US3617273A - Competing color developer process and composition - Google Patents

Competing color developer process and composition Download PDF

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Publication number
US3617273A
US3617273A US835224A US3617273DA US3617273A US 3617273 A US3617273 A US 3617273A US 835224 A US835224 A US 835224A US 3617273D A US3617273D A US 3617273DA US 3617273 A US3617273 A US 3617273A
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United States
Prior art keywords
hydroxyanilinomethyl
color
developing agent
pyridine
competing
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Expired - Lifetime
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US835224A
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English (en)
Inventor
Atsuaki Arai
Mitsugu Tanaka
Haruhiko Iwano
Isao Shimamura
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • 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
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/29—Development processes or agents therefor
    • G03C5/30—Developers
    • G03C5/3021—Developers with oxydisable hydroxyl or amine groups linked to an aromatic ring

Definitions

  • X is hydrogen, alkyl, hydroxylalkyl, phenyl or halogen
  • Y is a substituted or unsubstituted N, S or 0 containing heterocyclic ring, and process for the use thereof.
  • the present invention relates to developer compositions for color photography, and more particularly, to a color-forming developer composition containing a novel water soluble competing developing agent.
  • reversal color photographic light-sensitive elements which are to be developed in a coupler-containing developer are, after exposure, subjected to black and white development, and then, after being subject to a reversal exposure, processed in a color developer which contains couplers.
  • This type of element usually has multiple emulsion layers which include three selective light-sensitive emulsion layers.
  • a sup port carries the following layers: 1) a lowermost red-sensitive emulsion layer, 2) a green-sensitive emulsion layer, 3) a yellow filter layer, 4) a blue-sensitive emulsion layer, and 5) an upper protective layer (formed on the support in the order given).
  • the color-forming developer used for developing such reversal color photographic Iigh'tsensitive elements usually comprises: 1) an alkaline aqueous solution containing a pphenylenediamine-type developing agent which has at least one primary amino group, 2) a color-forming coupler, and 3) additives, such as an alkali metal sulfite, e.g. sodium sultite, an alkali metal sulfite, e.g. sodium sultite, an alkali metal sulfite, e.g. sodium sultite, an alkali metal sulfite, e.g. sodium sultite, an alkali metal sulfite, e.g. sodium sultite, an alkali metal sulfite, e.g. sodium sultite, an alkali metal sulfite, e.g. sodium sultite, an alkali metal sulfite
  • I alkali metal bromide e.g. sodium bromide, an alkali metal iodide, etc.
  • color-forming developer compositions contain a phenolic or naphtholic coupler as a cyan dyeformer, a pyrazolone coupler as a magenta dye-former, and an open-chain ketomethylene coupler as a yellow dye-former.
  • a competing developing agent When subjecting a reversal color photographic element to cyan development using a color-forming developer containing a color former or coupler, to suppress the formation of cyan fogs in the green-sensitive and the blue-sensitive emulsion layers, a competing developing agent is incorporated into the cyan developer.
  • N-benzyl-p-aminophenol is widely used as one such "competing developing agent.” It is generally known that the competing developing agent will reduce an oxidized color developing agent to the state of the original developing agent, and will reduce an exposed silver halide into metallic silver. The competing developing agent will thus contribute to suppressing cyan contamination in the blue-sensitive emulsion layer and, in particular, in the green-sensitive emulsion layer, thus yielding a correct red reproduction of the subject photographed. This is due to the fact that the competing developing agent and the color developing agent will both compete for reaction with the exposed silver halide.
  • a competing developing agent to be employed in photographic processing must be capable of increasing the red contrast by removing cyan contamination, and also must be capable of increasing the sensitivity of the red-sensitive emulsion layer. Furthermore, the competing developing agent must not reduce the maximum density of the red-sensitive emulsion layer, must not reduce the high degree of clarity of the cyan color developing agent, and must not reduce the photographic properties of the emulsion without also reducing the stability of the cyan developer.
  • Another object is to provide a color developer composition containing a novel competing developing agent which will yield a high purity red reproduction, and which will also increase the sensitivity of a red-sensitive emulsion layer.
  • a still further object is to provide a competing developing agent which will not reduce the maximum density of a red-sensitive emulsion layer, will not reduce the clarity of a cyan color developing agent and which will not reduce the photographic properties of the emulsion, such as reversal sensitivity, red purity, and the red filter density-blue filter density ratio, without reducing the stability of the cyan developer.
  • the water-soluble competing developing agents of the present inventign include those represented by the formula:
  • X represents a hydrogen atom, an alkyl group having from one to four carbon atoms such as methyl, ethyl, propyl,
  • Y represents a heterocyclic ring having at least one N, S or 0 atom, such as pyrrole, pyrazole, imidazole, pyridine, pyrimidine, indole, thiophene, furan, oxazole, etc.
  • the heterocyclic ring may be substituted by an alkyl group having from one to four carbon atoms or a benzyl group.
  • the color developer composition of the present invention comprises, therefore, (A) a primary aromatic amino developing agent, (8) a color-forming coupler, (C) an alkali, and (D) a water-soluble competing developing agent having the formula (I).
  • the competing developing agents of this invention are used to advantage in color developer solutions for processing color photographic elements in instances where it is desirable to control color'contrast, fog, etc.
  • the competing developing agents of the present invention are unexpectedly better than some known competing developing agents and are valuable for use in color photographic processing.
  • a cyan color developer which contains a p-phenylenediamine type color developing agent
  • the cyan .developer used in this invention exhibits an excellent cyan fog preventing property and an excellent red reproduction of the original.
  • the color developer containing the competing developing agent of this invention shows better stability or gives less degradation of its properties and provides images having good photographic characteristics when the developer is stored or repeatedly used for a long period of time.
  • the concentration of the competing developing agents of this invention will vary, depending upon the type and concentration of the color developing agent and coupler used in the color developer, and will also vary with the pH of the color developer. However, in general, a concentration of 0.0l-5.0 g./liter of developer is preferably employed. Further, it has been found that the most effective concentration utilized is about 0. l-l .0 g./liter.
  • the competing developing agents of this invention are commonly used in the form of salts, such as the hydrochloride, which are more stable than the free amine.
  • the competing developing agents of this invention can be effectively used in any cyan color developer, magenta color developer, or yellow color developer, but it is most effectively used in a cyan color developer.
  • the color developing agent used in the color developer composition of this invention is generally a p-phenylenediamine derivative, such as: N,N-diethyl-p-phenylenediamine sulfite; N,N-diethyl-3-methyl-p-phenylenediamine hydrochloride; 4-amino-3-methyl-N-ethyl-N-methanesulfonamido ethylaniline sulfate; 4-amino-3-methyl-N-ethyl-N- hydroxyethyl-aniline sulfate; N-ethyl-N-hydroxyethyl-p-phenylenediamine sulfate, etc.
  • the p-aminophenols and their substituted materials may also be used.
  • color formers used in this invention there are: 2,4-dichloro-l-naphthol; 2,4-dich1oro-5 tolylsulfonamido-l-naphthol; l-oxy-2-benzylnaphthamide; 2,6-dibromo-l,S-dihydroxynaphthalene; benzoylacetanilide; O-benzoyl-4-(p-toluenesulfonamido)acetanilide; 1-phenyl-3- (m-nitrobenzoyl-amino)--pyrazolone; and cyanoacetyl coumaron.
  • other color formers which are conventionally utilized, may be employed in this invention.
  • the free amines were converted to the salts such as the sulfate or the hydrochloride by the known procedure in the art.
  • a multilayer color photographic film was formed of the following layers (in the order given) on a photographic film support: (1) a red-sensitive gelatino silver iodo-bromide emulsion layer, (2) a green-sensitive gelatino silver iodobromide emulsion layer, (3) a blue-absorbing yellow filter layer comprising colloidal silver, and (4) a blue-sensitive gelatino silver iodobromide emulsion layer.
  • This film was exposed by means of a sensitometer, and subjected to the following processes:
  • compositions of the processing baths used in the above processes are as follows:
  • Magenta Color Developer Sodium sulfite 5.0 g. 2-Amino-5-N.N-diethylaminotoluene hydrochloride 2.0 g. Potassium bromide 0.8 g. l-phenyl-3'(m-nitrobenzoylamino)-5- pyrozolone l.4 g. Sodium hydroxide 2.0 g. n-Butylamine 5.0 ml. Water to make I000 ml.
  • the competing developing agents shown inthe following table were (individually) added to the cyan color developer, and the effect of the competing developing agents on the photographic properties of the film was measured.
  • the photographic properties of the processed film are shown in the following table, with each of the three competing developing agents, in which: (I) the reversal sensitivity is shown by the inverse logarithm of the amount of exposure at which the coupling density obtained corresponds to L0; (2) the purity of the red color reproduction is shown by the ratio of the red filter density to the green filter density (D,/D,,) of a portion of the film exposed to red light (called red patch); and (3) the ratio of the red filter density to the blue filter density (D /D of said portion is also shown.
  • the ratio D,/D,, or D,/D is a value which illustrates the color purity of a reproduced color when a red object is reproduced in a color photograph, and the smaller that this value is, the better the reproduction.
  • EXAMPLE ll Using the same basic procedures as in example l. a cyan color development was carried out. After being washed with water for eight minutes after the cyan development, the cyandeveloped color film was subjected to bleaching, washing and fixing. as in example 1. to provide cyan-colored images. in this case, the photographic properties of the color photographs which were improved by the competing developing agent of this invention were measured. The results thereof are shown in the following table.
  • the reversal sensitivity (A) relates to the red-sensitive emulsion layer
  • the cyan contamination density (B) is shown by the sum of the cyan coupling density in the portion of the green-sensitive emulsion layer exposed to red light and the cyan coupling density in the portion of the blue-sensitive emulsion layer exposed to red light.
  • These two light sensitive emulsion layers are ones which will not be developed to any extent in a cyan color development, and, hence, cyan coupling these portions causes undesirable developing fogs in the green-sensitive emulsion layer to be magenta coupled and undesirable fogs in the blue-sensitive emulsion layer to be yellow coupled.
  • the cyan coupling causes color turbidity, which results in a degrading of the quality of the color photographic image.
  • Cyan Color Developer The photographic properties obtained by adding the competing developing agent of this invention to the cyan developer were compared with those obtained by adding.
  • a conventional competing developing agent N- benzyl-p-aminophenol hydrochloride.
  • the amount and the type of competing developing agent used are shown below:
  • the competing developing agent of this invention illustrated an excellent effect during this experiment, when compared with the known competing developing agent.
  • a color developer composition comprising (1) a primary aromatic amino developing agent, (2) a color-forming coupler, (3) an alkali, and (4alkali a water-soluble competing developing agent having the formula:
  • X represents a member selected from the class consisting of a hydrogen atom, an alkyl group having from one to four carbon atoms, a hydroxyalkyl group having from one to four carbon atoms, a phenyl group and a halogen atom
  • Y represents a substituted or unsubstituted heterocyclic ring having at least one N, S or O atom, said heterocyclic ring, when substituted, being substituted with a member selected from the class consisting of an alkyl group having from one to four carbon atoms, and a benzyl group.
  • composition of claim 1 wherein said composition additionally contains a member selected from the class consisting of an alkali metal bromide, an alkali metal sulfite, and alkali metal iodide.
  • coupler is selected from the class consisting of phenolic couplers, naphtholic couplers, pyrazolone couplers, coumarone couplers and the open-chain ketomethylene couplers.
  • HOG-NH-GH -Y wherein X represents a member selected from the class consisting of a hydrogen atom, an alkyl group having from one to four carbon atoms, a hydroxyalkyl group having from one to four carbon atoms, a phenyl group and a halogen atom and Y represents a substituted or unsubstituted heterocyclic ring having at least one N, S or O atom, said heterocyclic ring, when substituted, being substituted with a member selected from the class consisting of an alkyl group having from one to four carbon atoms and a benzyl group.
  • one of said baths is a yellow developer, and contains B-(p-hydroxyanilinomethyl)pyridine as the competing develo inga ent.
  • one of said baths is a magenta developer
  • conwater-soluble competing developing agent is selected from the class consisting of B-(p-hydroxyanilinomethyl)-pyridine a-(phydroxyanilinomethyl)pyridine, y-(p-hydroxyanilinomethyl)pyridine, a-(p-hydroxyanilinomethyl)furan, B-(3-methyl-4-hydroxyanilinomethyl)pyridine, [3-(3-phenyl-4 -hydroxyanilinomethyl)furan, a-(p-hydroxyanilinomethyl) thiophene, 2-(p-hydroxyanilinomethyl)-5-methylthiophene, l-benzyl-3-(p-hydroxyanilinomethyl)indole, a-(3chloro-4- hydroxyanilinomethyl)furan and a-(3-methyl-4-hydroxyanilinomethyl)furan said competing developing agent being present in an amount of 0.01 to 5.0 g./liter of the
  • a composition for preparing a color developer solution comprising (1) a primary aromatic amino developing agent, and (2) a water-soluble competing developing agent having the formula:
  • X represents a member selected from the class consisting of a hydrogen atom, an alkyl group having from one to four carbon atoms, a hydroxyalkyl group having from one to four carbon atoms, a phenyl group and a halogen atom
  • Y represents a substituted or unsubstituted heterocyclic ring having at least one N, S or O atom, said heterocyclic ring, when substituted, being substituted with a member selected from the class consisting of an alkyl group having from one to four carbon atoms and a benzyl group.
  • composition of claim 10 wherein said competing developing agent is selected from the class consisting of B-(phydroxyanilinomethyl)pyridine, a-(p-hydroxyanilinomethyl)pyridine, -y-(p-hydroxyanilinomethyl)pyridine, a-(p-hydroxyanilinomethyl)furan, B-(3-methyl-4-hydroxyanilinomethyl)pyridine, B-(3-phenyl-4 -hydroxyanilinomethyl)furan, a-(phydroxyanilinomethyl)thiophene, 2-(p-hydroxyanilinomethyl)-5- methylthiophene, l-benzyl-3-(p-hydroxyanilinomethyl)indole, a-(3-chloro-4-hydroxyanilinomethyl)furan and a-(3- methyl-4-hydroxyanilinomethyl)furan.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
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US835224A 1968-06-20 1969-06-20 Competing color developer process and composition Expired - Lifetime US3617273A (en)

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DE (1) DE1931333B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
FR (1) FR2011329B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
GB (1) GB1244696A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4161406A (en) * 1977-12-07 1979-07-17 Philip A. Hunt Chemical Corp. Solution and method for processing high speed video news film
US4543322A (en) * 1983-03-31 1985-09-24 Fuji Photo Film Co., Ltd. Process for the processing of color photographic silver halide light-sensitive material
US5695914A (en) * 1995-09-15 1997-12-09 Eastman Kodak Company Process of forming a dye image
EP2518063A1 (en) * 2006-12-21 2012-10-31 Sloan-Kettering Institute For Cancer Research Pyridazinones and furan-containing compounds
US20210340138A1 (en) * 2014-02-20 2021-11-04 Novita Pharmaceuticals, Inc. Compounds and methods for inhibiting fascin
US11866440B2 (en) 2012-08-22 2024-01-09 Cornell University Methods for inhibiting fascin

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3141771A (en) * 1961-02-01 1964-07-21 Eastman Kodak Co Aldehyde scavengers for photographic silver halide developers
US3300305A (en) * 1962-10-25 1967-01-24 Eastman Kodak Co Color developers containing competing developing agents

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3141771A (en) * 1961-02-01 1964-07-21 Eastman Kodak Co Aldehyde scavengers for photographic silver halide developers
US3300305A (en) * 1962-10-25 1967-01-24 Eastman Kodak Co Color developers containing competing developing agents

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4161406A (en) * 1977-12-07 1979-07-17 Philip A. Hunt Chemical Corp. Solution and method for processing high speed video news film
US4543322A (en) * 1983-03-31 1985-09-24 Fuji Photo Film Co., Ltd. Process for the processing of color photographic silver halide light-sensitive material
US5695914A (en) * 1995-09-15 1997-12-09 Eastman Kodak Company Process of forming a dye image
EP2518063A1 (en) * 2006-12-21 2012-10-31 Sloan-Kettering Institute For Cancer Research Pyridazinones and furan-containing compounds
US11866440B2 (en) 2012-08-22 2024-01-09 Cornell University Methods for inhibiting fascin
US12384791B2 (en) 2012-08-22 2025-08-12 Novita Pharmaceuticals, Inc. Methods for inhibiting fascin
US20210340138A1 (en) * 2014-02-20 2021-11-04 Novita Pharmaceuticals, Inc. Compounds and methods for inhibiting fascin
US11858929B2 (en) * 2014-02-20 2024-01-02 Cornell University Compounds and methods for inhibiting fascin
US12168658B2 (en) 2014-02-20 2024-12-17 Novita Pharmaceuticals, Inc. Compounds and methods for inhibiting fascin

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FR2011329A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1970-02-27
DE1931333B2 (de) 1978-04-06
DE1931333A1 (de) 1970-01-02
GB1244696A (en) 1971-09-02
FR2011329B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1976-10-01
NL6909362A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1969-12-23

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