US2884325A - Process for the production of a yellow mask image in magenta-colored photographic images - Google Patents

Process for the production of a yellow mask image in magenta-colored photographic images Download PDF

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Publication number
US2884325A
US2884325A US492053A US49205355A US2884325A US 2884325 A US2884325 A US 2884325A US 492053 A US492053 A US 492053A US 49205355 A US49205355 A US 49205355A US 2884325 A US2884325 A US 2884325A
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magenta
image
yellow
aldehyde
production
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US492053A
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Burgardt Lothar
Reckziegel Erich
Wahl Ottmar
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Agfa Gevaert NV
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Agfa AG
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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
    • G03C7/18—Processes for the correction of the colour image in subtractive colour photography

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  • This invention relates to a process for the correction of photographic color images and more particularly to a process for the correction of magenta photographic images produced by the process of color forming development.
  • azomethine dyes which are generally used for the production of magenta-colored images according to the process of color forming development, do not have a perfect absorption. They absorb light in the green range of the spectrum as well as some of the light in the blue range of the spectrum. This fact obviously leads to a color defect in the negative-positive process.
  • magenta dyestuffs which are formed by color-forming development from pyrazolones.
  • Such masking images may be produced by transforming the color couplers contained in a silver halide layer after color forming development into yellow dyestuffs.
  • a process has already been proposed which is characterised in that the light-sensitive material, which contains a diffusion-resisting pyrazolone or a similar compound containing an active methylene group as magenta color-former, is treated after exposure and color development with an aromatic aldehyde of the benzene or naphthalene series which contains an auxochromic group, or with a functional derivative of such an aldehyde.
  • the residual color coupler in such a case is transformed by the aldehyde to form a yellow dyestulf, which serves as a color mask for correcting the undesired secondary absorption of the image dye.
  • Appropriate compounds for carrying out this process are monoand di-substituted p-aminobenzaldehydes and the anils, arylhydrazones or bisulphite reaction products of such aldehydes, which are alkali-soluble as a result of suitable substituents, for example, sulphonic groups.
  • the yellow masking image dyes obtained by this process have the disadvantage, however, that their absorption is not restricted to the blue part of the spectrum, but also extend to the green part thereof. However, an undesirable flattening of the gradation of the magenta image dyestufi is caused by this absorption in the green part of the spectrum.
  • aldehydes are particularly suitable, because they lead to styryl dyestuffs, which are of shorter wavelength in their absorption than the corresponding dyes with substituted aminobenzaldehydes and therefore cannot be the cause of a disadvantageous flattening in the gradation of the magenta dyestufi image.
  • heterocyclic aldehyes are particularly valuable for the purpose in question, because the use thereof, independently of the duration of their action on the photographic material does not lead to overmasking, i.e. a positive yellow image with higher density than that of the secondary absorption of the magenta image dyestuffs formed from pyrazolones.
  • the secondary absorptions of these magenta image dyestuffs and the yellow masking dyes which are formed have in fact substantially the same color density.
  • aldehydes examples include: u-pyrrole aldehyde, 2.4-diphenylpyrrole-S-aldehyde, ,G-indole aldehyde, indole-3- aldehyde-carboxylic acid, 1-methyl-2-phenylindole-3- aldehyde, N- (carboxyethyl)-carbazole-3-aldehyde, N- ethyl-carbazole-3-aldehyde-sulphonic acid and N-ethylcarbazole-3-aldehyde.
  • the anils are produced according to known processes.
  • aniline derivatives which carry positive substituents, such as, for example, hydroxy-, alkoxyor dialkylamino-groups.
  • Sparingly soluble aldehydes are transformed into alkali-soluble compounds by reaction with aniline-sulphonic acids.
  • the process according to the invention is particularly suitable for the production of yellow masking images in photographic multi-layer materials which contain color couplers for the production of yellow, magenta and cyan color couplers in three superimposed silver halide layers which are sensitive to diflferent regions of the spectrum.
  • Appropriate couplers for the production of magneta images are the well known pyrazolones-S, for ex- 1 (4-phenoxy-5-sulphophenyl)-3-heptadecyl-5- pyrazolone.
  • couplers such as cyanacetyl compounds.
  • Example 1 The following multi-layer light sensitive material is used:
  • a transparent support is coated with a layer of a red sensitive silver halide emulsion containing 20 grams per litre of the cyan color forming coupler having the formula:
  • a layer of a green sensitive silver halide emulsion layer containing per litre 15 grams of the magenta color forming coupler 1-(4- phenoxy'sulphophenyl)-3-heptadecyl-5-pyrazolone.
  • a yellow filter layer of colloidal silver and thereupon an optically not sensitized silver halide layer 3 is coated, which contains per litre the following yellow color forming coupler:
  • This film is exposed to an object to be reproduced and developed in a developer solution of the following composition:
  • the material After rinsing, the material is bathed in an 0.5% slightly alkaline solution of m-"nethoxy-anil of fl-indolealdehyde- 2-carboxylic acid. The film is then bleached, fixed and washed in the conventional manner. The material thus treated now contains a positive yellow color image serving as a mask in the green-sensitive layer, in addition to its cyan, magenta and yellow negative component images.
  • the ,B-indolealdehyde-Z-carboxylic acid is obtained from e-indole-carboxylic acid ethyl ether according to the process disclosed in J. Am. Chem. Soc. 68 (1946), 1156.
  • Example 2 instead of the said solution of m-methoxy-anil of [3- indole-aldehyde-Z-carho-xylic acid referred to in Example 1, there may equally well be employed an 0.5-1% weakly alkaline solution of m-dimethyl amino-anil of N-ethylcarbazole-3-aldehyde-sulphonic acid for the production of the yellow masking image.
  • N-ethyl-carbazole-3-aldehyde sulphonic acid is obtained in the following manner:
  • Example 3 Instead of the said solution of m-methoxy-anil of fi-indole-aldehyde-Z-carboxylic acid referred to in Example 1, there is employed an 0.5 Weakly alkaline solution of m-hydroxyanil of ot-pyrrole aldehyde for the production of the masking image.
  • the a-pyrrol-aldehyde is obtained according to the process disclosed in Berichte der- Deutschen Chemischenmaschine 51 (1928), 1078.
  • Example 4 A multi-layer material, in which the bottom red-sensitive silver halide layer with blue-green component has coated thereon a green-sensitive silver halide layer with yellow component, above which is a yellow filter layer and an unsensitised silver halide layer with a pyrazolone as magenta dyestuif former, is exposed and developed as in Example 1.
  • the material After being rinsed, the material is treated with an 0.5-1% weakly alkaline solution of the m-sulphanil of N- ethyl-carbaZole-3-aldehyde, bleached, fixed and washed.
  • the film now contains a negative magenta image in the top coating, opposite-whichis a yellow masking image.
  • Example 5 instead of the solution mentioned in Example 4 for the production of a yellow masking image, there may equally well be employed a weakly alkaline solution of a sulphanil of 1-methyl-2-phenyl-indole-3-aldchyde. This aldehyde is obtained by the process disclosed in German patent specification 614,325.
  • Example 6 instead of the solution mentioned in Example 4, the masking image may be produced by using the weakly alkaline solution of m-hydroxyanil of 2.4-diphenyl-pyrrol- S-aldehyde. This aldehyde is obtained by the process disclosed in J. Chem. Soc. (London) 1943, p. 596.
  • Example 7 For the production of a duplicate negative, three positive black-and-white separation records produced from a multi-color negative are successively exposed by means of three partial color record filters on to a multi-layer material which has a bottom red-sensitive silver halide layer with a cyan color forming coupler, above this a greensensitive silver halide layer with a yellow color forming coupler and a top layer of an unsensitised silver halide layer with a pyrazolone as magneta color forming coupler, all layers containing tartrazinc as filter dyestutf instead of using a separate filter layer.
  • the color forming couplers may be the same as those disclosed in Example 1.
  • the material thus exposed is developed in a developer of the following composition:
  • the multi-layer material contains a negative blue-green image in the bottom coating, a negative yellow image in the middle coating and a negative magenta image with a yellow masking image in the top coating.
  • a process for the production of a yellow masking image for a magenta-colored image comprising develop ing an imagewise-exposed silver halide emulsion layer, containing a magenta color-forming coupler having an active methylene group, with a primary aromatic amino developing agent to form a magenta dye image, and reacting the residual color-forming coupler with an aldehyde to produce a yellow styryl dyestufi masking image, said aldehyde being selected from the group consisting of pyrrolealdehydes, indole-aldehydes, carbazole aldehydes and anils thereof.
  • magenta colorforming coupler is a pyrazolone.
  • a process for the production of a yellow masking image for a magenta-colored image which comprises developing an imagewise-exposed photographic material comprising a transparent base and a plurality of superimposed silver halide emulsion layers coated on said base, one of said layers containing a magenta-color-forming coupler having an active methylene group, with a primary aromatic amino developing agent to form a magenta dye image in said layer containing said magenta color-forming coupler, and reacting the residual colorforming coupler with an aldehyde to produce a yellow styryl dyestuif image, said aldehyde being selected from the group consisting of pyrrole aldehydes, indole aldehydes, carbazole aldehydes and anils thereof,
  • aldehyde concomprises a red-sensitive silver halide layer containing a (aims a Sulfonic acid group bonded to a cyclic carbon cyan color-forming coupler, another of said layers comatomprlses a green-sensitwe sllver halide layer sltuated above References Cited in the file of this patent said red-sensitive layer, and a third layer comprises an 5 unsensitized silver halide layer situated above said green- UNITED STATES PATENTS sensitive layer, one of said last-mentioned layers con- 1,731,966 Ballauf 0 taining pyrazolone as a magenta color-forming coupler.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Materials For Photolithography (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US492053A 1954-03-05 1955-03-03 Process for the production of a yellow mask image in magenta-colored photographic images Expired - Lifetime US2884325A (en)

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DE333209X 1954-03-05

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BE (1) BE536088A (en(2012))
CH (1) CH333209A (en(2012))
FR (1) FR1120007A (en(2012))
GB (1) GB765280A (en(2012))

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2998312A (en) * 1955-01-28 1961-08-29 Ici Ltd New process for colour photography
US3543291A (en) * 1967-02-17 1970-11-24 Bolls & King Photolithography

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1781966A (en) * 1925-01-16 1930-11-18 Gen Aniline Works Inc Carbazole-indophenol compounds and process of preparing the same
US1898445A (en) * 1931-03-23 1933-02-21 Gen Aniline Works Inc Indophenols of the benzocarbazole series and process of making same
US1954452A (en) * 1930-03-19 1934-04-10 Leopold D Mannes Method of making color photographs
US2252718A (en) * 1937-11-19 1941-08-19 Eastman Kodak Co Reversal process of color photography
US2304939A (en) * 1939-01-23 1942-12-15 Eastman Kodak Co Multilayer photographic material containing color formers
US2663638A (en) * 1948-09-15 1953-12-22 Ici Ltd Color correction of multicolor film by integral styryl dye masking images
US2704709A (en) * 1949-07-16 1955-03-22 Gen Aniline & Film Corp Masking process for multilayer photographic color film

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1781966A (en) * 1925-01-16 1930-11-18 Gen Aniline Works Inc Carbazole-indophenol compounds and process of preparing the same
US1954452A (en) * 1930-03-19 1934-04-10 Leopold D Mannes Method of making color photographs
US1898445A (en) * 1931-03-23 1933-02-21 Gen Aniline Works Inc Indophenols of the benzocarbazole series and process of making same
US2252718A (en) * 1937-11-19 1941-08-19 Eastman Kodak Co Reversal process of color photography
US2304939A (en) * 1939-01-23 1942-12-15 Eastman Kodak Co Multilayer photographic material containing color formers
US2663638A (en) * 1948-09-15 1953-12-22 Ici Ltd Color correction of multicolor film by integral styryl dye masking images
US2704709A (en) * 1949-07-16 1955-03-22 Gen Aniline & Film Corp Masking process for multilayer photographic color film

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2998312A (en) * 1955-01-28 1961-08-29 Ici Ltd New process for colour photography
US3543291A (en) * 1967-02-17 1970-11-24 Bolls & King Photolithography

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CH333209A (de) 1958-10-15
GB765280A (en) 1957-01-09
BE536088A (en(2012))
FR1120007A (fr) 1956-06-28

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