GB865721A - Improvements in and relating to photographic colour development and photographic emulsions containing colour couplers - Google Patents
Improvements in and relating to photographic colour development and photographic emulsions containing colour couplersInfo
- Publication number
- GB865721A GB865721A GB32419/57A GB3241957A GB865721A GB 865721 A GB865721 A GB 865721A GB 32419/57 A GB32419/57 A GB 32419/57A GB 3241957 A GB3241957 A GB 3241957A GB 865721 A GB865721 A GB 865721A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrazolone
- hydroxyethyl
- chloride
- amino
- prepared
- 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
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
- G03C7/38—Couplers containing compounds with active methylene groups in rings
- G03C7/384—Couplers containing compounds with active methylene groups in rings in pyrazolone rings
Abstract
1- (b -Hydroxyethyl)-3- [a -(p-palmitamidophenoxy) acetamido]-5-pyrazolone is prepared by refluxing the corresponding 3-[a -(aminophenoxy) acetamido]-5-pyrazolone in acetonitrile with palmitoyl chloride in the presence of N; p N-dimethylaniline, and hydrolysing the triacylated product with aqueous sodium or potassium hydroxide followed by acidification with acetic acid. The corresponding 3-[a -(2; 4-di-t (or n) amylphenoxy) acetamido]-, 3-palmitamido-, and 3-tetracosanamido-5-pyrazolones are similarly obtained from 1-(b -hydroxyethyl)-3-amino-5-pyrazolone by treatment with a -(2; 4-di-t (or n)- amylphenoxy) acetyl chloride, palmitoyl chloride or tetracosyl chloride respectively. 1-[b - 2; 4- Di-n (or t)- amylphenoxyacetoxy) ethyl]-3-(2; 4-di-n (or t)- amylphenoxyacetamido)-5-(2; 4-di-n (or t)- amylphenoxy acetoxy)- pyrazole is prepared by refluxing 1-(b -hydroxyethyl)-3-amino-5-pyrazolone in acetonitrile with 2; 4-di-n- (or t)-amylphenoxyacetyl chloride in the presence of N; N-dimethyl anilide. Hydrolysis of the product with 2 equivalents of sodium hydroxide in aqueous ethanol gives 1-(b -hydroxyethyl)-3-(2; 4-di-n-amylphenoxyacetamido)-5-pyrazolone. 1-(b -Octanoloxyethyl)-3-(2; 4-di-n-amylphenoxyacetamido)-5-(octanoyloxy) pyrazole is prepared by acylating the corresponding 1-(b -hydroxymethyl)-3-substituted-5-pyrazolone with 2 equivalents of octanoyl chloride. 1, 5-diacylated pyrazoles are similarly made from 1-(b -hydroxyethyl)-3-(21, 4-di-n-amylphenoxyacetamido)-5-pyrazolone using phenylacetyl chloride or phenoxyacetyl chloride as the acylating agent. 1-(b -Hydroxyethyl)-3-)p-[m-(2; 4-di-t-amylphenoxy-acetamido) benzamido] phenoxy-acetamido(-5-pyrazolone is obtained by treating 1-(b -hydroxyethyl)-3-(p-nitro-phenoxyacetamido)-5-pyrazolone with benzoyl chloride to give a dibenzoyl derivative, reducing the nitro group with hydrogen under pressure and palladium on charcoal catalyst, acylating the product with m-2; 4-di-t-amylphenoxyacetamido) benzoyl chloride, and hydrolysing the triacylated compound with sodium hydroxide as above to remove the benzoyl groups. 1-(b -Phenyl (or methyl)- b -hydroxyethyl)-3-(p-nitro phenoxy acetamido)-5-pyrazolone is prepared by treating 1-(b -phenyl (or methyl)-b -hydroxyethyl)-3-amino-5-pyrazolone with one equivalent of p-nitrophenoxyacetyl chloride in acetonitrile. 1-(b -hydroxymethyl)-3-amino-5-pyrazolone may be similarly treated. The products may be reduced to the amino compounds with hydrogen under pressure, and the amino compound obtained from the 1-(b -methyl-b - hydroxyethyl)-3- substituted-5-pyrazolone may subsequently be reacted with 2; 4-dit-amylphenoxy-acetyl chloride to give 1-(b -hydroxypropyl)-3-[4-(2; 4-di-t-amylphenoxyacetamido) phenoxyacetamido]-5-pyrazolone. 1- (b - Benzoyloxyethyl)-3- benzamido-5-pyrazolone is prepared by acylating 1-(b -hydroxyethyl)-3-amino-5-pyrazolone with benzoyl chloride and hydrolysing the product with sodium hydroxide. 1-(b -Hydroxyethyl)-3- (p-nitrobenzamido)-5-pyrazolone is prepared by acylating 1-(b -hydroxyethyl)-3-amino-5-pyrazolone with 2-nitrobenzoyl chloride and hydrolysing the product with sodium hydroxide. 1-(b -Hydroxyethyl)-3-amino-5-pyrazolone is prepared by mixing b -hydroxyethylhydrabine and ethyl-b -ethoxy-b -iminopropionate in acetic acid. The corresponding 1-(b -phenyl (or methyl)-b -hydroxyethyl)-3-amino-5-pyrazolones are similarly prepared from b -phenyl (or methyl)-b -hydroxyethylhydrazine. Specifications 524,154, 524,554, 524,555, 536,577, 541,589, 649,660, 680,488, 843,497 and 865,720 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US619151A US2865748A (en) | 1956-10-30 | 1956-10-30 | 3-acylamido-5-pyrazolone and 3-acylamido-5-acyloxypyrazole couplers for color photography |
Publications (1)
Publication Number | Publication Date |
---|---|
GB865721A true GB865721A (en) | 1961-04-19 |
Family
ID=24480672
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB32419/57A Expired GB865721A (en) | 1956-10-30 | 1957-10-17 | Improvements in and relating to photographic colour development and photographic emulsions containing colour couplers |
Country Status (4)
Country | Link |
---|---|
US (1) | US2865748A (en) |
BE (1) | BE561952A (en) |
FR (1) | FR1196010A (en) |
GB (1) | GB865721A (en) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE560907A (en) * | 1956-09-18 | |||
US3498789A (en) * | 1967-03-13 | 1970-03-03 | Eastman Kodak Co | Photographic element having a novel filter layer thereon |
DE2336721A1 (en) * | 1973-07-19 | 1975-02-06 | Agfa Gevaert Ag | COLOR PHOTOGRAPHIC MULTI-LAYER MATERIAL WITH IMPROVED COLOR DENSITY |
DE2523882A1 (en) * | 1975-05-30 | 1976-12-16 | Agfa Gevaert Ag | LIGHT-SENSITIVE MATERIAL WITH NEW 3-ANILINO-5-PYRAZOLYLALKYL OR. -ARYLCARBONATE COUPLERS |
JPS5913730B2 (en) * | 1979-09-05 | 1984-03-31 | 富士写真フイルム株式会社 | Color image forming method |
US4283472A (en) * | 1980-02-26 | 1981-08-11 | Eastman Kodak Company | Silver halide elements containing blocked pyrazolone magenta dye-forming couplers |
US4310618A (en) * | 1980-05-30 | 1982-01-12 | Eastman Kodak Company | Silver halide photographic material and process utilizing blocked dye-forming couplers |
US4345085A (en) * | 1980-12-29 | 1982-08-17 | Eastman Kodak Company | Method for preparing 2-pyrazolin-5-ones from 1,2,4-oxadiazoles |
US4374253A (en) * | 1981-09-28 | 1983-02-15 | Eastman Kodak Company | Method for preparing 1-aryl-3-arylamino-2-pyrazolin-5-ones from N-aryl-3-arylamino-3-oximinopropionamides |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE531589A (en) * | 1953-09-02 | |||
BE542011A (en) * | 1954-10-14 |
-
0
- BE BE561952D patent/BE561952A/xx unknown
-
1956
- 1956-10-30 US US619151A patent/US2865748A/en not_active Expired - Lifetime
-
1957
- 1957-10-17 GB GB32419/57A patent/GB865721A/en not_active Expired
- 1957-10-28 FR FR1196010D patent/FR1196010A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
US2865748A (en) | 1958-12-23 |
BE561952A (en) | |
FR1196010A (en) | 1959-11-20 |
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