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
  • G03C7/3231—Couplers containing an indazolone ring

Definitions

• This invention relates to a. process for the production of color photographic images by color development in the presence of a color coupler, to photographic developers, photographic material containing such couplers, and photographic images obtained by such a process.
• a colored image may be formedv by developing a reducible silver salt image in the presence of a compound which during the development couples with the oxidation product of the developing agent and forms a dyestufi which is deposited on the developed silver grains.
• magenta image may also be obtained when a compound is used as a color coupler which does not contain such. an active methylene group.
• a further object of this invention is to provide new photographic developers containing a color coupler.
• Another object of the invention is to provide new photographic material containing a color coupler.
• a reducible silver salt image is developed with a primary aromatic amino developing agent in the presence of a compound corresponding to the following Formula I:
• aromatic nucleus may be isocyclic, heterocyclic
• the polycyclic nucleus completed by Z may contain at least one further -NH-NH-CO- group so as to have a double indazolone compound.
• the compound, as completed by Z may-- also contain two or more nuclei linked by a chemical bound or by a bior poly-valent atom or group, such as Bearing in mind that the new color coupler may be represented by Formula II, it is believed that coupling with the oxidation products of the developing agent occurs at the N-atom in ortho-- position to the OH group. This assumption is These formulae are analogous to the formula LV of Baker for 2-substituted indazolone (J.
• Color couplers according to Formula I may be obtained by causing a molecule of water to split off from aromatic, dihydro-aromatic or heterocyclic monoor poly-(orthohydrazino carboxylic acids) according to the method described by I K. Pfannsteil and J. Janecke in Berichte 751 Sometimes, the preparation of one of said hydrazino acids yields directly the corresponding indazolone because the hydrazino acid although occurring at an intermediate stage cannot be isolated.
• the color coupler according. to my present invention may also be obtained in a manner anal be written in many tautomeric forms, one of which is represented by the following Formula Most of these color coupler are converted into a yellow product when in an oxidizing medium such as a bath for removal of the silver so that a yellow reversal image, which results from the oxidation of th residual color coupler in the bath for removing the silver, is added to the dyestuff image formed on color development. If this is undesirable, the formation of the yellow product may be avoided by treating the color developed emulsion layer, before removing the silver, with a bath containing formaldehyde, a formaldehyde-yielding compound, or another aldehyde. Such an aldehyde is supposed to react with the --NHNHCO group of the coupler, avoiding in this way any subsequent coupling or formation of yellow oxidation products.
• the dyestufis obtained on color development with the color couplers according to the present invention are more stable to acid than those obtained with the known pyrazolones, and those which contain a substituent rendering them fast to diffusion are not removable from the emulsion layer by washing.
• the said new color couplers may further .be
• colloid layer used in the developing solution or in a colloid layer, in the latter case either in a lightg-sensitive layer or in a non-light-sensitive layer adjacent to a sensitive layer or separated therefrom by a water-permeable colloid layer.
• the aromatic amino compounds which may be used as developing agent in. accordance with the present invention include the mono-, diand tri-amino aryl compounds.
• the monoamino developing agents may be .mentioned scope thereof.
• Example 1 1.1 g. indazolone according to Formula IV:
• Example 2 1 g. 4-chloro-indazolone according to Formula V:
• Example 3 11 g. 3.5dichloro-2-amino benzoic acid are dissolved in 50 cc. of a concentrated aqueous so- .lution of hydrochloric acid and 350 cc. water.
• Example 5 8.5 g. 4-sulfo-1-amino benzol-2-carboxylic acid are dispersed in 32 cc. of a concentrated aqueous solution of hydrochloric acid. successively, 64 cc. of an aqueous solution of sodium nitrite 5% are added to the suspension, and then 225 cc. water. The whole is brought slowly into 480 cc. of a solution of S02 while S02 gas is continuously conducted into that solution. After complete addition, S02 is introduced for yet half an hour. Next, the volume of the mixture is reduced to about 150 cc. by evaporation. The mixture is cooled and filtered with suction. The product separated is'recrystallized in a little amount of water. It melts above 300 C. and is believed to be indazolone-5-sulfonic acid corresponding to Formula VIII:
• An exposedpositive motion picture film is developed in the color developer thus prepared and a bluish magenta image is formed.
• Example 6 6.6 g. B-amino-indazolone-hydrochloride, prepared according to Berichte (1912) 1107, and 5.1 g. 2-chlorobenzothiazole are dissolved in cc. absolute ethanol. The solution is evaporated on the water bath. The residue is washed by boiling with ether and then with water. The washed residue is dissolved in 200 cc. ethanol. The volume of the solution is reduced to 20 cc. The product which precipitates after cooling is filtered with suction. It melts at 252255 C. After washing by boiling with water and then with acetone, the melting point may be raised to 270-272 C.
• the product is believed to be 6(2'-benzothiazolyl amino)indazolone according to Formula 2 g. of this indazolone derivative are dissolved in 20 cc. of a methanolic solution of potassium hydroxide N and added to 1 litre of a mixture of equal parts of the following solutions:
• Example 8 A mixture of 5.5 g. G-aminoindazolone-hydrochloride, 3.7 g. phthalic acid anhydride and 5 cc. pyridine is heated for 30 minutes at 180 C. on an oil bath. The mixture is cooled and the solid mass obtained is washed by boiling with water and next with acetone. Melting point is 304-305 C. N content calculated 15.05, found 14.79. The product is believed to be fi-phthal-imido indazolone corresponding to Formula X1:
• Example 10 A solution of 1.1 g. 6-amino-indazolone-hydrochloride and 1.1 g. of the copolymer of styrene and maleic acid anhydride in 5.5 cc. pyridine is boiled for 5 hours. The reaction mixture is washed with boiling water, and then with boiling methanol. A product melting above 300 C. and corresponding to Formula XIII:
• Example 11 3.2 g. S-amino-indazolone hydrochloride prepared according to Berichte 75 (1942) 1107, 6 g. stearic acid chloride and 45 cc. pyridine are refluxed for 5 hours. The residue is washed by boiling first with water, then with acetone and finally with methanol. 5 stearoyl-amino indazolone melting at 218-220 C. and corresponding to- Formula XIV:
• Example 12 0.2 g. of the bis-indazolone derivative called hereinafter 5-(indazolonyl-5') -indazolone, corresponding to Formula XV:
• Example 13 0.2 g. 2-6-dimethyl-4-hydrazino nicotinic anhydride corresponding to Formula XVI:
• Example 14 XVII OH-NH 1 g. of this product is dissolved in cc. of an aqueous solution of potassium hydroxide N/2 and added to 100 cc. of an emulsion for positive motion picture film. This emulsion is coated onto a 10 tained by mixing equal parts of the following solutions:
• Example 16 To 14 g. diamino diphenyl methane dicarboxylic acid and 40 cc. concentrated aqueous solution of hydrochloric acid, 35 cc. of an aqueous solution of sodium nitrite 10% are added while cooling with ice. The reaction mixture is filtered. The filtrate is added in 30 minutes drop by drop to 400 cc. of a saturated aqueous solution of sulphurous anhydride while cooling with icewater and conducting S02 into the reaction mixture. After complete addition, introduction of S02 is continued for another 30 minutes. 400 cc. water are then added and the whole is boiled for one hour, whereupon the mixture is filtered and the filtrate cooled. The precipitate is recrystallized from ethyl alcohol. The S-methylene-bis- (indazolone) obtained corresponds to Formula XIX:
• Photographic developer containing a primary aromatic amino developing agent and a color coupler having a formula selected from the group consisting of For'mulaI:
• A'photographicdeveloper containing a primary aromatic amino developing agent and 5- (indazolonyl-B') -indazolone.
• a photographic material comprising a silver halide emulsion layer and a colloid layer, containing an octadecenyl-succinyl-amino-indazolone.
• a photographic material comprising a silver an teutom r c. fo m of o m la I.v wh Z re ent he n n-m atom r ui for co et n an erqm c ucleus,-

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• Silver Salt Photography Or Processing Solution Therefor (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)

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Citations (6)

• 0
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  • NL NL84810D patent/NL84810C/xx active
  • BE BE514576D patent/BE514576A/xx unknown
  • NL NLAANVRAGE7709088,A patent/NL172896B/xx unknown
  • NL NL717100393A patent/NL150078B/xx unknown
  • BE BE492307D patent/BE492307A/xx unknown
• 1948
  • 1948-11-23 GB GB30406/48A patent/GB663190A/en not_active Expired
• 1949
  • 1949-11-21 FR FR1015150D patent/FR1015150A/fr not_active Expired
  • 1949-11-22 US US128913A patent/US2673801A/en not_active Expired - Lifetime
  • 1949-11-22 CH CH283789D patent/CH283789A/fr unknown
  • 1949-11-24 DE DEG457A patent/DE814996C/de not_active Expired
• 1951
  • 1951-10-03 GB GB23087/51A patent/GB720284A/en not_active Expired
• 1952
  • 1952-10-02 CH CH304621D patent/CH304621A/fr unknown
  • 1952-10-02 FR FR64640D patent/FR64640E/fr not_active Expired
  • 1952-10-03 DE DEG9910A patent/DE918484C/de not_active Expired

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