EP0309158B1 - Photographisches Eintragungsmaterial mit einer ein purpurrotes Farbbild bildenden Kupplerverbindung - Google Patents

Photographisches Eintragungsmaterial mit einer ein purpurrotes Farbbild bildenden Kupplerverbindung Download PDF

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Publication number
EP0309158B1
EP0309158B1 EP19880308567 EP88308567A EP0309158B1 EP 0309158 B1 EP0309158 B1 EP 0309158B1 EP 19880308567 EP19880308567 EP 19880308567 EP 88308567 A EP88308567 A EP 88308567A EP 0309158 B1 EP0309158 B1 EP 0309158B1
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Prior art keywords
carbon atoms
recording material
group
photographic recording
coupler
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EP19880308567
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French (fr)
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EP0309158A1 (de
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Paul Barrett C/O Eastman Kodak Company Merkel
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Eastman Kodak Co
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Eastman Kodak Co
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    • 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

  • This invention relates to a color photographic silver halide recording material.
  • the invention relates to an improved photographic recording material containing a magenta dye image-forming coupler compound.
  • Color photographic recording materials generaly contain silver halide emulsion layers sensitized to each of the blue, green and red regions of the visible spectrum, with each layer having associated therewith a color-forming compound which, respectively, yields a yellow, magenta or cyan dye.
  • the quality of the resulting color image is primarily based on the dye hues obtained from the respective color-forming compounds.
  • Magenta dye image-forming couplers are frequently employed to provide desired magenta dye images.
  • a problem encountered with such couplers is that the spectral absorption characteristics of dyes obtained therefrom may not have the particular absorption maximum and distribution that are desired.
  • a dye which is obtained may have an absorption maximum as little as several nanometers removed from the optimum desired value, and therefore will not have the desired hue, notwithstanding this slight difference in absorption characteristics.
  • a resulting dye may have an absorption maximum which is considerably shorter than a desired value.
  • Coupler solvents are known to cause shifts in absorption values of dyes.
  • U.S. Patent 3,676,137 describes use of a phosphate ester of a high boiling coupler solvent to shift absorption of a cyan dye to a shorter wavelength in order to reduce excessive red wavelength absorption.
  • Japanese Patent Publication No. 59(1984) - 102234 describes the use of high boiling phenolic compounds to shift the spectral absorption of 2,5-diacylaminophenol cyan dye-forming coupler compounds to longer wavelengths.
  • a phenolic compound of this publication does not provide a sufficient level of hue shifting as compared with that obtained with the present invention.
  • Japanese Patent Publication No. 59(1984) - 204041 describes use of urea compounds with cyan dye image-forming couplers to improve light fastness, to reduce unwanted green absorption and to reduce loss of density caused by bleach operations in dyes obtained from such couplers.
  • This publication also suggests addition of other compounds that form dyes by oxidative coupling with primary amine color developing agents, such as magenta and yellow coupler compounds.
  • magenta and yellow coupler compounds such as magenta and yellow coupler compounds.
  • particular urea compounds can be used to alter absorption characteristics of dyes derived from magenta dye forming coupler compounds.
  • the object of the present invention is to provide a color photographic silver halide recording material having the capability of imparting slight as well as relatively large alterations in absorption properties of a magenta dye to obtain a spectral absorption value different from the inherent absorption characteristics of the dye.
  • a color photographic recording material which comprises a support having thereon a light-sensitive silver halide emulsion layer, a magenta dye image-forming coupler capable of forming a dye by reaction with oxidized color developing agent and, associated with the coupler, a urea compound which is capable of altering the spectral absorption of the magenta dye formed from the coupler, said urea compound having the structural formula: wherein;
  • This invention also relates to a color photographic record comprising a magenta dye formed by a coupling reaction between a magenta dye image-forming coupler and oxidized silver halide developing agent, which recording material comprises, in association with the dye, a urea compound having the structural formula: wherein;
  • the most preferred urea compounds are those where R 1 is an alkyl group having from about 4 to about 10 carbon atoms and where R 2 is hydrogen.
  • R 3 substituents can be alkyl or alkoxy groups having from 1 to about 20 carbon atoms, preferably from 1 to about 12 carbon atoms, which groups can be straight or branched chain and which can be substituted.
  • Substituents which can be present on the R 1 and R 2 groups include halogen atoms, such as chlorine and bromine, and alkoxy or carboalkoxy groups wherein the total number of carbon atoms in such groups is from 2 to about 12.
  • R 1 is aryl the substituents can also be alkyl, preferably alkyl having from 1 to about 12 carbon atoms.
  • Electron-withdrawing groups represented by R 3 include -CN, -N0 2 , a halogen atom, and -S0 2R 4 ,
  • R 4 is an alkyl or an alkoxy group having from 1 to about 20 carbon atoms or an aryl or an aryloxy group having from about 6 to about 12 carbon atoms.
  • Chlorine is a preferred halogen substituent on the phenyl group inasmuch as it provides good stability properties and is least expensive to manufacture.
  • the described urea compounds can be easily synthesized in quantitative yield by adding amines to isocyanates according to the procedures known in the art. Two or more urea compounds may be used in combination to alter the spectral absorption properties of magenta dyes as described herein.
  • the quantity of a urea compound which can be employed with a magenta dye image-forming compound either alone or in combination with known coupler solvents there are no particular restrictions on the quantity of a urea compound which can be employed with a magenta dye image-forming compound either alone or in combination with known coupler solvents.
  • the quantity of urea compound, with respect to each part by weight of the magenta coupler be from 0.05 to 10 parts, preferably from 0.2 to 3 parts by weight of the coupler compound.
  • the amount of urea compound increases, relative to the amount of magenta coupler compound employed, there is usually a detectable increase in the extent of hue shift in the magenta dye.
  • the particular choice of magenta coupler, of urea compound or the presence of one or more coupler solvents all tend to influence the type and the extent of spectral absorption change in the resulting magenta dye.
  • the coupler can first be dissolved in one or more known coupler solvents, such as di-n-butyl phthalate (DBP), and then be mixed with a urea compound as described herein. If desired, the magenta coupler compound can be mixed with a urea compound where these compounds are sufficiently compatible so that known coupler solvents may not be needed. The resulting mixture or solution is then dispersed in aqueous gelatin, preferably containing a surfactant, and the dispersion is added to a silver halide emulsion which can then be coated by known techniques.
  • DBP di-n-butyl phthalate
  • Specific urea compounds which are useful for shifting the absorption values of magenta dyes obtained from the reaction of magenta dye-forming couplers with oxidized color developing agent include the following:
  • Couplers which form magenta dyes upon reaction with oxidized color developing agents are described in such representative patents and publications as: U.S. Patent Nos. 1,969,479; 2,311,082; 2,343,703; 2,369,489; 2,600,788; 2,908,573; 3,061,432; 3,062,653; 3,152,896; 3,519,429; 3,725,067; 4,443,536; European Patent Publication 170164; European Patent Publication Nos. 177,765; and copending U. S. Patent Applications Ser. No. 23,517 of S. Normandin et al, filed March 9, 1987; Ser. No. 23,518 of R. Romanet et al, filed March 9, 1987; No. 23,519 of A. Bowne et al, filed March 9, 1987 and Ser. No. 23,520 of A. Bowne et al, filed March 9, 1987.
  • Preferred magenta couplers include pyrazolones having the structural formulae: and pyrazolotriazoles having the structural formulae: or pyrazolobenzimidazoles having the structural formulae: and and indazoles having the structural formula: wherein
  • magenta dye forming coupler compounds which are useful in the practice of this invention include:
  • Photographic elements in which the photographic couplers of this invention are incorporated can be simple elements comprising a support and a single silver halide emulsion layer, or they can be multilayer, multicolor elements.
  • the coupler compounds of this invention can be incorporated in the silver halide emulsion layer or in another layer, such as an adjacent layer, where they will come into reactive association with oxidized color developing agent which has developed silver halide in the emulsion layer.
  • the silver halide emulsion layer can contain, or have associated therewith, other photographic coupler compounds, such as color forming couplers, colored masking couplers, etc. These other photographic coupler compounds can form dyes of the same or different color and hue as the photographic coupler compounds of this invention. Additionally, the silver halide emulsion layer can contain addenda conventionally contained in such layers.
  • a typical multilayer, multicolor photographic element comprises a support having thereon a red-sensitive silver halide emulsion layer having associated therewith a cyan dye image-forming coupler compound, a green-sensitive silver halide emulsion layer having associated therewith a magenta dye image-forming coupler compound and a blue-sensitive silver halide emulsion layer having associated therewith a yellow dye image-forming coupler compound, wherein the magenta dye image-forming coupler compound has associated therewith a urea compound as described herein.
  • Each silver halide emulsion layer can be composed of one or more layers and the layers can be arranged in different locations with respect to one another. Typical arrangements are described in U.S. Patent Nos. 3,227,554; 3,620,747; 3,843,369; and 4,400,463 and in U.K. Patent No. 923,045.
  • the light sensitive silver halide emulsions can include coarse, regular or fine grain silver halide crystals or mixtures thereof and can be comprised of such silver halides as silver chloride, silver bromide, silver bromoiodide, silver chlorobromide, silver chloroiodide, silver chlorobromoiodide and mixtures thereof.
  • the emulsions can be negative-working or direct-positive emulsions. They can form latent images predominantly on the surface of the silver halide grains or predominantly on the interior of the silver halide grains. They can be chemically and spectrally sensitized.
  • the emulsions typically will be gelatin emulsions although other hydrophilic colloids can be used in accordance with usual practice.
  • the support can be of any suitable material used with photographic elements.
  • a flexible support is employed, such as a polymeric film or paper support.
  • Such supports include cellulose nitrate, cellulose acetate, polyvinylacetal, polyethylene terephthalate, polycarbonate and resinous materials as well as glass, paper or metal.
  • Paper supports can be acetylated or coated with baryta and/or an a-olefin polymer, particularly a polymer of an a-olefin containing 2 to 10 carbon atoms such as polyethylene, polypropylene or ethylene-butene copolymers.
  • association is intended to mean that materials can be in either the same or different layers, so long as the materials are accessible to one another.
  • Single layer coatings containing silver bromoiodide emulsion (6.5 mole % I) comprising unsensitized polydisperse medium-large grains (0.91 gAg/m 2 ) were prepared on cellulose acetate-butyrate supports. Each layer also contained gelatin (3.8 g/m 2 ) and the magenta coupler C-4 (1.3 g/m 2 ) as described above. The coupler was dispersed in di-n-butyl phthalate (DBP) (1.3 g/m 2 when used alone) or in combination of DBP and a urea compound (each at 0.65 g/m 2 ) as described below in Table 1. Each coating was exposed imagewise through a graduated-density test object to provide a maximum density image and was processed at 33 C employing the color developer solution described below, and then subjected to 1.5 minutes in the bleach-fix bath described below, washed and dried.
  • DBP di-n-butyl phthalate
  • a urea compound each at 0.65
  • Example 2 This example is similar to Example 1, except that pyrazolotriazole magenta coupler C-14 (1.3 g/m 2 ) as described above, was used:

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

Claims (10)

1. Farbphotographisches Aufzeichnungsmaterial mit einem Träger, auf dem sich befinden eine lichtempfindliche Silberhalogenidemulsionsschicht, ein ein purpurrotes Farbstoffbild liefernder Kuppler, der einen Farbstoff durch Umsetzung mit oxidierter Farbentwicklerverbindung zu erzeugen vermag und eine dem Kuppler zugeordnete Harnstoffverbindung, welche die spektrale Absorption des aus dem Kuppler gebildeten Purpurrotfarbstoffes zu verändern vermag, wobei die Harnstoffverbindung der folgenden Strukturformel entspricht:
Figure imgb0077
worin bedeuten:
R1 eine substituierte oder unsubstituierte Alkylgruppe oder Arylgruppe mit 6 bis 12 Kohlenstoffatomen, die gegebenenfalls durch Halogen, Alkoxy-oder Carbalkoxygruppen mit 2 bis 12 Kohlenstoffatomen substituiert sein kann oder durch Alkyl mit 1 bis 12 Kohlenstoffatomen;
R2 Wasserstoff oder eine substituierte oder unsubstituierte Alkylgruppe;
R3 eine unsubstituierte oder substituierte Alkyl- oder Alkoxygruppe mit 1 bis 20 Kohlenstoffatomen oder eine elektronenabziehende Gruppe bestehend aus -CN, -N02, einem Halogenatom, -COR4 oder -S02R4, worin R4 für eine Alkyl- oder Alkoxygruppe mit 1 bis 20 Kohlenstoffatomen steht oder eine Aryl- oder eine Aryloxygruppe mit 6 bis 12 Kohlenstoffatomen, und
n gleich 0 bis 3.
2. Photographisches Aufzeichnungsmaterial nach Anspruch 1, worin R3 für Chlor steht.
3. Photographisches Aufzeichnungsmaterial nach einem der Ansprüche 1 oder 2, worin R4 eine Alkylgruppe mit 1 bis 12 Kohlenstoffatomen ist.
4. Photographisches Aufzeichnungsmaterial nach einem der Ansprüche 1 bis 3, worin R1 eine Alkylgruppe mit 1 bis 20 Kohlenstoffatomen darstellt oder eine Arylgruppe mit 6 bis 12 Kohlenstoffatomen.
5. Photographisches Aufzeichnungsmaterial nach einem der Ansprüche 1 bis 4, worin R2 eine Alkylgruppe mit 1 bis 20 Kohlenstoffatomen ist.
6. Photographisches Aufzeichnungsmaterial nach einem der Ansprüche 1 bis 5, worin R1 eine Alkylgruppe mit 4 bis 10 Kohlenstoffatomen ist, und R2 für Wasserstoff steht.
7. Photographisches Aufzeichnungsmaterial nach einem der Ansprüche 1 bis 6, worin der ein purpurrotes Farbstoffbild liefernde Kuppler eine Pyrazolon-, Pyrazolotriazol-, Pyrazolobenzimidazol- oder Indazolverbindung ist.
8. Photographisches Aufzeichnungsmaterial nach einem der Ansprüche 1 bis 7, worin die Harnstoffverbindung in einer Konzentration von 0,05 bis 10, vorzugsweise von 0,2 bis 3 Gewichtsteilen Kupplerverbindung vorliegt.
9. Photographisches Aufzeichnungsmaterial nach Anspruch 1, 7 oder 8, worin die Harnstoffverbindung eine der folgenden Strukturformeln aufweist:
Figure imgb0078
oder
Figure imgb0079
oder
Figure imgb0080
oder
Figure imgb0081
10. Farbphotographische Aufzeichnung mit einem purpurroten Farbstoff, der durch Kupplungsreaktion zwischen einem ein purpurrotes Farbstoffbild liefernden Kuppler und oxidierter Silberhalogenidentwicklerverbindung erzeugt worden ist, wobei das Aufzeichnungsmaterial in Verbindung mit dem Farbstoff eine Harnstoffverbindung nach einem der Ansprüche 1 bis 9 enthält.
EP19880308567 1987-09-21 1988-09-16 Photographisches Eintragungsmaterial mit einer ein purpurrotes Farbbild bildenden Kupplerverbindung Expired - Lifetime EP0309158B1 (de)

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US9917187A 1987-09-21 1987-09-21
US99171 1987-09-21

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Publication number Priority date Publication date Assignee Title
JP2876075B2 (ja) * 1989-05-25 1999-03-31 富士写真フイルム株式会社 ハロゲン化銀カラー写真感光材料
JP3089579B2 (ja) * 1993-01-11 2000-09-18 富士写真フイルム株式会社 ハロゲン化銀カラー写真感光材料及びカラー画像形成方法
KR101093031B1 (ko) 2003-10-23 2011-12-13 후지필름 가부시키가이샤 잉크젯 기록용 마젠타 잉크 및 잉크셋
JP5785799B2 (ja) 2010-07-30 2015-09-30 富士フイルム株式会社 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物
JP5866150B2 (ja) 2010-07-30 2016-02-17 富士フイルム株式会社 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物
JP2014198816A (ja) 2012-09-26 2014-10-23 富士フイルム株式会社 アゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物

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JPS5810738A (ja) * 1981-07-13 1983-01-21 Fuji Photo Film Co Ltd ハロゲン化銀カラ−感光材料
JPS62157031A (ja) * 1985-12-28 1987-07-13 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料
JPH0812408B2 (ja) * 1986-11-19 1996-02-07 コニカ株式会社 迅速処理に適したハロゲン化銀写真感光材料

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DE3878368T2 (de) 1993-09-09
DE3878368D1 (de) 1993-03-25
JPH01101547A (ja) 1989-04-19

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