US2808329A - Photographic color correction using colored and uncolored couplers - Google Patents

Photographic color correction using colored and uncolored couplers Download PDF

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Publication number
US2808329A
US2808329A US470499A US47049954A US2808329A US 2808329 A US2808329 A US 2808329A US 470499 A US470499 A US 470499A US 47049954 A US47049954 A US 47049954A US 2808329 A US2808329 A US 2808329A
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US
United States
Prior art keywords
group
colored
coupler
color
uncolored
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 - Lifetime
Application number
US470499A
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English (en)
Inventor
Keith E Whitmore
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
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Eastman Kodak Co
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
Priority to BE550154D priority Critical patent/BE550154A/xx
Priority to NL202187D priority patent/NL202187A/xx
Priority to NL113830D priority patent/NL113830C/xx
Priority to BE540231D priority patent/BE540231A/xx
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US470499A priority patent/US2808329A/en
Priority to FR1146556D priority patent/FR1146556A/fr
Priority to GB21652/55A priority patent/GB783730A/en
Priority to US528516A priority patent/US2860974A/en
Priority to CH345532D priority patent/CH345532A/de
Priority to DEE11571A priority patent/DE964655C/de
Priority to GB37198/55A priority patent/GB853922A/en
Priority to DEE12808A priority patent/DE1008574B/de
Priority to FR72012D priority patent/FR72012E/fr
Application granted granted Critical
Publication of US2808329A publication Critical patent/US2808329A/en
Priority to FR769833A priority patent/FR73828E/fr
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • G03C7/32—Colour coupling substances
    • G03C7/333—Coloured coupling substances, e.g. for the correction of the coloured image
    • G03C7/3335—Coloured coupling substances, e.g. for the correction of the coloured image containing an azo chromophore

Definitions

  • This invention relates to color photography and'particularly to color correction by incorporating in a silver halide emulsion a mixture of colored and uncolored couplers.
  • colored photographic images may be formed by using a developer which produces a colored compound on development.
  • the colored compound thus formed is deposited adjacent the silver grains of the silver image during development.
  • a colored image may be formed by adding to certain developing solutions or by incorporating in the silver halide emulsion a compound which couples during development with the oxidation product of the developing agent and forms a colored compound which is likewise adjacent the silver grains of the silver image during development.
  • a color forming compound or coupler Such a compound which is employed in conjunction with the developing agent for the "silver andwhich couples with the oxidation product of the developing agent during development is referred to herein as a color forming compound or coupler.
  • the invention is, therefore, particularly adaptable to color photographic elements employing a plurality of superimposed silver halide emulsion layers wherein at least one layer or, if desired, all the layers contains a combination of at least one colored coupler and at least one uncolored coupler. 7
  • an object of the invention to provide a new colorphotographic'element having a plurality of superimposed silver halide layers sensitized to different colors and wherein. atleast. one layer contains a combination of a colored coupler and an uncolored couplerc
  • Another object is to provide a color photographic element of the above kind wherein color correction is attained by a new method of masking.
  • Another object is to provide a process for preparing the said new element.
  • I prepare color photographic elements by coating in any order two or more differently sensitized silver halide emulsions, for example, sensitized to the blue, green and red, over one another and, if desired, separated by inert or colored gelatin layers, onto a suitable.
  • photographic supportmaterial such as films or sheets of cellulose acetate, cellulose mixed esters, cellulose nitrate, cellulose ether, synthetic resin materials such as polyesters, polyamides, etc.,. paper materials, glass plates, and the like.
  • the preferred photographic color element contains three differently sensitized silver halide emulsion layers in the order of a bottom red-sensitized layer next to the support, a middle green-sensitized layer and a top blue:sensitize d layer. While suitable combinations of the colored and uncolored. couplers may be incorporated in any one or allot these layers, a preferred form of my invention is to include a suitable yellow colored coupler, together with a. suitable uncolored couplerin the green-sensitized layer, a suitable magenta colored-coupler with an uncolored coupler in the blue-sensitive layer and a suitable orange colored coupler with an uncolored coupler in the red sensitized layer.
  • Suitable colored couplers which react with developers of the ph'enylene diamine type to give water-soluble dyes. include a wide variety of nondiffusing azo type yellow, orange and magentacolored couplers. Those which are particularly useful in this invention may be represented by the following generalformulas-L and OONHR;
  • R1, R3 and R4 are simple or complex alkyl or aryl groups or combinations of these containing one or more solubilizing groups such as sulfo or carboxy groups, and R2 represents a ballasting group.
  • R1, R3 and R4 are simple or complex alkyl or aryl groups or combinations of these containing one or more solubilizing groups such as sulfo or carboxy groups, and R2 represents a ballasting group.
  • Vitturn is 1-p-sulfophenyl-3-methyl-4-p-laurylphenylazo-S-pyrazolone which coupler on incorporation into a silver halide emulsion, followed by exposure and development with a p-amino dirnethylaniline developing solution is converted in the exposed areas to a water-soluble, dit fusible azo methine dye which will wash out of the film.
  • This soluble dye may be represented by the following structural formula:
  • N G-NHC O 1-pheny1-3- (3-sulfobenzamido) 4-(4-octadecy1oxyphenylazo)- 5-pyrnzolone 1pheny1-3- (Z-carboxybenzamido) 4- (4-dodecyloxypheuylazo) o-pyrazolone 1 (4-su1fophenyl) -3-Inethyl- ⁇ 4- [4 (l-cert. buty1)phenoxy] pheny1azo ⁇ -5-pyrazo1one
  • This compound can be prepared by the general procedure of above compound (2).
  • Typical compou-ndssof structure II include those such as:
  • the compounds furnishing the ballast group R2 are prepared, for example, as described in the following example:
  • 3-amino-2-naphthoic acid is dissolved in an excess of n-amyl alcohol and dry hydrogen chloride is passed into the mixture. After refluxing several .hours, the excess alcohol is removed by vacuum distillation and the residue stirred in a sodium carbonate'sol-ution. The product is collected on a filter and dried.
  • the compounds furnishing the ballast group, prepared according to Example 4 are diazotized and then coupled in a basic medium such as pyridine, sodium hydroxide or acetic acid-i-sodium acetate with the solubilized compounds prepared according to above Examples 1-3, and the azo dyes which form are collected and purified.
  • a basic medium such as pyridine, sodium hydroxide or acetic acid-i-sodium acetate
  • Suitable uncolored non-diffusing couplers for use in my invention include any of those described in United States Patent No. 2,298,443, dated October 13, 1942, of A. Weissberger.
  • Example 4 parts by weight of an uncolored coupler, N-(pbenzoylacetaminobenzeiiesulfonyl)-N-( phenylpropyl)- p-toluidine, dissolved in 8 parts of di-n-butyl phthalate were dispersed in 17 parts by weight of a aqueous gelatin solution.
  • the developer composition was as follows:
  • Example 6 This example was carried out the same as Example 5, except that the uncolored coupler, 1-hydroXy-2-[8(2',4'- di-tert. amylphenoxy)-n-butyl]-naphthamide (prepared according to U. S. Patent No. 2,474,293, dated June 28, 1949, of A. Weissberger et al.), which reacts with N- ethyl-N-(B-sulfonamidoethyl)*3-methyl-4-aminoaniline to produce a cyan dye having an appreciable amount of green and blue absorption, was substituted for the uncolored coupler employed in Example 5. The emulsion was coated and processed as in Example 5. Sensitometric tests indicated that this particular sample showed excellent color correction.
  • the uncolored coupler 1-hydroXy-2-[8(2',4'- di-tert. amylphenoxy)-n-butyl]-naphthamide (prepared according to U. S.
  • Example 7 This example illustrates a coating made with a solvent type of dispersion.
  • An uncolored coupler, 1- (2',4',6-t'richlorophenyl) -3- 3 "- (2"',4'-di-te(rt. amylphenoxy-acet. amido)-benzamido]-5-pyrazolone (prepared according to U. S. Patent No. 2,600,788, dated June 17, 1952, of A.
  • the coating was processed as in above Example 5. Sensitometric tests of the sample showed excellent color correction.
  • Example 8 This example was carried out the same as Exam ner,
  • amyl phenoxyacetamido) -benzamido]-5-pyrazol0ne an uncoloredcoupler yielding a magenta dye, dissolved in tricresyl phosphate, was added to the green-sensitive silver halide emulsion and coated as the middle layer, (3) a mixture of N-(p-benzoylacetaminobenzenesulfonyl) -N- (y-phenylpropyl)-p-toluidine, an uncolored coupler yielding a yellow dye and 1-hydroxy-4-(2-amyloxycarbonyl-3- naphthylazo')'-N- [fl(2-carboxybenzamido) ethyl] Z-naphthamide, a magenta-colored coupler yielding a soluble dye, dissolvedin di-n-butyl-phthalate, was added to an unsensitized silver halide emulsion and coated over a vellnw filterlayer.
  • R1, R3 and R4 each represents a member selected from the group consisting of an alkyl group and an aryl group, said group having at least one solubilizing group attached thereto selected from the group consisting of a carboxy group, a sulfo group, an alkali metal carboxy group, an alkali metal sulfo group, an ammonium carboxy group and an ammonium sulfo group, and R2 represents an aromatic radical having attached thereto an alkyl group of from 4 to 15 carbon atoms, which comprises exposing said element and developing it to form color images from said uncolored and said colored colorforming couplers in the exposed portions and simultaneously to split said colored color former at the azo group, thus forming a soluble dye which is removed from the emulsion layer, leaving the uncoupled portion of
  • the said uncolored color-forming coupler is l(2',4',6'-trichlorophenyl)-3-[3"-(2,4'di-tert. amido)-benzamido]-5-pyrazolone and the said colored amplphenoxy-acetcolor-forming coupler is the trimethylbenzyl ammonium salt of l-phenyl-3-(Z-carboxybenzamido)-4-(4dodecyloxyphenylazo -5-pyraz0lone.
  • R1, R3 and R4 each represents a member selected from the group consisting of an alkyl group and an aryl group, said group having at least one solubilizing group attached thereto selected from the group consisting of a carboxy group, a sulfo group, an alkali metal carboxy group, an alkali metal sulfo group, an ammonium carboxy group and an ammonium sulfo group, and R2 epresents an aromatic radical containing an alkyl group of from 4 to 15 carbon atoms, which comprises exposing said element and developing it with a primary aromatic amine developing agent to form color images in the bluesensitized layer from said uncolored and said colored color-forming couplers in the exposed portions and simultaneously to split said colored color former at the azo group, thus forming a soluble dye which is removed from the blue-sensitized emulsion layer, leaving the uncoupled portion of said colored color-former as a mask in the said blue-sensitized emulsion
  • a photographic element comprising a support having thereon at least one silver halide emulsion layer which contains at least one uncolored color-forming coupler which is reactive with the oxidation product of a primary aromatic amine developing agent to form a non-diffusible dye in the said layer and which further contains at least one colored color-forming coupler selected from the groups consisting of those represented by the following general formulas:
  • R1, R3 and R4 each represents a member selected from the group consisting of an alkyl group and an aryl group, said group having at least one solubilizing group attached thereto selected from the group consisting of a carboxy group, a sulfo group, an alkali metal carboxy group, an alkali metal sulfo group, an ammonium carboxy group and an ammonium sulfo group, and R2 represents an aromatic radical containing an alkyl group of from 4 to l5 carbon atoms.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US470499A 1954-11-22 1954-11-22 Photographic color correction using colored and uncolored couplers Expired - Lifetime US2808329A (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
BE550154D BE550154A (en)) 1954-11-22
NL202187D NL202187A (en)) 1954-11-22
NL113830D NL113830C (en)) 1954-11-22
BE540231D BE540231A (en)) 1954-11-22
US470499A US2808329A (en) 1954-11-22 1954-11-22 Photographic color correction using colored and uncolored couplers
FR1146556D FR1146556A (fr) 1954-11-22 1955-07-26 Procédé pour la photographie en couleurs et produit pour sa mise en oeuvre
GB21652/55A GB783730A (en) 1954-11-22 1955-07-27 Improvements in colour photographic processes and materials
US528516A US2860974A (en) 1954-11-22 1955-08-15 Photographic color correction process
CH345532D CH345532A (de) 1954-11-22 1955-10-03 Verfahren zur Herstellung von subtraktiven photographischen Dreifarbenbildern und Mittel zu seiner Ausführung
DEE11571A DE964655C (de) 1954-11-22 1955-11-22 Verfahren zur Herstellung eines Maskenbildes in einem photographischen Mehrschichtenmaterial mit Halogensilberemulsionsschichten
GB37198/55A GB853922A (en) 1954-11-22 1955-12-29 Improvements in colour photographic processes and materials
DEE12808A DE1008574B (de) 1954-11-22 1956-08-10 Verfahren zur Herstellung eines Maskenbildes in einem photographischen Mehrschichtenmaterial
FR72012D FR72012E (fr) 1954-11-22 1956-08-14 Procédé pour la photographie en couleurs et produit pour sa mise en oeuvre
FR769833A FR73828E (fr) 1954-11-22 1958-07-08 Procédé pour la photographie en couleurs et produit pour sa mise en oeuvre

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US470499A US2808329A (en) 1954-11-22 1954-11-22 Photographic color correction using colored and uncolored couplers

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US528516A Expired - Lifetime US2860974A (en) 1954-11-22 1955-08-15 Photographic color correction process

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US528516A Expired - Lifetime US2860974A (en) 1954-11-22 1955-08-15 Photographic color correction process

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BE (2) BE540231A (en))
CH (1) CH345532A (en))
DE (2) DE964655C (en))
FR (3) FR1146556A (en))
GB (2) GB783730A (en))
NL (2) NL113830C (en))

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2908573A (en) * 1956-07-25 1959-10-13 Eastman Kodak Co Photographic color couplers containing mono-n-alkyl groups
US3028238A (en) * 1957-01-29 1962-04-03 Agfa Ag Color photography
US3051568A (en) * 1955-12-06 1962-08-28 Edward K Kaprelian Offset electrophotography
US3148062A (en) * 1959-04-06 1964-09-08 Eastman Kodak Co Photographic elements and processes using splittable couplers
US3227551A (en) * 1959-04-06 1966-01-04 Eastman Kodak Co Photographic color reproduction process and element
US3227550A (en) * 1962-09-07 1966-01-04 Eastman Kodak Co Photographic color reproduction process and element
US3285747A (en) * 1964-08-26 1966-11-15 Gen Analine & Film Corp Color formers containing a m-alkyl-phenoxyacyl group
US3459552A (en) * 1965-02-03 1969-08-05 Fuji Photo Film Co Ltd Silver halide emulsions containing magenta-colored cyan couplers
US3658545A (en) * 1968-12-20 1972-04-25 Konishiroku Photo Ind Light-sensitive silver halide color photographic material containing cyan couplers
US3859095A (en) * 1969-12-13 1975-01-07 Agfa Gevaert Ag Color-photographic material with improved color reproduction
US3926634A (en) * 1973-03-27 1975-12-16 Fuji Photo Film Co Ltd Color silver halide photographic materials containing couplers having an oleophilic group
US4002477A (en) * 1973-11-28 1977-01-11 Eastman Kodak Company Diffusion transfer processes and elements using or containing inert transitional metal complex oxidizing agents
US4042394A (en) * 1973-05-07 1977-08-16 Eastman Kodak Company Photographic dye image stabilization
US4777120A (en) * 1987-05-18 1988-10-11 Eastman Kodak Company Photographic element and process comprising a masking coupler
US4871655A (en) * 1987-01-16 1989-10-03 Konica Corporation Light-sensitive silver halide color photographic material containing multi-functional dye
US5100760A (en) * 1986-02-24 1992-03-31 Fuji Photo Film Co., Ltd. Light-sensitive material containing silver halide, reducing agent and polymerizable compound
US5399468A (en) * 1990-12-21 1995-03-21 Eastman Kodak Company Color photographic silver halide duplicating element and process
US6010839A (en) * 1998-06-26 2000-01-04 Eastman Kodak Company Color photographic elements containing yellow-colored magenta dye-forming masking couplers
US6132943A (en) * 1999-10-14 2000-10-17 Eastman Kodak Company Color photographic elements containing yellow-colored magenta dye-forming masking couplers

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3230083A (en) * 1959-04-02 1966-01-18 Polaroid Corp Photographic processes and products
US3230084A (en) * 1959-05-18 1966-01-18 Polaroid Corp Novel photographic products and processes
US3135609A (en) * 1960-06-29 1964-06-02 Gen Aniline & Film Corp 1-hydroxy-2-naphthamide couplers for color photography
CA699092A (en) * 1961-04-06 1964-12-01 Polaroid Corporation Photographic products, processes and compositions
US3230082A (en) * 1962-05-14 1966-01-18 Polaroid Corp Color processes and products
US3418121A (en) * 1964-11-11 1968-12-24 Fuji Photo Film Co Ltd Photographic developer composition containing 2-(o-propionamido-beta-phenylethyl) - 1 - hydroxynaphthamide as a color former
US3307947A (en) * 1964-12-16 1967-03-07 Polaroid Corp Photographic products and processes
JPS4817890B1 (en)) * 1969-07-16 1973-06-01
JPH05504425A (ja) * 1990-12-19 1993-07-08 イーストマン コダック カンパニー 写真材料用アゾアニリンマスキングカプラー類
EP0574090A1 (en) 1992-06-12 1993-12-15 Eastman Kodak Company One equivalent couplers and low pKa release dyes

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2428054A (en) * 1945-08-30 1947-09-30 Eastman Kodak Co Photographic color correction using colored couplers
US2435616A (en) * 1944-07-07 1948-02-10 Eastman Kodak Co Elimination coupling with azosubstituted couplers

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE496951A (en)) * 1949-07-15

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2435616A (en) * 1944-07-07 1948-02-10 Eastman Kodak Co Elimination coupling with azosubstituted couplers
US2428054A (en) * 1945-08-30 1947-09-30 Eastman Kodak Co Photographic color correction using colored couplers

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3051568A (en) * 1955-12-06 1962-08-28 Edward K Kaprelian Offset electrophotography
US2908573A (en) * 1956-07-25 1959-10-13 Eastman Kodak Co Photographic color couplers containing mono-n-alkyl groups
US3028238A (en) * 1957-01-29 1962-04-03 Agfa Ag Color photography
US3148062A (en) * 1959-04-06 1964-09-08 Eastman Kodak Co Photographic elements and processes using splittable couplers
US3227551A (en) * 1959-04-06 1966-01-04 Eastman Kodak Co Photographic color reproduction process and element
US3227554A (en) * 1959-04-06 1966-01-04 Eastman Kodak Co Photographic elements and processes utilizing mercaptan-forming couplers
US3227550A (en) * 1962-09-07 1966-01-04 Eastman Kodak Co Photographic color reproduction process and element
US3285747A (en) * 1964-08-26 1966-11-15 Gen Analine & Film Corp Color formers containing a m-alkyl-phenoxyacyl group
US3459552A (en) * 1965-02-03 1969-08-05 Fuji Photo Film Co Ltd Silver halide emulsions containing magenta-colored cyan couplers
US3658545A (en) * 1968-12-20 1972-04-25 Konishiroku Photo Ind Light-sensitive silver halide color photographic material containing cyan couplers
US3859095A (en) * 1969-12-13 1975-01-07 Agfa Gevaert Ag Color-photographic material with improved color reproduction
US3926634A (en) * 1973-03-27 1975-12-16 Fuji Photo Film Co Ltd Color silver halide photographic materials containing couplers having an oleophilic group
US4042394A (en) * 1973-05-07 1977-08-16 Eastman Kodak Company Photographic dye image stabilization
US4002477A (en) * 1973-11-28 1977-01-11 Eastman Kodak Company Diffusion transfer processes and elements using or containing inert transitional metal complex oxidizing agents
US5100760A (en) * 1986-02-24 1992-03-31 Fuji Photo Film Co., Ltd. Light-sensitive material containing silver halide, reducing agent and polymerizable compound
US4871655A (en) * 1987-01-16 1989-10-03 Konica Corporation Light-sensitive silver halide color photographic material containing multi-functional dye
US4777120A (en) * 1987-05-18 1988-10-11 Eastman Kodak Company Photographic element and process comprising a masking coupler
US5399468A (en) * 1990-12-21 1995-03-21 Eastman Kodak Company Color photographic silver halide duplicating element and process
US6010839A (en) * 1998-06-26 2000-01-04 Eastman Kodak Company Color photographic elements containing yellow-colored magenta dye-forming masking couplers
US6132943A (en) * 1999-10-14 2000-10-17 Eastman Kodak Company Color photographic elements containing yellow-colored magenta dye-forming masking couplers

Also Published As

Publication number Publication date
US2860974A (en) 1958-11-18
FR1146556A (fr) 1957-11-13
FR72012E (fr) 1960-03-21
BE550154A (en))
CH345532A (de) 1960-03-31
DE1008574B (de) 1957-05-16
GB783730A (en) 1957-09-25
BE540231A (en))
DE964655C (de) 1957-05-23
GB853922A (en) 1960-11-09
FR73828E (fr) 1960-09-12
NL202187A (en))
NL113830C (en))

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