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

• This invention relates to the preparation of photographic yellow dye images by photographic color-forming development.
• the color formers embraced by the above formula are new entities in that the prior art does not show 5-amin'o Z-naphthols acylated with aroyl groups in thel-position.
• the resulting S-acetamido-l-aroyl-Z-naphthol is then treated with an acid or base to hydrolyze the acetamido group to the free amine in order to obtain the S-amino-l-aroyl-Z-naphthol.
• the color formers as herein described can either be incorporated in the emulsion or in the developer. If the former is desired, the color former should contain a group to prevent diffusion or wandering from its location in the photographic emulsions. Examples of such non-diffusing color formers are represented by compounds of Formulae 6, 7, 8 and'9. I This invention may be carried out so as to use the color developing method for producing colored negatives, colored positives, or reverse images. These methods are general and conventional in the art and their efiicacy is dependent upon the point at which color development takes place.
• the filtrate was. warmed and diluted with an equal volume of water, then set aside to. cool and crystallize. After chilling; the crystalline solids were collected on a Biichner funnel, washed once with aqueous methanol and dried. The yield of orangeyellow product was 87% of theory.
• Example 11 fi-AMING-I-Q-CHLOROBENZOYD2-NAPHTHOL- COMPOUND 2 1-(2-chlorobenzoyl)-5-acetamido-2-naphthol (0.5 g.) was placed in a 50 ml. round bottom flask with 25 ml. of a mixture consisting of equalvolumes of ethanol and concentrated hydrochloric acid. After refluxing for 2-3 5 hours, the solution was allowed to cool and made alkaline with 6 N sodium hydroxide solution. After charcoaling and filtering, the filtrate was acidified with acetic acid.
• the orange-red product was collected by filtration, Washed with water and recrystallized by dissolving in a small 10 amount of boiling methanol, diluting to cloud point with water, and setting aside to cool and crystallize.
• the yield of brick-red product was 0.3 g. with a melting point of 155 C.
• orange filtrate was acidified with acetic acid and the resulting solids collected and washed with water.
• the wet filter cake was dissolved in about 100 ml. of hot methanol, charcoaled and filtered.
• the filtrate was diluted with an equal volume of hot water and set aside to cool and crystallize;
• the yield of orange colored product was 2.1 g. and had a melting point of 200 C. l Analysis.Nitro2en-calc.: 5.01. Found: 5.04.
• Example IV 5-AMINO-1-PMETHOXYBENZOYL-g-NAPHTHOL- COMPOUND 4 OOHa I i OH NH Q5 2
• 1-(4-methoxybenzoyl)-5-acetamido-2-naphthol (2.5 g.) was placed in a flask containing 20 ml. of a solution consisting of equal volumes of, ethanol and hydrochloric acid.
• the resulting solution was refluxed for three hours 10 and then made alkaline with 6 N sodium hydroxide solution.
• the filtrate was acidified with acetic acid, the solids collected by filtration and washed with water.
• the damp filter cake was recrystallized from acetic acid.
• the yield of crystalline 3; product was 0.3 g. with a. meltingpoint of 235 C.
• hydrous aluminum chloride (0.2 mole) was then added portionwise with stirring. When the addition was completed, the reaction was heated on a steam bath for 1 hour. The resulting dark reaction "mixture was poured into about 250 ml. of ice and hydrochloric acid, diluted to about 7 50 mlQand made strongly alkaline with sodium hydroxide solution. After filtering from a slight amount of insoluble material, the layers were separated and the aqueous phase acidified with aceticacid. After collecting the resulting solids on 'a Biichner funnel and washing with water, the damp cake was dissolved in about 250 ml. of hot pyridine containing a small amount of acetic acid, charcoaled and filtered. The hot filtrate was diluted to the cloud point with water and set aside to cool and crystallize. ice and the solids collected by filtration, washed with diluted ethanol, and dried. The yield of pale yellow 7 crystalline produce was 53.3% of theory.
• The mixture was then chilled in Into a 100 ml., 3-necked flask, fitted with a stirrer and thermometer, was placed 25 ml. of dry tetrachloroethane. S-acetamido-Z-naphthol (0.025 mole) was suspended therein followed by 2-chlorobenzoyl chloride (0.025 mole). Anhydrous aluminum chloride powder (0.1 mole) was added portionwise to the chilled suspension (ice bath) with stirring.
• Example X To 100 ml. of a developer solution made up as follows:
• the strip After the strip had been washed free of hypo, it was treated in a 5% solution of sodium carbonate until the reddish-magenta image was completely converted to a brilliant yellow dye image, about 1 minute being sufficient for the conversion.
• the so obtained yellow image was stable to washing and dried, showed excellent light fastness and displayed no tendency to undergo a spectral shift when subjected to conditions as low as pH 5.
• the coupler may be incorporated in the photographic silver halide emulsion in which case one of the non-diffusing type is advantageously employed such as those represented by Formula 7 or 9.
• NHC O CnHas 4. The process of producing yellow azine dyestuff images by color-forming development which comprises exposing a silver halide emulsion and developing the same with a 2,4-diamino-aniline in the presence of a color former having the following formula:
• R is selected from the class consistinglof hy- 6.
• the -proccss as defined inclaim 4owhcrcin thc color dro'gfi, nitro,alkoxy,.alkyl and .-NHR' whcrcinoR' is former has the following formula: :7 selected from the class consisting of alkyl 'and aliphatic l i, I NEcocnHiu, acyl groups. I 5;
• the process as defined in claim 4 whcreinrthe color 5 former has the following formula: 1

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Citations (2)

• 0
  • BE BE576817D patent/BE576817A/xx unknown
  • DE DENDAT1069470D patent/DE1069470B/de active Pending
• 1958
  • 1958-04-03 US US726288A patent/US2921851A/en not_active Expired - Lifetime
• 1959
  • 1959-03-20 GB GB9839/59A patent/GB865032A/en not_active Expired

Patent Citations (2)

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