US2186685A - Photographic color picture - Google Patents

Photographic color picture Download PDF

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Publication number
US2186685A
US2186685A US265759A US26575939A US2186685A US 2186685 A US2186685 A US 2186685A US 265759 A US265759 A US 265759A US 26575939 A US26575939 A US 26575939A US 2186685 A US2186685 A US 2186685A
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US
United States
Prior art keywords
photographic
methyl
dyestufi
blue
emulsion
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US265759A
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English (en)
Inventor
Schneider Wilhelm
Loleit Hans
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
GAF Chemicals Corp
Original Assignee
Agfa Ansco Corp
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Publication date
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Publication of US2186685A publication Critical patent/US2186685A/en
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Classifications

    • 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
    • G03C7/36—Couplers containing compounds with active methylene groups
    • G03C7/38—Couplers containing compounds with active methylene groups in rings
    • G03C7/381—Heterocyclic compounds
    • G03C7/3815—Heterocyclic compounds with one heterocyclic ring

Definitions

  • Our present invention relates to the manufacture of photographic color pictures.
  • dyestufi formers compounds which during the development with a developer containing a free amino-group, for instance para-phenylenediamine or para-aminophenol, yield a dyestufl' image on the silver image.
  • a free amino-group for instance para-phenylenediamine or para-aminophenol
  • yields a dyestufl' image on the silver image For obtaining blue 10- dyestufls there have hitherto been used by preference phenols and naphthols and derivatives thereof.
  • These dyestufl formers yield during development blue to blue-green quinoneimine dyeapplication describes components which contain Our present invention has for one object to provide a process of making blue-violet and redviolet photographic pictures.
  • Another object of our invention is to provide a process of producing such pictures wherein 20 there are used as dyestufi formers compounds of the general formula V or substituted phenylene.
  • a further object of this invention is the provision of a dyestufi forming developer which contains such dyestufi former.
  • dyestufl? components may be added to the developer or to the emulsion.
  • the component When the component is added to the developing solution it is recommended that it should first be dissolved in an organic solvent,-forinstance alcohol or acetone, and this solution should be added to the developer.
  • the components are prepared by reacting the internal anhydride of a poly- ;basic organic acid, such as the anhydrides of maleic acid, succinic acid, pyrotartaric acid and 20 the like containing for example a long aliphatic chain, i. e. of at least 5 carbon atoms such as octadecylene, isodecylene, iso-nonylene' and the like with a color former containing a reactive group
  • the ring of the anhydride is thereby split in such a manner that one CO-group unites with the reactive group and the other forms a carboxy group.
  • the color former there may be used p-amino-aceto-acetic anilide, 4-amino-1-phenyl-3-methyl-5- pyrazolone, l-amino-5-naphthol and the like.
  • anhydride there may be used octadecylene succinic acid anhydride a-dodecylea-hexahydrobenzene-pyro-tartaric. acid anhydride and the like.
  • the radicles which impart fastness-to difiusion may be introduced in a manner in itself known, for example by way of amino-, hydroxy- 0r carboxyl-groups, with the formation of an acid amide or an ester.
  • Silver halide emulsion layers comprising such dyestufi components may be applied singly or together with other layers on one or both sides of a carrier to produce a multi-layer material in which the layers are sensitized for difierent regions of the spectrum.
  • the silver halide emulsion layers containing the dyestuff formers may be united with other layers generally used in the production of photographic materials, for example filter layers, antihalation layers, matting layers, backing layers. They may also be combined with photographic layers in which color pictures are to be produced by any other process for instance by the silver bleaching out dyestufi process or the toning process.
  • binding agent for the photographic emulsions gelatin or any other colloid usual in photographic practice may be used.
  • Example 1 An exposedsilver halide emulsion layer is developed with a developer of the following composition: 1.6 grams 2-methyl-pyrro1e-3- carboxylic acid ethyl ester of the formula HCC.CO 0 Calls Methanol cc 60 Para-diethylaminoaniline hydrochloride grams 2 Crystalliz'ed sodium carbonate do Anhydrous sodium sulfite do 2 Potassium bromide do 0.2
  • Example 3 An exposed silver halide emulsion layer is developed with a developer of the following composition:
  • Example 6 0.5 gram of 2.5-dimethylindole is dissolved in methanol and added to 100 cc. of a solution having the composition described in Example 5; The film is developed and worked-up in the same manner as mentioned in Example 5. A red-violet picture is obtained.
  • Example 7 0.5 gram of 2-methyl-4-phenyl- 3-acetylpyrrole is dissolved in methanol and added to 100 cc. of a solution having the composition described in Example 5.” The film is developed and worked up in the same manner as mentioned in Example 5.' A blue picture is obtained.
  • Example 8 0.5 gram of 2-methyl-4-phenyl- 3-cinnamoylpyrrole is dissolved in methanol and added to 100 cc. of a solution having the composition described in Example 5. The film is developed and worked up in the same manner as mentioned in Example 5. A blue-violet picture is obtained.
  • Example 9 -0.5 gram of 2-methyl-4-phenylpyrrole-3-carboxylic acid is dissolved in methanol and added to 100 cc. of a solution having the composition described in Example 5. The film is developed and worked up .in the same manner as mentioned in Example 5. A blue-violet picture is obtained.
  • Example 10 0.5 gram of 2.4-dimethyl-3-acetylpyrrole is dissolved in methanol and added to cc; of a solution having the composition described in Example 5. The film is developed and worked up in the same manner as mentioned in Example 5. A blue-violet picture is obtained.
  • Example 11 0.5 gram of 2-me'thyl-4-phenyl- 3-benzoylpyrrole is dissolved in methanol and added to 100 cc. of a solution having the composition described in Example 5. The film is developed and worked up in the same manner as mentioned in Example 5. A blue-violet picture is obtained.
  • Example 13-2 methyl-4 phenyl-3-acetylpyremulsion may be used for the manufacture of a multi layer material. A blue-violet picture is obtained in this emulsion layer.
  • step which comprises causing as the dyestufl wherein R is a member selected from the class consisting of hydrogen, alkyl, aryl, aralkyl, carboxyl, esterified carboxyl, and aminated carboxyl and x is a member selected from the class consisting of vinylene, substituted vinylene, phenylene, and substituted phenylene, to react with the oxidation product of an aromatic developer.
  • the step which comprises developing the exposed photographic silver halide emulsion with an aromatic amino developer containing as the dyestufi former a compound of the general formula x o-om f Y wherein" I R is a member selected from the class consist ing of hydrogen, alkyl, aryl, aralkyl, carboxyl, esterified ca'rbcxyl, and aminated carboxyl and x is a member selected from the class consisting of vinylene, substituted vinylene, phenylene, and substituted phenylene.
  • step 3 which comprises exposing a photographic silver halide emulsion containing as the dyestufl iormer a compound of the general formula wherein R is a member selected from the class consisting of hydrogen, alkyl, aryl, aralkyl, carboxyl, esterified carboxyl, and aminated car- C boxyl and Q X is a member selected from the class consist- .ing of vinylene, substituted vinylene, phenylene, and substituted phenylene,
  • said compound containing a radicle imparting thereto i'astness to diffusion with respect to the w wherein binding agent of said emulsion, and developing said emulsion with an aromatic amino developer.
  • Silver halide emulsion for color photography comprising a compound 01 the generaliormula R is a member selected from the class consisting of hydrogen, alkyl, aryl, aralkyl, carboxyl, esterified carboxyl, and aminated carboxyl and X is a member selected from the class consisting of vinylene, substituted vinylene, phenyl ene, and substituted phenylene, said compound containing a radicle imparting thereto fastness to difiusion with respect to the binding agent of said emulsion.
  • a dyestufi forming developer comprising an aqueous solution containing an aromatic amino developing agent and a compound of the general formula R is a member selected from the class consist- .ing of hydrogen, alkyl, aryl, aralkyl, carboxyl, esterified carboxyl, and aminated car- I boxylic acid ethyl ester with undecylamine;
  • a silver halide emulsion ior color photography containing as the color forming component a 2-methyl-indole substituted in 5-position by a member of the group consisting of methyl and hydrogen, said indole having attached thereto a. radicle which renders the indole fast to difiusion with respect to the binding agent of the emulsion.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US265759A 1938-04-09 1939-04-03 Photographic color picture Expired - Lifetime US2186685A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI0061049 1938-04-09

Publications (1)

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US2186685A true US2186685A (en) 1940-01-09

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US265759A Expired - Lifetime US2186685A (en) 1938-04-09 1939-04-03 Photographic color picture

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US (1) US2186685A (enrdf_load_stackoverflow)
BE (1) BE433731A (enrdf_load_stackoverflow)
FR (1) FR852842A (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2532744A (en) * 1945-07-04 1950-12-05 Gen Aniline & Film Corp Diazotype containing as the azo component a quaternary salt of 2-methyl-6-methoxy-benzoselenazole
US5227287A (en) * 1990-11-26 1993-07-13 Fuji Photo Film Co., Ltd. Color-forming coupler and a silver halide color photographic material containing the same
US5260181A (en) * 1990-11-22 1993-11-09 Fuji Photo Film Co., Ltd. Color-forming coupler and a silver halide color photographic material containing the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2532744A (en) * 1945-07-04 1950-12-05 Gen Aniline & Film Corp Diazotype containing as the azo component a quaternary salt of 2-methyl-6-methoxy-benzoselenazole
US5260181A (en) * 1990-11-22 1993-11-09 Fuji Photo Film Co., Ltd. Color-forming coupler and a silver halide color photographic material containing the same
US5227287A (en) * 1990-11-26 1993-07-13 Fuji Photo Film Co., Ltd. Color-forming coupler and a silver halide color photographic material containing the same

Also Published As

Publication number Publication date
FR852842A (fr) 1940-03-04
BE433731A (enrdf_load_stackoverflow)

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