EP0098072B1 - Color photographic elements containing scavengers for oxidized developing agents - Google Patents

Color photographic elements containing scavengers for oxidized developing agents Download PDF

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Publication number
EP0098072B1
EP0098072B1 EP19830303424 EP83303424A EP0098072B1 EP 0098072 B1 EP0098072 B1 EP 0098072B1 EP 19830303424 EP19830303424 EP 19830303424 EP 83303424 A EP83303424 A EP 83303424A EP 0098072 B1 EP0098072 B1 EP 0098072B1
Authority
EP
European Patent Office
Prior art keywords
scavenger
silver halide
photographic element
dye
carbon atoms
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.)
Expired
Application number
EP19830303424
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0098072A2 (en
EP0098072A3 (en
Inventor
Robert Edward Ross
Wilbur Seth Gaugh
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.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
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Filing date
Publication date
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of EP0098072A2 publication Critical patent/EP0098072A2/en
Publication of EP0098072A3 publication Critical patent/EP0098072A3/en
Application granted granted Critical
Publication of EP0098072B1 publication Critical patent/EP0098072B1/en
Expired legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/392—Additives
    • G03C7/39208—Organic compounds
    • G03C7/39212—Carbocyclic
    • G03C7/39216—Carbocyclic with OH groups

Definitions

  • This invention relates to color photographic elements containing scavengers for oxidized developing agents.
  • a color photographic element comprising a support, at least one silver halide emulsion layer and a scavenger for oxidized developing agent, characterized in that the scavenger is a 2,4-disulfonamidophenol or an alkali labile precursor of such phenol.
  • the scavenger is a 2,4-disulfonamidophenol or an alkali labile precursor of such phenol.
  • Preferred sulfonamidophenol scavengers for oxidized color developing agents used in the present invention can be represented by the structural formula: wherein:
  • Each R 1 is individually alkyl of 1 to 30 carbon atoms, aryl of 6 to 30 carbon atoms or heterocyclyl of 5 to 30 atoms containing one or more ring heteroatoms selected from nitrogen, oxygen, sulfur and selenium; and
  • R 2 , R 3 and R 4 are each individually hydrogen, halogen, alkyl of 1 to 30 carbon atoms, alkoxy of 1 to 30 carbon atoms, aryl of 6 to 30 carbon atoms or aryloxy of 6 to 30 carbon atoms, the scavenger being of sufficient bulk so as to be non-diffusible in the layers of the element.
  • Especially preferred sulfonamidophenol scavengers have the structural formula: wherein:
  • R 2 , R 3 and R 4 are each individually hydrogen, alkyl of 1 to 30 carbon atoms or alkoxy of 1 to 30 carbon atoms.
  • R 3 is alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms and R 2 and R 4 are hydrogen.
  • G is a hydroxy group or an alkali labile precursor of a hydroxy group.
  • the hydrogen atom of the hydroxy group is replaced with a blocking group which is removed upon contact with base.
  • Typical blocking groups are removable by hydrolysis or by intramolecular nucleophilic displacement.
  • Typical groups removable by hydrolysis are acyl groups such as aliphatic and aromatic carbonyl and sulfonyl groups.
  • Typical groups removable by intramolecular nucleophilic displacement are described in U.S. Patent 4,310,612.
  • alkyl, alkoxy, aryl, and aryloxy substituents described above can be further substituted.
  • substituents include halogen, nitro, alkyl, aryl, alkenyl, alkoxy, aryloxy, alkenyloxy, heterocyclyl, alkylcarbonyl, arylcarbonyl, alkenylcarbonyl, alkylsulfonyl, arylsulfonyl, alkenylsulfonyl, amino, aminocarbonyl, aminosulfonyl, carboxy, alkoxycarbonyl, aryloxycarbonyl, alkenyloxycarbonyl, and the like.
  • alkyl is inclusive of, e.g., arylalkyl and aryloxyalkyl
  • aryl is inclusive of, e.g., alkaryl and alkoxyaryl.
  • the alkenyl groups referred to above can also be substituted, e.g. aralkenyl.
  • the amine portions of these further substituents include primary, secondary, and tertiary amines as well as acylated amines.
  • the compounds used in the present invention are known compounds or similar to known compounds and can be prepared by known reactions.
  • a 2,4-diaminophenol is reacted with the appropriate sulfonyl halide.
  • a 2-amino-4-nitrophenol or a 4-amino-2-nitrophenol is reacted with an appropriate sulfonyl halide to attach one of the groups to the amino substituent, the nitro group is then reduced and a second sulfonyl halide is attached to the amino group formed by reduction of the nitro group.
  • the blocking group can be attached to the hydroxy either before or after attachement of the sulfonamido groups. Representative preparations are shown in the working examples.
  • the scavengers used in this invention can be used in the ways and for the purposes that scavengers for oxidized developing agent are employed in the art. They can be incorporated in a silver halide emulsion layer of the photographic element or in a separate layer of the element. When incorporated in a separate layer, that layer is preferably an interlayer between silver halide emulsion layers although it can be an undercoat layer coated below all of the silver halide emulsion layers or an overcoat layer coated above all of the silver halide emulsion layers.
  • the amount of scavenger compound employed will depend upon the particular purpose for which the scavenger is to be used and the degree of scavenging desired. Typically useful results are obtained when the scavenger is employed in an amount of between 5 and 2000 mg/sq. meter.
  • the scavenger can be incorporated in photographic elements by techniques known in the art.
  • the scavenger is dissolved in a high boiling solvent, such as a water insoluble coupler solvent and then dispersed either in a silver halide emulsion layer or in a separate vehicle such as gelatin.
  • a high boiling solvent such as a water insoluble coupler solvent
  • Typical useful coupler solvents are moderately polar solvents such as tritolylphosphate, di-N-butylphthalate, diethyllauramide, 2,4-dipentylphenol, and the like.
  • Typical vehicles are gelatin, and other hydrophilic colloids commonly employed in silver halide photographic elements. These vehicles are described in Research Disclosure, December 1978, Item No. 17643, Section IX.
  • the scavengers can be introduced into the element in a polymeric latex. Suitable techniques for dispersing the scavengers in a latex are described in U.S. Patents 4,203,716 and 4,214,047 and in Research Disclosure, July 1977, Item 15930 and July 1980, Item 19551.
  • the photographic elements of the present invention can be simple monochrome color elements comprising a support bearing a layer of the silver halide emulsion, or they can be multicolor multilayer elements. They can be designed for processing with separate solutions or for in-camera processing.
  • Multicolor elements contain dye image-forming units sensitive to each of the three primary regions of the spectrum. Each unit can be comprised of a single emulsion layer or of multiple emulsion layers sensitive to a given region of the spectrum.
  • the layers of the element, including the layers of the image-forming units can be arranged in various orders as known in the art.
  • the emulsion or emulsions can be disposed as one or more segmented layers, e.g., as by the use of microvessels or microcells, as described in Belgian Patent 881,513.
  • a preferred photographic element comprises a support bearing at least one blue-sensitive silver halide emulsion layer having associated therewith a yellow image dye-providing material, at least one green-sensitive silver halide emulsion layer having associated therewith a magenta image dye-providing material and at least one red-sensitive silver halide emulsion layer having associated therewith a cyan image dye-providing material, the element containing a scavenger of this invention.
  • the scavenger is in an interlayer between silver halide emulsion layers sensitive to different regions of the visible spectrum although it can be in a silver halide emulsion layer or in an interlayer between silver halide emulsion layers sensitive to the same region of the visible spectrum.
  • the photographic elements of the present invention can contain additional layers conventional in photographic elements, such as overcoat layers, spacer layers, filter layers, antihalation layers, pH lowering layers (sometimes referred to as acid layers and neutralizing layers), timing layers, opaque reflecting layer, opaque light-absorbing layers and the like.
  • the support can be any suitable support used with photographic elements. Typical supports include polymeric films, paper (including polymer-coated paper), glass and the like. Details regarding supports and other layers of the photographic elements of this invention are contained in Research Disclosure, December 1978, Item 17643, referred to above.
  • the light-sensitive silver halide emulsions employed in the photographic elements of this invention can include coarse, regular or fine grain silver halide crystals or mixtures thereof and can be comprised of such silver halides as silver chloride, silver bromide, silver bromoiodide, silver chlorobromide, silver chloroiodide, silver chlorobromoiodide, and mixtures thereof.
  • the emulsions can be negative working or direct positive emulsions. They can form latent images predominantly on the surface of the silver halide grains or in the interior of the silver halide grains. They can be chemically and spectrally sensitized in accordance with usual practices.
  • the emulsions typically will be gelatin emulsions although other hydrophilic colloids can be used in accordance with usual practice. Details regarding the silver halide emulsions are contained in Research Disclosure, Item 17643, December, 1978 and the references listed therein.
  • the photographic silver halide emulsions can contain other addenda conventional in the photographic art.
  • Useful addenda are described, for example, in Research Disclosure, December 1978, Item 17643.
  • Useful addenda include spectral sensitizing dyes and desensitizers, antifoggants, masking couplers, DIR (developement inhibitor-releasing) couplers, DIR compounds, anti-stain agents, image dye stabilizers, absorbing materials such as filter dyes and UV absorbers, light scattering materials, coating aids, plasticizers and lubricants.
  • the dye-image-providing material employed in the photographic element can be incorporated in the silver halide emulsion layer or in a separate layer associated with the emulsion layer.
  • the dye-image-providing material can be any of a number known in the art, such as dye-forming couplers, bleachable dyes, dye developers and redox dye-releasers, and the particular one employed will depend on the nature of the element and the type of image desired.
  • Dye-image-providing materials employed with conventional color materials designed for processing with separate solutions are preferably dye-forming couplers; i.e., compounds which couple with oxidized developing agent to form a dye.
  • Preferred couplers which form cyan dye images are phenols and naphthols.
  • Preferred couplers which form magenta dye images are pyrazolones and pyrazolotriazoles.
  • Preferred couplers which form yellow dye images are benzoylacetanilides and pivalylacetanilides.
  • Dye-image-providing materials useful in diffusion transfer film units contain a dye group and a monitoring group.
  • the monitoring group in the presence of an alkaline processing solution and as a function of a silver halide development, is responsible for a change in mobility of the dye group.
  • These dye-image-providing materials can be initially mobile and rendered immobile as a function of silver halide development, as described in U.S. Patent 2,983,606. Alternatively, they can be initially immobile and rendered mobile, in the presence of an alkaline processing solution, as a function of silver halide development. This latter class of. materials include redox dye-releasing compounds.
  • the monitoring group is a carrier from which the dye is released as a direct function of silver halide development or as an inverse function of silver halide development, 3-pyrazolidones such as 1-phenyl-3-pyrazolidone and 1-phenyl-4,4-dimethyl-3-pyrazolidone being preferred developing agents.
  • 3-pyrazolidones such as 1-phenyl-3-pyrazolidone and 1-phenyl-4,4-dimethyl-3-pyrazolidone being preferred developing agents.
  • Compounds which release dye as a direct function of silver halide development are referred to as negative-working release compounds, while compounds which release dye are an inverse function of silver halide development are referred to as positive-working release compounds.
  • a preferred class of negative-working release compounds are the ortho or para sulfonamidophenols and naphthols described in U.S. Patents 4,054,312, 4,055,428 and 4,076,529.
  • the dye group is attached to a sulfonamido group which is ortho or para to the phenolic hydroxy group and is released by hydrolysis after oxidation of the sulfonamido compound during developement.
  • a preferred class of positive-working release compounds are the nitrobenzene and quinone compounds described in U.S. Patent 4,139,379.
  • the dye group is attached to an electrophilic cleavage group, such as a carbamate group, ortho to the nitro group or the quinone oxygen, and is released upon reduction of the compound by an electron donor compound contained in the element or the processing composition, unless the electron donor is oxidized during development.
  • the developing agents which can be used to develop the photographic elements of this invention, the oxidized form of which can be reduced by the scavengers of this invention, include aminohydroxy- pyrazoles, aminophenols and phenylene diamines. Some developing agents, when used for certain applications, are referred to in the art as electron transfer agents. The particular developing agent employed will depend on the particular type of photographic element to be processed.
  • Representative preferred color developing agents include: 4-amino-N-ethyl-N-a-hydroxy-ethyl-3- toluidine, N,N-diethyl-p-phenylenediamine, 3-methyl-N,N-diethyl-p-phenylenediamine, 3-methoxy-N,N-diethyl-p-phenylenediamine and N,N,N',N'-tetramethyl-p-phenylenediamine.
  • non-diffusible used herein has the meaning commonly applied to the term in photography and denotes materials that for all practical purposes do not migrate or wander through organic colloid layers such as gelatin in an alkaline medium, in photographic elements and preferably when processed in a medium having a pH of 10 or greater.
  • diffusible has the converse meaning and denotes the materials having the property of diffusing effectively through the colloid layers of photographic elements in an alkaline medium.
  • scavenger compounds used in the photographic elements of this invention with respect to their effectiveness as interlayer scavengers for oxidized color developing agents a color negative test photographic element was employed represented by the following schematic structure:
  • the hardener is bis(vinylsulfonylmethyl)ether and the couplers have the following structures:
  • Yellow Coupler Cyan Coupler: Couplers and test compounds were coated as dispersions in dibutylphthalate or comparable coupler solvent.
  • oxidized color developing agent originating in the emulsion layer as the exposed silver halide develops, can react with the yellow coupler to form a yellow dye. It can also migrate through the interlayer to the cyan layer to react with coupler there to form a cyan dye. Reactive test compounds in the interlayer can also react with oxidized color developing agent, thus limiting cyan dye formation to the cyan layer.
  • the scavenger compound reduce oxidized developing agent rather than coupling with it, since the latter reaction can result in unwanted dye stain.
  • Scavenging efficiency of each test compound was determined by measuring the developed density ratio of cyan dye (at 665 nm) to yellow dye (at 450 nm).
  • the more active scavenger compounds used in the invention reduce this red/blue density ratio to about 0.20 from a control value (no scavenger in the interlayer) of about 0.40.
  • control and comparison compounds at equimolar levels show less scavenging ability and greater propensity for undesired coupling to form dye than do the scavenger compounds used in the invention.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Medicinal Preparation (AREA)
EP19830303424 1982-06-18 1983-06-14 Color photographic elements containing scavengers for oxidized developing agents Expired EP0098072B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US38999482A 1982-06-18 1982-06-18
US389994 1982-06-18

Publications (3)

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EP0098072A2 EP0098072A2 (en) 1984-01-11
EP0098072A3 EP0098072A3 (en) 1984-03-28
EP0098072B1 true EP0098072B1 (en) 1986-10-01

Family

ID=23540598

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EP19830303424 Expired EP0098072B1 (en) 1982-06-18 1983-06-14 Color photographic elements containing scavengers for oxidized developing agents

Country Status (4)

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EP (1) EP0098072B1 (enrdf_load_stackoverflow)
JP (1) JPS595247A (enrdf_load_stackoverflow)
CA (1) CA1193129A (enrdf_load_stackoverflow)
DE (1) DE3366572D1 (enrdf_load_stackoverflow)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59192246A (ja) * 1983-04-15 1984-10-31 Fuji Photo Film Co Ltd カラ−写真感光材料
JPS59192247A (ja) * 1983-04-15 1984-10-31 Fuji Photo Film Co Ltd カラ−写真感光材料
JPS59195239A (ja) * 1983-04-19 1984-11-06 Fuji Photo Film Co Ltd カラ−写真感光材料
JPS59204039A (ja) * 1983-05-04 1984-11-19 Fuji Photo Film Co Ltd カラ−写真感光材料
JPS59222836A (ja) * 1983-05-31 1984-12-14 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料
JPS60118836A (ja) * 1983-11-30 1985-06-26 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料
JPS60118835A (ja) * 1983-11-30 1985-06-26 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料
JPS6197768A (ja) * 1984-10-18 1986-05-16 Nippon Denki Kanji Syst Kk メモリアドレス方式
JPS6240455A (ja) * 1985-08-16 1987-02-21 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料
JPS6249349A (ja) * 1985-08-23 1987-03-04 Konishiroku Photo Ind Co Ltd ハロゲン化銀カラ−写真感光材料
JPS62127734A (ja) * 1985-11-27 1987-06-10 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料
JPS63153548A (ja) * 1986-12-17 1988-06-25 Konica Corp ハロゲン化銀カラ−写真感光材料
CA1338796C (en) * 1987-01-28 1996-12-17 Nobuo Furutachi Color photographs, a process for preparing them and color photographic materials employed therefor
JP2613380B2 (ja) * 1987-01-31 1997-05-28 コニカ株式会社 粒状性の改良されたハロゲン化銀カラー写真感光材料
JPS63254442A (ja) * 1987-04-13 1988-10-21 Fuji Photo Film Co Ltd 感光材料
US4927744A (en) * 1988-08-05 1990-05-22 Eastman Kodak Company Photographic element having solid particle dispersion oxidized developer scavenger
JPH07117737B2 (ja) * 1988-08-12 1995-12-18 富士写真フイルム株式会社 ハロゲン化銀カラー写真感光材料の処理方法
DE4140946A1 (de) * 1991-12-12 1993-06-17 Agfa Gevaert Ag Farbfotografisches aufzeichnungsmaterial
JPH06167775A (ja) * 1992-11-30 1994-06-14 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料及び画像形成方法
EP0708932A1 (en) * 1994-05-16 1996-05-01 Eastman Kodak Company Photographic element having reduced dye stain
EP0764876B1 (en) * 1995-09-22 2002-12-11 Fuji Photo Film Co., Ltd. Silver halide photographic material

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4205987A (en) * 1978-11-15 1980-06-03 Eastman Kodak Company Sulfonamido phenol scavenger compounds

Also Published As

Publication number Publication date
JPH0311456B2 (enrdf_load_stackoverflow) 1991-02-18
JPS595247A (ja) 1984-01-12
DE3366572D1 (en) 1986-11-06
EP0098072A2 (en) 1984-01-11
EP0098072A3 (en) 1984-03-28
CA1193129A (en) 1985-09-10

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