US3274001A - Process for the production of integral color correction masks - Google Patents
Process for the production of integral color correction masks Download PDFInfo
- Publication number
- US3274001A US3274001A US421988A US42198864A US3274001A US 3274001 A US3274001 A US 3274001A US 421988 A US421988 A US 421988A US 42198864 A US42198864 A US 42198864A US 3274001 A US3274001 A US 3274001A
- Authority
- US
- United States
- Prior art keywords
- color
- diazonium salt
- developer
- silver halide
- coupler
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 30
- 239000012954 diazonium Substances 0.000 claims description 23
- 230000000873 masking effect Effects 0.000 claims description 17
- -1 AMINO Chemical class 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- 239000000839 emulsion Substances 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 8
- 229910052709 silver Inorganic materials 0.000 claims description 8
- 239000004332 silver Substances 0.000 claims description 8
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims description 7
- 229960004909 aminosalicylic acid Drugs 0.000 claims description 7
- 239000000975 dye Substances 0.000 description 9
- QKQMGEMTKMXWKQ-UHFFFAOYSA-N 5-amino-2-hydroxy-3-nitrobenzoic acid Chemical compound NC1=CC(C(O)=O)=C(O)C([N+]([O-])=O)=C1 QKQMGEMTKMXWKQ-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000009102 absorption Effects 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NBGAYCYFNGPNPV-UHFFFAOYSA-N 2-aminooxybenzoic acid Chemical class NOC1=CC=CC=C1C(O)=O NBGAYCYFNGPNPV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 229960004050 aminobenzoic acid Drugs 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- AYLDJQABCMPYEN-UHFFFAOYSA-N (4-azaniumylphenyl)-diethylazanium;sulfate Chemical compound OS(O)(=O)=O.CCN(CC)C1=CC=C(N)C=C1 AYLDJQABCMPYEN-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- KBLAMUYRMZPYLS-UHFFFAOYSA-N 2,3-bis(2-methylpropyl)naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 KBLAMUYRMZPYLS-UHFFFAOYSA-N 0.000 description 1
- HTXLCLCKNKNHEC-UHFFFAOYSA-N 3-amino-2-hydroxy-5-methylbenzoic acid Chemical compound CC1=CC(N)=C(O)C(C(O)=O)=C1 HTXLCLCKNKNHEC-UHFFFAOYSA-N 0.000 description 1
- QNNBPYYOVDUTTK-UHFFFAOYSA-N 6h-imidazo[4,5-e]indazol-2-one Chemical class C12=NC(=O)N=C2C=CC2=C1C=NN2 QNNBPYYOVDUTTK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- LOCAIGRSOJUCTB-UHFFFAOYSA-N indazol-3-one Chemical class C1=CC=C2C(=O)N=NC2=C1 LOCAIGRSOJUCTB-UHFFFAOYSA-N 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 1
- 229960004963 mesalazine Drugs 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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
- G03C7/18—Processes for the correction of the colour image in subtractive colour photography
Definitions
- This invention relates to a process of color correction of subtractive colors in color photographic multilayer materials by forming integral color correction masks in the layer. This is accomplished by reacting the residual color couplers with diazonium compounds derived from an amino salicylic acid.
- the subtractive colors are yellow, magenta and cyan.
- the yellow color coupler is incorporated into the blue-sensitive layer, the magenta color coupler into the green-sensitive layer and the cyan color coupler into the red-sensitive layer.
- the yellow dyestuff corresponds approximately to theoretical requirements necessary for its light absorption, this is not the case with the cyan and the magenta dyestuffs.
- the deficiency of the cyan and magenta color couplers lead to errors in the color reproduction.
- the masking images are formed in the photographic layers in the form of so-called integral color correction masks.
- the masking images which are produced are of a contrast opposite in sign to that of the partial images, since the density of the masking dye in any area of the layer is inversely proportional to the density of the dye of the primary partial image.
- Diazonium salts which are derived from aminosalicylic acids in solid form are quite resistant to shock, and stable in solid and dissolved form. According to a preferred embodiment of this invention the stability and storability can be improved quite considerably by mixing the diazonium compounds with alkyl-naphthalene sulfonic acids. Suitable sulfonic acids are, for example: diisobutyl-naphthalene sulfonic acid.
- the proportions of the diazonium salt and the alkyl naphthalene sulfonic acid is not critical and can be selected in accordance with the properties of the diazonium compound. It has been found that generally from about 0.1 part by weight to about 1 part by weight of the alkyl naphthalene sulfonic acid per part by weight of the diazonium compound are quite sufiicient to obtain the desired improvement of the stability.
- the diazonium salts of aminosalicylic acids are particularly advantageous in that they do not react with the residual color-coupler for the yellow partial image. On the other hand they form a yellow dyestufi with the residual coupler for the magenta-colored partial image and, in the case of substitution by nitro groups, they form a reddish-violet dyestuff with the residual coupler for the cyan partial image.
- diazonium salts derived from aminosalicylic acid of the following formula NHt wherein R hydrogen, alkyl preferably alkyl having up to 3 carbon atoms or nitro.
- Suitable compounds are:
- the mixture is then stirred for another hour and finally the diazonium salt is suction-filtered.
- the salt obtained is first of all washed with 600 cc. of alcohol and then with 300 cc. of ether. About 30 g. of dry diazonium salt are obtained. This is mixed with finely powdered sodium diisobutylnaphthalene sulfonate in a ratio by weight of 1:1.
- the diazonium salt mixture is used either after the usual color processing in a special bath, advantageously at pH 5.5, or it is added to a photographic processing bath, e.g., a bleaching bath, and the operation can in this way be effected without using an additional bath.
- a photographic processing bath e.g., a bleaching bath
- the process of the invention can be applied to any conventional color photographic materials which contain magenta and/ or cyan color couplers capable of reacting with the oxydation products of primary aliphatic amino developers to form a dye.
- color photographic materials which contain the color couplers in a diffusion-resistant form.
- Suitable are color couplers which are substituted by long-chain aliphatic groups and water solubilizing groups and which are distributed homogeneously in the layer, as well as color couplers which are soluble in organic solvents in which they are first dissolve-d and which combination is then dispersed in a finely divided state throughout the emulsion layer.
- Suitable solvents for this purpose are, for example, tries-ters of phosphoric or diesters of phthalic acids.
- Suitable are the usual aromatic amino developers such as p-phenylendiamin type developers, especially the N,N- dialkyl-p-phenylen diamines.
- the process of the present invention can generally be used for compensating the undesired absorption of the dyes produced by reaction of usual cyan or magenta couplers the oxidation products of color-forming developers.
- magenta couplers are, for example, those derived from pyrazolone, in particular l-phenyl-pyrazolone as described, for example, in British Patent No.
- Cyan couplers which can be reacted with the diazonium compounds according to the process of the present invention are particularly phenol or naphthol couplers.
- Example 1 An exposed multilayer color photographic film, of which the blue-sensitive silver halide layer contains 4-stearoyl aminobenzoylacetanilide 3', 5 dicarboxylic acid, the green-sensitive layer contains 1-(4'phenoxy-3'- sulfo)-phenyl-3-stearyl-5-pyrazolone, and the red-sensitive silver halide emulsion layer contains 2'-N-methyl-N- octadecyl-5-sulfo-l-hydroxynaphthoic acid-(2)-anilide, is processed as follows:
- the film is rinsed between the baths and after passing through the masking bath. After this processing, the film contains a yellow masked image in the magenta image layer, in addition to the partial image, and a reddishviolet masked image in the cyan image layer.
- Example 2 Layer structure of the color film and color development bath as in Example 1.
- Example 3 If the diazonium salt of 2-hydroxy-4-methyl-S-aminobenzoic acid is used as masking component and if the processing step is carried out as in Example 1 or 2, the processed film contains a positive yellow masking image and a negative magenta image in the green-sensitive layer.
- Example 4 The diazonium salt of 2-hydroxy-3-amino-S-nitrobenzoic acid is used as masking component. After processing as in Example 1 or 2, a yellow masking image is obtained in the magenta layer and a reddish-violet masking image in the cyan layer.
- Example 5 The diazonium salt of 2-hydroxy-3-amino-5-methylbenzoic acid is used as masking component. Processing as in Example 1 or 2 provides a yellow masking image in the magenta layer.
- Example 6 The diazonium salt of 2-hydroxy-5-aminobenzoic acid is used. After processing as described in Example 1 or 2, a yellow masking image is obtained in the magenta layer.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA45117A DE1195163B (de) | 1964-01-30 | 1964-01-30 | Verfahren zur Herstellung maskierter farben-photographischer Bilder |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3274001A true US3274001A (en) | 1966-09-20 |
Family
ID=6934552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US421988A Expired - Lifetime US3274001A (en) | 1964-01-30 | 1964-12-29 | Process for the production of integral color correction masks |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3274001A (en)) |
| BE (1) | BE659015A (en)) |
| CH (1) | CH442983A (en)) |
| DE (1) | DE1195163B (en)) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4598221A (en) * | 1985-01-23 | 1986-07-01 | Lawson William J | Permanent magnet motor having rockable rotor magnets |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2629658A (en) * | 1948-08-11 | 1953-02-24 | Gen Aniline & Film Corp | Silver halide emulsions containing nondiffusing azo dyes |
| US2663637A (en) * | 1948-08-20 | 1953-12-22 | Ici Ltd | Process of producing integral color correction masks |
-
1964
- 1964-01-30 DE DEA45117A patent/DE1195163B/de active Pending
- 1964-12-29 US US421988A patent/US3274001A/en not_active Expired - Lifetime
-
1965
- 1965-01-08 CH CH26865A patent/CH442983A/de unknown
- 1965-01-29 BE BE659015D patent/BE659015A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2629658A (en) * | 1948-08-11 | 1953-02-24 | Gen Aniline & Film Corp | Silver halide emulsions containing nondiffusing azo dyes |
| US2663637A (en) * | 1948-08-20 | 1953-12-22 | Ici Ltd | Process of producing integral color correction masks |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4598221A (en) * | 1985-01-23 | 1986-07-01 | Lawson William J | Permanent magnet motor having rockable rotor magnets |
Also Published As
| Publication number | Publication date |
|---|---|
| BE659015A (en)) | 1965-07-29 |
| DE1195163B (de) | 1965-06-16 |
| CH442983A (de) | 1967-08-31 |
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