GB880862A - Improvements in or relating to the production of coloured photographic images - Google Patents
Improvements in or relating to the production of coloured photographic imagesInfo
- Publication number
- GB880862A GB880862A GB3960856A GB3960856A GB880862A GB 880862 A GB880862 A GB 880862A GB 3960856 A GB3960856 A GB 3960856A GB 3960856 A GB3960856 A GB 3960856A GB 880862 A GB880862 A GB 880862A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- methyl
- pyrazolone
- pentadecyl
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
- C07D231/48—Oxygen atom in position 3 or 5 and nitrogen atom in position 4 with hydrocarbon radicals attached to said nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
- C07D231/50—Acylated on said nitrogen atom
-
- 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
- G03C7/18—Processes for the correction of the colour image in subtractive colour photography
-
- 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
- G03C7/34—Couplers containing phenols
- G03C7/344—Naphtholic couplers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Abstract
2 - Phenyl - 3 - methyl - 4 - amino - pyrazolone - 5 is prepared by reducing the corresponding 4-phenylazo derivative with hydrogen and a nickel catalyst. Similarly, 1-benzoyl-2-phenyl-3-methyl- and 1-phenylsulphonyl-2-phenyl-3-methyl-, 4-phenylazo-5-pyrazolones are reduced to the corresponding 4-amino compounds. 2 - p (a - hexadecenyl - succinylamido) phenyl - 3-methyl-4-amino-pyrazolone-5 is similarly prepared from the 4-phenylazo compound using palladium as catalyst. Reduction of 1-phenyl-3 pentadecyl-4-phenylazo-5-pyrazolone with zinc in acetic acid and acetic anhydride gives the 4-diacetylamino derivative. 1 - phenyl - 2 - hexadecyl - 3 - methyl - 4 - amino-5-pyrazolone is prepared by treating 1-phenyl-2-hexadecyl-3-methyl-5-parazolone with sodium nitrite and concentrated hydrochloric acid to give the 4-nitroso compound and reducing this with hydrogen and nickel catalyst. Similarly, 1 - phenyl - 2 - methyl - 3 - pentadecyl -, 1 - phenyl - 2 - methyl - 3 - [m - (a - hexadecenyl - succinyl - amido) phenyl]-, and the methyl ester of 1-[ - p (succinylamido) phenyl] - 2 - methyl - 3 - pentadecyl-, 5-pyrazolones are converted to the 4-nitroso compounds which are then reduced to the 4-amino compounds (in the latter mentioned case with zinc and hydrochloric acid). 1-Benzoyl-(or 1-phenylsulphonyl) 2-phenyl-3-methyl-4-phenylazo-5-pyrazolone is prepared by adding benzoyl chloride (or benzene sulphonyl chloride) to 2-phenyl-3-methyl-4-phenylazo-5-pyrazolone in the presence of aqueous sodium hydroxide. 1- Phenyl - 2 - hexadecyl - 3 - methyl - 5 - pyrazolone is prepared by fusing 1-phenyl-3-methyl-5-pyrazolone with cetyl-p-toluene sulphonate. Similarly, 1-phenyl-3-pentadecyl-(or 3-p-nitrophenyl) and in 1-p-nitrophenyl-3-pentadecyl-4-pyrazolones are fused with methyl-p-toluene sulphonate to give the 2-methyl derivatives. 1-Phenyl-2-methyl-3-p-nitrobenzoylamino-5 - pyrazolone is prepared by adding p-nitrobenzoyl chloride and aqueous sodium hydroxide to 1 - phenyl - 2 - methyl - 3 - amino - 5 - pyrazolone. The product is reduced to the 3-p-aminobenzoylamino derivative with H2 and nickel catalyst and then reacted with a -hexadecenyl succinic anhydride to give the 3-[p-(a -hexadecenylsuccinylamido) benzoylamino]-5-pyrazolone. By reacting this with the diazonium sulphate from p-chloroaniline and reducing with zinc and hydrochloric acid, 1 - phenyl - 2 - methyl - 3 - [p - (a - hexa - decenylsuccinylamido) benzoylamino] - 4 - amino - 5-pyrazolone is formed. 2-p-nitrophenyl-3-methyl-5-pyrazolone is prepared by adding phosphorus trichloride to a -acetyl-b -(p-nitrophenyl)-hydrazine and acetoacetic acid ethyl ester. The product is reduced to the 2-p-aminophenyl derivative with H2 and nickel catalyst and then reacted with a -hexadecenyl succinic anhydride to give the 2-[p-(a -hexadecenylsuccinylamido) phenyl]-5 - pyrazolone. By reacting this with the diazonium sulphate from dichloroaniline, 2-[p-(a -hexadecenylsuccinylamido) phenyl] - 3 - methyl - 4 - dichlorophenylazo - 5-pyrazolone is obtained. Similarly, 1-phenyl-2-methyl - 3 - p - nitrophenyl - 5 - pyrazolone is reduced with hydrogen and nickel and reacted with a -hexadecenyl succinic anhydride to give 1- phenyl - 2 - methyl - 3 - [p - (a - hexadecenyl - succinylamido) phenyl] - 5 - pyrazolone; and 1 - p - nitrophenyl-2-methyl-3-pentadecyl-5-pyrazolone is similarly reduced and treated with b -carbomethoxy-propionyl chloride to give 1-[p-(b -carbomethoxy-propionylamino) phenyl]-2-methyl-3-pentadeceyl-5-pyrazolone. 1 - Phenyl - 2 - methyl - 3 - pentadecyl - 4 - carbethoxyamino-5-pyrazolone is prepared by reacting the 4-amino derivative with chloroformic acid ethyl ester. 1- p - nitrophenyl - 3 - pentadecyl - 5 - pyrazolone is prepared by refluxing p-nitrophenyl hydrazine with palmitoyl acetic acid methyl ester in iso propanol. 1 - Phenyl - 3 - pentadecyl - 4 - phenylazo - 5 - pyrazolone is prepared from 1-phenyl-3-pentadecyl-5-pyrazolone and a diazinium salt of aniline. 1 - Phenyl - 2 - (a - sulphopropyl) - 3 - penta - decyl-4-amino-5-pyrozolone is prepared by treating 1 - phenyl - 3 - pentadecyl - 4 - diacetylamino - 5 - pyrazolone with n-propane sultone and then hydrolysing the acetyl groups.
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE563474D BE563474A (en) | 1956-12-31 | 1957-12-24 | |
US705508A US3012884A (en) | 1956-12-31 | 1957-12-27 | Production of colored photographic images |
FR1207422D FR1207422A (en) | 1956-12-31 | 1957-12-30 | Process for the production of color photographic images |
DEG23643A DE1063900B (en) | 1956-12-31 | 1957-12-31 | Process for the preparation of color masked photographic color images by color development |
US70914A US3013879A (en) | 1956-12-31 | 1960-11-22 | Production of color photographic images |
GB23203/61A GB975930A (en) | 1956-12-31 | 1961-06-27 | Improvements in or relating to the production of coloured photographic images |
FR874185A FR81106E (en) | 1956-12-31 | 1961-09-26 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEG30580A DE1119666B (en) | 1960-09-27 | 1960-09-27 | Process for the preparation of color masked photographic color images by color development |
Publications (1)
Publication Number | Publication Date |
---|---|
GB880862A true GB880862A (en) | 1961-10-25 |
Family
ID=7124049
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3960856A Expired GB880862A (en) | 1956-12-31 | 1956-12-31 | Improvements in or relating to the production of coloured photographic images |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE1119666B (en) |
GB (1) | GB880862A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113058529A (en) * | 2021-03-30 | 2021-07-02 | 河北冀衡药业股份有限公司 | Continuous preparation method of 4-nitrosoantipyrine |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1282458B (en) * | 1964-10-03 | 1968-11-07 | Wolfen Filmfab Veb | Process for producing color corrected color photographic images |
-
1956
- 1956-12-31 GB GB3960856A patent/GB880862A/en not_active Expired
-
1960
- 1960-09-27 DE DEG30580A patent/DE1119666B/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113058529A (en) * | 2021-03-30 | 2021-07-02 | 河北冀衡药业股份有限公司 | Continuous preparation method of 4-nitrosoantipyrine |
CN113058529B (en) * | 2021-03-30 | 2023-01-31 | 河北冀衡药业股份有限公司 | Continuous preparation method of 4-nitrosoantipyrine |
Also Published As
Publication number | Publication date |
---|---|
DE1119666B (en) | 1961-12-14 |
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