GB757368A - Photographic silver halide emulsions containing colour couplers and the method of producing coloured photographic images therein - Google Patents
Photographic silver halide emulsions containing colour couplers and the method of producing coloured photographic images thereinInfo
- Publication number
- GB757368A GB757368A GB8538/54A GB853854A GB757368A GB 757368 A GB757368 A GB 757368A GB 8538/54 A GB8538/54 A GB 8538/54A GB 853854 A GB853854 A GB 853854A GB 757368 A GB757368 A GB 757368A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzamido
- tert
- amylphenoxy
- phenyl
- chloro
- 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
Links
- -1 silver halide Chemical class 0.000 title abstract 8
- 239000000839 emulsion Substances 0.000 title 1
- 229910052709 silver Inorganic materials 0.000 title 1
- 239000004332 silver Substances 0.000 title 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 239000007983 Tris buffer Substances 0.000 abstract 3
- 229960001413 acetanilide Drugs 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- XWEBTVZIZWEJOO-UHFFFAOYSA-N 3-chlorosulfonylbenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 XWEBTVZIZWEJOO-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-methyl-PhOH Natural products CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 abstract 2
- FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract 2
- PRPJEXLNOGLBCN-UHFFFAOYSA-N phenyl 4-chloro-1-hydroxynaphthalene-2-carboxylate Chemical compound C1=C(Cl)C2=CC=CC=C2C(O)=C1C(=O)OC1=CC=CC=C1 PRPJEXLNOGLBCN-UHFFFAOYSA-N 0.000 abstract 2
- JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 abstract 1
- YXARGXWBZQVHGH-UHFFFAOYSA-N 3-(1H-pyrazol-5-yloxymethyl)benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C=1C=C(COC2=NNC=C2)C=CC1 YXARGXWBZQVHGH-UHFFFAOYSA-N 0.000 abstract 1
- ZXUBKRFDYPFNRZ-UHFFFAOYSA-N 3-[[5-[(3-chlorosulfonylbenzoyl)amino]-2-phenylpyrazol-3-yl]oxymethyl]benzenesulfonyl chloride Chemical compound C1(=CC=CC=C1)N1N=C(C=C1OCC1=CC(=CC=C1)S(=O)(=O)Cl)NC(C1=CC(=CC=C1)S(=O)(=O)Cl)=O ZXUBKRFDYPFNRZ-UHFFFAOYSA-N 0.000 abstract 1
- PVKNQGWSRAGMNM-UHFFFAOYSA-N 5-amino-2-phenyl-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1C1=CC=CC=C1 PVKNQGWSRAGMNM-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- 229950006098 orthocaine Drugs 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 abstract 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 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
- G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1 - Hydroxy - 4 - chloro - N - (b - {4 - [2 - (2:4 - di - tert - amylphenoxy) - 5 - (3:5 - di - b - hy - droxyethylsulphamylbenzamido) - benzamido] - phenyl} - ethyl) - - naphthamide is prepared by reacting 1 - hydroxy - 4 - chloro - N - (b - {4-[2-(2:4 - di - tert. - amylphenoxy) - 5 - (3:5 - di - chlorosulphonylbenzamido) - benzamido] - phenyl} - ethyl) - 2 - naphthamide with a large excess of ethanolamine in dioxane. 1-Hydroxy-4 - chloro - N - (b - {4 - [2 - (2:4 - di - tert.-amylphenoxy) - 5 - {3:5 - [di - (di - b - hydroxyethyl - sulphamyl)]} - benzamido] - phenyl} - ethyl) - 2 - naphthamide, 1 - hydroxy - 4 - chloro - N - (b -{4-[2 - (2:4 - di - tert. - amylphenoxy) - 5 - (3:5-bis-{N - [tri - (hydroxymethyl) - methyl] - sulphamyl}-benzamido) - benzamido] - phenyl} - ethyl) - 2 - napthamide, 1 - hydroxy - 4 - chloro - N - (b -{4-[2 - (2:4 - di - tert. - amylphenoxy) - 5 - (3:5-bis-{N - [a :a - di - (hydroxymethyl) - ethyl] - sulphamyl) - benzamido) - benzamido] - phenyl}-ethyl) - 2 - naphthamide, 1 - hydroxy - 4 - chloro - N - [b - { 3 - [bis - (b - hydroxyethyl)-sulphamyl]-benzamido} - ethyl] - 2 - naphthamide, 1 - hydroxy - N - (b - {4 - [2 - (2:4 - di - tert. - amylphenoxy) - 5 - (m - [tris - {N - [hydroxymethyl] - methyl] - sulphamyl} - benzamido) - benzamido] - phenyl} - ethyl) - 2 - naphthamide, 1 - hydroxy - 4-chloro - N - [b - (4 - {2 - [2:4 - di - tert. - amyl - phenoxy] - 5 - [3 - (b - hydroxyethylsulphamyl) - benzamido] - benzamido} - phenyl) - ethyl] - 2 - naphthamide, 1 - hydroxy - 4 - chloro - N - {b -(4-[5 - {3 - [bis - (b - hydroxyethyl) - sulphamyl] - benzamido} - 2 - (2:4 - di - tert. - amylphenoxy) - benzamido] - phenyl) - ethyl} - 2 - naphthamide, 1 - hydroxy - 4 - chloro - N - [b - {2 - (2:4 - di - tert. - amylphenoxy) - 5 - [3 - (b - hydroxyethylsul - phamyl) - benzamido] - benzamido} - ethyl] - 2 - naphthamide, 1 - hydroxy - 4 - chloro - N - {b -[5-{3 - [bis - (b - hydroxyethyl) - sulphamyl] - benz - amido} - 2 - (2:4 - di - tert. - amylphenoxy)-benz-amido] - ethyl} - 2 - naphthamide, 2:4 - dichloro-6 - {2 - [2:4 - di - tert. - amylphenoxy) - 5 - [3-(b -hydroxyethylsulphamyl) - benzamido] - benzamido } - 3 - methylphenol, 2:4 - dichloro - 6 - {2-[2:4-di - tert. - amylphenoxy] - 5 - [3 - (di - b -hydroxyethylsulphamyl) - benzamido] - benzamido} - 3 - methylphenol, 6 - [2 - (2:4 - di - tert. - amyl - phenoxy) - 5 - {3 - [tris - (hydroxymethyl)-methylsulphamyl] - benzamido} - benzamido] - 2:4 - di - chloro - 3 - methylphenol, 1 - phenyl - 3 - {3-[2-(2:4 - di - tert. - amylphenoxy) - 5 - (3:5 - di - b - hydroxyethylsulphamylbenzamido) - benzamido] - benzamido} - 5 - pyrazolone, 1 - phenyl - 3 - }3 - [5 - {3:5 - bis - [tris - (hydroxymethyl) - methyl]-sulphamylbenzamido} - 2 - (2:4 - di - tert. - amyl - phenoxy) - benzamido] - benzamido} - 5 - pyrazolone, 1 - phenyl - 3 - {3 - [2 - (2:4 - di - tert.-amylphenoxy) - 5 - (3 - [tris - (hydroxymethyl) - methyl - sulphamyl] - benzamido) - benzamido] - benz - amido} - 5 - pyrazolone, 1 - phenyl - 3 - {3 - [5 - {3 - [bis - (b - hydroxyethyl) - sulphamyl] - benz - amido} - 2 - (2:4 - di - tert. - amylphenoxy - benzamido] - benzamido} - 5 - pyrazolone, 1-phenyl - 3 - [3 - {2 - [2:4 - di - tert. - amylphen - oxy] - 5 - [3 - (b - hydroxyethylsulphamyl) - benz - amido] - benzamido} - benzamido] - 5 - pyrazolone, (2 - methoxybenzoyl) - 4 - [5 - {3 - [bis - (b - hy - droxyethyl) - sulphamyl] - benzamido} - 2 - (2:4 - di - tert. - amylphenoxy) - benzamido] - acetanilide, and (2 - methoxybenzoyl) - 4 - {2 - [2:4 - di-tert.-amylphenoxy] - 5 - [3 - (b - hydroxyethylsul - phamyl) - benzamido] - benzamido} - acetanilide are similarly prepared. 1 - Phenyl - 3 - [3 - (b - hydroxyethylsulphamyl)-benzamido] -5-pyrazolone is prepared by reacting 1 - phenyl - 3 - (3 - chlorosulphonylbenzamido)-5 - (3 - chlorosulphonylbenzoxy) - pyrazole in dioxane with ethanolamine and pyridine, and heating an ethanol solution of the product with aqueous sodium hydrosulphite. 1-Phenyl-3-{3-[bis - (b - hydroxyethyl) - sulphamyl] - benzamido}-5-pyrazolone is similarly prepared. 1 - Hydroxy - 4 - chloro - N - (b - {4 - [2 - (2:4-di - tert. - amylphenoxy) - 5 - (3:5 - dichlorosul - phonylbenzamido) - benzamido] - phenyl}-ethyl)-2-naphthamide is prepared by reacting together 1 - hydroxy - 4 - chloro - N - (b - (4 - (2 - (2:4-ditert. - amylphenoxy) - 5 - aminobenzamido-phenyl) - ethyl) - 2 - naphthamide and 3:5 - di - chlorosulphonylbenzoyl chloride in dioxane in presence of quinoline. 1 - Hydroxy - N - (b -{4-[2-(2:4 - di - teert. - amylphenoxy) - 5 - (3 - chloro - sulphonylbenzamido) - benzamido] - phenyl}-ethyl) - 2 - naphthamide, 1 - hydroxy - 4 - chloro-N - {b - [2 - (2:4 - di - tert. - amylphenoxy) - 5 - (3 - chlorosulphonylbenzamido) - benzamido] - ethyl} - 2 - naphthamide, 6 - [5 - (3 - chlorosulph - onylbenzamido) - 2 - (2:4 - di - tert. - amylphen - oxy) - benzamido] - 2:4 - dichlor - 3 - methyl - phenol, 1 - phenyl - 3 - {3 - [2 - (2:4 - di - tert. - amylphenoxy) - 5 - (3:5 - dichlorosulphonylbenz - amido) - benzamido] - benzamido} - 5 - pyrazolone, the corresponding 3-chlorosulphonyl compound, and (2 - methoxybenzoyl) - 4 - [5 - (3 - chlorosul - phonylbenzamido) - 2 - (2:4 - di - tert. - amyl - phenoxy)-benzamido]-acetanilide are similarly prepared. 1 - Hydroxy - 4 - chloro - N - (b - {4 - [2 - (2:4-di - tert. - amylphenoxy) - 5 - aminobenzamido]-phenyl} - ethyl) - 2 - naphthamide is prepared by reducing with hydrogen the corresponding 5-nitrobenzamido compound, itself prepared by reacting 1 - hydroxy - 4 - chloro - [b - (4 - amino - phenyl) - ethyl] - 2 - naphthamide with 2-(2:4-di - tert. - amylphenoxy) - 5 - nitrobenzoyl chloride. 1 - Hydroxy - 4 - chloro - N - {b - [2 - (2:4 - di - tert. - amylphenoxy) - 5 - aminobenz - amido] - ethyl} - 2 - naphthamide and 1-phenyl-3 - {3 - [2 - (2:4 - di - tert. - amylphenoxy) - 5 - amino] - benzamido} - benzamido - 5 - pyrazolone and the corresponding nitro compounds are similarly prepared. 1 - Hydroxy - 4 - chloro - N - [b - (4 - amino - phenyl) - ethyl] - 2 - naphthamide is prepared by reducing with hydrogen 1-hydroxy-4-chloro-N-(b - (4 - nitrophenyl - ethyl) - 2 - naphthamide, itself prepared by heating together 4-nitro-b -phenethylamine and phenyl 1 - hydroxy - 4 - chloro-2-naphthoate. 1-Hydroxy - 4 - chloro - N - [b - (3 - chlorosul - phonylbenzamido)-ethyl]-2-naphthamide is prepared by refluxing with m-chlorosulphonylbenzoyl chloride and dioxane 1-hydroxy-4-chloro - 2 - b - aminoethylnaphthamide, itself prepared by reacting phenyl 1-hydroxy-4-chloro-2-naphthoate with ethylenediamine in benzene. 2:4 - Dichloro - 3 - methyl - 6 - [3 - amino - 6 - (2:4-di-tert.-amylphenoxy) - benzamido] - phenol is prepared by reducing with iron and acetic acid the corresponding 3-nitro compound, itself prepared by reacting 2-amino-4:6-dichloro-5-methylphenol hydrochloride with 2-(2:4-di-tert.-amylphenoxy)-5-nitrobenzoyl chloride. 4-(2 - Methoxybenzoylacetamido) - 2 - (2:4 - di-tert.-amylphenoxy)-5-aminobenzanilide and the corresponding 5-nitro compound are similarly prepared. 1 - Phenyl - 3 - (3 - chlorosulphonylbenzamido)-5 - (3 - chlorosulphonylbenzoxypyrazole is prepared by heating together 1-phenyl-3-amino-5-pyrazolone and m - chlorosulphonylbenzoyl chloride in ethyl oxalate. Specifications 531,246, 664,580, [both in Group IV], and 711,488, [Group IV (a)], are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US344884A US2710803A (en) | 1953-03-26 | 1953-03-26 | Color couplers containing hydroxyalkyl groups |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB757368A true GB757368A (en) | 1956-09-19 |
Family
ID=23352476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8538/54A Expired GB757368A (en) | 1953-03-26 | 1954-03-24 | Photographic silver halide emulsions containing colour couplers and the method of producing coloured photographic images therein |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2710803A (en) |
| FR (1) | FR1098307A (en) |
| GB (1) | GB757368A (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3135609A (en) * | 1960-06-29 | 1964-06-02 | Gen Aniline & Film Corp | 1-hydroxy-2-naphthamide couplers for color photography |
| US3183095A (en) * | 1960-07-01 | 1965-05-11 | Gen Aniline & Film Corp | Color couplers containing a tertiary amino group |
| GB997500A (en) * | 1963-06-17 | 1965-07-07 | Ilford Ltd | Improvements in or relating to colour couplers and to their production and use in colour photography |
| NL133047C (en) * | 1963-06-17 | |||
| US3711546A (en) * | 1966-12-02 | 1973-01-16 | M Simon | N-(ortho-substituted benzene or naphthalene carboxamidoethyle)para-phenylene diamines as coupler-developers |
| US4198235A (en) * | 1975-02-07 | 1980-04-15 | Agfa-Gevaert, A.G. | Dye diffusion transfer process employing compounds that release sulfonamide dye providing radicals |
| TW201920081A (en) | 2017-07-11 | 2019-06-01 | 美商維泰克斯製藥公司 | Carboxamide as a sodium channel regulator |
| WO2020146612A1 (en) | 2019-01-10 | 2020-07-16 | Vertex Pharmaceuticals Incorporated | Esters and carbamates as modulators of sodium channels |
| US12441703B2 (en) | 2019-01-10 | 2025-10-14 | Vertex Pharmaceuticals Incorporated | Carboxamides as modulators of sodium channels |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB531312A (en) * | 1939-03-31 | 1941-01-01 | Eastman Kodak Co | Improvements in and relating to colour forming developers and processes of colour development |
-
1953
- 1953-03-26 US US344884A patent/US2710803A/en not_active Expired - Lifetime
-
1954
- 1954-03-24 GB GB8538/54A patent/GB757368A/en not_active Expired
- 1954-03-26 FR FR1098307D patent/FR1098307A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1098307A (en) | 1955-07-22 |
| US2710803A (en) | 1955-06-14 |
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