EP0345839A1 - Einen Purpurfarbstoff freisetzende Verbindungen - Google Patents

Einen Purpurfarbstoff freisetzende Verbindungen Download PDF

Info

Publication number
EP0345839A1
EP0345839A1 EP89201201A EP89201201A EP0345839A1 EP 0345839 A1 EP0345839 A1 EP 0345839A1 EP 89201201 A EP89201201 A EP 89201201A EP 89201201 A EP89201201 A EP 89201201A EP 0345839 A1 EP0345839 A1 EP 0345839A1
Authority
EP
European Patent Office
Prior art keywords
dye
silver halide
group
releasing compound
image
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.)
Withdrawn
Application number
EP89201201A
Other languages
English (en)
French (fr)
Inventor
Wilhelmus Janssens
Luc Jerome Vanmaele
Immo Boie
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 NV
Original Assignee
Agfa Gevaert NV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Agfa Gevaert NV filed Critical Agfa Gevaert NV
Publication of EP0345839A1 publication Critical patent/EP0345839A1/de
Withdrawn legal-status Critical Current

Links

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
    • G03C8/10—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds of dyes or their precursors

Definitions

  • the present invention relates to a process for the production of diffusion transfer images with non-diffusible magenta dye-releasing compounds, to such dye-releasing compounds, and to photographic elements incorporating them.
  • Dye diffusion transfer imaging can be carried out in a number of ways but all dye diffusion transfer imaging systems are based on the same principle of modifying the solubility of the dyes as a function of the amount of photosensitive silver halide developed.
  • the dye-image-producing compounds are either initially mobile in alkaline aqueous media and become immobilized during processing, or initially immobile and become mobilized during processing.
  • a dye-developer system based on redox-controlled solubility change (ref. e.g. US-A 2 983 606) was the first commercially introduced dye diffusion transfer system.
  • Oxidizable dye-releasing compounds that after oxidation release a dye moiety by hydrolysis are known, e.g., from DE-A 2,242,762, DE-A 2,406,664, DE-A 2,505,246, DE-A 2,613,005, DE-A 2,645,656 and Research Disclosure publications Nos. 15,157 (November 1976), 16,654 (April 1977) and 17,736 (January 1979).
  • dye-releasing compounds are described in which the dye moiety is linked most frequently to an oxidizable carrier moiety through a sulphonamido group. The dye released from such compounds thus contains a sulphamoyl group.
  • Oxidizable dye-releasing compounds that in oxidized form release a dye moiety by intramolecular displacement reaction are described, e.g. in US-A 3,443,940.
  • the dye released from these compounds contains a sulphinate group.
  • Oxidizable dye-releasing compounds that in oxidized form are stable but in reduced state set free a dye moiety by an elimination reaction are described in DE-A 2,823,159 and DE-A 2,854,946.
  • Compounds of this type can be used in reduced form in an unexposed silver halide emulsion material and can be called IHO-compounds, IHO being an acronym for "Inhibited Hydrolysis by Oxidation".
  • IHR-compounds Reducible dye-releasing compounds that after reduction set free a dye moiety
  • IHR Reducible dye-releasing compounds that after reduction set free a dye moiety
  • Reducible quinone-type IHR-compounds which after reduction can undergo a dye release with an intramolecular nucleophilic displacement reaction, are described in DE-A 2,809,716 wherein these compounds are called BEND-compounds, BEND standing for "Ballasted Electron-accepting Nucleophilic Displacement".
  • Particularly useful dye-releasing compounds are the redox-controlled dye-releasing compounds, which can be represented by: BALL-REDOX-DYE wherein : BALL represents a moiety with ballast residue for immobilizing the dye-releasing compound in a hydrophilic colloid layer, REDOX represents a redox-active group, i.e. a group that under the circumstances of alkaline silver halide development is oxidizable or reducible and depending on the oxidized or reduced state brings about a dye release by an elimination reaction,nucleophilic displacement reaction, hydrolysis, or cleavage reaction, DYE represents a diffusible dye moiety or a precursor thereof.
  • Coloured compounds for use in a dye diffusion transfer process include e.g. triphenylmethane, xanthene, azo, azomethine, anthraquinone, alizarine, merocyanine, quinoline or cyanine dye structures.
  • a mono-azo-dye group as described e.g. in US-A 3,725,062.
  • colour couplers which are capable of forming azomethine dyes derived from pyrazolo-azoles by reaction with an oxidized aromatic primary amino developing agent.
  • colour couplers which are capable of forming azomethine dyes derived from pyrazolo-azoles by reaction with an oxidized aromatic primary amino developing agent.
  • (CAR-L1-) moieties from which in oxidized form by a non-chromogenic reaction in alkaline medium a dye moiety can be split off, can be selected from e.g. the following groups including such groups in substituted form:
  • brackets are released together with the dye moiety (not represented), and remain with the dye moiety as groups promoting diffusion.
  • the dye release proceeds directly proportionally to the rate of formation of the oxidation products of developing agent used in the development of silver halide.
  • Said compounds are therefore negative-working in that they undergo dye release in correspondence with the exposed portions of a negative-working silver halide emulsion layer.
  • an image reversal is needed, which may be based on the use of positive-working layers containing a direct-positive silver halide emulsion or on the silver salt complex diffusion transfer process by selection of a proper layer assemblage as described e.g. in EP-A 0,003,376.
  • (CAR-L1-) moieties from which in alkaline medium a dye moiety can be set free after reduction, can be selected from the following groups including such groups in substituted form:
  • the groups within brackets are functional groups that are split off together with the dye moiety (not shown). These functional groups can be separated from the chromophoric group of the dye by a linking member having no influence on the absorption properties of the dye.
  • the functional group may be of importance to determine the diffusion-mobility and/or capability of the released dye to be mordanted.
  • Useful linking members are, e.g., alkylene and arylene groups.
  • Ballast groups that confer resistance to diffusion are groups that allow the compounds according to the present invention to be incorporated in non-diffusing form in the hydrophilic colloids customarily used in photographic elements.
  • Organic groups which generally carry straight-chain or branched-chain aliphatic groups and also isocyclic or heterocyclic or aromatic groups mostly having from 8 to 20 carbon atoms are preferred for this purpose. These groups are attached either directly or indirectly e.g. through one of the following groups : -NHCO-; -NHSO2-; -NR-, in which R represents hydrogen or alkyl; -O-; -S-; or -SO2-.
  • the group conferring resistance to diffusion may additionally carry groups that confer solubility in water, e.g.
  • sulpho groups or carboxy groups may also be present in anionic form. Since the diffusion properties depend on the molecular size of the compound as a whole, it is sufficient in certain cases, e.g. when the molecule has a considerable size, to use one or more short-chain groups as groups conferring resistance to diffusion or to use no such group at all.
  • magenta dye-releasing compounds are quinone-type IHR-compounds, from which a diffusible magenta dye moiety is released by reduction and hydrolysis.
  • BALLAST stands for a ballasting group making the compound non-diffusing in a hydrophilic colloid medium under wet alkaline conditions, such as a long-chain alkyl group e.g. n-hexadecyl.
  • BALLAST may stand for i.a. a lower alkyl group e.g. methyl.
  • diffusible as used herein stands for "having the property of diffusing effectively through colloid layers of photographic elements in alkaline liquid medium.
  • mobile has the same meaning.
  • non-diffusible and immobile have the opposite meaning.
  • magenta dye-releasing compounds for use in the process according to the present invention are listed in the following Table 1.
  • the dye-releasing compounds 2, 3, and 4 can be prepared as described for dye-releasing compound 1 with the only difference that instead of 2-amino-5-diethylaminotoluene hydrochloride (Compound (1.d)) the following compounds are used respectively: - N-ethyl-N-(Beta-hydroxy-ethyl)-m-toluidine sulphate, - 4-amino-N-ethyl-N-(Beta-methylsulphonamido-ethyl)-m-toluidine sesquisulphate monohydrate, and - N,N-dimethyl-p-phenylene diamine hydrochloride.
  • Compound (1.d) 2-amino-5-diethylaminotoluene hydrochloride
  • Pyrazolo-azole and imidazo-azole intermediate compounds e.g. Compound (1.b) and starting compounds needed for preparing these can be synthesized as described in DE Patent Application N° 3,610,702, which corresponds to the US Serial N° ........ .
  • dye-releasing compounds for use in accordance with the present invention and corresponding to the above general formula I can be prepared analogously or by techniques known in the art starting with the appropriate chemicals i.e. with the proper carrier part intermediates and the dye part intermediates that are specific for the present invention.
  • the compounds according to the present invention are useful in a dye diffusion transfer process and for that purpose are used in operative association with a photosensitive silver halide emulsion layer, preferably of the negative-working type, i.e. of the type giving a silver image in the photo-exposed areas.
  • a photographic element for dye image production comprises a support carrying at least one photosensitive alkali-permeable hydrophilic colloid silver halide emulsion layer and in operative association therewith at least one dye-releasing compound, characterized in that said dye-releasing compound corresponds to the above general formula I.
  • operative association is meant that the release of the diffusible magenta azomethine dye from the dye-releasing compound can proceed in dependence on and as a function of the development of the silver halide emulsion layer.
  • the dye-releasing compound need not be present in the silver halide emulsion layer itself but may be contained in another layer that is in water-permeable relationship therewith.
  • the present invention also provides a photographic element that comprises a support carrying (1) a red-sensitive silver halide emulsion layer having operatively associated therewith a dye-releasing compound that initially is non-diffusing in an alkali-permeable colloid medium and from which, inversely proportional to the development of the image-wise exposed silver halide by a silver halide developing agent in alkaline conditions and a redox-reaction, a cyan dye is split off in diffusible state, (2) a green-sensitive silver halide emulsion layer having operatively associated therewith a dye-releasing compound corresponding to the above general formula I, which dye-releasing compound is initially non-diffusing in an alkali-permeable colloid medium and from which, inversely proportional to the development of the image-wise exposed silver halide by a silver halide developing agent in alkaline conditions and a redox-reaction, a magenta azomethine dye is
  • magenta azomethine dyes of pyrazolo-azoles and imidazo-azoles split off in diffusible state from the dye-releasing compounds of the present invention have a very satisfactory absorption in the green part of the spectrum and at the same time low side-absorptions in the orange-red part and especially in the blue-violet part of the spectrum.
  • the dye group(s) may be associated with substituents that form a shifted dye.
  • Shifted dyes as described in e.g. US-A 3,260,597 include compounds, the light-absorption characteristics of which are found to be shifted hypsochromically or bathochromically when subjected to a different environment such as a change of the pK a of the compound, or removal of a group such as a hydrolyzable acyl group linked to an atom of the chromophoric system and affecting the chromophore resonance structure.
  • the shifted dyes can be incorporated directly in a silver halide emulsion layer or even on the exposure side thereof without substantial absorption of light used in recording. After exposure, the dye is shifted to the appropriate colour, e.g. by hydrolytic removal of said acyl group.
  • the colour diffusion transfer process in accordance with the present invention is carried out preferably in conjunction with a mixture of reducing agents, at least one of which is a compound called electron-donor (ED-compound) and at least one of which is a compound called electron-transfer agent (ETA-compound).
  • ED-compound electron-donor
  • ETA-compound electron-transfer agent
  • the ED-compound is preferably non-diffusing.
  • it preferably carries a ballasting group, so that it remains within the layer(s), in which it has to transfer an electron to the quinone-type compound.
  • a non-diffusing ED-compound is incorporated into each silver halide emulsion layer that contains a non-diffusing IHR-quinone-­type compound.
  • suitable ED-compounds are ascorbyl palmitate and 2,5-bis-(1′,1′,3′,3′-tetramethylbutyl)-hydroquinone.
  • Other ED-compounds have been disclosed in US-A 4,139,379 and in published DE-A 2,947,425.
  • an electron-donor precursor compound EDP-compound
  • ETA-compounds include hydroquinone compounds, aminophenol compounds, catechol compounds, phenylene diamines, and 3-pyrazolidinones such as e.g. 1,4-dimethyl-3-pyrazolidinone, 4-methyl-­3-pyrazolidinone, 4,4-dimethyl-3-pyrazolidinone, 1-(2-trifluoroethyl)-­4,4-dimethyl-3-pyrazolidinone, and 5-methyl-3-pyrazolidinone, and especially 1-aryl-3-pyrazolidinone compounds such as e.g.
  • the above-mentioned ETA-compounds or combinations thereof can be contained in the liquid processing composition or can be contained at least partially in any hydrophilic colloid layer or layers of the photographic element e.g. the photosensitive silver halide emulsion layer(s), interlayers, or in the image-receiving layer.
  • the above-mentioned 1-aryl-­3-pyrazolidinones are very appropriate representatives.
  • several representatives of these 1-aryl-3-pyrazolidinones have a poor solubility in aqueous compositions or solutions.
  • ETA-compounds having a poor solubility were incorporated in the form of a dispersion into hydrophilic colloid layer compositions, the dispersion usually being made in a sand mill or a ball mill.
  • this method of working often brought about a deterioration of certain photographic characteristics in that it caused fogging and gave rise to losses in speed, density, and gradation.
  • the above-mentioned 1-aryl-­3-pyrazolidinones can be dispersed with the aid of at least one known oil-former such as an alkyl ester of phthalic acid e.g. dibutyl phthalate or a phosphoric acid ester e.g. tricresyl phosphate or any other oil-former such as those described in EP-A 0,176,628, which corresponds with the US Serial N° 06/780,585, in EP-A 86-202066.6, which corresponds with the US Serial N° 07/110,798, in US-A 4,430,422, or in the literature referred to in the above documents.
  • an oil-former such as an alkyl ester of phthalic acid e.g. dibutyl phthalate or a phosphoric acid ester e.g. tricresyl phosphate or any other oil-former such as those described in EP-A 0,176,628, which corresponds with the US Serial N° 06/780,
  • the above-mentioned 1-aryl-3-pyrazolidinone ETA-compounds can be incorporated successfully into a hydrophilic colloid layer by dissolving them in at least oil-type-solvent or oil-former, adding the resulting solution to an aqueous phase containing gelatin and a dispersing agent, passing the mixture through a homogenizing apparatus so that a dispersion of the oily solution in an aqueous medium is formed, mixing the dispersion with a hydrophilic colloid composition, and coating the resulting composition in the usual manner.
  • the dissolution of the coupler in the oil-former may be facilitated by the use of an auxiliary low-boiling water-immiscible solvent e.g. a lower alkyl acetate, which is removed afterwards by evaporation.
  • the auxiliary solvent can also be a water-soluble organic solvent e.g. methanol.
  • the selection of the specifically used ETA-compound(s) is, of course, determined by the particular electron-donor and dye-releasing compound used in the process and the processing conditions for the particular photographic element.
  • the concentration of ED-compound or EDP-compound in the photographic element may vary within a broad range but is in the molar range of e.g. 1:1 to 8:1 in respect of the dye-releasing compound.
  • the ETA-compound may be present in the alkaline aqueous liquid used in the development step, but is preferably present in a non-photosensitive hydrophilic colloid layer adjacent to at least one silver halide emulsion layer.
  • a silver halide solvent e.g. thiosulphate
  • a silver halide solvent is used to mobilize unexposed silver halide in complexed form for helping to neutralize (i.e. oxidize by physical development) such excess unoxidized developing agent in the photo-exposed areas where unaffected developing agent (ETA-compound) should no longer be available for entering into reaction with the dye-releasing compound directly or through the applied ED-compound.
  • scavengers can be used for such interception. They can be incorporated in non-diffusible state into the photographic element, e.g. in interlayers between the imaging layers. Suitable scavengers for that purpose have been described in e.g. US-A 4,205,987 and EP-A 0,029,546.
  • the dye-releasing compounds and optionally ED-compounds or EDP-compounds can be incorporated into the photographic element by addition to the coating composition(s) of at least one layer thereof. They can be added according to usual methods e.g. according to methods known for incorporating colour couplers into silver halide emulsion elements.
  • the amount of dye-releasing compound coated per m2 may vary within wide limits and depends on the maximum colour density desired.
  • the support of the photographic elements used according to the present invention may be of any material as long as it is dimensionally stable and does not adversely affect the photographic properties of the elements.
  • Typical flexible sheet materials for forming the support are paper e.g. single-side or twin-side Alpha-olefin-polymer-coated paper such as polyethylene-coated paper and polypropylene-coated paper.
  • Other flexible sheet support materials are e.g. cellulose nitrate film, cellulose acetate film, polyvinyl acetal film, polystyrene film, polyethylene terephthalate film, polycarbonate film, and related films or resinous materials.
  • the support usually has a thickness of approximately 0.05 to 0.15 mm.
  • the image-receiving layer can form part of a separate image-receiving element or form an integral part of the silver halide emulsion element.
  • an alkali-permeable light-shielding layer e.g. a layer containing white pigment particles is applied customarily between the image-receiving layer and the silver halide emulsion layer(s).
  • any material can be employed as image-receiving layer in dye diffusion transfer photography, provided it performs the desired function of mordanting or otherwise fixing the diffused dye(s).
  • the selection of the particular material to be used is, of course, determined by the nature of the dye(s) to be mordanted.
  • the image-receiving layer can be composed of or contain basic polymeric mordants such as polymers of amino-guanidine derivatives of vinyl methyl ketone such as described in US-A 2,882,156 of Louis M.Minsk, issued April 14, 1959, and basic polymeric mordants and derivatives, e.g.
  • Suitable mordanting binders include e.g. guanylhydrazone derivatives of acyl styrene polymers as described in e.g. published DE-A 2,009,498 filed February 28, 1970 by Agfa-Gevaert A.G. In general, however, other binders e.g.
  • Effective mordanting compositions are long-chain quaternary ammonium or phosphonium compounds or ternary sulphonium compounds, e.g. those described in US-A 3,271,147 of Walter M.Bush and 3,271,148 of Keith E.Whitmore, both issued September 6, 1966, and cetyltrimethyl-ammonium bromide.
  • non-polymeric phosphonium compounds may be recommendable to prevent them from bleeding out of the image-receiving layer during storage thereof and especially during storage at increased temperature and high relative humidity.
  • a stabilizer for the mordanting agent is added to the composition of the image-receiving layer.
  • An appropriate stabilizer is e.g. co(n-butyl acrylate/2-acrylamido-2-methyl-propane sulphonic acid) (80/20 % parts by weight and 84/16 mol %).
  • Certain metal salts and their hydroxides that form sparingly soluble compounds with the acid dyes can also be used as dye mordants.
  • the dye mordants are dispersed in one of the usual hydrophilic binders for the image-receiving layer, e.g. in gelatin, polyvinyl pyrrolidone, or partly or completely hydrolysed cellulose esters.
  • the image-receiving layer which preferably is permeable to an alkaline solution, is transparent and has a thickness of approximately 4 to 10 ⁇ m.
  • the image-receiving layer can also contain other additives such as ultraviolet-absorbing substances to protect the mordanted dye images from fading, brightening agents e.g. stilbenes, coumarins, triazines, oxazoles, or dye stabilizers such as the chromanols and alkyl-phenols.
  • the stability to light of a dye image formed in the image-receiving layer of an image receptor element is usually better, when the pH-value in the dye image remains alkaline.
  • the pH-value of the dye image in the image-receiving layer is usually lowered to avoid any further diffusion of dyes to the white image areas.
  • the pH of the layer can within a short time after imbibition be lowered from about 14 - 13 to 11 but preferably to 7 - 5.
  • polymeric acids as disclosed in US-A 3,362,819, or solid acids or metal salts e.g.
  • the acid for lowering the pH can be incorporated into a layer, which can be coated with an inert timing or spacer layer that times or controls the pH-reduction proportionally to the rate, at which alkali diffuses through this inert spacer layer.
  • timing layers include gelatin, polyvinyl alcohol, or any of the colloids disclosed in US-A 3,455,686.
  • the timing layer can be effective in evening out the reaction rates over a wide range of temperatures. For instance, premature pH-reduction is prevented, when imbibition is effected at temperatures above room temperature, e.g. at 35° to 37°C.
  • the thickness of the timing layer is usually comprised between approximately 2.5 and 18 ⁇ m .
  • the timing layer comprises a hydrolysable polymer or a mixture of such polymers, which are hydrolysed slowly by the processing liquid.
  • hydrolysable polymers are e.g. polyvinyl acetate, polyamides, or cellulose esters.
  • An alkaline aqueous processing liquid employed in the production of dye images according to the present invention may be a conventional aqueous solution of an alkaline substance e.g. sodium hydroxide, sodium carbonate or an amine such as diethylamine.
  • an alkaline substance e.g. sodium hydroxide, sodium carbonate or an amine such as diethylamine.
  • this alkaline aqueous processing liquid has a pH above 11.
  • the alkaline aqueous processing liquid contains the diffusible developing agent that effects the reduction of the silver halide, e.g. ascorbic acid or a 3-pyrazolidinone developing agent such as 1-phenyl-4-methyl-3-pyrazolidinone.
  • the diffusible developing agent that effects the reduction of the silver halide, e.g. ascorbic acid or a 3-pyrazolidinone developing agent such as 1-phenyl-4-methyl-3-pyrazolidinone.
  • the alkaline aqueous processing liquid used in accordance with the process of the invention may also contain a desensitizing agent such as methylene blue, a nitro-substituted heterocyclic compound, or a 4,4′-bispyridinium salt, to ensure that the photographic element is not further exposed after its removal from the camera for processing.
  • a desensitizing agent such as methylene blue, a nitro-substituted heterocyclic compound, or a 4,4′-bispyridinium salt
  • the alkaline aqueous processing liquid preferably also contains a viscosity-increasing compound such as a high-molecular-weight polymer, e.g. a water-soluble ether inert to alkaline solutions such as hydroxyethylcellulose or alkali metal salts of carboxymethylcellulose e.g. sodium carboxymethylcellulose.
  • a concentration of viscosity-increasing compound of approximately 1 to 5 % by weight of the alkaline aqueous processing liquid is preferred. It imparts a viscosity of about 100 mPa.s to about 200,000 mPa.s.
  • Processing can proceed in a tray developing unit as is contained, e.g., in an ordinary silver complex diffusion transfer (DTR) apparatus, in which contact between the image-wise exposed photosensitive element and a separate dye image-receiving element is effected after sufficient absorption of processing liquid by these elements has taken place.
  • DTR silver complex diffusion transfer
  • a suitable apparatus for this purpose is the COPYPROOF CP 42 DTR-developing apparatus.
  • COPYPROOF is a trade mark of Agfa-Gevaert N.V., Antwerp, Belgium.
  • the alkaline aqueous processing liquid can be applied from at least one rupturable container, which may itself form part of said element, or by spraying.
  • rupturable containers that can be employed are those disclosed in US-A 2,543,181 of Edwin H.Land, issued February 27, 1951, 2,643,886 of Ulrich L. di Ghilini, issued June 30, 1953, 2,653,732 of Edwin H.Land, issued September 29, 1953, 2,723,051 of William J.McCune Jr., issued November 8, 1955, 3,056,492 and 3,056,491, both of John E.Campbell, issued October 2, 1962, and 3,152,515 of Edwin H.Land, issued October 13, 1964.
  • such containers comprise a rectangular sheet of fluid- and air-impervious material folded longitudinally upon itself to form two walls that are sealed to one another along their longitudinal and end margins to form a cavity in which processing liquid is contained.
  • the development temperature normally is room temperature, i.e. approximately 20 °C, but according to a particular embodiment the dye-releasing compounds according to the present invention can be used in a so-called photothermographic dye diffusion transfer method, e.g. of the type described in EP-A 0,120,306 and DE-A 3,215,485.
  • the image formation comprises image-wise exposing a light-sensitive element and heating it in the presence of a small amount of water, said element comprising a support and provided thereon light-sensitive silver halide in a binder, a reducing agent capable of reducing the light-sensitive silver halide, and at least one of the dye-releasing compounds according to the present invention.
  • a photographic element which contains a combination of silver halide and silver benzotriazolate, a developing agent, a said dye-releasing compound, and a base precursor releasing a base upon heating as described in e.g. GB-A 998,949.
  • the image-wise exposed photographic element is wet with water as the sole processing liquid and placed in contact with an image-receiving element.
  • the thus formed sandwich is subjected to heat, so that development of the exposed silver halide and transfer of image-wise released dye can take place.
  • the heat-induced development of the exposed silver halide proceeds in the presence of a thermal solvent.
  • thermal solvents examples have been described in Research Disclosure publications, October 1976, item 15 027, November 1976, item 15 108 and June 1978 item 17 029, in DE-OS 3 529 930 and 3 529 934 and in EP-A 119,615 and 112,512.
  • Thermal solvents are solid at room temperature (20°C) but play the role of a good solvent for water-soluble compounds in molten form by their relatively strong dipole moment.
  • a number of photographic elements were prepared as follows. Strips of subbed polyethylene terephthalate support having a thickness of 0.1 mm were coated with the following layers in the given order: 1) an alkali-permeable photosensitive silver halide hydrophilic colloid emulsion layer containing: gelatin 2.0 g AgCl expressed as AgNO3 0.6 g magenta dye-releasing compound as defined in Table 2 0.36 mmol/m2 ED-compound corresponding to structural formula XIII 0.3 g 2) protective layer containing: gelatin 2.5 g 1-phenyl-4-methyl-pyrazolidin-3-one 0.250 g
  • magenta dye-releasing compounds 1, 2, 3, and 6 of the present invention For comparison with the magenta dye-releasing compounds 1, 2, 3, and 6 of the present invention the following magenta dye-releasing compound (called Comparison hereinafter) disclosed in US-A 4,496,645 and corresponding to the following structural formula was entered in the test:
  • Each strip was exposed image-wise, placed in contact with a COPYCOLOR CCP image-receiving element, and together fed through a CP 38 diffusion transfer processing apparatus containing in its tray a COPYCOLOR CC 292 bath.
  • COPYCOLOR and CP 38 are trade marks of Agfa-Gevaert N.V., Antwerp, Belgium.
  • the contact time was 60 s.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
EP89201201A 1988-06-07 1989-05-12 Einen Purpurfarbstoff freisetzende Verbindungen Withdrawn EP0345839A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP88201154 1988-06-07
EP88201154 1988-06-07

Publications (1)

Publication Number Publication Date
EP0345839A1 true EP0345839A1 (de) 1989-12-13

Family

ID=8199802

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89201201A Withdrawn EP0345839A1 (de) 1988-06-07 1989-05-12 Einen Purpurfarbstoff freisetzende Verbindungen

Country Status (2)

Country Link
EP (1) EP0345839A1 (de)
JP (1) JPH0229646A (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5238797A (en) * 1991-08-26 1993-08-24 Konica Corporation Silver halide color photographic light-sensitive material containing a 1-pentahalogenophenyl-substituted 5-pyrazolone colored magenta coupler
WO1994003835A1 (en) * 1992-07-31 1994-02-17 Polaroid Corporation Thermally developable photosensitive material

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3698897A (en) * 1971-07-06 1972-10-17 Eastman Kodak Co Diffusion transfer processes and film units comprising compounds which are cleavable upon oxidation in alkali media to produce diffusible dyes or dye precursors
US4183753A (en) * 1977-08-05 1980-01-15 Eastman Kodak Company Photographic products and processes employing metal complexed azo dyes
EP0012908A2 (de) * 1978-12-20 1980-07-09 Agfa-Gevaert AG Fotografisches Farbdiffusionsübertragungsverfahren und hierfür geeignetes fotografisches Aufzeichnungsmaterial
GB2061537A (en) * 1979-07-26 1981-05-13 Kodak Ltd Photographic colour diffusion transfer processes of reproduction and developers therefor
JPS59231539A (ja) * 1983-06-14 1984-12-26 Konishiroku Photo Ind Co Ltd 熱現像カラ−拡散転写感光材料

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3698897A (en) * 1971-07-06 1972-10-17 Eastman Kodak Co Diffusion transfer processes and film units comprising compounds which are cleavable upon oxidation in alkali media to produce diffusible dyes or dye precursors
US4183753A (en) * 1977-08-05 1980-01-15 Eastman Kodak Company Photographic products and processes employing metal complexed azo dyes
EP0012908A2 (de) * 1978-12-20 1980-07-09 Agfa-Gevaert AG Fotografisches Farbdiffusionsübertragungsverfahren und hierfür geeignetes fotografisches Aufzeichnungsmaterial
GB2061537A (en) * 1979-07-26 1981-05-13 Kodak Ltd Photographic colour diffusion transfer processes of reproduction and developers therefor
JPS59231539A (ja) * 1983-06-14 1984-12-26 Konishiroku Photo Ind Co Ltd 熱現像カラ−拡散転写感光材料

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN, vol.9, no. 109 (P-355)[1832], 14th May 1985; & JP-A-59 231 539 (KONISHIROKU SHASHIN KOGYO K.K.) 26-12-1984 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5238797A (en) * 1991-08-26 1993-08-24 Konica Corporation Silver halide color photographic light-sensitive material containing a 1-pentahalogenophenyl-substituted 5-pyrazolone colored magenta coupler
WO1994003835A1 (en) * 1992-07-31 1994-02-17 Polaroid Corporation Thermally developable photosensitive material
US5316887A (en) * 1992-07-31 1994-05-31 Polaroid Corporation Thermally developable photosensitive material
US5415970A (en) * 1992-07-31 1995-05-16 Polaroid Corporation Image-recording material
US5430156A (en) * 1992-07-31 1995-07-04 Polaroid Corporation Color-providing compound having two or more cyclic 1,3 sulfur-nitrogen groups and two or more color-providing moieties

Also Published As

Publication number Publication date
JPH0229646A (ja) 1990-01-31

Similar Documents

Publication Publication Date Title
EP0292618B1 (de) Photographisches Element, das zur Verwendung in einem Farbdiffusionübertragungsverfahren Verbindungen enthält
EP0059269B1 (de) Photographische Elemente, die blockierte Farbstoffe oder blockierte Farbstoffe freisetzende Verbindungen enthalten, und Verfahren, in denen diese verwendet werden
JPH0115860B2 (de)
US4450223A (en) Diffusion transfer material and process
US4663273A (en) Non-diffusing compounds capable of releasing a diffusible dye or dye precursor compound with multiple dye units
US4605613A (en) Ballasted dye compounds with linkages containing three aromatic nuclei for use in a dye diffusion transfer process and element
GB2090990A (en) Photographic recording material
US4369243A (en) Photographic recording material for diffusion processes and useful non-diffusing sulfilimine compounds
EP0109701B1 (de) Diffusionübertragungsmaterial
CA1174671A (en) Image dye-providing materials, photographic products and processes
EP0010001B1 (de) Eine Farbstoff freisetzende Verbindung mit verschobener Absorption enthaltendes photographisches Aufzeichnungsmaterial
GB1593728A (en) Photographic light-sensitive sheet material for the colour diffusion transfer process
EP0219892B1 (de) Organische Verbindungen zur Verwendung in einem Farbstoffdiffusionsübertragungsverfahren und photographische Elemente, welche dieselben enthalten
EP0345839A1 (de) Einen Purpurfarbstoff freisetzende Verbindungen
EP0177982B1 (de) Verfahren zur Herstellung von Diffusionsübertragungsbildern mittels Purpurfarbstoff freisetzender diffusionsfester Verbindungen
US4777124A (en) Azo dye compounds for use in a dye diffusion transfer process and photographic elements incorporating them
EP0124915B1 (de) Photographisches Silberhalogenidmaterial, das eine geballastete Elektronendonor-Vorläuferverbindung enthält
US4748108A (en) Yellow dye-releasing azo compounds for use in the production of diffusion transfer color images
US4855223A (en) Organic compounds for use in a dye diffusion transfer process and photographic elements incorporating them
US4436810A (en) Color-photographic recording material containing non-diffusing electron donor precursor compounds
JPS59131932A (ja) 画像形成方法
EP0216957A1 (de) Blau-grünfarbstofffreisetzende Verbindungen zur Verwendung bei der Herstellung von Diffusions-Übertragungsfarbbildern
JPH0740131B2 (ja) カラ−写真感光材料
JPS60176039A (ja) 染料拡散転写法に使用する化合物およびそれらを混入した写真材料
JPS5834446A (ja) カラ−写真記録材料

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): BE DE FR GB

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 19900614