US2449966A - Integral mask for color film - Google Patents

Integral mask for color film Download PDF

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Publication number
US2449966A
US2449966A US533910A US53391044A US2449966A US 2449966 A US2449966 A US 2449966A US 533910 A US533910 A US 533910A US 53391044 A US53391044 A US 53391044A US 2449966 A US2449966 A US 2449966A
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United States
Prior art keywords
dye
coupler
color
image
light
Prior art date
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Expired - Lifetime
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US533910A
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English (en)
Inventor
Jr Wesley T Hanson
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
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Publication date
Priority to BE476358D priority Critical patent/BE476358A/xx
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US533910A priority patent/US2449966A/en
Priority to FR950284D priority patent/FR950284A/fr
Application granted granted Critical
Publication of US2449966A publication Critical patent/US2449966A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/32Colour coupling substances
    • G03C7/333Coloured coupling substances, e.g. for the correction of the coloured image
    • G03C7/3335Coloured coupling substances, e.g. for the correction of the coloured image containing an azo chromophore

Definitions

  • This invention relates to photography and particularly to a method for securing color correction in color transparencies used for printing.
  • the cyan dye which should absorb red light and transmit green and blue light usually absorbs a small amount of green and blue light as well as a major proportion of red light.
  • the magenta dye which should absorb green light and transmit blue and red light usually absorbs a considerable amount of blue light and a small amount of red light.
  • the yellow dye which should absorb blue light and transmit green and red light is usually satisfactory although some-- times it absorbs a small amount of green light.
  • the dye in the negative perior making corrected my invention by incorporating in the sensitive the dye may be emulsion layer a colored material especially a color coupler which absorbs the undesired absorption of a dye reduced in image form in the layer.
  • the colored material is a coupler, produced by coupling from the coupler itself thereby destroying the coupler in the portions of the layer in which an image is formed and leaving the coupler unailected in the remaining portions of the layer.
  • Figure 1 is a, graph illustrating the spectral absorption of representative dyes used in subtractive color processes.
  • Figure 2 is a graphic representation of the relative absorptions of representative subtractive dyes obtained by plotting the exposure expressed logarithmically against the optical density in various regions of the spectrum.
  • Figure 3 is a representation, partly sectional and partly graphical, of a photographic layer employing the correction method of my invention and showing the correction obtained on printing.
  • Figure 1 shows the absorption curves of typical subtractive dyes, yellow, magenta and cyan. If the optical density of each or these dyesat various wave lengths is determined, the graphs shownin Figure i may be obtained.
  • the yellow dye absorption is principally in the blue region between 400 and 500 millimicrons, although there is some absorption in the green region between 500 and 600 millimicrons.
  • the magenta dye absorbs principally in the green region, although there is a considerable absorption in the blue region and a smaller absorption in the red region between 600 and 700 millimicrons.
  • the cyan dye absorbs principally in the red region, although there is a considerable absorption in both the blue and the green spectral regions. These characteristics are fairly common to dyes generally used.
  • the absorption of the dyes of Figure l in the various regions of the spectrum are illustrated in the graphs of Figure 2.
  • the separate graphs indicate the absorption gamma of each dye in one of the three regions of the visible spectrum.
  • the horizontal rows 01 parts Y for example illustrate the absorptions of the yellow dye in the blue, green and red regions of the spectrum.
  • the principal or major absorption of the dye is indicated by a solid line, and the minor absorptions by dotted lines.
  • the graph YB therefore illustrates. the absorption of the yellow dye in the blue region
  • the graph MG illustrates the absorption of the magenta dye in the green region
  • the graph CR illustrates the absorption of the cyan dye in the red region.
  • the curves of Figure 2 are H and D curves of the dye images in various spectral regions and are said to represent absorption gamma, that is, the H and D curve of the dye image as read by light of any spectral region.
  • the curve YB represents the absorption gamma of the yellow dye whenread by blue light.
  • Figure 3 is in the form of a cross-section of an emulsion layer containing dye images. according to my invention, the dye images being illustrated Color couplersby means 01' their absorption gamma for the purpose oi illustration.
  • Figure 3 are portions of the same layer but are separated for purposes oi! clarity in illustration.
  • the emulsion layer contains a cyan dye image, the red absorption gamma 0! which is illustrated by curve 5.
  • the cyan dye image has minor absorptions of green and blue light as illustrated by the-absorption gamma I and 1 respectively. These curves correspond to the curves CR, CG, and CB, respectively, but are superposed in Figure 3.
  • the coloring material represented at 8 has blue and green light absorption, it adds to the blue and green absorption of the cyan dye as represented at 6 and 'l and therefore produces the same result as removing the absorptions represented at 6 and I, by converting them into non-image-forming, overall blue-green absorbers.
  • the coupler need not be incorporated in a. waterpermeable, water-insoluble solvent as described in those patents but may be incorporated in insoluble or non-difiusing form in the emulsion.
  • the coupler is colored so that it absorbs light prior to coupling but upon coupling is converted to a form which absorbs the color desired for the final dye image.
  • the color of the original coupler is chosen so that it absorbs light of the same color as the undesired absorption of the dye formed from it. In this way, the colored coupler can correct for the improper absorption of the coupled dyes and thus effect complete masking.
  • the cyan coupler should be red, orange or yellow, the magenta coupler yellow or green and the yellow coupler magenta or blue. The reason for choosing-these colors is apparent from a consideration of Figure 2 of the drawing.
  • the red, orange, or yellow coupler used for the cyan dye absorbs blue or blue and green lightwhich the cyan dye also absorbs but which it should transmit.
  • the yellow coupler used for the magenta dye absorbs 'blue light which the magenta dye absorbs but which it should transmit.
  • the magenta coupler used for the yellow dye absorbs green light which the yellow dye absorbs to a small extent but which it shouldtransmit.
  • Coupled CcBrN ⁇ l in-N N-c.nr-on 4 Ycllowm. Magenta.
  • CoKr-CO-H-N NCQKI man .Do.
  • Analternative method of introducing the correcting image into the emulsion layer is to use, instead of a colored coupler, a dye which can be bleached in the presenceof silver. If such dye is introduced into the emulsion layer along with the coupler, the choice of coupler is not limited to the color which it has before coupling, and there is also a. wider choice of bleachable dyes. If a red or orange dye is incorporated in the red-v sensitive layer for example, a positive image will be obtained from this dye if, after negative color development, the film is immersed in a bleached bath which destroys the masking dye in the presence of silver but does not affect the dye formed by coloring. In the presence of the negative silver image, the dye will be bleached and will leave a positive image.
  • the masking image used according to my invention is oi sign opposite to that o! the image dye.
  • the image dye is a negative, the masking dye will be a positive and vice versa.
  • I refer in the claims to a negative color image it is to be understood that I mean that it is negative with regardto the masking image orof opposite sign. It may be. any image which-is printed either from a negative or a positive.
  • Example sensitive layer containing a coupler yielding a magenta dye image (4) yellow filter layer, and (5) blue-sensitive layer containing a coupler yielding a yellow dye image.
  • This example will showa material in-which a colored coupler is used in the green-sensitive layer to provide a corrected magenta dye image. The details of the preparation of the several layers are given in the following paragraphs.
  • the coupler employed is 5(N-benzyl-N-naphthalene sulfonamino) 1-naphthol, dispersed in ethyl N ,N-di-m butyl carbamate, and the emulsion to which it is added is red-sensitized by known means.
  • this ,layer is 1-phenyl-3-n-pentadecyl-4-p-me thoxyphenylazo-S-pyrazolone.
  • This coupler is yellow and reacts with the oxidized developer to produce a magenta dye.
  • "the negative of the coupler are dissolved in 22.5 g. of tri-ocresylphosphate by gentle warming and this solution is emulsified with 40 cc. oi. 2% gelatin solution containing 1.5 g. of tri-isopropylnaphthalone sulfonate by passing the whole mixture through a colloid mill several times. The resulting emulsion is added to 1,000 cc. of a melted silver halide emulsion which has beensensitized to green. and the mixture coated over the redsensitive layer described above.
  • Yellow-filter lawn-This layer contains yellow colloidal silver a known from the prior art.
  • the composite coating prepared in the above manner is developed in the following solution, after exposing in the normal manner:
  • the time of development will depend on the nature of the particular silver halide emulsions employed. Development is followed by an acid hardening fixing bath and a silver removal bath according to well known practices.
  • the processed material thus obtained will contain a normal negative image in cyan dye in the red-sensitive layer, and a normal negative image in yellow dye in the blue-sensitive layer.
  • the green-sensitive layer will contain a negative image in magenta dye, and the residual coupler will make a reversed image of yellow coupler.
  • This negative image can be printed onto a normal multi-layer printing material for the production of three-color photographs.
  • the sensitive layer may be treated with a diazonium salt solution prior to color development in order to produce the colored coupler in the layer.
  • a diazonium salt solution may be used for this purpose, and the time during the production of the film to which the reaction with the diazonium solution is carried out may also be modified. Either of these conditions may be changed to give a number of diii'erent results.
  • the diazo coupling can be carried out when only part of the layers have been coated, that is, when only the red-sensitive layer or only the redand green-sensitive layers have been coated.
  • Diazo coupling 01' the complete multi-layer material can also be carried out at difierent times, such as before or after exposure. In the case of multilayer coatings, the character of the couplers and sults and will vary according to the desired ab-'.
  • the masking method which I propose to use has all the advantages of known masking methods with the additional advantages of the colored mask described in Evans U. S. application Serial No. 413,442, now U. S. Patent 2,376,132, and the advantages of an integral mask. Lack 01' registry between the mask and the picture image is no problem with my invention.
  • said colored coupler absorbing light in at least one of said minor absorption regions but absorbing no substantial amount of light in said major absorption region, which comprises exposing said layers to light and developing at least said layer containing said colored coupler by color development with a primary aromatic amino developing agent, said color development resulting in splitting off the chromophore-containing group of said colored coupler where said dye image is formed by coupling, leaving in the undeveloped regions of said one layer colored coupler absorbing light in said minor absorption region or said dye image.
  • the method oi. forming a color corrected image in a photographic element having superposed silver halide emulsion layers sensitive to different regions of the visible spectrum, at least one of said layers containing a dispersion in a water-permeable, water-insoluble solvent, of a colored color coupler for color-forming development having a chromophore-containing group in the position in the coupler which is reactive with the oxidation product of a primary aromatic amino developing agent, said chromophore-consion of the residual group taining group being split of!
  • the method 01 forming a color corrected image in a photographic element having superposed silver halide emulsion layers sensitive to diflerent regions of the visible spectrum, at least one of said layers containing a colored color coupler for color-forming development having an azo group in the position in the coupler which is reactive with the oxidation product of a primary aromatic amino developing agent, said azo group being split oil with simultaneous conversion of the residual group of the colored coupler to coupled dye by color development to form a cyan dye image which absorbs a major proportion of red light and a minor proportion of blue and green light, said coupler absorbing blue and green light but absorbing no substantial amount of red light, which comprises exposing said layers to light and developing at least said layer containing said colored with a primary aromatic amino developing agent, said color development resulting in splitting oi! the azo group and destruction oi the color of said colored coupler where said cyan image is formed, leaving blue-green absorbing coupler in the undeveloped regions of said one layer.
  • one of said color separations being formed by color development of said red colored coupler to a cyan dye, said color development resulting in splitting off the azo group and destruction of the color of said coupler where said cyan dye image is formed, leaving red colored coupler inthe undeveloped regions of said one layer.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US533910A 1944-05-03 1944-05-03 Integral mask for color film Expired - Lifetime US2449966A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
BE476358D BE476358A (pt) 1944-05-03
US533910A US2449966A (en) 1944-05-03 1944-05-03 Integral mask for color film
FR950284D FR950284A (fr) 1944-05-03 1946-08-29 Perfectionnements à la correction des couleurs par masque dans la photographie en couleurs

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Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2578333A (en) * 1949-06-28 1951-12-11 Eastman Kodak Co Photographic color correction process
US2584349A (en) * 1944-11-10 1952-02-05 Gen Aniline & Film Corp Color forming development with an aromatic primary amino developer and alpha-[4-sulfophenylazo]-aceto-acet-2-4-dichloroanilide
US2628902A (en) * 1947-04-29 1953-02-17 Raibourn Paul Process of producing colored photographs
US2629657A (en) * 1944-05-03 1953-02-24 Gen Aniline & Film Corp Multicolor negative film with integral masking images
US2629658A (en) * 1948-08-11 1953-02-24 Gen Aniline & Film Corp Silver halide emulsions containing nondiffusing azo dyes
US2633422A (en) * 1948-04-21 1953-03-31 Du Pont Process for making integral color correction masks
US2663637A (en) * 1948-08-20 1953-12-22 Ici Ltd Process of producing integral color correction masks
US2663638A (en) * 1948-09-15 1953-12-22 Ici Ltd Color correction of multicolor film by integral styryl dye masking images
US2681856A (en) * 1949-04-04 1954-06-22 Gaspar Photographic material and process for making an azo dye bleachout image
US2688541A (en) * 1950-11-20 1954-09-07 Ici Ltd Light-sensitive color photographic material
US2688538A (en) * 1949-07-15 1954-09-07 Ici Ltd Photographic elements and process of color correction utilizing styryl dyes as couplers
US2688539A (en) * 1951-11-08 1954-09-07 Gen Aniline & Film Corp Integral masking of photographic silver halide emulsions arranged in contiguous layers and containing colorless color formers and azo substituted coupling components
US2688540A (en) * 1950-11-20 1954-09-07 Ici Ltd Process for color photography
US2694008A (en) * 1948-10-22 1954-11-09 Agfa Ag Fur Photofabrikation Process for the production of colored masks in photographic color material
US2697036A (en) * 1949-11-23 1954-12-14 Eastman Kodak Co Multilayer photographic film having improved resolving power
US2697662A (en) * 1951-07-24 1954-12-21 Du Pont Color correction processes
US2704709A (en) * 1949-07-16 1955-03-22 Gen Aniline & Film Corp Masking process for multilayer photographic color film
US2763549A (en) * 1951-11-03 1956-09-18 Eastman Kodak Co False-color or false-sensitized photographic film containing colored couplers
US2774668A (en) * 1953-05-28 1956-12-18 Polaroid Corp Process and product for forming color images from complete dyes
US2823998A (en) * 1949-12-13 1958-02-18 Gevaert Photo Prod Nv Process and material for producing photographic multi-color images
DE1063900B (de) * 1956-12-31 1959-08-20 Gevaert Photo Prod Nv Verfahren zur Herstellung von farbmaskierten photographischen Farbenbildern durch Farbentwicklung
US3141773A (en) * 1957-02-12 1964-07-21 Agfa Ag Process and photographic material for the production of photographic records and copies which are corrected for tone value
DE2415132A1 (de) * 1973-03-31 1974-10-10 Konishiroku Photo Ind Farbiger photographischer purpurrotkuppler und diesen enthaltendes farbphotographisches silberhalogenid-aufzeichnungsmaterial
US4555477A (en) * 1985-01-02 1985-11-26 Eastman Kodak Company Photographic element and process utilizing metal complex color masking dyes
US4557998A (en) * 1985-01-02 1985-12-10 Eastman Kodak Company Colorless ligand-releasing monomers and polymers and their use to provide dyes with metal ions
US4680356A (en) * 1985-01-02 1987-07-14 Eastman Kodak Company Colorless ligand-releasing monomers and polymers and their use to provide dyes with metal ions
US4729943A (en) * 1985-12-09 1988-03-08 Eastman Kodak Company Color image-forming photographic reversal element with improved interimage effects
US4749641A (en) * 1986-09-15 1988-06-07 Eastman Kodak Company Imaging element containing dye masking coupler
US4774181A (en) * 1987-06-25 1988-09-27 Eastman Kodak Company Imaging element containing fluorescent dye-releasing coupler compound
US4777120A (en) * 1987-05-18 1988-10-11 Eastman Kodak Company Photographic element and process comprising a masking coupler
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
US5270156A (en) * 1991-10-11 1993-12-14 Konica Corporation Silver halide color photographic light sensitive material
US5972585A (en) * 1998-01-21 1999-10-26 Eastman Kodak Company Color negatives adapted for visual inspection
US6337176B1 (en) * 1999-09-29 2002-01-08 Fuji Photo Film Co., Ltd. Silver halide color photographic lightsensitive material

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102016121685A1 (de) 2016-11-11 2018-05-17 Krones Ag Vorrichtung zum Erwärmen von Kunststoffvorformlingen mit Abschirmplatte

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB503824A (en) * 1936-07-07 1939-04-11 Kodak Ltd Process of colour photography
US2193931A (en) * 1936-03-24 1940-03-19 Bela Gaspar Process for producing multicolored photographic images
US2241413A (en) * 1937-03-23 1941-05-13 Chromogen Inc Photographic printing process and image for use therein
US2307162A (en) * 1939-06-06 1943-01-05 Gen Aniline & Film Corp Process for the production of color images

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2193931A (en) * 1936-03-24 1940-03-19 Bela Gaspar Process for producing multicolored photographic images
GB503824A (en) * 1936-07-07 1939-04-11 Kodak Ltd Process of colour photography
US2241413A (en) * 1937-03-23 1941-05-13 Chromogen Inc Photographic printing process and image for use therein
US2307162A (en) * 1939-06-06 1943-01-05 Gen Aniline & Film Corp Process for the production of color images

Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2629657A (en) * 1944-05-03 1953-02-24 Gen Aniline & Film Corp Multicolor negative film with integral masking images
US2584349A (en) * 1944-11-10 1952-02-05 Gen Aniline & Film Corp Color forming development with an aromatic primary amino developer and alpha-[4-sulfophenylazo]-aceto-acet-2-4-dichloroanilide
US2628902A (en) * 1947-04-29 1953-02-17 Raibourn Paul Process of producing colored photographs
US2633422A (en) * 1948-04-21 1953-03-31 Du Pont Process for making integral color correction masks
US2629658A (en) * 1948-08-11 1953-02-24 Gen Aniline & Film Corp Silver halide emulsions containing nondiffusing azo dyes
US2663637A (en) * 1948-08-20 1953-12-22 Ici Ltd Process of producing integral color correction masks
US2663638A (en) * 1948-09-15 1953-12-22 Ici Ltd Color correction of multicolor film by integral styryl dye masking images
US2694008A (en) * 1948-10-22 1954-11-09 Agfa Ag Fur Photofabrikation Process for the production of colored masks in photographic color material
US2681856A (en) * 1949-04-04 1954-06-22 Gaspar Photographic material and process for making an azo dye bleachout image
US2578333A (en) * 1949-06-28 1951-12-11 Eastman Kodak Co Photographic color correction process
US2688538A (en) * 1949-07-15 1954-09-07 Ici Ltd Photographic elements and process of color correction utilizing styryl dyes as couplers
US2704709A (en) * 1949-07-16 1955-03-22 Gen Aniline & Film Corp Masking process for multilayer photographic color film
US2697036A (en) * 1949-11-23 1954-12-14 Eastman Kodak Co Multilayer photographic film having improved resolving power
US2823998A (en) * 1949-12-13 1958-02-18 Gevaert Photo Prod Nv Process and material for producing photographic multi-color images
US2688541A (en) * 1950-11-20 1954-09-07 Ici Ltd Light-sensitive color photographic material
US2688540A (en) * 1950-11-20 1954-09-07 Ici Ltd Process for color photography
US2697662A (en) * 1951-07-24 1954-12-21 Du Pont Color correction processes
US2763549A (en) * 1951-11-03 1956-09-18 Eastman Kodak Co False-color or false-sensitized photographic film containing colored couplers
US2688539A (en) * 1951-11-08 1954-09-07 Gen Aniline & Film Corp Integral masking of photographic silver halide emulsions arranged in contiguous layers and containing colorless color formers and azo substituted coupling components
US2774668A (en) * 1953-05-28 1956-12-18 Polaroid Corp Process and product for forming color images from complete dyes
DE1063900B (de) * 1956-12-31 1959-08-20 Gevaert Photo Prod Nv Verfahren zur Herstellung von farbmaskierten photographischen Farbenbildern durch Farbentwicklung
US3141773A (en) * 1957-02-12 1964-07-21 Agfa Ag Process and photographic material for the production of photographic records and copies which are corrected for tone value
DE2415132A1 (de) * 1973-03-31 1974-10-10 Konishiroku Photo Ind Farbiger photographischer purpurrotkuppler und diesen enthaltendes farbphotographisches silberhalogenid-aufzeichnungsmaterial
US4555477A (en) * 1985-01-02 1985-11-26 Eastman Kodak Company Photographic element and process utilizing metal complex color masking dyes
US4557998A (en) * 1985-01-02 1985-12-10 Eastman Kodak Company Colorless ligand-releasing monomers and polymers and their use to provide dyes with metal ions
US4680356A (en) * 1985-01-02 1987-07-14 Eastman Kodak Company Colorless ligand-releasing monomers and polymers and their use to provide dyes with metal ions
US4729943A (en) * 1985-12-09 1988-03-08 Eastman Kodak Company Color image-forming photographic reversal element with improved interimage effects
US4749641A (en) * 1986-09-15 1988-06-07 Eastman Kodak Company Imaging element containing dye masking coupler
US4777120A (en) * 1987-05-18 1988-10-11 Eastman Kodak Company Photographic element and process comprising a masking coupler
US4774181A (en) * 1987-06-25 1988-09-27 Eastman Kodak Company Imaging element containing fluorescent dye-releasing coupler compound
EP0296794A2 (en) * 1987-06-25 1988-12-28 EASTMAN KODAK COMPANY (a New Jersey corporation) Imaging element containing fluorescent dye-releasing coupler compound
EP0296794A3 (en) * 1987-06-25 1989-11-08 Eastman Kodak Company (A New Jersey Corporation) Imaging element containing fluorescent dye-releasing coupler compound
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
US5270156A (en) * 1991-10-11 1993-12-14 Konica Corporation Silver halide color photographic light sensitive material
US5972585A (en) * 1998-01-21 1999-10-26 Eastman Kodak Company Color negatives adapted for visual inspection
US6337176B1 (en) * 1999-09-29 2002-01-08 Fuji Photo Film Co., Ltd. Silver halide color photographic lightsensitive material

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FR950284A (fr) 1949-09-22
BE476358A (pt)

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