EP0309819A2 - Matériau de reproduction photographique couleur - Google Patents

Matériau de reproduction photographique couleur Download PDF

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Publication number
EP0309819A2
EP0309819A2 EP88115078A EP88115078A EP0309819A2 EP 0309819 A2 EP0309819 A2 EP 0309819A2 EP 88115078 A EP88115078 A EP 88115078A EP 88115078 A EP88115078 A EP 88115078A EP 0309819 A2 EP0309819 A2 EP 0309819A2
Authority
EP
European Patent Office
Prior art keywords
coupler
color
recording material
couplers
purple
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.)
Granted
Application number
EP88115078A
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German (de)
English (en)
Other versions
EP0309819A3 (en
EP0309819B1 (fr
Inventor
Günter Dr. Renner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Agfa Gevaert AG
Original Assignee
Agfa Gevaert AG
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Filing date
Publication date
Application filed by Agfa Gevaert AG filed Critical Agfa Gevaert AG
Publication of EP0309819A2 publication Critical patent/EP0309819A2/fr
Publication of EP0309819A3 publication Critical patent/EP0309819A3/de
Application granted granted Critical
Publication of EP0309819B1 publication Critical patent/EP0309819B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/392—Additives
    • G03C7/39208—Organic compounds
    • G03C7/39236—Organic compounds with a function having at least two elements among nitrogen, sulfur or oxygen
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/32—Colour coupling substances
    • G03C7/36—Couplers containing compounds with active methylene groups
    • G03C7/38—Couplers containing compounds with active methylene groups in rings
    • G03C7/384—Couplers containing compounds with active methylene groups in rings in pyrazolone rings

Definitions

  • the invention relates to a color photographic recording material with at least one silver halide emulsion layer and at least one layer to which a purple coupler of the pyrazolone type is assigned.
  • a purple coupler i.e. compounds which are derived from pyrazolone-5 are generally used as color couplers which are suitable for producing the purple color image.
  • Common purple couplers are, for example, pyrazoion-5 compounds. which are substituted in the 3-position by an acylamino group.
  • 3-anilinopyrazolone-5-couplers are characterized by low secondary densities in both the red and blue spectral range, by heating, tropical and storage cabinet stability, by excellent light stability of the azomethine dyes formed with p-phenylenediamines and by high reactivity and coupling activity.
  • 2-equivalent purple couplers were used in which a substituent is introduced into the coupling position of the pyrazolone-type purple coupler and is split off as an escape group during color development. Couplers of this type are described, for example, in US Pat. Nos. 3,311,476, 3,419,391, 3,617,291 and 3,926,631 and in DE-A 25 36 191, 26 51 363 and 27 03 589. Further magenta couplers in which a substituent, in particular an aryl radical, is attached to the coupling position by a sulfur atom are described in US Pat. Nos. 3,214,437, 4,032,346, 3,227,554, 3,701,783 and 4,383,027 in EP-A 0 081 768, in JA 34044/78 and in DE-A 29 44 601 and 33 18 759.
  • Such 2-equivalent couplers couple in normal processing with a sufficiently high color formation rate, which has a favorable effect in terms of saving silver and couplers.
  • Various syntheses are known for producing such 2-equivalent polymer couplers. According to one of these methods, suitable thiophenol, for example, is converted to sulfenyl chloride and reacted with a sulfinic acid, in particular an aromatic sulfinic acid. The thiosulfonic acid ester obtained in this way can then be converted with the 4-equivalent purple coupler in alcoholic alkaline medium to the desired 2-equivalent coupler (DE-A-3 241 886). This method gives good results. Nevertheless, it is not yet satisfactory insofar as the 2-equivalent purple couplers synthesized after this suffice after recrystallization to a degree of purity of the photographic requirements and can hardly be obtained in yields above 70%.
  • the invention has for its object to provide a color photographic recording material with which even with shortened processing immediately after processing, color images with a high color density are obtained, the color coordination of which no longer changes significantly after the processing is completed.
  • the recording material should have all the advantages of 2-equivalent purple couplers and the purple couplers used should be easily accessible.
  • the thiosulfonic acid ester compound used according to the invention preferably corresponds to formula II
  • R 3 and R 4 are independently alkyl, aralkyl, aryl or a heterocyclic group.
  • An alkyl group represented by R 3 or R 4 can contain up to 20 C atoms, for example, and can be straight-chain or branched. It can also be substituted, for example by halogen, amino, alkoxycarbonyl, alkylsulfonyl, aryl or a heterocyclic group.
  • An aryl group represented by R 3 or R 4 is, for example, a phenyl group which can be substituted, for example by halogen, alkyl, alkoxy, aroxy, alkylthio, amino, acylamino, sulfonamides, carbamoyl, sulfamoyl or a heterocyclic group.
  • a heterocyclic group can be, for example: quinolyl, pyrazolyl, tetrazolyl, triazolyl, imidazolyl, benzimidazolyl, tetrahydrofuryl, pyridyl, whereby these heterocyclic groups can be substituted, e.g. with halogen, alkyl, alkoxy, alkylthio, acylamino or aryl.
  • R 3 sulfinic acid component
  • R 4 thiol component
  • the compounds of formula II are known and can be synthesized by methods as described in Houben Weyl, Methods of Organic Chemistry, Vol. E11, p. 1113 ff. Processes in which sulfinic acids or their salts are reacted with sulfenoic acid halides are preferred. Compounds of formula II are also described in DE-A-32 41 886.
  • Coupler (I) and thiosulfonic acid ester (11) are generally used in a molar ratio between 0.25: 1 and 2.0: 1, preferably between 0.7: 1 and 1.2: 1 and in particular in an approximately equimolar amount.
  • Photographic recording materials with a purple layer obtained in this way have sensitometric properties such as color yield and gradation and stability properties, as would be expected from the use of 2-equivalent purple couplers. Surprisingly, these recording materials do not have the disadvantage of delayed dye formation and the subsequent change in gradation that is characteristic of 2-equivalent purple couplers. In this respect, the recording materials with the magenta layers according to the invention behave much more than if they contained unchanged 4-equivalent magenta couplers.
  • the 4-equivalent purple couplers (I) and the compounds of the formula II are worked together in a known manner, if appropriate with the aid of suitable oil formers, in a casting solution for a silver halide emulsion layer or another colloid layer.
  • 4-equivalent purple couplers and thiosulfonic acid esters can be added to a hydrophilic colloid solution from separate solutions or from a common solution in a suitable coupler solvent (oil former), if appropriate in the presence of a wetting or dispersing agent.
  • the oil formers are substances that generally boil above 180 * C and have good dissolving power for the substances to be dispersed. These include the esters of glutaric acid. Adipic acid, phthalic acid, sebacic acid, succinic acid, maleic acid, fumaric acid, isophthalic acid. Terephthalic acid and phosphoric acid or the esters of glycerol, as well as paraffin and fluorinated paraffin are preferably used because these compounds are chemically stable and very easily accessible, can be handled very easily and have no adverse effect on the light-sensitive materials when the dispersions are used for photographic purposes.
  • oil formers For example, the following are frequently used as oil formers: tricresyl phosphate, triphenyl phosphate, dibutyl phthalate, di-n-octyl phtha lat, di-2-ethylhexyl phthalate, glycerol tributyrate, glycerol tripropionate, dioctyl sebacate, paraffin and fluorinated paraffin.
  • Monoesters of fatty succinic acids have also proven to be advantageous. Such compounds are described in US-A-3,689,271.
  • carboxylic acid dialkylamides such as, for example, diethyllauramide, palmitic acid diethylamide and phthalic acid dialkylamides are also suitable as oil formers.
  • the compounds of formula 11 or the sulfinic acids possibly formed therefrom have oil-forming properties or have a favorable effect on the stability of the coupler dispersion present in the dried layer.
  • the presence of the sulfinic acids formed can furthermore be advantageous because of their action as antioxidants. Since they are generally not photographically inert - for example, under certain conditions they can reduce blue-green indoaniline dyes to the leuco dyes - it is sometimes advantageous to choose diffusion-resistant sulfinic acids, e.g. a sulfinic acid with at least 16 carbon atoms.
  • the hydrophilic casting solution can of course contain other conventional additives in addition to the binder.
  • the coupler and thiosulfonic acid ester solution need not be directly dispersed in the casting solution for the silver halide emulsion layer or other water permeable layer; Rather, it can also be advantageously first dispersed in an aqueous, non-photosensitive solution of a hydrophilic colloid, whereupon the mixture obtained, after removal of the low-boiling organic solvents used, is mixed with the casting solution for the photosensitive silver halide emulsion layer or another water-permeable layer before application.
  • the light-sensitive silver halide emulsions used in the light-sensitive layers can contain chloride, bromide and iodide or mixtures thereof as the halide. These are preferably chloride-rich emulsions with a bromide content of less than 1 mol%.
  • the emulsions can be heterodisperse or else monodisperse emulsions, which preferably have an average grain size of 0.3 /..Lm to 1.2 ⁇ m.
  • the silver halide grains can also have a layered grain structure.
  • the emulsions can be chemically and or spectrally sensitized in the usual way; they can also be stabilized by suitable additives. Suitable chemical sensitizers, spectral sensitizing dyes and stabilizers are described, for example, in Research Disclosure 17643 (December 1978); Reference is made in particular to chapters 111, IV and Vl.
  • the color photographic recording material according to the invention preferably contains at least one silver halide emulsion layer for recording light from each of the three spectral ranges red, green and blue, which is spectrally sensitized in a known manner by means of suitable sensitizing dyes.
  • a layer which is not sensitive to light is generally arranged between layers of different spectral sensitivity and can contain means for preventing the incorrect diffusion of developer oxidation products. If there are several silver halide emulsion layers of the same spectral sensitivity, these can be directly adjacent to one another or be arranged such that a light-sensitive layer with a different spectral sensitivity is located between them (DE-A-19 58 709, DE-A-25 30 645, DE-A -26 22 922).
  • Color photographic recording materials according to the invention usually contain, in spatial and spectral assignment to the silver halide emulsion layers of different spectral sensitivity, color couplers for producing the different partial color images cyan, purple and yellow, the purple coupler generally being assigned to a green-sensitive silver halide emulsion layer.
  • Color coupler is in such a spatial relationship to the silver halide emulsion layer that an interaction between them is possible which permits an image-wise match between the silver image formed during development and the color image generated from the color coupler. This is generally achieved by the fact that the color coupler is contained in the silver halide emulsion layer itself or in a possibly non-light-sensitive binder layer adjacent to it.
  • Spectral assignment is understood to mean that the spectral sensitivity of each of the light-sensitive silver halide emulsion layers and the color of the partial color image generated from the spatially assigned color coupler are in a specific relationship to one another, with each of the spectral sensitivities (red, green, blue) having a different color of the relevant partial color image (in general, for example, the colors cyan, purple or yellow in this order).
  • red-sensitive silver halide emulsion layers are therefore assigned at least one non-diffusing color coupler for producing the blue-green partial color image, usually a coupler of the phenol or a-naphthol type.
  • Green-sensitive silver halide emulsion layers are assigned at least one non-diffusing color coupler for generating the purple partial color image, which according to the invention is a 4-equivalent purple coupler together with a thiosul fonic acid ester has been incorporated into the relevant layer in addition to the 2 equivalent used according to the invention.
  • blue-sensitive silver halide emulsion layers are assigned at least one non-diffusing color coupler for producing the yellow partial color image, usually a color coupler with an open-chain ketomethylene grouping.
  • Color couplers of this type are known in large numbers and are described in a large number of patents. Examples include the publications “Farbkuppler” by W. PELZ in “Mitanderen aus der Anlagen Anlagenslaboratorien der Agfa, Leverkusen / München", volume 111, page 111 (1961) and by K. VENKATARAMAN in "The Chemistry of Synthetic Dyes", Vol 4, 341 to 387, Academic Press (1971).
  • the usual supports e.g. Cellulose ester supports, e.g. Cellulose acetate and polyester.
  • paper supports which can optionally be coated, e.g. with polyolefins, especially with polyethylene or polypropylene.
  • polyolefins especially with polyethylene or polypropylene.
  • hydrophilic film-forming agents are suitable as protective colloid or binder for the layers of the recording material, e.g. Proteins, especially gelatin. Casting aids and plasticizers can be used. Reference is made to Research Disclosure 17643, Chapter IX, XI and XII.
  • the layers of the photographic material can be hardened in the usual manner, for example with hardeners which contain at least two reactive oxirane, aziridine or acryloyl groups. Furthermore, it is also possible to harden the layers in accordance with the process described in DE-A-22 18 009. It is also possible to harden the photographic layers or the color photographic multilayer materials with hardeners of the diazin, triazine or 1,2-dihydroquinoline series or with hardeners of the vinyl sulfone type. Other suitable curing agents are known from DE-A-24 39 551, DE-A-22 25 230, DE-A-24 39 551 and also from Research Disclosure 17 643, Chapter X. The stabilizing effect of the oil formers according to the invention is particularly pronounced when hardening agents which activate carboxyl groups, e.g. Carbamoylpyridinium or carbamoyloxypyridinium salts can be used.
  • hardening agents which activate carboxyl groups e.g. Carbamoylpyri
  • Suitable color developer substances for the material according to the invention are in particular those of the p-phenylenediamine type, e.g. 4-amino-N, N-diethyl-aniline hydrochloride, 4-amino-3-methyl-N-ethyl-Np- (methanesulfonamido) -ethylaniline sulfate hydrate, 4-amino-3-methyl-N-ethyl-N- ⁇ - hydroxyethylaniline sulfate, 4-amino-N-ethyl-N- (2-methoxyethyl) -m-toluidine-di-p-toluenesulfonic acid and N-ethyl-N- ⁇ -hydroxyethyl-p-phenylenediamine. Further useful color developers are described, for example, in J.Amer.Chem.Soc. 73, 3100 (1951) and in G. Haist, Modern Photographic Processing, 1979, John
  • the material is usually bleached and fixed. Bleaching and fixing can be carried out separately or together.
  • the usual compounds can be used as bleaching agents, for example Fe 3i salts and Fe 3+ complex salts such as ferricyanides, dichromates, water-soluble cobalt complexes etc.
  • Iron-III complexes of aminopolycarboxylic acids in particular, for example, ethylenediaminetetraacetic acid, nitrilotriacetic acid, iminodiacetic acid, N- Hydroxyethylethylenediamine triacetic acid, alkyliminodicarboxylic acids and corresponding phosphonic acids.
  • Persulphates are also suitable as bleaching agents.
  • Color photographic materials were prepared and processed as follows.
  • Alkylthiosulfonic esters as given in Table 1 are dissolved in the same amount by weight of dibutyl phthalate and three times the amount by weight of ethyl acetate in the presence of 0.15 g of sulfosuccinic acid dioctyl ester at a temperature of 50 to 75 ° C. The solution is then in 150 g of 7.5 wt .-% aqueous solution, about 40 * C stirred warm gelatin solution.
  • the dispersate prepared under a) is mixed with a silver halide emulsion which contains 8.2 g of silver in the form of silver bromide, 9.2 g of gelatin and 0.04 g of sodium dodecylbenzenesulfonate. The total volume is adjusted to 350 ml with water.
  • the casting solution prepared in this way is poured onto a layer of cellulose triacetate.
  • the layer structure is dried at 50 to 60 ° C.
  • Table 1 shows the color yield FA, the sensitivity E and the gradation y for numerous material samples.
  • Color coupler dispersion gates are produced similarly to Example 1 and a silver chloride emulsion is added in such a way that casting solutions with 20 g of magenta coupler, 12.5 g of silver and 54 g of gelatin are obtained. These casting solutions are cast onto a layer support made of paper coated on both sides with polyethylene in a similar manner to a silver coating (Ag) of approximately 0.3 gim 2 .
  • Example 1 The layers are cured and dried as in Example 1.
  • Samples of the layers are exposed with a step wedge and processed as follows.
  • Table 2 shows the gradation y 2 and the maximum color density D max for many of the material samples obtained in this way, one for the freshly processed material and the other after storage for 10 days.
  • y 2 is the gradation in the upper part of the color density curve and is determined as the slope of the straight line that intersects the color density curve at points B and C, where A is the curve point that is 0.1 density units above fog, B is the curve point that corresponds to 0.8 log It units higher exposure than A, and C is the curve point corresponding to 0.8 log It units exposure higher than B.
  • the maximum color density D max of the freshly processed material is also given (in brackets) as a percentage, in each case based on the corresponding value D max of the same sample after 10 days of storage.
  • the mixtures according to the invention consisting of 4-equivalent purple coupler and thiosulfonic acid ester give advantageous sensitometric results when measured immediately after processing, both in comparison with the 4-equivalent purple coupler alone and also in comparison with the corresponding 2-equivalent purple coupler alone .
  • the sensitometric values After 10 days of storage, practically no change in the sensitometric values was observed in the samples according to the invention as well as in the comparison samples which contained the 4-equivalent purple coupler alone, while in the comparison samples which contained the 2-equivalent purple coupler alone, the sensitometric values within increase sharply from 10 days to the level of the sensitometric values of the samples according to the invention.
  • the recording material according to the invention does not have the disadvantage of delayed dye formation in the short-term processing that is otherwise observed when using 2-equivalent purple couplers.
  • a layer support made of paper coated on both sides with polyethylene was provided with the following layers.
  • the quantities given relate to 1 m 2 .
  • the amounts of coupler and silver halide in layer 4 apply in the event that the magenta coupler is a 4-equivalent coupler without added thiosulfonic acid ester. If a thiosulfonic acid ester is added or if a 2-equivalent purple coupler is used, the amount of coupler applied is 0.5 mmol and the corresponding amount of silver chloride corresponds to 450 mg AgN0 3 .
  • the samples were exposed to the same extent behind a grayscale wedge with white light and processed in accordance with the short-term process described in Example 2.
  • the samples thus obtained were freshly assessed visually and measured densitometrically.
  • light stability tests were carried out using a xenon lamp.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
EP88115078A 1987-09-26 1988-09-15 Matériau de reproduction photographique couleur Expired - Lifetime EP0309819B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3732512 1987-09-26
DE19873732512 DE3732512A1 (de) 1987-09-26 1987-09-26 Farbfotografisches aufzeichnungsmaterial

Publications (3)

Publication Number Publication Date
EP0309819A2 true EP0309819A2 (fr) 1989-04-05
EP0309819A3 EP0309819A3 (en) 1990-01-17
EP0309819B1 EP0309819B1 (fr) 1993-11-10

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ID=6336969

Family Applications (1)

Application Number Title Priority Date Filing Date
EP88115078A Expired - Lifetime EP0309819B1 (fr) 1987-09-26 1988-09-15 Matériau de reproduction photographique couleur

Country Status (4)

Country Link
US (1) US4868099A (fr)
EP (1) EP0309819B1 (fr)
JP (1) JPH01121855A (fr)
DE (2) DE3732512A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0248671A (ja) * 1988-08-11 1990-02-19 Fuji Electric Co Ltd 電子写真用感光体
US5491053A (en) * 1994-12-23 1996-02-13 Eastman Kodak Company Chromogenic black-and-white motion picture film
GB9626331D0 (en) * 1996-12-19 1997-02-05 Kodak Ltd Photographic recording materials and their use in redox amplification
JP3835091B2 (ja) * 1999-12-16 2006-10-18 コニカミノルタホールディングス株式会社 ハロゲン化銀カラー写真感光材料

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5618943B2 (fr) * 1973-04-25 1981-05-02
JPS5116924A (en) * 1974-08-01 1976-02-10 Fuji Photo Film Co Ltd Shashinyomazentakapuraa
JPS5827486B2 (ja) * 1977-06-03 1983-06-09 富士写真フイルム株式会社 ハロゲン化銀写真乳剤
US4207393A (en) * 1979-03-09 1980-06-10 Minnesota Mining And Manufacturing Company Photographic contrast enhancers
JPH0625135B2 (ja) * 1981-11-18 1994-04-06 コニカ株式会社 マゼンタカプラ−の製造方法

Also Published As

Publication number Publication date
EP0309819A3 (en) 1990-01-17
JPH01121855A (ja) 1989-05-15
DE3732512A1 (de) 1989-04-06
EP0309819B1 (fr) 1993-11-10
DE3885562D1 (de) 1993-12-16
US4868099A (en) 1989-09-19

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