US2994607A - Process for the production of color-corrected color photographic images - Google Patents

Process for the production of color-corrected color photographic images Download PDF

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Publication number
US2994607A
US2994607A US697403A US69740357A US2994607A US 2994607 A US2994607 A US 2994607A US 697403 A US697403 A US 697403A US 69740357 A US69740357 A US 69740357A US 2994607 A US2994607 A US 2994607A
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Prior art keywords
color
image
coupler
magenta
residual
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English (en)
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Loffler Karl
Pelz Willibald
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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
    • C07C311/49—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution

Definitions

  • the color couplers or components which are used in such multi-layer systems belong to various classes of compounds; thus, derivatives of aeeto-acetic acid or benzoyl acetic acid, such as for example benzoyl acetic acid amides, are used as yellow couplers, derivatives of pyrazolone, cyanacetophone, isoxazolone and oxythionaphthene are used as magenta couplers, and rerivativesot phenol or a-naphthol are usually used as cyan couplers.
  • derivatives of aeeto-acetic acid or benzoyl acetic acid such as for example benzoyl acetic acid amides
  • derivatives of pyrazolone, cyanacetophone, isoxazolone and oxythionaphthene are used as magenta couplers
  • rerivativesot phenol or a-naphthol are usually used as cyan couplers
  • this process consists in that the color images are treated with a solution of an azide, preferably an aqueous solution, the azide reacting with the residual color component.
  • an aralkyl radical for example benzyl
  • an acyl radical for example -CONH it being possible for one or both of the hydrogen atoms to be substituted by any desired organic radicals for example alkyl, such as methyl, ethyl, propyl, butyl; aryl, such as phenyl, tolyl; cycloalkyl, such as cycloheXyl; aralkyl, such as benzyl;
  • sulphonyl radical for example of the general formula Z.SO in which Z is a substituted or unsubstituted alkyl, such as methyl, ethyl, butyl, allyl; substituted or unsubstituted aryl, for example phenyl, aralkyl, for example benzyl,; cycloalkyl, such as cyclohexyl, a heterocyclic radical or a radical of the formula in which R and R represent like or different substituents, for example the aforementioned alkyl, aryl, aralkyl, cycloalkyl radicals, or guanidyl radi cal, for example H2N.C- i.
  • the process of the present invention offers the following advantages:
  • the azides do not form any colored compounds with the binder of the layers, and the gelatine, for example, remains completely clear and colorless.
  • the color density of the yellow masking dye is usually much too high, which from a photographic point of view leads to considerable difiiculties, since the defective absorption of the image dyestutt" is over-compensated.
  • the mask gradation conforms to theoretical requirements and consequently provides optimum color correction. Since the treatment in the masking bath can con .tinue as long as required without any danger of overmasking, the danger of color fluctuation is much smaller, whereas it is necessary to maintain narrow tolerances as regards time, temperature and concentration of the masking baths in the known masking processes.
  • azides are suitable for forming the masking dye images.
  • a requirement is that they should 'be sufficiently soluble and stable to allow them to be used in the form of photographic baths. Consequently, the azides which are most suitable are those which are soluble in water or in a mixture of water with organic solvents which are soluble in water, and have the best possible stability both in solid form and in solution.
  • These conditions are met by a considerable number of azides, particularly by sulphonyl azides.
  • these azides those which are derived from aromatic sulphonic acids of which the aromatic radical carries sulphonic acid and/or carboxyl groups as substituents are particularly valuable because of their stability and solubility.
  • the reactivity is generally in the range between the weakly acid and strongly alkaline.
  • the azides are preferably applied in the form of their solutions in water or a mixture of water with organic solvents which are soluble in water, such as aliphatic lower alcohols, acetone or other ketones, dioxane, tetrahydrofurane, glycolmonomethylether or other ethers, and amines such as triethanolamine.
  • the pH value may vary between 5 and 12, it is preferably adjusted to 7.5 to 9.5.
  • the concentration of the azide may vary within 5 wide limits and amounts preferably to 0.5 to 2.5%.
  • the azide masking baths are used after the color de- -velopment, for example subsequent to the rinsing which follows the color development, or after one of the subsequent baths which are usual in the processing of color photographic materials. It is advisable to use them after the bleaching and fixing of the images, because then it is readily possible to judge the images before the masking, and the masking itself can take place inthe light. It is only important that previously no change of the residual component shall have taken place which excludes .a reaction with azide. Such a change can for example be caused by bleaching baths which contain potassium ferricyanide as bleaching agent. The use of such baths can reduce the reactivity With azides by oxidation of the residual component.
  • a solution of 3.65 g. of sodium azide in 25 cc. of water is slowly added to a solution of 13.7 g. of 2-chlorobenzoic acid-S-sulphochloride in 15 cc. of methanol together with 29 cc. of a 10% aqueous sodium hydroxide solution so as to keep the pH value of the reaction mixture at about 7.
  • the reaction mixture is filtered over charcoal and acidified.
  • the sulphonyl azide precipitates and is isolated by filtration. Melting point: 128-130 C.
  • Example 2 An exposed multi-layer color film, the blue-sensitive silver halide layer of which contains p-methoxy-benzoylaceto-(2-N-methyl-N-octadecylamino-S-sulpho) anilide, the green-sensitive silver halide layer of which contains 1-(3'-w-sulphomethyl phenyl)-3-stearyl-5-pyrazolone and 10 g. of methane sulphonyl azide,
  • bleaching and fixing is carried out for 8 minutes with the bleach fixing bat-h as described in Example l.
  • the film is thoroughly rinsed between the baths and following the treatment in the bleach fixing bath. After being processed, the film contains a yellow masking image in the magenta image layer.
  • the methane sulphonyl azide is prepared as follows: A solution of 12 g. of methane sulphonyl chloride in 20 cc. of acetone is slowly added to a solution of 10 g. of sodium azide in 100 cc. of water at 2530 C. The reaction mixture is allowed to stand for 14 hours. Thereafter, it is diluted with 300 cc. of water. The oil which separates is isolated by steam distillation.
  • Example 3 A multi-layer film built up as described in Example 1 but containing p-octadecenyl-succinylamino-w-cyanacetophenone as the magenta component instead of the one described in Example 1, is treated for 6 minutes after the bleaching and fixing operation in a masking bath having the following composition:
  • the film After processing, the film contains in the green-sensitive layer amagenta image and a yellow image which is negative thereto.
  • the dimethylamino-sulphonyl azide is prepared according to the process disclosed in Example 2 while replacing the methane sulphonylchloride by 14.5 g. of dimethylamino-sulphonylchloride.
  • Example 4 An exposed film as in Example 2, but with 1-(4- methoxy-3-sulpho) phenyl-3-heptadecyl-5-pyrazolone, is color-developed and bleached and fixed in the same way. A yellow mask is thereafter formed by treatment for 10 minutes in a bath (pH 8.4) of the following composition:
  • magenta image is so masked that an equal quantity of blue is absorbed independently of the magenta density at any area of the image.
  • the 2-azidobenzthiazole-S-sulphonic acid is prepared as follows:
  • Example 5 The process of Example 1 is repeated while using as a masking bath a 3% aqueous solution of guanylazidnitrate (Annalen 380, p. 135) in which the developed film is bathed after bleaching and fixing for 3 minutes. The film is then treated for 5 minutes in a aqueous solulution of sodium carbonate. There is obtained a yellow masking image in the layer containing the magenta partial image.
  • Example 6 The exposed and developed multi-layer material of Example 2 is bleached for 5 minutes in a bath of the following composition:
  • the material is fixed in a solution of 200 g. of Na 'S O in 1000 cc. of water and then treated for 9 minutes in a solution of 6 g. of 2-azidobenzthiazole-6-sulphonic acid and 3.5 g. of sodium carbonate in 1000 cc. of water (pH value 8.8).
  • the Z-azidobenzthiazol-6sulphonic acid is prepared by the process disclosed in Example 6, while using instead of 2-azidobenzthiazole-5- sulphonic acid the same amount of 2-azidobenzthiazole- 6-sulphonic acid.
  • the latter compound is obtained by slowly adding while stirring .20 g. of 2-hydrazinobenzthia zole to 45 cc. of oleum (20%), whereby solution takes place and pouring the solution after 10 minutes into ice water, sucking off the precipitate formed and washing the latter first with a little water and then with methanol.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US697403A 1956-11-20 1957-11-19 Process for the production of color-corrected color photographic images Expired - Lifetime US2994607A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEA26055A DE1030181B (de) 1956-11-20 1956-11-20 Verfahren zur Herstellung farbkorrigierter farbenphotographischer Bilder in Schichten, die Farbkomponenten enthalten, die mit den Oxydationsprodukten von primaere Amino-gruppen enthaltenden Entwicklungs-substanzen Farbstoffe bilden

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US (1) US2994607A (de)
CH (1) CH365614A (de)
DE (1) DE1030181B (de)
FR (1) FR1188615A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3245788A (en) * 1959-11-13 1966-04-12 Gevaert Photo Prod Nv Production of color photographic images

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2633422A (en) * 1948-04-21 1953-03-31 Du Pont Process for making integral color correction masks
US2690968A (en) * 1952-10-04 1954-10-05 Powers Chemco Inc Development of diazo and azide sensitized colloids

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2633422A (en) * 1948-04-21 1953-03-31 Du Pont Process for making integral color correction masks
US2690968A (en) * 1952-10-04 1954-10-05 Powers Chemco Inc Development of diazo and azide sensitized colloids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3245788A (en) * 1959-11-13 1966-04-12 Gevaert Photo Prod Nv Production of color photographic images

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DE1030181B (de) 1958-05-14
FR1188615A (fr) 1959-09-24
CH365614A (de) 1962-11-15

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