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
  • G03C7/39232—Organic compounds with an oxygen-containing function

Definitions

• the invention relates to a photographic recording material with at least one silver halide layer which contains certain hydroquinone diethers as light stabilizers in one layer.
• color photographic images by chromogenic development, i.e. by developing imagewise exposed silver halide emulsion layers in the presence of suitable color couplers by means of suitable color-forming developer substances - so-called color developers - the oxidation product of the developer substances which forms in accordance with the silver image reacting with the color coupler to form a dye image.
• color developers i.e. by developing imagewise exposed silver halide emulsion layers in the presence of suitable color couplers by means of suitable color-forming developer substances - so-called color developers - the oxidation product of the developer substances which forms in accordance with the silver image reacting with the color coupler to form a dye image.
• Aromatic compounds containing primary amino groups especially those of the p-phenylenediamine type, are usually used as color developers.
• magenta dyes produced from pyrazoloazole couplers bleach particularly strongly, while the cyan dyes produced from phenolic couplers proved to be particularly unaffected in this regard.
• Suitable light-stabilizing additives are essentially phenolic compounds, in particular derivatives of hydroquinone, which are either added to the couplers or linked to the coupler molecules in the form of substituents (DE-B-1 547 803, DE-A-26 17 826, DE-A -29 52 511, JP-N 53 070 822, JP-N 54 070 830, JP-N 54 073 032).
• Hydroquinone dialkyl ethers have also been described as light stabilizers, e.g. in US-A 4 588 679 and US-A 4 735 893.
• the known light stabilizers do not yet meet the requirements placed on them in every respect.
• the invention has for its object to provide a color photographic recording material which contains silver halide emulsion layers with associated cyan, magenta or yellow couplers and has been stabilized by adding a light stabilizer against fading of the chromogen-formed dye under the influence of light.
• An alkyl radical represented by R 1 to R 6 can be straight-chain or branched, unsubstituted or substituted and can contain up to 18 carbon atoms; Examples are methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, tert-amyl, hexyl, tert-hexyl, octyl, dodecyl; Examples of substituents are halogen (eg chlorine), hydroxy, alkoxy, alkoxycarbonyl, dialkylamino.
• a cycloalkyl radical represented by R 1 , R 3 or R 4 is in particular cyclohexyl or cyclopentyl.
• An aryl radical represented by R 1 , R 3 or R 4 is in particular phenyl, optionally substituted, for example with alkylsulfonyl, alkyl and / or alkoxy.
• An acyl radical represented by or contained in R 3 , R 4 or R 5 is derived from an aliphatic or aromatic mono- or dicarboxylic acid, from a carbonic acid monoester or from a carbamic acid, examples of such acyl radicals are acetyl, 2-ethylhexanoyl, p-hydroxybenzoyl , Nn-butylcarbamoyl, Nt-butylcarbamoyl, N-dodecylcarbamoyl, hexyloxycarbonyl, dodecyloxycarbonyl.
• An acyl radical represented by R 5 can also be derived from phosphoric acid, phosphonic acid or phosphorous acid.
• the hydroquinone diether compound corresponds to the formula I, in which at least one of the radicals R 3 and R 4 is tertiary alkyl.
• the hydroquinone diether compound corresponds to the formula I in which -XR 5 is -OH, -O-CH 2 -CH 2 -OH or -O-acyl, the acyl radical being derived from aliphatic or aromatic carboxylic acids, from Carbamic acid, carbonic acid monoesters or phosphoric acid, phosphonic acid or phosphorous acid.
• the hydroquinone diether compound corresponds to the formula I in which n is 0 or 1.
• hydroquinone diether compounds according to the invention are given below.
• An alkyl radical represented by R 26 or R 51 is an alkyl radical, as can also be represented by R 1 to R 6 .
• An alkyl radical represented by R 31 or R 32 can be straight-chain or branched and contain up to 18 carbon atoms.
• a cycloalkyl radical represented by R 31 , R 32 or R 51 is a cycloalkyl radical, as can also be represented by R 1 , R 3 or R 4 .
• An aryl radical represented by R 51 is an aryl radical, as can also be represented by R 1 , R 3 or R 4 .
• An acyl radical represented by R 26 is an acyl radical, as can also be represented by R 3 , R 4 or R 5 .
• R 41 and R 42 for H or alkyl
• the color photographic recording material according to the invention contains a sequence of several light-sensitive silver halide emulsion layers with respectively assigned color couplers and optionally further auxiliary layers such as in particular protective layers and non-light-sensitive binder layers arranged between the light-sensitive layers, wherein according to the present invention at least one of the light-sensitive silver halide emulsion layers present combines a compound of the formula I according to the invention in combination is associated with a color coupler.
• a compound of the formula I according to the invention is preferably used in combination with at least one compound of one of the formulas 11, 111, IV and V.
• synergistic effects occur, i.e.
• the azomethine dyes produced during development are protected even better against light by a combination of a compound of the formula I and a compound of one of the formulas 11, 111, IV and V than by a compound of the formula I alone.
• the compounds of the formula I are used here with compounds of the formulas 11, 111, IV and V in a ratio of 1:10 to 10: 1, preferably 1: 4 to 4: 1.
• the compounds of the formulas I, II, 111, IV and V used according to the invention act primarily as light stabilizers, i.e.
• the azomethine dyes formed from the color coupler in the chromogenic development have a considerably increased stability in the presence of light against them.
• all or part of the compounds according to the invention also take on the function of an oil former for the color coupler, i.e. they can be used alone or together with other known oil formers as coupler solvents.
• the compounds according to the invention preferably make up 50 to 100% by weight of the total amount of oil former in the respective layer. Accordingly, they are preferably used in 0.2 to 2 times the amount by weight based on the color coupler used with them.
• further oil formers are not required at all, or only in a small amount if necessary, has a favorable effect on the layer loading and / or the total layer thickness of the recording materials according to the invention.
• the compounds of the formulas I to V used according to the invention are used as a solution in aprotic (hydrophobic) solvents, e.g. Ethyl acetate, when incorporated into the casting solution for the layer in question, together with the respective color coupler.
• aprotic (hydrophobic) solvents e.g. Ethyl acetate
• the incorporation is carried out in the usual manner, it being possible, if appropriate, to use further auxiliary solvents and / or high-boiling coupler solvents, so-called oil formers.
• the silver halide present as a light-sensitive component in the photographic recording material according to the invention can contain chloride, bromide or iodide or mixtures thereof as the halide.
• the halide content of at least one layer can consist of 0 to 15 mol% of iodide, 0 to 100 mol% of chloride and 0 to 100 mol% of bromide.
• silver bromide iodide emulsions are usually used; in the case of color negative and color reversal paper, silver chloride bromide emulsions with a high chloride content are used up to pure silver chloride emulsions.
• It can be predominantly compact crystals, e.g. are regular cubic or octahedral or can have transitional forms.
• platelet-shaped crystals can preferably also be present, the average ratio of diameter to thickness of which is preferably at least 5: 1, the diameter of a grain being defined as the diameter of a circle with a circle content corresponding to the projected area of the grain.
• the layers can also have tabular silver halide crystals in which the ratio of diameter to thickness is substantially greater than 5: 1, e.g. 12: 1 to 30: 1.
• the silver halide grains can also have a multi-layered grain structure, in the simplest case with an inner and an outer grain area (core / shell), the halide composition and / or other modifications, such as e.g. Doping of the individual grain areas are different.
• the average grain size of the emulsions is preferably between 0.2 .mu.m and 2.0 .mu.m, the grain size distribution can be both homo- and heterodisperse. Homodisperse grain size distribution means that 95% of the grains do not deviate from the mean grain size by more than ⁇ 30%.
• the emulsions can also contain other silver salts, e.g. contain organic silver salts such as silver benzotriazolate or silver behenate.
• Two or more kinds of silver halide emulsions, which are prepared separately, can be used as a mixture.
• 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 contains at least one red-sensitive, at least one green-sensitive and at least one blue-sensitive silver halide emulsion layer.
• the light-sensitive layers are through in a known manner suitable sensitizing dyes spectrally sensitized; In the case of the blue-sensitive silver halide emulsion layer, it is not necessary to add sensitizing dyes because of the inherent sensitivity.
• Suitable green sensitizers are, for example, 9-ethylcarbocyanines with benzoxazole, naphthoxazole or a benzoxazole and a benzthiazole as basic end groups, and also benzimidazocarbocyanines, which may also be further substituted and must likewise contain at least one sulfoalkyl group on the heterocyclic nitrogen.
• Each of the said photosensitive layers can consist of a single layer or in a known manner, e.g. in the so-called double-layer arrangement, also comprise two or more silver halide emulsion partial layers (DE-C-1 121 470).
• red-sensitive silver halide emulsion layers are usually arranged closer to the support than green-sensitive silver halide emulsion layers and these in turn are closer than blue-sensitive layers, a non-light-sensitive yellow filter layer generally being located between green-sensitive layers and blue-sensitive layers.
• other arrangements are also conceivable, e.g. for color paper.
• a non-light-sensitive intermediate layer 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, they 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-1 958 709, DE-A-2 530 645, DE-A -2 622 922).
• 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, magenta and yellow, at least one of the color couplers together with one of the compounds of the formula I according to the invention, preferably in combination with at least one compound of formulas II, III, IV and V, is assigned to the silver halide emulsion layer in question.
• Color coupler is in such a spatial relationship with 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 produced from the color coupler.
• This is usually achieved by the fact that the color coupler together with the hydroquinone diether compound of the formula I, preferably in combination with at least one compound of one of the formulas II, III, IV and V, is contained in the silver halide emulsion layer itself or in an adjacent, possibly non-photosensitive, layer Binder layer.
• 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 respective partial color image (in general, for example, the colors cyan, magenta or yellow in this order).
• Couplers of the formula VI are referred to collectively as pyrazoloazole couplers. These are understood to mean in particular couplers which are derived from imidazolo [1,2-b] pyrazole, imidazolo [3,4-b] pyrazole, pyrazolo- [2,3-b] pyrazole, pyrazolo [3,2-c] - 1,2,4-triazole, pyrazolo [2,3-b] -1,2,4-triazole, pyrazolo [2,3-c] -1,2,3-triazole or pyrazolo [2,3-d] tetrazole.
• the corresponding structures are given below by the formulas Vla to Vlg.
• radicals R 61 , S, T and U represent hydrogen, alkyl, aralkyl, aryl, alkoxy, aroxy, alkylthio, arylthio, amino, anilino, acylamino, cyano, alkoxycarbonyl, carbamoyl , Sulfamoyl, where these radicals can be further substituted.
• Y represents hydrogen or a radical which can be split off on color coupling, such as a halogen atom or a preferably cyclic group attached to the coupling point via an oxygen atom, a sulfur atom or a nitrogen atom.
• the coupling to the coupling point of the coupler molecule can either be directly via an atom which is part of a ring, e.g. B. a nitrogen atom, or indirectly via an intermediate link.
• Such cleavable groups are known in large numbers, for. B. as escape groups of 2 equivalent magnetic couplers.
• cleavable groups linked via oxygen correspond to the formula - 0 - R62 in which R 62 represents an acyclic or cyclic organic radical, for example alkyl, aryl, a heterocyclic group or acyl which is derived, for example, from an organic carbon or sulfonic acid.
• R 62 denotes an optionally substituted phenyl group.
• heterocyclic rings which are connected to the coupling site of the purple coupler via a ring nitrogen atom.
• the heterocyclic rings often contain groups adjacent to the nitrogen atom activating the bond to the coupler molecule, e.g. B. carbonyl or sulfonyl groups or double bonds.
• the cleavable group is attached to the coupling site of the coupler via a sulfur atom, it can be the remainder of a diffusible carbocyclic or heterocyclic mercapto compound which is able to inhibit the development of silver halide.
• Such inhibitor residues have been widely described as a cleavable group attached to the coupling site of couplers, including magenta couplers, e.g. in US-A-3,227,554.
• pyrazoloazole couplers of the formulas Vla to Vlg those of the formulas Vld and Vle are preferably used according to the invention together with a hydroquinone diether compound of the formula I.
• at least one of the radicals R 6 'and S or at least one of the radicals R 6 ' and T preferably represents a secondary alkyl or tertiary alkyl radical, ie a radical of the formula wherein R 63 and R 64 are alkyl and R 65 is H or a substituent.
• Possible substituents are alkyl, aryl, cycloalkyl, hydroxy, halogen, -COOH, -S03H, -S02H, alkoxy, aryloxy, alkylthio, arylthio, nitro, sulfonyl, sulfamoyl, sulfonylamino, acylamino, carbamoyl, acyloxy, alkoxycarbonyl, aryloxycarbamoyl, ureido Carbamoyloxy, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyloxy and aryloxycarbonyloxy.
• Preferred substituents are alkyl, sulfonyl, sulfonylamino, sulfamoyl, ureido, acylamino, carbamoyl, alkoxy, aryloxy and alkoxycarbonylamino.
• pyrazoloazole couplers of the formula VI are:
• the color couplers can be 4-equivalent couplers, but also 2-equivalent couplers.
• the latter are derived from the 4-equivalent couplers in that they contain a substituent in the coupling point, which is split off during the coupling.
• the 2-equivalent couplers include those that are colorless, as well as those that have an intensive intrinsic color that disappears when the color is coupled or is replaced by the color of the image dye produced (mask coupler), but also the white couplers that are used Reaction with color developer oxidation products yield essentially colorless products.
• the 2-equivalent couplers also include those couplers that contain a cleavable residue in the coupling point, which is released upon reaction with color developer oxidation products and thereby either directly or after one or more further groups have been cleaved from the primarily cleaved residue (e.g. DE-A-27 03 145, DE-A-28 55 697, DE-A-31 05 026, DE-A-33 19 428), a certain desired photographic effectiveness unfolds, e.g. as a development inhibitor or accelerator.
• Examples of such 2-equivalent couplers are the known DIR couplers as well as DAR or. FAR coupler.
• the couplers used in particular the magenta couplers of the pyrazoloazole type, preferably used according to the invention, for example of the formulas (Vld) and (Vle), can also be in polymeric form, e.g. are used as polymer latex.
• High molecular weight color couplers are described, for example, in DE-C-1 297 417, DE-A-24 07 569, DE-A-31 48 125, DE-A-32 17 200, DE-A-33 20 079, DE-A- 33 24 932, DE-A-33 31 743, DE-A-33 40 376, EP-A-27 284, US-A-4 080 211.
• the high molecular weight color couplers are generally produced by polymerizing ethylenically unsaturated monomeric color couplers .
• the color couplers used can also be those which provide dyes with poor or restricted mobility.
• Weak or restricted mobility means mobility that is dimensioned such that the contours of the discrete dye spots formed in the chromogenic development run and are smeared into one another.
• This degree of mobility is to be distinguished on the one hand from the usual case of complete immobility in photographic layers, which is sought in conventional photographic recording materials for the color couplers or the dyes produced therefrom, in order to achieve the highest possible sharpness, and on the other hand from the case of complete mobility of the dyes, which is sought, for example, in color diffusion processes.
• the last-mentioned dyes usually have at least one group that make them soluble in the alkaline medium.
• the extent of the weak mobility sought according to the invention can be controlled by varying substituents, for example in order to influence the solubility in the organic medium of the oil former or the affinity for the binder matrix in a targeted manner.
• the color photographic recording material of the present invention can contain further additives, for example antioxidants, dye-stabilizing agents and agents for influencing the mechanical and electrostatic properties and UV absorbers.
• additional compounds are advantageously combined with the compounds according to the invention, i.e. used in the same binder layer or in adjacent binder layers.
• Examples are aryl-substituted benzotriazole compounds (US-A-3 533 794), 4-thiazolidone compounds (US-A-3 314 794 and 3 352 681), benzophenone compounds (JP-A-2784/71), cinnamic acid ester compounds (US-A-3 705 805 and 3,707,375), butadiene compounds (US-A-4,045,229) or benzoxazole compounds (US-A-3,700,455).
• Ultraviolet absorbing couplers such as a-naphthol type cyan couplers
• ultraviolet absorbing polymers can also be used. These ultraviolet absorbents can be fixed in a special layer by pickling.
• the color photographic recording material according to the invention which contains a color coupler and a compound of the formula I associated with at least one silver halide emulsion layer, is developed with a color developer compound.
• All developer compounds which have the ability in the form of their oxidation product to react with color couplers to form azomethine dyes can be used as the color developer compound.
• Suitable color developer compounds are aromatic compounds of the p-phenylenediamine type containing at least one primary amino group, for example N, N-dialkyl-p-phenylenediamines, such as N, N-diethyl-p-phenylenediamine, 1- (N-ethyl-N-methylsulfonamidoethyl) -3 -methyl-p-phenylenediamine, 1- (N-ethyl-N-hydroxyethyl-3-methyl-p-phenylenediamine, 1- (N-ethyl-N-3-hydroxypropyl) -3-methyl-p-phenylenediamine and 1- (N-ethyl-N-methoxyethyl) -3-methyl-p-phenylenediamine.
• N, N-dialkyl-p-phenylenediamines such as N, N-diethyl-p-phenylenediamine, 1- (N-ethyl-N-methylsul
• 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 3 + salts and Fe 3 + complex salts such as ferricyanides, dichromates, water-soluble cobalt complexes, etc.
• Particularly preferred are iron III complexes of aminopolycarboxylic acids, in particular, for example, ethylenediaminetetraacetic acid, N-hydroxyethylethylenediamine triacetic acid, alkyliminodicarboxylic acids and of corresponding phosphonic acids.
• Persulphates are also suitable as bleaching agents.
• a color photographic recording material suitable for a rapid processing process was produced by applying the following layers in the order given to a support made of paper coated on both sides with polyethylene.
• the quantities given relate to 1 m 2 .
• the corresponding amounts of AgN0 3 are given for the silver halide application.
• UV absorber UV-1 The following compound (UV absorber UV-1) was used in layers 5 and 7.
• Samples 2 to 9 were produced in the same way as sample 1, with the difference that an additional 0.31 g of light stabilizer of the structural formulas VP-1 to VP-3 or light stabilizer according to the invention of the structural formula I was added to the layer 4.
• coupler VI-1 was replaced by other couplers of formula VI in the amount shown in the table below.
• coupler VI-23 0.34 g of DBP and 0.04 g of TKP were additionally replaced in the 4th layer by 0.38 g of 2,4-di-tert-pentylphenol (samples 18 to 20).
• samples 11 to 12, 15 to 16 and 19 with coupler of the formula VI were added to 0.31 g of light stabilizer of the formula I.
• Samples 2-4, 13, 17 and 20 contained a comparison compound of one of the formulas VP-1, VP-2, VP-3.
• the example shows that the light stability of the image dyes is significantly improved by the compounds of the formula I according to the invention.
• Sample 14 serves as a comparison as described under Example 1.
• Samples 21 to 23 according to the invention differ from sample 14 in that DBP and TKP in the green-sensitive layer were replaced by 0.4 g of light stabilizers of the formula I. Processing and testing were carried out as described in Example 1 (Table 2).
• Example 2 shows that the light stabilizers of the formula I according to the invention can be used as oil formers in combination with pyrazoloazole couplers. Sensitivity, gradation and maximum density are comparable to DBP / TKP, the light stability is significantly increased.
• Color photographic recording materials for reversal processing were produced by successively applying the layers listed below on a cellulose triacetate support provided with an adhesive layer.
• Example 3 0.87 g hardening agent carbamoylpyridinium salt CAS Reg.No. 65411-60-1
• Example 3 the following compounds are used in addition to the compounds already mentioned:
• Samples 25 and 26 according to the invention were produced in the same way as sample 24, with the difference that the oil-forming agent TKP in layers 6 and 7 was replaced by compounds 1-14 and I-17.
• sample 27 coupler VI-7 was replaced by coupler VI-14, TKP (comparison) served as an oil former.
• Samples 28 to 30 according to the invention differed from sample 27 in that TKP in layers 6 and 7 was replaced by compounds 1-4, 1-14 and 1-17.
• the example shows that the compounds of the formula I according to the invention made it possible to significantly increase the light stability of the image dyes in color reversal films. Sensitivity, gradation and maximum density were not adversely affected.
• a color photographic recording material suitable for a rapid processing process was produced as in Example 1, sample 1, with the difference that in layer 4 instead of magenta coupler VI-1 the magenta coupler VI-6 in an amount of 0.41 g and instead of the oil former mixture exclusively 0 , 38 g CPM were used (sample 31).
• Sample 32-52 was produced in the same way as sample 31, with the difference that the light stabilizers VP-1, VP-3, VP-4 or light stabilizers according to the invention, which are given in table 1, were additionally added to layer 4.
• Example 4 shows that the use of light stabilizers of the formula I can improve the light stability (samples 33, 34, 35, 38) and that the light stability achieved by compounds of the formula I can be further improved if the compounds of the formula I in combination be used with compounds of formulas II, III, IV and V (samples 39-52).
• Sample 31 from Example 4 serves as a comparison.
• Samples 53-59 are produced in the same way as sample 31 from example 4, with the difference that the oil former in layer 4 is replaced by compounds of the formula I according to the invention and further compounds of one of the formulas II, 111, IV and V or the comparison compound VP-3 are added.
• Example 5 shows that the light stabilizers of the formula I according to the invention can additionally take on the function of an oil former without any adverse effects on sensitivity, gradation and maximum density being observed.
• the light stability is again significantly increased by the combination according to the invention with compounds of the formula II, III, IV or V.
• the comparative compound VP-3 is significantly less effective here.
• Samples 61-72 were prepared in the same manner as Sample 60, with the difference that the light stabilizers shown in Table 6 were added to layer 3.
• the magenta coupler VI-1 was also replaced by the ones listed in Table 6 (VI-5, VI-23).
• Example 6 shows the improvement in light stability through the use of compounds of the formula I (samples 61, 66, 70) and the again increased effectiveness when combined with compounds of one of the formulas II, III, IV and V as light stabilizers.
• the compounds VP-1, VP-3 and VP-4 used as a comparison are significantly less effective.

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• 1993
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