US2945761A - Reactivity of couplers incorporated in photographic emulsions - Google Patents
Reactivity of couplers incorporated in photographic emulsions Download PDFInfo
- Publication number
- US2945761A US2945761A US674621A US67462157A US2945761A US 2945761 A US2945761 A US 2945761A US 674621 A US674621 A US 674621A US 67462157 A US67462157 A US 67462157A US 2945761 A US2945761 A US 2945761A
- Authority
- US
- United States
- Prior art keywords
- amino groups
- per liter
- reactivity
- solution
- developer
- 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
- 239000000839 emulsion Substances 0.000 title description 17
- 230000009257 reactivity Effects 0.000 title description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 12
- -1 AMINO GROUPS Chemical group 0.000 claims description 9
- 150000004982 aromatic amines Chemical class 0.000 claims description 8
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- ZNPSUQQXTRRSBM-UHFFFAOYSA-N 4-n-Pentylphenol Chemical compound CCCCCC1=CC=C(O)C=C1 ZNPSUQQXTRRSBM-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 1
- MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 description 1
- ZRVDHZHTIDPBRG-UHFFFAOYSA-N 4-methylphenol;phenol Chemical compound OC1=CC=CC=C1.CC1=CC=C(O)C=C1 ZRVDHZHTIDPBRG-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- PJWDOKOIVGPKDM-UHFFFAOYSA-N O.S(=O)(=O)(O)O.NC1=CC(=CC=C1)C.S(=O)(=O)(O)O.S(=O)(=O)(O)O.NC1=CC(=CC=C1)C.O Chemical compound O.S(=O)(=O)(O)O.NC1=CC(=CC=C1)C.S(=O)(=O)(O)O.S(=O)(=O)(O)O.NC1=CC(=CC=C1)C.O PJWDOKOIVGPKDM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 1
- 238000012550 audit Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- NHQVTOYJPBRYNG-UHFFFAOYSA-M sodium;2,4,7-tri(propan-2-yl)naphthalene-1-sulfonate Chemical compound [Na+].CC(C)C1=CC(C(C)C)=C(S([O-])(=O)=O)C2=CC(C(C)C)=CC=C21 NHQVTOYJPBRYNG-UHFFFAOYSA-M 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
- G03C7/30—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
-
- 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
- G03C7/407—Development processes or agents therefor
- G03C7/413—Developers
Definitions
- the concentration of the p-alkylphenol or other hydroxy compound in the developer should-be from about 0.1 gram to about grams per liter. A preferred amount is about 1 gram per liter of developer.
- My invention is useful 'with emulsions containing any of the couplers described in Jelley and Patent 2,322,027 or 'Fierke and Che'chak U'.S.Patent 2,801,171.
- the following couplers are typical of those which may be incorporated in the emulsion.
- N-(4 benzoylacetaminobenzenesulfonyl) N (7- phenylpropyl)-p-toluidine (U.S. Patent 2,298,443).
- Example 1 One hundred grams of couplers Nos. 1 to 7 were each dissolved in 250 cc. of ethyl acetate at the reflux tem perature of ethyl acetate. The solutions were poured into a solution containing 800 cc. of 10% gelatin solution and cc. of 5% Alkanol B solution (sodium triisopropyl naphthalene sulfonate) and then milled five times in a colloid mill. Fifty cc. of 'water was used to rinse the mill. The dispersions were set up on a chilled plate at 40 F., noodled and air-dried at 78 C. and 50% relative humidity.
- Alkanol B solution sodium triisopropyl naphthalene sulfonate
- Example 2 The emulsion coatings of Example 1 were exposed and developed in a developer of the following composition:
- Samples of the coatings were also exposed and developed in a developer of the same composition to which had been added 1 gram per liter of p-n-amylphenol.
- Example 3 Devel- Devel- Devel- D evel- Developer Deveioper oper p oper Coupler oper p-amyl oper n-octyl tert.an1- -sec.-
- the compounds of my invention are of value for incorporation in developers in which the coupler is incorporated in the developing solution.
- developers of this type there is a great increase in dye density, particularly in the denser regions of the scale.
- the p-alkylphenols may also be incorporated in black-and-white developers.
- couplers or folor-forming compounds used in the process of my invention are of the type which couple upon development with the oxidation product of primary aromatic amino developing agents.
- An aqueous photographic color developing solution capable of producing dye images of increased density, comprising an aromatic amine developing agent containing only two amino groups, said amino groups being in para relationship and at least one of said amino groups being a primary amino group, and from 0.1 to grams 4 per liter of solution of a hydroxy compound selected from the class consisting of p-alkylphenols containing from 7 to 11 carbon atoms, in which the alkyl group contains from 1 to 5 carbon atoms, an n-octyl alcohol.
- An aqueous photographic color developing solution capable of producing dye images of increased density, comprising an aromatic amine developing agent containing only two amino groups, said amino groups being in para relationship and at least one of said amino groups being a primary amino group, and from 0.1 to 15 grams per liter of solution of a p-alkylphenol containing from 7 to 11 carbon atoms, in which the alkyl group contains from 1 to 5 carbon atoms.
- An aqueous photographic color developing solution capable of producing dye images of increased density comprising an aromatic amine developing agent containing only two amino groups, said amino groups being in para relationship and at least one of said amino groups being a primary amino group, and from 0.1 to 15 grams per liter of solution of p-n-amylphenol.
- An aqueous photographic color developing solution capable of producing dye images of increased density, comprising an aromatic amine developing agent containing only two amino groups, said amino groups being in para relationship and at least one of said amino groups being a primary amino group, and from 0.1 to 15 grams 'per liter of solution of p-cresol.
- An aqueous photographic color developing solution capable of producing dye images of increased density, comprising an aromatic amine developing agent containing only two amino groups, said amino groups being in para relationship and at least one of said amino groups being a primary amino group, and from 0.1 to 15 grams per liter of solution of p-tert. amylphenol.
- An aqueous photographic color developing solution capable of producing dye images of increased density comprising an aromatic amine developing agent containing only two amino groups, said amino groups being in para relationship and at least one of said amino groups being a primary amino group, and from 0.1 to 15 grams per liter of solution of p-sec. butylphenol. 7.
- An aqueous photographic color developing solution capable of producing dye images of increased density comprising an aromatic amine developing agent containing only two amino groups, said amino groups being in para relationship and at least one of said amino groups being a primary amino group, and from 0.1 to 15 grams per liter of solution of n-octyl alcohol.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US674621A US2945761A (en) | 1957-07-29 | 1957-07-29 | Reactivity of couplers incorporated in photographic emulsions |
| FR1200657D FR1200657A (fr) | 1957-07-29 | 1958-07-28 | Nouveau révélateur pour la photographie en couleurs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US674621A US2945761A (en) | 1957-07-29 | 1957-07-29 | Reactivity of couplers incorporated in photographic emulsions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2945761A true US2945761A (en) | 1960-07-19 |
Family
ID=24707309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US674621A Expired - Lifetime US2945761A (en) | 1957-07-29 | 1957-07-29 | Reactivity of couplers incorporated in photographic emulsions |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2945761A (fr) |
| FR (1) | FR1200657A (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1285312B (de) * | 1963-10-26 | 1968-12-12 | Agfa Ag | Verfahren zur Entwicklungsbeschleunigung eines mehrschichtigen farbphotographischen Materials |
| US4965179A (en) * | 1985-04-19 | 1990-10-23 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2486440A (en) * | 1946-01-10 | 1949-11-01 | Gen Aniline & Film Corp | Production of phenazonium dyestuff images |
| US2594917A (en) * | 1949-12-16 | 1952-04-29 | Gen Aniline & Film Corp | Suppression of proximity development with azine color developers |
| US2835579A (en) * | 1955-08-31 | 1958-05-20 | Eastman Kodak Co | N-alkyl and acylphenol coupler solvents for color photography |
-
1957
- 1957-07-29 US US674621A patent/US2945761A/en not_active Expired - Lifetime
-
1958
- 1958-07-28 FR FR1200657D patent/FR1200657A/fr not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2486440A (en) * | 1946-01-10 | 1949-11-01 | Gen Aniline & Film Corp | Production of phenazonium dyestuff images |
| US2570116A (en) * | 1946-01-10 | 1951-10-02 | Gen Aniline & Film Corp | Color developers for the production of azine dye images |
| US2594917A (en) * | 1949-12-16 | 1952-04-29 | Gen Aniline & Film Corp | Suppression of proximity development with azine color developers |
| US2835579A (en) * | 1955-08-31 | 1958-05-20 | Eastman Kodak Co | N-alkyl and acylphenol coupler solvents for color photography |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1285312B (de) * | 1963-10-26 | 1968-12-12 | Agfa Ag | Verfahren zur Entwicklungsbeschleunigung eines mehrschichtigen farbphotographischen Materials |
| US4965179A (en) * | 1985-04-19 | 1990-10-23 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1200657A (fr) | 1959-12-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2401713A (en) | Color photography | |
| US4292400A (en) | Photographic silver halide development in the presence of thioether development activators | |
| EP0029722A1 (fr) | Procédé pour le développement d'un matériau photographique en couleurs aux halogénures d'argent | |
| US3141771A (en) | Aldehyde scavengers for photographic silver halide developers | |
| US4865956A (en) | Photographic elements containing a bleach accelerator precursor | |
| US2356486A (en) | Stain prevention in color photography | |
| US2933391A (en) | Photographic emulsions containing 5-pyrazolone coupler compounds | |
| US2725290A (en) | Development of multi-layer color films with developers containing mercapto azoles | |
| JPS5814668B2 (ja) | シヤシンヨウゲンゾウヤク | |
| US2945761A (en) | Reactivity of couplers incorporated in photographic emulsions | |
| US2478400A (en) | Silver halide photographic emulsion with developer and color coupler dispersed therein | |
| US4760016A (en) | Silver halide color photographic light-sensitive material | |
| US3189452A (en) | Color-forming photographic process utilizing a bleach-fix followed by a bleach | |
| US3113864A (en) | Reducing fog in reversal color films processed in developers containing couplers | |
| US2937086A (en) | Multilayer reversal color material | |
| US3161513A (en) | Photographic developer compositions containing an antistain agent | |
| JPS6335970B2 (fr) | ||
| US2356475A (en) | Phenolic and naphtholic couplers containing sulphonamide groups | |
| GB666107A (en) | Improvements in colour photography | |
| US2596755A (en) | Aromatic color couplers containing mercaptan and hydroxyl groups | |
| US2544640A (en) | Mixed grain photographic emulsions | |
| US4710454A (en) | Photographic recording material and a process for the production of photographic images | |
| US4514494A (en) | Photographic color material incorporating developing agents for color development | |
| US3126282A (en) | Najcoj-hzo | |
| US2133937A (en) | Color photography |