GB605724A - 4, 4-bis (pyrazolone) couplers for colour photography - Google Patents
4, 4-bis (pyrazolone) couplers for colour photographyInfo
- Publication number
- GB605724A GB605724A GB23658/45A GB2365845A GB605724A GB 605724 A GB605724 A GB 605724A GB 23658/45 A GB23658/45 A GB 23658/45A GB 2365845 A GB2365845 A GB 2365845A GB 605724 A GB605724 A GB 605724A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrazolone
- bis
- sulphonic acid
- phenyl
- methyl
- 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
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)
- Cosmetics (AREA)
Abstract
Compounds of the formula <FORM:0605724/IV(b)/1> wherein R represents H or an alkyl, aryl, arylamino, acetarylamido, or aralkyl group, and R1H or an alkyl, aryl, aralkyl, or heterocyclic group are prepared by refluxing together the corresponding mono-pyrazolone with phenylhydrazine. R may be methyl, ethyl, propyl, butyl, octyl, decyl, heptadecyl, octadecyl, stearyl or other alkyl radical containing up to 24 carbon atoms, carbalkoxyalkyl (e.g. acetic ethyl ester), alkoxycarboxy (e.g. carbomethoxy, carbethoxy and carbopropoxy), phenyl, naphthyl, anthranyl, diphenyl, benzyl, methylbenzyl, ethylbenzyl, amylamino, acetanilido, acetanisido, acetdimethylanilido, acetnaphthylamido, or sulphamylphenylamino, and R1 may be one of the alkyl, aryl, or aralkyl specified for R or thiazolyl, benzthiazolyl, quinolyl, pyridyl, or naphthathiazolyl. The alkyl, aryl, aralkyl, or amino substituted aryl radicals given for R and R1 may be substituted by chlorine, bromine, iodine, acetamido, imino, nitro, alkoxy (e.g. methoxy, ethoxy, propoxy, or butoxy), amino (e.g. primary amino, secondary amino such as methylamino and phenylamino, or tertiary amino such as dimethylamino or diphenylamino), sulphonamino, sulphonic acid, or carboxylic acid groups. 4 : 41-Bis-(phenyl-3-methyl-5-pyrazolone) is prepared by refluxing together 1-phenyl-3-methyl - 5 - pyrazolone and phenylhydrazine. 4 : 41-Bis-(3-methyl-5-pyrazolone), 4 : 41-bis-(1-phenyl-3-phenyl-5-pyrazolone), 4 : 41-bis-(1-p-tolyl-3-methyl-5-pyrazolone), 4 : 41-bis-(1-41-ethoxyphenyl-3-methyl-5-pyrazolone), 4 : 41-bis-(1-41-nitrophenyl-3-methyl-5-pyrazolone), 4 : 41-bis - (1 - (-naphtyl-41-sulpho)-3-methyl-5-pyrazolone), 4 : 41-bis-(1 - 41-sulphophenyl-3-methyl-5-pyrazolone), 4 : 41-bis-(1-phenyl-3-heptadecyl-5-pyrazolone), 4 : 41-bia-(1-41-sulphophenyl-3-heptadecyl-5-pyrazolone), 4 : 41-bis-(1-phenyl-5-pyrazolone-3-acetic ethyl ester), 4 : 41-bis-(1-b -naphthyl-3-p-chloroacetanilido-5-pyrazolone), 4 : 41-bis-(1-phenyl-3-acet- -naphthylamido-5-pyrazolone), 4 : 41-bis-(3-anilino-5-pyrazolone), 4 : 41-bis-(1-phenyl-3-p-anisylamino 5-pyrazolone), 4 : 41-bis-(1-31-carboxyphenyl-3-heptadecyl-5-pyrazolone), 4 : 41-bis-(1- -quinolyl-3-anilino-5-pyrazolone), and 4 : 41-bis-(1-ethanesulphonic acid - 3 - methyl - 5 - pyrazolone) are similarly prepared. Other bis-pyrazolones referred to are 4 : 41-bis-(1-x-naphthyl-3-methyl-5-pyrazolone), 4 : 41-bis-(1-bromophenyl-3-methyl-5-pyrazolone), 4 : 41-bis-(1-phenyl-3-acetanilido-5-pyrazolone), 4 : 41-bis-5-pyrazolone, 4 : 41-bis-(1-phenyl-3-p-chloracetanilido-5-pyrazolone), 4 : 41-bis-(1-b -naphthyl-3-acetic ethyl ester-5-pyrazolone), 4 : 41-bis-(1-b -naphthyl-3-acet-o-anisido-5-pyrazolone), 4 : 41-bis-(1-p-tolyl-3-(acet-21 : 41-dimethylanilido)-5-pyrazolone), 4 : 41-bis-(1-acetyl-3-anilino-5-pyrazolone), 4 : 41-bis-(3 - o - bromanilino - 5 - pyrazolone), 4 : 41-bis-(3-n-amylamino-5-pyrazolone), 4 : 41-bis-(1-benzoyl-3-anilino-5-pyrazolone), 4 : 41-bis-(1-phenyl-3-anilino-5-pyrazolone), 4 : 41-bis-(1-phenyl-3-p-sulphamylphenylamino-5-pyrazolone), 4 : 41-bis-(1-phenyl-3-p-(p-tert.-amylphenoxy) - phenylamino - 5 - pyrazolone), 4 : 41-bis-(1-31-sulphophenyl-3-heptadecyl-5-pyrazolone), 4 : 41-bis-(1-31-carboxyphenyl-3-undecyl-5-pyrazolone), 4 : 41-bis-(1-ethanesulphonic acid-3-p-nitrophenyl-5-pyrazolone), 4 : 41-bis-(1-ethanesulphonic acid-3-heptadecy-5-pyrazolone), 4 : 41-bis-(1-21-benzthiazolyl-3-anilino-5-pyrazolone), 4 : 41-bis-(1- -pyridyl-3-anilino-5-pyrazolone), 4 : 41-bis-(3-methyl-5-pyrazolone), 4 : 41-bis-(1-(21-methylphenyl-51-sulphonic acid - 3 - heptadecyl - 5 - pyrazolone), 4 : 41-bis-(1-(21-methoxyphenyl-51-sulphonic acid)-3-(31-stearylaminophenyl)-5-pyrazolone), and 4 : 41-bis-(1-(21-phenoxyphenyl-31-sodium sulphonate)-3-heptadecyl-5-pyrazolone). 4 - Nitrophenoxybenzene - 2 - sulphonic acid is prepared by boiling together 1-chloro-4-nitrobenzene-2-sulphonic acid, phenol, sodium carbonate and water. 4 - Aminophenoxybenzene-2-sulphonic acid is prepared by reducing 4-nitrophenoxybenzene-2-sulphonic acid with iron and HCl. 4-Phenoxyphenylhydrazine-3-sulphonic acid is prepared by reducing diazotized 4-aminophenoxybenzene-2-sulphonic acid with sodium bisulphite and potassium hydroxide and heating with HCl. 1 - (41-Phenoxyphenyl-31-sulphonic acid)-3-heptadecyl-5-pyrazolone is prepared by heating 4-phenoxyphenylhydrazine-3-sulphonic acid with ethyl stearyl acetate and glacial acetic acid. 2 - Methylphenylhydrazine - 5 - sulphonic acid (from 2-methylaniline-5-sulphonic acid), 1-(21-methylphenyl-51-sulphonic acid)-3-heptadecyl-5-pyrazolone, 2-methoxyphenylhydrazine-5-sulphonic acid, 1-(21-methoxyphenyl-51-sulphonic acid)-3-(31-nitrophenyl)-5-pyrazolone (using ethyl 3-nitrobenzoylacetate), 1 - (21-methoxyphenyl-51-sulphonic acid)-3-(31-aminophenyl)-5-pyrazolone, and 1 - (21-methoxyphenyl-51-sulphonic acid)-3-(31-stearylaminophenyl)-5-pyrazolone are similarly prepared. 1-(21-Benzthiazolyl)-3-amino-5-pyrazolone is prepared by refluxing together 2-benzthiazolylhydrazine, ethyl cyanacetate, sodium methylate and ethanol. 1-(21-Benzthiazolyl)-3-anilino-5-pyrazolone is prepared by refluxing together 1-(21-benzthiazolyl)-3-amino-5-pyrazolone and aniline. 1-(a -Quinolyl)-3-amino-5-pyrazolone, 1-(x-Quinolyl)-3-anilino-5-pyrazolone, 1-(a -pyridyl)-3-amino-5 pyrazolone, and 1 - (x-pyridyl)-3-anilino-5-pyrazolone are similarly prepared. 1-(-Naphthyl-41-sulphonic acid)-3-methyl-5-pyrazolone is prepared by condensing a -naphthylhydrazine-4-sulphonic acid with ethyl acetoacetate.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US556273A US2411951A (en) | 1944-09-28 | 1944-09-28 | 4,4'-bis (pyrazolone) couplers for color photography |
Publications (1)
Publication Number | Publication Date |
---|---|
GB605724A true GB605724A (en) | 1948-07-29 |
Family
ID=24220639
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB23658/45A Expired GB605724A (en) | 1944-09-28 | 1945-09-13 | 4, 4-bis (pyrazolone) couplers for colour photography |
Country Status (3)
Country | Link |
---|---|
US (1) | US2411951A (en) |
DE (1) | DE885197C (en) |
GB (1) | GB605724A (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2691659A (en) * | 1954-10-12 | Process for preparation of | ||
BE516241A (en) * | 1951-12-15 | |||
GB784422A (en) * | 1955-01-29 | 1957-10-09 | Ilford Ltd | Improvements in or relating to colour photography |
BE572971A (en) * | 1957-11-14 | |||
CA2696016A1 (en) * | 2007-07-13 | 2009-01-22 | Addex Pharma S.A. | Novel heteroaromatic derivatives and their use as positive allosteric modulators of metabotropic glutamate receptors |
CN102180833B (en) * | 2010-07-29 | 2012-05-30 | 南京长澳医药科技有限公司 | Preparation method and detection method for edaravone dimer and tautomer thereof |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB513596A (en) * | 1938-04-08 | 1939-10-17 | John David Kendall | Improvements in and relating to the production of coloured photographic images by colour development |
-
1944
- 1944-09-28 US US556273A patent/US2411951A/en not_active Expired - Lifetime
-
1945
- 1945-09-13 GB GB23658/45A patent/GB605724A/en not_active Expired
-
1949
- 1949-01-01 DE DEP29295A patent/DE885197C/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
US2411951A (en) | 1946-12-03 |
DE885197C (en) | 1953-08-03 |
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