US2897079A - Production of colored photographic images with oxodiazole couplers - Google Patents
Production of colored photographic images with oxodiazole couplers Download PDFInfo
- Publication number
- US2897079A US2897079A US647473A US64747357A US2897079A US 2897079 A US2897079 A US 2897079A US 647473 A US647473 A US 647473A US 64747357 A US64747357 A US 64747357A US 2897079 A US2897079 A US 2897079A
- Authority
- US
- United States
- Prior art keywords
- color coupler
- production
- photographic
- water
- couplers
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 title 1
- -1 AMINO Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 239000004332 silver Substances 0.000 description 6
- GEQZTCMVWVDEDF-UHFFFAOYSA-N 2-cyanoacetyl chloride Chemical compound ClC(=O)CC#N GEQZTCMVWVDEDF-UHFFFAOYSA-N 0.000 description 5
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical class C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000005840 aryl radicals Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BBNNLJMGPASZPD-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonylacetonitrile Chemical compound CC1=CC=C(S(=O)(=O)CC#N)C=C1 BBNNLJMGPASZPD-UHFFFAOYSA-N 0.000 description 1
- OSASMATTWIPBNX-UHFFFAOYSA-N 2-(4-nitrophenyl)sulfonylacetonitrile Chemical compound [O-][N+](=O)C1=CC=C(S(=O)(=O)CC#N)C=C1 OSASMATTWIPBNX-UHFFFAOYSA-N 0.000 description 1
- GCABLKFGYPIVFC-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)-3-oxopropanenitrile Chemical compound C1=CC=C2OC(C(CC#N)=O)=CC2=C1 GCABLKFGYPIVFC-UHFFFAOYSA-N 0.000 description 1
- 241001460678 Napo <wasp> Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- ZPEOWHYBZZPAEJ-UHFFFAOYSA-N n'-hydroxy-2-(4-methylphenyl)sulfonylethanimidamide Chemical compound CC1=CC=C(S(=O)(=O)CC(N)=NO)C=C1 ZPEOWHYBZZPAEJ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 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
- G03C7/32—Colour coupling substances
- G03C7/36—Couplers containing compounds with active methylene groups
Definitions
- the present invention relates to a process for the manufacture of colored photographic images by color development in the presence of a color coupler, to photographic developers or to photographic material which contain such color coupler, and to photographic images obtained according to this process.
- Magenta colored images are usually obtained by development in the presence of compounds which contain an active methylene group, for example compounds whereinthe methylene group is connected at one side with a heterocyclic ring and at the other side with another group capable of activating a methylene group such as a cyan group.
- compounds which contain an active methylene group for example compounds whereinthe methylene group is connected at one side with a heterocyclic ring and at the other side with another group capable of activating a methylene group such as a cyan group.
- Such compounds are for instance oxodiazolyl-Z-acetonitrile and cyano-acetyl coumarone.
- Another object of this invention is to provide new photographic developers containing a color coupler.
- a further obqect is to provide new photographic material containing a color coupler.
- a reducible silver salt image is developed with an aromatic amino developing agent in the presence of a compound according to the formula obtained by reaction of HONH with nitriles (RSO CH --CN).
- RSO CH --CN nitriles
- the latter are obtained by reaction of chloro-acetonitrile with the sodium salts of sulphinic acids (RSO H).
- color couplers according to the present invention during color development may arise from adding to the photographic material or to the developer, a compound which differs from the color coupler only because in the active CH -group one or two hydrogen atoms are replaced by a group splitting oif either before development occurs by the action of the alkali in the developing solution or during the color development.
- the color couplers of the present invention may be added to the developer or to a colloid layer, either to a light-sensitive silver halide emulsion layer or to a nonlight-sensitive layer, adjacent to a sensitive layer or separated therefrom by a permeable colloid layer. They are, however, particularly suited for use in -the developer as illustrated hereinafter.
- aromatic amino compounds which according to the present invention are used as developing agents, com-- prise mono-, diand tri-amino aryl compounds, particularly N:N-dialkyl-para-phenylene diamines and derivatives such as N:N-dialkyl-N-sulphoor carboxy-methylpara-phenylene diamines.
- An exposed photographic film strip, coated with a A silver halied emulsion layer, is developed in a bath of the following composition:
- solution B is added to solution A and water developed image is rinsed for 30 minutes an the silver is bleached in the following bath:
- the image is rinsed again for 10 minutes and then fixed Y and again rinsed for 30' minutes.
- Beta-naphthyl-sulphonyl-acetarnidoxirne, melting at 143 C. is prepared as described by J. Troger and P. Volkmer (loc. cit.). 26.4 g. (0.1 mol) of this amidoxime are treated with 15 g. (0.15 mol) cyanoacetyl chloride in ethereal solution. After heating for 2 /2 hours on the waterbath, the precipitate is filtered off, Washed with an aqueous solution of H SO N and next with water until neutral reaction of the wash water, boiled in a minimum of acetic acid and poured into water. A color coupler, corresponding to Formula I, wherein R beta-naphthyl, and melting at 122124 C., is obtained.
- EXAMPLE 3 p-Nitrophenyl-sulphonyl-acetonitrile melting at 159 160 C. and the corresponding amidoxime melting at 195 196 C. are prepared by the same method as described by J. Troger and P. Volkrner (loc. cit.) for beta-naphthylsulphonyl-aceto-amidoxime.
- EXAMPLE 4 by nitration of p-tolylsulphonyl-acetonitrile and melting 'at 115-116 C. is transformed into the corresponding amidoxime melting at 152 C. by the method of I. Troger and P. Volkmer (c. cit.).
- a mixture of 27.3 g. (0.1 mol) of this amidoxirne, suspended in 200 cm. anhydrous ether, and g. (0.15 mol) cyano-acetyl chloride are refluxed for 9 hours on the water bath.
- the precipitate is filtered off, washed with an aqueous solution of H SO N and with water, boiled in acetic acid and poured into Water. After recrystallization from a mixture of water and acetone, a color coupler corresponding to Formula I, wherein R:3-nitro-4methylphenyl, and melting at 149-150 C. is obtained.
- EXAMPLE 6 The developing solution given in Example 1 may be replaced by the following:
- solution B is added to solution A and water is added to the resulting solution to 1000 9 111.
- a process for the production of a colored photographic image which comprises developing a reducible silver salt image in a photographic element by means of a primary aromatic amino developing agent in the presence of a color coupler having the following formula:
- R represents a member selected from the group consisting of an alkyl radical and an aryl radical.
- a process for the production of a colored photographic image which comprises developing a reducible silver salt image in a photographic element by means of a primary aromatic amino developing agent in the presence of a color coupler having the following formula:
- Photographic developer containing a primary arowherein R represents a member selected from the group consisting of an alkyl radical and an aryl radical.
- Photographic developer containing a primary aromatic amino developing agent and a color coupler having the following formula:
- a photographic material comprising at least one silver halide emulsion layer, one of the layers containign a color coupler having the following formula:
- R represents a member selected from the group consisting of an alkyl radical and an aryl radical.
- a photographic material comprising at least one silver halide emulsion layer and at least one other colloid layer, one of said layers containing a color coupler having the following formula:
- R aryl
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9106/56A GB817286A (en) | 1956-03-23 | Improvements in or relating to the production of colour photographic images |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2897079A true US2897079A (en) | 1959-07-28 |
Family
ID=9865468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US647473A Expired - Lifetime US2897079A (en) | 1956-03-23 | 1957-03-21 | Production of colored photographic images with oxodiazole couplers |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2897079A (en)van) |
| BE (1) | BE555915A (en)van) |
| DE (1) | DE1045230B (en)van) |
| FR (1) | FR1169942A (en)van) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3277155A (en) * | 1960-08-24 | 1966-10-04 | Eastman Kodak Co | Monofluoro-beta-ketoacetanilide couplers for color photography |
| US3351468A (en) * | 1963-01-19 | 1967-11-07 | Ciba Ltd | Thiophene compounds used as color couplers for magenta dyestuffs |
| US4148801A (en) * | 1978-07-03 | 1979-04-10 | American Home Products Corporation | 3-[(Chlorophenylsulfonyl)methyl]-1,2,4-oxadiazole-5-carboxylic acid derivatives |
| US4871652A (en) * | 1988-09-07 | 1989-10-03 | Eastman Kodak Company | Photographic silver halide material and process |
| US5066576A (en) * | 1989-10-03 | 1991-11-19 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| US5162196A (en) * | 1989-11-20 | 1992-11-10 | Fuji Photo Film Co., Ltd. | Color coupler for photography and silver halide photographic material comprising the same |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2380809A (en) * | 1939-12-11 | 1945-07-31 | Verkinderen Honore | Color couplers for photographic color development |
| GB638039A (en) * | 1947-12-03 | 1950-05-31 | Gevaert Photo Producten Naamlo | Improvements in and relating to the production of colour photographic images |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2369489A (en) * | 1941-09-25 | 1945-02-13 | Eastman Kodak Co | Acylated amino pyrazolone couplers |
-
0
- BE BE555915D patent/BE555915A/xx unknown
-
1957
- 1957-03-19 DE DEG21731A patent/DE1045230B/de active Pending
- 1957-03-21 US US647473A patent/US2897079A/en not_active Expired - Lifetime
- 1957-03-22 FR FR1169942D patent/FR1169942A/fr not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2380809A (en) * | 1939-12-11 | 1945-07-31 | Verkinderen Honore | Color couplers for photographic color development |
| GB638039A (en) * | 1947-12-03 | 1950-05-31 | Gevaert Photo Producten Naamlo | Improvements in and relating to the production of colour photographic images |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3277155A (en) * | 1960-08-24 | 1966-10-04 | Eastman Kodak Co | Monofluoro-beta-ketoacetanilide couplers for color photography |
| US3351468A (en) * | 1963-01-19 | 1967-11-07 | Ciba Ltd | Thiophene compounds used as color couplers for magenta dyestuffs |
| US4148801A (en) * | 1978-07-03 | 1979-04-10 | American Home Products Corporation | 3-[(Chlorophenylsulfonyl)methyl]-1,2,4-oxadiazole-5-carboxylic acid derivatives |
| US4871652A (en) * | 1988-09-07 | 1989-10-03 | Eastman Kodak Company | Photographic silver halide material and process |
| US5066576A (en) * | 1989-10-03 | 1991-11-19 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| US5162196A (en) * | 1989-11-20 | 1992-11-10 | Fuji Photo Film Co., Ltd. | Color coupler for photography and silver halide photographic material comprising the same |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1169942A (fr) | 1959-01-07 |
| BE555915A (en)van) | |
| DE1045230B (de) | 1958-11-27 |
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