US3211552A - Multilayer photographic element for color photography - Google Patents

Multilayer photographic element for color photography Download PDF

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US3211552A
US3211552A US113100A US11310061A US3211552A US 3211552 A US3211552 A US 3211552A US 113100 A US113100 A US 113100A US 11310061 A US11310061 A US 11310061A US 3211552 A US3211552 A US 3211552A
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color
gelatin
forming
layer
silver halide
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US113100A
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Chu Victor Fu-Hua
Firestine John Charles
Umberger Jacob Quentin
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EIDP Inc
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EI Du Pont de Nemours and Co
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Priority to NL278981D priority Critical patent/NL278981A/xx
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to US113100A priority patent/US3211552A/en
Priority to GB20101/62A priority patent/GB995364A/en
Priority to DEP29486A priority patent/DE1154717B/de
Priority to FR899003A priority patent/FR1332611A/fr
Priority to ES277758A priority patent/ES277758A1/es
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Publication of US3211552A publication Critical patent/US3211552A/en
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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
    • G03C7/327—Macromolecular coupling substances
    • G03C7/3275—Polymers obtained by reactions involving only carbon-to-carbon unsaturated bonds, e.g. vinyl polymers

Definitions

  • This invention relates to color photography and more particularly to multicolor elements for chromogenic development.
  • a multilayer color film e.g., monopack or integral tripack
  • that portion of the image recorded in the inner or lower layers it is theoretically impossible for that portion of the image recorded in the inner or lower layers to be equivalent, in such qualities as sharpness and resolving power, to images recorded in monolayer films.
  • the use of color separation negatives permits each image record to be carried in an outer layer, but the problems of image registration in printing have created a greater demand for the monopack multicolor films.
  • Such films are essential for multicolor reversal processes using color development.
  • An object of this invention is to provide improvements in the field of photography and more particularly in multilayer elements for chromogenic development. Another object is to provide multilayer color films for chromogenic development which have both high resolving power values and the processing simplicity of integral coupler emulsions. A further object is to provide such films which can be readily made by using conventional chemical apparatus, and aqueous coating and drying apparatus. A still further object is to provide high-speed color reversal films of the foregoing types. Still further objects will be apparent from the following description of the invention.
  • the improved multicolor elements of this invention comprise a support, e.g., film, plate or paper, bearing a plurality (preferably three) of differentially sensitized silver halide emulsion layers having an integral emulsion thickness (6) not more than 12.5 microns and preferably 7.6 to 12.5 microns, each adapted to record images from light in a different region of the visible spectrum and containing a water-permeable binder comprising gelatin and a compatible color-forming vinyl addition polymer containing a plurality of color-former nuclei capable of forming a quinoneimine, azomethine or an azo dye upon color-coupling development of a silver salt image, the etfective color-forming equivalent weight of the binder being not more than 1750, preferably 5001750, said addition polymer also containing a plurality of watersolubilizing anionic groups so that the polymer remains in solution in water at 25 C.
  • a support e.g., film, plate or paper
  • the modified gelatino-silver halide emulsion layers may contain, as shown in the working examples below, about 7 to 25 parts by weight of the compatible color former per about 10 to 30 parts by weight of gelatin.
  • the color-former nuclei are extralinear, being linked to a carbon atom of the wholly carbon chain by various linkages including amide, ether and cyclic acetal linkages.
  • the pH can be adjusted by addition of alkali, e.g., NaOH, KOH, Na CO or K CO In these films, the thickness, 8, is as defined in the Eggert and Grossman reference.
  • novel elements of the invention may also contain a yellow filter stratum or layer and, in the case of color reversal films, the blue-sensitive layer should be outermost and the remaining silver halide layers adapted to record in the red and green regions of the spectrum being disposed in any order and preferably all on the same side of the support.
  • the color-formers in the blue, green and red regions of the spectrum in general, should yield dyes upon development complementary in color to the utilized sensitivity of the respective silver halide emulsion layers.
  • equivalent weight is meant the number of grams of color-forming polymer containing one gram molecular weight of the active color-forming nucleus or coupling group, e.g., reactive methylene group.
  • the equivalent weight can be determined from ultraviolet spectral analysis of a solution of the anionic color-former, as follows:
  • the effective coupling equivalent weight is a measure of the efiiciency of the total binder-color-former system, in yielding thin color emulsions. It is defined as the quotient obtained when color-former equivalent weight is divided by the fraction of the total binder comprised of color-former. The lower the effective equivalent Weigh the more efficient is the color-former in forming thin layers.
  • the thickness, A has been defined above in reference to the article by Eggert and Grossman.
  • At least one of the gelatin/col-or-forming polymer silver halide emulsions can have admixed therewith a plasticizer, e.g., glycerine, diethylene gylcol, triethylene glycol, tricresyl phosphate, dimethyl sebacate, dioctyl phthalate (Flexol DOP), triethylene glycol di-Z-ethylhexoate, ethyl phthalyl ethyl glycolate, and oand p-toluene ethyl sulfonamide.
  • a plasticizer e.g., glycerine, diethylene gylcol, triethylene glycol, tricresyl phosphate, dimethyl sebacate, dioctyl phthalate (Flexol DOP), triethylene glycol di-Z-ethylhexoate, ethyl phthalyl ethyl glycolate,
  • the preferred color-forming elements of the invention also contain a flexibilizing polymer which acts as a third binder component.
  • this third binder component should be an addition polymer of relatively low melting point and free from ionized groups and primary amide groups.
  • This third polymer component acts as a co-binder for silver halide along with gelatin and the compatible polymeric color-former.
  • Eifective equivalent weight is as defined previously, whether for a twoor a three-component binder system, and the same upper limit of 1750 applies.
  • This third binder may be liquid and water-soluble at 25 C., i.e., liquid copolymers of ethylene and propylene oxides with Saybolt viscosities of 900 to 90,000 Universal seconds are useful, but preferably is water-insoluble and is present in the form of a dispersion of small, solid particles having an average diameter of less than l-micron.
  • the mixed binder comprised of gelatin, polymeric colorformer, and flexibilizing polymer forms a continuous blend when the dry film is viewed under an ordinary microscope.
  • Silver halide emulsion layers having the three-component binder have the advantage over layers containing two component binders in that they have improved flexibility and reduced tendency to curl.
  • the layers moreover, can be made uniform in image-yielding properties and extremely thin, e.g., in the order of 2.5 to 5.0 microns.
  • Useful polymeric color-formers contain recurring colorformer nuclei and recurring anionic grougs, e.g., carboxylic or sulfonic acid groups or the corresponding Na, K, NH amine or quaternary ammonium salts, which confer water-soluble properties to the color-former.
  • Color-formers of this type may be vinyl or vinylidene type addition polymers having a wholly carbon chain or backbone to which there are attached extralinear groups containing the solubilizing groups and the color-former nuclei.
  • color-former nuclei are meant nuclei containing groups which are capable of coupling with oxidation products or aromatic primary amine developing agents, e.g., p-phenylenediamine, formed during the development of silver salt images, to form a quinoneimine, azomethine or in some instances an azo dye image.
  • the nuclei have a structure which may be represented by the formula:
  • nuclei are found in the reactive methylene dye intermediates and in aromatic hydroxyl compounds and includes the reactive ethanol groups. These groups occur in phenols, naphthols, acylacetamides, cyanoacetyles, beta-ketoesters, pyrazolones, homophthalimides, coumaranones, indoxyls, thioindoxyls, and indazolones.
  • Polymeric color-formers having the prescribed low equivalent weights which satisfy the above requirements include those disclosed in Firestine and Umberger, Ser. No. 21,959 filed April 3, 1060 (US. Patent 3,163,625, Dec. 29, 1964), and those obtainable by substituting for the l-phenyl-3-methacrylamido-5-pyrazolone monomeric reactant in the processes thereof, p-(cyanoacetyl)methacrylanilide or 6-methacrylamidoindazolone; in Schoenthaler and Warfield, Ser. No. 586,636 filed Sept. 27, 1960, abandoned and replaced by continuation-in-part application Ser. No. 394,040, filed Sept. 2, 1964, and in Umberger application for Dye Intermediates, Ser. No.
  • the film element is re-exposed to light and then developed in an aqueous alkaline developer solution of the type disclosed in Example I of Jennings US. Patent 2,397,865, Apr. 2, 1946.
  • aqueous alkaline developer solution of the type disclosed in Example I of Jennings US. Patent 2,397,865, Apr. 2, 1946.
  • any of the other color-developing agents described in said Jennings patent can be used.
  • the preferred developer solutions however, have a higher content of sodium sulfite and contain 20 to 60 grams of sodium sulfite (anhydrous basis) per liter of solution.
  • the color developer solutions may also contain a small proportion of an organic solvent, e.g., benzyl alcohol, benzyl amine, dimethyl formamide, to insure solubility of the developing agent and to insure full development of maximum dye density, particularly in emulsions relatively high in their ratio of synthetic polymer to gelatin.
  • an organic solvent e.g., benzyl alcohol, benzyl amine, dimethyl formamide
  • Useful low melting, non-ionized, synthetic vinyl polymers capable of serving as a co-binder with gelatin and a polyanionic color-former to improve the flexibility of the film, include the preferred class of alkyl acrylates and methacrylates, e.g., polymers and copolymers of methyl, ethyl, butyl, ethylhexyl acrylate and methyl and butyl methacrylate.
  • acrylic acid can be used in small amounts in the preparation of the copolymers in order to modify properties of the copolymer.
  • polymers can be made from the vinyl esters, such as the acetate, propionate, etc., the vinyl and vinylidene halides such as vinylidene chloride; styrene and substituted styrenes; the dienes such as butadiene; acrylonitrile; alkenes such as ethylene or propylene, and the like.
  • vinyl esters such as the acetate, propionate, etc.
  • vinyl and vinylidene halides such as vinylidene chloride
  • styrene and substituted styrenes such as butadiene
  • acrylonitrile alkenes such as ethylene or propylene, and the like.
  • water-insoluble polymers are added as dispersions of fine particle size obtained by techniques of emulsion polymerization known in the art, such as the use of adequate concentrations of surfactants, the mode of stirring, the concentrations of reactants, temperature, rate of addition of monomer, etc., and by dispersing a preformed polymer, e.g., polyethylene, with suitable surfactants.
  • a preformed polymer e.g., polyethylene
  • Preferred amphoteric dispersing agents and procedures for preparing the dispersions are disclosed in Nottorf, U.S. Ser. No. 94,989 filed March 13, 1961.
  • dispersing agents are other amphoteric compounds such as betaines, e.g., C-cetyl betaine, taurines, glycines, etc., as well as the anionic dispersing agents such as sodium dodecyl sulfate, dodecylbenzene sulfonic acid, naphthalenesulfonic acid condensed into a polyanion with formaldehyde, sodium isopropylnaphthalene-sulfonic acid and sodium dioctylsulfosuccinate.
  • betaines e.g., C-cetyl betaine
  • taurines e.g., glycines, etc.
  • anionic dispersing agents such as sodium dodecyl sulfate, dodecylbenzene sulfonic acid, naphthalenesulfonic acid condensed into a polyanion with formaldehyde, sodium isopropylnaphthalen
  • a hydrophobic film support e.g., cellulose acetate, cellulose triacetate, cellulose propionate, cellulose butyrate, cellulose acetatebutyrate, etc., or a superpolymer such as nylon, polyvinyl chloride, polyester, e.g., polyethylene terephthalate, polycarbonate, etc., glass, wood, paper, etc., suitably subbed to provide proper adhesion with layers to be coated thereon, is coated on one surface with a non-halation layer comprising gelatin in which there is dispersed colloidal silver capable of absorbing light of all visible wavelengths.
  • a non-halation layer comprising gelatin in which there is dispersed colloidal silver capable of absorbing light of all visible wavelengths.
  • Coated in order on the non-halation layer are a gelatinosilver halide emulsion layer sensitive to blue and red light and containing a polyanionic cyan color-former, a gelatin separator layer, a gelatino-silver halide emulsion layer sensitive to blue and green light and containing a polyanionic magenta color-former, a gelatin layer containing a blue light-absorbing material, e.g., colloidal silver, a gelatino-silver halide emulsion layer sensitive to blue light and containing a polyanionic yellow colorformer, and a gelatin anti-abrasion layer.
  • the silver halide layers have the characteristics and thickness defined above.
  • the light-sensitive emulsion layers may be arranged with respect to the support in other manners and with other arrangements of spectral sensitivities and colorformers as is known in the art. Suitable other layer arrangements are disclosed in U.S. Patents 2,397,864, 2,927,019 and 2,927,024, and in assignees Blanchard U.S. application Ser. No. 672,495 filed July 17, 1957 (U.S. Patent 2,997,388, Aug. 22, 1961). However, the advantages of the thin emulsion layers of this invention will be most appreciated in a configuration in which the uppermost light-sensitive layer contains a yellow color-former.
  • Film C with no blue record emulsion, resolved 100 lines per millimeter
  • Film A with a thin blue record emulsion and a thin separator layer, resolved lines per millimeter
  • Film B with relatively thick blue record emulsion and thick filter layer, resolved only 60 lines per millimeter.
  • the photosensitive silver halide crystals are still formed in a limited amount of gelatin to effect the ripen- 7 ing and sensitizing of gelatino-silver halide emulsions.
  • the blend of gelatin and polymeric color-former constitutes a continuous phase (on a microscopic scale) and together with the two polymers, one of natural origin and the other synthetic, share the binder function for the silver halide crystals.
  • the color developers employed in processing are unusually high in sodium sulfite content, viz., 20 to 60 grams of anhydrous Na SO are employed per liter of developer solution as compared with the more normal range 2 to grams per liter employed heretofore.
  • the high-sulfite color developers help to prevent interlayer color contamination caused by migration of color-formers and oxidized developer molecules and yield processed film free from haze due to prevention of excessive emulsion swelling in alkaline developers.
  • a significant dye density is obtained in View of the known action of sulfite ion to prevent color-coupling by reacting with oxidized developer.
  • a cellulose triacetate photographic film base support having a conventional substratum and coated thereon a non-halation layer comprised of 7 rng./dm. of bone gelatin and 3.5 mg./dm. of a colloidal silver dispersion absorbing light of all visible wave lengths.
  • Film 1 employed a polyanion cyan color-former of the polyvinyl ether type, shown in Example I of assignees copending Umberger application entitled, Dye Intermediates, Ser. No. 113,101 filed May 29, 1961 (abandoned Dec. 17, 1964, and replaced by application Ser. No. 419,227, Dec.
  • Film 2 employed a polyanion cyan color-former of the polyvinyl acetal type described in Example I of assignees Schoenthaler and Warfield application Ser. No. 58,636, filed Sept. 27, 1960 (abandoned Oct. 24, 1964, and replaced by continuation-in-part application Ser. No. 394,040 filed Sept. 2, 1964).
  • Film 3 employed a polyanion cyan color-former of the polyrnethacrylhydrazide type prepared by a procedure similar to that shown in Example I of assignees copending application of Firestine and Umberger U.S. Ser. No. 21,959,
  • a separator layer comprised of a solution of bone gelatin containing the normal additives, saponin surfactant plus chrome alum hardener, coated over all of Films 1, 2, 3 and 4 at a coating weight of 20 mg. gelatin/ dm.
  • the coating weights of Ag halide, gelatin and colorformer were 32 mg./dm. 17 mg./dm. and 9.6 mg./ dm. respectively, and effective coupling equivalent weight was computed to be 970.
  • a gelatino-silver bromo-iodide emulsion layer sensitive to blue light containing 1.7 mole percent silver iodide and 98.3 mole percent silver bromide and containing a polyanion benzoylacetanilide yellow colorformer prepared by transacetalization of 100 parts of low viscosity 99% hydrolyzed polyvinyl alcohol with 120 parts of m-benzoylacetamidobenzaldehyde ethylene glycol acetal and 50 parts of o-sulfobenzaldehyde in an ethanol-water reaction medium with p-toluenesulfonic acid to pH 1.7 as acetalization catalyst to yield a color-former of 775 equivalent weight.
  • the coating weights of silver halide, gelatin, and color-former were 25 mg./dm. 10 mg./dm and 25 rng./drn. respectively, which is computed to be 1090 effective coupling equivalent weight.
  • the four films just described were slit to a width of 32 mm., conventionally perforated, slit to 16 mm. width and exposed in an S-mm. camera.
  • the films were processed by reversal with all solutions at 70 F. First they were developed in a conventional black and white, pmethylaminophenolhydroquinone developer, then treated with an acid shortstop bath, water washed, and re-exposed by flashing to white light.
  • the four films were compared for image definition by projecting on a screen using, as a control, a commercially available S-mm. color reversal film with non-integral couplers, i.e., a film processed with the couplers in the developer solutions.
  • the 8-mm. screen projection a severe test for image definition, showed the four coatings essentially equivalent to the control. This is a consequence of similar total emulsion thickness determined to be about 15 microns (excluding the antihalation layer) for all five films including the control.
  • the abrasion layer was doubled in thickness of gelatin and hardened with chrome alum plus formaldehyde rather than just chrome alum as in the previous examples, and thus clear S-mm. projection results were obtained after exposure and processing.
  • the actual coating weights employed for this yellow emulsion were 20 mg/dm. silver halide, 30 rng./dm. gelatin, and 16 mg./dm. color-former. These data yield an eifective coupling equivalent Weight computed to be 1750.
  • EXAMPLE III A film was coated similar to Film 1 of Example II but with the addition of 12 mg./dm. of polyethylacrylate to the cyan layer, 6 mg./dm. to the magenta layer, and 15 mg./dm. to the yellow emulsion layer.
  • the polyethyl acrylate was added as a 30% by weight aqueous dispersion using disodium-N-tallow-beta-iminodipropionate as the dispersing agent, made according to Procedure A of Nottorf, U.S. Ser. No. 94,989, filed March 13, 1961 (U8.
  • Patent 3,142,568, July 28, 1964 The effective coupling equivalent weights were increased by the addition of this third binder component but still did not become higher than 1750 as shown in Table II below.
  • Dispersions of polybu-tylacrylate and poly-2-ethylhexylacrylate prepared similarly by emulsion polymerization, with disodium-N-tallow-beta-iminodipropionate as a dispersing agent, performed in equivalent fashion to the polyethylacrylate latex in improving flexibility of blended gelatin and polyanion color-former binder.
  • EXAMPLE IV The advantages of high sulfite content of the color developer solution were demonstrated by comparing film strips of Film 1 of Example II with strips from two other films which differed only in the amounts of the magenta emulsion coated as layer (b).
  • the low coating weight film had a silver halide coating weight of 24 rng./dm. in the magenta layer
  • Film 1 of Example II had a silver halide coating weight of 34 mg./dm.
  • the high coating weight film had a silver halide coating weight of 40 mg./ dm.
  • the film strips from the three films were exposed and processed as described in Example II except for the variation in concentration of the color-developing agent and of the anhydrous sodium sulfite in the color developing solution.
  • flexibilizing materials include polyethylene dispersed with oleic acid and suitable neutralizing amine, the butadiene/acrylonitrile polymers of US. 2,836,494, and the polymers of Potter et al. US. 2,376,005.
  • this invention is particularly applicable to negative and reversal color films which are designed for exposure in a camera, it is also useful in other color films which may have other than the conventional layer arrangements.
  • the thin layers made possible by this invention can be used advantageously in negative, positive or reversal color films which may be for cine or still use, in transparencies, prints for viewing by reflected light, intermediate films, etc.
  • the invention is not limited to the specific light-sensitive material described in the above detailed examples.
  • Various other simple and mixed silver halides may be used as the light-senitive materials in like manner. Mixtures of silver bromides, chlorides, and/ or iodides can be made by adding mixtures of soluble salts of these halides in like manner.
  • Other useful soluble halides include calcium bromide, potassium iodide, sodium and potassium chlorides and iodides, etc.
  • Inert ingredients e.g., pigments, colloidal silver, polymer latices, matting agents, etc. may be present in all of the element layers including the support.
  • the element may also contain chemical sensitizers, optical sensitizers, coating aid-s, anti-foggants, non-halation dyes and pigments, brightening agents as known to the art, etc.
  • the elements of this invention possess many advantages in physical properties, especially in that preferred embodiment involving the tri-component binder system for silver halide grains as described in Example III.
  • Such elements are unusually tough, particularly when Wet, and are able to undergo treatment in aqueous processing solutions with excellent resistance to abrasion. With their good flexibility, the emulsion have little tendency to crack, even at low relative humidity.
  • a multilayer photographic, camera-speed film for color photography comprising a film support bearing, in order (1) a red-sensitive silver halide emulsion layer,
  • said emulsion layers having an integral thickness, 6, of not more than 12.5 microns and containing a Water-permeable colloid binder comprising gelatin and a compatible, water-soluble color forming vinyl addition copolymer containing a plurality of color-coupling nuclei of a monomer containing a nucleous capable of forming a dye selected from the group consisting of quinoneimine and azomethine dyes upon color-coupling development of an exposed silver salt image, the color-forming addition copolymers of the respective red-, green-, and blue-sensitive layers being of a 1-hydroxy-N-(B-vinyloxyethyl)-2-naphthamide, a l-phenyl-3-methacrylamido-S-pyrazolone and a methacrylamidobenzoylacetanilide, respectively;

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
US113100A 1961-05-29 1961-05-29 Multilayer photographic element for color photography Expired - Lifetime US3211552A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
NL278981D NL278981A (is") 1961-05-29
US113100A US3211552A (en) 1961-05-29 1961-05-29 Multilayer photographic element for color photography
GB20101/62A GB995364A (en) 1961-05-29 1962-05-24 Improvements relating to colour photography
DEP29486A DE1154717B (de) 1961-05-29 1962-05-25 Photographisches Mehrschichtenfarbmaterial und Verfahren zur Herstellung von Farbbildern hiermit
FR899003A FR1332611A (fr) 1961-05-29 1962-05-28 Perfectionnements à la photographie en couleur
ES277758A ES277758A1 (es) 1961-05-29 1962-05-28 Procedimiento de preparación de un elemento de capas múltiples para fotografía en color

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DE (1) DE1154717B (is")
ES (1) ES277758A1 (is")
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3342592A (en) * 1963-06-14 1967-09-19 Du Pont Photographic color films and processes
US3359102A (en) * 1963-04-05 1967-12-19 Gevaert Photo Prod Nv Optical brightening of photographic materials
US3361565A (en) * 1964-01-21 1968-01-02 Du Pont Silver halide photographic element containing a polyanionic color former and a gelatin antiabrasion layer
US3370952A (en) * 1964-09-23 1968-02-27 Du Pont Color formers
US3424583A (en) * 1963-08-14 1969-01-28 Du Pont Photographic color reversal films
US4080211A (en) * 1964-06-23 1978-03-21 Agfa-Gevaert N.V. Polymerization of monomeric color couplets
US4455366A (en) * 1982-06-04 1984-06-19 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US5084373A (en) * 1987-02-05 1992-01-28 Konica Corporation Light-sensitive color photographic material improved on the sharpness and graininess thereof
CN115745848A (zh) * 2022-12-07 2023-03-07 上海优合生物科技有限公司 一种氨基胍的加工合成工艺

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US2380033A (en) * 1938-10-05 1945-07-10 Du Pont Photographic elements containing polyvinyl acetal color formers
US2423460A (en) * 1944-03-31 1947-07-08 Du Pont Photographic elements containing polyamide dye intermediate layers
US2463838A (en) * 1943-02-18 1949-03-08 Du Pont Polymeric color couplers
US2489655A (en) * 1948-04-05 1949-11-29 Du Pont Polymeric color formers
US2828204A (en) * 1953-06-23 1958-03-25 Du Pont Polyvinyl acetal silver halide emulsion containing polyvinyl acetal color formers
US2976294A (en) * 1959-01-26 1961-03-21 Du Pont Dye intermediates
US3070442A (en) * 1958-07-18 1962-12-25 Du Pont Process for producing colored polymeric relief images and elements therefor
US3073699A (en) * 1959-03-17 1963-01-15 Du Pont Addition polymerizable dye-forming compositions, elements, and processes

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2380033A (en) * 1938-10-05 1945-07-10 Du Pont Photographic elements containing polyvinyl acetal color formers
US2463838A (en) * 1943-02-18 1949-03-08 Du Pont Polymeric color couplers
US2423460A (en) * 1944-03-31 1947-07-08 Du Pont Photographic elements containing polyamide dye intermediate layers
US2489655A (en) * 1948-04-05 1949-11-29 Du Pont Polymeric color formers
US2828204A (en) * 1953-06-23 1958-03-25 Du Pont Polyvinyl acetal silver halide emulsion containing polyvinyl acetal color formers
US3070442A (en) * 1958-07-18 1962-12-25 Du Pont Process for producing colored polymeric relief images and elements therefor
US2976294A (en) * 1959-01-26 1961-03-21 Du Pont Dye intermediates
US3073699A (en) * 1959-03-17 1963-01-15 Du Pont Addition polymerizable dye-forming compositions, elements, and processes

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3359102A (en) * 1963-04-05 1967-12-19 Gevaert Photo Prod Nv Optical brightening of photographic materials
US3342592A (en) * 1963-06-14 1967-09-19 Du Pont Photographic color films and processes
US3424583A (en) * 1963-08-14 1969-01-28 Du Pont Photographic color reversal films
US3361565A (en) * 1964-01-21 1968-01-02 Du Pont Silver halide photographic element containing a polyanionic color former and a gelatin antiabrasion layer
US4080211A (en) * 1964-06-23 1978-03-21 Agfa-Gevaert N.V. Polymerization of monomeric color couplets
US3370952A (en) * 1964-09-23 1968-02-27 Du Pont Color formers
US3444110A (en) * 1964-09-23 1969-05-13 Du Pont Polymeric color formers and process of preparing same
US4455366A (en) * 1982-06-04 1984-06-19 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US5084373A (en) * 1987-02-05 1992-01-28 Konica Corporation Light-sensitive color photographic material improved on the sharpness and graininess thereof
CN115745848A (zh) * 2022-12-07 2023-03-07 上海优合生物科技有限公司 一种氨基胍的加工合成工艺

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ES277758A1 (es) 1963-01-16
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