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
  • G03C7/3244—Couplers forming azinic dyes; Specific developers therefor

Definitions

• Patented Sept. 19, 1950 PRODUCTION OF YELLOW DYEIMAGESBY.
• the present invention relates; to the preparation of yellow dye images by photographic color forming development.
• a permanent'yel'low dye image can be produced simultaneously with the cyan and maenta azine dye images by color forming development with a 2.4-diamirxo aniline in the presence of a keto methylene compound providing that the pH of the photographic element subaniline in the presence of a colon former which is preferably an aromatic compound containing at least one hydroxyl, group linked to the aromatic structure.
• a colon former which is preferably an aromatic compound containing at least one hydroxyl, group linked to the aromatic structure.
• hydroxy alkyll- such as hydroxy ethyl
• sulfo alkyl such as sulfomethyl, sulfopropyl, sulfobutyl and the like, or an aromatic radical such as aryl, i. e., phenyl, naphthyl and the like, carboxy aryl, i. e., carboxy phenyl, carboxy naphthyl and the like, sulfo aryl, i.
• alkoxy aryl such as methoxy phenyl, methoxy naphthyl, ethoxy phenyl, butyroxy phenyl and the like, alkyl aryl such as toluyl, ethylphenyl, propylphenyl and the like, carboxy alkylaryl, such as carboxy methyl phenyl, carboxy' ethyl phenyl and the like, carboxy alkoxy aryl, such as carboxy methoxy phenyl, carboxy ethoxy phenyl, hydroxy alkyl aryl such as hydroxy methyl phenyl, hydroxy ethyl phenyl and the like, and hydroxy a1- koxy aryl such as hydroxy methoxy phenyl, hydroxy ethoxy phenyl and the like, R is an aromatic or aliphatic
• the color former which is utilized for the for- H2 mation of the yellow dye image upon development is any open chain keto methylene compound, i. e., any compound containing in a straight chain a methylene group which is activated by one or more keto groups or by a keto group and a cyano or SO2 group.
• the benzimidazole compounds 1. e., Nos. 13 and 32, are new products. Such compounds are produced, taking compound 32, for example, by
• keto methylene compounds are well known, and are used, for example, as
• Compound 13 is made .in the same manner excepting that 2--(4' -,aminophenyl)--l-octadecylbenzimidazole--sulfonic acid is replaced by .2- .(3' aminophenyl) -1-octadecylbenzimidazole 5- :sulfonic acid. 1
• the parent benzimidazole is prepared byheating a 3-amino-4-alkylamino benzene sulfonic or :carboxylic acid with the -de- ⁇ sired nitro benzenecarboxylic acid chloride in the presence ,of pyridine or any .other suitable :acid binding agent.
• the .nitro group in the benbimidazole is then reduced 'to an amino group.
• Preparation of the intermediate is analogous to 'the :method described iin .copending application Serial (No. 745,113, filed April 30, 1947, with :the "exception that the l -hydroxy-2enaphthoylchloride is replaced by the desired nitro-benzoyl chloride followed by reduction of thenitro group after ring closure.
• the alkali treatment step leading toyellowrdye image formation is conducted before final "washing and drying and involves merely the subjection of the photographic element being processed to the action of @an aqueous solution of a. water rsoluble alkali, such as sodium carbonate, potassium carbonate and the like. As the pH of the photographic elementincreases, the yellow image appears as a result roftthe transformation of the previously formed magenta image.
• the particular stage at which the alkali treatment is interposed may varydepending upon the nature of the fixing bath employed. Generally speaking, such alkali treatment will be a final phase of the processing operation and will usually lbelsucceeded by the final wash and drying. This order will always prevail 'where the fixing bath is acidic. If, however, the fixing bath is neutral, then the alkali treatment may follow bleaching and precede fixing. In any case, the
• the process may be carriedrout by utilizing the color formers in the color forming developer or in the silver-halide emulsion.
• the color formers are'loca'ted in the emulsion and are so constituted that they do not difluse therefrom .during the photographic processing.
• the color formers may be rendered fast to ,dif- ,insion in the emulsions by methods usually employedin the art, for example, those described in Unitedv States Patents Nos.
• the process may be utilized for the formation "0;? ,negative :color images, positive color images,
• the yellow dye images produced by the present invention have excellent light fastness and brilliance and very adequately complement the magenta and cyan dyes produced by the azine process.
• Example 1 To 100 ml. of a developer solution made up as follows:
• Example 2 A photographic silver halide emulsion containing as a non-difiusing color former p-cyanoacetyl-B-octadecenyl-succinalic acid having the following constitution:
• Example 3 The procedure is the same as in Example 1 excepting that the developer is made up of equal parts of 4.6-di-(phenylamino)-metanilic acid silver halide emulsion in the presence of an open chain keto methylene compound with a 2.4-diamino-aniline in which the nitrogen atoms in 2- and 4-positions have directly linked thereto a carbon atom of a radical selected from the class consisting of aliphatic and aromatic radicals, bleaching and fixing said emulsion, and adjusting the pH of the emulsion in a final phase of the processing operation by treatment with an alkali untilthe yellow image manifests itself when the emulsion has been previously subjected to an acidic treating bath.
• a radical selected from the class consisting of aliphatic and aromatic radicals
• the process of producing yellow dye images which are resistant to splitting by strong mineral acids which comprises developing a devolopable silver halide emulsion in the presence of an open chain keto methylene compound with a 2.4-diamino-aniline in which the nitrogen atoms in 2- and 4-positions are directly linked to the carbon atom of a radical selected from the class consisting of aliphatic and aromatic radicals, bleaching the silver formed by such development, fixing the silver salts by an acid hardening fixing bath, and subsequently adjusting the pH of the emulsion by treatment with an alkali until the yellow image manifests itself.

Landscapes

• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)

Priority Applications (6)

Applications Claiming Priority (1)

Publications (1)

Family

ID=22071952

Family Applications (1)

Country Status (6)

Cited By (4)

Citations (1)

• 0
  • BE BE492847D patent/BE492847A/xx unknown
• 1948
  • 1948-12-22 US US66825A patent/US2522802A/en not_active Expired - Lifetime
• 1949
  • 1949-12-12 GB GB31880/49A patent/GB662419A/en not_active Expired
  • 1949-12-16 DE DEG607A patent/DE827901C/de not_active Expired
  • 1949-12-20 FR FR1003992D patent/FR1003992A/fr not_active Expired
  • 1949-12-22 CH CH289721D patent/CH289721A/fr unknown

Patent Citations (1)

Also Published As

Similar Documents