbstoffe erzeugenden Kupplern
JPS62129858A (ja) ハロゲン化銀カラ−写真材料の処理方法
JPH0561168A (ja) ハロゲン化銀カラー写真感光材料
EP0464682A1 (de) Photographisches Element
JPS6275449A (ja) ハロゲン化銀カラ−写真感光材料
JPH0427947A (ja) ハロゲン化銀カラー写真感光材料

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19930210

AK Designated contracting states

Kind code of ref document: A1

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

17Q First examination report despatched

Effective date: 19930903

RBV Designated contracting states (corrected)

Designated state(s): DE FR GB

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): DE FR GB

REF Corresponds to:

Ref document number: 69108037

Country of ref document: DE

Date of ref document: 19950413

ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 19980702

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19980806

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19980827

Year of fee payment: 8

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19990809

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 19990809

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20000428

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20000601

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST