US2312004A - Production of photographic and cinematographic color images - Google Patents

Production of photographic and cinematographic color images Download PDF

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Publication number
US2312004A
US2312004A US355458A US35545840A US2312004A US 2312004 A US2312004 A US 2312004A US 355458 A US355458 A US 355458A US 35545840 A US35545840 A US 35545840A US 2312004 A US2312004 A US 2312004A
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United States
Prior art keywords
color
acid
color formers
photographic
former
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Expired - Lifetime
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US355458A
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English (en)
Inventor
Schneider Wilhelm
Frohlich Alfred
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GAF Chemicals Corp
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General Aniline and Film Corp
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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
    • G03C7/34Couplers containing phenols
    • G03C7/344Naphtholic couplers

Definitions

  • This invention relates to the production of photographic and cinematographic color images.
  • photographic and cine matographic color images there are generally employed silver halide emulsions to which before casting or during any stage of the manufacturing process there are added dyestuif components fast to diffusion which may be converted into a color image after exposure of the photographic emulsion by a suitable process, directly or indirectly, by means of the latent image or silver image.
  • Suitable color formers have been described in great numbers.
  • Patent 2,178,612 color formers with radicals of high polymeric acids in U. S. Patent 2,186,849 color formers with long carbon chains, in U. S. Patent 2,179,244 color formers with polypeptide radicals, in U. S. Patent 2,186,732 color formers with carbohydrate radicals, in U. S. Patent 2,186,733 color formers with resin acid radicals, in U. S. Patent 2,186,851 color formers with bile acid radicals, in U. S. Patent 2,280,722 color formers with substituents having several members, in which besides the initialand end members the same carbon-arrangements occur several times being connected by hetero atoms, such as for instance polyethylene imineor polyethylene oxide radicals, finally in U. S.
  • these color formers there is accomplished the union of the color former-molecule with the molecule-radicals effecting fastness to diffusion from a practical view point mostly in the form of an acid amide linkage, and it is immaterial on which of the reactants the aminoor acid group is found.
  • Color formers of this kind are for instance the following compounds which are selected at will from the great number of known dyestuffs described in former patent applications:
  • a-hydroxy-naphthoic acid benzidide the reaction products of a-hydroxy-naphthoic acid with 4,4'-diamino stilbene 1,2,3,4-xylenol-car- 'boxylic acid with dodecylamine, fi-methoxy-salicylic acid with octadecylamine, salicylic acid with cerylamine, a-hydroxy-naphthoic acid with abietylamine, the condensation product from stearic acid and u-hydroiw-naphthoyl-4-amino- 3-sulfo acid anilide, the reaction products of 2- amino-l-naphthol with abietic acid, 1-amino-8- naphthol with cholanic acid, 1-amino-8-naphthol-6,7-disulfo acid with lauric acid, 1-amino-8- naphthol-7-sulfo acid wily
  • color formers are most suitable for the manufacture of multicolor photographic material for multicolor photography, especially in silver halide emulsion layers, which according to U. S. Patents 2,148,979 and 2,148,980 are sensitized with sensitizers the sensitizing effect of which is not influenced by the color formers.
  • These color formers show a considerable disadvantage which becomes evident especially when the material manufactured with these color formers is stored under conditions prevailing in warm countries. To store photographic materials containing these color formers in warm countries, changes the sensitization of the photographic material. Consequently insufiicient and absolutely incorrect color reproduction is obtained therefrom.
  • Another object is to manufacture color formers not injuring the sensitization of the photographic emulsion.
  • a further object is to manufacture a photo- This tendency of the color images containing color overcome when such color formers fast to diffusion are employed, which do not influence fundamentally the sensitivity of the silver halide emulsions,
  • the acid hydrogen of the imino group may be present in the following atom groupings: -NHCO-, -CONH, -SO2NH-, -NH-SO2--, NH-CO-NH and -NH-CS-NH.
  • dyestufi components fast to diffusion which in orthoor peri-position to the hydroxyl group participating in the formation of the dyestuff do not contain any radicals with free iminohydrcgen.
  • suitable color formers are those which are obtained by the action of a primary amine fast to diffusion on an aromatic hydroxy acid capable of coupling, in which the acid group is not located in a position ortho or peri to the hydroxyl group, color formers which are obtained by the action of secondary amines fast to diffusion on compounds containing hydroxy groups and capable of coupling, color formers which are obtained by the action of carboxylic acids or sulfo acids fast to diffusion on secondary amino groups of color components containing hydroxy groups, color formers which are obtained by the action of carboxylic acids or sulfo acids or their derivatives fast to diffusion on primary amino groups being not in orthoor peri-position to the hydroxy group of the dyestuff component, color formers with imino groups which are not in ortho- Or periposition to the
  • Color formers are for instance the reaction products of 1- amino-S-naphthol-B-sulfo acid with palmitic acid, m-hydroxybenzoic acid with oleylamine, oz-
  • hydroxy-naphthoic acid with methyldodecylgroups furthermore condensation products from salicyclic acid and phenols and reaction products of hydroxy carboxylic acids with such polyamides as contain preferably secondary amino groups.
  • color formers and molecule radicals effecting fastness to diffusion which were already proposed in former U.
  • the color formers may con tain, besides the radicalsv effecting fastness to diffusion, groups effecting increased water-solubility, such as carboxy-, sulfoor hydroxyl groups.
  • the color formers according to the present invention show contrary to the color components hitherto proposed the surprising effect that they exhibit no affinity whatsoever to the silver halide grain, or in other words they do not prevent tinting of the silver halide grains by the sensitizers.
  • the sensitization is therefore influenced in no constitution there may be combined, generally way.
  • This property of the color components which guarantees the good keeping quality of the emulsion containing the same even under trying weather conditions may be clearly seen from the fact that for the same degree of sensitization is effected whether the color component is added to the emulsion before or after the sensitizer.
  • materials for color photography of increased keeping quality even under unfavorable storage conditions may be manufactured.
  • the silver halide emulsions containing color formers fast to diffusion may be subjected before casting to a short washing process and may be worked up into photographic layers in a known manner. These layers may be arranged on one or both sides of a support, one on top of the other, and may be sensitized for different spectral regions.
  • the silver halide emulsions can also be worked up according to U. S. Patent 2,186,730 by arranging on a support, in the form of minute particles, differently sensitized emulsions containing different color formers.
  • the production of the color images may be accomplished in different ways, for instance according to U. S. Patents Nos. 2,179,228, 2,179,238, 2,186,849, 2,178,612 and U. S. patent application Ser. No. 111,250, filed November 17, 1936.
  • the color images may be produced by a simple color forming development or by reversal development according to U. S. Patents 2,179,234 and 2,229,137.
  • a process for the production of a color photographic silver halide emulsion containing a sensitizer and a dyestufi former fast to diffusion comprising adding to a photographic silver halide emulsion a phenolic dyestuff former having linked to a carbon atom of the nucleus thereof a radical rendering the dyestuff former fast to diifusion, said radical being linked to a carbon atom of the phenolic dyestufi' former in a position other than that selected from the class consisting of the orthoand peri-positions to the phenolic hydroxy group by a linkage selected from the class consisting of NHCO, CONH, SO2NH-, NHSO2-, --NHCONH and NHCSNH and then adding to said silver halide emulsion a sensltizer therefor.
  • the dyestuff former is the reaction product of a primary amine fast to diflusion and an aromatic hydroxy acid, the acid group of which is in a position other than a position selected from the class consisting of the orthoand pen-positions to the hydroxy group.
  • the dyestuff former is the reaction product of a secondary amine fast to difiusion and an aromatic hydroxy acid in which the acid group is in a position other than a position selected from the class consisting of the orthoand peri-positions to the hydroxy group.
  • WILHELM SCHNEIDER WILHELM SCHNEIDER. ALFRED FR6HLICH.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US355458A 1939-07-05 1940-09-05 Production of photographic and cinematographic color images Expired - Lifetime US2312004A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI0065042 1939-07-05

Publications (1)

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US2312004A true US2312004A (en) 1943-02-23

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US355458A Expired - Lifetime US2312004A (en) 1939-07-05 1940-09-05 Production of photographic and cinematographic color images

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US (1) US2312004A (xx)
BE (1) BE439619A (xx)
CH (1) CH232633A (xx)
FR (1) FR870911A (xx)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2536010A (en) * 1947-07-11 1950-12-26 Gen Aniline & Film Corp Preparation of azine dyestuff images
US2641612A (en) * 1949-07-15 1953-06-09 Chemie Linz Ag Vanillic acid diethylamide

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2536010A (en) * 1947-07-11 1950-12-26 Gen Aniline & Film Corp Preparation of azine dyestuff images
US2641612A (en) * 1949-07-15 1953-06-09 Chemie Linz Ag Vanillic acid diethylamide

Also Published As

Publication number Publication date
BE439619A (xx)
FR870911A (fr) 1942-03-30
CH232633A (de) 1944-06-15

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