EP0176845B1 - Matériau d'enregistrement photographique - Google Patents

Matériau d'enregistrement photographique Download PDF

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Publication number
EP0176845B1
EP0176845B1 EP85111669A EP85111669A EP0176845B1 EP 0176845 B1 EP0176845 B1 EP 0176845B1 EP 85111669 A EP85111669 A EP 85111669A EP 85111669 A EP85111669 A EP 85111669A EP 0176845 B1 EP0176845 B1 EP 0176845B1
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EP
European Patent Office
Prior art keywords
color
couplers
alkyl
coupler
silver halide
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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
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EP85111669A
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German (de)
English (en)
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EP0176845A3 (en
EP0176845A2 (fr
Inventor
Günter Dr. Renner
Werner Dr. Liebe
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Agfa Gevaert AG
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Agfa Gevaert AG
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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
    • G03C7/39212—Carbocyclic
    • G03C7/39216—Carbocyclic with OH groups

Definitions

  • the invention relates to a photographic recording material with at least one silver halide emulsion layer, which contains novel light stabilizers for the image dyes produced during chromogenic development, in particular for yellow or pupil-colored azomethine dyes.
  • Suitable light-stabilizing agents 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).
  • DE-A-21 46 668 describes compounds with which the light stability of chromogenically produced image dyes, and to a small extent also of the yellow dyes, can be improved.
  • the invention is based on the object of specifying novel light stabilizers for photographic recording materials, in particular those which are suitable for improving the light stability of the yellow image dyes produced from yellow couplers.
  • group G is either a hydroxyl group or an alkali-labile precursor group of a hydroxyl group.
  • An alkali-labile precursor group of a hydroxyl group means a group which undergoes a conversion under the conditions of alkaline development and thereby forms a hydroxyl group.
  • Typical examples of this are "acylated hydroxyl groups" which are hydrolyzed by alkali during development, the blocking acyl group being split off.
  • Blocking acyl groups are derived, for example, from aliphatic or aromatic carboxylic or sulfonic acids; Examples include acetyl, dichloroacetyl, alkoxycarbonyl, pyruvoyl.
  • the radical represented by X which cannot be split off under the conditions of chromogenic development can be, for example, an alkyl, alkoxycarbonyl, carbamoyl, acylamino, sulfamoyl, alkylsulfonyl or arylsulfonyl radical.
  • Those residues which are particularly suitable under the conditions of chromogenic development, i.e. at pH values between 9 and 12 not only cannot be split off, but they also do not give the light-stabilizing compound any oxidizability under these conditions (e.g. through subsequent products of development).
  • alkyl radicals mentioned can be straight-chain or branched and contain up to 18 carbon atoms or more; Examples are methyl, ethyl, t-butyl, 1,1,3,3-tetramethylbutyl, n-dodecyl or n-tridecyl. Such alkyl radicals can also be contained in the alkoxycarbonyl, carbamoyl, acylamino, sulfamoyl and alkylsulfonyl radicals mentioned.
  • the alkyl radicals represented by R ', R 2 or Z can be straight-chain or branched and can contain up to 20 C atoms and optionally further substituents.
  • substituents are, for example, phenoxy groups, which in turn can be further substituted by alkyl, alkoxy, hydroxyl or halogen.
  • An aralkyl radical represented by R 2 is, for example, benzyl; an aryl radical represented by R 2 is, for example, phenyl.
  • An alkoxy or alkylamino radical represented by R 3 can contain a straight-chain or branched, optionally substituted alkyl radical having up to 20 carbon atoms.
  • An arylamino radical represented by R 3 is, for example, an anilino radical which may contain further substituents, such as halogen, nitro or alkyl.
  • a halogen substituent represented by Z is, for example, chlorine or bromine.
  • An acylamino group represented by Z is derived from aliphatic or aromatic carboxylic or sulfonic acids.
  • the group t-CsH17 in the compounds S-20 to S-23 is an alkyl radical of the following structure
  • the compounds of formula I to be used according to the invention can be prepared by known methods, e.g. by acylation or sulfonation of the corresponding o-aminophenols, in dipolar aprotic solvents such as dimethylformamide, dimethylacetamide, hexamethylphosphoric acid triamide, N-methylpyrolidone or the like. or in dipolar solvents such as acetone, methyl ethyl ketone, acetonitrile or in protic solvents such as alcohols with the addition of base.
  • dipolar aprotic solvents such as dimethylformamide, dimethylacetamide, hexamethylphosphoric acid triamide, N-methylpyrolidone or the like.
  • dipolar solvents such as acetone, methyl ethyl ketone, acetonitrile
  • protic solvents such as alcohols with the addition of base.
  • the color photographic recording materials according to the invention are preferably multilayer materials which have a plurality of silver halide emulsion layers or emulsion layer units with different spectral sensitivity.
  • Emulsion layer units are understood to mean laminates of 2 or more silver halide emulsion layers of the same spectral sensitivity.
  • Each of the light-sensitive silver halide emulsion layers or emulsion layer units mentioned is assigned a color coupler which can react with color developer oxidation products to form a non-diffusing dye.
  • the color couplers are expediently non-diffusing and are to be accommodated in the light-sensitive layer itself or in close proximity here.
  • the color couplers assigned to the two or more partial layers of an emulsion layer unit do not necessarily have to be identical. You should only at the Color development gives the same color, usually a color that is complementary to the color of the light to which the photosensitive silver halide emulsion layers are sensitive.
  • the red-sensitive silver halide emulsion layers are therefore each 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.
  • a coupler of the phenol or a-naphthol type usually a coupler of the phenol or a-naphthol type.
  • Particularly noteworthy are, for example, cyan couplers as described in US-A-2,474,293, US-A-2,367,531, US-A-2,895,826, US-A-3,772,002, EP-A-0 028 099 , EP-A-0 112 514.
  • the green-sensitive silver halide emulsion layers each contain at least one non-diffusing color coupler for producing the purple partial color image, color couplers of the 5-pyrazolone or indazolone type usually being used. Particularly noteworthy are, for example, purple couplers as described in US Pat. No. 2,600,788, US Pat. No. 4,383,027, DE-A-1,547,803, DE-A-1,810,464, DE-A-2,084,665, DE-A-3 226 163.
  • the blue-sensitive silver halide emulsion layers each contain at least one non-diffusing color coupler for producing the yellow partial color image, usually a color coupler with an open-chain ketomethylene grouping.
  • a color coupler with an open-chain ketomethylene grouping are particularly noteworthy.
  • yellow couplers as described in US Pat. No. 3,408,194, DE-A-2,329,587, DE-A-2,456,976.
  • Color couplers of these types are known in large numbers and are described in a large number of patents. Examples include the publications “Color Coupler” by W. Pelz, "Messages from the research laboratories of Agfa, Leverkusen / Kunststoff", Volume 111 (1961) p. 111 and K. Venkataraman in “The Chemistry of Synthetic Dyes", Vol. 4, 341 to 387, Academic Press (1971).
  • the color couplers can be either conventional 4-equivalent couplers or 2-equivalent couplers, which require a smaller amount of silver halide to produce the color.
  • 2-equivalent couplers 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 which can be used according to the present invention include both those which are practically colorless and those which have an intense inherent color which disappears when the color is coupled or is replaced by the color of the image dye produced.
  • the latter couplers can also be present in the light-sensitive silver halide emulsion layers and serve there as mask couplers to compensate for the undesired secondary densities of the image dyes.
  • the 2-equivalent couplers include the known DIR couplers, which are couplers that contain a detachable residue in the coupling point, which is released as a diffusible development inhibitor or precursor of a development inhibitor when reacted with color developer oxidation products.
  • color coupler mixtures can be used to set a desired color or reactivity.
  • water-soluble couplers can be used in combination with hydrophobic water-insoluble couplers.
  • the same methods that are also used for the incorporation of the compounds according to the invention are suitable for incorporating the couplers into the layers of the color photographic recording material.
  • one of the known emulsification methods is advantageously used for incorporating hydrophobic color couplers, in which, for example, color couplers are optionally dissolved in an organic solvent in the presence of a high-boiling coupler solvent or oil former and then dispersed in a gelatin solution.
  • high-boiling coupler solvents are dibutyl phthalate and tricresyl phosphate.
  • Further coupler solvents are described, for example, in US-A-2,322,927, US-A-3,689,271, US-A-3,764,336 and US-A-3,765,897.
  • aqueous dispersions of the hydrophobic couplers It is also possible to prepare aqueous dispersions of the hydrophobic couplers and to add them to the respective casting solutions.
  • aqueous slurries of the couplers are finely ground, for example by intensive stirring with the addition of sharp-edged sand and / or by using ultrasound.
  • the compounds according to the invention are preferably used together with yellow couplers; however, effects are also achieved when used in combination with magenta couplers or with cyan couplers.
  • they can be dissolved in an oil former together with the respective color couplers and added to the respective casting solution in the form of such a common solution.
  • they can also be added to the casting solution in the form of a separate solution in an oil former.
  • Advantageous results can be achieved if 5 to 200% by weight, preferably 20 to 100% by weight, of the compound according to the invention, in each case based on the amount of the color coupler used, are used.
  • Compound I and the assigned color coupler are preferably in the same layer. However, it is also possible to introduce them into adjacent layers.
  • the color photographic recording material can additionally contain other known stabilizing agents, for example UV absorbers and agents which fade the dyes, in particular under the action of light, Prevent or delay heat or moisture.
  • stabilizing agents for example UV absorbers and agents which fade the dyes, in particular under the action of light, Prevent or delay heat or moisture.
  • UV absorbers for example, phenol derivatives, hydroquinone derivatives, p-alkoxyphenol derivatives, pyrogallol derivatives, gallic acid derivatives, 5-hydroxycoumaran derivatives, 6-hydroxychromane derivatives and 5-hydroxyindane derivatives have been described as being suitable for this purpose.
  • the compound according to the invention is preferably used in combination with yellow couplers.
  • yellow couplers are in particular hydrophobic yellow couplers with good solubility in hydrophobic or hydrophilic oil formers.
  • the yellow couplers are preferably derived from a-pivaloyl or a-benzoyiacetanilides. Examples of such yellow couplers are listed below.
  • the intermediate layers arranged between the light-sensitive silver halide emulsion layers, the binder of which preferably consists of gelatin, may contain compounds which are capable of reacting with color developer oxidation products and which thus prevent undesired diffusion of the color developer oxidation products.
  • examples of such compounds are non-diffusing reducing agents, e.g. Hydroquinone derivatives which, when reacted with the color developer oxidation products, do not give any dye remaining in the layers, or color couplers which give a soluble dye which is washed out of the layers during color photographic processing.
  • suitable compounds for suppressing the undesired diffusion of color developer oxidation products are described, for example, in the monograph "Stabilization of Photographic Silver Halide Emulsions" by E. J. Birr, The Focal Press, 1st Edition 1974, pages 116 to 122.
  • the recording materials according to the invention can be developed with the usual color developer compounds, in particular those of the p-phenylenediamine series with a primary amino group, e.g. 4-amino-N, N-dimethylaniline, 4-amino-N, N-diethylaniline, 4-amino-3-methyl-N, N-diethylaniline, 4-amino-3-methyl-N-methyl-N- (ß -methylsulfonamidoethyl) aniline, 4-amino-N-ethyl-N- (ß-hydroxyethyl) aniline, 4-amino-3-methyl-N-ethyl-N- (ß-hydroxyethyl) aniline, 4-amino- 3-methyl-N-ethyl-N- (ß-methoxyethyl) aniline, 4-amino-3-methyl-N-ethyl-N- (ß-methylsulfonamidoethyl) aniline, 4-amino
  • Color photographic materials were prepared as follows.
  • the emulsify produced under a is mixed with a silver halide emulsion which contains 8.2 g of silver in the form of silver halide, 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 material After drying, the material is exposed behind a step wedge and color developed as usual.
  • the processed samples are then covered with a UV protective film and irradiated in a Xenotest device to determine the light fastness (40% relative humidity; 25 ° C; 100,000 Ix.h.).
  • the UV protective film was made as follows. A layer of 1.5 g of gelatin, 0.65 g of compound A (UV absorber) of the following formula was placed on a transparent cellulose triacetate film provided with an adhesive layer
  • Developer A contains 2-amino-5- (N-ethyl-N-methanesulfonamidoethylamino) toluene as a color developer.
  • Developer B contains 2-amino-5- (N-ethyl-N-hydroxyethylamino) toluene as a color developer. substance. The results (percentage decrease in color density) are shown in Table 1.
  • Example 2 The procedure was as in Example 1.
  • the following compounds were also tested, which were known as light-stabilizing agents for the purple dyes produced from pyrazolone couplers.
  • Compound S-3 also has a certain stabilizing effect on the lightfastness of the magenta and cyan dyes. Naturally, this effect is comparatively small with the already more stable cyan dyes.
  • An instant hardening agent is hardened by covering it with a 10% strength aqueous solution.
  • Recording material 1 is obtained.
  • Recording material 2 is also prepared in a corresponding manner, with the only difference that layer 1 additionally contains 0.22 g of compound S-3.
  • the yellow color parts obtained were measured and the levels of the densities 0.8 and 1.0 were marked.
  • the wedges were then irradiated in a Xenotest device with a quantity of light of 15.10 6 1x.h.
  • the marked steps were then measured again. The results are shown in the table.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (3)

1. Matériau d'enregistrement photographique en couleurs avec au moins une couche d'émulsion d'halogénure d'argent et un coupleur en couleur y associé, carctérisé en ce qu'il contient, dans une couche d'émulsion d'halogénure d'argent ou dans une couche non photosensible de liant voisine de cette dernière, une combinaison d'un coupleur en couleur et d'un composé de formule générale 1
Figure imgb0073
dans laquelle
G représente un groupe hydroxy ou un groupe instable en milieu alcalin, précurseur d'un groupe hydroxyle
X représente un substituant qui n'est pas séparé dans les conditions du développement chromogène
Y représente un reste répondant à l'une des formules suivantes:
―SO2―NR1―R2
―CO―NR1―R2
-NR'-CO-R3
―NR1―SO2―R3
(R' = hydrogène ou alkyle
R2 = alkyle, aralkyle ou aryle,
R3 = alkoxy, aroxy, alkylamino, arylamino ou un reste tel qu'indiqué pour R2);
Z représente l'hydrogène, un groupe alkyle, alcoxy, un halogène ou un groupe acylamino;
n représente 1 ou 2.
2. Matériau d'enregistrement selon la revendication 1, caractérisé en ce que le coupleur en couleur est un coupleur en jaune.
3. Matériau d'enregistrement selon la revendication 1 ou 2, caractérisé en ce que dans la formule 1 de la revendication 1, X représente un reste alkyle, alcoxycarbonyle, carbamoyle, sulfamoyle, alkylsulfonyle ou arylsulfonyle.
EP85111669A 1984-09-27 1985-09-16 Matériau d'enregistrement photographique Expired - Lifetime EP0176845B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19843435443 DE3435443A1 (de) 1984-09-27 1984-09-27 Fotografisches aufzeichnungsmaterial
DE3435443 1984-09-27

Publications (3)

Publication Number Publication Date
EP0176845A2 EP0176845A2 (fr) 1986-04-09
EP0176845A3 EP0176845A3 (en) 1988-09-21
EP0176845B1 true EP0176845B1 (fr) 1991-02-06

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US (1) US4656125A (fr)
EP (1) EP0176845B1 (fr)
JP (1) JPH0713737B2 (fr)
DE (2) DE3435443A1 (fr)

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US4745049A (en) * 1986-04-11 1988-05-17 Konishiroku Photo Industry Co., Ltd. Silver halide photographic light-sensitive material
DE3918547A1 (de) * 1989-06-07 1990-12-13 Agfa Gevaert Ag Farbfotografisches silberhalogenidmaterial
GB9010966D0 (en) * 1990-05-16 1990-07-04 Kodak Ltd Photographic material comprising a magenta dye image forming coupler combination
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EP0176845A3 (en) 1988-09-21
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EP0176845A2 (fr) 1986-04-09
JPS6186750A (ja) 1986-05-02
US4656125A (en) 1987-04-07

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