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

• a subtractive multi-color image is. composed of at least two dyestur't images.
• the dyestuffs should in theory completely absorb the visible light rays in one third of the spectrum and transmit them in the remaining two thirds.
• the dyestuffs commercially available do not fulfil these spectral requirements. For instance, the blue-green dyestuffs do not sufliciently absorb all red rays as desired, and moreover they show an undesirable absorption of the green and especially blue rays. show an insufficient absorption an undesirable blue-absorption.
• Said complementary image may consistof acolored color coupler which remains after color development, or of a dyestuif which, after treatment by the silver dyestuff bleach process, is left in the photographic. material at all points where no silver is or of a dyestuftproduced by azo-coupling or other coupling reaction with the residual color coupler. Since undesirable absorption occurs chiefly in the blue, the complementary image, in most cases, must be yellow. Schinzel, U. S. Patent 2,306,410, describes the formation of blue lignone dyes by oxidation of arylmethyl-pyrazolone, but it is added in this prior patent that the formation of the upper yellow part image in this manner presents diificulties.
• An object of my invention is a newprocess for the production of photographic multi-colored images.
• a further object is anew process for the production of photographic multi-colored images with improved color rendering.
• Another object is a new process for the production of photographic multi-colored images comprising one or more color-correction images.
• a photographic multi-colored image with improved color reproduction properties is obtained as follows:
• a photographic material which contains at least two silver halide emulsion layers sensitive to ditfe'rent re-
• the magenta dyestuffs consisting of a colored substance, the ab- This deviation, however, can be neutralized formed on development,
• the photographic material contains three silver halide emulsion layers sensitive to different regions of the visible spectrum. One of these. layers is sensitive to blue light only and contains a yellow color coupler.
• Another of these layers is sensitive to green light and contains a magenta color couple'rwhich by oxidation is converted into a yellow' product.
• the third layer is sensitive to red light and contains a cyan color coupler which by oxidation is converted intoa yellow, orange or red substance; If one of the red and green sensitive layers is also sensitive to blue light, it is separated from the first mentioned layer by a yellow filter layer.
• Color couplers which by oxidation are converted into a colored substance are for. instance the color couplers according to Formula I or a tautomeric form thereof wherein A is O and Z is the atoms necessary to complete an isoor heterocyclic ring or a ring system.
• Such color couplers are described in my co-pending application Serial No. 128,913, filed November 22, 1949, now Patent No. 2,673,801.
• the active group for the color development is believed to be the -CONHNH group. This group is converted in the oxidizing bath into an azo-chromophor.
• These color couplers may also namely, an ethenol, i. e.
• A may represent NR, R being H, a hydrocarbon radical or' an acylgroup;
• color couplers which by oxidation. are converted into a colored substance are the compounds according to Formula II amido-pyrazolone.
• oxidizabl'ecolor couplers which may be used in the performance of thisinvention are the color conplers which contain an urazol or guanazol" group, obtained, for instance, by causing a hydrazo-dicarbonamide to react with a color coupler containing, an amino group,
• Still further oxidizable color couplers are the acylor cyan acetyl hydrazones of isatine or polyisatine or of other ketones or of aldehydes etc., such as described in Patents 2,375,344 and 2,527,476 and in the co-pending application Serial No. 734,852 of Philibert L. Merckx, now Patent No. 2,540,401 as well as the beta-aryl-hydrazino-beta-imino propionic acid esters wherein the aryl group may also be a heterocyclic group (I1. Am. Chem. Soc. 66 (1944), 1853).
• couplers may be represented by the formula wherein X is CN, acyl, carbalkoxy, or another electronegative group; A is O or NR, R being H, a hydrocarbon radical, or an acyl group; R is H, a hydrocarbon, or a heterocyclic group; R is a heterocyclic group; or R and R together complete an isoor a heterocyclic ring.
• XCHzCA-NH-N C RQH (IVE) wherein X, A, R and R have the same significance as above.
• cyano-acetylhydrazone of mono-bromoisatin (U. S. Patent 2,527,476) may be written according to Formula IV:
• the color coupler to be used yields a too strongly absorbing oxidation product, it may be mixed with a color coupler which forms no colored oxidation product.
• the oxidizing bath may be a special one, containing, for instance, potassium ferricyanide, potassium bichromate or potassium periodide, or it may be the usual bleach bath for removing the silver.
• oxidizable color couplers may be used in the reversal process as well as in the negative-positive process.
• Example 1 13 g. amino-indazolone-hydrochloride, 18 g. octadecenyl succinic acid anhydride and com. pyridine are thoroughly mixed and heated for 30 minutes at a temperature between 170 and 190 C. The product of this reaction is treated thrice with /2 litre of boiling water and each time the water is decanted. Next, l Product Such color couplers is recollected by filtration with suction and recrystallised from methanol. A product corresponding to the FormulaV G. NzN-diethyl-p-phenylene diamine hydrochloride--- 6 Water to 500 com.
• Potassium ferricyanide 50 Potassium bromide 3 Water to 1000 ccm.
• Example 2 5 g. 3-amino-5-pyrazolone (prepared as described in 11. Am. Chem. Soc. 71 (1949), 987), 19.5 g. octadecenyl succinic acid anhydride and 4 ccm. pyridine are heated for 30 minutes at a temperature between and C. The reaction mixture is poured into warm water. The product precipitated is filtered with suction and recrystallised from a mixture of ethanol and water in a proportion of 3/1. The product obtained corresponds to Formula VI I NH Melting point 145-147" c.
• Example 3 7.4 g. l-hydroxy-Z-naphthoic acid, 2 g. guanazol and 20 ccm. chlorobenzene are heated at 75 C. 1.4 g. phosphorus trichloride are slowly added. The mixture is treated for 30 minutes on the water bath and then on the flame until all hydrochloric acid vapors are eliminated. The mixture is then cooled and filtered with suction. The precipitate is recrystallized in aqueous ethanol (1/1). A product represented by the Formula VII (VII) OH OH I HN--I
• Example 4 5.3 g. l-hydroxy-Z-naphthoic acid phenyl ester and 4 g,,guanazol are heated for 30 minutes at 180-190 C. After cooling, the mixtureis boiledwith ethanol. Next,
• NzN-diethyl-p-phenylene diamine hydrochloride 6 Water to 500 ccm.
• Example 5 A multi-layer material is made by employing the usual arrangement of sensitive layers as follows:
• Example 6 is obtained.
• a multilayer material is made by employing the usual arrangement of sensitive layers as follows:
• Process for the production of a photographic multicolored image which comprises exposing to light a photo graphic material containing at least two silver halide emulsion layers sensitive to different regions of the visible spectrum, at least one of these layers containing a color coupler which is able to form, by reaction with the oxidation product of a primary aromatic amino developing agent, a dyestuft" image undesirably absorbing in the blue region of the visible spectrum and more strongly absorbing in another part of the visible spectrum, and which color coupler by oxidation is converted into a blue-absorbing colored substance practically not absorbing in said other part of the visible spectrum, which process further comprises developing at least that layer containing said color coupler with a primary aromatic amino developing agent, and treating at least the remaining color coupler of this layer in an oxidizing bath, said color coupler containing a -NH-NH-CA- group within a ring, wherein A is a member selected from the group consisting of O, NH, N linked to a hydrocarbon radical, and N linked to an acyl group.
• Process for the production of a photographic multicolored image which comprises exposing to light a photographic material containing three silver halide emulsion layers sensitive to different regions of the visible spectrum, one of these layers being sensitive to blue light only and containing a yellow color coupler, another of the three layers being sensitive to green light only and containing a magenta color coupler which, by oxidation, is converted into a yellow product, the third of said layers being sensitive to red light only and containing a cyan color coupler which, by oxidation, is converted into a substance selected from the group consisting of red, orange and yellow substances, which process further comprises developing that material with a primary aromatic amino developing agent, and treating it in an oxidizing bath, said color coupler containing a NHNHCA-- group within a ring, wherein A is a member selected from the group consisting of O, NH, N linked to a hydrocarbon radical, and N linked to an acyl group.
• Process for the production of a photographic multicolored image which comprises exposing to light a photographic material containing three silver halide emulsion layers sensitive to diiierent regions of the visible spectrum, one of these layers being sensitive to blue light only and containing a yellow color coupler, another of the three layers being sensitive to blue and green light and containing a magenta color coupler which, by'oxidation, is converted into a yellow product, the third of the three layers being sensitive to blue and red light and containing a cyan color coupler which, by oxidation, is converted into a substance selected from the group consisting of red, orange and yellow substances, said material further containing a yellow filter layer between the layer sensitive to blue only and the other sensitive layers, which process further comprises developing that material 'with a primary aromatic amino developing agent, and treating it in an oxidizing bath, said color 9 coupler containing a --NH--NHCA- group within a ring, wherein A is a member selected from the group consisting of O, NH, N linked to a hydrocarbon
• Photographic material which comprises at least two silver halide emulsion layers sensitive to different regions of the visible spectrum, at least one of these layers containing a color coupler which is able to form, by reaction with the oxidation product of a primary aromatic amino developing agent, a dyestuff image undesirably absorbing in the blue region of the visible spectrum and more strongly absorbing in another part of the visible spectrum, and which color coupler by oxidation is converted into a blue-absorbing colored substance practically not absorbing in said other part of the visible spectrum, said color coupler, moreover, containing, a -NHNH-CA- group within a ring, wherein A is a member selected from the group consisting of O, NH, N linked to a hydrocarbon radical, and N linked to an acyl group.
• Photographic material which comprises three silver 20 halide emulsion layers sensitive to different regions of the visible spectrum, one of said layers being sensitive to blue light only and containing a yellow color coupler, another of the three layers being sensitive to green light only and containing a magenta color coupler which, by oxidation, is converted into a yellow product, the third of said layers being sensitive to red light only and containing a cyan color coupler which, by oxidation, is converted into a substance selected from the group consisting of red, orange and yellow substances, said color coupler, moreover, containing a NH-NHCA-- group within a ring, wherein A is a member selected from the group consisting of O, NH, N linked to a hydrocarbon radical, and N linked to an acyl group.
• oxidation is converted into a substance selected from the group consisting of red, orange and yellow substances, said material further containing a yellow filter layer between the layer sensitive to blue only and the other sensitive layers, said color coupler, moreover, containing a 5 NHNH-CA- group within a ring, wherein A is a member selected from the group consisting of O, NH, N linked to a hydrocarbon radical, and N linked to an acyl group.

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

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Citations (4)

• 0
  • BE BE499957D patent/BE499957A/xx unknown
• 1949
  • 1949-12-13 GB GB31977/49A patent/GB685061A/en not_active Expired
• 1950
  • 1950-12-12 US US200491A patent/US2823998A/en not_active Expired - Lifetime
  • 1950-12-13 FR FR1138704D patent/FR1138704A/fr not_active Expired

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