GB595314A - Improvements in photographic colour forming developers and process of colour development - Google Patents
Improvements in photographic colour forming developers and process of colour developmentInfo
- Publication number
- GB595314A GB595314A GB2142244A GB2142244A GB595314A GB 595314 A GB595314 A GB 595314A GB 2142244 A GB2142244 A GB 2142244A GB 2142244 A GB2142244 A GB 2142244A GB 595314 A GB595314 A GB 595314A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- toluidide
- tert
- anisoylacet
- chlorobenzenesulphonyl
- 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
- 238000000034 method Methods 0.000 title 1
- GCWYXRHXGLFVFE-UHFFFAOYSA-N 4-hydroxy-2,6-dimethylaniline Chemical compound CC1=CC(O)=CC(C)=C1N GCWYXRHXGLFVFE-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 3
- -1 3 - amino - 4 - chlorobenzenesulphonyl Chemical group 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 235000019441 ethanol Nutrition 0.000 abstract 2
- 239000001632 sodium acetate Substances 0.000 abstract 2
- 235000017281 sodium acetate Nutrition 0.000 abstract 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 abstract 1
- IPOVOSHRRIJKBR-UHFFFAOYSA-N 2-ethylpropanedioyl dichloride Chemical compound CCC(C(Cl)=O)C(Cl)=O IPOVOSHRRIJKBR-UHFFFAOYSA-N 0.000 abstract 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 abstract 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-Toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 1
- 229940040526 Anhydrous Sodium Acetate Drugs 0.000 abstract 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N Bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 abstract 1
- OURDMBOTRRFIBR-UHFFFAOYSA-N C(CC)OC1=C(C(=O)CC(=O)OCC)C=CC=C1 Chemical compound C(CC)OC1=C(C(=O)CC(=O)OCC)C=CC=C1 OURDMBOTRRFIBR-UHFFFAOYSA-N 0.000 abstract 1
- JFPDOJSUSFJRNY-UHFFFAOYSA-N COC1=C(CCC(=O)NC2=CC=CC=C2)C=C(C=C1)C Chemical compound COC1=C(CCC(=O)NC2=CC=CC=C2)C=C(C=C1)C JFPDOJSUSFJRNY-UHFFFAOYSA-N 0.000 abstract 1
- LWAYASXDHDEGAO-UHFFFAOYSA-N N-(4-amino-2-chlorophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1Cl LWAYASXDHDEGAO-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000003518 caustics Substances 0.000 abstract 1
- CPRIMQOWBJLQFD-UHFFFAOYSA-N ethyl 3-(2-methoxy-5-methylphenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC(C)=CC=C1OC CPRIMQOWBJLQFD-UHFFFAOYSA-N 0.000 abstract 1
- KROPYAVVJDXRPH-UHFFFAOYSA-N ethyl 3-(2-methoxyphenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1OC KROPYAVVJDXRPH-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000011874 heated mixture Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- CIFXXSVGKCRQHZ-UHFFFAOYSA-N methyl 2-propoxybenzoate Chemical compound CCCOC1=CC=CC=C1C(=O)OC CIFXXSVGKCRQHZ-UHFFFAOYSA-N 0.000 abstract 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 1
- 229940080818 propionamide Drugs 0.000 abstract 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical compound [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 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
- G03C7/36—Couplers containing compounds with active methylene groups
- G03C7/362—Benzoyl-acetanilide couplers
Abstract
N - (3 - (o1 - Anisoylbenzoylacet) - amino - 4 - chlorobenzenesulphonyl) - N - (g - phenyl - n - propyl) - p - toluidide is prepared by adding N - (3 - amino - 4 - chlorobenzenesulphonyl) - N - (g - phenyl - n - propyl) - p - toluidide to a heated mixture of ethyl o - methoxybenzoylacetate and bromobenzene. O-Anisoylacetanilide, 2 - methoxy - 5 - methylbenzylacetanilide, N - 2 - methoxybenzoylaceto - N1 - a - (41 - butylphenoxy) - propionyl - p - phenylenediamine, N - 2 - methoxybenzoylaceto - N 1 - a - (41 - butylphenoxy) - propionyl - m - phenylenediamine, N - 2 - n - propoxybenzoylaceto - N1 - a - (41 - butylphenoxy) - propionyl - p - phenylenediamine, N - 2 - methoxybenzoylaceto - N - a - (41 - amylphenoxy) - n - butyryl - p - phenylenediamine, N - 2 - methoxybenzoylaceto - N1 - a - (41 - amylphenoxy)-propionyl - p - phenylenediamine, N - ((4 - o - anisoylacet) - aminobenzenesulphonyl) - N - (g - phenyl - n - propyl) - p - toluidide, o - anisoylacet - o1 - chloranilide, 2 - methoxy - 5 - methyl benzoylacet-o-chloranilide, N-(4-(o-anisoylacet)-anino - 31 - chlorobenzenesulphonyl) - N - methyl-p - toludine, 1 - (o - anisoylacet) - amino - 2 - chloro - 4 - (a - (p - butylphenoxy) - propionyl - aminobenzene, N - (4 - (o - anisoylacet) - amino - 3 - chlorobenzenesulphonyl) - N - methyl - p - chloranilide, N - (4 - (o1 - anisoylacet) - amino - 3-chlorobenzenesulphonyl) - N - methylanilide, N-(4 - (o1 - anisoylacet) - amino - 3 - chlorobenzenesulphonyl) - p - toluidide, N - (4 - (o1 - anisoylacet) - amino - 3 - chlorobenzenesulphonyl) - p - phenylaniline, N - (4 - (o1 - anisoylacet) - amino-3 - chlorobenzenesulphonyl) - p - tert. - amylanilide, 1 - (o - anisoylacet) - amino - 2 - chloro - 4 - (p1 - toluenesulphonyl) - aminobenzene, N-(4-(o1 - anisoylacet) - amino - 3 - chlorobenzenesulphonyl) - N - (g - phenyl - n - propyl - p - toluidide and 21 - methoxybenzoylacet - 2 - chloro - 4 - nitranilide are similarly prepared. N - 4 - (o1 - Anisoylchloracet) - amino - 3 - chlorobenzenesulphonyl) - N - (g - phenyl - n - propyl) - p - toluidide is prepared by chlorinating N - 4 - (o1 - anisoylacet) - amino - 3 - chlorobenzenesulphonyl) - N - (g - phenyl - n - propyl)-p-toluidide in chloroform solution with sulphuryl chloride. 1 - (o - Anisoylacet) - amino - 2 - chloro - 4 - acetylthioglycollylaminobenzene is prepared by condensing 4-(21-methoxybenzoylacetamino)-3-chloraniline with acetylthioglycollyl chloride in the presence of sodium acetate or quinoline. Ethyl 2-methoxy-5-methylbenzoylacetate is prepared by reacting ethyl malonyl chloride and p-methoxytoluene in benzene in the presence of anhydrous aluminium chloride. Ethyl o-propoxybenzoylacetate is prepared from methyl o-n-propoxybenzoate and ethyl acetate in the presence of sodium. Acetylthioglycollyl chloride is prepared by reacting acetylthioglycollic acid with thionyl chloride. 4 - (a - (41 - tert. - Butylphenoxy) - n - propionamido) - aniline is prepared by reducing N - (a - (41 - tert. - butylphenoxy) - n - propionyl) - 4 - nitraniline in ethyl alcohol with hydrogen in presence of Raney nickel. 3-(a -(41 - tert. - Butylphenoxy) - n - propionamide) - aniline, 4 - (a - (41 - tert. - amylphenoxy) - butyramido) - aniline, 4 - (a - (41 - tert. - amylphenoxy)-propionamido) - aniline, 4 - (a - (41 - tert. - butylphenoxy) - propionamido) - 2 - chloraniline, 4-(21 - methoxybenzoylacetamino) - 3 - chloraniline hydrochloride, and N-(3-amino-4-chlorobenzenesulphonyl) - N - g - phenyl - n - propyl - p - toluidide are similarly prepared. 41 - Amino - 31 - chloro - p - toluenesulphonanilide is prepared by refluxing together 41-acetamido - 31 - p - toluenesulphonanilide, concentrated hydrochloric acid, and ethyl alcohol, and pouring into aqueous caustic alkali. 4 - Amino - 3 - chlorobenzenesulphonmethyl-3 - chlorobenzenesulphonmethyl - p1 -chloroanilide, 4 - amino - 3 - chlorobenzenesulphonmethyl - 41 - toluidide, 4 - amino - 3 - chlorobenzenesulphon - p1 - toluidide, N - (4 - amino - 3 - chlorobenzenesulphon) - 41 - tert. - amylanilide, N - (41 - amino-3 - chlorobenzenesulphon) - N - g - phenylpropyl - p1-toluidide, and N-(p-aminobenzenesulphon)-N - g - phenyl - n - propyl - p - toluidide are similarly prepared. N - (a - (41 - tert. - Butylphenoxy) - n - propionyl) - 4 - nitraniline is prepared by reacting together p-nitraniline, and a -(p-tert.-butylphenoxy)-n-propionyl chloride in the presence of acetic acid and anhydrous sodium acetate. N - (a - (41 - tert. - Butylphenoxy) - n - propionyl) - 3 - nitraniline, N - (a - (41 - tert. - amylphenoxy) - n - butyryl) - 4 - nitraniline, N - (a - (41 - tert. - amylphenoxy) - n - propionyl) - 4 - nitraniline, N - (a - (41 - tert. - butylphenoxy)-n-propionyl) - 3 - chloro - 4 - nitraniline, and N - (4 - chloro - 3 - nitrobenzenesulphonyl) - N - a - phenyl - n - propyl - p - toluidide are similarly prepared. 41 - Acetamino - 31 - chloro - p - toluenesulphonanilide is prepared by heating together 4-acetamino-3-chloroaniline and p-toluenesulphonyl chloride in presence of acetic acid and anhdrous sodium acetate. 4-Acetamino-3-chlorobenzenesulphonmethylanilide, 4 - (41 - acetamino - 31 - chlorobenzenesulphonamide) - diphenyl, 41 - acetamino - 31 - chlorobenzenesulphomethyl - 4 - chloranilide, 41 - acetamino - 31 - chlorobenzenesulphonmethyl - 4 - toluidide, 4 - (41 - acetamino-31 - chlorobenzenesulphon) - toluidide, N - (41 - acetamino - 31 - chlorobenzenesulphon) - 4 - tert.-amylanilide, N - (41 - acetamino - 31 - chlorobenzenesulphonyl) - N - g - phenylpropyl - p - toluidide and N - (p - acetaminobenzenesulphon)-N - g - phenyl - n - propyl - p - toluidide are similarly prepared. Specifications 427,472, 427,516, 427,518, 427,520, 440,032, 440,089, 447,092, 507,841, 524,154, 524,555, 540,366, 540,368, 541,589, and 545,448, [all in Group XX], are referred to.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR959910D FR959910A (en) | 1944-11-02 | ||
| US531124A US2407210A (en) | 1944-04-14 | 1944-04-14 | Color couplers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB595314A true GB595314A (en) | 1947-12-02 |
Family
ID=1736188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2142244A Expired GB595314A (en) | 1944-04-14 | 1944-11-02 | Improvements in photographic colour forming developers and process of colour development |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB595314A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3510306A (en) * | 1965-06-09 | 1970-05-05 | Fuji Photo Film Co Ltd | Developing process for color photography |
| US3619189A (en) * | 1969-01-22 | 1971-11-09 | Fuji Photo Film Co Ltd | Color photographic developing process |
-
1944
- 1944-11-02 GB GB2142244A patent/GB595314A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3510306A (en) * | 1965-06-09 | 1970-05-05 | Fuji Photo Film Co Ltd | Developing process for color photography |
| US3619189A (en) * | 1969-01-22 | 1971-11-09 | Fuji Photo Film Co Ltd | Color photographic developing process |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB680488A (en) | Improvements in colour photographic couplers | |
| GB680474A (en) | Improvements in and relating to colour forming developers and processes of colour development | |
| GB825311A (en) | Photographic silver halide emulsions and photographic developers containing colour couplers and method of producing coloured photographic images | |
| GB627814A (en) | Improvements in colour photographic development and colour-forming developers | |
| GB956261A (en) | Pyrazolone colour couplers | |
| ES246901A1 (en) | Aniline derivatives | |
| GB745704A (en) | Ultraviolet radiation absorbing compounds and photographic elements containing such compounds | |
| GB595314A (en) | Improvements in photographic colour forming developers and process of colour development | |
| GB585780A (en) | Improvements in or relating to the production of pyrazolones | |
| GB840731A (en) | Improvements in photographic processes | |
| GB598174A (en) | Improvements in and relating to photographic colour forming developers and processesof colour development | |
| GB748189A (en) | Method of protecting multilayer colour photographic elements against the action of ultraviolet radiation | |
| GB705652A (en) | Manufacture of 3-aminopropane compounds | |
| GB651749A (en) | Improvements in photographic developers | |
| GB759869A (en) | Method of making photographic emulsions for colour photography | |
| GB737112A (en) | Improvements in photographic colour couplers and photographic emulsions and developers containing them | |
| GB808276A (en) | Improvements in or relating to colour couplers for colour photography | |
| GB595844A (en) | Improvements in and relating to the production and processing of photographic materials | |
| ES266308A1 (en) | Permanent reproductions and their preparation | |
| GB699112A (en) | Improvements relating to materials for photographic diazotype printing | |
| GB626467A (en) | Sensitising photographic silver halide emulsions | |
| GB619507A (en) | Improvements in and relating to the manufacture of products adapted for use in colour photography and of photographic images in colour | |
| GB808046A (en) | Novel substituted pyridone-acetic acid derivatives and process for the manufacture thereof | |
| GB651424A (en) | Improvements in colour photographic materials | |
| GB468188A (en) | Manufacture of oxybenzofluorenones |