US2657139A - Process of removing color developer stain in azine dye images - Google Patents

Process of removing color developer stain in azine dye images Download PDF

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Publication number
US2657139A
US2657139A US202437A US20243750A US2657139A US 2657139 A US2657139 A US 2657139A US 202437 A US202437 A US 202437A US 20243750 A US20243750 A US 20243750A US 2657139 A US2657139 A US 2657139A
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color
acid
emulsion
stain
azine
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US202437A
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James E Bates
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GAF Chemicals Corp
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General Aniline and Film Corp
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Priority to BE507902D priority Critical patent/BE507902A/xx
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Priority to US202437A priority patent/US2657139A/en
Priority to DEG7657A priority patent/DE900782C/en
Priority to GB29514/51A priority patent/GB701341A/en
Priority to FR1047081D priority patent/FR1047081A/en
Priority to CH295701D priority patent/CH295701A/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
    • G03C7/3046—Processing baths not provided for elsewhere, e.g. final or intermediate washings

Definitions

  • This invention relates to photographic rinse baths for removing color developer stains from azine dyestuif images following color forming development with ZA-diaminoaniline developing agents.
  • azine dyestuif images are produced by color developing silver halide emulsions containing azine color formers with a ZA-diaminoaniline developing agent. The procedure of this process is fully described in U. S. P. 2,486,440.
  • the ZA-diaminoaniline developing agents employed therein possess one disadvantage which causes a somewhat serious problem.
  • the disadvantage occurs in the development of the multilayer color film of the azine type and is manifested especially when the aromatic trianiino developing solution is old and badly oxidized by leaving a developer stain in the processed film.
  • This stain in most cases is quite substantive to gelatin but can under certain circumstances be to some extent removed by excessively long water washing after color development.
  • This developer stain is observed particularly in the highlights or Whites of the processed film. In the color developed areas of the film, it produces a serious loss in color brilliance and a degradation of color rendition.
  • the developer contributes in no small degree to the loss of storage stability of the final color image, including both the socalled light, humidity, and heat fading characteristics.
  • rinse baths consisting of aqueous solutions of water soluble open-chain mono-, di-, and tribasic acids, such as acetic,
  • the above objects are accomplished by treating an azine multilayer color film, after color forming development with an aqueous rinse bath containing from 0.1 to 10% of formaldehyde and from 0.1 to 10% of a Water-soluble acid, such as hydrochloric, phosphoric, acetic, maleic, citric, acrylic, oxalic, tartaric, and the like.
  • a Water-soluble acid such as hydrochloric, phosphoric, acetic, maleic, citric, acrylic, oxalic, tartaric, and the like.
  • the pH of the resulting rinse bath is immaterial and in these concentrations, and in the presence of formaldehyde, the acid does not form an insoluble complex with the residual ZA-diaminoaniline developing agent retained by the film, i. e., does not precipitate it upon the film or in the layers thereof.
  • the color formers utilized contain a group rendering them non-migratory in the emulsion. Examples of such compounds are:
  • Color formers capable of producing magenta dyestuff images are also described in the above identified application and in USP 2,524,741.
  • these color formers are 6-halogen-8-hydroxyquinolines, and particularly those which are non-migratory in the emulsions.
  • Examp1es of the latter type compounds are:
  • Color formers for the cyan image are also described in USP 2,570,1 6, issued October 2, 1951, and in USP 2,445,252, issued July 13, 1948.
  • these color formers are aryl-J-acid derivatives, particularly those containing a group rendering the color former non-migratory in the emulsion.
  • Examples of the latter compounds are: dodecyl urethane of fi-sulfoethyl-J-acid tetradecyl urethane of p-anisyl-J-acid Z-hexadecyl urethane of phenyl-J-acid 4-stearoylamino-J-acid, and the like.
  • Example I A red sensitive emulsion containing phenyl-J- acid-N-octadecyl urethane was exposed and the latent image developed in a black and white developer, re-exposed, and the residual silver halide developed in a solution of the following composition:
  • the film was washed, bleached in a ferricyanide bleach, and fixed in an acid hardening solution. There is obtained a cyan positive dye image completely free from stain and stable against accelerated adverse storage conditions.
  • Example I I Grams Sodium carbonate (monohydrate) 40 Sodium sulfite 60 Potassium bromide 5 Pyridine 16 Benzylamine 1 4 (B hydroxyethylamino) 6 phenyl amino-metanilic acid 5 Water to make 1000 cc.
  • the film was washed, bleached in a ferricyanide bleach, and fixed in an acid hardening fixer solution. There was obtained a multicolor film containing stain-free positive dye images of excellent brilliance and freedom from color degradation.
  • Example III An integral tripack of essentially the same composition as in Example II was exposed and color developed for minutes to a negative image in a solution of the following composition:
  • Hydroxylamine hydrochloride 1 4 4,8 hydroxyethylamino) -6-benzylamin0- metanilic acid 6 Water to make 1000 cc.
  • the film was washed, bleached in a ierricyanide bleach, and fixed in an acid hardening hypo solution. There was obtained a brilliant negative dye image completely free from stain and color degradation. The negative did not acquire additional stain nor become subject to color degradation during three weeks accelerated aging at relative humidity and F.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)

Description

Patented Oct. 27, 1953 PROCESS OF REMOVING COLOR DEVEL- OPER STAIN IN AZINE DYE IMAGES James E. Bates, Chenango Bridge, N. Y., assignor to General Aniline & Film Corporation, New York, N. Y., a corporation of Delaware N Drawing. Application December 22, 1950, Serial No. 202,437
6 Claims.
This invention relates to photographic rinse baths for removing color developer stains from azine dyestuif images following color forming development with ZA-diaminoaniline developing agents.
It is known that azine dyestuif images are produced by color developing silver halide emulsions containing azine color formers with a ZA-diaminoaniline developing agent. The procedure of this process is fully described in U. S. P. 2,486,440.
Despite the many recognized advantages of this process, the ZA-diaminoaniline developing agents employed therein possess one disadvantage which causes a somewhat serious problem. The disadvantage occurs in the development of the multilayer color film of the azine type and is manifested especially when the aromatic trianiino developing solution is old and badly oxidized by leaving a developer stain in the processed film. This stain in most cases is quite substantive to gelatin but can under certain circumstances be to some extent removed by excessively long water washing after color development. This developer stain is observed particularly in the highlights or Whites of the processed film. In the color developed areas of the film, it produces a serious loss in color brilliance and a degradation of color rendition. Moreover, the developer contributes in no small degree to the loss of storage stability of the final color image, including both the socalled light, humidity, and heat fading characteristics.
In a multi-layer color film of the azine type which is composed of three layers colored yellow, magenta, and cyan, an ideal red reproduction would be composed of images wholly contained in the yellow and magenta layers and with a minimum of density in the cyan layer. Inasmuch as 2,4-diaminoanilines, as a general class, are oxidized quite readily by air and the residual color developing agent is oxidized by the bleaching steps subsequent to normal color development, an appreciable degradation of the red manifests itself by a stain density formed in the cyan layer.
To overcome the excessive washing time and the formation of stain, rinse baths consisting of aqueous solutions of water soluble open-chain mono-, di-, and tribasic acids, such as acetic,
citric, maleic, etc., have been suggested. Shortstop baths containing these acids are, however, ineffective when applied to the azine process since they minimize the solubility of the 2,4- diaminoaniline color developers and lead to a product of extremely poor color rendition. Rinse baths of aqueous solutions of aliphatic aldehydes 2 and diketones, such as formaldehyde, paraformaldehyde, and the like, have also been proposed but these are also ineffective since a falsification of color occurs.
It is an object of the present invention to provide a simple and economical method of eliminating color stain and degradation from azine dyestufi images obtained by color forming development with 2,4-diaminoaniline developing agents. Other objects and advantages will appear hereinafter.
The above objects are accomplished by treating an azine multilayer color film, after color forming development with an aqueous rinse bath containing from 0.1 to 10% of formaldehyde and from 0.1 to 10% of a Water-soluble acid, such as hydrochloric, phosphoric, acetic, maleic, citric, acrylic, oxalic, tartaric, and the like. The pH of the resulting rinse bath is immaterial and in these concentrations, and in the presence of formaldehyde, the acid does not form an insoluble complex with the residual ZA-diaminoaniline developing agent retained by the film, i. e., does not precipitate it upon the film or in the layers thereof. The presence of the Water-soluble acid tends to cause the formaldehyde to form a watersoluble 2,4-diaminoaniline-formaldehyde complex which is readily washed from the emulsion by one or two water rinses after the processing steps have been completed.
The 2,4-diaminoanilines which are utilized as the color developers for the production of azine dyestufi images are of the type described in the aforementioned Patent 2,486,440 and in application Serial No. 101,913, filed June 28, 19%, now Patent No. 2,570,116, and entitled Color Developers for the Production of Azine Dye Images." Specific examples of such developing agents are:
-(B-hydroxyethylamino) 6 (4'-carb0xymethoxyphenylamino) -metanilic acid -(carboxymethylamino) 6 (i-'-methoxyphenylamino) -metanilic acid 2- s-sulfoethylamino) -4-phenylamino aniline 4,6-di(/s-hydroxyethylaminol -metanilic acid 4-(5 hydroxyethylamino) -6phenylamino-metanilic acid .Z-(B-hydroxyethylamino) 4 (fi sulfoethylamino) -5-methy1 aniline 4-(B-hydroxy-e-methylethylamino) 6 phenylamino-metanilic acid e-ls-dflhydroxyethyl)ethylaminol 5 (3-ethoxyphenylamino) -metanilic acid 4-(5 hydroxyethylamino) 6 methylaminometanilic acid 4-(sulfomethylamino) 6 methylphenylaminometanilic acid -(c hydroxyethylamino) 6 methylaminometanilic acid Color formers which are used with the aforementioned developers to give yellow azine dye images are also described in the aforementioned application Serial No. 101,913. These compounds are typified by the fact that they are open-chain ketomethylene compounds. Examples of such compounds are:
Acetoacetanilide N- l -naphthylacetoacetamide N,N' -ethylenebisacetoacetamide p,p'-bi o-acetoacetaniside N-2-naphthylbenzoylacetamide p,p -bi-acetoacetanilide a,a-terephthaloylbis (3 chloro 4,6 dimethoxyacetanilide) a-benzoylacetaniiide Preferably, the color formers utilized contain a group rendering them non-migratory in the emulsion. Examples of such compounds are:
2 (m benzoylacetamidophenyl) l octadecyl- 5-benzimidazolesulfonic acid 3,3 ureylenebis 5 p benzoylacetamidobenzamide-benzenesulfonic acid 2 p benzoylacetamidobenearnido 6 stearoylamino-p-toluenesulfonic acid 2 (p benzoylacetamidophenyl l octadecyl- 5-benzimidazo1esulfonic acid p cyanoacetyl 3 octadecenylsuccinalic acid.
Color formers capable of producing magenta dyestuff images are also described in the above identified application and in USP 2,524,741. Preferably, these color formers are 6-halogen-8-hydroxyquinolines, and particularly those which are non-migratory in the emulsions. Examp1es of the latter type compounds are:
6 stearoylamino 2 (2 phenyl 6 bromo- 8' hydroxycinchoninoyl) aminotoluene 4- sulfonic acid 2 phenyl 6 chloro 8 hydroxycinchoninoyloctadecyl taurine 6 decoxy 3 (2 phenyl 6 bromo 8 hydroxycinchoninoyl) amino benzenesulfonic acid.
2 (3 stearoylaminophenyl) 6 bromo 8- hydroxycinchoninic acid 2 stearoylamino 6 (6 chloro 8 hydroxycinchoninoyl) aminotoluene 4 sulfonic acid, and the like.
Color formers for the cyan image are also described in USP 2,570,1 6, issued October 2, 1951, and in USP 2,445,252, issued July 13, 1948. Preferably, these color formers are aryl-J-acid derivatives, particularly those containing a group rendering the color former non-migratory in the emulsion. Examples of the latter compounds are: dodecyl urethane of fi-sulfoethyl-J-acid tetradecyl urethane of p-anisyl-J-acid Z-hexadecyl urethane of phenyl-J-acid 4-stearoylamino-J-acid, and the like.
By employing an acidified formaldehyde solution, a substantial improvement in color brilliance and rendition is obtained. This is attributable to the fact that formaldehyde forms a highly soluble complex with the color developer in an acid solution, and as a consequence, reduces color degradation and leads to improved color brilliance.
The following examples describe in detail the method for accomplishing the above objects. It is to be understood, however, that they are exemplary only and they are not to be construed as being limitative.
Example I A red sensitive emulsion containing phenyl-J- acid-N-octadecyl urethane was exposed and the latent image developed in a black and white developer, re-exposed, and the residual silver halide developed in a solution of the following composition:
Grams Sodium carbonate (monohydrate) 40 Sodium sulfite 40 Sodium sulfate 50 Ethylenediamine l5 Z-aminopyridine 10 4 (B hydroxyethylamino) 6 methylamino-metanilic acid 5 Water to make 1000 cc.
After color development, the layer was rinsed, and treated for 5 minutes in a bath of the following composition:
Hydrochloric acid grams 5 Formaldehyde 0% aqueous solution) cc 10 Water to make 1000 cc.
The film was washed, bleached in a ferricyanide bleach, and fixed in an acid hardening solution. There is obtained a cyan positive dye image completely free from stain and stable against accelerated adverse storage conditions.
Example I I Grams Sodium carbonate (monohydrate) 40 Sodium sulfite 60 Potassium bromide 5 Pyridine 16 Benzylamine 1 4 (B hydroxyethylamino) 6 phenyl amino-metanilic acid 5 Water to make 1000 cc.
After color development, the film was rinsed and treated for 5 minutes in a bath of the following composition:
Acetic acid grams 10 Formaldehyde l0% aqueous solution) cc 40 Water to make 1000 cc.
The film was washed, bleached in a ferricyanide bleach, and fixed in an acid hardening fixer solution. There was obtained a multicolor film containing stain-free positive dye images of excellent brilliance and freedom from color degradation.
Example III An integral tripack of essentially the same composition as in Example II was exposed and color developed for minutes to a negative image in a solution of the following composition:
Grams Trisodium phosphate Sodium sulfite 40 Potassium bromide 12.5
Hydroxylamine hydrochloride 1 4 4,8 hydroxyethylamino) -6-benzylamin0- metanilic acid 6 Water to make 1000 cc.
After development, the film was rinsed and treated in a bath of the following composition:
Citric acid grams 10 Formaldehyde (40% aqueous solution) cc 20 Water to make 1000 cc.
The film was washed, bleached in a ierricyanide bleach, and fixed in an acid hardening hypo solution. There was obtained a brilliant negative dye image completely free from stain and color degradation. The negative did not acquire additional stain nor become subject to color degradation during three weeks accelerated aging at relative humidity and F.
It will be obvious to any one skilled in the art that many modifications, such as substituting equivalent materials and varying the proportions of materials used, are within the spirit and scope of the invention as defined in the appended claims.
I claim:
1. In the process of eliminating stain in the production of subtractively colored azine dye images in a silver-halide emulsion involving ex- 'posure of said emulsion, color developing the same in a ZA-diaminoaniline developer in the presence of a color former to produce a subtractively colored azine dye image, bleaching, fixing and washing said emulsion, the improvement which comprises interpolating between the color development and bleaching step a rinsing of the color developed emulsion with an aqueous solution containing from 0.1 to 10% of formaldehyde and 0.1 to 10% of a water soluble acid.
2. The process according to claim 1 wherein the acid is acetic.
3. The process according to claim 1 the acid is hydrochloric.
4. The process according to claim the acid is maleic.
5. The process according to claim the acid is citric.
6. The process according to claim 1 the acid is acrylic.
wherein 1 wherein 1 wherein wherein JAMES E. BATES.
References Cited in the file of this patent UNITED STATES PATENTS Harsh Aug. 15, 1950

Claims (1)

1. IN THE PROCESS OF ELIMINATING STAIN IN THE PRODUCTION OF SUBTRACTIVELY COLORED AZINE DYE IMAGES IN A SILVER-HALIDE EMULSION INVOLVING EXPOSURE OF SAID EMULSION, COLOR DEVELOPING IN THE SAME IN A 2,4-DIAMINOANILINE DEVELOPER IN THE PRESENCE OF A COLOR FORMER TO PRODUCE A SUBTRACTIVELY COLORED AZINE DYE IMAGE, BLEACHING, FIXING AND WASHING SAID EMULSION, THE IMPROVEMENT WHICH COMPRISES INTERPOLATING BETWEEN THE COLOR DEVELOPMENT AND BLEACHING STEP A RINSING OF THE COLOR DEVELOPED EMULSION WITH AN AQUEOUS SOLUTION CONTAINING FROM 0.1 TO 10% OF FORMALDEHYDE AND 0.1 TO 10% OF A WATER SOLUBLE ACID
US202437A 1950-12-22 1950-12-22 Process of removing color developer stain in azine dye images Expired - Lifetime US2657139A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BE507902D BE507902A (en) 1950-12-22
US202437A US2657139A (en) 1950-12-22 1950-12-22 Process of removing color developer stain in azine dye images
DEG7657A DE900782C (en) 1950-12-22 1951-12-14 Process for the production of subtractive azine dye images in halogen silver emulsion layers
GB29514/51A GB701341A (en) 1950-12-22 1951-12-17 Process of avoiding color developer stain in the formation of azine dye images
FR1047081D FR1047081A (en) 1950-12-22 1951-12-21 Method of removing color developer stains from azine dye images
CH295701D CH295701A (en) 1950-12-22 1951-12-22 Process for removing stains and preventing color degradation from images of phenazonium dyes.

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US202437A US2657139A (en) 1950-12-22 1950-12-22 Process of removing color developer stain in azine dye images

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DE (1) DE900782C (en)
FR (1) FR1047081A (en)
GB (1) GB701341A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2827375A (en) * 1954-03-26 1958-03-18 Gen Aniline & Film Corp Polyamines as short stop agents for azinte color developers
DE1056478B (en) * 1956-11-05 1959-04-30 Eastman Kodak Co Process for preserving color photographic color developer solutions
US2980536A (en) * 1956-07-02 1961-04-18 Morton Chemical Co Photographic shortstop compositions
US3140177A (en) * 1960-11-10 1964-07-07 Eastman Kodak Co Processing color photographic materials
US3649277A (en) * 1967-10-02 1972-03-14 Fuji Photo Film Co Ltd Water-washing accelerating composition for silver halide color photographic light sensitive elements
US3909267A (en) * 1972-12-13 1975-09-30 Fuji Photo Film Co Ltd Stabilization process for color photographic materials

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2367548A (en) * 1942-09-04 1945-01-16 Eastman Kodak Co Hardening and stain prevention process in color photography
US2515121A (en) * 1945-11-08 1950-07-11 Gen Aniline & Film Corp Process for preventing stains in photographic color material by treatment with basic acids immediately prior to drying
US2518686A (en) * 1945-11-08 1950-08-15 Gen Aniline & Film Corp Aldehyde antistain baths for developed color photographic material

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2367548A (en) * 1942-09-04 1945-01-16 Eastman Kodak Co Hardening and stain prevention process in color photography
US2515121A (en) * 1945-11-08 1950-07-11 Gen Aniline & Film Corp Process for preventing stains in photographic color material by treatment with basic acids immediately prior to drying
US2518686A (en) * 1945-11-08 1950-08-15 Gen Aniline & Film Corp Aldehyde antistain baths for developed color photographic material

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2827375A (en) * 1954-03-26 1958-03-18 Gen Aniline & Film Corp Polyamines as short stop agents for azinte color developers
US2980536A (en) * 1956-07-02 1961-04-18 Morton Chemical Co Photographic shortstop compositions
DE1056478B (en) * 1956-11-05 1959-04-30 Eastman Kodak Co Process for preserving color photographic color developer solutions
US3140177A (en) * 1960-11-10 1964-07-07 Eastman Kodak Co Processing color photographic materials
US3649277A (en) * 1967-10-02 1972-03-14 Fuji Photo Film Co Ltd Water-washing accelerating composition for silver halide color photographic light sensitive elements
US3909267A (en) * 1972-12-13 1975-09-30 Fuji Photo Film Co Ltd Stabilization process for color photographic materials

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Publication number Publication date
BE507902A (en)
DE900782C (en) 1954-01-04
GB701341A (en) 1953-12-23
CH295701A (en) 1954-01-15
FR1047081A (en) 1953-12-10

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