Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
  • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
  • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
  • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
• • 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
  • G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific
• • 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
  • G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor

Definitions

• This invention relates to a method of incorporating photographic chemical compounds, particularly color couplers in hydrophilic colloids, and especially in light sensitive silver halide gelatin photographic emulsions.
• the incorporation into the emulsion of long chain high molecular weight couplers containing salt-forming groups poses a number of difliculties.
• the corol formers are dissolved in a water, or water-alcohol solution, of an alkali metal hydroxide such as aqueous sodium hydroxide or alcoholic potassium sydroxide, and then added to the emulsions as a so-called coating final, as one of the last additives just prior to coating.
• a further object of this invention is to provide a method of incorporating in a hydrophilic, photographic colloid, color formers which are stable to diifusion and have an acid group as a substituent.
• a further object of the invention involves the uniform 7 distribution of a color former in a liquid photographic gelatin silver halide emulsion while insuring that the viscosity of said silver halide emulsion does not increase materially on holding.
• a still further object of this invention comprises a light sensitive gelatin silver halide emulsion containing a color former uniformly distributed through the gel matrix without the use of an alkali metal hydroxide solvent.
• the color formers are dissolved in dimethyl sulfoxide.
• the dimethyl sulfoxide solution of the color former is then diluted with water which may also contain other coating finals.
• the aqueous dimethyl sulfoxide solution is then added directly to a melted gelatin silver halide emulsion with 07 adequate stirring.
• the solution of tin and the resulting mixture combined with a melted gelatin silver halide emulsion.
• dimethyl sulfoxide employed varies somewhat with different color formers. In general amounts ranging from 5 to 35 parts by weight of dimethyl sulfoxide per 10 parts by weight of color'former have been found to be most satisfactory.
• the usual coating aids, stabilizers and wetting agents such as saponin and/or synthetic surfactants which may be of the anionic, cationic, non-ionic or amphoteric type, are add ed prior to the addition of the color formers.
• wetting agents are those described in United States Patents 1,970,578, 2,118,059, 2,240,476 and 2,768,894.
• the color formers which have the strongest tendency to increase the viscosity on holding contain in their molecule, a jbenzimidazole nucleus which is substituted on the nitrogen atom in the 1-position by an alkyl chain of at least 10 carbon atoms and substituted in the 5-position by a water solubilizing group, in which the benzirnidazole nucleus is connected through its carbon atom in the 2- position to the residue of a color forming residue which is reactive with the oxidation products of a primary amino developing agent and contains a reactive methylene or ethenol or phenolic hydroxyl group.
• color formers which contain a benzimidazole nucleus as part of the molecule and which are capable of forming dye images upon development with a dialkylamino-aniline developing agent are illustrated by the following structural formulae:
• R is a hydroxy aromatic radical, such as substituted or unsubstituted hydroxynaphthyl, hydroxyphenyl
• Suitable examples of color formers embraced by these general formulae are disclosed in United States Patents 2,545,687 and 2,547,307, in which their method of preparation is also described;
• R R and R have the same values as above;
• R is'hydrogen, a carboxyalkyl, allyl or lower alkyl group; andR- is an allyl, lower alkyl, aryl or heterocyclic group.
• the resultant solution was diluted with 3750 milliliters of water and added to ten kilograms of a liquid gelatin silver halide emulsion sensitized to red light and containing about 8 percent of gelatin, 3 percent of silver bromoiodide, plus small amounts of saponin and sodium tetradecyl sulfate as wetting agents.
• the color former was dissolved in 200 milliliters of 4 percent sodium hydroxide solution which was diluted with 3800 milliliters of water prior to addition of the emulsion.
• Viscosity measurements were taken at various holding times (40 C.) with the followingresults:
• Control (Sodium Hydroxide) Test (Dimethyl Sulfoxide) Time Relative Time Relative viscosity viscosity Q Hour 86.2 0 Hour 106. 6 V 2 Hours 113.8 2 Hours 112. 8 3 Hours 119.0 3 Hours 114. 2 4 Hours. 124. 2 4 Hours 113. S 5 Hours 129.0 5 Hours I v 113 .0
• the emulsion with the dimethyl sulfoxide solvent wascoated onto a base and dried. It gave a coating of even thickness and even maximum density after development.
• the control emulsion due to its continued increase in viscosity, showed variations in the developed color den sities between the start and the end of the coating.
• Example I A u L-- Example 111 Example I was repeated except that a blue sensitive silver halide emulsion was used which contained 20 grams of the yellow color former, 2-(4'-benzoylacetaminophenyl)-1-octa-clecylbenzimidazole-S-sulfonic acid having the following structural formula:
• Example IV Example 111 was repeated with the exception that the 20 grams of 2-(4'-benzoylacetaminophenyl)-1-octadecylbenzimidazole-S-sulfonic acid were replaced by 25 grams of 2 [(3',5-dibenzoylacetamino)phenyl]-l-octadecylbenzimidazole-S-sulfonic acid having the following struc-
• the viscosity of the emulsion containing the dimethyl sulfoxide did not increase during a 5 hour holding period at 40 C. However, the viscosity of the material prepared with sodium hydroxide, increased by about 60 percent during the same holding time.
• Example V Sixty grams of the magenta color former 2-[4-(6-bromo S-hydroxy-Z-(2-sulfophenyl)-cinchoninoyl)-aminophenyl]-l-octadecyl-S-snlfonbenzimidazole, having the following structural formula:
• R is the residue of the color forming molecule and contains a group selected from the class consisting of methylene, ethanol and phenolic hydroxy groups capable of reacting with the oxidation products of the primary amino developing agent;
• R is an aliphatic hydrocarbon radical containing at least 10 carbon atoms;
• R is a water solubilizing group and the carbon in the 2-position of said benzimidazole radical is linked to the residue of the color forming molecule which contains a reactive group selected from the group consisting of methylene, ethenol and phenolic hydroxy groups which comprises dissolving said color former in dimethyl sulfoxide, diluting the color former solution thus obtained with an aqueous solution of a surface active agent and adding the resultant solution to a liquid gelatin silver halide emulsion prior to coating the latter upon a support.
• R is a hydroxy aromatic radical, thehydroxy I group being nuclearly attached and said radical being linked to the benzimidiazole nucleus in an ortho position. to said hydroxy group; R is an alkyl chain of at least 10,
• said color former is l-0ctadecyl-2[Z'-(l'-hydroxynaphthyl) ]-benzimindazole-5-sulfonic acid.

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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)
• Compositions Of Macromolecular Compounds (AREA)

Priority Applications (5)

Applications Claiming Priority (1)

Publications (1)

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Family Applications (1)

Country Status (3)

Cited By (7)

Citations (4)

• 1959
  • 1959-09-30 US US843374A patent/US3050394A/en not_active Expired - Lifetime
• 1960
  • 1960-09-19 GB GB32147/60A patent/GB912969A/en not_active Expired
  • 1960-09-28 DE DEG30585A patent/DE1116533B/de active Pending

Patent Citations (4)

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