US3515557A - Photographic color film and process of making same - Google Patents

Photographic color film and process of making same Download PDF

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Publication number
US3515557A
US3515557A US447573A US3515557DA US3515557A US 3515557 A US3515557 A US 3515557A US 447573 A US447573 A US 447573A US 3515557D A US3515557D A US 3515557DA US 3515557 A US3515557 A US 3515557A
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color
coupler
lipophilic
hydrophilic
parts
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Victor F H Chu
Jacob Quentin Umberger
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EIDP Inc
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EI Du Pont de Nemours and Co
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    • 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
    • G03C7/3225—Combination of couplers of different kinds, e.g. yellow and magenta couplers in a same layer or in different layers of the photographic material

Definitions

  • a photographic color film comprising a support, a light-sensitive gelatino-silver halide layer which rs essen tially sensitive to one primary region of the visible spectrum and contains a lipophilic color coupler dispersed in a continuous phase of a hydrophilic color coupler containing at least one solubilizing carboxylic or sulfonic group, both of said color couplers being capable of forming the same dye color which is complementary to said primary color region, at least one of the color couplers being polymeric and the ratio of said hydrophilic to lipophilic coupler being about 30 to 300 parts of hydrophrlrc to about 100 parts of lipophilic color coupler.
  • This invention relates to color photography and more particularly to multilayer films for color photography. Still more particularly this invention relates to multilayer color photographic films, the light sensitive layers of which contain lipophilic and hydrophilic color couplers in separate phases. In another aspect, this invention relates to processes for the manufacture of multilayer color films comprising light sensitive layers containing lipophilic and hydrophilic color couplers in separate hases.
  • P The art of color photography is highly developed, and many photographic systems for recording images in color are known. The most widely accepted system at the present time is the so-called color reversal process of substrative color photography.
  • Integral-coupler multilayer color reversal films are well known and comprise, basically, a film support having coated thereon in order, a redsensitive gelatino-silver halide layer containing a cyan color coupler, a green-sensitive gelatino-silver halide layer containing a magenta color coupler, a yellow filter layer, and, finally, a blue-sensitive gelatino-silver halide layer containing a yellow color coupler.
  • Other auxiliary layers such as antihalation layers, separator layers and antiabrasion layers may also be present in the film element.
  • Color negative films are similar to reversal but have an additional requirement-colored couplers for color correction or masking.
  • Another method is to encapsulate the molecule in a polymer or high-boiling solvent which is water insoluble but dispersible in the hydrophilic colloid carrier, for the silver halide, e.g., gelatin.
  • Still another Patented June 2, 1970 ice method is to attach the color coupler molecule to the linear chain of a synthetic polymer which is either compatible with or dispersible in the colloid carrier for the silver halide.
  • couplers which may be made nondiffusible by one of the above methods fall into two very important groups; namely, water-soluble or hydrophilic and oil-soluble or lipophilic.
  • Hydrophilic couplers ordinarily have one or more water-solubilizing groups such as sulfonic or carboxylic groups in the molecule and the lipophilic couplers are devoid of such groups.
  • water-solubilizing groups such as sulfonic or carboxylic groups
  • the lipophilic couplers are devoid of such groups.
  • the hydrophilic or lipophilic characterization can affect the sensitometric nature which may or may not be desirable in the quality of the final color reproduction.
  • the prior art acknowledges the fact that nondifiusible hydrophilic color couplers containing the above mentioned acid groups have a strong tendency to react with gelatin when they are in solution.
  • One attempt to produce layers having good flexibility is by dispersing polymeric latices, e.g., polyethylacrylate, in the gelatin emulsion layers, but layer thickness is thereby increased.
  • polymeric latices e.g., polyethylacrylate
  • hydrophilic couplers they tend to influence the development rates. For example some magenta color couplers cause development acceleration whereas some cyan couplers retard development.
  • a substantially water-insoluble lipophilic coupler is preferably dissolved in a low-boiling solvent with or without a small amount of high-boiling solvent and dispersing the solution in a gelatino-silver halide emulsion containing a water soluble color coupler, it is possible to obtain films having thin, hard coatings of 0.0005 inch or less which are flexible, and can be developed to give colored images having good dye density and high resolution.
  • the low-boiling solvents are those which generally are volatile near the boiling point of water and preferably below it.
  • Exemplary of such solvents are methyl, ethyl, propyl and butylacetates; methyl propionate; ethyl and butyl formate; methylene chloride; nitromethane and nitroethane.
  • Other low-boiling solvents are known in the art.
  • the amount of low-boiling point solvent required depends upon the solubility of the lipophilic color coupler in the solvent under normal atmospheric conditions.
  • the amount of such solvent is usually no more than that needed to place the desired amount of lipophilic color coupler into the aqueous silver halide emulsion and to produce fine dispersions.
  • the ratio of the two types of couplers may vary over a wide range but in general the hydrophilic coupler may be used in amounts of at least 30 to 300 and preferably from 50 to 200 parts per 100 parts of the lipophilic couplers.
  • the two types of couplers may be chosen from either the monornolecular type containing weighting groups or the polymeric type as described above.
  • the high-boiling solvents which may be used with the lipophilic couplers are those having a double-bonded or semi-polar oxygen in their structure and boiling point above 200 C. They are particularly useful because of their plasticizing action on gelatin and hydrophilic couplers.
  • esters such as phthalates; N,N-dialkylarnides; sulfones; phosphate esters, e.g., tributyl phosphate; N-alkylated urethanes and mixtures thereof.
  • these highboiling solvents is optional because surprisingly, it has been found that lipophilic couplers, particularly those monomolecular types which contain large weighting groups have a plasticizing action on the gelatino-silver halide emulsion system. It then requires only the use of low-boiling solvents to effect dissolution and dispersion of the lipophilic color coupler in the emulsion.
  • the amount of high-boiling solvent may very from to 100 parts per 100'parts of lipophilic coupler.
  • EXAMPLE I This example illustrates the improvement in flexibility in a typical cyan color coupler-containing gelatin layer using a mixture of lipophilic and hydrophilic couplers as compared to using a hydrophilic color coupler alone.
  • a dispersion was made using a lipophilic cyan color coupler having the formula
  • n @fio ounomn The coupler in an amount of 6.5 grams was dissolved in 37.5 mils of ethyl acetate heated to 150 F.
  • the solution was dispersed by means of a Waring blendor into 300 mls. of a 5% aqueous gelatin solution containing 10 mls. of a 10% aqueous solution of an alkylated sodium naphthalene sulfonate as a surfactant.
  • the temperature of the mixture was maintained at 150 F. during the blending operation. Heating to 190 F. removed the ethyl acetate.
  • a sufficient amount of this mixture and also of the hydrophilic cyan color coupler copolymer described above were used to make a dispersion containing:
  • the resulting dispersion was coated on the polyethylene terephthalate film support to give a dried layer thickness of approximately 0.00032 inch. Both coatings were sea-- soned under room conditions for several weeks and then subjected to the wedge-brittleness test described by P. Z. Adelstein in Journal of Photographic Science and Engineering, vol. 1, No. 2, October 1957, pages 63-68 under conditions of 10% relative humidity.
  • the emulsion crack diameter for the gelatin layer containing the hydrophilic cyan color coupler alone was 0.39 inch while that of the gelatin layer containing the mixture of hydrophilic and lipophilic couplers was 0.23 inch.
  • a gelatin layer containing 60 parts of the lipophilic coupler, only, per parts of gelatin and coated to give a dried layer of 0.00033 inch in thickness showed a tendency for the color-coupler particles to aggregate excessively during color development as evinced by graininess pattern seen on 8 mm. color projection.
  • Example II Example I was repeated except that in the case of gelatin containing the hydrophilic coupler alone there was dispersed in the gelatin 20 parts of tributyl phosphate.
  • the lipophilic coupler was dispersed by using 20 parts of tributyl phosphate for dissolution in place of the ethyl acetate.
  • the dispersions were accomplished by means of a Waring blendor. No heating was required since ethyl acetate was absent.
  • the crack diameter of the hydrophilic couplergelatin-tributyl phosphate layer was 0.25 inch while that of the gelatin layer containing lipophilic and hydrophilic couplers and tributyl phosphate was 0.18 inch.
  • a color reversal film was prepared comprising the following:
  • a cellulose triacetate photographic 'film base support having a conventional substratum and coated thereon a non-halation layer comprised of 7 mg./dm. of bone gelatin and 3.5 mg./dm. of a colloidal silver dispersion absorbing light of all visible wave lengths.
  • a separator layer comprised of a solution of bone gelatin containing normal additives, saponin surfactant plus chrome alum hardener, coated over the cyan layer at a coating weight of 20 rug/dm. of gelatin.
  • the total calculated thickness of the layers was 0.0005 inch.
  • EXAMPLE V This example illustrates the superior results obtained in utilizing lipophilic and hydrophilic polymeric color (A) A color reversal film was prepared as described in (A) of Example IV except that the film support was 0.004 inch thick and constructed as disclosed in Example IV of Alles, US. Pat. 2,779,689 and the final structure of the film had the following characteristics:
  • Antiabrasion Yellow mgJdmfi. 17 11 Yellow filter layer, as described in Ohu et al.,
  • the lipophilic yellow copolymeric color coupler obtained by copolymerizing 1.0 mole of the above monomer with 1.5 moles of Z-ethylhexyl acrylate.
  • the resulting lipophilic yellow color coupler copolymer was introduced into the gelatino-silver halide emulsion in the same manner as the above lipophilic cyan color coupler copolymer.
  • the three silver halide emulsions were so constructed and coated that the quantities of silver halide calculated as silver bromide, total lipophilic and hydrophilic color coupler and gelatin were of approximately the same coating weight as in the color film A above.
  • the lipophilic color coupler was introduced into the gelatino-silver bromoiodide emulsion by first dissolving 400 grams of the copolymer in 4000 ml. ethyl acetate and 120 mls. of di-isobutyl phthalate and introducing this solution with high speed stirring into an aqueous gelatin solution containing 120 grams of gelatin, 7000 ml. of distilled water and 320 ml. of a 10% aqueous solution of sodium lauryl sulfate.
  • the processing solutions have the following formulations:
  • EXAMPLE VI This example illustrates the use of a hydrophilic cyan polymeric color coupler in conjunction with a lipophilic colored color coupler in a dispersed phase for the purpose of color correction which is useful in color negative films.
  • a lipophilic colored color coupler was prepared by dissolving 10 grams of the color coupler:
  • Solution (A) was added to solution ,(B) at 100-105 F. and thoroughly dispersed by means of a high speed homomixer.
  • the resulting dispersion of 3 types of cyan couplers was added to a gelatino-sil-ver bromoiodide in the manner taught by the above examples and could be used in the manufacture of extremely thin, flexible high definition photographic color films.
  • EXAMPLE VIII This example illustrates the use of anionic surface active couplers to disperse and incorporate into gelatino silver halide emulsions lipophilic polymeric couplers which were found to be very soluble in solvents such as organic esters. These uniquely soluble lipophilic polymers are prepared by addition polymerization of a coupler where the color-coupling group Q is attached to a polymerizable vinyl group via the connecting bivalent radial A taken from O- and 0 II ....o
  • Coatings of 25 mg./dm. of silver halide were prepared from emulsions of composition:
  • Films A, B, C and D were exposed in a sensitometer and processed in the first or black-and-white developer of Example V. It was observed that the rate of development of silver in film A was retarded, relative to the control D, presumably due to the naphthal structure of the hydrophilic coupler. In film B with the majority of the naphthol now in the lipophilic dispersed phase, the development inhibition was lessened. Film C exhibited rapid development suggesting that this hydrophilic polymer coupler accelerates the development of silver.
  • EXAMPLE IX A color reversal film was prepared as described in (A) of Example IV except that the blue sensitive emulsion (6) contained per 120 parts of gelatin, 117 parts of benzoylacetanilide yellow color former shown in (6) and 685 parts of the yellow color former formed by polymerizing 1 mole of the monomer, p-methacrylaminebenzoylacetanilide and 2 moles of ethyl acrylate.
  • the lipophilic coupler was dispersed by dissolving in a 168/ 14-0 ethanol/water solution at pH 11.35 and adjusting the pH to 6.3 after mixing the color formers.
  • the emulsion was coated to give a total color former coating weight of about 24 mg./dm.
  • a dispersed phase lipophilic compound in a continuous phase of a hydrophilic compound is applicable to other aspects of photographic color film elements than to the incorporation.
  • color couplers For example one may incorporate a hydrophilic polymeric color coupler in a continuous phase and a lipophilic color coupler dispersed by means of a soaplike weighted color coupler containing anionic groups which have surfactant characteristics.
  • the invention may be used for the incorporation of both lipophilic and hydrophilic filter dyes and ultraviolet absorbing dyes and stabilizers in emulsion layers and filter layers which can bring about improvements in definition, color rendition and aging stability.
  • the process of the invention may also be used to incorporate dyes in photographic color films which are used to form color images by the catalytic or dye bleach-out system. It will also be evident that the invention is applicable to any of the vast number of color couplers which may be obtained in both lipophilic and hydrophilic forms.
  • the invention is not limited to gelatin layers or to gelatino-silver halide emulsion layers. It may also be used in silver halide systems utilizing other natural or synthetic colloids. As will be apparent from the examples the invention may not only be used for color reversal systems but can be just as readily utilized in conventional negative-positive systems of subtractive color photography.
  • the mixed hydrophilic-lipophilic couplers of this invention lessen the need for exceedingly fine dispersions of the lipophilic coupler since it comprises only part of the total image-forming coupler.
  • the need for ethyl acetate as auxiliary to the high-boiler for dispersion is lessened.
  • the safety hazard, cost and complexity of removing ethyl acetate can be avoided.
  • the mixed couplers of this invention permit formation of neutral-colored developed dyes images. They permit control of relative rates of dye development in the hydrophilic and lipophilic phases via control of the amount of oil in the droplets and solvent such as benzyl alcohol in the color developer.
  • This invention allows the achievement of an optimum balance between emulsion thinness and flexibility with no loss in resolution in the resulting color images.
  • it combines the flexibility of the dispersed oil-droplet system of lipophilic color coupler incorporation with the high definition of compatible or continuous phase hydrophilic color coupler systems without the disadvantages of excessive softness of the dispersed systems and the brittleness of the continuous phase systems.
  • a further advantage flowing from the invention is that the black-and-white development rates for each of the constituent layers, yellow, cyan and magenta in color reversal films can be much more uniform by adjustment in each layer of the ratio hydrophilic to lipophilic couplers.
  • a thin, flexible multilayer photographic color film comprising a support bearing three silver halide layers and a yellow filter layer which have a total thickness no greater than 0.0005 inch and are so disposed and sensitized that each silver halide layer is essentially sensitive to a difierent primary color region of the visible spectrum, each of said silver halide layers containing a hydrophilic color coupler containing at least one solubilizing carboxylie or sulfonic group in a continuous phase and a lipophilic color coupler devoid of such groups dispersed in the continuous phase, both of said couplers form the same dye color which is essentially complementary to the primary color that exposes the silver halide in the individual layer, at least one of said color couplers being polymeric and having a vinyl chain of atoms with recurring color coupler groups attached to units of the chain of atoms, and the ratio of said couplers being about 30 to 300 parts of hydrophilic coupler to about parts of said lipophilic coupler.
  • each of said silver halide layers contains up to 100 parts of high-boiling point plasticizer to about 100 parts of said lipophilic coupler.
  • a photographic color film comprising a support, a light-sensitive gelatino-silver halide layer which is essentially sensitive to one primary region of the visible spectrum and contains a lipophilic polymeric color coupler having a vinyl chain of atoms with recurring color coupler groups attached to units of the chain of atoms, said coupler being dispersed in a continuous phase of an anionic surfactant which is a hydrophilic color coupler, both of said color couplers being capable of forming the same dye color which is complementary to said primary color region and the ratio of said hydrophilic to lipophilic coupler being about 30 to 300 parts of hydrophilic to about 100 parts of lipophilic color coupler.
  • a photographic color film comprising a support, a light-sensitive gelatino-silver halide layer which is essentially sensitive to one primary region of the visible spectrum and contain a lipophilic polymeric color coupler having a vinyl chain of atoms with recurring color coupler groups attached to units of the chain of atoms, said couple being dispersed in a continuous phase of a hydrophilic color coupler and an anionic surfactant which is a hydrophilic color coupler, all of said color couplers being capable of forming the same dye color which is complementary to said primary color region and the ratio of said hydrophilic to lipophilic coupler being about 30 to 300 parts of hydrophilic to about 100 parts of lipophilic color coupler.
  • a process for preparing a color photographic emulsion which comprises stirring a hydrophilic color coupler containing at least one carboxylic or sulfonic group with an aqueous gelatin solution containing silver halide which is sensitive to a primary color region of the visible spectrum, dispersing into another aqueous gelatin solution a lipophilic color coupler free from solubilizing groups dissolved in an organic solvent having a boiling point less than the standard boiling point of Water, and mixing said solutions together to give a ratio of about 30 to 300 parts of said hydrophilic color coupler to about 100 parts of said lipophilic color coupler, both of said color couplers being capable of forming the same color dye which is complementary to the color region sensitivity of said silver halide, and at least one of said color couplers is polymeric and having a vinyl chain of atoms with recurring color coupler groups attached to units of the chain of atoms.
  • lipophilic color coupler is dissolved in a mixture of said organic solvent and a high-boiling point liquid plasticizer capable of dissolving said lipophilic coupler.
  • a process for preparing a multilayer photographic color film which comprises making three separate hydrophilic-lipophilic color couplers containing silver halide emulsions as defined in claim 5 where each separate emulsion is sensitized to a different primary color of the visible spectrum, coating each of said emulsions and a yellow filter layer in the desired order on the same surface of a support and drying said element at a temperature greater than the boiling point of said low-boiling solvent.
  • a hydrophilic color coupler containing at least one solubilizing carboxylic or sulfonic group as a continuous phase and a lipophilic color coupler devoid of such groups, dispersing it in the continuous phase of each of said silver halide layers in combined amount to give the desired color density in each layer, at least one of said color formers being polymeric and having a vinyl chain of atoms with recurring color coupler groups attached to units of the chain,'said color couplers being capable of forming the same dye color which is complementary to the color region sensitivity of the silver halide layer in Which the couplers are placed and the ratio of couplers to one another being about 30 to 300 parts of hydrophilic coupler to about parts of lipophilic coupler.

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US447573A 1965-04-12 1965-04-12 Photographic color film and process of making same Expired - Lifetime US3515557A (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0007593A1 (de) * 1978-08-01 1980-02-06 Agfa-Gevaert AG Farbfotografisches Entwicklungsverfahren
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
US5051346A (en) * 1985-02-16 1991-09-24 Konishiroku Photo Industry Co., Ltd. Light-sensitive photographic material comprising lipophilic coupler hydrophilic coupler and diffusion inhibitor releasing
US20090305048A1 (en) * 2006-03-23 2009-12-10 Rhodia Operations Process for the treatment of a hydrophobic surface by an aqueous phase

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2322027A (en) * 1940-02-24 1943-06-15 Eastman Kodak Co Color photography
US2801170A (en) * 1954-12-20 1957-07-30 Eastman Kodak Co Preparation of color former dispersions
US2852381A (en) * 1953-10-13 1958-09-16 Eastman Kodak Co Photographic emulsions containing polymeric color formers
US3249431A (en) * 1960-03-29 1966-05-03 Gevaert Photo Prod Nv Production of color photographic images

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE565852A (en:Method) * 1957-03-20
CH450916A (de) * 1964-06-12 1968-05-15 Ferrania Spa Verfahren zur Herstellung von farbphotographischen Materialien

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2322027A (en) * 1940-02-24 1943-06-15 Eastman Kodak Co Color photography
US2852381A (en) * 1953-10-13 1958-09-16 Eastman Kodak Co Photographic emulsions containing polymeric color formers
US2801170A (en) * 1954-12-20 1957-07-30 Eastman Kodak Co Preparation of color former dispersions
US3249431A (en) * 1960-03-29 1966-05-03 Gevaert Photo Prod Nv Production of color photographic images

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0007593A1 (de) * 1978-08-01 1980-02-06 Agfa-Gevaert AG Farbfotografisches Entwicklungsverfahren
US4297438A (en) * 1978-08-01 1981-10-27 Agfa-Gevaert Aktiengesellschaft Color-photographic development process
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
US5051346A (en) * 1985-02-16 1991-09-24 Konishiroku Photo Industry Co., Ltd. Light-sensitive photographic material comprising lipophilic coupler hydrophilic coupler and diffusion inhibitor releasing
US20090305048A1 (en) * 2006-03-23 2009-12-10 Rhodia Operations Process for the treatment of a hydrophobic surface by an aqueous phase
US8222304B2 (en) * 2006-03-23 2012-07-17 Rhodia Operations Process for the treatment of a hydrophobic surface by an aqueous phase
US8946306B2 (en) 2006-03-23 2015-02-03 Rhodia Operations Process for the treatment of a hydrophobic surface by an aqueous phase
EP1996655B1 (en) * 2006-03-23 2019-10-02 Rhodia Opérations A process for the treatment of a hydrophobic surface by an aqueous phase

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DE1572133B1 (de) 1971-05-06

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