EP0142086B1 - Farbfotografisches Aufzeichnungsmaterial zur Herstellung farbiger Aufsichtsbilder - Google Patents

Farbfotografisches Aufzeichnungsmaterial zur Herstellung farbiger Aufsichtsbilder Download PDF

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Publication number
EP0142086B1
EP0142086B1 EP84112972A EP84112972A EP0142086B1 EP 0142086 B1 EP0142086 B1 EP 0142086B1 EP 84112972 A EP84112972 A EP 84112972A EP 84112972 A EP84112972 A EP 84112972A EP 0142086 B1 EP0142086 B1 EP 0142086B1
Authority
EP
European Patent Office
Prior art keywords
alkyl
coupler
color
colour
following formula
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
Application number
EP84112972A
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German (de)
English (en)
French (fr)
Other versions
EP0142086A3 (en
EP0142086A2 (de
Inventor
Erich Dr. Wolff
Günter Dr. Renner
Friedrich-Wilhelm Dr. Kunitz
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
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Agfa Gevaert AG
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Publication date
Application filed by Agfa Gevaert AG filed Critical Agfa Gevaert AG
Publication of EP0142086A2 publication Critical patent/EP0142086A2/de
Publication of EP0142086A3 publication Critical patent/EP0142086A3/de
Application granted granted Critical
Publication of EP0142086B1 publication Critical patent/EP0142086B1/de
Expired legal-status Critical Current

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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
    • G03C7/32—Colour coupling substances
    • G03C7/3225—Combination of couplers of different kinds, e.g. yellow and magenta couplers in a same layer or in different layers of the photographic material

Definitions

  • the invention relates to a light-sensitive color photographic recording material with a light-reflecting layer support and at least three light-sensitive silver halide emulsion layers of different spectral sensitivity arranged thereon, to which a cyan coupler, a magenta coupler and a yellow coupler are each spectrally assigned.
  • a recording material is obtained that provides color-neutral images with high storage stability.
  • the color couplers and the dyes obtained therefrom by chromogenic development In practice, a number of requirements are placed on the color couplers and on the dyes obtained therefrom by chromogenic development.
  • the coupling speed of the color couplers with the oxidation product of the color developer should be as high as possible.
  • the color couplers and the dyes obtained from them must be sufficiently stable to light, elevated temperature and moisture. This applies to both unprocessed and processed recording materials. For example, the residual coupler still present in the image whites of the processed recording material must not turn yellow.
  • the dyes should be sufficiently resistant to gaseous reducing or oxidizing agents. They must also be firmly anchored in the image layer and should separate as fine a grain as possible during the chromogenic development. Furthermore, the mechanical properties of the layers must not be impaired by the color couplers.
  • the dyes resulting from the color couplers in the chromogenic development must have a favorable absorption curve with a maximum that corresponds to the color of the desired partial image
  • a cyan dye should almost completely absorb red light and largely let blue and green light pass, a purple dye almost completely absorb green light and let blue and red light pass largely, and a yellow dye should almost completely absorb blue light and let green and red light pass largely.
  • At least one predominantly blue-sensitive, one predominantly green-sensitive and one predominantly red-sensitive silver halide emulsion layer are layered one on top of the other on a layer support. If the blue-sensitive layer is arranged at the top of the layer structure, there can be a layer with a yellow filter dye underneath and above the green- or red-sensitive layers. Furthermore, intermediate layers can be arranged between two silver halide emulsion layers of different spectral sensitivity. As a rule, non-diffusing color couplers are spectrally assigned to the light-sensitive silver halide emulsion layers.
  • the usual spectral assignment provides that the absorption range of the dye formed from the color coupler during development essentially corresponds to the range of the predominant spectral sensitivity of the assigned silver halide emulsion.
  • a yellow coupler is assigned to the predominantly blue-sensitive silver halide emulsion layer
  • a purple coupler to the predominantly green-sensitive silver halide emulsion layer
  • a cyan coupler to the predominantly red-sensitive silver halide emulsion layer.
  • the photosensitive layers are usually layered on an opaque light-reflecting substrate when producing overlay images.
  • UV absorbers such as hydroxyphenylbenzotriazoles, hydroxybenzophenones, benzalmalonic acid derivatives or benzalcyanoacetic acid esters, or by antioxidants, radical scavengers, metal deactivators, peroxidizers or peroxide, which act as dye stabilizers.
  • improvements have been achieved, for. B. by sterically hindered phenyl p-hydroxybenzoate, hydroxyphenylbenzoetriazole, or sterically hindered amines.
  • FR-A-2 274 958 describes a silver halide color photographic material whose yellow couplers, magenta couplers and cyan couplers have substantially the same high color formation rate and which is improved in storage stability and other properties.
  • the invention has for its object to provide a color photographic marking material with embedded color couplers for the three partial color images teal, purple and yellow, which is characterized by an improved stability of the image dyes both against light and against heat and moisture and which is characterized in particular by the fact that the Dark fading is improved.
  • the decrease in color density in the three partial color images cyan, purple and yellow should also occur as evenly and synchronously as possible, so that overall an image that is as neutral gray as possible, even with longer storage under normal conditions of storage in living rooms and with increased heat and moisture is retained.
  • magenta coupler is a 3-anilinopyrazolone coupler and the yellow coupler is a 2-equivalent yellow coupler derived from pivaloylacetanilide.
  • An acyl radical represented by R 4 is in particular an acyl radical which is derived from aliphatic or aromatic carboxylic acids, in particular alkyl-, alkoxy- or aroxy-substituted carboxylic acids.
  • the cyan coupler corresponds to formula II
  • the magenta coupler corresponds to formula III
  • the yellow coupler corresponds to formula IV.
  • acylamino radicals as represented, for example, by R 9 or Y, the acyl radical is derived from an aliphatic or aromatic carboxylic or sulfonic acid, or from carbamic acid or a carbonic acid semi-ester.
  • R 9 preferably has the structure -NH-CO- R 21 where R 21 is a diffusion-resistant alkyl or alkoxy radical.
  • a cycloimido radical represented by R 9 is, for example, a phthalimido, tetrahydrophthalimido or succinimido radical which is substituted by a diffusion-resistant aliphatic group.
  • An aroxyalkyl radical represented by R 17 preferably has a structure as defined for R 5 .
  • cyan couplers that can be used according to the invention in combination with the corresponding magenta couplers and yellow couplers are listed below:
  • magenta couplers that can be used according to the invention in combination with corresponding cyan couplers and yellow couplers are listed below:
  • yellow couplers that can be used according to the invention in combination with corresponding cyan couplers and magenta couplers are listed below:
  • Suitable cyan couplers are described, for example, in US-A-3,772,002. These cyan couplers are known to provide cyan dyes with increased stability against moist heat. Intermediates which are suitable for the production of these cyan couplers can be obtained, for example, by processes which are analogous to those described in DE-A-3 216 804.
  • Suitable purple couplers are described, for example, in DE-C-1 797 083, DE-A-2 301 705, DE-A-2 300 221, DE-A -2 408 655 and DE-A-2 644 538.
  • Suitable yellow couplers are described, for example in DE-B-1 124 365, DE-A -2 329 587, DE-A-2 433 812, DE-A-2 528 638 and DE-A -2 842 063.
  • the color couplers mentioned are incorporated into the color photographic recording materials in a customary manner according to the known emulsification techniques, in each case in association with a spectral sensitization corresponding to a silver halide emulsion layer.
  • Assignment is to be understood to mean that the mutual spatial arrangement of the silver halide emulsion and color coupler is of such a type that an interaction between them is possible during development, which permits an image-like correspondence between the silver image formed and the dye image.
  • the color coupler is usually embedded in the silver halide emulsion layer itself or in a layer adjacent to it.
  • the color photographic recording material according to the invention can also contain other suitable additives in a known manner, for. B. in the form of UV absorbers, antioxidants, radical scavengers, metal deactivators or peroxide decomposers.
  • suitable additives for. B. in the form of UV absorbers, antioxidants, radical scavengers, metal deactivators or peroxide decomposers. Examples include hydroxyphenylbenzotriazoles, stilbene derivatives, hydroxychromanes, sterically hindered amines or phenols and certain metal chelates.
  • Such compounds can be embedded in one or more layers of the color photographic recording material according to the invention.
  • the cyan coupler is a 2-equivalent coupler
  • the purple coupler is a 4-equivalent coupler
  • the yellow coupler is a 2-equivalent coupler. If 4-equivalent blue-green couplers, 2-equivalent purple couplers or 4-equivalent yellow couplers are used instead, this must be taken into account by adjusting the silver / coupler ratio accordingly.
  • the samples produced and processed in this way were tested for their light fastness and heat resistance. To determine the light fastness, the samples were irradiated in a Xenotest device (40% RH; 25 ° C; 5 x 10 6 lx.h). The percentage decrease in density at the original density 1.0 measured behind the blue, green or red filter and the resulting visual color impression (color cast) is entered in Table 1.
  • Samples 1, 2 and 4 to 10 show a clear color cast after irradiation due to the bleaching of one or two image dyes.
  • samples 3 and 11 to 15 images with a neutral image impression are obtained, but in particular in sample 11 the absolute amount of the decrease in color density is unacceptably high.
  • Samples 3 and 12 to 15 would be acceptable from the standpoint of lightfastness alone, but they are not satisfactory in terms of their dark fading behavior as shown in Table 2.
  • Samples 16 to 24 according to the invention only fade to a small extent and retain their neutral gray image impression.
  • the deviation from neutral gray during irradiation in the xenotest device (.10 6 Ix. H.) Is shown in FIG. 1 for some samples. Starting from the neutral gray point in the center of the diagram, the percentage declines for the colors yellow, purple and teal are successively entered in the diagram and added graphically. The total percentage deviation from the neutral gray point is obtained from this for each sample.
  • the inner hexagon indicates the deviation by 10%; the outer hexagon indicates the deviation by 40%.
  • the points marked with numbers represent the behavior of the corresponding samples.
  • Samples 4, 5, 6, 8 and 10 bleach so much when irradiated that the viewer perceives a color cast after a short time of irradiation.
  • Samples 3 and 15 fade to neutral gray when irradiated, but in the dark fading test (Table 2) they show an unacceptably high unevenness in the decrease in the two most important dyes, purple and teal, which leads to a color cast.
  • sample 11 bleaches neutral gray, it also shows an acceptable color decline in the dark fading test (Table 2), but the bleaching occurs when irradiated so quickly that the colored image impression disappears after a short time.
  • Samples 23 and 24 according to the invention lie within the "10%" hexagon in the xenon test, moreover give only a slight decrease in absolute density under the specified conditions and furthermore show a slow and uniform decrease in density of the two dyes under consideration in the dark fading test.
  • shelf life is given as about 10 years in terms of tolerable color matching (SPSE Synposium, Ottawa, August 29 to September 1, 1982).
  • the durability (dark storage) at 25 ° C of color photographic recording materials can according to Arrhenius can be determined by extrapolation from the values listed in Table 2 together with other values determined at different temperatures and for other times (Bard et al, Kodak JAPE 6 (1980), pp. 42 to 45). This results in supervisory materials with the coupler combinations according to the invention a shelf life of around 55 years determined by extrapolation when stored in the dark.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
EP84112972A 1983-11-08 1984-10-27 Farbfotografisches Aufzeichnungsmaterial zur Herstellung farbiger Aufsichtsbilder Expired EP0142086B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3340270 1983-11-08
DE19833340270 DE3340270A1 (de) 1983-11-08 1983-11-08 Farbfotografisches aufzeichnungsmaterial zur herstellung farbiger aufsichtsbilder

Publications (3)

Publication Number Publication Date
EP0142086A2 EP0142086A2 (de) 1985-05-22
EP0142086A3 EP0142086A3 (en) 1988-03-16
EP0142086B1 true EP0142086B1 (de) 1989-09-13

Family

ID=6213690

Family Applications (1)

Application Number Title Priority Date Filing Date
EP84112972A Expired EP0142086B1 (de) 1983-11-08 1984-10-27 Farbfotografisches Aufzeichnungsmaterial zur Herstellung farbiger Aufsichtsbilder

Country Status (4)

Country Link
US (1) US4581324A (cg-RX-API-DMAC7.html)
EP (1) EP0142086B1 (cg-RX-API-DMAC7.html)
JP (1) JPS60117249A (cg-RX-API-DMAC7.html)
DE (2) DE3340270A1 (cg-RX-API-DMAC7.html)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3585044D1 (de) * 1984-03-29 1992-02-13 Konishiroku Photo Ind Photographisches silberhalogenidmaterial.
JPS60209735A (ja) * 1984-04-03 1985-10-22 Konishiroku Photo Ind Co Ltd ハロゲン化銀カラ−写真感光材料
JPS619653A (ja) * 1984-06-25 1986-01-17 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真感光材料
JPS6139045A (ja) * 1984-07-31 1986-02-25 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真感光材料
JPS6199141A (ja) * 1984-10-22 1986-05-17 Konishiroku Photo Ind Co Ltd ハロゲン化銀カラ−写真感光材料
JPH0715568B2 (ja) 1986-01-20 1995-02-22 コニカ株式会社 ハロゲン化銀カラ−写真感光材料
JPS6344658A (ja) * 1986-08-13 1988-02-25 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真感光材料
JPH0820711B2 (ja) * 1988-03-10 1996-03-04 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
JP2838549B2 (ja) * 1989-09-15 1998-12-16 コニカ株式会社 ハロゲン化銀写真感光材料及びカラー画像形成方法
JP2863790B2 (ja) * 1989-10-19 1999-03-03 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
JP2518193Y2 (ja) * 1993-03-30 1996-11-20 株式会社アイコ 電気ショック玩具
US5891613A (en) * 1997-08-22 1999-04-06 Eastman Kodak Company Silver halide light-sensitive element
US5879867A (en) * 1997-08-22 1999-03-09 Eastman Kodak Company Silver halide light-sensitive element
US8283482B2 (en) 2007-04-04 2012-10-09 Kao Corporation Method for producing cross-coupling compound
US8629314B2 (en) 2007-12-18 2014-01-14 Ethicon, Inc. Surgical barriers having adhesion inhibiting properties
US8299316B2 (en) 2007-12-18 2012-10-30 Ethicon, Inc. Hemostatic device

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE603213A (cg-RX-API-DMAC7.html) 1960-04-28
DE1797083C3 (de) 1968-08-14 1979-11-29 Agfa-Gevaert Ag, 5090 Leverkusen Photographisches Verfahren zur Herstellung von farbigen Bildern
JPS5039654B1 (cg-RX-API-DMAC7.html) 1971-04-07 1975-12-18
US3772002A (en) * 1971-10-14 1973-11-13 Minnesota Mining & Mfg Phenolic couplers
DE2300221A1 (de) 1973-01-04 1974-07-18 Agfa Gevaert Ag Verfahren zur herstellung von 3anilino-pyrazolonen-(5)
DE2301705A1 (de) 1973-01-13 1974-07-25 Agfa Gevaert Ag Photographisches material mit einemulgierten farbkupplern und verfahren zu ihrer herstellung
IT985825B (it) 1973-02-23 1974-12-20 Indesit Ricevitore di segnali televisivi
DE2329587C2 (de) 1973-06-09 1984-06-20 Agfa-Gevaert Ag, 5090 Leverkusen Farbphotographisches Aufzeichnungsmaterial
JPS5125733B2 (cg-RX-API-DMAC7.html) 1973-07-16 1976-08-02
JPS532777B2 (cg-RX-API-DMAC7.html) * 1974-06-17 1978-01-31
IT1018702B (it) 1974-06-26 1977-10-20 Minnesota Mining & Mfg Copulanti fotografici pivalilaceta nilidici elementi fotografici che comprendono tali copulanti e.o i co loranti formati per sviluppo cromo geno di detti copulanti e metodo per formare una immagine fotografi ca a coloranti in presenza di det ti copulanti
JPS5242726A (en) 1975-10-01 1977-04-02 Fuji Photo Film Co Ltd Photographic magenta color forming coupler
CA1099559A (en) 1977-09-29 1981-04-21 Mario Fryberg 1,2,4-triazole derivatives substituted with a thio or seleno group in the 5-position
JPS57173835A (en) * 1981-04-20 1982-10-26 Fuji Photo Film Co Ltd Silver halide color photosensitive material
JPS57198459A (en) * 1981-06-01 1982-12-06 Fuji Photo Film Co Ltd Color photographic sensitive material
JPS58208745A (ja) * 1982-05-28 1983-12-05 Konishiroku Photo Ind Co Ltd カラ−写真感光材料

Also Published As

Publication number Publication date
JPS60117249A (ja) 1985-06-24
JPH0525108B2 (cg-RX-API-DMAC7.html) 1993-04-09
DE3479762D1 (en) 1989-10-19
DE3340270A1 (de) 1985-05-15
US4581324A (en) 1986-04-08
EP0142086A3 (en) 1988-03-16
EP0142086A2 (de) 1985-05-22

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