EP0032699B1 - Matériau d'enregistrement pour la photographie en couleurs contenant un composé formateur de colorant émulsionné et hydrophile - Google Patents

Matériau d'enregistrement pour la photographie en couleurs contenant un composé formateur de colorant émulsionné et hydrophile Download PDF

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Publication number
EP0032699B1
EP0032699B1 EP81100149A EP81100149A EP0032699B1 EP 0032699 B1 EP0032699 B1 EP 0032699B1 EP 81100149 A EP81100149 A EP 81100149A EP 81100149 A EP81100149 A EP 81100149A EP 0032699 B1 EP0032699 B1 EP 0032699B1
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Prior art keywords
recording material
hydrophilic
colour
material according
aliphatic
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EP81100149A
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German (de)
English (en)
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EP0032699A1 (fr
Inventor
Fritz Dr. Nittel
Hans Dr. Langen
Erwin Dr. Ranz
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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
    • G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
    • G03C8/02—Photosensitive materials characterised by the image-forming section
    • G03C8/08—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds
    • 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
    • G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor
    • G03C7/3885—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor characterised by the use of a specific solvent
    • 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

  • the invention relates to a color photographic recording material which, in association with at least one light-sensitive sitber halide emulsion layer, contains an emulsified hydrophilic coloring compound.
  • Hydrophilic color couplers and other coloring compounds are generally added to the photographic casting solutions in the form of an aqueous or aqueous-alcoholic solution.
  • the required amounts of alkali are used in the preparation of the solutions, provided the coupler is not already present in water-soluble form as the alkali salt.
  • Hydrophilic color couplers are often characterized by particularly high coupling speeds and are therefore very desirable in the production of highly sensitive color photographic recording materials.
  • serious disadvantages occur in the incorporation of hydrophilic compounds from aqueous-alkaline solution in photographic layers, insofar as the high salt content in the emulsion caused by the neutralization of the alkaline solutions causes poor flatness and high brittleness of the materials.
  • the casting solutions generally have to be diluted strongly with water in order to compensate for the increase in viscosity due to the reaction of the sulfo groups or carboxyl groups with the amino groups of the gelatin.
  • this method makes it difficult to produce layers with a desired high packing density on color couplers or other coloring compounds.
  • hydrophilic couplers are dissolved together with bisepoxides in oil paintings and dispersed in the silver halide emulsion in the presence of wetting agents.
  • hydrophilic couplers can be incorporated by emulsification, the undesirable increase in viscosity of the casting solution cannot be prevented because the bisepoxides used are gelatin hardening agents and react with the amino groups of the gelatin, which also causes an increase in viscosity.
  • the invention has for its object to provide a color photographic recording material which contains hydrophilic coloring compounds, without having the disadvantages shown above.
  • a color photographic recording material with at least one light-sensitive silver halide emulsion layer and a dispersion of a solution of a hydrophilic, non-diffusing coloring compound in an oil former which is present in it or in an adjacent, non-light-sensitive binder layer, which is characterized in that the oil former contains an aliphatic tertiary hydroxyamine in which at least two of the aliphatic groups present carry a hydroxyl group.
  • the alkylene groups mentioned (R ', R 2 ) and the alkyl or alkenyl groups (R 3 ) can be straight-chain or branched and contain, for example, methyl side groups.
  • the alkylene radicals represented by R 'and R 2 are preferably those which can be derived from the addition of ethylene oxide or propylene oxide to ammonia or primary R'-NH 2 .
  • aliphatic tertiary hydroxyamines are listed below:
  • the aliphatic tertiary hydroxyamines used according to the invention are known compounds which are referred to, for example, in Beilstein (Syst. No. 353 and 354).
  • the color photographic recording material according to the invention generally contains at least three differently spectrally sensitized silver halide emulsion layer units, each of which in turn can consist of one silver halide emulsion layer or several silver halide emulsion partial layers.
  • the color photographic recording material according to the invention contains coloring compounds, that is, compounds which provide image dyes in the course of photographic development. This includes both conventional color couplers and those compounds which, in the course of development, provide diffusing image dyes or their precursors which, after diffusion transfer, produce a color image in an image-receiving layer.
  • the color-providing compounds are selected such that the image dyes produced during processing have a color which is approximately complementary to the color of the light to which the associated silver halide emulsion layers are sensitive.
  • the color-imparting compounds assigned to the red-sensitive layers accordingly provide blue-green image dyes
  • the color-imparting compounds assigned to the green-sensitive layers provide purple-colored image dyes
  • those to the blue-sensitive ones Colored compounds assigned to layers provide yellow image dyes.
  • “Assignment” and “assigned” is understood to mean that the mutual arrangement of the silver halide emulsion layer and coloring compound is of such a nature that an interaction between them is possible, on the one hand an image-like correspondence between the silver image formed or the image-based distribution of the undeveloped silver halide and on the other hand allows the image-wise distribution of image dye formed. This is generally achieved by incorporating the coloring compound either in a light-sensitive silver halide emulsion layer itself or in a non-light-sensitive binder layer adjacent to it. Separating layers can be arranged between silver halide emulsion layer units of different spectral sensitivity, each of which comprises at least one silver halide emulsion layer and at least one coloring compound assigned to it.
  • the coloring compounds are introduced into the respective layers in a non-diffusing form.
  • This can be done by the usual incorporation methods, whereby hydrophilic coloring compounds are added mainly in the form of aqueous alkaline solutions and hydrophobic coloring compounds mainly in emulsified form using oil paintings.
  • the color photographic recording material now contains, in association with at least one silver halide emulsion layer, a non-diffusing, hydrophilic coloring compound in emulsified form.
  • coloring is considered to be those coloring compounds which, because of their content of alkali-solubilizing groups, are too insoluble in the organic auxiliary solvents used in the incorporation, such as ethanol, ethyl acetate, diethyl carbonate, and above all in the oil images under consideration have to allow the formation of stable Emulgate.
  • These couplers generally have an excessively high tendency to crystallize in the finished emulsified or in the emulsified form in the cast layer, if it is possible at all to get them in organic solution, which results in a clouding of the layer and a marked deterioration in the photographic properties. in particular the achievable maximum color density.
  • tertiary aliphatic hydroxyamines used according to the invention which presumably react with the alkali-solubilizing groups to form tertiary organic ammonium salts, it is possible to significantly reduce the hydrophilicity of the coloring compounds and thus to decisively improve the solubility in the organic auxiliary solvents and the oil former.
  • Particularly suitable hydrophilic coloring compounds are those which contain a sulfo group and / or one or more other alkali-solubilizing groups such as carboxyl groups (-COOH) or sulfonamide groups (-NH-S0 2 -) in their molecule.
  • the incorporation method according to the invention is equally suitable for incorporating non-diffusing color couplers, from which non-diffusing image dyes are produced by the chromogenic development process, as well as for non-diffusing coloring compounds for the color diffusion transfer process, from which diffusing dyes are released during photographic processing.
  • the color couplers used according to the invention can be either conventional 4-equivalent couplers or 2-equivalent couplers, in which a smaller amount of silver halide is required 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 additionally 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.
  • Known white couplers are also to be counted among the 2-equivalent couplers, but they do not give any dye on reaction with color developer oxidation products.
  • the 2-equivalent couplers include the known DIR couplers, which are couplers that contain a removable residue in the coupling site, which is released as a diffusing development inhibitor when reacted with color developer oxidation products.
  • the non-diffusing, diffusing dyes liberating coloring compounds which can also be incorporated by the method according to the invention, are compounds in which a potentially diffusible dye or dye precursor residue is bound to a carrier residue afflicted with a diffusion-proofing group, such compounds being present by the presence a sulfo group or one or two other alkali solubilizing groups so hy are drophilic that they cannot be emulsified by the usual methods.
  • the carrier residues mentioned are of such a type that they release either a predominantly in oxidized form or predominantly in non-oxidized form, or as a result of a coupling with developer oxidation products, a diffusing dye residue.
  • hydrophilic coloring compounds which according to the invention can be present in emulsified form in the layers of the color photographic recording material:
  • Suitable oil formers are the customary, more or less hydrophobic, high-boiling compounds also known as coupler solvents, as described, for example, in US-A-2322027. Special mention should be made here, for example, of dibutyl phthalate (OF-1) and tricresyl phosphate (OF-2).
  • oil formers containing carboxyl groups can also be used, e.g. B.
  • the at least one carboxyl group-containing succinic acid derivatives of US-A-3689271, US-A-3 764336 and US-A-3 765 897 are given below as oil formers OF-3 to OF-10.
  • oil formers OF-3 to OF-10 are given below as oil formers OF-3 to OF-10.
  • the oil formers can also have a clearly hydrophilic character in the presence of carboxyl groups, as the example of the last-mentioned compounds shows, it is a common feature of all oil formers that they form a second separate phase in the form of small droplets when incorporated into a hydrophilic colloid binder which is retained in the alkaline medium even under the conditions of photographic development.
  • the oil formers are used in an amount of 0.1 to 2 parts by weight, preferably about 1 part by weight, per part by weight of hydrophilic coloring compounds. Particular advantages are obtained according to the invention in particular when the oil former used has a free carboxyl group and a part of the molecule which shows a certain structural similarity to the tertiary aliphatic hydroxyamine used according to the invention.
  • Such oil formers which are used with particular preference in accordance with the invention can be obtained by reacting ⁇ -alkyl succinic anhydride with tertiary aliphatic hydroxyamines of the formula (I). Oil formers of this type are also described in US-A-3,689,271. Examples of such oil formers are contained in the following formula collection as oil formers OF-3 to OF-8.
  • the coloring compounds together with at least one compound of the formula (I) and the oil former under consideration are expediently first in an organic auxiliary solvent such as ethanol, ethyl acetate, diethyl carbonate, acetone or mixtures thereof.
  • an organic auxiliary solvent such as ethanol, ethyl acetate, diethyl carbonate, acetone or mixtures thereof.
  • a mixture of 80 parts of ethyl acetate and 20 parts of ethanol or a mixture of 80 parts of diethyl carbonate and 20 parts of ethanol has proven to be advantageous.
  • the amount of tertiary aliphatic hydroxyamine required generally depends on the number of alkali-solubilizing groups in the hydrophilic coloring compound and can be easily determined by simple experiments.
  • Optimal results are obtained, for example, if the tertiary aliphatic hydroxyamine is used in 0.5 to 2 times the motar amount of the hydrophilic coloring compound used.
  • the oil former is used in an amount of 0.1 to 2 parts by weight per part by weight of hydrophilic coloring compound.
  • the organic solution obtained is in a hydrophilic colloid, for. B. emulsified in a silver halide emulsion or in a gelatin solution which can be added to a silver halide emulsion at a later point in time or, if appropriate, is poured into a non-light-sensitive layer after admixing further substances.
  • hydrophilic coloring compounds in emulsified form.
  • the invention thus also allows hydrophilic and hydrophobic coloring compounds, e.g. B. hydrophilic and hydrophobic color couplers, side by side in the form of a common emulsifier.
  • the bracketed values in Table 1 are viscosity values which were measured in the same way on the pure emulsions (without admixing the silver halide emulsion).
  • 200 ml of a 5% aqueous alkaline solution of the coupler CP-3 were mixed with 100 ml of 10% gelatin solution; pH 6.4.
  • the development was carried out in a conventional manner using N-butyl-N- ⁇ -sulfobutyl-p-phenylenediamine as the developer substance.
  • a corresponding material was produced with the alkaline coupler CP-3. A sample of each of the materials thus produced was exposed and developed in the fresh state and a second sample after storage (2 days; 60 ° C.; 60% relative atmospheric humidity).
  • the maximum color density Dmax and the density loss A Dmax during storage are given in Table 2.
  • Emulsifier of a hydrophilic and a hydrophobic yellow coupler Emulsifier of a hydrophilic and a hydrophobic yellow coupler.
  • Yellow coupler X is a hydrophobic yellow coupler of the formula:
  • the oil phase obtained was emulsified in 1000 ml of a 5% gelatin solution with 0.5 g of Na-dodecylbenzenesulfate, mixed with a silver halide emulsion with an AgNO 3 / coupler ratio of 1: 1.5 and poured onto a paper support; Silver coating 0.54 g AgNO 3 / m 2 .
  • the maximum color densities shown in Table 3 were measured. In this example, optimal color yield is obtained at a coupler ratio of 20:80 (hydrophilic / hydrophobic).
  • Emulsifier of a hydrophilic and a hydrophobic magenta coupler Emulsifier of a hydrophilic and a hydrophobic magenta coupler.
  • 50 g of the hydrophobic coupler Y were dissolved in 160 ml of diethyl carbonate and 50 g of tricresyl phosphate (OF-2).
  • the solution obtained was emulsified in 500 ml of a 10% gelatin solution with the addition of 25 g of a 10% solution of sodium alkylnaphthalene sulfonate.

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

Claims (7)

1. Elément d'enregistrement de photographie en couleurs comportant au moins une couche d'émulsion photosensible à l'halogénure d'argent et, en une dispersion située dans cette couche ou dans une couche voisine d'un agent liant non photosensible, une solution d'un composé chromogène hydrophile non diffusible dans un agent formateur d'huile, caractérisé en ce que l'agent formateur d'huile contient une hydroxylamine aliphatique tertiaire dans laquelle au moins deux des groupes aliphatiques présents comportent un groupe hydroxy.
2. Elément d'enregistrement suivant la revendication 1, caractérisé en ce que l'hydroxylamine aliphatique tertiaire répond à la formule suivante:
Figure imgb0041
dans laquelle
R' et R2 représentent des groupes alkylène identiques ou différents, éventuellement interrompus par des atomes d'oxygène et contenant 1 à 4 atomes de carbone, et
R3 représente un groupe alkyle ou alcényle éventuellement interrompu par des atomes d'oxygène, contenant 1 à 18 atomes de carbone et éventuellement substitué par un groupe hydroxy.
3. Elément d'enregistrement suivant la revendication 1, caractérisé en ce que le composé chromogène hydrophile contient un groupe sulfo et/ou un ou deux groupes carboxy (-COOH) ou sulfonamido (-NH-S02-).
4. Elément d'enregistrement suivant la revendication 1, caractérisé en ce que l'hydroxylamine aliphatique tertiaire est présente en une quantité molaire égale à 0,5-2 fois celle du composé chromogène hydrophile.
5. Elément d'enregistrement suivant la revendication 1, caractérisé en ce que le composé chromogène hydrophile est un copulant chromogène hydrophile.
6. Elément d'enregistrement suivant la revendication 5, caractérisé en ce que, outre le copulant chromogène hydrophile et l'hydroxylamine aliphatique tertiaire, un copulant chromogène hydrophobe est dissous dans l'agent formateur d'huile.
7. Elément d'enregistrement suivant la revendication 1, caractérisé en ce que l'agent formateur d'huile est un produit réactionnel d'une hydroxylamine aliphatique tertiaire dans laquelle au moins deux des groupes aliphatiques présents comportent un groupe hydroxy, avec un anhydride d'acide succinique comportant, en position a, un radical aliphatique conférant une résistance à la diffusion.
EP81100149A 1980-01-22 1981-01-10 Matériau d'enregistrement pour la photographie en couleurs contenant un composé formateur de colorant émulsionné et hydrophile Expired EP0032699B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3002201 1980-01-22
DE19803002201 DE3002201A1 (de) 1980-01-22 1980-01-22 Farbfotografisches aufzeichnungsmaterial mit einer emulgierten hydrophilen farbgebenden verbindung

Publications (2)

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EP0032699A1 EP0032699A1 (fr) 1981-07-29
EP0032699B1 true EP0032699B1 (fr) 1982-11-10

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EP81100149A Expired EP0032699B1 (fr) 1980-01-22 1981-01-10 Matériau d'enregistrement pour la photographie en couleurs contenant un composé formateur de colorant émulsionné et hydrophile

Country Status (5)

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US (1) US4368259A (fr)
EP (1) EP0032699B1 (fr)
JP (1) JPS56106245A (fr)
CA (1) CA1155702A (fr)
DE (2) DE3002201A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3130079A1 (de) * 1981-07-30 1983-02-17 Agfa-Gevaert Ag, 5090 Leverkusen Farbfotografisches aufzeichnungsmaterial
JPH0614176B2 (ja) * 1984-07-09 1994-02-23 コニカ株式会社 ハロゲン化銀カラ−写真感光材料
JPS628148A (ja) * 1985-07-04 1987-01-16 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料
JPH07119986B2 (ja) * 1987-05-15 1995-12-20 富士写真フイルム株式会社 ハロゲン化銀感光材料
EP0550359A1 (fr) * 1991-12-30 1993-07-07 Eastman Kodak Company Méthode pour la formation de matériaux photographiques en couleur ayant une grande reactivité pour le couplage et une sensibilité réduite du pH du révélateur couleur
JPH06273907A (ja) * 1993-03-18 1994-09-30 Fuji Photo Film Co Ltd カラー拡散転写感光材料

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3335011A (en) * 1962-03-23 1967-08-08 Pavelle Corp Production of stabilized dispersions of color couplers for photographic materials
DE1772192C2 (de) * 1968-04-11 1983-03-17 Agfa-Gevaert Ag, 5090 Leverkusen Verfahren zur Herstellung von lichtempfindlichen und nicht lichtempfindlichen Schichten für photographische Aufzeichnungsmaterialien
DE2042659A1 (de) * 1970-08-28 1972-03-02 Agfa-Gevaert Ag, 5090 Leverkusen Einlagerungsverfahren
DE2049689A1 (de) * 1970-10-09 1972-07-20 Agfa-Gevaert Ag, 5090 Leverkusen Einlagerungsverfahren
US4252894A (en) * 1975-10-22 1981-02-24 Gaf Corporation Hydrophilic color coupler composition containing diepoxide

Also Published As

Publication number Publication date
CA1155702A (fr) 1983-10-25
EP0032699A1 (fr) 1981-07-29
US4368259A (en) 1983-01-11
DE3002201A1 (de) 1981-07-23
JPS56106245A (en) 1981-08-24
DE3160006D1 (en) 1982-12-16

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